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The School Tramp

(From "Boy" to " Boy oh Boy!!")

Chapter 1 - The School Tramp

I was a virgin. I did not want to be a virgin. I asked my sister for help, and that was a mistake. Well, at the time I thought it was a mistake, but it turned out to be the best mistake that I ever made.

I was nineteen years old at the time and entering my junior year of high school. Yes, my junior year. I had been very sick when I was six and had missed two years of school. So, when I started my junior year, my sister who was only eighteen was starting her senior year at the same high school. Heck, Bigelow was such a small town that there was only one high school.

As a result of being sick, I was also much smaller than would be expected. I was only five foot four, and while I was quite strong for my size, I looked very thin and, yes, you guessed it, even a bit effeminate - or cute, as my sister constantly reminded me. She kept telling me I would make a much better younger sister, rather than older brother. She'd always had that idea in her head and that is where the mistake comes in, but I will get to that in a minute.

Back to being a virgin, and not wanting to be a virgin....

Becky Winters was the school tramp. She was a senior and was supposedly Dwight Moore's girlfriend. Dwight was the star receiver on the football team. But everyone knew that Becky would put out for anyone who took her on a date. It was said that she'd had sex with almost all the guys in the Senior class and over half of the guys in the Junior class. She was also supposed to have blown or fucked over half of the male teachers at the school, including the principal and vice-principal.

I said she'd had sex with over half of the guys in the Junior Class., right? Well, I was not one of them. I was too shy around girls, partly due to my height, and just because, well, I was a geek, a nerd, a nobody. My school marks were terrific - but that was because I had no personal life. I did not go out for any sports, I did not go to school dances or any social events. I was too shy. My only friends were the other guys who were called geeks and nerds by the supposedly hip, cool kids who hung out front of the school smoking all day.

I spent a couple days after school in the Chess Club and Math Club with a half dozen other shy and awkward guys. I spent my weekends in my bedroom studying so I could go to University in a couple years, or playing video games online with the geeks from elsewhere who never went outside. Also, I had discovered online porn recently and had easily figured out how to not leave any trace for mom to find when she periodically checked the sites I was visiting. Looking at the pictures, and the videos, made me finally realize that there was something missing in my life.

I could not talk to a girl unless she talked to me first. I'd had exactly one date in my whole life and that was with my cousin, Lucille, when her family visited ours last Christmas. And that was a humiliating experience that I will not explain further.

I was determined to end my virginity and the best way to do that, I figured, was to go out on a date with Becky Winters. I was convinced that if I did, I would finally get my cock inside a pussy! I was too shy to ask Becky out though and so I asked my sister to help me out, by speaking to Becky for me.

I haven't told you about my sister Cassandra yet, have I? As I said, Cassie had just turned eighteen in the summer. She stood five foot eight, had long black hair and a gorgeous face. Cassie had been dating Johnny Long, the quarterback of the football team for the past two years. (And yes, predictably, Cassie is the head cheerleader.) As of a month ago, she had been wearing Johnny's school ring and the two of them had been fucking like animals in her bedroom a couple nights a week ever since.

Mom took Cassie to the doctor and made sure she was on the pill. Mom was very open minded and realized that her horny daughter would be banging away with one or more boys as soon as she was of age and so she made sure her daughter was well protected.

Mom had even bought me a box of condoms and had THAT awkward conversation with me when I turned eighteen last year. Dad had run out on us when I was only ten and so Mom struggled with raising her two kids. (Mom said he had run off with a woman from the next town, but I had been taunted recently by the Barlow twins who told me that their dad had said my dad was a fruit and had run away with another man!)

I'm pretty sure she was disappointed in me for NOT bringing any girls back to my room, but she never said so, in so many words.

Oh, my name is Carl by the way; Carl Barton.

So anyway, I asked Cassie to get me a date with Becky, the school tramp. I even told her that I wanted the date so that I could lose my virginity. Cassie giggled and turned things around on me.

She turned it into a bet. It doesn't matter what the wager was, just the stakes - If I won, then she would set me up on a date with Becky, and would guarantee that I would have sex with her; and if I lost... well, if I lost then she should set me up with the date of HER choice and I would have to do whatever she said on the date, but she would also guarantee that I would have sex.

So, either way I would lose my virginity!

A no lose bet, right? More like a no win bet, as it turned out!

Well I lost the bet of course, and so, no date with Becky Winters.

But it did explain why, the next Saturday night, I was dressed in a bra, panties, dark stockings, short short skirt, blouse and two inch heels, with a bracelet on my wrist and wearing clip-on earrings. I was wearing lipstick and eye shadow and my long blonde hair was conditioned and pulled back in a ponytail. I was carrying a small clutch purse which contained keys, lipstick, makeup compact and identification.

I was nervously waiting for my sister to come down and join me, to wait for our dates with Johnny and his out of town friend, Kenny.

Chapter 2 - The Date

When my sister told me I would be going on a date with a boy, it did not surprise me. She could be an evil bitch when she wanted to be (which was often!), and she had always told me I would look cute as a girl. She chose a weekend when Mom was out of town and then got her boyfriend Johnny to find me a date. The day of the date she spent a couple hours getting me ready. I won't bore you with the details except to tell you that after she was finished with me, I was definitely cute - more than cute! I was a knockout. The nerdy boy was gone and the hot girl was revealed.

I had to stop looking at myself in the mirror because I kept getting a hard-on in my panties. Not only did it not look becoming for a girl in a tight skirt to have a penis outline, but it kept leaving wet spots that took several minutes to dry!

The boys picked us up on time. Cassie introduced me as Sindy, her cousin. I thought she meant Cindy, but she emphasized that I spelled it with an S, as in Sin, since I was a naughty girl all the time! I blushed as Kenny's smile broadened.

We drove to our nearby big city, Springfield, twenty miles away. During the drive Cassie snuggled up to Johnny who drove and Kenny and I sat far apart in the back seat making idle conversation. Kenny was definitely cute himself, in a boy way of course and seemed a bit shy.

We stopped for burgers on the way and then went to a dance club. The music was seriously thumping inside! At the door we all got asked for ID. I nervously showed the bouncer my Carl ID. He looked me over, smiled, and waved us all inside.

The lights were flashing, the bass beat was so low that the floors vibrated, the dry ice was creating clouds of smoky steam on the dance floor. We grabbed a table and the boys went to buy us drinks. Cassie told me not be nervous and just enjoy the night out. I had never been to a place like this as a boy, and I was excited to be here. I sputtered at my first sip of my drink, never having had alcohol before. Kenny laughed. He was even more cute when he laughed.

He and I sat talking as Johnny and Cassie went to dance. After ten minutes I realized that Kenny was too shy to ask me to dance, so I grabbed his hand and dragged him to the dance floor. I had never danced in my life, but the small amount of alcohol emboldened me. I was going to enjoy myself, dammit!

We were on the dance floor for twenty minutes, that first time - and I ran back to the table several times for more of my drink. Kenny was actually fun to dance with and every once in awhile his hands would touch my wrist, or waist - never for long, but each time it sent a thrill through me.

When we all began to get tired, we returned to the table, but just for a moment. Cassie dragged me off to the powder room. Well, we didn't actually go to the washroom. Instead we went outside to the smoking area so that Cassie could have a nasty cigarette. While she smoked, she asked if I was having a good time, and did I like Kenny? I told her yes to both questions. She asked me if I liked Kenny enough to let him kiss me at the end of the date. I'd already been thinking of this, and told her yes.

When we went back inside, we discovered that our seats were taken up by a couple of Johnny's teammates and the boys were avidly talking with each other. Cassie bought us drinks and we took them up to the dance floor, put them on a sideboard, and danced with each other for the next half hour.

Well, not quite with each other, since other boys kept coming up and asking if they could dance with us. I found it quite fun dancing with different boys - tall ones, short ones. Heck a couple of them were at least in their thirties! These older guys all wanted to dance much closer and had their hands around my waist a lot of the time. I found it strangely stimulating to have guys touching me so much.

Two or three of the boys were friends of Cassie, from her senior class. Several of the boys asked if they could call me. I was too polite to say no, but I didn't give out my phone number - I didn't want them phoning Carl! I did let a couple of them give me their email addresses. And I even gave Cassie's email address to a really good looking guy named Jeremy. When I wanted to get out on a date again, he might be... wait, I was thinking of doing this again?!?

When I complained to Cassie that the heels were starting to hurt my feet, we went outside for a smoke break again. Cassie giggled at all the attention I was receiving and told me that even after a couple of hours, I was holding up well. My mind was buzzing from the three drinks I had had, and I had to admit that it had been fun flirting with the guys.

One of the girls who also out in the smoking area was Becky Winters, the school tramp who I had hoped to have a date with. I realized that I actually looked better than she did!. However she was smoking a cigarette and looking extremely slutty. I was jealous of that look. I was also jealous of her for having a man sitting beside her, his arm around her waist and his lips locked to hers every time she was not puffing on her cigarette.

I asked Cassie for a cigarette. She looked at me in amusement but handed me one. She lit it for me. I tried to hold the cigarette like Becky did, and inhaled for my first time. I then had a two minute hacking and coughing fit as Cassie laughed loudly. But I did finish my first cigarette and was determined to eventually be able to match that sexy look that Becky had!

Back inside, we danced with the boys some more. Kenny was now much bolder and held my hand a good deal of the time. I squeezed his hand several times and this made him smile a lot. At one point he held me very close and whispered that he was having a great time. I realized with a start that he had a boner and it was pressing against my thigh. I pulled back from him, because I realized that I too was hard in my panties and did not want to be pressing my own cock against him!

After awhile we changed partners and I was dancing with Johnny. Johnny was much more handsome than Kenny and a much smoother dancer. While Kenny looked at me with innocent eyes, Johnny stared at me with lust. As we danced, his hands caressed my arms and his hands touched my hips repeatedly. I was definitely getting hot and bothered dancing with Johnny. Deciding to be a bit of a tease, I actually let my hand slide along his pants and I gave his hard cock a subtle squeeze! Johnny gave a startled groan and grinned at me. I don't know if Cassie noticed my "handling" of her boyfriend, or if she was just tired, but she decreed that it was time for us to head home.

Cassie was staggering quite a bit. While I had had three drinks, she'd had at least twice that much, as well as some shots that various guys had bought her on the dance floor.

Chapter 3 - First Kiss, and more

As we drove home, Cassie was sitting as close to Johnny as the two front seats would allow. She was constantly kissing his neck and running her fingers through his hair. From the back it was hard to see what she was doing with her other hand, but it appeared to be in his lap.

In the back seat, Kenny and I were sitting side by side with every part of my right side, up tight against his left side. We were holding hands and talking in small whispers.

After a prodding glance back from Cassie, I turned my head and kissed the shy Kenny on the lips. He kissed me back eagerly. I had never kissed anyone like this before and did not care that my first kiss was with a boy. Soon our hands were caressing each other's bodies as we mashed lips hungrily. I soon found Kenny's tongue in my mouth and our tongues jostled and played with each other as we took turns sucking on each other's tongues!

A few minutes later Johnny pulled off the highway and parked the car along a dark country road. Evidently he and Cassie were very familiar with this spot. My sister and her boyfriend were soon exchanging their own deep kisses. Meanwhile, I found myself laying on the back seat with Kenny lying on top of me. As we continued to kiss, he worked his hand under my blouse and unsnapped my bra. Shortly after, my blouse was undone and Kenny was licking at one of my nipples.

Of course, being a boy, I was flat chested, but Kenny did not seem to mind. As he flicked his tongue across first one and then the other nipple, they stood up firmly pert. I groaned and Kenny moved up and covered my mouth with his own as his fingers continued to tease my nipples. I could not see what Cassie was up to in the front seat, but by her position I assumed that her head was buried in Johnny's lap, meaning she was probably sucking on his cock.

Well, in for a penny, in for a pound! I could feel Kenny's hard cock pressing against my thigh, and I had quite the stiff rod of my own. I didn't need Kenny shifting position and suddenly feeling my dick pressing against him, so I flipped us around such that I was on top. Kenny put up no protest as I undid his belt, and then his zipper, pulled down his pants and then his underwear.

Kenny's cock sprang erect. It was about five inches long and already very messy with all the precum he had been leaking. Kenny muttered something like, oh yeah babe, suck it! Cassie's head briefly rose up and she looked back at me, grinning broadly and nodding at me to go ahead. She watched as my lips slid down on a cock for the very first time, giggled, and then went back to her own cocksucking.

I was a boy, dressed as a girl. Should I have been doing this?

Um, let me put that another way.

I was a nerdy boy, dressed as a hot girl! From the moment I saw Sindy in the mirror, I knew I was going to enjoy being a girl for the night, much more than I had ever enjoyed being a boy. I had decided I would do whatever it took to have the best time possible. I liked Kenny, and I was eager to be the best girl I could be for him.

I eagerly kissed, and slurped and sucked on his cock. I bobbed my head up and down and swirled my tongue along that nice warm stick of meat. I had never had a blowjob, but had watched several on my computer. II knew what felt right. Kenny guided me with his grunts and his groans, and his hands were holding my head at times.

As I bobbed my head up and down, I looked forward again and realized that Johnny had adjusted the rear view mirror so that he could watch the rear seat action. I gazed directly into his eyes as I took Kenny's cock from my mouth and kissed the head. I then blew a kiss at Johnny who grinned and winked at me. Cassie still seemed to have her head in Johnny's lap, but appeared to not be moving.

Moments later, Kenny started breathing hard. His leg muscles went rigid and he panted that he was cumming! I held just the head of his cock in my mouth as he spurted three strong jets of cum into my mouth. Without thought, I swallowed his cum and then I licked the rest of his juices off of his dick head. As we straightened up our clothing, I noticed that Kenny was no longer interested in kissing me. I guess he did not like my cum breath!

Johnny was arranging Cassie in her seat. Apparently the alcohol had gotten to her and she had passed out with his cock in her mouth.

It was a short drive back to Bigelow. We dropped Kenny off at the house of the friends he was staying with. I got out of the car and we hugged (no goodnight kiss!). He asked if we could call me when he came to town again. I said that it would depend on if I was visiting Cassie at the same time. He gave me his email address, and I gave him Cassie's. He kissed me on the cheek.

Back in the car, Johnny and I were both silent and Cassie was passed out. When we got to my house, I helped Johnny get Cassie out of the car, and he took her upstairs. Since they had been lovers for a couple months now, I had no problem with him stripping her and putting her to bed.

I waited up to say goodnight to Johnny. I assumed he was not going to stay over, since Cassie was in no shape to have headboard thumping sex with him. As I waited I scrounged in Cassie's purse for a cigarette, and I grabbed a coke from the fridge.

Chapter 4 - Johnny

When Johnny came back downstairs he was feeling chatty, so I handed him another coke and we sat on the couch, side by side. I explained that I would be sleeping on the couch while visiting my cousins. My aunt was out of town, Cassie was sound asleep in her room and, I assumed, Carl was asleep in his. Johnny made as if to get up and leave, but I told him to sit down, I enjoyed his company.

We chatted about the evening and the club. I told Johnny I had a great time and that I had never been to a club like that "back home." He told me that I looked really hot, even better than Cassie had described when she asked him to set me up on a date. I told him that I thought he was pretty hunky and it was too bad that Cassie had dibs on him. I leaned in to him slightly and he met me halfway, our lips meeting in a delicious tender kiss.

For the next five minutes we kissed and sucked each other's tongues. My hands roamed over his strong back and then reached for his belt. I giggled and said that I noticed that Cassie had not finished sucking him off, coyly asking him if he would like me to finish the job for him? In reply, Johnny rolled down his jeans and underwear and spread his legs. For the first time in my life, but by no means the last, I knelt in front of a man and worshipped his cock.

Johnny had a nice firm seven inch dick and I eagerly engulfed it in my mouth. This was my second cock of the night and it seemed so much more alive - firmer, spongier, tastier. While I sucked up and down its length, my fingers toyed with Johnny's balls. Johnny moaned appreciatively and I could tell he was getting close to shooting his load. But then he pulled my head off of his cock.

Johnny pulled me up on his lap and I sat straddling him. His mouth hungrily found mine and we kissed passionately. I felt his rampant cock rubbing along my ass crack. Then he said, I want to fuck you, Carl!
He knew! He knew I was Carl, not Sindy. And he still wanted to fuck me! I stood, took his hand and led him up to my bedroom. He explained that he had known who I was all evening - Cassie had explained the bet and during the evening had expressed disbelief to Johnny at how easily I had passed as a girl.

I pushed Johnny onto my bed and took my clutch person into the upstairs bathroom. I spent five minutes touching up my lipstick and makeup. I nervously looked through the medicine cabinet and found an old jar of Vaseline which I took with me to my bedroom. Johnny was naked on my bed and he helped me to strip off my blouse, skirt and panties. When my erect cock bobbed into view, framed by my stockings, it did not phase him at all. We kissed some more as he lay me down on the bed.

Johnny pushed my legs back and used his fingers to massage some of the Vaseline around and into my asshole. As his fingers pushed inside of me, I felt an electric tingle. He lathered more lube onto his firm cock and then he lay down upon me. We kissed a great deal more until I was feeling comfortable and I told him I was ready.

I spread my legs wide as my man placed the head of his cock at the entrance to my ass and then he slowly pushed. At first my anal ring resisted, but suddenly the head was inside me. Johnny paused for a moment to give me a chance to get used to the feeling. Then he pushed some more and slid another couple of inches inside of me. I grunted at the pain, but nodded encouragement at him. He slid back out a bit and then in again, further. Slowly over the next couple of minutes, he worked his cock back and forth, in and out and I got used to the feeling of being so very full. At one point, his cock slid over something inside of me, and I saw stars! A minute later he did it again. I soon figured out how, and where, and each time Johnny fucked into me, I wriggled my bottom so that he rubbed against that same spot.

Johnny moaned, telling me that I was so fucking tight! He loved jamming his pecker into my sweet ass pussy, as he called it! I wrapped my legs around his back and pulled his head down for another delectable kiss. My man started fucking me harder and faster. I was moaning and shouting. My nails dug into his back at one point and he howled with pain.

I was moaning and cursing him as he pounded away at my ass, his cock rubbing hard along my pressure point. My own cock was rigid between us. Finally Johnny buried himself deep inside of me and I could feel his cum gushing into my ass. My man was seeding me!

Johnny collapsed on top of me and then moved his weight onto the bed beside me. His cock slipped out of my ass and lay on my thigh. We cuddled and kissed tenderly for several minutes.

After a few minutes Johnny got dressed and I walked him down to the front door. I was just wearing my stockings and heels, the rest of my girl clothes having been strewn around my room. My cock was limp. I kissed Johnny tenderly on the lips as he left.

I walked back up to my room, my ass hurting, but in a nice way, as I did so. I looked in on Cassie. She was fast asleep. Johnny's howls and my groans had not disturbed her drunken slumber.

I lay on my bed, recalling the evening. I had had a great time at the club, sucked off two boys and been fucked in the ass. What more could a girl ask for on her first date?

In all of the excitement of the evening, I had not cum myself. I returned to the bathroom and fixed up my makeup one more time. I then went to mom's room and sat at the end of her bed, looking at myself in the full length mirror. I lit another one of Cassie's cigarettes (I was going to have to get some of my own!). I still wanted to practise that wanton slut look that I had seen on Becky Winters. I posed a couple of different ways and practised blowing out the smoke provocatively. I giggled as I realized that I was trying to emulate the school slut!

As I stared in the mirror I saw a sexy blonde schoolgirl, dressed only in dark stocking and heels, with a cute cock sticking out from her groin. I grabbed hold of that cock and beat myself off. As I reached my climax, my cum geysered high into the air several times.

I slept well that night, dreaming of Johnny, and Kenny, and Jeremy, and oh so many other boys!

Chapter 5 - Lust

The next morning Cassie was groggy and could not remember how she got home and into bed. It was a relief to know that she did not have any memory of me banging her boyfriend. I told her I had had a great time. It was pretty obvious to her that Sindy was not just a one-date wonder. She hugged me and said she would enjoy having a part time sister!

I helped her to wash the clothes I had worn and in turn she sat down with me and gave me some tips on applying makeup. When she finished she dressed me in some of her smaller clothes, suitable for daytime wear and then she drove us in her car to the local cheap mall and I spent a couple hundred dollars of my savings on a bunch of girl clothes for me - some to be worn daytime, and some hotter outfits for evenings.

When we got home, Cassie had several emails from men trying to contact me. She gave me the email addresses. In my room I set up a separate hotmail account for Sindy and replied to two or three of the guys. One was Kenny, one was Jeremy who had caught my eye.

I was still walking uncomfortably at school on Monday, but by Wednesday my ass was fine. All I had were the memories of my glorious first ass fuck!

I saw a lot of Johnny during the week. He and Cassie were always together at school, always walking hand in hand. I found many excuses to talk to Cassie and each time Johnny smiled at me. Once we briefly touched fingers and my heart skipped a beat.

My email conversation with Kenny faded into nothing in a couple of days. He had gotten what he wanted from me. I was already learning about men!

But, I talked to Jeremy a few times by instant messenger online and agreed to meet him for a date on Saturday night. Cassie agreed to help sneak me out of the house, since Mom was going to be home. I spent a nervous hour putting on my makeup and then my panties, stocking, bra, dress and heels. I had bought a larger bra and filled a couple of balloons with bird seed to give me a larger bosom. I made sure to not fill the balloons very full, since I was still a developing girl!

Cassie helped me put my hair in a ponytail again and then distracted mom as I left the house and hid in the back seat of her car. Cassie came out and a couple blocks away I hopped into the front seat with her. We shared a cigarette as she drove me to my date.

Jeremy lived in Seneca, the next town over, and he met me at a small restaurant. Cassie drove off for her own date with Johnny.

We sat in a booth as we ate our meal and talked animatedly. I knew I looked pretty sexy and Jeremy had a hard time keeping his eyes off of me. We each had a drink, and then another - being a boy, Jeremy was drinking beer, but I had a margarita, then a cosmopolitan. Drinking girl drinks was fun! As the alcohol began to affect me, I scooted closer to Jeremy and was soon holding his hand under the table.

We then went to a movie at the town's multiplex. As we sat there in the dark, I was starting to feel horny and leaned over and kissed Jeremy on the lips. He squeezed my hand tighter and tentatively kissed me back. Fortunately the theatre was fairly empty and so no one was sitting behind us, to complain of us blocking their view. We ignored the rest of the movie and kissed and kissed. At one point, I rested my hand on Jeremy's pant leg, right on top of his rigid cock, and squeezed. For the next several minutes I massaged his dick and he squirmed and moaned in my mouth.

When the movie was done, we hopped into Jeremy's car and he drove to a dark laneway, where we resumed our kissing. I unzipped Jeremy's pants and grabbed hold of his cock. Thinking back, I realized that this had been my goal for the evening. I was eager to try sucking on another cock! I rolled my fingers around the glans a few times, but when I went to suck on it, I realized that my position was too awkward - Jeremy drove a manual transmission and the damn stick shift was in the way.

We hurriedly got into the back seat. Jeremy was such a sight, almost tripping over his pants! I then put his cock in my mouth and bobbed my head up and down hungrily. It took only five minutes until Jeremy pushed my head down hard on his dick and he splashed his cum down my throat. As we finished, I licked the rest of his cum off of his penis and teased the head with my tongue.

Back in the front seat, we held hands as Jeremy drove me to the local hotel, where I got out in order to get a cab home at the cab stand there. Much as I liked Jeremy, I was not ready to let him know where I lived. He was a gentleman and got out and opened the car door for me. As we parted I turned my head so he could kiss me on the cheek, but he instead gave me a full deep kiss on the lips, with tongue. This was a boy who did not mind kissing a gal with cum on her breath!

As I left the cab I looked at my watch. I was late enough that Mom was already in bed, but I still tip toed delicately upstairs to be sure I did not wake her. I stopped off in the bathroom to tidy up my makeup and then sat in my room, wondering why I was concerned about how I looked.

Fifteen minutes later, the door downstairs thumped open, and I could hear Johnny and Cassie coming home. Ten minutes after that there was a faint tapping at my door. I opened it a crack and peered out. It was Johnny. I let him in.

He smiled at me and then kissed me hungrily. I put my arms around him and we swapped tongues for the next five minutes. Johnny explained that he had made sure Cassie had a lot to drink, and she had passed out as soon as they got to her room. Blue balls again?, I asked Johnny. He nodded and a minute later I was on my knees with his beautiful cock between my lips. Five minutes later I was once again on my back on my bed, and my sweet man had his cock buried to the hilt in my ass. The first time we did this, we had sex. This time, we made love.

My eyes smouldered as I made small mewling sounds as his cock drove in and out of me. Johnny whispered about how beautiful I looked, and how fucking sexy I was. We made love face to face, alternating tender kisses and deep tongue probing kisses.

My cock was incredibly hard and bounced against each of our chests as Johnny thrust in and out of me. Johnny then surprised me by taking my cock in his hand and slowly running his hand up and down it, pausing to tease the head.

I had to stifle my groans of lust to be sure Mom did not hear me! But it was only moments until I huskily whispered, I'm going to cum! Johnny's balls were also churning, and just as my cock spurted its fuck cream, I felt Johnny let loose his own torrent of jism deep in my bowels! We both mewed our love for each other as we spurted our cummies!

It took fifteen minutes of cuddling for our heart rates to return to normal. Johnny's cock felt so delicious in my ass, even deflated, and I was disappointed when it finally slipped out of me.

Johnny quietly left of my room, and got back into bed with Cassie.

I removed the rest of my stockings, etc and went to the bathroom to clean off my makeup.

I was back in bed soon and trying to drift off to sleep. But I heard noises from the next room, which I realized was the head board banging against the wall. Cassie had evidently woken up and Johnny was now banging my sister.

I did not mind sharing Johnny with my sister. Or course, if she found out, she might not like sharing him with me!

Chapter 6 - Skulking around

On Monday at school Johnny managed to pass me a note asking me to put together a bag of clothes and makeup and meet him after classes the next day.

Now that football season was over, the cheerleaders were practising cheers for the basketball team. Johnny did not play basketball. So he had two hours when he was free from Cassie and he wanted to see Sindy!

When the final bell for the day rang, I got my Sindy bag from my locker and hopped in Johnny's car. We drove over to Seneca - just far enough away that it was unlikely any of our classmates would see us - and he got the key to a service station washroom. I spent 20 minutes changing clothes and putting on my makeup and lipstick.

We then drove to a local burger joint and had some food while holding hands. Well, we held hands for the first few minutes. After that I was eating my burger and fries with one hand, while my other hand was under the table, squeezing Johnny's cock through his jeans. It was fun watching him squirm and drip mustard from his burger onto his shirt. He got me back by smearing a bit of ketchup on my face when he kissed me between bites.

I had a raging hardon of my own in my panties which I tried to calm down when I went to the washroom to remove the ketchup and fix my lipstick.

The sun was setting early those days. On the drive back, Johnny found a laneway and we parked hidden from the main road. We kissed frantically for a few minutes and then Johnny suggested we get out of the car. He bent me over the trunk of the car and pulled down my panties. Back at the service station I had lubed up my ass. Johnny stood behind me and slowly pushed his cock into my ass. The previous times we had fucked I had been on my back on a bed. This was my first time being stuck from behind, and standing.

I missed kissing while fucking, but Johnny did get even deeper into me than he had before. Wow! And when I shimmied my ass, I was able to get him sliding along that pleasure point. I was seeing stars and he vigorously pounded into my ass pussy! Johnny grabbed hold of my hips and set to jack hammering into me. It only took five minutes and he was spurting into my bowels! My own cock was not stimulated by being squeezed against the hard metal of the car, but I was content, knowing that my man had used me so well!

We repeated this again on Thursday after school. That time a farmer drove by us on his tractor, and just waved as he watched the young stud hammer away at his blonde girlfriend!

Chapter 7 - Frat Boys

Earlier in the week I had told Cassie that I was eager to get out on the weekend again as Sindy but had not yet decided on who to go out with. As far as Cassie knew I had only been dressed as Sindy a couple of times and sucked off my dates each time. When I told her that I had let Jeremy fuck me in the ass (not true, it was Johnny, but I could not tell her that!), and I had liked it, her jaw dropped. She told me that she definitely had to watch me get ass fucked!

The next day she said that she had found a college guy to invite us to a frat house party on the Saturday night. Johnny was going to be off doing stuff with a bunch of his friends, so it would be a girls' night out for Cassie and Sindy, and she was sure that I would be able to get as much sex as I wanted!

Getting out of the house on Saturday night was easy. Mom had a date and was long gone by the time that Cassie and I were ready to go out. Cassie helped me pick out an outfit that was more risque (can you say slutty?) than any I had worn before. I was wearing a black waist cincher and a short black skirt over black stockings. My heels were four inches this time. Cassie did up my makeup to accentuate my dark eyes. My long hair was again pulled back in a ponytail.

I had found a piece of clothing called a gaff. A loop went around my penis head and I then pulled my cock back between my thighs, giving me a smooth front. No erections for me tonight, but also less chance of unsightly bulges.

The frat house was in Springfield and Cassie drove, but only after I got her to promise that she would not drink much - she had to be able to drive home!

We did each have one drink before we left. In the car, between cigarettes, Cassie pulled out a joint. I had never done any kind of drugs or such before (remember, as a boy, I was a geek!), but what the fuck, I was exploring my feminine side and so we shared a few hits and got a bit giggly as we drove to the party!

When we reached the frat house, there were several people entering and we had to wait because they were checking id and stamping hands of the people who were old enough to drink. (Once we were inside no one paid attention to the hand stamps, it was all part of some administration bullshit). The guy checking the identifications was a really cute, bulky blond guy. The only id that I had was my Carl driver's license. He looked at me in surprise as he looked more closely at my face. Then he told me his name was Danny and he looked forward to seeing me inside later. He also told me to be careful.

The frat house was huge. It had four floors and a basement. There had to be at least sixty people on the ground floor and I could see more going up and down the stairs. All the gals looked incredibly hot and they were all being pursued by guys. Cassie and I were barely inside the door when we were handed glasses of home made punch. I took a sip and the potent alcohol almost knocked my panties off!

For the next hour Cassie and I were chatted up by most of the guys in the place. The music was thumping and we danced with several guys. Most took the opportunity to paw me on the ass and grind their pelvises into my thigh. If I was not wearing the gaff, my own cock would have been rock solid from being around all these hunky men.

Cassie's objective for the evening was to watch me being fucked by a guy, and I was eager to get that happening. We could have both dragged just one guy up to a room, but Cassie was extremely horny herself. After about ninety minutes and several drinks, we found ourselves dancing with two hot studs who were both eagerly kissing us and fondling our butts. Cassie grinned and nodded at me. She took my hand and led me towards the stairs. We asked the boys if they wanted to join us in a private room upstairs, and they eagerly followed.

It took awhile to find an empty room. We found most doors locked. Those that were open already had a guy and girl fucking or sucking each other. But one of our studs actually lived here and we went up to his room on the third floor.

When we got in the room, the guys pushed us back on the beds and began kissing and groping us. After a couple minutes they got off of us and Cassie and I were laying there. My hand touched hers and she squeezed mine. The guys suggested that it would be pretty hot if we two girls made out with each other. Cassie grinned and pulled me to her, her mouth seeking mine. For the next five minutes we traded passionate kisses and our hands wandered each other's bodies. She pulled off her top and undid her bra and pulled my mouth to her tit. For the first time ever, I was sucking on a girl's nipple, and it was my sister's nipple! Cassie teased me by running her fingers along my trapped cock in my panties. I groaned against the teet in my mouth.

By this time the guys had their shoes, pants and underwear off. Cassie and I knelt in front of them, and eagerly took their rods into our mouths. Cassie was sucking on Dave's nice 7 inch member, but Bruce's cock in my mouth was a disappointing four inches.

Dave pulled Cassie up, pushed her on her back, whipped off her panties, and in moments had his dick deep in her pussy. He was grunting and groaning as he pumped away at her. Bruce pulled me to my feet, but I had to explain to him that I was on the rag that week, so he could not fuck my pussy - but he could have my ass if he wanted. His disappointed frown turned into an excited grin.

Cassie pushed her beau off of her, saying she needed to help me. I braced myself against one of the desks in the room. Cassie knelt, and flipped up my skirt and pulled my panties down enough to expose my lubed asshole, but still keeping my cock hidden. Bruce was eager to plunge in to me. Cassie took him in her mouth and bobbed her head on his cock a couple of times to add even more lubrication. She then guided his cock to my asshole and watched as the cock easily sank into my boipussy.
Cassie stared fascinated as Bruce pulled back and then sank deep inside me again. Well, as deep as a four inch cock would go. I loved the feel of a cock in my ass, but this one was frustratingly small!

Dave had Cassie lean against the desk beside me and he thrust his cock back into her hot quim. As the two frat mates pounded our butts side by side, Cassie and I held hands and kissed passionately, swapping tongues eagerly. Cassie's hand squeezed mine hard as she came twice in quick succession. I was frustrated though. Bruce was enthusiastic, but lacked any technique and no matter how much I wiggled, I could not get his cock rubbing across my prostate with any consistency.

One thing that I DID like though was that Bruce grabbed my long pony tail and wrapped it around his hand. He kept yanking on it while he was thumping away at my ass! This helped him get his tiny dick into me a bit deeper. I actually liked the feeling of being dominated in this way!

Dave and Bruce both grunted and groaned and then shouted as they came. When they were done, they both left the room quickly, telling us to pull the door closed behind us. Cassie and I rearranged our clothing. As we made our way back downstairs, Cassie told me how hot I had looked. She giggled as she pointed to the cum running down my leg from my messy panties!

Chapter 8 - Contest

When we reached the ground floor, it seemed like most of the party had vanished. But we followed noises and found the stairs to the basement. As we descended, my heels rapped loudly on the steps. I still marvelled that is was ME wearing those heels. A crying girl rushed past us going up the stairs, away from the crowd in the basement.

The basement was mostly one large room and there were about 70 guys and gals forming a circle. One girl knelt in the centre of the circle. A guy was standing in the middle, asking for a volunteer, since the other contestant had chickened out. Several guys were standing around the inside of the circle, looking very eager, but most of the girls were looking at the floor, trying not to be noticed. When the guy mentioned that the winning gal stood to win at least $400, Cassie pushed me from behind and I found myself stumbling into the centre of the circle!

I glared at Cassie as everyone in the room cheered. The guy led me to kneel down two feet away from the other gal. I looked at her and realized that it was Becky Winters, the high school tramp. She smiled at me and wiggled her fingers in a brief wave. I smiled back. I was sure she did not realize I was Carl Barton.

The organizer explained that we were going to have a blow job contest. Every guy who wanted a blow job had to put in twenty-five dollars and that went to the gal who managed to make him cum, regardless of whether she won or lost. Each of the spectators who was watching had to put in five dollars. The contest would last for twenty minutes, and whichever gal got the most guys to cum, got to take home the spectator money.

The interested guys put in their money, and they put their names in a hat. To be fair, names would be drawn at random. Oh, and one last thing said the guy in charge. In order to be sure that the guys actually came, there was no swallowing. The guys had to pull out and ejaculate on the girl's face!

Well, I had wanted more sex, and I was in for it now!

Names were drawn from the hat and the first two guys stepped forward. They dropped their pants and pulled their underwear down to their knees. Becky and I each had a limp cock hanging in front of our faces . Someone had a stop watch and when they shouted GO, I immediately drew that first cock into my mouth. It took me two minutes of sucking and fisting of that dick before the guy stuttered that he was coming and he pulled out of my mouth and shot three streams of cum onto my cheek. When the second guy stepped forward I saw that Becky had a rope of cum across her nose and was working on her second cock.

My second and third cocks were fairly small and I managed to get each of them off in three or four minutes each. The second guy squirted on my chin, but I forgot myself with the third and let him cum in my mouth. I swallowed before I remembered and so he did not count towards my total!

As my number four stepped up, the crowd all giggled and clapped. I looked over at Becky to see her mouth up against her man's groin. As I watched she pulled back and a seven inch cock emerged from her mouth. She had deep throated the guy. I had never tried that, but I knew I was going to have to do that soon - but not in the middle of a contest. Becky's face had a good coating of cum on it already.

At one point I noticed several people with their cell phones out, taking pictures. Cassie was one of them. I made sure to pose for her briefly at one point, with a cock poking solidly into my cheek and sticky ropes of cum across my nose and eyebrows!

My fourth cock was a nice six inches, but he shot pretty quickly. One squirt went into my hair, but two powerful jets of cum hit my left eye. I used my finger to clear my eye, and then licked the cum off my finger.

Two or three cocks later, I glanced at Becky again. I saw her working hard on her current cock. The guy she was sucking looked to be pretty drunk and I think he has having trouble staying hard. Becky pulled down her tube top and her large tits popped out. They were gorgeous breasts, though very round and obviously fake. But that just added to Becky's overall trampiness. Becky dragged the guy's cock across her nipples and moaned. Her guy needed no more than that as he suddenly shot his jism across her tits. Becky reached for her next cock as my next one stepped forward.

The guy with the stop watch told everyone that there were three minutes left and that Becky and I were tied with seven successful blowjobs each.

My next cock stepped forward. He was big. He was black. He was hung. I looked up into the eyes of Dwight Moore, Becky's boyfriend. Yes, Becky's boyfriend had not only brought her to a frat party where she was blowing strange cocks, but he was also participating by being sucked off by her competitor.

I could see why a tramp like Becky kept Dwight as her steady boyfriend. His cock was huge. Erect it was at least ten inches and seemed as thick as a soda can. I could barely fit the knob of his cock in my mouth! I ran my hands and tongue along the solid truncheon. I wondered if I would be able to fit that thing in my ass if he ever tried to fuck me!

But for the moment, I had to get him off! I twirled my tongue around his glans, and I sucked on the head of his dick while my hands pumped up and down his shaft. The crowd cheered as Becky's guy came, his cum dripping onto her cheek and nose. The crowd counted down the seconds to the end of the twenty minutes, urging me on. I had a hard grasp on Dwight's balls and could feel the tension in his legs, telling me that he was going to shoot, but time was called before he did.

I had lost, but I was not giving up. I continued to suck and spit on Dwight's shaft. Now that time was up and his girlfriend had won, Dwight was eager to shoot. He grasped my head and began to shove his cock into my mouth. My hands were gripping his ass tight as he finally shot a thick load and I eagerly swallowed bolt after bolt after bolt of hot jism.

I smiled as I stood. The crowd applauded and Becky hugged me. I was handed $175, including Dwight's money and Becky was given her suck money, plus $350 from the crowd. The organizer then offered us each twenty five dollars more if we would lick the cum off of each other's face. Becky declined, but I said I would do it if they gave me the whole fifty bucks. The guy nodded and for the next few minutes I eagerly licked all of the thick jism off of Becky's face, and the cum that had been splashed across her large fake tits. I managed to tease her nipples with my fingers which made her moan. I kissed her on the lips and she eagerly kissed me back.

Becky Winters, the school tramp, had kissed me!

I collected my extra fifty bucks and everyone moved upstairs to resume the party. I found an empty washroom, washed my face and touched up my makeup.

Chapter 9 - Danny

The party was in full swing again. Cassie and I got separated on the dance floor and I spent the next half hour dancing and talking with various guys. All the guys were showing a LOT more interest in me and it was hard to keep their hands off of my ass as we danced. Several asked me to go to a private room with them, but I just wanted to dance for awhile. At one point I found Cassie again. Her hair was dishevelled. I wiped a bit of cum off of her chin and had her lick my finger. She giggled and said she had just blown this really cute second year college student.

A few minutes later, I felt a tap on my shoulder and turned to face a grinning Danny. Remember, he was the guy checking id at the door? The one I said was hunky and cute? Well, he still was, and I felt my heart beat a bit faster as he asked me to dance. It took only three minutes for him to suggest that we go up to his room. With him I WAS in the mood. I asked if my cousin could come up with us, as she wanted to watch.

Once the three of us were in Danny's room and he had locked the door, Cassie plopped herself down in his desk chair, and Danny kissed me deeply. I wasted little time in getting on my knees, getting his cock out and jamming it into my mouth.

Cassie pulled her panties down and was slowly frigging her clit with the fingers of one hand, and was every once in awhile clicking pictures on her cell phone with the other. Danny quickly removed all of his clothing and I realized that below the eyebrows he was completely hairless. He had even removed all of the hair from his cock and the rest of his groin. I found the sight of his bare hairless cock highly intoxicating and I knew I was going to have to do the same to myself!

Danny made to remove my skirt and Cassie started to protest. But I told her to relax as Danny knew my secret. As he deftly removed my gaff and my cock sprung free after an evening of neglected torment, Danny admitted that he was gay. Danny pushed me back onto the bed and we fell into an embrace, kissing hungrily. I reached for his cock and he reached for mine. Johnny had briefly fisted my cock once when we made love, but other than that, this was the first time that another person had touched my prick. Danny's hand was both gentle and firm as he stroked me. I moaned in lust, and Danny moved down my body and took my cock into his mouth.

Another first! And oh god, did it feel so damn sweet to have his tongue and mouth moving up and down on my dick. Now I knew first hand why the guys liked it so much when I sucked them off!

Danny spun around and presented his own cock to my mouth. I enveloped it hungrily and we were soon both eagerly devouring each other's cocks. I heard Cassie get up and soon she was taking closeup pictures of my mouth bobbing on Danny's dick. I tried to get Danny's shaft into my throat, like I had seen Becky do, but I gagged and could not. I definitely needed practise before I was going to get a dick down in my throat!

My own cock was close to shooting and I told Danny. This made him bob his head on my cock more vigorously and shortly thereafter my back arched and I shot my thick load into his mouth. As I lay there panting he reversed position again and kissed me long and lovingly. He pushed my own cum into my mouth and we swapped it back and forth before each swallowing some of it..

Danny reached into his bedside drawer and pulled out a tube of lube. He squirted quite a bit on my asshole and worked it in with his fingers. He thrust first one, then two, then three fingers inside of me, and I realized it felt quite nice to be fingered by someone who knew what he was doing.

He had me kneel on his bed and squatted behind me. Cassie moved forward and took the lube and ran her fingers up and down Danny's cock, making it slick. Wanting a very close view, she then scooted underneath me, her groin at my head, and her head underneath my dick and balls. She squealed in excitement as, just inches above her face, Danny pushed his cock against my anus. The head popped in easily and he slowly sank his entire, beautiful, thick, juicy seven inches all the way into my ass.

Oh fuck, did that feel good!

Cassie oo'd and ah'd as she watched my asshole pucker outwards as Danny pulled back, my ass trying to hold on to the invader. Her left hand began to frig her clit again as her right hand squeezed my balls. I squirmed and she giggled.

For several minutes I was lost in pure bliss as Danny's steady strokes rubbed his thick rod against my prostate. I shivered in ecstasy. I needed both hands to steady myself against the persistent pounding. Danny had both of his hands on my hips steadying himself, so I was surprised when I felt another hand grasp my cock and start pulling and stroking it.

My own sister was jerking me off as a man pounded the shit out of my ass!

When Danny noticed this, he pushed my head downwards. My arms collapsed and I found myself with my face up against Cassie's muff. If sis was willing to fist my dick, I guess I had to be "polite" to her. I gave her cunt a few tentative licks. She moaned and used her free hand to push my face more firmly into her crotch.

But I had taken only a couple of licks before Danny changed things around. Grasping hold of me, he rolled over on his back. His cock slipped out of my ass. He told me to sit on his cock. This was new for me, being on top. I steadied his cock with one hand as I lowered myself on his dick. It slid inside me easily but when I bent down to kiss him it slipped out again. I turned around with my back to his face, and dropped onto his cock again. This time, he slid inside and stayed.

In fact, my weight dropping on his cock, drove his dick deeper into me than any cock had ever been before. With his strong hands under my thighs, Danny helped me to bounce up and down on his dick. I was seeing stars as his dick ran across my prostate.

Cassie was on the floor taking pictures of the lewd sight on me dressed as Sindy (well, undressed as Sindy!) bouncing up and down on a man's dick as my own stiff rigid rod bounced around wildly.

Suddenly Danny's strong hands held me positioned in mid air and he furiously rammed his cock in and out of me. He screamed that he was cumming and I felt my bowels being washed by his cum. My own dickie let loose and I fountained six or seven streams of goo high into the air.

We collapsed on the bed, both of us gasping for air. As we started to regain our breath, Danny reached into his bedside drawer again and pulled something out. As his softening cock slithered out of my ass, he pushed a butt plug up inside me. I had never seen one of these before (and would not actually see this one until I got home.) As he kissed me, Danny suggested that I keep the plug in my ass until I got home. That way I could enjoy the feeling of his cum sloshing around inside of me for awhile longer.

We were momentarily distracted by soft moans from the floor. Cassie had just frigged herself to her own climax, and collapsed giggling onto the carpet.

Danny and I exchanged email addresses before Cassie and I straightened ourselves up. Danny decided that he was just going to stay in his room for the rest of the night.

As Cassie and I descended once again to the ground floor, I was walking strangely, due to the plug in my ass. And of course, because of the pounding my ass had just taken.

The party was winding down and we decided to leave. We paused outside to each have a cigarette. As we smoked, Cassie told me that I had been utterly, fucking amazing! When she had suggested that I dress up for one date, she had never thought I would turn into such a cock hound! I blushed at the term, but had to admit to her that I enjoyed being a cock tease and was eager for more outrageous experiences! Carl had been boring for SO long. Sindy wanted excitement!

As we ground our cigarettes under our high heels, Cassie gave me a long passionate kiss and we swapped tongues hungrily. She gave my cock a gentle squeeze and then we hopped into the car.

On the way home, I made sure she stayed awake behind the wheel. At one point she confided in me that over the last few weeks Johnny had been hinting to her that he would like to try fucking her in the ass. She had no idea why that idea had suddenly come into his head (of course, I knew why!) and she had resisted any suggestions. But after watching me enjoy it so much......

My ride home had been a bit uncomfortable due to the butt plug in my ass. I had squirmed about on the seat a few times. When we got home I headed straight for the bathroom. It took me a few tries to properly grip the base of the plug so that I could pull it out. Thankfully I was sitting on the toilet because as I got the thing out, Danny's lovely cum slid out of my ass and into the bowl.

I washed off the plug and then brushed my teeth. As I did, I could feel the air wafting up into my ass. Lying in bed, I was very conscious of my ass gaping open. It was not an unpleasant feeling. As I drifted off to sleep that night, I tried to recall the number of guys I had had sex with, but kept losing track. God, I think I was becoming addicted to sex!

Chapter 10 - Revelations

The next week was eventful. Once again on Tuesday I met up with Johnny after school so that we could share a few moments of pleasure together. I think I enjoyed the kissing just as much as I did the feeling of his long cock stuffed up my pleasure canal! But I was feeling guilty about having sex with my sister's boyfriend. I needed a steady boyfriend of my own, or rather I needed a steady COCK of my own!

Danny looked to be a good candidate for a steady boyfriend, particularly because he had no problem with my cock. We began talking by email and tentatively set up a date for the next Saturday night.

On the Wednesday, I skipped out of my afternoon classes and Cassie took me shopping. I had my winnings, or rather "losings" from the blow job contest, plus some other money I had set aside. First visit was to one of her hair salons and Cassie convinced me to get my hair dyed just a bit more blonde with some silver highlights streaked through it. We also had my eyebrows tweezed a little bit into slightly more feminine arches. My nails were trimmed and buffed and a clear varnish applied. I liked the femme make over stuff, but still had to live my daily life as Carl.

Remembering how much I liked Danny's hairless groin, I also was brave and got a Brazilian wax - all the hair was stripped from my groin. That night when I got home, I posed in front of the mirror and admired my hairless cock and balls. There was something very erotic about the hairlessness and it did not take long before I pulled out my bottle of lube and knelt on the floor positioning the head of my dildo at my ass.

The dildo... one of my other purchases. Cassie and I bought me a couple more cute outfits, plus some accessories like fishnet stockings. Our final stop was an adult sex shop where we wandered around for awhile. I eventually purchased some flavoured lube, a couple of shemale DVDs from the discount bin and a seven inch rubber cock. I had always thought of dildos as being long plastic vibrators, and I was surprised to find realistic looking cocks. I wanted one to practise deep throating, but knew it would also end up in my ass a lot. The dildo came with a suction cup base.

So indeed that night, I had the dildo attached to my bedroom wall about eighteen inches off the floor and I pushed my ass back on to it and it sank slowly into my ass. For the next ten minutes I pounded my ass back and forth on the fake cock as I ran my hands along my hairless cock. My orgasm was great, but the whole experience left me empty. I needed a warm body attached to that cock!
Sadly, Johnny was not able to meet up with me on the Thursday night, so I spent that evening practising my deep throat technique on the dildo. I thought I was making good progress, but the rubber dick did not slide as easily past the pack of my throat as I imagined a real cock would. I resisted sticking the dildo to the wall and ramming my bottom back and forth on it, since Mom had a bunch of neighbours downstairs in the living room, and my groans and banging around might raise too much curiosity!

There was one negative aspect to the week. My grades. During the past several weeks Sindy had been taking over my life. My evenings were spent out on dates, or on the internet reading up on girl fashions or browsing porn sites. I had not been putting in the hours of study and homework which had been normal for me. I was an A student up until then, but this week I got back the results of tests in all of my classes and suddenly I was getting Cs and even some Ds!

I was going to have to find more Carl time, and let Sindy out a bit less, if I wanted to be able to keep up my grades this year, and next, and get into a good university! But Sindy was having so much fun! A conundrum I was going to have to solve. I wanted the fun, but also wanted the good grades!

I had another surprise this week, and did not know if it was a good one or a bad one. Danny and I confirmed our date for Saturday night. Cassie would drive me downtown and Danny would pick me up there. But... he wanted a date with Carl, not with Sindy. Danny said he was gay and was interested in guys, not gals, and so he wanted to spend time with me as Carl. I was a bit taken aback, but agreed.

On Saturday night I shaved and showered and put on some nice boy clothes. Boy, was it different getting ready as Carl. Half an hour tops to get ready, instead of the two hours that Sindy needed! Mom was a bit taken aback by my new hair colour and fresh scrubbed appearance, but was thrilled that I was going out on a date, though I did not tell her it was with a guy! I do think she wondered though.... with my more feminine hair and eyebrows, she might be having thoughts that her son was discovering he was gay! Hmmm.....

It didn't help that I was walking with a bit of swish to my step too. Carl had asked me to wear the butt plug he had left inside of me the previous weekend. So after my shower I had lubed up my ass and slowly shoved the plug up inside my rectum until my anal ring had clamped around the base. It was both pleasant and unpleasant to be walking around with that thick plastic stuck inside of me and, indeed, it was difficult to walk straight.

Mom's own date picked her up just a few minutes before Cassie and I left. I was surprised to see that it was Mr. Henderson, the principal of my high school. That made me very nervous, but I realized it was a reaction to his authority. It was like Mom was dating the enemy!

Mr. Henderson was a widower whose wife had died about eight years ago, before he had moved to Bigelow and taken over as principal at our school. I knew this because his son, Stevie Henderson was in my junior class and we were friends. His daughter Karen was in Cassie's senior class and those two hung out together sometimes.

I knew Mom had more than one guy who she was seeing. I guess she was serious enough about Mr. Henderson since she had an overnight case packed. Apparently the two of them were going out of town to see a Sunday football game somewhere far enough away that they would not be back until late the next evening.

I haven't really told you anything about my Mom yet, have I? Well her name is Miriam Barton and she is about 5 foot 5 with long dark hair. She is attractive, but not gorgeous. Her best feature, to my mind, is her long legs which she is not shy about showing off, either by wearing short skirts or by wearing patterned stockings. As a nerdy teenager, the occasional glimpse of my mom's dark stockinged legs over the years has been about the only sexual thrill I ever got in person. Cassie has obviously taken after her, which has disappointed her because both have not got much in the way of tits.

Mom had a tough time raising two kids but we seemed to be turning out okay. Mom DID let her hair down a bit on the weekends, often going out on dates with men, or going to bars with one or another of her girlfriends. Sometimes she would stay out overnight. Sometimes I would hear grunts and moans from her room as one of her men friends banged her.

Um, by girlfriends, I mean friends who are women. I don't mean mom is gay, a lesbian. Though I guess I do sometimes wonder if she might have a bit of fun with one or two of them sometimes. Anyway, I am getting distracted......

Mr. Henderson smiled at me and complimented me on my appearance. He said that the chess club and math clubs (for which he was the responsible teacher) had missed me the last couple of weeks, which brought a frown to mother's face. She was obviously wondering why I was missing some after school activities which I told her I HAD been attending. I couldn't very well tell her that instead of solving equations and moving rooks around a chessboard, I had been swallowing my sister's boyfriend's cock and screaming loudly as he rammed that same cock up my bum chute!

Johnny picked up Cassie and I up and drove us downtown. Johnny was a bit surprised to see me going out as Carl, and even called me squirt in an almost insulting way. They hung around with me until Danny drove up and I hopped in Danny's car.

Danny drove us into Springfield and we first went to a pretty nice pizza place for dinner. While we ate we talked animatedly and Danny told me how good I looked, and how he liked me much better as Carl than when I was dressed as a girl. Danny was dressed very smartly. While we were reaching for pizza slices and garlic bread, his hand managed to brush mine a few times, but I did not feel any thrill at all. If I had been dressed as Sindy we would probably have been holding hands across the table by the time dinner was done.

He noticed me squirming around on my seat from time to time and smiled, realizing it was because of the plug that I had up my bum. He whispered in my ear that he hoped I was enjoying the plug, and he knew that he would definitely enjoy replacing it with his thick dick at the end of the evening!

We then went to an art house film. It was in a small movie theatre but there were still only about a dozen seats filled. It was almost two hours long and was very good in spots. Danny held my hand in the dark, but I did not squeeze his hand at all. At one point he turned his head to kiss me, but I found that to be a good time to blow my nose in a tissue. I was feeling very unsettled, but could not place my finger on why. Danny was a great looking guy and had a very good personality, but somehow I was not getting into this date. Heck, on what I would now term to be a normal date night (my, how things had changed in just a few weeks!) I would have had my tongue down his throat, and his cock in my hands by now!

After the film, Danny took me to a gay club. Once we were inside there were very few girls to be seen and in fact, it was hard to tell if the couple of girls WERE girls. There were guys at the bar, guys at the tables, guys on the dance floor. There were fat guys, skinny guys, tall guys, big black guys, guys in leathers and chains, slim guys with limp wrists. The place was lively, and the booze was flowing. The music was loud and the dance floor was jumping. We found a table and Danny went to buy us a couple of drinks. While he did a few guys eyed me up and a couple said hello. But when he got back, Danny made it clear that I was his.

We sat and drank our drinks. We held hands. We went up and danced a few times and Danny held me very close. It was obvious that he was into me - he was constantly rubbing his large boner against me as we danced. It was a fun place.

But I was not feeling the love.

Around midnight we went out to the smoking area and Danny lit up after asking me if I wanted one. I automatically told him I did not smoke, and then wondered why I had said that. It was dark outside and in the shadows you could just make out several couples holding hands or kissing - all guys.

We returned to the dance floor and as it got later, you could see more guys grinding against each other. Danny began grabbing my butt and grinding his cock on me. He kissed me tenderly on the forehead and when I looked up his mouth pressed against mine and his tongue probed my mouth. I kissed him back, eagerly trying to find a connection with him, but failed.

I hurried from the dance floor and made my way to the washrooms in the back. Back here out of direct view of the main club area there were a few couples being a bit bolder. I passed a young guy on his knees who had his mouth jammed down on the cock of a chubby guy wearing leathers. And beside them was another young guy, cross-dressed and looking cute, who was also slurping on the dick of his date. I felt nothing watching the former, but I very much wished I was the pretty boy.

And that was when it hit me.

I went back to Danny and dragged him out of the club, asking him to drive me home. On the way, I began to cry and he pulled over to ask me why. I told him I had had a nice time, but that I had felt uncomfortable all evening. Finally I had figured it out. I was not gay. As Carl, I was not comfortable kissing a guy. Carl did not smoke. Carl was a nerd, a geek, a loner.

But Sindy was outgoing, alive, and definitely a cock tease. Sindy loved having sex with guys. I realized that I wanted to be Sindy as much as possible. I did not like Carl, and wanted Carl to go away.

I was a girl at heart.

I wasn't gay. I liked being Sindy. That did not mean I wanted to be a girl. At least I didn't think it did, but I knew that I had to be femmed up to be interested in a guy.

We talked for a long time and Danny was very understanding. But Danny WAS gay, and he wanted a boyfriend, not a girlfriend.

I told Danny where I lived and he dropped me off at the corner near my house.

I never saw him again although we did have contact on the internet from time to time.

Inside I tapped on Cassie's door and opened it a crack. This time, Johnny was fast asleep, but Cassie was awake. She slid out of bed, put on a robe and came to my room with me. I again cried and told her about the evening and my revelation. I was pretty much a wreck from all my sobbing, but Cassie held me tight and listened attentively, nodding at the right times.

She helped me get undressed and then put on a pair of frilly panties and tucked me in to bed. The lace felt nice against my cock as I drifted off to sleep. At some point during the night I got up and went to the bathroom. I had to remove Danny's plug from my ass. The thought of him made me teary again, but I managed to fall back to sleep fairly quickly.

Chapter 11 - Girl Fun

When I woke up in the morning I was aware of three sensations. I was hungry. My panties felt wonderful on my woody. And I was horny as hell.

Cassie's door was open a crack as I tiptoed past. I could see she was sleeping alone - Johnny had slipped out of the house sometime during the night. I made my way to the fridge and helped myself to sandwich fixings. It was still just mid morning. While I was hungry for more, I did not feel like cooking eggs or anything.

When I saw the cucumbers and carrots and zucchinis in the fridge, my cock got very erect in my panties, but I decided I wanted to concentrate on food for the moment. I made coffee and sat at the kitchen table eating and wondering what to do with the day.

Mom was gone until evening. I did not know what Cassie's plans were. I began to plan my own day, which would involve considerable time with my dildo, practising makeup, and browsing websites for fashions that I liked. I might even find some porn to jerk off to.

I knew I had some Carl homework which had to be turned in the next day, but after last night I really needed a Sinful Sindy day!

I showered away the sweat from last night, but kept my hair in a shower cap. I did not want to have to take several hours to get it fully dry. Cassie was still sound asleep as I grabbed various items from bags under my bed where I hid them from mom and then made my way to mom's room. She had a makeup mirror and a full length mirror.

I thought about putting on a pair of black lace panties, because I LOVED the feel of the lace on my cock, but instead I put on the fishnet panty hose that I had bought during the week. I then slipped on a pair of three inch heels and I practised walking and posing in front of mom's mirror. My legs looked SO sexy in the fishnets and my rigid cock bulged out the crotch area. I was dying to grab my cock, but resisted the urge.

Now that I was in Sindy mode, I desperately wanted a cigarette, but I resisted as mom was a non-smoker and would have a fit if she smelled smoke in her room.

I opened my makeup bag, sat at mom's makeup mirror and practised apply my foundation, lipstick and eye makeup. I tried my eyeshadow, liner and mascara several different ways. I played with the lighting of the mirror to see which styling of makeup worked best under bright lighting, dim lighting, etc.

After almost three quarters of an hour, I was desperate for a cigarette and for a cum!

I gathered everything up carefully and went back to my room. I removed my fishnets so that I would not rip them, but I replaced them with some sheer black nylon leggings and put the heels back on. I made myself comfortable on the bed and lubed up my ass. I then took my thick rubber dildo and worked the head of it past my anal ring. Before sliding it in further, I lit a cigarette. I lay back and as I smoked I languidly worked the fake cock slowing in and out of my ass. I blissfully daydreamed of Johnny and Danny and the guys from the fraternity, all drilling their cocks into my ass, as I practised sexily dragging on my cigarette, and fucking myself with the dildo. I had actually only had two different guys fuck me, and Danny only once, but I knew I wanted many more cocks up my boipussy - many many many MANY more!

Once the cigarette was done, I lifted my legs so that I had even better access and I used one hand to shove the rubber cock inside me, while using the other to strum my erect cock. As I pulled the dick out and shoved it in harder, I was grunting and groaning but I was not getting the nice action that I wanted - my prostate was not being stroked!

I was just contemplating pulling the dildo out and fastening it to the wall, when my sister cleared her throat from the doorway. She was wearing a flimsy nighty as she sauntered into the room. Need a hand, she asked, as she grabbed hold of the dildo and thrust it back up inside of me. She gave me a few more pushes and pulls before she collapsed on the bed beside me, giggling.

She kissed me tenderly and hugged me, complimenting me on my makeup, particularly my eyes. She confessed to me that last night she had let Johnny fuck her in the ass. It had felt.... uncomfortable, but not unpleasant, and had not resulted in any orgasm for her. Johnny though had found it to be wonderful, praising her ass as being the tightest thing he had ever fucked (I was jealous, and was going to have to have words with that man!)

I told her that I absolutely LOVED having a man laying on top of me, or kneeling behind me, and shoving his prick up my bottom. It felt so wonderful to be connected to another person that way. Of course, I could see that women would have the same sense of bonding with a pussy and would not need a man in their ass. But me, I really wanted a man's cock sunk deep in my ass, whether from the front, or behind, or even if I was riding on top of him.

I really missed not being fucked last night. I really needed a good fucking, I told her. Do you really mean that, she asked me? I nodded. She smirked and walked out of the room saying she would be right back. She definitely walked slightly lopsided, her ass sore from her own dicking the night before.

She was gone for a few minutes. When she returned she was wearing a strapon harness, with an eight inch plastic penis. Where did you get that?, I asked her. She told me that she got it from mom's secret stash of sex toys. I did not know she had a secret stash, but evidently Cassie had found it quite some time ago and had been borrowing from it from time to time.

Cassie said she had no idea who mom had been fucking with it, or who had been fucking mom, but it smelled and tasted like pussy! She told me to get on my knees, and I did. Cassie immediately shoved the rubber dick in my mouth, telling me to suck it and get it nice and wet, because she intended to drive it deep into my boipussy!

It did indeed taste strange. Was this my first taste of a pussy other than Cassie's? And was it mom's dried juices that I was tasting? I put that thought aside as Cassie fucked my face. I could see that what she was wearing was actually a double-headed dildo, which fit through a ring to give it some support. She had sunk one end (I did not know how long it was) into her own cunt.

Cassie pushed me back onto the bed, and pushed my legs back so that my knees were at my ears. She giggled as she placed the head of the dong at the entrance to my boipussy and she pushed inside. She was surprised at how easily it slipped inside me and how quickly my ass gobbled up the full length! She had never fucked anyone in this way before, but she soon got into a good rhythm of thrusting in and out of me while holding onto my ankles.

When she ran out of energy she collapsed on top of me, the dildo still deep inside both of us. We kissed hungrily, swapping tongues and spit. When she gained a bit of strength she thrust into me for a few more minutes, Her mouth was beside my ear and she kept whispering to me, telling me that I was such a sexy ass slut and how much she loved fucking me!

When she was finally too tired to continue, we lay beside each other smoking.

I told her I had loved the fucking, but it had still not satisfied me. She in turn said she had like the power that she felt when she was on top, and she wanted to do this again. She also said she liked looking into my pretty face while doing it - she now understood the power that a guy felt when fucking his girlfriend.

I admitted to still being horny. Cassie got a mischievous look and slid down the bed. She played with my cock for a couple of minutes and then, making up her mind, she proceeded to give me a blow job that lasted only two minutes before I exploded in her mouth. She swallowed.

This was only the second time I'd ever been sucked off, and I loved it. But I still had not fucked a girl. When I mentioned that to Cassie, she told me bluntly that she was NOT going to let me fuck her. She did say that, considering how much of a slut I had become in the last several weeks, she could not imagine me staying a virgin too much longer. I countered with the fact that I preferred the girl's role in sex, but she figured that sometime soon, I would get a chance.

She did ask if I had to choose, would I want to fuck someone, or be fucked? I told her that the decision was easy. I LOVED having a cock up my ass and would choose that anytime!

We jumped in the shower together and caressed and kissed a lot. Afterwards we spent another hour with Cassie helping me practise my makeup some more.

We did some girl laundry and got the place tidied up, my bags once again hidden under my bed, before Mr. Henderson dropped Mom off late that evening.

Chapter 12 - Love is Fleeting

On Monday I managed to get Johnny alone for a few minutes and told him that the next night I did not want just a couple hour quickie with him somewhere. I wanted the entire evening. He said he would work something out. We were alone in the hallway and so I pulled his head down and kissed him tenderly. As we kissed, I rubbed my hand across his hard dick. Yes, I was in Carl mode, but I was comfortable with Johnny and did not mind showing him affection, teasing him a bit, knowing that it would be Sindy who delivered the full goods!
So the next day, Cassie was steamed because Johnny was not going to be meeting her after cheerleading practise was over; but I was pleased.

Johnny picked me up and as usual we drove over to Seneca, the next town over. But this time he rented a room at a rundown hotel called the Ambassador. I told him to go grab some food on his own and to leave me alone for an hour so that I could get ready for him.

I spent that hour putting on my makeup, making my eyes look very smoky. My lipstick was immaculate. I painted my fingernails the same crimson colour. I pulled on my black panties, garters and sheer black hose and stepped into my three inch heels. I sprayed on perfume. And of course I lubed up my ass. I planned to give Johnny's cock a good long sucking and then have him give me a good anal probing for a couple of hours.

I was ready, and a bit nervous when Johnny arrived back. He tapped hesitantly on the door. When I opened it a crack, the first thing I saw was a single red rose which he handed to me. My man had bought me a flower!

I embraced him, and we hungrily kissed. He told me I looked stunningly beautiful. All thoughts of a slow buildup were gone. I had to have his cock inside me. Right away.

I pulled Johnny down on the bed and practically ripped off his pants. I pulled off my panties. I put a pillow under my bottom and spread my legs wide. Johnny eagerly placed his glans against my boipussy hole and pushed. He easily sank all the way to the bottom, his balls resting on my ass cheeks. I pulled him down on top of me and he lay on me as he slowly pulled his cock back out and then speared me again. Our lips kissed frantically, my hands caressed his back. His own hands steadied him so that he did not crush me, and so he could keep a good angle for penetration. I whispered that I loved him, and he said it back to me! My man LOVED me! I was in heaven as he ground his dick into me. My hands grabbed his butt cheeks as I tried to pull him even deeper into me.

At one point we rolled over and I was on top, lifting my ass off of him, and then thrusting down, skewering myself on his rampant truncheon. All the time I was kissing my darling man and whispering words of love. I kept telling him I wanted him to fuck me forever.

On my back again, my knees were pushed back beside my head and Johnny pummelled my ass. Finally, with a grunt and a violent shaking, he came and I felt my ass flooded with my sweet wonderful man's seed! He collapsed on me and we lay there exhausted. We continued to cuddle until I finally had to get up and sit on the toilet, expelling his cum. I brought a wash cloth back to the bed and washed his dick. Under my ministrations it quickly revived.

We cuddled some more and Johnny played with the rose, dragging it down my chest... circling my nipples with the red petals. All the while, he tenderly rained kisses on my eyelids, on my nose, my lips, and my pert nipples. My cock was flaccid on my belly. Johnny made no move to touch it. That was fine, I thought. Men don't play with girl's pricklets. I giggled at the thought and Johnny kissed me again.

I was ready for round two and pushed him back on the bed, so that his back was propped against the headboard. I wanted him to watch. I crawled between his thighs, which he spread wide. I grasped his lovely dick in my hands and spit on it. I used both hands to lube up his cock, and it quickly rose to full mast. I stared deep into his eyes as I began to suck on that lovely piece of man meat. I bobbed my head a few times and then, it was the moment of truth. I smiled broadly at Johnny, making sure he was watching and then I sank my head onto his cock and went lower and lower and lower. The tip of his cock hit the back of my throat, but I opened up, and I let his dick sink down into my throat. I held my breath as I took more and more of his dick into me, until my lips touched the hairs at the base of his cock. I had done it!

I had deep throated all of my man's yummy dick.

I held myself there for ten seconds and then backed off, gasping for air as the head left my mouth. Johnny looked at me in astonishment, but I quickly went back down on his dick taking it fully into my throat again. I bobbed my head up and down several times. Johnny moaned huskily.

For the next ten minutes I used my mouth and hands on Johnny's dick, bringing him to the brink of cumming, and then not letting him cum. He moaned a lot and pleaded to cum. I took him deep in my throat a couple more times. Finally when I decided to let him cum... I played with his glans until he pushed firmly on my head and I took him all the way in again. He shouted and I felt his cock pulse as he dumped a huge load directly down my throat and into my stomach.

I was disappointed. I had wanted to taste my man's cum again. In future, I would have to make sure I always pulled back so that he came in my mouth!.

Johnny lay panting. I tried to lick his spent penis head, but he groaned. The pleasure was too much for him. I giggled as I went to the small table and ate the sandwich Johnny had brought back for me, all the time admiring the rose he had bought me.

I watched Johnny and his wonderful lithe body. As I ate, he flipped on the tv set and found a basketball game to watch. I lit a cigarette and lay on the bed, snuggling up to him. I was content, happy, pleased to be thinking about a possible future with a sweet guy like Johnny. I loved his big dick. I loved HIM!

But what is love to one, may just be lust to the other!

We would have to get back to real life soon. But I had gone without a dick in my ass for several days and just one fucking was not going to be enough for me tonight. I knelt between my man's legs and began to lick and suck on his cock. When it rose to full length, I scrunched forward and sat on his dick. My ass was becoming so used to being fucked, that there was little resistance and I sank straight down. I bottomed out with Johnny's cock feeling wondrously, deliciously sensual in my bottom. As Johnny tried to look past me at the game, I bounced on his dick!

I took the remote control from him and turned the tv off. He complained mockingly, but then he pulled my face to his and kissed me long and hard. I grabbed his nipples and twisted them He yelled in surprise and threw me off of him. But it was in jest.

He rolled over on me, laughing, his dick sliding along my belly and duelling briefly with my own hard cock. I had gotten no pleasure from my dicklet tonight,, but I did not need any, so long as Johnny continued to pound my boipussy. And he did!

Johnny got me up on all fours and knelt behind me. He placed his dick head at the entrance to my pleasure palace and thrust forward, spearing me solidly! He grabbed my hips and began to pound away at me. His violent motion scooted me forward on the bed and soon, instead of being on all fours, I was pinned against the wall at the head of the bed, my chest hard against the wall, my arms and legs splayed out.

Johnny vigorously banged away at me. His lips were at my ear and he alternated between telling me how much he loved me, and calling me his dirty little whore. God, the dirty talk really turned me on, but not as much as hearing how much he loved me!

And then... as he continued to thrust inside of me, he told me that he had been telling some of his buddies about this cute boy who liked to dress as a girl and who he had been banging on a regular basis. His friends were not turned off, and in fact, were also interested in meeting me. As Johnny stroked his cock through my back passage, he told me that I would have a lot of fun with his friends.

So, he didn't love me! He was just using me, he just thought of me as a cheap cum dump! All of his tender words were just play acting. Things that he said to keep me happy. I sobbed briefly, but Johnny thought I was sniffling from my awkward position. He pulled me back further and once again I was on all fours. Johnny... no longer my DEAR Johnny.... sank his cock inside of me and came, splashing his jism deep into my bowels.

I ran to the bathroom and was sullen for the next half hour as I removed my makeup and nail polish, slowly returning to my everyday Carl appearance. I could hear the game back on the tv set as Johnny waited for me.

I was quiet on the way home. Had I really expected Johnny to love me? To be my boyfriend? Hadn't I been saying to myself that I needed to get a man of my own? And, that I needed to find more guys to fuck?

When he dropped me off a few blocks from my house, I kissed Johnny. It was the last time I would kiss him tenderly. Yes, we might fuck, but I would never think of him with tenderness again. I told him that, yes, I would be interested in meeting some of his friends.

I had lost a lover... a man I thought that I loved. But I might have just gained a few more cocks to keep my hungry ass satisfied.

As I walked into the house, I said hi to Mom and some man I did not know, who were lounging in the living room. I think I interrupted them kissing and cuddling. I did not know the man. Just one of mom's endless dates I guess.

Music was thumping behind Cassie's door but I did not disturb her. I took a long leisurely bath, making sure to clean my ass out throughly. When I climbed in to bed, I put on a pair of pretty pink panties and drifted off to sleep.

Chapter 13 - Discovered

Despite my disappointment, I was not going to give up my twice weekly fuckings by Johnny. I might see him in a new light now, but I figured I still needed the delight of his dick reaming my ass - at least until I could find one or more regular replacements.

After school on Thursday, I grabbed my Sindy bag from my locker and was going to meet Johnny a couple blocks away from school as usual. But he had been delayed and so I ran into him in a hallway. He was on his way to his car in the parking lot. He was looking so good that I just had to kiss him. The hallways were deserted, so I pulled him into a classroom doorway indentation and pulled his lips to mine. He hungrily kissed me back and he moaned as I grabbed his penis. I could not resist and so we kissed for a couple of minutes.

At least a minute too long as it turned out!

A deep voice suddenly called out Johnny's name. We untangled and looked up in surprise to see Coach Grogan coming down the hallway. I guess his assistant was running the basketball practise. He shouted and swore when he realized that Johnny had been kissing another MALE student! He opened the classroom door and hauled Johnny inside.

Coach Grogan told me that we were both in big trouble. He told me to go to his office and wait for him there. Once he was done talking to Johnny, he wanted to talk to me and get my side of things. But right off the bat, he figured we were both facing a suspension for a long period of time!

He slammed the classroom door. I was almost in tears as I walked to his office, let myself in, and then sat down in the dark to wait. I did not want to see Johnny ruined and lose his chance at a football scholarship. Heck, I did not want to see my own college chances disappear either, even though I would still have my senior year to try to put this behind me.

As I sat, I began to remember some of the rumours about Coach Grogan, and I made a decision. I turned on the lights and then opened my Sindy bag. I quickly put on my Sindy clothes and using a mirror in the corner I quickly applied my eyeshadow and lipstick. I then turned the lights back off and waited.

I had been alone in the office for about twenty minutes. I had lit a cigarette in order to calm my nerves. It was odd though, I was nervous as hell, but excited too. My dick was rigid and poking out of the top of my panties.

The office door suddenly opened. Coach was a bit disconcerted to find the light off and to smell cigarette smoke. He cursed at me and then turned on the light. He was startled to find a young girl sitting behind his desk, rather than the Barton boy he had been expecting. I stood up and he gasped, seeing that I was dressed in a short top which left my navel exposed, underneath which were cute lace panties, and long legs sheathed in black nylons, all on top of three inch high heels. He was speechless as I walked around the desk, and sat there, my legs spread lewdly, revealing my aching cock, prettily displayed between my thighs, with the head poking up.

I then got off the desk, and leaned over it, pulling my panties down fully. I reached behind with both hands and spread my ass cheeks, so he could see my ass pucker, which was lubed and ready for action. I turned back around and Coach moaned as he saw my pretty cock, standing at attention.

I'd had a cigarette between my lips. I took a final puff and blew smoke in the air sexily, like I had watched Becky Winters do, then dropped it and crushed the butt under the toe of my heels.

I giggled like a young girl and asked Coach if he liked what he saw, but he only stammered. I told him that Carl had gone home and that Carl had asked his cousin, Sinful Sindy to keep the Coach company instead. Coach tentatively reached out a hand, I thought he wanted to touch me to see if I was real. Instead he grabbed me by the shoulder. I thought he was mad, but no, he pushed me to my knees. He turned back to his office door and locked it. Then he undid his belt.

I reached up and pulled down his zipper, eager to get at what lay inside his briefs. As his pants came down, I could see the outline of a large thick cock which was already getting hard.. As he pulled down his shorts, his black cock bounced free. It was only the second black cock I had seen up close and it was a good ten inches in length. I was in heaven!

I took his large dick in both hands and engulfed the knob in my mouth. His cock was delicious. I bobbed my head up and down and slowly took more of it into my mouth. My hands alternated between running up and down his thick powerful thighs, and holding and caressing his thick balls. I had to taste those balls and so I took first one and then the other into my mouth, humming on them. They tasted divine. Coach was an active man and after a day of exercising with the various classes he taught, he was hot and sweaty and his balls were rank with his man flavour.

Coach picked me up and lay me down on his desk. He turned me over on my back and had my head hang off of the desk. His finger tweaked at my nipples as he pushed his cock into my mouth and began to fuck my mouth as if it was a pussy. I grimaced as he twisted my little nubbins. He cursed me, telling me that I was no better than all the other slutty students who came on to him. He said he had fucked all of them too, especially that tramp, Becky Winters. But this was the first time one of the male students had turned him on enough to be fed his dick!

And feed it to me he did! He slid that dick in and out of my mouth, my lipstick spreading over his dark chocolate cock. He pushed further and further and finally, despite the thickness, I was able to open my throat and he slid even further inside of me. A couple strokes later, and he was fully down my throat, his ball bag hanging over my nostrils. I tried to inhale his musky scent, but his cock down my throat cut off all of my oxygen.

He pulled back out and I gobbled up the head of his dick, licking up the precum.

Coach picked up the phone, calling someone, whom he said needed to come to his office for a serious discussion. Damn! I had thought I might be able to talk my way out of a suspension - well, fuck my way out of it, actually!

I took a deep breath as Coach again thrust his cock fully into my throat. He began to saw his cock back and forth, but never taking it past my gag point. After 45 seconds I began to feel like I was blacking out, and began to pound my hands on his ass. Another half minute passed and I thought he was trying to suffocate me. But finally he pulled out of me and I lay there gasping for air.

He picked me up and took me to the couch that was in the corner of his office. He put me on all fours on the couch, my ass facing towards him. He placed the head of his dick at my pucker and then thrust inside of me. He did not stop until his full length was embedded fully in my ass.

His cock went further up inside of me than any cock before it. I was stuffed full and fucking loved it. I moaned at him, and pushed back. He leaned forward and told me that he had known I was a slut when he saw me kissing Johnny, and that the only way to deal with a slut was to fuck her!. He grabbed my pony tail and pulled my head back hard as he began to thrust his cock in and out of my boipussy!

Then he grabbed me around the throat and was practically strangling me as he pounded away at me.

I managed to move my ass back and forth and ensured that he was rubbing fully across my prostate. Coach's large dark cock felt wonderful inside my ass and I urged him on. I shouted my pleasure, but his hand clamped across my mouth. He reminded me that there were still plenty of people in the school. I nodded and he released my mouth.

A moment later there was a knock on his office door and someone shook the doorknob. Then I heard a key at the lock and the door opened. Principal Henderson walked into the room, was startled by what he saw, but quickly locked the door, took off his jacket and began to pull his pants down.

Who? he began to ask. Coach Grogan pulled my head around so that Mr. Henderson could get a look at my face. The principal also caught a glimpse of my erect cock bobbing against my belly as the Coach's cock continued to slide in and out of me. Coach Grogan said that I was the Barton boy's "cousin", Insatiable Sindy. You could hear the quote marks around the word cousin. Miriam's boy?, asked the principal. Coach nodded

Principal Henderson looked startled, but that did not stop him from lifting my face up to get a good look at me. Very nice, he said, lovely makeup. Sculpted eyebrows. I thought you were looking a bit faggy the other night. Very fetching. Well I never expected this! he said as he stuffed his cock in my mouth.

For the first time ever, but nowhere near the last time, I had two cocks inside of me. I later found out that this was called spit roasting. I was slightly disturbed that I was being used as a sex toy by the two most powerful men in the school, but only briefly.

As I gobbled up more and more of the principal's dick, I realized that I was sucking off my mom's boyfriend - well, one of her boyfriends. Not only was I regularly fucking my sister's regular guy, but now I was about to drain the balls of my mom's beau!

The two men traded some lewd banter, commenting about what a sissy boy I was. I reached up and caressed the principal's balls and he shoved even deeper inside my mouth. I also managed to take him all the way down my throat, but he did not try to gag me. In a few moments he gushed his cum down my throat.

As he collapsed back onto the couch, Coach Grogan picked me up in his arms as he stood up. Remember, I was only five four and thin - not very heavy at all. He spun me around so that I was facing him. He positioned me so that my legs were over his arms and my legs were spread wide. He then lowered me down and speared my ass with his amazing cock. He then began to raise and lower me as he thrust his cock upwards. I was bouncing on his cock, face to face with him.

Coach was not a handsome man. Too many years of sports injuries had gnarled his face. But I took his head in both hands and pulled his lips to mine. I kissed him hungrily, but then had to bury my head against his neck as he set up a furious pace with his cock in my boipussy.

Finally he thrust me downwards, his cock drove deep inside of me and with a loud grunt, he spewed his cum deeper into my bowels than anyone had before. Somewhere along the line my own cock had jetted its jism across his chest, but I had barely noticed. The bliss from the ass pounding had masked the joy of my own cumming.
Coach lifted me off of his dick and his cum immediately started running out of my ass. As he set me down my legs wobbled. Coach told the principal I had a fine tight ass and asked if he wanted a piece of that. Principal Henderson was already putting his pants back on. He said he would get into my ass another time but he did not feel like taking sloppy seconds at the moment.

They both talked to me for a few minutes, ensuring that I was not going to tell anyone about what had just happened. I assured them that I was not going to, so long as we could come to an agreement. They agreed that there would be no suspensions or punishments for Johnny or I. But they both wanted to see me again. I nodded in agreement and the principal left.

I had one more deal for Coach Grogan though. I put my panties back on, and sat on his couch. I lit a cigarette and relished in the feel of his cum oozing out of my ass and puddling in my panties underneath me.

I asked the coach if the rumours were true that he was giving some of the male students steroids to improve their performance. I told him that I did not need an answer about that, but I was wondering if his sources also had access to female hormones. If so, I wanted him to get me some. He smiled and said he would see what he could do. I should check with him at the beginning of the week.

He said that in return, he wanted to give me a weekly injection. He grabbed his cock and waggled it at me. I knew what kind of injection he meant, and I was more than willing to trade a bit of ass for the hormones.

Coach left and I changed back to my Carl clothes and headed home.

Mom was out when I got home. I tossed my Sindy bag under the bed and stripped to take a shower. The hot water felt wonderful on my body and I stood there for a good long time. When I got out and dried myself off, I realized that a bunch of my body fuzz was growing back including around my cock, and I decided that I would need to go for another waxing soon. I felt behind me, and then used mom's hand mirror that was always in the bathroom. I bent and twisted and finally managed to get a look at my asshole to confirm what my probing fingers had told me. My ass was still tightly closed. I had been afraid that the pounding from Coach might have left me gaping open, but my ass was young and resilient. I had a lot more fucking to do before it would begin to gape open and start looking like a pussy!

Back in my room I toyed with my cock a bit while I browsed some bondage and fetish sites, looking at all the interesting leather and other erotic wear. I had cum once that evening, without anyone touching my dick. I did love the feeling of my cock being played with, but I so much more loved my ass to be filled. With that thought, I grabbed my thick dildo and slid it easily up my butt. I climbed into bed and slowly wanked myself off as I worked the rubber cock in and out of my ass. I came into a tissue, then reached over and turned out the light. I fell asleep with the wonderful feeling of the dildo still firmly lodged in my back side.

Chapter 14 - Money

Saturday night turned out to be a significant night in my young life - or should I say in Sindy's life. Sindy was starting to consume me. Carl was starting to fade away.

Mom was heading off for an overnight with Mr. Henderson again. Cassie was going out for a girl's night with several of her classmates. That usually meant that she would be bringing some new guy back to her bedroom for the first time. So Johnny was at loose ends and he asked me if I wanted to get together again in a room at the Ambassador. I was still mad at him from Tuesday, but I was hungry for cock and had no other ideas for Saturday night and so I said sure.

The out of town football game was a lot further away so mom and principal Henderson were flying. He picked her up early Saturday afternoon. He came upstairs to chat with her as she finished packing her bag. He looked into my room and found me at my computer looking at various website. He stepped into my room and in a loud voice he complimented me on Thursday night. I looked up startled, and he added that my game at the Chess Club was the best he had seen in quite some time. He was complimenting me on my cock sucking at the same time as covering for me. He leaned down and whispered in my ear that I should not make any plans for Tuesday after school as I was going to have detention in his office!

I waited an hour after Mom left just to be sure that she was not returning for anything she had forgotten, and then I started transforming into Sindy. Cassie and I had to share the bathroom and mom's makeup mirror, but we managed well. I started with a long bubble bath and Id shave my arms, legs and as much as my groin area as I could reach. Much as I wanted another waxing, I could not afford it right now. When I was mostly done, I called to Cassie and she came in and shaved the bits of my groin that I could not reach.

Of course, she had to hold and move my penis around to get underneath and around it. She also shaved around my asshole. I did not have much in the way of hair, but it was nice to be smooth again.

Cassie teased me and got my penis erect, even taking the head into her mouth a couple of times. I implored her to suck me off, but she said no - though promising that if I was a naughty girl, perhaps later on that night she might relieve me.

She was curious about who my date was that night. I told her is was another one of the guys from the frat party we had gone to. We had been in touch by email and he was eager to see Sindy again. Cassie told me again that she was sorry things had not worked out between Danny and me, and she knew how much I wanted a boyfriend of my own, just like she had Johnny. I told her not to worry, I was having fun dating a bunch of different guys.

Cassie and I both left the house around nine pm. She was picked up by a car containing four of her classmates, including Karen Henderson, the principal's daughter. It seems she was eager to get out and play, while her dad was away!

I called a taxi. The driver looked at me with hungry eyes in the rear view mirror as we drove. I did look pretty foxy, I had to admit. The driver did not mind if I smoked in his cab, so I lit up a cigarette and practised blowing smoke rings, This got the driver's attention and he asked me if I was going to meet a date. We chatted for a few minutes and the conversation got suggestive. I eventually realized that he was trying to determine if I was a hooker. It was a fun ride over to Seneca as we chatted and teased.

When we got to the hotel the cab fare was forty dollars. That would pretty much drain all of the cash that I had in my purse. Johnny had promised to pay me back when he arrived, but I was still uncomfortable with the thought of having no money. My mind played back over my conversation with the cab driver and I smiled.

The cab driver was about fifty years old, had a pock marked face, a shaggy mustache and a fairly large beer belly, but he also had a dick.

We had parked off to the side of the Ambassador and it was dark. A few moments later I had dragged a piece of cardboard over by the cab. The cabbie was leaning back against his cab with his pants down. I had his cock in my mouth and was sucking him off in return for not paying him his fare. He offered me twenty dollars more if I would smoke while sucking him off. I shrugged, lit up a cigarette and alternated sucking on the ciggie and going down on his dick. This is the first time I encountered any kind of fetish.

It did not take long before he sprayed his cum into my mouth. I leaned back, showed him the cum in my mouth. I then took a deep drag on the cigarette, swallowed his cum, opened my mouth to show him it was gone, and then exhaled the smoke. I swear that his cock dry jerked several times!

Along with the twenty dollar bill, Carlos gave me his business card and told me that I could ride free anytime I wished, so long as I would blow him each time. I thanked him, told him he had a lovely cock (not really!) and told him I looked forward to a budding friendship.

That was the first time I took money for sex. I did not feel bad about it at all!

Chapter 15 - More Than I Had Bargained For

While I was in the cab, Johnny had texted the hotel room number to me. I bypassed the front desk and went straight to the elevators. When I got to the room, Johnny was waiting for me. He swept me into his arms and kissed me eagerly, and I kissed him back, but he was a bit cold to me too.

From the next room over I could hear the shouts of a bunch of guys as they watched a hockey game that was much too loud. The hotel room walls were very thin.

Johnny sat me down on the bed and asked me if I remembered what he had said the other night, about some of the other guys wanting to meet me. I said yes, and it was okay if he had them email me and I could set up a date.

Well, that wasn't exactly what he had had in mind he said, and he got up and opened the door to the connecting room. He took my hand and pulled me inside that room. There I found five of his classmates from the senior class. They had a bunch of pizza boxes and beer and, despite the windows being open, you could smell that they had been smoking pot too.

Upon seeing me, the guys have out hoots and hollers and started yelling, me first!

I pushed Johnny back into the first room and asked him what the fuck was going on? He said that the guys had said they could not wait to meet me. Cassie had told him about my blowjob contest at the frat house a couple weeks back, and so Johnny was sure that I would not mind giving his team mates the same treatment. I looked at him in disbelief! I told him that there had been plenty of witnesses there and it had been a controlled environment. It was unlikely that anyone there was going to lift up my skirt and find out my secret. Johnny told me that he had already told the guys that I had a dick and they were already cool with it!

I was still hesitant, but I HAD been looking forward to getting screwed by Johnny and drinking his cum. I had found it interesting to have sex with the coach and principal at the same time on Thursday night and here I now had the opportunity to not only suck off six guys, but to hopefully get fucked by several in the same evening.

We returned to the other room. One of the guys handed me a beer as Johnny nodded at them and they all cheered again.

Over the next fifteen minutes I mingled with the guys and ate pizza. They all treated me as if I was a girl. If anyone recognized me as Carl Barton, no one said a word. As I moved from guy to guy, each one was eager to touch me and kiss me. I kissed a few gently, but was careful not to get too frisky, yet.

But eventually they turned down the sound on the game and turned on some music. Someone handed me some pot and I inhaled a few times. That and the beer had me giddy and I was soon doing a strip tease. When I had my top and skirt off, all the guys oo'd an ah'd as they watched me roll my panties down past my stockings (yes I wore them over top) and my hard little prickie sprung to full attention.

I fell to my knees in front of Douglas and pulled his zipper down. I pushed his jeans down and fished his cock out of his underwear. I looked up into his eyes as I took the head of his dick in my mouth and then I swallowed his entire length. He looked amazed as I mashed my lips against his pubes. I then began to bob my head up and down.

But I did not manage to suck him long. Another hand pulled my head to the side and Jake stuffed his dick into my mouth. Soon I had all five guys standing in a circle and I moved from cock to cock to cock, sucking on each in turn as I would fist two other cocks at the same time. Johnny sat off to the side, drinking a beer and watching his teammates.

This went on for about ten minutes. I eagerly gobbled one dick and then another. When two cocks were close together, I tried to jam both of them in my mouth at the same time, but the guys seemed shy about have their dicks touching each other.

Then Gabe picked me up and tossed me on the bed. I was barely up on all fours before Gabe started working his cock inside my ass. Lucas moved in front of me and jammed his cock into my mouth and I was forced forward onto his cock as Gabe began to pound my ass.

For the next two hours I fucked and sucked the guys repeatedly in a variety of combinations. Some guys came in my ass, some in my mouth. Some spewed their jism on my face. When I was fucked on my back, I was able to suck another guy and fist one or two others.

The guys were frantic at first, but after the first hour they slowed down a bit. I was draining their energy as well as their balls.

Johnny had just sat there watching most of the time. But late in the activities, I was riding on top of Ted's dick. He was pretty tired, but I still needed more cock. I was on top of him, bouncing up and down trying to jam his cock ever deeper into my hungry ass, when I felt a hand push me forward. Johnny was behind me and I realized that he was trying to jam his cock into my ass, which was already quite full of Ted.

But Johnny persisted and soon he has managed to work is cock into my boipussy. I now had two cocks stuffed into my ass. Ted was motionless beneath me but Johnny began fucking me furiously. I moaned as he rubbed my prostate and for the first time that night I gushed my jism on Ted's chest. Johnny yelled that my ass was so fucking tight, and then both he and Ted blew their loads into my bowels!

All of the guys looked pretty drained, but Douglas was up for more. As the other guys all sat exhausted, their dicks all shrunken, Douglas took me by the hand into the other room and he fucked me on the other bed. He was on top of me, and as he lanced his cock in and out of my ass, he kissed me, despite my face being caked with dried cum and my lipstick being a mess. I nuzzled his neck and urged him on, rolling my hips and trying to increase the pleasure he was getting from me.

This was going to be a long fuck. He had cum several times already, so we talked casually about some school stuff. He told me that he had been amazed when Johnny had told him that the nerd Carl Barton liked to dress up like a girl and was a damn hot fuck! And then he mentioned that he had paid Johnny a hundred bucks to party with me tonight. I asked him to repeat that, and he told me that all of the guys had paid Johnny for the evening.

So not only was Johnny not in love with me, but he was a blabbermouth, AND he was pimping me out!

I was done for the night. More than done. I flipped Douglas over, moved down his body and took his cock in my mouth and hands. It only took a minute before Douglas's cum spewed weakly from his balls.

I told Johnny and the boys that I was done for the night. No one objected strongly. I took off my stockings and jumped into the shower in one room. When I emerged, I inspected my clothes and other than having a run in one stocking, everything looked fine. I spent a few minutes redoing my makeup.

The other guys were all gone when I opened the door to the adjoining suite. Only Johnny remained. I won't go into the details, but I screamed at him and reamed him out good. I got him to turn over the five hundred dollars he had collected for selling my ass to his friends. I also took another forty dollars from his wallet to cover my cab fare to the hotel, and another forty dollars to cover my cab fare home. He argued that he needed some of the money to pay for the room, but I told him that he was a shit and that I did not care.

I had already called Carlos and knew that I had wasted enough time. I ran from the room, took the elevator down. It was midnight when I got in Carlos cab and we drove away.

I put on a bright happy face as Carlos and I chatted amiably on the drive home. At one point I asked Carlos to pull over into a laneway, and I got in the front seat and blew him.

When he dropped me off in front of the house, I realized I'd had quite an evening. I had six hundred dollars in my clutch purse, I had blown five guys at least a dozen times and had my ass fucked eight or a dozen times. It has been hard to keep count.

One thing I was sure of though, I was never going to date Johnny again!

Chapter 16 - The Evening is Not Done Yet

As I climbed the stairs to the second floor, I could hear my sister grunting and groaning. She had obviously dragged some guy home to have some fun. Yes, Johnny was her boyfriend, but she was not exclusive to him and it was hard to imagine her going the weekend without a cock inside of her. I guess I took after her to some extent!

Her door was open a crack. I was about to walk past and just head to my room when she cried out, oh fuck me that feels so good! Jam it deeper! But I realized that was NOT my sister's voice. I had just assumed that the female voice was hers. I backed up and opened her door a bit wider.

Cassie was on the bed, but it was not her being fucked. Instead my sister was naked and had mom's strapon harness around her waist. She was laying on top of another girl and was ramming the double headed dildo into the other girl's pussy, while hungrily kissing her on the mouth!

My sister was fucking another girl!

The other girl was very vocal, telling my sister to ram the big cock deep into her pussy. Cassie had worked up a good sweat. While she pistoned the cock into the other girl, her one hand was twisting at the gal's sizable boob.

I opened the door a bit more to get a better view and I guess I made too much noise, because the other girl suddenly got startled and looked right at me. She pushed Cassie off of her, the dildo pulling out of her cunt with an audible squish. She asked Cassie, who is that?

Cassie smiled and beckoned me into the room, introducing me as her cousin Sindy. I was surprised to see that the other girl was Karen Henderson, the principal's daughter. I sat on the bed and compared the two. Cassie as thin, but athletic, with small breasts. On the other hand Karen would be politely described as plump. She was pudgy, short and had very large breasts. Her boobs were big, soft and almost pillowy - not like the large breasts that I had seen on Becky Winters at the frat party. Becky's were obviously implants, whereas Karen's were very very natural.

We sat and talked for a bit. After a couple minutes, Cassie reached into her drawer and pulled out a baggie that contained a few rolled joints and she lit one up. I was surprised that she would do that in front of the principal's daughter. The girls laughed at me and it was nice watching Karen's boobs jiggle. Cassie told me that she bought her stuff from Karen. Apparently she was supplying about a dozen of the girls and guys in school.

As we smoked the joint and talked some more, Karen and Cassie began lightly touching and caressing. Cassie kissed me deeply and soon I was kissing Karen too. Karen told me that she was a lesbian and had been hitting on Cassie for a couple of months, never expecting Cassie to respond. Cassie gave me a long lingering kiss as she said that, after fucking me a few days back, she had liked the feeling and wondered what it might be like to fuck another girl. So she had gone out tonight with the idea that she might bring Karen home with her tonight, and it had worked out that way.

Karen raised an eyebrow at hearing that Cassie had fucked her cousin. She asked me if I was a lesbian, and I said no, I had only started having sex about six weeks earlier and I loved fucking with guys - my experience with Cassie has been out of frustration, but I had enjoyed it.

Karen still did not realize that I was really a boy underneath my sexy outfit. She dragged me to her and enveloped me in her softness. Her tongue probed my mouth and I hungrily kissed her. My hands went to her breasts and my mouth soon followed. I took one then the other of her fat nipples into my mouth and she moaned lustily.
I asked Karen if she has always been into girls and she said yes - she had never even kissed a boy. She thought that they were too hard and angular. She had always been drawn to females. I asked her what she might think of a pretty boy, and she said that she did not know. She would have to think about that if she ever found one.

She pushed me lower and spread her legs wide. I found myself staring at her pussy for a moment, before she pulled my face to it and told me to eat her. I eagerly began lapping at her cunt. At the same time, Cassie moved behind me. She flipped up my skirt and pulled my panties down, and off of me. She lubed up my ass, and then sank her fake cock deep into me, causing me to moan into Karen's cunt.

Karen urged Cassie on, telling her to ram that cock into my pussy - nor realizing that it was actually in my boipussy!

We worked ourselves into a frenzy for the next five minutes and then Cassie pulled me upright and whipped off my skirt. With her cock still lodged in my ass, my own cock was standing at stiff attention. Karen gasped in surprise, only then realizing that Sindy was actually Carl. She giggled as she realized that Cassie was actually stuffing her cock up her BROTHER's ass!

Karen murmured that I WAS a pretty boy and then did not hesitate to take my cock in her mouth and begin to suck me. Cassie removed the dick from my ass and lay back to watch Karen fellate her brother. Cassie lit up another joint and we all shared it as we hugged and kissed and caressed each other.

We were all very mellow when Cassie mentioned that Karen was a virgin to boys - she had had plenty of dildos up her pussy, but never a cock - and that Sindy was a virgin to girl - I had had lots of boys up my butt, but had never put my cock in a girl. Perhaps we needed to each help each other out?

And so it was that after yet another joint and a lot of kissing, I slid my cock into its first pussy and brought a gal to delightful bliss for the first time in my life. It was an interesting experience, and Karen's pussy did wonderful things to my boy cock. When I shot my load deep inside of her, I groaned and fireworks lit up my brain

But I have to honestly say, I felt SO much better when it was someone else filling MY asspussy with their jism!

(Aside: As you are aware, this IS a story. So no one gets pregnant, and no one catches any disease!)

Karen was pleased with the experiment, but said that she would prefer to stick with pretty girls, although for a boy, I was darn cute!

We all petted and caressed for awhile longer. Karen was fascinated that Cassie and I were having sex with each other, but Cassie clarified that she would not let me fuck her. Karen asked if she just meant her pussy, wondering if Cassie might let me fuck her in the ass. Cassie admitted to having let Johnny take her ass cherry the past weekend and having enjoyed it. She looked at me, and said that she did not know.. perhaps.

It was time to call it a night and so I told the girls goodnight. It took me twenty minutes in the bathroom to get cleaned up. I put on a nighty when I went to bed and drifted off to sleep.

At about four in the morning, Karen came into my room and crawled in bed with me. We cuddled and kissed a bit and then we both fell asleep. It was nice sleeping with a large warm pillow!

Chapter 17 - Sunday with Karen

When I woke up around ten or so, Karen was gone. As I made my way to the bathroom to shower, I heard the two girls in Cassie's room, moaning and groaning. I took a quick peek in and found that this time Karen was fucking Cassie. Karen waved at me and blew me a kiss. Cassie beckoned me in to the room, but I declined. I told them I would have breakfast on the table for them in an hour.

I put on some light makeup and a pair of girl jeans and a simple top.

At breakfast Cassie said that she had plans with other people for the day and would be leaving shortly. Karen asked me if I would like to hang out with her for the day. I knew that I had a lot of Carl homework to do - my grades were really plummeting - but spending the entire day as Sindy with a new girl friend was much more appealing and I said sure!

Cassie left shortly after that. Karen and I went upstairs and for an hour she helped me practise my makeup some more. Her approach was different than Cassie's and I learned a few different tricks. In the end, my makeup was a bit more garish, and a bit more slutty. That was how Karen said she liked her girlfriends, slutty.

We smoked two joints while we did this and I had quite a buzz on. As we drove around in Karen's car we had yet another joint. I ended up telling Karen what had happened with Johnny the night before - how he had pimped me out to his classmates and how I had made him give me the money.

As we drove around for the next hour or so, Karen was having very short conversations with people on her cellphone and we were frequently stopping to chat with friends here and there. Many were classmates of mine or her. I said hi to all of them, and none realized that the sexy gal in the passenger seat was Carl from school. But I realized that they were not really paying attention to me. I finally realized that Karen was making the rounds, delivering pot to various customers!

When I mentioned that I had made five hundred bucks from Johnny the night before (I did not mention the cab fare I got from him, nor the twenty I had made from blowing Carlos) Karen told me that I should never be ashamed of making money. I had killer looks and there were men and women out there who would pay to be with me. She told me I was foolish to give my ass and mouth away for free.

Karen told me that she had over twenty thousand dollars in a bank account that her dad did not know about. Most of it was from selling weed, but she also had regular gigs with a few housewives in her neighbourhood who paid her for sex with them.

I'd only had a sex life for less than two months, and had been enjoying the attention too much to think about whether I could get any benefits from it! But what Karen said made sense!

The money I had made last night was burning a hole in my pocket book and I told Karen I wanted to go shopping. She giggled and said she had a better idea. Ten minutes later we parked the car and she took me into a tattoo and piercing parlour. Karen wanted to add a new tat onto her ankle and so I hung around for a half hour while the young heavily tattooed proprietor used his machine to etch the new design onto her leg.

While the work was being done, Karen kept urging me to get inked. I finally gave in and when she was done, I had the guy put two small paw prints just above my left hip. It wasn't much, but it was a start.

However, I had also been intrigued by something else that I had seen on several gals in the porn videos I had been watching online and Karen agreed that we had time.

So I asked the guy to pierce my belly button. For fucking jeezus christ, but that HURT! Normally he would have just put a rod into the piercing and told me to come back in a couple weeks to replace it with some jewellery, but I sweet talked him into putting in a long dangly shiny bauble right away. It was my first girl jewellery!

When I say sweet talked, I had actually taken Karen's discussion to heart - when he was done, the buy put a closed sign on the door and I went into the storage room with him and pulled down his pants and blew him. He was not handsome, nor particularly likeable - but when he was ready to cum, I let him jerk off onto my face and he gave me the tattoo and his labour for doing the piercing for free. I had to pay for the jewellery since the store owner would be checking the books.

I used the washroom to clean up my face and reapply my lipstick. When I came out I found the guy sucking on Karen's tits. She had gotten her tattoo for free as well!

After that we drove back to Karen's house. Her dad and my mom would not be back until about 6 am the next morning, so we had the place to ourselves. We smoked another joint and then spent a half hour just kissing and gently cuddling with each other. Despite being a confirmed lesbian, Karen went down on me and sucked my cock until it was almost ready to explode. She then lay back and let me put my dick inside of her and we fucked for about fifteen minutes before I squirted inside of her.

As we lay there panting, she told me that she had enjoyed being fucked more than she thought she would, but she still preferred eating pussy and fucking other girls with her strapon. She wanted to be the one in charge. I told her that I also enjoyed fucking her, but that I truly loved having a big strong guy ramming his cock up my ass.

We grinned at each other and a few minutes later it was my turn to be on my back, with my legs up on Karen's shoulders as she drove her large rubber cock in and out of my tight ass! We fucked missionary style and doggie style. She stood me up and bent me over the dining room table and slammed her cock into me. She was loud and vocal as she came many times from having the nubbin on the base of her cock rubbing against her clit. I spurted my own jism twice more, once on the dining room table, and once on her kitchen counter!

When she drove me home, I have her a hundred dollars and she gave me several joints. She was now my supplier too!

Chapter 18 - Double Injections

On Monday I was called to the school office and handed a note which would excuse me from my classes at two pm. I was to go see Coach Grogan at that time. I showed up at his office and the Coach told me to come in and close the door. He was sitting behind his desk and as I approached he pushed himself back a bit and I saw that he had his dick out and was playing with it so that it was already hard. He told me to get on my knees and suck him.

I hesitate and then explained that I could not do that as Carl. I would need to go to my locker and get a few things to become Sindy. He said we did not have a lot of time. I hurried to my locker and grabbed my change bag. Back at the Coach's office, after locking the door, I pulled off my pants and shorts and put on a pair of panties. Coach smirked that those would not be staying on for very long. I took out a tube of lipstick and rouged my lips. I then closed my eyes and let Sindy slowly creep into my mind. I was ready.

I knelt and twirled my tongue around the head of that wonderful large black cock. I ran my hands up and down its length and caressed Coach's balls as I began to fuck my mouth down on his cock. Deeper, Coach said, and I obliged him my pushing my head lower and lower and lower until my nose was nestled in his pubic hair.

As I blew him, Coach caressed my head, running his hands through my hair. He told me he had the hormones for me and that each Monday I should come to his office for two injections in my ass. One being his prick, and the other being a needle. He told me his supplier had come up with something new and these hormones were fast acting. Almost immediately my skin should start to soften. Within a month, my ass should start retaining fat and grow rounder, and my tits should start showing signs of growth. Coach said that normally a girl like me should expect to be able to grow tits one size smaller than her mother's. He said that would not help me much since my mother's tits were so small. He said that he knew someone who would give me implants if I ever wanted them, but they would cost about five grand. I had not really thought about having my own breasts before. The idea was... exciting.

Coach pulled me up and backed me up against an empty wall. He lifted one of my legs and held it high as he aimed his cock at my pucker. He slid into me easily and sank his shaft easily into my ass. His was the biggest cock I had taken so far, but he slid easily inside of me. Coach used his other hand to twist my nipples. He seemed delighted by my bauble dancing from my belly button.

His cock slid across my prostate and I was seeing stars as he roughly fucked me against the wall. It took only five minutes before he spasmed and my ass filled with his cum. When his cock slid out, the cum ran down my leg.

Coach told me to bend over his desk and he took a syringe out of his drawer, filled it from a vial and then jabbed me saying that he figured that was the smallest prick I'd yet had in my ass!

I took a few minutes in his private washroom to clean up the cum, remove my lipstick and try to get the rest of his cum out of my ass. When I returned to class I was wearing the panties, rather than my Carl underwear. For the rest of the afternoon I made occasional squishing noises, as residual cum leaked out of my ass and made my panties moist.

Chapter 19 - Expanding Horizons

On Tuesday I met up after school with Douglas, one of Johnny's five friends who had gangbanged me at the Ambassador. A couple of the guys had contacted me by email. Douglas was the quickest to ask if we could get together just one on one. I told him that he would have to either get us a room at the Ambassador in Seneca or he would have to buy me some dinner. He opted for the hotel room. I think he was afraid of being seen with me in public, not being comfortable yet with the boy part of me.

I told mom I was going to go study with one of my friends and would not be back until close to eleven. She scolded me for staying out late with school the next day, but also seemed relieved that she would not have to put up with me around the house for the evening.

I walked a block away and met Carlos whom I had called earlier. I had not told him that it was Sindy who was calling and so he figured he was just picking up a regular fare. I got in and told him where to drive me. As we drove I pulled out my makeup compact and put on some lipstick and a bit of eyeshadow. Carlos was watching me in the mirror, puzzled. But when I took out a cigarette and lit and then said hello to him in my Sindy voice, he looked back in surprise. You are boy? he asked me? Do I look like a boy, Carlos? No, no. I just surprised is all! He replied.

Carlos was now one of the growing number of people who knew that Sindy and Carl were the same person. He did not seem disturbed at all when I pulled down his pants and blew him in return for the cab ride. Once again he gave me an extra twenty bucks for smoking while I sucked him off.

Douglas let me in the room and was a bit puzzled by my half-boy half-girl appearance. I told him to go for a walk and come back in a half hour. I used that time to change into the Sindy outfit I had brought along and to finish my makeup which I had crudely started in the car.

When Douglas returned he found me laying on the bed wearing nothing more than some frilly panties and dark stockings and heels. He hastily climbed on the bed and kissed me tentatively. I kissed him back as I removed his clothing. I took his prick in my mouth and was gobbling on his juicy cock just five minutes after he had come back into the room. No nice preliminaries for this boy. He was eager!

I realized how eager a couple moments later when I felt his hand grasp my cock and start to stroke it. I asked him if he had done this before and he muttered no, but said he had always wondered what it would be like to touch another guy's cock. I told him I was NOT another guy, and he stammered that he had not meant that I was a guy... just that he had been curious. His touch felt nice and we played with each other's cocks for awhile. I moved to take him in my mouth again and he swung around so that his face was in my crotch, and he hesitantly licked MY pricklet!

Soon we were both sucking eagerly on each other's hot dicks. Douglas may have been an amateur, but his mouth was warm and felt as nice as Cassie's and Karen's, and even Danny's had.

I pushed my head all the way down on Douglas's dick. He tried to do the same to me, but he choked and sputtered!

I lay back and wrapped my legs around Dougie's back, pulling his groin to mine. We ground our cocks against each other for a few minutes. Then I said to him, fuck me. Just that simple. And that is what he did. With no resistance at all, his cock slid up into my back passage and he was comfortably inserted inside me. He leaned his head down and kissed my lips. I sucked his tongue hungrily and he began to thrust his cock in and out of me. I pulled his head further down and he sucked on one nipple, and then the other. I shivered in delight.

After ten minutes of bliss, Dougie was ready to squirt. He pumped a nice load into my ass and collapsed on me.

A few minutes of rest and I thought Dougie might be done. But instead he rolled over and asked me if I would fuck him in the ass. He knew I liked being fucked a lot, and just as he had been curious about touching another guy's dick and sucking on one... he had done those, and figured maybe he should go all the way and see if he liked having a cock in his ass!

I told him I did not want to. I wanted to be the girl, not the guy. But he pleaded with me and I remembered that Cassie had gotten off so much on fucking me in the ass, that she had gone out and fucked Karen a few nights later!

I went to my bag and retrieved my bottle of lube. I had not needed it lately - it seemed that spit was all I now needed to get cocks to fit into my butt. But Doug had never even tried putting a carrot up his ass, so he was bound to be tight.

I put a couple of pillows underneath Doug's ass. I might have gotten better position if I tried to do this doggie style with him, but he wanted to watch, which meant bending him over backwards. I used a couple of fingers to smear the lube around his asshole and to push lube inside. While I did that, Dougie used lube to moisten my dick and work it to full attention.

As to fucking other people, I was a virgin other than my escapades with Karen a couple days earlier. Now here I was pushing the head of my cockette against Doug's anus, and meeting stiff resistance. Doug grunted in protest, and I almost thought we were going to stop. But I pushed a bit harder and finally my glans pushed past his sphincter. Once that was accomplished, steady pressure allowed me to sink another two inches inside him.

He told me to wait, wait, wait.. and I did pause and let him get used to the feeling. Then I pulled back a bit and pushed some more. Over the next ten minutes I slowly pushed and pulled my cock inside his ass as he grew accustomed to it. I cannot say that that time gave me a lot of pleasure. It was like having my cockette squeezed by a tight velvet vise which kept trying to push me out. Finally my entire five inches were firmly in Doug's ass. Doug was no longer complaining of pain so I took this as a sign and began to pull back and thrust harder. At the same time I wiggled my cock around as best as I could, trying to be sure I found his prostate.

I knew I had found my target when Doug began to moan in pleasure and lick his lips. His eyes were shut most of the time, but I could tell that he was beginning to like the fucking. His own six inch cock was very rigid and I grabbed hold of it and began to stroke him.

His ass was definitely a lot tighter than Karen's cunt had been. I guess anal muscles are firmer than pussy muscles. After another five minutes, Doug's face scrunched up, his leg muscles tightened, and he sprayed his cum onto his chest. This all caused his sphincter to grip my pricklet tightly and I shouted as I fountained my own cream into his rear.

We both lay panting on the bed for several minutes and then Dougie hurriedly dressed and left. Later that night I introduced Danny and Doug to each other by email. Doug never asked me out again. (Two months later I got an email from Danny thanking me for sending Doug his way. Doug had just recently told all his friends that he was gay and introduced Danny to his family as his boyfriend!)
I was going to clean myself up and call Carlos to drive me home, when I realized it was still only nine pm - I could still safely stay out for another couple of hours.

There was a bar just down the street from the hotel. I fixed up my makeup, put on the blouse and skirt that I would have worn if Doug had taken me to dinner and I went out to the bar. I would I would have one drink and then I would head home. I left my bag and boy clothes in the room.

In the Kat Klub, I sat at the bar and ordered a cosmopolitan. I lit a cigarette, crossed my legs and looked around the place. There were maybe a couple dozen people there, most talking to each other, although a few guys and gals seemed to be on their own. A couple guys gave me questioning looks and one even had the bartender give me another cosmo. The guy was probably at least forty and had already had a few too many. He came over and sat beside me. We chatted and I eventually realized that he thought I was a hooker. He confirmed it when he asked me how much it would cost him to fuck me for an hour.

While I pretended to think about his offer, I lit another cigarette and took a closer look around me. I realized that many of the girls in the place were most likely hookers and most of the men were potential customers. This was not the innocent bar I had taken it to be.

I told him that I was not interested... tonight. In fact, his offer was tempting but I had to get home sooner than an hour long fuck would permit. And besides, I wasn't sure that I felt safe.

I left the bar and on the walk back to the hotel I asked Carlos to pick me up. I suggested though that he park and come up to the room, since I could give him his blow job up there much better than in his cab on the way home.

Five minutes later Carlos was squatted in a chair in the room, holding my head down onto his cock as he fucked my face vigorously. He was grunting and groaning and telling me I was a prettyboy, and that all sissy boys need a man to fuck their faces! But before he came, he pushed me off of his dick and I went sprawling on the floor. He picked me up and threw me on the bed. Before I could react, he had ripped my stockings as he roughly pulled my panties down.

He pushed me face down onto the bed and positioned my ass so that is was high in the air. Then he surprised me by pulling one hundred dollars out of his pocket and waving it in front of my mashed face. Is this enough, he asked? I said yes and right away he pushed his cock into my ass! He had no style, but he had stamina. He pushed and pulled, thrust and pistoned his dick in and out of my ass for the next fifteen minutes. He pushed me down on the bed, bent me over the table, pushed me up against the wall. We were all over the room as his cock pounded me. But finally he jammed his cock into me hard, and he jetted his hot cream into my bowels.

Almost instantly he became meek again and kept apologizing for being so rough. He even tossed another fifty dollars on the bed. I told him that I would need ten minutes to change and he should wait in the taxi.

Ten minutes later I was back in Carl mode carrying my Sindy bag and with an extra $170 in my pocket that had not been there at the beginning of the night. My nest egg was growing! I hopped into the back seat of the cab, leaned forward and gave Carlos a peck on the cheek and then leaned back as he drove me home.

Chapter 20 - Detention

The other night Principal Henderson has whispered in my ear that I would have detention on Wednesday after school. Well it was not quite detention, just a call to his office which was handed to me as a note during the day. As the final bell rang, I grabbed my Sindy bag from my locker and went to the school offices. I had to wait on a hard chair for ten minutes outside his door while he finished up with some other students.

When I was let into his office he surprised me by having me sit in the chair across the desk from him, and then talking to me about my grades. He asked me what I had planned when I left high school in a year and a half. I told him that my mom did not have much money, but I hoped to get a scholarship to go to university to study chemistry or biology, or maybe even some kind of engineering.

Looking in my file, he shook his head. He told me that up until this year my marks would have qualified me for a scholarship, but at the moment every one of my teachers was reporting a failing grade this year. I HAD realized this, but I could not tell him that I was no longer studying at all because instead Sindy was out chasing men to get them to fuck her!

He then asked to see the bag I had brought along. I opened my Sindy bag and he inspected the makeup, the bra and nylons and basic girl clothes. He came out from behind is desk and locked his office door. He then sat on the edge of the desk in front of me and put his finger under my chin and lifted my head. Lovely eyes and lips he said. He handed me the lipstick and told me to put some on. As he did so he pulled down his pants and shorts and his stiff cock bobbed in front of my face.

He said that he did not think that he had ever had sex with both a mother and her son before. He then pushed his cock into my mouth and I began to suck him.

While I bobbed my head on his cock he told me that he thought he could solve my marks problem. He asked me if I had heard that Becky Winters had left school. I had noticed she was not around, but thought she was sick. He told me that she had become pregnant and that she and her boyfriend Dwight Moore were going to get married and had decided it would be best if they moved to another city. They were hoping it would be a nice black baby, so that Dwight could be confident he was the father, but Becky fucked so many other guys, that they would never ever be sure.

This left a problem though. Becky had been having regular sex with several of the teachers and they were all asking the Principal to find them a replacement who would be able to satisfy their needs but also be able to keep her mouth shut, well, other than when it was filled with cock.

Principal Henderson asked me if I would be interested in filling that position. In return, they would promise that my grades would be good enough to get my scholarship, even if I failed every single exam that was set for me.

My mouth was full of his dick, so I just smiled and nodded. When I could I asked him what he got out of this? He laughed and said that he was just a broker in the deal, but he got a commission - which meant that once a week he would want my services. He might ask me to suck him off under his desk, or he might take me to a hotel for an evening.

He asked me if it was going to be a problem, what with him dating my mother from time to time. Would I have a problem being fucked by my mothers-fucker, so to speak! I told him it would not bother me at all. I actually found it to be kinky, I told him.

He then pulled me to my feet and asked me to put on my nylons and heels. He also handed me a school cheerleaders sweater and skirt. He said that I should not bother with the panties.

I also lubed up my ass and two minutes later he had me bent over his desk and was ramming my bum with his stiff rod. Only a few minutes later, he spilled his seed inside of me, and a few minutes later I was out the door.

Over the next couple of weeks I had my first encounters with each of my teachers. These were mostly in their classrooms behind locked doors. The teachers who were not married generally took me back to their homes, and one rented a hotel room.

None of my teachers was interested in my boy equipment, and it did not bother any of them either. I did get compliments on how much tighter my ass was than Becky's pussy. I gathered that a few of them had similar arrangements with other students too, but I did not really care. What I cared was that I suddenly had an even wider assortment of cocks available to fuck me silly! Principal Henderson thought he was helping out his teachers, but he was definitely giving me more of what I wanted! Cassie had called me a cockhound, and she was right!

This is where I have to stop telling you about every single one of my meetings, but rather to just hit the highlights. But you can be assured that I now had at least one fucking every day, sometimes two and sometimes more, with plenty of sucking and my own cum spurting mixed in!

But I will tell you a bit about some of my teachers.

Mr. Jenkins was the most traditional. He wanted to sit and cuddle and kiss with Sindy for awhile before I went down on him and he eventually porked my butt!

Mr. Konstantin never fucked me. He did like me to suck him, but mainly he just wanted me to wear nylons and rub his cock between my feet until he gushed his cum!

Mr. Carpenter would fuck me sometimes, but really he just liked to watch me suck his cock. He liked me to wear bright lipstick and to be sure that I left lots of it on his cock as I slurped on it.

Mr. Strickland must have thought he was an old English professor. He mostly wanted to bend me over his knees, pull down my panties and whack my bottom with a wooden ruler. Of course, he also eventually worked two or three fingers up my ass in order to make me squirm.

I even serviced Mrs. Bumgartner. She was an elderly crone and I winced the first time that she told me I had to eat out her wrinkled pussy. But it quickly softened under my tongue and she was quite tasty. And she sure knew how to use a strap on. I think she fucked my ass better than any of my male teachers, the only disappointment being that it was cold rubber ploughing me, rather than warm flesh!

Chapter 21 - Baked

As I mentioned, from now on I am not going to tell you about ever single bit of sex I had. I am just going to hit the highlights. I now was seeing my teachers and several of the guys from my pimped out orgy that Johnny had arranged. Plus word seemed to be leaking out and I was getting emails from strangers looking to hook up. My own classmates were starting to look at me peculiarly and so I wondered if there was gossip around the school.

I was having my weekly jab of hormones from Coach and I could feel the hormones working inside. I had also started tweezing my eyebrows and had gotten my hair coloured even lighter. I still had to wear Carl clothes to school of course, but I now found myself having better taste, and with a bit more money in my pocket I had improved my wardrobe. However I realized that all of this was making Carl look much more effeminate. And you know what, I did not care!

Christmas was coming up very soon and I had gotten out and picked up some nice presents for mom and Cassie. I wondered what they were going to get me.

On the Saturday before Christmas, the whole family was going out, but separately.

Mom was being picked up by one of the women from her office and they were going to a Christmas function at her boss' house.

Cassie was going out somewhere with Johnny. I barely said anything to Johnny these days. A couple times when he stayed overnight with Cassie I heard him tapping lightly at my door in the wee hours, but I just ignored him.

And me... well, it was going to be a girl's night out. Karen Henderson was picking me up in her car and we were going to go to a bar and dance the night away - me looking for a cute guy to fuck, and her.... well, she would be looking for a cute gal to fuck!

Mom was gone early which gave me time to get dressed at home. Karen came over early enough to help me with my makeup and once again she had me looking pretty slutty. That was fine with me. I wanted the guys to know I was hungry for them! Karen also helped me lube up my ass and insert my butt plug. She thought it would be a real giggle to see me squirming all evening!

We never made it to a dance club. We did not drive into Springfield but rather drove only as far as Seneca. I soon figured out that Karen was again making the rounds, dropping off weed to various of her customers. We smoked a couple of joints in the car and eventually we stopped off at the Kat Klub for a couple of drinks. I had mentioned the place to Karen and she was curious to see it. We were there for only a half hour but we were approached by several guys, first trying to get into our panties for free and then offering us money. One older guy was particularly cute and so I let him take me out to his car and I sucked him off for forty bucks. But we got out of there soon after. The other gals in the place were giving us hostile glares. I suspected they were regulars who did not like competition from young amateurs.

I found I liked being able to put a bit of extra money in my purse and figured I would be back.

Both of us were a bit drunk but the weed was wearing off. Karen just drove us a couple miles out of town to Blueberry Hill, a lookout point that was popular with our classmates. It was a bit early and there were only a couple of other cars there. Karen fired up some kind of bong and we both took a couple of strong hits. We talked a bit, cuddled a bit, made out a bit. We had more weed. Soon I got soppy and began crying, telling Karen that I was all confused. Sindy was taking over my life and I liked it SO much. I just wished that Carl could go away forever.

We toked some more and the car became thick with fumes. We were totally ripped, stoned, baked! Cars around us came and went and we just sat there and talked about my family life, her family life, the woman who had first seduced her, how strict her father was, how she had gotten into selling weed.... just good girl talk. With some heavy petting tossed in. Occasionally Karen would reach into my panties and grab the base of the butt plug and move it about inside of me, making me squeal with pleasure.

I played with her large gorgeous tits for awhile. It made me realize that I really did want breasts of my own. But visions of Becky Winter's rock hard fake jugs kept coming to mind. Karen's boobs were nice and jiggly and fun to play with, but Becky's bullets had slut appeal!

I was nuzzling and sucking on one of her nipples and Karen was moaning softly when I heard a sudden knocking on the car window. I looked up and was surprised to see a female cop peering in the window and beckoning Karen to roll the window down. I looked out my window and there was a male trooper, shining a flashlight in the window! When Karen opened her window a cloud of sickly sweet funky air hit the female cop in the face and she coughed!

A few minutes later, I was sitting in the passenger seat of the cop car with the Patrolman Dick Hooper while Karen was in the back seat of her own car with the female officer. In the cop car the officer asked me my name and asked me for my identification. I told him my name was Sindy. When he asked me my last name I told him it was Barton. He took a close look at me and asked me if my mom was Miriam Barton from Bigelow. I said yes and he said he thought that Miriam's daughter was named Cassandra, not Sindy.

I giggled a bit, still quite high from the dope we had been smoking. Office Hooper asked me what was so funny. When I tried to hug my pocket book close to my chest he took it from me forcefully and searched it. He found a joint, which he put into his shirt pocket, and then he found my id. His eyebrows raised when he read that my real name was Carl. He again took a hard look at me and then nodded and handed me back my purse. He asked me if my mom knew what I was up to. I giggled again, and said no.

I thought I was in serious trouble, but then a grin broke out on his face and he told me to relax. He took the cop car's lighter and lit up the joint, inhaling deeply. He told me that he and his partner were off duty and they had arranged to meet Karen up here to buy some weed from her. She was their supplier too. His partner was a lesbian and so was having a bit of fun with Karen in the other car as well.

He looked at me and said that he might have asked me if I was a lesbian too, but, now that he knew my secret, he wondered if I was more interested in men than in girls! He leaned over and kissed me at the same time forcing some of the weed smoke into me. We sat there and necked for awhile. Dick had a full mustache, which tickled me. It was the first time I had ever kissed a man with facial hair, other than just stubble.

He asked if he could see my cock. I pulled down my panties and held my skirt back so he could see and stroke my dicklet. He continued to kiss me as he teased my cock head. Then he noticed I was squirming. Reaching lower down he discovered the plug in my ass. This amused him.

He pulled my head down into his lap and released his cock from his regulation trousers. It was already quite stiff and I mewed and giggled again as I opened wide and took his dick all the way down my throat on first gulp. He gasped at how far down his cock my face had plunged, but groaned encouragement at me. For the next five minutes I licked and sucked on his gorgeous meat stick. But I wanted more.

While Karen and I had enjoyed ourselves that evening, I had gone out expecting to find a dick to fuck me and finally I had one in my grasp - we, in my mouth at the moment. I managed to lean Dick's seat back enough that was able to straddle his lap and then I sat down facing him, letting his cock slide into my boycunt that had been held open by the butt plug that I had just pulled out and flopped onto the passenger seat.

Dick's cock was fairly thick and felt oh so very nice as I let myself sink down on it. Dick grabbed my ass and helped me to raise and lower myself on his cock. It was awkward because I had to lean against him since the roof of the car did not let me sit fully upright on him. I squeezed my ass muscles and shimmied my butt on his lap for the next ten minutes. Just before Dick spurted his cum into my ass, the car doors opened and Karen and the woman cop both peered in to see what we were up to. Karen stroked my arms and murmured encouraging words as I fucked myself on Dick's... well, on Dick's dick! Finally I let out a soft moan as my own cockette spurted my cream onto Dick's chest. With this, I clamped my ass hard around his pistoning cock, and he shot his wad deep into my boipussy!

I retrieved my butt plug before the cops drove away. Karen and I helped each other get dressed again. I noticed that she had a violent hickey on her neck that I had not left there. We were both tired, but were much more sober and less stoned after that experience, enough so that Karen felt comfortable driving me home. But she was not in good enough shape to make it back to her own house AND past her sleeping father. So Karen came upstairs with me.

As we crept up the stairs, I could hear a lot of noise from both my mother's room and from behind Cassie's door. They had both gotten lucky and brought men home with them. I cleaned off my makeup and climbed in bed with Karen. We kissed a little bit, but we were still both pretty buzzed and we each slowly drifted off to sleep. I was on my side with Karen spooning me from the back. It felt so nice to have her big soft pillows against me.

In the morning I heard lots of activity from other parts of the house as Karen and I slowly woke up. There was a knock on my door and Cassie poked her head inside saying that breakfast would be on the table in fifteen minutes. We both quickly washed enough to be presentable. Karen dressed in her clothes from the previous night and I put on some good Carl clothes..

When we got to the kitchen, Mom beamed with delight as I led Karen into the room, hand in hand. I was surprised to find four women in the kitchen already. It turns out that Mom and Cassie had each brought home a woman lover last night. Mom was sitting beside Mrs. Morton who worked with her but was not the co-worker who had picked her up last night. Cassie was passing some toast to Angela Simpkins, a cute girl from my junior class who was looking rather smitten with Cassie.
As we had light awkward conversation around the table, Mom was looking puzzled. I suddenly realized that I had not removed the nail polish from two of my fingers, and when I looked down at my bare feet I saw that all of my toenails were still painted bright red. Mom smiled at me and mouthed, "we'll talk" but fortunately we were all busy with our respective friends after breakfast. Mom drove Mrs. Morton home to her husband. Cassie and Angela went up to her room for a bit more fun. I saw Karen out to her car. When we opened the door it still smelled extremely funky. We kissed each other on the cheek and then she drove off.

I went back to bed until mid-afternoon. Mom did not return until after dinner and I fled to my room, claiming I had to study.

Chapter 22 - Christmas Surprises

Mom knew I was avoiding having a discussion with her and it seemed she was happy enough to let things coast for the time being.

Christmas and a two week school break were coming up in a week. Two days before we were done for the holidays we got our mid term reports. When I took my report home, Mom was delighted to see all the As and A-s on the report. Of course, she didn't know that I had got those for sucking and fucking, rather than for studying hard.

By this point I was having sex with several of my classmates and teachers on a regular basis. The hormone injections I was getting from Coach Grogan were having an effect. I had never really had to shave much, and now I did not have to shave at all. My emotions were much more volatile and I found myself crying a lot more. Also giggling, but of course, that was also because I was getting high a great deal of the time. I was giving Karen a lot of money these days in exchange for a lot of weed which I was smoking every night before heading home after getting my ass fucked.

I was also noticing that my Carl jeans and other pants were not fitting well anymore. My hips and ass were getting larger. In fact, I asked both mom and Cassie for new larger jeans for Christmas.

All three of us were out of the house on Christmas eve. Cassie was over at Johnny's house with his family. Mom had been disappointed earlier in the day when Mr. Henderson had called up to cancel their date for the evening, so she went over to a neighbour's house where several neighbours got together to celebrate the holiday.

Me? I went out to a nice dinner at a fancy restaurant and then to an elegant hotel room in Springfield. I was dressed in a stunning "little black dress" which my date had purchased for me. Prior to arriving at the restaurant my date and I had each snorted a line of coke in his car. This was my first experience with harder drugs, and I had been a bit reluctant. But my date had insisted that I would not get hooked if I tried it just once. It was definitely a different experience. I noticed that all of my food tasted so much better. My date and I played footsie in the fancy restaurant.

When we got to the hotel room, I was absolutely gagging to get Mr. Henderson's cock down my throat. Yes, the principal had cancelled his date with my mom so that he could take ME out and fuck me silly. And he did. Fuck me I mean. Several times. I was well and truly fucked. Fucked fucked fucked. Or did I say that already? My head was a bit screwed up from the coke and the joint I smoked in bed afterwards. When we were done and Jordan was showering - we were finally on a first name basis - I told him that there was a big favour that I might want from him. I told him that I had been thinking of living as Sindy full time, and if I did, I would need his help at the school. He laughed at this and I asked him what was funny. He just chortled and said that I should ask him again in a week.

He also told me that I was going to have to face my mother about this sooner or later. I told him I was getting ready to do that. He smiled again.

I lit another cigarette just as he finished dressing. He leaned down and gave me a quick kiss on the cheek, and then he left.

I had asked him to not drive me home. Rather a few minutes later Carlos came into the room. He had been so good to me over the past weeks that I had promised him a Christmas bonus. He had tried to clean himself up a bit, but he still looked scruffy, had a raspy beard and smelled bad. But I had grown fond of the big lummox.

For the next hour we had rough hard sex which seemed to be the only way he knew how to fuck. By the end I had a few bruises, and had bit my tongue. But Carlos had come three times, once in my mouth and twice in my quite well used ass.

Carlos waited out in his cab as I changed back to Carl. Carlos drove me back to Bigelow. As I got out of his cab, he handed me an envelope with a Christmas card in it. It was a nativity scene since Carlos was very religious (he had several crosses dangling from his rear view mirror). There was also a picture of his wife and two children. I guess it was the card that his family gave to all of their friends this year. I gave him a big hug and a peck on the cheek and wished him a merry Christmas! As he drove away, I took the three hundred dollar bills out of the card and put them in my purse and tossed the card in the trash!

Christmas morning I slept quite well. Cassie woke me up with a kiss on the forehead and told me that mom would have breakfast in half an hour. I hopped into the shower and scrubbed away any lingering cum from the night before. As I soaped up my chest I noticed that my nipples were puffy and sensitive. My ass was definitely feeling much bigger too. I took special care to soap up my ass and stuck a couple fingers deep inside to get extra clean.

Feeling a bit frisky, I put on a pair of panties under my jeans. Those jeans were very difficult to get over my growing butt!. I looked in the mirror and longed to put on some eyeshadow and lipstick. I was going to have to have a talk with mom real soon.

But that talk came much sooner than I expected.

On Christmas morning there were normally only a few presents under the tree. This morning there were a lot of them. Mom was a bit coy about handing them all out first. So Mom and Cassie each opened the presents that I gave them, and Mom opened her present from Cassie.

She then handed me a wrapped present to open. When I had torn the paper and opened the box I found a pair of jeans - but they had a pattern of flowers and butterflies on the back pocket and down the leg. I realized they were girl jeans. Puzzled I looked at Mom and she had tears in her eyes as she said, Merry Christmas Sindy!

She knew! Mom explained that over the past couple of months she had known that something was up, something was different. She had been pleased when I had finally begun dating girls like Karen, but she had realized that perhaps it was just not girls, when she found all the cum stains in my bedding. And then she had found my Sindy bag under my bed. Plus the time a week ago when I had missed removing some nail polish had not been the first time.

And she had noticed my wider hips and even through my t-shirt she had noticed my growing tits. So she had finally confronted Cassie a couple weeks back and got the full story from her. Well, not the FULL story as it turned out. Cassie had not told Mom that I was a cock slut, as I was later relieved to hear from her. Cassie had told mom about my first date, and then that after that I had been going out as Sindy and found I enjoyed being Sindy much more than I liked being Carl.

I hugged Mom and she asked me if I was truly happy as Sindy - she had been so worried when I was buried in my room all the time as Carl. I told her that, yes, being Sindy was fantastic and it was harder and harder to pretend to be Carl anymore - hence the hormones.

It turned out that the other presents were all from Mom to Sindy. Mom had bought me lots of panties and bras, blouses and skirts - she had gone quite overboard in buying me a whole wardrobe of nice, reserved, young women's clothes.

I cried more as I opened each box. Half of everything was going to have to go back because it was the wrong size, and most of it was much more conservative than I was going to want to wear. The last box Mom handed to me was small. I opened it and I found a new id card, in the name of Cindy Barton. Mom had arranged a name change for me! And, she said, she had arranged with Mr. Henderson - whom she reminded me she was dating some times (and whom, I did not tell her, had fucked my ass soundly the night before!) for me to return to school as Cindy after the holidays!

I hugged her tightly and she suggested that I go upstairs and change so that she could meet her elder daughter properly. Cassie and Mom both helped me carry all of my gifts upstairs and I then spent the next hour looking through everything more closely and deciding what to wear first.

It took another hour for me dress, put on my makeup and fix my hair properly. Cassie helped me with all of this a bit. I was nervous as hell and gasping for a cigarette! In the end I wore only a pair of panties that Mom gave me. If Mom was going to meet Sindy (yes, despite my legal name beginning with a C, I would still think of myself with an S, for sin, sex and seduction) I figured she should get used to a bit more sexy version. I wore dark stockings and a garter belt, three inch heels, a short black skirt and a tight top that left my navel exposed.

Mom's eyebrows rose as I came downstairs, particularly when she say my pierced belly button and dangler. But she hugged me and complimented me. I excused myself and went outside for a cigarette. Cassie joined me. Another surprise for mom, both of her daughters smoked, although it could not have been too much of a shock, since most of the Sindy clothes she found would have been covered in the smell of tobacco.

Back inside Mom complimented me on the ease with which I walked in my heels and told me my legs looked very nice. She told me she had arranged for me to see a doctor in Springfield who would assess me and put me on a proper hormone regimen. We hugged and both cried a bit more.

What I didn't tell her was that I was perfectly happy to be a girl with a big clittie. I did want the hormones. I did want the body curves and breasts of a woman, but I had no desire to give up my cock. While I LOVED the attention of men, and having my bottom filled with their cocks, I had begun using my own dick more, in girls and sometimes in guys. And whether I was fucking, or being sucked, or someone was just teasing my dick with their hands, I loved the pleasure it gave me. I did not need a vagina to be fucked, so I planned to keep my pretty cockette!

Mom spent a good deal of the day cooking a great turkey dinner. Late in the afternoon the Hendersons came over to have dinner with us. In the car on the way over, Jordan told Stevie and Karen that they were in for a surprise - they would be meeting Miriam's new daughter, and then he explained to them that Carl now wanted to be known as Cindy.

When they arrived, Karen hugged and kissed me. Jordan gave me a gentle, principal-like hug. Stevie, the only Henderson who knew nothing about Sindy beforehand, just stared at me and stuttered, then finally told me that I looked hot. I guess it was quite a shock for him. He and I had been in school clubs together for the past few years, had swapped comic books, had played hundreds of hours of video games. And now one of his best friends had decided to be a girl!

Dinner was terrific and we all sat around watching a bit of tv afterwards. We took a break and all of us pitched in to help clean up the table and the dishes. We three girls (I was one of the girls now!!) went outside a few times for cigarettes and once we went around the block where we could smoke a joint)

Stevie said practically nothing to me all evening. He just stared. I realized that he was just a loser like so many of the other guys at school. Heck, like I had been before I discovered how pretty I could be. I promptly put him out of my mind.

At 9 pm the Hendersons left. Mom went with them. She and Jordan were going over to the house of one of the other teachers at school after they dropped Karen and Stevie off at home.

When they were gone, Cassie took me by the hand and took me up to her bedroom. I was emotionally exhausted from the revelations of the day, but always had time for my pretty sister. Cassie told me that I had not noticed that she had not given me my present yet. She handed me a box which I opened to find a new strap on harness and thick dildo shaped like a realistic black cock.

She kissed me, at first tenderly and then more aggressively. For the next ten minutes we wrestled on the bed, lips on lips, lips on nipples, my fingers caressing her pussy, her fingers wrapped around my cock. My nipples were increasingly sensitive and I squirmed when she bit them. I was panting good and asked her to put the harness on and fuck me. But instead she told ME to put it on and fuck her! She had decided that I should fuck her, but as she would never let me put my cock in her pussy, she had bought me the harness and cock to use on her. It was a bit awkward to place the dildo above my own boyclit, but I managed and soon, I was on top of my own sister, ramming the thick black dick in and out of her pussy. We locked lips and sucked tongues as she moaned lustily. We did this for twenty minutes and I began to get a bit bored. Honest, I loved to pleasure my sister, but neither my cock nor my boipussy were getting any stimulation.

Sis realized my mind was drifting and asked me if I was ready for my second present. I nodded and she told me to leave the harness on, but to remove the fake cock. She reached over and pulled me close. She took my dicklette in her mouth and sucked me to a stiff erection. As she did she took some lube from the drawer beside the bed and used her fingers to lube up my ass. She turned me around and worked the big cock slowly into my ass pussy. It was big, but I had had lots of cock in me by this point and it slid in nicely... all nine inches of it disappeared. She then moved a couple pieces of the harness around and the base of the dildo clicked into place. She let go and the harness was holding the entire length of the cock inside of me!

I squirmed around on the bed. My actions caused the dick to slide around inside of me. It felt wonderful.

Cassie then told me to get on my knees. I panted while doing so, more pleasure rippling through me. She again took the bottle of lube, but this time she pushed the liquid into her own ass. She then presented her ass to me, telling me that THIS was my second present - she wanted her older sister to fuck her in her ass.

I positioned my cock at her butt chute, and pushed in. I met resistance, and she groaned a bit in pain, but I persevered. I knew she had let Johnny do this with her more than once, and Karen had told me that SHE had fucked Cassie's ass with a dildo, but sis was still not very experienced at taking a cock back there, so I was slow and patient. When I was a few inches in, she urged me to push harder, and soon I was all the way in, and then I was fucking my lovely sister vigorously. Her fingernails dug into my back at times, and her heels pulled my butt tightly to hers at times.

We kissed enthusiastically, and we both shouted loudly at times. It was a blissful ten minutes and then I finally pushed deep into Cassie and squirted a whole days worth of jism into her bowels! God, an ass was SO much tighter than a cunt!

We lay there snuggling for awhile and then we returned to bed to cuddle for awhile.

Finally I put on a new nightie that Mom had bought for me and slipped under the covers.

Tomorrow was a new day, and a new life!

Chapter 23 - Girl Power!

Ten days to prepare for going back to school did not seem like long enough.

All of my boy clothes got stuffed into bags and given to charity. We repainted my room in bright colours and I got new sheets and bedspread in various shades of reds, pinks and autumn colours. My drawers were filled with panties and stockings and other frillies. The hangars in my closet held my few dresses, but I knew the closet would soon be full.

Cassie and Karen went with me to the mall where I got my ears pierced multiple times. I bought myself a cute ankle bracelet as well as a bunch of other inexpensive earrings and necklaces. I went to the tattoo parlour and added more paw prints, now leading up my side, and also down one ass cheek, curling around towards my asshole.

We went to the salon where I had a complete body waxing again. I also had my hair cut and dyed. I no longer needed the pony tail so that I could appear boy or girl at different times. I got a nice sexy shoulder length cut, with bangs, which I just loved. And my hair was dyed platinum blonde.

I got into my first girl fight with mom when she found me smoking in my room. Even with the windows open she refused to let me "stink up the whole house." This was just the start of my deteriorating relationship with mom.

I was very nervous when school started. Cassie stayed close by me on the first day, but by the end of the second day pretty much everything was normal - well, as normal as things can be for a hot girl! No one seemed to have any problem with Carl suddenly becoming Sindy. Most of the guys were too shy to come up and talk to me (at least, out in the open), but all of the girls were eager to welcome me and make me feel like one of them. Almost everyone figured I had already had a sex change operation. Those girls who asked to see my dick, well I showed my cock to them. The guys generally got to see it only if they took me out on a date and fucked me. Which was a lot of them.

I was having sex on a regular basis, and by regular I mean two and sometimes three times a day. Teachers, principal, fellow students... they all wanted a piece of me. And I was loving it. My boipussy was stuffed so full of cock that I was in heaven. I was also quite high a lot of the time. Karen was keeping me well supplied with weed, so long as I could pay her for it.

Mom drove me to my first appointment with the doctor in Springfield. After that I made my own way over - either Cassie or Karen drove me, or one of the guys I was going to fuck after the appointment. And sometimes Carlos drove me in his cab.

The doctor was disappointing. He did not like the hormones that Coach Grogan was giving me. He thought I had good development, but thought that the drugs could be damaging my liver and other organs. He wanted to put me on other 'mones and cut the dosage way down to better manage my transition. He was disturbed to hear that I wanted to talk about breast implants already. He figured I needed at least a year of psychological evaluation before that step. To keep mom happy I just nodded and said yes and told him to go ahead and order me the new meds.

Then I went to Coach Grogan and told him I wanted him to double my weekly injections. I also got the name of the doctor whom he said would do my breasts for me.

Coach Grogan's cock was still the largest dick that was fucking me on a regular basis. Principal Henderson was not giving me "detention" quite as often, but by now most of the guys on the football and basketball teams had talked to each other and had come knocking at my backdoor (yes, I mean my hershey highway) and I had let them in, willingly!

Over the next couple of months I developed a routine. I studied very little, preferring mostly to hang out with Karen and a number of the other cool girls. During daytime, we skipped a lot of classes and went shopping, or just went to someone's house and got high while we talked about which guys we were all dating and fucking. When we compared notes, I had to be modest and say I was having sex only a couple time each week. I could not tell them about the teachers, nor that I was being fucked by most of the girls' boyfriends!
If we were at school, we were usually hanging around the front, smoking and making fun of the nebbish kids who actually went to classes!

Mom did not know any of this of course. She thought I was working hard. This was proven by all the wonderful test marks that I kept getting back from all the teachers who I was sucking and fucking for better grades.

Mom had no idea that I was such a cock slut. She did know that I was having sex, both with guys and girls. She most often saw me with Karen, but to keep her from being too curious I asked Jamal to sleep over several times. Jamal was one of the stars of the basketball team. He was not the tallest of the black players on the team, but after having sex with all five of the starters at the same time after one game, I knew that Jamal had the biggest dick. He was also smart, bright and articulate. So it was good to have him over once in awhile and pretend that he was my boyfriend. Jamal was happy to help me out, provided that I let him fuck my ass whenever he wanted, and also so long as I shared some weed each time!

One of the people who became a close friend during this time was Dougie. He was the first guy I ever fucked in the ass, and then I turned him over to Danny, remember? Well Dougie and Danny were definitely an item. Dougie came out to his classmates as gay, and over time he began to act more effeminate, adding a bit of swish to his step (I suspected that Danny had Dougie wearing a butt plug most of the time). If you looked at him closely you could see he was usually wearing a bit of lip gloss and eye liner, and clear polish on his nails. His mannerisms also began to take on a bit of.., um how do I put this.. well, he was acting more and more like a stereotypical fairy! But I enjoyed his company!

I began to drink a fair bit when I was out on dates. Cosmopolitans and chocolate martinis were my favourites! However, I would drink anything that a man would buy me, and so I sampled a lot of different alcohols. I can't say that I liked single malts, but I never turned down a drink from a guy. Many nights I came home ripped and would end up puking loudly in the bathroom. Mom really disliked having to clean up after me in the morning. And I really hated it when she shouted at me when I was hungover!

But I had been a nerd for nineteen years and now I loved being a party girl! So what if I drank a bit too much, smoked a bit too much, fucked every guy and gal who asked me for the time. Life was to be lived!!!!!

All of this was going on during the week. Friday and Saturday nights were different.

I had gone to see Coach's plastic surgeon friend. He had me strip naked and took a long look at me. He asked me what my realistic long term goals were and I told him the truth. I wanted to look like the most beautiful girl, but keep my dick. I wanted a nice round ass, and nice large tits. I told him that my fantasy was to have nice hard fake looking breasts, what I called porn star tits! He raised his eyebrows at this. He said most women wanted breasts that no one could tell were fake. I told him that I wanted everyone to know that my breasts were fake and I wanted them big.

He looked me over and said that this could be done. He also looked at my face and told me that I had a very attractive face, but that as I got older it would get even more angular and masculine. He suggested that I consider having some work done on it soon, to stave that off.

He told me that the breasts that I wanted... the size that I wanted.. would have to be done in stages, so that the skin could stretch and grow.

The first part of the procedure, to insert the smaller implants and to touch up my face a little bit would cost five grand, with another five grand needed after that. He said that when I had the money I should call and he would schedule me for a day or two after that.

He also told me that I should stay on the hormones to get the effect on my skin and some body shaping, but after a certain point I would need to get off of them because they would affect my ability to get an erection. Careful monitoring and using the hormones on an off should achieve the results that I was looking for.

I told him that it might be awhile before I could come up with the money. He just smiled and said that a pretty girl like me could come up with the money pretty quickly if I put my mind to it.

He also gave me a business card of someone he thought I should email. It was for a video production company in California. I did not recognize the name, but when I got home and googled them, I discovered that the company made porn films specializing in shemale series, including several that featured young performers barely over he legal age, like "Bang My Teen Tranny Ass", and "My Daughter Has a Dick". This was NOT something I was interested in. I stuck the card away in a drawer.

But his comments did get me thinking. If I wanted boobs sometime soon, I needed some money. And I knew how I was going to get it.

The first Friday night, I asked Karen to go along with me. I put on a skimpy skirt and tarted myself up real slutty. Mom practically screamed at me when I left the house dressed like that! She was getting to be SUCH a bitch! But after a ciggie and then a joint in Karen's car, I was feeling much more mellow. We drove over to the Kat Klub and went inside. We sat at the bar and ordered a couple of cosmopolitans. It did not take long before the first guy hit on me. I was nervous and I sent him away, disappointed, after a bit of conversation.

Karen was talking to one of the other girls in the place when the second guy hit on me. He was a lot older than me, but definitely cute in a distinguished way. He wanted to know how much it would cost for a fuck and I told him we should talk outside.

Fifteen minutes later he had paid for a room at the Ambassador and I had two hundred bucks in my purse. I was on my knees sucking on his cock and enjoying the taste of fresh meat. He almost blew his load, but he had paid to fuck me, so I laid him down and sat my boycunt down on his dick without him realizing he was in my ass, rather than in a pussy. It was another ten minute ride before he blew his load and then the guilt and shame took over and he practically ran out of there without even washing off. I wondered what he would think when he got home and his dick smelled of ass instead of pussy!

Before I went back to the Klub I opened a vial that I had bought from Karen and poured some powder on the bathroom counter. I formed it into a line and then snorted the coke. I'd told myself that I would only use cocaine on special occasions, and fucking my first stranger for money certainly counted as special!

When I got back to the bar, Karen was being rather friendly with the gal she had met. They were both touching each other provocatively. But when I ordered drinks for both of them and myself, they toned it down. Another couple of gals came over and suggested that we all move to a table.

They were all working girls, eager to get money from the guys who came into the Klub looking for a bit of relief. To my relief, they did not mind that I was there, also trying to make some bucks. They did however want to make sure that I was not undercutting their prices. They did not mind some competition, so long as it was fair. We talked about prices for blow jobs and fucking and such and I agreed to charge the going rate, or even more if I could get it.

The girls were also stunned to find out that I was transgender, a shemale in their own terms. They knew several customers who would be interested and said that they would steer them to me. They wondered about Karen, and Karen told them that she was just there for support for the night, and she was only into other women. The gals said that they could send some customers her way too, if she wanted, but she declined. She said she made enough money selling weed, and she proved it by selling some bags to the other gals there.

Karen left soon after, with the other girls promising to look after me on my first evening as a working girl. I had two more customers that night. One was just a quick blowjob in the parking lot, and the other was a guy who liked a girl with a dick. I took him back to the hotel room which was already paid for and he came in my ass once, and on my tender small breasts a second time.

The second guy asked for my email address so that we could work out some timing other than weekends.

It was late when Carlos picked me up to take me home. I'm afraid I had had too many chocolate martinis and was very drunk as he drove me home and so, for the first time, Carlos did not get his blow job!

I stumbled up the stairs and threw up before I got to the toilet! Mom was going to be pissed off again!

It took most of the next day for me to get over my hangover and I promised myself I would go easy that night. I was back at the Kat Klub again that night and I went back most Friday and Saturday nights.

One thing that I noticed was that the guys who approached me were often turned off if I seemed too intelligent. They seemed to like a gal who was a bit of a bubble head; who seemed to have only half a brain. It was not hard for me to just use short words and giggle a lot when they talked to me. And it was fairly easy to pretend to be ditzy after I had a couple of drinks in me, and had had a couple of joints. I began to enjoy playing the airhead!

I also realized that I had lost all interest in my studies. I had no ambition to go to college! So I went to each of my teachers and told them that I no longer cared about the marks. I told them it would probably be best if they continued to give me good grades, but I really did not care. Instead I wanted some money from each of them if they wanted me to continue providing them with sexual favours.

One teacher stopped seeing me. The rest went to Principal Henderson for a discussion, and then started paying up. When I got paid, I gave Jordan twenty percent, as we had agreed!

It took me seven weeks to raise the money that I needed. It would have been only six weeks but I also had to raise money to pay Karen for the weed that I was getting from her, and the bit of coke from time to time too.. Only a tiny bit mind you. I wasn't going to get myself hooked on the stuff, honest!

And so, I called the plastic surgeon and a couple days later I took the day off school. It was just simple day surgery. He cut me just underneath my developing breasts and inserted the very round, very firm implants. At the same time he used his implements to shape my nose a little bit and he dabbed just a bit of collagen under my lips in strategic places to make my lips a bit fuller.

He talked about how next time he would like to make my lips fuller still, and how he would like to enhance my cheek bones and perhaps alter my eyebrow ridges a bit.

When I got home I went straight to bed and did not encounter mom until the next morning. My chest was bandaged, as was my nose. She instantly knew what I had done and she broke down crying. She told me I was out of control! She wished she had never given me permission to become Sindy. I told her I didn't care what the fuck she liked or did not like. This was my life and I was going to live it how I wanted to!

I went to my room and opened my window and lit up a joint and tried to calm down. I admit that the pain from my chest and from my nose did not have me in the best of moods.

I went back to bed and slept most of the day.

When Mom came home from work, I had dinner ready for her. I hugged her and told her I was sorry for saying the nasty things I had said. She forgave me, but still wanted to scold me for what I had done. But she knew that this would only make us shout again, and what was done, was done. We ate in silence.

A week later all of the bandages came off. I put on one of the new bras I had bought and wore a low cut top in order to show off my new tits at school. Everyone oo'd and ah'd. My nose was now shorter and upturned slightly. My lips were thicker.

But it was my breasts that got the most attention, of course. They were each about the size of a softball, nice and round and firm. As I said, I had no interest in nice soft boobs. I wanted obvious fake tits and that is what I had. My nipples were stretched a bit too, but when I got excited they perked right up and were very evident even through my bra and blouse.

Principal Henderson was the first man to put his cock past my new lips. Coach Grogan was the first man to slap his large cock between my tits and fuck them.

That night I preened in front of my full length mirror and adored my new hard firm tits. I plunged my dildo in and out of my ass as I masturbated furiously!

It was so nice having tits. I loved having them sucked on and I just adored having a man use them as handles to hold onto firmly while he jackhammered into my ass from behind! And of course, they increased my business on Friday and Saturday nights.

I continued picking up guys at the Kat Klub on weekend nights. As I mentioned earlier, I was having fun dumbing myself down and playing the airheaded bimbo to these guys. It snared the guys who thought they could take advantage of me.

Many of the guys who sought me out knew about my big secret in my panties. Some did not care, some wanted me to fuck them! I charged extra when a guy wanted me to fuck him, or if he wanted to suck me - and those guys gladly paid. Sometimes a few of us gals would go to a party and we would have to split the take. Karen drove me over some evenings, usually because she wanted to drop off some weed to many of the other working girls who had become regular customers.

Chapter 24 - The School Tramp

Life was strained in our house from then on. Mom was constantly angry at me, and I was mad at her.

I was not very happy either, having lost my direction. What DID I want to do with my life? Truthfully, as I said before, I did not have any plan except to suck and fuck and smoke weed. I wanted my next surgery. I wanted larger boobs. In addition to the facial modifications, the doc had also suggested moving some fat around on my body, onto my ass, to give me an even fuller figure.

I was doing my best to earn the money for the surgery. Mom would object again, but I had no intention of telling her when I was going to have it done.

I was being much more select about whom I was fucking lately. Well, let me correct that. Anyone with the right money could have my ass or mouth. But I was more picky about who I would fuck for free, or for the price of a nice dinner. I dated very few schoolmates now.

I did get one scare. One Saturday night I had just gotten back to the Kat Klub after being fucked by a chubby business man. That had put another hundred and fifty bucks towards the bigger boob fund. I had the keys to the Ambassador room, so I was hoping to be able to make some more money on my back before the night was done. I was talking to Candice, another of the working girls, when a good looking guy came up and bought us both drinks. He asked how much we would charge for both of us to do him at once and we worked out a price. We took the guy back to the room and just after he paid us and I put my share of the money away, he pulled out a badge and told us we were under arrest for being hookers!

This was going to mean being hauled down to the police station and held in a cell while the cops called my Mom! I definitely did not want her finding out about my weekend activities! The undercover cop called for a cop car to take Candice and I to the station and the holding cells. A few minutes later Patrolman Dick Hooper and his female partner walked through the door. Dick took a long hard look at me - I had tits and a new nose now - and asked me if I was Sindy! I nodded, almost in tears. Dick took the first cop aside and talked to him for a bit. The first cop turned back to us and said that he was not going to pursue the incident further, since officer Hooper had vouched for me. The cop and Dick's partner left with Candice leaving Dick and I alone in the room.

Dick opened my purse and took out a joint. He also fingered something else that was in there. We sat and smoked the joint together. He told me I was looking very fine and reached for his belt. I knew the price I had to pay, so I knelt and gave him a quick blow job, swallowing his cum at the end.

Dick told me that if I got in trouble like this again, I should call him from the station, rather than a lawyer. However, he said, I needed to be careful. He had found the small vial of coke in my purse and told me that he could get me off of a prostitution charge, but if I was caught with coke there was nothing he could do for me. I thanked him with a kiss on the cheek and then called Carlos and had him drive me home. I'd had enough excitement for the night.

A couple days later I was standing outside the school smoking with the other cool girls. Not a joint, just a cigarette. I did have a mild buzz from some coke I had snorted about an hour earlier.

Stevie Henderson came up the sidewalk towards us and tried to speak to me. He stammered something, and I mimicked his stutter. He got all red and ran off. I think the dweeb was actually crying! I laughed and shouted after him that he was a pansy. All my friends had a good giggle at that!

At the end of the school day, Karen and I were sharing a joint behind the sports field bleachers. I had just finished sucking off one of my teachers and needed the joint to relax. I told her about her brother and she said that she had told him that it was hopeless, but he had persisted anyway.

I asked her, what was hopeless? She said that Stevie had approached her the day before and said he was going to ask me out on a date? A date, I echoed? Yes, she replied. Stevie had confessed that he was a virgin (well, duh! after all he WAS a nerd - what girl would want to date him!). He had asked Karen for her help, to ask me if I would go out with him. Karen had said that he should ask himself if he truly wanted a date.

Why me, I asked her. What made him think that I would go out with him. Yes, we had been friends when we were both guys, but now.. well, I was so far beyond him!

Karen looked at me and told me. Stevie had told her that I was the School Tramp. He figured that if anyone would go out with him, it was me! He'd heard I had fucked most of the guys, and a lot of the girls, in the junior and senior classes, and even some of the teachers. So surely, he reasoned, I would be willing to go out with him, and he could lose his virginity.

Karen and I laughed at that.

But he was right, in less than six months, I had gone from wanting to lose MY virginity to Becky Winters, the School Tramp, to becoming the School Tramp myself!

Chapter 25 - Happy Birthday to Me!

My birthday was in early March and Mom, being Mom, tried her best to mend fences with me. Unfortunately, this ultimately led to her finding out just how big a slut her new daughter was!

I had seen a poster at the Kat Klub for a strip club in Springfield where there was an upcoming event that I thought would be a hoot to go to.

The club was called the Cradle and was a typical female strip club. Twice a year, including this Saturday night, they kept the men out and let only women in - to see the male strippers that they brought in. Sort of Chippendales, but not with that trademarked name. The club found it to be good business because the women spent a LOT of money, and also, once the show was over, at midnight, a lot more guys showed up and paid for admission, knowing that there were a bunch of horny gals inside!

Mom agreed to treat Cassie and I to an evening out, and Karen was going to join us as well. If you have not guessed already, Karen was my closest friend amongst all the other girls at school. Mom approved of her because she was Jordan's daughter. Mom knew that Karen was a lesbian, and was fine with that. Of course if she had known that Karen was the biggest seller of weed in the city and that she was selling other drugs too, she would have freaked.
Karen and I drove into Springfield together early in the day and did some shopping. We also met up with her supplier. This was at a house in one of the rundown sections of the city. We went inside and were met by Jade, a large black woman and her husband Dwayne who were in their thirties. She was a nice looking woman but decidedly on the heavy side. Apparently money was not the only payment Karen was making today. Jade led Karen into the next room, where she lay back on the bed. Karen knelt down and soon had her face buried in the fat woman's quim, eating her out.

From where I sat on the couch, I watched as Karen slobbered over the very meaty cunt, and then watched as she also used her fingers to flick Jade's clit. This soon turned into Karen sucking the clit and shoving a couple fingers into Jade's cunt - which became three fingers, then four, and then I watched as Karen folded her thumb into her palm and slowly pushed her entire fist into Jade's pussy. Jade squirmed about as Karen flexed her fist inside the black cunt, slowly rolled her wrist back and forth and then began to fuck Jade vigorously with her fist! God, but didn't that look... interesting. I wondered what it would be like to have cock in my ass that could squirm around that much. I wondered what it might feel like to have a fist in my ass! I guess that was possible!

As I watched this, I sat on the couch sharing a reefer with Dwayne. It was some damn good shit. He kept trying to put his hand on my thigh and suggesting that we go upstairs to another bedroom. I might be a cock slut, but I was not crazy. This guy's face was pock marked and his arms were covered in needle tracks. I was definitely not interested. He persisted and got more aggressive and finally I pulled down my panties enough for him to see my cock! That made him move to the table in the dining room!

Karen finished with Jade, who lay back panting as Karen used the bathroom to wash up.

Karen was careful with her driving after that, not wanting to get stopped for a traffic offense and perhaps have the car searched! Of course we sampled the weed and just before dinner we both snorted a bit of coke. Hey, it was my birthday! I deserved a treat!

We met Mom and Cassie at a nice restaurant. I had a couple of drinks and perhaps got a bit unruly. Especially when Cassie went on and on about Johnny. Cassie was again talking about how she and Johnny might get married soon. School would be over in a couple months and they would both be graduating. Cassie's marks were not good enough to go to college, but mom had arranged for her to get an office job in Springfield. Johnny would be going to college there and so they had talked about getting married and moving into married student housing there!

I of course new that Johnny was a piece of shit! He was not good enough for my sis, but any time I tried to warn her about her darling boyfriend she would just ignore me. I held my tongue at dinner as much as possible, but I did let a couple of comments escape in side whispers to Karen. Mom looked at my sternly and decided it was best to pay the bill and get out of there, hoping to break that line of conversation.

The Cradle was only two blocks from the restaurant and so we walked. Mom and Karen had both parked in a parking garage between the two places. I was a bit unsteady on my feet, but I linked arms with Karen and we made it fine to the club. Mom was a bit frustrated at having to stand around outside the club while Karen and I finished our cigarettes.

Inside we had a reserved table for four near the front. They did not normally reserve tables, but Cassie had called ahead and told them that it was my birthday, so they had made an exception. When we arrived they checked our ID, and my new Cindy identification still had Carl's birthday on it, today. It seemed unusual that there were ushers in nice suits, but one of them who introduced himself as Troy led us to our table. He was tall, handsome, not much older than I, and well built. He complimented me on my looks, wished me happy birthday, and definitely ogled my tits. I could almost see him drooling. I turned my face to him and let my airhead personality take over. I giggled and asked if I could feel his muscle. He held out his arm, and bent it making a large muscle. I said not THAT one and giggled again! Being a sexy tease was such fun!

A couple minutes later the lights went down and the dancers/strippers came onstage. I realized then that the waiters/ushers WERE the strippers!

What followed was seventy-five minutes of yelling and screaming from the all-female audience as eight handsome hunks took the stage one at a time, and in groups, stripping down to almost nothing in time to steady thumping beats. Waitresses wandered through the room, replenishing drink orders and cleaning up the empties. I had two or three more cosmopolitans and was definitely feeling no pain!

The guys stripped right down to tiny briefs and thongs which covered their cocks, but did not hide the shape or girth. I guess there was some kind of law that said they could not be completely naked, but what that law was I was not sure. Then the host made an announcement that if the women made enough noise, the guys had a special treat for them. Spotlights showed that all of the doors were being closed. I realized this was for show, but it was quite effective.

Then all eight dancers came out on stage, fully dressed and began to wander through the audience, touching the women on their shoulders and elbows, and allowing the women to grope at their crotches. As the music continued the guys danced amongst the tables slowly removing their clothes until the only thing they were wearing was their tiny briefs. They all made their way to the stage, turned their backs to the crowd and suddenly tore off their tearaway briefs. Then they turned back to the crowd of hollering and hooting women to proudly display their might erections. None of the guys were smaller than six inches; all were thick.

I did not know where they had come from, but each of the guys had a can of whipped cream in his hands. They all spread out amongst the audience and each guy approached a different table. He would squirt a little bit of whipped cream on the tip of his dick and stand in front of a table. If one of the gals there motioned, he would step beside her and... well, some of the gals giggled and swiped the cream off quickly with a finger. Some women would take hold of the knob and scoop the cream off with her hand, before the guy reapplied the cream and faced the next gal at the table.

Some women were bold enough to lick the cream off of the cock. When they did that, the guy would apply more whipped cream and offer his cock to the same woman again. Most just blushed and turned away.

I was having a wonderful time, shouting and encouraging the women at the tables around us. I was quite plastered at this point, almost falling out of my chair at times.

And then Troy approached our table. Troy had a beautiful cock, and an interesting cock! It was eight inches long and it flared - it was narrower at the base, then thickened in the shaft, before tapering a bit again, reaching the nice mushroom helmet. He sprayed whipped cream on the tip and then presented his cock to Karen. Karen just shook her head. He swivelled to Cassie and Cassie put her hand around his cock and licked the cream off, her tongue not really touching Troy's cock. She giggled as she sat back, and Karen hugged her. Troy looked disappointed.

Troy reapplied the cream and approached Mom and raised an eyebrow at her. I had figured mom would shake her head, but she had also been drinking and was hollering along with everyone else. Mom did not use any hands, but opened wide and took the head and an extra inch of Troy's cock into her mouth. As he pulled back out, you could hear a pop from the suction, and then her tongue reached out for a final tickle at his cock head. Mom blushed!

Well I certainly had to outdo Mom! When Troy turned to me, I took the can of whipped cream out of his hand, used one hand to pull his dick down straight, and then squeezed out a thin line of cream from the tip of his cock, along to top to his pubic hair. I handed the can back to him, and he looked at me questioningly. With little hesitation I took his glans in my mouth and then I pushed, and slowly slid his entire eight inches into my mouth and down into my throat.

As my lips nuzzled his pubic hair, the tables around us went silent. I held my position for about thirty seconds, during which you could hear everyone breathing, and then I slowly pulled back, making sure that my upper lip dragged along his cock and cleaned all of the whipped cream off! As his cock left my mouth, all the women around us let out a roar and a loud cheer. I sat back satisfied.

I looked at Mom and she was stunned. I realized that this was the first time she had ever seen me as a sexual creature. Up until then I was her son, then her new daughter, and at times her unruly brat. She knew that I was dating Jamal and that he stayed overnight sometimes. She must have assumed I was having sex with him. (She certainly did not know that I was fucking multiple guys every day!) But this was the first time that she had seen me actually have any kind of sex with a guy. It was sinking in on her, that her little boy was now a big girl. And she was about to get an even deeper shock!

The emcee had the lighting guy turn the spotlight on me and asked me to stand. He introduced me to the audience as Sindy and told them it was my birthday, which got some polite applause. He then told everyone that I had just done something remarkable, which the couple tables around us had seen. He asked those tables if they thought the rest of the crowd would be interested in seeing it too, and all the women there yelled yes! He then asked me if I would be willing to repeat what I had done for the rest of the club!

Mom said no, no, but I just stared her down. I put on my now familiar vacant airhead expression and told him, sure! To a round of applause I was led to the centre of the stage. A short bench was brought out and I was asked to kneel on it. Then another one of the dancers, a Latin looking guy whom they introduced as Sanjay stepped forward. I saw that he had the longest cock of all the guys, probably about ten inches.

I took one more look over at my table. Karen and Cassie was watching me eagerly. Mom was staring too, but it was hard to read her emotion. It could have been dread... but I think it was shame and disgust. Quite frankly I did not care. I just knew that I had a nice beautiful cock in front of me. I opened wide, Sanjay moved his hip forwards and his cock head touched my lips. I stuck out my tongue and swirled it around his glans. I then reached my hand out, put it on his ass, and nudged him forward. He lunged a bit, and I took all ten inches down my throat in one gulp.

The women in the audience shouted and stomped their feet as Sanjay fucked his cock in and out of my mouth. I was loving the feeling of his delicious cock and was getting off on the chanting. As we continued, Troy walked up behind me and tapped me on the ass. I stopped sucking briefly. I looked back and nodded that it was okay for Troy to lift my skirt. I lifted one knee and then the other so that Troy could remove my panties.

My cock dangled down, but due to the skirt the audience could not see that I had a dick. Troy's eyebrows raised in surprise, but he was not deterred. I turned my head back again and mouthed, Fuck Me!, and Troy did. He put the head of his cock at my asshole and slid easily inside of me. The music thumped to a lively beat, and all of the women in the crowd were cheering, egging the guys on to fuck me faster and harder. At one point Sanjay pulled my blouse down and freed my tits from my bra. The perfect round globes bounced as I was fucked from both ends!

The guys were true professionals. This was not just a public fucking, but also a performance for the crowd. They ground their hips and were pretty much dancing as they skewered me from both ends!

The boys together lasted about seven minutes. Anything more than that would have lost the audience's attention, and the guys knew how to play to the crowd. Sanjay pulled his cock from my mouth and then used his hand for another half minute, finally blowing several streams of hot jizz across my face. The crowd groaned along with Sanjay.

Troy still had me stuck on his wonderful cock. He whispered in my ear asking permission. I was too cock crazed to care at the moment. All I knew was that my ass was getting a right royal pounding from a superb man dick. I said yes, yes, anything yes, just fuck me!

Troy stood up, lifting my light five foot four frame so that I was in his arms facing the audience, my skirt pulled aside - and all of the women say my own dick standing rigid, and that Troy's cock was shoved up my bruised arse and not inside a pussy as they had expected. The room was silent for five seconds, and then the women started yelling, fuck that bitch, and other obscenities even louder.

I looked over at my table and saw mom putting on her coat. She was still staring at me, but she had a look of loathing on her face! Cassie looked awe struck!

I grunted, I groaned, I shot my own stream of cum high in the air, as Troy raised and lowered me on his dick. Finally, with a low rumble, he thrust me down on his cock and grunted loudly, his face and legs straining as he came inside of me! The audience was quiet... unsure as to whether they had seen the climax of our act. Troy lifted me off of his dick and when he did, his cum ran out of my ass and pooled on the floor of the stage. The crowd erupted!

Troy put me down gently and we hugged. My legs were weak, my knees were wobbly. I gathered up my clothes and turned back to the table, just in time to see Mom pulling Cassie out the door. Karen gave me a hug. I sat down to gather my strength and slowly put my clothes on.

Karen hugged me and gave me words of encouragement, but also warned me that my Mom had been spitting mad at me. I shook it off as no big deal. Sooner or later Mom was going to find out that I was not a sweet innocent virgin girl and now was just as good a time as any.

Karen then apologized saying that she could not give me a lift home. One of the women from another table was lagging behind. Evidently Karen had made a new friend and would be spending the rest of the evening, and all night, with her! I told her it was fine, I would just get a hotel room for the night and get Carlos to give me a lift in the morning.

When Karen left, I sat there for a bit, but the management chased me out, since they had to set up for the rest of the evening.

Outside the door, I ran into Troy who had showered and was presentable. I let my face go vacant and began to cry a bit. He asked me what was wrong and I told him that the other people in my group had run out on me. I was all alone and had no way to get home!

He took me back to his hotel room. We cuddled together for awhile, before I kissed him and he kissed me back. As we sat entwined, he told me that he was bisexual and had sex just as often with men as he did with women. I was a bit of both, and so he was delighted to find me there with him. We soon ended up in bed, and I found myself on my back, with a sweet handsome sexy man, rutting his cock in my back passage for what seemed like an hour before we both shot our loads. We nuzzled and cuddled some more as we drifted off to sleep.

Chapter 26 - A Job Offer

In the morning I woke Troy up with one of my amazing blow jobs. This is when I found out that Troy had a fetish, which was that instead of letting me suck his cum out of him, he found it an incredible turn on to splash his cum across my face. Whenever we fucked, whether in my ass, or down my throat, he always wanted to pull out at the last second and splooge on my face.

When we finished, Troy left the hotel room, saying he was going to find us some breakfast. I washed up a bit and then crawled back into bed. I smoked a joint and then lay my head back. A half hour later I was awoken as he placed a tray of food on the bed.

Troy asked me how I had gone from being a boy to being a knockout shemale. I decided it was best if I continued to play the dumb airhead and so I told him, in small words, that my sister had tricked me into it and I had found that I liked being a cute girl! And then I found out that I really really liked having sex with guys!

As we talked we ate, and our hands touched as we reached for the same things at the same time. This led to us holding hands while we finished up. When the food was done, Troy moved the tray onto the floor and we embraced passionately. Soon he was fucking my face hard as I lay on my back with my head hanging backwards off of the bed. He was still amazed at how my throat easily accommodated his cock. It did not take long for him to cream his load across my face.

We showered together, which led to him soaping up my ass and driving his cock deep into my bowels. We skidded around in the shower stall, since the floor and walls were all slippery. This time he came inside of me! I chased him out of the shower after that so that I could get myself completely clean - inside and out. After the shower, I had to put back on the same clothes I had worn the night before. I did have my makeup with me.

Troy had to check out of the hotel after that. Downstairs in the lobby we met up with the other guys from his strip act. These guys had a large van which they used to drive them from city to city. Troy had two more weeks on the road before he would fly back to Los Angeles where he lived. Troy told the guys that he was going to spend a few more hours with me, and would meet them back at the hotel at 6 pm, when they would grab some grub to eat on the drive to the next city.

Troy and I walked around for a couple of hours, holding hands, and kissing every once in awhile. Here was a guy who I could really get into, could consider as boyfriend material, and he only came to my city twice a year!

As we talked, I remembered to keep everything that I said simple. Men did not like smart girls, I had found out. So I made sure to keep my words short and pause when talking to make it look like I was thinking hard.

As we talked and I got more comfortable with Troy I told him about my surgery for boobs and fixing my nose and that I hoped to have more surgery soon to intensify my femininity. He said that it must cost a lot of money and I found myself telling him how I had made the money for my first surgery. He was not surprised nor did he tell me that hooking was wrong. In fact, he admitted that sometimes he took money from women for sex, and from men too.

When he found out that I was eager to get my boobs enlarged again sooner rather than later, he said that he had an idea that he thought I would like.

Soon we were back at the Cradle. The place looked pretty dingy in the daylight. There were a couple of staff restocking the bar and one older guy mopping the floor of the stage. Troy led me into a back corridor and knocked on an office door. A voice told us to go in.

A fat man sat at a desk, smoking on a stinky cigar. He recognized Troy and they shook hands. Troy introduced me as Sindy and introduced the man as Mr. Gambetti, the owner of the Cradle. Gambetti sat back down, looking me over and expressed surprise at seeing me again. He remembered me from the previous night.

Troy suggested that Mr. Gambetti might want to hire me for the club. I blinked my eyes in surprise and kept my dumb blonde look on my face.

Troy told us both that he had to leave. He told me that he would be in touch by email. We kissed and then he was gone.

Gambetti asked me if I had ever danced in public before. Had I ever stripped? I told him that I had not, but I was a quick learner and I was not shy in public. Gambetti practically laughed, realizing that any gal who would let herself be fucked on stage was definitely not shy.
He told me that he had never before hired a chick with a dick, but he could see where I might be a hit with some of the patrons, even after the novelty wore off. I told him that I was still in school in Bigelow. He said that was no problem as the club was not open early in the week.

He told me that if he took me on, he would expect me to be in the club Thursday Friday and Saturday nights, and sometimes on Sundays. The club hours were nine to two, but on slow nights I could leave at midnight if I wanted.

He told me the club did not pay me any wages at all, so that technically I was not an employee and they could not be held responsible for my actions. Yeah, the club got busted four or five times a year, but the charges never stuck.

I would be on stage dancing twice a night, and would wait on tables and serve drinks when I wasn't on stage or otherwise occupied. And by otherwise occupied, he meant that there were rooms down this back corridor where girls could take patrons who wanted private lap dances, or anything else they might agree to. There was also a stairway to the second floor where there were four rooms with couches or beds.

I got to keep all of the tips that I made while dancing and serving drinks. That was my pay. If I made any deals with patrons, I had to give the house thirty bucks every time I used a ground floor room, and seventy five bucks each time I used one of the second floor rooms. What happened between me and whoever I took up there was my business. He grinned at that!

He told me that on a good week, I could walk out of there with a thousand dollars of my own money, if I was nice to the customers, and they were nice to me!

I told him that I was not looking for a long-term job. I was only looking to make enough money for bigger boobs and some other enhancements. He told me to strip and I did, my cock hanging limply. He walked around me and poked my hard tits. I told him that my plans were to get some fat injections in the ass, and to get tits at least twice the size of what I had now, plus plumping up my lips even more.

He pushed me down to my knees and undid his pants. He waved his dick in my face. His whole body stank of stale cigar smoke and sweat, but I did not hesitate in taking his fat cock into my mouth and working it over real good. He let me suck on him for only a couple of minutes before he pulled me up. I thought he was going to bend me over his desk and fuck me. But instead, he told me to climb up on his lap. He leaned back in his chair a bit and I climbed up facing him, and lowered my dick onto his prick. He then sat back and told me to ride him. While I was fucking myself on his dick he was mauling my tits - squeezing them in his big paws, and sucking savagely on one nipple and then the other. And taking puffs on his obnoxious cigar all the time. Up close he smelled even fouler, but I realized that I wanted this job. It was a way of making steady money doing what I enjoyed, and was definitely a step up from working the punters at the bar at the Kat Klub.

While he was fucking me and grabbing me with his smelly greasy hands, Gambetti was also swearing at me, calling me a dirty whore, a fuck slut. He seemed to love foul language and trying to humiliate people. The only thing he said that did make an impression on me, was when he told me that my ass was even tighter than my boyfriend's. Apparently Gambetti preferred ass to pussy (something that most of the other strippers confirmed to me once I knew them better - he'd had his cock in all of their asses at one time or another). Also it seemed that Troy was one of his favourites when the male strippers performed at his club.

It took fifteen minutes to get him off. He dumped a heavy load of cum up my ass. I did not get any pleasure from the fucking, but I did get a job out of it!

As I tidied myself up and dressed, Gambetti told me that if I signed on, and I proved to be a good earner - meaning that I made HIM a lot of money, then in three weeks he would loan me the money I needed for the tits, bum, lips and whatever. I could pay him back by turning over two hundred ad fifty bucks each week until my debt was paid to him. He told me that he doubted I would need the loan though. He suspected that I would be earning quite a bit of money for myself, and for him.

We shook, and that was how I became an exotic dancer!

Chapter 27 - Dancing Queen

School was now SO absolutely fucking boring! Carl the nerd had liked the structure that school gave to his life. But Sindy had no interest in math, or geography or economics. Boring boring boring. School had now become just a place for me to hang out with my friends and get some good fucks behind the bleachers or from one of my teachers.

Once I started dancing at the Cradle and was getting money for sex in the back rooms, I realized that I was stupid to just give my ass away for free at school. I needed money for my bigger boobs fund, but also because I was now giving Karen a lot of money for weed, and for some blow from time to time, despite patrolman Dick Hooper's warnings. Oh, I made sure never to be carrying very much with me!

But I stopped giving my ass away at school. One or two of the guys would approach me but usually left angry when I told them how much I wanted. I was still getting lots of sex during the week. Coach Grogan was still ramming me on Mondays along with my double dose of hormones.

Jordan, the principal, was not a frequent visitor to my ass anymore though. Our schedules clashed too much and he was getting a bit more serious about mom. I guess guilt over diddling her former son was keeping him away too. I wasn't too pleased with this development really. Jordan was a nice fuck even though he was an older man. It was hard to believe but I was jealous of mom, and a royally pissed off at Jordan.

I went to the Kat Klub a couple more times to earn a bit of money, but soon stopped. I was now having to go midweek, and there were not many guys looking for hookups on those nights. Most of those evenings were spent in the company of men who had become regular customers... the few who could sneak out on their wives midweek

I never showed mom my test results anymore. They were coming back as either Ds or just as incompletes. Since I was no longer fucking any of my teachers, none of them gave me decent marks.

My debut at the Cradle had been a big success. Gambetti had decided my first night of stripping would be the Saturday night. Thursday and Friday and early Saturday I just waited on tables. I got my ass pinched and groped a lot. I made a nice amount in tips, but despite getting offers to take me in the back, Gambetti told me that the private rooms were off limits to me until my big debut.

A couple of the other girls gave me private lessons before the club opened on those nights, and I watched the girls stripping as I served drinks. None of the other girls knew my big secret though, not until the grand unveiling at the climax of my first strip on the Saturday night. Gambetti's voice introduced me to the audience by the stage name he had thought of for me: Sindy Suxxx!

I can't say that my first try at stripping in front of an audience was much of a success. I was nervous and dancing in four inch heels is a challenge for anyone. But everyone was delighted when my tits were revealed. And once I was down to my thong only, and then pulled that off, the crowd went silent, and then they roared with applause and laughter. I danced for the next five minutes with an incredibly hard erection sticking out from my groin. Despite being revealed as a shemale, the audience applauded and egged me on, just as much as they did any of the other girls, and the money handed to me and thrown on stage was just as good!

I left the stage to some standing ovations! And quite a few standing erections too!

When I went back out on the floor, I had several men eager to spend some personal time with me. Over the next hour I took three guys to the back room and charged them fifty bucks each for lap dances, and each took me up on a blow job for additional money.

I took a break to wait on tables. Now that my cock had been revealed, my waitress outfit consisted of a minimal bra and a pair of sheer panties that my cock could easily be seen through.

I danced a second set that night as well. I also took four guys up the back stairs, and up the back passage too, if you know what I mean!

At the end of the night I paid Gambetti his cut and also sucked him off. He did not cum very much, so I suspected that a few of the other girls had drunk at the same trough before me!

By the third week Gambetti admitted that I was a hit. The place was even busier than ever on Friday and Saturday nights because the guys were coming to see me! Gambetti had me start dancing a third set each night, and I was sharing top billing with one of the other gals.

I was also having fun playing at being a dim witted bimbo at the club. As Carl I had always been pretty sharp, but that had not gotten me anywhere in life. Men definitely felt threatened when their pretty women seemed too bright and so I found it much easier to extract more drinks and money out of my customers if I did not think too hard. Of course, being high on weed, and taking a snort of coke each night before getting on stage all left me pretty muzzy headed anyway. There were even a couple times when I forgot to get the money from the guys before they put their cocks in my mouth and between my tits!

In addition to the actual sex, I found it to be such a fucking turn on to give guys a lap dance. I would take them to the back room, get their money, and then spend the next ten minutes in front of them and on their laps, grinding my ass down on their hard cocks, trapped in their pants, and rubbing my tits across their face!

After my third weekend, Gambetti called me up to his office. We had a ritual by this point. I knew that before we would talk any business I had to blow him, so I got on my knees and took his cock in my mouth. I also pulled down my top so he could look at my firm tits while I sucked.

Once I got him off, and swallowed - he always made sure I swallowed his foul slime - once I swallowed, he showed me a loan agreement and asked me how much money I needed. He was making good on his promise to fund my next round of surgery. But I declined. He had been right when we first met. I had already saved up almost enough money for the surgery. I figured that three more weeks of earnings would be enough for me to be able to afford my larger tits without going in debt to this sleaze.

I told Gambetti that I had already talked to the doctor and that when I had the surgery I would need three weeks off from the club in order to heal up. We looked at the calendar and agreed on which three weeks off I would take.

I figured I should thank him for his support and so I bent over the desk and let Gambetti sink his cock into my boipussy and fuck me from behind. While I sucked him off almost every time I saw him, this was only the second time Gambetti had fucked me. This time, with him pounding me from the rear, I could work his cock against my prostate and get some pleasure of my own. As he fucked me, I lit up one of my cigarettes. I needed something in my mouth!

Three weeks later, I did indeed have enough money for the surgery. It had been a bit close though. The rain had been heavy one weekend and so the crowd at the Cradle was a lot smaller than usual. So the next week, I had gone to the Kat Klub almost every night, looking for some extra money, and I had also called up many of my regulars. I got home way past two am every night and mom was furious with me!

Well she was going to get even madder at me, but thankfully I would not be around to see her explode!

Chapter 28 - A Bit of Revenge

One unsettling development was that I had a falling out with Karen and it was a serious one. Though why the fuck she really cared, I do not know. But of course, I had to get my own back at her, and I did! On her and her dad in fact.

Jordan's defection from my attention was really bothering me. He had not fucked me in a couple of weeks. I liked his hard cock in my mouth, and ass. But I also liked the nice hotels and restaurants that he took me to when we went out. He was about the only guy who treated me like a real woman.

I guess this was too much on my mind one time when Karen and I got together. One Thursday night I left the Cradle early because Karen came to Springfield to pick me up. She had actually gone into the city to make a pick up from Jade and Dwayne and offered to give me a lift home. It was a slow night. I had only taken one guy into a back room for a lap dance and a blow job, and only one other guy had taken me upstairs to fuck my ass. Gambetti agreed that it was a slow night and, once I blew him too, he agreed I could leave early.

Karen pulled her car over on the way home and we toked up on her bong pretty good. I think we sat there for over an hour just getting mellow and talking about life. I had told her I was close to having enough money to get my next surgery. She told me she was happy with the ample tit flesh she had come by naturally. We got talking about our bodies and then about the various men (in my case) and women (her) we had been having sex with, and somehow it slipped out that I had been fucking with her father, or rather, that he had been ramming his stiff cock up my butt, repeatedly!

As I say, I don't know why it should bother her, but she went fucking ape shit crazy on me, yelling and screaming. It was like I had somehow invaded her family life! She swore at me and told me that I shouldn't have anything to do with her dad again!

As it turned out, Jordan did not want to see me, but I was not going to tell Karen this! What fucking business was it of hers as to who I sucked and fucked!

Karen dropped me off at home and drove away in a huff. Later I was concerned about losing my supplier for weed and coke, but Karen was not that kind of gal. We did not hang around much after that, but she still sold me dope, though she charged me more.

That night though, I was steaming mad myself at her reaction. At her, and at her father. Hell, at the whole Henderson family - Jordan, Karen and even Stevie. Poor little virgin Stevie who was too shy to ask me out on a date.

Hmm... now there was an idea. Maybe I could have some fun with Stevie, and get some of my own back on his family!

The next school day Karen was not talking to me. I hung out in front of the school with a few of the other cool girls, but when Karen saw us, she just hurried past. I flipped my middle finger at her back and muttered fuck you under my breath. A couple of the other girls noticed and asked what was wrong, but I did not tell them

After classes, I waited in the hallway outside of the math lab. I knew it was math club night, Carl used to be a regular. I had been such a dweeb back then!. When Stevie came along and saw me, he hesitated. But I put on my sweet smile, batted my eyelashes at him, and made sure that he got a good luck down my ample cleavage. I told him I was so sorry about laughing at him the other week, and asked if what his sister had told me was true, that he wanted to go on a date with me? He blushed and stammered, yes.

I reached my hand down and gently cupped his rigid cock in his pants and told him that I would love to have him take me out and I suggested that we get together on the following Monday night. He moaned, and I suspected he had just cum in his pants. He nodded and ran off.

We talked by email over the next couple of days. I danced at the Cradle as usual on Thursday to Sunday and made some plans in advance for the Monday night.

When Monday rolled around, I went home and changed and picked up a bag. As I went out the door, Mom was yelling at Cassie about something for a change and so I made a quick escape. Carlos picked me up and we headed downtown to pick up Stevie. Stevie was cleaned up and wearing his best shirt and pants, and even a tie. He was even carrying a small bunch of flowers which he gave me. He was very nervous. I had Carlos drive us over to the Ambassador hotel in Seneca. When we left the cab, I gave Carlos a peck on the cheek, promising him a special treat on the ride home. I left Stevie's flowers in the back seat. I did not forget them, I just had no use for them.

I checked us into a room, and then Stevie and I walked to the Kat Klub where we sat and had a nice light dinner. With the food I made sure to have three drinks myself and put a couple of sweet drinks into Stevie as well. He'd had beer before but never a cosmopolitan, nor a margarita. I gave tentative waves to a couple of the other working girls who were in early. But they picked up my signals that I wanted to be left alone with my... date.

Stevie had been my best friend for several years, until Cassie had made me dress up as Sindy for a date and my whole world had changed. We had grown apart as I began spending more evenings sucking and fucking. By Christmas time when I had become Sindy permanently I had written Stevie off as just one of the losers at school.

I had to admit that for a guy who had never had a date with a girl, Stevie was trying hard. He actually found things to talk about, and did not stammer. Even though he was a bit over eighteen, he did not have to shave much, but even that was nice and smooth. He offered to take me to a movie or do something else, but I told him that was not a good idea for first date. We would not be able to talk, and he would not be able to look at my boobies. That made him flush.

I told him that I knew that the main reason he asked me out was because he wanted to lose his virginity. He nodded hesitantly at that. I told him that was okay, because I was eager to take his virginity. However I twisted the conversation around so that I was talking to him more about myself for awhile. I told him how Carl had been unhappy, without knowing it. It was only when I started playing at being Sindy that I was really happy... and the more time I spent as Sindy, the happier I was.

I made sure that Stevie paid the bill and we started to walk back to the Ambassador, but I took the long way. I had time to finish a cigarette. We held hands as we walked, Stevie's hand gripping mine very tightly. When we got to an isolated spot, I lit up a joint and took a couple of good long pulls on it, then handed it to Stevie. He shook his head, and so I leaned forward and kissed him, exhaling smoke into his mouth. He gasped and coughed. Then he reluctantly took the joint and toked on it himself. He said that he had stolen a joint from his sister once and tried it, but did not like it. I intended to make sure that by the end of the night he definitely enjoyed weed as well as several other things!

When we got back to the hotel room, I had convinced Stevie that becoming Sindy had been the best thing that could possibly have happened to me. When I looked him in the eye, I could see he was a bit glazed and I lit up a second joint and we shared that. Between puffs we kissed a bit, sharing the intoxicating smoke between us. I think this was the first time Stevie had ever kissed a girl and I wanted to be sure he related the pleasure of kissing with the sensation of being high.

I then told Stevie that we could have sex. He looked eager. Or, I said..... Or, he asked?

I told Stevie that I would have sex with him. I would love to suck on his cock. I grabbed his cock in his pants, and he squirmed. I would let him fuck my boipussy. But we would do it only this time. He should have no delusions about us having sex again. And he could go back to fantasizing about girls, and jerking off alone at home. Or..... Or, he asked?

Or, I said, I could help him to be like me. I could show him how to dress up nicely as a girl, and introduce him to some nice boys who would love to have a good time with him. It was his choice. Did he want to have one night of fun, or did he want me to open the door for him to escape his nerd world and start to have lots of sex and fun?
Five minutes later, Stevie was naked and pulling up his first pair of panties.

Chapter 29 - Make Mine Mink

The booze and the weed kept Stevie fairly complacent as I helped him dress in the outfit I had brought for him. Stockings and garterbelt, sheer see through blouse and a nice dark skirt. Stevie was built like his sister, Karen, a bit overweight. I was not going for glamorous in his look, just feminine. In future he could find his own natural look. I spent several minutes on his makeup and then ran some mousse through his short blonde hair Modest two inch heels went on his feet.

In truth, he looked much more like a pretty boy than a girl, but it was a modest start.

When I finally let him take a look in a mirror, he was unsteady on his feet, from both the weed and the unfamiliarity with heels. I had him walk back and forth several time, before giving him a big hug and a light kiss on the cheek. His boner was rigid in his panties, pressed against my thigh.

I asked him if he had thought of a girl name for himself. He thought Stephanie would be fine. But I told him that Cassie had named me, and she had called me Sindy with an S. This had set the tone for my entire girl life. So I told Stevie that I was going to pick his girl name, and that name was going to be... Mink. Because I expected him to fuck like a mink and enjoy himself!

I cuddled up to Mink and asked him if he was ready for a bit of fun. He was clumsy as he tried to grab my waist and pull me to him. But I pushed him away. I gave us each another hit from my bong (Mink was quite adept at inhaling now) and then pushed Mink back on the couch. I then went to the door to the connecting room and opened it. Three large men came into the room. These were George, Harry and Amos, three of my regular customers. When I had explained what I had planned for the evening they had all been eager to help out.

Mink was looking a bit uncertain and nervous. I told George to go sit with him while I stood in front of him with Harry and Amos. I asked Mink if he had ever seen anyone actually have sex before and he shook his head no. I told him I thought it was time he got a treat.

I was not thinking of Mink as a SHE at this point. If Mink kept dressing I am sure in time he would be a she, but frankly I did not care. I just wanted to corrupt him enough tonight and fuck up his family! That is why I had a couple of video cameras placed discretely around the room, to pick up the action!)

I knelt in front of Harry and Amos and they lowered their pants, kicking them out of the way. I eagerly took both of their cocks in my hands and then eagerly sucked them in turns into my mouth. I did not try to deep throat them. I was not trying to scare Mink, but rather was showing him how pleasurable a blow job could be. When I looked over, George was sitting with his arm around Mink and his other hand was running up and down the new sissy's stockinged leg. George then turned the pussy boy's head with his finger and kissed him on the lips. Mink was hesitant. But then George's fingers stroked his rigid cock in his panties. Mink moaned and returned the kiss.

Meanwhile I was now on all fours, and was sucking on Amos while Harry got behind me and thrust his cock easily into my ass. I saw Mink's eyes widen as he saw me being pounded. I was very vocal in my enthusiasm, telling Harry to fuck me hard. I wanted to be sure that Mink knew this was enjoyable. George was avidly kissing Mink, who was eagerly accepting his tongue into his mouth. George's hand was cupped on Mink's hard dick, squeezing it and massaging it. Mink moaned lustily. George lifted his ass and removed his pants and underwear. He then took Mink's hand and placed it on his dick. Mink balked at first, but once his palm hit the slick rod, he wrapped his hand around it and began to slide his hand along its length.

I was lost in my own pleasure for a few minutes. Harry was ramming my bottom good and was hitting my prostate just right. He grabbed hold of my softball titties and tweaked my nipples as he pounded me.

When I next looked over at the couch, Mink was on all fours and had George's cock in his mouth, eagerly sucking. Amos had pulled Mink's panties down and while he wanked the sheboy's cock with one hand, he was using a couple of fingers to shove some lube into Mink's asshole. I eagerly watched the slight panic on Mink's face as Amos slowly pushed his cock at his asshole. I had done it, I thought - I had actually gotten the nebbish so stoned and turned on that he was letting two men fuck him at the same time!

I had enticed the men to the session this evening by promising them that they would get first crack at a virgin. Well, I say promised, but actually I sold Stevie's virginity to them. George had paid me three hundred bucks to be the first guy ever to fuck her mouth, and Amos had given me five hundred bucks to be the first cock in her ass. Harry was just along to fuck me and to get sloppy seconds on Stevie, er, Mink.

Yeah, I had had a fit when Johnny had pimped out my ass, but you know, I really did not have any moral dilemma from making money off of Stevie. It served the little shit right for being such a pansy ass.

Over the next ninety minutes the three men and I kept Mink busy in the middle of a sissy orgy. Mink had his ass fucked at least four times (five?) and sucked off each guy at least twice. Most of the time he was being fucked at both ends at the same time, but sometimes I was keeping two guys busy myself.

At one point Mink and I were sucking on the same dick, swapping it back and forth, and kissing a bit. I'm not sure if Mink ever realized that he and I never had sex during the evening. We kissed, and I squeezed his cock through his clothes early on, but I never touched his cock, and he never fucked or sucked me!

I do know that Mink ended up with several loads of cum up his bum hole, and plenty in his belly too. He also came several times, and had squealed in delight as the cocks rubbed his prostate to sissy heaven!

It was close to midnight when I led a still quite stoned Stevie out to Carlos's cab which was parked in a cark corner of the Ambassador's parking lot. Before we got in, I introduced Stevie more fully to Carlos. This included having Stevie kneel in front of Carlos and suck him off. When he finished, I noticed that Stevie had a string of cum in his hair. I did not remove it. He could wear it to bed that night as a badge of honour.

Stevie did not show up for school the next day. When I asked her, Karen grudgingly told me that her brother had come home very late the previous night and had told his mom in the morning that he was too sick to go to school.

The next day, Stevie was again very shy about speaking to me. But I dragged him behind the school bleachers. I shared a joint with him and got him to admit that he had really had a good time the other night. He did like being Mink, but he was uncertain as to whether he could get anyone else interested in him. I told him not to worry.

As I mentioned, I had stopped fucking most of the guys and teachers in the school. I figured that if I gave him a bit more encouragement, I could prod Stevie into being a cock slut too. I got both Jamal and Dougie to ask Stevie out that week. They both told me afterwards that Mink had been eager to fuck and suck with them. I figured that word of mouth would get around and Stevie would be able to be Mink as much as he wanted.

Chapter 30 - Bigger, Better Boobs and Butt!

Mom was going to be livid when she saw my surgical bandages again. I didn't think I would be able to put up with her screaming at me, when I was newly ... enhanced... so I arranged with Cherry, one of the other strippers at the Cradle, to stay at her place while I healed. So the morning of my surgery I packed a couple of bags which I took to Cherry's small apartment in Springfield. On the way out the door, I left Mom a note telling her I would be back in three weeks, but not where I was going, nor did I leave her any way of contacting me. (She sent me several emails, but I deleted them all without opening them)

I was going to miss three crucial weeks of school. When I got back, there would just be two more weeks of classes, including final exams. But I did not give a flying fuck about school anymore!

The only reason I would go back into the school after my latest surgery would be to show off my new body to all my girlfriends!

The surgery went fine. As I mentioned, I got my breast implants removed and much much larger ones inserted. The doc moved some fat off of my waist and into my butt, adding some other fat as well. He increased the collagen in my lips to make them even more plump. He also did some work on my cheekbones and my eyebrow ridge to feminize my face further. There was still more work he wanted to do on my face... but that would wait for another time, and more money.

I slept on Cherry's couch... well, when I was able to sleep. My new body shape... large tits and large ass, required me to get used to new sleeping positions. During the daytime, I was walking around even though I was quite sore. I would put on my four inch heels and practise walking. Each of my new tits was as large as a small cantaloupe. And nice and round and oh so fake looking. I spent long periods of time gazing at my tits in the mirror, fondling my own breasts and stretched nipples. My boobs were absolutely fucking gorgeous!

My ass was an amazing sight too. Although I had had nice tits after my last surgery, I still had a slim boy's butt. Yes, the hormones had been helping to give me a bit of curves, but now, I had a nice fleshy tush. While my new tits were firm and hard, my ass was now soft and spongy, and when I spanked myself, you could see ripples! God the guys were going to love banging my bottom!

Both my tits and my bottom were heavier than in the past, and I needed lots of practise in heels, finding my new centre of gravity and equilibrium.

Everything was wrapped up in bandages for the first week. The bandages on my butt and tits came off then, but my facial bandages remained for another week.

As soon as the bandages came off of my tits I went to the tattoo and piercing parlour. I had both of my nipples pierced and had thick studs put through each nipple. I also got a nice big tramp stamp across my lower back, just above my new ass. I figured that this was the time... while I was fully healing and not able to have sex on my back... this was the perfect time to get the tattoo done. I got a very fancy Celtic looking design with the words "Slut for Cock" interwoven. The words were hard to read unless you concentrated real hard. I figured most guys would be staring at my new ass long enough to get the message!

The most frustrating thing during all of this of course was the lack of sex. No one banging my new ass, no one sucking on my tits, no cock sliding past my new lips! Fortunately, Cherry was as much into pot as I was, and so she did not mind me smoking lots of weed while she was out. She had a day job at a grocery store so I did not see her much of the day. On weekend nights she was dancing at the Cradle of course. Week nights she was entertaining generous men whenever they called her up. She had a second bedroom, and that was where she took care of, ahem, business.

Cherry had her own website and the men called her up on the number she had listed on there. It sounded like a pretty safe way to find johns, rather than having to hang around a bar like the Kat Klub, or even worse, hustling on street corners.

There was one other benefit from my surgery. When I started dancing at the Cradle, I started noticing that my cockette was having a more difficult time getting and staying hard. Having it hard while I danced was much more erotic for me, and also seemed to bring in more tips. Also some of the guys who paid me for sex, wanted to suck on it, or even have me fuck them. Of course, if I used my cock, I charged them more. But as I said, I was starting to have difficulties in that department. And that was natural, due to the hormones.

But my surgeon told me to stay off the hormones for three weeks before surgery, and during my recovery time. He told me I could go back on them if I wanted, but based on my goals, he did not see me needing them. The surgery was giving me the curves that I wanted. And he realized that I wanted my dicklette to get stiffies!

So I was off of the hormones, and my little stick was standing proudly at attention again!

When my face bandages were off and the swelling had finally gone down, I looked fucking gorgeous! My face was now truly feminine. My lips were much fuller, but not a caricature. I went to the hair salon and they helped me complete my new look. My eyebrows were almost completely shaved and I pencilled in new lush lines. I changed my hair from the platinum I had been wearing to a more natural blonde, but I had it cut and then permed.

When I got done I have very much of a classic Barbie, bimbo look about me. Large fake breasts spilling out of my small top, short short hot pants, long legs, large ass. I was a dream doll for any man looking to find his porn princess!

To thank her for her hospitality I let Cherry be the first person to suck and slobber on my new tits. Fuck, but they were so sensitive! She had some large tits herself and it was interesting rubbing our large breast mounds together when I lay on top of her fucking her pussy with my cock!

I had no particular man in my life at the moment and so on the final Saturday night of my recovery I went to the Cradle to visit with my new friends, the other strippers there. They all hugged me and groped my new ass and tits. I giggled a lot and continued to play the dumb blonde. I also went in the back room and snorted some coke with a couple of the gals whom I had started supplying with blow that Karen was supplying to me.

I went upstairs to see Gambetti. He was pleased to see me, and very pleased to see the results of my surgery. In less than five minutes he had me stripped and sitting in a chair while he stood in front of me and fucked his cock between my melons. And they were indeed melons now. Nice large round hard boobs! I licked and sucked on his dick head as it popped out of my cleavage. But this did not last long. He bent me over his desk and rammed his cock up my butt. I loved the sensation of my new larger ass cheeks rippling as he pounded my butt. I swore and cursed at Gambetti, urging him on... telling him to fuck me faster, deeper, harder. When he was about to cum, I had him pull out and took the head of his dirty cock into my mouth. It had been almost three weeks since I had tasted cum, and I sucked his sweet load out of his cock and savoured the flavour and texture before swallowing.

Gambetti told me I would now be the main featured dancer at his bar and he already had a new name for me SinDD StaXXX. I loved it!

Chapter 31 - Burning Bridges

It was time to go home and face Mom.

On the Sunday I packed up my bag, hugged Cherry and called Carlos to give me a ride home. Carlos was speechless when he saw Sindy model 2! I gave him a big hug, a long kiss and squeezed his hard cock through his pants. On the drive back to Bigelow, it was hard for him to contain his eagerness to get to our usual discrete driveway where he could pull of so that I could blow him. As usual he gave me an additional twenty bucks to smoke while I sucked him off.

This was hardly necessary, since it seemed I was smoking almost non-stop now. Not only was I hooked on the nicotine, but I was convinced it made me look even dumber and sexier.

When I walked into the house pulling my wheeled suitcase, I was dressed in my now everyday casual wear. Short black skirt to show off my large ass. Four inch heels to show off my legs. I had thought about wearing a low cut top to show off my magnificent cleavage. But instead I wore an incredibly tight top which hugged my new jugs. My new nipple rings were clearly outlined through the tight material. I had chosen heavy large rings because they emphasized my sluttiness even more! My top also was cut short so that my belly button dangler was visible as was my tramp stamp. I knew the impression I wanted to make on mom!

I did not hear anyone at home, which was strange because the drive and street were filled with cars. I then realized that everyone was in the backyard. I walked through the house and out into the yard. About twenty people stared at me in surprise, and then it dawned on mom and Cassie that I was Sindy, returned.

They were astonished, and I could see that Mom was angry. But both of them hugged me, followed by Karen, and Jordan Henderson, and Johnny. Stevie looked at me mischievously and gave me a discrete thumbs up! There were about 15 other friends and neighbours in the yard and a barbecue was in progress. Mom muttered under her breath that I should behave myself and that we would be having a very serious talk after everyone had gone home.

I lit up a cigarette and perched on the end of a table as all of the guys in the yard found a reason to come up to me and say hello - primarily to ogle my tits. Karen had visited me once in Springfield to deliver some weed and a bit of coke to me, so was not startled by my new appearance. She was still standoffish, still steamed at me for fucking her father.

To everyone's surprise, Stevie and I wandered off together, first out front and then around the block where we smoked a couple of joints. Stevie was looking pretty good. It looked like he had lost a few pounds, and his complexion was much cleaner. After we were done the joint, he asked me for a cigarette. He told me that Dougie had gotten him hooked on ciggies. He was getting out as Mink a fair bit he said, and had several regular boyfriends who were using his ass regularly.

He filled me in about the barbecue. It was a celebration... earlier Cassie and Johnny had announced that they would be getting married in a month. No big surprise there!

But there was a surprise. Mom and Jordan Henderson had also announced that THEY would be tying the knot later in the summer. Karen and Stevie and I would be stepsiblings!

Stevie knew that I despised Johnny. But he did not know that a couple months back I had regularly been taking his father's cock down my throat and up my ass!

I really did not think that either man was good enough for my sister or my mom. Eventually the men would fool around and the women would be heartbroken, and probably left for penniless too.

I needed to make sure that neither wedding took place. I needed a plan or two.

Jordan made things easy for me. Soon after everyone had had their fill of burgers and potato salad, Jordan cornered me in the kitchen where I had gone to get away from all of the women's glares. I loved the men stripping me with their eyes, but did not like the evil jealous looks that I got from their bitches! Jordan briefly fondled my large jugs, toying with the nipple rings through my top and told me that he had to see me again. He said he desperately wanted to see and fuck my new enhanced body. I asked him when was the next time he was supposed to be seeing my mom. He said, Tuesday night when they were going to dinner with some people from her work. I told him that if he wanted to see me it would have to be Tuesday night - he would have to cancel plans with my mom. He dithered, but eventually agreed.

I'd had enough of this party! I head up to my room and locked myself in. It had been quite awhile since I had used my suction cup dildo on my ass, so I lit up a joint, stuck the dildo to the wall and backed my ass onto it. I squealed and moaned in pleasure as I wiggled and shimmied my new larger ass on the rubber cock, rubbing my prostate delightfully. If anyone downstairs heard my screams of pleasure, well, I didn't care!
The next morning, I was up early enough that I avoided mom and the blowup that would happen if she saw the slutty outfit I had picked out for school. I walked the several blocks to school. Normally I would have met up with Karen this early and we would have driven up to Blueberry Hill, the make out point where we would have each snorted a couple lines of coke. Instead I had to do a line in the deserted school washroom.

When I came back out of the school, all the girls rushed to me and admired my new figure. Jordan... Principal Henderson called me into his office and scolded me for my attire. He said that low top, bare midriff, short skirt and four inch heels were inappropriate school attire. He forbade me to go to classes dressed as I was. Well fuck him! This made what I was about to do even easier.

So I did not go to classes. I just hung out in front of the school, smoking and laughing with my pals.

When classes ended, I did go inside and went to Coach Grogan's office. But not alone. I had asked Stevie to bring along a bag with his Mink clothes and he went with me. When we got to Coach's office he was not there and so I had Stevie change and helped him put on a bit of makeup. I then had him wait in a closet.

When Coach came in, he was amazed at my huge knockers. I let him lay me down on his couch, squat over my chest, and pound his cock between my tits. He loved hooking his fingers in my nipple rings and pulling and twisting my jugs! He also lifted me in the air, and settled my ass down on his cock, raising and lowering me, pounding his cock into my ass as my new soft ass cheeks quivered. As always he was a delightful fuck, and I squirted my own sissy juice high into the air at the same time as he squirted his jism up into me. I could see Mink's face peeking out of the closet every once in awhile, a look of envy and lust on his face!

When Coach reached for the syringe to inject my hormones, I told him I did not want the injections anymore, and told him that today was the last time I would be letting him fuck me for free. I told him I would love it if he would call me and we could arrange to meet elsewhere, but he would be paying my regular rates from then on. He hugged and kissed me and wished me luck. I then told him I had a surprise, and motioned for Mink to come out of hiding.

Coach was startled, and then disbelieving as he realized that this new crossdresser was principal Henderson's son! But Coach's dick began to rise again! I told Coach that Mink was a bit shy, but he wanted the same deal that I had had.

In truth, I had never discussed this with Mink, but I wanted to screw up the Henderson family even more if I could. I told Mink to drop his panties and bend over the desk. I watched as Coach gave Mink his first injection of the super strong hormones. I told Mink to thank Coach Grogan, and he did, by dropping to his knees and taking that impressive black cock into his mouth. I took a few pics with my cell phone and a short video.

As I left the office, I hear Coach telling Mink how much he was looking forward to fucking him up the butt!

I'm sure Coach would have called me up and been a regular customer for my ass, but the way that things went down soon after, I don't think I ended up being one of his favourite people.

That night Mom caught up to me and we had a roaring argument. It was nothing that I had not expected. She still figured I had a future at school. She just did not see things my way. I only wanted to fuck and suck.. although I put it in much more polite terms for her. In the end I finally flipped my middle finger up at her, told her she could go screw herself and then slammed my bedroom door. I did not have any money dates arranged for that night, so I just stayed in.

Fuck her, I thought. So I had no problem smoking cigarettes and having a few hits off of my bong. I really didn't care if I stunk up her house!

I did not expect to be living there much longer. I contacted Cherry and she said that she would be willing to share her apartment with me. I could have the other bedroom if I split the rent with her.

Tuesday night I put on a little black dress which showed off my ample boob cleavage and my ample ass as well. I also wore dark garter belt and stockings and five inch stiletto heels. I told mom I was going on a hot date and to not wait up for me. She was going out herself, to dinner with work friends. She was steamed because Jordan had cancelled with no excuse other than that he was busy, but she was going alone anyway.

Carlos picked me up and we stopped along the drive for his usual reward. As we entered Seneca, I was inspecting myself in my compact mirror and cleaning up the small flecks of Carlos's cum off of my face. Carlos dropped me off at a very fancy restaurant where Jordan was waiting. We had wine and very nice meals. All of the men's eyes in the place were on me and my very tight dress. Afterwards, Jordan checked us in to a very expensive hotel. As he freshened up in the bathroom, I figured out where to position the two small video cameras I had brought along with me. The two cameras captured all of the action over the next two hours as mom's fiancee fucked the living shit out of my ass! Oh, I sucked his cock a lot too, taking it all the way down my throat. But most of the time, his hard dick was buried in my boipussy. I was on my back, up against the wall, across the small desk and riding on top.

The next day when I edited the videos together I particularly liked and featured the moving images of me riding on top of his cock, pumping my ass up and down on his cock, my large firm tits rigid on my chest, but my boyclit bouncing and waving around wildly.

As I put together the DVD, I also included many still images I had discretely taken from past meetings with Principal Henderson. The pictures had been taken over many months, so that it was very clear that Jordan had not just now been tempted by me, but rather he had also been fucking me when I had small tits and even back when I had no tits whatsoever, back when I had just started dressing. The earliest pics showed me still to be just a crossdressing boy - very cute, but a young man, nonetheless.

I put the DVD away for safekeeping. I would need it in a day or two.

Chapter 32 - Pounding Nails in the Coffin

Things got excruciating around the house when my final marks for the school year showed up. I had clearly failed every class and failed the school year. When Mom asked me point blank if I had been sleeping with my teachers, I told her that that is exactly what I had been doing, up to a point, and then I had decided I did not care, and so my marks had plummeted.

Mom broke down in tears and I just walked away from her on my four inch heels.

Cassie and I still hung out together at times, but as you know I now was spending much more time with Mink. Although I had turned him on to sex, booze and weed only a couple weeks ago, he was a fast learner and eager for more new experiences. I still never touched him, but we went on several double dates with some of my better paying customers. Of course I never told him the men were paying for his company and kept the money for myself. I was still taking discrete pictures and videos of him having sex. In particular I was training him to call all of the older men he fucked "daddy" and to be very vocal while cumming!

My sister Cassie was beginning to sound too much like mom - telling me I was drinking too much, getting high too much, and she told me I was fucking too much! She was much more privy to my private life than mom was. She was getting to be a bit too high and mighty for me so I had no qualms about finally making her see the light about Johnny. I of course knew that Johnny was a piece of shit! He was not good enough for my sis, but any time I tried to warn her about her darling fiance she would just ignore me.

So one day at school, I nuzzled up to Johnny, rubbed my enormous tits against him and told him I was no longer mad at him. Cassie had already told him that she was not going to see him that night. I told him that Cassie was going to be out until midnight, and Mom was away overnight. In fact, I knew that they were out together and would be home by ten. I grabbed his dick through his jeans and let him look down my top at my new cleavage and he agreed to see me that evening.

I made Johnny take me out to a nice dinner. While we ate I had his dick out of his pants under the table and was stroking him. I might be mad at him. I might think he was a louse. But he still had a nice cock! By nine we were back at the house and up in my room. He was very turned on by the sight of my melon sized mounds as I sucked on his cock. He got behind me and pounded his cock into my ass. My ass cheeks jiggled delightfully.

Johnny came twice - boy, he had stamina! We smoked some weed together and cuddled for awhile. When it was close to ten, I told him that I wanted him to fuck me again. His cock was up and willing. I told him that this time I wanted him to fuck me downstairs, bent over the dining room table. I led him down the stairs by his dick. I turned up the music loud on the stereo.

I was wearing dark stockings and garter belt and four inch heels. I leaned against the table, and Johnny rammed his cock up my bum chute and was fucking me furiously when mom and Cassie walked in the front door! Johnny did not notice them at first. Mom let out a gasp. Johnny's lubed cock was pistoning in and out of my ass, and I was panting in heat!

Five minutes later, Johnny was still trying to make apologies. I had immediately gone upstairs and put on a pair of slacks and a low cut blouse. I lit up a cigarette and walked back downstairs. Mom and Cassie were both screaming at me, Cassie calling me a cunt, and Mom asking me what the fuck I had thought I was doing!

I handed Cassie an envelope. Inside she would find other pictures of Johnny fucking me over the past several months. I handed Mom an envelope containing the DVD I had put together showing her finance porking me. I did not wait for them to look at the contents. I just picked up the two suitcases which I had already packed and had waiting by the front door. I took the suitcases out to Carlos' waiting cab and we drove away.

I had Carlos stop at a mailbox and dropped in two envelopes containing the same DVD. One was addressed to Jordan at the school and the other to Cassie at home. Each DVD contained lots of pics and videos of sweet Stevie dressed as Mink and fucking and sucking a variety of men. I especially liked the videos I shot of Mink telling his daddy to fuck him hard, since I had been sure to not get the man's head in the shot. Cassie would be wondering if it really was her father fucking the shit out of his own son!

I had destroyed the chances of Cassie marrying Johnny, and of mom marrying Jordan Henderson. Plus I had outed wimpy Stevie to his family. I was delighted. The Barton and Henderson families had fucked with the wrong gal, and I made them pay!

I never set foot in Bigelow again until after mom died.

Chapter 33 - Cherry gives me a helping hand

I settled down into a pretty stable life living with Cherry, for about six weeks. Thursday to Saturday nights I was stripping and waiting tables at the Cradle. My enhanced boobs and butt brought in a lot of cash and made me even more popular in the back room and upstairs. All the guys were fascinated by my giant jugs. The thick rings through the nipples were a sensation too.

I also saw regular customers on the other nights of the week, including some of the guys who I knew from the Kat Klub

During the daytime, I rested mostly. Oh, I got my hair done and my nails. But I spent most of the day time in a marijuana fuelled haze. I saved the coke for the evenings before I entertained a guest at home, or before I went on stage at the Cradle.

I was emailing regularly with Troy. We had both really enjoyed each others company and we suspected we could have something special if only we were both living in the same city. We talked about me flying to see him a couple weekends later, in one of the cities where he and the guys would be dancing.

Gambetti was thrilled that SinDD StaXXX was bringing in so many punters. I was happy with the arrangement and could have quite happily stayed dancing and hooking at the Cradle for several more months.

A couple days after moving to Springfield, I was almost completely out of weed and coke. Karen would not be talking to me again any time soon, much less selling me any dope. I thought of asking one of the other gals at the club if they know someone I could trust to supply me, but instead I figured I would go right to the source.

When Jade opened her door to peek through the crack, I had to explain who I was. I'd been through my second operation since I had been to her place with Karen. She was reluctant to open the door to me, but when Dwayne looked over her shoulder and saw my giant boobs, he pushed past her and invited me in.

Fifteen minutes later, I was sharing a giant reefer with Dwayne and Jade. They had listened to me and agreed to sell me some of their stuff. I was taking just enough to satisfy me for a week. They were not interested in selling me small quantities though. If I came back again, they wanted me to take enough to sell on to other gals at the club, other customers, heck, anyone I wanted to. If I wanted weed and coke from them, I had to pass some one. When we talked price I realized that I could make enough money that the stuff I used myself would pretty much be free. I liked that idea. I did not take a larger quantity with me this time, because I had not brought enough cash with me for a larger quantity.

Jade also wanted me to service her the same as I had seen Karen doing for her. So she took me into her messy bedroom and spread her large black legs. I got on my knees and soon after I wound myself licking and sucking on the largest, and smelliest, cunt I had ever buried my face in. I remembered what else Karen had done and soon I had worked several fingers into Jade's quim, and them, folding my thumb in to my palm, I buried my entire fist inside of her. I had never done this to anyone before. There was some pressure around my wrist itself but my hand felt very flexible. I was able to turn my hand anyway I wanted. I was also able to open and close my hand. Moving my hand back and forth, and changing the shape of my hand brought moans and groans from Jade.

While I was kneeling, I felt my skirt being pulled down. Looking back I saw that Dwayne had his cock out and I knew what he intended. I wanted to resist. He looked just as skanky and strung out at the first time I saw him. But with my fist buried in his girlfriend, I could not really get away. And I did not want to piss off the people who had just agreed to start supplying me with the drugs that I needed. So I resigned myself and did not fight when Dwayne pulled my panties down.

I heard him gasp when he saw my erect cock. I guess he had forgotten my little secret from when I was there last. But he was doped up enough that he did not care. It would have been nice if he had used some lube, but he place his cockhead at my sphincter and pushed himself inside. My ass was still tight, but it was now loose enough to take in a dry cock.

I did go back the next week with much more money. Each time I went back, I tried to buy as much weed and blow as I could so I could go longer without having to get fucked by Dwayne.

I was curious about fisting though. A couple days later Cherry and I were both lounging around the apartment. I pulled out some weed and we smoked a couple of joints together. We cuddled a bit and I let Cherry fondle and suck on my tits. I moved down to her pussy and began to suck and lick. I used my fingers on her clit, then as I flicked it with my tongue, I inserted two, then three fingers into her pussy. I tried to work four into her, but she told me to stop. She asked me what I was doing and I told her what I had done with Jade.

Cherry said she had no desire to have her pussy stretched by having a hand in there, but did express some curiosity about my ass. So we changed positions and she grabbed a bottle of lube and my large dildo. Soon she had me on my back, with pillow under my ass and my butt high in the air. I needed to watch this! She vigorously shoved my dildo in and out of my ass. She swatted playfully at my erect cock, but I wanted her attention on my ass.

She removed the dildo and lubed up her hand. She worked two and then three fingers inside of me. Then she folded her fingers and thumb as tiny as possible, and twisted her fingers around and around in my asshole, slowly pushing in. My ass resisted, but it had taken several thick cocks in its time and without too much effort, Cherry's wrist passed the resistance and her entire hand was suddenly in my ass!

I felt so fucking full! The feeling was both incredible and... weird. Cherry kept pushing and she manage to slowly get about half of her forearm inside of me! But the best part was when she flexed her hand, and then twisted it as she moved her hand in and out of me. The sensations were like nothing I had ever experienced from a cock. And then on one of her twists, she rubbed against my prostate and I almost fainted! My hard cock spurted its load all over my chest and face!

I gave her directions.... in a bit.. out... around a bit... and finally she had her fingers rubbing against my prostate... She massaged and squeezed my ass lining right at my prostate. I moaned and came a second time in two minutes! Oh fuck, was it intense!

I had to tell her enough.... enough! And she pulled her fist out of my ass with a loud plop. That was absolutely incredible and I knew that I was going to have fists up my ass many many more times!

Chapter 34 - Moving On

Life in Springfield was good for about six weeks. I was making lots of money at the Cradle. I was seeing lots of customers on the other evenings. I was not fucking as much as I had been back in Bigelow, but it was much more rewarding!

I was also making good money pushing weed and coke to regular customers.

Troy and I were getting along great online and I was hoping to visit him in LA in a week or two when he would be done his latest tour. Then out of the blue, he asked me to move in with him in LA. He said that there was a porn film producer whom he was doing work for - mostly gay films, some bisexual, who wanted to hire some shemales for his stable. Troy had showed him my latest pics and the guy was eager to have me in his films.

Troy and I had got along great for one evening and the next morning. But I had no idea if I was ready to move in with him! I told him I needed a few days to think.

I really meant to get back to him the next day, but it turned out it took me a week since I could not get to a computer before then.

That was on a Saturday and I danced my usual shift at the Cradle that night. As usual, I took along some coke which I sold on to some of my regular customers when they took me upstairs. I made terrific money from some of these guys. I took them upstairs where they put money on the dresser to fuck my ass and my mouth, and then afterwards they gave me even more money for a baggie with some white powder in it!

Towards the end of the evening, I was approached by one of my regulars who introduced me to a friend of his. My regular was looking a bit nervous, but I didn't pay much attention. I took his friend Jimmy into the back room since he said that tonight he was only interested in a lap dance. Jimmy was enthusiastic as I ground my ass on his hard cock. He paid me extra to suck on my hard tits and twist my nipple rings. When he paid me, he said that his friend had told him I could supply him with a bit of weed, and some harder stuff. I told him... maybe, but I did not have anything with me. (That was the truth, I had sold on all the stuff I had brought with me that night)
He asked if he could get some from me another night, and we made a date for him to come by my apartment the next night. I told him how much money to bring and that the price included him paying for a round of fucking my ass, since I thought he looked cute.

Sunday night Jimmy showed up on time and although I rubbed up against him a lot, he was only interested in the coke. So I took his money, gave him the baggie and he was out the door. A minute later there was knock and I figured he had changed his mind. I opened the door to find Jimmy, and two uniformed cops. Jimmy showed me his badge and then the three of them ransacked my place. They found a lot of coke and weed since I had only just gone to see Jade and Dwayne the day before!

I was arrested and taken down to the precinct house. Once I was processed I ended up in the city jail. I called a lawyer - one of my regular johns. He talked to me, and then passed me on to a guy who cost a hell of a lot of money. I was in jail for three days, including being up before a judge for the charges to be read. I had to go THREE FUCKING DAYS with no cigarettes, no weed, no coke.... and no makeup!

I was looking at serious charges for possession and distribution. I told my lawyer everything and he was able to make a deal. I got immunity from prosecution and from testifying. But in order to get that I had to give up Jade and Dwayne as my suppliers. Once the cops raided and busted them I was free to go. Oh, and though I didn't have to, I gave up Karen to as one of my suppliers.

The next day the papers had stories about the major raids. One ran a picture of Karen being led away in handcuffs. The article also mentioned that several cops had been arrested, naming Dick Hooper and his partner in particular.

I knew this state was going to get very hot for me.

I phoned Troy and told him I was moving to LA!

I packed my bags, gave Cherry a big hug and caught the first plane to California!

Epilogue

This is where I am going to end my detailed story. In a ten month period I had gone from being a nerd with my nose in my books, to being an oversexed anal slut bimbo shemale with my nose constantly in white powder!

I moved in with Troy in West Hollywood. I did go to work in porn films. I started in a few bisexual videos, and soon graduated to several shemale lines. Troy was my partner in many films, but he was also very much in demand for gay movies as well. It seemed he loved having his ass pounded by thick hard cocks just as much as I did!

I soon got well known for being fisted regularly in my films... first just by gals, but then by men, and soon I was taking very large objects up my ass in specialty fetish videos.

While starring in these films I was enjoying the fringes of the Hollywood scene. I got friendly with several stars of tv sitcoms and various films. I was seen on several red carpets before movie premieres, and I was fucked thoroughly by some big hollywood names.

I paid good money to have a fancy website that promoted my porn career, and my outcall services. I often made a thousand bucks a night from just one rich john. I found myself flying to Europe a couple times, to be the trophy girlfriend for a long long weekend.

Troy and I were getting along well. I loved the way he pounded my ass on film, and he was a wonderful and caring lover when we were home together. He was often on the road though and so I was on my own a lot. He did not mind that I was selling my ass and mouth to earn a living - he was too!

Life was fantastic for about a year and a half!

However, I was living life very large. I was drinking a lot and using a lot of coke, ecstasy and any other drugs that came my way. There were many times when I would wake up without knowing what I had done the previous twelve hours.

I began missing my shooting schedules, or showing up drunk. Punters would phone me up after seeing my website, but I would then not show up or would not look my best. I got a bad reputation on online reviews and the calls from my website dried up.

Troy tried to help me, but he was not around enough. And I resented him for being sober. One time I called him a sanctimonious bastard and slapped him. Two days later he was in a car accident and he died! I totally fell apart at that point. I still had a drop dead body, well, mostly. I had put on twenty pounds of weight. At five foot six, that was a lot, and my tummy and face showed it! No one wanted me in porn films due to my drinking, drugs and memory problems. I swear I no longer had to act the part of a dim witted bimbo. The weed and drugs had burned out an awful lot of brain cells!

I found a low budget guy and started doing fetish videos for the internet. These involved me taking large dildos up my ass, and also lots of self fisting! My vids were popular and I made some good money from the passworded website. But a lot of my videos got pirated and ended up on torrent sites for free and my income shrank again.

At nights I began working the street corners with the other shemale hookers. There is was easy to pick up johns, but I was not making the money that I used to! I usually ended up the night slouched over a bar in some dive and finally going home with whoever would pay my bar tab for the evening.

I'm not going to tell you about the next six months. Just take it as given that I sank about as far as a human being could go - I started being able to tell different brands of dog food apart at my lowest point.

I finally ended up in AA. At the same time I had a couple of surgeries to sew my ass back together. I had regular prolapses as a result of all the large objects pulling my ass apart.

In AA, I went through all of the stages, including making apologies to all the people I had hurt along the way. This meant begging Cassie for money and travelling back to Bigelow and Springfield. Mom had died a year or two earlier. Cassie greeted me tearfully and I met her new husband and her baby son. I visited Karen in prison. She did not want to talk to me, but faced me through the glass long enough to spit at me.

Jordan Henderson had moved away from Springfield. Coach Grogan had survived all of the scandal and was now principal.

Stevie had not followed in my footsteps completely. He, or rather she, had abandoned the Mink name, and was now known as Stephanie. She was still a bit of a slut when it came to men, but she was able to control her urges. She was a chemical engineering major at State University at Springfield.

Most surprising, Johnny Long held no grudges towards me and thanked me for apologizing to him.

I returned to California and continued my recovery. I discovered that there was government funding for sex change surgery for people in my financially distressed condition. I still loved being fucked, but could not endanger my ass and my life anymore. As much as I loved my cock, I made the decision to have SRS. At the same time I had my giant bosom reduced down to much more modest levels. I also had laser therapy to erase or obscure my more lewd tattoos.

I kept in touch with Cassie and also, strangely with Johnny. Johnny even came out to visit me while I recovered from my SRS.

When I was fully healed, I visited Bigelow again and I seduced Johnny. He was the first man to fuck my new pussy, and he was just as sweet a lover as I remembered.

My Johnny. My first love. Well, my first crush.

Johnny and I got married and I moved back to Bigelow. Only a few people knew that the new Mrs Johnny Long used to be Sindy Barton, or Carl Barton for that matter.

Cassie was happy for me. Cassie, the sister who had made me the woman I had become.

The End
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