After having read many submissions about one's first time I've decided to tell you about my last time dressing as a sexy woman. To get to the finale, I need to give you a little background.

I am a 35 year old white male that stands 5'7" tall and weigh in at 140 pounds. I stay very fit with lots of competitive cycling, swimming and running, all sports I've indulged in since high school. These physical activities keep my legs and butt very toned while providing a ready-made excuse to remain totally smooth.

My initial foray into women's clothing was sneaking some of my good looking older sister's panties to jack-off with when I was 18 years old.

One morning when I had a pair of her panties wrapped around my cock as I was stroking it under my blankets, my mom knocked on the door and said she was doing laundry and wanted my bedding.

She opened the door to come into my room to get the sheets and noticed I was red faced and breathing hard. Mom asked what was wrong and I said I didn't feel very good. She felt my forehead and said I want to take your temperature.

As she walked into the jack & jill bathroom that my sister and I shared, the only way I could think of hiding my big sis's panties was to put them on then pull my boxer briefs over them.

Mom came back moments later, took my temp, found it normal and told me to go take a cold shower. I walked into the bathroom and closed and locked the door and for the first time in about a minute took a breath.

First thing that I noticed was how good sis's panties felt good on my ass and cock. I dropped my boxer/briefs and took a look at my panty covered bottom. I loved how her silk panties looked on me. It only took me a minute to finish off what I started in my bed squirting large amounts of cum into her panties.

This initial panty incident lead to me trying, liking and wearing many different items out of my big sister's lingerie drawers. String bikini panties, thongs, slips, panty hose, nylons & garter belt, bras, bustier, you name it I was trying it on.

That was followed by her club clothes, short skirts, tight tops, spandex pants, anyway you get the idea.

One weekend when the entire family was at the lake but I stayed home to not miss swimming practice, I got all dressed up and decided to put on make-up to see if I could make myself passable.

You understand the progression. I don't want to burden you with the details as this is not a story of how I began but rather the night that determined I stop.

Briefly, I learned to dress, and then learned to put on make-up that was not only passable but sexy, to talking on the internet, to experimenting with going out in public, to giving my first blowjob, to finally losing my anal virginity.

I continued to play as a woman throughout college and up to just a couple of years ago. While I dressed frequently, I didn't have many physical encounters, less than ten in total. Just enough to know that I enjoyed being submissive and pleasing my partner just like my girlfriends pleased me.

Back to the final night of my being a gurl.

While on a trip for business, I meet a guy on Craigslist, Damon, and we exchanged a number of emails.

I always told the truth in that I was a passable cross dresser and enjoyed pleasing my man both orally and by giving him my tight ass. Even though I thoroughly enjoyed being treated like a woman, I wasn't into kissing and always played safe.

He said he was totally fine with that and wanted me to meet him at his hotel bar. Damon told me he was 6'1" and weighed 215-220 and had a 7" average cock. My limited experienced had taught me that I enjoyed the length more than the girth of a man's pleasure stick, so I thought he was about the perfect size.

I took my time preparing for our date. Long scented bath, shaved totally smooth everywhere, followed by a dusting of baby powder before I began my make-up.

I kept my dirty blonde hair fairly simple by brushing it back and pulling it back into a short pony tail. Next I painted my toe and finger nails a hot red. When they were dried I carefully made up my face with eyeliner, mascara, two-toned eye shadow and blush before walking thru sprits of Chanel perfume.

Now it was time to dress. First I put on my black thigh high nylons with a lace trimmed top, then a sexy pink and white garter belt. I attached the garters then slipped on a pair of Victoria Secret's silk string bikini panties in black with a jewel encrusted keyhole that nestled just above the top of my ass crack. Next came my black semi-sheer bra with pink trim. I slipped in my very realistic 34C breast forms.

I had chosen a white silk blouse that would allow you to see my black bra through it if you looked hard. I slid a black nylon/spandex lace trimmed slip up my legs and over my tight ass before putting on my tight black rear zipped skirt. My skirt came to mid-thigh and hugged my ass like a glove.

Silver earrings, two bracelets, a silver belt and silver sequined 4" strappy sandals completed my ensemble. Wet look red lipstick to match my nails and another dusting of Chanel and I was ready to go meet my "date". I not only thought I looked hot but knew it, sexy but classy.

As I pulled up to the hotel to park my car the valets were all jockeying for rights to open my door. As the young man opened my door I pivoted in my seat slipping my long legs out and letting my tight skirt ride up high enough to give him a glimpse of my stocking tops.

He struggled to bring his eyes up from my legs even when I stood up and handed him the keys. I pulled a couple of dollars out of my black and silver clutch purse to give him and he mumbled that I didn't need to tip him, he was happy to help me anyway he could.

I walked into the bar swinging my hips making my ass undulate looking around for my date. Damon spotted me and quickly came to the front of the bar and escorted me back to his table with a hand on the small of my back. We chatted a bit, flirted a lot, drank perhaps too much (at least me) and even danced to a couple of songs before Damon invited me up to his room. I agreed as that was the reason I was meeting him in the first place.

Damon escorted me to the elevator, his hand in the middle of my back grazing the top of my ass as we walked. There was another couple waiting for the elevator with us. Both gentlemen allowed us ladies to enter first then they joined us in the cramped space. The other couple got off on the 3rd floor but my guy's room was on the 11th. Once the other two got off the lift and the doors closed, Damon put his arms around me from behind and pulled me back against him. I could feel that he was as excited as I was with his erection pushing into my ass and back. His hands were roaming over my taunt stomach and up to my breasts while he was nibbling on my neck. I was so hot!

The doors opened and Damon led me to his room, opened the door and let me into a nice upscale bedroom. It wasn't a suite but there was and an adjoining room with the door closed. His hand, now firmly on my ass directed me to the king size bed. We sat on the bed and his hands started roving over my legs, breasts, back and ass. He kept telling me how hot he thought I looked and how horny he was and that he was going to make sure this was a night I would never forget!

Damon stood up, dropped his pants and briefs to the floor and stood directly in front of me with his nice 7" cut cock right at my face level. On hindsight I think this is about when he changed from being the gentleman to be very dominant. Damon instructed me to suck his cock.

I eagerly reached out and took his throbbing cock in my hand. Bending my head down I licked the tip of his manhood and followed that with running my tongue up and down the length of his shaft. Next I looked up at him as I slowly wrapped my painted red lips around the head of his dick and slid down the length taking him entirely into my mouth and throat. Damon groaned and put two hands in my hair and started working his shaft in and out of my mouth using it as a receptacle for his pleasure. Since when I am dressed I am submissive in nature this was a real turn on for me.

As Damon continued fucking my mouth he started talking dirty to me. Calling me a sexy slut, telling me he can't wait to take my ass, even saying to me that he knows I want a cock in my mouth and ass at the same time. All this talk just built the excitement for me. I'd even wondered what it would feel like to be filled from both ends at the same time but never had the courage to try to make it happen.

Damon eventually pushed me backwards on the bed and crawled up into almost a 69 position with him on top. He kept filling my mouth with his big cock while his hands wandered up and down my legs. My legs involuntarily parted for him as I was moaning on his cock. He kept telling me I needed a dick in my ass and mouth at the same time.

Suddenly, he pulled his cock out of my mouth, flipped me over and started groping my ass. As Damon was working my ass over he was now asking me if I wanted a cock in my mouth and ass at the same time. He continued talking dirty to me as he unzipped my skirt and pulled it down off my legs tossing it on the chair. Although he remarked how sexy I was in my slip it wasn't very long before it joined my skirt in the chair.

Damon was really working my ass with his strong hands.

He told me to take my blouse off before he ripped it off of me. I quickly started unbuttoning my top but almost tore it myself when he slid a wet finger into my rectum. I jumped pretty hard as I wasn't prepared for that to happen yet. He just laughed and again told me I should have a dick in my mouth and that way I couldn't yelp. He kept saying you'd like that wouldn't you slut and such.

When I had my top off he told me to stand and turn around so he could see the entire package. I did as he wished. Here I was in a room with a man I hardly knew dressed in panties, garter belt, nylons, bra and high heels acting like a stripper on her brass pole.

When I had my ass to him he reached up and grabbed my waist with both hands pulling me back towards him. Again he said, "You want a dick in your mouth and ass at the same time, don't you bitch?" When I didn't answer he slapped my ass hard enough to make me jump again and I'm sure leave his hand print on my right cheek. Damon said "Answer me slut, I've asked you a question." With that he gave my left cheek a ringing slap. Not enjoying having my pert ass spanked, I answered him, yes; I'd like to have your cock in my mouth and ass at the same time. I didn't think anything about it at that time, just thought it was dirty talk.

With that Damon pulled my panty aside again and pushed his finger into my ass again. He started working it in and out and it was beginning to feel really good. I felt extremely sexy dressed as I was and this big strong guy wanting me so bad that he wanted to put his cock in my mouth and ass at the same time.

I felt a cool liquid running down the crack of my ass and came to the realization that Damon was applying some lube to his finger. He kept working his magic finger in and out and then slipped a second finger past my sphincter muscle.

This was tight and hurt a little but he kept working it until it felt better and better. I was grinding my ass back to his fingers and he kept up the dirty talk calling me his slut and two cock bitch. He pulled both fingers out and I felt empty and must have whined a little because he said "don't worry bitch, a good slut should get what she wants and deserves."

He tore a condom open and put it on his raging hard on. With that done he dribble some lube all over his big cock and pulled me down onto his lap. He pushed my back forward and put the head of his cock at my anal entrance. With a slight raise of his hips he pushed the head into my tight passage. Damon kept pushing his cock up into me until he was fully in me. I felt really full but it didn't hurt too much. Damon had me rise up and lower down on his cock making me fuck him faster and faster. He kept telling me that I was a sexy slut and that I needed lots of cock. Anytime I didn't answer him he gave one of my ass cheeks a good solid slap which made me answer in a hurry.

Damon lifted me off of his prick and told me to lie on my back on the bed. He said he was going to make sure I got everything I wanted. He grabbed my feet and pulled me to a corner of the bed leaving my ass hanging of the end of the bed and my head of the side of the bed. Damon then put my legs on his shoulders and pushed his cock deep into my ass.

He started fucking me with reckless abandon. I loved every minute of it and was trying my best to fuck him back by rotating my hips and clenching my butt. I was moaning loudly when he again asked, "You want a dick in your mouth while I'm fucking your ass?" Knowing my already red ass would get another smack I answer "Yes, yes I want your cock in my mouth and ass at the same time."

Next thing I know there was a large dick hanging over my face and Damon and the owner of this big cock are high fiving. Damon said to the new guy "I told you she was hot and would be up for it." And to me he said "You wanted a cock in your mouth while I am fucking you so start sucking slut."

With that he started spanking my ass until I reached out and put the strangers cock in my mouth. Damon then said "I told you I would give you what you want." The cock in my mouth started to get hard and it was longer and thicker than the one fucking my ass. I was happy that it was in my mouth and not in my ass. I guess it was about 8" long and quite thick.

Damon was really pounding my ass now and I was getting into being double stuffed once I got over being scared. The guy in my mouth, I heard Damon call him Richard, wasn't too rough as he let me suck him and guide the pace. Damon was fucking me so hard now that it felt like his cock was in my stomach.

Damon shoved my legs almost to my head, buried himself deep into my bowels and erupted into the condom. He shot several loads of cum into the condom, let my legs down and then pulled his cock from my well fucked bottom.

Richard had been in my mouth for 5-10 minutes and massaging my fake tits and stomach all this time. When Damon pulled out, so did Richard.

I was a limp rag on the bed but still felt incredibly sexy dressed and fucked as I was. Richard walked around the bed and high fived Damon again. He said, "Man you really fucked this bitch good, look at her hole gapping open. She really likes the cock."

He picked up one leg then the other and started running his hands up and down my nylon cover legs. I should have known what was going to happen next but wasn't thinking. Next thing I felt is the head of his big cock against my sphincter muscle and him trying to push it into me.

I cried out, "Stop, you aren't wearing a condom, you're too big, I'm too sore." Richard replied that he had a condom on and I would love it, I couldn't leave him this way. He also said we will get a dick in your mouth so don't worry.

He kept pushing until he forced that big cock into my sore ass. I yelped in pain and clenched my ass tight. I was trying to push him off of me but he was too big. Damon came back from the bathroom and stuck his cock in my face and told me to suck it or else.

I knew I'd get an ass beating if I didn't do as he said so I opened my mouth as Richard continued forcing his monster cock up my backdoor chute. Richard had about half his cock in me and started fucking me slow and easy. Damon had his balls lying across my nose and his whole cock in my mouth.

Both the guys kept commenting that I was a good piece of ass that really liked having two cocks in me at the same time. Every tenth stroke or so Richard would go a little deeper into my dark passage. After about 5 minutes of slow fucking he was complete inside me.

Another couple of minutes of slow fucking and my ass muscles started to relax and his big cock was beginning to feel good. Damon started really fucking my mouth telling me how hot I looked with a cock in my mouth and ass. It wasn't long until Damon was squirting a large load into my mouth. Swallowing was something that I had never done but I wasn't given much choice as Damon had two hands full of hair and his cock almost down my throat when he erupted.

Once Damon was done shooting into my mouth he pulled out and I thought went back to the bathroom. It was about this time that Richard started hammering my butthole.

Since I had loosened up it was feeling good and I was moaning out load. He had me almost bent in half and I guess I was being kind of loud because Richard said, "This slut needs a cock in her mouth."

I thought he was talking out loud or to Damon but then all of sudden there is not one but two huge black cocks slapping me in the face and I'm being told in no uncertain terms to get my mouth around one of them.

These two guys (Ty and Charles) must have been in the adjoining room with Richard. I didn't respond quickly enough and I now have my ass which is already full of cock being slapped by two black men at the same time. I open my mouth and am able to get about half of Charles cock into my mouth. Ty takes one of my hands and puts it on his cock telling me to jack him off. His cock is by far the largest of the group. Bigger than anything I've ever seen in person both in length and girth.

Richard is laughing crazily as he pounds my ass. I see Damon sitting in a chair and hear him say I told you I was going to make sure you got everything you could want. Richard is really working deep in my bowels, grinding and rotating his hips until he fills his condom and pulls out.

There isn't even a moments hesitation after Richard pulls out, Charles pulls out of my mouth, wraps his cock in a condom, flips me over to where I am on all fours. I'm begging him not to fuck me, telling him he can cum in my mouth. His answer is, "I'll fuck you and cum where I want slut." Before I can respond Ty is slapping his monster cock in my face. Charles starts smacking my ass telling me you better get some of that black cock in your mouth bitch.

I can barely get Ty's cock head in my mouth. I mean it seems huge. Charles has a couple of fingers in my rectum and is stretching me open. It isn't long before he pulls his fingers out and brings his big tool to my back door. I don't think there is any way that thing is going to fit into me when I feel the head pop into me. I tried to scream around Ty's dick but can hardly get anything out.

I'm trying to scoot forward to get away from Charles assault but by doing that I am pushing forward onto Ty's monster cock. Charles isn't exactly patient in pushing his big cock into me. At least he was generous with the lube. It felt like I was being split in two but he kept pushing in deeper.

Charles would pull out an inch and push in two. He kept this up until I think he was all the way in my ass and then he start to fuck. Wish there was another word for it because he was like an animal rutting. He was pounding away at my ass thinking of nothing but his own pleasure.

At some point Ty pulled his log out of my mouth. I'm not sure how long Charles screwed me, I may have even passed out, but eventually he came. I could feel his big cock pulsing in my bowels and was afraid that with the copious amounts of sperm he was shooting that the condom would break.

When Charles was done he just pulled out and walked away. I collapsed onto my stomach. I wanted to get up but wasn't sure my legs would hold me.

I must have been delirious as I had forgotten about Ty, but he hadn't forgotten about me. He grabbed me by the ankles and flipped me over. He said, "When I'm done with you, you won't walk right for a week."

With that said, he put my ankles over my head and pushed his plum sized head against my already stretched asshole. He was holding his cock in one hand and my legs over my head in his other while he forced that thing into my butt. If I though Charles was splitting me in half, Ty felt like a Louisville Slugger baseball bat being pushed into my hole. I was screaming and crying. Somebody stuffed a cock in my mouth, it was either Damon or Richard as it was a white cock. Ty just kept working his big black cock deeper into my bowels. At some point, I'm not sure if he ever got entirely in me, he started stroking in and out of my ass. There is no describing the feeling of having something like that up in your intestines or the pain associated with a dick this size.
Regardless, it didn't matter to Ty as I was just a receptacle for his monster cock. He fucked me hard and relentlessly until he was satisfied. Whomever was in my mouth had finished and cum in my mouth a good 15 minutes before Ty was satisfied. When Ty pulled out if felt like a truck had driven out of my rectum. I felt relief and strangely longing but not for something that big again.

The four guys told me to get dressed and get out. They did allow me to use the bathrooms and I cleaned myself up the best I could. I had blood on my rectum, my makeup was ruined and at some point my beautiful panties had been ripped off of me.

I'm sure the young man at the valet desk was a lot less impressed when I half stumbled and half walked bow-legged to the stand to give him my claim check. I don't think he desired me anymore.

That was the end of my dressing as a woman. Ty was right, I did walk funny for quite a while. While the element of danger and unknown was always part of the excitement I found out that It can be a scary and dangerous world out there. I consider myself lucky that they all wore condoms and only a couple came in my mouth.