"I need a boyfriend discretion is a must.

I am a closet transsexual.

I prefer to be called by my female name and to be dressed up as a woman. For discretion reasons I cannot always do that.

I need a man in my life to satisfy my sexual needs on a very regular basis.

I need to be forced to submit to your cock. To be forced to worship it. To be made to service it orally and to be taken anally.

As you can see from the photos, this is how I prefer to dress and my penis is small. You need to be much more well endowed than me.

You need to be muscular, well built and respectful.

I am attached so as I said, discretion is a must.

If this turns you on and you can be the man for me, please get back to me."

"Perfect," exclaimed Denise. "This text includes the edits that Naughty wanted," she added.

"Ok, here goes," I muttered hesitantly as I clicked 'update' and then clicked the 'post' button so that my profile would go live. My profile. On a transsexual dating site. My stomach twisted into a knot. Naughty was adding a regular boyfriend to my humiliation. Or rather I was being forced to find myself a boyfriend.

"Well, I've got to get back to work," stated Denise, my super hot brunette secretary. The one I was being forced to have an affair with. Forced by Naughty.

I watched her as she slipped out of my office. Such a hot brunette. Every man's fantasy. Today her shapely body was covered by a light blue frilly blouse, unbuttoned just enough that you could catch a glimpse of her lacy dark blue bra. She also wore a pleated navy blue skirt that almost came down to her knees. It hid the lacy dark blue garter belt that held up her dark blue stockings. Her feet were clad in dark blue heels. Hoop earrings and large thick bracelets completed her look.

As the door closed behind her I returned to my thoughts. I looked back on the past five weeks and how things had progressed. From being blackmailed into masturbating while wearing lacy lingerie, like I have under my suit now, at the beginning to last week when on our business trip I was transformed into a 'woman' and was forced to seduce men and submit to their cocks. Naughty had said I was being trained. That I was his/her favourite project. Project being trained for what? That was something I really did not want to dwell on too much. Especially after meeting Jerome and Janine.

I shuddered.

My penis stirred.

Denise had also been gang banged. She had wanted more big black cocks. Until then. She really did not want that to happen. Naughty showed that he/she would not only push the limits but that Naughty could cross the line. To protect Denise from that ever happening again I asked Naughty to work out a deal. Part of this deal hinged on me getting myself a regular boyfriend to service.

Dolled up as a girl.

Weekly.

My stomach churned.

My penis stirred more.

It was Monday, 1 pm in the afternoon. I too should be refocusing on work. But I couldn't. I thought about the fact that I still did not know who Naughty was. I also thought back to last Friday and to making the deal. Part of me remembered that Naughty did not have to do this but he/she did. Still it did not make me happy to accept the conditions.

And when on the car ride home Denise finally asked what deal I had made to protect her, I couldn't even tell her. That was part of the deal. We had been holding hands all the way home and when she brought up the deal, she held my hand tighter and thanked me for taking care of her.

She rightly figured out that the boyfriend thing was part of it. Almost as soon as she read the chat posting this morning that Naughty wanted me to pick myself out one. She again tried to pry the details out from me and again I reminded her that I could not. All that I could admit was that I had made a deal to protect her from gang bangs and that more details than that could void the deal.

That had brought about a loving and passionate kiss from my secretary.

As I breathed in, I could still taste Denise's juices and her boyfriend's cum in my mouth. My mind flashed back to the beginning of lunch when I had been told to eat her out on my couch as usual. She was as horny as ever since her boyfriend had not made her climax over the weekend.

He just filled her with his cum.

Again and again and again.

Only fake climaxes for her.

Again.

She desperately had needed my tongue. I could tell that she was well fucked, six times she claimed, and that she had not cleaned herself down there. Naughty had forbade her to, until after I had eaten her and cleaned her out with my tongue.

As I shifted in my seat I felt the butt plug vibrating away in my ass. It reminded me of my situation. It made me feel horny. I thought of the matching egg buried in Denise's pussy. Vibrating away to keep her horny too. My conflicting emotions over my love for my wife Emma and for my girlfriend Denise welled up in me.

Thoughts of the this upcoming weekend's party slipped into my mind. When I had asked Naughty for more details I didn't find out too much. I was to be away from my family from 4 pm Saturday till maybe Sunday afternoon.

Naughty also said: "I will give you more details about the party later. Rest assured though by the end both your jaw and ass will be quite sore."

That did not reassure me. Not at all. Sounded worse than my night with the Japanese businessmen.

Since Emma had a yoga thing too, I would have to make arrangements for my children, and Denise would have to tell her boyfriend something.

I had to get focused on my work. Even if just to give me a respite from these issues. I really did have lots to do after having been away from the office for a week.

Somehow I managed to get myself into my work. I had loaded a client's information into my brain and seemed to be getting the head space to focus on it.

"Ding!"

My phone went off. I looked at the screen, it was from the dating site. Someone had replied to my ad. Naughty had said that I needed that setting on. I needed to know when a man sent me a reply. Why? To know how many were interested Naughty had said.

It was only 1:15.

It only took 15 minutes to get my first reply.

My heart leapt into my stomach, this was really going to happen. I was going to get a steady boyfriend. Forced to get, I corrected myself. Images of a muscular man with a large cock wanting regular servicing flooded my mind.

My penis stirred.

I needed to not think about it. I got back to my client's file again. No problems but still I had stuff to take care of.

"Ding!"

I looked at my phone. Another reply. I had just got my work focus back. Once again I began thinking of the prospect that lay before me. Another man was interested in my sexual services.

I had to work. It needed to get done. I began to re-read my notes. My work came back to me.

"Ding!"

A third man had replied to my ad. Looking at my phone confirmed it. I really had hoped that no one would reply or that they would not be suitable in Naughty's eyes. I had hoped that-

"Ding!"

A fourth man.

It was 1:30.

Four in 15 minutes. Yes Four.

Part of me was amazed. Part of me was flattered that I was that popular. But most of me was sickened by this turn of events.

I turned back to my screen. I needed to not think about it.

"Ding!"

Another man wanted me as Shauna. Now there was little chance that none would fit the bill. My sinking feeling told me that.

I was going to become another man's secret girlfriend.

His mistress.

His regular hot Lay.

That really began to sink in. Images of me dating a man took over my thoughts. How would it work? Logistics? I also wondered. How could I be the Shauna of last week on a regular basis for my man.

Yes. My man.

How would I be able to become the Shauna in the photos and in my ad on a regular basis given that I have a wife and family?

That I could not answer yet.

My penis stirred more.

As hard as it was I forced myself back into my work. So many thoughts. So many questions. So much happening in my forced-upon-me secret life.

"Ding!" Another man replying.

I wanted to bury my head in my hands. And I had thought things were bad last week.

Somehow I had gotten back into my work. Off and on. All afternoon my phone would ding every so often. I lost count after 40.

Yep 40.

As Denise stuck her head in the door and flashed me a smile with her luscious lips, I noticed that it was just past 4:30. I had not seen her in hours. Denise had recused herself from me so that I could try and get work done, I was sure of it.

"Is it time?" she asked with a knowing look.

It was. We were supposed to log in and begin checking out the replies together.

She pulled up a chair beside mine, took my hand and squeezed it a little. As I looked into her eyes she smiled a little and said reassuringly "it'll be ok, we'll get through this."

The 'we' part did make me feel better.

Even though our affair had been forced upon us we have grown together through it. Even though I am married and never wanted an affair I do love her. She knows that I am doing this for her. To protect her from what Naughty could do to her again. And I know she appreciated it and loved me more because of it.

I squeezed her hand in return.

"Here goes!" I uttered nervously and then reluctantly logged in.

There were 47 messages in my inbox, each with a profile picture attached. We drilled through them and took a quick look one by one.

A number of them we could eliminate right off the bat. Several of them were pot bellied middle aged men. A few were in their 60's. Some younger but seemingly arrogant etc. Sadly enough most said they had wives. They must have felt something lacking in their lives. Why else look for a mistress?

Yes a mistress.

That word caught in my throat. Not only was I having an affair with my secretary, but I was going to become another man's mistress. The affair was forced on me but it was easier to cheat on my wife with a super hot babe like Denise. Had I not already been married, dating Denise would have made me feel like the luckiest man in the world.

This new affair would be very different. The reality of it hit home as we began to see "good" candidates. Muscular men with large cocks. Interested in dating me. I would have to eagerly suck on a real man's big cock. Hungrily swallow his seed. Buck back and meet his thrusts as he fucks my ass. And sincerely thank him for it.

My stomach churned.

My penis stirred.

I had been told to narrow it down to my top three to five candidates, but to be ready to add extras if more good candidates came forth this evening or tomorrow.

By 5:00 surprisingly we had it down to five.

Naughty texted me and told me to start up a videochat and set up a screen share. That is video for him/her to see us, but just text as a reply to us. The screen share so that Naughty could see the same as us from my dating account.

"How many replies?" queried Naughty with no real greeting.

"47 from this afternoon, two more since we logged in, five of which could be good candidates," I mentioned as matter-of-factly as I could.

"Wow, that's great!" Naughty typed in reply. "I knew you would garner interest. Now strip off your man clothes. Denise help him. Do it now."

Denise and I rose from our seats. She moved in close and planted a wet kiss on my lips, then began unbuttoning my shirt. Her kisses and gentle touch always excited me. Having this hot brunette undress me was amazing.

My penis became hard very fast.

As Denise pulled my dark blue shirt off, my white lace bra became revealed.

She leaned in and kissed me with her succulent lips again as she unbuckled my pants and slid them down. As she bent to pull them down her face was right in front of my pantied groin. Cotton panties with a white lace garter belt attached to white stockings.

Denise lightly rubbed my hardon through my panties. That thrilled me and sent a chill down my spine.

After I was out of my last vestiges of man clothes, namely my socks and shoes, Denise helped me into my white high heels. As she stood up, she planted another sensuous, wet kiss on my lips and lightly rubbed the front of my panties again.

She almost made me forget about what we were here to do.

"Did some send a nude picture of themselves?" Naughty asked.

"Yes, each of the five sent at least one picture," I said aloud.

"Good. Now reply to these candidates and ask for more nude pictures. Do it now."

I did as I was bid. Then my phone pinged. It was Emma, my wife.

"I need to go soon, Emma has yoga tonight," I brought up, hoping it would help end this session.

"Yes, that she does," replied Naughty. "Text her back and tell her you have lots to catch up on. She can call Jon and have him babysit till you get back," Naughty added.

My face went blank. Wait, How does Naughty know our babysitter's name? How does Naughty know -

Before I could continue that thought, Naughty must have seen the look on my face.

"Do it now," he/she typed.

I knew well enough not to hesitate. A few texts back and forth and Emma had reluctantly agreed and then confirmed that he would be coming over.

"Now Denise," Naughty began, "go to the profile and bring up the photos of one of the candidates. Shauna, pull down your panties. Do it now"

I hooked my thumbs into the sides of my panties and tugged them down, over the tops of my stockings and bent over to pull them down to my ankles. My now semi-hard penis popped out.

"Here's the first one," Denise mentioned, almost like a realtor showing a client photos of a property.

The man was white skinned with short blonde hair. His face was blurred. He seemed tallish with an athletic build. His cock was hard and looked decently big. Bigger than mine that's for sure.

"Shauna stroke yourself while looking at him. Denise read his description. Do it now."

I began to stroke my penis while looking at his picture. My eyes kept drifting to his manly cock. My own penis stiffened in my hand. I began to feel very embarrassed.

"He says he works varied hours and is married. He likes hiking, bike riding and working out at the gym. He's 6'2", 180. Blue eyes, blonde hair. He would like someone he could meet up with for quality time each week," said Denise.

My penis was slightly stiffer. I kept stroking. After a few minutes Naughty told Denise to bring up the next profile.

This man had a similar build with brown hair and a goatee. His cock seemed a little larger.

My penis grew a bit more as I kept focussing on his manhood. Reluctantly I kept stroking while staring at the image of this naked man.

And his cock.

"He states that he is into culture and the arts. His wife does not appreciate the opera or orchestras like he does. He would like someone to enjoy them with him. Someone who is heavily into oral and available weekly for discrete encounters. 6'1", brown eyes, brown hair, 190."

My penis kept responding to my stroking. The thought that I was stroking to pictures of men made me shudder inside. Whether forced or not, I was still doing it and getting hard.

After a few minute we moved on to the third. Another blonde. More muscular with thick, hairy forearms and chest. His cock was about as long as the others but thicker.

"He likes sports. Football, baseball and hockey. He plays and watches. He also likes bedroom sports much more than his wife. He also goes to the gym a lot. 6'3", 210. Blonde hair, green eyes. He likes his partners feminine and wants a discrete, long term relationship

Denise brought up his second and third photos which focused more on his long thick cock.

"I think Shauna likes this one better," declared Denise with an unexpected amount of glee in her voice.

I looked down and noticed to my embarrassment that my hardon was much more pronounced than before. I also felt my orgasm beginning to build.

"Keep stroking but don't cum yet Shauna," Naughty typed. "Zoom in on the cock that Shauna might later be servicing. Let her get a great view to masturbate to. Do it now."

I felt so humiliated as my orgasm was building in my groin and very stiff penis. Stiff from stroking to pictures of naked men while I was dressed in lingerie.

"Turn her butt plug up to the next setting," added Naughty. "Do it now."

The vibrations in my ass increased in speed. My breath soon quickened. A slight moan escaped my lips.

I kept stroking while staring at that large manly cock. It was thick and veiny. There was a dense matt of blond hair around its base and covering his large balls.

My orgasm began to well up in me as I stared at that manly cock while stroking my penis. I stopped just in time.

"Good girl, you are learning well. This one should be one of the finalists," typed Naughty.

Denise moved on to the fourth candidate.

He had brown hair, a fairly muscular build, a very hairy body and a long cock. It seemed thinner but with a mushroom shaped head. He was stroking it in the selfie.

"He likes golf, watching football and baseball and playing tennis. His wife is a prominent local person so discretion is a must. He is looking for someone to go on his business trips with him. 6', 185, brown eyes, 45 years old."

My penis shrunk a bit from the lack of attention even though all the masturbating was keeping me hornier than hell. That feeling embarrassed me and the realization that I almost came while staring at another man's cock and hairy balls.

As the feeling of orgasm had subsided enough I began stroking again. My penis stiffened a bit more but not like before.

After a few minutes Denise moved on to the fifth candidate. He was a large black man with a big, thick cock. He was very muscular with no facial hair.

"Interested in movies, dinners and dancing. Looking for someone to pamper and treat like a lady," stated Denise.

My penis grew in my hand and I tried to stroke it a bit lighter.

Denise scrolled to the next picture, a closeup of his thick, manly cock.

My penis got harder and bigger.

"You do like big black cocks!" Naughty typed.

No I don't, I told myself.

My penis betrayed me as it was just as stiff and erect now as ever.

My breath quickened a little.

"Scroll through his other pictures Denise," commanded Naughty.

The next one up was an undershot view of his cock and big hairy balls. It was the view that I had of Mikes cock as I knelt before him and worshiped the underside of his cock.

I felt my orgasm welling up in me again. I wanted to stop stroking. I wanted to stop looking at real men's large cocks and balls while stroking my own smaller penis. I wanted to not be clad in lacy white lingerie while masturbating.

My breathing picked up even more.

My orgasm was welling up inside me. I needed to stop soon.

I let go go my penis just in time. I was breathing faster than I thought.

"Good. Keep that image on the screen Denise," typed Naughty.

After a few minutes I could start up again. Naughty knew it. "Focus on that manly cock and balls and imagine what it would be like to lick it, suck on it and make it throb in your mouth as it spews a big load of goopey cum in your mouth and start stroking again," he/she typed.

Once more I wrapped my right hand around my mostly hard penis and began stroking. I stared at the black cock that was definitely larger and much more manly than mine.

This was sick and humiliating I thought to myself. Clad in lingerie, standing beside my super hot secretary and being forced to masturbate to the pictures of another man's large cock and hairy balls. All caught on camera for Naughty to use later.

My penis became fully stiff in no time. It betrayed me.

Involuntarily I was breathing faster.

I needed to cum. I really did.

I stared at that manly, black cock. I could smell its muskiness. I could taste it in my mouth. I could feel it throbbing.
My own orgasm was welling up inside me again. This was torture.

I stared at that black cock and kept stroking. I could taste his seed.

My stomach churned at the thought.

I was about to cum.

Just as I took my hand off my penis, to my surprise Denise took the tip in her mouth. She continued stroking and licked around my head.

"Uhhhhn!" I exclaimed as I erupted in an explosive orgasm. I pumped stream after stream of jism into her willing mouth.

It was a great release.

After I finished she got up. Some of my cum was on her lips. She had a naughty smile as she leaned into me and we began kissing. Reluctantly I opened my mouth as she pressed her lips against mine and I took a mouthful of my own cum. As I swallowed her tongue worked more and more of that gooey liquid into my mouth. I could see that her eyes had squinted into a smile.

As we finished, Denise licked her lips seductively. "You taste so good lover," she added.

I looked at Naughty's messages. I could see that Denise had been told to finish me as I masturbated to another man's cock.

I felt so humiliated.

Standing here clad I lacy white lingerie and high heels. Standing here having just masturbated while looking at naked pictures of hunky men. Cumming while imagining sucking off a well endowed black man. Swallowing my own cum from Denise's mouth. Still tasting the cum in my mouth and on my lips.

All forced by Naughty.

But humiliating still.

"Great job Shauna, now time to head home. Leave your phone on so that you know how many more are replying. You can pick one for yourself tomorrow."

All evening my phone would ping every half hour or so. It even pinged when Emma crawled in bed beside me. I had wanted to pretend to be asleep but I had to grab my phone so she wouldn't.

Emma had come home very late from yoga and I didn't want her to feel bad about spending extra time having fun. She deserved it. Over the past few months she always came home late but very satisfied. A bit nervous about her lateness, but satisfied nonetheless. Like I do after we make love.

"What's that Hun?" Emma queried as I put the phone back on my nightstand.

"Just an email notice from work. A pesky client of mine is up late and worried about his account is all. Just monitoring it as my boss asked me to is all." I replied. A lie. A flat out lie to my loving wife. It made me feel so bad having to lie to her. She seemed to buy it though.

"My friends really wanted to -" Emma began.

"As long as you had fun, it's all ok," I said as I interrupted her. "No worries. You need to have time for your friends after yoga. You always come home happy, and that's good," I added.

Emma then snuggled up to me. "Thanks," she replied.

I felt like such a heel. Cheating and lying to her. And all she wanted to do was love me.

The next morning when I arrived, Denise greeted me with a smile and a twinkle in her eyes. Her attire was hot, but secretarial, as usual: a light pink blouse, a peach coloured skirt with light pink stockings and heels.

"Good morning," she chirped happily with a more flirtatious smile when I got to her desk. As she followed me into my office, she added "We have things to do according to Naughty."

She had closed the door after her and turned me to face her. There were no cameras on. No mics to pick up audio.

Denise wrapped her arms around my neck and drew my face to hers. She placed several wet kisses on my lips that surely smeared her pink lipstick a little. As I returned her affections we kissed deeply and our tongues entwined.

As she broke our embrace Denise looked me square in the eyes. "Thank you for going through with this. I know that you are being forced to take on a male lover in order to protect me." She paused. "You don't know how much I truly appreciate it," she added and planted more wet kisses on my lips before I could reply.

Yes I was being forced to take a secret boyfriend to service regularly as part of my deal with Naughty. Her appreciation mollified my negative feelings about it and reminded me what it really was about.

When she broke our embrace she began unbuttoning my shirt and helped me into my pink lingerie set. Lacy bra, garter belt, stockings and pink panties. When I returned from giving myself an enema she playfully inserted my buttplug and I her egg. We both set them to vibrate at the first setting.

"Ok. Before we start work we need to check on the new replies and check out the nude photos that you had asked some to send you. These and others from their profiles we are to make into a slideshow."

"Great," I said sarcastically. "I assume for me to masturbate to later."

"Maybe," replied Denise matter of factly as she cocked her head to the side. "Afterwards you will need to decide which man you will meet first and contact him."

There were a lot of nude photos and it seemed to take forever to make them into a slideshow. Luckily none of the new respondents fit the bill, so we had our five for me to pick from.

Afterwards I got to my actual work and left picking a man till later. There was lots to do and luckily I was better able to get focussed on work today.

Before I knew it, it was 4:30 and Denise was closing the door behind her as she came into my office. Part of me had dreaded this all day. Time to pick a man. A man for me to secretly date and to service sexually while Naughty likely watched and recorded.

Naughty had me strip down to my lingerie and don my pink heels as usual. Then we had to review the five candidates. Before Naughty let me choose I had to masturbate while watching the slideshow. I had to edge myself. Three times.

No cumming though.

Then was the moment of truth.

"Tell me," began Naughty,"which man do you want to meet?"

Part of me cringed inside. Severely. It was bad enough to have to submit to another man's cock and to have to service him sexually. Now it was taken to a new level. I would have to pick the man myself.

Images of all five men flashed through my head. Naked. That made my stomach churn. I hesitated.

"So, who will it be?" Typed Naughty impatiently. "Say it out loud."

"I will pick ," I hesitated again, my heart began to race, "the black man," I looked down at my feet, I could not meet Denise's gaze.

"So clearly and louder state which man you want to meet and if he is the right one to offer your body to regularly?" Typed Naughty.

Denise took my hand and squeezed it reassuringly. I looked into her eyes and could feel her love for me.

"I want to meet the black man. If I think he is the one, I will offer my mouth and my ass to him unconditionally. I will service his sexual needs and swallow all of his seed." I said clearly and confidently.

"Good, now write him a response," came the tert response from Naughty. "Ask to meet him tomorrow night at that new coffee shop near Denise's place. Do it now."

I wrote him as Naughty had asked.

"Now, take Denise to the couch and satisfy her while we wait a bit for a reply. Do it now."

As I got up Denise took me by the hand. I could sense the sexual tension in her. She was eager with anticipation. We turned the webcam towards the couch as we knew we had to so that Naughty could record it.

We sat down on the couch and began to make out. As we kissed sensuously I began to unbutton her blouse. Beneath it was a lacy light pink bra, much like mine. Soon that was unhooked and off.

She giggled a little then moaned softly as I began lightly licking her nipples. Her breasts were so perfect. Mounds that protruded nicely from her chest. Sizeable, but not too large, and perky with soft nipples and areolas. Her skin itself was smooth and milky white.

I went from teasing her by licking around them to nibbling on them, sucking lightly and then her favourite: suckling on them. She was loving the attention and getting very aroused.

"I need you down here," she expressed huskily as she gently pushed my head towards her lap. "I need your tongue. I need it now," she commanded.

I slid off the couch and between her pink stockinged legs. She lifted her skirt to reveal a soaked pair of panties. I reached up under her skirt, hooked my thumbs in each side and pulled them over her lacy pink garter belt, over her pink stockinged legs and off.

She then spread her legs invitingly and I dove in on her sopping wet dark bush. I breathed in the aroma of her womanhood. Hers smelled of pussy mixed with sweat. I licked her slit from the bottom to the top and tasted her sweet nectar.

A shiver went through her body as I did this. A light moan escaped her lips. I looked up and saw that she was already almost in a trance. She was tweaking her nipples with her hands head tilted back and eyes closed.

What a hot view of this heavenly creature. All I could do was stare. Suddenly she released her right breast and pushed my head towards her womanhood.

"I said I need your tongue now" she reiterated lustily.

I dove into her luscious wet pussy with my tongue. I tongue fucked her vagina, lapping up all of the juices that flowed from it.

"That feels soooo good," she uttered. Her breathing got faster.

I then began to lightly lick Denise's bloated clit. That brought about deep moans from her immediately.

I circled her knob with my tongue and lavished it with a heavy dose of saliva.

Shivers ran through her body and she moaned heavily. I could see that her pretty face was flushed and her tits were covered in red marks as she worked them over.

I dove into her pussy again and was rewarded with fresh juice. Alternating back and forth between her clit and her pussy was driving her crazy.

She really loved my tongue.

I really loved eating her out.

I felt as if on a high when eating her.

"Uhhhhn," she moaned out loudly. Her breathing was faster than before. She was nearing her orgasm. Then it hit her

"Uhhhhhhhn!" Denise exclaimed as her thighs clamped down on my head and her whole body spasmed over and over again. I didn't stop licking her clit until her legs went limp and she lifted my head up.

"That was awesome as usual," she declared with a satisfied look. Her hair was tussled, her pink lipstick smeared, her perfect breasts looked manhandled. She seemed to be in heaven.

She pulled me up and into her on the couch. We kissed and cuddled.

My penis was rock hard.

After a few minutes I broke from our embrace and went to check the computer. Naughty as usual mentioned that I had done a good job. And I had received a reply. I arranged a 7:30 pm meeting at the coffee shop.

My heart raced and my stomach churned all night. I told Emma that I had extra catch-up work to do the next day and would be home perhaps quite late.

The next day went as I mostly as expected. When I got to work I donned my lingerie and Denise put my vibrating buttplug in. I put her vibrating egg in. Several times I had to masturbate to the edge while watching the nude slideshow. I so wanted to just cum but not to pictures of men and their manly cocks.

I did not go down on Denise at lunch though as Naughty wanted me to just keep edging myself while looking at the muscular men with large, thick cocks.

As I worked my thoughts kept going back to my upcoming date that evening. I would have to decide if I wanted this man to be my steady secret boyfriend.

Wanted.

What a phrase to use. Me picking a man for myself. The man that I wanted.

This all made me feel sick.

Then the day took an unexpected turn in the video chat with Naughty.

"Shauna, After you masturbate to your nude photo collection, but not cum, you are to change out of your lingerie and go with Denise to her place where she will transform you into the the full Shauna. Makeup, wig, hot looking outfit. The works." Naughty typed

"Huh?" exclaimed Denise out loud.

We both were floored. Up to now our affair had been basically confined to my office, other than when we were out of town. I figured I would be meeting my new boyfriend at a hotel in the future but did not think beyond that. The last time "we" were together outside of my office we were caught holding hands coming out of a lingerie shop by my coworker Mitch.

"Yes, you read correctly. You two are to go to Denise's place and there Shauna will be transformed into her real self for her date."

Another bombshell. I was to be dolled up as a woman. And go out in public. In my own town. My stomach turned over and tied itself in a knot. My heart leaped into my throat.

"What if someone recognizes me?" I asked without hesitation. This was literally too close to home.

I had imagined meeting him as me and only dressing up for our future rendezvous AT the rendezvous. In other words, get to the hotels first, get ready for my man there and then after he had left revert back to Shaun.

"If you do a good enough job, like at the bar last week, you should be fine. Become Shauna, and then no one should recognize Shaun," Naughty replied.

I swallowed the lump that was in my throat. Every time I thought that Naughty had done the worst to me, I was wrong. He/she took it to another level. My heart sank deep into my knotted stomach. This was going to happen.

I had no choice.

Or Emma and everyone I knew would get videos of me in lingerie, servicing other men's sexual needs.

My life would be over.

So I was to go out in public as the female Shauna. That hit me like a ton of bricks. After that revelation everything seemed surreal. Kind of like watching a movie.

As I was taking all that in I watched Denise have a conversation with Naughty. Denise was concerned about her boyfriend coming over. Naughty countered that he usually had a boys night out on Wednesday and that Denise had better ensure that it would happen.

Denise calmed down when her boyfriend confirmed that he would not have time for her as he was going out with the boys.

She was also told that I was not to eat her now. I could see that left her feeling frustrated and at least a little horny. She was used to being eaten by me every work day. We left work at 5 pm, each in our own car.

I knew where she lived as I had dropped her off before, but had never actually been in her place. Nice small apartment building, with only eight units on three floors, with the manager in an expanded basement suite by the laundry room. Denise's place was a spacious 2 bedroom. She had had a roommate before she said but the girl moved back home when she got laid off at her job. Her former boyfriend then began dating Denise.

I found out that she had set up my lingerie and clothes in her spare bedroom closet. It felt weird to see my outfits again. Yes, my outfits. And my wig.

Denise had me take a quick shave and shower and brought out only some of my lingerie to wear. Then she sat me down at her vanity with my back to her mirror. It felt so wrong to be in Denise's bedroom. Another woman's room. Not to have sex but still I was in another woman's room. The woman I was having an affair with. Forced but an affair nonetheless.

Her room was coated in pink. Pink bedsheets, pillows, light pink walls etc. Sitting there in my black panties and my lacy black bra with her about to do my makeup made me feel so feminine. So submissive.

Everything still seemed surreal as Denise applied foundation, blush, eyeliner, mascara and bright red lipstick. I was in a daze.

"Besides hiding Shaun from those who might know him," Denise said slowly as she expertly and with meticulous care applied my makeup. "If you think he's the right man for you, you want him to pick you too," she added.

That brought me back to the here and now. The right man for me. My man.

Yes MY man.

I suddenly felt very nervous.

I would have to convince him that I was the right woman for him to have an affair with. I would have to seduce him. That reality suddenly hit me.

If I did not seem to want him, to truly want him, he might not want me.

"Naughty is forcing you to take a boyfriend. Whether you like it or not. Better to get a good one rather than a bad one," continued Denise.

"Wouldn't you rather suck the cock of a man you can stomach, and maybe get along with, rather than one you truly don't like. You can make the best of the situation. Or not," Denise said bluntly yet calmly as she continued detailing my face.

My nervousness went through the roof. The reality of it hit me again. It would not be a 'one night stand' like last week's encounters.

I would be sucking the cock of the same man, being fucked by the same man, going out with the same man. Every week. I would have to make him desire me. I felt like a bride getting cold feet on her wedding day.

I would be like Janine.

No, I would become Janine.

This was what I was being trained for.

Were my breasts going to be grown larger, was I to be truly feminized?

I felt so trapped. So helpless.

Denise must have sensed my sudden dread. She stopped and looked straight into my eyes.

"If it's this hard on you, call the whole deal off. I wouldn't hold it against you. " Denise declared sounding truly sincere. "The thought that you want to protect me and tried is good enough for me," she added with a hint of shakiness in her voice.

We both sat there in silence for a few moments.

"Yes, I can endure more of those..., um...," she hesitated and I could see tears welling up in her eyes, "...parties...," she uttered shakily, "and get used to it, if need be," she finished trying, but failing, to sound firm.

That really snapped me out of my funk.

"No, no way." I replied.

I had almost forgotten why I was doing this. Maybe this was part of Naughty's plan all along? Or not. But I did have to protect my Denise from gang bangs. Period. That brought my resolve back. I had a purpose. It was not about me. It was for Denise.

For my Denise.

"No, you are not going through that again. It is better that I go through this a thousand times rather than see you go through that again," I countered with a resolved firmness.

Tears were still welling up in her eyes as she stared right into mine.

"Are you sure?" queried Denise "are you sure you can really do this weekly for months, or maybe longer?"

This was all happening so fast. I was filled with so many conflicting emotions. About Emma, Denise, where Naughty was forcing me to go, about -

"Yes. Finish me up and let's get going," I said. I couldn't think about things now, I had to make things happen.

Denise hugged me again, this time more tightly than ever, her head resting on my shoulder.

"Thank you. You don't know how much I appreciate this. I so wish I could repay you," she declared "I could cuddle with you forever," she uttered quietly after some hesitation.

"You're the knight I always dreamed of," I heard her whisper to herself.

The warmth that overcame me helped dull my other feelings.

When our embrace ended, she wiped her eyes then finished my makeup and quickly applied some red nails. She told me not to turn around, then disappeared into the other room. She came back a few minutes later with some black clothes. Apparently she had been told to do more shopping for me after we got back from our trip.

Denise gave me a black lacy garter belt and opaque black stockings. Then she put a black blouse and pleated black skirt on me. Next came a pair of black heels.

She fitted my brunette wig on and stepped back to check me out. She had me turn from side to side for her. It still felt weird modelling woman's clothes for Denise. She added a pair of red bracelets to each of my wrists and a small black purse and turned me to the mirror.

Again to my amazement I was staring at a hot looking brunette. Definitely a Shauna, not a Shaun.

I felt so self conscious going outside like this, but less about being recognized.

As Denise opened the door and I stepped into the hallway/stairwell of her apartment, I felt a slight rush of air over my stockinged legs. The cool, sensuous feeling on my stockinged legs sent a chill down my spine. I felt the tug of my garters on my stockings as I walked in my heels.
"Come," Denise suggested as she took me by the hand and began down the stairs.

I felt so feminine walking in my lacy lingerie with a skirt, blouse and accessories. So feminine. Every fibre of my being was alive. I expected everyone would look at me. Everyone would see a man wearing woman's clothing. My face felt flushed. I felt so ashamed. I felt like I was in a trance.

Both Denise's and my heels clacked on the stairs. To my amazement I walked much better than before, even going down stairs in heels. It was becoming part of me to walk as a woman in heels.

That sent a chill down my spine.

As we approached the landing by the front door, a thirty-ish man entered. He was casually dressed in jeans and a t-shirt. Average height and build with light brown hair.

His eyes washed over my body. I felt so embarrassed walking in woman's clothing.

"Hi Denise," he said with a smile as he turned his gaze to my companion.

"Hi Leonard," Denise replied with just as friendly a smile.

"And who is your friend?" Leonard asked was he sized me up from head to toe. My heart began to race. My embarrassment climbed to another level.

"This is Shauna," Denise mentioned as she nodded her head towards me.

Butterflies welled up in my stomach. Now I had to meet people as Shauna. Not just in name, but in look as well. I was truly becoming Shauna.

"Hello Shauna," Leonard stated as he extended his hand to me. Instinctively I shook his hand with my right. The two bracelets that matched my red nails clattered lightly.

"Hi," I mustered in my best girly voice in response.

He looked me in the eye and smiled warmly.

I felt so embarrassed. I knew that I was blushing, even if the makeup likely covered it up.

"We should get together for coffee sometime," Leonard announced as he turned back to Denise. "And maybe you would like to join us Shauna," he added with a smile to me.

"Yes, that sounds good," answered Denise for both of us. "Have a good evening!" she added as she turned and continued down the stairs, pulling me along behind her. I managed a slight smile as I passed by him.

"See you both later," Leonard replied.

A wave of relief washed over me as we got to the bottom of the stairs. Denise leaned back to me a little.

"You see? Nothing to worry about. Leonard accepted you as Shauna," she whispered loudly to me. "He even was hitting on you," she added with a giggle.

When Denise opened the door to the small underground parkade another rush of air went through me. Over my stockinged legs and under my skirt. It felt cool and gave my legs a silky, sensual feel.

The parking stalls were tight as it was not a big building. Four stalls on the front wall and two by the entrance by the back wall.

"I am lucky to have one of the underground stalls. I feel safer in here at night than in the parking lot out back for the rest of the tenants," mentioned Denise. We got into her car and soon we were passing by the back lot and into the alleyway. Afterwards we passed by the front of the building.

I felt so relieved that I didn't have to go out the front door dolled up like this. I thanked Denise for not making me walk the two blocks to the coffee shop. She smiled and squeezed my hand in reply.

Traffic was light and before I knew it, we were parking right by the door. The coffee shop was a large place and we picked the dim lit corner I had told him to meet me at. At least I had the luck that neither the tables there nor the leather easy chairs and couch were occupied.

There were a fair number of people there. Several looked our way. Yes, two women in skirts and heels usually do draw attention. Attention that I did not want.

Again I felt so embarrassed. Again my face felt so flushed. My heart had leapt into my throat when I had stepped out of the car and out into the public for all to see. Now I felt it thumping away in my chest under my bra and blouse.

I felt as though every eye was on me. That all would know I was a man in drag.

I looked down and avoided the gaze of the men we had to pass by to get to the far corner. Even then I felt their eyes on my legs and my skirt covered ass. I knew they would be looking at us, how could they not? I overheard one whisper "What hot legs they both have," and another quietly added "I wish I were with them."

My heart beat faster and I felt warm all over. I also felt flattered to my surprise. Luckily we were soon out of earshot of them and made it to the corner.

Nervously, I sat down on the leather couch. It felt cool on my stockinged legs.

"You're doing great," Denise commented as my heart began beating slower. But only a bit. "Stay here, I will get us something to drink. It will be ok."

Denise got us decafs then sat at a table nearby. My hands shook a little as I took a sip of the hot beverage. The men kept ogling us. I averted their gaze. I remembered why I was here and I started up an audio recording program on my phone and placed it in my slightly open purse. Naughty wanted to listen to the date. And likely record it for posterity.

Ugh.

Time seemed to go so slow. I was sure that those guys were still looking at us. A quick glance confirmed that. I began to wonder if they suspected that I was actually a man.

After a few minutes a black man entered the shop. It had to be him. My heart began to race again. He looked around, as if it were his first time here, then came over.

It wasn't him.

"Hey don't I know you from somewhere?" He began with a smile, obviously a bad pickup line.

"No, I don't think so," I replied nervously in my best girlish voice.

He sat on the same couch kind of close to me. He was obviously checking me out. I was beginning to feel scared. This was not part of the plan.

Suddenly he leaned over to me.

"Look, I'd like to get to know you," he began, "we could become-" he continued as he was reaching for my thigh.

I was mortified. What to do? I began to shake. How do I get out of this situation? How do I not draw attention to myself? At least not more than my look already has.

He didn't reach my leg as another man grabbed his arm. I looked up to see the man from the dating site.

"She's with me," he stated firmly. "I suggest you find some place else to sit," he asserted commandingly. I felt a wave of relief wash over me. The first one since I entered the coffee shop.

The first man looked up, startled. Then he withdrew his hand and got up to leave. My date stood firm and smiled a confident smile. He was built. The other man not.

As soon as this man was on his way out of the shop, the man I was here to meet turned and offered his hand to me. I smiled and reached mine out. To my surprise he didn't shake it, rather he gently took my hand in his larger one and brought it to his lips.

After he kissed it, he smiled and stated "My name is Jason."

"Shauna," I offered in reply in a bit of a shaky girl voice.

My stomach was full of butterflies.

"May I sit down?" Jason asked very politely.

"Yes," I replied about to get up.

He motioned for me to stay sitting as he sat down beside me. He turned to me and only half sat on the soft leather couch.

"You are even better looking than in your pictures, I am so glad we've met up," he said with a smile.

I sized him up without thinking about it. He was wearing a black business suit, with a white shirt and a red tie. His body seemed to be ready to burst out of it. His chest was broad and even his neck looked muscular. He had a friendly looking, clean shaven face and short hair.

"I played middle linebacker in college," he added as he noticed me checking him out.

"I'm sorry," I responded, "I didn't mean to stare." I said regaining my best girly voice and some of my composure.

"You look handsome," I found myself remarking.

"Thanks," he replied. "Look, I'm not good at this," he began. "I have never stepped out of my marriage. My wife does not like sex much anymore it seems, nor does she seem to want to go out a lot, other than social affairs to be seen at. What I need is someone who can satisfy my needs in bed and spend some time together. I'm not looking to get divorced, I just need someone to make my life complete. I hope I'm what your looking for."

I did not know what I was going to say either but I thought there would be more small talk first. I was glad I did not have to suffer through that. But then again, it would have delayed what I would have to say.

I felt so nervous. Like I was on my first date. His presence made me feel so - so not manly. I felt so feminine. So submissive.

"I," I began tentatively, "am also married." I added trying to gather my thoughts. I glanced down where my wedding ring should have been. I had taken it off as I always did when dressed as Shauna. I suddenly felt so naked without it.

"I too am lacking something in my marriage. I love my wife, but need something more," I paused. I really did love Emma. I really didn't want more. Images of my wife Emma flashed through my brain. My busty, blonde, good looking wife.

I wished I could be sitting on my couch, resting my head on her big, soft chest while watching some inane television show with her. Any television show. Like we have often done in our pyjamas. Her large chest looks so good in a bra but feels so pillowy when out of one.

"I need a man in my life, I need a man to worship sexually, as I declared in my profile," I hesitated as that was hard for me to say.

It was hard to hear me say.

The butterflies turned into a knot.

The next was even harder. "I need a man to satisfy me sexually, on a regular basis. Not as a man but like a woman. Something that my wife can't do."

My stomach churned.

This brought a big smile to his face.

"I also need discretion, as my wife can never find out," I added.

This felt so humiliating. So utterly humiliating.

"I do too," he replied. He then placed his large hand on my knee.

A shiver ran up my spine.

This was really happening.

The next part took all my courage. I reached out and put my hand on his leg in return. He smiled back at me. My heart began to race again.

Jason removed his hand from my leg, took my hand and placed it on his crotch. He had a nice sized bulge. It felt semi firm.

My face felt totally flushed.

"You like?" He said with a smile.

"Uh, huh," I mumbled softly, knowing that I had to.

"Would you like to see it?" He suddenly asked.

Things were moving so fast. My heart pounded in my chest. Another moment of truth.

"Uh, huh," I replied submissively not meeting his gaze.

"Let's go to my car." He suggested and reached out his hand to me.

"Uh, huh," I responded feeling the blood leave my head as I put my hand in his and let him help me up to my feet.

I blushed.

I glanced over at Denise who smiled and slightly nodded her head.

Unsteadily on my heals I let him lead me out of the cafe. A few of the other patrons looked me up as we passed by. Some smiled. That made me blush even more. The guys from before grinned knowingly as we approached. I looked down at my feet in shame.

Thankfully we got to his car fairly quickly. It was a modern mustang. He opened the door for me and folded the seat forward so I could get in the back. In heels it was more challenging than I had imagined. He stuffed himself in beside me. I placed my purse at my feet.

My heart was racing. I had just willingly gotten into the backseat of a car with a horny, hunky man. A thrill ran through my body at what might happen.

A thrill? My stomach turned in knots. I felt full of mixed emotions. Horrified at what might be about to happen. Thrilled by the obvious sexual tension.

"I have not done anything like this," Jason began with a smile, "since I was first dating my wife."

I readjusted myself in the seat as it was awkward to sit here in heels. As I did so I moved into him. He reached his arm around and in behind me and I wound up nestled under his left arm.

"Is this comfortable for you Shauna?" He asked politely.

"Yes," I replied nervously.

"I would be s bit more comfortable if you would help me with my belt buckle," he professed sounding a slight bit nervous himself.

He began fumbling with his belt with his right hand and I shifted a bit to reach across with my left. This pressed me even more into him. I could feel his muscularity through his clothes. he was truly built and seemed to be in as good a shape as he likely was in college. As I started helping him with my nailed left hand I looked up at him.

He leaned down and brought his lips to mine.

Both a chill and a thrill ran down my spine. I still was turned off by the thought of kissing another man. Really turned off. But Naughty was forcing me to do this.

I opened my mouth and let his tongue enter my mouth as I kissed him. Hesitantly at first but the more we kissed the more he got into it. I knew I needed to reciprocate so I forced myself to be just as eager.

At least his mouth tasted good. He had brushed his teeth before we met with a minty toothpaste.

After a bit more fumbling on both our parts, his pants were open and his mostly erect cock sprang out.

"I have needs. Can you satisfy them Shauna?" He asked quietly, barely pulling his lips from mine.

"Uh huh," I replied as lustfully as I could.

Immediately he guided my nail clad hand to his erection.

It felt very warm in my hand and I could feel it throb in my light grip. He was as big and about as thick as Mike Brown. His balls were as hairy as in the pictures.

He moaned lightly as I began to stroke him.

"Mmmmm, I like that," he moaned quietly as he resumed kissing me.

My stomach churned as here I was making out with this muscular man.

My penis was rock hard in my panties.

Once again it betrayed me.

After only a few strokes I could feel some sticky pre-cum on my fingers. He hadn't been touched like this in awhile. I could feel his excitement.

I broke from our kiss and looked down at his dark manhood.

I had to admit to myself It was a hot view. A neatly manicured feminine hand, replete with red nails was wrapped around a big, thick, black cock. And was stroking it.

My stomach still turned over as it was My hand stroking this man's cock.

"Your cock is so nice," I asserted huskily. I cringed inside as I said it.

"Your soft hand feels so good," he replied.

It was now or never, I told myself as my heart still raced. This man seemed like a not bad choice. I could definitely get worse.

I leaned over his big, thick cock. The muskiness of his manhood wafted into my nostrils.

I licked the tip of his cock. It tasted slightly salty from his pre-cum. He gasped then moaned in response. I kept stroking his now completely stiff cock.

I wrapped my lips around the large head of his manhood. I sucked lightly as I licked it. He moaned even more.

I began stroking faster and taking more of him in my mouth as I began to bob up and down on his big manly cock.

He moaned more and breathed faster.

"That feels so good Shauna, too good," he exhaled between moans.

He was almost ready to cum, I could tell.

Then all of a sudden his cock throbbed and his body stiffened.

"Uhhhhnnn!" He exclaimed as his cock exploded in my mouth. I slurped, sucked and swallowed as he kept cumming.

After taking his big load in my mouth i was still sucking on his manly cock when he lightly motioned me to stop.

"It feels sensitive," he explained.

"That was the best blowjob I have ever had," he said with a smile as he looked into my eyes. "My wife does not do that anymore."

It was definitely a fast one, I thought to myself.

I licked the dribble of cum from my lipstick smeared lips and smiled in return. His taste did not turn my stomach like I wanted it to. In fact his seed tasted better than most that I had swallowed.

"I would like us to start dating," he stated firmly.

This was moving fast.

My mind raced. I had just blown a man I had picked up through the internet. Naughty was forcing me to take a boyfriend. I didn't want one. I am a man. But made up like a woman. But, if I must have my own boyfriend - I guess he would probably be a good choice.

The man inside of me screamed no! Faintly. But I knew I needed to say yes.

"I would like that too," I replied. He drew me into his arms, we hugged briefly and I agreed to meet up with him next week and to take the ad down.

I had my boyfriend. That made me feel so weird. No, much more than weird.

Soon I was passing by Denise's apartment building and then back inside where she returned me back to Shaun from Shauna.

Just after she finished, I got a text from Naughty.

"Great job tonight. You are progressing well," typed Naughty. "You have now chosen a boyfriend that you can service and be satisfied sexually by," he/she added.

I could still taste his seed in my mouth. I knew I would be tasting it on a regular basis as I satisfied his carnal desires. But I would be satisfied by him sexually?

"Remember to have the kids looked after for the weekend as you two will be attending my party this Saturday," typed Naughty.

That redirected my thoughts. Party. More sex. Anal and oral. A chill ran down my spine.

"Yes all is set, " I replied.

The party. I had been trying to forget about that. Maybe I would get to meet Naughty? That thought perked me up.

My heart leaped into my throat. I had to find out.

"Will you be there?" I asked hesitantly.

There was a long pause.

"Yes," typed Naughty.

Denise's face brightened as we looked at each other.

"But I won't reveal myself as Naughty to you. Not yet," Naughty added.

Maybe not. He/she should be at his/her own party. Maybe I will at least figure out who you are I thought to myself.

Denise and I had no time to discuss this as I had to get home. We kissed and I left. As I was crossing the street to my car I noticed that a man in a parked car seemed to be watching me. I dismissed it as paranoia. Would I look at someone crossing the street after dark? Probably.

My thoughts returned to the event filled day and the upcoming party.

Would I meet Naughty at the party?

Would I know it?