My VideoChat Error Ch 16

"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.