tagTransgender & CrossdressersFrom Her Ex-Boss to her Bitch Pt. 03

From Her Ex-Boss to her Bitch Pt. 03


This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on.


Pete had been taken in by Rachel, encouraged along the way, with a little titillation and confessions of her bisexuality. For a married man he had admitted too much and allowed himself to be taken further along the submissive road than he should have allowed. As Rachel had brought him into her web, he was now trapped.

"Seriously Pete, I would never have picked you for a gay sissy, I fancied you. I thought we might have something, I was hoping something might happen tonight, but thought you fancied Rachel. Fuck I wanted to suck you and have you fuck me in the ass."

Now she was really messing with his mind, tempting him again, he was so horny he thought what she said might be true, Claire had flirted with him, but what he didn't know was that this was all part of Rachel's plan.

"Claire I fancy you and Rachel, but I never even thought you could fancy me, Rachel tricked me into it Claire, I don't know how the hell this happened."

"Hold on Pete, so you're saying little old Rachel forced you into all of these clothes against your will. What did she do, give you a roofie and carry your body up here on her own and then strip you and dress you. It bloody doesn't look like that. Shit what on earth would your wife say if she could see you now?"

She was holding a iphone pointed at him and he heard the unmistakable click of photo's being taken. Now there were two people who could blackmail him, shittttttttt. How had this gone so wrong.

"So tell me the whole fucking truth or I'm going to send this photo and some video straight to your wife from a blocked number, see how you explain this away."

"Ok, Ok Claire, please, please don't send it, I'll tell you the truth, fuck this is awful."

"Awful it maybe, but I assure you it will get a whole lot worse if you don't tell me the whole truth now. She'll be horrified, unless she's into all this kinky shit too?"

"No she's not at all, she doesn't have a clue, I promise, I'll tell you the truth, can you just undo the straps first."

"Hell no, just tell me the truth, what happened after I left."

"Ok, well Rachel wanted to talk more intimately and she told me about her sex life."


"She told me she was bi and that she liked cock and pussies and that in her view most people were like that."

"Fucking hell, what did you say?"

"I said that her admission turned me on, but that I thought it was different for girls, I said it was more ok for them to be Bi. But not for guys to be Bi as people would think they were gay. She then told me she knew lots of straight guys who loved cock in their mouths and assholes. Then she told me it was my turn to confess something, so I admitted to her, that I was a complete bottom."

"What the fuck is a bottom, this is all new to me." As Claire said this her pussy was getting wetter and wetter, she'd need some release soon, but that shouldn't be a problem.

"It means I like strong women to dominate be and be in total charge, sexually."

"In charge? in that they dress you as a woman and lock you up. Like you are restrained now?"

"Well more make me worship their bodies and other things."

"So not dressing as a woman and bondage? Really?"

"Well yes I like that too."

"I'm guessing there is more to it than that, tell me everything, or the message goes."

"Alright, just don't send it. Rachel likes to turn big sub guys like me into sissies and dress them up to humiliate them completely, she also likes to use strap-ons on them. She thinks big guys like me with small cocks make perfect Sissies to train."

"Now finally we're getting somewhere, so she likes to fuck sissy boys, and you're one of her Sissy bois. And she said you've got a small cock, I can't really tell with the clothes you have on, your package is gone?"

"That's what Mistress Rachel does she, makes small cocks disappear in her Sissies."

"Fuck so you call her Mistress Rachel, wow, now I'm beginning to believe you, have you seen the size of some of strap-ons over there, fuck they are massive. Do you know what you've got yourself into."

Claire walked over and picked a huge black dildo up, 3 inches in diameter. "Fuck Pete could you even get this in your mouth let alone your asshole, it's fucking huge, I couldn't even hope to get this in my tight pussy."

He looked across, just being able to see with the constraints of the collar. Jesus they all looked massive.

"Fuck no Claire, that's for show, no one could take something that big." He knew he couldn't quite take that but didn't want Claire to have any idea of what he actually could take.

"Well Pete I think I need a little more than that, tell me just what you like, in detail this is fascinating. In fact I confess it's a complete turn on. You have me very moist."

She pulled a chair up and sat down to the side of him crossing her legs. He didn't notice the stockings or the high heels.

Each time he thought he'd said too much, she's tempt him in with a little comment, "I fancied you", "You have me very moist." Just so he focussed on the fact he still wanted very much to fuck Claire. If he'd not been pissed and high on poppers, he'd probably have realized something was totally amiss, but in his hazy condition all he wanted to do was not have his wife see the pictures or video, he thought the best thing to do was to tell Claire enough to placate her. Where the fuck was Rachel.

"Ok, Ok I get turned on being forcibly dressed as a sissy and being humiliated and love to have strap-ons used on me."

"In your mouth or your asshole?" again he should have realized that suddenly this was getting way more sexual, but his mind was too hazy for that.

"Both Claire, in both, God I love to be fucked in both holes." Now the thoughts and poppers had him descending into sub space, he was just where Claire wanted him to be. Miss Rachel would be pleased.

"What else do you like."

Now he was getting more and more horny and couldn't help himself as a sub descending into sub space, now it was all about satisfaction, his brain was no longer calibrating the answers, it was simply giving them.

"I like to be queened and smothered and totally restrained in bondage."

"Well the bondage is pretty self-evident, but what the hell is queening when it's at home."

"It's when a Mistress sits on your face and forces the sub to lick and worship her pussy. Stopping the sub from breathing for a while."

"Fucking hell there's a special name for that, I just thought it was muff diving, does that include ass licking."

"Yes it does, although that's called rimming."

"And you like doing that too? You really like licking a girls asshole?"

"Yes I love being made to lick a Dommes's asshole."

"What about guys, do you like licking their assholes."

"Fuck, no I'm straight Claire, this sissy thing is mainly just Rachel's idea." The concept of being gay, brought his indignance back for a second, his last defence.

"I have to say Pete you don't look very straight at the moment, you look pretty fucking gay to me. Don't say the sissy thing is Rachel's idea, you've already admitted it turns you on, haven't you.

"Yes Claire I have sorry. But I'm not gay, I love pussy Claire." He really was pissed now and just blurting out the first things that came into his head. He was getting in deeper and deeper and it was all on cam.

"Ahhh so you love pussy, but not cock, are you sure, you did say that you liked strap-ons in your mouth surely that's a substitute for a real cock."

"No honestly it's the humiliation of pretending it's a cock, it's never about wanting the real thing."

"I think Freud would strongly disagree with that, I think you want real cock, don't you."

"Fuck Claire, will you just set me free."

"No, I want to know the truth Pete, if I'm not sending this to your wife I need to know the full truth. Just a few more questions, I expect the truth on these. If I even suspect that you're lying I'll press send, you understand."

"Yes Claire."

"So have you ever been with a man, sexually.?"

Pete had to tell her the truth. "Yes I have."

"Did you suck his cock?"

Fuck why did she have to ask that. "Yes."

"Fuck you really are a dirty fucking little slut, aren't you."

"Did you like being forced to suck his cock, Did he cum in your mouth."

Two nods.

"Ohhhh my Goddd. Did he piss in your mouth."

Pete vaguely realized he hadn't even told Rachel this, but nodded his head all the same. Shit that had been one hell of a session with TV Mistress Denise in Sydney.

"So then you really are bisexual pete?" her mouth was now next to his ear whispering into it seductively.

He shook his head. "But you suck men's cocks, you let them fuck you in your ass-pussy, you drink their piss and you eat their cum, don't you think that makes you bisexual at the very least or maybe just fucking gay."

This time her argument made sense and he simply nodded his head.

"That's what I thought slut. A dirty bisexual, depraved, submissive, cross dressing sissy, in need of lots and lots of hard training, wouldn't you agree bitch." She was stroking the back of his head as she said this.

He nodded, broken. He'd admitted it all, what the fuck would happen now.

Claire stood and dropped her coat to the floor.

Ohhhh fuck, what the fuck was this, she looked amazing, jeez what would Rachel think if she came in now

She walked closer to him and stood with her pussy just an inch from his nose. Then she reached under her pussy and unzipped her pvc panties from the back to the front, showing off her glistening pussy, right in front of her in all its moist glory, framed by the open zip.

He breathed one of the most unmistakable and horny smells to a man, even to a sissy.

"Now bitch if you don't want me to press send on the video I just took of you, then get licking and fucking make me happy."

Fuck he was in deep now, maybe giving her an orgasm might get him free.

He tried to lean forward but couldn't move, so she moved forward onto his tongue. It was an uncomfortable position for both of them, but Claire was still enjoying his efforts. Her shaved young pussy was like ambrosia to pete he feasted on it, licking and sucking for all he was worth.

"Well hello, what have we here." Rachel had been watching every second and was very pleased that Claire managed to get some more information from sissy, that would come in useful for the blackmail and make the film all the better to sell. Rachel had found that truly breaking someone over the course of a few films, taking them further and further by way of blackmail always helped the films to sell more.

Just as importantly, getting a guy who outwardly looked so strong and so straight and taking them from their usual cocky confident selves and reducing them to a cock sucking sissies in reality and filming it all. Alpha men loved that shit and would pay dearly for these outwardly straight ones, who she actually turned on film. She had one guy, quite small and athletically built with a huge cock, who loved to take out big guys, who looked like they could finish him in a fight, have a business lunch with them and then begin to make them serve him in public. Before he took them to a dungeon to break them all over again. She was sure pete would make a suitable sissy for this guy, although he'd need some serious training anally and orally to be able to satisfy this guy.

"Well I found your sissy and thought I'd use her talents."

" I guess that makes sense, sissy keep licking until Claire cums."

This was getting weirder and weirder for Pete, but he kept on licking as ordered and didn't even notice that Claire had called him a sissy.

She managed to grind onto his face, smearing it completely in her juices and using his tongue to her delight, as she came, she shuddered, holding onto his ears and pulling his face deep into her pussy. She squirted down his throat and he lapped everything up that he could including the stream of piss she couldn't hold in.

Claire rested there for a minute and then Rachel walked around to her side, they both knelt down in front of Pete's face.

Mistress Rachel looked into his drunken eyes and their two faces were only inches away from his. Rachel then reached forward and licked Claires juices from his face.

"Now do you see Sissy, Claire's one of my Subs, she's been in on this whole thing from the start you silly, sissy slut."

The realization finally dawned he'd been completely fooled by Claire and so worried about being exposed by her that he'd admitted way more than he should have.

Rachel turned to Claire and they kissed passionately right in front of his nose. A deep hungry animalistic kiss full of yearning. Fuck they were so hot these two. For one stupid moment he thought shit, I get to serve both of them how good is this, then the fact this was actually a set up hit him. Fuck what did they really have planned.

"There are a few problems though slut."

"Problems Mistress Rachel?"

"Well you lied to Claire didn't you."

"No Mistress Rachel, I didn't lie."

"Well you did say that I tricked you into this, is that what actually happened?."

"No Mistress Rachel it's not true, I'm sorry. I asked for this, I wanted this and more."

"That's better slut, now tell Claire and I, exactly what experience you've really had with men and how you felt at the time, we want to know every little detail this time slut. I think you've left incidences out of the story, haven't you slut?"

"Sorry Mistress, I have, yes." Amber took a moment to think, but it was too hard, now she just had to own up to everything. It might even be a relief to get this all off her chest.

My first time was with a TV slave brought into a session by the Mistress and she face fucked me for a long time, but had a condom on."

"Ok, but had you asked the Mistress to bring the slave in or did she just do it herself."

Now he knew he was more and more fucked. "I requested it Mistress."

"I thought as much and the next time."

"I was sent by a Mistress K, who I used to cyber with, to a gay sauna in London."

"Ohh my that is a big deal, how did you feel about that, when she told you to go."

"Massively nervous, I'd never been to one, didn't know how things worked and how in heavens name I was going to get fucked by a guy, which is what she ordered me to do. I confess I was mainly worried that no one would fancy me and I'd go back to my hotel with my modesty intact and that she'd be disappointed in me."

"Ohhhh fuck this has me horny again, what happened." Claire was plainly enjoying his discomfort as much as Mistress Rachel.

"It was under the arches in Waterloo, I'd googled it and checked out what I needed to do, she'd told me to wear my locker key on my right ankle as that showed to everyone that I was a bottom. I was beyond nervous, had my bottle of poppers to keep me high and took a few big sniffs and wrapped the towel around me and headed to the sauna."

"I was looking for guys with their keys on the left of their body but most were on the right. I went into the actual sauna and sat down and closed my eyes. There were a couple of guys next to me who were obviously getting on well but I felt like the odd one out and was just about to leave when a small dark haired guy came in. He looked Italian and was maybe 5 8" and athletically built. Aside from being small he was younger than me and handsome. I thought I had no chance and was just deciding to leave, when he looked straight into my eyes."

"Go on slut, what happened next?."

"He nodded his head slightly and I was scared stiff and sort of nodded back. I had no idea what to do next. Then he looked at me again and got up to walk out, I followed him, thinking I must be getting the signals wrong."

"He turned and said follow me, and held out his hand, which I took in mine. He led the way to the room he'd obviously booked and unlocked it. We still hadn't said what either of us was after. Once in the room it became clear. Although I was much bigger than him and could have easily overpowered him, he wanted to physically dominate me and that's why he liked big submissive guys, to add to the thrill."

"He locked the door, pulled my towel off me and pushed me face down onto the black pleather bed. It had obviously just been cleaned and smelled of cleaning fluid."

"I just said condom."

"And he said yes and I could hear him putting one on. Then he said give me your hands and I put them behind my back, he wrapped a piece of cord around them, effectively imprisoning my arms."

"And how did you feel as this was all going on Sissy." Rachel was trying to find out just how experienced she really was.

"Well I was afraid, but so fucking excited, and really pleased that a good looking guy wanted to fuck me. I was also very excited as I knew it would please Mistress K a massive amount."

"There you have it Claire, he wants to be a gay sissy slut and to please his Mistress, this is perfect, carry on slut, make Claire drip some more."

"So he put his fingers in my ass and then started to push his cock head in a little."

"I screamed out and he slapped my ass hard and passed me my towel, saying bite on this bitch, you will take my cock after turning me on, you whore."

"Ohhh how did that make you feel." This time it was Claire digging.

"Well I was doing it for my Mistress K, but still worried about what I was getting myself into. But very turned on too."

"But it was too late for those sorts of worries, just after I'd sniffed on my bottle of poppers, he pushed my head to the side and then put all his weight on that hand pinning my head to the bed as he rammed into me. His other hand holding the cord tied around my hands, I was helpless."

"He wasn't big, just 6 inches or so and so I took it quite easily and the pain turned to pleasure quite quickly. Then he held me down and fucked me until he came."

"Still with the condom?"

"Yes he took it off and threw it away. He warned me about some of the people in there saying that they'd take advantage of someone as naïve as me. I then thought that's just what he'd done. He ordered me to give him my number in case he wanted a return match. So I gave it to him, thinking what a dick I was, as I did that."

"Did you see him again?"

"Yes Mistress K said I had to drop everything if he wanted me again, she ordered me to serve him however he wanted if he rang. I was having dinner with two colleagues two nights later when he rang and ordered me back to my hotel room. He ordered me to leave an envelope with a key card at reception for him and to be naked on the bed with pillows under my stomach face down for when he came in."

"And you did what he said? Did you suck his cock this time?"

"I did what he said, I was ready for him and he came in stripped and plunged his fingers into my ass hole then tried to get me to suck his cock, I just couldn't go through with that, when he tried I just forced him off. That was the last I saw of him. When I told Mistress K, she said we were over."

"So you have trouble with the commitment needed to properly and regularly suck cock Sissy, would that be fair to say." As Mistress said this he knew she only wanted and would accept one answer and that would lead further down the spiral of depravity she had planned for her slut."

"Yes Mistress I would say I have commitment issues when it comes to sucking cocks."

"Well what do you think Claire, do you think we can help Sissy overcome her commitment issues and become a true whore cock sucker?"

"Fuck yes, but I wonder if she's holding other experiences back."

His heart sank, how the fuck could she know that.

"Well Slut is Claire right?"

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