From Her Ex-Boss to her Bitch

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.”
“And???”
“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?”
“There was another session with a Mistress in London and a TV Mistress too.?
“What was her name.”
“Mistress Caprice, from Australia.”
“Ok tell us everything that happened during that session.”
Claire had been searching on her phone and showed pete a picture of Mistress Caprice on the Serious Mistresses website. “Is this her?”
“Yes Miss Claire it is. I’d had a session with her a year or two ago and she’d threatened to bring in a Master Stephen as I was just about to cum from the massive strap-on fucking she gave me. I was horrified and tried to get out of my bonds as I had the biggest most intense orgasm I’d ever had. She laughed and said she was only joking, but the thought stayed with me and I secretly wished that she had forced me and brought him in to force me.”
“Now you are finally telling the truth, we’ll be able to help you so much more knowing the whole truth. So you fantasised about that actually happening for years before you went back to see her.”
“Yes I did Mistress Rachel, then next time I rang her I said I’d like a session with Master Stephen too.”
“How did she respond?”
“She remembered the first session and seemed excited, I got the feeling that she liked taking subs to the next level of humiliation. I arrived and she looked amazing, he wasn’t there and I was worried that he wouldn’t be in the session. But she ordered me to strip and said, “Now I remember you better, you took some pretty big toys last time, so you’ll manage to take Master I think.”
“You must have been pretty turned on slut?”
“I was the horniest I’d ever been, as I stripped my cock was as hard and big as it had ever been.”
“So still small then?” Rachel took every opportunity to humiliate her new Sissy.
“Yes Mistress Rachel it was still small. Then she had me kneel and fed me two very big hits of poppers and then sat on a fucking bench as she asked me the last few questions.”
“Tell us what she asked you, exactly as you remember it Sissy.”
“She asked if I wanted condoms or bareback.”
“And your response?”
“I hesitated and then whispered bareback please Mistress Caprice.”
Claire let out a slight noise of pleasure.
“She looked at me and said, I thought as much slut, you want to truly taste his manly cock as it goes down your throat don’t you slut?”
“I answered yes, looking at the floor.”
“And did you manage to go through with it that time.”
“Yes Mistress Rachel I did, he fucked my face as I was restrained, she pissed into my mouth as he fucked my pussy and then he finished off in my mouth.”
“Did he cum in your mouth Sissy?” this was important to Rachel, she needed this.
“Yes Mistress he did.”
“Then what?”
“Mistress Caprice was by my ear and said one word, “Swallow.””
“And did you do as you were instructed slut.”
“Yes I did Mistress Claire I swallowed every last drop.”
“Now we have our breakthrough Claire, it seems Sissy really is a faggot and just didn’t completely know it or admit it to herself, the evidence seems pretty self-evident to me. I think she maybe still has a hurdle to get over or a blockage to get past to become a true cocksucking whore, but I think we can break down the hurdle or train the blockage out of her, with some aggressive treatments, don’t you?”
Cocksucking whore, shit this was going so much further than Sissy initially wanted, where the fuck was this going to end?
“Fuck yes Mistress Claire, I think with the tailored programme you designed, we’ll break her sissy mind and have her craving cocks and cum before morning.”
Fucking hell, this was going to go on all night, were they mad.
“Did you stay hydrated Claire, I think Sissy will need a good drink.”
“I did Miss Rachel yes, my bladder is fit to burst, I’m afraid I let out a little when I came just then.”
“Ok get the funnel and fit it. Now Sissy we are going to do quite a lot of training tonight and as you’re in town again tomorrow night we’ll carry on then. First I need to know if you can and indeed will drink a lot of piss for me, OK.”
He felt he had no choice, he felt defeated. “Yes Mistress I can and I will.”
Claire was fitting the funnel and told him to open wide as she fitted the tube into his mouth, pushing it to the back of his mouth. She clamped it in place and then stepped onto a couple of boxes to get enough height to piss directly into the funnel. She sighed as she released her pent up piss and filled the funnel to near the brim, well over a litre of fresh warm piss.
As they looked at sissy drinking and the bubbles of air coming up through the piss, the two girls knew they’d broken another barrier. It was one thing to have a woman piss on your body or on your cock as a man, but a totally different thing altogether to be turned into a urinal. It broke so many subs minds, when faced with over a litre of piss, they just whimpered and broke into pieces. The moment sissy had admitted to having a Mistress pissing directly into her mouth, Rachel had decided she was likely to be a suitable candidate for a urinal. These were not that common amongst male subs.
If she took this particular embarrassment well, and wasn’t completely broken by it, one of Rachel’s more depraved clients would no doubt find a use for Sissy. Sissy urinals had become all the rage in some of the more weird and wildly kinky clubs.
Pete had no choice, he concentrated on trying to get Claire’s piss down his throat, not an easy thing to achieve with the tube down his throat. This was not his idea of fun at all, but there was absolutely nothing he could do about this.
“Ok Claire, time for some serious training now, as Sissy continues to drink I want her milked, caged and ready for some anal training. Ohh and by the way I’ve just thought of the perfect name for our Sissy as the truth of just how deep she is in this dawns on her, as she drinks pints of your warm piss, how about Amber. How beautifully ironic is that.”
“I love it Miss Rachel, Amber the Sissy piss slut, how fucking perfect.”
Rachel pulled a chair up to be next to Amber’s head whilst she carried on drinking and Claire began to prepare things behind Amber.
“Now Amber, you know your new name, I trust you like it.”
Amber gave a small nod.
“Whenever you’re are with Claire or I, even in public you will respond to Amber and on the phone with me. This is who you are to me now, unless it’s in front of your wife or family, you are Amber the Sissy piss slut.”
“You’re drinking this so well, I’m pleased with your progress in such a short time, I can see this will go on the website as one of your talents. Because that’s what this is all about, you see. Every moment since you walked across my threshold has been videoed, every dirty utterance from your slut mouth is now recorded to either be sold to my clients or shown to your family and friends. I suggest the former is less scary for you that the latter, wouldn’t you agree.”
Again a simple nod. Then a moan from Ambers spread lips into the funnel as she felt the zip at her crotch being zipped open and felt Claire pull her popper shrivelled cock out and retract her foreskin hard. Then she felt Claires beautiful lips on the head of her small cock. The feeling was incredible. Claire inserted a lubed finger into her pussy and that elicited another deep moan.
“Ahhhh I see Claire is now sucking your little sissy clit, to milk you of your sissy cum and is also opening your pussy with her finger, in a second she’ll have a dildo up there, and she’ll use that in conjunction with her mouth to milk your prostate and get every drop of juice out of you. You’ll enjoy this stage but possibly not what comes after this.”
She smiled into his eyes as she said this, Amber kept on drinking, wondering would it ever end. All she’d wanted was a flirt and some fun at the start of the evening, then as they chatted she’d hoped to taste Rachel’s pussy and maybe to feel her strap-on in her pussy, but now it seemed that might be the tamest thing that would happen.
Her cock had grown to its biggest state for the night and the feeling was amazing, Claire’s ministrations were simply amazing as she deep-throated Amber.
“Hey Miss Rachel, look at this, even erect Ambers clit is still so, so small.
Rachel took hold of Ambers cock and wanked it hard a few times, then told Claire to get back to work.
“Now it’s important that you listen to this Amber, your cock doesn’t even fill my hand, I only need a couple of fingers and my thumb to wank you off. It could never satisfy as woman, your wife must be horny as hell if that is all she has to amuse her. Unless of course she has a big cocked boyfriend, but enough of that, we can make sure her needs are taken care of in time.”
“For now we have to train you to satisfy men, tonight I will turn it into a clit and nothing more. You’ll be grateful in the end, we will free your inner slut. You’ll like that.”
Amber moaned with a throat full of piss trying to indicate that she didn’t want that.
“I know Amber, you want me to do that for you, to make you a true Sissy and to free you to worship your betters, don’t worry soon you’ll have no cock and feel very different I promise. Tonight will be a real transformation for you, mentally as well as physically.”
Then Amber felt a good 8 inch long thick dildo pushing at her pussy entrance, gently opening her pussy hole little by little until her pussy gave way quickly with the effect of the poppers relaxing her hole. As Claire rammed it in one single motion all the way in Amber moaned with a mix of pleasure and pain. Over the years she’d used a lot of dildo’s on herself and now she couldn’t hide that from Mistress Rachel. It was there for all to see, just the ease with which she’d taken a good sized dildo.
“There you go slut, how easily did you take that, you dirty little fucking whore, I think you’ve been understating your anal experiences haven’t you slut. You bitch, now I’m really going to fuck you hard. Don’t ever fucking lie to me again whore.”
“Then again I am pleased with you, that ability, once I’ve stretched you further really will open you to the big clients. The ones who really like a Sissy with a huge pussy and the capability to take a lot of punishment and very big cocks. You’re already exceeding even my dirty expectations.”
Ohh fuck, men and clients, what on earth had she got herself into. Amber was worried now, but also very, very horny.
Rachel stood and walked around the back of Amber.
“Claire hand me the bigger dildo, I need Amber to feel some pain as she comes and to help her associate pain with pleasure. For her they are now one and the same. You focus on milking her clit and then getting it converted fully as we discussed and I’ll work on this bigger dildo to stretch and give her the pain she needs so much, is she close to spurting.”
“Quite close I think Miss, but not there yet.”
“Ok well here goes, this one is another ½ in diameter and that means another 1 ½ inches in circumference so another 1 ½ inches of gape, let’s see if she can take it.” As she was talking she lubed up the next black dildo.
With that Mistress pulled the first dildo out in one swift motion, leaving Ambers pussy gaping. She replaced it at Ambers pussy entrance with the bigger lubed up dildo.
She put the base of the dildo against her mons pubis to feel the pressure as she would if she were wearing a strap on and began to press forward.
Amber was screaming into the piss funnel now, she’d nearly drained the funnel, but the sensitive feelings of her cock head as Claire intermittently nibbled on it and the complete stretching of her pussy as Mistress Rachel relentlessly but slowly pressed forward were completely intense. She was incapable of taking this bigger cock, it was being stopped by her pussy walls.
The as she came in Claires mouth her pussy relaxed and opened slightly wider and welcomed Mistress Rachel’s cock in.
“Ummmmmm fucking hell that’s more like it slut, fuck your pussy has some room in it.” Mistress Rachel said this as she then pushed inch after inch of the 10 inch dildo in, each one coinciding with another long sucking stroke on Ambers rapidly deflating cock by Claire.
Claires mouth was then removed from Ambers cock and she stood in front of Amber and as Amber prepared to suck down the last drops of piss, Claire released her mouth full of Ambers Sissy juice right next to the drain in the funnel so that with the last mouthful of piss Amber also consumed all her sissy juice.
“Good girl Amber, it’s not the same as proper protein from a real man, but still a little bit of protein for you. Now swallow it all down piss slut.”
Now that she’d drunk all the liquid, Rachel was still stroking the big cock in and out of her, corkscrewing it around and moving it from side to side, opening her new Sissy slut as wide as she could. Amber was moaning as pain took over from pleasure, the boundaries being blurred by Rachel.
“Are you ready to turn her baby cock into her clit Claire.”
Claire was already back in place kneeling by Ambers cock with a miniscule chastity cage in her hand. Claire pulled her heavy balls through the tight ring one by one, then pushed the flaccid clit through the hole too before pulling the foreskin tightly back and inserting the urethral plug and the 1 inch long cage which would only allow Ambers clit to be a maximum of 1 inch long when it was fully engorged. This level of confinement was extreme, but Rachel had chosen it to make the absolute most of the humiliation of this big guy. To destroy his manhood completely.
“Fuck Claire, I just realized there needs to be a little extra pain for Amber for lying to us, lube the plug up with this.” Rachel handed Claire a jar of Tiger Balm.
“Ohhhhh that is perfect Miss Rachel.” Claire was almost giggling at the prospect.
Amber couldn’t see and so didn’t know what was happening, did Mistress mean a lubed up butt plug? Then she smelled the unmistakable aroma of tiger balm and guessed what she might be in for. Fuck, fuck, fuck. She moaned into the funnel gag again as the heavily coated urethral plug was slid into place and then she heard a click as the outside lock clicked into place.
Then as the inside of her urethra warmed the Tiger Balm up, the intense burning sensation began inside her clit. It was absolute agony. But if she’d realized at least she couldn’t feel pain from the dildo any more.
Claire stood up. “It’s done Mistress, Sissy Amber has the smallest sissy clitty you’ll have ever seen, the mini cage is perfect for her, you were right as ever. And boy will her clit be on fire now. I’ve taken some pictures from below for her various profiles. I can’t wait to show this to her wife one day.”
Amber couldn’t believe what she was hearing, she was doing what they wanted and they were still talking about her wife finding out.
“Funny as soon as I felt her package through her jeans I was sure it was all balls and no cock, how right I was. The bigger cocked clients will simply love the contrast and enjoy torturing those big balls, although I confess I like to see them tucked inside her body and hidden.”
Mistress Rachel squatted down to have a look at the new clit.
“Ohhhhhhh my, how cute is that. Just those big bouncing soft squeezable balls and then an inch long clitoral head. Perfect. Now time to work on her pussy training. We’ll need her to be capable of taking very big insertions. Get everything ready for her please Claire. Oh and Claire pass me that Tiger Balm will you.”
Mistress Rachel then spread a liberal amount of Tiger balm under the rim of Ambers clit, so that if the foreskin could retract in time from its currently engorged state, it would simply trap a good layer of Tiger Balm under it, to continue the torture. She hated being lied to. Now Amber knew that.
“Now slut, you’ve no doubt watched many Sissy Hypno videos on the Anna Malice site, am I right slut?”
Amber tried to say yes Mistress but all that came out through the funnel was ummm.
“Thought as much you dirty little bitch. Well I’m not going to get you to watch one, you’re going to be in one, which once Claire has edited it and added music will go up on the web today for discerning viewers. With my voice whispering your commends in your ear.”
“So both Claire and I will be suggesting things to you and breaking down your barriers as the other of us continues to stretch and open you pussy. The pain in your clit will take a lot of your focus and brain power, but I need you to think of cocks, big cocks, if you can focus on that it will make the pain go away a little. Do you understand Amber.”
Two groans into the funnel were all she could do to say yes Mistress.
“Now to get rid of that blockage in your mind. I’ve always said show me a curious cock sucker and give them enough poppers and then you have a cock whore.”
“So Claire get the mask to go over her nose and soak it completely. It’ll get you and I a little high too, but that will just make for more energetic fucking of Amber.”
“Yes Miss here it is, I take it you want the extra strength ones Miss?”
“Yes definitely Pig Sweat for what I want from this session please Claire, lets got the whole hog as Amber requested.”
Claire smiled and poured some Pig Sweat onto two cotton balls soaking them both and then dropped it into the breathing bag on the rebreather. When they placed this over Ambers mouth and nostrils all that would circulate in her breathing was pure poppers. This would completely soak her sissy brain in poppers in a way she’d never experienced, which was why Rachel had saved it for the session where Rachel intended to erase the blockage in Amber’s sub conscious.
She fitted the mask over Ambers nose and Amber took in one long breath and felt her whole body almost melt into the bench. Her face flushed, her clit shrank more and her pussy became even more hungry. The mask was left on and she simply recycled her popper breaths for nearly a minute. The only time Amber had felt anything like this was when she had been given poppers through a gas mask. She closed her eyes and saw the usual black background in front of her eyes, with the tell-tale hole which always appeared in front of her eyes, she always felt this was her asshole when she was this high, seeing the hole grow and the raw red edge to it always made her think of her pussy and want it to be stretched further and further.
“There we go now we take it off, can’t have you having too much, it’ll go back on in a minute when you oxygen levels are back up.
Continued on the next page (link Below)