From Her Ex-Boss to her Bitch Pt. 03

"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.