tagTransgender & CrossdressersFrom Her Ex-Boss to her Bitch Pt. 05

From Her Ex-Boss to her Bitch Pt. 05


This story includes extreme themes of sissification, interracial domination, watersports, cock sucking, if any of these themes are not your thing, please don't read it.


"I think you should have tattoo on your back above your pussy cheeks and another above your little Sissy clit."

"But I couldn't do that Master, my wife would see." Amber was almost begging, although the idea excited her, she'd seen the online pages dedicated to white sub male whores who wanted to be branded and used, but her real life would never cope with that.

Curtis smiled knowing he would have started Rachel thinking...

And indeed he had, Rachel was now contemplating just how she could bring Pete/Ambers wife into their kinky fold. She'd need Claire to befriend her and suss out the next subject for Rachel's training.

Maybe she'd turn out to be a sub too and Rachel could rent them out as a couple, or maybe she might awaken a dominant spirit in Emma his wife, or just make her submissive to black cock but dominant to her sissy husband.

How perfect would that be, Rachel could have them tattooed with matching jack and Queen of Spades tattoos, to mark them both for use by each and every Black man who saw the tattoos.

But most all she now knew that she would definitely get Amber tattooed in some place, at some time. The jack of spades with a lower case white j dominated by a big Black spade, signifying a completely submissive white sissy or boi for the exclusive use of any black superior Masters who chose to fuck her sissy holes at any time they chose, once they had seen the tattoos.

What Rachel loved most of all was that if the tattoo was on show then any black man at all, was at liberty to use the white slut, right there and then. It showed the Sissy slut had absolutely no choice whatsoever.

But that would come later, a lot more training to go before that stage for this slut. Rachel was dripping wet at the thought.

Max bent down in front of Amber,

"Put your left leg over my shoulder so that your lower leg is over my back and the underneath of your knee is on my shoulder, then hold onto my neck and lift the other one over my other shoulder."

This proved easier said than done, but she managed it with his help, her clit dangling dripping in its cage on Max's chest.

He then carried her over to where Curtis was sitting, his cock rock hard once more and Max lowered Amber towards his cock until Curtis took some of the weight on his hands and guided the head of his cock to Ambers gaping and dripping hole. The head was swallowed up easily by her cum soaked pussy.

The two guys then waited, hoping that the dawning realisation of what was about to happen would sink into Ambers pig sweat soaked sissy brain.

Just as she started to look wide eyed and began to vocalise a question to Max, he lifted her half and inch and then almost threw her off him, so that Curtis could pull Amber down with the help of gravity in one long earth-shattering descent onto his full 10 inch rod.

The scream that came out of her mouth was almost silent, so high pitched was it. She couldn't catch her breath, she was in absolute pain and that combined with the most intense feeling of fulfilment she'd ever had. As Rachel had said, pain with pleasure, was Ambers lot now. Never any pleasure without some increasing level of pain for their slut.

Curtis held her to him, reaching for her long nipples and working on those to pinch and twist, Amber writhing on his lap just as he wanted, forcing his cock to squirm inside her raped, raw stretched pussy.

He then began to lift her off him, his hands on her ass cheeks, raising her a few inches in the air before letting her drop to be completely impaled on his magnificent black rod once more.

"I think the way you are taking this cock, shows that you do need some tattoo's bitch. You'ree the perfect white sissy jack to black Masters, this is what you were born for, white slut girl, isn't it?"

"Yes Master it is, I was born to be a Blackkkkkkkkkk Masterrrrrrrrrrssssssss fuckkkkkkkkksluttttttttttt."

"Exactly slut, which is why I'm quite sure Mistress Rachel will have you booked in to see a tattooist real soon, so you can be marked forever as a truly inferior white cock whore for every superior Black Motherfucker that wants to ream your slutty holes."

"You need a fucking big tramp stamp bitch. So everyone knows what a whore you are, whenever you are naked. If I had my way you'd have a big one on your wrist for all to see all the time.

He repeated his fucking by lifting her and then dropping her over and over again, until the inevitable happened, Amber's first Sissygasm turned out to be the most intense orgasm of her life, her clit totally caged and impaled on the urethral plug, meant there were no big spurts.

Her Sissy juice dribbled from her clit and coated her cage. Her entire body was wracked with the shudders of her first anal Sissygasm. She writhed on Curtis's cock taking him further along the journey.

She was spent and impaled but euphoric. It had happened she had made it to the promised Sissy land.

Rachel in the other room zoomed the camera in to catch the moment for posterity and more importantly for Ambers future advert pages on various kinky hook up sites. Focussing on her moans and whimpers, her look of total satiation, absolute elation mixed with intense pain.

For Rachel the very first anal orgasm a Sissy had, just from pure anal stimulation was a truly defining moment in that Sissies journey. Many in her experience never achieved this Sissy Nirvana, Amber had got there so, so quickly, she was a perfect Sissy student.

It signified that in future a Sissy would never ever have a cock orgasm again. Now Ambers only pleasure was linked forever, to hard anal fucking and pleasing men and multiple cocks, pleasing their betters and their Mistresses.

Amber was being split in half by the massive cock inside her, but the pain just seemed right to her, to go with the almighty Sissygasm she had just had. As Curtis continued to thrust, his cock rubbing against Ambers prostate with each and every stroke, he milked her, getting every last drop of sissy juice from her sissy nuts.

With the last thrust he shot his load deep inside her pussy. "Now you truly are a white Sissy whore for superior Black cock, you've just been bred you bitch. Now the itch I have just planted inside you will be insatiable, you'll need black cum in your stomach and your Sissy bitch pussy. You'll need the taste of it, without it you'll suffer withdrawal symptoms, the itch won't go away now, or ever bitch, the only satisfaction will come from another load of Black spunk."

Amber was at her most suggestive and simply nodded. She'd watched countless self-hypnosis videos and Curtis's comments simply blended with the messages she'd taken on over the years whilst she was impaled on dildos and dressed for action.

Curtis and Max had done their jobs, but both wanted to wreck this whore much more than they already had. Fuck, this white slut sissy deserved to know well and truly who her superiors were and Curtis was determined to show her that in some lessons she'd never ever forget.

Rachel came back into the room and stood in front of Amber who saw her Mistress and smiled, hoping she had pleased her. Claire stood by her side, piss and juices still glistening on her face.

"So Amber you said to me, that you would never consider yourself a Sissy, just a man who liked to bottom, is that still the cases Sissy?"

"No Mistress Rachel, I apologise for ever saying such a silly stupid thing, now I'm a complete Sissy whore for you and black cocks."

"That's my good girl, well done, you should be proud of your progress, now the training can really begin. Curtis, Max, Claire and myself are going to go hard at you for two hours until you are completely and utterly broken and filled with cum and piss, your pussy red raw and stretched wider than it is now." She said this smiling into Ambers eyes.

Then Claire will escort you back to your hotel for a few hours sleep. Then you can get your work done as quickly as possible and we'll do it all again tomorrow night, to really make you a whore, how does that sound to you slut."

"That sounds wonderful thankyou Mistress." Amber felt pretty broken already and couldn't imagine another two hours of this intensity, but nor did she question her Mistresses instructions. She now knew and accepted that this was her true destiny and fate. There were no more questions in her addled horny mind.

It then dawned on her that her clit was still trying to get hard, despite having had her Sissygasm, it was straining it's little purple head against the cage bars, pulling on the urethral plug. She was momentarily amazed at the horniness that was washing over her, normally she would be spent and ready for sleep, but most importantly normally she would be consumed with guilt after she came, desperate to get free and out of her Sissy costume.

But now she wanted more black cock and more black cum. The hunger growing deep within her every minute, the itch gnawing at her soul. She could feel the itch inside her pussy growing by the minute, she needed more cock and cum.

As she realised this, she also noticed that Curtis's huge manhood was also stirring again and growing back to full size. She marvelled at his recovery time and shockingly realised that she actually really wanted more cock, needed more Black cock.

She wasn't kept waiting for long. As Rachel sat by her head to whisper into her ears, Max took up position with his lube, ass juice and cum covered cock in front of Ambers mouth.

Rachel said "Claire gather up as much of Ambers sissy juices and coat Max's cock head with it please, try not to waste any."

Claire knelt down and scooped up the cream, liberally coating Max's cockhead with it.

"Now Amber, what do you want more than anything in the world right now?"

"Please Mistress let me feed from Max's Black cock, please have him breed my throat and fill my Sissy belly with his Black mans cum."

"Good Girl, now savour the mixed tastes of your Sissygasm, your pussy juices, lube and then seek and search out Max's cum, milk it from his python and get your reward. Then you'll just want more and more, forever."

"Yes Mistress, more Black cum for this Sissy, please have me fed."

Curtis held Ambers hands by his thighs, holding her fully impaled balls deep on his cock, whilst Max began to fuck her sissy face for all he was worth. Once he had her mouth open far enough he simply pistoned in and out until he finally got his cock head beyond the back of her throat to much gagging and retching from Amber.

She simply allowed her throat to be used as a cunt, as his cock was liberally coated in her throat mucus. Then with each thrust more came out of her mouth and nose once more coating her face in her fuckslut's mask of depravity.

As with most Bulls, the second load of bull semen took a lot more coaxing out. BY the time he finally came, Amber could barely breath even when his thick cock was not wedged firmly down her throat. Her nose was covered in the slut snot and breathing was extremely difficult.

Finally he slammed in one more time and held her head on his impaled cock balls dangling on her chin. His cock pumped 5 or six times depositing his cum deep into Amber's throat. She gagged hard on his cock but swallowed partially as she had no choice. But as he withdrew she leaned forward trying to get every last vestige of cum from his cock, sucking and licking for dear life. Now the hunger was growing.

Ok Curtis unless you need to cum again I suggest we lock Amber into the stirrups and start the real stretching and get her working as a urinal too, I don't know about you but I need a piss."

Curtis smiled and stood, with Amber still firmly impaled on his cock, "I'll just walk her over to the bench." As he did so, he lowered himself on each step holding Amber's ass cheeks and lifting her off his cock to then thrust deep once again, with each step she cried out in both pain and pleasure.

Then he lifted her off his cock and lay her on the gynae table, she was slightly sitting up but her legs held up high in stirrups. Her pussy, now gaping and red and raw, the juices and Curtis's load oozing out, only to be caught in Claires hand and smeared into Ambers mouth.

"Keep that in your mouth bitch, don't swallow yet." Then she smeared the last of the cum and pussy juices into Ambers nostrils, literally filling them with Curtis's cum.

"There that's better Amber, now you'll be able to smell your man's cum for the next few hours with every breath."

With each breath, cum bubbles came out of Ambers nostrils making it hard for her to breathe through her nose, but also saturating her senses with the intensely wonderful smell of a real Black man's essence. It seemed right to Amber to have all of her sissy senses dominated by a Black man and his cock and cum.

Claire strapped down a thick leather belt over her waist crushing Amber's clit cage, then fastened her knees and ankles to the stirrups, finally she strapped a large strap across her chest which pushed her budding sissy titties up making her erect nipples project somewhat obscenely, then cuffed her hands by her sides to the Gynae table.

Rachel then walked towards Amber having picked up a large metal object from one of the tables she held it up for Ambers viewing pleasure.

"Now this is a medical anal spreader, lots of people use a speculum or even an equine speculum, but this is the real bad boy Amber, I'm going to fit this in your pussy and then we'll take it in turns to open it a little wider, every few minutes until we have you 3and a half inches wide by then end of tonight. Tomorrow night you'll go still further."

"Oh slut I should have said it opens to 5.5 inches wide."

For the first time, Amber was truly frightened, 3.5 inches was serious, but fuck was Mistress Rachel really serious about 5.5 inches, that was insane.

Amber's pussy was still gaping and Mistress Rachel easily fitted in the two loops of metal, one of which sat inside the other until the racheting system was used to prise them apart. "The difference between this and the usual speculum slut is that the opening part, opens much wider, not the arms inside you so we can get you much more open and ready for fisting.

Rachel simply pushed the arms straight into Ambers welcoming cum lubed pussy and started to rotate the screw to ratchet the arms apart until at 2.5 inches in diameter she felt some resistance from Ambers pussy ring. She simply smiled and ratcheted the implement a little wider, eliciting a moan from Amber which was stifled as Claire standing at Amber's head fitted her with the penis gag of the piss urinal funnel and strapped the funnel to the front of Amber's head.

Amber could smell cum and taste cum, Curtis was in her every hole now. Then to finish of his domination of this jack of spades sissy, Claire handed him and empty 2 litre jug.

"Time to syphon the python and give Sissy her drink Curtis."

"Thought you'd never ask, I'm bursting." Curtis lifted the heavy black snake into the jug and let forth a long streaming of deep amber coloured piss."

Claire held the jug for him, loving watching him piss, she was getting wetter, just at the thought of giving Amber her amber nectar, she loved making sluts total pissoirs.

She reached up and drained the nearly full 2 litres into the funnel as Amber began to gulp to recycle the fluid.

Amber was focussed completely on trying to ingest gulp after gulp of piss, when the pain from her pussy increased ten-fold.

She couldn't scream with the penis gag in her mouth, but still managed a long moan. Rachel had increased the spread to close to 3 inches, an eye watering amount for Amber, Rachel looked to Claire.

"Get Max filling the jug and feed sissy some more Pig Sweat, she's going to need a lot. Ohh and put some clover clamps on, I want her to not know what to concentrate on."

Claire reached over to the table and picked up some Japanese clover clamps and fitted them hanging down vertically from Ambers tight erect nipples. The reason she hung them downwards then became crystal clear to Amber as Claire lifted the connecting chain and clipped it into a catch on the urinal funnel now the clover clamps which had been facing down were pulled horizontal and so bit into her nipples in an excruciating way.

She passed Max the jug asking him to fill it and to top Ambers funnel up.

As Rachel had summised, now Amber could barely concentrate to focus on the pain, was it her stretched open pussy, her nipples or her clit. Pain and more pain for this slut, so as Claire opened two bottles of Pig sweat and held them to Ambers cum sodden nostrils, she tried with all of her being to get as much Pig Sweat on board as possible. Each gulp of piss was followed by a long intake of breath.

Rachel was fingering around the metal prongs in her pussy and exclaimed. "Wow as she took the last lot of poppers on board you could see her pussy visibly relax another half an inch, this is fabulous we should easily get her to 3 and a half inches in the next hour. Give her more Claire, lots more. But make sure she doesn't go thirsty, my bladders pretty full again, so drain me in a minute and fill Ambers glass up again.

Rachel continued to ratchet the spreader bit by bit, turning the screw and marvelling at how efficient it was and wondering how wide she'd be able to get Claire's asshole with this, that would be fun too. But for now to concentrate on Amber.

Max finished filling the funnel and Claire took the jug and placed it under Rachel's pussy so she could relieve herself at her leisure.

Rachel still fingering the raw edges of Ambers pussy, exhaled and let her strong stream go into the jug. If Ambers nostrils had not been full of Pig Sweat and cum she'd have be able to smell the aroma of Rachel's fresh piss, as it was she was only going to taste it.

Amber was now full to bursting and couldn't ask any permission and so just had to let her bladder go and piss herself, another bit of control being purposely removed from her by her new Mistress.

"Claire pass me the big jug."

Claire passed over a 10 litre jug and Rachel placed it under the constant dribble of piss coming from Ambers clit cage to catch as much as possible.

"Ok one last turn of the screw on this and we can leave her for a bit, I feel an itch inside my pussy that needs scratching Curtis and I think Claire has one in her Ass for you Max."

Claire gulped at this, fuck Max's thick cock in my tight ass she thought.

"Claire use my piss to top up the funnel and then we'll leave Amber to her job as the urinal."

Claire took the smaller jug and filled the funnel for Amber to drink.

Amber was broken, her mind incapable of any rational thought, her pussy as wide open as it had ever been dripping with cum and lube, her nipples on fire with the lifted clamps digging in. Her clit trying to harden in its minute prison. Then the piss, the constant piss, she continued to focus on one mouthful at a time, drinking down as much as she could. Her bladder was so full that now a constant stream of piss was leaking from her clit into the jug below her.

The four of them left the room and went back into the office with the cameras all showing Amber in all her bondage piss drinking, gaping pussy glory.

"Curtis you sit on the chair over there, I want to sit on your lap with your wonderful cock deep inside my pussy, but I want to look into Claire's eyes as Max enters her tight little shithole."

Curtis did as he was told and Rachel lined up her dripping pussy with his cock head and sank down all the way sighing with pleasure as she went lower.

"Claire on all fours right in front of me, now bitch."

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