tagTranssexuals & CrossdressersFrom Her Ex-Boss to her Bitch Pt. 06

From Her Ex-Boss to her Bitch Pt. 06


Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it.


It had all started when on a night out on business Pete had flirted with two younger women he knew, one of them Rachel was ex-employee, the other Claire a friend of hers. He'd only meant to have a bit of fun, but it had gone so much further.

Pete had been taken in by Rachel, lured into her trap, encouraged along the way, with a little titillation, a lot of flirting and once she realised he might have sub tendencies, she'd taken it further, much further.

Tempting him on with the promise of sexual delights, she confessed her bisexuality to him and then her naturally dominant role and her interest and enjoyment of BDSM. He simply fell for her trap and admitted more about himself and his own proclivities, bit by bit. Admitting way more than a married man ever should. First he admitted to his submissive nature and then fell for each extra little trap she set, having him plug himself in the bar toilets, kissing him fully and caressing his cock. Then she started to play on his submissive nature how as a small cocked guy he was bound to be submissive in her experience.

That was how a couple of hours later he found himself dressed fully as a latex Sissy slut, shaved of hair below his waist and strapped to a bondage bench in her training room. He heard Rachel leave the apartment to pick up some other things she needed.

That was where Claire from earlier that evening found him and then the shit had really started.

Then Rachel had made him admit to what he really wanted live on camera. "Please Mistress make me your whore slut, use me as a bitch and train me to take more than I've ever taken, I beg you, fill my pussy and mouth with your strap-ons, make me lick you and worship you."

"Ummm not bad for a first time, you'll get better and ask for more and more depraved things as time goes on."

Now after a few hours of aggressive fucking and sucking on big cocks who Rachel had brought in to help with Ambers training, here the newly created Sissy slut, Amber was being fisted by her new Mistress.

As Mistress Rachel continued to fist fuck Amber, she kept on working on her Sissy's suggestable mind.

"Look at your clit in its tiny little cage, the metal suits it, it looks cute. It could simply never satisfy a woman, could it Amber?"

"No Mistress my clit couldn't satisfy a woman properly." She managed to moan out for her Mistress.

"Well not even properly Amber, it couldn't satisfy a woman at all. Your wife must be horny as hell, if that is all she has to amuse her. Does she cum when you fuck her."

Amber turned her head away in shame "No Mistress Rachel, she doesn't ever cum, when I fuck her."

"Don't be silly Amber, that was a rhetorical question, you don't need to tell me, I know its true Sissy, it's obvious. Unless of course she has a big cocked boyfriend, then she would cum, wouldn't she. How about it ,would she like a Big Black cocked Bull to fuck her properly, to really stretch her unsatisfied pussy and make her scream with ecstasy?"

"She's not into any of this Mistress, she doesn't know about me at all. Please she can't know any of this."

"She doesn't know that you're a cock sucking, cum guzzling dirty little Sissy bitch, who loves being a cum and piss soaked whore for men, is that what you're saying."

"Yes Mistress, I am saying that, she doesn't have a clue about any of this. Please, please, please don't tell her about Amber."

"Answer my question right now slut, wouldn't she love having a Big Black Bull cock to fuck her senseless."

"Nooooo Mistress I don't think she'd be into that, she's totally vanilla, please don't tell her any of this, I beg you. She doesn't care about sex at all Mistress."

"I don't believe that for a minute Slut, she's just stopped bothering with you as your so pathetic and you don't have a cock, you have a little clitty. But remember that's my decision, to tell her any of this, isn't it slut, not yours, you do know that, don't you?"

"Yes Mistress Rachel, I do understand, but it would end my marriage. Please, please, please don't tell her any of this." Amber was crying softly now, still being fisted slowly by her Mistress and moaning with each stroke.

"Ohh I don't think so, from what Claire has told me of your wife, I think she might love to have some Big Black cock on call for her to use, or she might love watching her Sissy husband sucking and worshipping Big Black juicy cocks, that might just make her very wet, we'll have to see in time. She might even be submissive to me, you never know Amber do you?"

As she asked the last question she increased the speed and force of the fisting working hard on Ambers Prostate, she wanted her to be as horny as possible as she continued to suggest ideas to Ambers very suggestible mind.

"Claire give her some big hits of Pig Sweat right now please. Soak her little Sissy Slut brain."

"Yes Miss Rachel."

Claire held the two bottles tight against Ambers nostrils "Breathe in bitch, soak that Sissy mind of yours, set free your inner Sissy piggie."

Amber did exactly as she was instructed taking in huge hits of her favourite poppers, in the state she was in facing these questions, she needed as much help as she could get. Loading her mind with their wonderful sensual effects. She needed as much as possible with the images of her wife on her knees sucking a succession of huge Black Cocks in here mind's eye.

Just as Rachel had wanted. Another way to destroy the last vestiges of the man, that pete had been.

"Now Claire is going to unstrap you and get you dressed decently for the walk to your hotel. You're going out completely enfemme for the first time. Be thankful it's the middle of the night, you shouldn't bump into too many people. And any you do should be the kind you'd want to see at this time of night."

"Claire will take you home and prepare you for bed and stay the rest of the night with you so that she can help you get ready for your day of work, tomorrow morning, how does that sound slut."

"That sounds wonderful, thankyou Mistress Rachel. But I've never been out dressed up before, and I look like a freakish whore in this outfit Mistress?"

"Well of course you do Amber, that's just what you are now, a silly little Sissy whore. Don't worry about it slut, you're dressed perfectly as a Sissy whore slut, just as you should be, be proud of who and what you've become." Rachel's tone left Amber in no doubt that she shouldn't disagree.

"Yes Mistress." Amber said that but didn't sound like she meant it, despite being as high as a kite.

"Don't worry Amber you'll have a long coat, but you will need to be walking as well as you possibly can in those lovely heels. That should be fun to watch."

"Thank you Mistress a coat would be lovely. God thankyooouuuuuu she moaned."

Rachel rotated her fist so that her fingers were pointing upwards and could work just on Ambers prostate. She uncurled her fingers and massaged it for a few minutes with her middle finger, rotating around the walnut of the prostate. Then as Ambers moans grew lounder and lounder Mistress Rachel began to use two fingers to rub from the bottom of the prostate to the top effectively milking Amber. Amber reached her second Sissygasm of the night, this time even more powerful as she imagined her wife being fucked by a big black cock as she watched on. Rachel revelled in how perfectly suggestive Amber was now.

Again Claire collected her sissy cum, sucking on the caged clit and taking it all into her lovely mouth before kissing Amber fully and depositing the load into her mouth.

"There a little more protein for slut. My only worry for your night's sleep and work tomorrow is how the itch that Curtis and Max implanted in your pussy and throat will grow overnight and then even more in your business meetings tomorrow. The itch in your pussy will become unbearable in the day, it'll feel like a burning, a yearning that can only be softened but the salve of cum, Black cock cum. The itch will grow and be constant, grow and be constant, you will need and long for cock and cum."

"Whenever you get a cock inside you the itch will start to go, bit by bit, with each hard stroke. But you have to make each cock cum deep inside your pussy or the itch will get even worse, once your pussy is being fucked they absolutely have to cum inside you or the itch will be unbearable. What do you need?"

"I need Black men's cum Mistress Rachel, I need bareback, I need to get fucked and have cum deep in my pussy. I need to be fucked by Big Black cock Mistress."

She smiled into Ambers hazy drugged eyes as she said this, Amber looked back at her Mistress nodding and breathing in huge hits of her Pig Sweat. Amber was looking deep into her Mistresses eyes and breathing in long, long intakes through her nostrils, loading her mind up and making it more and more suggestible with every breath. The taste of cum in her mouth, on her swollen lips and deep in her throat.

Rachel had explained to Claire that the heady mixture of very heavy duty poppers, the taste of cum in her throat, the smell of cum in her nostrils, anal fisting and prostate massage and then the inevitable Sissygasm all combined with hypnotic suggestion from her Mistress, would have a very intense, long lasting effect on Amber. Amber wouldn't be able to get away from the suggestions Rachel was planting deep in her sub conscious. They would become part of Ambers psyche.

She also felt they were very likely to be a permanent effects, where there would simply no going back for Amber, not going back to her old boring life as Pete, now Amber would always be there under the surface desperate to be her true whorish self. She would have to reconcile herself to becoming this dirtiest version of herself.

Previously when Pete had been in a poorly cleaned mens urinal, the smell of stale piss would have turned his stomach, he'd once been for a session with a TV Mistress and it was the smell of stale piss that made him turn tail and run away.

Now though whenever Amber smelled the faintest hint of piss, as she stood at a urinal and breathed in, or when she smelled cum or tasted it, when anything at all was in her ass pussy, or she just looked at an Alpha males package in his trousers, there would be effects for her. Simple aromas, tastes, just the appearances could become a stressor which would bring the dirty slut Amber out to play, even if serious vanilla Pete was in a business meeting or meeting with the bank, he'd have to fight the urges in his sub-conscious.

A wild thought hit Mistress Rachel as she realised it was even possible that having a good shit with a firm stool would probably turn her Sissy on in future. Just the fact that she felt her pussy lips being opened even by a solid bowel movement might be enough to turn her on and make her itch.

That thought excited Rachel, she'd never even contemplated taking a slut this far, to even be turned on uncontrollably as she went about her daily business just sitting on a toilet. Now that was an idea she had to implant, too much fun not to.

With absolutely no control at all, Amber each time she sat to take a shit, would feel intensely turned on, the mundane would become arousing. Now that she had thought about it, Rachel wanted to deeply embed that thought in Ambers malleable Sissy mind, to add it to the list of ideas and responses she was going to implant into Ambers sub-conscious under hypnosis.. Fuck she was enjoying this so much.

Rachel had explained to Claire even just the tell-tale bulge through trousers, especially of a Black guy or Black cock would awaken the itch, making Amber squirm. Rachel had studied hypnosis and although far from an expert she'd seen how suggestible Sissies like Amber were in the right super stimulated circumstances.

This situation had all the right circumstances to suggest ideas to Amber which would have genuine involuntary physiological reactions in the future. Rachel was planting hypnotic triggers deep into Ambers sub conscious. Amber wouldn't remember them being implanted, but would have visceral reactions to the triggers Rachel suggested.

"Only cum, and even better Black cum will make your pussy stop itching for a while, then you'll need another fix. Cum will be your salvation." "Say it!!"

"Cum will be my salvation."

"Your throat and stomach will feel like you have awful heartburn, intense heartburn, debilitating heartburn, cum will be your Gaviscon, your medicine, slurp that down your throat and you'll get some relief for a while."

"Yes Mistress Rachel, cum will be my medicine."

"The only other thing that will help will be piss, but it will only help for a little while and you'll need a lot of it, but if you cannot get cum at least piss will help reduce the itch."

"Yes Mistress Rachel piss will help, but I'll need lots of it."

"Now you know you need poppers, you need your Pig Sweat, but it has one big down side, it makes the itch much worse, even though you know that, the desire and need for your sissy juice will overcome the downside. Whenever you get a chance you'll still want your Pig Sweat, in between meetings, through the day you'll need a fix as often as you can. Do you understand me Amber."

"Yes Mistress Rachel, I fully understand that I'll need Pig Sweat through the day and night." Amber was panting at the sensory overload, she was spent, but being given no respite. This was the time in Rachel's experience that sluts were at their most suggestable. Utterly spent, exhausted but still undergoing massive stimulation, their barriers fell at these times.

As Amber responded, Rachel began to remove her wrist and then stopped as Ambers pussy opened up to its fullest extent once more as Rachel neared her knuckles. She realised this was her chance.

"Amber now close your eyes and concentrate on you pussy closing onto my hand, then opening wider as you bear down. Can you do that for me Amber."

"Yes Mistress I feel it closing on your wrist and now I'm bearing down and it's opening again ohhhhhhhhhhhhh."

"Don't think about my wrist Amber, think about you pussy opening, embrace the feeling, as it opens wider, just like when you sit as a Sissy always must, on the toilet and you bear down to have a shit, remember the feeling."

Rachel was going slowly in and out with her wrist, matching the strokes to Ambers breaths of Pig Sweat.

As she pulled her fist to the widest point at the knuckles, Ambers pussy stretched and then Rachel took them out a little further letting Ambers pussy gape widely, looking as though it was gasping for air. Amber moaned as Rachel took her fingers from her pussy, now she felt bereft, empty and lost. Then back in went Rachel's fist.

"Now again focus on your pussy opening up, just like it does when you have a big shit, I can you feel you bearing down to get the big shit opening your pussy Amber, do that for me Amber."

Amber groaned "ohhhhhhhhhhhhhhh yes Mistress the shit is opening me wide, ummmmmmmm."

"Every time you bear down like that to have a shit the itch will grow ten times worse, do you understand."

"Yes Mistress, ten times worse, ten times worse, every time I have a shit."

"Then you'll need poppers, take them every time you go to the toilet, As soon as you drop your trousers and take you lovely sissy panties down, open a bottle of Pig Sweat and take 5 huge sniffs to help you go to the toilet, it will open your pussy nice and wide."

"You'll need your Sissy juice throughout the day and night, whenever you can, even though they will make the itch more intense."

"You need your Pig Sweat don't you Amber."

"I need my Pig Sweat Mistress." Each time, Rachel reiterated the hypnotic trigger.

Curtis was standing in all his naked, hard cocked glory next to Rachel, she turned to his cock and held her arm next to it.

"See Amber this is what a real cock looks like, a real man's cock, not like your shaved little clitty. Look at it Sissy, it's nearly as big as my lower arm, this cock can satisfy your wife, yours never can. But you need this cock, you want this cock, don't you, look at it, can you feel the itch inside."

Before Rachel had even mentioned the itch, Amber had already felt it, with the poppers and seeing Curtis's magnificent cock again, she longed for cum, her pussy was now itching deep inside and her stomach feeling unsettled, she knew what she needed.

"Please let me suck him Mistress, I need his cum, feed me please Mistress, let him fuck me hard and fill me with his cum."

"Not yet Amber, I think we'll let you sort that out later, how does your itch feel slut."

"It's deep inside my pussy Mistress Rachel, I need a cock in it noowwwwwwwwww pleeeeeassssssssse."

Rachel smiled "I know my little Sissy Darling, it will always be deep inside you forever, you know that is mine and Curtis's present to you. You came in here with a complete blockage about sucking cock, well we've replaced that with a deep seated need for cock and cum. Aren't you a lucky girl."

"Yes Mistress, I'm a very lucky girl. But please, I need cock now, pleaaassee."

"Sometimes it's good to need and then to fully understand just how important cock is going to be for you forever in the future. By the time Claire has you back in the hotel room, it'll really be a deep craving for you, but I'm sure Claire will help with that, won't you Claire."

"Off course I will Amber, I'm there to help your transition."

"Please can we go now, please Mistress." Amber was getting desperate already.

"Hold on slut, I have more to say. What I'm really pleased with is that once I've stretched you a bit further tomorrow night, it really will open you to the big clients. The ones who love 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."

"I knew right from the start you'd be good, but didn't dream you'd be this good, well done you."

Amber had a faint memory that Mistress Rachel had said something similar before, and that last time she had been scared out of her wits by what Mistress Rachel had said. The difference was now when she heard it she was proud. Proud to be a huge cock taking Sissy faggot whore for her Mistress.

"Now we can plug you for the walk home, would you like that Amber."

"God yes please Mistress, please fill me again. Stretch me to help the itch to go."

"Now Amber the stretching will help a little but what you really need is cock and cum, that's what you crave isn't it."

"God Yes Mistress Rachel I need a cock in my pussy and my mouth please."

"As I said not yet, you'll have to try and find some on your way home, won't you slut."

"Yes Mistress I will try my hardest."

"I'm sure you will slut, quite confident of that now. Well that is if you want any relief from that awful itching." Rachel smiled as she said that. "Claire find a good sized plug and fill this bitch up for the walk home, I want her as bow legged as possible on the walk to her hotel."

"Yes Mistress will do."

Claire went over to the bench to look for the right plug, she wanted to make sure she pleased Mistress. She picked up the Acorn plug by Square peg, a bronze coloured 6 inch long plug but with a big ridge to stimulate the sphincter just above the snap back.

"Mistress do you think the large or the extra-large, if I remember the ridge is 3.5 inches in diameter on the X Large."

"Fuck then the extra-large it is, I want to get her over 4 inches tomorrow, so best to maintain the level we already have, I think."

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