tagTransgender & CrossdressersFrom Her Ex-Boss to her Bitch Pt. 07

From Her Ex-Boss to her Bitch Pt. 07


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, one an ex-employee. He'd only meant to have a bit of fun, but it had gone so much further. Rachel had lured him into her trap, she realised he had submissive tendencies and then bit by bit had him admit to more and more, tempting him on with the promise of sexual delights. His rock hard cock made him admit to way more than he should have.

That was how he found himself dressed fully as a latex Sissy slut, shaved of all his hair below his waist and strapped to a bondage bench where Claire had found him and the shit had really hit the fan.

Now here he was a few hours later having had the most intense training and hypnosis session with many triggers planted in his Sissy sub-conscious. He was now a she and ready to take a walk on the wild side and her first tottering steps as the Sissy whore she was being turned into.

As they left the apartment, Amber was just focussing on walking in a safe yet sexy way, now that she was programmed to try and find as many Alpha male mates as possible, she knew the hip sway was important for a sissy slut. The massive butt plug reaming her pussy did made walking normally particularly difficult though.

As they walked out into the night, the cold night air hit them, it was now 3am and very few people were about. "Now Amber have some more hits of your Pig Sweat and that will help focus your mind to get the fix or fixes you need."

Amber took 4 long hits on the two bottles and was once again as high as a kite and horny as hell.

Claire took her arm and they walked off down the street. Or in Ambers cases sashayed, trying her utmost to walk like a whore and make sure she was on show.

"Now Amber, there won't be many guys around at the moment, so I suggest that we walk down through the gay district and past the sauna, there always seem to be guys around there, at this time of night, how does that sound?"

"Perfect thanks Miss Claire, I really need some cum soon, my heartburn is bad and the itch is getting worse despite the plug." Amber sounded genuinely worried.

"Don't worry Amber, we'll get you some cum and maybe even some cock, let's go and get you and your itch sorted.

They swayed off down the road hand in hand, from the back simply a pair of slutty girls on the town, looking to get fucked.

The street lighting got worse as they walked from the nicer part of town into the seedier bit where the gay Sauna was. They passed adult stores, a strip joint and some bars until they reached the sauna, a sign on the outside simply read Subway, with no illumination, just a blank door so as to not advertise what sinful depraved delights lay behind the door.

As they crossed the street, Amber was getting more and more nervous.

"What if they don't like Sissies Miss Claire, they are gay after all."

"Don't worry your silly sissy brain about that Amber, these men love having their cocks blown above all else. I'm sure you'll get a fix to settle your stomach slut."

"Yes Miss, I hope so."

"Ok I'll wait here, you go over to the door and ask the next guy who comes out if he'd like a blowjob."

"Really, on my own Miss, are you sure Miss Claire?"

"Yes slut you're the one who needs the fix of cum after all, not me."

"Yes Miss Claire."

Amber tottered over to the door, extremely nervous, but the itch in her stomach and pussy were becoming all-consuming, she had to satisfy them.

She stood, looking the part of a drag queen hooker, albeit a classy one, on a street corner touting for business, which in a way she was.

The first guy to come out of the sauna, was a heavy set business man, still sweating from his obvious exertions in the sauna, whatever they might have been.

"Please Sir might I be of use to you?"

Amber just didn't really know what to say, she wasn't used to soliciting, although Claire knew full well she'd better get used to it and undoubtedly would become highly proficient at it as the whore she was being transformed into, by Mistress Rachel.

The guy looked lecherously at Amber, obviously admiring the slut he saw in front of him, he carefully looked her up and down and lasciviously licked his lips.

"Ohhhh yes I think you can be of amusement to me, what were you thinking of slut?"

Amber was suddenly worried that this guy might not know he was a sissy, fuck then if could get nasty, what would happen then?

Then she realised that her voice surely would have given her away.

"I was thinking that you might want a blow job Sir?"

"Ohh were you, you filthy little slut and how much would that be?"

"It's free Sir, I just need to be fed come cum please."

As Claire looked on surreptitiously, recording the conversation for Rachel, she knew they had Amber totally now, how could she just have offered a free blowjob to a completely random gay stranger. She would become the complete sissy whore they'd hoped she would be. Of all the filming they had done this was the most damning. There was no way Pete could explain what Amber had just done on cam, without any form of apparent duress.

"Ohh well that's perfect slut, I have a number of loads of cum for you, I'll happily feed you, but they aren't in my cock. How does that sound?"

In Ambers addled state she wasn't sure what he meant and just stood there dumbfounded.

Claire stepped over the road and said "That will be perfect thanks Sir, I'm with this Sissy and looking after her, she'll be more than happy to service you and to feed on your loads. Do you think around the back in the alley would be best?"

Ohh so you're with this sissy too, do you come as a pair?" now he was getting seedier and more lecherous by the second.

"No I'm afraid not, I don't, you couldn't possibly afford me, but Amber here, is free of charge tonight, do you want to fill her mouth or not?" Claire sounded stern to say the least and almost pissed off with him.

"Sorry no offense meant Miss, yes that would be lovely to get rid of all this cum, it'll make my clean up at home much less messy."

With that he began to waddle around the back of the sauna and along to take up a position behind the overflowing rubbish skip.

Amber and Claire followed him, Amber still unsure of what she was supposed to do, Claire relishing the utter degradation of Amber she was about to witness and film for her Mistress.

The guy simply took off one shoe, undid his belt and trousers, dropped one leg of his trousers and stepped out of that leg, then he lowered the tight PVC panties he was wearing and stepped one leg out slipping his shoe back on his now, looking quite ridiculous with one leg in his panties and trousers and the other naked save for his sock and shoe.

"Now on your knees Sissy, it's feeding time." He was plainly turned on by this thought, with his stubby little circumcised cock rock hard now.

Amber looked to Claire for reassurance and Claire simply smiled at Amber and nodded, still recording the entire process.

Amber gingerly got to her knees, which was much harder than she'd anticipated with her huge heels on. She still wasn't sure what was going to happen next. If only she'd been aware enough to realise the stage she had reached, where her major concerns as she knelt on the floor were, would she ruin her stockings and would she scuff the front of her shoes, not the level of depravity that she'd sunk to. But she was too far gone on poppers and the deep yearning for cum too even consider that situation.

Then the guy brought her back to reality as he said "Open wide you dirty fucking bitch" and turned away from her and began to back up and squat directly onto her upturned face.

The smell of sweat, showers, piss and cum assaulted Ambers nostrils. Normally she'd have been recoiling from such a cocktail of aromas, but by now she was desperate for cum, her training and hypnosis triggers had her literally on heat, like the animal she was becoming.

She opened her mouth wide and stuck out her tongue as the man pulled the sweaty globes of his ass cheeks wide apart and lowered his ass hole directly onto Amber's tongue as he squatted down.

As her world became a dark sweaty, cum and piss soaked reality she began to slurp at his ass, working her face deeper into the gap in her buttocks, she licked every drop that came out, she wormed her tongue right into his raw swollen ass hole. She couldn't see his hole, but could feel the swelling of his ass lips, as she caressed his ravaged cunt with her tongue. She tasted the multiple loads of cum that had been deposited in his boi pussy, whilst he had been in the sling room in the sauna. He plainly enjoyed the rimming, groaning and loving it, moving his ass in time to her thrusts with her tongue.

As could be clearly seen from the filming Amber hadn't been forced, she had simply dropped to her knees looking eager, she wasn't tied up, or restrained in anyway, her tongue was delving deep into his raw swollen hole searching out her food. She was in pig heaven and that was clear for any viewer to see. She could never ever claim that she'd been forced into this, it showed her as the true whorish slut she had become over just a few hours. Claire longed to watch this with Emma, Amber's wife. Just the thought of the total shock that Emma would feel when she witnessed her husbands alter ego, would be enough to make Claire cum on the spot, fuck that was going to be fun.

Claire was truly impressed by how Amber had responded to Mistress Rachel's training, she was the perfect candidate. Claire addressed the guy, "Please force as much cum out as you can for the slut, I've instructed her not to swallow until your empty Sir."

"Ummm how lovely is this and her tongue worming its way in my mancunt, fucking fabulous, you have a good one here. She seems desperate for it."

"I know, she'll make good money for us, I'd love to know, how many loads do you have in your man cunt tonight?"

"Ummm 4, ohh no make that 5 with the spitroast I had. Will that be enough for your little sissy sluts hunger."

"No she'll need more but this will be the perfect start, any black cum or all white?"

"Two black guys, one with a very curved cock which he deposited his cum deep inside me, ohhhh that felt so good as he held my thighs tight against him and filled me with his manjuice, I'm guessing that will be the last load out into your sluts waiting piggie mouth."

As he said this he was squirming on Ambers tongue and squeezing his asshole, bearing down to squirt globules of the 5 loads of cum into Ambers eager mouth. True to her promise, Amber didn't swallow just kept filling her mouth up more with each globule.

As he moaned on her face, his cock remained rock hard, only small but rock hard. He was loving her ministrations.

Finally he stood up off her and began to get dressed, Amber simply knelt there, her head tilted back and mouth wide open full of cum and lube.

"Smile for Mistress Rachel", Claire instructed as she continued to video, being careful not to get the guys face in the video only Ambers.

"Now you may swallow and salve that itch of yours slut. At least there is some black cum in there slut."

Amber did as instructed and swallowed savouring the taste and the slimy texture and the receding heartburn she felt. The itch deep in her pussy still affected her though. The sheer dirtiness of the act washed over her, instead of revulsion, she felt pride at being the best Sissy slut she could be, a true cum guzzling whore for Mistress Rachel.

The guy bent down to Ambers eye level and kissed her hard, his tongue delving into her Sissy cock throat like a snake, probing and tasting the juices, sweat and multiple loads of cum which still coated her mouth.

"What a fucking lovely cum whore you have here, please can I give you my card, I'd be interested in using her in the future if she is for hire." He looked expectantly into Claire's Eyes.

She simply smiled, nodded, taking his card and looking at the name and said "Of course you can Gerald, we'll be building up a set of VIP regulars with the dirtiest of proclivities that Amber will be able to satisfy, we'd love to have you as one of those."

"Thanks for that, I shall look forward to being much, much dirtier with her in future. Ohhhh just the thought has my cock twitching again in anticipation."

"I can have her suck you if you'd like Gerald, still free tonight as a one off."

"Ohh would you, that's a lovely offer, I'd like that I don't like to cum whilst I'm being fucked I save that for when I'm at home, I may need some anal stimulation at the same time though just to get off."

"This just gets better and better Gerald, Amber would love to finger your man cunt as she sucks you I'm sure, wouldn't you Amber, just to get your next load of cum."

Amber looked up her make up smeared with sweat and cum, her lips glistening with her Sissy lip gloss.

"Yes Miss Claire that would be lovely thank you." Again all on cam, clearly a very happy whore, just doing her job, not the slightest suggestion of duress. Aside from her dilated pupils which gave away her popper status to those who knew.

Gerald moved forward to present his hard stubby cock to Amber, she simply open her mouth and as instructed as she took the cock fully down her throat in one swift movement, she reached her right hand between his legs and then up between the sweating cum streaked butt cheeks wriggling her fingers as he adjusted his stance to have his feet wide apart to grant her access to his sloppy hole.

As he thrust quickly and harshly into her mouth, both hands clamped on the back of her head making Amber gag, despite the small size of his cock, Claire could plainly see he was loving the sound of the gagging he was inducing, as most men seemed to.

Amber carried on as she was programmed to, wriggling he fingers in and upwards searching for his prostate, made easier by how ravaged his hole was. She found the enlarged prostate and massaged it for all she was worth, not because she wanted this over, but just because she didn't just want her fix now, she needed it.

She worshipped him as though he were a beautiful stud and milked every last drop of cum from his balls as he held himself at the back of her throat, injecting his jizz straight into her throat. He called out Jesus as he came which made Claire smile at the little scene in front of her which she was eagerly filming. She was quite sure that Mistress Rachel would consider this to be a perfect advert for Ambers wares for a certain type of sleazy client.

Ambers fingers were still working in and out of her clients man pussy as he finished cumming, draining the last few drops for her, before Gerald withdrew from the sluts swollen lips.

"Fuckkkkk this girl is good, I will be back to use her again, thank you so much for choosing me, ummmmmm."

Claire simply said "That's Ambers absolute pleasure Gerald, can she do anything else for you tonight?"

"Well I could do with a piss, does she drink?"

"Hell yes Gerald, Amber loves to be a urinal for men, don't you Amber."

Amber simply opened her mouth wide open and nodded, then tilted her head back to show the cum in her mouth.

"If you can top up her mouth and then I'll have her swallow your cum and piss and you can fill it again and again until your bladder is empty, how does that sound?'

"Bloody wonderful thanks Miss."

Gerald held his softening cock and the dribble began as he filled her mouth to the brim with warm salty piss."

"Now swallow Amber."

Amber simply closed her mouth and swallowed theatrically.

"The prefect hole I'd say." Gerald then filled her mouth once again and repeated this process 5 times until his bladder was empty.

"What a perfect end to a perfect night, thank you." Gerald looked like the cat that got the cream.

"Well maybe next time you're at the Sauna, you could buy Amber's use for the night and take her with you as you slave, how would that be?"

"Really that would be very sexy, could I have her dressed just as she is today?"

"Of course, in fact on the website, you'll be able to choose her clothes and the various restraints and locks, any equipment you might like her to wear or bring. You could have her plugged or empty, if you choose to have her plugged you can choose the actual plug, gagged or not, choose the hair colour and the chastity cage as you wish. You choose your perfect sissy slut for the night. And what's more you get all the keys to the locks."

"So kind of like a real time video game?"

"Exactly, you can customise her as you see fit. In fact you can even have her sent with a full to bursting bladder if you like. Choose if she's had an enema, been milked, all sorts of kinky options." Rachel had mentioned to Claire that this was her longer term idea, but Claire decided to run with it and Gerald certainly seemed to love the idea.

"That sounds simply wonderful, I'll definitely want to use her again, that's for sure."

"Great to hear Gerald, I'll send through an email tomorrow and I should have said though Amber isn't based here, but whenever she's in town we'll post the dates and let you know so you can get booked in first if you like."

'That sounds lovely, I'll eagerly look forward to having her in my clutches again and using her with some other friends."

"Well there is the chance that she might have an hour or two available tomorrow afternoon or evening?"

"Then just let me know once you have it confirmed please."

"The website won't be up and running, but I can give you all the options to choose from if that works for you?"

"Sounds delightful, my dear, have a lovely rest of the night."

"Ohh we will, we will, still not time for bed for this slut yet."

"Aren't you a lucky slut." He smiled at Ambers smeared up turned face."

"Yes Sir I am a lucky slut, very lucky." Amber was listening to the website comments of Claire, with excitement, she really was taking to this debauchery.

"Up you get Amber, here take my arm."

Claire helped her up and took her arm once more. "Oooooh we'll be needing new stockings, won't you slut, we'll have to get you knee pads for all the kneeling you'll be doing."

"Yes Miss Claire."

"Now let's go and get some cock at your hotel if we can for you. But before we set off here's some more Pig Sweat for you." She held the open bottle to Ambers left nostril, closing her right nostril with her other hand and Amber too in a long desperate breath as Claire counted to 10. "Now hold that in until I say." She closed Ambers left nostril holding the bottle to her right and told her to let the breath out and then breath in again for the count of ten.

The impact of the poppers as Amber let out the long breath after the count, was intense, she was wobbly on her feet and felt great, but the itch deep in her pussy simply got stronger, nagging at her.

"Please Miss Claire I really, really need to get fucked hard and soon please."

"Then let's go bitch and get you some cock."

They walked on to the hotel, although more accurately Amber tottered on her towering heels to the hotel. Although they looked out for any suitable beau's for Amber, the streets were deserted. Amber was getting desperate at the thought of trying to sleep with the itch still increasing in intensity, which she genuinely believed it would.

"Looks like you might be in luck Amber." Claire was nodding her head in the direction of the reception desk as Amber pressed her key card to the door release to get into the warmth of the reception area. A young stocky black guy manned the desk, looking up from his computer to see the two beauties walking in. "Now don't waste your chance slut, you need this, sell yourself to him."

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