Saving Amy

By Amanda Stern

Published on Apr 4, 2018

Transgender

Please find enclosed a story for inclusion in the Transgender Control section. It is a continuation of a story that started with Saving Amy.

  • Amanda Stern

SAVING AMY PART 2: TIFFANY'S RETURN

  • Eric is haunted by the memories and after-effects of his enforced work for the SiFu Club. But as he battles his demons, and his choices narrow, he agrees once again to be transformed into Tiffany ... *

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Eric was thinking about the business card when he was summoned to see the managing partner. He thought about it again as he was clearing out his desk. And it was still on his mind as he arrived home with the small box of possessions that seemed a meagre memento of his two years at the law firm.

He went to his desk, opened the drawer and found the item that was the only tangible reminder of his enforced period of work for the Sissyfuckers Club - aside, that was, from the large deposit in his bank account. Not that he needed the card to remember what had been done to him. Or to count the losses it had caused, which included his dignity, his self-respect, his girlfriend, and now his job.

But he still couldn't help replaying that dreadful day and night, as he had done almost constantly since it had happened a couple of months ago. Seized while on a cycling holiday, he had been tricked into serving as a maid for a group of male diners. Thinking that he was taking the place of a young waitress called Amy, apparently kidnapped at the same time, he allowed himself to be dressed and made up as a sexy French maid.

He was forced to suck the dinner guests' cocks and swallow their cum, and then be anally penetrated over and over again. He had thought the crowning humiliation was to have to eat out Amy, who it turned out was not a victim at all, but the daughter of the event organiser. But no, that came on the way home when, dressed now as a hooker, he had to negotiate a lift back to his hotel.

He had hitched a ride with an overweight slob of a truck driver, who had been only too happy to accept a blowjob as payment. But if having to wrap his tired lips around the driver's disgustingly dirty cock had not been enough, worse was to come. When they reached the next truck stop, the driver insisted that he could go no further that night. Eric was forced to seek help from three grinning men, who he strongly suspected had been contacted by the first driver.

Although they were prepared to take him the rest of the way in their van, the price this time was much more than a blowjob. He had to let each of them fuck him twice, though they insisted on paying him for the second time. The amount of money they stuffed into his bra though was a derisory amount, to reflect the fact that he was, as they put it, "just a cheap sissy whore". By the time they dropped him off outside his hotel, his abused asshole was aching and so stretched that he could not stem the constant flow of leaking sperm.

Even then, his troubles were not at an end. Although he had his room key, he was challenged going through the hotel lobby by the young woman working on the reception desk. She must have thought he was an escort making a late night call. Embarrassed beyond belief, he had to identify himself and spin her a tale about being at a fancy dress party, while cum steadily dribbled down his legs and soaked his fishnet stockings.

Finally back in his room, he found a bag waiting for him with all the clothes and personal effects that had been taken from him by his captors. At this point he wanted nothing more than to wash away the makeup, the spunk and the shame that had been accumulating all evening. But he still had two problems: the blonde wig glued to his head, and the false tits just as firmly affixed to his shaved chest.

He dealt with the wig by using the cutter on his electric shaver. But while that got rid of the long blonde tresses he had been given, he also had to take a lot of his own brown locks as well, so entangled had they become. In the end, so unsightly was the result that he was forced to shave the whole lot off.

He had less luck with the boobs. For some reason, he couldn't bring himself to try and cut them off - it just felt a bit like self-mutilation, somehow. And he had nothing with which to soften the glue. In the end he left them as they were, finally had the much-needed shower and went to bed. But he struggled to sleep, so traumatised was he feeling. And when he did doze off, he kept being woken up by the unfamiliar feel of the mounds of gel.

The following day, he had to tape them down as best he could and then go out in his baggiest sweatshirt to find the solvent he needed to loosen the glue. The rest of what should have been his holiday was spent hiding in his room, trying to come to terms with what had happened to him. He struggled to eat anything, because of what seemed to be a persistent taste of semen in his mouth. And even as his anal passage returned to something like its normal shape, he couldn't shake the sense of being empty back there. He had spent less than a day with a butt plug and then a succession of cocks inside it, and yet their absence now seemed somehow abnormal.

If he hoped that a return to work and a normal routine would banish his demons, he was to be bitterly disappointed. His girlfriend was the first to go. It was not so much the complete disappearance of their sex life, a product of his inability to face any kind of physical intimacy. Rather, it was his refusal to discuss what had happened to him, which she took (perhaps correctly) as a sign of his lack of trust in her.

It was the same at work. Everyone could see that something had happened to him. The HR manager practically begged him to tell her what it was. But when he could not and would not provide an excuse for his plummeting performance and perpetual state of distraction, the firm had no choice but to let him go.

It was the business card. In the end, it all came back to that. He had received it from the man he knew only as Vance, the one who had been responsible for his abduction, and for directing his perverted performance as Tiffany the bimbo maid. In their final conversation on that horrible night, he had calmly told Eric both about the large payment he was receiving for his performance and the recording that would be released if he tried to go to the police.

But Vance had also given Eric a card that would allow him to contact the perverted organisation he ran, the Sissyfuckers Club, "if you decide you want to be Tiffany again".

If you decide you want to be Tiffany again. Those words haunted Eric. There had not been a day since that he had not replayed them in his mind, over and over. Vance was a powerful and physically imposing man who had masterfully controlled Eric and taken personal responsibility for deflowering him. Why would he have said that, unless he thought that Eric was the sort of person who might actually like to be dressed as a woman and treated as a cheap whore?

And just as importantly, why had Eric even taken the card? Or at least, not torn it up or thrown it away as soon as he had the chance? Why had he taken it home with him? Why did he keep looking at it and wondering whether to use the email address on it?

In the rational part of Eric's brain, there might have been good answers to all these questions. But that part was simply not working right now. As it was, the more that he did not dismiss even the possibility of getting back in touch with his captors, the more it seemed to him that they had correctly identified him as the sort of person who would willingly submit again to their control.

It still took a further three months after losing his job before Eric finally cracked and sent the email. He had stopped exercising, his bicycle never touched since the day he had left it chained up outside the mountain-top cafe. He rarely now ate more than one meal a day. As a result, his already lean frame had lost a lot of its definition and he was as thin as a rake. He had also stopped shaving, whether on his face or elsewhere, so that he now had a tangled beard and a light covering of fuzz on his torso and limbs.

With no income, he was rapidly consuming his savings. He simply could not bear to apply for jobs, so convinced was he that anyone seeing him would instantly recognise him for what he really was - or for what, at least, he feared he had become.

When he did finally send the email, in the ultimate act of desperation, it simply said: "If I wanted to be Tiffany again, what would I need to do?" He didn't sign the email, and he sent it from a new account that did not reveal his name. Nevertheless, when the reply came a few hours later, it was addressed to him as Eric and directed him to be at a particular cafe the following morning.

He very nearly didn't go. He spent a sleepless night replaying all kinds of alternative options that involved failing to turn up and seeking other ways to get his life back on track. Yet he kept coming round to one thought: if I don't give it another try, how will I know if Tiffany is who I'm really meant to be?

When he arrived at the cafe his cheeks were once again burning with the shame and humiliation that had become constant companions since his capture. He ordered a glass of water from a waitress who gave him a disgusted look at his parsimony and sat down at a table to wait. A few minutes after the appointed time, he was joined by a familiar figure.

"Holy shit Tiff", said Nancy, "you look awful. Are you okay?" Although she was grinning , he chose to accept her statement of concern at face value.

Of all the people he'd met that day at the remote mansion, she was perhaps the only one who hadn't treated him badly - or at least given the impression of wanting to. She'd dressed and made him up as Tiffany, playing the role of another captive with aplomb. And after the big reveal, she'd been perfectly happy to enjoy his tongue between her legs. There was nothing feigned about her orgasm, he was pretty sure. Even so, and in stark contrast to her younger sister Amy, she'd given no indication that she was enjoying his humiliation. Which, he reflected, probably made her as good a choice as any to send to this meeting.

So he contented himself with a murmured answer. "No - I wouldn't be here if I was."

The grin faded from her face and she slid a hand across the table and rested it on his. "I know", she said quietly, "and for what it's worth, I'm sorry it had to be you." She left the hand there for a moment, until the waitress reappeared with a cup of coffee for her. She took a mouthful or two, then suddenly, as if a switch had been flicked, was all business.

"Okay", she said, "you wanted to know what to do about bringing Tiffany out of retirement." Mercifully, she kept her voice low, so much so that he had to strain to hear her. "Four things, that's all. First of all, you need to sign this contract." She pulled a sheaf of paper out of her bag, together with a pen, and put them on the table in front of him.

"Second, you need to get rid of all that hair." She waved a hand vaguely at his beard, as well as his forearms. "You'll go to a clinic of ours, they'll take care of you. Third, start taking these tablets, once a day before bed." She tossed him a bottle of pills, which he fumbled and had to retrieve from the floor. "What's in them?" he asked, but she ignored him.

"And fourth, you need to be ready for an assignment some time in the next two or three weeks. It will be a probationary job. You do it properly, you start getting regular work at the SiFu Club." She noticed his puzzled reaction to the name. "That's the , ah, polite name we give it in public, right?" He nodded. "Here", she continued, "take this phone - we'll use it to get in touch, and you'll also find it has details of your appointments at the clinic."

Eric took the proffered phone, staring at it dubiously. "What kind of clinic? And what sort of assignment will it be? Will I -"

"Look", she said, cutting him off, and reaching over to flip over a few pages of the contract, "why don't you take a look at what you'll make for your probationary job. See that figure there?" She jabbed a finger first at one line, then at another. "And that's your new salary if it works out - not counting tips and bonuses of course."

She waited until he had looked at the relevant clauses, then asked conversationally: "Are those the kind of amounts that might induce you to just sign the fucking contract and not ask any more questions, do you think?"

Eric was still staring at the figures. He swallowed convulsively and gave a nod. "Okay then", she said.

As if in a trance, Eric picked up the pen and turned to the signature page at the back. Years of legal training were telling him that you should never sign a contract without reading it properly - and taking time to think about it. He made one last effort. "Do you think I should sign this?" he asked weakly.

When he looked up, she was staring out of the window. "Yeah", she said reflectively, "you really should."

It was as if the past few months had all been pushing Eric to this point, where he consigned himself to the unknown. But it had to be better than what he was living with. And at least he'd find out if this was who he really was. He signed the contract and pushed it across the table, his eyes down. By the time he looked up, Nancy had gone, leaving only the pills and the phone.

Eric was not at all sure that he'd made the right decision. And his concerns only intensified after his first visit to the beauty clinic, which despite presenting to the public as a normal business quite clearly had close connections to the SiFu Club.

He was not just given a full body waxing, but told he must return for laser treatments that would suppress further hair growth. He had thought they might shave off the unruly mop on this head as well. But instead it was given a page boy cut and dyed blonde, while his nails received their first ever manicure. He was scolded for the neglect of his health and given diet supplements to improve it, together with a makeup kit and instructions on how to apply it. He was also carefully measured, including for shoes, and given a pair of high-heeled pumps to take home.

All of this was extremely worrying. And yet at the same time, he felt better simply for having made a decision. His sleep improved and so, after a few days on the supplements, did his general health. And the mere fact of being told what to do gave him some sense of structure and purpose in his daily life. He took his medicine, assiduously practised both doing his own makeup and walking in heels, and went back to the clinic when instructed. He was also emailing regular reports on his progress, including photos, to the Club.

Even so, it came as a shock when, a few weeks into his new routine, the summons came for his probationary assignment. He was met at the clinic by Nancy, who took one look at his anxious expression and gave him some tablets to take. "They'll help you calm down", was the only explanation she would give. And, truth to tell, Eric did soon feel a little more relaxed. The worry was still there, but he felt more able to keep it at a safe distance - which was just as well, given what happened next.

He was a little surprised to be led into a treatment room, where a doctor and a nurse we're waiting. When he asked what was going on, he was told that he needed "a few injections". This turned out to be a radical understatement. There were a couple to puff up his lips, several more to do the same to his buttocks and, most bizarrely and painfully of all, the injection of large quantities of some kind of fluid into each side of his chest. As the solution was pumped into him, he both felt and saw the flesh underneath his nipples rise. The conical mounds that resulted looked far from natural, but they were unmistakably breasts.

He should, he knew, have been screaming blue murder about this. He tried to get Nancy to stop the treatment. She had followed him into the treatment room and literally held his hand through the worst of the pain. But she had simply said: "This is what the client likes - and besides, you agreed to this in your contract. Anyway, it's only temporary - they'll be gone by tomorrow, all right?" In his chemically dampened state, he could see no option other than to accept her explanation and grit his teeth through the rest of the procedure.

While he was recovering from his stint as a pin cushion, Nancy did his makeup. She praised his efforts to learn how to do it himself, from which he gathered she had seen the photos he had been submitting. But she also made it clear he wasn't yet adept enough to prepare his own face for an assignment. As at the mansion, she went for a look with bold colours that highlighted his blue eyes, though rather than pink this time for his lips (and also nails) she opted for a ruby red.

Next came the clothes. There was a matching set of satin underwear in scarlet and black. Eric tucked away his cock into the panties and was then helped on with the bra. The feeling settling his new breasts into the cups was bizarre, yet also somehow comforting. Far better to have these strange and unbalancing new protrusions safely encased in satin than jiggling freely in front of him. Sheer black stockings clung to his hairless legs, attached to the suspender belt that completed the lingerie.

Over the top of these he wore a simple but elegant black cocktail dress, with a skirt that was just long enough to cover his stocking tops and yet which would reveal them if he crossed his legs. The dress featured a checkerboard cut-out design running down each side and around the hem. Completing the outfit were a pair of black high-heeled sandals, with straps which twisted around his calves, gold earrings and a gold necklace.

Nancy led him to a floor length mirror to show him the results. "I'd say Tiffany was back, wouldn't you?" she asked with a broad smile on her face. She'd been called him "Tiff", in a teasing sort of way. But this was the first time she'd used the full name.

Tiffany looked at her reflection and nodded. She was still dreading what was to come on the assignment. The last time had been horrible, and this could well turn out to be even worse. There was a part of her that was horrified at the choice she had made to submit again to this humiliation. But she could still admire the skill with which she'd been transformed. She really did look very glamorous ...

"So what do I have to do?" she asked, unable to keep the anxiety from her voice. Nancy looked at her watch. "We've still got about twenty minutes before the limo gets here. Let's head out to the foyer to wait and I'll give you a few details."

As they reached the entrance hall to the building in which the clinic was located , Tiffany looked around anxiously. This was a public area and, even though it was now early evening, there were still a few people around. She was worried about being seen, and indeed she attracted quite a few stares. But they seemed on the whole to be admiring rather than accusing in nature, which came as a relief.

As they sat together on a bench, Nancy explained what was about to happen. To Tiffany's immense relief, she learned that she would not be entertaining a group of men this time, but having dinner with a single client, at his house.

"Just dinner?" she asked hopefully. Nancy laughed. "That's a no, honey, there will very definitely be afters ... Oh, that reminds me, time for you to take this." She dug into her handbag and came out with a little capsule, which she handed over. "Do you need a glass of water?"

Tiffany shook her head and swallowed the capsule. "What's in it?"

Nancy's grin widened. "Just something to put some lead in your pencil, so to speak. It's got a delayed release, so it shouldn't kick in until after dinner. But if I were you, I wouldn't linger too much over dessert."

Tiffany frowned. "So it's not going to be like last time, when I couldn't, um ..."

"Get it up?" supplied Nancy. "No, with that working it's magic you won't be able to hold it down, I shouldn't think."

"So why the difference?" asked Tiffany. She wasn't at all sure that this was welcome news at all. At the mansion, she had been given a drug that prevented her from getting an erection. Although she'd still had several orgasms, thanks to the relentless stimulation of her prostate, they had been immensely frustrating, with cum just dribbling out of her limp penis. She didn't want to experience that again. But nor did the idea of having her ardour artificially stimulated appeal either.

"Well", explained Nancy, "the client's a bottom as well as a top, you see." When Tiffany stared at her blankly, she laughed, "Seriously, you don't know what that means? Well, a bottom is someone who likes being fucked. The top does the fucking. So he'll expect there to be a bit of give and take, right?"

"O-kay", said Tiffany slowly, thinking the exact opposite. More to change the topic than because she was especially interested in knowing the answer, she asked: "So, er, do I get a script, like last time? You know, stuff to learn?"

"Nope", said Nancy. "You know your name, and that's it really."

"But what do I say if he asks me about myself?" It occurred to Tiffany that while she certainly wouldn't miss the humiliating answers she was forced to give at the mansion, they did at least obviate the need to say anything about her real self.

"Up to you", responded Nancy. "You can make shit up if you like. Or tell him the truth. He's a long-time member of the Club, so it's not as if he doesn't know that our sissies have - how shall I put it - other lives."

Tiffany flushed slightly at the description, but simply nodded to show she understood. They sat in silence after that until the promised limousine arrived. As she got into the car, Nancy said: "The driver will bring you back here in the morning, okay? You'll be able to, ah, change back and then go home."

"The morning?" said Tiffany. "You mean like, one or two o'clock?"

Nancy laughed. "No, more like nine or ten. Depends how long you lie in, really."

"So I'll have to sleep with him then?" asked Tiffany, her heart sinking. She was pretty sure she knew the answer.

"Well, yeah", said Nancy, still grinning. "Only I don't know how much actual sleeping you'll be doing, if you get my drift? Anyway, good luck and I'll see you tomorrow." She closed the door and the car pulled away.

The ride took about twenty minutes and Tiffany did not spend much time peering out of the tinted windows to see where she was going. She was too preoccupied with thoughts of what she was getting into. Even so though, as the limo turned into the driveway of an impressive looking house, she thought she vaguely recognised it. Surely she couldn't have been here before ... could she? Well, not as Tiffany, she thought. She would have smiled if she hadn't been feeling so anxious. Even with the chemical assistance from the clinic, she was a bundle of nerves as she rang the bell.

The door opened to reveal a handsome, middle-aged man. He smiled warmly and said: "You must be Tiffany. Do come in, dear."

Tiffany simply stood and stared. She had last seen tonight's client on the day that Eric lost his job. He was the managing partner who had made the decision ...

To be continued

Next: Chapter 3


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