T-Girl in Training (closed for DoctorT and Wolfy)

[DoctorT]

Cal Wilson had been a lousy Marine, but he made a pretty good criminal. A dishonourable discharge for insubordination and violence had left him on the streets with not much to his name in his mid-20s, but after that he had turned his life around, working his way from bouncer to bodyguard, occasional mercenary work, and from there into the outer reaches of organised criminal gangs, who could pay well for people with the skills they were looking for who could keep their mouths shut and stay out of trouble with the cops. He'd also found an outlet for his more aggressive side in sadomasochistic relationships, being able to control and channel himself into training submissives to be compliant little fuck toys. An added bonus was that his connections gave him a ready market for trained sex slaves once he was bored with them. Usually they were young women, often with messup personal lives, lost and aimless, occasionally runaways, looking for father figures, occasionally they were more mature women, curious to experiment but finding they had bitten off more than they could chew. And sometimes they were transsexuals and cross-dressers. Cal hadn't been sure about that to begin with, but for the right kind of wealthy pervert a chick with a dick was worth even more than a real girl. Moreover, he'd found them often easier to train, more willing, more needy, less bratty, and that simplified matters considerably. They could be harder to find, though; often teenage boys would cross-dress in secret, still nerving themselves to tell friends or family or to go out in public. It had only been by chance that he had driven past Taylor's house one early evening, while their bedroom light was on but the curtains still open, and seen her preening in front of a mirror in her skimpy little outfit. He'd noted her address down, and while he completed work on his latest project - 'Penny', a blonde cheerleader with a wild streak who had turned into one of the biggest sluts he had ever encountered - he researched Taylor off and on; social media accounts, friends and family. That was how he knew her parents were out for a fortnight at some family get-together, and she was alone in the house, probably getting her rocks off in one of her favourite outfits. Penny had recently gone to a collector in Arizona, leaving Cal without a current project, so this seemed like the perfect opportunity to see if he couldn't sweep Taylor into his net.

He checked the street as he got out of his anonymous car, but this part of suburbia was deathly quiet at this time of night. He walked quietly to the side of the house, letting himself into the back garden, where he pulled the ski mask over his face. He knew that she wouldn't have set the external security - she was notoriously lax about that - and the back door yielded easily to his lock picks. He slid the door quietly and listened, gauging where she would be.

 

[Wolfy]

Taylor was tiny for a guy, only about a hundred twenty pounds or so, short for his age - a fact that led to relentless bullying. It could have always been worse, however -- as no one yet knew she was trans. Tonight, like every-night she had the house to himself, Taylor spent his time raiding his sisters closet and makeup. He gave a wink to the reflection in the mirror, sticking his naked butt out a bit and smirking. It wasn't so bad to have a more feminine build when you enjoyed being feminine. Taylor batted eyelashes at her reflection, long, mascara-laden lashes flashed back, framed with oh-so-elegant winged eyeliner. She smirked, her tongue poked out between the luscious crimson lipstick expertly covering deliciously plump lips.

Taylor had been up most of night, she'd spent a few hours getting ready before binging on Netflix and popcorn. Her parents were in France for the summer, and her sister had decided to take summer courses up at Washington state. When she had been told she'd be getting most of the summer at home alone it took everything in her to contain the excitement. It wasn't that she wanted to be away from them all, it was just... She'd never come out to them that she was trans. It was a difficult thing to bring up at the dinner table, and her parents were traditional enough she wasn't exactly certain how they'd take it. Getting sent to therapy was not her idea of a good family bonding experience -- this summer, however, was a perfect opportunity for her to be.... her.

A clap of thunder broke the stillness of the night, Taylor jumped and then laughed at herself for being silly. Fresh out of the bathtub, and smelling like strawberry body wash and lotion, she took a long look at herself in the mirror. Bright mischievous brown eyes scanned the reflection A little short with curly brown hair falling about the shoulders, sleek build, perfectly arched eyebrows, lushly long lashes fluttering back at her.

Skipping to her sister's closet, Taylor pulled out a lacy black garter belt and matching thigh-highs, sliding both on with slow, sensual purpose, enjoying every moment of the material sliding over their legs. A short black pleated miniskirt, cute lacy white top and pair of thigh-high stiletto boots later and Taylor was already feeling better. She gave her sister's full-length mirror quick kiss and gave her reflection a wink. With the grace of someone who'd obviously spent a lot of time in heels, she skipped down to the kitchen and grabbed a bottle of wine before planting herself in the recliner and switching on Netflix. Tonight was a self-care night, and so far it was exceeding her expectations.

 

[DoctorT]

Cal headed towards the living room, drawn by the sound and flickering light of the widescreen TV. He crouched in the darkness of the half-opened doorway to the corridor leading to the kitchen for a few minutes, watching Taylor, with her back to him, enjoying her outfit, especially the slutty little miniskirt and stockings and the long, high heeled boots. She was going to be a complete natural, he could tell. He filmed her for a while on his phone, recording her drinking wine, eating popcorn, watching TV. He had the syringe of propofol ready in his pocket; his initial plan had just been to sneak up, grab her, and hold her while the anaesthetic did its work. Sometimes as little as ten seconds was all it needed. But as he watched her, considering, he wondered if he would actually need it tonight. He wondered what kind of needs Taylor had, and how she had thought about meeting them. He started recalibrating his plans, wondering if he could even get her to walk out of here with him. Of course, the syringe full of the drug was always there as a backup if he needed it. But for now he decided to take a risk, pulled off the ski mask and stuffed it into his coat pocket and stood up, walking quietly into the room until she glanced around and noticed him. He caught the sudden panic in her eyes at having a large dark-clad intruder in the house, and quickly reached forward to grab her as she tried to get up from the chair, awkward in her heels.

"Shhhh!" he said, moving behind her, tight against her, bringing one gloved hand up to her mouth to stop her from screaming, and using the other to pin her arms to her body. "I'm not going to hurt you, I promise. Just relax, don't struggle. Besides - I don't think you want the neighbours to come around and see you dressed like this, do you... Taylor? It could be a bit awkward. I just want to talk. So relax, I'm going to let you go in a minute, and I need you to be calm and quiet. Scream and I *will* hurt you. And that's a promise, too." He tried to put enough menace into his tone that he would cow the young transvestite, but he guessed that the physical difference in size and build between them was probably enough on its own. "Are you going to be a good girl, Taylor?"

 

[Wolfy]

Taylor's heart was a jackhammer, pounding away in her chest. What the fuck? Fuck, fuck, fuck, fuck, fuck! She tried squirming, tried to bite him. A shiver ran down her spine as she tried to size up whoever the hell this was. They knew he was huge and strong, and ballsy. But what the hell is going on? What did he want here? She kicked at his shins, tried to dig her nails into his body, anything to inflict some sensation that might cause him to lose his grip. "You think you're gonna rob my home? You picked the wrong household asshole. Now you'll fucking put me the fuck down is what you'll do, and get the hell out of my house if you don't want me to scream so loud every neighbor on this street will wake up!" She hissed. "I think the exposure will be a lot more fucking awkward for you than it will me!" she took a deep breath, and opened her mouth, "HE--"

 

[DoctorT]

Cal rolled his eyes. This has not been one of his better decisions. He was getting soft and careless. Lesson learned. He jammed his hand back into Taylor's mouth, grimacing slightly as her teeth dug into the leather glove, penetrating it very slightly and causing some major discomfort as he dug in his pocket for the syringe and jammed it into her thigh, pushing the plunger home and starting to count. By the time he reached fifteen she was already starting to fall limply as a dead weight in his arms, but he held it to a count of 60 before he finally decided she wasn't playing possum and let her drop to the floor. He shook his left hand and examined the bite marks in the glove.

"Son of a *bitch*!" he muttered, rubbing the indentations. He looked down at the girl slumped on the floor. "You're going to regret that, you stupid little sissy bitch," he told her uncomprehending form. He checked his watch. The dose should keep her out for about 40 minutes. He needed to be a long way from here by that time. He headed to the front door, leaving it ajar, and headed across the street to his car, getting in and backing it up the driveway of Taylor's parents' house, as close to the front door as he could. He popped the trunk and and grabbed a bag from inside it and took it back into the house with him. Once back inside, he checked Taylor's pulse one last time to make sure he hadn't overestimated the anaesthetic dose, then rolled her onto her front on the living room floor and pulled her arms behind her, fastening her wrists together with a pair of handcuffs. He tied her ankles and knees with nylon rope. A large 3" ballgag was pushed into her mouth, and he tightened the strap behind her hair.

He headed upstairs, and had a rapid root through the rooms there. He found what had to be Taylor's room and threw a few items into his bag - toiletries, personal electronic items, some clothes, but not too many. He left that for his sister's room, grabbing handfuls of underwear, the sexier the better, short skirts and little tops, makeup, shoes, dildos, vibrators. He wanted to make sure it looked like Taylor had absconded and taken half his sister's wardrobe with him. He left the laptop, and made sure that it wasn't password protected. The browsing history would hopefully speak for itself - once Taylor was listed missing, they'd discover she was trans and assume she'd run away from home.

Finally satisfied, he dumped the bag in the back of his car and headed back to Taylor, still unconscious. He switched off the TV and all of the lights in the house, threw the popcorn into the bin and emptied the wine bottle down the kitchen sink. He dropped the dirty glasses and plates in the dishwasher and went back to the darkened living room, where Taylor was still lying. Cal smiled. "Time to say goodbye to your old life, sweetie," he told her, bending down and lifting her light frame easily, hoisting her onto his shoulder. He headed back to the trunk of his car, which he had left open, and gently eased her into it, torso and head first, then lifting her legs in and bending them to fit within the confines of the confined space, before slamming it shut with her in it.

He allowed himself a fairly contented sigh as he checked one more time up and down the street, then pulled away and drove off into the night.

Cal's place was a farmhouse a few miles out of town. It stood in 20 acres of its own land - most of the land had been sold off by the farmer before he finally quit farming for good and sold off the main building, but there was still enough to make it private and discreet. By the time Cal pulled off the small rural route that served the farm and up the driveway to the main farm building, his 40 minutes were about up, and Taylor would be groggily coming to in the trunk. However, it had been quite the night, and the little bitch deserved a lesson for biting him, so he decided to leave her there until morning. It was gone 9 am when he finally had been up, exercised, breakfasted and showered, and wandered out to the car to open the trunk.

"Good morning," he said brightly. "I hope you had a terrible night. That's what comes of being a cunt. Now, this time, we can start over. You can stop being a cunt, or I can carry on hurting you. Your choice, baby."

 

[Wolfy]

Soft, muffled cries escaped the trunk as Taylor rolled around in the darkness. Her jaw was aching from her gag, knees and legs bruised from kicking against the trunk till she'd tired herself out. Tears and mascara stained her cheeks as she whimpered in response.

What did this creep want with her? Why was he doing this? Taylor's parents weren't super rich and she herself didn't have much in any accounts.

Why was he doing this? What was he planning on doing with her?

Taylor gave a soft begging whimper from inside the trunk in response to his question.

 

[DoctorT]

"Okay then," Cal said, taking her whimper as some measure of submission. He reached down and slipped a blindfold around her eyes, tying it off behind her head, then lifted her gently out of the trunk, and carried her into the farm building. Taylor had a sense of open rooms and wooden floorboards and then he carried her carefully down a flight of wooden steps into a cool, slightly damp basement. They passed through a doorway or opening into a second room where the sound seemed deadened. Cal turned her upright and sat her in a metal chair, apparently bolted to the floor, but there was a cushion as a concession to comfort.

The room was dingy and a bit dusty and there was junk around the walls. It wasn't the main 'sex dungeon', which was actually considerably cleaner and nicer, just an old storeroom that Cal liked to use to put new arrivals in the right frame of mind. He picked up a heavy bladed knife from the table and advanced on Taylor. Had she been able to see him, it might have looked menacing, but he didn't bother to stop and run the knife across her skin or anything melodramatic. Instead he just used it to bend down and cut the ropes secuing her ankles and knees, so that he could move her legs to the ankle straps on the bottom of the chair legs, to secure her legs there. Once she was securely shackled to the chair, he did the same with her wrists, unlocking the handcuffs and moving each arm to the leather wrist cuffs on the metal arms of chair. Once she was securely strapped down, he first removed the blindfold, showing Taylor the dingy room that she was now being held in, and then finally reached behind her head and unbuckled the gag, pulling it free and allowing her aching jaw some relief.

"So," Cal said, conversationally, "I imagine you're full of questions. What's going on, who am I, am I going to kill you - all of that? Who I am doesn't matter. I'm the guy who picked you, that's all. For now, you can just call me: 'Sir'. Am I a serial killer? No, but that doesn't mean I'm not dangerous. Right now you probably think I'm just some sick pervert, and sure, I'm that too. But once you're out the other side of this, I guarantee you that you'll look back on all of this with fondness, as I helped you uncover your true self, the one you don't dare to show the world. What I'm doing is helping you become what you really, truly are underneath. Oh, you'll kick and scream at first. Letting go of your old life is a difficult and painful process. But I'll be here to guide you, and set you on the right path when you stumble. Sometimes with the carrot, sometimes with the stick. But first things first - I imagine you're pretty hungry and thirsty, and you'd like to use the bathroom, am I right? So these are things I can give you, but you have to ask nicely. Why don't you try that?"

 

[Wolfy]

Taylor worked her sore jaw, and looked around the dank, dingy room. She strained her ears, only Cal's voice came back to her. Well, that and the thundering of her heart. She tested the bindings keeping her in the chair, they didn't budge. How long had they been in the car? How far away was she from home? From anyone? She thought hard but it was no use, no telling how long she'd been unconscious. Hell from the room she was now in she couldn't even tell if it was night or day. Was she even in the same state? Hunger pains jolted her hard but she suppressed them. It wouldn't be the first time they'd skipped a meal.

She looked back at Cal, his words bounced around inside her head. What the hell was this nutjob talking about? 'On the other side of this?' Her thoughts raced back, how long had she been gone again? It didn't matter, when her parents came home they'd find the house empty, son gone. There'd be a search. News. Police. All Taylor had to do was wait. Someone would find them. Eventually. They had too. She'd been kidnapped for christ's sake.

Taylor stayed silent, eyeing Cal suspiciously. Fuck him. Letting go of her old life? Absolutely not. She was going to get out of this, and she'd laugh smugly when this asshole was in jail. "You won't get away with this." she warned, looking him right in the eye. "You know that don't you? My parents won't just sit by as they find their kid is missing."

 

[DoctorT]

Cal smirked as Taylor started giving him lip. That wouldn't last long.

"You're not missing," he told her. "Your parents are in France and your sister is in Washington State. No-one will miss you for at least two weeks, and even when they do come back, they'll find you've run away, taking half your sister's wardrobe. You've left an apologetic note telling them about being a trannny, how you couldn't tell them to their faces, but you have to go off and find yourself. You'll try to stay in touch, and they shouldn't worry too much about you. Your phone will eventually be found in Florida. They'll get emails now and again telling them everything is fine. You're still just about a minor, so there'd be a statutory police search. But even if your parents do get the nerve to report you missing, the police won't mark it down as serious; there's no indication of foul play or third party involvement. The search will be perfunctory, and it sure as hell won't reach here. Bottom line - this is your life now, and you'd better get used to it."

He cracked his knuckles. "Anyway, I offered you a deal, and you chose to refuse it, and you didn't call me 'Sir' like I told you to, so it's probably about time you find out what happens when you do that, I guess."

He walked around behind her and unshackled one hand from the chair, bringing it around in front of her to fasten it to her other wrist, then released that wrist from the chair, so that her hands were now cuffed in front of her. He pulled a nylon rope through the cuffs and passed it over the hook in the ceiling, pulling her arms up above her head as far as they would go, then tied the rope off. Then he released her legs from the chair and cuffed them together, before returning to the rope, pulling it up again so that Taylor was now forced onto her feet, and eventually onto tiptoes. Cal reached for the fastener of the miniskirt and unzipped it, letting the skirt slide down her stockinged legs and long leather boots to the floor.

Next he walked out into the next room, returning with a bag, from which he pulled a long leather strap, split from about halfway down. Cal swished it through the air a few times, enjoying the sound.

"So this is what happens to mouthy bitches who won't do as they're told," he said, and swung the strap with the full force of his arm to crack against Taylor's exposed bottom.

He left it a few seconds for the force of the blow to fully register, then did it again. And again. And again. Switching the target up and down a little, to cover her exposed thighs above the stocking tops, and to make sure that every inch of her pert little rump felt the full force of the tawse. He didn't bother to count, or set any kind of limit, he just kept on leathering her ass until she was crying and begging for him to stop, and then he carried on some more, just to prove that she didn't get to control when that happened. Finally, breathing slightly more heavily, he stopped and surveyed his handiwork, Taylor's bottom and thighs now a red and purple mess of weals, some of which were starting to darken towards bruises.

"Okay," Cal said, moving back to stand in front of Taylor. "So let's try again. Would you like something to eat and drink and to use the bathroom, Taylor?"

 

[Wolfy]

Days, weeks, a month passed. Taylor wasn't even sure what constituted a day anymore. The only real-time she could get any sense of it was when she caught a glimpse of sunlight or darkness out a window when she was allowed anyplace other than the basement. She was forced to clean and tend to Cal's needs, a servent, no more like a slave. She cooked. She entertained him. Was smacked around when she stepped out of line, and every day she bent over as Cal pushed the sharp tip of a needle into her bottom and flooded its contents into her body. Taylor didn't ask what it was, and Cal didn't offer. But as the weeks went on, and she spent all her time as a girl, the change in her was becoming evident.

Taylor had always looked feminine. Slight build, long legs but too short for his age, far too small of a frame. This, however, was different. Fat shifted and settled around her hips, gradually flaring out her figurer. Her already rounded bottom grew plump and heart-shaped. Her nipples grew tender then puffy, as budding breasts started to form, first an A cup, then a B. Soon from behind she looked obviously enough like a teenage girl. Taylor blushed every time she looked in the mirror.

She was becoming more comfortable in her skin than ever before -- and yet her life was quickly becoming more and more complicated. Cal tracked her progress, measured her figure weekly and noted it on a clipboard. Checked the tenderness and responsiveness of her breasts and bottom, noted if and when she became aroused. She practiced giving a blowjob on a dildo.

Occasionally she caught glimpses of her medical and dental records. School records. Notes charted on her home, habits, the coming and going of her family and friends. Social Security Number. How did Cal get all that? She wondered how long he'd been eyeing her, planning this. Part of her still waited for her to wake up. This couldn't be real. She had to wake up one day, and she'd be in her bed. But it never happened.

 

[DoctorT]

Cal was a patient man, and knew that this could be a long haul, so he let Taylor into things relatively gently, to get her used to being confined, and to get her used to obeying his orders. The rule was quite simple - if she obeyed, and called him 'sir', then good things happened, if she didn't, then bad things happened. In spite of some initial rebelliousness, the thrashings and deprivations took their toll on Taylor, and it only took a few days for her to settle into the routine of doing as she was told, eating when she was told, and asking permission to use the bathroom. Nights were spent chained on a bed if she was a good girl, or naked in a small dog cage if she was a bad one. Meals came on a table if she was a good girl, or in a bowl on the floor if she wasn't. During the evenings and nights he left her laptop running out of her reach in the room, now wiped of everything except Taylor's copious collection of TV/TS porn. Every night she slept to flickering images of T-girls fucking and sucking. It was all the entertainment she was allowed.

During the days she got to move around the house a little to cook and clean, usually with legs shackled and handcuffs fastened to a waist belt. The place was quite spacious and through the windows Taylor could see fields and trees, but no human habitation, or other people. The doors and windows were all locked. Taylor got to wear a little French maid outfit when she did the cooking and cleaning, complete with pinafore and fishnet stockings, and it occasionally amused Cal to make her say: "oui, monsieur," or "non, monsieur", when she did so, in a terrible French accent.

The hormone therapy he had started immediately after capture, and was pleased at how well and how quickly she had responded. She was soon developing genuine breasts and starting to look more female in silhouette. Still, he maintained a rigorous beauty regimen for her, making her shave and wax all hair off everywhere except her head at least once a week, and begin each day with moisturisers and make-up. It was important for her to get used to looking pretty. Clothes - if she wasn't wearing the maid outfit - would be laid out for her to wear, always pretty and girly. Cal paid special attention to high heels, getting her used to walking and moving in them all the time. Some days they would be locked on and not removed until bedtime. Her hair he made her grow out, although she was allowed to keep the wig for the time being until her real hair became long enough.

After a couple of weeks of getting her used to obedience, he started on the sex training. This began with sucking a dildo, sometimes for an hour or more at a time. A series of lines were marked along it at inch-long intervals, and every day Taylor had to leave a lipstick ring at the next line, until finally she was taking the dildo all the way down and into the back of her throat, where he would make her keep it for what felt like ages, practicing with overcoming her gag reflex. As usual, failure led to punishment. He also made sure that she kept her ass lubricated and a butt plug inside during the day, so that she could feel it as she moved, and gradually started increasing the girth of the plugs as she became more comfortable with them.

Eventually he felt it was time for Taylor to start moving on to the next stage of training. He called her before him in the living room one morning while she was going about her chores, and made her kneel down in front of him.

"So, Taylor, how do you feel about how things are going?"

"I think you're progressing well. It's about time you moved on from plastic cocks, I think. I'm going to start you on real cocks today. How do you feel about that? Why don't you crawl over here and see what you can achieve with your pretty mouth." He patted his crotch.