Trapped in Number Six

By Zenna Swallows

Published on Feb 8, 2020

Transgender

TRAPPED IN NUMBER 6, PART 2

by Zenna

As Dylan sat in the front seat of the car parked discreetly behind the toilet block, he wasn't sure whether to be horrified at what had just happened, or terrified about what was still to come. In the end, he settled for both.

His brain kept cycling back and forward. Back to the events of the last hour, in which a simple stop to relieve himself had turned into an ordeal. He had been forced by some evil-looking men to give one of them a blowjob, using a glory hole in cubicle number 6. And then he'd had to repeat the process, only this time while wearing lipstick and girls' clothes, and answering to the name of Natalie. Involuntarily, he glanced downwards. He couldn't see much in the dim light. But he could feel well enough what he was wearing - the lacy tank top, the denim skirt that barely covered the top of his thighs, the cotton panties, and the wedge-heeled sandals in which he had struggled to walk.

Thinking about all that was bad enough, but then his brain kept snapping forward to the "lift home" the men had promised, with the clear indication that he was going to have to do something else either to or for them. Dylan really didn't want to think about what that might be - but his imagination was throwing up possibilities nonetheless. And they weren't pleasant ones.

He looked around. He'd been led to this car and told to get in, but then left alone. The men had disappeared and as far as he knew the door was unlocked. His hand strayed to the handle but then stopped. He couldn't leave. For one thing, he had no money or phone, and he was dressed like a girl. Where his own clothes and possessions were, he had no clue.

And for another, there was the video. The one the men had taken of him dressed like this and sucking a big cock, while he himself received a blowjob from a blonde girl - the same one who'd given him the clothes he was now wearing and applied his bubblegum pink lipstick. Goodness only knew what damage they could do to him if that got loose on the internet ...

Even so, he was feeling scared enough to make a desperate run for it, and was just reaching for the handle when the door on the driver's side opened. To his surprise, the girl got in. He stared at her as she strapped herself in and pressed the ignition button. She gave him a quick glance, her expression tense and serious. "You okay?" she asked, in a throaty voice that on any other occasion would have struck Dylan as sexy.

He stared back at her, but didn't answer. She shook her head ruefully. "Stupid question - of course you're not." She gave him a tight smile, then concentrated on backing the vehicle up and setting it on the track that led up to the main road. "In case you're wondering", she added, "we're headed to a friend's place. It's not far."

There was silence as the car began to make its way through the streets surrounding the park that Dylan had been walking through when he made his fateful decision to take a piss - relief that he had never actually got, as his bladder was currently reminding him. Although it was late, there were still many people around and Dylan tried to sink down in his seat, hoping not to be seen.

"Couldn't ..." His voice cracked as he started to speak, but he cleared his throat and tried again. "Couldn't you just take me home? Please?"

"I'm sorry babe", the girl replied. "Orders from the boss." She sounded genuinely regretful.

"Is your boss ... one of those men I just met?"

She gave a sardonic laugh. "Them? No. They're just muscle. But they'll come after you if you don't do what you're told. And then they'll come after me. So I'm really hoping you're not going to give me any trouble, right?" She glanced sideways at him and he gave a mute nod. "Good decision. By the way, I'm Holly."

He glanced sideways at her in the dim light provided by the streetlights and occasional neon signs. She was in her late teens, pretty in a slightly hard sort of way, the crop top and tight shorts she was wearing showing off the curves of her ripe young body.

Unbidden, an image came to him of Holly in the cubicle with him, her busy mouth working on his own cock even as he serviced the one sticking through the glory hole. She had done it, she said, to make things "easier" for him. He had certainly found it easy to shoot his load into her mouth. Not that she had to work all that hard to arouse him. For reasons he was still trying not to think about, the act of fellating the two men had been a turn-on itself ...

As much as anything to distract himself from the feeling of his cock coming back to life inside his panties, he murmured: "I'm Dylan."

"No you're not", said Holly flatly. "Not at the moment anyway. You know your name, right?"

Dylan was silent for a moment and then said. "So I've got to keep being Natalie, but only for a while?" The name came out like a curse. Holly had tricked him into coming up with it, when she'd asked him about the prettiest girl in his class at school, but then used it to identify him - as if he really was a girl, under the clothes and lipstick. Yet at the same time, he couldn't help letting a tiny degree of hope leak into his voice at the prospect of his ordeal coming to an end.

"If you do what you're told", answered Holly. "Okay, here we are." She drove down a ramp into a car park at the base of an apartment complex, got out of the car and led Dylan towards a lift. He was grateful that nobody seemed to be around to see him. A couple of minutes later, he was being ushered into a sparsely furnished living room. Strange noises were emanating from one of the inside rooms. "What the hell is that?" asked Dylan.

"That", said Holly with a grin, "is Katja. Come and see." She knocked on one of the internal doors that led off the lounge and, without waiting for any response, opened it. Dylan, still struggling to cope with his heels, tottered across the room to join her and looked over Holly's shoulder into what was evidently a bedroom.

The sight that met his eyes was utterly unexpected. There was a naked girl on the bed, behind and facing what looked to be a camera on a tripod, and with a laptop next to her. She was very obviously and very noisily in the process of masturbating, with her legs spread wide and several fingers buried deep into her glistening cunt. Her body was almost painfully thin, with breasts that were hardly more than bumps, and her long black hair was complemented by heavy, dark makeup. Her face lit up with a smile as she noticed the two arrivals, though she did not interrupt what she was doing.

"Hey Kat", called Holly, "this is Natalie." The dark-haired girl gave Dylan a quick nod, ignoring his stunned stare, but then focused her attention on Holly. "I'll just be few minutes", she said between moans. "Want to help me finish?" Her voice had some kind of middle or eastern European accent.

"Sure", replied the blonde enthusiastically. "Want to join us Natalie?" she inquired, moving forward and climbing onto the bed.

"Uh, no thanks" answered Dylan, still stunned at the sight in front of him. He watched, entranced, as Holly waved to the camera, then exchanged a deep, passionate kiss with the brunette. Realising that his cock was rising to attention and in the process lifting up his skirt, he looked around frantically and then stumbled across the room to sit on a chair positioned in front of a dressing table. He was careful not to get within what he assumed to be the camera's field of vision. Perching himself on the seat, he very firmly crossed his legs.

By the time he looked back to the action on the bed, he saw that Holly had released one of her plump breasts from the confines of her top and was feeding it to Katja, who was lapping at it enthusiastically when not taking a break to type on her computer. Meanwhile, the blonde had her hand between the brunette's legs and was gently rubbing the glistening slit.

As Dylan watched, Katja spoke in a teasing way to the camera and seemed to be soliciting both messages and money from what he assumed was some kind of audience. But after a few minutes, she announced: "It's time guys, I can't hold it any longer!" Taking that as a cue, Holly abandoned any kind of restraint and began mashing her hand against her friend's pussy. The orgasm that quickly ensued seemed to Dylan to be considerably longer and stronger than any he'd ever seen from his own girlfriends. Maybe Katja was a great actor - or maybe there was something he wasn't doing right. He was pretty sure he knew which explanation was more likely.

At any event, it was all he could do not to grab his throbbing cock and seek his own release. And that feeling only grew when, at Katja's urging, Holly (though not without some difficulty) peeled off her shorts and opened her legs to admit the slim girl's questing tongue. That too resulted in fairly quick order in another shattering climax.

The girls kissed and cuddled for a while as they got their breath back. Then there was time for a few last messages, both verbal and through the computer, before they were waving to the camera and then switching it off.

As she got off the bed and stepped back into her shorts, tugging hard to pull them over her well padded bottom, Holly laughed at the tense expression on Dylan's face and his firmly crossed legs. "Did you enjoy the show Natalie?" she asked, rather archly.

Ignoring the question, Dylan gestured at the camera and asked: "Who ... I mean, who is this for?"

It was Katja who answered. "Whoever want to pay", she said with a shrug. "Not that we get the moneys. But our boss give us little bit if we do it one time a week, same with beautiful friend Holly." She grinned at the blonde. "Some time we play together, like now, that the best fun."

Her expression turned serious, however, as she glanced at Dylan and then back at her friend. "This the one, yeah?" Holly nodded. Before Dylan could ask what she meant, Katja, who was still naked, inclined her head to him and instructed: "Come with me." She walked out of the bedroom, and turned to see if he was following her. At a curt nod from Holly, Dylan got up from the chair, desperately trying to conceal his erection.

His efforts were clearly in vain, because the blonde laughed and said: "Don't worry about that just now - although you'll need it later." This was another comment that Dylan chose to ignore- he really didn't want to think about where this might be going. Instead, he followed the brunette into the bathroom, where she told him to strip his clothes off and get in the shower. He was relieved to be out of the shoes in particular, though painfully aware his modestly sized organ was sticking straight out from his body.

His discomfort grew as Katja got into the shower stall with him. It was impossible to avoid contact with her, but she seemed to ignore that and concentrated instead on ensuring that he washed all over and used a bottle of makeup remover to get rid of his lipstick. She also made him use several courses of a floral-scented shampoo and conditioner on his hair. But she didn't stop there. Producing two razors and some shaving foam, she peered critically at his face. "You not start shaving yet?" she asked with a sly grin.

Dylan met this with a dignified silence. He had never been particularly hairy, but he had just enough to muster a wispy moustache if he let it grow. When she told him to shave his face and neck, he had enough practice to do it comfortably. But he was startled when instructed to shave his chest, arms and armpits as well, while Katja set to work on his legs. "What's going on?" he inquired, more than a little alarmed.

"You got to lose hair, Natalie", she said firmly. "Orders from boss. And what boss says goes, understand?" She gave him a sharp look and he nodded miserably before starting on the light pelt that covered his arms. "But what am I going to tell my family?" he pleaded.

"What, you walk round naked at home?" scoffed Katja. "Just keep clothes on. Or say you doing swimming race. Or you catch disease and hair fall out ... Now, less talk, more shave."

Soon enough, Dylan's whole body had been depilated, with the exception of a small and neatly shaped tuft of pubic hair. Katja, with practised if slightly scary efficiency, had cleared away the rest, casually working around the stiff cock that still jutted out from Dylan's groin. Regardless of how frightening the situation, it was clearly still quite happy to register its approval at being naked in a shower with a sexy young woman.

Finally, the ordeal was over and Dylan was able to escape the shower and towel himself dry, before donning a kimono-like robe proffered by Katja, who slipped into one herself. But while it was relief to no longer be naked, he now had to deal with the reality of his newly hairless body, which felt - well, strange, especially when the soft fabric of the robe moved against his skin.

And he quickly discovered he would face a new challenge, as he was led back to the dressing table in the bedroom. "Katja here is going to do a proper makeup job on you, Natalie", announced Holly, as Dylan's heart sank. "She's really good - does a lot of work in the theatre when she's not, well, on her back." The two girls giggled, as the subject of what was clearly going to be an exercise in further feminisation listened in stony silence.

"Thing is though", continued the blonde, "we do want you to have a bit of a choice about how you look. So you have three options. You can be what you might call a girly girl - you know, lots of curls, flowers, plenty of pink, you get the idea. Or you can go a bit Goth, like your lovely makeup artist. Or we could aim for the slutty schoolgirl. That last one's my favourite! But don't let that put you off ... So, gorgeous, what's it to be?"

Dylan did not feel gorgeous. And he certainly didn't want to look gorgeous - not like this anyway. But it seemed he had no choice. He was stuck in this house without his possessions, an appalling video of him (or at least a video of him doing appalling things) was just waiting to be shared with who knew how many people - and then there was the threat of those men coming back.

He chose what he thought would be the lesser evil. "Um, goth please", he said in a voice that was as timid as it was resigned.

Katja clapped her hands. "Good decision Natalie!" She bent down to plant a lingering kiss on his lips and then, ignoring his blush, set to her task with the same swift efficiency she had displayed in the shower.

As she worked, Holly sat on the bed and watched. After a while, she spoke. "Natalie, can I ask you something?"

"Do I have a choice?" responded Dylan. The blonde girl ignored his grumbling tone. "Back there in the toilet block, you looked like ... like you really knew what you were doing. You've definitely given a blowjob before, anyway."

Dylan reddened again, or would have done if his cheeks weren't being coated with various creams and powders. He caught Holly's eye in the mirror, but then looked away. "Come on", she pressed, "you can tell us. It's just between us girls, it'll be our little secret ... You're into guys, right?"

"No!" The protest seemed to have been wrung out of Dylan without conscious volition. "No", he repeated with considerably less vehemence. "Not guys in general. Just ... one guy." There was a pause, and he added: "Sam."

And before he knew it, and for reasons he couldn't fully understand, he was telling her the story he had never revealed to anyone. About his youthful "diversion" with his best friend. About their experiments with each other, and how what started as an exercise in mutual pleasure somehow transformed into Dylan taking responsibility for granting each of them the relief they sought. About the hopeless passion Dylan had developed for the blonde boy whose touch he so craved, yet chose never to communicate to the object of his desire. And about the relief he felt when the relationship fizzled out and a succession of new girlfriends proved to him that he was not really "like that".

"So you never let him fuck you?" asked Katja, who was in the process of applying copious quantities of mascara to his lashes. "No", said Dylan quietly, trying his hardest to stay as still as she had demanded.

"But you wanted him to", put in Holly. It was a statement, not a question.

"I ... I don't know, honestly" said Dylan, with a slightly helpless tone. "But if he'd wanted to, I'd have let him, that's for sure." There was silence for a while, before the two girls started talking about the respective merits of various types of cosmetic. Dylan was relieved that he didn't have to dwell any further on what had undoubtedly been the most confusing and difficult time of his young life. Up until tonight at any rate, he mentally amended.

Eventually, Katja's work was complete. Dylan stared at her handiwork, staggered at the transformation he had undergone. He was now wearing a wig of long, jet black hair which almost completely covered one side of his face, while leaving the other free. His eyebrows had been darkened to match, and trimmed and reshaped to form inviting arches. The black liner and mascara combined with the heavy dark blue shadow on his lids to make his eyes seem startlingly large. And in his pale face, which somehow seemed to have been reshaped to accentuate his cheekbones and soften his jaw, the dark purple lipstick stood out like a beacon, its colour matched by the paint that now adorned both his fingernails and toenails.

The effect was astonishing. Dylan could swear he was looking at a girl. He could easily believe this really was the face of someone called Natalie.

As if reading his mind, Holly asked: "What's your name?" He parted his purple lips to answer, but she held up a finger. "Tell me in the voice that you think someone with that name would use."

He nodded, paused for a moment to think and then said: "Natalie." Or rather he tried to; it came out as more of a squeak. He tried a few more times, until he settled on a soft, slightly higher version of his voice. It wasn't girlish exactly, but it certainly didn't sound masculine either. "My name is Natalie", he enunciated with more confidence.

"And what do you like doing Natalie?" He hesitated, but then gave the answer he knew was expected of him. "I like sucking boys' cocks. And men's too", he amended, ignoring the renewed blush that he could certainly feel, even if it couldn't be seen under all the layers of makeup.

"And if you found a special man, who you really liked, what would you want him to do?" asked Holly. He closed his eyes for a second, then opened them, mildly surprised that his mascara-encrusted lashes did not stay glued together. "I'd want him to fuck me", he answered softly, his voice shaking slightly as he did.

"Good", said Holly firmly. She looked round at her friend, who was grinning her approval. "Now for some clothes. Kat, what are you thinking?"

"I have perfect outfit", said the slim brunette. This turned out to be a black mini-dress with an elaborate pattern of cutouts, a black thong that barely covered what was left of Dylan's manhood (now mercifully quiescent, so that it could be safely tucked away), fishnet stockings that clung to Dylan's legs as if holding him captive, and studded black sandals with spiked heels and elaborate straps that wound up his calves.

He had no idea how he could possibly walk in these last. But fortunately, no sooner had he put them on than he was instructed to get up on the bed and find a comfortable position, facing the camera. "You're going to do a screen test", announced Holly. As if sensing the objection that was coming, she added. "Do it, and do it well, and you get to go home. I promise, okay?"

Dylan gave what we was sure must be his hundredth reluctant nod for the night. "Okay", continued the blonde, "what we want you to do is imagine you're talking to Sam. Tell him how much you want his cock, how badly you want him to fuck you. Only you don't call him by name, and you use the Natalie voice, yeah? And while you're doing that, you need to play with yourself, stroke that cock of yours until you come. Only not too fast. We want you to take your time and get good and turned on. Got all that?"

He nodded his head miserably. "Okay then, why we don't we give it a go?" said Holly in what she clearly hoped was an encouraging tone.

It went badly at first. Dylan was genuinely trying, but he also felt nervous to the point of nausea, not least because of his concern that if he couldn't do this right, he would somehow have to get home dressed as a girl and then introduce Natalie to his family. But then Katja had the bright idea of taking a break, opening a bottle of wine and just chatting for a while about both the challenge and fun of sucking cocks.

It was quite clear that both Holly and her friend made a living from sex - and not just from performing alone or with each other in front of a camera. They were both honest about the risks and downsides of what they did, but they also genuinely enjoyed their work when it was with the right partner. Talking to them about his experiences with Sam tapped into feelings that Dylan had never explored with anyone, himself included. And just as he had been able to use his memory of enjoying Sam's hard cock to get through his trial back at the toilet block, so now sharing it with the two girls made it easier to imagine himself as one of them.

By the time he got back on the bed, and got some tips from Katia about how to position himself and talk to the camera, Dylan was feeling lightheaded, but also more than a little turned on. That sensation only increased when the girls deployed what they jokingly called their "secret weapon".

This turned out to be a bright purple device with a thin flexible shaft, a small curved bulb at one end and a short crosspiece at the other. Dylan had no idea what it might be until he was instructed to bend over and Holly, with the help of some lubricating gel, slid it into his ass.

He had never experienced the feeling of having his rear invaded in this way, and the device felt tight and uncomfortable at first, even though it wasn't particularly big. But all that changed when Holly triggered a remote switch and the bulb began to vibrate. The squeal that he produced sent the two women into fits of laughter, and there was much teasing about how he should "take it like a girl". But once the intensity had been adjusted to a point where Dylan could bear it, he found that it was having an incredible effect in stimulating what he was told was his prostate gland.

From there, it was back onto the bed and in front of the camera. It took a while for Dylan to resist the urge to react to the delicious sensations in his rear by pumping his cock. Gradually, however, he settled down - and after a while, he found that he could start talking to the camera with a lot more conviction.

He imagined that he was surprising Sam, asking him if he liked what Natalie was wearing - the lovely dress, the sexy stockings, the high heels. He talked about his bright purple lipstick, and how good it would look as he opened his mouth to receive the stiff cock that he was so desperate to taste. Then he asked if maybe the special person he was talking too wanted to return the favour. And with that he lifted up the dress, reached into his panties and drew out the very tangible evidence that he too was hard and waiting to be played with.

He played with himself then for a little while, using some oil he'd been given to moisten his hands, but remembered his instructions and didn't go too far. Careful not to snag his heels, he turned himself over and presented his butt to the camera, lifting the dress up to reveal it. "Wouldn't you like to fuck this sweet ass?" he breathed in his softest, highest voice. "Wouldn't you to like to feel yourself, buried deep inside me? Because that's where I want you - inside me, fucking me as hard as you can." And with that he reached back between his legs and began to stroke himself again, pulling his stiff tool down so that it could clearly be seem.

Behind the camera, Holly and Katja exchanged delighted grins. They could hardly believe what they were witnessing - though the blonde had the presence of mind to check that the camera was indeed recording. It would be criminal to miss capturing this.

As Dylan pumped his hand with increasing urgency and started to pant, the girls realised that he was nearing his climax. At a nod from Holly, Katja called out softly for the feminised young man to turn back over and "finish it off". At the same time, Holly dialled up the speed of the vibrator in his bottom.

Dylan did as he was told, and before long all attempt to talk to the camera was forgotten as he concentrated on the pressure rising inside him and the astonishing jolts of pleasure that were coursing through his pelvis. His hand became a blur on his engorged cock and his pelvis thrust up and down, as if to ram the anal vibrator further inside him.

And then he was coming ... spectacularly. The first two jets of spunk reached as far as his chin, the rest spending themselves on his chest and belly - or rather, on the black dress that covered them. And he screamed with pleasure, not the low grunt he would normally have produced, but something much higher. Holly shook her head in admiration. Somehow, even in the extremity of what was plainly a shattering climax, Dylan had remembered that it was Natalie who was supposed to be coming, not him.

After an exhausted moment, Dylan opened his eyes to find Katja beaming and giving him the thumbs up sign. But Holly was signalling that there was something else he should be doing. He nodded and then, with a long and meaningful glance at the camera, he began scooping up the little puddles and drops of cum that he had spurted so enthusiastically, and using his fingers to feed them into his mouth. When he was all done, he swallowed convulsively and opened his mouth to reveal that it was all gone. Then, and only then, did Holly start laughing and applauding ...

It was an hour later when Holly left to take Dylan back home. They had given him another couple of drinks and chatted with him for a while, for all the world like three girls on a particularly raunchy night out together. Then they had cleaned him up, taking great care to remove all traces of makeup. Surprisingly, however, Dylan had suggested they leave his fingernails painted. He liked the look, he said, and he could pretend he'd lost a bet with one of his mates. If that was unexpected, so too was the change in his manner. He seemed to have stopped being the scared little boy, or at least forgotten to be afraid. But there was also a sense of realignment, the idea that he might really want to be someone else ...

Left alone in the apartment, Katja grinned to herself. Her report was going to be a lot easier than she might have expected at the start of the night. She located her phone and rang the special number she'd been given. In the interests of security, it changed regularly. When the person she was calling answered, she began to speak.

"Hello boss, it's me ... Yes, all good, Holly's just running her home now. Couldn't have gone any better, she was outstanding, best we've ever seen for a newbie ..." All trace of her European accent was gone, the voice cultured and precise.

"No, she didn't notice the camera on the dressing table. We got some fantastic material with her talking about sucking her friend's cock. The subscribers'll love it! And when you see what she did on the bed, well, you'll love it as much as they do!"

She listened for a moment, then continued: "A little bit. We slipped a pick-me-up into her wine. Or two actually. She had no idea again. Not very observant! But she's absolutely ready to do it again. You have to offer her a regular job, she'll make us a fortune ... Yes, Holly thinks so too. Just watch the video and tell me I'm wrong! ... Okay, will do."

Katja put her phone down, looked at it thoughtfully for a moment, then picked up a glass and drained the wine left in it. She was already thinking about what they might do with the young man who had been so thoroughly tricked and transformed in a single night. With her mind abuzz with ideas, she went off to start editing Natalie's first video ...

To be continued ...

*Like the story? *Feel free to email any comments to me at zennaswallows@gmail.com zennaswallows@gmail.com. And please think about making a donation to help support the great work Nifty does in bringing us stories like this one.

xoxo Zenna

Next: Chapter 3


Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate