Trapped in Number Six Pt. 02

Dylan gave what he 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?"

She inclined her head towards his groin. "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, 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 ...