Brothel Feminisation Pt. 01

"Further."

He shivered, doing so.

"And again."

That time, he rested his hands on his knees, pushing back a little. If he was trying to show off, how would he look?

She chuckled behind him.

"Better. Now, this will be cool."

She was surprisingly gentle as she pressed the lubricated tip to the small, blue butt plug to his anal ring, teasing it inside. That was most likely why she was a trainer, for her skill and expertise, but he still quivered as it sank into him. It was small and easy to take and a part of Sam yearned for something bigger, something he could really feel inside him. Of course, the narrower neck of the plug along with the flared base kept it in place, nicely secured there.

"Mmmph..."

"There's a good girl."

Girl? He gasped, sucking in a breathy inhalation. Was he a girl? Why did it feel good to be called a girl? He couldn't say, head drifting a little, sinking deeper into his role.

All he had to do was listen. If he listened well and obeyed, he would be good for the brothel. And he would get a far more exciting, enticing life than he would have otherwise.

"On the bed, on all fours," she said, wiping off her hands once the butt plug was well seated inside him. "Your first lesson is in sucking cock."

There wasn't much for Sam to think about that one in hindsight, since he had never had a dick in his mouth before. She used a sex toy on him, the smooth, velvety silicone moulded so it had the veins and shape of a real cock, even down to the shape around the head. Yet he still drooled around it much more than the other brothel prostitute beside him had, saliva streaking down from the corners of his lips and mucking up his chin.

"Mmph... Hmph..."

"Deeper..." His trainer tilted the dildo up, pushing it to the back of his throat. "Swallow...now!"

"Unff!"

It was harder than he could ever have expected to suppress his gag reflex, but he tried. There was nothing else for him to think about and most certainly nothing for him to worry about. And there was something settling in that too as he was given his first lesson in sucking cock, a toy ground into his mouth even as he tried to lap over it and cradle it on his tongue. His fantasies, however, looked to never have the chance to live up to reality.

For his reality was going to turn out so much better for him.

She tested his anal use as well, removing the butt plug for a time to use several different dildos on him. His cock didn't even get hard as she penetrated him, though it was as if the whole experience was not about his pleasure, not about that lure of orgasm, regardless of how hot his blood flowed and how his heart sang for the moment. It was more than sex -- it was about giving and it was about serving. There, he could have all the sex he ever could take. So, why even try to rush something that was coming either way?

"Nnnggghhh..."

He didn't want toys only inside his backside, however, trying to convey that to his trainer -- but she just brushed him inside, teaching him to relax, instructing him on different techniques and how to control his muscles more effectively.

"You'll get a client in time," she told him, for he didn't really have any say and it was up to her to decide what he was ready for. "There'll be a nice batch of guys coming by tomorrow. A few of them can use you. And then you'll see how you feel about everything."

"Agh... Yes, ma'am."

That was the most comfortable way for him to address his trainer, though everything felt a little easier already, a goal in mind and set for him. As he didn't have customers to service at the brothel that day, he spent time in his room with the toys, working the dildos deep into him, riding them on the floor with the bases pressed down hard into the floorboards just to keep them stable.

His cock swelled a little, but he did not climax, panting softly, wondering if the injection and the drugs from the butt plug had anything to do with that. He didn't mind though, as long as he was good, as long as he could lean into the things he was waiting to do, already imagining a big man bending him over and fucking him rough and hard with long, driving strokes of his cock.

Sam started socialising with some of the other brothel girls, though he found a room where clothing options were managed on long racks for them, giving them some agency. More luxurious items, of course, were behind doors that those with promotions could access: yet another reason for him to rise through the ranks.

Not that he was looking for anything -- but Sam wasn't going to let his nerves rule him, oh no. He would see where he could go, a crop top and a pair of feminine briefs on for dinner, taking his pills dutifully. Of course, the butt plug was in place, but he had to be bolder than he'd ever been before.

For the first time in a long time, Sam went to sleep looking forward to the next day.

Continued in part two of three...