short Crossdresser captions.

A Cheerleader for a term...

Mark wished he'd never made this bet in the first place, posing in the embarrassingly short cheer outfit with his hands on his hips and lipstick on his lips. He had his twin sister Courtney were always making bets and complaining about school. Courtney complained about being objectified and flirted with, or having rumors spread about her. While Mark complained more about how he couldn't find any good friends and was ridiculed for no particular reason.

Eventually he said, "girls have it so much easier... Especially popular cheerleaders like you!" This was all it took.

"How about you prove it!" She smirked, "last one term as a cheerleader girl and I'll admit you've got the easier life! If not, you have to be on the cheer squad until college!"

"Fine." He shrugged, only really agreeing because he knew that she wouldn't be able to make him passable.

But after some fairly unusual methods, a Chinese tuck and injections in his hips, lips and chest and Melissa was the spitting image of his sister, well after the corset from TG Inc and the extension (also from TG Inc).

She got him a place on the team and he had to admit that it was difficult to train after the exhaustion of a school day, mixed with having to put up with guys and trying to stop the knickers he was in from riding up! So after just a week and four guys asking him in dates he gave up, but he had misinterpreted her, he thought she would get the glory as well as rejoining the team as Mark again.

But she wanted him to try everything, so he was forced on a date with the "jockiest boy who's asked her out" (as he described himself).

The date ended with a kiss and Melissa knew that he wasn't gonna like rejection, so they went on another date. Courtney joked that "three dates equals sex!"

He thought that this was all just her way of scaring him more, but when he found himself on his bed, in her underwear, with him climbing on top of her he knew that it was too late for him to back out.

After a few minutes of making out, he moved to her knickers and pulled them off to see his dick (small from female hormones he'd started taking) tucked in an usual way.

It took a lot of crying and some begging for him to make a deal. He would stay as Melissa and every night would do everything he wanted, while also being sexy until a few years after college.

Courtney had warned him.