He loves it big (sissy)

John took a picture of himself. With some makeup and a dress, he could almost pass as a woman, if it wasn't for his cock pushing against the fabric.

"Damn, you look nice." His roommate commented as he walked in his bedroom.

Evan was his bully for a long time. So, when he got paired as roommate in the dorm of the college, John really though that it would be a difficult year. But then everything changed when he forced him to put on a night dress, fishnet stockings and some makeup. Evan became confused and stopped being mean, he even became kinder and gentle.

Catching on that change of attitude, John took that opportunity to get closer to him, acting more feminine to confuse him even more. Which led to a kiss, some foreplay and his cock in his ass, pounding it like a bitch. For both of them, it was a strange night.

Some sort of friendship grew after that, and the relationship got switched on its head. Evan was getting nicer, especially when John was dressed like a woman and John started to look more into his feminine side.

"Do you think I should dress more like this?" He asked Evan, after his roommate barged in.

"Abso-fucking-ly, you look amazing."

In a way, it pleased John who became more and more bold with him. Dressing sex, getting close to him, just so he could fuck him again. At some point, that relationship looked more like a couple than friends. There was no trace of bully and victim in this new dynamic.

Still, Evan wasn't looking that he would show that relation outside the dorm room. That's why, John took a drastic decision. The summer Holidays were long enough to get plastic surgery and become Jane, the "new" girl with nice fake tits.

Evan fucked his newfound girlfriend, using her tight ass again and again, making her moan and cum like a woman.

He didn't mind going out with her after that.