I've always been bored watching my girlfriend's soccer matches. After a game, she invited some of her teammates over, and they made me into a cheerleader. From a dress to pom-poms, I had to do whatever they said. This short, gender-swap role play has feminization, first-time sissy action and lots of adult fun.

When Charlie’s friend Vanessa crashes his gaming party and whines about the boys never wanting to have a night on the town, Charlie shoots back that he’d love to go out if he could get the kind of romantic attention she does for just one night. Without missing a beat, Vanessa offers to give him just that chance and see just what it’s like to be a gorgeous girl on the town. With his soft looks and slender body, she thinks she could make him into a rather pretty girl.... Why not, Charlie wonders? It might be fun.

It’s Christmas break. Gorgeous Piper loves nerdy Jake’s passion for buying her clothes, but her intuition tells her he does it not only because he loves her so much but also because of his hidden desire to wear them himself. She buys her love everything needed for crossdressing and transforming Jake into Jackie, her girlfriend. That afternoon, she enlightens him in the nuances of presenting his feminine side and immerses him in the pleasures of catering to his feminine persona.

When Sam puts out an ad for a new roommate, he wasn't expecting a gorgeous woman like Jessa to answer! But her cash is good and she wants the room, so even though it's kind of weird, he agrees to take on a female housemate. The only problem is going to be keeping a lid on his tendency to wear women's clothing now and again...especially since Jessa asked him to handle the laundry! Sam can't resist a hot pair of panties, and soon, he finds himself falling back onto old habits. But when Jessa catches him dressed up in her lingerie, rather than being disgusted, she thinks it's hot.

Prom is approaching, and Jeremy has his eye on Amanda. Well, every guy has his eye on Amanda, and a few of the girls too. She’s the hottest girl in school, so Jeremy doesn’t actually think he has a shot.