A 16yo boy loses a bet and has to dress like a girl and hang out with his buddies for a night. He decides to really fuck with their head and enlist the help of his sister to make him really look hot. His group of straight friends don't have much luck with the girls and are floored to see how sexy he turns out to be. If they didn't know he was their friend they would have thought he was a real girl. Overnight he goes from being just another one of the guys to being the most popular boy in their clique. To maintain that position he will have to continue to dress up.
I can play the cross-dresser or his best friend.
This can also be played with him dressing up for his female friends instead.
Two best friends are having little success with girls. Mostly due to spending most of their time with each other. Talking to girls without becoming tongue tied is almost impossible to them. Then one night in a chat room they find just how popular they are with perverts. They find what it is like to be treated like a prince and not just a couple of losers.