I don't remember if it was here or on Fictionmania, but a couple of years ago I read a story of a boy who liked to dress as a girl. Once while dressed, he received a call from a relative, I believe a cousin. While talking with him, she kind of figured out what was going on. When they were together later, she asked him about it and he admitted it. She assisted him. At the end of the school year, they both worked at a resort along a river that was owned by relatives in her family and he worked the entire summer as a girl.