Short version, it came from losing a bet.
Long version...as penalty for losing to one of my exes at Guitar Hero, I had to put on her clothes, let her do my makeup, and then leave all that on until my uncle (with whom I lived at the time) came home from work. At first, I was mortified at what I had allowed to happen...but I had one of those full-body mirrors, and she demanded I stand in front of it and look. When I finally pried my eyes off my face and looked, I instantly thought, "Well hellooooooo there madame, where have you been all these years?".
Funniest thing about it was, she bragged about that one to so many people that when I came out, even though we'd been separated for over two years, my friends immediately started blowing up her phone and her facebook account asking her what the

kind of sick crap she'd done to me post-breakup. They initially thought it was a coping mechanism...bahahaha.