About 30 years ago, the band I was in played a Halloween show in a college town bar (the place was huge, and packed with costumed revelers). The band hit the stage wearing our typical early '80's rock star wannabe attire... except for our new keyboard player. He decided to come to his first gig with us wearing a dress, wig, make-up, heels... the whole nine yards. Needless to say we were pretty stunned at his transformation.
The next week wasn't Halloween anymore, but out he sashayed in another one of his fabulous outfits! He turned out to be a crossdresser.