One of my closest childhood neighborhood friends, about two years older than I, did more than the usual amount of snooping in his mom's closet as a child and at least into his teenage years. He would occasionally show me some of the lingerie items he had acquired -- I suspect raiding neighbor's clotheslines and such may have been involved. He went out as a girl on Halloween a couple of times. I haven't seen him for decades now, and I have no idea if he still dresses up.
Another friend from high school was not quite as public about it, but he had a far greater amount of knowledge about the local drag scene than I think most teenagers could have acquired innocently. I'd love to talk with him about it now, but unfortunately he died a couple of years ago.
I also sincerely wonder about my grandfather -- actually, a step-grandfather, not a blood relative, but certainly a major figure in my life growing up. He was a very gentle, rather feminine soul, and is the only person I know who owned a copy of Harry Benjamin's _The Transsexual Phenomenon_ shortly after it was published in 1966. In his later years, he received estrogen treatment for prostate cancer -- a standard therapy in those days -- which definitely had a physically feminizing effect, but I don't know if he would have chosen this on his own. I never saw him dressed but have often wondered about what went on when I wasn't around.
- Diane