To some extent i did but sure would have done so completely if given both the opportunity and safety to do so. I wore as many of my sister's things as she would allow. Sometime in my HS years i stopped raiding my mom and sister's underwear drawer and started buying my own. I was bullied a bit but then i also played sports which helped mitigate that. Indeed my non-standard way of presenting myself at times, attracted a lot of people and they would ask me questions etc. This was in the 80s.
In grade school i played with only girls and would wear feminine things if i could, i remember begging my older sister to purchase a pair of girls pants for me from a garage sales and she did.
I high school hung out with two groups of friends, the jocks because i was on teams and pretty good at athletics and the "dungeons and dragons" players, who were pretty close to a counterculture back then and use to role playing and more open to alternative ideas. My heros included David Bowie and Prince because both of those guys dressed androgynous. After i saw "Purple Rain" i ran out and bought a ruffled white shirt and pinned the collar closed with a rhinestone broach. I was all about standing out and all about contradictions.
My sister accepted me first, my mom was pretty reluctant at first but did by the time i was in college. She kept thinking it was a phase for me, but finally realized it was not. I lived with my sister for a summer when i was about 19 and she helped me dress, learn some makeup, put colors together etc.