When I was 10 years old I dressed as a woman.
But it was just one night and it was Halloween.
That was the end of my crossdressing days.
Whew....that’s a relief.....LOL.
I was a cheerleader for the junior senior Powderpuff game in high school. I did not make a good looking girl, but I did have impressive breasts LOL
I borrowed a skirt from a girl I was dating, and then borrowed a bra from the girl that lived next door to me because she was quite busty.
For those of you don’t know what the Powder Puff game is, it’s when the junior and senior girls play a game of flag football and the boys dress up as cheerleaders. This was in 1969. If memory serves, after reverting to my normal mode of dress my date and I went out and did some serious making out. Serious for 1969 I mean.