My First Time...My first time dressed as a girl was on Halloween. It was the early 70's, and my Mom and aunt thought it would be cute to dress my cousin and I as girl for Halloween. We wore the latest 70's fashion -- we each wore turtleneck bodysuits, pantyhose, mini skirts, go go boots, and cute little wigs. It felt amazing to walk around the neighborhood dressed like that. We got many compliments on our outfits, and I never wanted to take it off.
I had another experience in college. My girlfriend and I were trying to think of costumes for a Halloween party and she said, "You can wear my ballet dance wear." I pretended not to know what she was talking about, but I knew. "You can wear my leotard and tights." I pretended to protest, but could not wait to wear her dance clothes. I wore a black leotard and pink tights with a little skirt to the party -- I have never had my *** pinched so many times in one night in my life!