The first time I went outside dressed was when I was 14 and with friends at a girls house. As the evening went on we all started to play truth or dare, after about 30 min the other boys left leaving me and 2 girls. We carried on and when I had to pay a forfeit the girls decided that I had to walk the length of the street and dressed as a girl. They thought this was so funny but to me it was heaven, they even dressed me.
It felt like I walking on air and the constant threat of being seen was such a thrill.