This may not match the aims of your blog. If it doesn't, just dump it.
I believe this is an OOTS First. I have known a few guys who played with dressing up as kids, I think it's amusing, even entertaining. But, ummm not for me.
When I was around 8 and 9 years old I sometimes went in my mother's closet and put on one of her dresses. I liked to play "lady" and clomp around the house in high heels. For Halloween one year I decided to dress as a woman, specifically my grandmother because she was very small. I borrowed one of her dresses and hats, got my mom's high heels and a big beaded purse. Also I wore a veil over my face. I thought I was really going to have fun. But my mother informed me that my father did not like for me to play "lady," so the plan fell through(he never mentioned it to me himself).
When I was in college, some of us went to New Orleans on Spring Break. I was intrigued by the female impersonators in the clubs - they were better-looking than the real women! I envied them getting all dolled up in women's clothes.