I did once when I was younger, I was hanging out with some female friends at thier house and as they were bored they decided to dress me up, I had long hair at the time. Spent ages inthe bedroom while they did my hair and makeup and dressing me in some sexy underwear. Then they sent me down to the living room where there old uncle was watching TV to flirt with him. His reaction was hilarious. Good times, would do again.