@NeroPR I've had a conversation on here with someone else on some other series about the time I found out my girlfriend actually owned dresses which she generally refused to wear because her mom was just one sidedly getting them for her. I was curious how she looked in them. So, the deal was that she'd wear one if I did.
I was also skinny and I have to say, any man who looks good crossdressing must've put some work into it or has some natural talent for it because it was pretty much exactly "too bad" on me. Although, we all (we showed her mom too) did bust a gut laughing at just how bad it looked on me so it wasn't like we had no fun at least.