Well, as a kid! I don't ever recall dressing up as a girl when I was little, does anyone often see little boys or know of boys that do (not that there is anything wrong with it, I just haven't heard of that much before)? Maybe for Halloween?
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Surprise! Little Tom Cruise used to like to dress up as Dorothy from the Wizard of Oz and other girls. I'd like to say that's pretty normal and that all my straight male friends did that as a kid...but, I'd be lying of course. The irony of Mr. FOD dressing up as Dorothy.
http://big24fan.blogspot.com/2005/08...f-dorothy.html