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I have cross-dressed at least thrice in my life, but never went out in the streets like that.
Twice when I was about 3 years old, and once when I was 6.
But I don't remember the one from me being 3 year old at all, and I only realized it through pictures in old album.

Well, actually, the only one that counts is the one when I was 6, because I did that intentionally.
But for the two times when I was about 3, I was actually forced to dress that way, and didn't even understand much at that time, so that shouldn't count. I even had lipstick and make-up on! XD
Even the second time, I only put on a dress over my already clothed body, so that's light type of cross-dressing.

I don't think I would have any wish to cross-dress in the future, unless it becomes necessary, or unless it all seems like a fun thing to me all of a sudden.
But I think that time may ever come, even though I wouldn't mind doing so for fun, but never in front of the public.
 
I put on my mom's high heels once and ran in them. It was a loooong time ago. But that's not crossdressing. That's just a kid being a dork.
 
No, I have not, and I never will. Why? I've had an epiphany about it right after I read 'Catcher in the Rye'. I'm serious, too. That, and I find it just wrong. xD
 
I want to, like really bad. D:
 
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