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Have you ever crossdressed?

Mooites

Take the Stage!
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Ever crossdressed?

I have no idea where to put this, so I'll put it here.

Its a simple question really, so answer if you feel comfortable with it.

For me, yes, Im a crossdresser. From fourth grade to sixth grade, I would only wear guys clothes. Guys shirts, big baggy shorts, and no bra. Yeah, that was me.

I still have a guyish personality apparently.
 
I think this should be moved to Outside the Box...

To answer your question, no. I'm a guy, and there's too much work involved wearing women's clothes.
 
Can't say I've ever thought to do it myself, but I also think that this thread belongs in Outside the Box. [Moves]
 
For me, I just wear men's jeans and sneakers
 
Only twice, at the end of camp disco (army cadets). A bunch of us did it first time round second time only the two of us. the first one a generic dress the second time a nurse outfit.(no pics)

It was fun but not something id do every day.
 
twice... both times there was a cherity auction to raise money for some cancer thing. The people who bought me both times dressed me up as a female. It was weird.

Women can get away with it easier than guys. Most of my female friends borrow their boyfriend's clothing because it is usually warmer than their stuff. They are able to claim that it is her's because women can wear jeans and t-shirts normally. Guys can't say the samething about skirts or dresses.
 
I'll do it occasionally as an everyday outfit or in gym class as a joke. xD I can't stand wearing my shorts so high up they go up my ass. :< It just ticks me off. I don't have a problem wearing gym shorts. I even wear baggy jeans occasionally. :<
 
I usually don't wear a bra, and most of my wardrobe consists of baggy pants and tshirts, typical guy clothes. But I'm not trying to pass as a guy, so would that count as crossdressing?
 
i dressed as a cheerleader once

Hey Deadpool! I think you look so nice and cute to see you as a boy dressed as a cheerleader. lol, That's lovely and adorable. I think crossdressing is ok, but usually girls do it. I don't think or believe I've ever crossdressed before and I'm a guy.
 
On our trip to Greece and Italy, we had a drama night in one of the conference rooms of the hotel in Rome we were staying at.

A group of us did a mocking skit of what our tour group looked like walking down the street. The girls overheard my impression of the ditziest girl in our group, so I got stuck playing her.

I borrowed some of her clothes, stuffed socks down my shirt and straightened my hair.

And now a bunch of students at my old highschool have leaked the photos.

-.-;;
 
Technically, I did. I would wear some of Prime's old shirts to work. But I really wasn't trying to pass as a guy. (Why throw out perfectly good shirts when I could use 'em? I was just recycling them.)
 
I want to dress up like a guy, but I would only do so at a con.
 
I crossdressed once, but that was for a play so I don't think it really counts. Crossdressing wouldn't really be my cup of tea, to be honest.
 
I crossplay Edward Elrich from FullMetal Alchemist. Normally, I tend to wear jeans and sneakers. I used to wear really guy shirts as well, but lately I've gotten used to being in the more 'girly' ones. The two parasitic lumps of flesh on my chest make it fairly obvious I'm a girl, so it's kinda hard for me to try as pass as a guy.
 
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