Poll: Crossdressing. Ever Done It?

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Xeros

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Aug 13, 2008
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Yes, in 2nd grade, I had to put on a dress for a relay race. Don't ask, don't fucking ask. I don't remember exactly why, but I do remember it was really fucking embarrassing, and the ridicule didn't end until I left the school. I wasn't all about that incident, but it was what started it, and eventually led to me being the class "fall guy". Fuck I hated that place.
 

The Stonker

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Feb 26, 2009
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I have put on makeup and gotten into a dress even gotten a guy to ask me out (yes I can make my voice sound like a girl and like a 40 year old man).

But I'm 16 and I did it with some friends we were just daring each other and hey they dared me to be a girl for a day and I said okay was kinda fun tho.
 

Croix Sinistre

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Oct 25, 2009
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I dont see the point, and I would really like to hear a good reason as to why a male would dress up as a woman.

Actually it baffles me more as to why a flannel wearing lumberjack with a burly beard would do it than a younger guy. It doesn't seem to far fetched for some teens or younger folks to do it. But still, I want to hear a good reason.

Daipire said:
Uh, no....

But I wouldn't mind a [hot] girl wearing my clothes. :)
I agree with this, i wouldnt mind a girlfriend wearing my (or just male) clothes, because i'd know how hot she was under all of it.
 

LongAndShort

I'm pretty good. Yourself?
May 11, 2009
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I was trying to impress a girl who looked a whole lot better when I was drunk.

I looked good though.
 

infinity_turtles

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Apr 17, 2010
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People treat you different(free drinks), you can have fun playing pretend, the breeze is very nice once you get used to it, girls find you much more interesting once they realize you're a guy ect ect...
 

Feste the Jester

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Jul 10, 2009
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I did it once for a middle school French Project where we dressed up for a fashion show and I decided why not.
 

SimuLord

Whom Gods Annoy
Aug 20, 2008
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No. Just...no.

I spend so much time trying to get women out of their clothes and generally think that the best place for women's clothing is on the floor, not on a body (hers OR mine!)

I have, however, seen underwear make a Heroic Sacrifice when a girl I once dated, who had what could be best described as "childbearing hips" decided that she'd try to wear my underwear because none of hers were clean. I had a 30-inch waist and weighed 150 pounds soaking wet at the time! Elastic bands do have their limits.
 

-Samurai-

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Oct 8, 2009
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I've been talked into it a few times while drinking. Nothing too big, though. Shirt, pants, skirt, dress. Nothing beyond that. Whatever, I was drinking.
 

Denamic

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Aug 19, 2009
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Not really...
I mean, not voluntarily.
I was visiting my girlfriend for a couple of months over Christmas and new years while she was studying in London.
And she had a few of her friends also come over for a few days...
1 guy with 5 drunken girls.
I didn't stand a chance.

They made me shave!
My beard!
Can you imagine the trauma?!
 

crypt-creature

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May 12, 2009
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It's not a big deal for me.

Being a woman, there isn't much that a guy can wear that is terribly different as far as anatomy. Even so it still isn't that shocking or awkward.

Now the other way around?
I'd feel more pity for men if so many of them weren't homophobic prats about the idea (not speaking of the people here, as it has been pleasantly civil).
 

Jack_Uzi

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Mar 18, 2009
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I must admit that thought came to my mind one time when I was at a friends house and I told them how strange it would be if we raided the closet of one of his roommates, wait until she got home while sitting on the coutch drinking beer and just enjoy the look on her face. (Guess we didn't like her verry much).

Don't know if I would have really done it if all of us did and I don't think it's got much to do with being straight or gay. Don't take yourself too seriously sometimes is all I can say on that subject.
 

spankcakes

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Mar 3, 2010
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Umm... Never done it, or as much as I remember myself, I've never experimented with that.

And I got nothing against people who enjoy it, whatever floats your boat, you know...
 

Sjakie

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Feb 17, 2010
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I once dressed up as little Red Riding Hood for 'Carnaval', as we call it. Everybody dresses up for 3 days in some weird/stupid/fun outfit. And drinks loads of alcohol while listening to stupid music and sleeping around secretly with people you always wanted to.

Cant find a picture of myself, so here is one of somebody who gets it:

I guess that counts as far as wearing womens clothes looks, for me that is...was. I do remember i kissed more strange girls then any year before, they all loved my red miniskirt and blond wig.
 

ohellynot

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Jun 26, 2008
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Krakyn said:
No, but I like traps. Some of them are even hotter than the chicks around them. Also, I'm straight.
And this chldren is what we call an oxymoron.
 

Snork Maiden

Snork snork
Nov 25, 2009
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Disclaimer: I am drunk in all these pictures. When I am drunk a good picture I do not take. That said there is nothing more fun than crossdressing.





infinity_turtles said:
People treat you different(free drinks), you can have fun playing pretend, the breeze is very nice once you get used to it, girls find you much more interesting once they realize you're a guy ect ect...
When I went out in drag for gay pride I got more girl attention in that evening (from girls of all orientations) then I probably have in the rest of my life combined.
 

Gigano

Whose Eyes Are Those Eyes?
Oct 15, 2009
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Nope, never really had any reason to do so. I wouldn't mind doing it for laughs if a performance or some other reason which it would benefit came up though (ran around in poorly made cow costumes for the entire introduction day at university with the rest of my class, so a dress would've been an improvement...), but I don't have any innate desire to feel/look silly otherwise (which I most certainly would in women's clothing).

I view it pretty much like I view cheese. I don't subjective like it myself, except in certain circumstances (pizza!), but I sure don't mind the least bit that others do.
 

HerrBobo

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Jun 3, 2008
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Not really. I'm mean I have worn g/f's gstrings, just to try them......and yes....maybe had a wank at the same time. I did have sex with one girl while wearing her knickers, but I think that is ok. I mean, I was still having sex......with a girl.