Would you cross-dress?

Maybe.
I don't know

Yeah, I have before for theatrical productions and costumes when I was younger.

No biggie...well, at least it used not to be: now I have boobs.

Been there and done that just to pass my PE [dance] in college since our course only has 4 women and 32 men.
Didn't make it and got a 4 [I think this equals a D] as my final average. I didn't look cute of course, but at least I looked better than my bearded, musclebound classmates in their one-piece gowns.
One had a boner during the session and did it ever look so wrong.

When i was younger my grandmother had a life sized doll (only just realized how creepy it was) and the hair had come off just like a wig. One day I decided to see if I could recognize myself if I wore the doll's dress and hair. I was one ugly looking little girl in the mirror. So to answer your question I have in private but not in public. And as for the present.... I wouldn't unless I got something of significant worth out of it.

I wouldn't do it unless some serious money is on the line. It's just by principle. I'm a man and proud to be a man. I have no interest whatsoever in dressing like a chick.

Fuck yeah I would. I ain't no pussy.

Not unless there was some payoff involved. And even then...

I will admit that I have put on ladies lingerie from time to time. in public once but it was under an overcoat. God that was a fun walk through the mall.

For a few cheap laughs I would.

I'd do it for a joke, or money.

Just cause, no.

To be honest, I've thought about it a couple of times, but if I was given I choice to I wouldn't. I don't want to risk some taking a picture, being caught, or just putting on girl stuff in the first place. I can't even imagine myself crossdressing

No I won't cross-dress both in public or in private.

There's this one time though I had a woman role in our English class play. Horrible.

I don't look good enough to be a trap.

I would, I think it would be fun. o u o

i'd trap...but i would look like Brittany Grinder

I look like a trap from behind thanks to my long hair.
The look on guys trying to pick me up being greeted by 'What's the matter bro?' and seeing my mug is priceless.

Well, I would.
I have actually before, especially when camping with my friends. But, I know I don't pull it off well enough. Would have to cut my hear. That and I look to feminine.

But yeah, it is fun.

I love the response this thread is getting. But I feel like there's a lot of potential discussion that is being missed out on. Primarily, why people want to cross-dress, or why people don't want to cross dress. I'm going to make a long post and pour my heart into it, people might laugh at me, or really question my motives/thoughts... but here goes anyway.

Why I personally want to cross-dress? I like to cross-dress simply because I want to look cute and want to appeal to the opposite gender with this "cute-ness".

What is cute to me? I love frilly dresses, gothic/sweet lolita style clothing, and lolita fashion. If you have looked at my user name, you may of already picked up on it, loli is cute to me. For me, wanting to look cute like a loli might related to my unreachable desire of always wanting to be a cute little girl. I've always suspected some (but not all) other loli-lovers might have similar desires but I've never confirmed it. So yeah, I want to be a cute little girl. Have your chuckle if you want.

Appeal to the opposite gender? You most likely have easily figured it out by now, but I will plainly say it: I am male. I want to dress in a cute dress to appeal to the female gender. Two big things to point out here which I know people will having glaring in their mind after reading the previous sentence:

1) I suspect some people might think all cross-dressers want to appeal to their own gender, and people may steer away from it labeling cross-dressing as primarily "gay" activity. Obviously I am not trying to appeal to the same gender, I am trying to appeal to the opposite gender; so bluntly not all cross-dressers do it for a "gay" reason. Of course others may do it for completely different non-gay or gay reasons. Attraction of x gender or any gender might not even be an influencing factor for cross-dressing for some. Just to be clear, I have nothing against people who cross-dress to appeal to the same gender.

2) I know people are going to question "does dressing up in a dress like a little girl really appeal to the female gender?" or find it strange that I think it would. Obviously not all females will find this type of action appealing. I assume some do... I hope.

So after all that... I gave my reasons for cross-dressing. So don't only say if you would cross-dress or not, say why you would or wouldn't too! I don't mind any criticism too, I know people are going to find some of my thoughts as absurdly "weird"/different. I don't mind if you say you think they are weird too! Any input is cool.