As an sometimes crossdresser, I know the percentage of men who regulary wear women’s clothing is quite small. What about the men who have crossdressed a handful of times or maybe just once? If you have worn women’s clothing, why and how often did you do it? What were other’s reactions to it? And were you at all tempted to crossdress more often?
My last year of college (94-95), the guys in my (all male) house had the idea of throwing a party where we’d all dress as women. I’m not sure why we thought this was a good idea. In any case, I borrowed a very comfortable green dress from my roommate’s girlfriend. I think I also put on some lipstick. I just remember that dress was really comfy. I haven’t had much of a reason or desire to cross dress since then.
ETA: it was a Mardi Gras party IIRC.
In college I attended a Beaux Arts costume ball as Transvestite Nazi Jesus. My roomates were theater majors, and they spent days with me in preparation: the dress and shoes, crown of thorns, armband, and over an hour of makeup.
Some downsides: some frat boys were waiting outside to beat me up, and I learned that lipstick bunches up in the corners of your mouth.
Oh yes, on several occasions. Here’s me in the bathroom of some disreputable Cap Hill club a couple years back. 
That was actually the first time I went out in public in drag – wasn’t even my idea, I was just at a friend’s place visiting and he said “Take off all your clothes, put these on, we’re going out” or words to that effect. Had a blast. I’ve done it on a couple other occasions as well, and I like to add a little bit of cross-dressing flair to my halloween costumes, like last year’s October Revolution devotchka.
I once dressed as a pregnant nun, for Halloween.
And when I was 5, my mother asked me what I wanted to be for Halloween. I replied “a witch.” So we created the most amazing, scary witch who won First Prize in school.
Did it once for a work Halloween contest. Won $200, realized Men are often piggish and that Women’s clothing can make it very difficult to pee.
I seriously doubt that I would be nearly as pretty now.
Capt
Hello
Serious question from a married woman, I am asking with respect, what do you like most about cross dressing, and are you attracted to other men women or other cross dressers? I figure as good a place as any to get less ignorant:)
I did drag a few times in my early 20’s. It was a lot of fun creating a persona. I quit doing it when I was bigger than a size 6 though.
Once. It was part of the freshman hazing ritual at my high school. This was in 1968. In 1972, when we were seniors, we had the practice stopped.
For very low values of crossdressing. I played a character in a play called “Love, Sex, and the IRS” that was forced to dress as a woman in an attempt to survive an IRS audit. It was a comedy, obviously, and my “crossdressing” was really bad. The performances were popular though, and we were held over an extra week, so there’s that.
In order for the term “crossdress” to have any meaning, we have to agree with the notion that there exists “women’s clothing” versus “men’s clothing”. I’m not saying there’s no such meaningful distinction, mind you, I’m just pointing that out. And while I’m doing so, I’ll point out that women who wear pants are not generally identified nowadays as “crossdressers”, although they once were.
I am malebodied. I like to wear skirts for a mixture of reasons:
a) they’re comfortable in the warmer weather;
b) I’m differently gendered and I like doing this as a gender expression
… but I don’t consider myself to be a crossdresser. There’s nothing except social custom that allocates skirts to femalebodied people. But I would consider it to be crossdressing if I put on a bra. The pragmatic purpose of a bra is to provide support for bodyparts that I, as a male, ain’t got. Even there, I suppose someone could counterargue that a bra has other purposes (adornment, decoration) and because of that it, too, is not intrinsically female wear, but to me it is.
I’ve dressed in drag a few times for shows or fancy dress parties. It was fun when I was in my teens and early 20s, but it’s not something I’d consider doing again, especially now that I work in a job where I have to maintain a certain level of decorum.
High school initiation if that counts, which it probably doesn’t. I know it was supposed to be embarrassing but I just played it as if I was in a Monty Python skit. Ruined their fun.
Rule #1: Never ever let them see you sweat.
Well if you really want to know I did a whole thread on it.
Yes I did want to know, I find it healthy the diversity of atheists, religious believers, polytheist, Buddhists, LBGT can all be part of a community here at the Dope.
That’s kind of cool.
I refused to do it when I was cast in a pantomime. They wanted me to play an Ugly Sister in Cinderella, but I refused to dress as a woman, so played a different male role instead. I still believe I’d feel very uncomfortable and awkward and embarrassed to wear women’s clothing.
That’s awesome. Why you didn’t choose that as your username, I’ll never understand.
I think it would be too long.
I’ve cross-dressed for fancy dress parties (as a nun, as an Elizabethan actor dressed as the Nurse from R&J, and a Rocky Horror themed party where I wore the full basque-type ensemble with stockings and heels)
So I guess “Transvestite Nazi Pedophile Vivisectionist Smoker’s Flatulence Jesus” would be out of the question?