A friend in college was a half man-half woman for Halloween. Very funny idea, and done well. Too well. Gradually people realized that his makeup on the female side was better than any of the real women at the party.
One year for Halloween I did. My wife put on my makeup, and we scrounged up plus-sized clothes.
Apparently I make a VERY ugly woman (which is interesting, because I’m reckoned a handsome guy); I got runner-up in the scariest costume category that year.
That’s so transgressive I think it cancels itself out at some point.
I would think a bra would be a clincher.
It does not surprise me that nobody (yet) is willing on a general message board to associate his username for all posterity with a bonafide cross-dressing persuasion. In the minds of many posters, it would cast his mental health into doubt, to be brought back and used against him later on.
When I was young, I don’t remember how old I would I have been but younger than 14 I happened across a bra. I tried it on to see what it looked like in the mirror.
Now I am going to melt from the embarrassment.
I once signed on to an acting group after my divorce when I was 40. Our coach asked that we all cross dress for one evening practice session. We were supposedly at a high society party and spent the night mingling as the opposite sex. I just felt ugly and a bit freakish mainly because of my body type.
Only for a high school senior video project for French class. I dressed up as my teacher and as a Catholic school girl. The main thing I discovered is how ungodly hot (as in temperature) leggings/pantyhose are. ETA: Oh, there actually was one more time–maybe when I was in fourth or fifth grade. I don’t know how much you want to count this, but I had to model a girl’s communion dress because I was the same size as my cousin in Poland. There is a picture of this embarrassing moment somewhere in one of my albums. Perhaps I’ll dig it up and throw it out there on a Facebook “throwback Thursday.” Actually, it may have been a confirmation dress and more like 6th or 7th grade, now that I think about it.
Well that rules me out. I could pass the pencil test.
And I still can, 33 years later. Pbbbt!
Halloween costume when I was 12 was “woman”. I put on a bra, high heels and makeup for that one. Probably the most crossdressed I’ve ever been.
In high school I wore a dress to school to shock people. Actually, it was just a long skirt and t-shirt. The next year, some dude came to school with the full prom attire, including poofy dress and makeup. :rolleyes: I already blazed the trail, dude, now you’re just hamming it up!
I’ve occasionally worn skirts since then, just because they’re comfortable. Especially at “burns” (which include Burning Man and its smaller regional events), where gender bending costumes are relatively common. Thinking about getting a cargo kilt though, just because I love pockets and can’t do without them for long.
None of that really counts as “crossdressing” in the “I get a kick out of dressing like a woman” sense, though.
I would hope that of all the places on the web, the denizens of the Dope would be more open-minded than to regard cross-dressing as a sign of mental illness.
In my case, I’ve already admitted to a diaper fetish, so why stop there?
As it happens, my fetish led to my interest in a narrow slice of the transvestite world. Erotica for ABDLs (Adult Babies/Diaper Lovers) often features adults dressed as little kids – and most of the time from what I’ve seen, it’s women dressed as little girls. Lest your mind be forming horrific ideas, let me say in a clear and loud voice that ABDLs have absolutely no connect whatsoever with pedophilia. Quite the contrary, the fascination for many hetero ABDL men involves becoming the little girl, stripped of authority and status and made to wear cute clothes (and a diaper). Seriously, search on Google-Images (or Pinterest) for ABDL and see what comes up. Among other things, for many ABDLs it has connections with bondage/domination, submission, humiliation, and related sexual interests.
In the course of exploring my interests, a few years ago I stumbled onto the Birch Place Shop (spoilered for some NSFW imagery and text in their catalog):
They have tons of cross-dressing stuff, but the overall bent is toward the “sissy” side of things which is distinct from run-of-the-mill “tried on my mom’s panties” cross-dressing and even from the “drag queen” genre. Lots of lace, frill, “gingerbread,” tons of pink, and so on. Check out their “adult baby” and “bondage” sections, and you’ll have a pretty good idea of it all.
So yes, I’ve been shopping there. And also on amazon, for things like stockings, bras, and cosmetics. From time to time I have the house to myself for a day or two, and I play dress up. Predictably, fantasy does not live up to reality – the reality being that women have years and years of practice in which to figure out what makeup and clothes make them look good, and they have a female body to boot, and I don’t have the time or wholly supportive environment (wife knows/tolerates but does not participate) in which to learn how to make my masculine, adult self disappear into an outfit. But it doesn’t stop me from trying, or from daydreaming about it a lot.
Well, since I’m kind of out and public about being a diagnosed, escaped and at-large-untreated paranoid schizophrenic, I think it’s fair to say I’m not intimidated by the prospect of my mental health being doubted 
Meh. I’ve just done it a few times because it’s hella fun, and I’m certainly not a bona fide drag queen, but if I were I’d see no reason to hide the fact. Keep in mind also that crossdressing or being a drag queen is very different from, for example, being transsexual and dressing according to your actual gender. A drag queen is not necessarily (but can be) FtM, and is not necessarily homosexual either. One way or the other, it’s just the clothes you put on, and if anybody would assume things about somebody’s mental health based only on the clothes they like to wear, I think they’re the crazy one.
Crossdressing would mean out in public, which I’ve never done. But, as a kid, I did play dress-up and was completely gender agnostic in my choices. Particularly I liked the challenge of walking around in high heels.
I also will point out that there are bras for men with gynecomastia. The article of clothing is not what makes it feminine, but the style. There are male skirts–as long as they are styled as kilts. There are male dresses–as long as they are styled as night shirts.
Crossdressing just requires you to intentionally present yourself as a gender other than your own. The “dress” part is a bit of a misnomer.
(And, yes, I guess that technically means the genderqueer are cross dressing when they hide themselves under binary gender. But, then again, how do you know they are hiding anything?)
For four years while in college, a friend and I dressed as women for Halloween. Each year we put more and more time into our costumes. By the fourth year, I was one smoking hot chick. I had shoulder-length hair at the time, so that helped make it look more “natural.”
We won costume contests at various bars dressed up like that, and I am still amazed at the amount of very positive female attention it got us. Very positive. On Halloween when girls dress up like slutty anything. Fun times, college.
The fourth and final year it also earned us an ass-whooping. A meat-headed bouncer at the bar we did our costume contest at saw us the next week at the bar, and assumed we were gay. He was watching us all night and waiting for a reason to throw me and my buddy out, and pound on us in the process. I forget what prompted it, but he ended up dragging me across the bar by my throat while pounding the shit out of the side of my face. Another buddy of mine happened to be the DJ there on Fridays and so got the goon fired the following week.
But there are clothes designed for male bodies and other clothes designed for female bodies. It’s mostly about style (which body parts to hide/accentuate) but there are some practical elements, too.
There was an episode of Oprah once where they taught women to “cross-dress” and go around looking like men. It usually took a combination of hats, fake mustaches/beards, and clothing.
But the biggest thing was the difference on how men and women walk, talk, sit, and even stand. Most people dont realize the differences.
Sooo… how **you **doin’ ?