Teach me about crossdressing/transvestism

In this thread, panache45 posted an OP that sparked my interest, and I sorta hijacked it for my own questions. The result of this was a lot of helpful posters trying to respond to several different topics at the same time. So I thought I’d bring my queries to a new thread and eliminate some of the juggling there.

I would like to learn more about crossdressing and/or transvestism. In the previously linked thread (and several others), there’s a lot of info about gender dysphoria, but I don’t THINK that’s what I am asking about. I’m also not talking about drag as a performance medium. What I would like to know is:

Are there women who crossdress? And if so, how can you tell? (Part two is asked somewhat tongue-in-cheek - I can tell the difference between “menswear-inspired” women’s clothing and men’s trousers.) Among men who crossdress, is it essential to your sexuality, or all-in-good-fun roleplaying? What sparks the desire, if you know - I mean, what is it about the clothing specifically that arouses a person? Or IS it more about gender identification than it is about the actual clothing? If you crossdress in private (without a partner as part of sex play), why?

It seems to me that there is a shame aspect in this that I am not understanding. Gays, lesbians, transgender people are more open than they used to be (as society gradually if somewhat grudgingly changes) but crossdressing seems to be very much “in the closet.” I should note that while I am very curious about this, I haven’t got a dog in this fight - personally, I could not care less what a person of any sex wears beyond whether or not they smell funny, and I’ve been attracted to and turned off by guys in skirts OR in trousers. I do not get why what people wear is an issue, but I think if I had a better understanding of the reasons behind that, I might.

Disclaimer: I do not want anyone to feel uncomfortable answering my questions - I’d rather see the thread die a quick death than put anyone on the spot. If I ask a question that is out of line, I fully expect to get verbally swatted for it; all I ask is that you assume my questions are out of ignorance (in the original sense of the word “ignorant.”)

I would think that the intent to appear masculine would be the key. A woman who wears a man’s oxford tied under her breasts or the teenage girl wearing men’s boxers as her lower outer garment isn’t attempting to appear more masculine, so they’re not really crossdressing.

Girls and women who typically dress in masculine styles and engage in typically masculine pursuits are called tomboys, a word that has an essentially neutral connotation so far as I know. I remember reading one article claiming that it’s next to impossible for a woman in our society to crossdress because that implies that the person is dressing in clothing generally considered appropriate only to the opposite sex. Since, in our society, there really are very few things that a man wears that would be considered inappropriate for a woman, that would seem to imply that outside of performance, it would be very difficult.

I’m not sure if I agree with this. I come back to the intent. A man who ties his oxford under his breasts could be said to be crossdressing even if it’s a man’s shirt. It’s the feminine expression that draws the attention rather than the masculine clothing.

For me, it was an essential expression of my sexuality. It was an early stage that eventually led to my discovery that I was gender dysphoric. I know you asked to focus the discussion on non-gender dysphoric crossdressing, but it can help one to uncerstand something by understanding what it is not.

For me it was about gender identification.

I derived satisfaction from knowing that I could look like a woman, but I was afraid of the possible consequences should I get “made” in public. Later on, I did dress with a partner, but it wasn’t really a part of sex play.

There is a sense that there is something “wrong” with men wearing women’s clothes. It’s different, it doesn’t fit our (meaning society’s) expectations for how a man behaves. If we can find a reasonable explanation for the behavior, it eases the discomfort. When I began wearing women’s clothes, it gave me the feeling that there was something wrong with me at the same time that it gave me some relief. I wanted to dress as a woman, but didn’t know why. It turns out that there was something wrong with me; I was gender dysphoric. Wearing women’s clothing was appropriate for me because I was a woman. It wasn’t the problem, it was part of the treatment for the problem. Realizing this relieved me of any guilt attached to the activity, because it was actually appropriate behavior for somebody in my situation.

A football player who dresses in a cheerleader outfit on Halloween? It’s a one time thing, done as a joke. A drag queen in a performance show? He’s gay, he’s not expected to act the way a hetero man does. Note that I’m not offereing these as my explanations, but as explanations that might be used by an observer to explain the behavior. Humans crave understanding, and want an explanation for things they cannot understand, and even if that explanation is unreasonable or illogical merely having it can ease our discomfort.

For the straight male, it becomes more difficult to offer an explanation that tells the dresser that this is ok, it’s normal because a or b or c. For some, it’s a paraphilia (fetish). This is an explanation, but it doesn’t offer a lot of relief because it just moves the motivation back a step–why is it sexually stimulating? We don’t know. Hetero men who dress up for reasons not related to gender identiy or sexual stimulation have the hardest time. In the absense of a reasonable explanation, we tend to try on possible ones until we find one that fits, and if we can’t do that, we make one fit. He must want to be a woman. No? He must be gay? No? It’s a fetish, he does it to get off. No? Then, uh, maybe he’s gay and he doesn’t know or he’s lying. Maybe he’s just sick.

(Again, please note that I am not making these claims for myself, just trying to give one possible explanation for why it upsets people).

We don’t question people’s motivations for doing things that are common beyond the basic level. I enjoy riding roller coasters. Why? Because I enjoy it, it’s exciting. I enjoy listening to Bach. Why? Because it helps me relax. People who don’t enjoy roller coasters or Bach might not understand why I do, but they’d generally accept those answers, vague as they may be, because those activities are “normal” and thus don’t cause others discomfort.

Now take the hetero crossdresser and ask him why he dresses. “I enjoy it; it’s exciting” or “It helps me relax” should logically be enough of an explanation, but because this activity comes outside of societal norms, because it makes others uncomfortable, they need a further explanation. In it’s absense, they fall back on the conclusion that there’s something wrong with it, although without being able to articulate exactly what it is that’s wrong with it. Turn the same deeper question back on the “It’s wrong” explanation, and you make the person who holds this position even more unfortable because they don’t know why it’s wrong. They may offer some rationalization, but the truth is that “It’s wrong” because it makes me uncomfortable and I don’t understand it.

This thought process may be taking place in the mind of an observer, but it can also go on in the mind of the crossdresser himself. He could be scared of being discovered, ashamed to be dressing up, and unable to understand why he wants to, but unable to resist because it brings him comfort.

Very true, and I appreciate hearing any knowledgeable input - I just didn’t want to hijack the other thread further or confuse anyone in THIS one.

You underestimate my capacity for curiosity :wink: . I wanna know “why” about just about everything. But seriously…

You know, I really hate the idea of anyone being frightened or ashamed of doing something that they enjoy (assuming of course that what they enjoy doesn’t fall into the category of causing harm to another.) And I think that may be where my questions come from - it’s less “why would someone crossdress?” than it is “why would anyone find that wrong?” So thank you for answering what I meant!

I still don’t really understand what need crossdressing fulfills for a hetero guy, and I’d still like to, so if anyone would like to chime in on that, please do. As a woman, when I dress up to go out I know why - I dress to accentuate my best features and definitely to attract the eye. I will wear pretty underclothes that no one will see because they make me feel attractive. There are certain fabrics I choose over others because they have a more sensuous or comfortable feel to them. I would guess it’s the same for transvestites, and the difference is that no one looks at me funny when I do it? Is there no “socially acceptable” clothing for men that would fulfill those feelings? And again, I go back to the dressing in private thing - is it that the clothing is specifically WOMEN’S clothing that is part of the need?

I should mention, I do know of a female transvestite, who falls somewhere in the gender dysphoria category - she is “straight” for lack of any better term (genetic female attracted to males) and uses the female pronouns for herself, but exclusively wears mens’ clothing, takes a male role in sex, and identifies herself as a transvestite. The only reason I mention it is, unless she TELLS someone she’s a transvestite, they usually don’t even notice, and when she tells people, their reaction is often “Aw. How cute!”

Well, if folks are coming out left and right as TG, might as well put another foot in the pool, so to speak.

I should preface this by saying that I do not currently crossdress and have never done so in a public setting. I don’t think about this aspect of myself much (more on that later). As such, my responses will be somewhat on-the-fly and I won’t be able to offer much in the way of personal anecdotal experience.

I rather thoroughly doubt that it is essential to my sexuality because effectively the last time (that I can remember) I crossdressed was in high school. In fact, I am reasonably certain that my crossdressing has been contained to two days, and one of them featured me wearing a dress just to see what my parents’ reaction would be. I was seven and they didn’t freak, they just told me to put my clothes back on.

Truthfully, I have given it (and some other stuff - let us say that I’m middle-of-the-road in more than one area. It’s terrifically confusing sometimes.) so little thought that I don’t know if it’s roleplaying or if it’s connected to another sense I have sometimes.

Cultural connonations? I’m probably not the best person to ask about this, because for … well, okay. Say in a typical week I give four hours’ thought to X topic. On the other hand, I might think about this topic - crossdressing - in relation to myself for a minute, if that. Part of it is how thoroughly confusing it makes everything in general and part of it is that it’s quite one thing to say “Hey, I’m bi.” It’s - to me, at least - suuuuuuuuuuch a different thing to say “I’ve worn women’s clothing and enjoyed it. I could see myself enjoying it again.”

(on gender ID vs actual clothing) My feeling, and this is something I would not use for forming a solid opinion to be used in groundbreaking research on the subject, is that it may well be related for some people and it may just be a coincidental fetish for others. However, my knowledge of this is so utterly limited that I’ll happily (and relievedly) concede this to anyone with a genuine clue.

I’m not entirely sure, beyond “it felt good,” why I did. I have some theories that look quite scary to me, but at the time I was about as mentally stable as Jame Gumb, so that to me is understandable and I am separated from those feelings now, Og bless. (This would be the place to mention that a random roll of personality dice is why I’m alive.)

The G(ay)L(esbian)B(isexual) of GLBTQA are very out in many places. We have a significant number of them here and out (in varying degrees) on this board. The T(ransgender, though for my money it’s transx - transgender, transsexual, transvestite, etc) aren’t as out, the Q are more out than the T and the A I don’t have enough anecdotal evidence to say.

When you’re out, you want to know enough about yourself, your identity, your sexuality - all of it - to be able to fight stereotypes, to be able to discuss something intelligently and without sounding confused or as though you’re still trying to figure it out. There’s a lot of discussion on GLB folk and some on T folk, but my bet is that there are so many distinct reasons (grouped under general umbrellas of ideas that encapsulate them for purposes of categorization) that it might not be the best thing to say “everyone does it for this reason” or something like that. To those who are critical of crossdressing, that comes across as weak and unconvincing and makes crossdressing look more like a vice than something of which one might be fond and that wouldn’t make the person a freak. That some folks already consider us GLB folk freaks certainly doesn’t help matters much.

There’s also the political nature of it, which is at least part of what causes many of us GLBT folk to be out. If you’re a private crossdresser, there isn’t a hell of a lot the government can do to stop you without incurring hellaciously bad PR, to put it mildly. I doubt a Defense of Clothing Act (or, perhaps more “realistically”, a Defense of Gender Act) would pass, for example, while no DOMA has yet failed if memory serves. There’s no disenfranchisement on the part of the government or specific, strong and loud demographics (such as the various conservative “pro-family” organizations) to limit the rights of crossdressers because nobody knows you’re a private crossdresser unless you tell 'em. Plus it’s not like you hear “Oh, he’s such a crossdresser” and as such nobody knows if you approve or disapprove of crossdressing. It comes up exceedingly rarely.

I have a feeling I’ve left this specific answer incomplete. If so, please feel free to ask more.

Gender roles. 's all I can tell you. Patriarchal society, subjugation of women - both of those are and have been dying out over the past many years, but they’re still very much here and fighting back - tell us that men should wear masculine clothing, should look masculine and women should do/be the opposite. Crossdressing throws a wrench in that the size of … well, something much larger than a garter belt.

If you have a question you think might cause discomfort, welcome to email me (“standard” disclaimer: I’m one person. I haven’t much of any idea how common my responses will be as compared to what others might say).

Number Six, your explanation of it is the best I’ve ever seen. The book Normal by Amy Bloom is a journalistic exploration of the world of crossdressing and transsexuality. She interviews a lot of people who crossdress, and it provides food for thought, but she doesn’t get to the bottom of explaining just what is going on and why. The phenomenological approach is great for beginning to get a grasp on a subject, but it doesn’t explain much.

Life On Wry’s question could only have come about in the past 60 years or so, when women were able to openly wear men’s clothing and have it accepted as unisex, as “normal.” Rosie the Riveter started it, if you ask me. Before that, there was no gender-neutral clothing. George Sand could mark herself out as a bold, edgy, devil-may-care female transvestite because of the stark dimorphia in 19th-century European clothing. What a disadvantage the female transvestite is at now, as in the example of Life On Wry’s friend: she’s invisible! Even if she wants to come out in the open with it, no one will notice.

Feminist theory offers the best explanation for Life On Wry’s puzzle. Analysis of gender power relations. Men have the power in this society. The implicit assumption is that power is the ultimate goal of human life. So if the less powerful gender wants to imitate the more powerful, at least it’s understandable. Why wouldn’t they want to try to get some of that power for themselves?

Even if at first it seems to blur the sacred gender boundaries, in fact it scarcely has affected the gender boundaries at all. Why? Because the underlying assumptions remain untouched: men still have the power. As long as it’s all one direction, as long as women are trying to imitate men and not vice versa, the men can feel secure in their gender’s power. So women in men’s clothing are accepted as having a place within that power structure: still a subordinate place, they are still women, still second-class male imitators. No threat to the system.

Now if men dress as women, the more powerful and privileged lowering themselves to the position of the subordinates, that seriously does shake the gender power structure. How could a man, born to power, willingly choose to demean himself? He becomes a gender traitor and must be punished severely to deter any eroding of men’s power over women. In Margaret Atwood’s novel The Handmaid’s Tale, “gender traitors” were strung up in public and their bodies left to hang as a warning.

It occured to me just a little bit ago that I posed my questions very awkwardly - “this is something people may find embarrassing, tell me why you do it.” :rolleyes: Actually, there’s probably no “right” way to pose those questions. I appreciate the answers, and Johanna, I’ll be looking for that Bloom book.

Number Six you’re absolutely right - “because” is reason enough, or should be.

There are those who want to appear and act completely like their opposite sex.
There are those who like to dress up completely as their opposite sex without wanting to appear to be a member of their opposite sex.
There are those who like to wear clothing of their opposite sex because it turns them on.
There are those who wear clothing that might be considered more appropriate for members of their opposite sex in order to shock or defy tradition.
There are those who wear clothing that traditionally belongs to the opposite sex without even considering the fact.
There are others I havn’t even thought of…

All of the above can have any of the sexual orientations that exist. There is only mild correlation between cross dressing and sexual orientation types.

Myself, I like to wear clothes that are interesting and that I (think I) look good in. I have never worn womens clothes, as all my clothes are my own, yet I happily dressed up as Adam Ant and wore a long pvc skirt on New Years Eve. I danced with some very sexy women, and just happen to be heterosexual, so was very happy with the result of my clothing choice.

And isn’t it just like me that I’d pick something like transvestism to be mildly jealous of? I would not say that to demean anyone who’s struggling with the world’s incapability or unwillingness to just ACCEPT differences. Being a girl means I can generally dress however I please without comment, but it also means that I don’t have an easy means of simply playing dress-up for my own pleasure. More to ponder.

LifeOnWry, you can still do the female transvestite dress-up, you just have to choose the right outfit. There’s still one outfit that unambiguously screams “MALE,” and that’s because it went out of date before unisex came in. So it exists preserved in the amber of time. I speak of the 1920s-style formal wear. You know, what the rich guys in the Marx Brothers movies wore when Groucho was poking fun at them. The tuxedo with tails, the boiled shirt (what the hell is a boiled shirt, anyway?), the top hat, spats, cane, and to top it off, of course, the monocle. Get all decked out in that, and I promise you, when people see you coming, they will ask “Who let that female transvestite in here?!” :wink:

If you ever saw the most obscure, forgotten movie made by Merchant and Ivory ages ago, Savages, remember the formal 1920s-style English upper class garden party in the mansion (again, being poked fun at). The woman and the guy who wore each other’s clothes? She succeeded as a female transvestite because she wore that 1920s-style formal tux and tails.

Oh yeah, and not to forget Marlene Dietrich. She knew.

Aha, but herein lies the rub. In my everyday dress, I’m pretty gender-neutral - jeans and sweaters or t-shirts in solid colors. When I go somewhere dressy, it’s generally black trousers and a blouse or sweater. I FEEL as though I’m dressing in drag when I go girly - flowers, lace, skirts, any of that kind of stuff and I feel, quite frankly, weird. (My ren faire garb is pretty traditionally girly, with skirt and corset, and I have for years referred to it as “going in drag.” And just for the record, my underwear is almost always excessively girly, which is in pretty stark contrast to everything else.) Since I’ve been dressing so casually for so long, the one time my husband came home from work to find me wearing a dress, he said, “What are you all dressed up for?” I was actually embarrassed to be caught dressing like a girl!

I would not equate my embarrassment with that of, say, a guy who “got caught” dressing in his wife’s clothing, but the only reason it’s not is because I actually am a girl. I know very very few women who dress girly with any kind of regularity - at the moment I honestly can’t think of ONE in my acquaintance. So I wonder, as time marches on, will “frill” eventually be the sole domain of transvestites?

As a girly-girl, I bloody well hope not!

Seconded.

Thirded.

LifeOnWry, if wearing a dress made you feel “girly” then maybe, in a way, you were crossdressing. You were just doing it within the roles of your own gender.

Of the two sexes, women have a broader palette for expressing themselves emotionally and/or sexually. Really, what meaning is there to a man saying that they’re feeling a little ‘metrosexual’ (or whatever) today, and would dressing the part make much of a difference? It seems plausible that a guy might want to take on part or all of a female role (‘stereotype’ might be a better, more common term) to provide an outlet to express some part of themselves that otherwise might find no other way to the surface.

And if dressing a little ‘metrosexual’ (or whatever) made a difference, would it be acceptable? Classical feminist theory may be a good place to begin discussing the issue in that men have traditionally positioned themselves to gain social power, but women have been able over the decades to gain social power without losing the personal power of self expression (actually, it seems that the range of accepted roles has expanded.) It seems that men, on the other hand, still risk a very real loss of power if they express themselves in ways that aren’t commonly recognized. To illustrate, I don’t think that there is anything that a woman could wear or any sort of role on a gender, sexual or sensual spectrum that a woman could take on that would guarantee her getting fired, divorced and/or expelled from most social organizations, but any deviation along these lines by a man could easily wreck his life in one or more ways. One might say that ‘crossdressing’ by women is accepted or even expected, while it is still taboo for men.

Sure, she’s straight, but would ‘stoney’ and/or ‘butch’ work to describe your friend?

I hesitate to group my experience in with those who feel a need that causes them shame, but I DO get the appeal of “ooh, this is a little naughty/risky and therefore exciting.” And I’m completely on board with “I like the way this feels, and it makes me feel sexy/special/attractive/whatever.” If you’ll forgive once again my crossthreading, one transgender person referred to crossdressing as a means to provide temporary relief for her gender dysphoria, which I take to mean, “This is how I feel I SHOULD look.” I get that, too, now.

What I think is still eluding me is that there is clothing intended for men that is sexy and sensual, a “little naughty.” But a guy who crossdresses isn’t getting what it is he needs from that. Which leads me to the (perhaps erroneous) conclusion that it’s something about the very girly-ness of stockings, skirts, and what I call frill, that is fulfilling that need.

I guess I do understand why someone would feel the need to stay in the closet where transvestism is concerned, but all the same it makes me a little sad for people who live in fear of discovery. I don’t know that there’s anything I can personally do to alleviate that, but I’ll just state for the record that I would stand up for someone’s right to wear whatever the hell they want.

I’ve never heard “stoney” before, and I think most people would assume “butch” when they see her. All I really know about this person is through a message board and reading her personal site. Met her in person briefly, and had I not known of her, I’d have said “effeminate teenage boy.” I do know she routinely wears what I can only call a prosthetic penis, self-identifies as a gay man trapped in a woman’s body, and is not at all interested in a sexual relationship with a woman.

You understood correctly.

Honestly, I’m not too familiar with the whole stone concept myself (being a straight guy may have something to do with that.) A friend once mentioned that his roommate described her relationships as stone butch-femme. He said that he saw a lot of commonalities with traditional marriages from the 1950s, where the roles were strictly defined.