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What it takes to be a crossdresser

What it Takes to Crossdress

I don't have to tell you, because you've been there and you know: it's not easy being a crossdresser. Nobody likes us.

Portrayals of male to female crossdressers in movies, television and literature, the primary exposure to the subject of crossdressing for most of the population, overwhelmingly portray crossdressing as either tragedy or farce. We are either the fringe element of society, and must be obliterated ("Dress To Kill", "Silence of the Lambs") , or we are utterly laughable, only no one is laughing with us, they are all laughing at us ("I Was A Male War Bride", "Some Like It Hot").

The only time male to female crossdressing is ever taken seriously in its context is when the context is gay men and crossdressing takes the form of drag. However, these stories typically focus more on the life and times of gay men, with crossdressing (drag) being a secondary sub-plot ("Pricilla, Queen of the Desert", "To Wong Foo").

To help you get to where I am with this, try to image Hollywood making a movie, and paying three top-name actors to be in it, about three heterosexual crossdressers driving to the Southern Comfort event in Atlanta and breaking down in some small, rural town along the way. Don't hold your breath.

When heterosexual men cross dress in movies, we have farce and slapstick. The other day I was perusing the bargain rack at the local Barnes and Noble and I found a small book on drag in the movies. The book was kinda cute: if you held it one way and read, it talked about men dressing as women in movies. If you flipped it over and turned it upside down, you could read backwards it and it talked about women dressing as men in movies. The two parts meet in the middle of the book.

In all cases, the women who dressed as men were serious characters with real problems that were solved by assuming the identity (and status) of a man. If the movie itself was a comedy, the women were by no means comical.

The male to females? Jerry Lewis, Milton Berle, The Marx Brothers, Lou Costello, Tony Curtis, Jack Lemon, Cary Grant. For these characters, wearing womens clothing was done in the context of being compromised. There was no choice, it wasn't the most desirable option, but it was the only way.

Literary fiction is not much better. In Tama Janowitz's "The Male Crossdresser's Support Group" the main character, a marginalized woman working for an Ad agency in New York City, finally breaks through in her profession when she presents herself as a man. In "Dreamhouse" by Alison Habens, a story about a young , '90s woman coming of age, a crossdresser who lives in the apartment downstairs is attacked and almost raped at a party, having been mistaken for a woman by a drunk partier.

Most people in this country will never meet and spend time getting to know a crossdresser. They may know people who are crossdressers, but they will never know this. All that they know about the subject will come to them second hand and vicariously. You can't blame these people for having the wrong conception.

So what about the gay community? Here too, I don't think there is any implicit acceptance. Sexual orientation is not inherently connected to gender. The image of the effeminate homosexual man is a stereotype. While it is the case that more and more gay and lesbian organizations are adopting policies that include "transgendered", I still don't believe that on the level of personal politics, a gay man or lesbian woman is particularly inclined to accept a crossdresser.

Many crossdressers think that their outings are limited to gay bars in their communities. I've been in my share of bars in the past 25 years, even working the door in one or two. People aren't the same in bars as they are at work or at home. You are just as likely to encounter trouble in a gay bar as you are in a straight bar.

Finally we come to our own little community, and boy is the house a mess! Recently, the Transgender Forum posed the following question to its readers: "What bothers you the most about the transgender community?"

Overwhelmingly, the response was the amount of in fighting between transvestites and transsexuals. Hands down, it was the number one complaint. In my own town here, I have seen this. There are two organizations here, one is a Tri-Ess affiliate, the other a so-called "open" group. Attendance in both groups is very low, sometimes no more than 4 or 5 attendees. Membership has been stagnant, with as many members joining each year as failing to renew. The Tri-Ess affiliate of course is limited in whom it can claim it serves, but most members of the Tri-Ess group belong to both groups. Attendance by partners is non-existent.

I wish I had a dollar for every time I heard the phrase "only a crossdresser" used in the past two years, sometimes by crossdressers themselves. Coming from a crossdresser, it sounds like an apology. From transsexuals, a put down. How many times have I listened to someone who has recently started taking hormones chirp "Just think, last year I was a crossdresser!" I mean, could you imagine Colin Powell going up to some unemployed black man living in an inner city neighborhood and saying, all smiles and bubbly, "Just think, 40 years ago I was a ghetto nigger!"

I've heard transsexuals say they don't like going out in public with transvestites because they always get read more easily when they are with us. Apparently it's harder to pass hanging around crossdressers. Well, at least transsexuals and transvestites have something in common: we both want to pass. Think about that as you draw into your opposite corners.

Just for the record, I'm no paragon of femininity (whatever that means), but I do OK in public, and I have gone out to restaurants and stores with some bug ugly transsexuals, and I took a lot of stares and snickers from people that hurt like hell and made my face flush with anger. And I'd do it again tomorrow.

The straight world doesn't like us, the gay community has no use for us, and even our own community would like us to go away. Strange, considering that as people, crossdressers are spouses, parents, employees, employers, homeowners, and business owners. We care for our families, do our jobs, get involved in our kids schools, take care of ourselves and burden no one. We don't do anything that would make us unlikable.

Oh, I forgot. We crossdress….

So here I am, a page and half into an article entitled "What it takes to be a crossdresser" and I haven't even begun to answer the question. Typical.

As has often been the case with other issues in my life, my awareness on this subject was brought into focus through my role as a father to my nine-year-old daughter

In another few years, her life is going to be turned upside down, and at the ripe old age of 12 or 13 she is going to have to make decisions about having sex, taking drugs, drinking alcohol, smoking cigarettes, how hard to work at her education. And most of the time she will be in the company of people who are going through the same turmoil as her, facing the same issues, challenges and threats. Can she turn to these peers for help and advice?

No fucking way!

As an adolescent, she will want to belong, simply for the sake of belonging. Often, she will have to decide whether she should behave like everyone else around her, or behave well. How will she do that? What will prevent this delicate young scion from being trampled into the ground by the myriad of messages assaulting her on a daily basis?

A little voice inside her head. A voice that calls to her, beckoning her to a place inside herself, where her self can live and grow in a safe, quiet, nurturing space. Where she can live with her self. Mary Phiffer, writing in Reviving Ophelia, chronicles the devastating effect our male-dominated, sex- and looks-oriented culture has on the self-esteem of adolescent girls.

A very wise friend of mine, who also happens to enjoy crossdressing, enlightened me to something in our language. We often think of humans as having five senses: sight, sound, touch, taste and smell. Yet we use phrases like "sense of humor" and "sense of direction." If these really are senses, they certainly can't be studied in a scientific manner like the five basic ones. So obviously medical science doesn't recognize them.

What about sense of self.

Do you have a sense of self if you let other people tell you who you are, what you are, what you should think, how you should feel? Can you distinguish between original ideas and thoughts that come from the self and reflect the workings of the self, or do other peoples words and ideas somehow become your own?

A strong sense of self becomes essential to survival when we pursue a path that those around us consider unpopular. Consider the sense of self that Jackie Robinson must have had, given that even his own teammates openly hoped for his failure. He belonged to a club called the Brooklyn Dodgers, but it didn't mean he was accepted. How many of his peers, both black and white, would have told him not to do it?

A strong sense of self is also essential when we join any group or organization that forms around narrow definitions of what its members should be. The pressure to conform under these conditions clashes directly with our notion of who we are as individuals.

Typically, when we talk about alienation, it is in the existential sense, of being alienated from other people, being alone. But the more devastating kind of alienation is the alienation from self and the loss of self to the collective body, the group.

Like the adolescent girl, crossdressers are under assault. The message is loud and clear and consistent. Everywhere we look, we are told how we are wrong. Even those closest to us, in the transgender community, use their knowledge of crossdressing to oppress.

This is not to say that trassexualism is to blame for al the problems crossdressers have. Far from it. Transsexualism is as much a creation of a thousand years of, first Christian, then scientific patriarchy as is the taboo of men wearing womens clothing. The existence of a clinical diagnosis for transsexualism and the medical technology to treat it makes crossdressers appear unwilling to seek help for their problem. In fact, many crossdressers don't see themselves as having a problem.

And it takes away a reason for crossdressing. In the transsexual model, wearing women's clothing allows the outward image to coincide with the inner image. Crossdressers, on the other hand, make no claims to want to be women. Therefore, the inner image remains masculine while the outer image changes. What's the point?

But I will add this. When done properly, by a crossdresser who devotes time and energy to learn how create a quality image, who learns the art of makeup use, who looks carefully at fashion and what is appropriate to wear for that individual, the outward appearance is frequently improved quite a bit. The proper use of makeup and clothing improves anyone's appearance, male or female.

I have met many attractive people who happen to be men wearing makeup and women's clothing. Not hot babes, just good looking people. Do they pass? Probably not, but they certainly look like they deserve respect. There is nothing unwholesome about their look or behavior at all.

True, many crossdressers (and transsexuals) don't know enough about how to use makeup, or what clothing looks best on them, or what is fashionable (in fashion) or what outfits go together, and their image suffers. But these are things that can be learned. By anyone. At all. We can all benefit from more practice.

Unfortunately, the very things that it takes to be a crossdresser, a strong sense of self and an independent nature, also make it hard to join together. It's not in the nature of this type of person to cling to the crowds. It is a community of captains, each in search of a crew, so to speak.

Jackie Robinson would have lived with much less stress in his life if he had stayed where he was in the Negro Leagues, out of society's sight, out of society's mind. But it wasn't in his nature. He put himself out there, chose a path for himself that was unpopular with almost everyone and he took the blows that went with it.

Jackie Robinson was a great ball player. He had a strong sense of self. He would have been great at anything he did.

Written by Yvonne, a married crossdresser with a supportive partner that lives in the Albany, New York area. Visit her site at:

Do you have a story you'd like to share about your experiences with crossdressing? Please send to and we will consider adding your story to our site.


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