Crossdressing 101

Originally appeared in Transgender Tapestry #101, Spring 2003.

Miqqi Alicia Gilbert

The name you will find on my birth certificate, driver?s license, and other official documents is Michael A. Gilbert. I?m a Full Professor in the Department of Philosophy of York University in Toronto, Canada. York is the third-largest university in Canada, and I?ve been there for a very long time. In addition to the aforementioned name, I have another, which can be found on my IFGE membership card, numerous event badges, and the articles and columns I write for the transgender community. That name is Miqqi Alicia Gilbert, and it?s been my chosen femme name for over 15 years now (before that I was known as Shelley). I?ve taken the name Miqqi Alicia because I?m a lifelong crossdresser who, unusually, is out and public about his pastime. I?m 56 years old, have been married a few times, once for 14 years and divorced, once for two and widowed, and currently for 13 and neverending.
I am, in many ways, perfectly ordinary. I love to play tennis, watch football, help preside over my wife?s marvelous dinner parties, travel, play with my little granddaughter, and otherwise do things most men my age enjoy doing?except that I also regularly like to dress up in women?s clothes, feminize my personality and mannerisms, and relate to the world from what I believe is a woman?s point of view. I?ve been doing that, one way or another, since I was little, and have no likelihood, desire, or intention of stopping. The practice has waxed and waned over the years, but has always been there, and I have learned that it will never go away. So I have decided for this column to try to answer some basic questions the typical female partner of a typical heterosexual crossdresser might have. The answers are my personal ones, and they are idiosyncratic, concocted, and possibly wrong, but above all, sincere. I love crossdressers and I love their partners, and I don?t believe either group has an easy row to hoe.

The questions I?ve chosen are: Why does he crossdress? Is he gay? Is he mentally unbalanced? What?s in it for him? What?s in it for me? What does the future hold? Obviously the answers can?t be long, but they will be painfully truthful? that I can promise.

Why does he crossdress? The answer is simple: he has to. We have a compulsion to adorn ourselves in women?s clothes, a compulsion that, in most cases, has been there as long as we can remember. No one chooses to be a crossdresser?no one wakes up and says, ?Hey, my life?s too simple, I?ll put on a dress and see what happens!? No, you do it, I do it, because I need to. If I don?t, then over time the pressure will build and I will become tense and stressed.

As for the deeper ?why,? as for what causes it? well, that?s anyone?s guess, and there are many, but none is compelling, and none will affect my being a crossdresser. So the simple answer stands, though it?s really complex, because no matter what he says, it will continue and will happen again. We have no choice.

Is he gay? No, he?s not gay, or at least not usually. He doesn?t want to be a woman so he can be with a man. In fact, he doesn?t want to be a woman at all?he wants to pretend he?s a woman sometimes. If he wanted to be a woman, he wouldn?t be a crossdresser; he?d be a transsexual, and that?s a whole other ball game (you?re telling me!?Ed.). Having said he?s not gay and doesn?t (typically) want to go to bed with other men, the story quickly gets more complicated. First of all, he might have sexual fantasies involving men, but would never actually do it (and please don?t ask him if he has those fantasies?that would be a mistake!) When I?m dressed, I do enjoy some harmless flirting, especially with gay men, who always seem to know how to treat a ?lady? to make him feel good. But I had to come to terms with my
resolute straightness after spending a week in San Francisco and not losing my heterosexual virginity. Like most CDs, my fantasies are bigger than my mouth.

Ah, well, he may not be gay, but is he mentally unbalanced? This, I?m pleased to say, is unarguably false. There is real, actual, scientific research showing that crossdressers have no more neuroses, mental illness, depression, anxiety, or what have you, than any random group of men. Of course, as a woman, you?ll know that any random group of men is fairly messed up, and I, for one, am really strange, but that?s just the luck of the draw, not crossdressing. And speaking of luck of the draw, it?s important to consider the other factors that may or may not be present in your partner: consideration, caring, love, sharing, involvement, commitment, persistence, communication, and a host of other traits. If he?s got all those and sometimes wears a brassiere, well, personally, I think you?re doing all right.

What?s in it for him? Most crossdressers talk about a sense of relaxation, a feeling of change and ease that comes over them when dressed. At different ages, the ?feeling? will be quite different. The younger he is, the more the erotic component comes into play?in numerous ways. After all, the clothes I?m wearing are women?s clothes, and women?s clothes are sexy?I?m actually wearing all those things that are so secret and forbidden?pantyhose, slips, bras and teddies. That?s a complex eroticism?I?m wearing the forbidden secret garments myself. And, there?s the thrill of the
forbidden: I?m doing something I?m definitely not supposed to do, and the consequences might be dire. In crossdressing fiction, what I call our silly stories, the consequences are always huge and always erotic.

Potentially, there may be more in it for him as well. I always try to get crossdressers to think and play with the aspects of womanness that are less than sexy: the wearing of high heels when you have to stand for a presentation for two hours; being an object of male lust whether you want to or not; being ignored or not taken seriously because you?re a woman; being responsible for more than your share of the housework and family; and on and on. Some of us tune into these aspects and really get insights into womanness as something other than garter belts, miniskirts, and boas. The mature crossdresser with a desire to learn can come to understand how you can?t always wear what you want, but must wear what you can. And ultimately, you?re the one to take him there.

What?s in it for me? This is a much more difficult question. One traditional answer is to say that if you give a lot of understanding and meet him and share his experience, then you can end up with a girlfriend you can share with, or a husband who understands shopping and fashion, or someone who can relate to your feminine side in a way not common for most men. But there are problems with this answer. First of all, your partner might not be sensitive to the issues women face?issues he hasn?t personally experienced?or he might not be able to understand much beyond the erotic thrill he gets, or he just might not be the sort of ?woman? you would choose as a friend. There?s no telling. On the other hand, it might be you who simply cannot relate to a partner who violates the gender laws in ways you cannot handle. You married or hooked up with a man, and that?s what you want. You?re heterosexual and the idea of your man looking like a woman is a total turnoff. No one but you can figure out what?s in for you: it may be nothing, or it may be a lot.

What does the future hold? Of course, every partner worries about the future. Isn?t this the first step toward really becoming a woman? Isn?t this going to lead to The Operation, when that lovely appendage to which you, if not he, is quite attached, will be removed? The simple answer is no. The vast majority of crossdressers are happy to be just that?men who sometimes put on women?s clothes. Now, I said I would be honest and I will be: there?s no absolute way to predict the future. There are some crossdressers who wake up one day and announce they?re not crossdressers at all, but transsexuals. It happens, and it?s often as much a surprise to the crossdresser as to his family. In other words, whatever happens, he?s not lying to you. But that is the exception, not the rule?by a long shot. In fact, I honestly believe that the easier time a man has being a crossdresser, the less likely it is that he will cross over to transsexualism?but that?s hardly scientific, and truly in the realm of hunch. So in general, the future probably holds pretty much what the past holds, which is not so bad a thing.

I guess the most important thing is the realization that the person, the human being, who under the clothing is the same person. Yes, when I dress en femme I?m violating some of the most rigid rules our society has to offer?those that separate men from women and males from females. But, I ask myself, why does my doing this so upset the social apple cart? What is so terrible about exploring my feminine side, about going into it, about living it? Why does this create so many stresses and difficulties for people who can?t relate, can?t understand my process? The only answers that really appear are the same ones that condemn anyone who is different, is an explorer, is a variant of the ordinary, of the ?normal.?

Speaking personally, there have been wonderful and fascinating benefits to being a crossdresser. I?ve met wonderful people, men who have a sensitivity and warmth far above the average. And I?ve met their partners, women who seem to define the very idea of what it means to love someone and to follow them anywhere. I?ve experienced what women experience when men deal with them, and I can roll my eyes with the best of them when men are being boys. But more than anything else, I have to
confess, I love being different. I love being a gender outlaw who is still, at my mature age, able to shock, be different, and have a good time outside the rules, outside the code, outside the ordinary. When a man wears a dress, let me tell you, he?s anything but ordinary.

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