Wedding Bells Are Imminent

Friday, May 08, 2009


I've read letters in your column from married people who wind up in trouble because they were not honest with their mate about a sexual issue. You seem to feel that many fringe desires are like a sexual orientation. They don't go away or change. With this advice in mind, I recently had a lengthy and painful conversation with my fiancée about my cross-dressing in women's clothes. This has been part of my life since I was a young teenager. I am fortunate to be a short, slender male with androgynous features, so I am even able to dress up and go out to lunch or go shopping without being detected.

My girlfriend is a very special woman (obviously, or I would not consider spending the rest of my life with her). She listened to everything I had to say. I was afraid she would break off our wedding plans, but she did not. She seems to feel that some of my problem is due to not having a sexual outlet. (Neither one of us has had very many sexual partners.) Her theory is that by dressing up like a woman, I am expressing the desire to have a woman in my life, and if I am able to enjoy her company and have sex with her on a regular basis, this will no longer be necessary. Or at least that it will become less important.

I would like to believe this is true. Even though my cross-dressing doesn't hurt anybody, I've lived with a certain amount of shame. I can't cut expenses by having a roommate because I can't afford to give up the privacy I need for "her" wardrobe. There are times when I seem to need to spend every possible moment in women's clothes, and then there are phases where I dress up maybe once or twice a week. I know I am not a transsexual. I have no sexual interest in men at all. I enjoy lovemaking with my fiancée. She has definitely made me more comfortable with the masculine side of myself. The news that I am going to get married has made my family very happy, and I am looking forward to being less lonely. Please tell me that you think we have a chance.


It's true that I question the idea that sexual orientation ought to be defined solely in terms of the gender or biological sex of one's preferred sex partners or romantic liaisons. I think of sexual orientation more in terms of the innate parameters of an individual's erotic desires and capacity for emotional bonding. This means that being a cross-dresser qualifies as a sexual orientation, or a sadomasochist, or some other type of fetishist. For some of us, a partner's gender may not be their most important feature. We may be looking for someone within a certain age range, or from a given class background, or from a certain ethnic or racial group. Someone of the "wrong gender" who possesses a highly desired, specific erotic skill set like being a good dominant might allow someone to cross the usual lines of traditionally-perceived sexual orientation.

But we don't need to settle this controversy before taking a look at your situation. Like most cross-dressers, you'd like to have a partner as well as engage in wearing women's clothes. By the way, the fact that you are erotically interested in women only does not preclude your being a transsexual. Transsexuals can be erotically drawn to women, men, other differently-gendered people, all or some of the above, or none of the above. The fact that you do not restrict your cross-dressing to private fantasy and masturbation makes me wonder if someday you might want to live full-time as a woman. You are already drawn to being perceived as a woman during nonsexual activity. Sexologists used to make a hard-and-fast distinction between transvestites and transsexuals, but my own life experience and clinical work as a therapist has introduced me to several people who began their gender odyssey as cross-dressers and eventually came to understand that they would be happier creating real, full-time lives in the gender that was once only a fantasy. I'm not saying this is what will happen to you—only suggesting that our self-understanding, for everyone, evolves and changes as we grow older, acquire more experience, and mull over the whole curious puzzle of what constitutes a life worth living.

How does your fiancée define her own sexual orientation? This could be an important factor in her ability to accept you. A woman who sees herself as 100% heterosexual will be turned off to the notion of sex with a biological male who is dressed as a woman. If you think you might want to explore sex with her while you are in girl mode, you ought to mention this to her and discuss it now. How would she feel about being perceived as bisexual or lesbian? Even if this activity never became public knowledge, it could affect her self-image. A change of this magnitude is sometimes best explored during couples counseling.

My experience also leads me to suspect that your fiancée, though well-intentioned, is almost certainly wrong about what will happen to your need to cross-dress once you are married and having regular sexual experiences with her. That need may be temporarily reduced, but it will probably reassert itself at some point in the relationship. It sounds to me as if she does not know a great deal about cross-dressing. But she also sounds like an intelligent woman with an open mind. She needs to do some more reading on this subject, talk to some experts in the field, and get more information about your own cross-dressing experiences. I doubt that she understands what a deep-seated need it is, or how often you do it and how many resources you have devoted to creating a life for your girl-persona. Do not minimize such things when you talk to her. This will only give her a false image of who you are and what she can expect if she is in a partnership with you.

If you are going to have a good marriage, she needs to go into it with her eyes wide open. Some women enjoy having boyfriends or husbands who are cross-dressers. They like having part-time girlfriends. They enjoy doing makeup and dressing up together. But most heterosexual women also want to have a partnership with a masculine man. Are you able to do both? Do you think you can meet her needs in that respect? Be honest with yourself and with her. If you are eventually going to resent her and feel that you have been faking it or playing a role that was not natural to you, it will eventually ruin your connection with one another. Once again, there's a lot of variation among cross-dressers regarding their enjoyment of heterosexual intercourse and having a masculine role in a partnership with a woman. Some cross-dressers need both aspects in order to feel balanced and well-rounded. Others prefer to spend a minimum amount of time in "boy space," and would give it up altogether if they could. Does your personality, in truth, make a good match with hers?

This is so important that I would even suggest delaying the marriage, if necessary, while you do this research together. Above all, don't make the mistake of having children together before you are sure that this partnership is workable and strong enough to handle the long-term commitment and stress of being parents.

Many kind, sweet, and honorable women have believed that they could cure their transvestite husbands by giving them the right kind of feminine attention. This almost never works. Once we find an enjoyable mode of sexual conduct, our natural tendency is to continue to enjoy it as often as possible. If that sexual conduct is a basic building block of one's sexuality and identity, it is virtually impossible to alter it without damaging the person's libido and personality. The more "deviant" a form of sexuality is perceived to be, the more likely it is to be a core piece of that person's selfhood. People don't engage in sexual behavior that is condemned and persecuted just for fun; the fact that a person is doing something that's seen as crazy, wrong, or sinful indicates its great importance.

Of course, I can only share what I believe or know. I am a fallible human being trying my best to understand a complicated and under-researched aspect of human behavior. I could never realistically claim to know everything about gender variation. So you must put what you know and believe up against my opinion and make your own decisions. I am very happy that you have found someone who loves you, and hope that the two of you will be able to form a partnership that will make both of you happy. But it wouldn't be ethical of me to blow sunshine up your skirt. I do apologize if what I've said sounds too negative or discouraging.

There's one more important factor to consider. If she is going to be understanding about your cross-dressing, what are you going to do in return? A fetish can ruin a relationship if it's one-sided. But if you can give as much as you get, you will strengthen the relationship. What does she need sexually or emotionally that you might be able to provide, which no one else can do as well for her? That's one of the important keys to making this a successful romance.

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