I have cross-dressed all my life. I am not gay, nor am I interested in experimenting. I was married for 18 years and hid my dressing for about 10. My (then) wife sort of accepted the fetish and even bought me clothing on occasion. We divorced when she found another man to be more interesting, and despite all her promises to keep my secret, everything came out in court.
I’ve been alone now for about 10 years, and the desire to cross-dress comes and goes, but I really would like a woman in my life.
What percentage of women might accept my fetish for what it is? How do I bring up the subject before either of us has some sort of emotional commitment to a relationship that might not work?
Dear Likes Dresses,
Flirt, don’t blurt!
I don’t think it’s very romantic or sexy to provide a prospective love match with a list of your erotic likes, dislikes and fetishes. You want sparks to fly or at least flutter during the buildup of discovering each other. Is a fetish one part of your personality that gets expressed in this process? Or is it an oddly shaped room in the attic of your house that needs pointing out to a prospective buyer?
Listing all your needs and fantasies in a personal ad, or at the beginning of a relationship, is probably efficient, but the other day I saw an ad placed by a girl who’s looking for a guy who will play with her hair while they’re kissing, and all I could think was, “How do you enjoy having your hair played with under such a contrived circumstance? Isn’t that sort of thing supposed to happen by accident?” Ditto for a million other physical and emotional discoveries that turn sex and dating into a lovely diversion.
I do not like to think that sexual compatibility in the context of love can be prearranged. But you do have to be realistic. If you have a taste for something not taken for granted by the local culture, it is probably wise to do the math. The chances that you’ll meet someone who likes an eccentric, refined pleasure aren’t as great as the chances of meeting someone who likes to hold hands at the movies. But if you harbor a kink that happens to be in vogue, you’re in luck because, like all other fashions, a sexual fad persuades many people to try something on for size. When something “strange” becomes a fad, a certain number will sample it just once while others discover a taste for something new. As it happens, cross-dressing men have become trendy — so the math is working for you in some respects. Ten years ago, women were not as familiar with male cross-dressing, but now it’s all around us.
The erotic buzz a woman can get from a cross-dressing guy may come as a surprise. And the more style and poise you have, the more appealing you will be. So it’s not a question of percentage — you can’t seriously think there’s a way to measure the number of women who go for this, can you? I prefer to ask, What percentage of cross-dressing men have a clue about what they’re doing, aesthetically? It’s a question of quality versus quantity. If you are among the elite number who has that special something when dressed like a gal, you are ahead of the game, and that’s more important than knowing how many women are willing to play. (That inane math stuff again!) Style can trump circumstance.
Do I seem to skirt the issue? Well, the thing is, you have a hobby or pleasure that not every woman will relate to and you need to avoid the sort who will run shrieking from the room. I think you need to include in your dating plans not just women who already know they like cross-dressing but women who might get into it because they’re turned on by you. I have noticed that effective cross-dressing men possess a twinkle in the eye and a flirtatious, playful intelligence that can be quite seductive.
It’s not about finding a woman who merely “accepts” cross-dressing. You don’t want a partner who looks at your cross-dressing as a “lie back and think of England” ritual that she tolerates. It’s about meeting a woman who likes you, is turned on by you — and you just happen to be a cross-dresser. You’re also looking for a woman who is open to new experiences and pleasures. Now you could, conceivably, hook up with a narrow personality who happens to be turned on by cross-dressing. Nothing wrong with that up to a point, but she might have little else in common with you. You need to have more in common to have a lasting interest in each other. If you make a fetish of your fetish and reduce your romantic needs to that alone, you risk settling for less than you deserve.
You could run a classified that defines you as a cross-dressing straight guy right upfront, or you can hint at the issue by mentioning favorite books, performers, movies and boutiques associated with cross-dressing. For example, if you advertise that you’re a man seeking a woman for a relationship and you’re a RuPaul fan, you’re saying a lot right there without being blunt. I prefer this imaginative approach — as opposed to presenting yourself as a person with a menu of needs — and you can use it in any conversation with a new girlfriend as a way to break the ice.
There is too much confession and not enough conversation in this world! Get into the habit of discussing your kinky secret without being personal. Your fetish is not just a personal issue — it’s a cultural phenomenon. Rather than blurt out, “By the way, I’m into cross-dressing. Can you handle it?” you might talk about the history of cross-dressing, the dating mores of female geishas and male kabuki performers, a new book that you saw (such as Miss Vera’s “Cross Dress for Success”) or the winner of this year’s Turner Prize — a potter, husband and father, Grayson Perry is also known for his cross-dressing skill. If you take up the subject of Perry, focus on how convincing he looks in a white dress, not how strange he might seem. Through conversation, you will soon find out how open or closed a woman’s mind is. Then you can decide whether — and when — to reveal your own interest. She might surprise you by knowing a few things about cross-dressing herself. Think of it as constructive flirting.
- – - – - – - – - – - -
Want more advice from Tracy? Read the Ask Tracy directory.
Have a question for Tracy? Send to: firstname.lastname@example.org.