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Question:
My boyfriend of 1 year has a history of having sex with pre-operative male cross-dressers. Neither of us understand the 'reasons' for his attraction and are seeking answers. Both of us are convinced of his heterosexuality, but I am not secure that this is something that will just 'go away' or perpetuate itself somehow. Can you tell us everything that you know about it and its origins? It is a great problem for me to understand. I am the only one he has ever told about it. He says that it is no big deal for him to 'stop going there,' but I am not secure. He has had ~20 partners in his life, and ~10 of them were these people. He thinks it has a bit to do with being safely fawned over...ego thing. It never involved a relationship, only quick sex. He admits to having slept with a couple WHILE in past relationships with women. He spent time in jail for ~3 years when 19-21. He swears that he's never been raped or abused. He does have quite a dominating and macho character.

Answer:
by Seth Prosterman:
(05/06/2004)
You have asked me to answer some fairly straight forward questions that I will try to answer. I will have to do some “reading between the lines” and make some of assumptions to get at some of the issues that concern you.

Your boyfriend has eroticized and been sexual with a number of pre-operative male to female crossdressers. Approximately, 50% of his partnered sexual encounters have been with transgendered persons, and that implies that these encounters are not random, and he has actively sought out such contact. I am hesitant to make definitive statements or jump to conclusions about your boyfriend without knowing his sexual history and development in greater detail.

With regard to reasons for the behavior, your boyfriend states that relating to crossdressers was a “safe” activity. Quick sex with little time for intimate connection. Hopefully, he will be able to develop a closer and more intimate relationship with you.

People have diverse sexual fantasies and interests. How he formed his erotic proclivities is difficult to say without a proper sex history. I would want to question his prison experiences to see if there are any clues there. If your boyfriend is able to enjoy sex with you, then I would not be too concerned about his sexual orientation. Eroticising crossdressers may have nothing to with his sexual orientation, it may be a “safe” way to express same-sex sexual feelings. If this is the case, then he may be bisexual. A large percentage of the population falls between totally straight and totally gay.

You mentioned that he has slept with a couple while in previous relationships. Does this mean that he has slept with 2 crossdressers or was he sexual with both members of a couple? I would suggest that you go with his own self-definition, as long as his behavior remains in sync.

I do not know if this behavior will just “go away” or perpetuate itself. He may be able to manage the behavior by expressing it through fantasy, rather than in real life. The question is, can he give it up without feeling angry or resentful? Perhaps, there may be ways that you can incorporate roll play and fantasy into your relationship to fulfill some of his desires for gender bending play. Playing with sexual fantasies is fun and will help keep your sexual relationship alive and passionate over the long haul.

Seth Prosterman, Ph.D., MFT

Reviewed by: Kathleen VanKirk DHS

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