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Transvestite boyfriend

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My boyfriend of a year revealed to me he has a fetish for tranvestives, and enjoys assuming a totally female role in sex (I’m a female, by the way, this is an otherwise heterosexual relationship). He only is interested in this during sex, and he came clean about it very shortly after we began dating, which I respect.He is thrilled I accept him. I can get into it a little I guess, but it’s not really “my thing”. Before, we had “regular” sex, and it took him a lot longer to reach orgasm. He has no problem when role-playing. I have never had an orgasm with any man I have ever been with, and lie about it. He is no exception. This is immensly frustrating for me, and I hate the idea of using sex toys or stimulants, and want to be able to orgasm “naturally”. After a year of living with him, I love him, but have become so frustrated, I’m really not attracted to him.Sex is now totally about him, I find it tedious, and regard it with the same sort of disdain as housework.Now, He wants to have a threesome with another transvestite. This raises more questions for me. Isn’t it a bad idea to inolve someone else in an exclusive realationship? Or could it be exciting and a good solution for our sexual problems? But then again, maybe this would make him totally reliant on a third party. One burning question I have is pretty obvious…could he be gay? And finally, what should I do about my condition? Is there any way to “learn” to orgasm, or is this relationship doomed?

Transvestite boyfriend

Answered by on -


The problem in your relationship is not that your boyfriend enjoys cross-dressing. The problem is that you two aren’t working together as a team to figure out what is sexually satisfying for both of you. In fairness to him, you said that you aren’t being frank with him about your needs and frustrations. From his point of view, he may believe that you not only accept his sexuality but are into the same kind of sexual explorations.

If this relationship is to have a chance, you need to tell your boyfriend how you feel. If he’s a quality guy, he will be willing to slow down and to help you learn how to orgasm. By all means, check with your doctor first, to make sure that there isn’t something physically amiss. Once it’s clear that you’re okay, the two of you can and should find ways to make sex as satisfying for you as it is for him. There are excellent self-help books on the subject. Please stop faking it and give yourself the time and attention you deserve so that you can truly enjoy the intimacy and the release of good sex. And by all means, don’t participate in things that are uncomfortable for you or that you think will distract the two of you from developing your relationship to the fullest.

I wish you well.
Dr. Marie

Transvestite boyfriend

Dr. Marie Hartwell-Walker

Dr. Marie is licensed as both a psychologist and marriage and family counselor. She specializes in couples and family therapy and parent education. Follow her on Facebook or Twitter.

APA Reference
Hartwell-Walker, D. (2018). Transvestite boyfriend. Psych Central. Retrieved on May 22, 2019, from
Scientifically Reviewed
Last updated: 8 May 2018
Last reviewed: By a member of our scientific advisory board on 8 May 2018
Published on Psych All rights reserved.