My boyfriend likes to dress in women's clothing. Is he gay or does he really wish he were a woman?

Question

He also has asked me to use a strap on on him while he's dressed up during sex. I've been as open minded as I can be considering I love this man. He claims to love women and was married before, but his relationships always end with the person leaving him for someone else. He never initiates having intercourse with me unless I drop hints. Sometimes I feel he just has intercourse with me to passify me so that I don't think he's gay or something. He doesn't seem as turned on unless he's dressed up and I refer to his private parts as a womens. He swears he's not attracted to men and loves women. I've asked him if he wants to be a woman, he says no, he likes his penis. I am an attractive sexual woman who gets hit on constantly. I feel I know the difference when a guy is really into me sexually. Something just doesn't feel right to me, regardless of how much he says he loves me and wants to be with me. It feels strange dressing up and then he's wearing a dress too. Who am I in this? Confused

Answer 1

Okay, this is a big question. Let me see if I can take it apart bit by bit.

1) No, it doesn't mean that he's gay if he likes to dress up in women's clothing and refer to his genitalia and body as female. There are tons of heterosexual crossdressers, and what you like to wear and who you like to pretend to be in bed have nothing to do with sexual orientation, which is about who you are sexually attracted to. Similarly with what sex acts he likes- there is nothing gay about wanting to be anally penetrated, unless you wish it were a man doing it instead of your woman with a strap-on. But I think you already know all of this, since you really do sound very open-minded.

2) As for if he wants to be a woman, well, things are a little more iffy. Usually, if someone asks if their cross-dressing husband or boyfriend wants to be a woman, my response is a simple "No.", because usually they don't. But in this case, he really does sound like he enjoys the pretense of being female. If he says he likes his penis, I would believe him- being transsexual doesn't necessarily mean that you hate and despise your biological genitals. I know many transwomen who even like their penises, and there is a good number of transwomen who choose not to get bottom surgery, what we call "non-operative" (as opposed to "pre-" or "post-operative"). So it's really hard to tell if he has transsexual desires, or is fine as he is.

I'd trust your gut. Your intuition is telling you something, and what it's saying is not necessarily that your boyfriend is gay or wants to be a woman, but rather that something in this relationship isn't working for you. I guess you have to ask yourself- in the end, does it matter his sexual orientation or his gender identity? What matters is if you feel comfortable being with him in this capacity, whether it's him in a guy's body or a woman's body or a guy's body in drag, whatever sex act the two of you happen to be doing. You say it feels a little strange, and if you can't learn to like it or accommodate him, then there's really nothing more for the relationship, in my opinion. If not having him initiate intercourse is a problem for you, it's a problem in itself, not because it means anything, right? Lots of completely normal men don't initiate sex, and if that's a problem for you, then it is what it is.

My point in case is that you aren't feeling satisfied for some reason. Doesn't matter what your boyfriend is, whether he's a pre-operative lesbian transsexual woman or a heterosexual crossdresser who likes his girlfriend to anally penetrate him . . . you aren't happy. You've either got to sit down with him and really talk this out, openly, honestly, and non-judgementally, or just let him know your feelings.

These books might help you:

My Husband Wears My Clothes: Crossdressing from the Perspective of a Wife by Peggy Ed.D Rudd

Head Over Heels: Wives Who Stay With Cross-Dressers and Transsexuals by Virginia Erhardt

My Husband Betty: Love, Sex, and Life with a Crossdresser by Helen Boyd

She's Not the Man I Married: My Life with a Transgender Husband by Helen Boyd

Hope that helps and good luck.

Answer 2

Dear Alice, I am a married man with a beautiful woman. I like to wear women's clothes and I make love to my wife dressed. Being gay is when one cross the line and interact with another person of the same sex. That's the definition of homosexual in essence. So if your boyfriend doesn't like other men he is not gay. he is a crossdresser. It is up to you if you want to continue with him and accepted as he is.

Answer 3

Sexuality and gender are two seperate things. He could be a straight crossdresser. He could be a lesbian transwoman. He could be a straight transwoman. He could be a gay crossdresser. What you need to do now though is have a discussion with him about his gender and sexuality. It's only fair for you to know the person that you're dating.