Cross dressing boyfriend

iVillage Member
Registered: 07-06-2004
Cross dressing boyfriend
2
Tue, 07-06-2004 - 5:28pm
My boyfriend and I have been living together for about two years, and things are generaly great. We're both pretty sexually adventurous (and both bi), and there's not much that we aren't willing to at least try.

We're also GREAT friends, and have been friends for what seems like forever. In point of fact, when I first met him, I thought he was gay, and we really became "girlfriends" as much as anything else before I found out he was interested in women. He's not effeminate per se, but he really "gets it", you know?

So I've got this great guy, the sex is great, and he can pound his chest and be manly one minute and curl up with a chick flick or go shopping the next. What could be better, right?

But he's a sometimes crossdresser. I don't just mean he wants to wear high heels and have sex, but once or twice a year (and ALWAYS at Halloween), he likes to get dressed up in elaborate costumes, and he's pretty convincing. He really gets into it, complete with shaving EVERYTHING, makeup, underwear, false hips and breasts - the whole works.

Now, I don't mind - its not a turn off, and I like the feminine side of him. Its fun to go shopping for outfits, and I can of get into it. He's a great shopping buddy! But its hard to think of him sexually when we do this. Its more like making over a best friend or little sister.

And that's the problem. For him, he's expressing a side of his personaility and sexuality, and he'd love to make love while he's dressed and in a feminine role. But even though I'm bi and he can be pretty passable, its still not the same. I'm wildly turned on by the masculine side of him, but his feminine side is my best friend, not a potential bed partner.

he says he understands, and he's OK with things, but I have mixed feelings about the whole thing. On the one hand, I wish I could get turned on by him/her, but on the other hand, I worry that he really wants something I can't give him - that he wants to be a real woman. How can I compete with that?

Is this common? How would you deal with it?

Avatar for katmandoo2001
iVillage Member
Registered: 03-26-2003
Wed, 07-07-2004 - 12:23pm
Well, you CAN'T and shouldn't feel that you must compete with his secret desires. None of us is guarenteed to get everything we might like in life, so you're not feeling sexual toward him in full regalia will just have to be one of his disappointments. So what? He can learn to deal with this, it's not the end of your relationship. We can't and shouldn't try to be everything to our partner anyway. That's why we seek out friends and family for things a partner can't fulfill.

Talk with him, ask him if he does want to change his sex and then decide where that will mean to your relationship.

iVillage Member
Registered: 04-21-2004
Wed, 07-07-2004 - 2:28pm
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