Would You Date A Man Who Liked To Wear Women’s Clothing?

My friend Mattie is in a relationship with the fella you see above — that would be Peter. Isn’t he gorgeous? Peter, aka. Pusse Couture, is a both a makeup artist and drag queen here in New York City. He also works at Luck Cheng’s around the corner from me, so whenever I need a dab of lovely in my life, I head that way. I also go hoping to figure out exactly how one walks in five inch heels without eating it every other step. I never learn a lesson; I just gaze and ponder.

I’ve often asked Mattie if it’s weird to him when Peter comes home in his attire and they start to get all hot and heavy. As a gay man, is it strange to peel the layers of stereotypical women’s clothing from your boyfriend when you’re clearly not into the ladies at all? “Not really. I know what’s underneath.” That was his answer.

I used to hang around this guy who would occasionally put on my clothes. I’d walk out of the bathroom and there he’d be in my underwear in the living room, trying his best to keep his balls in my tiny cotton boy shorts. The first time made me think of Silence of the Lambs, the second time I laughed, and by the third, fourth and other times that followed, it just seemed strange to me. Sometimes he’d remove them soon after he put them on, other times he’d keep them on all night if we weren’t going out. He’d also put on other other articles of my clothing from time to time and wear them around the apartment, but that was done in more of a fat-shaming way because I wasn’t as skinny as he was. He was swell.

But the underwear thing — what would compel a man to put on ladies’ undies? With all that “stuff” they have down there, it can’t be comfortable at all. And aesthetically, as a straight woman, it’s a complete turn off and, yes, makes me think of this scene from Silence of the Lambs, although he isn’t wearing underwear and is, instead, just pulling the “man-gina.” Granted, this is one of my favorite movies in the world, but it’s not what I want to be thinking about when I’m fucking my boyfriend.


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Photo: Leland Bobbe

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    • Sam

      In high school, I did date a fellah who regularly wore dresses. I found it sensitive-seeming and endearing (then he hit me in the face, but that’s a whole other story). In general, it didn’t bother me–in fact, the only thing that bother3ed me was it was almost always the same ugly dress. He never wanted to wear any others. It was like that Seinfekd episode where Jerry meets a woman who’s always wearing the same outfit…

      • Amanda Chatel

        Actually, in high school I had a crush on Opie… and Opie wore skirts, because he loved Nirvana. Kurt rockin’ a dress is totally fine… because HE COULD DO NO WRONG.

      • Sam

        Kurt rockin’ 0% clothes would have been fine, too…but he did make a dress WORK.

    • Sugar

      Absolutely. The strange thing is that you mentioned Silence of the Lambs like it’s a bad thing, when I actually have a MASSIVE crush on Ted Levine.
      And Noel Fielding.
      and Marc Bolan….
      and any man who is free and open to all sexuality.

      • Amanda Chatel

        No no… I’m totally with you on the Tend Levine thing. But that’s also because I have a thing for sociopaths. I date Patrick Bateman every night in my dreams.

      • Sugar

        Yeah… but I’m hot for him on Monk. Even fat, old and bald and that man is delicious.

      • Amanda Chatel

        Hahaha! That’s awesome.

    • Lastango

      Meh. Up close, dragsters are like bodybuilders… interesting at first, but it’s always all about them.

    • woo

      Hey guys,

      Probably good at this point to distinguish between drag queens, transgender and straight crossdressing.

      Drag queen is a performance thing, generally it’s gay men (though not always) who are going ‘drag’, not trying to pass as women.

      Transgender is when somebody shifts their gender role from m to f, or f to m. Transgender is an umbrella that includes things like transsexual (actually making physical changes such as breast implants/reductions), crossdressing and genderfucking (kind of like androgyny).

      Crossdressing is when a person dresses in the clothing of the gender opposite to their physical sex, but doesn’t necessarily want to realign their gender (ie they still present as male or female despite wearing clothing that typically belongs to the other gender).

      I now know all of this because my partner of six years told me, a couple of weeks ago, that he is fairly sure he is transgender. So he has been wearing femme clothing around the house, and learning about makeup (he’s better at it than me now, the bitch) and has even bought some pretty good fake tits. It’s weird having p in v sex when both people have tits. But he is so so so much happier, and I’ve seen a whole new side that I’d never seen before, and I love him more for it!

      So in conclusion, although I previously would have been an ‘if he’s a pro, fine’, I’m now ‘heck yes, because I fucking love him and want him to be happy’.