I was playing dress-up this evening

… as is my wont. Usually it’s so that I can try to look pretty in the slews of femmey clothing that I can’t afford to buy and will never wear in public, but that look so attractive I can’t resist. From the neck down, I think my body is attractive, and it’s fun to see what I could look like if I wore clothes that displayed it. 

Of course, I also have a head that doesn’t look like a pretty girl’s head, and the head more usually fits the outward, butch, not-at-all-attractive appearance. So tonight, after I paraded in front of my mirror in a couple dresses, I decided to see just how butch I could look. I was going for butch woman, not cross-dressing. I put on a black men’s dress shirt, black men’s dress pants, a black belt and this women’s brown leather jacket I’ve got, one of the few expensive clothing items my mom bought me in an attempt to make me wear women’s clothes. But weirdly enough, I looked in the mirror and for a split second I saw a guy’s face staring back at me. Of course, it quickly evolved into my own face, but it was distinctly bizarre to see a face that was not mine.

This is interesting, how what I see from the neck down influences what I see from the neck up. Between my usual clothes from the Target boys’ section, my dress-up girly clothes from Charlotte Russe and my “butch” outfit, not to mention my naked self, I’d managed to make my face look like four different people’s faces. However, it’s only in my standard attire that it looks like me. In the butch clothes, it looked like someone else’s face, but a face that “matched” — when I’m naked, with my female figure, or in clothes that fit the figure, I see a face and haircut that look like they’re on the wrong body — it just makes me feel that much more keenly how much I regret not being attractive in the conventional sense.

I think once or twice I’ve been told by a woman who likes women that I am attractive, or that a particular set of clothing makes me look attractive, or something like that, and I get all excited because it means that I could be sexually appealing to someone. But for all intents and purposes, I am bisexual — it hurts my feelings ridiculously that no straight man has ever told me I am attractive. (I firmly maintain that the only boyfriend I’ve had is in the closet.) And as much as it would be wonderful to have a girlfriend who thought I was hot, or something like that, no matter how hard I try I can’t just pretend to be gay. The opinion of guys matters to me too.

As my mother would say, “You can’t have it both ways.” If I want to be attractive to men, I need to play the game, like so many women do. I need to wear makeup, style my hair, wear clothes that show off my body, fuck, even wear underwear that’s not the most conservative style Target sells. And I don’t want to do these things, because I can’t be a feminine woman any more than I can be gay. Going through a day in lipstick and hose, pretending to be a different person, is more agonizing than thinking I’m ugly.

As I once said jokingly to someone, I think I need to develop some really weird fetish and film myself indulging in it and put it on the Internet so that there will be some subset of people who think I’m hot. (Which brings me to the topic of how the Internet has taught me how vanilla I really am, despite all my masochism and submission and whatnot. But that’s definitely another post.)

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2 Responses to “I was playing dress-up this evening”

  1. (Here through Trinity, reading through archives. Also bi and kinky. Hi!)

    Men who go for less feminine women exist, really they do. But I’d be very surprised if high school (even the most progressive high school, which it sounds like yours is not) brought them out of the woodwork. I suspect that you’re more likely to find such men in communities that generally value less-mainstream traits.

    For me, high school guys were generally put off by the grades and awkwardness, even though I was pretty feminine in appearance then. In college (I went to a small science/engineering school) I buzzed my head at the beginning of my senior year. There were men who definitely liked it, and my boyfriend’s attitude was, “Your body, your decision. Oo, can I fuzz your head now?”

    Which is to say, your mother is wrong on this one.

  2. Pleased to meet you!

    I hope things will change in college. And I really think they will.

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