I’ve never been a manly man. When I was younger, I watched quite a bit of television. I remember lots of the imagery I was presented with quite vividly. In almost every case, I wanted to be the girls. Growing up, I quickly learned that wanting to be more like the girls was a desire frowned upon by pretty much everybody else—not least of all, by the girls.

These days, the same things still come up in daily conversation as they did in years past. “I wish I could lose ten more pounds—I don’t feel pretty,” I hear women say all the time. In response, everyone simultaneously begins talking about the oppressive nature of our culture’s media campaigns. “Oh, come on. You don’t have to look like every model in the magazines. You’re smart, you’re kind; of course you’re hot,” they’ll say to her in an effort to comfort and sympathize.

Most of the time, I think women’s self-image issues are physically, though not emotionally, unfounded. All but one of my girlfriends were, to use the obvious example, heavier than the BMI charts would have them feel comfortable about. My femdom fantasies have always been tilted toward larger girls. Hula dancers were an ironic motif, but I attribute this mostly to the healthier, more attractive weight Hawaiian girls tend to carry. I’ll never understand the fetish for stick-figure girls. That can be sexy but I think women are sexier if they’re shapely.

Issues men may have with their body image, however, are almost never even recognized. If they are, they discuss how unmanly boys feel and offer ways to feel more manly. Nothing we see in our culture tells boys that it’s okay to want to feel pretty, to want to be treated in ways similar to the way we see people treating girls. If a boy, like me, wanted that, they call him a sissy and expect him to want to feel bad about it. I find this fact, an association often cited between cross-dressing and humiliation, nothing less than repulsive.

Furthermore, every time I’ve ever hinted at having body image issues of any kind at all, a very strange thing happens. Rather than address these issues, people turn to my girlfriend and give her a once-over. Then, they turn back to me. “How can you think of yourself as not attractive?” They ask, puzzled. “Your girlfriend is so hot.”

Granted, my girlfriend is hot. But what, pray tell, does that have to do with my own self-image? You’ve just told me that my own self-image should be measured by how hot my girlfriend is. Call me crazy, but my girlfriend’s attractiveness should not be the scale by which I measure my own.

Is that what you’d say to a fat girl, by the way? Oh, you’re totally sexy because your boyfriend is super skinny. What kind of logic is that? It’s not only completely missing the point, it doesn’t make her feel better. In fact, it often makes her feel worse. And that’s exactly what doing that does to me: it makes me feel worse.

Why is it a taboo to discuss men on the basis of their looks? Even in romance novels, where the gallant and obligatorily handsome man plays center stage, most descriptions about his looks center on his other attributes. His strong muscles. His virile penis. His healthy hair. It’s not about the way he looks, it’s about what he can offer in every other realm; wealth, health, or power. Even here, men’s sexual attractiveness is being judged on everything except their looks. This is crazy.

To top it off, even the pretty men, who were called the derogatory term “twinks” in gay slang for quite a while, are usually portrayed in as decidedly not delicate a manner as possible; sweating profusely, working out, doing some manly chore, or otherwise being rough and tumble. The message? Be ruggedly handsome, sure, but don’t be pretty.

By this culture’s dogma, being pretty is a woman’s job. Women are the ones who are “supposed to” do the attracting; men are supposed to be attracted. But this is insulting, and unfair. Wanting to feel pretty often goes hand-in-hand with wanting to be pursued. The emotions are the same: love me, I’m precious. But being pursued is the woman’s job, as if they are the only ones allowed to feel as though they are precious and worthy of loving attentions.

This whole fucked-up mess does a lot of things for men. It makes us get paid more at work. It makes it easier for us to attract people into old age (where, I’m sorry, looks are just not going to follow). It makes it harder to objectify us in ways we don’t want. And, unfortunately, it makes it a lot harder for us to talk about body image issues—especially if you’re like me and you don’t even want to have the traditional Vin-Diesel-the-body-builder look and instead want to look like the lithe, nubile, pretty young things you only see cast in the gender role of supreme femininity.

Well, I have a confession to make. I like dressing up as a girl because, in part, it makes me feel pretty. It does this because putting on frilly panties is the only time I feel the culture in which I live is telling me that I might actually get away with being pretty.

This confession, low and behold, is not uncommon. Men who want to feel pretty end up wanting to emulate women because we have no other choice. Why can men, secure in their masculinity, not also be pretty? Even the dictionary is stupendously unhelpful here. Defining “pretty” results in this definition from Princeton’s web dictionary:

pleasing by delicacy or grace; not imposing; “pretty girl”; “pretty song”; “pretty room”

(Emphasis added by yours truly.)

I have been called graceful. I have also been called delicate. I’ve been called pleasing a bunch more times than these other two things combined.

People I don’t know ask me if I dye my hair when they look at its color in the sun (I don’t). They ask me if I’ve ever played the piano when they notice the way my fingers curl around cups as I drink (I haven’t). They have remarked on how carefully I treat all my belongings, and how thoughtful I am when I am hosting a guest. But they have never called me pretty.

It may surprise some of you to hear this, but Eileen is actually the first person I have known that has called me pretty. She is fond of my ass and these days I might call it one of the prettiest parts of me, but it was not always this way.

One night many years ago, well before I even consciously thought about why I kept wanting to feel pretty, I was lounging with my then-girlfriend in the bedroom I shared with my brother. I remember only a single sentence from the conversation we had that night. It was this sentence that my girlfriend said to me that cued six years of body image issues centered around my butt: “I would like it if your ass was firmer.”

What did firmer mean, anyway? It meant that I should have more of a boy’s body. I didn’t have a muscular gluteus maximus; I didn’t have the body of a strong, rugged, self-respecting man. But you know what, I didn’t want that body, either. And that should’ve been okay.

Addendum: For those interested in a bit more academic self-education (the best kind, if you ask me), I would highly suggest reading the Wikipedia articles on sissyphobia and effeminacy, for a start.

A particular passage of interest is cited below, and serves as a wonderful example of the fact that cultural ideals change with time. My message in this post, if you are to take one from it that I did not actually intend when I started, would be to stay aware of this constantly changing cultural stereotype—in all cultures and in all situations—and to avoid letting cultural noncompliance result in prejudiced or oppressive actions of any kind.

Pre-Stonewall “closet” culture accepted homosexuality as effeminate behaviour, and thus emphasized camp, drag, and swish including an interest in fashion (Henry, 1955; West, 1977) and decorating (Fischer 1972; White 1980; Henry 1955, 304). Masculine gay men did exist but were marginalised (Warren 1972, 1974; Helmer 1963) and formed their own communities, such as leather and Western (Goldstein, 1975), and/or donned working class outfits (Fischer, 1972) such as sailor uniforms (Cory and LeRoy, 1963). (Levine, 1998, p.21-23, 56)

Post-Stonewall, “clone culture” became dominant and effeminacy is now marginalised. One indicator of this is a definite preference shown in personal ads for masculine-behaving men (Bailey et al 1997).

My personal experiences written above are likely the result of my interaction with New York City’s leather subculture, as that community is my primary social outlet (for now).