Not Everyone Fits Into Those Pre-Determined Gender Boxes

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Russell O’Connor has never neatly fit into the traditional “masculine” box, and because of that, he’s been ridiculed his whole life.

When we speak about gender, we are speaking about the masculine and the feminine. What on earth do we mean by the “masculine” and the “feminine”?

Those of us who live unhappily in a world with only these categories can find this kind of question especially difficult. It’s widely understood now that masculinity and femininity are social categories rather than biological or anatomical ones. But they are no less real for that. If you want to know why they matter, then reflect on this for a bit: The easiest way to tell whether something is “feminine” is to ask yourself how likely a boy who expressed interest in it would be to get teased, taunted, ridiculed, or ostracized for doing so.

Gender classifications are consequential. Even if gender were as objective as most people seem to think it is, what would matter about it most would still be its normative significance. The culture in which I grew up and presently live attaches a tremendous number of should’s and must’s to one’s classification as male and female. The people who live in our culture are so attached to these norms that we do not need to appoint a Gender Police to enforce them. Our friends, neighbors, and co-workers are happy to do the work, and, if they won’t, there will always be some stranger who will volunteer for the job.

That shit hurts, and it has lasting effects.

Much of my life, I have been attracted to things that our culture regards as feminine. That is, I have been attracted to things that have made me an easy object of ridicule. I have a distinct memory, from when I was about 6, of being invited over to my friend Bitsy’s house. Not terribly surprisingly, she wanted to play with dolls, and I was happy to join her. We didn’t have such things in my house, since I had only brothers. I don’t know if Bitsy’s parents were upset by my enthusiasm, or, if they told my parents, and they were upset, or what. But I never got to go to Bitsy’s house again.

The next year, we moved away. And then, several years later, we moved back. I had forgotten all about Bitsy until she turned up in my freshman English class that fall. I didn’t know if she’d remember me, but I didn’t know anyone, so I was hopeful that she might. It turned out she did remember me, and she took the opportunity to tell everyone in the school that I liked to play with dolls. Nice welcome for the new kid!

At home, I enjoyed various sorts of needlework, which was a hobby of my mother’s. One summer, I embroidered a landscape scene on the back of a denim jacket I had. I wore it to school one day, and one of the boys asked where I’d gotten it. I was thrilled he liked it so, proudly, I told him I’d made it. He stopped liking it right about then, and I don’t believe I ever wore that jacket again.

And so on.

By the time I went to college, my “feminine” interests were thoroughly repressed. It was only in my most private moments that they would emerge at all. Lacking any other outlet, the “feminine” parts of my personality started to manifest as a desire to cross-dress. My first, very tentative exploration of those feelings had been as a teenager, when my parents were out of town, and I took the opportunity to try on some of my mother’s clothing. My first serious girlfriend, in college, regarded that sort of thing as kinky, so it would occasionally enter our sex play. But it never went very far.

The longer my “feminine” orientation was repressed, the more secretive it became, especially since my first wife was utterly uninterested in that part of me. By the time I married my second wife, cross-dressing had become a private obsession. Lee knew about it, and she supported it, but she wasn’t really involved in it. There was too much shame attached to my experience of myself as feminine for me to be able to trust her with who I really was. And it did not help that the transgressive nature of what I was doing was a powerful aphrodisiac.

The way in which my feelings about myself as a gendered person have interacted with my sexuality is one of the things that has made it hardest for me to resolve my gender confusion. The repression of my femininity and its consequent sexualization not only triggered my inbred sense of Catholic shame, but made me doubt how deep my feelings really were. It became easy to think I didn’t really have a “feminine side” but just a fetish. I worried, too, that maybe I was gay. I have no problem with gay people. But if I was gay, that would mean I’d been living a lie for a very long time. And yet I felt no attraction to men.

We talk about sexual orientation the wrong way. The equal marriage movement has worked very hard to make it clear that being gay is more about love than it is about sex. So we ought to at least distinguish “romantic” orientation, which is about who you might love, from sexual orientation, which is about with whom you might be physically intimate. Either way, though, it’s not that some of us are attracted to people of the same sex, and some to people of the opposite sex. Rather, some of us are attracted to men, and some to women, instead or as well. That is true to my experience. I’m attracted to women. I’m “gynephilic.” My gender has nothing to do with it. The feminine parts of me are just as attracted to women as the masculine parts are.

With that realization, I was at least able to distinguish my questions about gender from questions about my sexual, and romantic, orientation. But it didn’t solve the problem entirely.

Gender, as I have said, is normative, and it is nowhere more normative than with respect to sexuality. Suppose I were to meet up with a woman in a hotel bar, and she were to express enthusiastic consent to a bit of sexual play. Though she hardly knew me, she would probably have a lot of expectations about the kind of sexual play in which I’d be interested, simply by virtue of the fact that she categorized me as male. To be honest, I would have similar expectations about her, too, on the grounds that she was female. And I think we all know very well that these are not just expectations: Men are supposed to have sex this way, and women are supposed to have sex that way. Penis-vagina sex isn’t just a good idea, you know. It’s the law. In too many places, still.

It’s not that I don’t like having sex in the ways men are “supposed” to have sex with women. But the feminine parts of me enjoy having sex in other ways, too, and one of those, for me, is being penetrated anally. There is nothing intrinsically feminine about such an activity. But it feels feminine to me, and many men express similar feelings. The first thing I ever read on Role/Reboot, in fact, was “The Night I Let My Wife Peg Me,” in which Eric Martin recounts his experience on the receiving end of a dildo strapped to his wife’s pelvis.

I used to spend a lot of time worrying about why I experienced anal play as feminine. It took me a long time to realize I’d been asking the wrong question. I had assumed that I was attracted to anal play first and then, for some reason, found it to be “feminine.” But that’s wrong. My femininity came first, and I then went in search of sexual activities that would tap into those feelings. Male sexuality is centered on the penis, so finding a way for my feminine self to have sex meant, for me, finding a way to have sex that didn’t involve my penis. Anal penetration fit the bill. And it has continued to do so. It took me years to learn how to orgasm just through prostate stimulation, but the orgasms I have that way seem to be a lot more like the orgasms women describe than my penis-centered orgasms are, and I think of them, and experience them, as my “feminine” orgasms.

I don’t expect that to make sense to everyone. Or even to anyone. As I’ve said, it’s taken years for it to make sense to me. But I do expect people to allow me my own experience and stop trying to fit me into some pre-determined box. I tried for a very long time to fit into one of those boxes, thinking the problem must be me. But the problem isn’t me. It’s the boxes. The real question is why people are so attached to the idea that men are like this, women are like that, and never the twain shall meet, that they resort to ridicule and even violence in an effort to enforce it.

That shit hurts, and it has lasting effects.

Russell O’Connor (not his real name) lives in New England. He is a father, a husband, a feminist, a leftist, a radical Christian, and a huge fan of both baseball and sex. He considers himself to be ambi-gendered, though he is uniformly gynophilic.

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