What Gender Means to Me As a Married Man Who Likes to Wear Women’s Clothing

Originally published on Role Reboot and republished here with permission.

(Content Note: Queerantagonistic slurs,

My wife used to say that she could tell how I was feeling by what was in the laundry basket: The more anxious I was, the more likely I was to cross-dress.

It wasn’t something I hid from Lee. In fact, I told her about it shortly after we met, and it wasn’t a big deal. But it wasn’t something that I shared with her, either. I didn’t know what to make of it.

If a friend had told me they cross-dressed, I’d have been fine with it. But it’s different when it’s you.

I wasn’t really much of a cross-dresser. Back then, my feminine wardrobe consisted of little more than a half dozen pairs of panties, a few sleep things, and two dresses. Cross-dressing rarely meant more than wearing panties under male clothing. But it was still something with which I was very uncomfortable: Why did I feel compelled to go there?

When I was a kid, boys didn’t accept me as one of them. I was fairly athletic, but I was also the smart kid, the geeky kid. What I was called, though, is “f*ggot.” I remember going to look it up in several dictionaries, none of which helped. But it was clear enough why it was directed at me.

I was also the effeminate kid. More than once, a friend of my mother’s would tell me how they envied my hair, how great it would look on a woman. I was even told what great legs I’d have if I were a woman.

So the other boys weren’t really saying I was gay. They were saying I was girly.

Throughout school and into college, my closest friends were always women. It was partly a matter of values. Few of the men I knew had any real respect for women. Misogyny was casual and open among them, especially in groups, and I couldn’t stomach it.

My female friends, on the other hand, were compassionate and sensitive. Conversation wasn’t a competition, but a way of sharing ourselves. And they cared about people. They were interested in people.

Even in adulthood, if I was in a group of men, I no more fit in than if it had been a group of Buddhist monks.

Eventually I realized that the reason I never felt like “one of the guys” is that I never really felt like a guy. In some way, I knew that all along, but it came as a revelation when I was finally able to focus it.

My feminine self, who had been imprisoned for forty-odd years, was finally set free, and she went wild. Not in public, but at home. I started to buy a lot of women’s clothing, and my feelings about gender were all I wanted to talk about. It was too much, too fast, both for me and for Lee, and we crashed.

Lee was worried that I was going to come out as transgender and begin a medical transition that she wasn’t ready for. I was angry that she wouldn’t listen to my reassurances. So one morning, after a nasty argument, I packed every piece of female clothing I owned into a suitcase and put it all into the basement.

I would be a man if it killed me.

That sort of “purge” is common among cross-dressers. But in my case, it wasn’t so much the result of shame, as of confusion. I had been reading quite a lot online. Blogs, support forums, academic papers, anything I could find. But none of what I was reading fit my experience.

I wasn’t transgender: I didn’t see myself as exclusively female any more than I saw myself as exclusively male. I wasn’t bigender: I didn’t have separate male and female sides, but just the one me. I wasn’t androgynous: I didn’t feel as if I were neither male nor female.

Somehow, I felt both male and female or, perhaps better, between male and female. The problem was to figure out what that meant to me and what it meant for my life.

My values, my interests, my personality – all that was already a mix of what would traditionally be seen as “male” and “female.” But I felt like I needed to do something to nurture my femininity, to honor it, to express it, and what felt right was changing how I dressed.

But why? Isn’t that just to accept some societal story about what the “feminine” is supposed to be like? And what are “male” and “female,” anyway?

Most theorists of gender will tell you that genders are social categories that are defined by what society expects of the people who are assigned to them, usually on the basis of natal sex: People with vaginas are supposed to act this way; people with penises, that way.

But the true nature of gender is hidden by a mythology that gives it a false objectivity: Gender isn’t just social, but is firmly grounded in biology. You know, women are hardwired to be caregivers; men, to sow their oats. So the social norms that govern gender are presented as not just appropriate, but inevitable.

However, gender norms vary enormously, both across societies and over time. Gender has something to do with biology, but the particular norms and expectations that constitute the two genders recognized in American society are a product of our history and our politics.

Once one understands the radical contingency of the norms and expectations associated with gender, it can come to seem surprising that anyone is comfortable with them.

But one isn’t just assigned a gender. One is socialized into it, and most people comfortably internalize the role they are expected to play. Those who don’t are subjected to social penalties, and most of the dissidents conform in the end.

But dissidents do remain. The norms and expectations that derive from one’s assignment as “male” or “female” touch on too many aspects of one’s personality and individuality for it to be otherwise.

When I say, then, that I don’t identify as male, what I mean is: The expectations people have of me, because they identify me as male, feel wrong. There’s something called “being treated like a man,” and I don’t want to be.

We all get this sort of thing. If Lee orders a Jack and Coke, she very often has to repeat: Coke, not diet. But in my case, the disconnect is more frequent, and it goes deeper.

I have spent so much of my life being criticized, chastised, and castigated for being or seeming feminine. Why was that so wrong? I was categorized as male, was expected to behave as such, and didn’t measure up.

But there is more, and worse. Women nowadays can engage in all sorts of “masculine” behaviors (including wearing clothing that is traditionally male) with far fewer consequences than a man who gravitates toward the feminine.

Why is that? It’s very simple: Our society regards what is feminine as inferior. A woman who acts in traditionally masculine ways is striving for what is better (even if it is not rightly hers). A man who acts in traditionally feminine ways is humiliating himself.

Well, I’m giving the finger to all that crap by wholeheartedly embracing what society deems “feminine.” I reject the expectation that people with vaginas must be “feminine.” I look forward to the day when all of us will have the freedom to be who we want to be. But if a woman wants to be “feminine,” one day or every day, then that’s her prerogative, and there is nothing wrong with it.

And that goes for men, too. Femininity is not inferior, and it’s not “unworthy” of a man to like pretty shirts or lacy underwear, or to enjoy wearing makeup or nail polish.

So I’m making changes slowly now, and with more thought. Lee has been amazingly supportive, but neither of us is dying to find out what would happen if I were to wear a pink floral sweater to the mall. Even our closest friends don’t know who I really am, not yet, though we’ve been open with our daughter about it.

For now, I’m “stealth.” In public, I present as male, but I still wear a lot of women’s clothing. You just wouldn’t know it from a casual glance. I always wear panties now, in colors to match my outfit, except when I fly or go to the doctor. When it’s cold, I’ll layer a camisole or a women’s tank top instead of a T-shirt. Almost all of my jeans are women’s, as are several of my shirts, though it’s often hard for me to find tops that are long enough (I’m on the tall side).

I love the soft fabrics and pretty patterns of women’s socks, and often wear knee highs and sometimes hose or tights. I’ve even got a pair of women’s loafers that look enough like European men’s shoes that I can wear them to work.

Lee found me some clear mascara that I like, and I’ve got several lipsticks that are close enough to my natural color that they’re not too obvious. For nail polish, I do clear or very lightly tinted on my fingers and, in the summer, on my toes. So, overall, I look a lot more feminine than I once did.

At home, I wear what I want: patterned blouses and sweaters, capris or women’s shorts, more girly jeans, an occasional skirt or dress. Pretty lounging pants and pink nightshirts. Classic pumps, strappy sandals, or cute flats. Dangly earrings. Proper makeup.

It’s not so much that I’ve changed inside, but there’s something about letting what’s inside out that has been very cathartic.

To be able now, after all these years, to look at myself in the mirror and actually see the woman within me, and not to be ashamed of her, but to embrace her and love her, is powerful. And wonderful.

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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.