Why I Dress (and Act) Like a Man

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Tired of being deferential to men in my relationships, I decided to create my own drag king persona.

Slow moving, slow talking, with a melancholy sense of humor, my lover was in many ways my ideal of a man. So when we were told to imitate a man in my drag king workshop, he was the person who came to mind.

A drag king workshop is what you might imagine: a gathering of women who want to learn how to dress and behave like men for performance. Less known, perhaps, than drag queens, the idea is nevertheless the same, exploring what it’s like to live beyond the confines of one gender.

The workshop coordinator described what we were doing as the performance of masculinity. “We start with the imitation,” she said, “then we go deeper.”

Leaning back slowly in my chair, I pictured myself as my lover, a cisgender man, talking to a woman dressed to receive him as I always have: pretty dress, light makeup, underwear off as a little surprise. It was taxing, this switch of roles, a kind of spiritual gymnastics. But the expansion in my body felt great — the open legs, arms and gestures — suggesting how much I usually compressed myself.

I signed up for the workshop because I was baffled and infuriated by the deferential role I kept playing in relationships. A grown, cisgender woman with a child and a career, I was still putting the needs and desires of my male partners before my own. As I careened through my 40s, this deference took an increasingly palpable toll. There was so much I still wanted to accomplish in my life, and I felt I never would unless I switched things up.

In the workshop, I relished the release of talking in the overtly sexual way my lover did with me, and the giddy laughter in response.

My lover and I had spent many exciting afternoons together, our gender roles often reflecting those of the characters in the reggaeton songs I liked: The cool dude on the sidewalk singing to the pretty woman up in her room.

Although neither of us was looking for a committed relationship, I liked him so much I found myself wondering if we might someday decide differently. But we both knew the value of this uncomplicated pleasure.

As foreigners in Buenos Aires (he is Cuban, I am American), we were lonelier than the locals. We didn’t have the layers of relationships people have in their home country, but that also meant we were freer to try on other selves.

The next time he and I met up, I found myself studying him, looking for clues. His walk. The way he picks up my hand as a cue to initiate sex. Will that also be my drag king’s first move?

Soon my drag king had acquired a goatee like his and began wearing the black tank top he had left at my house.

I was enchanted with this person, his confidence, even jauntiness. He was like a distant echo of myself down long corridors, the person I was before puberty hit.

Three weeks into my class, I would rush home from dropping my son at his father’s, cancel the plumber, postpone a meeting to see a friend, tear off my clothes and wrap the athletic tape around my breasts, crushing them down. Put on a dark button-down shirt, plaid pants, snakeskin boots.

In the bathroom mirror, I’d thicken my eyebrows, sketch the hairs of a shadow mustache. Last step, I’d stuff a pair of rolled-up socks into my underwear, adjust the package, and there he was.

The next time my lover was coming over, I stood staring at my closet of dresses. I put on a Lilly Pulitzer, an impeccably preserved hand-me-down, pink with white fluting. But instead of feeling like it was made for me, I squirmed inside it.

I took it off and put on shorts and a T-shirt.

Did my lover notice the difference? He didn’t say.

The following week, I cut my hair short. I loved it, a dark soft cap.

“Sophisticated,” my lover said.

I longed to tell him about my drag king, but I was afraid if I did, we would never be able to get back to our delightful afternoons.

Finally, one day, heart pounding, I told him. He was surprised but curious. I showed him photos.

Did he recognize himself? He started imitating the way different Cuban men behave, strutting across my kitchen as the civil servant, chest in, butt in, then the pimp, chest out, arms swaying. Suddenly we were there; more than any other time he’d told me about Cuba, I could picture the streets, the island light, as I followed him, copying his moves.

One day after the workshop, not ready to return to myself, I left in drag and walked the half-hour home along Corrientes Avenue, lined with pizza joints and tango bars. Dressed as a man, I felt as if nothing, and no one, could mess with me.

I looked straight at people instead of being looked at. A woman in tight jeans: I checked out her butt. I felt her discomfort, a touch of fear. She averted her eyes, scurried to get out of my way, just as I had been doing my whole life. This felt wrong, as if I were betraying my kind. But also exhilarating. How was it possible that I had this power?

A few men looked at me sidelong, as if sensing something funny. But their looks didn’t provoke the usual fear or desire to please.

I took photos of myself beside a movie poster of a woman with big made-up eyes, lips slightly parted, a hint of cleavage. I was now the man beside the beautiful woman. I sent friends the photos, to which they responded: “Who’s the guy?” Even my closest friends had no idea who I was.

Of course, it’s tricky to generalize the so-called male experience. When I mentioned my walk to an Argentine male friend, he said, “That’s your fantasy of what a man feels. He may be walking down the street thinking, ‘I don’t have a job.’”

And my lover, who is Black, said, “You were imitating a certain kind of man.”

My lover had told me about his experiences in Buenos Aires, where there is a very small Black population, entering cafes and seeing people reach fearfully for their cellphones. I had been able to feel comfortable, even unassailable, in public space in a way I never had as a woman. But had I been Black or brown, my experience, my lover reminded me, would likely feel different.

At the end of the workshop, we put on a show. As I rehearsed, lip syncing reggaeton songs as my drag king, I could feel my libido rise as I became that guy, singing to the pretty woman in her window.

When my lover and I met, the female role felt increasingly less real to me, less meaningful, as if I were playacting the woman he wanted.

Rolling with it, he suggested he and my drag king go out for beers. When I said we could also kiss in public, he balked.

He offered to take photos of my king, suggesting looks I wouldn’t have thought of. Afterward, in the bathroom, I stared in the mirror. I didn’t know what to do. Stay as my drag king, or dress up as that woman?

“Send me a photo,” my lover messaged me. In the past, I would take naked ones, wearing only a thick gold necklace. But the only selfies I was taking these days were of my king.

I offered to send some photos of me as man. “But I don’t think that’s what you’re asking for.”

“Haha,” he answered, “send me the most feminine one.”

I did.

“I would have liked to see you without a mustache,” he wrote, “but you’re beautiful.”

I felt so much more attractive as my drag king, but my drag king wasn’t attractive to him.

Even as he was losing me, I was losing him. I wanted to be him more than I wanted to be with him.

The day I came home from a trip, my lover and I had a tentative plan to meet, but I canceled on the way in from the airport. I had been buttoned-up on my travels, and the first thing I did when I walked in the door was shed my shirt and bra and cinch the athletic tape around my chest. I applied the thin mustache, the thick eyebrows, the goatee. I found my king’s package in my sock drawer and stuffed it in.

His gaze, direct in the mirror, a little “Come here,” a little “Get lost,” a hint of amusement around the mouth. Looking at him, I felt a libido surge, accompanied by a sense of utter ease with myself.

This was the man I wanted to see tonight.

Maxine Swann, a writer in Buenos Aires, is working on a memoir about her drag king experience.

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