Adventures in Femininity: Confessions of a Female Drag Queen

illustration by John Leavitt

I’m not a tomboy or a butch or a transsexual, but femininity has never come naturally to me. Ever since fourth grade, when other girls began to wear bras and jelly bracelets and black-and-white cow-printed dresses, I have looked upon feminine adornments and mannerisms as alien rites. Early in my career as an XX-human, however, I stumbled on an outlet for my ambivalence and alienation: drag.

The solace of my adolescence was a game called “Tea Ladies,” which I invented with three other anti-girlie girls the summer I turned 13. We had escaped middle school to backpack in the Sierras, far above the clouds of hair spray; one morning, as we dug trenches around our tents in a hailstorm, one of us inquired in a fluty British accent, “Would you like a cup of tea?” Soon the woods rang with falsetto phrases like “Exquisite,” “Yes, dearie,” and “Lovely peaches on your hat.” Monty Python’s masculine dames had inspired us, and the parody of vapid ladies made us feel superior. Besides, we got to enjoy the delicacies of femininity without any of the pressures.

In high school, I developed yet another drag act: “valley girl.” “Oh my God, OK,” I would thrust my breasts forward and gape, “so I was, like, totally at the mall last weekend? No, you don’t understand, there was this guy. Oh my God, I was, like, so embarrassed I wanted to die. No, this guy. Oh my God, you don’t even know.” I babbled like Strawberry Shortcake on speed, but I never once supplied a verb for the subject “guy.”

In college women’s studies courses, it dawned on me that millions of women shared my alienation: If femininity was the uniform of slavery, then the fact that I recoiled from it showed my sanity. I soon noticed that I was attracted to women, and forthwith cut my hair, donned cargo pants, and moved to San Francisco. Yet femininity continued to fascinate me. The queer community introduced me, at last, to adult drag. At the Trannyshack club night, burly queens in slinky dresses crooned; at the office Halloween party, the male secretary breezed through in a bathrobe and a towel hairdo as “Terry Cloth.” Even biological women played up artificiality with Technicolor makeup, purple hair, or a pink mini-skirt with a spiked belt and boxers underneath.

A few years into my San Francisco education in deviance, I picked up a copy of The Lazy Crossdresser, wherein the author exhorted readers to ignore the rules, “learn the secrets of femininity, and become the girl you’ve always wanted to be.” I made a friend, a crossdresser named Jamie, who lived that ideal: Jamie enjoyed mini-skirts, stockings, a female pronoun, and a cloud of white-gold hair despite her six-foot height and flat chest. Part of me wanted to smirk when she and I met for scones at an English teahouse. Jamie primped while I showed up in jeans. This white, well-off biological male had to bear both the lower status of girliness and the stigma of not quite passing. The truth, however, was that Jamie had what I didn’t: a gender that felt authentic. Some days she dazzled; others, she looked vulnerable in worn baby-doll flats, chipped nail polish, and the barest hint of stubble. She ate peanut tofu with indelicate speed and shrugged her shoulders almost to her ears. Jamie didn’t conform to some external femininity; she pleased herself. Why couldn’t I?

One night, outside my neighborhood lesbian bar, a friend introduced me to a transgender man named Sam, a slight, handsome, dark-bearded fellow—gentle and kind. We began to date. With his testosterone-induced broad shoulders and surgically flattened chest, Sam passed for male in his day job as a pediatrician. On the street, people smiled at us—the cuddling, wholesome straight couple.

Sam liked femmes, but he rarely praised my hints of femininity. As a teenager, he had curled and hair-sprayed his bangs under duress. His parents still kept a picture of him as a bridesmaid in green satin—Sam wanted to spare me any such trauma. Yet even without encouragement, girlie things began to call to me. Soon, I found myself skipping haircuts and happening into thrift stores to try on glittery shirts. If so many other queers could act out gender on their own terms, perhaps I could too.

Every year, Sam’s fellow hospital residents staged a dance they called “The Prom.” This year, I walked in on his arm, clad in a clingy, vintage black dress with beaded fringe. My hair lay smooth against my shoulders. I had shaved my legs—at least in large patches—and donned nylons. That particular feminine casing must have gone out of style while I was immersed in lesbianism; everyone else went bare-legged. I had applied my only makeup, lipstick that my Spanish host sister gave me when I was 18. (She had tried to educate me about such things before she became a nun.) For a strapless bra, I wore a hand-me-down from an ex-girlfriend, a size 34B. I was a 32A, so I kept retiring to hitch myself up and check for lumpiness.

Sam and I floated among the hosts of straight people, ate our salmon dinners, and began to dance. I ground my hips to hip hop and twisted to “YMCA” in the enthusiastic manner I usually reserved for the mirror. For the most part, the sexist scorn I had aimed at the tea lady and the valley girl had faded. If femininity was mine to play with, why disparage it? It still felt alien, but I no longer imagined an icy judge peering down at my failures. As a girly-girl impersonator, I could pick my costume at will and wear it in a spirit of mischief. In my clingy dress with a gold scarf around my neck, I felt at ease and slightly aroused. I sat down for dessert with my hands in my lap, aware of the warmth of my belly through the polyester fabric. Even my various faux pas held a certain erotic energy. The folds of my belly, my less-than-spotless face, my slight mustache, the clumsy way I handled my purse all showed that the dorky real me was irrepressible. The other ladies in cocktail dresses and blush seemed to dance with less gusto.

I let myself imagine that my disguise had won out: The imposter had her day. But perhaps I flattered myself in believing that I was different. To what extent were we all imposters? Did the other women at that dance feel that femininity was alien? Maybe they had simply refined their disguises. I began to lean toward the postmodern suspicion that there were no natural femmes. Perhaps, as Berkeley theorist Judith Butler argued, gender was drag. But could femininity really be an act that we made up as we went along? If femininity consisted only of individual whims, then it lost its appeal as a mysterious absolute. As male poets through the ages had, I had always seen it as a force to be admired from afar. Now when I strutted, encased in soft, black fabric, I still seemed to brush up against something electric, unknown.

That night it felt possible to both imitate an archetype and design my own. A sense of my own power filled me, yet I also sensed an elusive ideal. Perhaps I was lost in hubristic delusions of having my cake and eating it too. But as my nylon thighs brushed each other and I balanced on my heels on the way to the car, I felt more natural as a drag queen than I ever had as a woman.

Anna Mills lives and writes in Menlo Park with her partner Sam and his lovely, lavish cat Spot. E-mail her at AnnaRMills