1.

So I walk into Forever 21, chain Mecca for the teenage set, and I’m feeling good—I mean, just look at me. It’s smack dab mid-winter, but Greg, like a gent, holds my coat. All I’m wearing’s that tiny pink dress with the crisscross straps and beneath it the sequined fishnet stockings. My arms are thick and toned in the overhead lights, and my calves are thick and muscular. I summon a saleslady and let her soak me all in.

“What’s a good sweater for someone of my build?”

She reaches for a rack, shows me a big, boxy dolman; I can tell that it’s cute but not what I’m looking for.

“Honey, the grunge era is on the line. It wants its sweater back. No, seriously, I appreciate that you’re trying to accommodate my shoulders (story of my life), but let’s show this waist some love too.”

I turn sideways, let her check out the tum.

“You see how tiny that is? Don’t tell me I did all that treadmilling for nothing.”

She goes for a while and when she comes back she’s got a cream-colored cable-knit. I can tell it’s a frost but I put it on just to humor her, shrug it over my do and fold the waist-hem so it cinches. Why’s she trying to lasso in my style? This is a sweater my nana might wear. I look reprovingly at the saleslady, expecting the note of apology in her eye … and she nods at me with huge, unwinking seriousness. Forget everything else, she seems to be saying. From one woman to another, that sweater is good.

I stare at the lady in the mirror, the one wearing the off-white oval-neck cable-knit sweater. She’s a formidable person, this lady, coy, contained, attractive. She’s prim and austere but not at all shy, and she has a high-paying job in an office with a dress code. She’s the kind of lady who scares me in everyday life.

The saleslady leans in and points to the sweater.

“One other thing about the stitching on this kind of sweater. It accentuates your bosom.”

Illustration by Wesley Ryan Clapp

2.

Every year I host a bitchin’ cross-dressing party; every year I have no trouble getting people to come. Boys and girls, gay and straight, just love to dress up. Boys especially seem to relish an evening in drag, which they treat as a free pass to complete social indulgence. They’re hissy and bitchy and catty and witty (or so they think) and they strut up and down the place hooting catcalls like Joan Rivers. No thought is so slight that they’ll hesitate to share it; no fancy so obnoxious that they won’t act it out.

These are the “queens.” Other boys take their cue from a quieter archetype. Instead of Joan Rivers on crack they’re Marilyn in Some Like it Hot, all folded hands and shy smiles and legs crossed on the couch. All they’ve done is step into a dress, but from the way that they act you’d think they’d been painstakingly Photoshopped: hairy legs depilated, bulbous knees smoothed, pale bony arms stretched into slinky Hepburn tubes. In their imagination, they’re as cute as kittens, and they’ll purr if you treat them as such.

Why do we act like this in drag? Are we expressing our feminine side? Or are we just mocking it? Drag performers are often attacked on these grounds. Drag (goes the claim) depends on boiling down femininity until nothing but a few hard, ugly stereotypes are left in the pot. In essence it’s just so much modern-day minstrelsy. Apologists reply that this view stems from a fundamental misapprehension: drag queens aren’t pretending to be “real” women at all. Queens occupy a sui generis category. Neither male nor female, they move outside the binary by hilariously combining what’s worst in both genders: vanity and cattiness on one side, arrogance and aggression on the other.

Moreover, point out apologists, it’s not only about the queens anyway. From a Hollywood trope and a gay male subculture, the drag show has become the cornerstone of your college’s genderfuck week. By drawing attention to the performed nature of gender, drag forces a new understanding on us: the only difference between the audience members and the queens onstage is that at the end of the night, it’s the audience that’s too afraid to take off their stifling, gendered costumes.

Or something like that. There are many different theories about drag’s subversive potential, none of which explain the sheer joy of doing it. To limit the scope of our discussion: why do cis-gendered men—not just cross-dressers and a subset of gay men, but, I hazard, nigh all of them—get a palpable thrill out of wearing a dress? It’s a riddle of surprising complexity, though the feeling of transgression’s surely part of the answer. My friends and I, who all enjoy the luxury of feeling comfortable in our birth-skins, confined our cross-dressing to a private house party, far removed from normative public life. Other societies, past and present, push it even farther away. They associate cross-dressing with religious rites. Certain days of the year, the deity blesses gender-play, but on all the rest it just pisses him off.

There’s the adrenaline kick of drag, the feeling of naughtiness from doing something (semi-) publicly wrong, and then there’s the psychoactive component, the part of drag that makes boys go delusional. Perhaps the clothes alone account for this. We pick signifiers of femininity that are as broad as Russia. Our flat chests and thin legs demand such attire, because the game would otherwise be too hard to sustain. But there’s more to it than that. We don’t want to be “proper women.” If there had been a pro makeup team at my party, offering gratis to do makeovers so complete that visually, at least, we’d all “pass” no problem, it’s as likely as not that we’d all turn down the offer, and not only for fear of questions about our normative maleness. It’s simply not as fun to be a real, adult woman. We’d rather cull our affects from a simpler category—the fat sheaf of stereotypes growing from the word “girl.”

And I defend our right to do it. Within our harvest of stereotypical appropriations, I think I see the seeds of real, new personalities. Look with what relish the boy bats his eyes—for the first time he can remember, he’s just been called cute. See the joy written on this bearded queen’s face—he’s just pleaded guilty to being a “saucy bitch.” And those two straight guys who we just caught French kissing? What’s the big deal, girls always make out at parties.

The question is not whether I contain repressed gender- and sex-urges. Of course I do—we all do—Freud taught us at least that. The question is whether, in the cellars of these urges, there’s enough psychic hay to feed a real, genuine, and totally other personality.

3.

Madison walks into DSW Union Square, not sad to be leaving the sidewalks. The looks and double takes have long since ceased to flatter. She senses their close attention to everything that’s off, her masculine gait and over-formed calves, her sneakers begrimed with the slush on the ground. God she hates those sneakers.

The bargain footwear at DSW is ordered up against the wall. Madison ascends the scale: size five, size six, seven. Women on benches are trying on shoes, small women mostly but some who are bigger than Madison. Size eight, size nine, ten. She wipes her sweaty palms in the fabric of her dress. Size eleven. No more.

“These are as big as it gets!” she titters anxiously. “Gosh, I hope elevens fit me.”

It’s a squeeze but her heels just make it. Delighted to fall within the scope of common womanhood, she takes to her feet too quickly and an ankle buckles. She’s tossed to the shoe rack: that’s zero points for style, Maddy, did you think you would just get wedges? Desire’s one thing, competence another. She teeters into a corner and begins to learn to walk.

Nobody’s yet given her cause for complaint, and nobody will for the rest of the evening. We live in the most jaded city on Earth, one that can make anyone feel unimportant. But as she paces in the corner, awkwardness exposed over the waist-high racks, she can feel heat prickles as her face grows red. She finds herself hoping that she excites their disgust. Their disgust she’d be proud to defy—far worse would be their sympathy. That they might be proud of her! That, in their heads, they’re celebrating her wobbly first steps on the long road to womanhood! It’s too embarrassing. And the road is so long. She could devote herself to drag, learn every trick of the trade, and still remain an amateur in the theater of the feminine.

4.

In progressive circles, a MTF transperson gets to be a ‘she’ more or less when she says so. “Respect my identity, don’t be a jerk,” is the idea. So we start calling her ‘she,’ just like she wants, and soon we’re saying ‘she’ even when she’s not around. Boom! She’s in the discourse, she’s accepted as reality; she’s involved in the writing of her own self-narrative. And if we withhold from her the pronoun she wants? If we can’t think of a way to talk about her? “To find,” writes Judith Butler, “that you are fundamentally unintelligible (indeed, that the laws of culture and of language find you to be an impossibility) is to find that you have not yet achieved access to the human, to find yourself speaking always and only as if you were human, but with the sense that you are not.”

Denying a human the right to feel human—that’s not our bag, us progressive people. But how to get the rest of society to play along? Smith College is progressive to a fault, yet they refused entry last year to Calliope Wong, a seventeen-year old pre-op transgender person who had female-presented for two years but still checked “male” on her FAFSA. The uproar on campus was immense, but Smith didn’t cave. One senses this was just the first of many such questions they’ll face.

Visiting campus a little while later, I asked students for their opinion of the incident. Most admitted membership in that silent majority that was at least somewhat sympathetic to the administration. “This is a women’s college,” went a typical argument, “and being a woman is about experiencing all the bullshit that women have to go through growing up. A person who started presenting female only recently can’t know about that.”

A Smith girl of my acquaintance was even less accepting of a “girl” named Roger at nearby Hampshire (where Smith students can take classes).

“Roger has the figure of a boy and the history of a boy. Frankly (and please excuse the problematic gender coding) he dresses like a boy. And yet he tells us on the first day of class that he identifies as a ‘she.’ I mean, c’mon.”

So there is more to gender than pronouncement. The category “she” must have some sort of integrity. How that integrity’s defined depends on the definer: Smith admins see it one way, queer Smithies another; Evangelical Christians take a stricter position. But they can all agree, there is no “she” without “not she.” Hence the YouTube tutorials on “TRANSformative“ makeup. Hence the recurring anxiety among MTFs: I can’t just be a dude in a dress; I can’t just be a “he” in drag.

Where lies the onus of change? On the individual who wants to be a she? Or on the society with vested hegemonic interests in the gender binary? The question is a vexed one. Obviously the old standards no long suffice, yet an MTF person doesn’t want our condescension. She works hard everyday to make us naturally call her “she.” Her conscious efforts to feminize seem to prove femininity a construct; yet the very fact she bothers trying seems to prove her soul a feminine one. “I chose to be a woman, and that makes me more of a woman than a lot of “real” women out there.” So says Gigi Gorgeous, YouTube star and transgender woman. In a way, we sense, Gigi’s lying, because she probably never chose to be a woman at all. Womanhood chose her. But in another way we completely get it, especially after perusing her videos: “Nails Nails Nails,” one is called. “My Lip Injections! (Before & After).” Not all transgendered women go to such great lengths to (literally) embody femininity. But every person who wants to be called “she” is treating, at least to some extent, the constructed tropes of stereotypical femininity like the true reflections of her unseen soul.

5.

Tina M. (The Lives of Transgender People by Genny Beemyn and Susan Rankin ): I know I am a man, but I like being a girl (emphasis added).

Stephen Burt (My Life as a Girl): Given my tastes, it might be better to say that I like dressing up as a girl.

Kate Bornstein (A Queer and Pleasant Danger): [My therapist] Mary said I should call myself a woman, not a girl.

I am certain that I cannot “wake up in the morning, look in the closet, and decide which gender I want to be today.” Maybe other people can; bi-genders, gender-fluids, and others claim this ability, though most would deny conscious premeditation. They report that the gender of the day just sort of flows through them. Well, here’s my report: give me three tequila doubles, shave my legs, and land me in a strapless pink thing, and “girliness” will flow out of me like water from a tap. I don’t regard this “girliness” with any ontological seriousness. I won’t presume to say that Madison was becoming a “woman.” But if there’s one thesis in this essay that I’ll surely have to stand by, it’s that there’s no woman in this world who wasn’t a girl first.

Look at it this way. Madison’s performance of femininity gained texture. It wasn’t just me in drag anymore, shouting out female stereotypes as if through a megaphone: Maddy had her own pleasures and anxieties, fears and proud moments, and from a hackneyed delight in the baubles of girliness she had already moved closer to a personality of nuance. She was beginning to learn more about the experience of being, which has everything to do with the way we present and the way in which we’re treated. She both feared and enjoyed the respect of the salespeople. And, foolish girl! she coughed up thirty bucks, really, for a cream-colored oval-neck cable-knit sweater. Like the saleslady said, it accentuates her bosom.

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