The First Time Dressing and Going Out as a Woman

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It was sophomore year, the Saturday before Halloween, 1994. I ended up on the top floor of the farthest entryway in Adams House, which I didn’t mind because the eaves made my room feel like a garret. I’d recently learned that word at a lecture on Virginia Woolf ’s A Room of One’s Own, where the professor proposed the garret as an ideal space for writers in search of quiet and contemplation. I felt inspired in that room, even though I occasionally bumped my head when I sat up in bed.

I’d skipped breakfast that day, so it was past noon by the time I shuffled into the dining hall. I hoped to see people I recognized after I got food, but when I didn’t, I sat alone at one of the square tables in the middle of that vast space with its dark wood paneling and red velvet curtains, hoping still that someone I knew would come along and join me. I had only lived in the house for six weeks and was slow to make friends.

At the next table, I overheard some juniors I didn’t know well talking about Drag Night, an Adams tradition I’d heard about but didn’t realize was happening over dinner that evening. They were planning to do a number to “It’s Raining Men.”

“We need to go to the thrift store to get costumes,” a compact blond man named Zach said.

“And he needs to shave,” a redheaded girl named Sarah commented. I sneaked a peek to see who she was talking about, someone whose name I didn’t know, who had dark curly hair and patches of stubble.

“It’ll be funnier if I don’t shave,” the guy said, who I immediately assumed was straight.

I wondered if I should ask to join their group, but I couldn’t rely on them not to laugh in my face or make excuses not to let me in. Anyway, just because I was gay didn’t mean I should automatically do drag. I’d never dressed in women’s clothes before, not even in private or, for that matter, gone out in costume for Halloween, since we didn’t have Halloween in the Philippines. No one at lunch seemed interested in asking me anyway.

I walked over to the mailboxes after my meal and ran into a girl I’d gotten friendly with the day I moved in, another sophomore named Lucy Bisognano.

“So,” she began, “what are you doing for Drag Night?”

“Just watching.”

“You have to at least dress up. Come over to my room. I have dresses that would probably fit you.”

I agreed to meet Lucy later that afternoon. Though I was excited to wear women’s clothes for the first time, I was even more thrilled that someone at Harvard cared enough to hang out with me, especially someone as popular as Lucy, small‑boned and fine‑featured yet unfailingly jovial, like a bird in mid‑flight. I was a poor kid who’d gone to a mediocre public school in Chino, California, in the smoggy, working‑class part of Los Angeles where my uncle worked as a nurse, so that was where we ended up when my family immigrated four years earlier. My brain and my will got me to Harvard, but I didn’t want to be the poor immigrant kid once I got there. I pretended to be like everyone else, did a good enough job with my accent to pass for white and native‑born but not a good enough job that I could keep other kids from thinking I was weird. Hardly anyone wanted to be my friend, and the few who did I didn’t really care for, not until Lucy came along.

A couple of hours before dinner and the Drag Night festivities, I knocked on the door of Lucy’s suite, and she led me through the halogen‑lit common room into her bedroom, where Monet and Degas posters livened up the beige walls. Her room barely fit her desk and single bed, which suited me fine because I liked being near her.

“I’m not sure what will fit you so let me just show you what I have.”

As I sat on Lucy’s bed, on a comforter adorned with tiny pink flowers I couldn’t identify—maybe peonies, or gardenias—she opened her closet door and pulled out dresses on hangers one by one, then draped them in front of her. I wanted to examine the details of those garments, admire the lace pattern of one and the pleating of another, but I would have needed to get really close, and it felt too early to expose my poor vision to my new friend. But she must have sensed a heightened reaction when she showed me a sleeveless dress made of black velvet, a fabric I immediately identified because its shade was darker than any other cloth, a depth of color I hadn’t known back home.

“I bet this would look great against your skin,” Lucy said.

She left the room so I could change. After I stripped down to my white briefs, I stepped into the dress, put my arms through the sleeve holes, and shivered at that forbidden thrill I’d only known about secondhand, of being a man in women’s clothes. I’d grown up seeing such men, had even worked with a few when I was a child actor in the Philippines, those bakla a staple of slapstick comedies on TV and in movies. But while my culture tolerated bakla, nobody ever took them seriously, so I wasn’t interested in being like them. But maybe because I knew I could dress up as a girl if I wanted to, I also didn’t really find the idea particularly exciting, not until I got to America and noticed how men dressing up as women seemed so much more taboo than it did back home.

I was able to zip the dress up most of the way, as it stretched to encompass my back, muscular from pull‑ups at the gym. The neckline scooped tastefully in front and was bordered in a shiny material, maybe satin, which I didn’t notice from afar. I looked down to observe that the dress ended a couple of inches above my knee and had a slit on one side. I remembered a woman on a talk show say that every girl needs a little black dress in her closet; this was the kind of dress she must have meant.

“I hate you,” Lucy said when she came back into the room and helped me zip up the rest of the way. “This looks way better on you than it does on me.”

As Lucy looked through her jewelry box to see what might work with my outfit, I recalled the moment a few years earlier, I must have been thirteen, when my cousin Baby walked in on me as I was about to put a shirt on in front of our old wooden house’s only mirror, attached to a weathered armoire.

“You have a woman’s waist,” she observed, as she brushed her palm down my side to demonstrate how my body curved in below my rib cage and then back out toward my hips. I smiled into the mirror at my cousin’s compliment and felt an echo of that pleasure with Lucy.

“Your hands are so dainty and small!” my friend marveled as she held one and slipped a gold bangle through my fingers. I looked down and noticed that my hand was indeed smaller than Lucy’s, though that was only because I was Asian. My hands weren’t particularly small by Filipino standards, but people judged my body differently in America, especially someone like Lucy, who didn’t know I was albino.

We sat on the bed as Lucy applied gray eyeshadow to my lids with a tiny, padded brush, then used a stick whose end reminded me of a spider’s legs to rub the tops and bottoms of my nearly white lashes with mascara, a cosmetic item I hadn’t known existed until that moment. She ordered me not to blink even though my eyes started to water, and I felt the heavy thickness of the substance when she was done. Lucy complimented what she called my “cupid’s bow” before she uncapped a black tube of bloodred lipstick and rubbed it against my lips. She stood up and looked under piles of papers on her desk until she found a gold‑and‑black hair ornament she called a barrette and affixed it to my short hair right above my forehead.

“You’re almost ready,” she said. “We just need some pumps.”

Lucy gave me a pair of narrow black shoes made of plastic that was as shiny as the velvet of my dress was matte, with heels that tapered at the bottom, a couple of inches high. When I stood up after I put them on, pleased that they fit, I also found that I didn’t have as much trouble walking in them as I expected. Lucy led me back to her common room, where she opened a closet door. With a flourish of her hands, she motioned me toward the mirror on the other side. When I ambled over, I realized I was looking down because I was afraid to fall, so I tilted my head upward to see myself. “Not bad,” I said. I didn’t look nearly as ridiculous as I expected. “Come on, you look great!” Lucy countered, and I smiled to please her, grateful she took so much effort to get me ready.

Lucy’s suite was in an entryway near the dining hall, and as we walked downstairs toward the Gold Room—the vestibule before the main eating area that was literally painted gold—I came upon a few guys wearing dresses. In makeup and wigs, the thick hair on their faces and arms looked out of place, their movements clumsy as they loomed above me despite my heels, which clattered on the emerald tile floor.

“Whoa, you look like a real woman,” Kit Clark observed as he greeted me in the Gold Room. “It’s almost too convincing.”

Kit came dressed in a turquoise medieval gown that swooped to the floor, his curly hair in a low ponytail. He would have made a plausible woman too if not for his stubble, and a chin that was even broader than mine.

“What do you mean, too convincing?” I asked.

“Drag is supposed to be ironic,” he replied. “You just look like a girl.”

I understood what he meant when Zach and his friends did their “It’s Raining Men” number that night and wore ridiculous blond wigs as they sashayed and stomped on a makeshift stage in the middle of the dining hall, fingers splayed and wrists bent. Other men performed classics like “I Will Survive” and more recent Top 40 hits like “Express Yourself” with that same ludicrous air that felt designed to make fun of women.

Still in my outfit, I went clubbing with some gay friends after dinner, who let me hang around because we were all queer and at Harvard, even though none of them gave me the time of day romantically.

“Drag is supposed to be ironic,” he replied. “You just look like a girl.”

There was a Central Square club named ManRay whose Liquid night on Saturdays catered to a mixed crowd, and, befitting the name, people were encouraged to gender‑bend. I’d gone there a few times in shiny tops or spandex bell‑bottoms, but this was the first time I’d bent my gender all the way.

It was amusing to see curious looks from men who gave off straight vibes as I danced to bands like New Order and Pet Shop Boys throughout the night. Though my feet started to hurt after a while, I enjoyed the way my heels made my butt wiggle as I walked out of the club. I didn’t have the money to take a cab, so I left shortly after midnight to catch the T before it closed and ambled down the brick pavement of Mount Auburn Street toward Adams, after I got out at Harvard Square.

I hadn’t had anything to drink, but even so, I was afraid of tripping because of the brick, my heels, the tiredness of my feet. I also realized it had been a mistake not to bring a jacket. It was an unusually warm fall night, but the temperature had turned chilly over the last several hours, and I had to hug myself for warmth. I was about a block away from my dorm entrance when I became aware of a rumbling sound, unusually close to the sidewalk, then the honk of a horn.

I kept walking, figuring the noise had nothing to do with me. But as I got closer to my house and the street got quieter, I began to hear yelling from several young men.

“Turn around!” I heard one of the voices say.

I paused and swiveled my head in their direction, where I saw figures so dimly lit they looked like shadows, crawling by in a giant, early‑model American car.

“Hey, beautiful!” someone from inside yelled.

“Come ride with us!” another said. I smiled and shook my head as I rested a hand on my cheek.

“Not tonight,” I replied, my voice suddenly breathy and high. I observed my thickened eyelashes bat before I turned around.

It was only when I started walking again that I felt the sting of fear. I consciously pieced together what my instinct had already computed, that these young men had mistaken me for a woman, and I played my part to appease them. I also became aware that if one of these men had decided to get out of the car and examine me more closely, they would realize the mistake they’d made, and that this would make them angry, maybe angry enough to use their fists, and that it would be my body and not just my heels against the bricks. A deep part of me knew that running might incite them to chase me, and the safest choice was to walk at an even pace.

I was just half a block away now, and instead of their shouts, my mind tuned in to the outlines of my world, the rectangles on the ground that were barely red in the darkness of that hour, the thick white lines of a crosswalk in the distance. Lucy had lent me a black beaded clutch, and when I finally got to my dorm entrance, I fumbled for the clasp before I was able to fish out my keys, the ones I had a hard time getting in the keyhole because of my weak eyes. I had learned to unlock the door by feel rather than sight.

I brushed the hole with a trembling finger then tried to fit my key into the slot for seconds when each gust of wind felt like a man’s breath, every failed jiggle like a trap I couldn’t get out of. I turned myself into a ghost like I did as a child, without a body and free of fear, when my mother beat me or left me locked in my room overnight. The voices of those men, so loud only a few seconds before, sounded as if they came from the other end of a long tunnel, slippery as I tried to crawl out. Finally, my key found the hole and I clicked the latch above the handle with my thumb, then opened the heavy door as fast as I could.

I ran into a wall of fluorescent light and was suddenly afraid my broad shoulders would give me away. I hurried down the hallway and out of sight, started the climb up to my room as my heels made an almost clanging sound when they reverberated on the circular stairway. I only felt safe once I closed the door to my suite, as physical sensation returned to my limbs and I realized how much my feet hurt. I went to my bedroom to take off my shoes, relieved that my roommates weren’t there to see me. I felt ashamed somehow, to have attracted attention and then gotten so scared. I would turn the incident into a good story at brunch the next day, how some straight guys followed me home because they thought I was a hot girl. But that night, I just wanted to live with the fear and shame on my own, without the need to transform my experience into a witty anecdote.

I sat on the bed and took off my heels, rubbed my feet as I reflected on how tired they were, how nervous I still was, as my palm gripped my chest and I felt my heartbeat slow to a normal pace before my fingers relaxed. Yet as I recalled my fear, there also grew in me a surprising, pleasant sensation, and I smiled despite myself, fascinated at the sudden feeling that the experience had been worth it. Those men were convinced I was a woman, and I became curious about what they saw.

I left my bed and crossed our empty common room to look at myself in the bathroom mirror. But my face was too hard, the fluorescent light too harsh up close. So I took a step back, and then another, and then a few more, until I only saw my face as a sketch whose details my imagination could fill. The colors were more pronounced than I was used to, my eyes and lips outlined in smoke and red. I noticed the pleasant semicircle of my dress’s neckline against my chest and imagined graceful clavicles I couldn’t see. Though I did see that my neck was thin and long, something I’d never paid attention to before. All evening, people had told me I looked like a real girl, and those anonymous men had given me proof, but it was only then, in that bathroom mirror, that I perceived a glimmer of what they saw.

From afar, I felt like a girl to myself, even a beautiful girl. I gazed at that reflection and imagined my face as a woman’s face, holding features in my mind that others had told me were feminine—my high cheekbones, pouty lips, small nose. I grinned to myself at the thought of my nose, which I’d pulled on since childhood, hoping it would grow, since Filipinos preferred sharp, protruding noses. But I realized that my nose was dainty on a white woman’s face, as I also became conscious that of course it was a white woman’s face I imagined in that reflection, one of those vivacious ballerinas who thrilled audiences night after night, or the heroine of a 19th‑century novel.

Though as I began to walk toward my reflection, more and more of my masculine features came into focus, my broad shoulders and strong jaw, my prominent brow and high hairline, receding slightly at the corners. By the time my hands touched the sink’s cold porcelain again, I couldn’t help but perceive myself as a man dressed as a woman, a fool who would have been laughed at and beaten up had those men looked at me close in the light and found out the truth. I felt the immediate urge to rub off the makeup, but something stopped me, and instead, I leaned even closer toward my reflection. I suddenly remembered that I didn’t always think of my face as a white person’s face, how it took years to convince myself that I was not the aberration other people wanted me to be, but was instead practically the same as the Americans I watched on TV. I also recalled how this was not the first time I’d seen a reflection and imagined myself as a white woman with golden hair.


From Fairest by Meredith Talusan, to be published on Mary 26, 2020 by Viking, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. Copyright © 2020 by Meredith Talusan.

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