“Endlessly Seductive, Endlessly Terrifying.” Lucy Sante on the Idea and Reality of Transition


Between February 28 and March 1, 2021, I sent the following text as an email attachment to around thirty people I considered my closest, most consistent, day‑to‑day friends. While I sent the emails out individually, the subject line was usually the same: “A bombshell.” I smirked at the unintentional pun and wondered whether anyone else would. It was simply titled “Lucy.”

The dam burst on February 16, when I uploaded Face‑App, for a laugh. I had tried the application a few years earlier, but something had gone wrong and it had returned a badly botched image. But I had a new phone, and I was curious. The gender‑swapping feature was the whole point for me, and the first picture I passed through it was the one I had tried before, taken for that occasion. This time it gave me a full‑face portrait of a Hudson Valley woman in midlife: strong, healthy, clean‑living. She also had lovely flowing chestnut hair and a very subtle makeup job. And her face was mine. No question about it—nose, mouth, eyes, brow, chin, barring a hint of enhancement here or there. She was me. When I saw her I felt something liquefy in the core of my body. I trembled from my shoulders to my crotch. I guessed that I had at last met my reckoning.

Very soon I was feeding every portrait and snapshot and ID‑card picture I possessed of myself into the magic gender portal. The first archival picture I tried, contemporaneous with my first memory of staring into a mirror and arranging my hair and expression to look like a girl, was an anxious, awkward studio portrait of a tween, all cowlicks and baby fat. The transformed result was a revelation: a happy little girl. Apart from her long black hair, very little had been done to transform Luc into Lucy; the biggest difference was how much more relaxed she looked. And so it generally went—I was having a much better time as a girl in that parallel life. I passed every era through the machine, experiencing one shock of recognition after another: That’s exactly who I would have been. The app sometimes returned blandly misjudged or grotesquely distorted images, but more often than not it weirdly seemed to guess what my hairstyle and fashion choices would have been in those years. The less altered the resulting images were, the deeper they plunged a dagger into my heart. That could have been me! Fifty years were under water, and I’d never get them back. My high‑school graduation portrait, a haughty near‑profile, hair waving off the brow and into a curl, became an impossibly delicate almond‑eyed fawn (age 17 was indeed the summit of my beauty, which is probably why my male incubus immediately grew a beard). Ten or twelve years later (there are regrettably few photos of me in my 20s; I’ve always been camera‑shy), I am a Lower East Side postpunk radical lesbian anarcha‑feminist with a Dutch‑boy bob and a pout. Here I am at a Sports Illustrated junket in Arizona, age 33, looking demure in a white sweater over a red polka‑dot dress, talking to a boy.

I was terrified, that is, of finding myself confronted by what I am confronting now.

There are many reasons why I repressed my lifelong desire to be a woman. It was, first of all, impossible. My parents would have called a priest and had me committed to some monastery, lettre de cachet–style. And the culture was far from prepared, of course. I knew about Christine Jorgensen when I was fairly young, but she seemed to be an isolated case. Mostly what you came across were aggressively vile jokes from Vegas comedians and the occasional titillating tabloid story. Nobody felt threatened by transgender people; on the contrary, they were viewed as hilarious sideshow acts—literally and otherwise, as in Weegee’s photographs. I kept searching for images or stories of girls like me, without much luck. I would swoon over pictures from Finocchio’s or Club 82 I might find in passing, but their stars mostly seemed to be gay men who changed back into male drag after the show. Over the years I consumed an impressive amount of material on transgender matters, from clinical studies to personal accounts (where are you, circa‑1984 issue of Actuel—or was it The Face?—that nearly broke my mind?), to new‑journalistic exposés to porn. Not much of the porn, though; it grossed me out. I researched the subject as deeply as I did any of my books, but my notes all had to be kept in my head.

I immediately disposed of all materials, because I was terrified of being seen. When with some regret I threw away a pseudo‑scientific piece of exploitation called The Transvestites, I made sure to bury it in the center of the trash bag. Until browsers made anonymous searching possible, I wiped the search memory on my computer every day. Why, you may ask, did I feel it necessary to go to such lengths? The short answer is that I’m mildly paranoid about writings on paper (or screen) because my mother regularly raided my room, reading anything in my handwriting and vetting all printed matter for anything that might even remotely allude to sex. I extended that caution to my friends, most of whom would surely have been sympathetic, because of the notion I long possessed that women would be disgusted and repelled by my transgender identity. Where did I get that one? It may be because until I was in my late teens I didn’t know many women, as an only child of isolated immigrants, and although I had one early romantic interest, I didn’t have a female friend until I was seventeen. It may also very well have come from proto‑TERF sentiments I picked up from feminist tracts. Needless to say, I was awful at sex. I did not know how to act like a man in bed. I wanted to see myself as a woman in the act of love, but I also had to repress the desire, while simultaneously trying earnestly to please my partner (because I almost never slept with anyone I didn’t love at least at first). Most of the time, the mass of contradictions prevented me from any but the most mechanical sexual fulfillment, and necessarily impeded my companion’s pleasure as well.

I was not at all attracted to men, and I spent enough time in gay environs in the ’70s to be sure of that. At puberty and afterward I was uncertain how to construct a masculine identity. I hated sports and dick jokes and beer‑chugging and the way men talked about women; my idea of hell was an evening with a bunch of guys. Over the years, from force of necessity, I created a male persona that was saturnine, cerebral, a bit remote, a bit owlish, possibly “quirky,” coming very close to asexual despite my best intentions. During those same years I thought about my trans identity every single day, sometimes all day long. I had a range of masturbation scenarios: cast as a girl in the school play, then persuaded to go out on the town in costume; hired as an assistant by a wealthy society woman who amuses herself by dressing me up as a girl; new roommate assigned to me in college has been dressing as a girl for years and has a full wardrobe. Yes, they were transvestite fantasies, but that was what seemed available. Just the idea of wearing women’s clothes made me dizzy, and I can count the number of times I dressed up (furtively, alone) on the fingers of one hand. I looked lovely, but I felt as though the entire world was looking on in contempt or repulsion or dire judgment. But then I couldn’t just wish myself into magically becoming a girl, could I? And when I truly probed my desire to have breasts and a vagina I was suffused with an existential terror.

Another reason for my repression was my sense that if I changed my gender it would obliterate every other thing I wanted to do in my life. I wanted to be a significant writer, and I did not want to be stuffed into a category, any category. At first, writing seemed to be a pursuit where one could hone a persona with words while evading inspection in the flesh, but marketing changed that, brutally, beginning in the ’80s; I could no longer hide there, and if I were transgender that fact would be the only thing anyone knew about me. Over the years, transgender people became gradually more visible in the media, and the coverage became a little bit less snide. I lived in New York City, so I saw transgender people often: the doo‑wop group that lived as women in the Whitehall Hotel on 100th Street, the two very polished party girls in tiger prints I saw one early morning in the subway. A few years later I passed through the same circles as Greer Lankton and Teri Toye, although I was too scared to ever talk to them; they seemed like mythological creatures come to earth. For that matter I was close for a while to Nan Goldin, who would have been certain to understand my story, but I never breathed a word. I would hear rumors that this or that person “dressed up,” and I would be forever ill at ease in their presence as a result—from envy, of course. My office in the late eighties and early nineties was a block from Tompkins Square Park, but I never so much as peeked in at Wigstock (I could hear it), and half a block from the Pyramid Club, but I never went there, either, except maybe to see some band. In those days the club had a black menu board on the sidewalk outside that read “Drink and be Mary.” I trembled every time I passed it. I’d occasionally see skits on the UHF porn channel by persons calling themselves “chicks with dicks,” and know they were somewhere in my neighborhood, maybe very close by. In the late nineties I was invited to the dinner after Nan’s Whitney opening, and seated at my table was the glorious Joey Gabriel; I’m not sure I spoke a word during the whole course of the evening.

Until these past few weeks, my repression kept me from seeing the phenomenon as a coherent whole.

I was terrified, that is, of finding myself confronted by what I am confronting now. Somehow now the dam has burst, the scales have fallen away, the fog has lifted. The various lists above give but a small idea of the vast scope of my investment in my transgender identity. I absorbed every factoid, every anecdote, every historical speculation, every scabrous rumor pertaining to the matter of boys changing into girls. I continually conjured up, reveled in, and suppressed images of myself as a woman. It was the consuming furnace at the center of my life. And yet, until these past few weeks, my repression kept me from seeing the phenomenon as a coherent whole. I wanted with every particle of my being to be a woman, and that thought was pasted to my windshield, and yet I looked through it, having trained myself to do so. Now that the floodgates have opened I am consumed by the thought in a new way. I have spoken frankly to my therapist about it, making her the first human being (after nine or ten previous shrinks) to hear those things from my lips. That gives the matter the force of reality. When I uploaded my first picture to FaceApp I felt liquid and melting in the core of my body. Now I feel a column of fire.

That should not, however, imply a steely resolve. Now that I have opened Pandora’s box, I cannot close it again, but have no idea what to do with the specters it has let loose. The idea of transitioning is endlessly seductive and endlessly terrifying. I take at least one selfie every day and transform it, and it feels as though the pictures are becoming ever more plausible. Yes, that’s clearly my face, every bit of it—my features are fortunately disposed, and even the contours of my face are not excessively large. With a bit of makeup, a course of estrogen, and a really nice wig I could look exactly like that, maybe. But will the fact that I can’t grow my own hair make me feel like a fake forever? It doesn’t take much to make me feel fake—the much improved social climate of the present, the very thing that has made this recent epiphany at all possible, also makes me think that others will see me as merely following a trend, maybe to stay relevant. And I am soon to turn 67. What if I look like a grotesque? Or merely pathetic? While I know that my friends and the people I know in publishing and the arts would be sympathetic, and that my main employer is exceptionally trans‑friendly, I worry about private reactions. I myself have not always been kind when someone in public life or on the periphery of my social orbit has transitioned in ways I thought less than successful or less than dignified. I’m worried about having the talk with my son, although like many members of his generation he has transgender friends and is very open to the subject. Most of all I worry about telling my partner, with whom I’ve shared an affectionate relationship that has slowly become more companionate over the past fourteen years. I don’t doubt her sympathy, but can also imagine her asking what her role might be, as if to say that I am living out a love affair with myself. And would she feel comfortable with my wearing feminine clothes and accessories while she wears mostly T‑shirts and jeans?

It’s a vast decision, with the power to affect every aspect of my life. Would I inadvertently destroy important things in my life as a consequence? I think about transitioning incessantly, look at sites for wigs and makeup and clothing as if I were actually shopping and not simply stocking the larder of my imagination. If it weren’t for COVID‑19 I would contrive some way of paying a visit to a transformation salon, but those places are all closed now. I keep wanting to be forced to transition by some circumstance, maybe my therapist telling me that it is crucial for my sanity. Anyway I’m starting here, by writing it down—something I’ve never done before—and by sending it to a very few people whom I trust and who I think will understand. My name is Lucy Marie Sante, only one letter added to my deadname.

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i heard her call my name

From I Heard Her Call My Name: A Memoir of Transition by Lucy Sante. Used with the permission of the publisher, Penguin Press, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. Copyright © 2024 by Lucy Sante.

Lucy Sante



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