Why can't sex as a woman be as effortless as it was before I transitioned?
Illustration by Kelsey Wroten
My twink gay boy peak was that summer between junior and senior year I spent in London on a literature research grant. In practice, this meant spending a couple hours a day at the British Library, then going cruising for guys around Old Compton Street, at clubs like G.A.Y. and the Fridge, and saunas like Pleasuredrome. It was the 90s and England hadn't yet discovered the gym, so my ectomorph muscles from my college free weight and sit-up routine stood out, and people mistook my American confidence for "masc," or, as we called it in those olden days, butch. I encountered stares and smiles everywhere I went, as if crossing the pond turned me into a whole new kind of man altogether, someone who didn't turn guys off because I was too slim and fey.
I was never truly comfortable with public sex, being an immigrant in fear of deportation, so the most I allowed myself to do in bars was make out, or grope, or get brought to other men's flats because I stayed at a hostel with European backpackers. But Pleasuredrome, being a gay sauna, condoned and even encouraged extracurriculars, allowing my brain to turn off my fear of public sex—especially in the steam room, where clouds of steam obscured whatever was in your hand or mouth.
I loved it there, because along with our clothes, those who entered shed our social, real-world shells. Whether bus driver or businessman, scholar or construction worker, we found communion in the contact of our bodies. Most of all, I loved the dynamic shifts in power that came from being sometimes the pursuer, sometimes the pursued—sometimes with the same person, which was even more exciting.
One guy in particular sticks out in my memory, Danny. He was someone who could have anyone he wanted if he were in America. Not only did he look like he could have been the model for Michelangelo's David, he exuded a kind of undeniably masculine energy, made obvious by the way he jumped straight into the wading pool while I dipped my toes on the side. He emerged from the water and used his upper body strength to hoist himself and sit right beside me.
"I'm from Liverpool," he said, and I imagined him kissing me when he pursed his lips to pronounce his place of origin. Imagination became reality a few minutes later as our tongues caressed each other, but he disappeared after I took a momentary dip in the water to cool off. I searched for him in the steam room and sauna, and had pretty much given up when I finally saw his face behind me in one of the bathroom mirrors. He pulled me into a toilet stall for a shag, in the days before Pleasuredrome rented out private rooms.
Back then, I thought hot sex was mainly about the techniques two people used to give and get pleasure, an arithmetic of interactions between body parts. Hookups for me were distinct from relationship prospects. This was still my mindset early in transition, after I'd slimmed down over the four years since that summer in London. By the time I presented as a woman, I was 5'6" and 120 pounds, my blond hair grown past my shoulders.
My first hookup in that new incarnation told me it was a perfect experience for him. He was curious about sex with a "lady" like me but didn't expect to be with one who was more attractive than most "normal" women. I went through my fair share of hot hookups that year or so between first presenting as a woman and getting surgery, reveling in the novelty of straight (or at least straightish) male attention, which used to be forbidden fruit when I had crushes on jocks in college.
Of the many men from that era, the one I still think about a lot is Rich. Boston Italian and adorable, he relished in being a gentleman, drove me to the front of restaurants before he parked, opened doors for me, lent me his jacket when I got cold. He had this fantasy of finding the perfect stealth girlfriend, someone he could bring to dinner with his Catholic parents—even marry someday—without them having any idea she's trans. It thrilled him that I was so passable, and that I harbored what he considered dirty fantasies, like doing it with him in my office after work. I snuck him in one night, and I remember how resplendent his body was even in fluorescent light as he sat naked in my office chair, and I knelt on the itchy gray carpet, basking in the joy of giving pleasure to a beautiful man.
"Suck my dick you dirty whore," he whispered as he pulled my hair. And for the minutes after, and other days and nights after that, I was little, dirty, naughty, and always a whore, a slut who couldn't wait to have his body, and all the while I dwelled in the paradox of loving how he treated me like any other girl and hating how a girl like me was called a whore for wanting so much of him. But as hot as he was, I wasn't ready for anything serious so early in transition, and he stopped calling after I told him I didn't want to be exclusive. I ran into him at a trans bar in Boston called Jacques one night, because a friend was competing in a pageant there, and he looked disappointed when I told him I'd booked my surgery.
I spent my post-op 20s sleeping not just with any old straight men, but the tall, dark, and handsome types whose gay equivalents would have never given me the time of day—at least not in gay America, with its clone circuit that I was too short, thin, and femme to join. At first I could still do the fuck and disappear routine, avoid the drama of needing to tell them I'm trans. But over time I stopped hooking up just for fun, even when I was single. I mostly ended up trying to date those men, even when this was ill-advised in retrospect, as I constantly confused a potential relationship with satisfying sex.
It's hard to isolate the factors that led to this change in behavior—the influence of other women I met, the hormonal shifts I experienced, watching too many rom-coms—but certainly one big factor was the way those men treated sex with me as a triumph, as though they'd turn my pussy into a trophy if they could. And maybe I fell into that heterosexual trap for a while, the game of man luring woman into bed, woman luring man into relationship, which then became my own trophy, my proof that I was a woman just like any other. I'd be the Venus to his Mars, rather than feeling like Pluto, not even sure if I was a planet or not.
When I was a gay man on the prowl, there was a symmetry in what I wanted from other men, a reciprocity of desire and a clearer divide between the times I met men just for sex and those when I became interested in dating them. As a woman, it got harder and harder to hook up just for fun without feeling like I was being judged even by the nicest guys—the long tail of patriarchy that labels women like me a slut always finding a way to show its ugly self. Maybe if I hadn't spent time as a gay man I wouldn't have known the difference and gotten over it. But because I know what it's like to be seen as a sexual equal without all that baggage, the load often feels too burdensome to carry.
Don't get me wrong, I'm happier now that the world sees me as a woman. But in this specific situation, where I see a guy I want but not for anything other than sex, I miss the relative equality of our gender positions. I miss how the sexual dynamics when I was a gay man—who ended up on top, who ended up wanting the other to leave afterward, who ended up wanting more—wasn't nearly as laden with cultural and unequal social assumptions, those that brand a woman who wants no-strings sex a nymphomaniac, while her male counterpart is just a man.
The last time I tried to have a purely casual fling was in grad school at Cornell with Ben, a former gymnast who became my regular partner in an experimental dance class. We ended up in close proximity a couple of times a week, and I loved the feeling of how effortlessly he lifted me. We had almost nothing in common besides our clear physical attraction—I was a literature nerd and he was in business management—so I was happy to hop into his bed with no expectations when he invited me over. I Facebook messaged him for a booty call after we'd hooked up a couple of times, and he messaged back to say he'd call and then didn't. When I told him that was annoying, he wrote a weirdly magnanimous and formal message that ended with "I do enjoy seeing you in class twice a week, but I will not be able to maintain a relation outside of class." All he needed to say was that he wanted to stop hooking up. His smugness reeked for weeks afterward, the way his chin turned slightly upward to look past me when we danced, while I stewed over being the one who wanted him more, the one who was rejected.
It would have been much easier to brush the whole thing off if we weren't part of the imbalanced gender dynamic we live with. It's a social construct that affects all my relationships with men, whether casual or romantic, even with those who consider themselves progressive and feminist. And because we live in the world we live in, it stands to reason that many of us are affected by similar kinds of fucked-up gender norms.
I ended up at a different branch of my gym a few weeks ago and accidentally walked into the men's locker room, because tasteful gym decor these days means tiny signs and an open entryway around a corner rather than a door. As I walked in, oblivious, I encountered the lithe grace of a man's sinewy brown back as he sat on a bench in just a towel. I was suddenly transported to days and nights when my first association with men's bodies in real space and time was pleasure, not ambivalence.
The spell only took half a second at most, before a voice behind me warned that I was in the wrong locker room, and the man turned his dark, wavy-haired head and smiled at me briefly before I retreated backward as if a tape on rewind. For a moment, I wanted to rewind back, back to those days of adventure and lust in London, where pleasure given and received didn't have to be so complicated. Then I remembered that I would also need to be a man in this rewound state. So I put on my swimsuit in the women's locker room and spent the next hour in the pool doing lap after lap until my shoulders ached well, as I basked in the joy of being in my own body, alone.