This Magazine

Progressive politics, ideas & culture

May-June 2019


Waiting for Miracles: A post-op trans girl on sex and love

Gwen Benaway

“I’ve turned all my sorrow into glass

It don’t leave no shadow”

            —Robyn, “Missing U”


A boy is driving me home from a poetry reading. I have a crush on him. We’ve been talking and hanging out for five months now, gradually learning each other’s lives and sharing small moments of softness. My sexual reassignment surgery happened three months ago and I can feel the ache between my legs as my body heals. I keep shifting positions in the front seat of his car, trying to sit without putting any pressure on my newly formed vulva.

It’s an early spring night. The highway is empty in the darkness between cities. It’s almost 10 pm, long after rush hour. I watch the headlights of the car illuminate brief flashes of farms as we drive past. I have the Google Maps opens my phone to give him directions as we navigate back to Toronto.

As he drives, we talk about love and what it means to care about someone. I ask him if he has ever looked at transsexual porn, something I always ask men that are romantically interested in me. I’m not sure what answer makes me feel better. If they say yes, I’m relieved because I know they find women like me attractive but worried because I don’t want to be just a kink. If they say no, I doubt that my vagina can ever live up to the cis women that they’ve slept with.

He replies that he’s never looked at transsexual porn before. He’s never even considered the possibility of dating a girl like me. The road seems to stretch infinitely before us but the space in the car feels like it’s collapsing around me. He keeps talking while I try to calm my racing heartbeats. He wonders aloud to himself if being attracted to me means that he’s “a little gay”. I don’t know what to say back to him, so I stay silent except for a small muttered “mmhmm.”.

I stare out the passenger window into the open space of the fields beside the highway as he keeps talking. I can feel the bottom of my stomach drop out of the car and disappear into the night sky. I lift my hand up to brush strands of my blonde hair back behind my ears. I think about the hours I spent in front of the mirror today getting ready for the reading, knowing that I would be with him. How much time I spent perfecting my makeup and my outfit, trying to conceal every remaining masculine feature of my face and body.

The ache between my thighs hurts more now. I can feel the dampness of my panties as my pad slowly fills with the fluid and blood from post surgical healing.  I try to distract myself from the pain and discomfort by thinking through his comments as the car winds it’s way back towards the city.

Maybe him desiring me is a little gay. I know I don’t look like a cis woman. There are moments when my laugh is too deep or tiny black hairs show above my lips. My face is angular, filled with strong lines that hormones and surgery haven’t completely erased. I’m not a man-and I don’t believe that I ever was one- but my womanhood is always in question by the world. What can I offer him that he couldn’t find a better version of with a cis woman?

I don’t say anything to him about what he said to me that night in the car. I focus on the rare joy of being with him and feeling temporarily human. The song “Hotline Bling” comes on the radio and he dances in the front seat to it, teasing me with his eyes as he makes fun of the stupid lyrics. What I love in him is small moments like this one, moments when he forgets the violence surrounding his body and is free inside it. When he drops me off at home, I hold onto him as tightly as I can for as long as he lets me, trying to be as close to joy as I can.

I’m haunted by our conversation in the car. Things between us are never the same again. I stop trusting him, even though I try to make excuses for what he said. Even now, almost a year later, I replay his words over and over in my mind. People would be quick to call him transphobic for suggesting that loving trans women is “gay” but I don’t think he is any more transphobic than the rest of society. It’s nice to imagine guys having the right response to a trans girl in every moment, but it’s not a realistic expectation.

What haunts me isn’t what he said anyway. It’s my own response that wounds me. I didn’t know what to say, because I don’t feel like enough of a woman to deserve better treatment. When we eventually stopped speaking to each other, I was heartbroken but strangely elated. After 8 months of intimacy, I didn’t have to worry about trying to be good enough anymore.

I wasn’t good enough. There’s a terrible comfort in accepting that nothing you do will ever liberate you from the oppression of transphobia. I got the surgery and tried my best to pass, taking vocal feminization lessons after work and watching hours of makeup tutorial videos online. But I’m not a cis girl and I don’t want to have to look like one to be worth loving.

Transmisogyny feels like the empty space along the highway, surrounding everything in the world and briefly visible in the headlights of my writing but never contained. Infinite, stretching between my body and the sky, drowning me. Whatever I say or don’t say, it always defines the limits of my love.


Sometimes I dream about him and me on that car ride. In the dream, we don’t speak to each other but ride in silence towards the Toronto skyline. I feel at peace even though the countryside is completely dark. He’s there with me always, caught in a horizon of the distant condo towers and the sound of the radio.

I hate waking up from my dreams of him but I always do. The waking world is relentless. It hungers for my life.

Not even my dreams are never big enough to save me.


Last fall, I wrote a paper for a class about trans women’s representations in porn. The class was about sex and pleasure, but none of the course readings acknowledged the existence of trans women. I sat through hours of class discussions about orgasms and queer cruising, wondering if a body like mine will ever be seen as real. Trying to resist our erasure from ideas of sex and pleasure, I decided to write my final paper by looking at a small sample of pornographic films featuring trans women.

I thought it would be an easy paper to write, but I was wrong. It was hard to view hours of trans women in porn, shifting through the comments by the mostly cis male viewers. Sometimes I cried over the images that I found. Sometimes, I sat alone in a coffee shop and stared at the blinking word processor before me, unsure of what to write. It wasn’t the explicit sexual content that upset me, but the unexpected moments of intimacy and tenderness between performers.

I was captivated by seeing trans women sharing softness with male partners. I never see men kiss trans women in my life. Aside from a few movies and television shows, trans women rarely appear as people of any romantic worth. I played the porn on my phone, skipping through the blow job and penetration scenes until I reached the end of films. After his orgasm, the male performer would make out with the trans woman, stroking her hair and holding her while she masturbated.

The intimate scenes have haunted me for months now. One performer, a mixed-race trans woman in her thirties with dirty blonde hair and an effervescent smile, is my favourite. Her voice sounded like mine, just at the bottom edge of a stereotypical feminine pitch. She is beautiful, but not “passable” as a cis woman. Her facial features were too strong and her hairline was a little too high. It’s obvious that not being “passable” was part of her erotic appeal to the porn site and it’s viewers, a beautiful trans woman that couldn’t be imagined as anything but “trans.”

Sometimes she would tease her partners, laughing at them and their machoism before fucking them. In other films, it seems like she isn’t enjoying herself, turning her face way from the camera and wincing in pain. I don’t want to imagine that I understand what her experience of her work is. It’s obvious that I am projecting my experiences onto her.

I don’t really know why she made the films. It’s possible that she did the films because she found them pleasurable. It could have been a purely economic decision or a mixture of pleasure and economics. Trans women have one of the highest unemployment rates and experience tremendous amounts of workplace discrimination. We often don’t have many other options to support ourselves but selling our sexual labour.

There is one film of hers which stands out to me. She is paired with another mixed-race performer, a younger cis man with intricate tattoos on his forearms and chest. Their chemistry is marked by tenderness between them. He kisses her whenever possible, lifting her head up to his.

In the last shots of the film, you can hear him whisper that she’s beautiful in her ear while she’s cumming, his fingers caught up in her mussed hair. She looks euphoric in her body. When she cums, the camera pans from her face down to her genitals. He’s holding her hands, wrapping them with his own. Maybe they are just good at their jobs, but something in the film shatters me with every viewing.

I have sometimes been like her. Briefly in the haze of sex and touch, I felt like a woman worth loving. Not anymore. Maybe I never will feel that way again. Pain and pleasure, violence and joy, a trans woman and cis man.

I watch the films again late at night, wondering “why are the things that we’re called more powerful than the things we feel?”


I’ve taken a break from romance or sex. I got sick of hearing the same script from partners, predicting their words before they even spoke them. Phrases like “I tried to be open to the idea of what you are” mingle with “I am wondering if it’s gay to be with you” in my memory. Before bottom surgery, my status as a “woman” felt more solid with partners. I think the unknown of my post-op vagina is more frightening to men than my penis was. Before surgery, they thought they knew what they were getting into.

People often assume that genital confirmation surgery means that you can stop being “trans,” but I haven’t felt any less “trans” since my surgery. If anything, having a vagina has made me feel more “trans.” Transmisogyny isn’t inverted by surgical changes to your external sex organs.

Sometimes I don’t feel like a woman. Not because my internal sense of my gender has shifted, but because I never have access to anything that other women do. It’s hard to experience sex or romance when you don’t feel like a person any more. I wake up in the morning and imagine my body disintegrating into the soil when I’m dead. It comforts me to remember that I won’t have to explain myself forever. I’ll die someday. All that will be left of my gender is the pronouns they pick for my funeral program.


I like my memories of that boy who drove me home. They float in and out of my head as I wander through my everyday life, distracting me from the mundane violence of cis people’s unwelcome stares.

Once he told me that he just wanted to take care of me. We were sitting in a Tim Horton’s after an art show. I watched his face as he spoke, his eyes lighting up with an emotion that looked like pride. I don’t know what he was proud of – wanting to love me or his own courage at telling me – but it stands out to me. I rarely see men look at me with pride or anything close to it.

He didn’t take care of me, but he wanted to. That matters more to me than how things ended. There were moments with him where I felt safe, trusting in his soft and careful presence without worrying about what might happen.

I never feel that way with men. I’m always terrified of them, sensing the unspoken debates running their minds about whether they could love a girl like me. When one of ex boyfriends broke up with me last summer, he chased after me down a city block, shouting “I tried to be open to what you are”.


Maybe that’s why I obsess over this one boy. He’s not particularly special, but there was always something about him that captivated me. Whenever he walked around with me, I could feel a restless worry inside his body, as if the world might suddenly swoop in and eat him whole. I feel the same constant anxiety in public, but I’ve never dated anyone until him who understand that part of me. Sometimes though, when he truly felt comfortable in a space, his body would suddenly open to the world like a small miracle. Once he leapt up onto a low concrete divider and walked its whole length beside me, gleeful and boyish.

I miss the small wonder of him as much as I miss the way his neck smelled. I felt more human when he was in my life. Beside him, I was just an ordinary girl, small in my body and filled with possibility. Now he’s gone and the ordinary part of me that loved him feels gone as well.


Cis readers and editors often pressure trans writers to speak on behalf of all of trans people, but I can only reflect my experiences. The danger of focusing solely on “representation” as a way to alleviate oppression is that the oppressor- cis audiences- holds all of the power. Cis people remake us into whatever they want, rewriting our images and stories into easily marketable products. Lured by the promise of fame and a chance to escape our oppression, we perform our parts until they get bored and we’re discarded.

In a cruel way, the dehumanization of writing essays like this one feels the same as the dehumanization of my experiences in sex and love. All I have to offer is a rare experience- a exotic thrill that lets cis people feel more radical than they are. Once cis people have read my work or fucked me, I’m worthless to them. I often wonder why I keep writing and going on dates, pretending that I can ever be more than an illicit fix, but it’s the only way I know how to survive.

I’m going to write a disclaimer sentence here to remind you that every trans person’s experience is different. No matter how hard I try to account for the gaps in my awareness, I can’t write a single essay that includes all possible nuances. The recent increase of trans representation within the media has been described as a “trans tipping point”, but girls like me still remain caught between two polarizing forms of representation. We are either the hyper sexualized gender rebel who challenges social order or the unthreatening desexualized icon with an inspirational message about inclusion and diversity.

The increase in trans representation has not translated to a lessening of the social stigma around dating us. There was a study done recently in Toronto on cisgender people’s attitude towards dating trans folks. It found that out of 958 Torontians, 87.5 percent of participants said they would not be open to dating someone who is trans. That means that only 1 in every 8 participants would even be open to dating with a trans person

But it’s not just the violence of transmisogyny and the complexities of trans girl desirability that complicate my love life. Throughout the process of my transition, I went through very traumatic experiences. Surgery—despite it’s joyful outcome for me—left me with an intense fear of hospitals and terrifying memories of blood, morphine, and transphobic doctors. The violence of transition lingers in the body, not dissolved by the pleasure of finally being embodied as myself.

How do you love through trauma? Explain experiences that few people will ever go through? Trust new partners after men have shamed and raped you? I think through these questions in between therapy sessions and hang outs with friends. I don’t have answers. There are trans women in my life with partners and healthy relationships, but I know how rare it is to find that. Of course, people remind me, love is just as possible for you as it is for anyone, as if things like systemic oppression and prejudice don’t influence our desires or possibilities for joy.

Hoping for a miracle in every intimate encounter isn’t a way to live your life. I’m not hoping for the miracle of monogamous love, but for any small moment with a partner where I feel human again. Everyone on Twitter has been retweeting quotes about valuing friendships as much as romantic partners. I agree with the idea, but their tweets feel like a judgement that there’s something else wrong with me beyond my transness: a perverse capitalist desire for pleasure and intimate touch.

I’m sure there are a million holes in my thinking. Maybe I need to change my hormones dosage. I probably haven’t read the right essay on love or tried hard enough to heal from my past abusive relationships. I resolve to order a rose quartz night light. I promise to deepen my conceptual understanding of Queer Theory and diligently interrogate my privileges with clear accountabilities. I want to be good, satisfied with the absence of gender-affirming sex and love because I’ve overcome the small hungry animal inside my skin and between my legs.

Instead of doing any of these things, I stare at the Instagram stories of that boy. I think I loved him and maybe he loved me. We can’t talk any more because being in the same room hurts too much. We fucked up, imagining that we could safely navigate the complexities of our lives. I pause the Instagram story and zoom in on his face. I try to remember how his hands felt in mine or what his voice sounded like on the phone, but I can’t.

That’s love, I guess. Holding onto the traces of something better than what you have. I want to know what it means to date when so few of us have ever actually known love. What happens when all we have to give each other is our pain? I try to remind myself to not obsess over the past. Stay hopeful, I say to the girl in the mirror, miracles can happen.

But they don’t. They never happen and I don’t think they ever will.


The trans porn actress has made about 40 films over the last four years, and I’ve watched them all. For a while, I wondered if my interest in her was sexual, but I think it’s just a way for me to remember what it felt like to be loved. When she cries out in joy or kisses her partners back with the same intensity, I see what it would have looked like if someone had been filming me with the people that I loved.

I don’t have any other videos or images to remember my joy by. As a trans woman, all of my partners keep me secret from the world. There’s one photo of me and that guy I still love. Aside from a few close friends, no one even knows we were ever together. Porn is the only space I have to remember what it felt like with him.

Maybe it’s wrong to cry from the images of a trans woman being lovingly kissed and held. In the back of my mind, I can already see the quote tweets saying that I erase Queer trans women or educating me on the nuances I’ve missed. I want to add more disclaimers, soften sentences until they ooze the right blend of affirmation and searing insight, but I’m tired. I can’t even explain how I feel as a woman, so how could I speak to anyone else’s experience of their lives?

All I really know is that I’ve been in love before. It felt good, I think. I can’t remember clearly now, but sometimes—in sad songs and porn videos—I feel it again for a moment. It hurts, but that good kind of hurt. The way you sometimes feel after sex. As if you’re made out of glass; worn out, aching, and confused, wondering how you will ever live through this persistent wanting.


A version of this essay appeared in our May-June 2019 Love & Sex issue

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