A Trans Man Remembers a Blissful Third Date

Illustration by Gica Tam

Our Real Erotica series is a collaboration with Aurore, to tease, educate, inspire, and celebrate sex, because sex can and should be good. These narratives are not written by erotica writers—instead, they are stories from real people, exploring their past encounters and giving tribute to the sex they loved. In our fourth installment, a transgender man, Ambrose Winter, reminisces on the surprising beauty of his first time.

When I was eighteen years old, a few years ago—I won’t divulge the precise number; a gentleman never reveals his age—one could say that I lost my virginity. There is a lot of cultural baggage attached to the word ‘virginity’, and I could sit here all day and talk about it, but I won’t. All I will say about the term is this—it did not feel like a loss. 

It happened the third date with the man who would, a couple of weeks later, become my first boyfriend. The previous date, we held hands for the first time, and when we got to my flat we kissed for the first time, which quickly evolved into his tongue teasing at my clit.

I had, of course, been nervous to sign up for Tinder. I’d never been in a relationship before, never kissed anyone before, not even jokingly as a child. I’m a transgender man who has had no medical intervention whatsoever and pass in the same manner as a six-year-old would pass an A-Level physics exam. I was terrified that people on Tinder would only like me as a girl, or not like me because I’m a trans man who doesn’t look masculine at all. But to my delight, and with a substantial boost to my ego, this wasn’t at all the case.

There are hardly any positive romance stories involving trans people in the media, and if there are, they’re often very feminine trans women or very masculine trans men. There are very little representations of non-binary people, or binary trans people who dabble in androgyny. The first positive romance, and indeed erotic, story I heard like that was my own.

At the beginning of my third date with him—let’s call him Ezra—he poured us both a rum and cola that only had a whisper of rum in it, partially because Ezra hated anything that tasted like alcohol and partially because there was a shivering, unspoken awareness between us that we were going to sleep together. We sat on his bed together, legs hanging over the edge, drinks clasped in our hands. The tension stretched like a string of caramel, both of us being too shy to broach the topic that hung in the air, and it was finally I that broke it. “Soooo…” 

I was still an inexperienced kisser, but my anxiety melted away in the face of my desire.

“Soooo,” Ezra replied, a lascivious smile on his face, an expression I found myself unconsciously mirroring. Suddenly, the gap between us had closed, even though I didn’t register either of us making a movement, it was as if there had been some sort of quantum leap. One of us knocked over an empty glass, but neither of us took any notice. In the background, the album Narrow Stairs by Death Cab for Cutie was playing, and even now I can’t listen to it without remembering that afternoon. 

I was still an inexperienced kisser, but my anxiety melted away in the face of my desire and Ezra’s urgent but gentle assistance, and my mouth moved against his almost intuitively. I shifted onto his lap, legs straddling him, the soft marshmallow roundness of his belly one of the loveliest things I’d ever felt.  

A hand slid up the back of my t-shirt, trailing fire along the surface of my skin. “You’re not wearing a bra,” said Ezra against the side of my throat, and my neck arched upwards slightly in response. “Were you expecting this to happen?”

“Yes,” I said, amused, “but I hardly ever wear a bra anyway. They just remind me that I have boobs.” 

“Oh, yeah, understandable. But I’m glad you were thinking about… us. This.”

“I’ve been thinking of little else since last week.” My hand attempted to roam beneath the waistband of his trousers, and I immediately learned that this maneuver was not nearly as easy as my erotica books would have me believe. “Fuck’s sake,” I said through gritted teeth as my wrist got stuck, fingertips just centimeters shy of Ezra’s cock. 

He giggled, a high little laugh that I didn’t expect to come from a six-foot man with a baritone voice, and it was the most endearing thing I’d ever heard. I resolved to make him do it more often. “Hang on, hang on—” We took a brief interlude to disrobe, the indie rock music still playing quietly in the background, delicate notes washing over me and creating an atmosphere that seemed almost dreamlike combined with my already hazy mind, whirling with lust and anticipation. 

My clothes had never felt so cumbersome, my fingers never so fumbling. When we finally—finally!—were nude, we tumbled back onto the bed, limbs entangled. I wrapped my hand around his cock and he whimpered, hips bucking involuntarily upwards. There was a fire burning in my lower stomach, and all I wanted was him, inside me, right now. 

Although I was a virgin, I was only minimally nervous. I was a virgin in the sense I had never had a penis inside my vagina, but I probably wouldn’t be considered a virgin in, say, Victorian times. When I was younger I’d had a fear of sex after I’d tried to insert a tampon when I was thirteen and found it impossible. I spent the rest of my adolescence focusing my solo adventures around my clit, but when I reached eighteen and began to start thinking about getting into the dating game, I realized I had to do something about it.

So I approached the problem in the way I approached any other; methodically and logically, starting with my pinky finger and gradually ascending until I could fit my index and middle in. I was ecstatic, because I’d thought there was something wrong, but I was wrong, and I finally drew blood with a glass dildo shaped like a tentacle (which was possibly the most on-brand thing I’ve ever done) and to my astonishment it didn’t hurt at all. 

And so, the only emotion I felt to any mentionable degree was desire. Overwhelming, all-encompassing desire. 

Ezra reached for a condom and lube on the bedside table, ripping the condom packet open with his teeth, which I found unbearably sexy. But to be honest, at the moment everything he did was sexy. He could sneeze and I would find it attractive. 

“Are you sure we need the lube? I mean…” I took his wrist, guiding his hand to my pussy. His fingers slid around my vulva, teasing at my entrance. “Feel how wet I am.”

"It’s your first time, and I want it to be amazing for you."

Ezra moaned lowly against my throat, a finger slipping inside. My hips rocked forward, trying to drive his finger in to the knuckle. “You are wet,” murmured Ezra, nipping lightly against my throat. “But we should use lube, just to be safe. It’s your first time, and I want it to be amazing for you.” 

“Okay,” I breathed.

“You wanna go on top? I don’t want to hurt you. It might be easier to set your own pace?” His hazel eyes were wide, and if anyone saw our expressions in the moment, they’d have thought it was Ezra who was the nervous virgin.

“I like the sound of that,” I purred, and Ezra relaxed. “Are you ready?”

“Absolutely,” Ezra replied, flashing me a wicked smile before falling backwards on the mattress, pulling me down with him. 

I took his cock in my hand, lining it up with my entrance before sinking down on him, my head tipped backwards as I let out a breathy moan, relishing the feeling of Ezra filling me up. There was a slight burn, which disappeared as I began riding him. 

I looked down at Ezra’s face, my pussy pulsing as I saw his eyes on mine. The thick curtains were drawn, but there was a tiny crack that threw a narrow shaft of golden sunlight over his face. This chiaroscuro, along with the dark curls fanned out over the ivory pillow, made him look like a figure from a Caravaggio painting. 

I came over and over, each orgasm rolling into the other until I was in a near-constant state of delirium, hands tightening on Ezra’s hips. He thrust his hips in tandem with mine, driving upwards into me furiously as he reached his own climax with a loud, gasping moan that I was pretty sure the neighbors heard, but by this point I couldn’t bring myself to care. 

“That was amazing,” I murmured sleepily as I flopped down next to him on the mattress, cuddling up to his side. “Everything I hoped my first time would be.” 

Ezra smiled at me tenderly, stroking a stray hair from my cheek. We both knew it was a terrible idea to fall asleep at midday, but as we lay in each other’s arms floating in a post-orgasmic bliss, it was the only thing we could do. Neither god nor mortal could have dragged us from that bed.