What I Learned That Afternoon with a Transvestite

I’d been opening and closing the same browser tab for weeks. There was an ad, a profile photo, a phone number, and a single line: “I keep you company, I listen, I enjoy.” Nothing else. The name was Sonia. The photo showed very little: a woman standing by a window, light falling in from the side, her features barely discernible.

It wasn’t the first time I’d moved through that territory, but it was the first time I seriously considered crossing it. I’d been with women for years, and later with men. The gay world had attracted me for a while, but in recent months I felt I was looking for something different, something I still didn’t know exactly how to name. When I saw that ad, something in my chest tightened in a way I knew well. I wanted a cock, but I wanted a cock in a woman’s body. I wanted tits, I wanted painted lips, I wanted stockings, and I wanted a hard dick waiting for me beneath the fabric.

I called her on a Thursday afternoon from the bathroom at work, with the water running to muffle the sound.

—Yes? —answered a soft voice, a little rough around the edges, with the unhurried cadence of someone in no rush.

—I saw your ad —I said, and the silence that followed was brief enough not to feel awkward.

—When would suit you? —she asked, without any preamble.

We set it for Saturday at five in the afternoon. She gave me an address downtown, in a neighborhood of old buildings with narrow balconies and stone facades. I hung up and stood there staring at the phone with the water still running, feeling as if I’d crossed an invisible line.

***

The building had an intercom. The buzzer sounded and the door buzzed open before I could say a single word. I climbed three floors up a staircase that smelled of damp wood and freshly brewed coffee. I knocked on the third-floor door and waited.

When she opened it, I had to reorganize what I was seeing.

Sonia was taller than me, though her heels added some of those centimeters. She wore a short black lace dress that ended mid-thigh, sheer stockings, and dark brown hair gathered into a messy bun with two strands escaping to brush her neck. Dark red lipstick. Eyes made up with a precision that was hard to ignore.

—Come in —she said, stepping aside.

The apartment was small but well cared for. There was a bookshelf full of books on the back wall, a floor lamp with warm light, and a wooden side table with a half-finished cup of tea. It looked nothing like what my imagination had built up over the course of the week.

—Do you want something to drink? —she asked from the kitchen.

—Whatever you have —I replied, sitting on the sofa.

She came back with two glasses of water and sat beside me with a calm that threw me off. There was no rush. She asked me my name, whether it was the first time I’d done something like this, where I was from. We talked for ten minutes like acquaintances running into each other by chance, and somewhere in that conversation most of my nerves slipped away.

—What would you like? —she asked at last, with a directness that wasn’t harsh.

—I don’t know exactly —I admitted. —I’ve been thinking about this for a while. It’s the first time I’ve been with someone like you.

She nodded without drama.

—Then we’ll go slow. You’re going to suck my cock, I’m going to fuck you, and you’re going to end up asking me for more. But step by step.

My mouth went dry all at once. I nodded without saying anything.

***

She was the one who came close first. She put her hand on my thigh, slowly slid it up to brush my crotch over my pants, and looked me in the eyes for a second that seemed longer than it was, pressing just enough to check that I was already hard. Then she kissed me. Her lips were soft and tasted like tea with honey. The kiss started out slow and immediately opened up: her tongue entered my mouth with expert calm, seeking mine, and her hand kept pressing through the fabric while she bit my lower lip.

When we pulled apart, her eyes were half-lidded and she had a slight smile.

—Take off your jacket —she said.

I took it off. She stood and began unzipping the back of her dress with a fluid movement, without turning around. The lace fell to the floor and she stood with her back to me for a moment, in a black silk thong and stockings held up with a garter belt of the same color.

She turned.

Her tits were small but real, with dark nipples already erect, pointing at me. The garter belt framed a narrow waist. And at the center of the silk thong there was a bulge that made no attempt to hide itself: the unmistakable shape of a cock pressed against the fabric, pushing the waistband up, with a small wet spot where the head was.

There it was. And it was exactly what I wanted to see.

She sat astride me and kissed me again, this time more intensely. Her hands unbuttoned my shirt with deftness while I circled her waist and felt the heat of her skin against mine. I grabbed her tits with both hands, pinched her nipples, and she let out a short moan into my mouth. I could feel her hard cock rubbing against my stomach through the silk, leaving me a warm, sticky trail. At some point in that sequence I fumbled the garter belt loose, and she laughed a little, without mockery.

—Here —she said, guiding my hands to the thong’s waistband.

I pulled the silk down and her cock sprang out all at once, hard, thick, with veins standing out and the head shining with pre-cum. It was bigger than the clothes had suggested, and seeing it there, emerging from a woman’s body with her tits out and the garter belt still on, hit me in the stomach like something physical. She took me to the floor, onto the rug, and began tracing my body with her mouth from my neck downward. Her tongue drew a slow line across my chest, sucked each of my nipples, went down my stomach without haste, learning the route. When she reached my belt she undid it without stopping, pulled down my pants and boxers in one movement, and my cock came out so hard it bounced against my belly.

—Look at you —she murmured, gripping me at the base. —You’re rock hard.

She took me fully into her mouth, all the way down, without hesitation. I felt the wet heat close around my cock and the edge of her throat pressing my tip. Her mouth was precise and unhurried. There was nothing mechanical in how she moved: she varied the rhythm, came up sucking hard and went down slowly, letting her tongue coil around the head, knowing exactly when to speed up and when to stop. Every so often she pulled back, spat on me, and jerked me with her hand slick with saliva while she took my balls into her mouth one after the other and sucked them carefully. I clung to the rug with my fingers, felt a hot thread rising from my base, and tried not to lose control too soon.

—Stop —I asked when I felt I was too close. —Stop, fuck, or I’ll come in your face.

She lifted her head and looked at me with a calm smile, her chin shiny with saliva and her red lips swollen.

—Good? —she asked, giving me a slow lick from my balls to the tip.

—Very good —I said, my voice rough. —Come here.

I rolled her onto the rug and yanked the thong all the way off. Her cock lay hard against her stomach, throbbing. I took it into my mouth without hesitation and felt it tense in my hands, felt it get even harder against my tongue. I’d never sucked a cock before and was surprised by how natural it felt: the weight, the salty taste of the liquid leaking from the tip, the taut skin of the head against my palate. She made a contained sound, almost surprised, and put a hand on my head, guiding me without forcing me, marking the rhythm with her hips. I sucked as best I could, swallowing saliva, letting her push a little deeper each time, until I felt the sting in my throat and pulled away coughing. She laughed softly and stroked the back of my neck.

—Easy. You learn.

I went back down, this time more slowly, and licked her balls while I jerked her cock against my face. The tip left clear wet marks on my cheek. We settled mouth to mouth on the rug in sixty-nine, each of us attending to the other with the same attention, and for a good while there was nothing else in the world but that exchange: two hard cocks, two hungry mouths, saliva dripping, muffled moans. She was still better than me, she sucked with a technique that made my toes curl inside my socks, but I tried hard and from the sounds she made I knew I was doing something right.

***

At some point we moved to the bed.

Sonia took a bottle of lube from the nightstand drawer, squeezed a generous amount into her hand, and slowly coated my cock, looking me in the face as she did it. Then she lay down on her stomach with a pillow under her hips, spread her legs, and looked at me over her shoulder.

—Do you want it? —she asked, parting her ass with both hands.

I didn’t need to answer. I knelt behind her, ran the tip of my cock between her cheeks a couple of times, and pressed it against her hole. I pushed slowly. She was hot, tight, tighter than I’d imagined, and yet she gave way with a familiarity that left no doubt she knew exactly how to open herself. I sank all the way in on one long stroke and held still for a second, my balls pressed against hers, trying not to finish right there.

—Move —she said with her face against the pillow. —Fuck me.

I started moving. I went slowly because it seemed like the right thing to do, but she didn’t need me to. Her body responded without resistance. I stopped several times to check her reaction; she made little approving sounds, moaned “like that, like that, harder,” and at one point put her hand on my hip to set the rhythm she wanted. I grabbed her hips with both hands and started thrusting for real, with the wet sound of skin slapping against skin and the bed creaking beneath us. I saw her slip her hand underneath to jerk herself off to the rhythm of my thrusts.

—I’m coming —I told her through clenched teeth. —I’m coming, Sonia.

—Inside —she panted. —Come inside me.

It didn’t take long. It was too much, and I’d been anticipating it for too long. I came in four long spurts, clenching my cock inside her, feeling it throb with each spasm. When I pulled out, a white thread slid free and ran down her thigh. I stayed still for a moment, breathing hard and eyes closed, trying to come back to the present.

She sat up, turned around, and turned me over with a firm hand on my shoulder. Her cock was still hard, shining with lube and her own desire.

—Now me.

I lay down on my stomach without thinking much about it. Sonia took her time preparing the ground with her fingers, pouring cold lube that made me clench my hips, going in first with one, then two, with a methodical patience that helped more than any verbal promise. She moved her fingers inside me searching for something, and when she found it a moan escaped me that I hadn’t intended to make.

—There it is —she murmured.

When she entered me, she did it with calculated slowness that left me breathless. The stretch burned at the edges and at the same time dissolved into a dull pressure spreading inward. I stayed still and let it happen. She sank all the way in, waited, and began moving with slow, deep thrusts, pressing her chest to my back, biting my shoulder without hurting me. Each time she touched me inside with the tip, something tightened in my belly in a new way.

—Breathe —she told me in my ear. —Let go.

She pushed harder. She slipped a hand underneath and grabbed my cock, which without me noticing had gotten hard again, and started jerking me in time with her thrusts. What I felt was hard to categorize. It wasn’t what I’d expected, neither in a bad sense nor in a good one. It was more complex, more internal, with a presence that spread in ways I hadn’t known were possible. I ended up coming again, this time in her hand, my face pressed into the pillow and a long moan that I didn’t know how to recognize as mine. A second later I felt her dig her nails into my hip and come too, inside me, with a hot gasp against my nape.

When it was over, she stayed on top of me for a few seconds, her forehead resting between my shoulders and her breathing gradually settling. The weight of her body was unexpectedly warm. She withdrew slowly and I felt the warm drip running between my ass cheeks.

—Are you okay? —she asked.

—Yes —I said. And it was true.

***

We lay there a while without hurrying. She went to the kitchen and came back with more water. We talked a little about nothing in particular: a series she was watching, the neighborhood, whether there had been traffic that afternoon. There was something about that after-conversation that felt unexpectedly comfortable, almost more than everything before it.

When I was getting dressed in the hallway, she remained leaning in the bedroom doorway, watching me button up my shirt with a calm expression.

—You can come back anytime you want —she said.

—I will —I promised.

And I meant it. I went down the three floors slowly, my head still full of everything that had just happened, and stepped out into the street where the afternoon sun fell slantwise over the stone balconies. It was an ordinary afternoon. Neighbors passed by carrying grocery bags. A dog waited tied to a post. Nobody knew anything.

***

I went back three weeks later.

The buzzer rang into emptiness. I rang several times. A neighbor coming down the stairs stopped and looked at me with an expression that wasn’t hostility but something like the quiet pity of someone who has already had to deliver that news before.

—The girl on the third floor left a few days ago —she said. —Just like that. Without telling anyone.

The ad had disappeared from the portal. The number was out of service. I went back down the three floors slowly and stood for a moment on the sidewalk, not really knowing where to go.

It wasn’t exactly sadness I felt. It was something more like the awareness that certain things exist only in a precise instant, and that trying to recover them afterward is always a mistake. There are encounters that can never continue and that for that very reason remain intact in memory, without the wear that repetition brings.

What had happened in that apartment was still real. It would remain so.