The Night a Transvestite Made Me Cross the Line

It was past midnight and I had a few wines in me. There had been a get-together at Marcos’s place, one of those gatherings that start with snacks and end with everyone shouting and nobody remembering what time it is. I left when there were only four of us left, got into my car with that warm feeling alcohol leaves behind when it still isn’t too much, and drove down the half-empty avenues with the window down.

I wasn’t looking for anything. Or that’s what I told myself. But that particular night my body was awake, hot, with an urgency I hadn’t been able to discharge all week. I drove slowly, unhurried, watching the corners as if I expected something to step out in front of me.

And something did.

Driving along a wide avenue, the light turned red and I stopped. I turned my head almost on impulse and saw her, standing against the wall of a closed shop, under the yellow light of a streetlamp. From a distance she looked spectacular: tall, with very long legs, her hair falling over her shoulders. I felt my stomach tighten.

The light changed to green and I didn’t pull off. Nobody was coming up behind me. I kept looking at her for a few seconds longer than I should have, and she, who knew that look better than I did, gave me a slight nod of her chin, as if to say, “Well?”

I parked a little badly by the curb and rolled down the passenger-side window.

—In a hurry? —she asked, bending down to look at me. Her voice was deep and soft at the same time, and her smile seemed to know too much.

—No —I said, and the word came out rougher than I expected.

We settled on the price right there, in a few words, no fuss. I opened the door and she got in. And only then, with the dome light on inside the car, did I realize something I had in fact already sensed from the sidewalk: she was trans.

I didn’t back away. Not at all. What had seduced me from the very first moment was still right there in front of me: those brown legs, toned, shining under the sheer stockings; the hips defined but not exaggerated; the narrow waist. Imagine a slender body, but carefully made, every curve in its place. She held my gaze without blinking, waiting to see what I would do with that information.

—Bianca —she said, and held out her hand as if we were closing a business deal.

—Nice to meet you —I replied, and we both laughed at how absurd the formality was.

I told her we should find a quiet place. I knew a love hotel a few blocks away, one of those with a covered garage and dim light in the room. I drove those few blocks with my hands a little tight on the wheel and her watching me from the side, amused, saying nothing.

***

The room was small, with a large bed taking up almost all of it, a mirror on the wall, and a warm light coming from a lamp with a slightly yellowed shade. As soon as we went in and I closed the door, Bianca came over, put her hands on my chest, and gently pushed me until I sat on the edge of the bed.

For a second I stayed still, my hands at my sides, not really knowing what to do with them. It had been a long time since I’d felt so exposed. It wasn’t the first time I’d paid to be with someone, but it was the first time my body was asking for something my mind still hadn’t fully accepted. Bianca noticed, because she took her time, unhurried, letting me breathe.

She knelt between my legs and slowly, deliberately pulled down my zipper, watching me the whole time. When she got me free, she leaned in and, before doing anything else, came up and kissed me on the mouth. I answered without thinking. We traded tongues slowly, hungrily, and it was a much better kiss than anyone would expect from a paid encounter.

Then she went back down. She started using her mouth in a way that left me breathless. She did it while looking at me, lifting her eyes every so often, then closing them as if she herself were enjoying it. There was care in it, a surrender, that had very little to do with the money we had agreed on.

—Do you want to see me naked? —she asked suddenly, pausing, her lips still close.

—Of course I do —I said.

She mentioned an extra and I said yes without hesitation. Even dressed, she looked incredible; I needed to see the rest.

I wasn’t wrong. She stood up, took off her clothes with the naturalness of someone who knows her body by heart, and what appeared was almost perfect. Brown skin, taut, gleaming faintly under the lamp light. I leaned in and kissed her chest, licked, sucked, and she let out a low, real sound that sent a chill up my back.

—Do you want to fuck me? —she asked, with a sideways smile.

—Yes —I said.

—It’ll cost you… —she started.

I didn’t let her finish. I turned her away from me and lowered my mouth to her ass: round, firm, smooth, with a clean, warm scent that drove me crazy. I spread her with my hands and worked her with my tongue, slowly at first, then with more hunger. My tongue was having a party. I explored every inch while she gripped the bed frame and arched her back.

I laid her on her back. I lifted her legs, got myself in position, and entered her from the front, looking her in the face. As I moved inside her, her expressions were those of someone who was really feeling it: mouth parted, eyes closing, hands reaching for my arms. I thrust slowly at first and then with everything I had, until I came with a shiver that ran down my legs.

I stayed on top of her for a few seconds, breathing hard, feeling her chest rise and fall against mine.

***

And then, with her head still resting on my shoulder, she asked me something that changed the whole night.

—And have you ever been penetrated?

—No —I answered firmly, almost defensively.

She said nothing. She just held me, kissed me again, slowly, deliciously, and with a gentle movement of her hips made me roll until I was on my back against the mattress. Shit, this is still going, I thought, my heart suddenly racing. But I didn’t say anything. I didn’t want to say no.

She sat up and knelt in front of me. She looked at me, and I saw her eyes drop slightly toward herself.

—Do you like it? —she asked, referring to her cock.

—Yes —I said, and it was true, even if the word trembled a little.

She leaned in and, without hurry, brought it to my mouth.

—Suck it —she said softly.

—How? —I asked, and I don’t know whether she heard my voice break or my whole inexperience.

—It’s not rocket science —she answered—. Open up and apply pressure with your lips. Not with your teeth, those hurt.

And I did. Clumsily at first, then a little less so. She thrust twice, slowly, and I felt the reflex to give back, but I held myself back. At the end she closed her eyes, let out a long sigh, and stayed still for a moment, as if savoring something I still didn’t fully understand.

Then she lay on top of me. I felt her weight, her hot skin, and immediately the tip of her cock searching for the entrance to my body. Everything clenched up from nerves.

—Please, slowly —I asked her, and my voice came out thin, almost childish.

—Relax —she said against my ear—. Tell me and I’ll stop.

She pushed. When the first part went in, I felt a terrible, sharp pain that made me clench my teeth and grip the sheets. Bianca stopped at once. She stayed completely still, waiting, stroking my side with one hand.

—No, take it out —I managed to say.

But instead she pushed again, carefully, and the rest went in. The pain was still there, but suddenly it was different: bearable, mixed with something I didn’t know how to name. She waited another moment, letting me get used to it, and only then did she start moving, slowly, measuring every thrust by my face.

Little by little the pain eased. It didn’t disappear completely, but it moved into the background, under a new, intense sensation that had me breathing in broken gasps and staring at the ceiling. Bianca sped up just a little, moaned against my neck, and finished inside me with a shudder I felt running through her whole body.

She stayed on top for a while, buried in my shoulder, both of us breathing unevenly. I put an arm around her back and held her without thinking, as if it were the most natural thing in the world.

—I’m going to see you again —I told her, and it wasn’t a question.

She lifted her head, looked at me with a tired, genuine smile, and didn’t answer. She only gave me a short kiss on the lips.

***

Bianca was with me three more times, at that same hotel or others like it. Each time it was different, calmer, more familiar. She was good to me from the start, patient with my nerves, attentive to what I still didn’t dare ask for out loud. I’m very grateful for that tenderness: she taught me something about myself without making me feel clumsy, without rushing me, without judging anything.

There wasn’t a fourth time. One night I went back to the same corner and she wasn’t there. I returned the next, and the next after that, driving slowly under the yellow streetlights like that first time, but the wall by the closed shop stayed empty. She stopped showing up in that area, and I never saw her again.

For a long time it was hard for me to think about those nights without getting defensive, without needing to explain them to myself. It took me a while to understand that I didn’t need to. What happened in that hotel room didn’t turn me into anything I wasn’t already; it just showed me without filters. Bianca didn’t seduce me with tricks or pretty words; she simply gave me permission to want what I wanted, and at that point in my life, that was worth more than anything I had ever arranged on a street corner.

Sometimes, when I stop at a traffic light at night and I’ve had a few wines in me, I turn my head toward the sidewalk almost without realizing it. I don’t really know what I’m looking for. Maybe her. Maybe just that version of myself that night, for the first time, dared not to say no.