My First Time Was with the Transvestite from an Ad

The ad took up half a column in the contact section of a national newspaper. “Explosive transvestite, super-hot and very well endowed, specialist in first-time bottoms, pain-free penetration.” I read it three times, standing at the station kiosk, and with each reading my mouth got drier and my hands clumsier. Something lodged in my chest and started pounding downward.

I had just gotten off the train in Seville for work. I didn’t know anyone, I had no plans until the next day, and suddenly all that existed was that number printed in cheap ink. I dialed it before thinking twice.

A woman’s voice answered on the second ring. South American accent, low, sweet, drawn-out, a voice that smiled as it spoke.

“Yes, sweetheart?” she said, as if she’d been expecting me for a while.

I blurted out, stumbling over myself, that I’d seen the ad, that I’d never done anything like this before. She didn’t let me finish.

“Easy, my love. If it’s your first time, we’ll go slowly. My place is very discreet. Nothing will hurt, I promise. You’ll leave here asking me for more.”

I hung up with my heart racing. This is insane, I thought, as I gave the taxi driver the address she’d told me. Turn around, go back to the hotel. But another part of me, the part that had spent years awake at night imagining exactly this, had already won the argument.

***

The taxi dropped me off on a narrow street in the center, with shuttered balconies and blinds pulled down. I called again, just as she had instructed.

“Third floor, right side,” she purred. “Knock three times. I’ve got something nice ready for you.”

I climbed the stairs slowly, holding onto the railing, counting the steps so I wouldn’t think. At each landing I promised myself I could still go back down, that no one was forcing me to do anything. And at each landing I kept going up. Three knocks with my knuckles. One eternal second. The door opened.

Yamila appeared in the doorway like an apparition. She was tall, much taller than me, dark-skinned and dark-haired, with full lips and eyes lined in black. She wore a tight miniskirt, black stockings, and a top that barely contained a generous breast. She kissed me twice, slowly, on the cheeks and, when she leaned in, I saw she was almost a head taller than I was.

“Come in, baby. Get comfortable.” She closed the door behind me. “Oh, you’re so nervous. Relax, man, I’m a specialist at breaking in boys like you.”

The apartment smelled of incense and sweet perfume. There was a big bed with dark sheets, a dim lamp, and little else. I didn’t know what to do with my hands, so I let them fall to my sides, feeling ridiculous and aroused in equal measure.

You can still leave, I told myself one last time. But my feet didn’t move, and she noticed. She took a step closer, smiling, fully aware that the doubt had already been lost.

“Let’s see, daddy, what’ve you got there?” She took my wallet from my hands with disarming ease, opened it, and smiled. “One hundred and fifty euros and a picture of your family. Forget about that for now. I’m keeping this.”

She tucked the bills into the nightstand drawer and came back to me. She started nibbling on my earlobe while unbuttoning my shirt one button at a time. Her hot breath slid down my neck.

“You’re so turned on,” she whispered. “Don’t you dare come yet. You’ve got a lot to learn tonight.”

She gently pushed me until I sat on the edge of the bed and then laid me back. She climbed astride me and ran her tongue over my chest, stopping at my nipples until she made me arch my back. I had no idea something like that could feel that way.

Then she straightened up, kneeling on the mattress, and slowly pulled down her skirt, looking me in the eyes the whole time. And there, freed from the fabric, appeared what the ad had promised: a thick, dark cock, still half asleep and already imposing. I stared at it like someone discovering something they’d been searching for a long time without even knowing it. I felt no disgust or fear. I felt an urgency that dried out my throat.

“Like what you see, first-timer?” She gave a soft laugh. “Come on, get closer. We’re going to take it slow.”

Yamila moved beside me, propped against the headboard, and offered me her member almost ceremoniously. She held it with one hand and brushed it over my cheek, my lips, my nose. She pulled the foreskin back and the glans emerged, broad and dark, shining under the lamp.

“Slowly,” she ordered. “First with your tongue. That’s it. Good boy.”

I kissed it first, clumsily, not really knowing what was expected of me. Then I licked from bottom to top and felt it harden with every stroke. The smell was intense, musky, masculine, and instead of making me pull away it pushed me forward. I opened my mouth and let it in. At first only the tip would fit; little by little I got used to it, growing more confident, taking more in with each movement.

It was strange to discover that something so dreaded could feel so natural. Every time she sighed, a rush of pride ran through me: I was doing it well, she liked it, and that turned me on more than anything else. I closed my eyes and let myself be carried by the rhythm, the weight, the heat.

“That’s it, my love, that’s it,” she panted, her voice already more broken. “You learn so well. It was inside you and you didn’t even know it.”

I could feel her getting harder and harder between my lips, hard as a hot bar. She held the back of my neck with one hand and set the pace, without forcing it, letting me breathe. My chest was soaked with saliva and my head was empty of everything except that moment.

***

Suddenly she pulled away. Her breathing was ragged and her eyes were blazing.

“I don’t want to finish yet,” she said. “I want to break you in properly.”

She stripped me the rest of the way with quick tugs, shoes, pants, everything, until I was completely naked on the sheets. She looked me up and down and clicked her tongue, amused.

“Turn around, daddy. On all fours. I want to see that little ass.”

I obeyed without a word, and that immediate obedience, that total surrender to whatever she decided, surprised even me. I was on all fours on someone else’s bed, in someone else’s city, my heart in my throat and a mixture of shame and desire I had never felt before.

“Lower your head,” she said softly. “Relax. Just let yourself go.”

I heard the drawer open. Then I felt a cold cream spreading between my buttocks, and then a finger, slippery and patient, making its way in. It didn’t hurt. On the contrary: a warm, new sensation ran up my spine. Yamila moved it in circles, stretching me, pulling it out to add more cream and go back in again.

“You’re so tight,” she murmured. “We’ll fix that.”

Then I felt the tip of her glans pressing where the finger had been. She ran it up and down the slit, brushing me without entering, until the waiting became unbearable.

“Please,” I heard myself say, in a thread of a voice. “Do it already.”

She pushed. A deep heat, a sharp stab that stole my breath. I clenched my teeth and let out a rough groan.

“Hang on, my love, hang on,” she told me, leaning over my back. “Breathe. The worst part is over.”

And she was right. The initial pain gave way, slowly turning into a fullness I hadn’t imagined possible. I felt filled, complete in a new way. Her chest warmed my back and her anxious breathing struck the back of my neck.

Something in my head finally gave up. I stopped resisting, stopped measuring every sensation, stopped wondering what all this meant for the man I had been until that afternoon. There was only the rocking motion, the heat, the voice speaking in my ear. I gripped the sheets with my fists and pushed back, seeking her, asking wordlessly for her not to stop.

“You feel so good, daddy,” she whispered. “You take me so well.”

She straightened again, grabbed my hips with both hands, and began to move slowly. She came almost all the way out and went back in with a little more firmness. Out and in. With each thrust, the fear dimmed and something else lit up. On one of those movements something exploded inside me, a deep, unknown pleasure that ran through my whole body. I was coming without anyone touching me, shaking against the sheets, startled and surrendered all at once.

Yamila noticed and let out a deep laugh of pure delight.

“Oh, but look at you. You came all by yourself, no hands.” She squeezed my hips harder. “That means you were born for this, darling.”

She sped up. Her breathing turned into broken gasps, her fingers dug into my skin, and with one deep thrust she went very still, vibrating inside me. I felt her shudder, heard her moan against my shoulder, and a new heat flooded my insides.

***

She let herself fall onto my back and we stayed like that for a long while, both of us breathless, stuck together by sweat. Then she slipped out of me slowly, carefully, and lay down beside me.

“See? It wasn’t such a big deal,” she said, stroking my hair. “You did very well for your first time.”

I was dazed, dizzy, not quite sure whether what I felt was regret or a strange, trembling happiness. I asked if I could stay a moment, recover, clean myself up.

“No, my love,” she replied, already getting up and gathering her skirt from the floor. “I’ve got another boy waiting, as nervous as you were when you arrived. But come back whenever you want. Now you know the way.”

I dressed in silence, my body still vibrating, and went down the stairs holding the railing, just as I had climbed them but now as someone else. The narrow street in Seville was empty and dark. I wandered aimlessly for a good while, disoriented, with the memory of that smell stuck to my skin and the uneasy certainty that, sooner or later, I would someday dial a number like that again.