My First Time with a Man Was More Than I Expected

I had been out of work for two weeks and had no idea what to do with so many free hours. I spent my time pacing around the apartment, opening the refrigerator without being hungry, checking my phone every five minutes as if someone might call me with good news. Nobody called. Meanwhile, my mind kept wandering elsewhere.

For months I had been circling around the same idea: I wanted to find out what it was like to be on the bottom, to feel someone else’s cock sliding into my ass all the way. I had imagined it so many times, hand on my dick and two fingers buried in my own asshole, that imagining it was no longer enough. One afternoon, after my third coffee, I opened one of those chats where people post pictures and wait. I uploaded one of my back and another of my buttocks, close-up, my ass spread with my free hand and my hole on display, the phone camera propped against the bathroom mirror.

A guy named Tobías messaged me a few minutes later. A picture of a smooth chest, defined arms, and a cock that looked drawn, thick and long, with prominent veins and shaved balls hanging heavily beneath it. I thought the picture had been doctored, but he sent it from two different angles, including one with his hard cock pressed against his abdomen, measuring it with his hand. We talked for a while. I told him it was my first time, that I was equally nervous and horny, that I wanted him to fuck me slowly and then hard. We agreed to meet the next day in the square across from the shopping center. Faces visible, no hotel rooms yet.

I arrived fifteen minutes early. I walked around the fountain three times, counting pigeons so I wouldn’t think. When I saw him approaching, my hands began to shake. He was taller in person and had the kind of confidence that came from gyms and money. He looked me up and down twice without even trying to hide it.

—I thought you were chubbier, sweetheart —he said, adjusting his jacket—. You won’t be able to handle me. I’m sorry, really, but we’d better leave it here.

I stood there with my reply stuck in my throat. The only thing that came out was an “okay” that sounded like a farewell at a funeral. I watched him walk away with the same firm stride he had arrived with. I walked back to the bus stop and sat on the bench staring at the ground, a strange heat rising into my face. I didn’t know whether it was shame, anger, or both tangled together.

At home I threw myself onto the bed fully dressed. It was seven in the evening, and outside there was almost no light left. I thought about taking a shower, cooking something, looking for a job properly for once. I did none of it. I opened the chat again.

This isn’t going to end like this.

I ran my finger down the list of people online. I stopped at a profile that said “versatile, own place, discreet.” No face picture, but a long, well-written description. I greeted him with a timid “hi.” He replied within seconds. His name was Damián, he lived in an area far from downtown, and his proposal was straightforward: I should come to his house that very night, sleep there, and return in the morning. No commitments, no pressure, “whatever happens.”

I said yes before fear could change my answer.

***

The taxi took almost an hour to reach the address. We left downtown, then the brightly lit avenues, then the neighborhoods with streetlamps, until we reached a dirt road where the houses stood separated by empty lots. The one at the end, white, with a yellow light above the door, was his. I gave the taxi driver an absurdly large tip, as if that could guarantee me a safe ride back, and got out.

Damián opened the door wearing a T-shirt and sweatpants. Bald, with a neat beard, shorter than me and considerably sturdier. He shook my hand first, then gave me a brief hug in which I felt the heavy bulge beneath his sweatpants pressed against my hip. He smelled of cheap cologne and sautéed onions.

—You got here just in time. I was finishing dinner —he said, motioning me inside.

The house was small and had very little furniture. A table, two chairs, a brown corduroy sofa, and a huge television mounted on the wall. We ate pasta with sauce and drank red wine from a carton. While I chewed, he calmly asked me everything: how I had made up my mind, what I had done before, what I was curious about. I told him about the square that same afternoon. He chuckled softly.

—Some guys are handsome and stupid at the same time. Don’t worry. I’ll fuck you however you want, and if you can take it, I’ll leave your ass wide open.

I explained that I had never been on the bottom. I had sucked, yes, and had touched myself with another man, but a whole cock inside my ass? Nothing. He nodded as if the information mattered to him and didn’t matter to him at the same time.

—Do you want to try a few things? —he asked—. I like games. But if you want me to stop at any point, stop me. I mean it. Let’s agree on a word. Something you can’t mistake for anything else.

I laughed nervously.

—Platform.

—Platform —he repeated—. If you say “platform,” I stop everything. Agreed?

***

After the shower he took me to the bedroom. The bed was wide and low, with gray sheets and four wooden posts at the corners. On the bedside table sat a closed plastic box that I avoided looking at directly. Damián turned on the television and played a video. Two men in a kitchen, in natural light: one of them, kneeling on the countertop, was letting himself be fucked from behind while gripping his cock and shooting in streams across the tiles. At first I felt embarrassed, and then I didn’t. I felt mine harden against the towel.

—Come here —he said, sitting on the edge of the bed.

He took off his shirt first, then his pants. It was medium-sized, neither big nor small, thick at the base, with a purple, gleaming glans, already half-hard, and he stroked it with his left hand while watching me. He spit into his palm and spread it up and down the shaft, and the foreskin slid back, leaving the swollen head exposed. I undressed more slowly, keeping my back to him part of the time. When I turned around, he beckoned with one finger.

—Come closer. Look at me. Come suck it.

I kissed him while sitting on his thighs. His tongue was soft and tasted of wine. He slipped one hand between my buttocks and ran his middle finger along the crack of my ass, up and down, pressing lightly against my hole each time it passed. He grabbed the back of my neck with a strength I hadn’t expected and lowered my head toward his crotch. I opened my mouth and took him in. His cock filled my tongue, hot and salty, smelling of soap and clean skin. I sucked him without thinking, slowly, eyes closed, my hand at the base of his shaft moving in the same rhythm as my mouth. I pulled it out with a wet pop, licked his balls one by one, took them into my mouth, and when I came back up he was already pushing my head down so I would swallow him whole. I gagged, my eyes filling with spit and tears, and ran my tongue over my lips when he let me breathe. Damián stroked my hair with a calmness that contrasted with the pressure of his hand.

—Good boy. That’s it, suck it properly, no teeth.

When he let me go, he lay face down and spread his legs. His buttocks were pale and parted, and in the middle was his pink, wrinkled asshole, looking at me.

—Tie me up —he said, nodding toward the plastic box.

Inside were soft ropes, the kind used for climbing but covered in fabric. He explained how to loop them around my wrists and ankles, how to leave knots tight enough to hold without cutting off circulation. He let himself be tied as if he were being fitted for a suit. When I finished, I looked at his buttocks. His asshole was slightly open, marked, as if it were the routine of many years. He told me he prepared himself every day, that it was part of the pleasure.

—Eat me first. Spit on it. Get your tongue right inside.

I spread his buttocks with my hands and pressed my mouth against the hole. I ran my tongue around it, first gently, then pointed it and pushed until it slipped inside. He tasted of soap and something more intimate, salty. Damián moaned and arched his back, offering himself to me more fully. I spit inside him twice and put in one finger. It slid all the way in without resistance. I added a second, then a third, and he moved against my hand, panting.

—Go in with your cock —he urged—. Get yourself used to it too.

I knelt behind him, took hold of my cock, and pressed it against his hole. I pushed slowly. It barely had to stretch him; his ass opened without protest and swallowed my entire cock in one thrust. He asked me to move hard anyway, not to be afraid of him. I did it for a while, driving into him with my hips, hearing the wet slap of skin against skin, watching his back tense and his arms pull against the ropes. Sweat showed across my chest. I gripped his waist and fucked him as if he were mine, until he stopped me with a gesture and pointed to a jar on the shelf.

—The oil. I want you to try something else.

What he asked me to do was fist him. I told him I didn’t dare. He explained it step by step: thumb inside, the other four fingers together, steady but gentle pressure, wait for him to yield, pull back when he complained, then push again. I coated my hand in oil all the way to the elbow. I pressed my joined fingers against his open asshole and pushed. My knuckles caught for a moment; he breathed deeply, relaxed, and my hand slipped in all at once. I did it with a knot in my throat. It took long minutes, slowly rotating my wrist, feeling his ass open and close around my fingers. When my hand went in completely, up to the wrist, I heard him release a deep moan that sent a shiver up my neck. His cock was rock-hard against the mattress, and a drop of pre-cum escaped and wet the sheets. It didn’t seem possible to me, and yet it was happening, right there in front of me, my fist buried to the wrist in the ass of a tied-up man.

—Keep it still. Leave it there for a while —he asked.

I obeyed. I felt the heat of Damián’s body closed around my fist, his heartbeat in my palm, the pulse of his asshole squeezing my wrist like a hungry mouth. I withdrew it even more carefully, twisting it, and the hole remained open for a few seconds, swollen and gleaming with oil, before closing again. Then I untied him.

***

He stretched his arms, sat on the edge of the bed, and kissed me deeply. I felt that something had changed between us. He held my face in both hands and kept me that way for a while, looking at me.

—Now you. Are you ready?

I nodded. And that was where I got the timing wrong. I thought he would start with his fingers, slowly, as I had read. But first he invited me to lie on my back, opened the box again, and took out a thick candle shaped like a penis, dark green. He showed it to me without smiling, as if he were showing me a tool.

—This first. So you can get acquainted.

He tied my wrists to the posts of the headboard. Then my ankles, spread apart, so wide that I felt my thighs stretch and my ass left raised, exposed completely. I felt exposed in a way I never had before, not even in my imagination when I had pictured it. He closed the curtains. The television light flickered across my chest while, on the screen, another man came in the face of a kneeling guy.

Damián coated his fingers with oil and ran them over my asshole, drawing slow circles, pressing lightly until one finger sank in to the knuckle. Then the second. He opened me with his fingertips, searching inside. He found a spot that made my hips jerk, and he smiled. He worked at it insistently until I began panting with my mouth open, my cock hard against my belly, wetting my navel. He pulled out his fingers.

The candle went in with difficulty, even with the oil. It burned from the very first inch, as if something hot and wide were being pushed into me at once. I complained, but he told me to breathe, to relax, to trust him. I tried. The candle moved up and down with a slow, stubborn rhythm, sinking a little deeper each time, until I felt its base strike between my buttocks. At some point I began to feel something that wasn’t only pain: a strange mixture, a new pulse deeper inside, a tingling that climbed my spine and made me curl my toes. I closed my eyes. He pulled it out and pushed it back in, all the way, slowly, again and again, and I heard myself moan involuntarily.

—You’re ready —he said, and pulled it out completely.

What came next was different from what I had imagined. He climbed on top of me, grabbed my legs behind the knees, folded them against my chest, and pushed. His cock was smaller than the candle, but he buried it in one thrust, without pausing, until I felt his balls pressed against my ass. I screamed. I didn’t have time to think of the word. I pulled at the ropes, but they didn’t give. He stayed still inside me, kissed my forehead, and told me to breathe, that it was done, that the worst part was the first minute. He stroked my hair. I felt his cock inside me, hard and pulsing, and my asshole burned as if it had been scorched from within.

He began to move slowly. He withdrew his cock until only the tip remained inside, then drove it back in to the hilt, setting the rhythm with his hips. The pain continued; it didn’t go away, but something in me stopped fighting. I closed my eyes and felt his breath against my ear, his beard scraping my neck, the weight of his body crushing me into the mattress, his balls slapping my buttocks every time he thrust. I cried without realizing it, fine tears, without sobbing. He wiped them away with his thumb while he pounded me.

—That’s it, open up for me. It’s yours now. You’ve got it inside you. Hold on, I’m going to fill you.

He sped up. I felt his abdominal muscles tightening against mine, his thighs against my thighs, the wet, obscene sound of his cock plunging in and out faster and faster. He grabbed my cock and jerked me off in the same rhythm. It took only seconds: I came without warning, thick streams splashing across my chest and chin, one reaching my shoulder, while my ass clenched around his cock in spasms. He let out a short laugh and kept fucking me harder and faster until his body went rigid. He came inside me with a short, almost embarrassed grunt, while I felt every pulse of his cock unloading inside me, shot after shot. He stayed on top of me until he softened. When he pulled out, it burned so badly I thought I was bleeding. I wasn’t. It was only my asshole, pulsing like a second heart, beating out of rhythm, his semen dripping down my perineum onto the sheets.

He untied me. He turned me onto my side and lay down behind me, embracing me. He kissed the nape of my neck, my shoulders, my back. He stroked my belly with his open palm, then moved lower and ran his fingers over my wet ass, without putting them inside, simply caressing my swollen hole as if soothing it. He didn’t ask for permission or explanations. We stayed like that for a long time without speaking, while the television continued playing videos with the sound off.

—Are you all right? —he finally asked.

—Yes. I think so.

—Don’t lie.

—I’m not lying.

I fell asleep pressed against his body, his breath in my hair, his seed still trickling between my buttocks and a dull ache that was no longer fear.

***

I woke up to sunlight and a swollen asshole. Damián was already in the kitchen. It smelled of coffee and toast. It was difficult to walk straight for the first few steps. When he saw me come in, he smiled as if nothing strange had happened between us, as if we were old friends.

We tried again in bed before breakfast. He put me on my knees, spread my buttocks with both hands, and ran his tongue over my still-sore hole, long and slowly, soothing me. When he pressed the tip of his cock against me and pushed, I twisted in pain at the slightest touch, and he stopped, pulled out, and kissed my lower back. He told me it was nothing, that my body would get used to it, that next time would be different, that next time he would fuck me all night without stopping. I told him yes, next time.

I ate breakfast in silence, listening to him talk about his work, his dog who was staying at a friend’s house, and the garden he wanted to plant out back. I ordered a taxi from his phone. When I said goodbye at the door, he grabbed me by the nape with the same force that had surprised me the night before and kissed me deeply, unhurriedly, sliding his tongue all the way into my mouth.

—Let me know when you want to come back.

—I will.

In the taxi home, watching the empty lots pass by the window, my ass still throbbing against the seat and the sticky dampness between my buttocks reminding me of every bump, I thought about the word we had agreed on. “Platform.” At no point had it crossed my mind to say it. That frightened me almost more than everything else.