My Confession: the Afternoon I Tried Being with a Man

That year I was going through a long dry spell without a partner. I didn’t complain too much: I had my job, my routine, my friends on weekends. But nights were another story. Between porn and masturbation, a question started to creep in that at first I could barely even phrase for myself. What would it feel like to be with a man? Not just to fuck him, but to let myself get fucked. To feel a hard cock forcing its way inside me, spilling into my ass.

The idea kept circling through my head during the day. In the office, driving, in the shower. At first I rejected it like you swat away a fly. Then I started looking for specific videos — mature guys opening up first-timers’ asses, thick cocks sinking in all the way to the balls, heavy loads dripping between butt cheeks — reading forums, saving private accounts in a folder nobody was ever going to open. I jerked off twice a night watching that stuff, with one finger up my ass, biting the pillow so I wouldn’t scream. And one ordinary Thursday, almost without thinking, I opened the chat and wrote to Damián.

I’d known Damián since university. He was the only openly gay friend in my close circle, and we had never talked about anything like that. But something told me it would be different with him. That he wouldn’t judge me, that he wouldn’t make a scene if I later regretted it, that he wouldn’t tell anyone.

“Got a minute?” I wrote.

“For you, always. What’s up?”

I went back and forth over it for a while. I sent him three messages and deleted them before sending. In the end I wrote the simplest thing possible: that I had a curiosity that had been chasing me for months, that I didn’t know who else to ask, that maybe we could talk in person.

We met at a café near his workplace. I arrived with a knot in my stomach. Damián showed up ten minutes later, dressed for the office, with that relaxed smile he always had. He ordered a cortado and looked at me straight on.

—All right, spit it out.

I don’t know how I said it. I remember stammering, getting several words stuck. I told him about the porn, about the fantasies, about wanting to try. I confessed that I wanted to get fucked, that I wanted to suck a real cock, that I wanted to know what it felt like to have someone else’s semen inside me. He listened without interrupting. When I finished, he didn’t even seem surprised.

—And what do you want? —he asked calmly—. Do you want me to explain it with a PowerPoint or help you figure it out?

I laughed. It was the first time I’d laughed the whole conversation.

—The second one, I guess.

—Then I propose something. A downtown motel, a weekday afternoon, no pressure. If you show up, you show up. If you back out halfway, that’s fine too. The only condition is that you go in knowing what you want.

***

We set the date for the following Thursday, at four in the afternoon. That week I didn’t sleep well a single night. At work I could barely concentrate. I imagined scenes and then got scared of imagining them, and then I’d imagine them again in even more detail: Damián’s cock going into me, my moans, my ass opening for him.

Back then I was a pretty ordinary guy: average height, a bit of a belly, brown skin, scruffy beard. I didn’t see myself as sexy, but I didn’t hate my reflection either. Damián was the opposite: taller, thinner, with the toned body of someone who goes to the gym four times a week. That difference made me nervous. It gave me the feeling he’d be doing me a favor.

On Thursday I left work at three. I showered twice. The second time I stuck two fingers up my ass with soap, trying to loosen myself up, imagining it was already his cock. I changed clothes three times. I got to the motel fifteen minutes early. I’ve always been obsessive about punctuality, but that afternoon punctuality was a way of not staying alone in my house with my head spinning.

Damián arrived right on four. He crossed the parking lot looking at his phone, and when he looked up, he smiled at me as if we were just going for coffee. That ease of his helped me more than any conversation beforehand.

We paid for three hours. They gave us a key on a green plastic keychain. The room was one of the cheap ones: a huge bed, a mirror on the ceiling, a bathroom with a shower and nothing else. It smelled like pine disinfectant.

He closed the door behind me and threw the bolt.

—Are you okay?

—I’m nervous —I admitted.

—Me too.

I didn’t quite believe him, but I liked that he said it.

He came closer slowly. He took my face in both hands and kissed me. It was my first kiss with a man. The first thing I noticed was the beard, that rough scrape I’d never felt before in another mouth. The second was that his tongue moved differently, with less hesitation. He shoved his tongue all the way in, bit my lip, sucked my mouth like he wanted to make it clear right from the start who was going to be in charge in there. It wasn’t a romantic movie kiss: it was a kiss that made it clear he knew exactly what he wanted, and that he was willing to wait for me.

When we pulled apart, my cock was already so hard it was pressing against my pants.

—That’s a good sign —he said, looking at my fly, and he squeezed the bulge with an open palm.

I laughed again, but the laugh died in my throat when he ran his hand over the fabric and I felt my dick throbbing against his fingers.

We got naked slowly. He helped me with my shirt, I took off his belt. When I opened his pants and pulled his boxer briefs down, his cock sprang out with a jerk, almost hitting my wrist. I was speechless for a few seconds. He had a defined chest, firm thighs, and between his legs a dark, thick cock, longer than mine, with prominent veins and a broad, shiny head. His balls hung heavy underneath, shaved close.

—Easy —he said when he saw my face—. We’ll take it step by step.

Without thinking too much, I reached out and grabbed it. It was heavy. I pulled the foreskin back and exposed the whole head; a transparent drop appeared at the tip and stuck to my thumb. Damián looked at me and ran a hand over my neck.

—If you want to taste it, taste it.

I knelt down. I don’t know where the impulse came from, but I knelt right there, between the door and the bed, and brought my mouth to his cock. I licked underneath it, along the thick vein running up to the head, and then took the tip between my lips. It tasted like clean skin and soap. Damián let out a long sigh and stroked my hair.

—That’s it. Slowly. Soak it with saliva.

I did as he said. I started sucking him the way I’d seen in hundreds of videos, moving up and down with my lips tight, trying not to scrape him with my teeth. The first time I took him all the way down I gagged and had to pull back coughing, strings of spit hanging from my mouth. Damián chuckled softly and wiped my chin with his thumb.

—Easy, champ. Nobody’s asking you to swallow it whole on the first go.

I tried again, slower. I licked his balls one by one, took them into my mouth, licked him from base to tip. When I looked up and saw him looking down at me, eyes half-lidded and mouth open, an arousal seized me that I had never felt in my life. I was liking it. I liked having him in my mouth. I liked the way his thighs tensed when my tongue reached a new spot.

He lifted me gently by the hair.

—Stop. If you keep going like that, you’re going to get my load in your face too early.

He made me lie face down on the bed. I felt him spread my legs carefully and kiss my back, my lower back, the start of my tailbone. When he went lower and pulled my ass cheeks apart with both hands, I stayed still, face buried in the pillow. He licked my ass. He licked my whole hole, in circles, pressing his tongue, then the tip right in the center, pushing inside. The sensation was new, wet, intimate, dirty, so dirty that a long moan escaped me into the sheet. I grabbed the sheets because I had no idea what else to do with my hands.

He ate my ass for a good while. When he lifted his head, my cock was dripping onto the mattress and my hole was open, pulsing, wet with saliva.

Then he turned me over.

—I want to see your face —he said.

He pulled a packet of lube out of his pants. He squirted a cold streak onto his fingers, smeared my asshole, and started easing in his index finger, slowly. At first I tensed up. It hurt a little, not because of the size but because my whole body was on guard. Damián didn’t rush. He kissed me while he did it, talked to me softly, told me to breathe.

—Breathe through your nose. Let the air out through your mouth. Again. Open up for me.

One finger. Two. Three. He spread me open like a fork, twisted his fingers inside me, searched for a spot I didn’t know I had, and when he found it I arched suddenly with a rough moan. He touched me there again and again, watching my face while sounds escaped me that I had never made before. With his other hand he grabbed my cock and stroked me, loose, without squeezing too hard, just keeping me on the edge. I don’t know how long passed. Inside me there was only one idea repeating like a prayer: let him move on already, stop prepping me, just finish fucking me in.

—Put it in me —I finally said, my voice raspy—. Please.

Damián smiled, pulled out his fingers, and settled himself between my legs. He lifted my knees, coated his cock with lube, and ran his hand over it a couple of times, wetting it. Then he pressed the head against my hole. I felt the heat, the pressure, the broad tip searching for the opening.

—Breathe.

He pushed. The head went in all at once and I let out a grunt clenched between my teeth. It burned. He stayed still, propped on his arms, letting me breathe. Then he pushed a little more. And more. I felt his cock entering me centimeter by centimeter, opening me from the inside, until I felt his hot balls against my ass.

—It’s all in —he whispered—. You’ve got it all.

I went a few seconds unable to speak, feeling it throb inside me. Then he started moving. Slow pullouts, firm thrusts. Every stroke tore a noise from my throat. At first I was embarrassed; then I stopped hearing myself. He was fucking me and I was spreading my legs so he could fuck me deeper.

—Look at me —he told me—. Look at me while I fuck you.

I opened my eyes. I looked at him. His hair was plastered to his forehead and his lips were parted, and he was pounding into me with his mouth a hand’s width from mine. He kissed me without stopping his movement. He bit my neck. He whispered in my ear things I won’t repeat out loud, about how tight my ass felt, about how hot I was inside, about how badly he wanted to come in me.

***

What came after lasted more than an hour. I’m not exaggerating. Damián had a control over himself I didn’t understand, a capacity to hold out that made the difference between inexperience and practice painfully clear to me. He put me on all fours, face smashed into the mattress and ass high in the air, and fucked me from behind with long thrusts, pulling almost all the way out before driving back in to the hilt. He slapped my ass more than once, not violently, with the firmness of someone keeping time, and each slap made me clamp down on his cock inside me. He laid me on my back with my legs over his shoulders, folded like a book, and there he drove into me even deeper, his balls hitting my ass with each thrust. He put me on my side, pressed against his chest, with one leg lifted, and fucked me slowly while pinching my nipples and stroking me at the same rhythm with his other hand.

At some point he pulled out and made me lick his balls again, sweaty, with my own taste mixed in with his. He made me suck him, wet with my own ass. I wasn’t disgusted. It made me want it more. I sucked him like a whore, watching him slide in and out of my mouth, until he grabbed my jaw and shoved it back in from underneath.

—You’re going to love it like this —he told me, and he mounted me on top of him.

Seated on him, with his cock buried all the way inside by my own weight, I started moving. Up and down, clumsy at first, finding the rhythm after a bit. Damián grabbed my hips and guided me, drove into me with a dark, fixed stare. I had my cock hard, bouncing against my stomach, and he reached out and started stroking me. Every downward slide of mine met one of his pulls. I felt everything rising in me. I warned him with a gasp that I was about to come and he sped up his fist.

—Come. Come on me.

I let out a long stream that splashed onto his chest, then another, then a smaller one, until I was left trembling on top of him with my breathing broken. I had never come like that, so hard, so deeply from inside. And he was still inside me, hard as a rock, waiting.

He laid me back on my back again, spread my legs, and fucked me again with a series of faster, rougher thrusts. My ass was so loosened by the orgasm that it offered almost no resistance. He drove in all the way every time, with a wet sound, while I wrapped my legs around his waist.

—I’m coming —he panted—. Inside?

—Inside —I told him without hesitation.

He sank to the hilt, went still, and I felt his cock throbbing inside me, pumping stream after stream of hot cum into my guts. It was an incredibly strange and incredibly good sensation, a thick heat filling me from within. He came for a long time, his mouth against my neck, biting me, groaning.

The only thing that surprised me about myself was how much I liked it. I had mentally prepared myself to endure it, to put up with the novelty, to record the experience as if it were an experiment. I was not prepared to enjoy it that way. To ask for more. To feel like my body was finding something it had been waiting for for years.

When he finally came out, a thick thread of semen dribbled from my ass onto the sheets. He stayed lying beside me for a long while, holding me from behind, his wet cock pressed to my hip. I had my eyes closed and could barely believe that had just happened.

—Do you regret it? —he asked at last.

—No.

—Would you do it again?

I took a couple of seconds to answer.

—Yes. Right now.

He laughed against the back of my neck.

—Give me half an hour, insatiable bastard.

We showered together in that tiny shower. He soaped my back and slipped his fingers into me again, playing, drawing more of his cum mixed with water out of me. I returned the favor on my knees, with my face level with his cock, sucking him for a while under the hot stream until he fucked me a second time, right there, against the tiles, shorter and more animal than the first. I came again without touching myself, my forehead against the wall and him biting my shoulder from behind.

We dressed slowly, unhurried, as if neither of us wanted it to end. Before we left, he kissed me again. A shorter kiss, cleaner, with less hunger. A goodbye kiss.

—Anything, let me know —he said at the door.

***

What happened between Damián and me didn’t turn into a relationship. I didn’t want it to, and I don’t think he did either. But over the following months we saw each other several more times. At his place, at mine, at another motel. Each encounter was a more relaxed version of the first, without that rookie tension I had that Thursday afternoon.

In time we stopped sleeping together and went back to being just friends. But there is something about that afternoon that still remains intact in my memory. It wasn’t just the sex. It was realizing I was more complex than I had told myself for thirty years. That desire doesn’t fit neatly into the boxes we want to put it in. That sometimes you need to walk through a door, in a downtown motel, at four on a Thursday afternoon, to understand who you are.

I still see Damián once or twice a year, at birthdays and gatherings. We greet each other with a quick hug and a smile only the two of us understand. Nobody around us suspects a thing and, meanwhile, we both know that afternoon exists, filed away somewhere between memory and the confession I’m making now.