The Stranger Who Taught Me to Enjoy Being with a Man

It’s been a long time since I last stopped by here, and although my time as a writer was brief, I always liked to boast that I had a good imagination for inventing situations, games, and desires. Today, however, I’m here to do something different. Today I don’t want to fantasize or embellish anything. Today I want to confess and remember, with all the honesty my memory allows me, the first time I was truly with another man.

Before getting into it, let me give a little context, which I promise not to drag out too much.

As long as I can remember, I was a boy with an awakened sexuality. Like almost everyone, I discovered pleasure through curiosity, through inexperience, through that urge to touch what’s forbidden. The difference, in my case, is that many of those early discoveries happened in the company of other boys, and I never found it uncomfortable. It seemed like the most natural thing in the world, because at that age most of the people around me were boys. I suppose that’s why I always treated my bisexuality with complete naturalness, although I must admit it was only with people outside my family. It wasn’t that I hid it; I just didn’t feel I owed anyone any explanations.

There’s one detail that matters for what comes next: my attraction to men was always above all sexual, rarely romantic, although I’m not unaware of the odd brief relationship. And to be precise, my preferred role in bed was always the receptive one.

That said, and apologizing for the length of the preamble, I’ll now tell you how my first complete experience with another man was, the one I still remember with a mix of turn-on and nostalgia.

***

I was twenty, about to turn twenty-one. It was the summer between my first year and my second, far from the village and my parents’ house, where I was obliged to return during the hot months. Living with my father was never easy: arguments, sour looks, replies that got out of hand. It wasn’t something particular to that year; it was the usual thing.

One afternoon, my parents decided to slip away for a couple of days and I was left alone with the laptop the whole family shared. As you can imagine, there wasn’t much caution when it came to watching porn on that shared machine, and even less in that first year we had a decent internet connection, without cutouts or phone calls interrupting it. That was the first time I dared to look for gay porn, something risky on a shared-use laptop, but that little bit of risk added its own share of turn-on.

I wasn’t going in completely blind. I had already had one or two experiences with boys, but that afternoon was the first time I remember clearly seeing a man enjoying having another one inside him. Almost instantly, the arousal mixed with a huge urge to feel exactly what I was watching. And yes, I admit it: on other occasions I had already tried inserting some object and enjoying it, but it had nothing to do with what I was expecting that afternoon.

I decided to go into the “gay” section of a chat site where I usually spent hours meeting people, with a sexual interest that was almost always secondary. This time it was the other way around. The excitement blinded me completely: I was alone at home, naked, jerking off every so often while I imagined myself with another man. I even used the same nickname I used in other rooms, without weighing the risk. Browsing among the categories, I found a room from my own province and thought the plan would be simple: meet a guy my age, talk, get each other worked up a bit, and little more. I had no idea what was going to happen, or who I would find, and that uncertainty made the temperature rise even more. Because if someone recognized me, the situation became dangerously exciting.

Nothing turned out the way I had imagined.

After a while announcing myself on the channel as a bisexual guy who just wanted to meet new people, someone wrote to me privately. What was already an aroused conversation for me started with the usual topics: tastes, fantasies, quirks. Each of his answers heated me up a little more. I don’t remember the exact moment, but it was him who offered to come to my place to help me “more efficiently” with my condition. And I admit I hesitated. I hesitated quite a lot.

I was talking to a complete stranger, eight years older than me, who also wanted me to receive him at the door completely naked. I couldn’t blame him entirely either: part of it had been my idea. But then there was the risk that my parents would come back early and we wouldn’t be able to hide what we were doing, and that danger only fed the turn-on that was already clouding my judgment. Of course, I ended up agreeing. I gave him my address and left his wish only half fulfilled: I put on a slightly long T-shirt, though not long enough.

***

He showed up at my building’s entrance barely twenty minutes after I told him how to get there. I was flushed, nervous, embarrassed and, above all, turned on. I opened the door without really knowing what I was going to find, and there he was, half hidden behind the door leaf. To me, he was already a grown man. I let him in quickly, in case some nosy neighbor was nearby.

He looked me over and pointed at my T-shirt, the shame T-shirt, with a half smile and his hands in his pockets. He also seemed a little awkward at first. It occurred to me that the best thing would be to buy a little time, so we went into the kitchen to smoke and chat as if my half-nakedness wasn’t there, obvious as day. And that actually helped me relax, to let myself be carried away by that man who was only looking for sex. I knew it perfectly well.

Soon after, we moved to the living room. It was the best place, and just thinking that that sofa was going to be used for a fuck between two men, something my father would never know about, gave me a strange, deep satisfaction. That’s why I chose precisely the place where he usually sat, as if that way I could piss him off more if he ever found out, which would never happen.

We kept talking for a short while until he started reaching under my T-shirt. I was covering my crotch with the fabric, but the bulge was so obvious that he took it as an invitation. And it was. When I felt his hand close around my cock, the shiver I had been waiting for ran through me. That was the starting gun.

—Fuck —slipped out of me, cutting off what I was saying all at once.

My face must have changed completely, because without thinking any more about it he lunged to kiss me while his hand kept moving up and down without pause. I remember how all the negative sensations evaporated and left only the turn-on, the excitement, and a wild urge to give in. I put my hands on his trousers to get them off him quickly, but I wasn’t as fast as he was, and with one tug he finished stripping me completely. His hands went wild all over my body.

Seated, with him a little on top of me, I managed to get my hand inside his trousers. I needed, I longed to show him what I could do with my tongue. It was a good one, thick and long, similar to mine if memory doesn’t fail me. As soon as he felt my hand gripping it like a door handle, he straightened up to take his trousers off once and for all.

I ended up on my knees on the sofa, next to him, holding it with my left hand. It wasn’t the first time I’d done that, but it was the first time it wasn’t a test, an experiment, or a tentative try. This time it was serious. I leaned over him, rested my head on his stomach, and there it was, right in front of me, throbbing against my hand. I dragged my fingers along the shaft until the head came out, so shiny it reflected the light, and took it straight into my mouth.

I started moving my head along its length, squeezing it with my lips, rubbing the head against my palate. I was eager to take the next step, but oral sex was always one of my favorite things and I enjoyed every second. Meanwhile, his hands traveled down my back to my buttocks, which seemed to please him. I don’t blame him: even today I boast about having a good ass.

***

I knew I couldn’t linger as much as I would have liked. The risk of interruption was still there, so we went straight to the main course. I sat up without letting go of his cock and looked at him smiling. I barely registered his expression, but he was leaning back, waiting. I can’t hold out any longer, I thought, and swung one leg over to straddle him.

He put a hand on my ass and opened it a little, as if to make the task easier. He tried to move to line himself up without using his hands, but I guessed that would be tricky.

—Slowly, please —I asked him, and I positioned it where it needed to be myself.

And he listened. More than that, he let me keep control at first, which is always the most delicate moment. I started to feel him entering little by little, opening me from within. I don’t remember any pain that time, but I do remember my first genuine moan of pleasure, sharp and ragged, stretching out until he stopped pushing, as if he were taking a breath halfway through. After that, with small back-and-forth movements, I helped each new thrust go a little deeper.

The more he went in, the more I wanted it; the more I wanted it, the more he pushed; and the more he pushed, the more I moaned. That exhausted the little self-control he had left. With his hands firm on my hips, he began to guide me, making me bounce on him as if I were riding him. He was all the way in now and the intensity kept rising with every movement.

I focused on the sounds, on the clash of our bodies, imagining what my back would look like from the outside, as if we were going to get caught at any moment. I shuddered, trapped between modesty, shame, and a turn-on I hadn’t expected. I was still rock hard, and with each bounce I saw my balls dropping onto his pelvis while my cock swung to the rhythm of us both.

Then he took the initiative. He lifted me a little, sat up, and put his feet on the edge of the sofa to control the movement himself, and I thought it was perfect. I leaned forward and let him decide everything: the speed, the force, when to stop and when to go on. I wasn’t thinking about anything anymore except how incredible it was. For several minutes he fucked me however he wanted, never taking his hands off my ass, until suddenly he stopped, leaned back, and seemed to want to leave the rest to me.

I only wanted to keep moaning, so I kept riding him without mercy. And then he grabbed my legs, pulled me down toward him, and thrust upward with his whole body. His face said it all: he was coming. Without warning, without saying a word, without having discussed it beforehand, he let all his cum stay inside me.

At first I wanted to get angry. It was a huge risk, and besides, I still wanted more. But without taking it out at any point, he decided it was my turn, and he started jerking me off before I could react. I was in ecstasy, enjoying both sides at once, unable to move. I ended up coming all over his bare chest, and with each convulsion he got another one inside, because he didn’t pull out until the very last moment.

***

From that day on I learned a modus operandi that would later lead me into other similar situations, but that encounter was special for being the first truly complete one, and the most pleasurable in a long time. Maybe I paid too little attention to safety, and I was lucky everything turned out well. Since then I’ve always tried to be more careful, except for one single, much more recent occasion. But I’ll leave that story for another account.

I hope you liked it.