My First Bisexual Threesome Was with a Couple Downtown

I reached the entrance of the building without really knowing whether I was going to have the nerve to go up. All afternoon I had been repeating to myself that I was going to regret it, that this was not for me, that I should turn around and go have a drink in any bar in the neighborhood instead. My name is Esteban, I’m forty-eight years old, and that afternoon I had a date with a couple I had met on a hookup site. I consider myself bisexual with very limited experience: one conversation that went nowhere, two failed encounters that ended in nothing, and one very specific memory that kept pushing me to keep looking.

The memory was from my last steady relationship. One night, she put a small vibrator in my ass while she gave me oral sex. I came in an orgasm that left me shaking, with the feeling that something had opened inside me. Since then, I couldn’t stop thinking about trying more. Not with a vibrator, but with a man. And if I could do it in a safe context, with a couple who already had this worked out between them, even better.

I went up in the elevator looking at myself in the mirror and not recognizing myself. I could still go back down and disappear. But I kept going. I rang the bell for apartment 4B and she opened the door in less than three seconds, as if she had been waiting for me behind it for a while.

I could give the name she introduced herself with, but it doesn’t matter: it was definitely not her real one. She had to be around thirty-three, no taller than five foot three, curvy without being fat, with dyed reddish-brown hair that suited her skin well. Pretty face, light eyes, the smile of a woman who knows exactly what she is doing. She was wearing a camisole with thin straps and shorts, barefoot.

—Come in, come in —she said, and closed the door behind me.

—Your partner? —I asked, my voice a little higher than normal.

—In the bathroom. He’ll be out now.

The apartment was one of those small downtown places, with walls freshly painted but already yellowing in the corners, thin laminate flooring, and a smell that mixed sandalwood incense and fresh coffee. She led me into the living room and offered me water. I was so nervous it showed when I swallowed.

—Do you want to leave? —she asked gently, without reproach—. It’s okay if you want to leave, really.

I thought about it. I really thought about it for two or three long seconds. Then I shook my head.

—I want to stay. But I want to meet him first.

—Relax, he’s coming.

And that’s when he came out of the hallway. Roughly my height, about five foot seven, average build with a bit of soft belly, kind face, short three-day beard. He was wearing only gray briefs. He smiled at me, shook my hand as if we were closing a business deal, and said:

—Make yourself comfortable. We’re here to have a good time, not to judge you.

That sentence loosened my shoulders more than anything else could have.

***

We went into a small bedroom, with a double bed taking up almost all the space and a little table with a couple of candles lit. She came over first. She hugged me around the waist, rested her face against my chest, and stayed like that for a couple of seconds. She smelled like something citrusy and soft. I lowered my hands to her ass and started squeezing it over the shorts.

—That’s what I like —she murmured.

I lifted her shirt and pulled it off over her head. She wasn’t wearing a bra. Her tits weren’t firm, but they were a good size and her nipple hardened almost instantly. I bent down and carefully bit one. She breathed harder, took my head in both hands, and held me there, as if telling me not to stop.

We were at that when I felt a naked body pressing against my back. He had come up behind me without me noticing. He wrapped his arms around my waist and I felt his cock, still soft, against my lower back. At that moment I told myself: you’re here now, you’re inside it now, so do it. I took my right hand back blindly until my fingers found him.

It’s strange to touch a cock that isn’t your own. The first thing I thought was that it felt heavier, that the thickness of the skin was different, that it felt hotter than I expected. I wrapped my hand around it and started moving it very slowly, not really knowing whether I was doing it right. He breathed into my ear and started unfastening my pants. When he got them down to my ankles, I could already feel him growing in my fist.

—Let’s go to the bed —she said—. I’m watching you and I’m getting insanely turned on.

The three of us finished undressing. I lay down on my back almost by inertia, and she knelt beside me and started stroking my cock with her open palm, slowly. Then she bent down and took it all the way into her mouth. She was good, very good. She had that calm way of sucking, building it up without rushing, looking into your eyes every now and then. For a moment I almost forgot about the husband.

But the husband knelt on the other side and came close to my face. His cock hung a few inches from my mouth, still half-hard. I was still working it with my hand and feeling it stiffening inside my fist. He was a little bigger than mine, with a glans that was slightly darker. I closed my eyes, opened my mouth, and took the step.

The first time you have a cock in your mouth, it’s disorienting. It is because of the taste, which really tastes like almost nothing, just a salty hint and little else. It is because of the size, which as soon as you have it inside seems twice as big. And it is because you realize you have no idea how to do it, even though it’s been done to you a hundred times. I started out uncoordinated, scraped my teeth against him, and he put a hand on the back of my neck gently.

—Easy. No teeth. Close your lips properly.

I nodded with his cock in my mouth and breathed through my nose. After a few seconds I found a rhythm. Head up, down, flat tongue, hand helping what my mouth couldn’t take. I started to enjoy it. Really enjoy it. Meanwhile, down below, she kept working mine as if nothing were happening, and the sensation of having two mouths working on you and a cock in your face was something I had not quite imagined before trying it. It was much more intense.

I slid my free hand underneath and touched her ass. Soft, hairless, firm. I ran my middle finger between her cheeks, found her anus, and pushed a little. He spread his legs a millimeter, without stopping, and that was all the answer I needed. I slipped the tip of my finger inside, slowly, and felt his whole body tense with pleasure.

***

After a while like that, she pulled me up and lay on her back on the bed, legs open. She pointed at her pussy with a finger and smiled at me.

—Your turn.

I positioned myself between her thighs on all fours and started eating her out. By then I was willing to stay there until my tongue went numb. She was wet, very wet, and she answered every movement with a sigh or a tug on my hair. I alternated: flat tongue over the clit, middle finger going in slowly, lips closing around it to suck.

I was so focused that I didn’t realize he had gotten up, rummaged through the nightstand, and moved in behind me. Not until I felt his hands on my hips. His thumb pressed gently between my butt cheeks. A stream of cold lube made me jerk. He laughed softly.

—Easy. We’ll go slow.

His finger went in first, up to the second knuckle. Then a second one. I kept eating her out, trying not to clamp my jaw shut when he opened me. Then I heard the rustle of the condom wrapper, the snap of the rubber, more lube, and finally, without fully warning me, the tip of his cock pressed against my anus.

—Stop —I told him at the first push—. Stop for a second.

He stopped. He waited. He didn’t pull his cock away, he simply waited. I took a deep breath, rested my forehead against the inside of her thigh, and tried to relax everything that was tense. Ten seconds later I told him to keep going.

The second time, he went in. Slowly, but he went in. And that was when I understood several things at once: that it hurt less than I had expected, that it felt much fuller than I remembered with the vibrator, that the pleasure was not just in the prostate but in the head too, in knowing you’re being opened by another man while your face is buried in his wife’s cunt.

He started moving. At first I asked him to go slower, because after a couple of thrusts he sped up and it was hard to keep up. But after that we found the rhythm. Him behind me, taking care with me, holding my hips; me with my mouth on her, my hands on her tits, squeezing her nipples; her with one leg over my shoulder and the other dangling off the bed, moaning softly and whispering things in my ear that I don’t even remember now.

***

We changed positions one more time. They asked me to lie on my back. He grabbed my legs, put them over his shoulders, and drove into me again in one movement, with no resistance now. She climbed on top of my face, bracing herself against the headboard, and lowered her pussy to his mouth. I was trapped between the two of them: above, her tongue working me; below, him buried inside me and hitting a spot that made my back arch.

I didn’t last long in that position. I couldn’t. I started to feel the orgasm rising from somewhere very deep, different from the usual one. I wanted to warn them, but she didn’t let me: she sucked me to the end, without taking me out, while he kept fucking me and I dug my heels into his back. I came with a muffled shout into her cunt. I literally went blind for a few seconds. When my vision came back into focus, the two of them were smiling at me with affection, still pressed against me.

—Welcome to the club —he said, patting my thigh.

***

After that came the wet wipes, trips to the bathroom in turns, a shared glass of water, and a ten-minute conversation sitting on the edge of the bed. I had arrived with the idea that, if I got up the nerve, I might try giving one of them a turn. But the truth is, the three of us ended up absolutely wrecked. Another time.

I got dressed, we exchanged contact info in case we ran into each other again, and I went back down to the entrance by the same stairs I had climbed a couple of hours earlier not knowing whether I’d be able to do it. I stepped out into the street and breathed the night air, the noise of the cars, the streetlights, everything the same as when I went in. I wasn’t.