When I Decided to Charge for Initiating Gay Men

I’ve been going to the same bar for ten years. It’s a quiet place downtown, with no gaudy neon and no music too loud, where men of a certain age go to drink a whiskey and be what they can’t be anywhere else. The bartenders know me, I know the regulars, and every so often someone new appears with that expression of someone crossing a door for the first time and not quite sure whether he’s going to regret it.

It was a Tuesday in October. Marcos arrived around nine, chose the stool beside me without looking anyone in the eye, and ordered a gin and tonic that he took too long to start drinking. He was forty-five, though I didn’t know that then. Dark suit, tie loosened, wedding ring on his finger. The kind of man who has a perfectly organized life outside that bar.

We started talking the way people do in bars, without much hurry. He told me he’d been married for twenty years, that he had two children in college, that he ran an import company that didn’t give him too many problems. He spoke well, calmly, with no obvious nerves. But when I asked what had brought him there, he took a moment to answer.

—I want to know what it’s like —he said at last, staring into his glass—. I’ve had dreams. I don’t know how else to explain it. I’ve dreamed that someone takes me up the ass, shoves it all the way in, and in that dream I don’t wake up uncomfortable. I wake up with a hard cock and wanting more.

I stayed silent for a moment, sizing him up.

—And you’ve never tried it?

—Never. I don’t even know how I’d begin.

When he went to the bathroom, I stared at my own glass for a while. I thought about telling him it wasn’t that complicated, that he just had to let it happen. But I thought better of it. There was something in the way he’d told it —the precision, the honesty— that gave me another idea. When he came back, I waited until he sat down before speaking.

—Look, there’s something I haven’t told you —I said—. I’ve got an apartment and free time. And it wouldn’t be the first time I’ve helped someone in a situation like yours.

He looked at me without fully understanding.

—What exactly does that mean?

—It means that, if you want, I can be your teacher. Calmly, no rush. One hundred and fifty dollars a session.

There was a long silence. Not the silence of someone about to say no, but of someone who has already made the decision and just needs to hear it out loud one more time before admitting it.

—Have you done this before?

I lied a little.

—A few times.

The truth was I never had. But something told me that didn’t matter. We made plans for the following Thursday at seven in the evening.

***

On Thursday at six I was nervous. I straightened the apartment twice. Bought new lubricant, put on clean sheets. Changed clothes. It was the first time I was going to be the teacher, but I couldn’t afford to look like it.

Marcos arrived at seven on the dot. He knocked on the door with his knuckles, not the bell, as if he didn’t want to make too much noise. He came in wearing the same suit as the other day, scented with cologne, hair combed back. He looked more serious than he had at the bar, but his hands didn’t tremble.

I offered him water. He accepted with a brief gesture and stood in the center of the living room, looking without really seeing anything. There was something that needed to happen before we began: he had to forget the suit, the children in college, the import company. He had to be present, not half-present.

—Are you okay? —I asked him.

—Yes. Just give me a second.

I waited. And after that second, he turned toward me and looked at me differently. That was enough.

I kissed him slowly. He didn’t pull back. His lips were tense at first, not quite knowing how to move, but within a few seconds something began to loosen. I slid my tongue into his mouth and he took it like a man who had spent years wondering what another man’s saliva tasted like. I cupped his jaw with one hand and felt him breathing deeper. With the other I grabbed his crotch over his pants and felt his cock already half-hard, pressed tight against the fabric. He closed his eyes and let out a low sound, like relief, when I squeezed his balls with my palm.

I undressed him slowly. The tie first, then the buttons of his shirt one by one. He didn’t help or resist, he simply let it happen. When I took off his shirt, I saw that his chest and abdomen were covered in dark hair. The body of a man who had once worked with his hands, even if now he spent his days behind a desk. I ran my tongue over his nipples, one and then the other, nibbling until they hardened, and he let out a short groan he couldn’t hold back.

His pants fell to the floor and he was left in his underwear, standing in front of me. He wasn’t a spectacularly built body, but there was something solid and real about him that was more attractive than any manufactured perfection. I pulled his briefs down with both hands and his cock sprang out, thick, the pink head peeking from the foreskin, a drop of fluid already shining at the tip. He had big balls, hanging low, covered by the same dark hair climbing up his belly.

I knelt in front of him. I noticed him holding his breath.

—Relax —I said—. You don’t have to do anything.

I took his cock in my hand and put it in my mouth without ceremony. First just the head, sucking it slowly, running my tongue under the glans, playing with the frenulum. He let out a long gasp and his hips moved forward involuntarily. I took him in little by little, centimeter by centimeter, until I felt the head touch the back of my throat. I pulled back, took him in again, pulled back once more, leaving a thread of saliva hanging between my lips and his glans. Then I licked his balls, took them into my mouth one by one, and went back to his cock, sucking him with rhythm, with my whole mouth, no teeth, while with my hand I stroked his ass.

By the time he was fully hard, his hands had found my head, not to push, but to steady himself, like someone needing support in a dizzy spell. I heard the first sound he made: it wasn’t quite a moan, more like a long exhale, as if he’d been holding his breath for years. His cock throbbed in my mouth; I let it go with a pop and saw it gleaming, swollen, the veins standing out.

—Fuck —he muttered—. No one’s ever sucked me like that.

I asked him to return the favor. He knelt without saying anything and took a moment to decide, like someone standing at the edge of a pool before diving in. When he did, he was clumsy at first, not quite knowing where to put his teeth, how to breathe. He choked the first two times he tried to swallow it all, and had to pull away coughing. I gave him directions in a calm voice, without hurry.

—Tongue underneath, don’t squeeze with your lips. Like that. Now breathe through your nose. Go lower. That’s it.

He learned fast, and he genuinely wanted to do it well. That made all the difference. Within a few minutes he was taking me in with ease, hand at the base, bobbing his head up and down at a rhythm he was finding on his own. He looked up at me with my cock in his mouth and that almost made me come right then and there. I stroked his hair and pulled him away before it was too late.

I took him to the bedroom. He lay face down on the bed without me asking, as if his body already knew what was coming even though his head hadn’t been there before. I ran my hands over his back, then his waist, his ass cheeks. He had the body of someone who exercised regularly but without obsession. I spread his ass cheeks with both hands and saw his hole for the first time: tight, virgin, surrounded by the same dark hair covering the rest of his body. I blew on it and felt him shiver.

I slipped in a finger, with lubricant, very slowly. He tensed immediately, the sphincter closing around my knuckle.

—Breathe —I said—. Loosen up. It won’t hurt if you don’t resist it.

He did, and the tension gradually gave way. The finger went all the way in and I started moving it in circles, opening him carefully. I slid in a second finger and he let out a muffled whimper into the pillow, but he didn’t ask me to stop. I searched for his prostate, that soft bulge inside, and when I found it and pressed, he arched his back sharply.

—What is that? —he said, almost frightened.

—That’s what you were looking for.

Then I used my tongue. I pressed my mouth to his hole and started licking it, opening it up, sucking it like I was kissing his mouth. I heard him say something under his breath that I couldn’t quite make out, but his body didn’t lie: he arched toward me instead of away, and started rocking his hips against my face. I grabbed his cock underneath and felt it rock hard, leaking pre-cum onto the sheets. I kept at it for several minutes, alternating tongue and fingers, until the sounds he made became less restrained and more honest. They weren’t whimpers anymore: they were open moans, filthy, from a guy getting his ass opened for the first time and discovering he’d wanted it for years.

—How are you doing? —I asked.

—I don’t know how I’m doing —he answered, face buried in the pillow—. Good. I think very good. Keep going, please.

I added more lubricant than probably necessary, because I preferred to err on the side of caution. I coated my cock well, until it was shining, and put some more on his ass with my fingers, pushing them all the way in so he’d take it inside. I positioned myself over him slowly, resting my weight on my arms. I pressed the head of my cock to his hole and pushed carefully, barely a centimeter, and waited. His breathing sped up all at once.

—Can I keep going?

—Yes —he said. Without hesitation—. Put it in me.

I entered him little by little, without haste, waiting between each movement for his body to adjust. I felt the sphincter close around the base of my head and then give way, swallow me, let me pass centimeter by centimeter. He let out a long moan, half pain, half something else, and grabbed the pillow with both hands. When I was fully inside, my balls resting against his ass cheeks, I stayed still for a moment. He didn’t move either. He just breathed, mouth open against the sheet.

—You’ve got it all the way in —I whispered in his ear—. How does it feel?

—Full —he murmured—. I feel full. Fuck.

Then we started moving. At first slowly, almost not moving at all, pulling it out only a little and pushing it back in. Then with more rhythm, as he relaxed and began pushing back, seeking me with his ass. He wasn’t speaking, but he made sounds that said more than any word: grunts, gasps, the occasional curse under his breath every time I drove it in deep. At some point he planted his forearms on the bed and lifted his hips toward me, putting his ass in my face, and something about that voluntary gesture, that conscious surrender, felt hugely satisfying. I grabbed his waist with both hands and started fucking him harder, with long thrusts, listening to the sound of my balls slapping his perineum.

—That’s it —he said, voice hoarse—. Like that, don’t stop.

I slipped a hand underneath and grabbed his cock: it was hard as a rock, slick with fluid. I started jerking him off to the rhythm of my thrusts, and he let out a broken moan that came from very deep inside him. We went on like that for about twenty minutes, changing pace, with him pushing back each time I pushed forward, until he started trembling all over.

—I’m going to come —he said, almost surprised—. Without touching myself, I’m going to come.

—Come —I told him, without stopping fucking him—. Come with my cock inside you.

I let go of his cock and grabbed his hips with both hands, hitting him harder, and after a few seconds he came: a long spurt onto the sheets, then another, while his ass clenched in spasms around my cock. He was the one who asked me to stop, in a hoarse voice, when he couldn’t take the stimulation anymore.

—I think that’s enough for today. Pull it out.

I eased out without rushing, my cock sliding out slowly, still shiny and hard. My body was on fire and my head was fully in the moment, something that doesn’t always happen. I knelt on the bed near his face and started jerking off fast, squeezing hard. He turned his head and looked at me, and when I asked without words, he opened his mouth. I came over him: the first two spurts on his tongue and lips, the rest on his neck and chest. He ran his thumb along the corner of his mouth to gather what had spilled there and took it into his mouth without thinking. It wasn’t awkward: he was looking at me with an expression that mixed exhaustion and something like gratitude.

Then he got dressed slowly, went to the bathroom, came back with wet hair and his shirt neatly buttoned. He took his jacket from the back of the chair and put it on with the automatic gesture of someone who’s been doing it for decades.

—How was it? —I asked, though I already knew the answer.

—Better than I expected —he said. And he meant it.

He left the money on the little table by the entrance and went out without ceremony. I closed the door and stood there for a moment leaning against it, staring silently at the apartment. I wasn’t sure I’d been a good teacher, but I was sure there was something there worth repeating.

***

Three weeks later, an acquaintance from the bar asked me, with a lot of roundaboutness and very little subtlety, whether what he’d heard was true. It was Tomás: twenty-two years old, a design student, skinny and tall, with the kind of smile that tells you the person knows exactly what they want but enjoys the process of getting there.

—How much? —he asked, without any preamble.

—One hundred and eighty.

—Why more than with the other guy?

—Because with the other guy it was the first time for me too.

He laughed. A short, genuine laugh I hadn’t expected. We made plans for the following Monday.

Tomás was different from Marcos in almost everything. Where Marcos had arrived contained and silent, Tomás arrived with too much energy and too many questions. He wanted to know how it was going to be, what he would feel, how much it would hurt. I calmed him down little by little, with patience, though at some point I had to ask him to stay still for a moment and breathe.

—Can I sit down? —he asked, looking at the bed with a mix of curiosity and nerves.

—That’s exactly what you’re going to do.

His body was completely different from Marcos’s. Slender, almost hairless, very pale, with that physical awkwardness young guys have when they don’t know what to do with their hands. His cock, though, was bigger than his body suggested: slim, long, cut, already semi-hard as soon as he’d taken his clothes off. But he had something Marcos didn’t: genuine curiosity, without fear disguised as indifference. He wanted to understand everything that was happening, not just live it.

I explained things as we went. First I showed him how to suck cock properly, guiding his head, teaching him to use his tongue, not to close his teeth, to look up when he had a cock in his mouth because that drives anyone crazy. He learned faster than Marcos. Then I licked his ass until it was dripping wet, alternating tongue and fingers, listening to him moan into the pillow with that high young-guy voice. When I slid in the first finger, he almost came just from that.

—It’s touching something inside me —he said, eyes wide.

—I know what it’s touching. Hold on.

I put on a condom, plenty of lubricant, and had him sit down on me at the edge of the bed, letting him control the pace of the penetration. He lowered himself slowly, hands on my shoulders, mouth open as he felt my cock go in. It took longer than usual, he stopped twice to ask if he was doing it right, and both times I told him yes. When he found the right angle and understood how to move, he didn’t want to stop: he started riding me with his hands braced back on my knees, his cock bouncing hard against his belly, head thrown back. He came onto my chest without touching himself, with a long shout, and kept riding me a few minutes more until I came inside the condom too, gripping his waist.

We had two sessions that afternoon, with a long break in between. In the second, he asked me to do him from behind, harder, without so much care, and I gave it to him exactly as he asked. When he left, he was much calmer than when he arrived, with that particular calm of someone who’s just closed a question that had been open for a long time.

***

In the two months that followed I took care of six more men. Different ages, different bodies, different reasons for being there. An architect of fifty who’d been living a double life for a decade and wanted to understand why, and ended up asking me to fuck him standing up against the bathroom wall, biting his fist so he wouldn’t scream. A twenty-five-year-old who was simply curious and wanted his first time to be with someone who knew what he was doing, and who turned out to be the kind who comes three times in one afternoon. A businessman who traveled to the city often and needed something he couldn’t seek where he lived, and who asked me to cum on his face the first time and in his ass the second.

Eight in total, counting Marcos, Tomás, and the six who came after. Fully booked for almost two months. Eight different cocks sucked, eight different asses opened patiently, eight different men moaning under my weight in the same bed.

I’m no expert at anything. I didn’t study any special technique or read manuals on the subject. I simply learned, over time, to go slowly, to read the other person’s body, not to push where there’s real resistance. To tell nervousness from rejection. To know when a guy is ready for two fingers and when he still needs one. To make the other person feel safe without needing to say it out loud.

What surprised me wasn’t the sex itself. What surprised me was what happened afterward, when they got dressed and left. Most left in silence, with that expression of someone who has just confirmed something they’d been wondering about for a long time. Not all of them came back. Not all of them needed to. But every single one left without regret.

That’s what stayed with me. Not the money. The silence of someone who has just understood something about himself he couldn’t have learned any other way. And the slightly unexpected certainty that there are trades that don’t appear on any list, but are needed anyway.