I Lost a Bet and Ended Up at a Bachelor Party

It all started with a stupid bet, one of those you accept without thinking through the consequences. It was Friday, and a few of us from college had gathered at Bruno’s apartment to play cards. We’d drunk enough for bad ideas to seem brilliant.

—Whoever loses the last hand does whatever the winner says —someone suggested, laughing. We all agreed without giving it a second thought.

I lost. And out of everyone at that table, the one who won was Bruno, my best friend, the only person who knew me well enough to know how far I was capable of going.

He looked at me over the cards with a crooked smile.

—I’ll tell you in private later what you have to do —he said, and went right back to shuffling as if nothing had happened.

Why won’t he just tell me right here?

I let it go, and we went on with the night: more drinks, music, someone trying to dance in the kitchen. After midnight, we started saying our goodbyes. Bruno, who was the only one with a car, dropped everyone off at home one by one. He left me for last, and only when we were alone did he bring it back up.

—The dare is for you to pass yourself off as an escort —he blurted out, staring ahead.

I was speechless. To be honest, I’d imagined he’d ask me for something between us, one of those things we’d already done before. I hadn’t expected this.

He explained that a friend of his was getting married and that, among them, they wanted to give him an unforgettable bachelor party. He’d talked about me, shown a couple of photos, and his friends had thought I was perfect. The chance to cash in the bet had landed in his lap.

—I still charge like a professional —I told him, pretending I was more confident than I felt—. This costs money.

—Don’t worry about that —he replied, and wrote down an address, a date, and a time for me to meet the organizer.

***

The day of the meeting, I found myself with a man in his forties, in a suit and tie, with that calm air of someone used to handling money. His name was Esteban. He invited me to lunch, we chatted about anything and everything, and, over coffee, he explained the details.

—You’re going to be the only woman there that night —he said, bluntly—. The idea is for everyone to have a good time. Whatever they ask for, within what you agree to.

I named my price. I said a figure that seemed high to me, almost provocative, expecting to scare him off. Esteban didn’t even flinch.

—Are you sure that’s all? —he asked with a half-smile—. Is this your first time doing this?

—It’s not my first time —I lied, holding his gaze—. And yes, that’s the price.

He laughed, amused.

—You didn’t even ask how many of us there’ll be.

It was true. It turned out there were seven, with the possibility of a couple more joining in because they were traveling in. I told him I’d been with several men at once before, that one more or one less didn’t change anything. He liked my attitude, he said, and promised to pay me even more than we’d agreed.

We closed the deal with conditions on both sides. His: a little show to start, that I be dressed well or in lingerie, and that I let them film it for private use, because they were all married men who didn’t want trouble. Mine were simple: medical tests for each of them, and that they not disappoint me.

Esteban burst out laughing.

—If any of them doesn’t satisfy you, I’ll take care of it —he said, and transferred a deposit to my account so I wouldn’t back out.

***

The day arrived. I went to the salon, got my nails done, did everything a woman does when she’s preparing for a long night. I’d already done the medical exam the day before. At home I took a long shower, got myself ready carefully knowing what was coming, and chose my outfit: a short miniskirt, fishnet stockings, black thong, a white top, and heels. I looked at myself in the mirror and for a second I didn’t recognize myself. I liked what I saw.

They picked me up at seven. The first person to see me was Esteban, who didn’t miss the chance to take my hand and spin me around.

—We’re going to have a great night tonight —he murmured, and as I got into the car he gave me a smack on the ass that made my skin tingle.

The apartment where the party would take place was on a high floor. They took me to a room to wait while everyone arrived, so I could surprise the groom. When I peeked out, I counted the men I’d have to please: most were over thirty-five, three were younger, all in suits, all good-looking. In the center, blindfolded, was the groom. Tomás, I learned later. Tall, average build, pleasant, with a nervous smile even though he couldn’t see a thing.

They put on music. They removed the blindfold just as I came walking toward him, pretending to be a runway model. My skirt rode up with every step, and I let it. Tomás froze, speechless, as if in shock.

I started to dance. I turned around, brushed my ass near his face, lowered myself slowly, stroking my legs. He still didn’t move.

—Aren’t you going to touch me, daddy? —I whispered in his ear, and sat down on his lap.

I felt him hard beneath his pants. I took his hands and placed them on my breasts. I turned a couple more times, told him he was going to have a night to remember, and got up to give the same treatment to the others, who watched every detail without missing a thing. I took off my top, then my skirt, until I was left in thong, stockings, and heels.

***

I remembered Bruno’s advice: the groom had to go first. I took Tomás by the tie and led him to the room.

I laid him back on the bed, sat on top of him, and started unbuttoning his shirt while I moved slowly. He was still motionless, not knowing what to do with his hands.

—Relax, you can touch me all you want —I told him.

He started with my breasts, awkwardly, squeezing too hard. Nerves, I suppose. I told him to take it easy, to enjoy himself without rushing. I kissed his neck, worked my way down his torso, his abdomen, while with my other hand I stroked him over his pants. When I loosened his belt and pulled everything down, I found him ready, a size that was easy enough to handle.

I ran my tongue in circles over the tip and he shuddered all over.

—Do you like it? —I asked.

—A lot —he could barely get out, his head thrown back.

I took more and more of him into my mouth. Then I knelt down and played with all of it, slowly, until he stopped me.

—Don’t. Don’t make me come. I want to be the first to taste you.

I got on all fours on the bed and arched my hips. Tomás looked at me for a second before entering in one smooth thrust. He held my hips and started slow, deep. He wasn’t bad at all. Little by little he sped up, until my ass was slapping against him and the moans came out of me on their own.

More confident now, he started playing with one finger elsewhere, in circles, testing.

—You want it there? —I asked, looking over my shoulder.

—I want to be the first —he said.

I got myself well lubricated with my mouth, went back into position, and asked him to go in slowly. He did, little by little, sliding the tip in and out until I gave all the way. When he reached the deepest point he pressed against me with a long sigh.

He didn’t last long; it was his first time like that. He warned me he was about to finish, and I knelt in time to take him in my mouth, holding him with my hand until the very last drop.

—Best gift in years —he said between laughs, exhausted.

***

We went out to the living room, where the rest were waiting with glasses of whiskey. They applauded when they saw us come out and asked Tomás if he liked his gift. He joked that he no longer felt like getting married. I sat down among them, and while they talked about their lives and wished the groom luck, hands started reaching for me: one on my leg, another on my ass.

Esteban asked me for a few photos. I agreed and struck a couple of poses for his enjoyment. Every comment they made to me heated me up a little more. On all fours, I crawled up to the one holding the phone, pulled down his pants, and found a very big, thick cock, the kind I like.

—Take good pictures like this —I told him, and took him into my mouth.

It was so thick it barely fit, but I tried anyway, licking the whole thing like an ice cream cone. While I did, the others moved closer, surrounding me, and suddenly there were hands everywhere and a line of men waiting their turn.

Among them one stood out: a tall guy with broad shoulders, bronze skin, in his thirties. He wasn’t the longest, but he was the thickest of them all, so much so I couldn’t wrap my hand around him. This one’s going to split me open, I thought, and I liked the idea more than I’d expected.

I threw myself into the task. Some liked to hold my head and set the rhythm; others preferred it slow, others deep. Meanwhile, someone settled underneath and started using his tongue between my legs, making me moan with both hands occupied. Another focused on my breasts.

Bruno took me to the sofa, sat down, and asked me to ride him. I started slowly, then harder, while two others came up on either side so I could take care of them with my mouth. We changed positions, partners, in a wheel that never stopped. Every so often I searched for the broad-shouldered one with my eyes, gauging when my turn with him would come.

—Relax —he told me when he caught me looking at him—. I know when it’s your turn.

***

The turn came. The others moved away and I was left alone in front of him, and he ordered me to get on all fours. Beforehand I asked for my bag and took out the lubricant: I coated his cock with both hands until not a single inch was dry, and then I prepared myself. He watched me with a patient smile.

—I’ll let you get away with the lube this once —he said—. I was going to put it in dry.

I got nervous. I knew what was coming. He slapped me a couple of times with it over my ass, heavy, before aiming. The first thrust drove me forward from the pressure, and it slipped out with a sound that made the others laugh. I took a breath on the sofa.

—Another position —I suggested.

—No. I want you like this.

I went back on all fours, spread myself open with both hands, and this time he went in slowly, pushing with one hand on my back so I couldn’t get away. I bit the edge of the sofa while I felt him working his way in, until he was all the way inside. The others clapped as if they’d won something.

He started slow but deep, feeling how I adjusted to his thickness. When he picked up the pace, the pain mixed with the pleasure in a way that made me scream. Esteban told me to shut up and, in a second, two more were at my sides offering me their mouths. I tried, but the thrusts left me unable to do anything but moan.

With time I got used to it. Since I’m small, he lifted me in his arms without coming out and carried me to the bed, where he kept going. After a while, the others demanded their share.

—She’s ready now —he said, standing up.

***

What followed was a succession I lost count of. Tomás again, then another, then two at once, one underneath and one behind, the first of several double penetrations that night. They changed places, came in and out, finished in my mouth, on my back, wherever I fell. The one with the thick cock was always the one I enjoyed most: hard, relentless, capable of making me scream and leaving me wanting more.

At some point I looked at my phone: it was after eleven. Three hours nonstop. I took a quick shower, put on something more comfortable, and went back to the living room, where Esteban welcomed me happily.

—You’ve got more stamina than most —he said—. But the night is still young. Stay in your thong, because this is just getting started.

I agreed. The party went on: some just drank, others took me to the room one by one or two by two. Three more arrived, just in from their trip, and I imposed the only condition that they use condoms because I didn’t have their test results. They didn’t object.

That’s how the dawn passed, between drinks, laughter, and bodies. The broad-shouldered one came looking for me again when almost everyone was asleep, waking me with his mouth and hands, unable to let me rest. By then I’d put on a numbing cream and let him do it, because, I admit it, I didn’t want him to stop either.

When I realized it, it was past six in the morning. I ended up worn out, sore, and marked all over, but more satisfied than I’d been in a long time. I asked to be taken home, and as the car pulled away with the sun coming up, I thought that of all the bets I’d ever lost in my life, none had worked out so much in my favor.