I Lost a Bet and Ended Up at a Bachelor Party

It all started with a stupid bet, one of those things you agree to without measuring the consequences. It was Friday, and a few of us from college had gotten together at Bruno’s apartment to play cards. We’d had enough to drink for bad ideas to seem brilliant.

—Whoever loses the last hand does whatever the winner says —someone proposed between laughs. We all agreed without thinking.

I lost. And of everyone at that table, the one who won was Bruno, my best friend, the only one 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 what you have to do later —he said, and went right on shuffling as if nothing had happened.

Why won’t he tell me right here?

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

—The challenge 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—he knew how much I liked it when he fucked me from behind while covering my mouth, he knew how easily I came the moment he bit my neck. This wasn’t what I expected.

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

—I charge like a professional anyway —I told him, pretending to be more sure of myself than I was—. This isn’t free.

—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 appointment I met a man in his forties, in a suit and tie, with that calm of someone used to handling money. His name was Esteban. He took me to lunch, we talked about anything and everything, and between coffees he explained the details.

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

I named my price. I said an amount that seemed high to me, almost a dare, hoping to scare him off. Esteban didn’t even blink.

—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 from out of town. I told him I’d already been with several men at the same time, that one more or one less didn’t change anything. He liked my attitude, he said, and promised to pay me even more than agreed.

We sealed the deal with conditions from both sides. His: a little show to start, that I’d be well dressed or in lingerie, and that I’d let them record 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 gave me an advance transfer so I wouldn’t change my mind.

***

The day arrived. I went to the hair salon, got my nails done, did everything a woman does when she’s getting ready for a long night. I already had the medical exam from the day before. At home I took a long shower, waxed myself carefully until my cunt was smooth and hairless, slid two fingers in with soap to make myself thoroughly clean inside, knowing they were going to enter me both ways. I chose the outfit: a short miniskirt, fishnet stockings, a black thong, a white top without a bra, and heels. I looked at myself in the mirror and for a second I didn’t recognize myself. My tits stood out hard against the fabric, the nipples already straining just from thinking about what was coming. I liked what I saw.

They picked me up at seven. The first one 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 very good night —he murmured, and as I got into the car he gave my ass a smack that made my skin prickle and my thighs clamp together.

The apartment where the party was being held was on an upper floor. They took me to a room to wait while everyone arrived, so they could surprise the groom. When I peeked out, I counted the men I’d have to satisfy: most of them over thirty-five, three younger ones, all in suits, all good-looking. In the center, blindfolded, was the groom. Tomás, I learned later. Tall, average build, nice-looking, with a nervous smile even though he couldn’t see a thing.

They put on music. They took off the blindfold just as I came walking toward him, pretending to be a runway model. My skirt rode up with each step and I let it. Tomás went rigid, mute, like he was in shock.

I started dancing. I turned around, brushed my ass close to his face, and slowly lowered myself, stroking my legs. He still hadn’t moved.

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

I could feel him hard beneath his pants, his cock pressing against the fabric, trapped between my ass cheeks. I took his hands and placed them on my tits, pressing them so he could feel the stiff nipples through my top. I gave him a couple more turns, grinding my ass against the bulge, whispering in his ear that he was in for a night to remember, that I was going to leave him dry. I got up to give the same to the others, who were watching every detail, some already with a hand in their crotch adjusting their dicks. I took off my top and my tits were bare, then the skirt, until I was left in my thong, stockings, and heels. One whistled, another tucked a bill into the thong strap and squeezed one of my ass cheeks with an open palm.

***

I remembered Bruno’s advice: the one getting married had to be 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 moving slowly, rubbing my already wet cunt over his pants. He still stayed still, not knowing what to do with his hands.

—Relax, you can touch me wherever you want. I’m yours tonight —I told him.

He started with my tits, awkwardly, squeezing too hard, twisting my nipples between his fingers. Nerves, I guess. I told him to calm down, to enjoy it without rushing, to lick them. He took them into his mouth one by one, sucking on them hungrily, and I buried my fingers in his hair to press him harder against my chest. I kissed his neck, moved down his torso, his abdomen, biting his skin, while with my other hand I stroked him over his pants. When I undone his belt and pulled everything down, his cock sprang hard against his abdomen: not the biggest, but a size that was easy to work with, thick at the base and with a red, swollen head.

I ran my tongue in circles over the tip and he shivered all over, a drop of fluid escaping that I licked slowly, looking him in the eyes.

—You like that, daddy? —I asked, sticking my tongue out so a strand of saliva hung from the tip.

—A lot —he barely managed, head thrown back.

I took him into my mouth little by little, pushing him down my throat until I felt him hit the back and gagged. I pulled off, spat a good amount of saliva onto the head, and used it as lube to jack him with my hand while I sucked his balls, one first, then the other, then both squeezed together inside my mouth. Then I knelt between his legs and played with everything, slowly, alternating hand and mouth, my tongue tracing the vein running up underneath, until he stopped me by grabbing my hair.

—Stop, don’t make me come. I want to be the first to taste you, I want to fuck you.

I got on all fours on the bed, arched my back, and pushed my hips high, showing off my cunt and ass. I ripped off my thong and threw it to the floor. Tomás stared at me for a second, got himself positioned behind me, and ran the tip along my wet lips before driving in all at once, deep to the hilt. I screamed with pleasure. He gripped my hips and started slow, deep, pulling almost all the way out and pushing back in until his balls were buried. 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, every thrust a wet slap of skin against skin.

—That’s it, come on, fuck me hard —I begged, looking over my shoulder, and he obeyed, grabbing my hair and yanking my head back.

More confident now, he brought his thumb to his mouth, wet it well, and started playing elsewhere, in circles around my asshole, testing.

—You want it there? —I asked him.

—I want to be the first in that ass too.

I made sure it was well lubricated with my mouth—I spat on it and worked it with my tongue from the balls to the tip—then got back in position and told him to go in slowly. I spread my ass cheeks with both hands for him. He did it little by little, resting the head on my asshole and pushing, sliding the tip in and out until the ring gave way completely with a burning sting that made me clench my teeth. When he reached the bottom, he pressed himself against me with a long sigh, still, letting me get used to the fullness.

—God, so tight —he groaned, and started moving, slow at first, then firmer, gripping my waist to pump my ass with real hunger.

I slid two fingers into my cunt while he fucked me from behind, and came like that, shaking all over, clenching around his cock with my hole. It didn’t last long; it was his first time like this. He warned me he was about to finish and I turned around quickly, knelt just in time to take him in my mouth, holding his cock with my hand until the last drop. He shot a thick load that filled my tongue, salty and heavy, and another that landed on my cheek. I swallowed it all while looking him in the eyes and licked the tip so nothing was left.

—Best gift in years —he said between laughs, exhausted, lying on his back on the bed.

***

We went out to the living room, where the others were waiting with glasses of whisky. They applauded when they saw us come out and asked Tomás if he liked his gift. He joked that he didn’t feel like getting married anymore. I sat down in the middle of them, naked except for my stockings and heels, and while they talked about their lives and wished the groom luck, hands started searching for me: one on my leg, another on my ass, another pinching a nipple and leaving it hard between his fingers, yet another slipping between my legs and prying my lips open to dig into my cunt.

Esteban asked me for some photos. I agreed and struck a couple of poses for his enjoyment: turned away, showing my ass spread open with both hands; lying on my back with my legs wide apart and two fingers sunk to the knuckles; sucking on my own nipples. Every comment they made got me a little hotter. On all fours, I crawled over to the one holding the phone, pulled down his pants, and found a very big, thick cock, the kind I like, with marked veins and heavy balls.

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

He was so thick it barely fit, my jaw ached, but I tried anyway, licking it all over like an ice cream, running my tongue up and down the shaft, hollowing my cheeks to suck it hard. I spat on it and my hand slid up and down with a wet sound they all liked. While I did that, the others came closer, circling around me, and all of a sudden there were hands everywhere and a court of hard cocks waiting their turn. I started jacking off two at a time, one in each hand, while I kept sucking on the thick one from the phone guy. Someone positioned himself behind me, spread my ass cheeks, and started licking my asshole, his hot tongue probing up and down, and I had to cling to the front man’s legs just to keep from falling from the shaking.

One stood out among them: a tall guy with broad shoulders, cinnamon skin, about thirty-something. He wasn’t the longest, but he was the thickest of them all, so thick I couldn’t wrap my hand around him—the fingers wouldn’t meet—thick as a forearm, with a purple head. This one’s going to split me open, I thought, and I liked the idea more than I expected. My mouth watered just looking at it.

I gave myself over to the task. Some liked to hold my head with both hands and set the pace, fucking my mouth without mercy until my eyes filled with tears and saliva dripped down my chin; others preferred it slow, wanted me to play with my tongue beneath the crown, others wanted it deep, until I choked. Meanwhile, someone had settled underneath, lying on his back between my legs, and started using his tongue on my clit, sucking it hard, sliding two fingers inside me and curling them, making me moan with both hands occupied jacking off cocks and my mouth full. Another focused on my tits, taking them into his mouth and biting them, tugging my nipples until I howled.

Bruno led me to the couch, sat down, and told me to ride him. I gripped his cock with my hand, lined it up with the entrance to my soaked cunt, and lowered myself slowly, feeling him open me up completely. When I had it all inside, I stayed still for a second, rolling my hips, savoring every inch. I started slow, then harder, bouncing on top of him, my tits slapping my face. Bruno grabbed my ass and squeezed it, spread it apart, licking his lips as he watched my cunt swallowing his cock.

—Just as horny as always —he told me in my ear, and bit my earlobe.

Two more came up from the sides to get serviced with my mouth. I alternated between one and the other, spitting on their tips, sucking their balls, while I kept pumping myself on Bruno. We changed positions, partners, in an endless cycle: they put me on my back on the couch with my legs spread as wide as possible while one drilled me from the front and I sucked another upside down, my throat open to swallow his cock whole. I ended up full of two loads of cum: one came inside me and I felt the hot spurts hitting the back of me, and at the same time the one I had in my mouth filled my face with a thick stream that ran down my chin to my tits. Every so often I searched with my eyes for the broad-shouldered one, gauging when my turn would come with him, and he smiled at me calmly, jacking off slowly, waiting.

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

***

My turn came. The others stepped aside and I was left alone in front of him, and he ordered me to get on all fours on the couch. First I asked for my purse and took out the lubricant: I smeared his cock with both hands until not a single inch was dry, sliding up and down the whole shaft, feeling the enormous weight between my fingers, and then I prepared myself, sliding in three well-lubricated fingers until I’d opened enough. He watched me with a patient smile, jacking off slowly.

—This time I’ll let the lubricant slide —he said—. I was going to shove it in dry.

I got nervous. I knew what was coming. He slapped my ass a couple of times with his cock, heavy as a stick, each dull blow making me clench my teeth, before aiming. The first thrust drove me forward under the pressure so much that it slipped out with a sound that drew laughter from the others. I took a breath on the couch, breathing deeply.

—Another position —I suggested.

—No. I want you like this, on all fours and wide open.

I got back on all fours, spread my cunt with both hands, tugging the lips outward, and this time it went in slowly, pushing with one hand on my back so I couldn’t escape. I felt the stretch like a hot burn climbing up my belly. I bit the couch edge while I felt him make his way in, centimeter by centimeter, until he was all the way inside. The others clapped as if they’d won something.

He started slow but deep, feeling how I got used to his thickness. Each thrust stole my breath, each withdrawal made me feel empty for a second before filling me all over again. When he intensified, the pain mixed with pleasure in a way that made me scream like I never had before, an animal scream I couldn’t hold back. Esteban told me to shut up, and in an instant two more were at my sides offering me their mouths. I grabbed one with each hand and took one into my mouth, but the thrusts from behind shook me so hard I could barely close my lips: saliva dripped from me, his cock banged against my face, slipping between my drool. I ended up with my mouth open, letting him hammer it on his own, using my face like it was just another cunt.

With time I got used to it, and the burning turned into a tingling that rose in waves. I felt myself coming again and yelled at him not to stop. My whole body convulsed around him as I came, trembling, clenching that enormous cock so tightly he let out a rough groan. Because I’m short, he lifted me in his arms without pulling out—hoisted me off the couch impaled on him like it was nothing—and carried me to the bed, where he kept going, flipping me onto my back with my legs against his chest so he could sink even deeper. That’s where he really split me open, pulling my legs, slapping my ass hard every so often and leaving the imprint of his fingers. After a long while, the others claimed their share.

—She’s ready —he said, getting up, and came out with a wet sound, leaving me empty and open.

***

What followed was a string of rounds I lost count of. Tomás again, more emboldened this time, fucking me from the side with my leg raised; then another who put me face down and drove into my ass without preamble; then two at once, one underneath with his cock buried in my cunt and another behind forcing his way into my asshole, the first of several double penetrations that night. I felt split down the middle, with the two cocks separated by barely a layer of skin, moving out of sync, and when they found the rhythm I came screaming between them, clenching them with everything I had. They changed places without pulling out all the way, passed me from one hand to another, went in and out, finished in my mouth, on my tits, on my back, in my ass, wherever they landed. I lost count of how many loads I swallowed and how many drenched me. I ended up with glossy, sticky skin, with strands of cum hanging from my chin and nipples.

The thick cock was always the one I enjoyed most: hard, relentless, capable of making me scream and leaving me wanting more. He grabbed me two more times amid the chaos, once in my cunt and once in my ass, and both times he made me come like crazy.

At some point I looked at my phone: it was past eleven. Three hours nonstop. I took a quick shower, letting the hot water rinse the cum from my hair, my tits, my ass, and slid in two fingers to clean myself out, feeling how swollen and open I was. I put on something more comfortable and went back to the living room, where Esteban greeted me delighted.

—You can hold out like few others —he said—. But the night is still young. Stay in your thong; this is just getting started.

I agreed. The party went on: some only drank, others took me to the room one at a time or two at a time. Three more arrived, just in from their trip, and I set the only condition of using condoms because I didn’t have their test results. They didn’t object. I sucked one until he came in my mouth, fucked another on top of him until he finished in two minutes, and let the third open my ass so he could put it in from behind while the first got hard again for me to suck him off.

That’s how the early morning passed, between drinks, laughter, and bodies. The broad-shouldered one came looking for me again when almost everyone was already asleep, waking me with his mouth buried between my legs, sucking my swollen clit, and his hands kneading my tits. Unable to let me rest. He slid it in slowly from the side, holding me from behind, driving his cock to the bottom with a slow, firm rhythm that made me come twice in a row before he finished inside me, filling my cunt with a deep groan against my neck. By then I’d already put on a numbing cream and let him do it, because, I confess, I didn’t want him to stop either.

When I realized what time it was, it was past six in the morning. I ended up exhausted, aching, and marked by hickeys, bites, and slaps, with my cunt and ass burning, but satisfied like I rarely ever was. I asked to be taken home and, as the car started with the sun coming up, I felt the cum still slipping inside my thighs and thought that of all the bets I’d ever lost in my life, none had worked out so much in my favor.