The Roughest Session I Agreed to for Money That Night

It all started with a chat on a Tuesday night. Tomás, my husband, manages my appointments, and I read the conversation over his shoulder while he typed in bed.

—Is Renata available tonight? —the client wrote.

—Yes, she’s here. Two thousand an hour, no tolerance. Whatever you hire, she leaves right after, she has another commitment —Tomás answered.

—The thing is, there’d be four of us. Is that okay?

—Four is three thousand. I’ll bring her and pick her up, so I’ll leave it at that price for you.

—Deal. Like last time, right? No agreed limits.

—Like last time. You know the conditions —Tomás closed, and set the phone on the nightstand.

My stomach dropped. Hugo was the man who had handled me hardest ever, and now there would be four. But I already had experience in this; I thought I could handle it, and the pay for two or three hours was worth it. Besides, in a week I was going to Punta Cana with my friends, and that trip wasn’t going to pay for itself.

***

For those reading me for the first time: I prefer to tell what happens to me without embellishment, so don’t expect polished prose. I live up north, I’m married, around thirty. I’m light-brown, slim, with shoulders a little broader than my frame, natural tits and a good hip line that the gym and a little tweaking rounded out without overdoing it. I take care of myself, I shave my pussy and ass completely smooth, and I look good without stopping looking real. Occupational hazards.

For that night I chose a pair of tight black vinyl pants, so fitted that underneath you could see white panties with ruffles and a little purple bow in front. On top, a thin beige camisole with straps and a V-neck that let the lace of my bra show through. Stiletto heels, dark makeup so my face could better endure the treatment that was surely waiting for me.

Tomás checked that I had the plug with me, as they had asked for. I had played forgetful and he sent me to put it in. I lubed it well and slowly pushed it into my ass, feeling the ring open until it swallowed it whole. The metal base stayed cold between my cheeks and the fullness made me squeeze my thighs with every step.

—You’re going to wait for me outside, right? —I asked once we were in the car—. I’m kind of scared. I feel like it’s going to be worse than last time.

—I’ll be right there. I already told them the conditions are the same. Besides, next week you’re going on a trip, so don’t start complaining —he answered, and squeezed my knee.

—I deserve it. I’ve worked a lot.

My parents think I stopped working and suspect how I cover my luxuries, but I’d make something up. It started as one of Tomás’s fantasies a couple of years ago; he liked it, I liked it even more, and it ended up becoming my way of life.

***

We arrived at the Imperial motel. Tomás gave the room number at the booth, parked, and we got out. The door opened and there was Hugo, exactly as I remembered him. He exchanged a curt greeting with my husband, paid for the first hour, and said that if we went over, he’d give me the rest directly. He said goodbye to Tomás and grabbed my arm without even greeting me, just scanning me from head to toe.

Inside were three other men. To keep things straight, I’ll call them this: Hugo, the skinny one, the old one, and the big one. The skinny one looked like Hugo but younger; the old one also had a certain family resemblance, older and with a heavy gaze; the big one was broad-shouldered and dressed like a rich kid. They smelled of cigarettes and beer, there was banda music playing low, the lights were dim. They’d been drinking for a while at one of their houses and, already drunk, decided to hire someone until they landed on me.

They sat me on the couch and they settled around me. They turned the TV down. They offered me a drink and a cigarette, which I declined with a smile. They were curious, like they’d been waiting a while to ask me questions.

—Is everything Hugo says about last time true? —the big one blurted out, the most interested.

I barely nodded. Hugo took out his phone and showed them a video he had recorded of me months earlier. I heard myself saying a bunch of nonsense while all four watched the screen more intently than they watched me. I laughed at how ridiculous I sounded, hearing my own voice moaning, “put your whole dick in me, give me more load,” while in the video my mouth was dripping with semen.

—And why are you into this if you’re married? —the skinny one asked when Hugo put the phone away.

—It started as a game with my husband. He liked it, I liked it even more, business started going well for me and I’m still here. I quit my job and now I have more time, honestly.

—And you can take what they do to you? —the big one insisted.

—It’s only for a while. It’s not common for them to ask me for what you want, but if you pay, I do it.

—And what do you like? —Hugo asked, leaning back.

—Being handled rough. I prefer it in my ass at the end, that way it hurts less because I’m already warmed up. I like being held by the hair, having a cock shoved in my mouth without warning, feeling the man is in charge. Sometimes you don’t even know what you want.

—Insulting her, spitting in her face, fucking her even if she screams —Hugo cut in, amused.

—Well… that too —I admitted, and it made me laugh how naturally they dealt with each other.

—Can we record you? —the skinny one asked.

—Sure. Though with a tip I cooperate more —I joked.

—Aren’t you scared we might go too far with you? —the old one said with a crooked smile—. We could rough you up here and nobody would know.

—I know you won’t do that. Behave —I answered, more confident than I felt.

The old one stood up and planted himself in front of me.

—Let’s see what’s off-limits.

—Marks where they can be seen. And especially not on the face.

—Not on the face, huh? —he repeated mockingly, and before he finished he slapped me so hard it snapped my face to the side.

It really hurt. I clenched my teeth and swallowed my anger. A silence fell.

—Oh, so it is allowed, little bitch —he smiled mockingly.

I only nodded. No use fighting one of them, much less all four. That was when I understood this wasn’t a game: they were really going to put me to work, and I was trapped and vulnerable.

***

—Let’s see the prize you brought us, this guy says —ordered the old one, snapping his fingers.

I stood up in front of them. Four fixed stares, in complete silence. I slowly pulled down my pants, left them bunched around my ankles, and bending over, offered them my ass. Two hands took advantage of it to touch me, squeeze my cheeks and slap them, the sound cracking dryly in the room. One finger slipped past the edge of my panties and brushed my already wet pussy, drawing a gasp from me I couldn’t hide.

—The bitch got hotter —Hugo commented, and I’m not going to lie, it turned me on.

I did the same with the panties and got myself onto the couch on all fours, elbows on the backrest, knees on the seat, wide open. The groping didn’t take long: I felt tugging on the plug, pulling it out a couple of inches and shoving it back in with a jerk, while another hand spread my pussy lips and worked me with two fingers. I was soaked. Their fingers went in and out with a wet sound that made the others laugh.

—Look how wet this whore is, she’s dripping already —the big one said, and stuck a third finger in me, curling them inside until I moaned.

The old one came up beside me, already with his dick out. He had it thick, veiny, with a reddened head pointing at my face.

—I saw how you suck cock. I want you to do better.

I opened my mouth and he shoved it in hard to the back. He gave me no mercy; he controlled everything, driving my head against his pelvis, fucking my mouth as if it were a pussy. He wasn’t enormous, but he filled me well and the head hit my uvula, making me gag when he forced too much. Tears were soon streaming down my cheeks, mixing with the spit already dripping from my chin. Another man spread my ass cheeks and played with the plug, pulling it all the way out to run his tongue over my open hole and then shoving it back in with a hard thrust. The others were undressing around me, pulling out their cocks and jerking off slowly while they waited their turn.

Hugo took me by the ears and forced the rhythm, making me swallow every inch. My mouth started making that rough, throat-filled sound, saliva running until it dripped between my tits.

—All she can say is “bua, bua” —he mocked, and the others laughed.

He pulled his dick out of my mouth and slapped my cheeks with it, leaving threads of spit and precum stuck to my face. He grabbed my hair, forced my mouth open, and spat inside. I swallowed without thinking.

They sat me on the floor, finished stripping me, and left me only my heels. With the back of my head against the couch, mouth pointed upward, I took the skinny one standing up, letting his weight drop until he sank his cock into my throat. Every thrust cut off my air and I felt his balls knocking against my nose. The old one took the chance to sit on the couch behind me, grab my tits from behind, and twist my nipples until I screamed with my mouth full. By then my face was a mess: mascara running in two black tracks, red eyes, lipstick smeared all over my jaw, panting for air every time the skinny one gave me a break. And that was barely the beginning.

***

The skinny one filmed me in close-up while he kept fucking me and directing me like I was in a porn video. The old one, meanwhile, dug into my story with cruelty front and center.

—Who knows you’re into this?

—My husband. An uncle and a couple of friends —I answered in a broken voice, as soon as the skinny one pulled his cock out to let me speak.

—The uncle has probably already fucked you.

I nodded and got another slap in reply.

—And your parents, do they know?

—No. They’d be ashamed.

—They won’t even want to talk to you —Hugo cut in, holding my hair to spit right in my face and slap me again—. You’re still the same piece of trash as last time.

I started sobbing. Two of them pretended to comfort me and hugged me while still groping me, one with fingers sunk into my pussy and the other squeezing my tits and pulling my nipples. I was furious and, at the same time, excited in a way I didn’t fully understand: I was so wet it was running down the insides of my thighs.

The skinny one lifted me and sat me on top of him on the couch, my back pressed against his chest, legs spread wide open, supported from under my knees. He yanked my head back by the hair, I felt the pull in my neck, and he speared me in one hard thrust. He had a good size, long and curved, and even though I was wet the stretch made me scream. He started bouncing me up and down on his dick with his hands on my thighs, impaling me to the hilt. The big one came up in front, yanked the plug out in one pull —the empty feeling made my eyes shut— and buried his cock in my stretched ass, bracing himself on my knees to give me thrust after thrust. A brutal double penetration. Despite everything, I was burning. It was exactly the kind of surrender I like, two cocks owning my two holes at once, feeling them rub against each other separated only by a wall of flesh. The room filled with moans, my own “yeah, yes, fuck me, like that, harder” mixed with their grunts and the wet slapping of two cocks splitting me open.

—Just look how tight the whore is, she’s about to come —the skinny one panted from below, biting my neck.

—She’s hot as hell both front and back —the big one replied, and stuck a finger in my mouth to pull at my cheek, warping my face while he kept fucking my ass.

The old one took out a marker and wrote something on my forehead that I would later read in the mirror. While they rocked me on their cocks, they threw questions at me and I only nodded to each insult, lost between humiliation and the pounding.

—Then I’ll do whatever the fuck I want to you, nobody gives a shit about you anyway —the old one finished, and shoved his dick into my mouth sideways, making me suck while the other two kept fucking me. Three holes occupied at once. A muffled moan escaped me and the skinny one took advantage, thrusting faster from below and wrenching spasms out of me.

I nodded again, mouth full.

***

They pulled me out between the three of them, legs trembling and holes open, and took me to the bed. Each took one of my limbs, face up, and covered my face with a pillow so I couldn’t see. Someone shoved a long vibrating toy straight into my pussy, its tip pressed against my G-spot, controlled remotely with a little remote. Another clipped weighted clamps onto my nipples —the metal bite made me shriek— and a third lashed the skin of my belly, thighs, and tits with a soft strap whip that snapped as it hit and left burning red lines behind.

—You like that, little slut?

—Yes —I panted, barely understandable under the pillow—. Give me more, don’t stop.

They turned the vibration up to max and my body began to shake in small convulsions. The nipple weights swayed with each spasm, tugging at me, and the vibrator was sunk so deep I could feel the motor thudding against my pubic bone. I was squirting in streams; I felt the liquid running down my perineum and soaking my ass and the sheet.

—Look how this dirty girl is leaking, she’s making a puddle —Hugo remarked.

—Say what you are —Hugo ordered, yanking the pillow away to look at my face.

—I’m your whore, I’m worth nothing, don’t stop fucking me —I repeated without thinking, in a hoarse voice—. Put it all in me, use me, spit on me, whatever you want.

—This old lady is crazy —the skinny one laughed.

—I already told you, go as far as you want —Hugo answered, and without taking the vibrator out he mounted me, sinking his cock into my mouth to the throat while the toy kept drilling my pussy.

The whip kept crossing my tits, the vibrator wouldn’t stop, Hugo’s cock blocked my air, and I couldn’t take it anymore. I came in a fierce orgasm nobody could hold back; I screamed with his cock inside me, the air went out of me, my body arched back, my heels digging into the sheet while I heard their laughter all around. I felt my pussy clenching brutally around the toy, squeezing it hard, and a warm rush ran down my thighs. Hugo pulled his cock out and finished spitting in my face while I trembled.

—The dirty girl came, she pissed herself too —the old one said, squeezing a clamp that was already killing me.

***

When I caught my breath, the skinny one ordered me to wait for them in the bathroom, squatting down. I went in on all fours, with the word written on my face and the nipple clamps still hanging from me, while they gave my ass a farewell slap. There, alone for a moment, I tore off the clamps —the sharp pain when blood rushed back to my nipples made me fold over— and became aware of the burning on my face, my ass, my cunt; my pussy was throbbing, my ass stayed open, I could feel everything swollen. I love being humiliated. If I ever quit this, it won’t be anytime soon.

They came in one by one. The big one sat me on the toilet and fucked me hard from above, forcing me to bounce on his cock while he squeezed my throat with one hand, barely letting me breathe. He finished in my pussy with a roar and left me dripping warm semen between my legs when he stood up. The old one came in with a cigarette, made me open my mouth, and let the ash fall inside; as soon as he pulled away, I spat it out. Then he grabbed my hair, put me on my knees, and shoved his cock into my mouth to the hilt, fucking my throat with both hands on my nape. He came without warning, unloading a thick stream onto my tongue that made me cough, and what little spilled from the corner of my mouth he scooped up with two fingers and put back into my mouth so I’d swallow it.

—Every last drop inside, little bitch.

The skinny one was next. He set me on my feet, bent me over the sink in front of the mirror —so I could see my marked face, the mascara smeared, the word written on my forehead— and rammed it into my ass in one thrust. I screamed. He was long and the burn brought fresh tears. He fucked my ass without mercy, gripping my hips, forcing me to look at myself in the reflection while he pounded me. With his other hand he pressed my neck against the fogged glass. He came inside my ass with a grunt, and I felt the hot stream flooding me from within. When he pulled out, he slapped my ass cheek and made me spread my hole with my fingers to film how his cum, mixed with the plug’s after hours, dribbled out of me.

—Just look at that, what a waste —he laughed, and stuck two fingers in to scoop up his own semen and smear it into my mouth.

Each one finished however he wanted, and between one and the next they cleaned me up with insults and hands in my hair, that strange mix of contempt and care that gets me every time.

The last was Hugo. He crouched down to my level and looked at me for a long while, in silence, with his hard cock in his hand.

—You’re disgusting. Take a shower, because I’m still left —he said.

I turned on the shower and the warm water eased me. I washed off the night’s sweat, the semen dripping down my thighs and ass, with Hugo watching me from the doorway, jerking off slowly. I was wrecked: everything hurt, my shoulder, my lower back, the irritated skin on my thighs, my nipples throbbing. He pointed at the toilet and I knew what he wanted. I gathered myself, bent over the lid on my own, my hands on the tank and my ass lifted toward him. He spat between my cheeks, guided himself with his hand, and shoved his cock into my ass with a dry thrust. I felt how the flesh, already destroyed by the first three, opened with no resistance. I would lift my head to breathe and he’d push it back down by pulling my hair. Curiously, with me he was the least rough. He fucked me at an even pace, grunting softly, until he came and left one last warm load inside my ass. He came out slowly, giving my ass a careless slap, and wiped his dick on my hip.

—What a good time one has with you —he said, now composed again.

***

I came out of the bathroom with the four of them still dripping inside my thighs. The other three were already dressed, watching TV, not paying me any attention. I couldn’t find my clothes, only my purse and my phone.

—My clothes, Hugo —I asked—. How are you going to take me out like this?

—Just get the hell out —he answered, and showed me the message he had sent Tomás: “come get her, we’re done.”

The old one appeared with a dog leash. Between the four of them they took me down to the garage and chained me to the stair railing with a padlock, the key out of my reach. Tomás would have to come in for me. They left me naked on the step, wet, in heels, with the leash around my neck, and that did piss me off: they had crossed the line.

When my husband arrived and saw me, he went for a tool from the truck and slashed one of their tires. I’m not going to lie, it made me happy, even though the fucking they gave me was something nobody could take back.

—Maybe think twice before giving them service again —he complained while covering me with his jacket—. They treated me badly and you still charged too little.

—Did they pay you for the extra hour?

—Yeah, I’ve got it here. But you should’ve seen what they did to me.

—I saw it, love —he replied, starting the car—. They sent me the videos.