first anal

I owed Jimmy money. I won’t get into why, or how much — it’s enough to say that I owed him, and there was no way I could pay it back. When he called I had no choice but to answer the phone.

“Well?” he asked. No preliminaries.

“I don’t have it.”

“Big surprise.”

“I need more time. Please.”

“I don’t think so.”

A frisson of fear rippled through me, and I felt my gut clench. “So what’s going to happen?”

“We’re going to have to work something out.”

“What do you mean?”

“You can pay it off in trade.”

“To you?”

His barking laugh reached my ear over the line. “You got a year?”

“Okay, so what then?”

“One night.”

“One night of what?”

“Of anything. After that, you’re free to go. You never see me again.”

It seemed too good to be true. “You won’t hurt me?”

“Well, not intentionally.”

I bit my lip and took a deep breath. “Alright. I’ll do it.”

He gave me a time and address and hung up.


He answered the door himself. It was your standard mid-rate motel room, located at the end of a long row and no doubt intentionally chosen for its remoteness from the rental office.

“Take your clothes off in the bathroom and leave your bag and clothes there, then come back out.”

I silently obeyed, sliding my skirt down to the white tile floor and unbuttoning my blouse with trembling hands. Naked, I caught my own eye in the mirror. A skittish, nervous woman with skin drawn tight in fear, face pale beneath the fluorescent lights. When I came out of the bathroom my hands came up to cover my breasts, flesh goose-pimpled in anticipation of Jimmy’s eyes upon me. He didn’t say a word, merely continued uncoiling the piece of rope that was draped over his thick forearm.

“Have a seat on the bed,” he said at last, barely glancing at me. I was so scared of what was going to happen to me that my stomach ached. The roughened fabric of the motel bedspread was cool against my bare ass and the lips of my pussy, and I pressed my knees tightly together and put my feet flat on the floor.

“Lie back.”

I did so, feeling my toes come up off the carpet.

“Knees up. Grab your ankles.”

I realized my eyes were closed. Whatever he was going to do to me, I didn’t want to see him do it.

“For God’s sake, relax.”

I opened my eyes, and saw him make a loop of rope. With deft movements he bound the length of my forearms alongside my calves.

“You can let go now, that should hold you.”

With a swift motion he leaned over and took hold of me, lifting my entire body as though I weighed nothing. He flipped me over onto my front, arranging me like a tripod with my knees spread wide and my ass in the air. My hair fell over my face, which was smashed down against the scratchy bedspread. A moment later one of the pillows from the bed was pushed beneath my head, relieving some of the pressure on my neck. With a little bit of wiggling I managed to put the pillow beneath my shoulders, shifting the weight of my upper body onto them. My face was still flattened against the bed, but at least my neck wasn’t holding my entire body up.

I felt a touch at my feet and jumped, terrified. Jimmy was pulling me back by my ankles, arranging me to his liking at the edge of the bed. I was horribly exposed, my bare ass open to the room and my hands bound to my ankles.

-Oh God, oh God….what now?- There was a sound of movement, and Jimmy sat down in the stuffed chair beside the bed. He reached over and brushed the hair out of my face.

“What are you going to do to me?” I managed, my voice rasping in my throat.

“I’m not going to do anything to you.”

There was a tap on the door and he stood, moving out of my view.

“Got the cash?”

“Right here.”

“Go ahead, you’re the first.”

“Aw, fuck yeah.”

The sound of a belt buckle being undone, then the unzipping of a fly. -Oh God, oh shit, fucking shit!- my brain screamed. I could scarcely move against my bindings, but every muscle in my body was tensed and quivering like plucked strings.

“We bagging tonight?”

Jimmy must have shrugged, because I heard the sound of an anticipatory breath being sucked in through the stranger’s clenched teeth.

I nearly jumped through the ceiling when he put his hand on my ass. “Whoa there,” he said, taking one cheek and giving it a little slap. He trailed a finger down my crack, running it lightly across my asshole to graze the cleft between my labia. A second finger joined the first, pushing apart the folds and insinuating themselves into my pussy. The roughened fingertips explored my hole, then retreated. He spit into his hand and drew the warm, slick fluid over my mound from top to bottom.

“Ready, baby?” he asked. Without pausing for an answer he moved against me, pressing the head of his cock against my cunt. I squeezed my eyes shut as he slid his length into me, pushing hard against the dry walls of my hole.

“Shit, that is tight,” he moaned, drawing back for another thrust. As he pushed his cock home he wrapped his hands around my hips, pulling my ass up against him and sinking his shaft in until I felt his balls slap against my pussy. I hadn’t been ready for him at all; my dry cunt was pulled back and forth with each thrust, pulling the flesh in and out as he moved his cock along the narrow passage. I must have gotten wet — maybe it was self defense — because within a few moments he was gliding in and out, hard cock reaching new depths every time he pushed into me.

“I knew you’d like it, baby,” he groaned. His hands grasped my waist, shoving my ass back onto him with each thrust. Every time his cock hit home I felt it deep in my abdomen, as though I were being stabbed. It was a dull, repetitive ache. -I’m being fucked by a stranger.- My mind reeled. -He has his cock in me. His cock is inside me.-

I could feel my lower limbs going numb as he fucked and fucked, my hands tied at my ankles and my elbows at my knees. The scratchy bedspread was burning my knees where they were pressed hard against it, rubbing against the fabric with every movement. Time seemed to stand still as I rocked back and forth on his cock, up and down, in and out, in and out. And then he grabbed me tight, fucked me fast, and I felt his balls against my pussy as they spasmed, shooting his load deep inside me.

“Fuuuuck,” he moaned, body shaking.

He pulled his softening penis out, and from the corner of my eye I could see drops of white cum spilling out of my cunt and onto the drab, flowered coverlet, beading on top of the fabric then slowly sinking through the weave.

Another knock on the door.

“Just in time,” Jimmy said to the newcomer. “Go for it.”

Again the clink of a belt buckle coming undone, the sound of a zipper coming down. Another cock head was drawn up and down my pussy lips, searching for my opening.

“Thanks for lubing her up, Joe.” A chorus of laughter.

The head of the newcomer’s cock began to slide deeper, teasing against my clit and then dipping briefly into my cunt. It came out again with a sucking pop, then pushed back inside. After a couple of test thrusts, he pushed it all the way in with a groan.


This one put his hands on the tops of my thighs, lifting my ass and tilting it up towards him. He pushed me back hard against his pelvis with every thrust. His cock is different from the last one, I thought. Every time he pushed into me I felt the head of his cock drag along the back of my cunt, rubbing at the tender flesh that separated my pussy from my ass. His ballsack hung lower, too, smacking wetly against my mound.

“That’s it baby, that’s it baby,” he said, increasing his pace. It became a mantra as he wound up, balls pulling up against him as he got ready to come. When he finally did he came hard, fucking me so fast I thought he’d fuck me raw. I felt the cum this time too, a hot jet deep inside me. As he pulled his cock out a rivulet of cum made its way up my stomach, clinging to my belly as it ran downhill towards my breasts.

My breasts. As I relaxed into my pose, ass high in the air, my shoulders sagged until the tips of my nipples just grazed the rough surface of the bedspread. When the anonymous man let go of my thighs my nipples swung down, making contact with the bed and sending a jab of shooting pleasure directly to my brain. -Don’t enjoy this,- I begged myself. -Don’t get turned on. Not now.-

I barely had time to think about it before another pair of hands grabbed me, pushing down on the small of my back to arch my ass even higher. My breasts pushed down against the bed, rubbing back and forth with every movement from behind. Another cock head, pushing at the opening to my cunt. When he pushed himself in I almost screamed. The cock was so big I felt like I was being torn in two. Pain shot up from my pussy, burning and stinging like nothing I’d ever felt. I gasped aloud.

“I thought so,” came a deep voice from behind me. “I wish I could stick around to see you try to walk tomorrow.”

I made some inarticulate sound and bit my lip, squeezing my eyes shut and resisting the urge to get away from him. All I could do was clench my ass cheeks together in a vain effort to keep him from hitting me quite so hard, quite so deep. The enormous cock pulled all the way out, and I began to breathe — until it slid all the way in again. I had never felt so full, so penetrated. I thought he’d turn me inside out with that enormous fucking cock. I sucked my breath in through my teeth, fighting back the pain.

One broad hand spanned the small of my back, exerting constant downward pressure and crushing my breasts flat. The buds of my nipples rolled back and forth against the coverlet, dragging ceaselessly along until I thought I could take no more. Then the discomfort transformed into ecstasy, my breasts heaving as my breath quickened.

“Holy shit, you’re gonna get her off,” came another, unfamiliar voice from behind me.

-Don’t cum. Don’t cum.- I fought against the urge, concentrating on the pain that was splitting my pussy instead. I won out; the monster cock spilled its load deep inside me, and when he took it out of my cunt I felt almost bereft to lose its unbelievable girth, felt like my pussy must be yawning wide open behind it. More cum dribbled out, dropping onto the bedspread and running up my belly in a glistening, exploratory finger.

“Give her a minute,” came Jimmy’s voice. I struggled to catch my breath, and lay panting against the mattress.

“Okay?” came another voice.


A warm touch on my ass. Fingers spread across one cheek, leaving the thumb to nestle along the crack. Then he moved the entire hand downward, cupping the weight of my ass and drawing the pad of his thumb over the pucker of my asshole. I felt it clench at his touch, winking and pursing as it instinctively tightened against invasion. The thumb went on, rubbing a line between the lips of my pussy all the way to my clit, where it drew a lazy circle around the nub of sensitive flesh.

“He almost had you there, didn’t he?” came the voice. I closed my eyes and kept my mouth shut. His other hand brushed the hair back out of my face, although I still couldn’t see him from the angle my head was smashed against the bed. He played with my clit a little, running his fingers lightly over it and slicking it with the other mens’ cum. My breath hitched in my throat.

Then his fingers moved to the opening of my pussy, teasing me by running them around the edge of the hole. He put both his thumbs in and stroked the inner walls, prompting me to clench my muscles against his digits. They pulled out, dripping with semen, and I felt the head of his cock against my opening.

As he slid in I sighed in palpable relief, realizing that while he wasn’t small, he was by no means as large as the cock I’d just taken. I relaxed, letting him fuck me just how he wanted, which was slow and deep. He caressed my ass as he did it, both hands sliding gently over the rounded flesh. Then that thumb ran down my crack again, coming to rest against my asshole and staying there, exerting just the slightest pressure against the puckered opening. I clenched up.

The thumb rested there innocently, however, and he kept fucking. Slowly I felt myself opening to him, the sphincter relaxing beneath his touch. The gentle digit rubbed ever so slightly back and forth over the tender pucker, and to my shock it felt incredible. The tip of his thumb began to slide up and down against my asshole, then subtly dipped in and out in time with his fucking. Soon his well-lubed digit was well inside, and I felt him slip it past the ring of muscle at my opening. I squeezed my ass shut against his thumb, and heard him sigh his approval as he fucked, beginning to speed up. His fingers spread across my ass cheek, and his thumb slid in and out of my ass with every thrust of his cock. The thumb curled, hooking itself against the ring of muscle and anchoring itself in my asshole. He twisted it around, sweeping the delicate flesh on the inside of my rectum. I came.

-Fuck.- I came hard. My pussy clenched tight around his cock in spasming waves, and three mens’ cum oozed out of my pussy to drip off his ballsack. I gasped for air, seeing stars as I reached the peak of my orgasm, and felt his thumb dig deeper into my ass to caress his own cock through the fleshy wall that separated the passages. -Oh, fuck! Oh, fuck!- I couldn’t stop coming. I felt as though my body would fly apart, leaving nothing behind.

A moment later he came too, spilling himself inside my cunt. His thumb inside my ass rubbed hard, pushing him even further as he milked the cum out of his cock. When he slipped his finger out of my ass I felt empty, the ring of muscle seizing uselessly against the cold air of the room. He pulled out.

“Well, Jimmy?” came another voice. “Can I change your mind with a little extra?”

I couldn’t hear if Jimmy replied. Blood was still rushing in my ears. I felt pressure against my asshole, and for a moment wondered if he was going to try to make me come again. Seconds later I realized it was a cock, pressed snugly against the opening of my ass. I tried to close my legs, but they were propped open too solidly for me to shift them. I whimpered as the head of the cock pushed insistently against my ass.

A hand came around to stroke my tingling clit, and for a moment I forgot the cock that was pressing against me — in that moment, he pushed the head in. I felt my ass clench tight around him, virgin flesh burning in pain. He stopped with only the head inside, and rocked back and forth with infinitesimal motions, until to my surprise I felt his balls pressed up against the mouth of my cunt. I blinked back tears — my ass stung like nothing I’d ever felt — but he paused and rubbed my clit again until I felt myself relaxing back onto his cock. Soon all I felt was the unreal fullness of his rod up my ass, filling me in a way I’d never known. He pulled back, the flesh of his member caressing slowly against the inside of my rectum. I felt the head leave me, and my ass closed tight again before it was forced to give way to another assault. I squeezed my eyes shut and felt myself tensing up, leaning forward in an attempt to stop him from pushing himself home. Again, his fingers on my clit. Balls slapping against my pussy lips. His pelvic bone coming up hard against my ass cheeks as he invaded my ass as far as he could go.

After a few more long, slow penetrative motions he stopped, his cock buried to the hilt in me. I sucked in a deep breath, taking advantage of the momentary reprieve. Then he put both hands around my waist, long fingers nearly meeting around the narrowest point of my torso. He grabbed me solidly with both hands, and then he pulled back and began to fuck me as hard as he could.

A kind of scream tore silently through my brain as I took the brutal pounding, my entire body wracked with the force of his possession. I felt my cheek scrape roughly against the bedspread, tearing at the delicate flesh. My nipples dragged back and forth across the coarse polyester until I thought they would bleed. After only a few such violent plunges my asshole crossed from excruciating pain to a kind of throbbing numbness, and I dreaded to think of the damage he might be wreaking back there. My hair flew into my eyes and mouth, sticking in saliva-soaked strands to my tongue and lips. I bit at it, feeling the grit of it between my teeth as he fucked the living daylights out of me.

I scarcely registered when he came, only noticing that when he pulled out I felt like an inside-out gym sock, hollow and filthy. When I opened one hesitant eye and looked past my hanging breast I saw a trickle of pink join the rivulet of cum that was crusting in layers on my belly.

“Worth the extra,” the voice said to Jimmy, and I heard the slap of cash on the table.

“Who’s next?” came Jimmy’s deep voice.

They fucked me. I don’t know how many. They fucked me, one by one, each sliding into me through the lube of each others’ sticky cum. Drops of their sweat fell onto the small of my back and traced a wet trail down my flesh to nestle between my anguished shoulder blades. My mouth was pressed into a puddle of drool that soaked the flowered coverlet beneath my head. My knees went completely numb, and my hands tingled with tiny pinpricks where they were bound to my ankles.

With each successive fucking I felt myself floating farther and farther away from the misused, tortured body in which I existed. I thought of other things while man after man fucked my cunt raw. A few tried my asshole, ramming their cocks deep into the forbidden flesh until they shuddered their orgasm and spurted hot cum, one on top of another, until both my holes were filled to the brim. Cum was everywhere; it gave way to each new cock with a sickening sound deep in my body, then welled out of the confines of my orifices to smear across the lips of my pussy, drip hesitantly off of my clit or run seeking down my belly to the cleft between my dangling breasts. With each thrust I felt the crusted semen crack and reform anew on the canvas of my flesh, a shattered mosaic of the leavings of men.

It seemed like hours had passed before the door stopped swinging, the men stopped coming. From outside the fluorescent glow of the porch lamp fought its way through the heavy drawn curtains, and the buzz of moths and whine of cicadas signaled the depth of the night.

Jimmy was sitting in the chair beside the bed. He was counting money, stacking bills neatly on the faux-wood table beside him. I watched his methodical movements as though hypnotized, not caring who I was or what happened to me next.

-Jimmy’s going to fuck me.-

The thought appeared suddenly, seemingly from nowhere. At once something welled inside me, and after all I’d been through my psyche broke; if Jimmy fucked me now, I’d lose it. Not one more. Not -one- more.

Jimmy stood up, and I shut my eyes tight. I felt the heat of his body as he bent over me, his chest pressing tight against my aching back. He reached back, fumbling at his pants. A jingle of metal against metal. He’s going to fuck me, and there’s nothing I can do about it. I wondered if he’d fuck my ass or my pussy — or both.

I collapsed like a rag doll onto the bed. The ropes had been neatly severed and there was Jimmy, utility knife in hand, tugging at my bonds. My tormented body sagged weakly, unaccustomed to liberty. Air forced its way out of my lungs savagely as my ribs hit the mattress.

“Take a shower,” he said, tossing a towel over me. Joints popping with every movement, I stood up. When my knees gave way beneath me he made no move to assist me, simply stepping aside as I steadied myself with a hand splayed across the sopping mattress.

In the bathroom I felt at my face, noted the subtle swelling and deep creases on the side where my head had pressed into the bed. One eye was nearly swollen shut. The pink of my areolas was marred by angry red burns where the coverlet had scratched deep into the tender skin. My knees were oozing crimson blood, which joined the trickling stream of red-white fluid dripping from my crotch.

May 2018
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