My Virgin Friend

I've known Tom since high school. We used to actually kind of dislike each other but grew closer in the years afterward. Nowadays, we drank and played board games about once a month or so, and him and a couple other friends were over at my place tonight. My girlfriend was out of town for the night, so we stayed up pretty late, each trying to outdo the other in building the longest road in Settlers of Catan. Eventually my other friends gave up, either with the excuse of having work the next morning or just being exhausted.

We continued drinking, and the topic turned to girls.

"How are things between you and your girlfriend?" Tom asked. "Sally?"

"Yeah, her name's Susan" I laughed. "They're good. She's pretty cool. How about you man, how are things in the romance world?"

"I mostly just stay at home and play video games man, or work" he replied. Tom, to be honest, had never had a girlfriend, and I wasn't even sure if he wasn't a virgin.

"Don't you want to meet anyone?"

"Yeah, I've been exercising and stuff, meditating, trying to improve myself. Your turn," he pointed to me, after finishing his turn by adding 2 new road pieces to his road.

Tom did look better these days. A 27-year old bearded landscaper now, he was slightly muscular, with brown tufts of hair and blue eyes. Still, I secretly felt it was somewhat nice of me, a 27-year old medical student do keep up acquaintances with him, who I knew others must call a loser.

"Fuck," he said. "I think you've got this in the bag... I needed the victory points from the longest road.

"Yeah, might be over, man. I'm feeling a bit sleepy too," I glanced over toward my bedroom. "Might tune out."

"Sure," he said. "I should probably head out too."

"There's no way I'm letting you drive this late. You can sleep on the couch."

"You sure?" he asked.

"Yeah, I'll get the blankets out. I'm just gonna smoke a joint before I go to bed too," I said, rising.

We went outside. The marijuana circulating in my head, my eyes were swimming a bit in the dark trees across the street. I could hear what Tom was saying, but only barely.

"...there's a girl I know, I'm her boss, pretty hot, wears these outfits... just so horny these days... aren't you, with Sally gone?"

"Yeah" I said absent-mindedly, then turning to look at him.

His eyes were sparkling in the night in a nice way, and the streetlight shone on his face to highlight the redness of his lips.

"Do you think I'm gay?" he asked suddenly.

I laughed, "Are you?"

"Nah, but I've been having some weird experiences lately."

"You're drunk," I giggled.

"Yeah, let's go inside, I need to sleep.

-

I awoke in the middle of the night, still slightly high to the sensation of someone fingering my ass, almost like a dream. I could feel the prickles of a beard against my butt, as a wet finger felt around half up my anus. My legs were spread, and a pair of hands were gently pulling apart my ass.

"Ungh," I could only moan, my head pressed into my pillow.

As I slowly began to wake up, I suddenly pulled at my hands to discover they were tied to my bedposts. I tried to move my feet then, and they were tied too. I was spread-eagled, unable to escape this wet finger from piercing me at my core.

I struggled, started yelling at my assailant, "What the fuck, man!"

Tom's voice replied, "Don't resist."

He pulled my head back, and stuffed the boxers he had pulled off me while I was sleeping into my mouth. Choked by the hot smell of them, I struggled even harder against the restraints.

It was then, his finger slipped out of my ass, and something new came to press there. I knew what it was. The tip felt heavy, and I puckered my hole completely, pushing my rear end back and forth away from it. In response, he began to spank me relentlessly with hard smacks, till eventually my cowering bum, burning with pain lay still.

I could feel drops of wet lube drop on my ass, and my eyes widened. My first thought was I had no idea how big he was, but before this thought even fully congealed, something was tearing me apart in pain, pushing its way like a wet baseball bat into my still puckered hole which hopelessly resisted, pushing against his tip. But still he pushed, and it hurt so much, like flesh was being torn, that I slipped in my resolve for one moment, loosened my body, and he slid into me, sending waves of fiery sensation throttling through my body as his penis entered me completely, prodding into my rectum, and places of my body I had never felt nerves sending any information from before.

Except that wasn't his whole cock, as with another push, I felt him in my belly, wide and thick, and his cool balls now slackly resting against burning flesh of my perineum. I sobbed into my boxers.

When he pulled out, I felt like a vital organ was being dragged out of me, but then he shoved it back in, again in 2 thrusts so as to fully ensheath himself in me. I tried to focus my attention away from the experience, imagining Tom being led away by the police, me pointing him out in court, Susan suddenly coming home—but oh, he was pounding away at my ass now, and my brain even felt unsafe, the way he was reaching into me. I could smell the sweat dripping off his body onto mine, could hear the sounds of his balls knocking against my own sweat-drenched ass, and his stomach slapping against my butt.

Eventually, he groaned like an animal and emptied himself inside me. My insides filled with warmth, and he slipperily withdrew himself from me. He went outside, closed the door, leaving me lying in a pool of sweat, my muscles impossibly sore and strained from resisting him, and still tied to the bed. My asshole gurgled out some of his cum through the night, and the rest came to rest deep inside me, making me feel like he was still inside me.

-

"Alex, Alex, are you here? I'm home," called Susan.

I had managed to cough out the boxers, and I moaned out, through sobs, "C-c-call the police. I've been r-r-raped by T-t-tom."

I heard her come running. I could imagine when she first saw me, the sight, me stretched out, dried cum covering my ass.

"Oh my god," she screamed. She broke down and came running to me, began untying me, but seemed to struggle with the cords.

"Call the police," I moaned out again.

Turning my head, painfully to the side, to my horror, I saw Tom standing in the doorway, watching us. I couldn't even say anything, my throat was so stuck in horror. He slowly walked up behind her, and slapped her hard on the side of the head. She fell on top of me, and was silent.

Then I could feel her body moving, her clothes behind removed.

"No, no, no—" I began to cry, before another smack sounded.

-

Her body was moving on top of mine. I could hear the sounds of their fuck, his balls slapping against her ass, her quietly moaning. Then he threw her off me. I could see her on the floor, ball-gagged and her arms bound painfully to her legs.

"Clean me off," he said coming to stand beside the bed. "Or I'll hurt her instead".

I shook my head, crying "Why are you doing this?"

He turned and kicked my girlfriend hard in the stomach. She choked out a moan, and her eyes widened. I did as I was told, licking my girlfriend's taste mixed with his stink off his impossibly large cock.

"Make me cum," he commanded.

I sobbed onto his cock, giving it tentative licks.

"In 10 seconds or I'll hurt her."

I took him in my mouth, pressed him as far as I could down into my throat, and he inserted himself deeper. I couldn't breathe, my nose choked with snot from crying and his penis blocking my throat. I almost vomited, but managed to work my tongue around to the underside of his cock, where I began giving desperate licks. As his penis pushed deeper inside me till I was licking his hairy balls, his cum spurted down my throat, stickily sliding into my stomach. When he told me to clean off his cock, I did so in my happy place, licking from base to tip, my throat still clogged with his seed.

-

I lay there for sometime, before he came back into the room. He pulled my bed so that the head of it was facing my girlfriend in the centre of the room. Then he pulled her up, and slipped inside her again to a painful grunt from her. Susan's breasts jiggled in front of my face, her bruised body shaking. I pressed my face down into the bed, trying to cry but I was out of tears.

"Watch, or I'll hurt her."

I couldn't, and heard the sound of slaps and punches. I looked up and into her whimpering eyes. I could see he was inside her ass. Her cunt was openly gaping, her labia hung limply, and cum was still leaking out from deep inside her. I knew she was a virgin there, and that she hated the idea of anal sex. I looked into her wet eyes, and she looked at me with a look of complete blankness, as if the humanity was leaving her as Tom pummelled into her bound and bruised body.

But then, something happened that turned my whole, sweaty body cold. Susan's trembling lips and her red visage, began to move in a direction I couldn't understand. In slow motion, the corners of her mouth turned upwards in a smile, as she looked straight into my eyes. Seeing the look of bewilderment on my face, Tom removed her ball gag, and untied her ropes.

"You stupid slut, the game's up now" he said to her.

"Yes," she moaned, her gaping cunt quaking from the still ongoing thrusts into her rectum, the pink lips of it trembling, and her pussy seeming to gasp as the cock slid in and out of her asshole.

"What... what the fuck is going on," I cried to her.

Her eyes only rolled back as I watched an orgasm creep its way slowly across her body, till liquid poured out of her vagina and her knees shaking, she rolled off his cock. I didn't even know she could squirt was one horrible thought that passed through my brain at that moment.

She squirmed on the floor for awhile, leaking out juices, before coming to. She got up, came over and kissed me on the forehead. Tom came up from behind her, dick smelling like ass sweat, and unloaded streams of wretched smelling cum onto my face, still frozen in shock. As the thick globs of cum dripped down my face, Susan greedily lapped at them, giving me a look as if she was helping, her tongue running along my cheek with a certain vigour.

"I'm sorry babe," she murmured to me. "I'm in love with his cock."

I looked at her, trying to find my girlfriend in those eyes. But they were swimming in ecstasy, her pupils completely dilated, and her eyes didn't hold mine for long, as they soon moved back to Tom's still rigid cock.

She came to my ear to whisper something. She hesitated. An escape plan? An explanation? Even an apology I would take.

"He can cum multiple times," she giggled into my ear.

A that moment, I felt something pressing against my asshole, and she watched my eyes widen and get wet as Tom's cock entered me.

"Who's tighter" she asked him.

"Definitely him, you raunchy whore," he replied.

Susan watched me intently as he moved in and out of me, asking eagerly, "How does it feel? Isn't it amazing?"

My head fell back against the bed. I was in an endless nightmare. After awhile of widening the gap between my cheeks, he groaned and released inside me.

"Don't worry, I still care about you" she whispered to me, then went around behind me, and I felt, to my utter embarrassment, her mouth pressed against my burning asshole, and her wet tongue slip inside me, wet and hungry. She sucked, like she was siphoning gas, the cum out of my heated asshole. I couldn't help but feel cum leaking out of my own cock.

Her mouth barely containing the cum, I watched her saunter off out of the room, her once precious-to-me ass bouncing with a new life.

"I win," Tom winked at me, as he watched her go.