r/gonewildstories • u/primed_anticipation • 18h ago
Cheating Fucking the cute hipster chick that wandered into my room after the huge party I threw [MF] NSFW
This took place back in the good ol’ days of my mid-20s. The world has changed a lot since then, and so have I; the me in this story is reckless and immature, and I don’t condone all of his behavior. Nevertheless, I have come to terms with it as an especially hot life lesson.
I've always been involved with my town’s local music scene, and one year it occurred to me that the street I lived on had enough bars and punk houses to throw an absolute banger of a block party. It took a lot of work to get off the ground, from booking all of the bands to getting the venues show-ready and on the same page. Word spread during the planning and promotion, and community hype seemed pretty high as party day approached. It took little effort to find a good volunteer crew from a simple blast of my socials.
One of those volunteers was Molly. She’s someone I knew vaguely from bumping into at shows, and whom I'd seen in the crowd at some of my band’s own. I never caught her age, but she seemed to be a little younger than me, maybe 22 at the time, and quite petite at about 5' 1. She ticked a lot of boxes for the hipster starter pack: a new hair color every other week; messy bangs; big, round, brown glasses that framed her big, round, brown eyes; and stick-and-poke tattoos all over her body that alluded to her esoteric tastes. She was a collage artist, and I always enjoyed seeing the striking fliers she made for shows around town.
I remembered seeing on social media that she had moved out-of-state with her boyfriend a few months ago, so I certainly wasn’t expecting to hear from her. She replied that she was back in town that weekend, thought it sounded fun and wanted to help. I gave her a shift at a ticket booth and didn't think much more of it.
The day of the party was a blur: exhausting, stressful, and exhilarating. The bands were all on point, all the venues were packed and the streets were flowing with beer and late-summer revelry. Everything was running exactly to schedule, and everything was going at best-case scenario. Even still, the sheer volume of people I had to communicate with to keep the party going kept me from fully being able to join it.
I didn’t see much of Molly, as I was darting from stage to stage all night, though she certainly caught my eye whenever she was nearby. She had a kind of a French thing going on. A red beret crowned her jet black, ponytailed hair. She matched it with a rouge lipstick that highlighted her full, pouting lips. Thigh-high socks covered most of her legs, but left a sexy band of peach-toned skin for me to admire below her short plaid skirt. Perhaps the most French part of her ensemble was the lack of bra. Her small, perky tits looked amazing against the tight horizontal black-and-white stripes of her shirt, with just a hint of nipple poking through.
Despite the fact that I could go into a paragraph of detail about how hot she looked, I was so focused on keeping operations smooth that I remained completely professional with her, and our interactions were limited to a boss/worker dynamic. She only worked the first half of the party, her relief replacing her sometime while I was away so she could enjoy the headliners and catch up with friends.
I also didn’t see much of Helen that night, though I wasn’t expecting to. We had been dating for two years, and with hindsight, the relationship had clearly already run its course but we were both too cowardly to call things off. We argued frequently, only occasionally enjoyed each other’s company, and worst of all, had infrequent and mediocre sex. Planning this party had only further driven a wedge between us. Her support was fickle and my incessant talking about it drained her. She left early, telling me she had a migraine and wishing the best of luck to me. I’d say I was disappointed had I expected more, but ultimately I wasn’t going to let her keep me from enjoying my night.
As the final bands were wrapping up, I began the all-important task of collecting the door money from the venues and kudos from my peers. There was way more of both than I was prepared for, but luckily my inflated ego buoyed the anxiety I felt walking around with thousands of dollars in my bag.
I finished the rounds at Pisshole, a large punk house that I had a room in and had served as one of the venues for the night. My housemates did a great job at directing everyone to the afterparty, so the place was totally emptied out. I went to my room, sat at my desk, emptied my bag, and basked in the mountain of tens and twenties I had before me. The afterparty was waiting, but I couldn’t resist taking some time to find out the grand total of my efforts.
Partway into my count, I heard footsteps from the living room and a voice calling my name. It was Molly. What was she doing here? I beckoned her into my room and asked her that very question. She lingered at the door frame and noticed all of the cash I was sitting with, causing her to stumble over her words. She was adorable, all flustered like that. I looked her up and down. Her hands were behind her back, giving me a nice view of her curves. Maybe I was imagining it, but her nipples were poking out more than before. Her gaze was heavy lidded and bloodshot, clearly high on some potent herb.
The whole night had also gotten me quite high: high on adrenaline, high on myself and my own triumphs, and yes, a little weed along the way. All the work for this party and all the strife with Helen meant I hadn’t drained my balls in weeks outside of a few weak wanks. And now, most unexpectedly, I had this hot, young art-hoe wandering alone into my bedroom, serving herself to me on a silver platter. It was an all-too-potent mixture of intoxicants that turned me into the most selfish and arrogant version of myself, and suddenly my whole being existed in the service of getting my dick in this woman as fast as possible.
She told me she just wanted to make sure she congratulated me before she departed for the night, as we didn’t get a chance to properly talk during the party. She talked at length about how much fun she had and how impressed she was with the caliber of music I had booked, all the while playing with her ponytail. Being the gracious recipient of accolades that I was, I thanked her profusely for her contributions to the evening, and indulged her in some behind-the-scenes gossip. She was giggling at whatever random crap was spewing out my mouth. What got the biggest giggle from her was, in response to her asking if I needed help with anything else, spreading my legs and asking her to come over to me.
“Didn’t I see you with your girlfriend earlier?” she asked teasingly. I looked her in the eyes and told her the truth.
“All I can think about right now is your mouth on my cock.”
She bit her lip as she got on her knees and between my legs. With her forearms resting on my thighs, she undid my pants and fished out my thick member. She took a moment to admire its size against her dainty hand, then wasted no more time getting it between her juicy lips.
At this point the reality of the situation caught up to me. I was cheating on my girlfriend, there’s more cash in my bedroom than I have in my checking account, and anyone could just wander in at any moment. I was in an absolutely crazy situation. I know I’m small potatoes in the grand scheme of things, but I felt like a sleazy Hollywood exec exploiting some impressionable starlet. It was repulsive in a way that made me want to crawl out of my skin.
Looking down at the hipster hottie giving me the best head of my life, I was able to forgive myself. Molly was a passionate performer, and she was running through all her greatest hits. She wasn’t afraid to slobber, sacrificing her makeup in her desire to give me pleasure. The chorus of giggles, hums and moans she vibrated around my cock were so cutely feminine and high-pitched that they made me start dueting with some low moans of my own. She knew the value of playing with my balls, lightly tickling them with her long, red nails, sending shivers down my spine. Instinctively, I put my hand on her beret, not quite guiding her pace, but letting her know that I planned to take charge soon.
She popped my cock out of her mouth to stroke it, and looked up at me with a dopey, stoned grin.
“Is this helping?” she cooed breathily, punctuating the sentence with a gentle kiss of my tip.
I grunted in affirmation as I pushed her face back down onto me. She moaned at my forcefulness and reached under her skirt to touch herself. Her moans got louder, and it seemed like an orgasm was imminent, but she quickly stopped and let it subside. She began a cycle of building up and denying herself the climax for a while, focusing on her pussy’s needs, relinquishing to me the pace of her facefucking. I think she was waiting for signs that I was about to come, but was ignorant to the fact that I never had from a blowjob. I’ve always needed pussy to have my nut, and hers was soon to be ripe for the taking.
She was cresting for the fourth time when I reached down into her shirt and gave her left nipple a sharp pinch with one hand while I pushed her head deep into my lap with the other, her nose brushing my pubes. It was a risky move, but one that paid off. The shock of everything brought her over the edge, and she moaned, shuddered and gagged deep down my shaft as her long-steeped orgasm wracked her body.
I released her head, and she released my cock. A wet mix of saliva and precum tethered us. She looked up at me in a daze, breathing heavily, not saying a word. Before me was a woman who’d been brought to completion, and was primed to take more still. In this primal moment the last rational neuron in my brain took over the megaphone.
“I don’t have a condom,” it said through my voice. I assume it was trying to explain to Molly why I wasn’t going to be able to fuck her tonight.
“I mean….I’m on birth control.”
That was good enough for the neuron. I picked Molly up from the floor, spun her around, and bent her over the money desk, adding her to the grand total of the night's earnings. She arched her back, fully playing the bitch in heat. I pulled down her disheveled panties and got my first feel for the sopping mess that I’d made of her cunt. Her moans picked right back up. She turned her head to look back at me, begging wordlessly with her doe eyes for me to fuck her.
Quickly I realized our height difference wasn’t going to work standing up like this, so I picked her up from the desk with ease and tossed her onto the bed, eliciting a little shriek from her. She got back on all fours, hitched up her plaid skirt, and started wiggling her ass at me. Her swaying pussy, framed between the hem of her skirt and the tops of her thigh-high socks, had me mesmerized. I got behind her, grabbed her by her tiny waist, and gave my cock what it’s been asking for since Molly entered my room.
She was the kind of tight that makes you see stars. Even with how wet she was, it took some time to fit every raw inch of me in her. Once I bottomed out, I grabbed a handful of her black ponytail and pulled, forcing her to stare up at the dim overhead light as I took full control of her body. I knew I wasn’t going to last long riding her bareback, so I took it slow and deliberate to start.
Without my cock in her mouth to muffle her, Molly turned out to be quite the screamer. This made me nervous, because I had no clue if or when my roommates would be coming home from the bar. Needing to silence her, I opted to switch from pulling her hair to pushing her face into the pillow. This was met with another squeal; maybe not muted enough to avoid getting caught, but it assuaged my guilt enough for me to get lost in the moment. I picked up my pace, feeling my own orgasm building up. I yanked her back up again by the ponytail, and whatever she was babbling into the pillow transformed into a string of loud, profane encouragement.
With one last squeeze from her pussy, I thrusted my full length as deep as I could into her and shot a biblical flood of cum inside her. The tension of our encounter, of the whole day, even the months leading up to that orgasm was a buildup of electricity that needed to be released that night, and she was my lucky little lightning rod. For those fleeting delusional seconds, balls emptied into someone I would never see again, I was on top of the world.
I let go of her hair and pulled out of her leaking cunt. I must have been the only one of us supporting her, as she immediately collapsed into a sweaty, well-fucked heap. I looked down at my bed. It was smeared in lipstick and mascara. Sense came rushing right back in to fill the vacuum. I never imagined myself capable of any of this, but was now on the other side of my actions, their consequences looming over my immediate future.
She got up and examined herself in my mirror. Her makeup was smudged all over her face, her lipstick smeared from her nose to her chin. Her ponytail was loose, strands of hair tangled up outside the scrunchie. Cum was still actively leaking down her thighs. She dabbed some away with tissues from her purse, but more trickled down to replace it.
The energy in the room got much colder, not just from me but from Molly. It only occurred to me then that I might not be the only cheater in the room. I gained nothing from inquiring further, so I kept my mouth shut.
She asked me if I could walk her to her car. I certainly wasn’t interested in putting my infidelity on full display by trotting this freshly-fucked slut around the block. It wasn’t my problem that people would know just from looking at her that someone else got lucky, as long as they didn’t find out who.
I grabbed a wad of cash from my desk without counting, and stuck it in the waistband of her skirt, suggesting she call an Uber. We both knew it was way more than an Uber cost, and what I was trying to tell her by giving it to her. She stared at the money for a long moment, contemplating how willing she was to be made a whore before giving me a disgusted look and depositing it in her purse. She pulled her phone out and within seconds had a car on its way to pick her up.
As I walked her to the front door, I thanked her again for all the help and slapped her ass farewell. The last sound I heard from her was a pitiful yelp before she gave me one last blushing look, and walked to the black SUV idling at the curb.