Halloween: My First Threesome [m/f/f, m/f] (long)

The story in question took place on Halloween, a few years ago, at a party that I threw with my roommate at the time, Mark. I'm sorry about the rather unreasonable length; I'm not great at editing myself.

It was a great time to be us, frankly. We were both seniors in college, single, in pretty decent shape, and had just leased an awesome two-bed-two-bath town home. My newly minted roommate and I decided to christen the apartment with a series of parties. They were mildly successful, but the first devolved into a police incident when one of our friends, blackout drunk, smashed our neighbor's window with the top of a lamp post. We never figured out where he got it from. The second one was fairly quiet; mostly people arriving, staying for an hour or so, and then heading out just as the next group arrived. So we were determined: this was fucking Halloween, and we were going to tear shit up. Plus, the benefit of being the one throwing the party? It's so much easier to get laid.

At the time I was sporting a massive mop of curly hair, so I went for my mainstay Halloween costume, which I'd spent a few years perfecting: Slash, of Guns n Roses fame. I had everything: the side-laced leather pants, the biker jacket all over with zippers, the Black Death vodka t-shirt, and the crowning jewel, which was my grandfather' top hat, around which is wrapped a concho belt I'd found at a thrift store. I rounded out the look with a liberal dousing of silver bangles, a pair of skull earrings, snakeskin cowboy boots with chains, and a pair of mirrored aviators. I was the spitting image of GNR's guitar gunslinger circa 1988. Mark, meanwhile, affected a nearly flawless mad scientist, teasing his shaggy mane of hair into a frizzy Doc Brown mess, and adorned himself with a mess of flashing LEDs under his bloodstained lab coat.

We drew up and pruned the guest list to perfection, mostly coworkers and a few old friends for comfort, with a roughly 60/40 girl/guy ratio. We purchased all manner of cheap, off brand booze, which we combined with equally off brand energy drinks to form a truly lethal variety of punch. Mark spent almost 16 straight hours making and perfecting a playlist, designed to take the energy of the party gradually upwards until it would peak around 2 AM, with the aim of getting the cops called, but only once.

I should take the time to mention here that there were three standouts on my side of the guest list: Dawn, Morgan, and Charlie.

Dawn was a girl who I'd known since day one of freshman year – we'd become friends instantly when she decided to take pity on my sorry, lonely ass at orientation (I was fresh from six years of homeschooling, and thus had a fair amount of stunted social growth to overcome). As I'd grown into myself and come out of my shell, she'd stayed with me, and we'd become quite close. When she broke up with her boyfriend over the summer, we started hooking up, but managed to maintain our friendship through it (though I'd later find out she was harboring serious feelings for me, but that's another story). Dawn was one of those girls who are proportioned just-so; small without being petite, breasts perfectly suited to her frame (around 32C), a nice, plump ass and pale skin, lightly dusted with freckles. She had a rather round face, shoulder-length brown hair, and the most perfect smile you could ever imagine. Out of everyone I've ever met, no one looks as perfectly happy as Dawn when she's smiling – it's infectious and just absolutely melts your heart when you see it.

Morgan was my boss, the assistant manager of the restaurant where I worked, and a total desire object. She had chin-length curly hair that changed color every few weeks, and was a dedicated athlete. Everything about her was sharp and defined, from her muscles to her facial structure and eyes to her personality. She didn't bullshit, and I'd never seen her let her hair down, so to speak, and that was partially why she was so attractive, I think; I wanted to see what she looked like all disheveled, face flushed, gasping and moaning and no longer in complete control.

Charlie was Morgan's little sister, and the newest addition to the crew at our little Italian restaurant. She was every bit as liberal as Morgan was conservative – very artistic and free spirited. She wasn't nearly as sharp as her sister, though whether that was a genuine lack of intelligence or simply a lack of touch with reality on her part, I'm not sure. She was, however, every bit as attractive: just as athletic, the same flawless, dusky skin and classically perfect features. If I had to compare her to someone, I'd say she looked like the love child of Audrey Hepburn and Mila Kunis; one that got all the good genes. Oh, and she had the most perfect ass I've ever seen in person, which has since become the yardstick by which I measure all my sexual partners (I'm an ass man, through and through).

I suppose I should take this opportunity to describe our heroes. Mark is tall, about 6'4", and at the time had a long mane of shaggy brown hair. He was a whippet thin strip of a man, but lean, with the well-defined physique of a dedicated cyclist. He also has the most piercing blue eyes that drive girls absolutely nuts. I was sort of the opposite: coming in at a mere 5'7", although I also had a large mop of brown curls at the time. I was built a bit more solidly, being an avid rock-climber. For those who are curious, I don't know about Mark, but my cock is perfectly average, almost exactly. 5.5", though decently thick.

People started arriving at 9, my friends Ben and Simon showed up shortly thereafter with the beer pong table, and by 11 our little place was packed to the brim. It was awesome: my bandmates showed up and we ended up playing an impromptu acoustic set to massive applause. We had a big table set up on our patio around which everyone sat, smoking and drinking and laughing and just generally having a great time. We got some Rock Band going, someone made pizza rolls, putting them on a wooden cutting board and setting the whole thing in the oven, which only caused a minor fire. Around 1, we got our wish: the cops showed up to tell us to keep it down. They were very civil, and told us that if they had to come back again they'd issue us a formal ticket, and a third visit would result in an arrest. We stashed the underage drinkers in the kitchen and carried on undeterred.

Throughout the evening I’d been splitting my attention between the three girls. Charlie was, oddly enough, the first person to show up, around 9:30. Perhaps capitalizing on her resemblance to Audrey Hepburn, she had elected to go as Holly Golightly from Breakfast At Tiffany’s, and holy shit did she look amazing. She had it down to a T – the slinky black dress, the elbow-length velvet gloves, her hair in a precise updo, sporting period-perfect jewelry. She was absolutely ravishing, every bit as stunning as Audrey herself. When I opened the door, I was struck dumb for a good four or five seconds, unable to do anything except drink in her looks. Mark and I quickly ushered her in, as if we were afraid that she might decide that she was too good for our slummy little get together and decide to go somewhere more befitting of her amazing appearance. We made that particular brand of awkward conversation that inevitably happens with the first arrivals at a party, gave her the tour, etc (both of us, in anticipation of pulling a girl, had cleaned our rooms down to the carpet fibers). She asked for a drink, and we introduced her to the punch, then took a shot. More people showed up, and things settled in smoothly. At one point I caught Mark’s eye, and he nodded – she was all mine if I could make it happen. He was more interested in Morgan, anyway.

Morgan arrived shortly thereafter, in a sort of nondescript slutty fairy costume. The gist of the outfit seemed to be to display as much skin as possible: thigh highs, neon-orange boyshorts, a sort of tutu thing that did absolutely nothing to cover her ass, and a cutoff white tank top that showed off her beautifully-defined abs. To our dismay, she also arrived with a date in tow. Or, at least, he seemed like a date – he was certainly possessive enough of her, keeping a hand firmly clamped to her waist throughout the night. Mark, not to be deterred by something as trivial as another man, did what he does best and began attempting to engineer a way to separate the two of them.

I’m not entirely sure how it went down, since by this time Dawn had arrived, and I was having a blast talking with her and Charlie, cracking jokes and snide remarks about other people’s costumes. Dawn had opted for a slightly more traditional outfit: slutty pirate. Knee high black boots, a miniscule skirt, a sort of red corset over a white blouse, topped off with a cheap foam tricorn hat. We’d managed to commandeer the one couch in the apartment, the rest of the group either sitting outside at the table, or lounging on the array of pillows we’d strewn all over the floor. Dawn was sitting in my lap, and Charlie on my right, draping her deliciously smooth legs over Dawn’s. As we laughed and talked, Dawn’s continual shifting on my lap caused a stirring in my pants, which, given how unmercifully tight my leather pants were, rapidly became uncomfortable. I was on the verge of making an excuse to get up and relocate (“perhaps to my bedroom, where we can actually hear each other?”), when a commotion became apparent outside. We stood up and rushed to the window that looked out onto the patio, where there was already a line of spectators.

Outside, Morgan’s date was pitching a fit at Mark, yelling something about how he’d “touched his woman” and how he needed to “get his own bitch”. Mark was standing back, just out of punching range, grinning like the Chesire Cat. Morgan got in between the two of them and told her date, in no uncertain terms, that she would not tolerate being referred to in such a way, and that he ought to take a cab home, as she was done with him. He demanded that they leave together, she told him to get lost, he tried to grab her arm, she shoved him back and went inside. Recognizing Mark’s handiwork, I took this as my cue to step in as one of the hosts. I went outside and told the guy that we were going to call him a cab, and that he needed to leave, or we were going to call the cops and have him removed. Presented with a united front, he glared at us before turning his back and walking out. Mark, eager to capitalize on the situation, immediately chased after Morgan and set to work laying down his particular dialect of manipulative charm.

I went back into the kitchen to grab another round of drinks for myself and the girls, but when I returned to the living room, they were nowhere to be found. I asked around, but no one could remember seeing them leave. I went up to my room, thinking that maybe they’d retired up there to get away from the commotion, but no dice. As I was about to head back downstairs, I was cornered by another of the restaurant staff, a delivery driver named Charles. Charles was so drunk that he was apparently convinced that I was actually Slash, and damn it, he wanted to hear some guitar playing. As I was fairly drunk myself, I decided to oblige, grabbed my guitar, and started playing a few GNR riffs while Charles cheered and fist-pumped – looking back on it, it was a thoroughly surreal scene.

Right at that moment, the door to my room burst open as Dawn and Charlie almost literally fell through it, entangled in each other’s arms, lips locked in what seemed almost like desperation (I later found out that while I was outside, they'd gone to the bathroom together to pee, and Charlie had made a move on Dawn, who was totally into it. After making out for a while and going down on each other in the bathroom, Dawn suggested they go and find me). My eyes nearly popped out of their sockets, and Charles and I could do nothing but stand there and watch as the two of them flopped onto my bed, frantically pawing at each other’s clothing. After what seemed like an eternity, but was probably no more than thirty seconds, Dawn disengaged herself from Charlie’s neck and looked up at me.

“Well, are you going to join us or what?”

I could have proposed to her right then. My immediate concern, however, switched to Charles. Before he had a chance to interpret the invitation as open, I dropped my guitar and literally kicked him out the door, slamming it shut and locking it behind him. I turned back to the girls, both of whom were now looking at me with eyes that would have made a monk renounce his vows on the spot. Through a haze of alcohol, growing lust, and sheer disbelief, I fought for words, any words.

“Are…are you sure?”

Dawn rolled her eyes and leaned over, grabbing my belt and dragging me towards the bed. As I realized that this was actually happening, my primal lizard brain took over. I shrugged off my jacket and hurled it across the room along with my hat. Dawn and Charlie rose to their knees in front of me and in one swift, concerted movement, actually ripped my pants off. They pulled so hard that the zipper and buttons snapped clean off, and I frantically helped them, struggling against the sticky leather clinging to my legs. I tugged my shirt over my head and, realizing that I was now the least dressed, dropped onto the bed to help the girls catch up. I went to work on Charlie first – she was now on her knees, lifting Dawn’s skirt and pressing her fingers to the rapidly dampening patch on her teal thong. I unzipped her dress, trailing a string of kisses down her beautifully toned back to the dimples above her hips. I yanked it off, ripping it a little, and quickly removed her navy blue panties, revealing her shaved pussy. It was just about perfect, with just a hint of her inner lips showing, already wet and ready. I traced a finger down her slit before sliding a finger into her, meeting no resistance, and dragged my lips across her ass, pausing to leave a hickey on her right cheek, like a brand. Charlie was now eagerly tonguing Dawn’s pussy, who was writhing and gasping, her fingers buried in Charlie’s immaculately styled hair. I tentatively licked Charlie’s asshole, revelling in the taste of her salty skin, and she paused in her endeavors as an appreciative shiver ran through her body. I added another finger and began to eat her ass in earnest, pumping my fingers in and out of her soaking wet hole in time with my tongue.

Dawn, meanwhile, had sat up and was removing what remained of her costume, trying to keep some semblance of control while Charlie’s tongue danced over her clit, eliciting moan after moan. We continued like that for a few minutes before Dawn pushed Charlie back and nodded over her shoulder at me. Charlie spun around and grabbed me by the shoulders, pulling me around and down onto my back. Dawn crawled around one side while Charlie threw her leg over my head, straddling my face. I planted my hands on her wonderfully firm ass and pulled her down onto my tongue, burying my face in her pussy, drinking deeply of her scent and taste. I felt Dawn’s hands tugging my boxer briefs down and lifted my hips obligingly. With another quick pull, she pulled them down past my knees, freeing my cock, which sprang to attention. I felt Dawn’s hot breath on my dick before her soft, wet mouth engulfed me, eliciting an involuntary moan as she swirled her tongue around the head. Charlie leaned down, laying prone on top of me and I felt a second tongue join Dawn’s as they licked my cock together, running their lips up and down my length.

Now that I had better access, I slid a pair of fingers into Charlie’s pussy while I began rubbing gentle circles on her asshole with my other hand. I continued to lick rapidly at her clit as I pressed a finger into her ass, going slowly so as not to hurt her. It became a battle to maintain concentration on what I was doing as the girls continued to do amazing things to my cock, taking turns sliding me into their mouth. Charlie began bobbing up and down on my dick while Dawn turned her attention to my balls, running her tongue over them before gently taking one, then the other, into her mouth. Every time I thrust my fingers into Charlie, she moaned around my cock, sending another thrumming lance of pleasure through me.I thanked any number of gods for the partial numbing effect of alcohol, otherwise I’m sure I would have cum within seconds from the tandem blowjob.

Just then, there was a knock on the door, loud and urgent. As one, we stopped what we were doing and shouted some variation of “Fuck off!”. I heard Mark’s voice, muffled through the door.

“Dude, let me in! We need a place to fuck and my door won’t lock!”

Grating against my frustration, I shouted back “Well, find somewhere else! We’re already fucking in here.” This got a giggle from the girls.

“Come on dude, we don’t have anywhere else to go. There’s someone throwing up in the upstairs bathroom. Come on, just let us in, we won’t get in your way.”

I sighed. “Charlie, is this going to weird you out, your sister…being in here?”

She just laughed “As long as there’s no chance of me touching her, I don’t care. It’s not the first time I’ve seen her naked.”

Mark knocked again, so hard the door shuddered in its frame.

I laid my head back against the pillow and shrugged. “Dawn, would you mind…?”

She got up and unlocked the door. I craned my head around Charlie’s leg and saw Mark leading Morgan into the room, both of them half-undressed, Morgan already sporting a few hickeys, dark spots on her already dusky skin. I waved my arm vaguely towards the other side of the room.

“Alright, go ahead and do your thing, just keep it to yourselves.” I caught a glimpse of Mark’s face, mouthing a silent “Thank you” as he shed the rest of his clothes, snatched a blanket off the bed, and led Morgan by the hand to the other side of the room. Annoyed as I was, I had to hand it to him; pulling someone like Morgan must have taken some serious skill.

The room was full of awkward silence as everyone waited for everyone else to resume their activities. Charlie broke the tension by shifting her hips backwards onto my face, smothering me with her pussy. I dove back in with abandon, running my tongue across her clit in a series of random patterns. Dawn grabbed my cock, now at half-mast, and began gently stroking it while she licked the underside of the head, coaxing life back into it. After a minute or so, we were all back in our own worlds, paying no attention to the other people fucking not more than ten feet away.

Once she’d gotten my dick back to its full hardness, Dawn sat up, still stroking, and pulled Charlie in for a kiss. I heard her whisper something, but with Charlie’s thighs locked over my ears, I couldn’t make out the words. The message became clear a second later as Charlie scooted forwards, shifting herself around the other way. Dawn reached over my head to the cigar box I kept next to my bedside lamp and pulled out a condom, which she passed to Charlie. Charlie rolled the rubber over my length, keeping her eyes locked with mine the whole time – to this day, I still think the sensation of someone else putting a condom on for me is one of the sexiest things I’ve ever felt, can’t explain why. Without another word, she positioned her hips and lowered herself down onto my cock. If her pussy looked good and tasted great, it felt even better. She had the perfect blend of slip and grip, just enough friction to make every single stroke feel amazing, but not so much that it ever felt uncomfortable.

She did a few exploratory up-and-downs, then planted her hands on my chest and went for it, driving her hips into mine with pneumatic regularity. I tried to move, to time my upward thrusts to match her downward ones, but she was so forceful that I gave up and just let her have me. Dawn straddled my face and I wrapped my hands around her thighs, pulling her down onto me. Dawn’s pussy was slightly more obvious than Charlie’s; her lips a little bigger, but she tasted just as good, if not better. Since we’d been fucking for several months by this point, I knew exactly what to do with Dawn, and immediately began sucking on her clit, tracing circles around it with my tongue. I bent my wrist at an improbable angle and pushed a couple of fingers into her, fucking her in time with Charlie’s bouncing hips. From across the room, I heard a gasp and then a moan, and craning my head to look over, saw Morgan on her knees, face buried in the carpet as Mark pushed his cock into her from behind. He had one of her arms pinned behind her back, the other holding a fistful of her auburn curls. Charlie’s hips slamming down onto me refocused my attention, and I dove back in between Dawn’s legs.

Although I suspect Charlie could have continued like that all night, I heard Dawn, between gasps and moans.

“Get….off…it’s my…turn…I want to…Ah!…I want…to fuck him…”

Charlie slid off my rock hard prick and pulled Dawn to her, stitching kisses down her neck and kneading her breasts roughly. I sat up, taking a moment to catch my breath now that I had access to air again, taking in the scene in front of me. Charlie and Dawn were now entangled on my bed, a knot of arms and legs and heavy breaths. Across the room, Mark was slamming his cock into Morgan with abandon, now holding her head up by her hair as she furiously rubbed her clit with one hand and supported herself with the other. I got up on my knees and grabbed Dawn’s hips, pulling her into a similar position. Charlie scooted over, spreading her legs in front of Dawn, who dived in as Charlie wrapped her hands around the back of her head. I grabbed another condom and rolled it on, adding a drop of lube for good measure, then slid my cock into Dawn’s sopping wet pussy.

I began thrusting, gently at first so as not to dislodge Dawn from her spot in between Charlie’s legs, before slowly ramping up my speed and force. Before long, I was hammering myself into her, my balls slapping against her clit, pumping a finger in and out of her ass in time with my thrusts. All three of us were gasping and moaning, riding an enormous wave of pleasure. I looked across at Mark, who looked back and gave me a cocky nod. I was grinning like an idiot – on some level, I still couldn’t quite believe this was happening.

I’d love to say that this threesome continued for hours, culminating in me jerking off onto Dawn and Charlie’s faces, before they licked each other clean and we collapsed in a sweaty, sated heap on my bed and drifted off to sleep. Unfortunately, some of the assholes we’d invited to the party decided that we’d had enough fun, and if they weren’t getting laid, then neither should we. I later learned that my windows were open, and everyone had congregated out on the patio to listen to us fuck.

A group of guys, led by my friend Stephen, stormed up the stairs and proceeded to literally kick my door down before barrelling into the room and dousing us all with beer, chanting “COOL IT OFF, COOL IT OFF KIDS!”. Fucking worthless sacks of shit. You’d think that as men they’d know enough about the sacred institution that is the drunken threesome to show a little respect. Ah well.

After that, the girls were too embarrassed and we were all too sober to try and get things going again. Charlie and Morgan got dressed and bolted as quickly as they could, while Dawn stayed behind to help clean up and kick everybody out at the end of the night.

After that, Charlie and I hooked up a few more times, and Dawn and I eventually ended up dating. We’re actually still together (she helped me remember a few crucial details of this recounting). If you’d like to hear more about some of our sexual adventures (such as other people we've fucked together; yes, she's absolutely the best wingman ever), let me know, and I’d be happy to oblige. In any case, I hope y’all enjoyed reading as much as I enjoyed writing it!

Source: reddit.com/r/gonewildstories/comments/337r8u/halloween_my_first_threesome_mff_mf_long