Work Text:
Dean knocked on the door again, leaning back to check the mailbox to make sure it was the right address. It was bad enough that he was late, wouldn’t do to go asking for an orgy at the wrong house too.
He rubbed his hands together against the chill building outside. He should have worn gloves. It was a late September night, with the sun long down, and the wind was starting to pick up. The wait was giving his nerves a chance to build up again. He'd gotten himself psyched all the way up for this on the drive over and now, standing on the wide porch of this vanilla looking house in this vanilla looking neighborhood, the tension was starting to creep back into his shoulders.
Dean glanced back at his car, one among a few others parked along the curb. He spied a yellow Gremlin and a sweet looking Harley among the lot. Maybe he could just turn around here, just drive off, pretend this never happened, find another way to spend what was left of his Saturday night.
Finally, just before Dean was starting to think plan B was the way to go, the door cracked open, revealing a harried looking young woman with suspicion in her eyes.
“Can I help you?” she clipped out.
“Uh, I'm here for the uh...” he trailed off, then, soto voce, “...orgy? I’m a friend of Chuck’s?” Dean stammered out.
Well, friend was kind of stretching it. If friend was what you called a person you vaguely knew from too many nights in the coffee shop, a person who asked your opinion on his weird ass novel ideas, who out of nowhere asked you if you might be interested in participating in an orgy? Then yes, he and Chuck were friends.
Her face brightened up at that, frown lines instantly disappearing. “Oh! You must be Dean!”
Dean chuckled a little, embarrassed for some reason. “Well, I don’t know if I must be, but...”
“You’re late,” she said flatly, clearly not impressed at his lame attempts at boyish charm. “The email clearly stated ten sharp. It's 10:07.”
Dean shuffled his feet a bit, glancing around the porch. “I had a little trouble finding the place. I’m not real familiar with this neighborhood.” He gave her his best grin, the kind that used to get him out of a smack down when he got caught stealing for the umpteenth time.
The woman gave him the stink eye up and down, then seemed to come to a decision. She opened the door a little wider.
“I guess I can make an exception this one time. You're lucky you’re cuter than Chuck said you were and that I'm a stickler for even numbers.”
His brain got caught for a second wondering how Chuck didn’t seem to think he was that cute before catching up and following the woman into the house.
It was much warmer inside than out and he took in his surroundings. Soft yellow walls, overstuffed couch, surprisingly tasteful art on the walls. He wasn’t sure what he thought an orgy house would look like, but this wasn’t it.
The woman led him down a short hallway to a room on the left where he saw piles of clothes and other personal belongings. She turned to face him.
“So, I’m Becky, Chuck’s girlfriend. He may have invited you but officially I'm in charge of these things. I assume you got my email?”
Dean nodded, remembering the surprisingly serious email he’d gotten a couple days after Chuck’s invite, listing the apparent do’s and don’ts of orgy etiquette, plus some suggestions on how to prepare, literally and in graphic detail, for the actual event. He even had to reply with a copy of his clean STD panel. He'd been both mortified and turned on in equal amounts.
“Good. So, this is where you’ll leave your clothes and other things, obviously. It keeps them from getting messy downstairs.” She gestured around the small room, pointing as she talked. “There’s a chair over there you can use.” Dean walked over to the chair, starting to take off his jacket as she spoke. He figured he might as well get this show on the road.
Becky reached out. “Let me see your hands.” She turned his palms over and inspected his fingers. He hadn’t quite gotten all the oil out from work but she seemed satisfied anyway. “Good, you cut your nails. Not everyone remembers to do that. It's more important than you think. One bad hangnail and things can go south pretty fast.” Dean grimaced, hoping she wouldn’t elaborate.
“Oh!” Becky threw her hands up, startling Dean a little. Woman was terrifying. She grabbed a small metal bucket from the table by the door. “Write your name down and put it in here. There's a kind of raffle at the end of the night and you know you wanna be included.”
A raffle? What kind of weird ass shit had Dean walked into? He shook his head, took the pen and paper she proffered, wrote his name down, and dutifully dropped it in the bucket atop the other slips of paper.
“Great! Now, I'll just leave you to get undressed and you’ll go down the stairs at the end of the hall. Can't miss it. Have fun!” Becky winked exaggeratedly at Dean and turned on her heel out of the room. Dean breathed a sigh of relief, still wondering what the fuck he’d gotten himself into. What if all the participants were like Becky? He'd half expected Chuck’s invitation to be a joke but now that he was here, the overwhelmingness of it all was getting to him. Sure, he’d hooked up with guys and girls both, even a drunken threesome that one time, but an orgy? A straight up, group sex porn fest with strangers? He was walking into unknown territory here and he was a bit worried he’d gotten in way over his head.
Dean shook himself, trying to get rid of the giant butterflies in his stomach. He’d done scarier shit than this before. Like that time in middle school he’d tackled the neighbor’s Yorkie thinking it was a werewolf. He could for sure handle this. He quickly divested himself of his clothes, pausing when he reached his black briefs. It felt so weird to be walking into a room full of strangers naked. But, he figured, they’d all be naked too. Even footing, so to speak. With a deep breath, he hauled those off too.
Dean peeked around the corner into the hall, checking for any signs of Becky, and caught sight of the stairs at the end. When she failed to appear, he turned and walked down the hall. Intellectually, he knew he was about to walk into something really hot, but physically, his dick wasn’t getting the message. It was currently threatening to creep back into his body like a reverse worm. He paused at the top of the stairs, gave himself a few strokes to calm down, then started to descend the carpeted steps.
He could hear the orgy before he could see any actual action. Lots of moaning, interspersed with curses and laughter, the sound of skin on skin, the thumps of bodies moving. He could see a table set against the wall facing the stairs, complete with bowls of various kinds of food, bottles of Gatorade and water, plus what looked like a shelf’s worth of different kinds of lube. Considerate of Becky to provide refreshments, he thought absently. At last, he reached the bottom of the stairs and was officially out of any excuses. He took a deep breath and turned the corner.
His eyes instantly lit upon the sectional couch full of writhing bodies. A few turned their heads to check out the newcomer, the blonde, the brunettes, but then turned back to whoever they were doing. He swept his eyes across the couch, taking in the action. Starting from the left side of the couch, he spotted a blonde woman on her knees, gagging on the cock of a giant. Another, shorter man was behind her, fucking her with a weirdly maniacal look on his face. Two female redheads were furiously making out while next to them a burly man was plowing a slender brunette like a wheelbarrow. Lastly, his eyes settled on a man fucking a dark-haired woman on the far end of the couch. He was arrested by the sight mainly because the man was staring him down. His sky-blue eyes never left Dean’s, though his grip on the woman tightened and his hips never stopped moving. With a smirk, he nodded at Dean to come over.
Dean gulped and walked over to the couple. It felt supremely awkward to be walking around with his dick hanging out but so was everyone else’s so he figured he should get over it.
The dark-haired man smiled and offered the hand that wasn’t tangled in the woman’s hair.
“Hi,” he said, “I’m Cas. This thorny beauty here is Meg.”
The woman, Meg, growled and threw her body back against Cas’. “What have I told you about calling me that?”
Cas chuckled. “Just because you don’t like it doesn’t make it any less true.” Cas looked up at Dean. “Am I right...?” he trailed off.
“Dean, uh, my name’s Dean, and uh, yeah, yeah, I agree,” he stammered, momentarily started by Cas’ directness. For some reason, he hadn’t even thought about exchanging names. The whole time, Cas never stopped twitching his hips up into Meg.
Cas grinned wolfishly. “Hello Dean.”
Dean felt like he was going to melt into the floor. Having accepted his bisexuality at a young age, he’d never been one to shy away from attention from either sex, which, with his uncommon looks, came often. However, he’d mostly kept his own affections close to the chest, so to speak. Now in his mid-twenties, he’d still never had what anyone would call a long-term relationship. He actually preferred it that way. But the way this man was looking at him, with those eyes, Dean could feel his knees weakening like a damsel in some chick flick.
“This your first time at one of these?” Cas asked. “You have that look about you, like a deer in the headlights.” He wrapped his palms around Meg’s breasts. “And what lovely headlights they are,” he joked.
Meg whipped her head around to glare as Cas but he quickly grabbed her hip with his left hand and shoved up hard, effectively silencing anything else she was going to say about her purported beauty. Instead she moaned, low in her throat, finally giving Dean’s flagging dick something to pay attention to. It didn’t escape Cas’ notice either.
“Would you like to join us? Meg may have a smart mouth but she’s good at putting it to other uses as well.” Cas swept his eyes up and down Dean’s body, smirking again as he made eye contact and pushed Meg forward.
The grunts and groans of the other people were suffusing Dean’s senses. This is what he came for after all.
“Yeah, yeah, if that’s alright with you, uh, Meg.” Dean mentally kicked himself. He was usually much more smooth, he promised.
Meg leered up at him and leaned forward, wrapping one arm around his waist and tugging him close. “Buddy, you don’t need to ask permission around here. It's a free for all. Give and take, you know?”
She leaned in and enveloped his soft dick in her mouth, pushing all the way down till her nose brushed the tense skin of his belly. Dean nearly bent in half at the crazy warm-wet feel of her tongue caressing the underside, his hands instantly fisting in her hair. As she withdrew to the tip, his dick finally got the message, hardening up to what he objectively knew was an impressive size. As she worked her way up and down, teeth scraping lightly, Dean closed his eyes, losing himself to the feel of a really good blowjob. Most girls he’d been with went for speed, thinking that if they bobbed their heads fast enough you wouldn’t notice that they weren’t actually doing that much. Meg, however, definitely knew what she was doing.
A hand touched his hip and he opened his eyes to see Cas staring back at him.
“She’s good, huh? It's the only way to keep her quiet most days.” Cas crinkled his eyes in a conspiratorial smile Dean felt strangely special to be a part of.
Meg made a sound of indignation around Dean’s dick and flipped Cas off but otherwise never stopped her ministrations.
Cas gripped her waist with both hands then and pistoned his hips into her in a wild motion, tilting her hips forward in a way that had her keening around Dean’s dick. She pulled off to gasp out her orgasm and Dean quickly took over, his hand stroking quickly over his length, attempting to follow her over. With his eyes closed, he startled when another hand joined his, though this one was not helping. His eyes flew open to see Cas squeezing his erection tightly at the base.
“Hold it, hold it,” he said, wide eyes never leaving Dean’s. “The name of the game here is stamina, at least for us. Have you ever edged before?” he asked.
Dean shook his head. He'd heard of it, but in his experience, the destination was usually more the point, not the journey.
“Well, you’re going to get a crash course here. Take a breather, at least for a few minutes. You don’t want to spend half the time you’re here recovering, you know.”
Meg, who’d crawled off Cas’s lap after she got to come, gave Dean a smug little smile. “Yeah, the patriarchy may rule the world but at least we women get to have multiple orgasms and no down time.” She made her way over to the threesome, tugging at the taller man and replacing the blonde’s mouth with her own.
Dean turned his attention back to Cas, who grabbed his wrist and pulled him down to his knees. When their erections brushed against each other, Dean hitched a gasp. “Yeah, no, I get it.”
Suddenly a small hand encroached on their space, wrapping around them and gliding up and down. Dean looked right and saw the smiling face of one of the redheads.
“Hey, Cas.” She bumped her shoulder against the other man’s and leaned in for a deep kiss. Cas sifted his fingers through her long hair and Dean had never been so jealous.
They finished and she turned to Dean next. “Hi, I’m Anna.” Dean was gifted a kiss of his own, full lips moving against his slightly chapped ones.
“This is Dean, it’s his first time,” Cas introduced.
Anna smiled again, warm and inviting. “Well, then let’s show him a good time.” She nudged herself between them, forcing Dean to stand again. With her back to Cas, she mounted him, long pale legs straddling his thick thighs. Cas stuck the fingers of his right hand into his mouth, coating them liberally before reaching down under and rubbing against her hole, already pretty loose from previous activity. When he was done, he took hold of his cock and guided it into her back entrance. The look of ecstasy on her face made Dean want to switch places.
When she was situated, she reached for Dean, pulling him forward and rubbing his dick up and down her slit, getting him nice and wet before pushing him in with a foot against his ass. He grabbed the backs of her knees to steady himself. He could feel Cas on the other side, not much between them. The feeling was intoxicating. He had more leverage than Cas and began to set the pace.
He leaned into her, bracing himself against the cradle of her hips, and rocked in and out. He could feel Cas’ balls underneath his, the light friction bringing sweat to the small of his back. The pressure made Anna feel incredibly tight around him and after the intense blowjob Meg had given him earlier, he didn’t feel like he would last long, Cas’ edging advice be damned.
Dean glanced up from where they were joined and saw Cas cradling Anna’s face to his, kissing her again. He also spotted the silver barbells piercing Anna’s pert nipples. He bent towards her, capturing one in his mouth and running his tongue along the cold metal. She broke off the kiss with a moan and grabbed his head, holding him tight against her breast. His distraction allowed Cas to take more control, grinding up into her and against Dean.
That was the last straw. He so wanted to last, so wanted to impress Cas, but the intensity was too much. He pulled out in an attempt to stop himself but the crest was right there and he rode it, coming over Anna’s stomach and thighs in thick spurts with a shuddery groan.
With deep breaths he came back to himself. “Fuck, I'm sorry, didn’t mean to do that.”
Cas just stared at him with those large eyes of his. With two fingers, he scooped up glops of Dean’s come and pushed it into Anna’s mouth. She sucked eagerly, whimpering softly around Cas’ fingers as he continued to drive into her asshole.
With his other hand, he grabbed Dean’s wrist and pulled him to sit next him on the couch. Dean's heart was still racing and he was glad for the chance to relax after being on his feet so long. He could see the other people at the far end of the couch. The very tall man was now bouncing on the dick of the shorter man while the burly dude shoved his dick down his throat. Meg and the blonde were ruthlessly fingering each other as the other redhead plucked Meg’s nipples. The fourth girl was nowhere to be seen and Dean assumed she was taking a break, something he felt in desperate need of.
Next to him, Cas pulled Anna’s hair back tight, wrapping his other arm around her belly as his thrusts became erratic. As his body froze in orgasm, he turned to Dean, finally giving him a taste of those lips he’d been so jealous of. It was artless and hard, just a mash of lips against lips, but Dean had never loved a kiss so much. He pushed his hand into Cas’ hair and Cas made a low noise in his throat, tilting into the touch. As his body calmed, he ended the kiss, gasping for air as Dean had been, rubbing his forehead against Dean’s. He pulled away, seemed to consider something, and then whispered into Anna’s other ear. She nodded and Cas turned back to Dean.
“If I asked you to do something, would you do it?” With that voice, Dean thought Cas could ask him to rob a bank and he’d do it.
“Of course.”
Cas smiled and swiftly lifted up Anna, still attached to him, and lowered her to hands and knees on the floor. Cas wrapped a hand around Dean’s left knee and whispered, “Come eat my come out of her.”
Dean felt dizzy with desire. If seeing Cas feed Anna Dean’s come earlier had been hot, this was like the sun. He fell to his knees beside Cas and put hands on each of Anna’s cheeks, spreading them wide as Cas eased his dripping dick out. Dean quickly leaned in to catch the liquid before it could follow. He wasn’t normally big on rimming, but if everyone here had followed the same instructions in Becky’s crazy email as he had, it would be fine. He laved his tongue across her gaping hole, muscles still spasming from Cas’ rough use of it.
Movement across the small of his back, a soft back and forth motion, told him that though Cas had just come, he was definitely still enjoying what he saw. Dean pushed Anna’s shoulder, urging her down on elbows, so he could more savor the overflowing cup before him. He didn’t think she had come either, for which he felt bad, so he inserted three fingers into her stretched pussy, making her tremble even more around his tongue.
When he added his thumb across her clit, the stimulation got to her and Dean could feel her squeezing rhythmically around his fingers, gasping into the carpet. He felt the air move over his shoulder and Cas spoke into his ear. "Mmm, I like a giver.”
Anna collapsed on the floor and Cas hauled him up to standing, clapping a hand on his shoulder.
“Come on, we deserve a break after that.”
With a slap to Anna’s upturned ass, Cas steered Dean towards the table in the corner. Cas immediately grabbed a Gatorade and handed it to Dean. “You’ll definitely want this, helps replenish all those electrolytes you spewed on Anna’s stomach.” He grinned at Dean.
“Thanks, dude.” Dean uncapped the bottle and gulped down half the contents while Cas started unpeeling a tangerine. “Interesting set up over here.”
Cas laughed. “Yeah, Becky takes her shit really seriously. All this stuff is supposed to help improve blood circulation or something. Nuts, berries, citrus, all supposed to get your blood flowing. She thinks it helps lower the refractory period.”
That reminded Dean that he was standing at a refreshments table fully naked next to another man, also fully naked. It was one thing in the middle of the action, but Dean’s nerves were starting to make a repeat appearance. He put the bottle back to his mouth and swallowed.
“You’re beautiful, you know that?”
Dean coughed, blushing hard at Cas’ words. He never was able to take a compliment.
“Shit, man,” he spluttered, “you can’t just say that to a guy.”
Cas squinted and cocked his head, clearly amused at Dean’s reaction. “You just went balls deep in a woman with me but that’s pushing your boundaries?”
Dean tossed his empty Gatorade bottle in the trash and grabbed a handful of sunflower seeds. He needed something to focus on.
“Would it make you feel better if I said you were handsome? Hot? Sexy?” Cas’ voice was getting lower with every word and it was doing things to Dean.
Dean's blush was moving down his chest. “I thought this was supposed to be break time, man.”
Cas blinked, taken aback. “You’re right, my apologies. Didn't mean to make you feel uncomfortable.” He took the final bite of his tangerine and tossed the peel.
Dean tried to resurrect the conversation. “So, how long have you been doing this? Coming here?”
Cas allowed it. “Little over a year. It’s a nice way to blow off steam, meet new people.” He glanced sideways at Dean, then gestured out to the rest of the group. “You met Meg and Anna already. That’s Jo,” he pointed at the blonde, “Bela,” the slender brunette, “and Charlie,” the other redhead, “with their mouths glued together.” Cas waggled his eyebrows. “The moose is Sam. The dude fucking him is Gabriel. And -”
“Hey, brother, you keeping the new guy all to yourself or can anyone get in on this?” Dean turned at the southern accent to see the brawny guy with the ten o’clock shadow.
Cas smiled, wide and genuine. “And this is Benny.” The Cajun wrapped an arm around Cas’ waist and pecked him on the cheek. “Benny, meet Dean. Be nice,” he admonished.
Benny turned his slate blue eyes to Dean and flashed a feral grin. He reached out and grabbed Dean’s hand, pulling him in till his arm wrapped around his neck. “Yeah, could definitely have some fun with you,” he drawled, scraping his eyes down and up. “Ready for another round, cher?”
The twitching of his dick made no question about that. Cas swatted him on the ass, telling him, “Don’t do anything I wouldn’t do,” as Benny grabbed a few lube packets from the bowl and led him back into the main room.
The couch was full of undulating bodies, their movements like waves cresting, so Benny led Dean to the carpeted floor, urging him on his back. Out of the corner of his eye, Dean saw Cas rejoin the others, wedging himself between Bela and Gabriel, who had migrated to the far end of the couch. He felt a small pang that was quickly eclipsed when Benny straddled his hips, nudging their cocks together, taking them in hand, and rubbing lazily. He leaned down and claimed Dean’s lips with a kiss, sloppy and full of promise.
“Fuck, boy, you taste like spun sugar,” Benny breathed, eyes blown as he looked down at Dean, heavy lidded and soft.
“You...” started Dean, blinking, “taste like the ocean.”
Benny ducked his head, hand reaching for the packets of lube he’d brought and ripping one open. He drizzled it over himself and Dean, easing the way for his callused fingers. Dean’s head thumped against the floor; the feel of the other man’s hand, rough and tender, was quickly bringing his previously spent erection back to life.
It didn’t take long for him to get fully hard again. The hand not jacking them off was trailing all down Dean’s side, petting and squeezing and driving him nuts. Dean fully expected Benny to top him, even started pulling his knees up when Benny opened the second packet of lube, but to his surprise, Benny rose to his own knees and reached around behind himself, gingerly working himself open.
Dean felt brave and dragged his hand up to join Benny’s, tracing around his hole, working his fingertips in. It didn’t take much. When Benny moaned, Dean grabbed his cock and hauled Benny down, angling himself up into the tight space. Spreading Benny’s ass cheeks, Dean speared him, pushing up as Benny pushed down, till he was fully seated.
“Oh shit, oh shit, oh shit....” It still hadn’t been that long since he came with Anna and everything was sensitive, lights exploding behind his eyelids.
“Come on, cowboy, gimme a good ride,” Benny slurred, drunk on the way Dean had stuffed him.
Never one to back down from a challenge, Dean planted his heels, grabbed Benny’s thighs, and thrust, once, twice, bucking Benny like the bronco he imagined he was. Man held on tight, Dean gave him that, pushing his feet under Dean’s ass to give himself more leverage. Dean grabbed his neck, hauling him down for a rough kiss, all tongue and teeth. Benny groaned into his mouth as Dean nailed his prostate over and over.
At the same time, Dean felt a kick at his ear. He broke off the kiss and looked up, just now noticing the legs on his left side. He was closer to the couch than he’d thought. Angling himself up on his elbow, he looked to see who the foot belonged to.
It was Cas, of course. Though he was just as occupied as Dean was, if not more so. Bela laid on the couch perpendicular to Cas, giving him what looked like one hell of a blowjob if the tight, white-knuckled hold Cas had on her hair was any indication. Stood above them on the couch was Gabriel, to whom Cas was giving a stellar looking blowjob of his own.
"You guys got room for one more in there?” A voice came from above their heads. Dean looked up behind Benny. It was the moose, Sam, and from his angle on the floor, Dean could see that everything lived up to the nickname.
Benny arched his back, head landing against Sam’s meaty thigh. “You know I always got room for you, ma crevette,” he purred.
Sam knelt behind Benny, between Dean’s legs, and it took him a surprisingly long minute to realize what was happening. Benny plastered himself to Dean’s chest as Sam’s sure fingers rubbed where Dean and Benny connected. Dean felt light headed, sure that if he wasn’t already lying down, he definitely would have fainted by now.
Sam squirted more lube on the base of Dean’s dick, working his hand in circles as Benny’s ass bounced staccato beats against It. He pressed fingers against Benny’s rim, slowly pulling him apart while Dean lay almost immobile, letting him make room.
At last, he moved in, guiding his massive cock inside Benny beside Dean’s. God, the pressure. Benny practically melted on Dean, a heap of sweat and hair. Sam hunched over Benny, taking over the rhythm from Dean, moving them both with his deep thrusts.
Dean felt like he was going to pop out of his skin. He was proud of himself for lasting this long already.
Jarringly, he felt Cas’ foot hit his ear again. Without thinking, he reached up with his left hand and grasped Cas’s foot, tightening his hold when Cas startled and tried to pull it back. His whole leg was shaking and Dean just bet he was close to coming. Knowing Cas and his edging philosophy, Dean was determined to win the second round. He turned his head and sucked Cas’ big toe into his mouth. Biting slightly, he swirled his tongue around, sloppily soaking the digit. At the same time, he wrapped a hand around Benny’s heretofore neglected cock, stroking steadily and strong. Sam picked up his pace and within seconds Dean could feel Benny clenching around them both. He braced himself up on his hands and groaned as he came in hot stripes all over Dean’s chest.
Sam held Benny’s limp body against his chest and fucked him harder. It was all Dean could do not to bust a nut with him, but he was still set on beating Cas. Stamina was the name of the game after all.
Eventually, after Dean had sucked that toe like a pro, Cas’ foot jerked in a familiar way, the faint moan Dean could hear letting him know he’d won. He let go of Cas’ foot with a wet plop and basked for a second. Then, without warning, Benny was pushed forward against him as Sam came, his cock pulsing hard against Dean’s. He thanked God Cas had come cause this tipped him right over the edge, his orgasm ripping down his spine, everything becoming way too tight, way too bright.
When Dean came back to himself, gulping deep breaths, Sam pulled out with a filthy sound, their come dripping down Dean’s dick and balls. Benny eased off too, landing on his side next to Dean. He seemed to have trouble catching his breath as well.
“Ah, cher,” he panted, “that was definitely something.”
Sam had managed to get to his giant feet somehow and brought back a small hand towel and some wet wipes. Dean ran it perfunctorily across his chest. While he didn’t want the sticky feeling of dried come, he also kind of liked being covered in so much bodily fluid. When he was done, he lazily turned over onto his still shaky hands and knees, intending to climb back up on the couch.
That was the plan, at least. The plan got derailed when he felt a soft hand in the small of his back. Turning his head, he saw Anna behind him, trailing her nails up and down his crack interestedly. She flicked her pretty eyes up to his in a question. Raising an eyebrow, he wagged his ass back and forth at her in answer. Turning back to the couch, he crawled forward enough he could grab a free leg daggling off the side. It happened to be attached to Jo. She moved to sitting in front of Dean, spreading her legs over his shoulders as he settled in.
Anna didn’t have to work hard at Dean’s ass, the way already being well lubricated from his and Sam’s come and sweat dripping. She easily worked in a finger, then a second, licking around the edges. Dean mimicked her moves on Jo, licking firmly against her clit as he jacked two fingers in her pussy. In his peripheral, he could see bodies moving around, flashes of hair. Anna's thumb was doing incredible things in his ass, brushing up against the bumpy parts inside him just enough to send tingles down his sensitive cock. Dean arched his back, craving more.
He didn’t know how long he’d been there when he heard moans from across the room, then a plaintive voice called out, “Cas, c’mere! Bring the new guy with you, too.” Dean turned his head and saw the other redhead, Charlie, on the other side of the room, sandwiched between Sam and Benny, who had miraculously regained their erections. Maybe Becky was on to something about that food. Gabriel was knelt in front of her, petting her hair and looking incredibly patient despite the angry looking hard on he was sporting.
“What, Charlie? I’m kind of in the middle of something. You appear to be as well.” Cas was reclined on the couch under Bela, mouth wet from her juices. Bela and Meg were laying siege to his dick, bringing it slowly back to life.
“I know but I wanna do something and I need you guys too. Pretty please?” Charlie’s puppy dog eyes were a force to be reckoned with.
Cas rolled his eyes and looked up at the girls. “Sorry, ladies, the queen beckons.” He extricated himself from the couch and grabbed Dean away from Anna and Jo as he passed. They pouted but quickly got over it when Meg and Bela pulled them over to their side of the couch.
Benny was laid underneath Charlie, licking rosy nipples and moving his hips in small circles. Sam was knelt behind her, pumping in and out of her asshole, occasionally reaching down to tickle Benny’s hairy balls. Dean looked back at the couch to see the other girls occupying themselves. If he had to guess, it looked like a race was starting, with Bela and Anna seeing who could get their partner off first with just lips and tongue. If Jo’s cries were anything to go by, Bela was winning.
When they approached, knee-walking, Charlie popped her lips off Gabe’s cock, spit trailing.
“Hey! I’m Charlie, by the way. So, my personal record is quadruple, but since Dean showed up, I want to try a quintuple penetration tonight.” At Dean’s blank look, she elaborated, “That means five dicks in me at once.”
Dean blanched while Cas looked intrigued. How she could say that with such an earnest face was beyond him.
“Don’t worry, I've been training for it for a while. I was hoping the opportunity would present itself at some point and here you are.”
Jo perked up from the couch, “God, Char, you’re such a slut. Makes us feel left out.” She and Meg put on pouty faces before giggling into Anna’s breasts.
“Oh, don’t worry ladies, next time I’ll bring enough double ended dildos we can have ourselves a daisy chain.”
Jo raised her eyebrows at that and looked contemplative. She nodded. “Okay, you’re forgiven.”
Cas just shook his head in amusement. “Okay, Charlie, where do you want us?”
“Gabriel, can you go join Sam? I think height-wise that would be better. You guys, come up here. I can take two in my mouth, for sure.”
Gabriel withdrew and moved around behind her. He crouched atop her, Sam pulling out to make room. Gabe inserted two fingers of each hand into her gaping hole, spreading it wide. He hocked a thick loogie into her for extra lubrication, swishing it around with his fingertips, before pushing the fat head of his cock inside.
Draping himself across her back, he made room for Sam to rejoin. Sam’s cock was longer and thick, just like the rest of him. After some liberal application of lube, he screwed himself in next to Gabriel, just barely. Charlie nearly lost her balance from the force.
“Oh shit, okay, okay, gimme a second,” Charlie panted. “You guys are a lot bigger than the dildos I have at home.”
Sam hooted and preened, smacking Gabriel on the ass, jostling everyone.
“Sam! Chill the fuck out!” Charlie yelled.
Gabriel snickered and bounced his ass back against Sam’s belly. “Yeah, Sam, chill the fuck out.”
Charlie rolled her eyes. “Men.”
Bela, who by now had won the race and was sitting pretty in Jo’s lap, pointed out the obvious. “Charlie, you’re the one currently attempting to stuff yourself with five dicks. Maybe don’t act like your shit doesn’t stink.”
Charlie sniped back, “Bela, just cause you say shit in a pretty accent, doesn’t mean you’re not still a bitch.” She paused. “Love you.”
“Love you too, darling.”
Dean side-eyed Cas and mouthed, “Bitches be crazy.”
Charlie took that moment to take Dean’s cock into her mouth, sucking enthusiastically for a minute before replacing her mouth with her hand and switching to Cas’. The guys in back had found a rhythm, sawing back and forth, which had Charlie humming in approval, her eyes closed in what to Dean looked like pure contentment. She eased him inside her hot mouth alongside Cas, getting both heads between her cherry lips. After a few nibbles, she popped off with a smack and shouted to Jo, “Get my camera from upstairs, would you?”
Dean blinked. “Camera?”
Charlie looked up at him. “Oh yeah, this shit’s going on my fridge next to my signed photo of Emma Watson. Gotta be proud of your accomplishments, you know.”
“It’s the little things, Dean,” Cas deadpanned.
Dean swallowed his laugh and watched Jo bound up the stairs and, quicker than he thought possible, back down with a Polaroid camera. Well, at least there wasn’t much chance of this getting online. Dean wasn’t a prude, obviously, but he never wanted to be one of those guys flashing his junk all over the internet.
Jo crouched on the side, raising the camera to her face. Charlie quickly engulfed Cas and Dean, startling a gasp out of Dean at the hot-wet sensation. He tried to remember to be gentle on her hair. “Guys, move those legs for me, I want to make sure I get the money shot.” Jo gestured frantically towards Sam and Gabriel. “Okay now Charlie, breathe out and breathe in... some penis.” She giggled at her own joke and clicked the camera.
“Jo, I think you’re missing your calling as a porn director. I know some people I could hook you up with if you’re interested...” Gabriel offered. Having just met the guy, Dean couldn’t tell if he was serious or not.
“Thanks Gabe,” she said, “but if they’re anything like you, I think I'll keep my day job.” She smiled faux sweetly.
Several shots later, she was done.
“Okay guys, you can get back to your regularly scheduled programming now.” Charlie sighed as Sam slowly withdrew with a squelch, followed by Benny, who rolled out from under her like a GI Joe. Gabriel stayed put. When Benny was clear, he pushed Charlie down flat to the floor, tipping her hips slightly, obviously chasing his own fun.
Cas grabbed Dean by his bicep and literally manhandled him over and up on the couch. Cas positioned him on his knees, facing the back, and pressed himself up against Dean’s back. His thighs were bracketing Dean’s, making him feel both trapped and secure at the same time.
“Alone at last. You must think you’re so cute, huh?” His breath was hot against Dean’s cheek.
“I think I'm adorable,” Dean bragged, desperate to feel every inch of this man.
“You’ve been driving me crazy all night, you know that?” he murmured into Dean’s ear, licking the shell and sucking on the lobe. “No, of course you don’t, mister don’t-call-me-beautiful. I think I'll call you whatever I want and you’ll like it, won’t you?”
What was Dean supposed to say to that, no? Instead, he just nodded like he was that bobble headed thing his boss kept on his desk, and wow, was thinking about Bobby definitely not the right thing to do at the moment.
Fingers nudged at his mouth and Dean eagerly took them in, getting them sloppy with spit, as Cas rained kisses across his shoulders. He could feel Cas’ hard dick against his crack, pushing insistently. He barely needed it after the attention Anna had given him earlier, but Cas took his fingers from Dean’s mouth and pushed them in his hole, pulling a gut deep moan out of Dean as he scissored them expertly. Cas seemed pleased to no end.
“That’s right, who’s my little cock slut?” Dean could hear the grin on his face.
Cas removed his fingers and angled himself into Dean, pushing the thick head of his cock against Dean’s stretched rim. When he popped in, Dean let out a full body shiver. Cas grasped his hip with one hand and wrapped his other around Dean’s neck again, forcing Dean's head back against his own. Cas barely moved, just worked his hips against Dean’s, slow and deep, feeling skin against skin for what seemed like miles. The other sounds in the room faded as Cas huffed in his ear, little puffs that punctuated his movements. Dean's cock was getting no attention whatsoever, trapped between Dean’s belly and the rough couch, leaking steadily. It was just enough friction to drive Dean out of his mind.
“Think it was cute how you grabbed my foot earlier? I know it was you. Damn near choked Bela cause of your little stunt. But honestly, you’re what drove me over the edge, that soft mouth of yours. So unexpected. Same with Anna. Seeing you come all over her, unable to help yourself. God, what a treat you are.”
Cas wrapped his full body around Dean, hugging him tight as he slid in and out. Every time he left, Dean’s channel sucked him back in like an old friend. Cas’ fingers trailed along his jawline, leaving sparks in their wake. Dean's eyes slid closed as he savored the feeling.
Just as he felt like he was about to melt into a pile of pudding, the lights blinked and a weird noise sounded through the room. Cas sighed and laid his head on Dean’s shoulder. “Goddammit.”
“What the fuck was that?” Dean asked.
“Becky’s version of a five-minute warning. Makes her feel cultured, I guess, like intermission at the ballet.”
“Warning for what?”
“It’s nearly midnight. Becky likes to warn us before coming down and ending things. Wants to make sure we’re all ready for the bucket.” Cas kept himself still inside Dean, unwilling to pull out until he absolutely had to. “Oh, the things I'll do to you when we have the time,” he said softly, just loud enough for Dean to hear.
Dean tried his best to ignore that and focused on the other thing. “Bucket?”
Cas let out a soft laugh. “You’ll see.” His cock made an obscene sound as he withdrew entirely from Dean, who immediately felt bereft. Everyone in the room was separating, moving to get food and drink or towel off. However, the atmosphere still felt tinged with excitement, like things weren’t quite over yet.
Dean settled down into the couch as Cas wandered off toward the table. Looking around the room, he noticed all the guys still seemed hard, lazily stroking themselves or each other. The girls also piled together again, petting each other softly and giggling quietly. Cas returned with a chocolate bar right as Becky stomped down the stairs holding the little metal pail she’d handed Dean earlier.
“Hello, everyone! I hope it’s been a good night,” she crowed. Dean found himself glad that Becky was merely the host of this thing and not a participant. Someone would have to keep her mouth stuffed the whole time.
Cas handed a piece of chocolate to Dean who ate it gratefully. They sat shoulder to shoulder on the couch, Cas having thrown his left leg over Dean’s right, keeping him anchored to his side. Dean tried to hide how much he liked it.
“And now for the finale, I present to you the come bucket!”
Dean still felt confused, and also like he was getting hearing damage from Becky’s screeching.
“Dean! Since you’re new, I'll explain. This is the bucket I had you put your name in earlier. Everyone does it. At the end of the night, I draw a name and that person gets to be the come bucket. That means all the guys get to come for the final time on their face. Sounds fun, right?”
Okay, he’d just been involved in a multiple penetration scenario but this was still the porniest thing he'd heard all night.
“Uh, yeah, sure, sounds super fun.” He even did a thumbs up. He could feel Cas silently laughing next to him.
Becky swirled her hand around in the bucket theatrically before drawing out a name.
“And the winner is...Dean! Wow, first time’s the charm, huh? You have nice handwriting.”
Dean blinked, stunned. Well, this sure was a turn of events. The girls catcalled from the couch: “Yeah, newbie’s the come bucket! Man, it’s times like these I wish I had a dick.”
He slid to his knees on the carpet, taking his cue from the guys coming to stand up around him. He'd always been a fan of come shots in porn, but now he was starting to rethink that stance. It was a lot more intimidating when you were the one on your knees receiving rather than giving.
The other men surrounded him, stroking themselves and his hair. He decided to just go with it. That had been his mantra for the night anyway. Why not keep it going?
Cas stood in front of him and as he opened his mouth and leaned his head back, he focused on those steely eyes. He reached up and added his hands to the mix, stroking up and down randomly, running his short nails along Sam’s balls, rubbing Gabriel’s thigh. All he could hear was the slap of skin on skin as these men he barely knew jacked off intensely above him. He had to admit, it felt pretty good knowing he was the sole object of their attention.
Benny let loose first, shooting his release across Dean’s cheek, letting it drip down his jaw and onto his collar bone. He was followed shortly by Gabriel, on his right side, who shot warm ropes across his nose and lips. Sam’s hand in his hair tightened as he came next, thick globs landing on his chin and running down the contours of his lips. Cas lasted a few seconds longer before squirting straight into Dean’s open mouth. When he was done, Dean smacked his lips, savoring the salty flavor.
He felt dazed. Above him was the sound of rustling and wheezing. He was afraid to open his eyes for fear he’d get come in them. So he jumped a little when he felt gentle hands on the sides of his face. He cracked open one eye to see Cas squatted down in front of him, nearly nose to nose. His knees bumped against Dean’s waist. He smirked that little smirk of his and leaned in and licked, long tongue running up and across Dean’s cheek, tasting the combined come on his face and looking like the cat that literally got the cream.
When he was done cleaning Dean’s face, long minutes later, he leaned in for a wet, sloppy kiss, Dean’s mouth still tinged with the remains of their come. He let out a sigh and relaxed into Cas’ hold. The other men had already turned away, chatting with each other and preparing to leave. Dean felt like they were in their own bubble, there on the floor.
After what felt like an eternity, he opened his eyes fully and focused on Cas’ face. They were now alone in the basement, everyone having already gone upstairs and possibly even left. Cas helped him to his feet and gave him a sly smile.
“I have to admit, in all this time she’s never drawn my name from the bucket. But looking at you, that blissed out face you have, it really makes me want to try sometime.”
“Or I could show you how it feels,” Dean blurted out. He instantly wished he could take it back. He was worried the moment had passed, now that the orgy was officially over. He felt stupid for presuming this absolute sex god would want anything to do with him outside this room. Cas was probably just being sweet on Dean because it was his first time. Dean remembered taking his first girlfriend’s virginity and being really into it and then breaking up with her the next day. There wasn’t always a correlation.
Cas’ smile got wider and he took Dean’s hand. “Think I might like that. Can I walk you up the stairs?” he asked, as if they were at the end of a first date and not two virtual strangers standing naked in a room which still stank of group sex.
Dean blushed and ducked his head. Cas took that for the yes it was and led him towards the stairs, grabbing a bottle of water on the way out. Dean couldn’t believe it was all over. He probably would never see this guy again, unless he decided to come back next month. He wasn’t sure about the rules now. Did he have a standing invite after the first time or was it invitation-only each month? How often did the group change? Everyone else seemed to know each other well, so how often did they have newbies like Dean? He was treated almost with curiosity by some members.
They entered the room where Dean had undressed to find just two piles of clothes left. His theory that everyone else had already left seemed confirmed. Dean felt strangely self-conscious as he pulled his briefs and jeans on. The leaving part was always the most difficult. He hadn’t thought that would be the case tonight, since everyone was in the same boat, but this connection he’d made with Cas, that he hoped was mutual, was messing with his head. It felt like there could be more.
When he was done getting dressed, he took a deep breath and turned around to see Cas pulling on a tan trench coat. Odd choice, but it seemed to suit him anyway. Brought out the blue in his eyes even more. Dean grabbed his own jacket, the leather one that was starting to get patchy in the elbows, and tried to figure out what to say. He was used to having sex with dudes, but not used to feeling like the girl.
Thankfully, Cas made the decision for him. Grabbing the phone out of Dean’s hand, he deftly typed something into it before handing it back. Dean glanced down at it: Castiel Krushnic plus his phone number. Hmm. Interesting name for an interesting dude.
“I’d like to continue where we left off earlier, if that’s okay with you,” Cas said, looking as cool and collected as the cucumbers Dean absolutely didn’t used to practice with.
“Yeah dude, totally. Awesome.” Dean just could not stop tripping over his feet with this guy. Thankfully, Cas didn’t seem to mind.
Dean followed him out to the porch where he’d had his little existential crisis earlier. He noticed one of the street lights was out, a lone spot of black in the otherwise well-lit neighborhood. Dean’s Impala and a grody looking Lincoln Continental were the only cars left at the curb. Dean huffed out a little laugh before he could catch himself.
“What, you got a problem with my car?” Cas said somewhat defensively.
“No! No, I just remember seeing a motorcycle when I got here and I was kind of hoping it was yours.” Dean would have loved to ride it behind Cas, his hands clutched tight around that firm waist.
“Nope, that belongs to Meg, believe it or not. A tough ride for a tough bitch, in her words.”
From the few minutes he’d really spent with her, Dean agreed with the assessment.
“So, uh, I guess I'll catch you later?” Dean dug the toe of his boot into the wooden steps, hesitant to leave.
Cas smiled wide and reached for the lapels of Dean’s jacket, pulling him in for another one of those brain-melting kisses Dean was starting to think was the norm, not the exception.
Forehead to forehead, Cas murmured, “You better or I'll come find you myself. I'm not one to be patient in my pleasures, and you, Dean, you are definitely a pleasure worth pursuing more of.”
Dean felt lightheaded, like that time he smoked pot for the first time in high school with his buddy Garth. Although this time, he was fairly sure he wasn’t hallucinating.
Cas left him stunned on the porch and strolled down the steps to his ugly-ass pimpmobile. Settling in to the driver’s seat, he started the car and leaned out the window with a wink.
“I’ll be seeing you.”