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Plan D for Dumbass

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Sam and Jess had joined them for dinner in their favorite local restaurant, and they'd all had enough drinks to be lightly buzzed.

Now they were back in Cas and Dean's cosy studio apartment for a night cap.

It wasn't a space designed to accommodate four adults, so Sam and Jess were headed to the motel up the street in a little while. 

The head of the bed was pushed up against one wall, and there was a round table with two chairs, as well as a small two-seater couch and one chair in front of the TV. There were two small rooms off the main area; a tiny kitchen and an equally tiny bathroom. 

Dean was over the fucking moon to have all his family together. He really did miss his step-brother. And Jess was really fun; he enjoyed her company more and more every time they saw each other. 

Dean was leaning against the wall, drink in hand. Sam and Jess were both sitting at the round table, and Cas was cross-legged on the end of the bed. They were trading stories and jokes, and generally having an awesome evening.

Dean looked over at his step-brother, who for some reason was suddenly shifting uncomfortably in his chair. Sam frowned and rubbed a hand down his face. 

"What's wrong, Sammy?" Dean asked.

"I, uh..." Sam huffed out a short, awkward laugh. "I'm not sure I can stay here much longer, Dean."

Dean frowned. "Why not?"

Sam looked over at Cas, then back down at his hands.

"I'm sorry," he said. "This is gonna be inappropriate, but... the smell."

Three confused faces stared at Sam.

He sighed.

"Of Cas," he specified, sounding exasperated at having to spell it out. "The smell of Cas. It's - stirring stuff in me which shouldn't get to be stirred any more."

Cas blushed, Dean smirked but couldn't help the little possessive feeling that crept up his spine, and Jess - to everyone's surprise - hardly reacted at all. 

Sam looked at her.

"I'm sorry, sweetie," he said. "I guess old habits and all that."

"Hey, no need to apologise," she smiled. "I bet he smells - really good, huh?"

The three boys looked at her in surprise.

"Are you kidding?" Sam asked her, with a kind of knowing half-smile.

"Kidding about what?" Dean frowned. "What's going on?"

"Oh, nothing," Jess said, aloof. "Excuse me for a minute."

She got up and headed to the bathroom. Once the door had closed, Dean turned back to his step-brother.

"Alright, spill, what am I missing here?"

Sam rubbed his chin and bottom lip with his hand.

"Well," he began. "Jess kinda has a - kink."

"A kink?" Cas raised a quizzical eyebrow.

"Yeah," Sam said, with a wry half-smile. "We discovered it by accident, I guess, when I was telling her about us. She, um, she likes the thought of it. Of us. All. Together."

Dean stood up.

"Excuse me," he said, a querying index finger raised in the air. "Are you saying that your girlfriend gets a kick out of imagining you screwing guys?"

"Yeah," Sam chuckled. "That's exactly what I'm saying."

Cas necked his drink. "A few more of these and she might get a live showing.”

Dean looked sharply at his Omega, and Sam's eyes went wide. 

"What?" Cas asked, defensively, though he sounded a bit worried that he'd pissed Dean off with the suggestion. "You're not going to tell me you don't still think about it? About the three of us?”

Dean frowned. "No, I - well, yeah, sometimes but I... Jesus, are we really discussing this?"

Dean couldn't deny that he did still occasionally indulge himself in memories of nights with Sam and Cas. The three of them used to spend literal hours exploring new realms of ecstasy, and even though he had no regrets about mating with Cas and it being just the two of them now, there was nothing wrong with replaying the trio's greatest hits in his head every now and then. 

But he didn't think it would ever be a thing again. If it was actually on the table, then that was - interesting.

The bathroom door opened and Jess returned.

"Sorry," she smiled, genuinely apologetic. "Didn't mean to cause an atmosphere."

"You didn't," Sam assured her. "Everything's cool."

Jess nodded, slowly.

"So... am I getting my live porn, or...?"

They all froze, then Dean laughed.

"I like you," he told her.

"Enough to share your mate?" she asked, tone revealing that she knew she was pushing it.

There was a tight silence.

"You - really wanna watch that?" Dean asked, quietly. "You'd be happy watching Sam, uh... playing with someone else?"

Jess sat down. 

"I'm not a possessive person, Dean," she shrugged. "I don't get jealous easily; maybe it's a Beta thing or maybe it's just who I am. I guess I'm a bit of a voyeuse. Frankly the idea of watching Sam getting all Alpha with you guys makes me really hot."

All three boys shifted nervously and chewed on their lips.

"Plus," Jess continued. "I hope you don't mind me saying this, but you are all really fucking sexy. Quite honestly just talking about it is making me a little bit wet."

There was complete silence as they all stared at her, open-mouthed.

Jessica coughed, and downed her drink.

Sam looked at Cas, who looked at Dean, who shrugged and smiled in a ‘permission granted’ way.

Then Dean looked back at Sam, who licked his lips. That action alone was enough to wake up some dormant feelings in the elder Winchester, and the decision was made.

"You wanna direct?" Dean asked Jess, quietly.

A naughty grin unfolded on her face, and she nodded, slowly.

Sam walked over to her and kissed her.

"I love you," he whispered, both hands on her cheeks.

"You too," she replied, sweetly. Then she pushed him away, sat back and crossed her legs. "Now take your shirt off."

The change in tone was evident to everyone. Game time. 

*

Cas slipped off the bed and over to the wall to dim the lights a little, as big Alpha Sam obeyed his beautiful, bossy Beta girlfriend.

The sight of that torso sent some thrilling memories through Cas, and he was suddenly very grateful that this family was so delightfully fucked up. 

He adored Dean with all his heart and soul, and if he never slept with anyone else his whole life, he wouldn't care. But the thought of recreating some of those awesome positions that are only possible with three...

"Come here, Dean," Jess instructed.

Dean stalked slowly towards his step-brother.

"Been a while since you two touched, huh?" Jess murmured.

They nodded.

Jess addressed Sam. "Take off his shirt," then Cas; "Come here, baby."

Sam slid his hands under Dean's shirt and lifted it over his head, as Cas hurriedly went to kneel down obediently next to Jessica's chair. She stroked her fingers through his hair. A Beta she may be, but she was intuitive and smart, and knew how to push a natural Omega's buttons.

"They're beautiful aren't they, Cas?" she purred. 

Cas was powerless to do anything but exhale heavily in agreement.

The Winchesters stood, staring into each other's eyes, chests heaving and anticipation buzzing in the space between them.

"Wanna watch them kiss?" Jess asked Cas, tugging gently on his hair.

He bit his lip in pleasure, and nodded.

Jess smiled at him, then beamed up at the Alphas.

"Kiss," she commanded, in a voice like velvet. "Slowly."

*

Sam ran his fingers along Dean's stomach, making Dean's muscles jump, and letting his hand come to rest just under his ribs. He gave a possessive squeeze, as Dean gently wrapped his fingers round the back of his step-brother's neck.

Dean's breath was getting heavier as he pulled Sam towards him. Thank god Jess was controlling this. It absolved him of any responsibility. He could enjoy this 3D trip down memory lane with no guilt. 

As his lips connected with Sam's, he moaned involuntarily and felt his dick harden inside his jeans. Sam tasted as he always had, except now he was mixed with something else - a taste and scent which must be Jessica. Dean hadn't kissed a girl since he was a young teenager, and the novelty of that taste on Sam's tongue was delicious. 

*

"Look, Cas," Jess was speaking softly, but her voice wavered with arousal. "Sam's hands are so strong round Dean, aren't they?"

Cas whimpered a little.

"I love those hands on me," Jess continued, fingers kneading through Cas' hair. "I love letting Sam hold me down to fuck me. Did you like it, Cas? Did he hold you down on his dick with those big hands?"

Cas closed his eyes. Damn, she was good.

"You want him again?" Jess whispered. "Want Sam's hands? His fingers? His cock?"

"Yes," Cas breathed.

Jessica stood up, and led Cas by the hand to the bed. Dean and Sam stopped kissing to watch what she was doing, but they kept their hands on each other.

Jess climbed up, sat against the headboard, and pulled Cas towards her.

"Take off your shirt," she instructed, "and turn around."

He did as he was told, threw his t shirt to the floor and turned to face the Winchesters.

"Lie back against me," Jess murmured in his ear.

So he did.

Jess had one hand playing with his hair, and she was running the fingertips of the other up and down his ribs.

Cas was panting, and staring from one Alpha to the other. Both of them were wide-eyed with lust.

"Come here," Jess told them.

The Alphas stalked towards the bed, hardened cocks pushing against the front of their jeans. Cas shivered with the anticipation. 

“Take off your pants and your underwear,” Jess commanded, casually, still gently tickling Cas’ sides.

Cas watched as Sam and Dean did as they were told. Seeing them obediently follow instructions was hot as fuck in itself, and his heartbeat raced as the two unfeasibly large cocks were exposed.

Sam grinned at Jess over Cas’ shoulder, and Cas wondered what her expression was right now. She sounded as though she was staying pretty cool, but surely no one could remain poker-faced at the sight of two naked Winchesters.

“What do you think, Cas?” Jess breathed. “You want them to touch you?”

Cas had lost his speech function sometime during the Winchesters’ strip tease, so he just nodded, and squirmed as slick started to leak from him.

Jess lifted one hand away from Cas’ skin, and beckoned to Sam with her forefinger.

Sam crawled up onto the bed. 

“Go ahead, baby,” Jess said, in a soft tone that sent tingles up and down Cas’ back and legs. “I want you to run your tongue all over Cas’ body.”

Cas whimpered, as Sam smirked mischievously and knelt on the bed at Cas’ hip. He leaned forward, and began to lay gentle kisses on Cas’ torso. Each one made Cas arch his back with pleasure. He looked over at Dean - his Alpha - to make sure this was still okay. Dean’s eyes were wide and dark, and he was breathing heavily. 

Always able to accurately read Cas’ mind, Dean smiled at him reassuringly, and winked. Cas tried to smile back, but with the ecstatic pleasure of Sam’s mouth on his skin, he could only manage a sort of contorted grimace. 

Sam nibbled lightly at Cas’ nipples, having evidently not forgotten all Cas’ trigger points, then ran his tongue all the way down from his sternum to his stomach.

“Take off his pants,” Jess demanded, voice sounding distinctly more flustered now.

Sam unbuttoned Cas’ jeans and tugged them down. Cas assisted by lifting his hips off the bed so Sam could get his pants over his ass. Though Jess hadn’t specified that Cas’ boxers should come off too, Sam removed them as well, and tossed the articles behind him to land in the existing heap of discarded clothing. 

“Come here, Dean,” came Jess’ voice.

Dean took the few steps it took to get him to the end of the bed, and stood awaiting further instruction. 

“Up here,” Jess clarified, and as Dean walked round to the head of the bed, she slid herself out from underneath Cas.

She eased him up gently and laid him back down again on the pillow, as she moved to kneel up at the side of him. She stroked her hand through his hair.

*

Dean stood on the other side, desperate to touch himself but forcing himself not to, to build up more tension and ultimately get a better payoff. He gazed into his Omega’s dilated pupils, and smiled. As much as he was going to enjoy this, his ultimate objective, as always, was for Cas to feel treasured and pleasured. 

Jess looked down at Sam, who was half lying on the end of the bed, between Cas’ legs.

“Suck him,” she whispered to her Alpha.

Dean watched Sam slide his mouth slowly down Cas’ dick, hands holding the outside of the Omega’s thighs. Cas gasped and arched his back, and Dean looked back to find him staring into his eyes.

“Aaahhh…! Saaaamm…” Cas cried.

Dean couldn’t, and didn't, resist leaning over on the bed to claim Cas’s mouth in a steamy kiss, despite not being instructed to do so by their ‘director’. He withdrew his tongue, then held Cas’ face close to his, and let his lips just brush against Cas’ as they breathed together.

“May I?” came Jess’ quiet voice.

Dean looked up. He nodded, and Cas turned his face towards his quasi-sister-in-law.

Jess pulled her shirt off over her head, then took off her bra. She leaned down to kiss Cas, dominant but tender.

*

Cas had never kissed a girl before. It was nice. Being a Beta, there was nothing overpowering about Jess’ base scent; she just smelled like perfume and shampoo. And also a little like Sam, for obvious reasons. Her lips were full and pouty, like Dean’s, but a little bit smoother. 

The combined sensations of being kissed by a topless girl for the first time, Sam’s mouth on his cock, and - oh fuck - Dean’s teeth on his nipple, were sending Cas into bliss overdrive. 

“You want Sam to fuck you, sweetie?” Jess asked, softly. 

Cas looked at Dean before answering. He really did want that, but the first sign of discomfort from his soulmate and he would end this immediately.

“I think he does,” Dean said, with a smile and another nip to Cas’ chest. 

Sam pulled off Cas’ dick with a sweeping lick, and knelt up on the bed between his legs. He pushed Cas’ thighs up, and bit his lip as he looked down. Cas stared up at him, wanting so badly to feel him inside him once again. 

“Go ahead,” Jess instructed, still stroking Cas’ hair. “Fuck him.”

Cas cried out as Sam's huge cock breached him for the first time in a long time. 

“Oh, Cas,” Sam breathed. “Fuck.”

“Go slow, baby,” Jess told her mate. “You've all gotta make this last for me.”

“Yes ma’am,” Sam answered, and holy Christ, that was sexy. 

Dean began to languidly kiss Cas’ neck, and Cas whimpered at the feeling of having the two Winchesters on him again. He wouldn't trade Dean for anything, but god, apparently he’d missed this more than he realised. 

“Cas?” Jess asked.

Cas looked at her, but didn't answer because he couldn't fucking talk right now. 

“Have you ever licked a girl out before?” 

Dean moaned into the skin on Cas’ neck, evidently liking that idea.

Cas shook his head. He'd never really been attracted to girls, but Jess was so beautiful and the atmosphere in the room right now was so hot. Why the hell not? 

Having got a nod of approval from Dean, Jess got up onto her knees. She pushed her skirt and panties off, then positioned herself above Cas’ face. She put her hands on the wall above his head, and lowered her body down. 

*

Watching his step-brother's girlfriend sit on his boyfriend's face hadn't exactly been on Dean's to-do list. But, here he was doing just that, standing by the bed with his fist wrapped round his dick. And it was unassailably hot. 

Jess groaned as Cas held her thighs and put his tongue to work. 

Mesmerized, Dean put out a hand to massage one of Jess’ gorgeous breasts. She sighed in pleasure, and closed her eyes. 

Sudden realisation that he'd touched his brother's mate without permission made Dean pull his hand back in a hurry, and he looked anxiously at Sam.

Rather than any sign of possessive angry Alpha, all Sam had in his face was pure lust.

“Come here,” Sam whispered, and Dean stepped towards him. 

He took in the old familiar sight of Sam screwing Cas, chest and stomach firm and defined, face glistening with sweat. He put his hand in Sam’s hair, and pulled him in for a kiss. 

Sam tasted so good, and it was so nice to sink into a good dirty kiss with him again. Kissing him slow and deep while feeling the movement of Sam's body rocking into Cas below them was sending all of Dean's blood right to his cock. It was overwhelming how turned on he was.

“You're still really fucking hot,” Dean said, voice low, and lips against Sam’s. 

Sam glanced at Jess, and Dean followed his eyeline. Jess was turning herself around to face them. 

She bent over at the waist, thighs either side of Cas’ face, til she was on all fours above him. She winked at the Winchesters as she lowered her mouth round Cas’ cock. 

Dean looked over at where his mate's face was obscured by Jess’ lower half. Cas was still holding on to her thighs, and Dean could see his head moving. He was obviously enjoying himself in there. 

Don't develop a taste for that, sweetheart, Dean thought to himself.

He heard Cas’ whine of pleasure as Jess initiated the sixty-nine. 

“Holy shit, Jess,” Sam breathed.

Jess licked up Cas’ shaft and round the head, before looking up at Sam.

“Fuck him harder now, baby,” she told her mate, with a naughty smile. “Make him scream into my pussy.”

All three men groaned at the filthy talk, and Sam did just as he was told. 

Dean suddenly became aware that he was the only one who didn't have his dick in anything, and he felt a little left out.

As if reading his mind, Jess reached out a hand to grab said dick, and stroked him firmly. She alternated between sucking Cas and leaning up to suck Dean, and Dean was still within kissing distance of Sam, so he indulged in that a bit more too. 

Fuck, this is some good shit. 

Soon, however, Jess totally lost her rhythm, and she put both hands on the bed either side of Cas’ legs.

“Oh god, oh god,” she was chanting. “I'm gonna come, I'm gonna come, oh fuck!”

Sam put a hand in Jess’ hair, petting her as she slid into orgasm.

“Yeah, baby,” he urged, still fucking steadily into Cas. “Come on, come all over Cas’s mouth.”

Dean moved away from them and crouched down on the floor, arms and face next to Cas on the bed. From this angle he could see Cas’ tongue and lips working on Jess’ pussy.  

“You're making her come, baby,” he encouraged, and Cas hummed in acknowledgement.

“You're so good,” Dean went on, stroking Cas’ hair. He knew his precious Omega would be needing some more reassuring praise by now. “Look at you licking her clit, making her so wet, she's gonna come just for you, baby, keep going, keep going...”

Jess yelled out, and her legs started to shake. 

“Yeeeeaah! Oh, ohhhhhhh!”

When she was done, she rolled off of Cas and onto her back. 

“Shit,” she breathed, sounding very satisfied. 

*

Cas’ face was dripping wet, and he felt pretty proud of himself considering that was his first attempt at cunnilingus. 

He was about to wipe his mouth with the back of his hand, when Sam was suddenly over him, kissing him, hungrily.

Sam and Cas hadn't kissed in so long, and Cas just melted into the sensation of it. He heard Dean moan in pleasure beside him, and he was glad the kiss looked as good as it felt.

Sam pulled up after a while, but his lips still grazed Cas’s as he spoke.

“Wanted to taste her on you,” Sam muttered, in explanation. “So fucking hot.”

Cas smiled, as Sam pulled up a little and started fucking Cas harder and faster.

"Fuck," Sam said, closing his eyes. "I'm really fucking close now." 

Jess knelt up and put her arms round Sam's neck, kissing the side of his face. 

"Slow down baby," she cooed. "Pull it back for me."

Cas felt Sam slow his thrusts, and was really impressed at how quick Sam was to please his gorgeous girlfriend. 

Cas looked at his own engorged cock, and had an idea. As a very happy Omega bottom, he’d never penetrated anyone, and now seemed like the time for it.

“Jess?” he said. “Wanna ride me?”

She licked her lips and asked; “That okay with everyone?” 

“Be my guest,” came Dean’s voice, and he pulled Cas in for a sloppy kiss.

“Fine with me as long as you face this way,” Cas heard Sam say.

He didn’t see Jess mount him, as he was still lost in Dean’s powerful kiss, but he sure felt it, and holy shit.

He cried out with the unfamiliar pleasure of that wet heat, and looked over to see Jess sinking down on him while wrapping her legs and arms around Sam, who was still fucking him slowly.

“That’s something I never thought I’d see,” Dean said next to him in a husky voice. 

Sam had his hands round Jess’ waist, and was bouncing her up and down and kissing her periodically, while still managing to keep a steady rhythm inside Cas. 

Dean chuckled next to Cas’ ear. “Pretty impressive there, Sammy”, he said, but Sam had far too much to concentrate on to respond. 

Dean turned back to Cas and licked and kissed his neck. “How do you feel, baby?” he asked.

“So good,” Cas sobbed. “I can’t tell you how it feels - to be inside someone and have someone else inside me at the same time.”

“It looks fucking amazing from here,” Dean smiled. “And hey, might as well go for the hat-trick.” 

He moved to standing, and held his cock next to Cas' mouth. Cas opened up greedily, and laved his tongue around Dean's shaft as Dean pushed it along the inside of his cheek. 

Cas would never get over this as long as he lived. Sam’s dick in his ass, Dean’s in his mouth, and his own in Jess’ pussy. This was like something out of the wildest pornos, and certainly not something he thought he’d be doing when he woke up this morning. There was so much ecstasy racing through his veins he didn’t know what to focus on. He didn’t feel close to orgasm though; he felt like he was just riding the waves of what he was feeling, and felt no urgency to rush to the finish. 

He focused on the sounds of Jess’ gasps, Sam’s choked grunts, and Dean’s soft praise. 

*

The feel of Cas’s mouth on his dick never felt any less phenomenal than it had the first time it had happened, and Dean sighed in relief at the feeling. 

“Good boy, Cas,” he murmured. The praise was a reflexive habit now, but he still meant every word. “So good, such a good boy for me.”

He looked up at Sam, who was grinning at him over Jess’ shoulder. 

"You thinking what I'm thinking?" Sam asked.

Dean laughed a little, knowing exactly what Sam wanted. It was his favorite position. 

"Sure thing, man." 

Dean extracted his cock from his mate's lips, and put his hands on Cas's shoulders to rotate him so that his head was slightly overhanging the side of the bed. 

Meanwhile, Sam had also pulled out at the other end, so he could reposition himself, kneeling on the covers facing Dean instead of standing on the floor. But not before effortlessly lifting his mate off Cas's dick. Dean shook his head a little, always surprised and impressed by Sam’s strength. 

Jess had slid back up the bed to watch, intrigued. 

The Winchester boys had discovered long ago that this was the best position for Cas to deep-throat. He had in turn discovered that the gagging sounds he was capable of making drove both the boys absolutely crazy. 

"You'll like this," Sam told Jess with a wink. 

Dean watched as Sam reinserted himself into Cas, and Cas groaned and lifted his knees. Dean spread his legs a little and moved closer to Cas' head, feeling Cas' hands grip his asscheeks. 

"Hold on," Jess said, crawling towards Cas' face. 

"I wanna feed you to him," she said to Dean, biting her lip. 

"Jesus, Jess," Dean chuckled, face feeling hot. "Anything you want."

Jess looked over her shoulder at Sam. 

"Is it okay if I get the full set and kiss Dean, too?"

Sam smiled. "I wouldn't dream of depriving either of you of the pleasure," he said.

Jess turned back to Dean, smiling, and knelt up to kiss him.

Dean leant into it happily, sliding his tongue over hers when she opened her mouth a little wider. He put his hand on her neck and hummed into the kiss. 

We're fucking weird, he thought. But thank god, cause this is all kinds of awesome.

They broke away at the same time, and grinned at each other. 

Dean looked over at Sam, who was thrusting slowly into Cas. Looking down, Dean saw Cas' beautiful face smiling up at him.

"Go ahead, Miss Moore," Dean told Jess. "Feed him my cock."

Jess ducked down and stroked Dean's already hard dick. She also helped herself to a taste, which Dean didn't object to at all. Hell, this was a fucking free-for-all now, she was more than welcome. 

"Open your mouth, Cas," Dean heard her instruct. 

Jess' soft strong fingers wrapped around him, and guided him into Cas' warm mouth. 

"Here you go, baby," Jess said to Cas. "Just what you wanted. Open wide for me, let him go all the way down."

Dean moaned and let his head roll back. He put his hands down on Cas's jaw as he slid past Cas's tongue and down his throat. Jess's hand had come away from his shaft, and she rolled his balls a little in her palm before sitting back on her knees to watch. 

"Fuck his mouth, Dean," came Sam's voice, sounding wrecked. "Please. It's been so long since I saw it. Make him make those sounds."

Dean felt Cas adjust himself beneath him, and he knew his mate was ready. 

Dean started slow, enjoying the nostalgic sensation of him and Sam both being inside Cas at the same time, then he began pounding into Cas' mouth, making him take it deep with every thrust. 

Cas started making those fucking amazing sounds, those filthy choking, gagging noises that make him sound like a professional pornstar. 

“Cas,” Jess said, running a finger over his nipples. “You’re going to come just like this, Cas. With one cock in your ass and one down your throat.”

Dean breathed more heavily as he listened to her talk. 

“Touch yourself, Cas,” she told him. “Stroke yourself for me.”

She looked up at Sam. “How does he feel?”

“So fucking good,” Sam answered, hands tight around Cas's legs. “Wet and tight. Holy shit.”

“You look so hot,” Jess said. “I’m so lucky.”

She then adjusted her position so she was high on her knees next to Dean.

"Hey," she said to him, gently removing one of his hands from Cas's face and holding his fingers. "Can I borrow these?" 

She looked into Dean's eyes as she slowly sucked two of his fingers into her mouth. 

Dean swallowed hard, hoping his dumbstruck expression would convey his consent. 

Apparently it did, since Jess drew his arm down, angled his hand between her thighs and knelt herself down on his fingers. The wet warmth of her pussy felt really nice, and Dean circled his fingers around inside it, stroking the wall of skin. She put her hands on his shoulder for balance.

"Fuck," she whispered, then looked back down at Cas.

“Come on baby,” she purred. “You can let go. Let's see how hard they can make you come." 

Dean felt as well as heard the desperate sounds Cas was making, and he watched greedily as Cas jerked himself off. Dean felt insanely close to spilling down his mate’s throat, but he wanted to hold off a little longer. He was splitting his focus between fucking Cas's throat and fingering Jess, and jesus he couldn't tell if it was all too much or not enough. 

Then, Jess did something that hurtled Dean over the threshold. She moved away from him, releasing his hand, bent forward over Cas's neck, and fucking kissed Dean’s cock through the skin of Cas’s throat.

Well that was it. Dean had never seen or felt anything like it in his whole life, and he came right there and then with a gasp, a shout, and a full-body shudder. The moment tipped Cas over the edge too, and he began to shake wildly, come pulsing out all over his fist.

“Holy fuck,” Dean heard Sam say. “Come here, Jess.”

Jess obeyed her Alpha, and lay down on her back next to Cas, head level with his knees. She put her hand between her legs, and rubbed herself as she looked up at Sam, who pulled out of Cas, and started to jerk himself above his girlfriend's face.

Dean left his dick in Cas’s mouth a few seconds longer, then pulled out and helped Cas sit up. They kissed, endorphins still shooting through them like electricity. 

They pulled apart just in time for Dean to see Sam coming all over Jess’ chest and neck with a low, breathy moan.

Without being asked, Cas immediately crawled over to her and started licking it all up. 

Dean and Sam both made noises of surprise and approval, and Jess was patently loving it, as she started to arch her back and rub herself faster.

“Yes, Cas,” she breathed. “Good boy.”

Despite just ejaculating, Dean was hard again within seconds watching Cas lick Sam's spunk off Jess' breasts. 

"Sam?" Dean asked, not even realising what he wanted until the words left him. "May I please get inside your girlfriend?"

Sam laughed as he wiped sweat off his forehead. "Seems only fair," he said, still panting for breath. "That okay baby girl?" 

Jess looked up at Dean and nodded. "Oh, yeah," she grinned. "That's very fucking okay. Come on Dean, show me what you got." 

*

Cas was still sucking come from Jess' nipple as Dean knelt up on the bed and pushed inside her. 

She gasped and her fingers flexed in the sheets as Dean guided one of her legs up to rest against his shoulder.

Cas watched his Alpha as he started fucking her, and any jealousy he might have expected to feel was nowhere to be seen. He just felt hornier than ever, even though he'd come less than a minute ago. 

"You guys look so good," Sam said, leaning against the wall at the side of the bed, lazily stroking himself even though he too had only just come. "You look so beautiful taking Dean's cock, Jess. Does he feel good?"

"Yeah," Jess breathed. 

"If he feels as good as he looks then you're a lucky girl," Sam told her, and Dean exhaled a short laugh at the compliment. 

Sam wasn't wrong though. Dean looked fucking fantastic. His face was so sexy, especially when he bit his lip, and his body looked sensational. Cas felt crazily blessed to call him his. 

Dean leaned forward to grab Jess by the waist, and he rolled them over so she was riding him. 

Cas watched for a while as Jess drew circles with her hips on Dean's cock, hands massaging her own breasts, hair falling round her face. She really was quite statuesque; no wonder Sam was so besotted. 

Dean was holding on to the front of her thighs, watching her with slightly glazed eyes. 

"That's it, babe," Sam said to Jess. "Ride him hard, good girl."

Cas looked over at Sam, and decided to take advantage of the situation before he lost his chance. There was one thing he'd kinda missed since Sam got with Jess...

He crawled over and licked the end of Sam's half-hard-again cock.

"Oh, yeah," Sam sighed, letting his head knock back again the wall. He put one hand down in Cas's hair, and pulled gently.

Cas sucked Sam to full hardness, relishing the feeling of his mouth filling with that huge dick. It was extra hot knowing that Jess was watching; he could hear her and Dean behind him making all sorts of pornographic vocal sounds.

"God, Cas," Sam moaned. 

Cas hummed, proud that he could still please Sam like this. He took it easy though, mindful of the throat-banging Dean had just given him.

Dean.

Cas realised he was starting to really crave his mate. The scent of his Alpha close to orgasm was filling his senses. 

He pulled away from Sam, after giving him one last lick and a smile, and crawled back towards Dean. He kissed him, and Dean reciprocated immediately.

“You okay?” Dean whispered.

“I think I might need to cut in,” Cas answered, looking apologetically at Jess. 

“Hey, go ahead,” Jess said immediately, sounding out of breath but happy. She held the base of Dean’s dick as she began to dismount. “I’ve been totally spoiled tonight, and I’m very grateful.”

She gave Cas a kiss on her way back to Sam. “He’s all yours.”

Cas pulled Dean up by his hands, and turned away from him on all fours; a wordless request which Dean was happy to grant.

As much as Cas had had an insanely blissful time tonight, and everything he’d experienced had felt so good, literally nothing would ever compare with Dean sliding inside him. He closed his eyes, acknowledging yet again just how perfect they were together. It felt so right, and so fucking good.

“Oh god, yes,” he breathed. “Dean.”

Cas heard sounds coming from the other side of the bed, and he assumed that meant that Sam and Jess were back at it. He opened his eyes and turned his head to look. Sam was holding Jess up against the wall to fuck her.

How the hell does he have the energy? Cas thought, fondly. Alphas really are something else.

Dean was drilling into Cas harder and harder now, and Cas’s whole body was tingling.

“Oh god,” he sighed, and put his forearms down on the bed, his hips angling up higher.

“Cas, Cas,” Dean was gasping. “I love you, I love you, fuck baby, fuck!”

Cas reached his arm through his legs to fondle Dean’s balls. “Come in me, Dean,” he begged, “Knot me, knot me, Alpha, please...”

“Yes, yes, yes!” Jessica yelled from her position against the wall. “Fuck me Sam, fuck me baby, give me your knot, I need it, yes, YES!”

Cas felt himself on the precipice of another climax, and started to stroke himself into it.

"Oh Dean, oh Dean, I'm coming!"

Cas's ecstasy was heightened by what had to rank as one of the world's greatest sounds; the simultaneous orgasmic screams of the two Winchester brothers.

 

* * * 

 

Somehow they all managed to find space to fall asleep on Dean and Cas’s bed. Dean and Sam’s respective knots went down during the night, and the four individuals woke up in a tangle of limbs and bedsheets.

There was some slightly awkward eye contact over breakfast; it’s always odd to lose yourself in front of people who haven’t seen you like that before, but mostly they just giggled at each other and smiled secretively at the memories they’d created. There was some residual horniness as well though no one had the energy to actually act on it.

Sam and Jess were flying back West in the evening, so they spent the day watching movies and eating at the diner and just hanging out as a family. 

An unconventional family, sure. But Dean couldn’t imagine loving anyone as much as he loved these three idiots. Especially his Cas, with whom he felt happier and more comfortable with each passing day.

And if he’d happened to pull Jess aside for some advice on engagement rings, well that was his business.