Archive of Our Own ^beta

Okay, so it's not like Dean's never come across this particular kink before. When you're sleeping with Gabriel, you tend to end up trying pretty much everything sooner or later. And it's not like he isn't aware that it's hot either- Gabriel fucking swears by it, rarely comes so hard as he does when they do it to him.

But having a fist up his own ass is new. And he's not entirely sure what he was thinking when he agreed to it. He only knows that right here, right now, he's lying back against Sam, and watching Cas and Gabriel slicking up their fingers with each other's wing oil. It's kind of a distracting sight- the two of them pressed close to each other, their wings fluttering and flashing white and grey and black, rustling every time they shudder. Castiel and Gabriel themselves are doing little more than touch with precise, well-practiced hands, searching out the oil glands with an accuracy born of complete familiarity and panting into each other's mouths, but it's filling the room with the smell of oil, thick and heady, and Sam's cock is fat and steadily dripping precome against the small of Dean's back.

Not that Dean's is doing much else, mind. Though he has the advantage- or maybe disadvantage- of Sam's hand wrapped around it, squeezing tight at the base while the other strokes over Dean's chest lightly and sort of distractedly. He wonders how it would feel to have that inside him, Sam's huge, calloused fingers slipping in until the knuckles push past his rim, then further, up to the wrist. How stretched-out it would leave him, how loose and sloppy and sore.

Sam nuzzles against his ear, humming a little amusedly like he knows what he's thinking. "You reckon you've got enough?"

There's no answer at first; both angels seem more than content to just carry on sharing oxygen. Then Cas pulls away, looking almost stoned, for want of a better word, and not a little reverent. His voice, when he speaks, is even lower and more gravelly than usual. "Yes."

"Get over here, then. I think someone's getting impatient." Sam nips Dean's earlobe for emphasis, and Dean glowers at him only until he sees Gabriel's face take on a downright predatory smirk.

"Oh, is he now?"

"Very," Sam tells him, tracking Gabriel's slow crawl over the bed towards them every bit as intently as Dean is. "You know how he gets. How greedy his hole is."

"Well, I suppose we mustn't let this state of affairs continue any longer than it has to, then." Gabriel licks at the tip of his fingers, Castiel's oil dribbling over his lips and down his chin. Dean swallows hard. "Whaddaya say, Deano?"

"I... please," he says, because he wants something, at least. He can make it stop if he wants to, he's learnt that by now (though it was hard at first, hard not to feel like he was letting everyone down if the pain got too much, or thoughts of Hell crept in around the edges), and he wants something in him, even if they don't go as far as planned.

Gabriel studies him for a moment, then nods. "You wanna do the honors, little bro?"

"Oh yes," says Castiel, and suddenly he's there, right in front of Dean, straddling one leg and leaning over to kiss and lick his way into his mouth. Dean is pliant between his two lovers, only moving a hand to clutch at Castiel's hair, feeling Sam thrust instinctively against his back at the sight, and again when Gabriel grabs his hair and ensures that his mouth, too, is occupied. There's oil dripping over them both,  but they're more than used to that- welcome it, even. The physical marks Castiel and Gabriel leave on them too often have to be covered to maintain a thin veneer of FBI-style respectability, but the smell- the smell can last for days.

They're taking their time tonight, which Dean supposes is kind of a given. It's not like they're gonna run out of oil, after all, even with the amount that's left behind when Castiel's hand swipes along Dean's chest and settles to toy with a nipple, or when Gabriel runs his up Dean's and Sam's sides alternately, just this side of tickling, both of them leaving Dean squirming and Sam gasping from the resultant friction against his dick.

Eventually, though, they run lower- Gabriel's hand to Dean's hip, then further down to trail along his thigh. Castiel takes his sweet time with things on his end, meandering down over Dean's stomach- smiling against his mouth when a brush of fingers causes the muscles there to twitch momentarily- and down through his pubes until finally, finally-

Well, he goes for Dean's balls in the end, rather than give anything more than a brief touch to his cock. But even with Sam's hand acting as a sort-of cockring, that's probably for the best. Dean grasps at his hair as he takes them in hand, tugging them gently, his thumb stroking across the skin and fingers travelling lower, to the skin behind and then to press against Dean's hole. There's only the one hand working Dean over for a moment- Castiel's other one is resting on his thigh, while Gabriel's reached away for a moment, but then Castiel moans, and as Dean pants and sighs back he knows exactly where Gabriel's hand's gone. Sure enough, when he brings it back to join Castiel's at Dean's hole, it's dripping wet again, and this time it's Castiel's turn to reach away, burying his fingers in Gabriel's wings again, breaking the kiss to watch his handiwork. Dean is entirely okay with this state of affairs- Gabriel's distracted enough by the touch that he's not even fingering him yet, and God he looks beautiful when he's gasping and shuddering like that.

"Fuck, Gabe," says Sam. Dean rather agrees. Maybe Sam should, after they've done this. Maybe he should, if he chickens out of it, or they both should- pump Gabriel full of their come while Castiel works his wings until he's screaming for the three of them.

But he's not gonna get ahead of himself just yet.

Eventually, the two of them turn their attention back to him, watching Dean carefully even as Gabriel presses close. "Still okay with this?"

Dean nods. Sam strokes a hand through his hair, then tugs, the jolt just this side of painful. "You sure about that?"

"Yeah." Dean swallows. "Yeah, I wanna do it." Or try, at least, but he thinks they get that. Castiel nods, his hand moving back down to rub circles around Dean's asshole again. Gabriel kisses him, open-mouthed and sloppy, with tiny, teasing flicks of tongue, glancing over to Castiel every so often to keep an eye on his progress. They all move when Castiel's first finger presses in, Dean arching, Sam groaning and rocking his hips again, Gabriel smirking and rolling with both movements. The same goes for the second, and the third, by which point Gabriel's busy kissing and biting a trail across Dean's chest. After that one, though...

"Gabriel."

"Ooh, my favourite part." Gabriel looks to be on the verge of clapping his hands together. "Well, second favorite. Third if you count it happening to me." Gabriel grins and gives Dean a brief, fleeting kiss before crawling over to sit by Castiel. They stare at Dean again, like he's gonna freak at any second and he's just hiding it really, really well (which, okay, wouldn't be all that improbable, but the scrutiny still makes him feel weird).

"Dean, are you sure...?"

"Yeah. Fuckin' give it to me, Gabe."

Gabriel grins. "That's what I like to hear." He snuggles close against Castiel, his wings sort of nuzzling against the other angel's as his hand joins his at Dean's hole. Dean tenses a little, just a little, when he pushes a finger inside, for all that Gabriel's are that much smaller than Cas'- he's only used to three, okay. Four's become more normal lately, even five, since they've been trying to work him up to this, but it's still new enough. Sam's hand starts to move on his cock though, in slow strokes and ever so lightly, while his other arm holds Dean close. He’s pressing kisses into his hair, across his cheek, to his jaw, to his earlobe. “I’ve got you, Dean,” he tells him, the words breathed out in puffs of hot air that make Dean shiver. “I’ve got you.”

And he has. Dean knows he does, knows the three other people in this room would never, ever hurt him, but it takes them saying it, sometimes. Takes them holding him down and demonstrating it, like this, for it to really sink in. He relaxes against Sam for it, his breath leaving him in a low moan as Gabriel crooks his finger and brings his thumb to bear on Dean's perineum. Sam's grip on his cock tightens at that, before Dean can do anything more than writhe and try to shove his hips down onto the fingers inside him. Castiel and Gabriel are having none of that, though, their free hands on Dean's thigh and hip, holding him down in a way that he's fairly sure is going to leave bruises, and which never fails to be completely and utterly hot.

Gabriel slips in another finger a little while after that, and Castiel withdraws one of his so that he can add a third, too. It's Gabriel who'll be doing this, they've decided. There's not that much difference in hand size between him and Castiel, granted, but according to him 'Every little counts', and since he's the only one with real experience here... yeah. They figured it was best to listen. Right now, Dean's just holding on for the ride, grasping at Sam's arms, at his hair, at Castiel's. He feels stretched beyond what's entirely comfortable, and he's still not sure what he thinks of that. He thinks he could learn to like it. Maybe. But he's withholding judgement for now.

Then Castiel gradually works his hand free, and Gabriel's hand is in up to the knuckle and beyond, and "Fuck-!"

Dean feels the weight of three gazes coming to bear on him. "You okay, Deano?" Gabriel's voice is light, but his hand is completely still. Dean takes a moment to figure out his answer before he nods. "Sure?"

He doesn't look at all convinced. Nor does Castiel, and Sam's hand is tightening in Dean's hair again. But he nods a second time, not quite trusting his voice.

"...alright then." The hand works deeper, and Dean swears he can feel every bone, every twitch of movement it makes inside him. Which shouldn’t be hot, he thinks, but it is. Gabriel is powerful, he fucking knows it, can feel it in the strength of his hand on his hip. He could rip him to pieces. And all that power is here, coiled up, restrained, and treating Dean like he’s something infinitely precious. Breakable, sure, but all the more to be valued and treasured for it.

Castiel presses himself along his side, running his hands all over him. “You’re doing wonderfully, Dean,” he tells him, Sam murmuring agreement, whispering how fucking hot Dean is into his ear, how much he loves him, how much they all do, and all the while Gabriel’s hand keeps inching forward until Dean’s hole slides that much further open around his wrist, swallows it in.

He takes his time working that hand into a fist, but there’s still several moments when Dean’s fairly sure he’s going to lose it just from that. He thinks there might be tears in his eyes, he’s not sure, but he doesn’t want to stop, doesn’t at all.

He trusts them. He trusts them infinitely, and that more than anything is what has him shivering and gasping, what punches an orgasm from him that leaves him quaking against Sam’s chest before Gabriel’s moved his fist even five times.

Okay, so maybe the orgasm had more to do with the intense physicality of everything, but Dean’s brain is too busy whiting out to start drawing lines between things. There’s no fun in that anyway.

By the time he comes down from the high, Gabriel is slowly, carefully working his hand back out, inch by inch. It’s kinda sore now, or at least it should be- Dean has the distinct feeling one or both of the angels is dampening that particular after effect, leaving him with the curious feeling of floating. Subspace, if you listen to Sam, which he rarely does- he doesn’t much care for the word, anyway.

He’s still being cuddled close, by Sam and Castiel both, and the moment Gabriel’s hand is out of him, the archangel is snapping his fingers, banishing the oil from his and Castiel’s hands and producing a thick quilt that he drags up with him as he crawls up to snuggle against Dean, opposite Castiel. When he kisses Dean, there’s chocolate in his mouth, sticky and half-melted and dribbling a little onto Dean’s cheek as it slides across Gabriel’s tongue to Dean’s, but a moment later that mess has been cleaned up, too.

He thinks Castiel might be purring, just a little bit.

The other three’s cocks are still distinctly hard against him, but they say nothing of it, for all that Dean’s already (sluggishly) thinking of things to get them to do to each other while he watches. They don’t tend to, at this point- this isn’t the most out of it Dean’s ever been after sex, but they also know that leaving him to come down from the high without a whole lot of touch is a bad idea. So they stay, wrapping him in warmth and safety and love, seconds stretching into minutes measured by the way Dean’s breathing slows and slows and slows until finally he uncurls, smirking.

“We,” he announces, “are totally doing that again.”