The biggest mistake Dean Winchester ever made was having a one night stand with a witch. He was pulling on his jeans around the time she woke up, and things descended rapidly. Before he knew what was happening she started shouting things about him learning the hard way what it was like to feel insignificant and used by someone he thought he had a connection with, followed by a bunch of crap in latin he didn’t understand.

The world goes dark.

He wakes up somewhere confined but soft, with a heavy weight on his chest and muffled sounds in the background. Whatever’s pressing down on him is doing so from feet to nearly his neck, a sagging and heavy weight that feels like skin when he pushes at it. Something tickles the back of his neck and his ear, he swats at it and catches it, hand curling around it and feeling out the texture to try and blindly figure out what it is. It’s rope-like, wirey, thick and it smells like sweat and ozone. It’s coming from the soft thing he’s laying on, and as his hand tries to track it back to the source it disappears under more skin-like spongey something. Heat emanates from above and below him, so oppressive that it only takes a minute before he starts to sweat.

Okay, yeah, time to get the hell outta here.

He gropes around blindly behind himself, thinking maybe he can drag himself out from whatever the weight is, but his hand presses into something rigid, unyielding, and clothlike. He’s gonna have to get this thing off his chest before he can get out, and so he starts with that, pressing his palms flat against it and heaving up with every ounce of strength he’s got in him. 

The whole room shifts suddenly, the fleshy mass beneath him rolling around a little. He sinks into the center of it, the weight on his chest bears down more so that it’s covering his face, and the two mounds rise up practically sealing him in whatever this space is.

Outside of this place, Castiel sits on a motel bed squirming. It’s just a little at first, with his brow screwed up in concentration and his fingertips probing absently at his crotch. It’s about this time Sam looks over, eyebrows shooting up, and after a surprised beat:

“Um. Cas? What the hell?”

“Something… feels… different. Tingling, or moving, I can’t tell, I think it… It feels good, but I don’t know-”

“Yeah, stop right there,” Sam says, holding up his palm, shaking his head. “That’s called a boner, and that’s not something you take care of while people are in the room.”

He slams his book closed, drags it up to his chest, and snatches his keys off the table. “Tell you what, I’m just gonna… head to the library for a couple of hours. You… jerk off or whatever it is angels do, get it out of your system, and then never talk about it again, okay?”

He departs the room without giving Castiel the chance to answer, and a few long minutes tick by while Cas considers this order. Ultimately, it’s the fact that whatever feels kind of good down there hasn’t stopped that drives him to follow through, and he reaches over to flip through the cable options until he finds what Dean calls softcore porn. He’s pretty sure he never wants to see what hardcore porn is.

Upon the screen, a pair of breasts bounce up and down as a woman takes it from behind. That combined with the constant stimulation is all it takes, and an angel gets an erection.

Back in Dean’s world, the thing pressing down on his chest gets heavier. It grows, expands, dragging across his chest and his face until he’s sandwiched between what he doesn’t realize is a half-hard dick and the balls beneath it. Something shifts again, and the world shakes gently up and down as Cas’s fingers wrap around himself from outside of his pants and gently jostle his package, feeling it out. Probing fingers massage into his hardening length, kneading it onto a furious Dean who scrambles all the harder to shove the thing off of him.

That sensation Cas very much likes, so he kneads harder, gripping himself over his clothes and digging fingers into what he doesn’t realize is Dean’s back. Some unyielding force smashes Dean into the hardening flesh above him, dragging him a little back and forth against it with the feeling of fabric wrapped in steel unrelenting, smashing, crushing him into heat and pliable skin.

After a couple of minutes, the feeling disappears thank god. It’s replaced not long after, though, with something new. A rumbling sound, a flood of light and fresh air, and then something invades his dark space. It’s about this time Dean starts putting two and two together, and he realizes that it’s probing fingers, an entire god damn massive hand exploring the cramped area he’s in. They don’t pull him from his place between cock and balls, not yet, in fact they dip around him and start massaging balls, pressing them up and rolling them so that they practically consume Dean within the sagging skin. They smash him into cock, seal him in between the two places, they erase any space and air and movement in teasing, absent rhythm.

Eventually, clever pads of fingertips find him but don’t tug him out. No, one finger pushes down so that he’s deep in between sack, and then start pressing the balls together again, rolling them around in a massive palm, smushing him and burying him in skin. Outside this space, the rumbling thunder of a groan sounds. 

The brutal battering stops and the hand retreats, leaving Dean a precious moment to gasp, to catch his breath, to wrap his arms around the slowly-rising cock above him to try and pull himself out of the quicksand-like skin of testicles beneath him.

Cas moans again at the sensation. He stopped just so he could lift up and work his trousers down a few inches, but he doesn’t even get the chance to remove his underwear before heat and pleasure spark at the stimulation. 

His fingers dip back into the confines of his boxers. Without the trousers blocking out all light, Dean gets full vision of the area around him streaming in through crosshatched fabric. He sees looming fingers dive in and start touching the head of a cock that curves up now that it’s only trapped by soft cotton. He sees them dip down and tries to scramble, but he doesn’t manage it before they’re pressing into his back and smashing him into semi-loose skin at the base of a dick, rubbing him in circles around a thick vein, and an echoing moan follows it.

They drag him up, fingertips pressing into his shoulder blades and his spine so hard they’re practically crushing. They make it to about mid-shaft before they start pressing him in again, rubbing out circles there, teasing and slow. Dean recognizes this as what it is: not the main event, but foreplay. Lazy self-exploration. It’s gonna get worse.

Fingertips move again, dragging him along skin up, up, up the shaft until he’s pressed into the frenulum just beneath cockhead, and apparently whoever this is really likes that. The sound that breaks above him is louder than the rest, and instead of just pressing him there the grip shifts so that he’s in the curl of the back of a set of knuckles and fingers wrap around both him and the dick properly. 

That’s when the fun begins. The guy starts jerking himself nice and slow, not dragging Dean up and down but rather gripping him tight in that one special sweet spot and slowly jerking him and the skin around it, rubbing it out nice and easy, taking his time with an arguably loose hold. Precum slips through the slit above him, rolls down the tip and coats his face and chest. He does his best to spit it out, to squirm and struggle to get a hand to his mouth so he can wipe it away.

It’s a mistake. Whoever’s gripping him likes that feeling, and the hand around him doubles down, gripping so tight it knocks the wind out of him, shaking him within the confines of his underwear, furiously masturbating without even shedding his fucking boxers.

Whoever this guy is, he must be a virgin because he’s still wearing clothes and Dean can tell that he’s close. Can tell because the vein above him is pulsing like mad, twitching, the muscles start to spasm, the fingers fluctuate in their grip from loose and fast to tight when a particularly hearty throb rolls through the dick above him. Dean can practically tell each wave of peaking pleasure by it, by the throb and the tight grip that follows, jerking through the wave of feeling he must be having.

In no time at all he grips down tight, spasms like crazy, and spills hot seed slick down his hand and Dean’s front. He’s got to fight to keep from drowning in it. He’s got to kick and squirm and struggle within the skin to get a hand to his mouth and frantically rub the sperm away. He twists, he smears his face along the skin of the dick beneath him in his struggle against the spilling seed.

Maybe if he hadn’t done that, Cas would have stopped with one. As it stands, angels don’t have a refractory period. The squirming against hyper-sensitive skin becomes slick, adding a whole new sensation to the mix. His cock never even gets the chance to go soft, he barely even flags a little after the orgasm.

Dean’s expecting it to be over, he’s expecting to go tumbling down, to get cleaned up, to anything, but the fingers around him don’t let up.

Light suddenly goes flooding in because Cas uses his free hand to shove his boxers down. He doesn’t look, though, he doesn’t even take his hand off of himself. He just starts carefully, slowly, lazily rubbing again. Basking in this new slick feeling he didn’t have the first go around, marveling that it’s somehow even better.

Dean, for his part, realizes who’s got him only when the hand jerking him slides him up the shaft all the way up to the head, skin bunching, his own head peeking over the tip of dick long enough to see the span of blazer, white dress shirt, tan trench coat, and then Castiel’s face. He’s reclined back on the pillows, hair tousled, eyes closed, lips parted, moaning like hell at Dean’s expense. 

Dean struggles with renewed vigor, mouth opening up to yell the angel’s name only to have himself drug straight back down the length of cock again until he’s at the base. Looks like Cas isn’t interested in smashing him in one spot anymore; now that he’s slick he rests more in the curve of fingers and dick slides over him instead like it’s fucking him. 

Cas passes his cock over Dean from base to tip, all the way up, all the way down, the head and the frenulum dragging over his face, his front, his chest, his crotch, his everything, enjoying the interesting friction his soaking wet body brings to the experience. Over and over again Cas fucks his fist, dragging himself back and forth over Dean and rolling in the pleasure of it.

It gets tighter. His hand goes steely, tightens up around himself, speeds up, but Dean’s caught in the curve of a knuckle without escape. He’s shaken, absolutely shaken back and forth over rock hard cock so unrelenting and so tight he can feel the vein splitting up between his legs, a brutal constant drag. 

He can hear Castiel peaking agan, his breath coming out rapidly, soft tsss and uhnnn sounds that pick up in frequency until suddenly he’s flying over himself, coming hard and heavy and jerking himself all the way through it. A second coating of come washes over Dean, who apparently doesn’t learn lessons the first go around.

He struggles, he squirms, Cas moans, and his fingers dig circles into himself again.

Cas jerks off with Dean in his hand twice more, because fucking angels is why. By the time he comes the fourth time Dean’s soaked to the bone, exhausted, and utterly limp in the angel’s hand. Too tired to fight, to struggle, to try and free himself. He misses his opportunity to escape, and Cas tucks himself back into his boxers before Dean gets a second chance. His freedom is decimated with the sound of a zipper rumbling closed again, and he’s trapped between cock and balls once more.

On the bright side, the fucking angel mojos himself clean and dry - no need to even go to the bathroom to clean himself off. No chance to discover Dean, and firmly assuming that any struggling sensations he feels mean it’s time to jerk off.

He discovers Dean three days later in a new motel on a new bed, having finally gotten around to completely stripping, jerking, and lifting up his hand to catch his cum in it- only to realize Dean was there a split second before finishing. 

He’s on the edge, one stroke away as he looks down at Dean’s exhausted body, covered in precum, with the knowledge that he’s what felt so good on the underside of Castiel’s cock. With the knowledge that he should stop and help the hunter, with a twinge of embarrassment, but…

So turned on that he jerks himself anyway, coming with a moan all over the small man in his cupped palm and fucking loving the sight of it.