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The More You Know

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They were right—he shouldn’t have joined them on this hunt.

Witches, as Dean puts it, are nasty. Jack knows that, now.

Attacked him from behind with a—spell? Curse? Nasty.

“You still sure you’re okay?” and as everyone hurries back into the Impala and Dean’s already got her engine roaring, Sam’s huge hand curls over Jack’s shoulder, and Jack nods, because, yeah, he’s fine. He thinks.

He feels a little funny, but that’s reasonable.

Dean growls, “Fuck, I need a drink,” and Jack can sympathize. Maybe not a drink in his case but a generous serving of cereal or a decent sundae instead, but, yeah.

They certainly earned a treat tonight.


The bunker quiets down after dinner, after everyone has trailed off into their own room to nurse any new (and old) wounds. Jack decides for a nice hot bath before bed. Even hours after the hunt, he can’t shake the shock.

Sam and Dean had already defeated her, only that one bullet away. A last try—desperate, maybe, that spell. As a nephilim, a simple spell shouldn’t get to him like this, but maybe this was a severe one. Maybe a human would have died from it.

In the bathroom, Jack’s shirt finds its new temporary home on the hanger by the door. His pants come off next.



He thinks he says that out loud.


Jack frowns, looks around—waddles in front of the nearby mirror and inspects further.

He concludes, “Huh,” and tilts his head. Hard to see like this. Maybe if he laid down…?

He remembers this…vaguely. From when he walked in on Dean and things were kinda awkward, and Jack didn’t even get to see anything right.

Feels nice to touch it, though. Like he’s tried with how his anatomy was before.

Jack cups his whole hand over it and rubs up-down. That feels good, too.

The bathtub is very suddenly, very ultimately, not interesting anymore.


Dean grumbles, “Yeah?” and Jack feels that pang of guilt, because Dean sounds like he was already sleeping when he knocked.

“Can I come in?”

“Yeah—what’s up, buddy?” Dean gets up on one elbow and rubs at his face while Jack lets himself in. “You okay?”

Jack explains, “Something very exciting happened,” and the look on Dean’s face tells him he probably looks a little too excited.

Jack closes the door behind him as Dean sits up all the way. “What’s going on, Jack?”

“It doesn’t hurt,” promises Jack, and lets the towel he’d wrapped around his hips drop to the floor.

Dean, who opened his mouth to say something, blinks.

Doesn’t close his mouth.

“It looks kinda funny, doesn’t it?” Jack splays his hands on either side, spreads it. “Have you seen something like this before?”

“I, uh—yeah,” stammers Dean, and covers his mouth with his hand. “Jack, what—how did…?”

“I think this is the witch’s work.”


“When she hit me, you remember? With the spell?”

“Yeah, I—Jack, could you cover yourself up, man, Jesus Christ…”

“Oh, is this inappropriate? Sorry.” Jack grabs his towel, refastens it. “The girls in your video though also did—"

“Jack,” Dean pleads.


“You remember when I said we won’t talk about it? Ever?”

Jack nods, proud. “Yes.”

Dean gives him a pregnant look.

“Oh. Oh! I am sorry.” Jack takes a seat next to him. Dean looks uncomfortable, but mostly tired. They had it worse. “But this is a special circumstance, Dean,” insists the nephilim. “Don’t you think?”

Deadpan, “I guess,” and Dean massages the bridge of his nose as he sighs. He gestures towards Jack. “We can, like, set Rowena on it tomorrow or sum. It can wait, right? Doesn’t hurt?”

“Yes, it doesn’t.”

“Good. Great.”

Jack considers this might be the part where he gets up and leaves. Lets Dean have his peace, his sleep.

He starts, “Can you—” but is cut off by Dean’s bellowed, “Go ask the freaking INTERNET!” and, okay, fair enough.

Dean is generous enough to donate his laptop for this noble cause under the condition that Jack uses a private session and never, quote, ‘never, in the history of ever, under any fucking circumstances, EVER’ talks to him about any of tonight.

Eternity is a queer concept to a five-month-old, but Jack does his best.

Jack holes up in his room. He starts with pictures, but the websites quickly show him videos instead. Most stuff looks violent and kinda painful, but something tells Jack that it’s still…good. For both the man and the woman. Or, the several men and the woman.

Cas had lectured him about porn and human sexuality, but Cas is not a reliable source when it comes to that kind of information. Jack already knows as much.

The videos he finds are not like the one he saw Dean watching. These ones are, well… rough.

The longer he watches, the more…warm he gets. A throb, odd and deep, and it puzzles him. He rubs his hand between his legs, where he’s changed now. Warm here, too, and… Oh.

He is very sure he did not soil himself.

Why, then…?

Jack frowns at the laptop, at the video. Huffs—confused, restless.

Dean’s second, “YEAH?” of the night sounds considerably less amicable, and he looks positively ready to kill when Jack barges in nevertheless. Starts, “Kid,” but Jack tells him, “Enough,” and Dean’s face softens.

Jack climbs into Dean’s bed.

“You will help me with this,” decides Jack. “Just like in the videos.”

Dean coos, “All right,” and Jack’s stomach twists. It’s not fair of him to use his powers. But this won’t hurt Dean, he’s sure. And they can pretend it never happened, after.

Jack’s on top of Dean, bare as the day he was born, and he’s not finished crawling all the way up before Dean’s already yanked him up by his arm, kicks the blanket aside.

“C’mere, then.”

Dean is warm. Jack drops on top of him, beds his cheek on to the worn-out cotton of that sleep tee. Dean tuts at him, helps him pull his leg up so he can reach between with more ease.

Dean’s fingers rub at him. Jack huffs.

“So fucking wet already. Shit.” Dean chuckles, low and close. “Some kinda vids you’ve been watching, huh?”

Jack wants to say: yeah, yeah he did, and they were…confusing. And that he wants that, all of that, but.

Dean’s circling his pointed fingers where the throbbing is worst, and Jack kinda…


“This what you need, huh?” and Jack gasps, fists his hands tighter into Dean’s tee with his mouth hanging open, and.


“Gonna make you feel real good, sweetheart.” Dean hikes Jack’s leg higher. “Don’t you worry.”

Those fingers slip deeper, further, and sink into Jack. Two at once and Jack’s body hitches at the surprising stretch, at the slight burn.

Dean makes an appreciative noise from somewhere low down his chest.

“Got a feeling you’re gonna return the fucking favor.”

Jack says, “Dean,” dumbly, empty, and he’s all out again once Dean hooks his fingers and grinds them inside and up.

Shudders, unable to move, to feel anything but—this.

“Get on your back for me, baby, c’mon,” and he doesn’t exactly wait for Jack to move by himself, kinda shoves and helps until they’ve got it. Until he can scoot down and down and he gets a hand into the back of Jack’s knee and signals him to hold it like that, and Jack complies with his heart beating in too many places at once.

Jack can’t tell which comes first—Dean, humming with pleasure as he closes his mouth over where Jack’s aching and wet, or Jack, gasping, whining with his fingers threading into Dean’s hair and pulling him in, more, don’t stop.

Dean settles between Jack’s spread legs like he’s done this a million times. Suckles at him for a beat (and more) before he flattens his tongue, laps up the heated line of Jack’s gash, and Jack hiccups his breath, has to get both hands on Dean’s head because he has to hold onto something.

Dean pushes his legs back and open for him.

“Dean, please…!”

A dismissive hum.

Dean slurps at him—loud, obscene.

Like in the videos.

“God, you’re so fucking wet.”

Jack nods, lost, eyes closed. Feels Dean pushing his fingers up inside him again while he licks at him like a dog, at that odd, hard-ish little point that’s so fucking sensitive, that makes Jack clench and shiver on every pass of Dean’s tongue, Dean’s lips.

Jack whines.

“You think my cock’s gonna fit in here?” and Dean emphasizes what he means by pumping his fingers, and Jack trembles again because, oh, he can tell how tight of a fit there is. “Kinda wanna find out.”

Jack nods, uselessly, because Dean’s already pushing his pajama pants down, not letting up on Jack’s pussy. Abandons it with a final, absurd slurp that leaves Jack’s stomach clenching, so he can push himself to his knees, can shuffle closer and stroke himself.

He’s hard, all the way. Thick and pulsing and gleaming wet at the top, and Jack sucks his bottom lip into his mouth to gnaw on it.

Dean keeps one thumb circling the hard little nub between Jack’s legs while he growls, feral and maybe impatient and Jack gets a hand down there to pull himself open, help him out.

“Fucking tiny,” muses Dean, rubs his wet cock through the soft folds of skin and up to where his thumb’s still tucked over, and Jack tilts his ass higher, more available.


“Hold yourself open, baby. Just like that, both hands.”

Jack does, of course.

Dean groans, “Fuck yeah,” both hands on Jack’s legs now to hold him down and open, not even gripping his cock and he rubs it over Jack’s pussy like that, loose and deliberate, and Jack groans low and small because he wants, he wants.

The fat head of Dean’s cock catches on his hole on every stroke but never fully pushes in. Always just a threat, a tease.

Again, choked-off, “Please,” and Dean has mercy, then.

Raises his hips and drops them, and his cock sinks in like a weight, forces past the initial clench and it doesn’t hurt, no, but it’s tight and a stretch and Jack whimpers, confused, surprised, everything, while Dean keeps sinking inch after inch inside.

“Good fucking pussy,” and Dean wouldn’t say that, wouldn’t say or do any of those things but that’s all right—wouldn’t groan like a caveman and bury Jack underneath himself and grind the last massive bit of his cock home, bump his heavy balls against Jack’s taint, but Jack’s okay with this. It’s safe and temporary and he can make Dean forget, make it like this never happened.

So it’s fine that Jack lets him kiss him. That he lets him lap into his mouth and eat at him while Dean rolls his hips, while he gets settled in the clench of Jack’s brand-new pussy.

“Fuck.” A testing, deep thrust. “Fuck, she better not gave you the full set, because no freaking way I’m pulling out.”

Jack makes a deep-gut sound around Dean’s tongue—the heavy taste of himself, the fat pulse of Dean’s raw cock tucked deep and tight, rubbing him out.

He doesn’t know exactly what most of what Dean says even means, but it makes him dizzy to hear it. Makes him clench and moan, makes his pussy suck at Dean’s cock like it desperately needs it.

Dean keeps babbling, “So sweet and tight,” while he starts moving for real, settles his knees and pumps his hips hard enough that the bed begins to creak. Has Jack’s legs till clutched and pushed back against Jack’s chest and fucks him in strict, tight strokes—fills Jack out completely and then some, so fucking thick and hard that Jack can feel every vein, every curve.

Swears he can feel Dean slicking him up, inside, with how good it is for him, too.

“Fuck, you keep milking me. So fucking hungry, aren’t you,” and it’s not a question, and Jack mewls upon Dean tucking his thumb back over that throbbing point, picking that tight circling motion back up and Jack seizes, can’t do anything but let Dean pound him out, loud and wet and fucking mean.

“Hey what’s—what the—” and Jack didn’t quite hear the door opening or Sam approaching, at all, but the shock fades into joy quickly, because—

why not?

“Hey, you mind?” and Sam’s right there, of course he is, hand ruffling Jack’s hair and Jack pulls him in by one belt loop, and Sam snickers sweet.

“You need some help with that?”

Dean growls. “Kid’s a goddamn vice.”

“Looks good,” comments Sam, trails one hand up Jack’s stomach. “Too bad she didn’t give him—oh.”

Jack’s whine is muffled by the quickly growing bulge Sam’s grinding up against his face; Sam kneads a mound of flesh that had been perfectly flat just a moment ago, and his hand is huge and Jack hiccups his breath.

“Cute. Little handfuls.”

“Fuck, keep that up, makes him nice and tight…”

“Like that?”

Two hands now, one for each tit. Jack mewls against Sam’s balls.

“Gonna make him come like that, Sammy.”

Sam tells him, “Let’s see it, Jack, come on,” and Jack doesn’t know what they even mean, just floats and moans and it’s so good, feels so so good and then something snaps, somehow, deep and intense and he gasps, overwhelmed, and Sam praises, “There you go,” and Dean just growls and keeps fucking him, and.

Sam helps holding him down, aids in making him take it, shaking and loud and Sam laughs, purrs, “That’s it,” and Jack can’t stop seizing over and over and over.

Sobs, pathetically, when Dean sits back and yanks his cock out of him, slaps it down over Jack’s pussy a couple times.

A whistle. “Shit.”

“Need a break?”

“You want a turn?”

“Sure, yeah.”

Dean offers, “Get it,” and it’s a fluid exchange; so very typical of them even though they’re not really ‘them’ right now.

Sam’s just…huge.

Has stepped out of his pants before even getting on the bed, pulls his tee over his head and tosses that away while he knees his way up between Jack’s legs. Jack reaches out for him and Sam laughs but indulges him—lets Jack squeeze his pecs, run his hands down his arms.

Sam trying to bull his way up his pussy though is not as pleasant.

Too-wide, too-thick, and Jack winces, and Sam frowns, grunts; frustrated.

“Jesus, that’s tight.”

“Told you.”

“Shh, I got you, it’s okay,” and Jack nods with his breath all wrecked and distorted, with his chest hitching for Sam’s palm engulfing one tit again, with Sam scooting low until he can bury his head in Jack’s lap.

Distraction comes in the form of Dean, grabbing Jack’s hair and his other available tit; and Jack looks up and gets his head turned, and Dean doesn’t waste much time before he dips his cock into Jack’s mouth. Jack splutters around it, around his own taste, while Sam truly starts his efforts, truly starts to suck and lap at him and Jack can’t even whine right with his mouth stuffed like it is. One hand up against Dean’s thigh, one buried in Sam’s hair.

Sam comments, “So cute,” in between drags of tongue, and Jack can’t tell up from down anymore. Is overwhelmed, maybe the two of them is a little much, maybe he shouldn’t…

Dean shoves himself deeper, grumbles, “All your holes so fucking bottomless for us,” and Jack tries to swallow and fails. Feels his spit bubbling up into the corner of his mouth, feels Dean’s cock stretching out his throat so so good. They’re both still kneading his tits, thumbing and toying with his nipples and Sam’s churning a bunch of fingers into him, now.

Rubs another lower, though, past his taint and over the clutch of his asshole.

“You tried his ass yet?”

Dean flirts, “Not yet,” and Jack flushes new, flushes deeper.

Gasps, “I-I’m gonna come again,” when Dean gives him the chance by pulling out, giving him a break, and Dean laughs, mean, and Sam hums all pleased up against Jack’s mound. “I’m, I’m gonna—”

“From having all those pretty holes toyed with? Yeah, we get it, Jack.” Dean squeezes his tit, hard.

Sam’s finger goes from rubbing to pushing into Jack’s ass, and that is so different, so good, and he convulses all over again.

They hold him down without effort, thanks to Jack’s own powers. Sam eats him out like a starved man, like there’s a sweet core he needs to get to, hums and groans like he truly really enjoys it, too; pumps his too-big fingers through the quiver of both of Jack’s holes like it’s nothing, like he doesn’t even care Jack’s already coming.

Dean’s the first to break the spell again. Gets his cock back down Jack’s throat while Jack’s still writhing, tips his head back with the grip in his hair so he can use him right, and his brother follows suit soon enough.

Gets back to his knees and gets his fingers out to instead grip at his cock, steady it so he can force it inside, finally.

It works now, it does, but not without struggle.

Sam has to fold Jack nearly in half. Groans, loud and unabashed, for the grip Jack’s insides have on him. Curses, “Fuck,” and pumps his hips to work himself deeper, and Jack shudders.

Sam puts one hand over Jack’s lower belly, just above his pubic bone.

“You feel that, Jack?”

Both Dean and Jack groan.

“Fuck, he bulges out?”

“Hell yeah.”

“Shit.” Jack can’t see, but they’re exchanging their hands—Dean’s, now, pressing down, fascinated, while Sam bumps his cock up into his guts, already stretching Jack’s pussy to its limit without a care. “Shit, that’s fucking hot.”

“Might have to use his ass, though.” Sam talks casually while he fucks into Jack. “This won’t work.”

“Don’t think he’d mind. Do you, huh?” and Jack coughs up drool and Dean’s precome, has Dean slapping the heavy weight of his cock down over his still-open, gasping mouth.

“Wanna eat him out while I open him up?”

Dean agrees, “Hell yeah,” without hesitation, like this was the plan all along and Jack throbs all anew, not only to the beat of Sam grinding into him.

They rearrange him easily. Like he’s just a toy, a doll, and to be honest he does feel weak-kneed, does feel whiplashed form the orgasms. Finds himself on all knees and elbows and face to face with Dean’s dick while Sam’s already burying his face in his ass, while Dean’s chuckling happy up against his clit from below.

“C’mere, get that back in your pretty mouth for me. Mmh. Good boy, Jack.”

Dean latches up onto his pussy as a reward, and Jack is glad they’re holding him up.

Jack struggles to focus on sucking Dean’s cock with both of their mouths on him, off-synch, and Sam’s impatient, inches a finger in next to his tongue nearly immediately.

Dean gets a hand on the back of Jack’s head to push him down, makes him take him deeper.

“This isn’t fucking kindergarten. Fucking suck it.”

Jack tries his best. Has tears clumping up his lashes and even though he wills his gag reflex away, his anatomy clearly still tells him his throat wasn’t made for anything of this girth.

Dean tastes amazing. Heavy and weird and addicting.

Sam praises, “Good fucking boy,” and spreads his cheeks with one hand, bangs two fingers of his other hand into his ass with ease. Jack materializes more slick, enough for it to be audible; enough for it to encourage Sam to give him three. “Fuck, such a greedy fucking hole.”

Sam sets up to replace his fingers with his cock, and Jack’s throat is too preoccupied to let them know, warn them.

He jolts, caught between them, with Sam’s monster cock pushing up into the too-slick heat of his ass and Dean nursing on his clit, still holding him down on his cock and Jack splutters, can’t go anywhere while he comes, and comes, and comes.

Sam slurs, “Fuck,” easy and throat-y as he pumps into Jack’s ass, slow and deliberate, still getting him used to the insane stretch. Thumbs along the sensitive rim of his hole, where they’re connected. “You came on that, Jack? On getting your cute little ass fucked?”

“Fuck, you think he can take us both?”

“Only one way to find out.”

“Shit.” Dean laughs. “Just like the good ol’ times, huh?”

Sam laughs, too. Builds up even thrusts already, pulls Jack nearly inside-out with it. “Get moving then, come on.”

But Dean stays where he is, just a little while longer. Sucks and laps at Jack’s overstimulated clit, and Jack feels him chuckling, feels his breath hitting him where he’s dripping and burning. Detaches himself, finally, and Jack feels a slight headache coming on from the grip Dean’s had on his hair, and he happily drops his head onto Dean’s shoulder once he can, once the hunter has laid himself out underneath him.

Meanwhile, Sam’s not stopped fucking him, not for a moment.

Bangs him out so so deep Jack’s dizzy with it, melts with it. Is nothing but this burn, this ache, the stretch where there shouldn’t be any.

“Hey, you still with us? Hey, kitten.” Dean squeezes Jack’s face between his fingers, shakes him. “You like it, huh? Like Sammy fucking your tight little ass?”

Jack slurs, “Uh-huh,” and can’t even brace himself for what’s coming, because Dean’s already fingering his way inside, already searches for the right angle to get his cock back into Jack’s pussy with Sam already pumping inside him.

“’S gonna get a whole lot more fun in just a sec,” promises Dean, and Sam has the presence to slow down a bit, let him figure things out. It works, then.

Nearly too tight, and if Jack wouldn’t have his powers it probably would be. Isn’t, though, not now, just enough that Dean can slot in, just the thinnest of walls between their cocks and Jack can feel that, can feel them rubbing against each other, so fucking hard and powerful and he whines, helpless, as they hold him open, rock into place, groan dirty little nothings.

“There you go, baby, good boy.”

“So fucking tight for us, can you tell?”

“Both of us all in your pretty little holes, huh,” and there’s fingers prodding at his mouth, so Jack opens that one up as well, lets them push inside, lets them stroke his tongue, the back of his throat.

Sam picks up his overlong thrusts, both hands on Jack’s hips to keep him in place, rock up into him right.

“Fuck. Tight fucking kid.”

Dean agrees wordlessly. Stirs three fingers in Jack’s mouth and bumps his hips, grinds his pelvis against Jack’s still-throbbing clit.

“Gonna fucking come in these pretty holes, baby. Get you so fucking full with it.”

Jack nods, agrees; anything.

Dean’s body is so fucking solid underneath Jack—all heated and cozy and his tee is damp with sweat (his own; Jack’s). Jack’s thighs ache from being spread so wide and he mewls upon Dean somehow finding one of his nipples, rubs and pinches hard at the squished-between-them flesh and whispers, “C’mon, sweet thing, c’mon,” and Jack doesn’t have any control over anything anymore, and maybe that’s okay.

His orgasm overcomes him slower this time, deeper. Rolls through him and he clenches so so hard around the two cocks stuffed too-deep inside of him, milks at them while the brothers groan like it hurts, and maybe it does, a little.

They curse him out, fuck him harder. Don’t hold back, use all they got, and they’re—strong. Keep him pinned while they use him and Dean’s still got his hand in Jack’s mouth, still has him open and drooling and it’s Sam who loses it first; who locks his hips and holds himself deep and growls like a beast, and Jack can’t exactly feel it over the general throb of his insides but he can feel that cock flexing, jumping, all trapped inside him.

Dean follows suit. Tenses so nicely under Jack’s lightweight and he circles his hips, rubs Jack out entirely while he empties.

Dean pulls out first, and it’s not too messy until Sam does, too. Jack shudders, shocked, at the wet-hot gush escaping him. It’s a lot.

“Fuck. Pretty,” murmurs Sam, thumbing some of it back into Jack’s ass. Dean helps Jack tilting his hips so gravity doesn’t make him lose all of it just now, pulls him wide for Sam’s eyes, Sam’s fingers.

Jack murmurs nonsense. Slurs it all into Dean’s neck, Dean’s tee.

“Shit,” Dean groans. “How am I still hard?”

“Right?” Sam sounds pained as he thumbs the head of his cock back inside Jack’s ass. “Fuck, still so tight. Like I’ve never even been in there.”

Jack squirms, weak, upon Sam pushing himself back in all the way, through the slick of his own load. Upon him reaching around, rubbing strict circles over Jack’s sore clit.

He feels his pussy leaking with Dean’s come, feels it bubbling up against Sam’s already heavy again balls.

Dean feels it, too. Pushes the solid head of his cock against the wet mouth of Jack’s pussy anew, pops it back in, plugs him up.

The brothers groan, satisfied. Hungry.

Their loads leak out around their fat, heavily-veined cocks, with nowhere else to go. They fuck most of it back in, deep and safe.

Sam promises, “Just one more, okay?” and, Dean adds, after a beat, “Maybe two.”

“H’okay,” croaks Jack, with a smile.