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Dean is sitting on the couch watching some old crappy horror movie, and maybe a little more drunk then he cares to admit. Which is why it takes him a while to realise that Jack is sitting awfully close.
Awkwardly close.
The movie, well the movie has this monster. This monster with tentacles. Which Dean really likes.
And apparently, Jack has noticed.
“So, you find them exciting?” Jack asks.
Dean shifts in his seat, squirming, when he answers.
“Yeah, well, you know, it would be somethin’ to come up against wouldn’t it?”
“So you want to fight it?”
“Not exactly.”
Jacks eyes scan his whole body, and go wide when they see the bulge in Dean’s pants. “Oh.”
“Sorry, this isn’t… we shouldn’t be talking about this.” Dean gets halfway to standing to leave when Jack's hand closes around his wrist.
“It’s okay, it’s fascinating.”
He encourages Dean back down to the couch, and Dean swivels around so they’re facing each other, leaning against the arm rest. Jacks hands start to wander, exploring and pinching Dean while his breath speeds up.
“What would you do if it really happened?” Jack asks.
“Probably freak out,” Dean chuckles.
“Really, why?”
And then Jacks finger twists in a way that fingers shouldn’t be able to twist and it keeps going further and longer, tickling, and curling around Dean’s knee.
Dean stares at the transparent prehensile limb that has extended out from Jack’s finger, growing from it. It’s covered in suckers, and it doesn’t look real but he can feel it, and it’s definitely real.
“What are you doing?”
“I think they call it ‘fulfilling a fantasy’” Jack says, with a smug grin.
“How are you doing it?”
“My grace.” He shrugs.
“Well, stop!”
“Don’t you want to?”
Jack’s other hand comes up to rest on Dean’s shoulder and he feels more tentacles wrapping around the back of his neck and shifting below his shirt collar. He moans. It feels exactly like he hoped and yet also nothing like he expected.
They’re not slimy, like he imagines real ones might be, and there’s a tingling warmth that follows wherever they touch, but the weight and texture and suckling pressure whenever a sucker pops onto his skin is perfect.
“It doesn’t seem right, you, this ain’t natural.” But his voice gives him away, all broken and groaning.
“I like it when you sound like this.”.
“I like feeling like this.” Dean breathes. What harm is a little fun really?
“You know you could feel a lot more without your clothes on.”
The idea is full of suggestion, implying so many things Dean’s aroused and alight brain can only begin to hope to imagine. He's thinking purely with his dick, and he knows this, but he’s sliding to the floor and fumbling at buttons before he has chance to care.
When Sam returns to the motel room he finds things are not how he left them. Which is the biggest understatement of all time.
Jack is crouching next to Dean who is butt naked, laid on the floor with a look of absolute bliss smoothing out his features. And he’s writhing.
“Jack, Jack, st-stop,” he says, somewhat unconvincingly. “We can’t, this is enough, you shouldn’t-”
“But you like, it don’t you?”
“Yeah,” Dean breathes, lifting his hips up, pumping them, making his hard and leaking cock wobble.
“Then I don’t see the problem, why don’t you want to feel good?”
“It, it’s not that,” Dean cuts off with a moan, eyes falling closed. “Only do it if… if you want to—”
“I want to, I like making you feel good.”
Dean makes a broken groaning, keening noise and throws his head back.
Which Sam’s cock really likes. A lot.
He steps further into the room, so far having gone unnoticed, and clears his throat.
Jack looks round with the biggest grin and Dean’s eyes fly open.
“Look!” Jack says with excitement.
“What exactly am I looking at?” Sam asks, moving to sit beside them.
“Sam! Sam Sam Sam,” Dean pants, chest heaving. “This kid, boy has fucking,” he moans, his words cut short, and rolls half way onto his side before flopping onto his back again. “Show him!” he waves at Jack.
“I… found something Dean likes,” Jack says shyly.
Sam watches in fascination as things materialise before his eyes. He can’t see them all at once, they shimmer and disappear in glowing sections. But there’s no mistaking that they’re tentacle shaped.
“Are you for real… Jack… how?” Sam asks, excitement mounting.
“It’s my grace, or my essence I’m not sure what you’d call it. But I can shape it, and Dean said he likes tentacles and…”
“And you just let him?” Sam asks, finally touching Dean’s sweaty forehead and sweeping aside his damp hair.
“Didn’t, didn’t give in, not at first, but,” he replies with a grin.
“Hmm, yeah, hard to resist your favourite fantasy ever isn’t it?”
Jack is watching intensely as the magical limbs circle and tease at Dean’s nipples, and caress his throat and trail between his legs. Sam sees two wrapped around each of Dean’s arms, twining all the way from his biceps down to his wrists, the suckers gently smacking and pulling against the inside of his wrists where he’s sensitive and loves being kissed.
Dean is melting like it's summer and eighty five degrees and not February and freezing.
Sam gets an idea, forming it in his mind with glee.
“Have you fucked him with them?”
Dean and Jack both go wide eyed.
Twenty minutes later with a basic course in male erogenous zones reaffirmed to Jack (who knew more than Sam gave him credit for, no stranger to the secrets of intimate bedroom antics apparently) Sam is delighted.
Dean is gone. Fucked open, glassy eyed, and limp. He has slick thighs from whatever grace-lube Jack used to ease the way and his body ripples under the pressure of every inch Sam has encouraged Jack to work inside.
His cock, which was already hard and bouncing earlier, is now swollen beyond belief. It strains and throbs and Sam wants to touch, but he also doesn’t want this to end.
He risks a glance at Jack and finds him ruffled, hair mussed and hands clenching on the rug and his knee. He's sitting right beside Dean, his leg brushing Dean's hip, hunched over and leaning forward to get even closer.
“Jack are you alright?”
Jack nods and shifts and that’s when Sam sees it, the tenting erection pushing up his jeans and caught in a presumably uncomfortably denim prison.
“Is this turning you on?” He asks incredulously.
“I feel them.” Jack breathes.
“What?”
“The tentacles, they’re me I can feel everything they do, feel them inside Dean.” he looks at Sam with lust blown pupils and Sam rocks backwards.
“God, that’s hot.” he growls. “Dean, he’s all inside you, he’s fucking you and his grace is all connected, it’s like he’s really in there.”
Dean groans, “Yeah, yeah, I can feel it, so… life like—”
“Feel good?” Sam teases.
“‘Mazing, gotta — need,”
“You gonna come?”
“Need more gimme more!” Dean begs.
Jack squashes closer, and the bulge in Dean’s belly grows incrementally bigger.
Minutes, or maybe seconds, maybe hours Sam isn’t quite sure, he has another idea.
“Fill his mouth,” he instructs. “Need to fuck his throat too.”
Jack twists around, twitching and sweating, and screws his face up in concentration. Sam sees more tentacle suckered limbs slither over Dean’s body, curling slow and sensuous, and then slipping around Dean’s face before dipping into his mouth. They disappear from sight then, but his jaw stretches wide and he groans in satisfaction again.
When he’s as full at both ends as Jack can make him, Sam gets him to pump. Thrusting the semi-invisible appendages in a pattern that Dean is caught between, rocking back and forth.
Dean’s throat fills up and he chokes, and his ass gets split open, legs falling wide to make as much room as possible.
“The two of you,” Sam croons. “So fucking perfect.”
Jack is falling apart too, his focus wavering as he succumbs to how Dean must feel, all tight and wet, hot and slick smooth.
Sam leans in, “Gonna finish you both off, yeah?”
He gets a closed eyed agreement from Dean and a breathy okay from Jack, and pinches Dean’s nose closed.
The reaction is instant, Dean whines, his legs squeeze closed a fraction, and he tilts his hips. Jack cries out, Sam watches him gasp under the pressure. Dean must be clenching so hard.
He gives Dean a couple of seconds to breathe, and then pinches again. Dean can’t even lift a hand to protest. He squirms wonderfully, his cock leaking and balls drawing up.
Sam runs two fingers up Dean’s cock, and down, and up again, and holds his nose between finger and thumb. He feels a very real and yet also incorporeal appendage slither alongside his fingers, circling Dean’s cock stroking around the head and then suckling.
Dean convulses, Jack yells, and there’s come coating Sam’s hand before he can count to twenty.
Sam releases Dean so he can catch his breath and eyes Jack, who is looking down at his jeans and the wet patch that’s darkening them.
“Did you come in your pants?” he asks. He thought Jack was fit to blow a load and it looks like he was right.
“I think… I think I did.”
“So fucking hot,” Sam leans forwards and kisses him, and then pushes Jacks face to Dean and lets Dean kiss him too.
When Jack falls back after letting the tentacles dissipate, and lays out exhausted in come encrusted pants, then it’s Sam’s turn to have some fun. He’s got a cock that’s eager to fuck after that display and he yanks his own pants down and flips Dean over in no time at all.
He tucks Dean’s knees underneath him, lifting his ass up and presses his shoulders down to the floor. Dean groans, so overworked that he can barely move.
“Nah-uh, no Sam, Sammy, too tender.”
“Think you can take it,” Sam replies, ghosting his lips over Dean’s neck, curling his fingers to dig into Dean’s hip.
“Fuck, so good--”
“Gonna fuck you Dean, gonna fill you up again.”
“Do it, do it, ‘m already ready,” Dean slurs.
“I know, you're all worked open and puffy, do you know what you look like? Such a fucked out mess, and this hole --” Sam thumbs at it, pressing the digit in and easing back out. “Barely resisting Dean, can you feel that?”
Dean flushes red, squirming again.
“Jack, have you seen him?”
“And heard him, and felt him,” Jack says happily. Looking up at Sam from his position on the floor, head lolling close to Dean’s shoulder.
“You did amazing, how’d you learn all this?” Sam asks as he pushes his cock into Dean, letting it glide slow and steady while Dean pants below him.
“Here and there, not much else to do sometimes.”
Jack looks exhausted, but bright eyed and bitten lip happy too, flush and pink in all the best places.
“Think you can do one more thing for me?” Sam asks, jerking his hips to elicit deep moans from Dean.
“Yes, anything.”
“Plug his cock.”
Dean bucks with a renewed burst of energy, trying to claw free, protesting. Sam shushes him with a hand on his head, pushing him into the carpet and ruffling his hair.
“He can take it, make one of those tentacles really thin, ease it up there with plenty of lubricant.”
Dean gasps and cries through the whole thing, over sensitised and mewling as Jack works a glowing, wriggling, alive and tiny tentacle further and further into Dean’s spent and sensitive cock. Sam encourages him to keep going until Dean yells all loud and breathy, as the makeshift sound must reach as far as it can go, filling all the way up. When Sam’s leans back he can see where it enters Dean, pulsing and zinging with energy.
“Can’t can’t, nnn, Sam!”
Sam rolls his hips, feeling the way Dean twitches around him, like heaven.
Dean can barely speak, the double onslaught of Sam-plus-tentacle so soon after coming himself making him drunk with stimulation.
“Too much, too mmmmnnn!”
“Just right Dean, just like this, hold on for me.”
“Is he okay?” Jack asks, breathing shallow as he feels Dean from inside his cock.
“He's having the time of his life, right?” Sam asks caressing Dean's back.
Dean nods, even as tears slip from his eyes.
“So gggg… you, please.” Dean moans.
Which is either a cry for more or a blissed out exclamation, probably both Sam decides.
He grips Dean's hips as firmly as he can, and tries to find the perfect angle. Jack curls a hand around Dean’s face, cupping his cheek, offering his support the best he can.
“All full up, so pretty, taking this so well,” Sam soothes.
He starts jerking in and out, short strokes but hard and fast, easing towards thrusting deeper.
“Over soon okay, hold on.”
Dean moans again, and Sam can see him holding back a wail, like it's caught in his chest and he doesn't want to let it out.
He’s going to pound Dean into the floor for all he is worth, and make him scream in pleasure-pain from his over-worked prostate and his sensitive ass. He’s going to come with Dean a limp and begging mess, impaled on his cock and whining.
He moves a hand to grip Dean’s spent balls and squeezes.
A sound punches out of Dean's mouth, a cry that's more air than noise and he clenches so tightly that Sam has to clutch the base of his own cock to not blow right then and there.
“Go ahead and yell Dean, show me how well fucked you are.”