#pining!dean

#dean winchester

#endverse!dean

#moc!dean

#demon!dean / deanmon

#teen!dean

#mechanic!dean

#younger!dean

#older!dean

#dad!dean

#husband!dean

#pining!dean

#soft!dean

#protective!dean

#jealous!dean

#drunk!dean

FIC TYPE

#dean winchester headcanon

#dean winchester drabble

#dean winchester oneshot

#dean winchester twoshot

#dean winchester series

#dean winchester series masterlist

VIBES

#dean winchester fluff / #dean fluff

#dean winchester angst / #dean angst

#dean winchester hurt/comfort / #dean hurt/confort

#dean winchester comfort / #dean comfort

what would dean do

Sam opens his eyes, grins at the camera. “Think I should take it off?” He pulls the zipper of his hoodie down a couple inches, bites his lip, drags it further until the N and F are separated. That’s enough to trail his hand up between his pecs, up his throat, pushing his head back as he draws his fingers up over his chin to tease at his lips. Pretends it’s someone else’s hand (pretends it’s dean’s) as he sucks the tip of his index finger in and moans softly. He brings his free hand up to squeeze his pec, and blushes again. It’s not a tit, but he’s been touching himself the way Dean touches girls for so long he’s not sure he can get off without it.

Slowly, he pulls his finger out of his mouth, makes it pop loudly before tugging the zipper down completely and shrugging out of the sleeves. “You’ve got a great bod, kid, let us get a good look,” the studio said, so he pauses there, flexing his muscles, running his hands over his abs and gasping as he tickles his own sides. Goes back to his chest to squeeze and tweak his nipple, pinches one hard and gives it a little twist that makes him gasp. His eyelids are heavy as he looks into the camera again.

“I like when it hurts, just a little.” He barely recognizes the husky voice as he confides in the camera. In the thousands, maybe millions of faceless men who are going to watch this. Sam lets his eyes fall shut and pictures Dean standing there. “Wish you could touch me.”

what would dean do

Sam lets his hands fall, caresses his dick through his sweatpants with a groan. “Ready for more?” He falls back onto the bed, lifts his hips to slide his sweatpants off his hips, scoots back as his cock springs free of the waistband to thump against his belly. It’s hard and heavy, aching for attention but he avoids touching it. Frames it in his hands as he kicks his sweatpants off to the floor, pressing on the base with his thumbs to make it stand straight in the air. “Big, huh?” is not false bragging. He knows what average is, in real life and in porn, knows that he’s larger than most. Knows that he looks even bigger shaved bare, like the studio instructed. “Too bad it’s wasted on me.”

He pulls a leg up, raising his ass a bit higher, feels the tension in his abs as he reaches around his thigh to grab a cheek. Spreads himself wide, shows his hole to the camera. “What I really like… I like playing with this.” He braces himself on one elbow, reaches further, and rubs just the tips of two fingers over his hole, dry. His dick twitches, precum beading at the tip and smearing on his skin. Sam presses lightly, then harder, gets a finger in halfway to the first joint. A quick glance over his shoulder and he’s able to stretch his arm back to the bottle of lube on his nightstand. He flicks the lid open with his thumb and drizzles slick over his fingers and hole, hissing slightly at the chill.

The lube makes everything slippery, lets his first finger sink in completely and he’s got a second shoved in with a happy sigh before he remembers what the studio said. “Go slow, make ‘em wait for it.” He pulls his fingers halfway out, shoves them back in, starts slowly fucking himself and crooks his fingers up to hit his prostate. His dick leaks out more precum, a steady drip like a string of drool from where the head bobs in the air to his belly. His hips jerk, fucking back at his fingers and he bites his lip. 

“Could come like this, but you’re here for something else, right?” Sam pants, pulling his eyes back to the camera. He doesn’t stop fingerfucking his ass, feeling the soft heat clenching around his knuckles, just adds another finger and moans at the stretch. “Betcha wanna see me take… something… a bit bigger.”

He presses his fingers tight into his hole, rubs against his prostate and moans as he reaches his other hand out, grabs the dildo standing on the stand. It’s as long as he is, thick as his wrist, and he doesn’t think about how he’d picked it for its resemblance to Dean as he brings it to his lips. The position isn’t the most comfortable, but his tests showed him that it gets his face in frame without losing his ass, lets the audience see him wrap his lips around the thick mushroom head of his dildo while his fingers continue to thrust and stretch in his hole. The chemical taste of the fake dick is familiar, hours of practice for his own sake and he’d never planned to show off on camera but it is what it is. Slowly, carefully, he pushes the dildo into his mouth, opening his throat for it, doesn’t stop until the balls are pressed against his chin and he’s gagging on the length down his throat.

When he pulls it out, it’s glistening with spit. He’s gasping for air and his eyes won’t focus. His lips feel swollen when he licks them, tries to speak and has to cough to clear his throat. “Need it now,” Sam manages to say, and he pulls his fingers out of his hole, teases around the rim with the cock. “Need you so much…”

Sam struggles to relax as he pushes the head against his hole, pushes out against it, gasps and pants and whines until it finally pops through the ring of muscle, then lays there, clenching around the shaft until the burn of toothicktoomuch subsides. He fumbles for the lube, finds the bottle in the rumpled blankets where he dropped it, drips more slick onto the dildo and pushes it in farther. His back arches as he gets the toy deeper, each fraction of an inch a struggle. It’s his first time fucking himself with anything other than fingers and he’s almost sobbing with the pleasurepain of it, tears streaming down his cheeks. “De…” 

did i say that out loud?

It doesn’t matter. He’s got the whole of it inside him, filling him more than he’s ever been, and he wants more. Wants to feel weight on top of him, pressing him into the mattress, wants someone else pulling the thick shaft out and thrusting it back in, wants to feel hips pressing into his, swiveling the way he used to see Dean swivel in girls. All he’s got is his hand and a heavy chunk of silicone, so he gets a good grasp on the balls and starts thrusting and grinding the dick into him.

what would dean do

He wraps his other hand around his own cock, squeezing tight at the base, stroking himself roughly in time to the thrusts. His hips jerk back onto the dildo and forward into his fist and he throws his head back, bites back a howl and turns it into a long, low moan. It’s hard to keep a rhythm and he gives up on that, focuses on the feel of being stretched wide and stuffed, grinds back to try and get it just a little deeper, and his vision goes white as he comes harder than he ever has, spattering up his chest and he feels a few drops land on his chin before he collapses, boneless, on the bed.

Sam takes several tries to roll over, pushing himself up on his elbows and knees, but he finally gets in the studio-requested position and lets the dildo slide slowly out of his slicked-up ass, lets the camera linger on his gaping, puffy hole for a long minute before standing up with a groan, walking on shaky legs to turn off the camera. He pulls out the tape before he can chicken out, shoves it in the pre-addressed envelope and wipes himself off before getting dressed and heading out to drop the envelope in the mail, and he resolutely doesn’t think about it as he heads back to the showers to scrub himself clean.

-

Dean pulls the package out of the PO box and tries to pretend he’s doing this for noble reasons as he shoves $5k of pool hustling and poker cash in an envelope to mail to Stanford. Tries to pretend he’s gonna destroy the tape without watching it, tries to ignore the fact that the last tape was worn out from watching it before he finally broke it in pieces and burned it by the side of the road.