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Title: Orgasm Buddy
Pairing: Sam/Tentacle Monster
Rating: NC-17/Adult
Word Count: 1900
Alternate Links: LJ || AO3 || SPNKink-Meme Prompt

Full List of Kinks and/or Warnings: Bondage, forced orgasm, tentacles, prostate milking, kidnapping, begging, crying, humiliation, barbed tentacles, telepathy, telepathic bond, witches, MotW, crack, humor, BAMF!Bobby.

Setting: No specific season, though Bobby is there.

Summary: Fill for an Anonymous Prompt. Dean listening to Sam scream. I don’t care too much about the context, could be anything, but I want to see Dean just listening to his little brother’s full-throated vocalization.



The sound of Sam screaming rips through him, vibrating in his chest. He's only fifteen feet away, but it might as well be miles for all Dean can help.

“Not again! Please! Not again!” Sam begs, lips bloody because he's bitten them raw in an attempt to stifle his screams.

Sam's tied to an old, splintered wooden table in the basement of a witch's house. He's naked, glistening with sweat, hair soaked with it, and there are tears of frustration leaking from his eyes.

Dean wishes it was him on the table instead of Sam. But he's tied to a St. Andrew's cross on the far side of the room. He can't move, and his throat's raw from screaming at the haggard old witch who's currently torturing his brother.

The witch chuckles, shaking her head. “You're only making it worse by fighting, honey.”

“No!” Sam screams, his voice nearly gone. “Please! Just give me a break! Just a few minutes!”

Dean winces as the witch picks up Sam's sore and overused dick, letting her “sweet little snookums” slither down her hand and onto Sam's dick. Dean has no idea what the thing is. It's slimy and he's counted at least eleven tentacles, but it doesn't seem to have a body. There are seven main tentacles with suckers on the underside, but there are also four tiny tentacles that seem more like antennae than anything else.

The tiny tentacles are so much worse than the bigger ones. They're why Sam is shaking his head, his bottom lip quivering, not because he's a pussy, but because he's been tied to the table for at least three hours and Dean lost count around the fifth orgasm nearly two hours ago. Dean's pretty sure Sam knows the exact number of orgasms he's had.

“Hey!” Dean barks, his throat burning with the effort. “Give him a break. Let it fuck my dick for a while.”

The witch looks over her shoulder at him. “Oh, sweetie, Sylvester isn't interested in your sperm, so you just wait like a good boy while my baby eats his fill, then I'll let the two of you go.”

Dean sputters for a moment, confused by what she just said. “He isn't interested? What the fuck?” It's not so much that Dean's offended. Well, okay, so maybe he's a little offended. What's wrong with his jizz? No, what's got his head spinning is the fact that the little creature wrapping itself around his brother's dick has a preference for who's jizz it sucks.

“Your brother's got old blood in him,” the witch says, the words oozing out of her mouth like she's the one craving Sam's jizz. “Sylvester likes the way he tastes and it'll mean he only needs to feed on one of you before we leave.”

“Oh, fuck!” Sam yelps as he lets his head fall back onto the table, his body going stiff as a board while Sylvester plays with the tip of Sam's cock.

Dean's seen it enough times by now that he knows it's about to shove one of the little tentacles inside Sam's piss hole while one of the larger tentacles works its way into Sam's ass, presumably to massage Sam's prostate, making the whole process faster.

“He's almost full,” the witch says as she pets one of the thing's tentacles. “Don't worry, honey,” she says in a motherly tone as she pats Sam's stomach, “he'll be done soon.”

Sam's already whimpering, squirming on the table. He's probably got a million splinters in his back, but that doesn't stop him from thrashing weakly, trying to pull himself free of the restraints.

“Hurts,” Sam whines. “Please stop. It hurts!”

Dean knows this isn't the worst thing someone could've done to Sam, but that doesn't stop him from feeling bad for him. Sam's balls have gotta be throbbing, his prostate is probably rubbed just as raw as his dick, and his legs keep cramping up, his arms and legs shaking in a way that says his body is close to giving up and just passing the fuck out.

“Oh, oh, oh, fuck, OW!” Sam screams as another orgasm is skillfully pulled from his body.

Dean gags a little as he watches Sylvester gulp and suck the jizz from Sam's dick. He's seen it happen plenty of times over the last three hours, but it still makes him gag every time. He doesn't want to know the mechanics of what's happening inside Sam's dick. Is the tiny tentacle a straw? Yeah, he's gonna try and think about something else.

Sam's shivering, panting, and possibly about to start crying from exhaustion, but Sylvester isn't climbing off him. Dean's tired just from watching what Sam's going through and fighting his own restraints.

“Take it off,” Sam whimpers. “Please. I can't... I c-I can't. I can't take it anymore. Please. Just take it off.”

“Almost done, honey,” the witch says.

Dean hears a loud thump, followed by a crash, the sound of old wood splintering and raining down the stairs.

“Two o'clock up!” Dean yells and one second later the witch's head is blown to bits and pieces, her body dropping to the floor.

Dean's glad Sam's lying flat on a table and that Bobby's a good shot. If Dean hadn't been able to give Bobby the command to shoot high and slightly to the right of the stairs, she might've had time to hurt Sam. Bobby comes stomping down the stairs, smoking shotgun in his hands.

“Get it off him, Bobby,” Dean says.

Bobby doesn't hesitate, just walks up to the table, sets his gun down to Sam's right, then gently starts prying the creature from Sam's dick.

“Ah! Bobby, wait!” Sam screams and Bobby lets go immediately. “It won't let go yet. You gotta wait.”

Bobby frowns, then looks to Dean. “What the Hell's he talking about?”

Dean sighs. “Sometimes it only feeds once. Other times it, I don't know, wants second helpings right away or something.”

“So you don't want me to try and get it off?” Bobby asks, pointing at the thing.

Sam shakes his head. “I want it off, but it's got these little barbs that are stuck... in me.”

“Gotcha,” Bobby says, holding up his hands in a surrendering gesture.

“Fuck,” Sam hisses, squeezing his eyes shut. “It fucking hurts!”

Bobby winces in sympathy as Sam's hips twitch, the stimulation too much after all this time. He leans over and starts to work on Sam's restraints, but Sam groans out a “no.” Bobby's right eyebrow arches up toward his receding hairline.

“If you untie me,” Sam gasps as the thing starts working on him, “I'll try to pull the little fucker off.”

“Okay,” Bobby says, then heads for Dean. “I'll just work on getting Dean loose while you finish over there.”

Sam whimpers a reply that may have been “not funny,” but was garbled and ended on a scream.

It takes about three minutes for Bobby to untie Dean. The witch had rope skills, that's for sure. Dean sags against Bobby, letting the man hold him up while he regains his ability to walk. Just as Dean nods, slapping Bobby's back to let him know he can make it on his own, a wailing scream from Sam makes them both flinch.

“Get it off!” Sam screams even as his body is thrashing about on the table. “Bobby! Fuck! Get it off! Get it off now!”

Dean and Bobby both hurry to the table just as Sylvester slithers over Sam's balls and onto his leg, looking for the witch. Bobby reaches out and grabs it, frowning when the thing coos and wraps all its tentacles around his wrist, snuggling up against Bobby's palm like it's happy to see him. Or feel him, because it doesn't seem to have eyes. But maybe it does. Dean doesn't know.

“You need some help?” Dean asks, pointing at the thing attached to Bobby's wrist.

Sylvester hums, which is really freaking Dean out because it doesn't even seem to have a mouth. The tentacles are rippling gently over Bobby's skin, almost like an affectionate touch.

Dean smirks. “Dude. I think it likes you.”

Sam snorts, so exhausted that he's struggling to keep his eyes open. “He didn't mean to hurt me. He really was hungry. And, ah... it kindafeltgoodthefirstfewtimes,” Sam quickly mumbles.

Dean looks down at his brother, amazed that there's still enough blood left in his upper body to allow Sam's cheeks to flush with embarrassment.

“And,” Sam drawls, cheeks turning an even darker shade of pink, “he's telepathic. Once's the barbs are in, I can sense what he's feeling.”

“It's sentient?” Bobby asks, eyes widening.

“Kinda like a really smart dog,” Sam replies with a feeble shrug. “He can send intentions or something like word pictures I guess. Helen, the witch, promised him all the jizz he could eat if he helped her find demon blood for her spells.”

“You've been-?” Dean starts, but Sam's glare stops him.

“No, I've not been sneaking around draining demons like a vampire,” Sam snarls. “I've got traces of it running throughout my body, which is why he thought I tasted good and he wanted to... eat me. He could smell it yesterday in the supermarket.”

“Wait,” Dean says, holding up a hand. “They were out shopping for a demon yesterday while we were picking up some sandwiches, and this little guy pointed you out of the crowd and said he wanted to take you home and suck your dick?” he asks, barely able to keep from giggling.

Sam sighs, closing his eyes and shaking his head. “Untie me so I can kick your ass.”

Dean chuckles. “You can't kick my ass because Sylvester spent the last three hours suckin' your dick.”

“Okay, untie me so I can sleep for a week,” Sam says, “then I'll get out of bed, take a long, hot shower, get into some comfortable clothes, and after that I'll kick your ass.”

“Deal,” Dean says as he starts untying Sam.

Sam snorts, nudging Dean with his left wrist after Dean gets it untied. Dean looks up, sees Sam motioning toward Bobby, then looks over at the man to see him petting the creature.

Bobby finally realizes both of them are staring at him and scowls. “He's scared!” Bobby growls, then turns around and stomps up the stairs, holding Sylvester close to his chest.

Sam looks up at Dean, eyes surprisingly wide considering how tired he is, then he rolls his eyes and shrugs, wrapping his arms around Dean's shoulders as they struggle to get him up.

Dean really would've appreciated some help getting his big-ass, naked brother up the stairs, but they still manage to make it. Bobby refuses to kill Sylvester and none of them ever mention the fact that the creature always looks well-fed.

And they fight over who gets to hold and pet Sylvester while they watch TV and unwind from hunts.

The End

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