we know that endverse!dean is absolutely batshit insane. if both sam and dean time traveled to 2014, do you think he’d kill 2009!dean to have the prize (sam’s hole) all for himself? ♡
I think he would most definitely try to. As soon as he'd get a glimpse of Sam he would know that he needs him and the only way he could have him was by killing the other Dean.
But I also think that 2009!Dean would obviously fight tooth and nail to keep Sam as his.
And maybe if Sam was there he'd try to convince them that they could just share him, that they could both use Sam and that there was no need to kill one another. Like begging and pleading that he could be good enough for both of them, that they could both unload, that he was there for them.
Wouldn't stop them from fighting and snarling at each other but maybe it would be enough to stop them from killing the other Dean...
What would happen if Sam was stuck in a room with Moc!Dean and Endverse!Dean?
Bad things to Sam's little hole, that much is clear.
After probably nearly beating eachother to death they would definitely both bully their way inside Sam, at the same time. There probably wouldn't be enough prep beforehand, no, rather at least one of them would make Sam deepthroat him too - make Sam gag and choke on it.
Guessing that both the Mark of Cain and being a Demon gives them extra stamina and maybe even a shorter recovery time, Sam would be absolutely destroyed by the end of it. Hole lose and red and leaking and maybe even a little bloody. His face would be smeared with cum and tears and spit. Fingerprints, bruises and bites littering him all over. Voice shot from the dicks down his throat but also hours of screaming and crying and whimpering.
And tbh Sam would only get to cum if he can do it untouched, I don't think that either Dean would care enough to make Sam deliberately cum.
MarginOfThought's Kinktober 2025 - Day 27: Gangbang (Sam x Dean x Endverse!Dean x HunterCorp!Dean)
This must be an angel fuckery thing again, like the time they got stuck at Sandover or something. Sam could otherwise not explain why he was staring at three different Dean’s right now.
“Uhm,” he gulped, looking from one to the other to the next Dean.
“Sam,” they said in unison and okay that was incredibly creepy.
And this must be angels or a dream because why would they look at him that way otherwise, like they… like they wanted to eat him alive.
“Sammy,” and that was his Dean, must have been.
“MY turn,” the one that looked like he had been through some shit said and stalked forward. “You gonna be a good little brother, Sam?”
“I-”
“Of course, he’s going to be a good little brother,” the last Dean, the preppy Dean grinned.
“What?” Sam asked, stepping back.
“You know, don’t you?” Rugged-Dean asked, stepping closer and pushed a hand in Sam’s hair, pulling him closer so he could kiss him roughly.
Sam tried to resist for a moment but when a second set of hands grabbed his ass he gave in. A tongue was roughly shoved into his mouth and Sam moaned, head tilting back at that Dean’s insistence.
The hands from behind him made quick work of his pants and soon Sam was naked from the waist down. He was forced to lean forward a little before two thumps indicating that the Dean behind him had dropped to his knees and soon Sam’s ass was spread, a hot tongue laving over his hole.
Sam groaned into Rugged-Dean’s mouth, earning himself a chuckle from all three.
“Okay, okay, my turn now,” one of them said and Sam thought it might’ve been his Dean.
He was forcefully turned around and marched to the bed in the room. He still felt perplexed, confused as to what was happening and he didn’t know why he was going along with all of this, why he was not fighting back or trying to get away - it just felt like something he had to do as he was stripped out of the last of his clothes and was put on his hands and knees. Preppy-Dean took his place behind Sam again and the tongue returned to his hole before he could process what was happening.
“Gonna take good care of you, Sammy,” his Dean said, lifting Sam’s jaw so he could push his erection against Sam’s mouth.
“Please,” Sam pleaded before opening his mouth and taking Dean's dick on his tongue. He sucked at the head, twirling his tongue around the crown and licked into the slit before Dean shoved more of his length inside.
Sam groaned not just at the feel of the hard flesh in his mouth but at the way that fingers had joined the tongue in his ass, opening him up.
“Sam,” Rugged-Dean said and Sam tried to look up as best he could, eyes already tearing up.
That Dean waved around his erection, motioning for Sam’s hand. Sam lifted one of his hands, wobbling a little while trying to steady himself on only one hand before he wrapped it around the waiting erection. He began jerking him off, struggling with finding a good rhythm while there were three fingers in his ass, pressing against his prostate and a dick lodged deep in his throat.
Breathing got harder and he looked up desperately at his Dean, sobbing out a breathy thanks when he pulled back, allowing Sam to take a deep breath.
“Think he’s ready,” Preppy-Dean said from behind him and the fingers inside him were pulled out.
There was some scrambling and fighting and Sam was pretty sure punches were thrown but all he could do was drop his head, close his eyes and just wait.
Strong, callused hands gripped his hips and a thick cock forced its way inside Sam, making him whine out at the stretch.
Sam lost some time after that, he was fucked roughly, pretty sure that there was some switching between the Dean’s but it wasn’t just his hole that was being stretched over and over again - the dicks in his mouth were making him gag and choke, cutting off his breath again and again.
He probably was whimpering, whining and crying but he couldn’t quite tell, too focused on keeping breathing and providing pleasure for his brothers.
“So fucking good, Sam, should always have you like this,” the Rugged-Dean grunted from behind him and Sam could feel him thrust in as deep as he could, rutting as he presumably came inside him if the groans were anything to go by.
There was some more shuffling and the dick in his mouth got abruptly pulled out as he got turned onto his back, legs pulled back before his Dean pushed inside him.
“Little loose there, Sammy,” he tutted but started fucking him nonetheless.
San whined in shame before the head of a cock was shoved against his lips again and he obediently swallowed it. He was rocked up the bed and right onto the dick before being pulled back again, a tear falling down the side of his face.
“Oh, Sam,” the Rugged-Dean said but it wasn’t in a very warm tone, wiping the tear roughly away. “Here, that should make it better,” he added before taking Sam’s dick in his hand, making him keen at the unexpected stimulation.
He was quickly brought to his orgasm, the firm strokes on his dick and the way his Dean was hitting his prostate making him try to curl up as his orgasm rushed through him and he choked on the dick in his throat.
Preppy-Dean thankfully pulled out, allowing Sam to breath before hot splatters of cum hit his face, open mouth, cheeks and he had to squeeze his eyes shut quickly.
Sam’s breath was heaving, the salty taste of cum on his tongue as he slowly blinked his eyes open a minute later.
“So pretty,” Preppy-Dean commented, stroking a finger through the cum painted on his cheek.
“Yeah,” his Dean agreed and Sam knew the tell-tale signs of his brother about to cum. He clenched down on Dean, hoping to give his brother more pleasure as he was bent almost in half, filling him up just like the other Dean had done.
He pulled out too quickly though, leaving Sam feeling empty as he stroked himself a few more times, cum splattering on Sam’s softening cock, mixing there with his own.
“What a show,” Rugged-Dean remarked. “You can go for another round, right, Sam? Be a good little brother?”
Preppy-Dean thankfully pulled out, allowing Sam to breath before hot splatters of cum hit his face, open mouth, cheeks and he had to squeeze his eyes shut quickly.
&
He pulled out too quickly though, leaving Sam feeling empty as he stroked himself a few more times, cum splattering on Sam’s softening cock, mixing there with his own.
