#top!adam

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We all know I don't like bigbrotherbottom!dean but I do like bigbrotherbottom!sam

Sam all pathetic and whiny as little brother Adam rails him 🥰

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MarginOfThought's Kinktober 2025 - Day 3: Threesome (Sam x Dean x Adam)

“Are- are you sure?” Adam asked, uncertainty clear in his tone. 

“Yes, Adam, he likes it, needs it in fact,” Dean assured him, a confident smile thrown his way. 

God this was fucked up, wasn’t it. But then again so was being resurrected and a whole load of other stuff he didn’t want to think about. Even more fucked up was the fact that he was jealous of Dean for the end of the deal he got. 

“I’m the oldest” He had told Adam when he had asked and the look on his face didn’t allow for any discussion about it. 

“Okay,” Adam mumbled, gripping the base of his dick before he thrust forward a little. 

Sam’s lips were soft and the inside of his older brother’s mouth hot and wet. Adam couldn’t hold back a groan at the way the head of his dick was enveloped in that soft heat, Sam’s tongue lapping at the sensitive crown. “Fuck,” he moan, hips stuttering forward. 

“Told you, it’d be good,” Dean said, smugly, his own hips working hard and pushing Sam's body forward on the bed and right onto Adam’s dick.

Sam in the meanwhile was making small mewling and whining sounds around Adam’s cock before he choked a little when it hit the back of his throat too fast. 

“Don’t pull out,” Dean immediately said, staring Adam down. “He can take it.”

Adam wasn’t so sure, especially not when he saw tears gathering in Sam’s eyes but he did as Dean commanded. Instead, he pushed in deeper, his balls hitting Sam’s face now too as he sunk all the way inside and into his older brother’s throat. 

“He loves taking care of his brothers,” Dean spoke up again, voice strained from his own pleasure. 

One of Dean’s hands was gripping Sam’s hip tight, pulling the big body along with every stroke while the other one had wandered all over Sam at first, pinching at a nipple and now teasing Sam’s own dick that was laying rock hard and nearly purple on his stomach, a pool of pre-cum collected under his belly bottom.

Sam did indeed look like he enjoyed it, dick twitching and hard, noises whiny but not pained and the blissful expression on his face was enough for Adam’s hips to jerk again. 

God this was so fucking fucked up. 

It was however not fucked up enough to stop him from thursting deep into Sam’s mouth, pulling out and smearing his cock along Sam’s lips before plunging back in again. Heat was gathering in his lower belly and Adam knew he would be coming soon. 

“He swallows,” Dean said, evidently having noticed just how close Adam was getting to his orgasm. 

“Fuck,” Adam groaned, pushing all the way balls deep back inside as he unloaded in his brother’s mouth, Sam’s throat working around him as he swallowed what Adam was giving him. 

The wet tongue felt overwhelming on his softening dick as he pulled out and he breathed harshly, leaning against the wall behind him as he caught his breath. 

He looked down at Sam, legs wrapped around Dean’s waist, being pushed and pulled roughly along the bed as the oldest brother was fucking into him. Sam smiled at Adam, upside down and with tears and spit over his face, some of Adam’s cum collected in the corners of his mouth. 

“Thank you,” Sam said hoarsely and Adam wasn’t quite sure if he came back from the dead right or not but maybe it didn’t matter either.

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MarginOfThought's Kinktober 2025 - Day 25: Double Penetration (Sam x Dean x Adam)

Having a third Winchester brother all of a sudden was still an adjustment and half of the time Dean acted like having Adam along was one big tiresome chore but Sam suspected that he kind of liked having another family member again. 

Dean certainly liked the other activities they engaged in as brothers.

Just like right now. 

Dean was three fingers deep in Sam’s ass while Sam himself had opened Adam up just enough to slip a plug inside. Adam had moaned so sweetly the last time and Dean had ordered Sam to prep Adam just enough that he would feel the stretch of the solid metal plug. 

Dean added a fourth finger inside Sam, making Sam keen out at the stretch, wondering why Dean was bothering with another finger when he usually would fuck Sam after three (or sometimes two). 

His older brother didn’t waste much more time though and soon his fingers were pulled out and replaced by Dean’s dick. 

“That’s good, Sammy,” Dean said, when Sam pushed back against him, seating his brother all the way inside him. 

Sam groaned as Dean changed the angle to hit his prostate just right, almost too much stimulation in such a short time. He looked up and saw Adam kneeling in front of him, hard dick jutting out as he lightly rocked on his heels, probably trying to get the plug to hit just the right spot inside himself. 

Dean ran his fingers along Sam’s rim, right where they were connected. “Think we can stretch this some more, don’t you?” 

“Wha-”

The fingers went from stroking to prodding and soon a finger was shoved inside along his dick. “Fuck,” Sam hissed out at the added stretch, not really painful but it wasn’t without discomfort either. 

“Yeah, we can stretch that little hole some more, Sammy,” Dean said confidently, pumping the finger in. 

Adam got up, the bed shifting as he kneeled next to Dean so he could see. A slimmer finger was pushed in alongside Dean’s, Sam panting heavily. 

“What do you say, huh?” Dean asked and Sam was pretty sure it wasn’t directed at him. “Think you can fit in right here, Adam? Think we can stretch Sammy enough to take both of us?”

Sam’s eyes widened, hole clenching reflexively at just the thought. “No, wait, hold on-”

“Yeah, I think we can,” Adam answered, another finger pushed inside Sam. 

The stretch was too much already, and this was probably nothing compared to a whole other dick, but with the way he was held and knowing his brothers he would have no choice but to take it.

“Lay down, Adam, c’mon,” Dean told him and their little brother complied, stretching out beside Sam. 

Dean smacked Sam’s flank before pulling out. “Hop on up, Sam. Ride your little brother.”

Hands held Sam’s hips as he shuffled over, leg thrown over Adam’s waist. The empty space inside him was filled with Adam’s dick, not as thick as Dean’s but it still made him moan.

“There you go. Now, c’mon, open up for me.”

One of Dean’s hands caressed Sam’s side while the other held his dick steady, pushing the blunt head against where Sam was already stretched. 

“I can’t,” Sam whined, trying to move away but Adam’s steady grip held him tight. 

“Yes, you can,” Dean assured him, pushing forward, the pressure increasing until the head suddenly popped inside. Sam cried out at the pressure-pain he felt but he was held still, Dean and Adam making soothing noises as Sam tried to get his breathing back under control. 

Once Dean deemed him adjusted enough, he pushed in deeper, making Sam whine and whimper at the increased stretch. “Taking us so well, Sam. So good for your brothers, Sammy,” Dean murmured into his ear. 

Adam slowly rocked his hips under him, pushing deeper inside even as Dean began to fuck him too, the push and pull so good but also aching deeply. 

“Fuck,” Adam moaned, hips stuttering already. “Shit, not gonna last, feel so fucking tight around me.”

“Yeah, c’mon, Adam, fill him up.”

Dean’s words encouraged Adam, making him thrust faster and wilder until he clutched at Sam tightly, pulling him down on his dick and moaning out loud. “Take it, Sam, take it,” he groaned, coming deep inside him. 

“Shit,” Dean hissed, hips getting faster too. “Such a good boy, Sammy, taking good care of your brothers.” Dean’s voice was breathy and broken and he shoved Sam up Adam’s chest as he rutted deep inside, adding to the mess their little brother had already left inside. 

“Fuck, we need to do that again,” Adam said breathlessly, throwing his head back.

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i know adam would be such a mouthy, cocky top similar to dean and because he's only like 19 and definitely inexperienced he is for sure beating sams pussy in the most sloppy, freaky way ever

Oh you know it, anon! He'd be all enthusiasm and vigor, sloppy and messy. He'd want to try everything once, even if Sam wasn't so sure about it but Sam would let him because he'd want to be a good big brother

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Kinktober Day 3: Threesome (Sam x Dean x Adam)

An Archive of Our Own, a project of the Organization for Transformative Works

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your double penetration fic was really good🚬goon material 🚬

Thank you, hope you had fun with it 😏♡︎

Link for anybody interested

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Kinktober Day 25: Double Penetration (Sam x Dean x Adam)

An Archive of Our Own, a project of the Organization for Transformative Works