Sam and Dean when they first met Adam and something just...clicked.
They felt the same thing they felt for each other for Adam; he was family.
They start ever so slightly and slowly trying to bring and ease him into the same dynamic and relationship they have for each other; faint touches on his thigh while they're teaching him something, hand grazes that might be just a bit too long to be normal when passing cups of coffee, and even offering their bodies on cold nights so they can all stay warm.
Soon enough, it works and Adam is reciprocating those same touches and glances. Glances that are pure hunger and lust.
One cold night, they're all in the same bed doing random stuff; just being close. Sam and Dean both lean in to give Adam a kiss on the cheek but Adam turns his head towards Sam accidentally and they kiss on the lips. That kiss soon turns into a make out session which then turns into their clothes flying across the room. No one knows what happened in the middle, too caught up in each other to.
They're frantically touching each others bodies, panting. Nothing truly happens, just hand and blowjobs and yet they all had the best orgasms that night.
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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.
once again bring up how underutilised adam milligan is wincest-wise. and i know it's because of how he's written in the show, but like, there is a whole other winchester brother??? dean should be thinking about that fact in the back of his mind 24/7 forever, imo.
Okay. Asking thoughts about Castiel went awesome. I got a lot of cool analysis about his role in the plot and cool points and just some of the best answers I've gotten in ages from so many people. So I'm going to try and see if I can repeat that, or at least come close.
What are your thoughts on Adam? His role in the plot, how he was handled, him as a character himself? And of course headcanons and whatnot.
- @schizosamwincester
I love Adam! I think the plot did him really goddamn dirty honestly. I know it's a story about Sam and Dean, but I really think that the family-as-horror element could have been further explored with Adam.
I headcanon Adam as having stronger Mommy issues than Daddy issues, given that to him John was your fairly run-of-the-mill absentee Dad while his Mom was a struggling single mother who had a kid with an older man. I think exploring the flip-side of single parenthood could have been really interesting - contrasting Adam's relatively safe childhood with his Mom vs Sam and Dean's unsafe childhood with John, and how they're all fucked up in different ways by those upbringings.
I have said before but I've been rotating the idea of Sam/Dean/Adam for a looooong time, specifically in a pseudo-family of Dad/Mom/Son. I love the concept of Sam and Dean attempting to like...re-parent Adam, creating their own little fucked up 'normal' family, except that their normal is still incestuous and weird. Like, even if you ignore that they're all brothers, their version of the Dad/Mom/Son dynamic still involves them fucking Adam as well as being his caretakers.
these boys: we don't need parents! we'll make our own family!
the angels watching them: i think they just invented twenty new sins
Thinking about a world where Adam is pulled out of the cage early without Michael and is unwillingly pulled into Sam and Dean's emotionally incestuous codependent relationship. He hates it, but his brothers have made too many enemies for it to be safe for him to live by himself and he doesn't have a certain angelic companion to help keep him safe. So he's kind of just stuck there, reluctantly playing a part in his brothers codependency because he doesn't really have a lot of options and occasionally lashing out at them whenever they cross a line he's uncomfortable with
Edited 04/15/2024: I made a little ficlet set in this universe.
Edited 07/26/2024: I've decided to rewrite the fic and am in the process of doing that, so the old one is going to be deleted.
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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.
I think Adam would not really participate but would want to direct them and watch. And he'd be into denial. Just take them to the edge and never let then fall or reach completion, just playing those mind games with them, frustrating them to no end.
Though realistically, I think he'd feel upset for being dragged into this mess and want to go his own way, grieve his parents, go to med school and live his life.
Okay I kinda like that idea, anon. Don't really know how Dean would take to being directed by his little brother but I do think that if Adam would definitely do it in denial (a guilty pleasure kinda thing).
But yeahh, realistically and tbh if he were sensible he would run away from the Winchesters as quickly as possible.
