#and maybe dean's mistaken about any similarities but it still gives sam some comfort

[chiisana-sukima]

Happy Wincest Wednesday!

What's one headcanon (cute, sexy, or otherwise) you have about the brothers and the Impala? Time spent in or on it, or things they've done in it, Sam indulging Dean somehow with it, or (etc)?

Happy Wincest Wednesday-Thursday, Phyn! Thank you so much for the ask. <3

I have so many headcanons about Sam, Dean and the Impala. The main one is that they're both very weirdcesty about it. They don't have a sexual relationship with--or even sexual thoughts about--each other. Obviously! That would be sick and bad, and especially in Dean's case, outright wrong. It would be the polar opposite of protecting and looking out for Sam, so clearly he would *never*.

...But it's hardly Dean's fault, or Sam's, that they've both banged chicks in Baby's back seat. That's just a natural outcome of the Impala being, for all those years, their only real home. And it's hardly his fault he's proud that Sam can pull such gorgeous babes, and that maybe when Sam was in high school and first started dating, Dean helped him out a bit by handing over the keys and telling him the best make out spots and giving him advice on what songs got which kinds of girls in the mood, and maybe even making sure he knew there were always extra condoms in the glove compartment (and although Dean *certainly* never looked in the glove box the next morning to see if Sam had gotten lucky, it's not his fault he has to replenish the supply so he does kinda keep track.) If he sometimes fantasizes just a little about some of Sam's chicks later himself when he's banging one out in the shower--about what they were like for Sam, maybe sweet and faux demure, laying on the worn back seat with their clothes still on but the door open to give Sam room to get his head up under their skirt, or maybe shameless and wild, going down on Sam at the drive in, with Sam still in the driver's seat and the soundtrack to whatever movie of the week was drowning out his cut off moans--well, if he thinks about those things on occasion, that's just because he's a red-blooded American man, and Sam has excellent taste in women.

Usually.

Sam usually has excellent taste in women.

There was the Ruby thing, of course. He knows--knows for certain, though he could never prove it--that when Sam would pocket Baby's keys and sneak out to get his fix while Dean seethed and pretended to sleep, that sometimes he and that demon bitch would bang right there in the Impala's back seat. Baby would stink of sulfur the next day, and Dean would hardly be able to contain his rage. But what was he supposed to say? "Alastair warned me you weren't the pure little Sammy I imagined and you'd get with any demon whore who'd give you what you wanted, so why didn't I come down off the rack and it could be me instead"? Obviously he couldn't say that. He only even thought it sometimes because Hell had fucked him up so bad.

And there was Rachel Nave. That one Dean had assumed was on him--so much so he'd still felt guilty years later and a djinn had made it the reason dream-him and dream-Sam were estranged. But okay, while he shouldn't have stolen Sam's prom date and definitely shouldn't have given in when she insisted she blow him parked behind the school only three days after said prom, it had all worked out fine. Yeah, Sam had been angry one of Rachel's friends saw the whole damn thing, but far from pulling him and Dean apart like maybe it should have, Sam had demanded Dean drive him to school the next day and pull Baby right up front; had paraded Dean around on his arm like--well. Like *Dean* was the prize in the exchange and there was no denying Sam won.

Anyway, that's all in the past now. These days, things between him and Sam are easy. Now when he gets an eyeful of a gorgeous naked babe like that Piper chick in Baby's back seat with Sam, it's just par for the course. She's hot, Sam's, you know, objectively hot too (what're you gonna do, Dean certainly can't help that). So whatever it's all about, maybe it's not exactly normal, and maybe Sam and him are both a little fucked up, but the world has bigger problems. It's only worth dwelling on in a good way.

[icefire149]

Certain parts of season 14 and 15 just rub me the wrong way. Everything about the shift when Mary dies again to set up conflict between Dean and Cas just doesn’t hit right. So here’s a new way I’d do it:

Jack still accidentally murders Mary, but after zipping around the Earth in a panic, he goes to Castiel. He has no fear that he’ll lose Cas over this. It’s Sam and Dean that he’s worried about. Especially Dean since he was horrible when he was born. Dean only more recently seemed like he really cared about him. He can’t mess this up. Jack brings Cas back to the house and explains what happened. 

We know Cas is a strategist and his mind would be in overdrive, because of course the Winchesters weren’t going to be okay with any of this. Hell, he’s barely keeping it together. Mary was his friend. But, Jack is his child and responsibility. And he loves him too much to let him suffer. So he devises a plan: Nick was trying to summon Lucifer from the Empty. He was succeeding. Jack and Mary were trying to stop him and Lucifer obliterated Mary. Jack wasn’t quick enough but he was able to send Lucifer back into the Empty and in a rage killed Nick. Now Jack is panicking because it’s still his fault, but not his fault. It’s Nick and Lucifer’s. And Jack while being mostly soulless is still a bit hesitant to weave such a lie to their family, but he agrees. Cas reassures him that the Winchesters will be devastated, but they’ll understand better this way. As a family, all of them will be able to grieve and move on eventually. Because: Nick shouldn’t have done what he did. It was high tension and everyone was upset, and it was inevitable an accident happened. It was just a terrible accident. 

Distraught, Jack asks if there’s anything they can do to fix things? If they can bring Mary back? If they had a body....maybe. This leads Jack to want to see Rowena to see if she could just bring Mary back. They decide to try, but stick to the story. Cas gets zapped back to his truck and Jack goes to Rowena. So we have the similar situation where Jack in a panic tries to force Rowena to fix things and she tries, but also still tips off the Winchesters. Still the magic doesn’t work and Jack is scared. Sam and Dean get to the house and are a mess trying to make heads or tails of the mess. Automatically the blame is on Jack. They’ve been worried about his soul. He must have gone completely dark side. And we’ll note that Dean is the one crawling out of his skin pacing and ranting. Sam is more withdrawn. Jack flies into Cas’ truck when he’s almost there. Cas goes into the house first. He tells Jack to wait in the truck. Cas bars the doorway with his body while he tries to explain the ‘tale’ Jack told him in the car and how devastated he is over Mary and terrified of what they, Sam & Dean, will do next. 

Dean believes Cas. It’s Cas. His anger rolls into grief & tears. His mom died. How did he get here where he has to bury her again. Cas comforts Dean with soft touch and words. He’s sorry. He’s so sorry. Cas gives into his own grief a bit. It’s Sam that continues to stand there in quiet rage. It’s like his whole lifetime of trauma is torn open again. And now there’s this new angry wound that’s only festered since Amara brought Mary back. Yes, he should be grateful that he’s gotten to know her at all, but.....it was never right. She never stayed long enough to really know him. Emotionally her bond with Dean was always stronger. He was always just a fly on the wall. She was his mom too. And now...even Cas is crying more than him. When the hell was she ever anything to him? Sam’s anger spirals, but he’s trying to keep it down. He keeps going over the house there. Something about everything isn’t sitting right with him. There’s something off. He knows it. 

So with the funeral and going home to the bunker, things feel flipped. Jack and Cas were most worried about Dean, but it’s Sam they should be worried about. Dean is angry and upset, but he’s not blaming Jack. He’s actually trying to be there for Jack. This development has Cas over the moon, because this is all he ever wanted. For them to be a family. While Dean fell into the cycle of his father’s anger when Cas died s12/13....this time he’s being what he/John should have been. And Sam is the one sinking into John’s cycle of anger. Sam’s the one drinking a bit more. He’s quiet, but there’s an anger that’s clearly there. He’s distancing himself from Jack and Cas. Eventually he blows up and admits that he blames Jack and his soullessness. For all they know he hurt her / let her get hurt purposely. Which gets Cas angry and Sam flat out admits that he doesn’t trust Cas’ word. Something feels off to him, and this isn’t the first time Cas has tried to go behind their backs. He has quite the history of it. 

This causes Sam, Dean, and Cas to go at it yelling. Jack overhears some and blames himself for ruining everything again. He’s been nothing but trouble for their family. Maybe it would be better if he just left. So he does. This ties us back to Jack being manipulated by Heaven. Dean and Cas are out trying to find him. All ties back in to Jack goes home and finds Sam alone in the bunker. And it’s easy to fall back into the trust Jack has always had with Sam. He’s always had Jack’s back. And he manipulates Jack, telling him that they’ve worked out a spell to bring Mary back. They altered the malak box spell work to harness and focus Jack’s powers. It should be enough. Dean and Cas will be back any minute with Rowena. Jack eagerly believes him and does as he’s told. Jack gets in the box and he stares up at Sam nervous. Sam tells him that there’s nothing to worry about anymore. Cas told them everything. They can fix things now. And Jack looks at him confused, everything? Sam presses that yes, Cas explained how it was an accident. Jack breathes a sigh of relief and then crumbles into tears, how he didn’t mean to. He asked her to stop, but she wouldn’t give him a moment to breathe and then..it was an accident. He didn’t mean to hurt her. And cold as ice Sam goes, I know, and closes the lid. Locking the box. 

It’s a while before Dean and Cas make it back. Jack has enough time to completely unravel in his grief, and anger, and realization that Sam lied and tricked him. Everyone keeps manipulating him and lying. Dean and Cas get back and start arguing with Sam. Just like in the show, Jack breaks out and leaves. Sam still goes into it explaining the truth he got from Jack. Cas LIED. He covered up Mary’s death. He’s known the truth all along. Dean refuses to believe Sam. He’s mistaken. 

Things roll into Moriah and Jack makes it so no one can lie. And because of that the truth finally comes out of Cas’ mouth. And Dean breaks. He tells Cas that he’s dead to him. Cas leaves to look for Jack on his own. Dean’s fury goes in on Jack. He never should have gotten attached. Jack was always a monster. All of this rolls into Chuck’s return and manipulation. He pushes Dean to kill Jack. And the puzzle pieces click into place for Sam. He realizes how much this is all a game to Chuck. Chuck pulled the strings to make every bad thing that’s happened in his life happen just for his own entertainment: Mom, their childhood, dad’s shitty parenting, Jess, demon deals, demon blood, Dean going to Hell, Ruby, the apocalypse, visions, unanswered prayers, EVERYTHING..... Chuck’s newest episode of entertainment was causing Jack to accidentally kill Mary and have to live with the consequences of losing his only family over it. Sam’s anger goes directly into Chuck. 

He needs to get to Dean. Meanwhile Dean finds Cas and Jack in the cemetery. Cas gets between them and tries to talk Dean down. Dean is shaking with fury. He’s never been this mad before. He hated Jack for being born and getting Cas killed, and then he grew to love the kid as family, and he hates him for making him feel this much. He killed his mom, and lied about it. Cas tries to explain that he was trying to protect all of them. He was trying to maintain their family. Dean coldly goes, there’s no family here to maintain. I’m a hunter. Saving people and hunting monsters is the family business, and....I see two monsters in front of me. And he holds the equalizer up, shakily. Jack sends Cas flying so he can approach Dean. He understands what Dean has to do. He accepts it and he’s sorry. Jack gets on his knees and waits. Dean can’t quite do it. He’s trying.

Sam and Chuck get there. Sam starts yelling how Chuck set this whole thing up. Chuck is trying to make Dean do this...for his own entertainment. And everything rolls back into what the actual show did. Dean can’t kill Jack and Sam shoots Chuck. Everything continues to roll similarly as s15 did, but the divorce arc is leaning heavily on Dean is angry about Cas betraying him. 

[misha-moose-dean-burger-lover]

for @bend-me-shape-me's spn advent calendar 2020. prompt: carols.

dedicated to @one-more-offbeat-anthem!! happy birthday <3

After Chuck's defeated, and Billie's gone, and the Empty has been bargained with (semantics, any of the Winchesters would say if you asked one of the four to elaborate) into returning Cas in exchange for eternal sleep, there's peace.

After they're done, and really done, there's time.

A moment to breathe, a minute to look at the clouds, and hours stretching endless, days on end, resonating with something resembling quiet.

And then, there's a guitar.

*

"Nope." Dean declares. "Never seen that thing in here before. And I once did Christmas inventory by myself, so I should know."

Sam snickers at Dean's cavalier tone. He'd been content to examine the instrument from a distance, unlike his brother, but that didn't mean he wasn't paying attention. "You had to do it yourself, Dean. Those were the exact words of the bet."

"I was drunk, and you hustled me!"

"You've known I play poker my entire life!"

"Well, yeah." Dean flashes his best shit-eating grin. "But you've sucked, your entire life, so —"

"— sure I have —"

"— your entire life has really just been a very long, very lame hustle!" Dean spreads his arms in a display of triumph. "And ergo, you hustled me into Christmas inventory-ing. The case is rested, your honor."

"That's not how you say —"

"Sam. Dean." Cas interjects, loud and exasperated. Sam shuts up immediately, eyes falling to his lap, while Dean exchanges a sheepish look with Cas (and Jack, who to his credit, seemed to be unaffected by the mini-feud. But that's less the part about him being God-Lite and more about him being himself. A kid who grew up watching his dads bicker endlessly and mostly, uneventfully, and has come to terms with it as a primary aspect of (at least, his) family.)

Cas, as usual, puts up with less of their crap. "Is this really necessary right now?"

Dean loves him for it, except when it's targeted at Dean and since that's kind of a lot, he isn't sure he loves it, or just loves Cas and generalises the things he does under the wider bracket of Cas.

"And if it's not," Cas goes on, using what is probably his I-led-garrisons-in-heaven voice, which automatically sends a shiver up Dean's spine. "Can we agree the guitar is, somehow, a recent addition and leave it at that?"

Sam nods slightly, apologetic. Dean just rolls his eyes, but it's a yes. (Everyone there knows it's a yes.)

"It's not cursed." Jack cuts in brightly. "Or out of the ordinary at all."

"So," Dean blinks. "We just happen to have an awesome new guitar show up, completely randomly, in this top secret Bunker no one know about, minus any ulterior motives or death curses?"

Jack grins. "Yes."

"Cool." Dean says immediately, and Sam huffs an amused laugh. He thinks he sees Cas smile as well, and a smirk grows on his face.

"Dibs."

*

Unsurprisingly, nobody counters his dibs, and Dean ends up taking the guitar to his room.

It's after a few days of insecurity, leading right into embarrassment, leading further to ignoring its existence, and further still to a mostly depressive array of memories — before it circles back to insecurity, and is about to repeat all over again, when he stops himself in his proverbial spiral, and decides to just friggin' do it.

That night, he picks up the pick.

Fiddles with it in his hands for a minute, and proceeds to abandon the idea again, because it does not feel right. Different shape, different weight.

And Dean Winchester's already enough of a misfit for this project, for his guitar pick to be a poor goddamn fit in his hand too.

But there's something about being so close that stirs up motivation in his heart, similar to the first day they found the damn thing, and next morning, he's out looking for a music shop in town.

That night, he finally plays.

It's uncertain — experimental — and he soon realizes why nobody ever says a damn thing about guitars when they say you never forget how to ride a bike.

But then, slowly, and really slowly at that, music seems to return to his fingers.

It isn't smooth by any chance, or even really accurate, but there's a faint tug in his brain that leads him to the next chord, and a twitch in his wrist that tells him when to strum, and he's awful, he's really friggin' awful, but even repeatedly saying so in his head refuses to dampen the overwhelming feeling that lights him up from the inside to start to feel like maybe he can play again. There's hope, and there's terrible, off-timed, broken music, and there's Dean in the middle of it, and maybe he can actually do this.

Recollection of how to play had come to his hands as they trembled, and tried, but the exhilaration of it, and the joy, only come back to his heart once he'd stopped, heart racing, adrenaline high, and unexplainable tears pricking his eyes.

Dean Winchester goes to bed that night, giddy in a way he hasn't been in years.

And outside his bedroom, his family of three exchange confused glances when the playing stopped abruptly, and then smiles when a sound that can only be said to bear semblance to a squeal, follows the silence.

(The first song Dean had played in over twenty five years had been Joy to the World.

It had also been the first song he'd ever learned — Cassie's choice, not his. Sam, Cas and Jack didn't know any of that. To them, it had just been a christmas carol. But there was also something so moving about that, soft in a way each of them knew Dean would fight against being, that they didn't realize they hadn't budged from Dean's door, long until faint snores replaced the quiet, and they left for their own beds, wordlessly already having decided on a plan for the next day.)

*

Cas knocks first on Dean's bedroom door, and all music immediately ceases. There's a yell from inside after ten seconds of a shuffling kind of silence.

"Yeah?"

"May I come in?" Cas asks.

Another pause.

Cas wonders worriedly if Sam and Jack were mistaken when they said that Cas had to be first, that he was their best shot at getting Dean to open up — the easiest past Dean's line of defense.

Then Dean says, a little quieter. "Yeah, sure."

Cas enters, gently closing the door behind himself before his eyes land on Dean — and he fights the urge to smile, because Dean hasn't kept away the guitar or anything. It's still on his lap, not in playing stance, with his arms folded over it — but he's not trying to hide it from Cas.

"Is everything okay?" Dean interrupts his reverie. Cas nods.

Neither of them say anything for a minute.

"Can I listen?"

Cas surprises himself with his own courage to ask — no twisted words or excuses to stay, just a simple question. Things were so rarely simple for them, but this wasn't a common occurrence either so it evened out.

"Y-yeah." Dean mutters.

Cas lights up.

"I suck, by the way." Dean adds, almost immediately. "But I'll suck less with time, I'm hoping. I mean, I'm supposed to, you know, but I — uh, I mean — maybe I —"

Cas realizes that he hadn't stopped smiling at Dean and that's what had made Dean falter, and he looks away, embarrassed.

"I'll just play, I guess." Dean manages smally, sounding as embarrassed as him.

"Please."

Dean clears his throat instead of playing.

"Yeah."

Cas can tell he's nervous. Even if he weren't good at, and very used to reading Dean, he could've gauged as much. And he wishes he had the right words, he really does, but he's aware a sincere speech of how much it means that Dean let him stay, and listen, would have the opposite effect of calming.

Then there's another knock on the door, and Cas relaxes.

"Dean?"

Sure enough, it's Jack.

Sam had explained how Dean was most likely, unfortunately, to deflect if he was there — "his denial fires up, Cas. I associate it with a parenting complex of some kind, and he just won't let go of it." — so the order had been decided as Cas, Jack and Sam. No overwhelming by arriving all three at once, or one after the other as if it were planned. No, they'd enter after some time, giving the previous person time to make Dean comfortable to them before the next enters.

Cas thinks it's a rather brilliant plan, and wonders if he should ask Sam to formulate a similar one to get Dean to open up about other things too. He doesn't, ultimately.

"Yeah?" Dean yells back.

"Have you seen Cas?"

That had been the plan.

"Yeah," Dean raises his voice to answer. "He, uh. He's right here. Come on in."

And Jack does, and eyes Cas with probably too much meaning (he means triumph) for Dean to not have noticed, before turning to the latter. "Oh. Were you about to play for Cas?"

Dean colors at that, his ears reddening almost instantly, and Cas files it away for pondering later.

"Can I be here too?"

And Dean's eyes widen a little — sign of anxiety, maybe understanding — and he licks his lips and then he nods. "I guess. I mean, okay, fine. But didn't you need Cas for something?" He adds, confused.

"I," Jack hesitates. Oh no, Cas thinks. Sam's prepared him for this, but Jack looks like he's about to, as Dean would say, wing it. And all-powerful or not, he knows his son is a terrible liar. "No, I just wanted to know if you'd seen him."

Dean narrows his eyes.

"Now I do know. That, uh, you've seen him." Jack braves on, determined to reach the bottom of the proverbial hole he'd dug for himself apparently. "So now, I don't need to know anything. Now I can stay."

Dean sighs.

"I can, right?"

There's a lightness in Dean's voice instead of tension when he says, "Yeah."

"Thank you." Jack says brightly, and all Cas can do is shake his head when Jack turns to him for feedback, and the both of them proceed to wear (nearly matching, but not on purpose) excited stares as they focus on Dean.

*

The final straw is when there's a third knock on the door, and Sam pokes his head in. One unconvincing "Where's everyone at?" later, he's joined Cas and Jack in staring with a unnecessary (and hopefully unintended) comfort-the-vic's-family smile at Dean.

God, he loves these dumbasses and would give his life for everyone present in the room, but none of them can act for shit.

It's glaringly obvious they've all respectively shown up to listen to him play.

Which is bullshit in itself, because Dean wasn't being modest when he told Cas he sucks — he does suck. But then, he doesn't think any of them would mind. Sam would probably unlock new levels of the puppy eyes if he knew how happy even playing awfully, made Dean. Jack would be blunt, of course, but undeterringly sweet. And Cas? He'd probably smile at him all the way through, just — that smile of his, that always seems to make time freeze and Dean's heart stutter.

So Dean decides magnanimously to not call them out.

Right away, anyway.

Instead, he turns to them with a question. "Any requests?"

(He can't play one of the only songs he remembers having learned without errors yet, so obviously asking for requests is the right way to go. But you see, once you've given up on impressing, it's only fair to see yourself to the end of the chaos.)

"Christmas carols." Jack answers before anyone else.

"It's May."

"Sam's," Jack swallows. Dean should really get on teaching the kid how to lie. "Sam's making me listen to carols."

"In May?" He asks his brother this time.

Sam shrugs, struggling to keep a diplomatic face.

"You're going to grow up to be the young adult who doesn't take off the Christmas lights in January." Dean informs Jack, who absorbs his words with all the seriousness Dean should have expected. "And, fine. We can do carols."

Cas speaks up. "Any carol you'd like, Dean."

"Nah," Dean shakes his head. "Jack requested it. We'll do what he says." And he insists to his conscience that he said so because he wants to make Jack happy, and not because he's well aware the kid isn't being subjected to carols by Sam in friggin' May, and probably doesn't know any.

"Oh." Jack's face falls. He looks at Sam in the most conspicuous way anyone's ever looked at anyone. "I —"

"Uhhuh?"

"Rudolph the Red-Nosed Reindeer!" Cas blurts, on behalf of Jack, and there's a two second gap where Sam facepalms and Jack exchanges a conspirational glance with Cas, and then Dean's throwing his head back and laughing.

And soon, Sam's joining in with an exasperated kind of chuckling as if he's gotten stuck in the wrong team but he doesn't regret a thing, and then Cas starts too, mostly from looking at Dean losing his shit (Dean strictly ignores thinking about that part and focuses on imprinting Cas's laugh to memory) and probably also because the ridiculosity of the entire situation probably struck him, and of course Jack's smiling at all of them, and it's, altogether, everything Dean could ever have wished for.

The evening ends with Dean playing Rudolph the Red-nosed Reindeer (of course) for at least an hour while consistently getting better at the repeating music, and although it's him humming under his breath (like he always has while playing) that starts it off, soon all of them are offering their own awful renditions to the chaos. Cas is off-key, Sam somehow manages to screw up the lyrics, and Jack is as flat as a friggin' plateau.

And it all comes together in a wholly unmelodious kind of awesome — to Dean the same way they say a mother's love comes through for an ugly child.

After Rudolph, it's Silent Night (another song Dean's learned, it hits him, once he's trying to find the right chord) and even Cas manages to look disappointed at the lyrics Sam and he come up with to make up for not knowing the real ones, and since Jack's never heard this one, he simply listens in rapt attention leaving Dean wondering if he probably ended up learning the wrong version on account of all his concentration.

And last of all, it's We Wish You A Merry Christmas, and Dean plays the chorus enough times that he's perfect at it, because for once, no one messes up the beat or the lyrics, and everyone has the most fun.

All in all, it's an evening to remember.

What Dean learns through it all is primarily the lesson that letting your family think they tricked you into having an audience is sometimes an excellent choice to make, and that things can be crap, but still be enjoyed. That doesn't mean he's not going to practice his ass off learning to play at least the choruses of the Led Zepp tracks he gifted Cas (the idea came to him in bed last night, and Cas has always sounded like he enjoyed them, okay?) so he can play them 'for Cas' as the kid so casually put — but then, some things are different from other things, just the way some love's different too.

And while some things are about efforts, and saying the words that scare you, others are about letting go, and singing carols in bright and sunny May.

The only thing Dean's sure about is that just about all of it comes down to being free.

[go-diane-winchester]

What is Sam's sexuality?

Someone sent this interesting statement regarding Dean and Sam's sexuality:

''Why do a lot of people say Dean is bi n everything when Jensen flat out tells people he is not?? Like yes its a headcanon but that's all it is Head-Canon, not Canon- out of all the characters we honestly should try to find out more on Sam seeing as when asked about his love life n stuff like that Jared say guys or girls and that he would have no problem with playing Sam as pan/bi-??? (May not be 100% accurate I just remember a video of Jared saying both Boys and Girls when in reference to Sam))''

Now that is something interesting.  The only people who question Dean's sexuality are, and always have been, the destihellers.  Normal fans of the show don't care enough, because a character's sexuality is not important to the story of Supernatural.  The most important relationship on this show is between the two brothers.  What they do with their sexual conquests does not impact their personal relationship with each other or even how they do their job.  They still hunt in the normal way, and they still save people.  As a levelheaded viewer, I will respect the canon and the fact that Dean is straight.  However, it would be fun to discuss Sam's sexuality in our little corner provided we don't take each other's words and start nagging CW to make Sam anything other than what he really is.  I am giving you my theory.  But it is still a theory which means, its just an opinion.  It just opens doors for more interpretation. 

When Dean is mistaken for a gay man, he reacts with great shock.  Sam, on the other hand, just smiles.  It amuses him.  It might be because ''this person hit the nail on the head''.  Or it might be because he is amused at how mistaken that person is.  He doesn't consider being called gay, an attack on his masculinity.   That might be the case with Dean because Dean is down home old fashioned when it comes to his sexuality.  He's not prejudiced.  He just would prefer not to be mistaken as something he is not.  That is why when Dean said ''the more troubling question is why do these people assume we are gay'', Sam's amusing baby brother response was ''well you are kind of butch.  Probably think you're overcompensating.''  He is trying to rib his big brother because he knows being called gay bothers Dean more than it does him. 

Sam slept with a demon.  He was in a state of terrible mourning.  It might have clouded his judgment.  However, the fact that the demon was in a female cadaver, might have motivated him.  I don't think this is proof of pansexuality because it would be insulting to assume that a pansexual will sleep with anyone, even a demon.  Remember, Ruby strategically edged closer to him by using his dead brother as a motivation.  Sam accessed a male cross roads demon to make a deal for his dead brother.  If kissing the demon would have brought his brother back, I think he would have done it.  None of this is proof his bi/pansexuality because emotional duress is a huge factor here, brought on by his love for his big brother.  Remove Sam's mourning and the entire scenario might not happen at all.  None of this reflects on Sam's sexuality. 

Sam being raped by Luci is still up for debate and I wish they would bring closure to this issue because it is not a joke.  However, being raped is no reflection on his sexuality.  He's just a victim, unless nothing happened and Luci is just being an expletive to annoy Sam. 

There has been no indication about Sam's sexuality in canon, except for this one exchange. 

Dean to Henrikson:  You kinky son of a b*tch.  We don't swing that way. 

Now, because we respect canon, we have to take this whole statement as true.  Dean is talking about both him and Sam.  I accept as true because I am not a heller and because canonically it makes sense.  Dean has raised Sam.  He knows about all of Sam's quirky little habits, about his likes, dislikes and embarrassing little fears.  He knows exactly which one of Sam's buttons to press.  If Sam was bi or pan, Dean would know.  On the flip side, like any other closeted person, Sam might have hid this side of himself from his brother, perhaps because he knows his brother well enough to know how to hide something like this from Dean. 

But then that hypothesis brings up the pertinent question of why.  What would be his reason for concealing something like this.  He didn't hide having sex with a cadaver.  Both he and Dean have died plenty of times.  Why would he hide this part of him from his brother in the face of death especially in the early years when they didn't know they were immune to death?  Is it because Dean is prejudiced?  Well, Dean didn't seem very prejudiced towards Charlie.  Is it because he is concerned that, because if this new development, Dean wouldn't understand how to react, and he doesn't want to make Dean more confused, considering what Dean has to deal with on a daily basis?  No, that doesn't make sense either because if he cared so much about not worrying his family, he wouldn't have gone to Stanford despite the fact that it tore the family apart. 

To date Sam has only taken a personal interest in three male characters.  Cas, Kevin and Jack.  Jack doesn't count here, because canonically Sam sees Jack as his child.  Then there is Kevin.  Even though there are a biased group of writers who didn't really focus on Sam's relationship with Kevin, some viewers may assume that Sam had a meaningful relationship with Kevin, whilst others will be offended by this because Kevin was a school kid and ''Sam would never do that''.  If you factor in Sam's affection for Kevin, it might explain his anger towards his brother when the whole Gadreel debacle happened.  Gadreel used his vessel to get close to Kevin and kill him.  Maybe that's why he was upset with his brother and blurted out his anger without meaning it. 

Sam and Kevin were very similar.  They were studious.  They were thrown into a situation they both did not want to be a part of.  They were afraid of being in said situation until they grew out of that fear.  They were very similar is temperament to each other.  Unfortunately, switching his phone off and leaving Kevin to suffer for a year is just bad writing and throws this whole theory out the window.  This is why it is difficult to analyze Sam's character and sexuality because Ross-Lemming and gang have done considerable damage in 7 years.  There is only one meaningful interaction between Sam and Kevin [a church scene] and the interaction was so emotional and affectionate on Sam's part, that Kevin actually thought Sam was hitting on him.  The Sam and Kevin storyline is one of the worst fanfic tragedies because of the bad writing in canon. 

Cas and Sam have an interesting story.  When Sam first met Cas, he fell all over himself just to greet the guy.  He was starstruck, for want of a better word.  There was even an emphasis to their handshake which is perhaps one of the most intimate handshakes I have ever seen between two male actors. 

It was as if he was meeting a legend.  Back in Season 4, Cas kind of was.  Now, not so much.  The legend is dead.  And Cas is a joke.  Cas and Sam have various similarities.  They have similar temperaments.  They have messed up spectacularly in the past, and both admit to it.  They both bonded over the fact that they accidentally caused major damage in the quest of trying to solve a problem.  They bonded over their pain.  And Cas reassured Sam that messing up and falling in Dean's eyes is something that Sam does not alone have a monopoly in.  Cas has messed up plenty.  He was trying to comfort Sam.  Most of the emotional heart to hearts seem to happen between Sam and Cas.  Dean is usually mocking Cas and Cas is usually getting confused by Dean. 

Castiel's dialogue either to or regarding Sam: 

Nothing is worth losing you.

The only person who has screwed up things more consistently than you, is me.

You wont take Sam Winchester.  I won't let you. 

You come near Sam Winchester, and I will kill you.   

I was lost until I took your pain.

The idea of Samstiel and Sastiel highly amused Sam.  In fact, I have very seldom seen Sam so enthusiastic about something.  Remember nobody pointed out that there was a pairing between him and Cas.  He did that on his own, and didn't appear repulsed by the idea of him and Cas together.  Dean on the other hand, is repulsed by any mention of fan fiction, even going so far as to break the fourth wall and glare at the guilty party when destiel is mentioned for the first and hopefully last time on Supernatural. 

Now Sam and Cas even share a child, and I think that is bringing them closer.  Unfortunately, Misha oversells the stupid dinghy destiel and leaves a more promising ship behind because he over-pandered to his lunatic fandom.  And giving into Sastiel made make them go full psycho.  Which is a terrible sign of his stupidity because if there is any slash pairing that makes any canonical sense, it is sastiel.  Destiel appears more like an arranged marriage for a green card.  Everything is forced on Castiel's part and faked on Dean's part, because both actors involved has different point of views regarding destiel and slash fiction. 

In conclusion, the only lingering indication of Sam's supposed bi/pansexuality seems to be his interaction with Cas.  Even then, it is just an analysis and not canon.  And it is just my overall analysis, which I am sure, is limited.  I don't know of any other subtext with regards to Sam's sexuality.  If anyone out there has a proper example, kindly comment.  I would like to know what is construed as bisexual Sam subtext. 

Edit:

The original commenter has sent this link to amino apps where this very topic was discussed.  Thank you dear.

https://aminoapps.com/c/supernatural/page/blog/sams-sexuality/4gCY_uoBpVrq58YXZeLkJG8V4ew15D