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Meg said "I feel so... clean" after kissing Cas (06x10) and Dean said "now I feel dirty" after hearing Sam making out with Ruby (04x09). What if it's literal: making out with a demon can make a human dirty, and making out with an angel can make them clean?
If in S05 timeline Dean thinks this might be one of the ways to purify Sam's demon blood, make him clean, or maybe Sam wants it, and they think it might be worth a try, so they propose that Cas needs to make out with Sam. Both Cas and Sam are a little uncomfortable at the thought, but it's strategic, so for Sam's sake (and maybe potentially, they think, by helping Sam get rid of the demon blood, he wouldn't be the ideal vessel for Lucifer, then they could solve the Lucifer problem and prevent the Apocalypse, so basically maybe this is the solution to save the world), they have to kiss. And Dean doesn't realize how uncomfortable this makes him to see and he doesn't understand why, just secretly having a gay panic moment, rationalizing it as just because it's his friend and his brother, and they have the manly rule of not talking about these kinds of intimate activities or relationships. But Dean knows it's not any relationship, just a strategic move, but he's still so unsettled by it. He doesn't know it's jealousy.
But they can't tell if it works or not. Sam doesn't feel any difference. Cas can still see Sam looks different (Anna has said Sam looks different after drinking so much demon blood, it changed him, angels can see demons' true faces when they're in the vessels (separate thoughts: that might mean demon-blood-drinking Sam might can also vaguely see Cas's true face, and it looks different from the vessel, and Sam mentions that to Dean in some casual talk, like "Did you notice Cas looks different", Dean doesn't, then as Sam elaborates, Dean realizes something must be wrong with Sam and he gets worried but also secretly jealous that he gets to see Cas's true face but Dean doesn't, that even makes Dean has a split second of thought wanting to try some demon blood just to see what Cas's true face looks like but he doesn't, of course.)), so it could be because Sam has been changed by the demon blood and demon sex too much that simply kissing isn't enough to fix/reverse/purify him, they have the horrifying realization that they might need angel sex. All of them are uncomfortable at the idea at first, but once again, this is strategic, so Cas is onboard first (which surprised Dean because this is probably not too long after S05E03 and he's seen how flattered Cas can get around the idea of sex and he's "never has the chance", but somehow right now he's agreeing so quickly. Dean doesn't realize he's annoyed/upset too, for no good reason.). Sam would be bitching a lot, but Dean would be like, some meds taste bitter but good for your health; you should've thought about this before you went to have sex with a demon; he's sure this can be worse, having sex with Cas can't possibly be worse than demon blood rehab. So they went to some motel room to do that; Dean's in the separate room feeling overwhelmed and aching and agonizing and just a mess, and he doesn't understand why, thinking maybe it's just because he's worried about Sam.
And they come out, Cas says he thinks this is working; he can see less demon blood in Sam, but it still exists; they should continue doing this until Sam is purified. Dean has no way but to agree (and keep aching so damn much). Sam isn't happy but stops complaining.
So they do that until Cas announces Sam's clean; Lucifer is officially pissed that Sam's no longer his ideal vessel; they basically reversed all of Azazel's effort from all these years ago. Dean's glad (that Sam's safe now) and relieved (that he doesn't have to think about Cas and Sam doing that again) and still a bit devastated (that "you're not going to die a virgin on my watch" but Cas's first time isn't with him), and he's startled to realize he's actually thinking that (hoping his first time is with him without realizing), and he starts to understand that's jealousy that he's feeling and he doesn't know what to do about it, and he doesn't know what Cas thinks about this whole thing with Sam (nothing, actually, Cas really only does it for practical outcome) or feels about it.
More aching and pining from Dean, maybe even thinking Cas loves Sam, and slowly realizes he's fallen for Cas, until he can't take it anymore and one day just bursts out miserably (something bitter, like maybe Cas was just in the middle of talking about something random, then similar to S06E03 Sam's bitter "You like him better or what", it's now Dean asking Cas if he likes Sam better or what, Cas answers very plainly, no, he and Dean share a more profound bond, then Dean huffs and snorts and blurts out bitterly, "Then why did you do it with Sam not me?" Cas gets surprised and thinks he's being unreasonable, be like, "You don't have demon blood in you that needs my cleaning." Dean's like, "You don't know that, maybe I do. How would you know, you didn't check." Just being ridiculous with each other. And Sam watching this exchange and has the sudden realization of, "Oh my God, Holy, you're in love with him." Dean's like, "What are you talking about. Shut up." Cas: "Are you?" Dean can't answer and stutters, and yeah he's really so in love and miserable this whole time. Cas doesn't realize that until now, and goes with a straight face, "Okay, I can do that with you too. If you want. Just to check. In case." Which is kinda uncharacteristically babbling and he's nervous, almost like in the brothel again, but he's watching Dean. And that startles Dean so much he wouldn't believe it. But things just, sort of, get sorted out automatically.) Then Dean just goes into the motel room with Cas and smirks at Sam as he closes the door, being so unimaginably happy. Sam just sighs, they're idiots.
what do they say? (a Dean/Cas fanfic)
Dean had asked Castiel if he knew what they say about big feet. He did not. But he intended to find out.
Rated: T / 6,201 words / Supernatural Special: Castiel #1 (Comic)
“You know what they say about big feet…”
Castiel hadn’t known what to make of Dean’s comment back when he made it, and in the time since he and the Winchesters slayed the skunk ape Dean never explained what he had meant about big feet.
He wondered if there were contextual clues he might have missed. But after reviewing their short interaction over and over again Castiel wasn’t closer to figuring out what Dean wanted to communicate. In fact, Dean’s sly smile, smoldering gaze, and purring voice served to confuse him further.
Castiel was driven to distraction by his obsession.
He resolved not to waste any more time thinking about Dean and big feet.
Somehow that caused him to only think of Dean and big feet.
His comment had lodged itself deep within Castiel’s mind and, despite how he pried, it refused to budge.
He was in hell.
Salvation was the stubborn bastard who got him stuck there.
His frustration soon became too much to bear, and Castiel snapped.
The Winchesters had sheltered at an unremarkable motel somewhere in the farthest tip of the Florida panhandle that evening. Dean sat on a bed cleaning his gun. Concentration marred his pleasant features, causing his face to divot, his freckles collapsing into creases and winking out of sight like the incandescent light bulbs with faulty wiring on the motel’s sign outside. Sam, meanwhile, counted their meager savings by hand from his spot on the other bed. Both were dressed in the standard uniform of plaid shirts and denim pants. Neither had an inclination that Castiel was in the room with them, watching for an opportunity to pounce from an invisible perch in the corner.
“Are you sure you don’t want something else?” Sam asked.
“Nope,” Dean said. “Burger’s fine.”
“Because we passed this Mediterranean place on the way over. Looked pretty interesting. Maybe we can –“
“Do we have Mediterranean money?”
Sam pouted at the change he cobbled together. From his vantage point Castiel saw that there were barely twenty dollars.
“Exactly. Now go to the diner down the road and get me a burger. And pie.”
“We don’t have money for pie either.”
“You don’t need money.” Dean looked at Sam as he twisted a patch rod round inside his gun’s bore. He leered and winked. “Flirt a little. Flex your muscles. Should get you at least two slices.”
“What if I don’t want pie?”
“Who said the second slice was for you?”
Sam flipped Dean off and left. He cursed after him but was drowned out by the heavy slam from the closing door.
It was just Dean and Castiel now.
This was the moment he’d been waiting for. But before he could act Dean set his gear beside him and looked in Castiel’s general direction.
Castiel tensed.
“Cas,” he said, “you can come out now.”
Damn. Dean had gotten better at sensing his presence.
“C’mon. Quit stalling.”
Castiel flapped his wings, exiting the interplanar space he hid in and fully materializing within the motel room. His trench coat snapped its hem while his tie was whipped by the slight squall his entrance caused. He withdrew his wings, and tamped down his wild, dark locks into something less ruffled with a quick swipe of his hand.
“Hello, Dean.”
(click here to continue reading)
I think we've said this before but after Mildred brings up that Dean is pining for someone, and we know Dean wants Amara dead when she's not around, Dean goes to bed and lays on the left (cas') side.
Before that as well, Sam brings up purgatory, a year where Dean pined after Cas while trying to save him.
Then he lays on Cas' side, thinking hard about... something.
Dean shoulda been Lucifer's vessel. If they'd been smart, they woulda done it like that.
Because Lucifer... Dean can understand him on a level that he will NEVER understand Michael. Michael the good son, the obedient soldier, the one who cast his own brother into the Cage on Daddy's say-so.
Dean mighta been raised to obey his dad's orders, but when the order was "kill Sam," well. There was no way he would follow that.
Lucifer, though... Lucifer wants Sam. Wants to possess him from the inside, and Dean's been dreaming of that his whole life. If Luci had popped into his dreams with his forked tongue, promising you'll get to feel Sam's insides if you say yes, Dean wouldn't have stopped to consider if it was a lie.
Lucifer woulda owned his ass, and Dean woulda been happy about it as long as he got to experience Sam.

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16/04/23
he knows this feeling all too well, he feels his heart begin to swell. handsome stranger, you have made his insides turn to jelly.
castiel’s version
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Daily Destiel 💙💚
Pining Dean. Follow your heart. 😔💔😊❤️
Thinking about how in this episode Dean made Cas smile because he want that Cas cast Lucifer out of him and there is just Dean pining over Cas even thought there was Amara 👀👀