The first time it happened, Dean had been very, very drunk, and Crowley had been confused.
Up to that point, it'd been a lovely day. Ruling Hell was hardly sunshine and lollipops all the time and Crowley had been itching for a vacation, but unfortunately, even the king needed a proper excuse to delegate the most urgent parts of his job and disappear for a few days. Or weeks, or months. Retrieving and wooing Hell's newest Knight was about as proper as excuses came, in this line of work.
Getting Dean out of the bunker was easy. He was very confused. Scared, of course, because he was definitely not feeling like himself; Crowley imagined he hadn't felt much like this since he'd been in Hell, under Alastair's oh-so-professional tutelage. Running, with someone who knew what he was going through, had sounded excellent to him. And, precious heart, he'd been so very worried about hurting dear Sammy. Or thought he should be, at least.
Crowley could honestly gag on the two of them sometimes, many possible dirty jokes not intended.
The plan was to ease Dean into things. Being a demon, working with Crowley. The best way to do that seemed to be to show him a good time. So Crowley brought him to the usual sorts of dives he haunted when he had nothing to kill or screw: karaoke, greasy food, booze too cheap to be watered down. He spent hours getting to know the new Dean, whom he enjoyed much more than the old one. Fewer inhibitions, because apparently that was indeed a possibility, and more inclinations towards aggression and violence. Again, amazingly, possible.
In the beginning, Dean was all concern for his brother. Sort of. Just like he was sort of worried about hurting him back at the bunker. You see, as a demon, one of Crowley's many exquisite talents was empathy. In the psychic sense, not the Hallmark Channel feelings-fest one. The emotions of other demons were no issue for him to read, strange and stunted though they might be compared to the riot of color that humans felt.
The truth was that Dean really didn't feel anything at all for Sam, and that puzzled him. Frightened him, even. He kept mentally reaching for the absence, aping the sensations and behaviors of guilt and worry and love even though he wasn't actually feeling them. He was adrift without that festering perversion of a brotherly bond that'd been his only constant for decades.
Crowley could be the new constant. Crowley, loyalty to Crowley's Hell, and copious amounts of murder on behalf of (you guessed it) Crowley.
That wouldn't happen overnight, though, and the very first order of business was a good, old-fashioned Rumspringa, because why should the Amish get to have all the fun?
Dean forgot about Sam very quickly once Crowley coaxed him into drinking and flirting and fighting and playing. He cleaned out the pockets of nearly everyone who thought they could best him at poker, darts, or especially pool, doled out rather serious injuries to those who couldn't accept he'd won fair and square with the help of his demonic reflexes, and fucked two separate loose women in bathrooms. And, of course, he imbibed. Crowley sat back and enjoyed himself, providing cash and company as needed.
He was initially surprised when the copious amounts of alcohol began affecting Dean. But he'd done a lot of research on Cain's transition into a demon, and thought he remembered something about human needs and traits persisting for a while. He'd been mostly focused on his excitement over possibly getting his own pet Knight of Hell for a very early Christmas present. The real shocker here was how long it took Dean to get drunk; Crowley was unsure if it was because of his species swap or if it was just the ungodly tolerance he'd built up over the years.
Once Dean was inebriated enough to be feeling sleepy, Crowley decided they needed to get a room. In an establishment that looked like it catered primarily to prostitutes and drug addicts, because might as well make Dean feel at home. One bed, for Dean and Dean alone, the suggestive eyebrow-waggling of the clerk be damned, because Crowley hadn't been afflicted with that sort of human weakness in...well, a good few months, at least.
He pitched Dean into bed and settled in for a long night of bad TV and making sure his brand-new killing machine didn't drown in his own vomit. Of course, as Winchesters were wont to do, Dean complicated things almost immediately, slurring out a garbled complaint about not being able to sleep without...something.
"If it's a nightcap you're wanting, far be it from me to stand between you and cirrhosis," Crowley said dryly, getting to his feet. He was sure he'd spied a corner store nearby where he could trade a twenty for enough rotgut to put Dean into a coma.
"No. Can' sleep alone," Dean mumbled. Drunkenly, of course. "Jus' doesn' work. Go'a have sunbody."
Crowley took a second to parse that. The intended meaning could be what he came up with, though.
"You must be joking," Crowley stated incredulously. "What happens on the nights you can't entice some waitress with depressingly-low standards home with you? D'you just sit up swilling whiskey and spanking the monkey 'til dawn?"
Something changed in Dean then, in the weak, pale little feelings spilling off him like dandruff, and Crowley couldn't quite put his finger on what it was. Part of it was the way the alcohol was muddling everything, part of it was that it wasn't something a demon should be going through. Another part was that Crowley didn't care enough to really focus on it.
Dean muttered a few phrases even mushier than the last couple. Crowley picked up "since Hell" and "not sex." Then something that sounded very much like "Sam."
Crowley's eyebrows shot straight up. He was shocked, in a mild sort of way. He was also quite pleased that he'd just won an obscene amount of money in one of Hell's many betting pools concerning the Winchesters.
The pleasure faded quickly. Crowley paced, rubbing his mouth and trying to come up with a solution. Dean needed to sleep. And as damaged as his goods were, Crowley was inclined to believe him when he said he couldn't do it alone.
"I'm assuming I can't just pay a lady of the evening to literally sleep with you?" he asked, pausing and taking his hand away from his face to look at Dean. The one green eye that wasn't smashed into the flat, stained pillow just blinked stickily at him. "Of course not."
Hissing out a long sigh through clenched teeth, Crowley reluctantly removed the jacket of his suit. It was a silk blend, several thousand dollars, one of Giorgio's finest, and he wasn't fond of the idea of Dean getting bodily fluids all over it. Kicking off his shoes and loosening his tie, Crowley climbed gingerly onto the bed, then laid stiffly on his back. "The things I do for you, squirrel."
Unfortunately, it seemed just having Crowley next to him wasn't good enough for his majesty. Sir Knight whinged and wiggled until Crowley wound up in a position he'd never dreamed he might find himself in: spooning Dean Winchester. Chest to back, hips to ass, one arm thrown limply over him and a knee even slotted between his legs.
The one mercy was that Dean quieted as soon as they were in position, dropping off immediately to leave Crowley trapped in a state of low-level horror, eyes darting awkwardly around the room and nose and mouth full of the gel-and-sweat smell of Dean's hair.
It took him hours to come to terms with the fact he was actually doing this.
A week and a half later, Crowley had been forced to acknowledge that the only way to keep Dean under control was to share a bed with him in exactly the way he wanted. If he flat-out refused, the Mark of Cain gave Dean the comfort he supposedly needed, and asserted itself in the form of extremely undesirable killing sprees. Humans, demons, monsters...no one was safe. And while Crowley honestly couldn't care less about the gore-soaked loss of life, even those lives that ostensibly belonged to him, it left a huge mess for him to clean up. It also reminded him, very annoyingly, that Dean was not doing what he wanted. So, chronically nauseated as it made Crowley, spooning it was.
It was so much of a headache. He was beginning to wonder if having a Knight of Hell on a leash was even worth all this. Especially because Dean wasn't terribly useful even when he was awake; booze, food, sex, and generally making an ass of himself were his only interests.
They were currently camped out at the bar that had fast become Dean's favorite, the one with karaoke, early in the evening. Dean finally seemed to have caught on to the fact Crowley was paying, and so was indulging in some decent scotch for once; Crowley was doing the same. Full-blooded demons ordinarily didn't have much of a palate, but taste and enjoyment of certain things could be re-learned over a period of years. It wasn't quite the same as being human, but then, nothing ever was.
Crowley had been mostly silent so far, brooding. Now he asked a question he'd been wanting to since that first night.
"So the rumors about you and your brother are true, then?"
"What d'you mean?" Dean had his eye on the bartender. The male bartender. Dean's mixed proclivities weren't news to Crowley, but him no longer shamefacedly hiding his taste for men was. He wished that were the most surprising thing about this whole experience.
"C'mon, Dean." Crowley tried to hit that playful, bro-y note Dean seemed to respond to so well in other people. "You know. You've had to've heard what everyone says about you two. I've said plenty to you myself, so..." Seeing the way Dean was looking at him, Crowley trailed awkwardly off. "You know."
"No," Dean said flatly. "I don't." Leaning forward, he folded his hands on the dirty table and gave Crowley his full attention. His head was cocked dangerously to the side, mouth held in a tight little non-smile. "How 'bout you explain it to me, Crowley?"
Crowley was, all of a sudden, painfully aware of the fact that he was a crossroads demon. Far above average, yes, a king, but still a crossroads demon. And he was sitting across from a Knight of Hell in possession of the First Blade, lingering human traits or no. He felt reasonably confident he could out-think Dean Winchester any day of the week, but in terms of raw power, Crowley was a toy car next to a Bugatti.
"Well. You know." Crowley was rapidly reevaluating this conversation, but doubted Dean would let him get away with a subject change. "You and Sam - "
Dean's reaction was immediate. "I don't wanna talk about him." He knocked back the rest of his scotch in one swallow, and Crowley resisted a strong urge to grimace. Then he motioned the bartender for more.
"I know. I'm just curious." Crowley tried desperately to keep things light. "I mean, sharing a be - "
"Who the fuck told you we sleep in the same bed?" Dean interrupted him harshly.
For the first time, Crowley considered that Dean might have been too drunk, each and every night, to remember what had happened. What he'd asked for, what he'd let slip. That was an upshot. Crowley shouldn't have said anything. "You - "
He faltered, noticing the way Dean's hand had just dipped inside his jacket, where the First Blade hung next to his heart. Crowley swallowed.
There was silence for a long, ulcer-inducing moment, silence Dean broke.
"We don't. We didn't. And I'm gone, he doesn't matter," Dean ground out in a low voice. That flickering something Crowley couldn't quite identify, bolder and richer than the demonic norm and usually only creeping out at night, was back in his emotions.
Dean didn't relax until another scotch was delivered, and then only just barely. His hand came out of his jacket, at least, which was really all Crowley cared about.
"Bring him up again," Dean started, bringing the scotch to his mouth, rocks glass dangling from his fingertips, "and I'll cut your heart out before you can even think about smoking away." His eyes flicked to black. "Got it?"
Crowley's kneejerk reaction would've been anger, if he hadn't gotten very good at controlling his emotions after centuries spent working with colleagues who could feel what he was. He wanted to tell Dean off, remind him he didn't give the orders and never had. But there was still the highly unfortunate fact of what Dean had become, and that, unfair as it was, a Knight could outrank a king in Hell if he wanted to.
Dean seemed to take Crowley's silence as acquiescence, which loosened him up the rest of the way. It was as if nothing had happened. He wanted to drink his scotch improperly and chat about his sexual prospects with nearly everyone in the bar, and didn't seem bothered at all by Crowley's monosyllabic answers.
Dejectedly nursing his own scotch, Crowley watched Dean drink, order wings, and double down on the bartender. Judging by how very uninterested that last one seemed, it was going to be another night up with the baby for Crowley, so to speak.
He didn't bring up the exact nature of Dean's relationship with Sam again, resigned to that being one pool he wasn't going to win anytime soon. He had plenty of suspicions, though. And he supposed he should be glad he was only having to fulfill Sam's PG-rated body-pillow duties rather than any other ones he might have.
To say Crowley was furious would be as big an understatement as calling Hell mildly unpleasant.
Countless hours wasted in bars and hotel rooms, watching Dean drink enough to poison the entire population of Ireland, have enough mediocre sex to make a nymphomaniac consider joining the clergy, and beg for enough honest-to-Crowley cuddling to bleed even Sam Winchester's soft heart dry. All for what?
A broken deal, a lost soul, and a spoiled brat who couldn't be bothered to show Crowley an ounce of the respect he deserved as a king or a friend. Apparently that was all his time and effort were worth.
Crowley had been trying to get a hold of Sam and make Dean a Winchester problem, as one did with things they didn't feel like handling, since the grand and chivalrous Knight wrapped up his tantrum and stalked out. But Sam wasn't picking up and Crowley couldn't find him. That was frustrating. Crowley was also quite frustrated with Dean, his demons, and most of all himself.
He was exhausted and soul-weary, despite his soul missing quite a few component parts. As a demon, the only cures were time and bloodshed, and Crowley simply didn't have the energy for the latter.
He didn't feel like dealing with all the other demons back in his court, either, so he'd booked a room for some downtime, at a motel questionable enough to make even the Winchesters balk...maybe. He was just tucking into a documentary marathon and a bourbon Dean definitely would not fully appreciate when there was a series of loud, haphazard thuds against the cheap door, shaking it in its frame. Crowley cursed to himself before reluctantly getting up.
Of course he knew who was on the other side without even looking through the peephole. He felt him. But for some staggeringly-stupid reason, Crowley opened the door anyway.
There was Dean, stupendously drunk and, from all appearances, fresh from a bath of assorted blood. Immediately, he fell heavy against Crowley. Crowley should've just shoved him back outside, and wondered why he didn't, but instead he dragged him in and dumped him on the bed with a symphony of creaking springs. Dean was absolutely swimming in that weird emotion he shouldn't have. But if Crowley hadn't cared before, he definitely couldn't be arsed to try and figure it out now.
"What happened to calling when you need to kill?" Crowley muttered sarcastically. Of course Dean didn't hear him.
Crowley didn't bother doing anything with the covers, or taking Dean's clothes off, or cleaning him up at all, despite the blood glistening wetly on his jeans and - wait. Fresh blood. And he'd just been all over Crowley.
With dawning horror, Crowley looked down at himself. Sure enough, Dean had gotten his mess down the front of a suit worth more than the entirety of his organs combined. Just because it was black didn't mean it wouldn't stain.
Crowley instantly began struggling out of his clothes, heading for the bathroom to throw them in the tub and cover them in cold water. But apparently, Dean's Knighthood had granted him telekinetic powers. He must not have been aware of them before now, because when he grabbed Crowley and yanked him down onto the bed without touching him, that was the first time Crowley had ever seen him move something with his mind.
Of course Crowley tried to get up. Several times. None of his attempts made it far before he was seized again and returned to the mattress. He couldn't even teleport. Finally, he was forced to give up, seething as he settled down into the position he'd learned Dean liked, shuddering at the liquid-pennies reek and weak tackiness of blood.
"The second I figure out how to get away from your whiskey-soaked carcass, that's it," Crowley hissed to Dean, far too mad to care he was a Knight anymore. "I'm doing what I should've done months ago and ending you. Hard. Then I'll mail you to your brother, piece by piece. With a series of witty limericks."
Dean just snored. He didn't even notice when Crowley spit on him.
Crowley spent several long hours being achingly, uselessly furious, roiling like the bastard love child of a hurricane and a tornado inside his meat suit. Then, inevitably, he began to calm down.
Much as he'd rather it didn't, a more even-keeled mood brought with it rational thinking. Crowley would suffer through a thousand more childhoods with his mother (arguably worse than the rack time that'd made him a demon) before he'd admit to enjoying holding a sleeping Dean, but there were far worse things he could be doing. The perspective did make him feel slightly better.
Additionally, among Crowley's very few faults, one was that he was a hopeless optimist. He started to think he could maybe fix all of this.
A Winchester or a Knight of Hell, either one separately, would be an invaluable card to have in his deck. But both together in one package? He'd never forgive himself if he let this slip through his fingers.
Crowley decided he needed to have a firm chat with Dean when he woke up. Establish control, remind Dean how Crowley cared for him, and how he could make him happy if he just obeyed. Not to mention what he could do to him if he didn't. Crowley had seen how Dean was with Alastair, heard how he was with John Winchester. They could've told him to jump and he would've done it instantly, blaming himself for not asking how high should he have been punished. Loathe as Crowley was to own up to it, a portion of the guilt for their relationship breaking down lay with him. He'd tried to set himself up as a friend or a companion rather than taking advantage of Dean's readily-apparent daddy issues. After all, Dean didn't obey Sam or Castiel's orders without question, did he?
They'd have to nip the cuddling in the bud. But honestly...if it couldn't be done, Crowley supposed that he could tolerate it. In the name of having the infernal equivalent of a heat-seeking missile under his thumb. Either that or bond Dean to some other hapless demon. But then there'd be the risk of disloyalty, wouldn't there?
Everything could be good again. Better, perfect. Just like Crowley had wanted it to be when he went and got Dean.
The thought was no sooner finished than Dean rolled over, in his sleep, and grabbed Crowley. Tightly. Crowley stiffened as Dean burrowed into his neck, stubble catching on Crowley's own. Had he still had a gag reflex, it would've kicked in the moment Dean happily sighed out, "Sammy."
There was certainly no room for Jesus between the two of them. They were so close, in fact, that Crowley could feel a large, obvious erection against his leg with no issue at all. It was barely contained by the denim of Dean's jeans.
Was this enough to win the pool? Crowley honestly didn't care right now.
"I changed my mind." Crowley finally regained his voice after abject disgust knocked the words right out of him. "You're going back to your walking, talking, extra-large love-doll of a brother first thing in the morning. I don't even have the patience to cut you up."
Dean just snuffled and held him tighter.