Work Text:
“Paint It Black"
The impossible had finally become possible. All it had taken was a demonic miracle.
The instant Dean's eyes had opened and shown pitch black, Crowley knew, for once, luck was with him.
He had what he'd always wanted: a Winchester to call his own.
Dean was in enough of a right mind, or perhaps a dark enough one, to leave his younger brother a note. One slip of paper to explain his absence.
That he had been willing to take the Impala too, the most convenient set of wheels, said much about the changing status quo.
Dean decided to drop the bombshell as they drove away from the bunker, eyeing Crowley closely as he sat beside him in the passenger seat.
“Did you know this would happen?”
Crowley saw no reason for any more subterfuge. “There was a distinct possibility, but you never know when it comes to those old legends what's really the truth or an embellished lie.”
Dean hadn't reacted badly thus far, and Crowley pushed further. “I rather hoped it was.”
At that, Dean’s eyes ticked over to him in what could have been annoyance or vague interest. It was hard reading his moods now. Too unpredictable.
That was demons for you.
But Dean was a cut above them, technically a Knight of Hell still trapped inside his meat suit. He couldn't smoke out, but Crowley would bet a large number of human souls that he was still subject to the whims of demons’ known weaknesses.
“Wanted me all to yourself, did you?” Dean asked semi-casually, a note of heavy suggestion in his voice that didn't escape Crowley's notice.
A tendril of excitement slowly crept up Crowley's spine. Was Dean Winchester, lady killer extraordinaire, flirting with him? It was a brand new world, wasn’t it?
Best to embrace it, Crowley thought. “I could do a great deal with you at my side,” he replied steadily. “As well as under me.”
Surprisingly, Dean laughed, clearly amused. “Now, there is a scenario I wouldn’t mind seeing play out.”
“You just let me know when.”
“You've never made a move before,” Dean said. “Not in all the years that Sam and I have known you.”
Crowley smirked. “And you boys have never killed me despite threatening to oh so many times. One wonders why.”
“Right back at you,” Dean replied, glancing at Crowley.
“You mean why haven't I had my way with either of you?” A small nod on Dean's part, Crowley scoffing in reply. “A demon does have some standards. Forcing someone just isn't that enticing.”
“And that's all?”
“That's all,” Crowley confirmed.
Dean was silent for a while, Crowley studying his profile in the darkness until he finally had to say something. “You two always think the worse of me. I merely run Hell, trying to keep everyone in line. There are rogues, for sure, but I've only broken a promise when necessary. That's more than I can say for you bloody Winchesters.”
“Still choking on some leftover humanity there?”
Crowley’s lips pressed into a thin line. He was mostly past that, but had to admit that there were traces of it that sometimes resurfaced at the most inconvenient of times.
“Nothing of the sort,” Crowley said dismissively. “I was merely stating facts.”
“Uh-huh.”
Crowley questioned where they were heade,d but kept the inquiry to himself. He could do business anywhere if he had to. Staying and guiding Dean into his demonic manhood was far more important, though.
He would have a lot of questions in the next few days, and Crowley was more than happy to provide answers.
The bar was garish and loud as they entered, Crowley looking down in distaste when his shoes stuck briefly to the floor, a silent testament to the fact that the establishment didn’t rank too highly on the cleanliness scale.
“Are you sure you wouldn’t rather go somewhere else?” Crowley asked, his position in the demon world affording him the best life had to offer. He only went to seedy bars like this when he wanted to be alone.
Dean’s gaze slid from the gaudy décor littering nearly every inch of the walls to Crowley. “I wanted a drink. We've been driving long enough, don’t you think?”
They’d left the bunker around dawn, the sun just starting to dip below the horizon when they stopped. How many states had been crossed was anyone’s guess.
The young red-haired waitress who came to the table they were sitting at was curvy and friendly, Dean immediately leaning towards her in unrestrained interest. There was no wedding ring on her finger, which apparently made her instantly available to Dean.
“Hey, I’m Sarah. What can I get you, boys?”
Crowley rolled his eyes as Dean grinned, turning on the charm. “I’m Dean. Two beers, please, Sarah.”
The look Sarah gave him was decidedly cool. “Back in a few.”
Dean looked a tiny bit disappointed as he sat back in his chair. Still, his good mood didn’t seem much affected by the waitress’s quick dismissal.
Sarah brought the beers back after a few minutes had passed before going on to tend to the other tables around the area.
Wanting to fill the silence and curious about his companion’s state of mind, Crowley risked a sip of beer. It was sour, making him hide a wince at the harsh taste. He much preferred the smooth burn of a barrel-aged whiskey.
“If I’m honest, I thought you’d be angry about all this,” Crowley said, weighing the tone of his words carefully. So far, Dean had been downright jovial about embracing his new nature. Crowley didn’t want to upset the apple cart if he could help it.
Dean startled him with his reply. “Why? You and the Blade freed me from everything that’s been weighing me down for years.”
He held up one finger, cutting off Crowley’s next words. “I mean, yeah, you lied about the Mark, but when haven’t you tried to pull one over on Sam and me? The only difference this time is I happen to like the end result. Anything wrong with that?”
Crowley smiled. “Nothing at all. Is there anything you'd like to do in particular?”
“Whatever I want. Eat, drink, screw around. Maybe actually enjoy road-tripping for once.”
“You mean goof off,” Crowley said, keeping any displeasure from his voice.
Dean stared at him, almost daring him to voice any protest. “This is the first time I’ve ever been free from any obligations. No hunting, no family, no morals. I'm having the time of my life here.”
Crowley couldn’t help pushing, trying to get a full glimpse into Dean’s mindset. “Don't you want to do more?”
Dean shook his head. “What part of no obligations don't you understand? I'll do what I want from now on. No one is ordering me around anymore.” He waved at Sarah when she came close to the table, but she ignored him. “Tonight's goal is to get on her good side, then come back tomorrow and really get to know Sarah better.”
Crowley mentally sighed. He knew even as a newly minted demon that Dean would be a handful, but hadn’t anticipated how long it might take to bring Dean around to his way of thinking.
Still, if there was anything Crowley had an excess of, it was patience. One didn’t become King of Hell overnight, after all.
For now, he sat back and watched the show.
They'd gotten two rooms in the fleabag motel situated across the way from the bar once it had closed up, Crowley marching off to his own, intent on checking in with his subordinates. Demons didn't sleep after all.
When Dean suddenly grabbed his arm, Crowley turned back curiously. There was a dangerous glint in Dean's eyes that he'd never seen before.
“What you said earlier in the car,” Dean said. “Put up or shut up.”
Crowley couldn’t quite believe his luck. He'd thought he would have to work much harder to coax Dean into bed. “Glad to, darling.”
Perhaps Dean was frustrated with his lack of progress with the waitress Sarah, the woman shooting down any attempt at deep conversation. Whatever the case, her loss was Crowley’s gain.
Dropping his arm, Dean followed Crowley into his room, shutting the door behind them.
He turned to regard Crowley, a look of utter seriousness on his face. “If you repeat what I'm about to tell you outside that door, we're through. I’ll leave and never come back.”
How overly dramatic.
Crowley started undoing the knot in his tie. “Have it your way then, Squirrel.”
“You'll have to take the lead here. It's unexplored territory for me,” Dean announced unceremoniously, sitting down on the end of the bed, missing Crowley's look of utter shock.
He'd thought at least he and the Angel had experimented a little with all the unresolved sexual tension between the mismatched pair. Talk about blue balls. Poor Castiel, but what a stroke of luck for Crowley.
He managed to regain his composure just as Dean looked over at him, having taken off his shoes and socks, a stern warning in his eyes. “If you say the word bitch once anywhere in my vicinity, I'll kill you.”
Believing Dean was fully capable of making good on his promise, Crowley raised his hand in the air. “I solemnly swear the term won't come up. Are there any other ultimatums you have for me?”
Dean's hands rested on the top of his jeans. “No, but it better be good.”
“Oh, it will be. Centuries of practice and all that.”
They fell into silence, gradually ditching the majority of their clothes until Dean and Crowley were down to their skivvies.
Not one to be self-conscious, especially since the meat suit Crowley wore was something he found desirable and had gone back to claim anytime he had to abandon it, he was more than ready to go nude until Dean cleared his throat when he made to do so.
“I've always been curious about something,” Dean started, gazing at Crowley.
Crowley waited in anticipation, finally motioning with his hand for Dean to continue when he seemed to hesitate a bit.
“Your demon deal was a bigger dick. Does your current host measure up to what you used to have back then?”
Crowley couldn't help chuckling. Of all the questions he anticipated, that had not been one he'd thought Dean would voice. “Worried it'll hurt?”
“No, but…” Dean's voice trailed off as Crowley pulled off his underwear, proudly displaying what lay beneath his waist. Already partially hard, it was a fine specimen, the likes of which were hard to find.
“Really?” Dean asked in disbelief, eyeing what lay underneath Crowley's midsection. “That is...” He trailed off into silence.
It was very close to what he'd had while living as a human, at least until Crowley's deal had run out and he'd been cast down to Hell. “You'll be loving every inch in no time.”
Dean scoffed as he rolled his eyes, shucking his own boxers. “Promises, promises.”
Despite indulging in rather unhealthy eating habits, Dean was in fine shape, with hardly an ounce of fat on him. He was also a bit bigger down under than Crowley had thought, and he wondered how it would feel if their roles were reversed.
Ignoring the delicious jerk in the pit of his stomach as he mulled the possibility over, Crowley put the matter aside. There would be other opportunities to explore exactly what Dean could do for him.
“Like what you see?” Dean asked confidently, resting one hand on his hip, his gaze full of heat.
Crowley walked towards him with intent. “I do, yes.”
Once he got close enough to feel the tip of Dean's cock brush against his stomach, Crowley leaned forward, grunting when Dean put a hand over his chin and mouth with a raised eyebrow.
He pushed Crowley back a touch. “Really? Are we going to start braiding each other's hair next?”
Crowley stopped, annoyance rising in him. “You'd prefer a different kind of kiss, then?”
“What did you have in mind?” Dean asked with interest.
Crowley went to his knees, a hand reaching out for Dean's cock. He hovered over it, purposely breathing out with his mouth, bathing it with hot air, knowing how sensitive such a thing could be.
Dean visibly shuddered as Crowley closed that last inch between them, his eyes about rolling back in his head. “Fuck me.”
Crowley retreated for a moment. “That is the idea.”
Dean's head tipped back as his hands fell onto Crowley, one on his shoulder and the other on top of his head. His breath hitched when Crowley went to work, working Dean's cock down his throat until he had taken most of it inside.
Carefully breathing through his nose, Crowley applied suction, Dean starting for a second as he began to pant in earnest. Crowley drew back as slowly as he could, even as he swept his tongue around Dean's cock, circling the head and everything below it.
He felt the long shudder that temporarily loosened Dean's knees before he got control of himself again, the hand upon Crowley's head clutching his hair tighter.
“You're…,” Dean ground out, his voice strained. “Really good at that.”
Of course, he was. Crowley wasn’t some inexperienced virgin in high school.
He looked up at Dean, the look of utter bliss on his face a joy to see. Crowley had honestly thought that once they got this far, Dean would find some excuse to cut things short, unable to handle gay sex.
But this was Dean Winchester. He took everything on regardless of how stupid or dangerous it was. Fooling around with Crowley was definitely the latter, and he really should have known better.
Dean moaned as Crowley continued his attentions, savoring the sound, resolving to pull more out of his companion.
Oh, he loved this. The way Dean had capitulated, how he trembled ever so slightly, sweat beading on his forehead. If Crowley couldn’t convert Dean by the end of the night, it would be a terrible waste.
Dean's voice went uneven for a second as he hung his head for one brief moment, and Crowley swallowed everything down, the salty taste nothing to him.
Sinking back onto the end of the bed as Crowley stood up, Dean panted, his face flushed. He eyed Crowley. “About what I would expect from a king.”
Was that a compliment or an insult? Knowing Dean, Crowley thought it could double as both. He licked his lips, sure that a little red was showing in his eyes.
“Turn over, Dean.”
The corners of Dean's mouth lifted. “Say please.”
Crowley narrowed his eyes, striving to keep his temper. He never begged for anything; such behavior was beneath someone of his station. However, he wanted the man sitting before him with a fierceness bordering on obsession. Years of maneuvering the boys into the right position, subtly influencing events in his favor.
Telling himself it was a rare exception, the likes of which would never happen again, Crowley bent forward and whispered, “Please.”
Dean's eyes lit up in triumph before he turned over onto his front, looking back at Crowley when he just stared at the tight ass he’d been granted permission to explore.
He was going where no man had ever gone before. Crowley felt positively giddy.
“Well, get to work.”
A dark joy rising in him, Crowley pushed outward with his mind, pressing Dean down into the bed as he lay flat on his stomach. He gently prodded at Dean’s backside, encountering tense muscles within.
He started to massage them with care as Dean's breathing deepened, his hands brunched up in the motel comforter. At one small touch upon his prostate, Dean groaned sharply. Power suddenly flooded the room until Crowley's telekinetic hold shattered.
Dean had fought him, had he? Crowley’s suspicions were confirmed as Dean twisted onto his side, shooting him a dirty look. “Enough with the Jedi mind tricks. They won't work on me.”
Crowley still tried again with no success. He filed the helpful factoid away. Best to keep on Dean's good side and not tempt fate.
He sighed. “You Winchesters,” he said. “Always making me get my hands dirty.”
“You really going to complain about having to do things the old-fashioned way?”
Crowley put his head to the side. “I prefer it, actually.” He walked to his coat and retrieved a tube of lube from one inner pocket. He always believed in being prepared. And now he could put a personal spin on things.
Dumping a fair amount of lube onto his fingers, Crowley proceeded to nudge one inside, quickly finding what he was looking for.
Dean shuddered, his heavy breathing betraying him. As demons, their libidos were significantly higher than humans', something which worked to their advantage in terms of stamina and lasting power.
He teased Dean mercilessly until he all but writhed on the bed, precum painting parts of the comforter. Crowley stepped forward, brushing his cock against Dean's ass for a second. He kissed the space between Dean's shoulder blades as well, tasting sweat and the remnants of body spray.
He wasn’t sure what Dean took offense at, simply that he went still, peering at Crowley with an expression that said he had pushed his luck.
Crowley ignored him and flicked his fingers inside Dean pointedly. The man's gaze went unsteady, the slight forgotten for now.
Deciding enough was enough, Crowley stepped back from Dean and took himself in hand, keeping a tight grip on one side of Dean's hips.
“Remember to breathe and relax, dear.”
“Don’t call me tha-"
Dean’s words died on his lips, tension raising in his muscles as Crowley moved forward, working every delicious inch as far as he could.
The lack of resistance on Dean’s part proved beyond a shadow of a doubt that all of Crowley’s hard work had been worth it.
Cain, the Mark, the First Blade. Dean's death hadn't been assured, but the stupidly reckless way he and Sam lived their lives meant Crowley merely had to wait for the inevitable mistake that would lead to their ruin.
That or Dean would fall deeper into the Blade's influence and convince Sam to mercy kill him. Either option would have worked for Crowley so long as the end result was the same.
One Dean Winchester under his thumb. Or cock as things happened. Crowley wasn’t picky, but he was greedy and rather pleased things had happened this way.
Dean was delightfully out of breath, all heat, tightness, and warmth that encased Crowley in the most intimate of ways.
Seated inside Dean, Crowley took a deep breath, not wanting to move just yet. He was all for prolonging the moment. “Good?”
The wild look in Dean's eyes cast his way went straight to the heart of Crowley, his chest going tight. Dean would never say it, but obviously he enjoyed the feeling of being filled up, of giving up control to someone else.
“Start moving, asshole.”
Crowley smiled. “Gladly.”
He took Dean at his word, setting at first a slow, measured pace, fire running through his nerves, at the pleasure there was to be had with every movement.
For it being his first time with a man, Dean was very accommodating. Not one complaint passed his lips as Crowley reveled in the oldest dance in the world. It wasn’t often he could render Dean Winchester breathless, and he relished it.
The sex was everything Crowley could have hoped for.
“Harder,” Dean growled, the muscles on his back flexing as Crowley grabbed one of his wrists. He pulled it backward, curving Dean’s back a little as the position afforded him a new angle, allowing Crowley to drive himself deeper.
Dean grunted, his expression slowly going soft, eyes half-lidded. The scene was gratifying, what little Crowley could see anyway, given he kept forcing half of Dean’s face into a pillow with each thrust.
The earnest grunts and groans he pulled from Dean made his head spin pleasantly, a sense of power and domination growing in him. He hadn’t even touched Dean’s cock so far, but he seemed close to finishing regardless.
Crowley strangled a moan when Dean jerked beneath him, his inner walls squeezing down on Crowley, pleasure lighting up all his senses.
He bit his lip, closing his eyes to maintain control until Dean had gone still, his breathing ragged. Crowley surged forward again, Dean letting out a low moan in return.
Crowley wasn’t at all surprised to see Dean rapidly become hard again. The touch of a hand on his arm stopped him as Dean twisted around onto his back, nearly straddling Crowley's lap.
Sweat dripped from his forehead as he looked Crowley straight in the eyes. “Is that all you've got? Big bad King of Hell can't satisfy one man?”
Crowley grabbed Dean's hair in one hand, the flash of pain on Dean’s face quick to vanish. “You watch yourself, boy. Have some respect.”
Dean pulled his head out of Crowley's grip, smirking. “You love it. No one else will talk to you like this.”
He wasn't wrong, but Crowley wasn’t going to admit it. “Be careful what you wish for.”
Crowley rocked forward, driving Dean's back into the bed, sparing him no mercy. His grip on Dean's hips was tight enough to bruise and draw blood in places, but Dean’s healing factor kicked in swiftly, undoing the damage in seconds.
He'd promised Dean howling, and by god, he was going to deliver.
Dean's breath was uneven, barely able to draw air in before it rushed out in long, strangled moans. His fingers were tight on Crowley's forearms, scratching lightly.
Crowley fought for every bit of control at his command, pausing when his own body threatened to break, then faster when Crowley felt the wave of threatening bliss relent.
He grunted, an increasing tension coiling tighter in his stomach and further below. He couldn't continue forever, though his stamina was far above a normal human’s. Crowley didn't know what level Dean plateaued at, but it had to be quite similar.
Grabbing Dean's cock, Crowley squeezed it lightly, the man under him moaning. Each movement brought them ever closer to breaking.
Dean abruptly shuddered, tossing his head to the side. Whiteness stained his upper stomach, Dean's eyes turning pitch black as he climaxed loudly.
The sight was enough to trigger Crowley's own finish, his vision going spotty as he pushed as deep as he could into Dean and finally let go.
A satisfying shudder racked his body, Crowley finding it hard to think past the pleasure that drowned him, burning along his nerves. Well aware that he'd been the first man to ever lay claim to Dean.
Dean’s breathing was strangled, sweat dripping down his chest. Crowley retreated from him, feeling worn out. Dean was a very demanding lover.
His breathing quieting with every second that passed, Crowley waited to see how Dean would react.
As usual, he wasn’t disappointed.
Slowly sitting up, Dean’s gaze locked onto Crowley. “Now it’s your turn.”
A flush of heat clutched Crowley, and his cock stirred back to life in record time. And his underlings wondered why he bothered with Dean in the first place.
This, this was why. It seemed Crowley was going to get to see Dean in action tonight after all.
He could hardly wait.
Crowley was spent.
While he'd worn Dean down, he'd returned the favor and then some. The whole night had been past his wildest expectations.
Lying on one side of the bed, the comforter they’d dirtied long since pushed to the floor, Dean glanced at Crowley curiously. “Why can't I teleport?”
Crowley laughed. “You think that kind of power comes for free? You have to work for it. The same goes for telekinesis and everything else. It doesn't come overnight.”
“Well, that's crap,” Dean muttered under his breath.
“No one said it would be easy. You may have gotten a step over demon kind by way of the Mark, but you still have a lot to learn.”
Raising an eyebrow, Dean glanced at him. “And you’ll teach me?”
“Of course. What else are friends for?” Crowley said, noting Dean’s quick smirk. “What?”
Dean looked amused. “Friends, huh? I can safely say I’ve never thought of you like that. That we’d go paint the town red together.”
Crowley had felt the exact opposite, and the sting of truth was hard to swallow.
“Of course,” Dean continued after a moment. “That was then. Now I’m seeing a whole new side of you.”
A stirring of hope rose in Crowley. “Oh?”
“Yeah, you’re not as useless as I thought you were,” Dean said gamely. “Your…unique talents are appreciated.” The swift glance at Crowley’s lower half didn’t go unnoticed.
“I’m all atwitter,” Crowley teased, thrilled the evening had turned out so well.
“Good,” Dean said, flopping onto his back. “You should be.”
Everything was absolutely perfect.
Now, the only matter that remained was convincing Dean that he belonged at Crowley’s side in every sense of the word. With centuries of experience in manipulating others, Crowley assumed he would have no issues.
After all, he’d already achieved a major victory and fully expected more in the future.