[FIC] How to Succeed in Business

Written for the 2012 Supernatural Rarepair Shipfest.

Supernatural. Dean/Crowley. Dean/Sam hints. Series canon AU (It’s a Terrible Life). Dubious consent due to identity (Dean doesn’t know Crowley’s a demon). Facefucking, deepthroating.

It’s happy hour and a stranger in a very nice suit buys Dean the most expensive drink he’s ever had. The guy has something else on his mind besides making a single serving friend, and it turns out he’s in sales too. (It’s a Terrible Life verse.)

How to Succeed in Business

Dean adjusted his tie and scowled. It had cost him a hundred bucks, was still brand new, and all day long it had felt like a snake coiled tightly around his neck. He adjusted the knot for the billionth time and smoothed a hand down his front; a cleanse was supposed to clear a guy out, not make him feel bloated.

Speaking of bloated, his inbox was straining at the seams. Email had been piling up like a snowbank in a mid-winter storm, a constant influx that he didn’t have the focus or willpower to do anything about. He drummed his fingers on his desk. This was so unlike him. He was a power worker, an absolute fucking wizard armed with a sales team and a bluetooth headset; he’d clawed his way up the corporate ladder with pure determination, a crap ton of elbow grease, and an innate skill at pleasing the higher ups. For him to ignore a set of hot leads and shrug off the week’s dip in team performance was completely out of character.

He took another swig from his sports bottle and blamed the slacker drone from IT who’d taken to either hitting on him or giving him calf eyes every time they were in the same room. Dean snorted. ’Don’t I know you?’ Jesus, talk about the worst pick up line in the entire history of pick up lines. Probably the only reason the dude ever got any dick at all was that he was built like a brick shithouse. Big and dumb was not Dean Smith’s type. When he strayed to that side of the fence, he liked a guy to have a few brain cells to rub together.

And a workplace romance? Please. That crap wasn’t even on his radar. Interoffice shenanigans led to sexual harassment suits and catty gossip. He punched the button for his voicemail and stood up from his desk, listening to the first rambling message of–fuck, twenty-four now–as he stared out the window. At the third offer from yet another Groupon clone he switched things up and fiddled with his watch instead of his tie. Maybe with the way he was feeling he just needed to let loose and hit a bathhouse or knock a few back at a cozy bar with the right atmosphere.


At half past five, Dean found himself on the other end of the city, warming a stool in the lobby bar of the nicest hotel near the tourist draws. The place down the block would be crawling with kids and guys in loud shirts and fanny packs, but at twenty bucks a cocktail the usual tourist types didn’t make it past the menu posted at the door. Most importantly, he fit in–no one looked twice at how expensive his suit was–and this far from the financial district, he didn’t need to worry about running into someone from Sandover. With a reputation for the best scotch tasting in town and plenty of eye-candy in the room, this was just what the doctor ordered. His eye kept straying towards the men–all that stupid IT guy’s fault–so a bathhouse might not have been a bad idea, but the night was still young.

It wasn’t that crowded, so Dean was a little surprised when a guy slid onto the stool next to him. He shifted to make a little more room. The guy wasn’t much of a looker, at least not in comparison to the rest of the Ken and Barbie happy hour show, but if his hairline was future-Dean’s biggest fear, his suit was as nice if not nicer than Dean’s D&G. Dean eyeballed him subtly; maybe he thought Dean was the right kind of conversation. Dean pulled a face as the guy scanned the bottles and ordered himself up a 30 year Macallan neat. He had to respect a guy who’d drop three Benjamins on a single drink.

“That one’s for you, boyo,” the man said, sliding the whiskey over. He tossed an amex to the bartender–definitely a nicer suit if he was treating strangers on a black card–and Dean’s eyebrows crept that much higher. “I’ll take the next one over, the Balvenie.”

Dean finished off the perfectly respectable drink he’d been sipping at and stared at what was the most expensive fifth of liquor he’d ever seen. “What’s the occasion?” he asked, waiting until the guy buying the drinks got his before raising his glass.

“Let’s just say I’m feeling generous. Some of the competition got out of the game quite recently.” If the deep rasp of his voice was doing things to Dean, the way the corners of his mouth curled up only amplified the feeling. “Cheers.”

“Cheers,” Dean echoed, raising his glass for a sip. Two hundred and fifty tasted a lot better than fifteen bucks, but not as amazing as he expected. Huh.

“It’s why I went with the Balvenie,” the guy said, reading Dean’s mind. He was watching his own reflection behind the bar, gaze flicking over to meet Dean’s in the mirror as he introduced himself: “Name’s Crowley.”

“Is that a first or a last?”

“Take your pick.”

“All right then, Crowley. I’m Dean. Thank you for the incredibly expensive drink,” he turned and extended his hand, but Crowley didn’t reciprocate and simply watched him with hooded eyes. Dean retracted the offer with an awkward laugh. He licked his lips. “Hope you don’t think I’m that easy.”

That smile again made Dean’s insides clench. He flashed a smile of his own, loose and easy, or he hoped it came off that way. Getting an instant bone for some dude that wasn’t even into him, fuck, he was as bad as Mr. Do-I-Know-You. He went back to staring at their reflections behind the bar where he wouldn’t be distracted by the prickle of a five o’clock shadow. The light does something funky for a second, makes the bright red shirt of the woman behind them flicker and jump, echo somehow in dark eyes that after a passing second Dean is less than half sure he saw.

“I don’t think you’re easy at all, Dean. But you present a unique opportunity,” Crowley paused, his eyes narrowing slightly as he gestured for Dean to lean in. Dean obliged, keenly aware when their shoulders were near to touching. Crowley’s mouth came near to touching him, hovering one hard shiver away from his ear. “You know, I’d give a lot for a man of your…talents.”

A violent mix of embarrassment, anger, and just about everything in-between ran along Dean’s skin like wildfire. He never should have joked about being easy. “I think you got the wrong idea, pal. You see what I’m wearing? You think I’m some kind of,” he dropped his voice to a grating whisper, “manwhore.

“Mostly we call them escorts these days, even the men,” Crowley said, unruffled. He leaned in again and it took all of Dean’s control not to jerk back and attract the attention of everyone around them. “LL Bean or Dolce, it doesn’t matter what’s on the surface, Dean. I knew the moment I first laid eyes on you that you were a filthy slut who could use a good hard cock shoved down his throat, and that’s why,” he pulled away easy as sin to sip at his drink, “if it’s your mouth I want, I won’t need to pay you a damn thing.”

Dean lost the ability to swallow, to think, to do anything other than stare slack-jawed and dumb. The problem was he’d pictured it–Crowley’s cock sliding into his mouth, as heavy and thick as his voice–and he couldn’t stop the knee-jerk reaction of wanting to go down on a guy that confident, even if he was a complete fucking asshole. Dean wasn’t as bad as Mr. Do-I-Know-You, he was worse.

“I’m listening.” Dean heard the words come out of him like he was standing two feet away from his own body. It was small comfort that he sounded steady enough when he couldn’t nut up and maintain eye contact.

“Of course you are, darling,” Crowley said, and Dean jumped when the heavy glass tumbler knocked back down on the bar. “Two minutes, men’s room. And whatever you do, don’t make it obvious.” He signalled the bartender as he stood. “One more for my friend here, whatever the gentleman wants.”

As Crowley moved past him, Dean caught a whiff of scent: sharp and metallic like a freshly struck match. Deja vu smacked him hard, a bit of sense memory that left a nagging feeling behind like Dean was missing something huge on the scale of ‘that’s no moon’. He shook off the feeling as the bartender approached. “I’ll take what he had. Leave the bottle.”

Two minutes later, on the dot–let no one ever say that Dean Smith was anything other than punctual–the bottle was on the floor next to the toilet and his hand was on Crowley’s dick. “Fuck,” Dean breathed, feeling Crowley get hard under a thin layer of superfine wool. “You’re hiding a monster aren’t you.”

“You have no idea,” Crowley purred. He widened his stance as he shoved Dean down to sit on the toilet seat.

It felt weird sitting on the crapper with his clothes on, but Dean stopped paying attention to that the second Crowley’s fly was down and his dick was out. Slowly, Dean jacked him hard, mesmerized by the slide and bunch of foreskin at the head. Crowley’s cock was living up to his fantasies. It wasn’t exactly porn-star huge, or large enough that Dean was worried about getting it in his mouth, but for a guy whose eyes came level to his chin, he was feeling a little out-gunned. “That is one big dick,” Dean said, licking his lips as he grasped it at the root. The foreskin pulled back enough for the tip to peek out nice and dark, and Dean stroked him a couple more times just to watch the way all that skin played out over the flare of the crown.

“I’ve had bigger,” Crowley said, shrugging. The look on his face was tough as balls to read. Dean wasn’t here to psychoanalyze the guy though, he was here to suck some dick.

“Well, size isn’t everything right?” Dean said. He licked a slow swirl around the head, slicking it up good before it was crammed into his mouth. He hummed appreciatively as he sucked in the tip, the taste of sweat and skin flooding onto his tongue. Fuck, but he’d forgotten just how much he loved the taste of dick. Weird how a guy could forget that, but he’d gotten used to prioritizing work, and keeping his department performing took a whole lot of blood, sweat, and overtime.

Dean forced himself to stop thinking about trend lines and the looming end of the fiscal quarter. He focused on dragging his fist up the length of Crowley’s dick, finding the thick bunch of foreskin a novelty worth exploiting as it bumped up against his lips. He swirled his tongue around again, slid it under all that extra skin and thought about what it must be like to jack off with an uncut dick. Shuddering, he pushed Crowley’s dick to the side and gave it a long lick up the shaft. “Dude, you’ve got a great cock. You taste fucking amazing. I could suck you like a goddamn popsicle all night.”

The hand that went to Dean’s chin forced him firmly to meet Crowley’s gaze. Crowley wasn’t scowling, but he clearly wasn’t impressed by Dean’s dirty talk either. He shoved a thumb into Dean’s mouth, and said, “Cut the flattery, pretty boy. If I was interested in conversation, I wouldn’t have asked you in here.”

Dean blinked several times in rapid succession as his emotions hovered somewhere between offended and overwhelmingly turned on. He couldn’t remember the last no-strings hookup he’d had, but he didn’t usually go for assholes. Or did he? Dean’s tongue quivered under Crowley’s thumb. What was his usual type of guy anyway? Smart was the only adjective that came to mind, and a sudden flush of guilt.

“My cock, your throat, and don’t tell me you can’t take it. I know without a doubt that you can, Mr. Smith.”

“Yes, sir,” he said, once Crowley slipped his thumb free. And it doesn’t register that he never told Crowley his last name until he has his hands braced on either side of the stall and the heat of his mouth is sliding back down the length of that fat cock, and by then higher thinking had pretty much escaped him. Another hard shiver ran down the length of Dean’s back; his jaw was going to ache like a motherfucker in the morning, but shit, it was worth it already. The last guy he blew had practically argued with him the whole time, or something, it was fuzzy–

A hand fisted in the hair on top of the head where the strands were just long enough to grab, and he moaned reflexively, the sound cut off a heartbeat later when Crowley thrust deep enough to make him gag. Crowley let him pull off and swallow the spit that wasn’t drooling down the sides of his mouth. “Gimme a little warning next time,” Dean snarled, but he was already going back for more, hungry for it and needing just a couple tries before he’s got his gag reflex under control enough that Crowley could fuck his face all he wanted.

This kind of thing took absolutely zero finesse, but he loved it anyway. Maybe he was a walking cliche of “power in the boardroom not the bedroom“ but there was something satisfying about going slack and just blinking away the water in his eyes as Crowley’s cock plowed into his mouth. Crowley had started slow with long thrusts that weren’t gentle but were measured–persistent and ever deeper–until Dean lost the tension in his muscles and it got full on easy. Occasionally the hand in Dean’s hard curled tighter, forced him down on Crowley’s dick in quick little bobs or held him there until he was close to choking. Only a minute, maybe two, had passed and Dean’s mouth felt raw, his lips abused, and his dick was hard as fucking diamonds; he was harder than he could ever remember being in his life.

He had no idea how this was going to go and the uncertainty of it turned him on even more. Crowley could go the polite route and grab some toilet paper, or maybe Dean would get a shot in the face, or and this was looking pretty likely, Crowley might not even tell him and give him a whole mouthful of come to swallow down.

Dean was fucking throbbing in his pants, and his tongue lolled out, sloppy and waiting for anything Crowley wanted whenever he pulled out all the way. He was panting whenever his mouth was free, and his fingers were shaky as he took the latest break to fumble at his own zip, dying to get a hand on his own cock. Before he could get his fly open, Crowley was clucking his tongue in disapproval: “You’d best be sure I get mine first.”

“Oh yeah?” Dean countered. He caught Crowley’s dick with his lips and slid his mouth down until there was nowhere else to go. Thick flesh twitched against his tongue and swelled in his throat. He pulled back again as he rubbed himself through his slacks. Crowley leaned against the stall door, a bit of colour on his cheeks and his breathing nearly matched Dean’s quick, harsh breaths. Dean grinned and set a hand to the outside of Crowley’s leg. “I don’t think we had any sort of deal about that, Mr. Crowley.”

Crowley’s gaze dropped quickly to meet Dean’s, his eyes narrowed and wary. Dean was puzzled, but the sudden tension in Crowley’s expression was gone in a flash. “Never mix business with pleasure, the saying goes. Ridiculous. But we’ll talk about that later.”

The deja vu smacked Dean again like a cold towel, but before he could wonder if maybe this was his own awkward ’do I know you’ moment, Crowley was telling him to pull his cock out and Dean shoved all his misgivings aside. His mouth flooded wet again as he unzipped and introduced little Dean to the party, and he had to swallow twice as he went down on Crowley again. As the bobbing rhythm of his head was met again by the push of Crowley’s hips, he stroked himself lightly. He kept hardly more than his fingertips running along his dick, partly because he was so turned on, and partly because he wasn’t sure if Crowley was going to snarl and tell him to keep his paws off.

But the next thing Crowley told him was to get ready, and that was worse. Anticipating a mouthful, Dean clamped down on the base of his dick, squirming as both of Crowley’s hands settled on his skull, and he tried very fucking hard not just come as the guy held him in place. Dean sucked in breath after breath through his nose, the inflow never quite enough as Crowley’s cock fucked into him over and over, leaving him on edge just dying for it while his drooling mouth left a spreading stain on Crowley’s slacks.

It was like fucking angels dropped out of heaven to sing in Dean’s ear when he got the mouthful he was waiting for. Crowley didn’t pump the load straight down his throat either, he pulled back to spit it right on Dean’s tongue, a messy dump of come that Dean couldn’t swallow fast enough. He could feel the last wave sliding from the corners of his mouth, heavier than the spit already glistening there, and Dean didn’t bother to wipe it away when he scrambled for a scrap of toilet paper to unload into himself.

Grinning like the cat that very much got the cream, Dean finally wiped his face. “So that was…,” he started.

“Not bad,” Crowley said. He undid his slacks fully, thumbing his boxers down to catch his dick with the waistband and tuck it neatly up against his belly. Swift and efficient, he made himself presentable, and just like that he looked like nothing even happened; the only giveaway was the thick shadow lined up beneath his zip and the wet stain of Dean’s spit. He flipped the latch and exited the stall, adding, “I’ve got a room if you want to share the rest of that bottle. We can even talk business after I’m done using all your holes. I’m in Sales also, since you failed to ask.”

Busy mentally undressing Crowley as he waited just outside the stall adjusting his cuffs, Dean processed the idea that he was being poached. Had that been Crowley’s game from the start? Best crossed signal of his life.Dean finished cleaning himself up and stood. “Are you– You think you can offer me something worth leaving Sandover for?”

“If you sign with me, you could own that miserable company. Hell, I’ll put it this way,” Crowley said, “a little tickle and kiss and I can make the next ten years the best years of your life.”

Confidence like that came with real power, and Fortune 100 wasn’t out of the question, not with how quickly he turned around international last year. Dean cleared his throat, possible opportunities dancing in his head like sweet little sugar plums. “You, uh, want to give me the number and I’ll wait five minutes?”

Crowley checked his appearance in the mirror and Dean swore there was something funky with his eyes again for a split second–what was with the lights in this place?–but in the next heartbeat all Dean saw was that same weighted look and curlicue smile. “Fuck discretion,” Crowley said, and gestured towards the door like a gentleman. “After you, Mr. Smith.”

One thought on “[FIC] How to Succeed in Business

  1. elendraug

    Holy fuck I just read this on my phone during my lunch break and ffffffff it’s gonna get me through the rest of my shift.

    Holy god

    DEAN SHOULD ALWAYS HAVE DICKS IN HIS MOUTH and wow I love this pairing. Your Crowley is perfect


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