Work Text:
The Risk
Dean was comfortable. Lots of people weren’t able to say they were getting by right now. So he was grateful that he had a job that while it wasn’t personally fulfilling, he was more than surviving (he was pretty well off considering) and able to help his brother out with school.
In fact, more so than the cushy apartment his paycheck got him, being able to send Sammy at least two thousand every month, free and clear – no worries, that was what kept him at Heaven.
So what if, when people asked him his job, he had to say he was a bartender. It didn’t matter if he saw their expressions fall slightly, if he could feel them losing respect for him for being in the service industry. Dean knew he was lucky as hell. He was a high-school dropout with a GED, and a go-get-em attitude. That was all he had to his name. Well, that and his cute face.
He could afford to rent a loft apartment in California in a swanky neighborhood. He could fill up Baby’s tank and drive the half-hour to work, and he only had to go four days a week. He had minimal bills, he could treat himself occasionally, and he could support his brother’s dream of graduating from Stanford Law.
His bed was never empty unless he wanted it to be, he had free time for his hobbies, and he was close enough to Sam to see him a few times a month.
He didn’t need anything else.
“Dean, I hate to ask this of you since I know you already did a private party this month, but I’ve got a very high profile client who wants to host a small gathering at the club Saturday night.” Dean smothered the sigh he wanted to heave loudly while his boss, Crowley, beat around the bush. “I know you’ve already done your days for the month as well but I’m willing to make it worth your while.”
He turned to the window, and thought about what he could do with extra money this month. The wall of windows in his loft were what made it cost as much as it did, but it was worth it because Dean had a view of the valley of Woodland Hills and could see down to Ventura Blvd.
“So?” Dean said succinctly, and he heard Crowley's accented tone turn honey sweet.
“As it’s you, darling and I want only the best, I’m willing to make this split fifty-fifty between me, and you and your partner. I’ll give up ten percent and make it thirty for you.”
Dean bit his lip and cursed internally. The split for the servers was usually twenty-twenty after Crowley pocketed his sixty. Goddamn it, he couldn’t turn down three grand. The cheapest parties Crowley hosted started at ten kay. That didn’t include bottle service, which would be a part of his take or the likely tips… fuck.
“Who am I working with?” He didn’t need to be able to see Crowley to imagine the smug curl of his lips. Of course he had known Dean wouldn’t say no. The extra ten percent alone was equal to a whole week’s work.
“I know you work excellently with Maxwell so he will be joining you. The gentlemen will be making a night of it, something about a late brunch the next day so I’d suggest you get some rest during the day and be prepared to pull an all-nighter. Shall we say, see you at the club at eight? Work begins at nine.”
By six am on Sunday he’d be home. With at least four grand because Dean was nothing if not charming. He could make a grand on tips and bottle service. He could send Sam more money this month and still keep a sizable lump for himself.
“See you Saturday, Crowley.” Dean rumbled out, barely catching his boss’ happy ‘toodles’ before he hung up. It wasn’t like he had a life beyond work anyway. There was no one to cancel on and if he lost one weekend of studying, did it really even matter? Was a fucking pipe dream anyway. He could use the time and money he was spending on food or alcohol or more online games…
A tiny breath expelled from him as he closed and put aside the child psychology book he had been reading, leaving it on his kitchenette counter.
Heaven was a deceptive looking place from the outside. Just another building on the strip, brick-wall facade, and blending well with all the businesses lining the boulevard. Inside though was a haven, a gentleman’s club for uptight, snooty businessmen who had money to waste on good looking men and women.
Dean just happened to be one of those good looking men.
So yeah, he wasn’t just a bartender. He wasn’t an escort or companion or whatever they were calling it these days either, but he just so happened to serve his drinks topless, in tuxedo pants with a bow around his neck.
The get-up he found himself getting into, at eight-thirty on a Saturday when he should be at home. Doing…something or the other. Instead of making sure he was covered in coconut oil lotion so he looked supple and glistening.
When it was a normal day’s work, he was in from ten am to six pm or three to eleven pm, serving brunch time alcoholics, after-work bozos, and ‘working late’ liars. There were always two guys and two girls on shift, and no one had to work more than sixteen days a month. There was no extra effort beyond minimal body hair. When it was a special night however… Well, the club didn’t close until the party ended. Those gatherings were more private. Those guests expected a certain standard, and the servers went all out. Crowley knew his groups and what they wanted, and only two staff worked those nights, for ‘intimacy’.
Dean had just been blessed with a face and figure that had Crowley calling him too often. If he counted private parties alone, in the last three years he’d made his yearly salary again. Not that he should complain – doing one every month meant an extra two or three thousand. He made more than the average job did, but it was chump change compared to what the people he served made.
He just felt… lost. He’s been doing this since he was twenty-four and his next birthday was fast approaching, and that would be four years. Most people did this for a year or two to make money and then moved on. Meanwhile Dean had nothing to move on to.
He no longer looked adorably boyish. Less of the come-ons he was getting now were about how twinky he looked and his cock-sucking lips. Now he was ‘handsome’ and men and women wanted to buy him dinner…again, he really wasn’t complaining about that one because it was a step up but it might as well be a sky-writer saying ‘you’re looking older’.
As if to drive that point home, Max Banes popped his head into Dean’s dressing room and gave him a wide grin.
“Dean, floor in twenty. You know Crowley’s in the back room, but he’s going to want us in the lobby to escort the guests in.”
Max was a cute twenty-three year old college grad with a dream. With a year under his belt, he was popular, had an infectious smile and loved to flirt. Hell, he flirted with Dean sometimes and Dean flirted back, laying it on heavy for their audience when they worked together. But yeah, he couldn’t work with Max without ‘daddy’ comments.
It was a clarion call that his time was up. He was getting too old for this.
But always in the back of his mind was: to what? Move on and do what? He wasn’t good at anything beyond talking a good game and being hot. And give his looks another ten years and that would probably fade too. By his late thirties, what would he have to offer anyone?
“Hey, Dean? You’re being spacey.” Max stepped inside with him and took the clip on bowtie from his limp fingers.
“What?” He blinked, taking a breath as Max looped the tab around his neck and put it on for him. Dean looked at the boy (he was a boy, barely older than Sam!) and swallowed in hesitation before speaking.
“You still on track for getting your car next year?” All the workers talked, so Dean knew why Max was here.
“Oh yeah. I might not even need to work the whole year, but I might do it to get some extra money.” Max took a step back and looked Dean over before giving a smiling nod of approval. “By 2021, Alicia and I are going to be long gone. I can’t lie, I’m looking forward to traveling to South America.”
“Don’t forget to post it all on your Instagram. So I can live through you.” Dean clapped him lightly on the shoulder, and Max laughed before leading them out into the hallway that led to the main club.
“You’ve got wheels already! I don’t know why you don’t take the road trip you’ve been talking about forever.” Dean ducked his head and tried not to flinch at the reminder. “You should do it soon too, if you’re really studying to take that teacher -”
“Game time. Game face.” Dean cut him off as they made it to the lobby. He flanked him and then turned to Max and launched into business mode. “You take the front half, I’ll take the back. If they ask for anything ‘off-menu’ it’s a no for me but feel free to casual-touch above the waist if it gets you more tips.”
Max nodded in agreement but voiced it as well with a ‘ditto’. He looked apologetic as he added. “Sorry about last time again by the way.” Dean waved it off, rolling his eyes and shaking himself up to get into character.
“What’s an ass smack between friends?” It had made their last party happy and gotten Max an extra hundred for doing what they couldn’t. Dean couldn’t begrudge the kid but that was why he had made it clear he didn’t want anything that wasn’t allowed in the rules tonight. He wasn’t in the mood.
He couldn’t show it though. So when the doorbell rang, Dean chanted in his head ‘smile, smile, smile’ and opened the door.
Why they all had to come together, gathered in a gaggle, Castiel really didn’t understand. But maybe it was a blessing in disguise as he got to hang back on the periphery while Michael and Lucas did an informal roll call. He listlessly lifted a hand to show he was there as Michael said his name, and couldn’t miss the way several faces lit up, quickly smothered, before the activity moved on.
Ah, yes. The joys of being unfortunate entertainment, Castiel fought the urge to huff and kept his head down as the door to the private club was opened, into a dark foyer. A deep whisky smooth voice spoke to those at the front while a young looking man, maybe early twenties, tackled coats and jackets in the back. Castiel declined removing his trench coat and shoved his hands into his pockets.
It was some sort of Chippendale knock-off club apparently. He would assume the other one was shirtless as well. Was it on purpose? Castiel didn’t think any of the other men here tonight were gay…? Luke might cruise here for the laughs, Benjamin was bisexual but…? It truly made no sense to do this gathering at a gay gentlemen’s club. He was about to sidle up to Michael to inquire when the deep-baritone voice invited them to fall into line and follow him.
Through another doorway, down a corridor to a door that was opened into a dark room, where two huge semi-circle leather couches dominated the space. Low table lamps and dim wall scones provided the ambiance, and Castiel got the idea of a private backroom lounge. Michael, Lucas, Raphael, and Uriel ended up on the first couch and Benjamin, Ishim, Joshua and himself on the other. Both of the gentlemen that had led them disappeared against the darkened side of the room for a moment as someone stepped forward. Castiel could hear glasses and bottles clinking in the dark.
“Welcome to Heaven gentlemen! My name is Crowley and I welcome you to the Bar Room. Mr. Shield has spared no expense tonight for your gathering - all you newcomers, so I hope if you enjoy the night, you might look into your own membership!” A few chuckles and a few weak claps met his pronouncement, while Castiel stared blankly.
“For your viewing pleasure tonight, and I do mean viewing only, but we’ll get to the rules later. Your servers are Dean,” A body stepped forward, tall, short cropped hair. Castiel couldn’t really see his face clearly except for a defined profile but his eyes roved down and he found himself intrigued by strong, black-fabric clad, bowed legs. “And Max.” Yes, the curly haired one that had been offering coat service. “There is no touching, no solicitation of any kind. Tips are encouraged if the staff do excellent work but don’t take it too far.” A finger wagged in the air and Castiel frowned even as others laughed again. “I hope next time you’ll allow us to show what fine servers we have to offer of the female persuasion as well.” That got more raucous cheering.
“Please, do enjoy yourselves gentlemen. And if you need to warn anyone you’re not making it home early tonight, do it now or hold your peace.” With an oily smile, Crowley took a bow and turned, walking out the way they had come. The two servers split apart promptly, apparently splitting the couches and Castiel noted tall and buff was the one headed their way.
Castiel edged his way to the other end of the couch, trying to tuck himself down futilely. As huge as it was with all the space between them, he was still aware of his colleagues, who were close enough to make this situation discomforting. This whole thing stank of a set-up. He wasn’t completely sure but he had a feeling this was at least partially for him. They had apparently had the choice of gender, and Michael had picked two male servers.
“Hello gentlemen. My name is Dean and I will be your server tonight.” Ishim was the first to fall under Dean’s attention and Castiel fidgeted, looking around and wondering what he was supposed to be doing while these two men plied them with drinks. Soft music played as a backdrop to the mysterious atmosphere and the cigars came out from the next couch.
Joshua, who was the closest at a good three feet away, gave him a look of commiseration and a small nod of solidarity. As the closest one to a friend he had in this group beyond Benjamin, that confirmed Castiel’s thoughts.
He spent the next fifteen minutes watching Dean move from man to man, sitting, chatting, fetching drinks. He almost forgot it would be his turn as he watched Dean present Joshua with a tumbler of pale amber liquid, and suddenly the profile in dark relief was stepping into the light of the scone behind him and his server was lit to full effect.
He was gorgeous . Dark green eyes and a mouth to sin for. Strong jaw, sharp chin, and even a slightly crooked nose made him more memorable. Jesus Christ! He had a focused gaze as he homed in on Castiel like a heat seeking missile. Smizing, Gabriel called it.
“And what will you be having tonight sir?”
“What are you doing here?” Castiel stared at him, awed and unaware of how brain damaged he had sounded.
“Excuse me?” The eyes narrowed slightly, the slight smile pulled down to neutral (and more of a pout now and that should be illegal) and the smize went away. The suspicion in this low tone of Dean’s voice made Castiel mentally go over his words.
“I mean… I’m sorry that came out wrong.” He removed his hands from his pockets and made the low gesture of peace, expression apologetic. “It’s just… you look like a model. Like you should be modeling or something…”
He could see Dean closing off in caution. The service industry, Mona-Lisa smile came back. “I don’t want to audition for a photo shoot or do a casting couch or whatever, dude.”
“No, no! I wasn’t trying to do that!” Castiel sat up straighter, offended. He assumed his honesty came through in his vehemence, as Dean, while still staring suspiciously, lost the fake smile.
“Well if it’s a pick-up line, it's unoriginal. Can’t tell you how many times I’ve heard ‘you should be a model’ before.” The eye-smile came back, and Dean finally sat down next to him.
“I’m sorry again. I just meant you don’t seem like you belong here?” A curious eyebrow raised in his direction, and Castiel got the feeling he was being questioned silently. “People are usually in jobs like this because they like the social aspect, meeting people, having fun flirting…”
“So why don’t I belong here?” Dean asked and thankfully seemed amused, the plush smile on his lips urging Castiel on.
“Well for one thing, I don’t think you enjoy the ‘playing of the game’ with your clientele, based on the first thing you assumed I was implying.” Dean’s brows both rose as Castiel air-quoted his assumption. “Playing off the flirting would seem the better tactic. Furthermore, you’re here wasting time with me.” With a touch of self-deprecation, Castiel bobbed his head in apology. “Even though I’m sure I’ve already offended you twice in less than five minutes.”
“Maybe I like being offended.” Dean shot back, and Castiel cocked his head at him before nodding over to the other side of the room.
“Your partner over there has already checked in with everyone on his couch twice.” Castiel gestured over to Max to illustrate. “He’s not as individually in-depth as you but he’s flitted around and made everyone easy with him. You, on the other hand, want everyone to be satisfied immediately. You’re a people pleaser.”
“Okay, Sherlock. That just shows we have different styles. And doesn’t being a people pleaser mean I’m perfect for the service industry?”
“I mean, it would if you liked the people you were dealing with.” Castiel shrugged and considered it a win as Dean snorted softly, shaking his head. “Shouldn’t you be going to the other gentlemen and plying your trade?”
“Nah, you seem the easily guilted type. You’ll buy a bottle,” Dean said flippantly.
“...A glass.” Castiel responded, not about to be bullied.
“Limited Edition Blue Label is sold by the bottle. Sorry,” Dean said sassily. His tone was not in the least bit sorry. He stared Castiel down, smile slowly widening as Castiel stared back.
The tiniest arch of one brow made Castiel huff out an exhale and he capitulated. “Fine. I’ll have a bottle of Blue Label.”
Smug satisfaction permeated off Dean as he stood, and Castiel watched him go, feeling a bit doe-eyed. Even the view of him leaving was fantastic… he swallowed and stood to shrug out of his coat, laying it on the couch next to himself. The lounge was A/C but he was feeling a touch warm.
A brief flick of a glance at his watch showed it was only 9:30, and he wondered how the time had gone by so slowly. It felt like he’d endured years of humiliation in front of Dean already. He shot a glance at his other couch-mates and they were drinking and having conversations with each other, and a look across the room showed the other couch wreathed in cigar smoke and low laughter. Castiel wondered if they were watching him and Dean from over there.
Dean returned with a gold box, tied with a red bow that he removed with a flourish that made one of his biceps flex. He walked up and stopped inches from Castiel’s knees, leaving him forced to look up sharply. “This Year Of The Pig commemorative bottle features genuine hand painted traditional art,” The hand that had removed the bow, ever so slowly yet confidently removed the bottle from the grip of its box. “Note the atypical color of the Johnny Walker label and the artisanal shape of the vessel…” The box was placed gently on the half moon table to the side of them without Dean even looking, and the bottle now cradled with both hands, presented to his face at Dean’s groin level. “This limited edition has a unique flavor profile of fruit and citrus with an aftertaste of smoky chocolate…”
Castiel strangled a moan as the seal on the bottle was torn with a sound not unlike the foil of a condom wrapper. The bottle thumped down with gentle finality on the table next to its box and Dean sat, with a smile that looked like the cat that got into the whole larder of cream.
“Would you like a glass?”
“Ye-yes, please.” Castiel cleared his throat and Dean smiled again, a wider one that hinted at teeth before leaving. He couldn’t look this time and instead pulled his coat into his lap, patting at his pocket for his wallet. He was going to feel tonight in so many ways…
Dean returned with a lowball glass with two cubes of ice and his curl of a smile and sat next to him again. Why he had to lean into Castiel’s space to reach for the bottle was not a mystery - it was part of the show obviously, but what was confusing was why he was still there.
Castiel had probably bought the most expensive whisky in the place because of a couple of bats from those ridiculous lashes. He had won. He could move on. Dean handed him the half-filled glass of whiskey and Castiel tentatively took it, careful not to touch their fingers.
“You make me very uncomfortable,” Castiel said it lowly, before taking a gulp of his drink, not looking at Dean.
“...I don’t know whether to ask if it’s a good discomfort or back off.” Dean responded somewhat wryly, trying to angle to catch his gaze. Castiel cut a look sideways at him and sipped again before speaking.
“I know you’re actually trying to make me comfortable and do your job but…” Castiel gestured slightly with his glass, trying not to bring attention to them. “All this and…” He jerked his head at Dean, taking in his bemused expression.
“You knew you were coming to a gentlemen’s club to pull an overnighter didn’t you?” He made a noise of assent as Dean pursed his lips at him. “What did you think was going to happen here? Cards?”
“If I may be brutally honest?” Dean made a ‘go-on’ gesture with his hand. “This is my first time being invited to one of Michael’s ‘meetings’.” Castiel was very aware of Dean looking at his hands, his wide, closed-mouth smile back in effect. He dropped them to his lap and fidgeted. “I was not expecting male servers as only two persons here are even open to uh, your persuasion. Also, I highly suspect I’m here for entertainment as well, as I have a habit of… offending people.”
Dean’s laugh caught him off-guard. The suddenness of it splitting Dean’s face disarmed him and Castiel was struck speechless as Dean ducked his head in amusement.
“Oh, I couldn’t imagine that, Mr. What Am I Doing Here.” Castiel caught the edges of his smile as he tucked it back away, closed-mouth professional and he wanted more.
Castiel pointed at one of his business partners over on the other couch. “At Luke’s bachelor party, I asked one of the strippers if her profession was related to her father leaving her as a child.”
“Oh. My. God !” Dean’s laughter rang out loudly and Castiel glowed internally as Dean laughed with his whole body, head thrown back before he controlled himself, covering his mouth from gusty laughter.
“My people skills are rusty.” Castiel shrugged and smiled, feeling strangely proud. Dean was having trouble getting back to the service smile; he had to look away from Castiel and duck his face. Castiel found he was fine with being the butt of the joke, just this once.
“You can’t be for real.” He found Dean looking at him with a soft smile, and was about to offer another terrible story when those green eyes slid off him.
Now the professional smile looked like a mask to Castiel. Dean looked back at him and said “Excuse me,” politely, before standing and making his way around to Ishim. Castiel found himself both relieved - he could breathe! Had he been holding his breath? - and bereft with the loss of Dean’s company.
He tossed back the dregs of the glass he was holding and poured himself another slightly fuller one. Joshua was looking at him questioningly, and not being sure how he would respond should Joshua voice his concern and check on Castiel’s well-being, he pushed his bottle of whiskey down toward his friend.
He was treated to watching Dean’s shadowy profile go back and forth from the bar a few times, and long periods of nothing to do as Dean sat with the others. Castiel kept pouring more drinks and worked his way through two more with Joshua’s help. By the time Joshua was back under Dean’s attention, Castiel’s chest was pleasantly warm and he watched unrepentantly. He coveted every blink, every smile.
By the time Dean got back to him over a half hour had passed, and it was minutes to eleven.
“You have returned,” Castiel said boldly as Dean stood between the half moon table and his knees. His head lolled back on the couch so he could look up this time. Sitting up to Dean’s crotch would be a bad idea.
“So I have.” Dean’s smile looked a little brighter for him. It could be his imagination but he thought so. “You’re only halfway through that bottle?”
“My tolerance for alcohol is quite high but I don’t enjoy just… chugging it.” Castiel pulled his coat more into his lap so Dean could sit closer. “Your recommendation was a good choice and should be savored. Would you like a glass?”
“Sure.” Dean sat and just the slightest relaxation of his slouched stance put their thighs into warm contact. A look was shot at him over a wide shoulder and Castiel smiled slowly, feeling his face lifting. The reach for the bottle came back successful and Castiel watched with wonder as Dean filled his glass, took it from him and then had a sip.
“Mm.” Dean swallowed, licked his lips and had a second sip while Castiel watched. Indecent.
He gave the glass back and reached forward again to place the bottle back on the table, pressing their thighs together for just one hot, long moment.
When he leaned back Castiel found himself dragging in a breath of air for holding it again.
“I didn’t realize how long I’d sat down with you earlier. Guess you were right about me being a people-pleaser, but it looks like the whisky did more of a job than I did with making you comfortable.” Dean’s smile was slow as he sat back too and Castiel was quick to reassure.
“No, I’m sure it was you. You recommended the bottle.” That got him a quick flash of a smile, teeth soon hidden again. Castiel was good with just holding Dean’s drink on his thigh, waiting for Dean to feel like moving again.
When Dean looked at him again, he proffered the glass silently and Dean rolled his eyes before taking it - their fingers touched this time - and having another sip. Castiel sighed happily as he got his glass back.
“Gotta watch you,” Dean said low and secret, “Apparently I do like offensive people.”
That made him smile, the idea Dean could like him when usually Castiel’s demeanor alone put people off, never mind when he actually opened his mouth.
“I don’t usually like people trying to read me. It’s bad enough already with my brat of a little brother.” Dean’s voice had a sarcastic edge to it but Castiel could hear and feel the fondness underlying.
“I have a bad habit of saying whatever comes to mind. It’s not so much a lack of filter as –” Saying what he thought or felt without keeping in mind platitudes, social niceties or decorum? “– well, I guess that is still a lack of filter. But I usually just state whatever I notice.”
“Yes I remember…the rusty with people thing.” Dean made air quotes with his fingers and turned his head to smile at Castiel. “But don’t let anybody make you a joke okay? You’re great.”
“Blunt is great.” And Dean swung his thigh into Castiel’s purposely.
“D-do you want another…?” Castiel lifted the tumbler again, more than willing to give Dean more whisky and watch him drink from his glass. The light brunette shook his head though, lifting it from the couch.
“One drink on duty for me. I have to keep you guys drinking, not get sloshed myself.” Dean smirked. “However…I might make it two if you buy a bottle of champagne.”
Castiel sat up and squinted. “Do you make money off of each bottle sold?” Castiel tilted his head at Dean and was rewarded with a wink.
“So you’re not just a pretty face.” Dean had just winked at him. Was that - and he called him pretty! Calling someone pretty was definitely - !
Castiel blinked owlishly, befuddled. “I don’t think I’ve ever been called pretty.” He found himself feeling awkwardly flattered and tried to shrug off the feeling. “I’m a financial analyst with a degree in actuarial science though so…yes, more than a pretty face.”
Dean grinned, and Castiel was too warm again. “I would have guessed accountant, or stock broker. But close enough I guess.”
Castiel wrinkled his nose as those were not really close at all and Dean laughed hard again, with his head thrown back. “God, you’re killing me. I meant you seem like a numbers guy.”
“What’s a numbers guy like?” Castiel pressed, genuinely curious. “You can say that…but I can’t say that you don’t look like you belong here?”
Dean got serious quickly, even the business smile tucked away from his pursed lips. He scrubbed his fists down his clothed thighs and sat up straight, putting inches that felt like miles between them.
“You look anal retentive like everything has to be just so and work out perfectly. And suits… it’s usually numbers guys.” He looked away and Castiel admired the crook of his nose, the arc of a cheekbone in a clenched jaw, the splay of eyelashes against skin. Upset and still gorgeous. “And look at me. There’s nothing about me that doesn’t belong here. This is what I’m good at.” A steely frown was leveled at him that made his knees weak.
“You’re definitely meant for more than here,” Castiel said reverently, breathless.
Too blunt again. Dean stared for a moment then stood and left wordlessly. Castiel hoped no one had seen that as he sank back into the chair again.
The next look at his watch showed it was almost eleven-thirty. Time was passing much faster now. Too fast because he needed to make it up to Dean. He said he didn’t like people reading him,and Castiel still had persisted in questioning his choice of profession. Even if it was obvious to him Dean didn’t like his job, if a career change was going to happen it would be neither his business nor his place to mention it.
Dean wasn’t wrong either about looking the part… Castiel looked from under his lids as Dean did his job admirably, delivering drinks to the other men and stopping to talk with each of them as he had with Castiel. Just not as long, not with the looks and none of the laughter.
Dean should have a job where he didn’t have to hide himself. He was so effervescent…
Castiel wondered more about Dean as he made his way closer to the bottom of his Johnny Walker bottle. Joshua had checked in a few minutes ago, and Castiel had said that Dean was upset with him. If he would be so kind as to let Dean know that he would like to have another drink with him. Joshua had patted his shoulder and gotten him a glass of water.
He had the briefest of naps after closing his eyes, so he didn’t have to watch Dean serve Ishim a glass of wine with the slightest exaggeration of a bow that put his ass to fine offset, right for Castiel.
He had just meant to not see - but had actually fallen asleep ever so briefly - because it hurt.
When he woke up he went to get himself his own glass of water and was intercepted by Max, who guided him back to his seat and gestured into the dark.
Castiel groaned happily as Max delivered his water for him, and maybe napped again after drinking it.
He woke up to a presence brushing by, jerking to awareness suddenly and catching Dean apparently having saved his coat from the floor. He was about to dart away again when Castiel called him back.
“I’m ready for the champagne now.”
Dean looked him over, snorted and turned on his heel with a grumble. He disappeared over to his dark wall again, and Castiel fisted at his hair and rubbed his fingers over his face.
The bottle and two glasses that Dean returned with were crystal and Castiel felt his wallet mourn even as he sat up eagerly.
“This is Krug’s Clos Du Mesnil- a Chardonnay champagne.” Dean presented the bottle, two handed with a slight tilt to his body. “This is a single vineyard, single grape vintage from the Krug’s vineyard in Champagne, France. The year is 1998 and with ripening, this wine has been said to have a dry fruity sweetness.”
Dean went for the cork remover and Castiel raised a hand in request.
“No need for all the… flexing.” Dean blinked and popped the cork perfunctorily allowing Castiel to continue to breathe.
“Well that’s fine then.” And Dean sat himself down at an angle to him, much too close and began to pour a glass, which he handed just maybe a fourths full, to Castiel. He poured the second for himself, and Castiel watched as he sniffed and then had his first sip.
His Adam’s apple had finished bobbing, and Castiel couldn’t hold this one thought anymore.
“You’re very beautiful.”
“Oh, you’re drunk already?” Dean expelled the cough of a laugh dryly. Castiel would not be denied.
“I just nursed a bottle of Blue Label for four hours.” So maybe yes, he was drunk… “But no. You’re honestly… quite handsome.”
He watched with some wonder as Dean seemed to flush, his complexion darkening as he ducked his face away. “Yeah, okay, whatever. Enjoy your champagne.”
Dean tried to leave but Castiel grabbed his wrist gently, careful not to jostle his wine glass.
“You said you’d have a glass with me.” He blinked up, feeling betrayed.
“Fuck…” Dean stared him down. “You get real forward when you’ve had some drinks in you, huh.”
“Forward?” Castiel tilted his head and let his hand slide off Dean’s wrist. “I’m not trying to… come on to you or pick you up. It’s…the truth.” Dean looked away, tipped his glass down his throat and sat down next to Castiel decisively, crowded close.
“Shut up.” Dean poured another glass and took deliberate, delicate sips, not looking at Castiel.
Who was very much looking at him. His lips were a crime. His eyes were a prison. Castiel imagined knowing Dean’s mind was like escaping Alcatraz - near impossible. He’d like to try.
“If you’re ever… interested in portfolio investments.” Confused, Dean looked over at Castiel who then started patting about in his coat. “That’s… my area. I have…” Wait no, wallet! He dug into it, pulling out both his credit card and a business card.
He held both of them out to Dean, the business card on top.
Dean blinked rapidly down at the cards held out to him, then back up at Castiel.
“ That would be a flirtation.” Castiel said, quite proud of himself again.
Dean’s jaw dropped a little, and then he shook his head and looked over to the other side of the room. He put his wine glass down and leaned in closer, facing Castiel head on.
“We don’t… we don’t do that here.” Dean licked his lips, eyes darting over Castiel’s face. “There’s no “fraternizing” with the clients.” His own air quotes were adorable as he swallowed heavily.
“I’m just offering… professional, financial advice.” Castiel nodded as he answered, perfectly succinct and not necessarily lying. The alcohol was finally getting to him as he felt his words coming slowly. “But if that’s not of interest…”
Dean snatched the cards, snake-strike fast when it looked like Castiel was going to take them back. He got up and walked away, and Castiel received his credit card and a receipt back in a little black binder from Max.
But not the business card.
Dean looked at him a lot as he passed by, little visual check-ins on him as Castiel and the rest of his couch polished off his extravagantly priced alcohol, but he didn't sit with Castiel again.
Finally drunk and tired of taunting himself with what he couldn’t have, Castiel called an Uber around 1:30am. The car arrived around two and Castiel tried not to have a staring match with Dean as he stood, before he turned and made his way out of the Bar Room.
Funnily enough, once Castiel Novak (and God, what a name!) had left, the rest of the party started to trickle out as well. By minutes to four – the host of the party Michael Shield was the last to go, after being poured into his car by his driver with Max’s help – everyone was gone, so Crowley let them leave the hour early, cash in hand.
Dean had sold two thousand five hundred in alcohol to Castiel alone (one kay for the whiskey, one point five for the champagne) so he had made off with eight hundred for bottle service plus a few random hundred dollar bills. All said and done he had made five thousand one hundred and fifty bucks - which was a record for him and he felt…
Fuck. He felt excited. Excited and nervous as hell about the card in his jeans pocket.
The money went into a deposit envelope and dropped off promptly at his bank. Plans for it were kind of hazy in Dean’s mind. What wasn’t unclear was what would happen if he dared to call Castiel’s number and follow through on…
Any of what they had been dancing around last night.
Because something had been there, right? It wasn’t just alcohol and a dark room because it had been there even before Castiel followed up with the champagne and challenged Dean to sit with him.
If Crowley found out Dean would be fired. That wasn’t even in question. He had seen a couple people lose this job for taking off-menu offers. It wasn’t like he hadn’t had some himself, but when he had measured an immediate twenty thousand to suck a guy’s cock versus a whole year’s pay and the steady job – it was never worth it.
Dean pointedly, pointedly did not consider if Castiel had been the type of guy to do that, if he would have turned down that kind of offer last night.
Because he had taken the card, hadn’t he? And it was a slippery slope. He would call, they might go out for coffee. Dean would find himself charmed against his will, again. He’d take him back to his apartment for drinks. Castiel would get forward again, and Dean would fuck him.
He would absolutely let Castiel fuck him… Dean covered his face with a loud groan. Fuck.
Dean wanted him. He didn’t quite know why and he should know better than to risk his livelihood…but Castiel had ‘shot’ his shot with the card…if Dean didn’t follow through, it would have been for nothing. All the wasted potential.
Even though he was sure Max had seen nothing and the cameras in the corners of the room had been blocked by his body, Dean’s paranoia ran high. If he did this, even a whisper of it couldn’t make it back to Crowley.
He knew he was going to call because he couldn’t make himself throw away the card. But he waited anyway.
“Morningstar, Shield, and Associates, this is Castiel speaking.” The gravelly rumble of his voice got Dean again, like a sucker punch to the gut.
He paused, swallowed and with a low sigh, charged in.
“Portfolio investments…” The silence hung for a moment. “I’m interested.”
“...Dean?” Hesitant confusion came over the line and Dean rolled his lip under his teeth before responding snarkily.
“Oh, you have other guys you used that line on?” He gave a choppy laugh and cut himself off quickly as silence hung ponderously between them.
“I…find myself pleasantly surprised.” God, Dean had forgotten how he sounded like he was discovering shit while he talked.
“Yeah, I’m surprised too.” He was surprised he was really doing this. But this guy’s smile had made his heart skip a beat and something about the offer of his card had felt momentous.
“It’s Thursday.” Castiel announced apropos of nothing but Dean figured he meant his wait since Saturday, or Sunday really.
“Yeah well risking my job if my boss found out about this needed three business days of consideration.”
“If we met outside of his establishment, I don’t understand why that would merit your dismissal.” Castiel sounded like he was settling in for a debate, and Dean couldn’t help smiling. “Why would the rules be so stringent?”
“Did we really meet outside his establishment? You’re not a lawyer, you know it’s not a technical loophole. Imagine this,” Dean blew an exhale out slowly. “I meet a guy at Heaven. I work a night with him. He gives me his number and we meet up outside of Heaven. Let’s say we fuck.” Dean smirked faintly as Castiel inhaled on the other end of the line. “Let’s say I get financial favors from this imaginary guy. And then I turn that into a hustle with multiple clients from Heaven. That’s what Crowley’s afraid of. A side ‘hustle’ with any of his clients would be bad for the club. Especially something so…disreputable.”
“That’s…not what this is.” Dean didn’t like how Castiel’s tone edged up in question.
“...no. But, I’m just saying,” Dean swallowed, licking his lips before continuing, “I’m already overthinking if this is a good idea or a terrible one and by the time I hang up I’ll probably regret this but I - I couldn’t help thinking I’d regret it more if I didn’t call.”
“I like you,” Castiel said suddenly, quickly. “I do not give out my card as a come on, I do not invite…attention. But you made me uncomfortable and I…realized I liked you.”
“Same?” Dean said awkwardly, face flushed hot and feeling second-hand embarrassment over the phone.
“Good. That’s…good.” The second ‘good’ came out stronger and then Castiel cleared his throat. “Is it okay then, if I save your number?”
“Umm, yeah. Text me. That’s how I usually communicate.” Dean leaned back on his bar chair and rubbed at his neck with his free hand. “So, uhh, we can arrange to meet or just keep talking, I don’t -”
“Dinner.” Fuck, why was his voice getting lower. Why did ‘dinner’ in that voice sound like a euphemism? “If you’re amenable?”
“Yeah. Din-dinner sounds good.” He was fucking stuttering. “I’ve gotta go. Just umm, text. Yeah. Okay -”
“Thank you for calling, Dean,” Castiel said, and Dean strangled out a sound vaguely like ‘bye’ before hanging up.
A few moments later, a text message from an unknown number came through on his phone.
‘This is my private number. Feel free to save this one in your phone. - Castiel’.
Dean lowered his head to his kitchenette counter… and laughed softly.