#rich!cas

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"Come on Ricky, you owe me that money!" Dean says on his phone, taking a step forward when the line of the coffee shop shortens. 

"I don't owe you shit, Dean. You still owe me the last three months of your rent," his ex landlord says on the phone.

"And I'll pay you, you know I will. But to get the money, I need a job, and to get that job I need some new clothes and-"

"Yeah yeah, I know the deal. You think no one has told me that one before? No bueno, man, I'm keeping your deposit," Ricky grumbles. 

Dean groans in frustration. "Come on, all I need is fifty dollars so I can buy a pair of pants without any holes in it. You give me fifty, I get the job and I pay you back, how does that sound?" he tries to negotiate. 

"Like a fucking lie," Ricky spits just before hanging up.

"No Ric-fuck!" 

The woman in front of him in line sends him a dark look. Dean rolls his eyes at her. Like she hasn't heard worse before. 

Ricky was his last shot. It was a long one, he really does owe that bastard some serious money. Guess he can kiss the job interview at two goodbye. It's some kind of assistant job. It sounds easy enough, buying coffee and picking dry cleaning and stuff. It was still a long shot anyway. Dean's only real job experience is being a bagger boy when he was seventeen and it lasted about two months before his dad decided to move them further east. 

So far, he'd always managed to get by doing repairs or cleaning at gas stops and motels. The older he gets and the harder it gets to find that kind of random job. People are more willing to give a few bucks in exchange for manual tasks to a kid than they are to a nearly thirty years old guy. Now they just tell him to fuck off. 

And since it's always been casual and off the book, the only official work experience he has is the bagger thing. He doesn't even have a high school diploma because he dropped out long before that. Not exactly a stellar resume. Which explains why he hasn't found work in eight month and is currently living in his car. Thank God he has Baby. 

He had been too ambitious thinking he could get his own place. It could only pay rent for about five months before he went broke. He's never had a home before, and had no idea that having an apartment cost so much. In motels, you don't exactly have to pay for water or heat or utilities. There was a bunch of stuff he hadn't planned for that ate up the last of his meagre savings. Ricky threw him out after three months when Dean couldn't scrape up enough money to pay rent anymore, putting a violent stop to Dean's pipe dream of living a normal life. He hoped it would be simpler to get a job if he had an actual address, had even thought about scrapping up enough to maybe get his GED. He's not sure what he's going to do now. 

He's always wanted to be a mechanic. If his dad ever taught him anything, it was how to take care of the Impala. John taught him all the basics and Dean got the knack of it. As a teen, he spent days reading car magazines and working on the Impala, trying to learn as much as he could about how cars worked and how to repair the different parts. He knows enough by now that he could easily work in a garage, but he's got no diploma, and hasn't found anyone willing to hire him on faith alone. 

The line of the coffee shop shortens again, the barista asking her order to the goody-two-shoes in front of him. Dean looks regretfully at the display of sandwiches. He searches his pockets and only comes up with three dollars. Of course, the cheapest piece of food cost four dollars. Dean sighs. Guess just a coffee will have to do today. 

He won't have another choice but to go to the soup kitchen tonight. He hates it there. The food is crap and he wants to punch the prancy people serving it. They always try to give him some Jesus bullshit with his food, like Jesus is ever gonna put a roof over his head and find him a decent job. Neither Jesus nor God nor whatever gives a crap about him. Not that he blames them. Hell, if they exist they're probably not big fans of the guy that used to slip into church as a kid to pick the lock of the donation box

"Just an americano, please," Dean says regretfully when the barista asks for his order. At least it will keep him warm and fill his stomach for a short while.

Halloween just went by and the weather is becoming really cold. He should use the last of Baby's tank to go as far south as he can before winter really hits. He probably won't get farther than Wichita though, and the thought makes him shiver. No one wants to get stuck for a winter in Wichita. Maybe he could go and see if he can make a few bucks at the nearest motel, that kind of place always needs a handyman's help. He hasn't tried the one on Corn Street yet. He's noticed only two lights are still working on their sign, he could offer to help with that. If he makes fifty bucks, he might be able to reach Austin. 

Dean stops on the sidewalk in front of the coffee shop, pondering if he should walk to the bar a few streets down or the motel. Sometimes Benny, the owner of the bar, lets him use the sink in the back to wash up. If he's lucky, he'll even get some leftovers from last night. It's generally just some stale pretzels, cold fries on good days, but it's still better than nothing. He's got two cans of beans and a car with an near empty tank to his name right now, so he's not picky. 

Dean takes a look at his watch. It's eleven thirty already, the leftovers are probably already in the trash at Benny's. The motel is probably his best bet. 

"I'll give you a hundred dollars if you pretend to be my boyfriend." comes a hoarse voice, way too close to his ear. 

Dean jumps, nearly spilling his coffee on himself. He spins to the right to face the man who just talked and is met with a pair of clear blue eyes. Way too close again. He waits a second for the man to take a step back as he realises as close Dean turning brought them, but the guy just continues to stare at him, head slightly tilted to the side. He's wearing an oversized trench coat over a dark blue suit that looks expensive. He's so close a gust of wind makes the bottom of his coat brushes Dean's shin. 

"Dude, personal space," Dean reproaches, taking a step back. "And fuck off, I don't swing that way," he adds, not meanly. It's not the first time he's getting hit on by a dude. Sadly, not even the weirdest. He's strictly into chicks though, so no dice.

"Two hundred bucks," the man insists. He looks ready to fall on his knees and beg, eyes going wider and wider as he throws a panicked look to the right of Dean's shoulder. "It won't take more than ten minutes and all you have to do is nod along," he begs, making Dean wonders if he's in danger somehow. Maybe he has a stalker or an abusive ex? 

Dean follows his eyes to a woman coming closer. She's very elegant in a grey pantsuit and a long white fur coat as she walks straight toward them. He can feel her eyes judging him even from thirty feet away, looking at him from head to toes. If he wasn't already self-aware of the number of holes in his jeans, he would definitely be under that gaze. 

"Five hundred dollars," the other man whispers just as the blond woman reaches them. 

"Castiel, dear, you should have told me we would have company, I would have notified the restaurant," the woman says, sending a clearly disapproving look toward Dean as she deposits a kiss on the other man's - (Castiel, apparently, what kind of name is that??) - cheek. 

"Mother, let me introduce you to my boyfriend," Castiel says, looking ill at ease. He's obviously not a very good liar. 

Dean blinks a few times as their attention turns toward him. Castiel seems to be trying to communicate something with his eyes, and Dean frowns in incomprehension for a moment before he gets the hint. 

"Huh. Dean. Winchester," he finally says. "Ma'am," he adds when she just continues to stare at him like he has grease smeared all over his face. He's pretty sure that she wouldn't want to touch his hand if he were to offer it to shake, so he doesn't. 

"Naomi Novak," she introduces herself. "What a delight to finally meet Castiel's new companion," Naomi says, her deadpan tone contradicting her words. "Of course, I would have preferred not to be ambushed by such an announcement. Castiel, you know, that Le Délice hates it when we change our reservation last minute. Who knows if they will even have a table for three," she declares, already composing a number on her phone. 

"It's okay, mother, Dean won't be joining us for lunch."

"Oh, is it because your attire isn't appropriate?" Castiel's mother asks, looking at the holes in Dean's jeans and the big leather jacket that used to be his dad's. "I assure you they won't say a word about it if you're with us," she reassures. 

Dean squirms a little, wondering what the hell is even happening. Ten minutes ago he was buying a coffee and going at his day like a perfectly normal person (well, albeit a homeless and jobless one). Now, his fashion sense is being criticized by the mother of a man who is pretending to be his boyfriend. Did a piano fall on his head or something? Has he finally lost his mind?

He looks to the man beside him. He's scratching the side of his neck in nervousness. The move makes his coat fall a little over his wrist, revealing a freaking Rolex watch. Dean looks back to the woman, eyes sliding on her diamond earrings and the huge rock around her neck. 

You know what? That's not okay. His stomach has been crying for food since last morning, and he's what? Supposed to help this stranger by saying no to free lunch at one of the most prestigious restaurants in town? Fuck no. He's gonna eat like a king and make a few hundred bucks off the back of those rich assholes. 

"In that case, it would be my pleasure to join you," Dean announces with his most charming smile. 

"What?" Castiel can't help but bark. "But y-your work thing?" he tries, sweating. The round panic eyes are back. Dean sends him his best shit eating grin. They both know he now either has to invite this stranger to lunch or reveal the lie to his mother. The guy is trapped and may as well continue to play along.

"It's not as important as a chance to finally get to know your mother, honey," Dean answers. "He's told me so many nice things about you, Naomi. Can I call you Naomi?"

"Of course, dear," Naomi says. She looks a little wide eyed too, probably thrown by Dean turning on the charm to the max.

"Perfect! We shall go now, we don't want to miss your reservation. I do hope it won't be too much of a bother for them to add a chair to your table," Dean says. He should probably tone it down with the pompous tone, because he nearly added an English accent here. 

Naomi leads the way, and Dean is going to follow when a hand grabbing his arm makes him fall a few steps behind. 

"What the hell are you doing?" Castiel hisses.

"Acting as your boyfriend?" Dean says innocently. By Castiel's glare, he's not fooled. 

"I asked you to nod silently for ten minutes, not to do method acting for a whole meal," he reproaches. Naomi sends a look behind her shoulder and Castiel smiles at her like there is no worries, indicating for her to lead the way, 

Dean shrugs. "I had some free time."

"I'm not giving you more money than planned, if that's your goal," Castiel says with a suspicious squint. 

"I'm fine with the five hundred as long as you're also paying for lunch," Dean says, wiggling his eyebrows as they walk toward the restaurant. Something passes on Castiel's face that Dean can't quite identify. The other man stares at him for so long that it's a wonder he doesn't trip. He finally relents with a long suffering sigh as they enter 'Le Délice'. 

Apparently, Naomi Novak is prominent enough that they don't mind changing her reservation after all. They're seated at a table near a legit indoor fountain. Dean is looking around, trying not to let show how impressed he is by the place. The walls are made of stone and covered in frescos that he always thought you couldn't see outside of a church or castle. A waiter gives him a leather covered menu and Dean opens it eagerly. After a few niceties to Naomi, they're asked what they want to drink. Dean has an inkling that he probably shouldn't ask for a beer in an establishment like this. 

"Same for me, please," he says after Castiel ordered some wine with a name Dean can't pronounce. At least, he hopes that's wine. Who knows. Hell, in this place the bottles of water are probably more expensive than his usual brand of beer. 

Dean starts to second guess his decision when he realizes that the menu is in french. What is it with rich people and France? He just wants a damn steak, how do you say that in french? Is there even steaks here or is it just frog legs and snails? Oh god, he hopes not. 

"I think I'll take the duck today," Naomi notes. "Nobody cooks it better than chef Francis. How about you Dean? Have you ever come here before?" There is a mean glint in her eyes that says she knows perfectly well he hasn't. Hell, from the side eyes he got from everyone as they crossed the room, everyone here knows he's not from their world. There are three holes in his jeans, threads hanging from the bottom and his dad's leather jacket probably should have ended up in the trash about three years ago. Even now, it's still too big for him and the sleeves are so scruffed that they're nearly paper thin. The original dark brown color has turned to a light beige in most places from wear. His scruff is just the bad side of too long now, and he hasn't had a haircut since April, strands starting to fall into his eyes. At least, he's wearing his best plaid shirt and managed to wash up last night, so he's not smelling too rank. Why would Castiel pick him out of all the people in the street at that moment to play his boyfriend? It makes no sense at all. From the guy's obvious discomfort as he hides behind his menu, he probably realizes it. 

"Actually, Naomi, duck sounds like a delicious idea," Dean says, voluntarily ignoring her question. To be honest, he’s never even eaten duck before, but it's poultry so it probably taste like chicken. You can't go wrong with chicken, right? His stomach certainly likes the idea, gurgling so loudly that he has to hide it behind a cough. 

Castiel ends up ordering some fish and soon their drinks arrive. Dean barely has time to sip at his red wine before Naomi pounces. 

"So, tell me everything, how did you two meet?"

Dean nearly chokes on his drink. Castiel seems to gulp down his whole glass. 

"We met at a coffee shop. Dean was in line in front of me and we started to talk," Castiel explains, not quite meeting anyone's eyes.

"How quaint!" Naomi exclaims, clasping her hands in delight. "I'm just sorry that you didn't tell me about it sooner, Castiel. How long have you been keeping this charming man a secret?"

"Not-," Castiel clears his throat, "-not long."

"Well, it's nice to finally meet you Dean. I sure wish this luncheon will give me the chance to learn everything about you."

Luncheon? Who even talks like that outside of Downton Abbey?

"I do hope I'll get to keep some mystery, we wouldn't want this guy to lose interest," Dean says with a wink. He pats Castiel's hand on the table. Should he hold it or something? How open on PDA are gay people those days? Not that he knows more about how heterosexual couple act in public anyway, especially in those crowds. It's probably safer to keep the PDA to a minimum here. 

"You have to at least tell me some things. For one, what career path are you on?" She looks like a shark circling her prey. 

"I'm a mechanic," he lies. He'd rather stay as close to the truth as possible. It's a little unfair that Castiel is letting him do all the talking when his initial demand was that he stayed silent, especially since it's his skin that Dean is apparently saving, but the guy looks like he's swallowed a potato whole. 

"Oh, that's...interesting," Naomi says in that insincere tone of hers. She looks like he told her he was fucking children’s corpses every full moon. He's two seconds away from telling her that he's actually jobless, penniless, and homeless, just to see her face, when Castiel intervenes. 

"How is Anna's engagement party coming on?" 

Thankfully, this seems to be a subject Naomi loves because she tells them about every aspect of the future party all the way through their meal. 

Duck, as it turns out, is actually very good. It's more like red meat than chicken, which is a great surprise. Although, Dean isn't a fan of the way rich people put tiny quantities of food in very large plates. He eats all the dinner rolls and scrapes every single bit of sauce out of his plate, yet he's still hungry by the end of it. He nearly starts crying when the waiter asks them if they'll take dessert and Naomi declines. He's starting to wonder if that little piece of duck was worth sitting through lunch with her. 

"That sounds like you're turning this into a wonderful event, mother, Anna must be delighted," Castiel compliments. 

"Oh, you know your sister," Naomi waves it off. "It sure feels like a nice opportunity to introduce your new beau to everyone."

Dean frowns. What's a beau? Is that him? That's not him, right?

"I wouldn't dare take any attention away from Anna," Castiel tries to refuse. 

"Don't be daft, you know your sister won't care. Everyone will be so happy that you've finally found-" she passes a long look, over Dean, like she's doubting anyone would actually approve of him. She certainly doesn't seem to, "-someone," she finishes lamely. 

"Oh shoot, I don't think I'm available that night," Dean tries to play off. 

"I'm not sure I've told you the date of it yet."

"Cas did," he says. The other man perks up at the surname, but whatever, 'Castiel' is a mouthful. "And I have this huh work thing, you know? Bummer," Dean says with a fake pout. 

"What kind of 'work thing' can a mechanic possibly have on a Saturday evening?"

Dean tenses up, pursing his lips. "One he can't get out of?"

"Nonsense, you're coming," Naomi brushes off. And that is that apparently. Shit. There is a vein about to pop on Castiel's forehead. "Castiel, dear, you look a little white. Was the fish okay?"

"I-Yeah-I-Actually, do you think we could possibly cut our lunch short? I am indeed feeling quite unwell."

"Of course, my dear," Naomi says, leaning forward until her hand touches his forehead. "You're as clammy as a fish. I should come home with you, and make sure you're okay," she announces, taking her napkin off her lap and deposing it on the table, ready to stand up. 

"No!" Castiel stops her, a little too brusquely. "I-Dean will take good care of me, don't worry," he says, getting up and grabbing Dean's arm so he does so too. Dean follows his lead, all too happy to get out of here. "Stay and enjoy your tea, mother."

"If you say so," Naomi says, sending an unsure look at Dean, obviously upset at being brushed off in his favor. "Call me this evening, or I'll worry all night."

"Of course, mother," Castiel acquiesces, kissing her cheek. Dean hovers behind him. Is he supposed to kiss her too? Wave hello? Shake her hand? 

"Dean," she says as what is apparently a sufficient goodbye. Thank God. "I'll be sure to see you on Saturday," she reminds just as they're walking away. 

Cas turns on him as soon as they're outside the restaurant. 

"What was that?!" he asks, not quite yelling. He starts pacing, rubbing a hand through his already pretty ruffled hair. 

"You owing me five hundred bucks? Dude, you're lucky I don't charge you more for the fresh hell I just lived through."

"You went through hell? You?!" his pacing gets faster and Dean has an idea that if he stops pacing he might punch him in the face. 

"That's what you get for asking this kind of stuff from a perfect stranger," Dean shrugs, pushing a pebble with the point of his shoe. His red sock is peeking out from a tiny hole near his big toe. It's such a contrast to how grand everything and everyone looked in there. It's making him feel like shit. He's maybe feeling a tiny bit guilty for trapping Castiel like that too. He doesn't seem like a bad guy, albeit one with a psycho mom.

Cas turns on him, eyes glaring and mouth open in what will probably be a flow of reproaches. He stops himself before he says anything though, seeming to deflate. He closes his eyes and takes a deep breathe instead, shoulders falling. "I'm sorry. You're right. I should be thanking you. I have no right to make you any reproach when I brought this on myself."

"It wasn't so bad, though, was it? I mean, I think I sold it?" Dean asks, a little hesitant. He even used pedantic talk and everything. 

"You did as well as could be expected."

"That's not much of a compliment…". 

"I shouldn't take more of your time," Cas apologizes, taking his wallet out. Dean goggles at the amount of cash in there. 

"You really shouldn't have that much cash on you, that's, like, asking for trouble."

Castiel squints at him like he's wondering if that means Dean is gonna rob him for a moment, before he hands him a wad of cash. 

Dean's eyes bulge out, "That's way more than five hundred dollars."

"There's also an advance in there to buy some clothes for the engagement party."

"The what now?" Dean blinks dumbly for a second until his brain catches up to what is happening. "Dude, no, I'm done!" 

"You were the one to push it so far in the first place," Castiel reminds. Accuses, really. 

"I just wanted to eat fancy food, okay! Not, like, go steady."

"There will be lots of food at my sister's engagement party," Castiel tries to persuade. Badly. 

Dean gives him a nonplussed look. The cash feels heavy in his hand. He's never had so much before. This could help him get a new start. What's a night of playing Downton Abbey compared to the many many nights he might not have to freeze his ass off in the backseat of his car thanks to it?

"Why are you even doing this anyway? And why would you choose me? Do I look that desperate for cash?"

"No," Cas says after what's definitely a too long pause. Dean scowls. "You were in front of me in the coffee shop line. I heard you talking on the phone. You said you needed some cash to buy a new outfit for a job interview. Begged, really."

"Where the fuck do you get on listening in on other people’s conversation?" 

"I didn't listen, I just heard."

"You know, what? Fuck you," Dean spits, "I don't need that bullshit in my life right now." He has enough cash to get to Austin and replenish his stock of food, even buy some new clothes. At least this way he can keep his dignity rather than being insulted by a bunch of rich assh-

"Please," Castiel begs, following him as Dean storms away. "You don't understand…"

"Oh I understand perfectly," Dean says, stopping and turning around so brusquely that they nearly bump into each other. "You think you can shit on other people from your high horse and that they'll still do your deed for a few hundred bucks. Well, I'm not your freaking puppet, man."

"I have never shitted on any-" he stops himself with a frustrated groan, before turning on the puppy dog eyes. "Dean, please. Listen to what I have to say at least?"

"I know what you're gonna say. I've seen that movie before, Cas. You're going to bring me to that party, so you can parade me around like I'm some earned price or some shit. Meanwhile you get to appease mommy dearest and the clan of hyenas putting pressure on you to find a husband, while still having the satisfaction of giving them a huge fuck you by bringing a guy like me instead of the golden boy they're dreaming of."

"I-" Castiel stops himself, pursing his lips. "That's actually not that far from the reality."

"Of course it isn't. Told you, I've seen that trope before. Except this is real life and your plan sucks, so you can keep your money and I'll keep my dignity. Just grow a pair and tell them all to fuck off, will ya?"

"You sure do like saying that to people," Castiel sulks. "Are you sure you can't do it for me?" 

"Oh believe me I would love to tell your mom to fuck off, but I like my balls attached to my body, so that's a hard pass."

Castiel laughs slightly at that and Dean can feel his own anger start to abate at the sound. "Good self-preservation instinct on your part," Cas mumbles. The puppy look is still there, except now it's making him feel like he's kicked the puppy.  

"You know, we're in the 21st century, right? You shouldn't feel pressured to the point of inventing a boyfriend. Who gives a shit about that nowadays?"

"My family does," Castiel answers in a long sigh. "You don't get it, how could you... I have three brothers, Dean," Castiel explains. "Two sisters. My little sister, who is just nineteen, just got engaged. I was already seen as the irremediably unwed one and now I…," he pauses, sending a nervous look at Dean, looking ashamed.

"Oh come on. How hard can it be? You're rich, objectively good looking. Do you have weird kinks or something?"

 "I-I wouldn't know. I've never even been in a relationship before," he confesses, looking at the ground.

"When you say 'relationship', you don't mean you've never…" Dean inquires. Cas' cheeks redden, and Dean blows like he just got punched. "Wow. That sucks."

"Yes, it's very pathetic."

"What? Eh no, it's not pathetic. Surprising, yeah. But, to each their own, you know?"

Cas inclines his head like he's not sure he does know. 

"I'm sorry I tried to drag you in all of this. You seem like a good man. You don't deserve-"

"-to be served on a platter to your family?" Dean asks, searching Castiel's gaze until they exchange a smile. 

"Yes. That." The man is still looking dejected. The money is still in Dean's hand. That duck really was good. Damn it.

"The food better be freaking awesome," Dean relents with a frustrated grunt. Castiel seems instantly relieved. "And you're not pretty woman-ing me," he warns, pointing a finger at the other man. "I'm choosing my own clothes and I don't give a shit if I don't know which fork to use for fish."

Castiel's head is tilted and he's blinking owlishly, like he doesn't understand a word that Dean is saying. Figures. He's not sure how he could convince anyone that he's this dork's boyfriend, honestly. Naomi certainly looked like she wasn't fooled. 

"I'm sorry for the way my mother behaved toward you. I assure you, being yourself will be amply sufficient to the task."

"Dude, the way y'all talk, where do you come from, Victorian England?"

"I-I don't think I have English ancestry, no. Why?"

They blink at each other for some time. 

"I must be a freaking masochist."

Cas' face scrunches up even more in incomprehension. 

"Okay, let's be clear on one thing from the start. This is not a lifetime movie and I'm straight, so: no falling in love, get it?"

"I get it, Dean," Castiel nods. 

Well, that's it then, apparently Dean is going to a fancy engagement party with his new boyfriend. What a weird day... 

Dean was interrupted in his grumblings by a guy walking up to him and Sam. 

“Winchester, isn’t it?” The guy asked Sam, obnoxiously. 

Dean bristled. This guy didn’t even know Sam’s name. Douchebag. 

“Yes, sir, it’s Sam.” Sam stuck out his hand for the man to shake. The man accepted, giving it a sharp shake. 

Then he turned his hard gaze to Dean. 

“And who is this?” The man said with a subtle sneer. 

“Oh, this is my brother, Dean Winchester. Dean, this is my boss, Michael Novak.” Sam introduced them. 

Ah! The ultimate douchebag. 

Neither man offered a hand to shake. They’d sussed each other already. 

“And what is it you do Dean?” Because you certainly don’t belong here. 

“I’m a kindergarten teacher.” Dean said, proudly 

Michael’s face soured further (if that was even possible). 

“Don’t they say that teaching kindergarten is like glorified babysitting?” Michael chortled. 

Dean’s eyes narrowed. This guy was already skating on thin fucking ice. And that ice just cracked. 

“Listen here, asshole.” Dean pointed a finger at the suited bastard. He could see Sam cringe and look at the floor next to him. But nothing would stop him now. “My kids are awesome. I’m teaching them to be even more awesome adults when they’re older. I just hope none of them turn into jumped up douchebags like you.”

“Dean!” Sam despaired. 

“Sorry, Sam.” Dean mumbled. But he wasn’t sorry. Not really. He was only sorry that he’d embarrassed his brother. He would never apologise for defending his choice of career. 

Dean chanced a glance at Michael. If the dude was a cartoon, he’d probably have steam coming out of his ears right about now. 

“I’m going to the bar.” Dean murmured, leaving Sam to apologise on his brother’s behalf. 

Dean hoped there wouldn’t be consequences for Sam after his outburst. He just hated it when people looked down on other people for their jobs. Basic respect for others was something he prioritises with his kindergarteners. It was a shame that some adults couldn’t seem to grasp the concept. 

He walked through the crowd of guests like a storm cloud towards the bar. 

Luckily, it seemed most of the attendees were relying on the waiters for their drink orders meaning the bar was empty save for the bartender. Dean slumped onto one of the stools. 

“What’re you after, Brother?” The guy asked as he made his way over to Dean. 

“Whatever isn’t that fancy shit everyone else sees to be having.” 

The bartender, Benny his name tag read, laughed a deep, rich laugh. “I feel that. How’s a good, smooth whiskey sound?”

“Finally, someone talking my language.” Dean smiled. 

Benny passed him over a tumbler of gorgeous brown liquid. 

Dean lifted it in silent cheers and downed it in one go, sucking his lips at the sharp burn it sent down his throat. “Another one where that came from, dude.” Dean slid the glass across the bar top back towards Benny. 

“You sure, Brother?” Benny questioned. 

“Sure as shit. I gotta get through this night somehow.” Dean mumbled. 

“It can’t be that bad, can it?” A voice that wasn’t Benny’s (or Sam’s for that matter) appeared from Dean’s right. 

Dean turned his head to find a dude around his age looking back at him with distinctive blue eyes. 

The guy had on a suit and tie much like that other people in the room. But, the tie was loosened and curled backwards towards the end. His top button was undone and his trenchcoat that blanketed the whole outfit seemed as though it was barely hanging on to his shoulders. 

How come this guy could come dressed like that but Dean couldn't loosen the tie that had been strangling him for two hours already. (The dude looked like he’d just had seven minutes in heaven with someone in the cleaning cupboard for god’s sake!)

Dean was snapped out of his judgement of the guy in front of him by Benny placing a fresh glass of whiskey on the counter. The bartenders gave him a wink and looked slyly over to the trenchcoat guy still standing, leaning against the bar. 

What was Benny trying to say? 

Dean didn’t have long to think it over as the bartender moved away to collect dirty glasses at the other end of the bar, leaving Dean and the trenchcoat guy alone. 

“So,” Trenchcoat Guy continued, perching himself on the seat next to Dean, “what are you doing here if this evening is so torturous to you?” The words were said, not with bitter condescension like Michael might have asked, but, it seemed, with genuine interest. 

Alright, Dean could play ball. Plus, this guy was hot. Dean would be thinking of a flirtatious answer if he wasn’t conscious of embarrassing Sam again by hitting on someone who is probably one of his co-workers.

“I’m here with my brother, Sam.” Dean explained. “He’s just started as an intern here. Wouldn’t kill the bastards to pay him though, he works harder than any kid I know.” 

Dean winced. He has gotta stop insulting the people Sam works with or for. 

“And I take it, this isn’t your usual environment to socialise in?” Trenchcoat Guy enquired. 

Dean huffed a laugh. “You could say that. Turns out I don’t so much enjoy being looked down on for my job, no matter how much I might love my brother.” 

Trenchcoat Guy frowned. “What happened?”

“Some dude called Michael made a dick comment about me being a kindergarten teacher. Told him exactly what I thought about his opinion and embarrassed my brother in the process. So I sought refuge at the bar.” 

Blue eyes darkened. “That’s appalling! I’m sorry that happened.” Trenchcoat Guy placed an earnest but comforting hand on Dean’s. “Being a teacher is incredibly admirable. You’re helping to shape and guide future members of society.” He assured. “There’s nothing more noble than that. Definitely not a lawyer who seems to see the money before the client.” 

Where had this guy come from? He seemed a little weird and dorky but also genuine and caring. 

Dean shrugged off the compliment. Just because he wasn’t okay with people disrespecting his job, didn’t mean he was comfortable being showered with praise and kind words. 

Instead, Dean flagged down Benny and asked for a beer, looking to Trenchcoat Guy to silently ask if he’d like one too. Trenchcoat Guy nodded. 

The two men kept eye contact as they took the first sips of their beers. Dean’s eyes fell to the way the guy’s lips shaped around the lip of the bottle. He flicked his eyes up again to find the guy had seen the movement. He knew exactly what he was doing to Dean, if the way he slowly licked lingering droplets of beer from his bottom lip was anything to go by. 

Any other day, any other time and Dean would have jumped at the chance to, well, jump this guy. But, he wouldn't do that to Sam. 

Instead, he cursed the fates for sending him this awesome guy at exactly the wrong time. Taking another sip of his beer, he moved to get up from his seat. He’d better go find Sam and check he hadn’t ruined his brother’s position in the company. 

He was about to open his mouth to bid the beautiful stranger goodbye when the guy’s eyes left Dean’s and locked onto something over Dean’s shoulder. The blood seemed to drain from his face. Frantic blue eyes snapped back to Dean’s.

“Kiss me.”

“What?” Dean asked, confused at the turn this had taken. He could feel his resolve slipping. Sam’s reputation be damned. 

The guy didn’t answer. 

Suddenly, his hand was on Dean’s cheek and he was placing a deep kiss on Dean’s lips. 

Dean had no idea what was going on but his night had improved dramatically in the last three seconds so he definitely wasn’t going to complain. He placed a hand on the guy’s waist, pulling him in closer to his own body. 

After a few heated moments, the guy pulled away. Though Dean kept the hand on his waist so he couldn’t move far. He wasn’t letting him go any time soon, that was for sure. 

“I’m sorry.” Trenchcoat Guy panted, chest rising to gulp down air that he’d been deprived of. “My assbutt of an ex was coming towards us.” He tried to step back out of Dean’s embrace. 

But Dean held his grip firm. 

“No need to apologise, dude.” Dean assured. 

Looking into the guy’s eyes, feeling his moving chest against his own, Dean could feel his will power slipping. 

Screw it. 

Dean pressed his forehead against the other man’s. “Stop me if you don’t want this.” He whispered before he placed his lips over the other man’s.

The kiss was deepened instantly. By who Dean wasn’t sure but at this point, he really didn’t care. 

Dean allowed himself to be manhandled against the bar, never breaking the passionate connection he had with this wonderful stranger. 

As if the guy could read his mind he softened the kiss to whisper briefly against Dean’s lips. “I’m Castiel, by the way.”

Dean’s brain was so preoccupied that he could barely stutter out his own name in return. 

“Hmm.” Castiel hummed against Dean’s lips. “I don’t want to be presumptuous, Dean. But I’d very much like it if you took me home. Right now.” 

They broke apart and Dean looked into Castiel’s eyes. The calm blue from before had been replaced with seductive black. 

Yep. This was definitely happening. 

“Let’s go.” Dean grabbed Castiel’s hand to drag him towards the exit. 

But Castiel stopped him. 

“What about your brother?”

Shit. Trust his downstairs brain to throw logic out the window and forget about his brother. 

But he dreaded seeing the look of disappointment on Sam’s face when he told him where he was going. And who with. 

“Don’t worry, Brother.” Benny’s voice spoke up from the bar. “I’ll find him and let know you’ve gone home.” 

Dean shot Benny a grateful look. “Thanks, man.” He tried not to weirded out that Benny had seen what had just gone down. 

He once again grabbed Castiel’s hand and tugged him towards the nearest exit. 

Once outside, Dean hailed a taxi. He would have loved to have shown Castiel his beautiful 67 Impala but he’d had a couple of drinks and there was no way he was going to risk driving home. Plus, even without the drinks, he wasn’t sure he’d be able to keep his hands to himself long enough to get back to his. 

As soon as they made it through Dean’s front door, he sobered slightly. As respectful and understanding as Castiel had been earlier, he was clearly used to the finer things in life if he was at the firm party. Dean and Sam’s apartment was a far cry from that. 

“It’s not much…” Dean explained. 

Castiel turned from where he’d been doing a quick scan of the main room to lock eyes with Dean. “The only thing I’m concerned with right now is where your bed is.”

Dean could only point towards the corridor leading to his room. 

Castiel gave Dean a dark look and pulled him along by his tie. Maybe ties weren’t so bad after all. 

*  *  *

The next morning, Dean awoke to the feel of bare skin against his own. 

The body on top of his shifted and he could feel a rumble travel up through it. 

“Good morning, Dean.” Castiel hummed. 

“Mornin’, Sunshine.” Dean sighed, nuzzling into Castiel’s dark hair and placing a kiss against his temple. 

Dean was about to suggest breakfast when he sensed the stomping moose steps of Sam coming down the corridor outside his room. 

“I don’t care if you’re hungover, I’m shouting at-” Sam stormed into the room. But he was cut off by the sight in front of him.

Dean cringed. Benny obviously hadn’t told Sam everything when they’d left last night. 

“Oh my god! Mr Novak!” Sam snapped himself back to reality. 

Dean turned to look at Castiel. Mr Novak? Was Castiel one of the stuck up sons of bitches sitting on a heck ton of money and not giving any of it to hard working interns like Sam? 

“Hello, Samuel.” Castiel greeted, lifting himself to sit against the headboard. “You can call me Castiel. I feel as though we’ve moved past the normal professional relationship now.” 

“Okay, Castiel.” Sam was clearly still in shock. “I’m just going to leave now.” He cleared his throat awkwardly and then ducked out of the room, closing the door softly behind him. 

Dean turned again to Castiel. “Okay, what just happened?” He asked, completely confused as hell. 

Castiel placed a hand on Dean’s. “I’ll explain everything but I think you need to go and make sure your brother is okay.” 

Dean was unsure. He didn’t want to just leave Castiel in his bed alone. 

“Go, Dean. I’ll wait here for you.” Castiel said, sensing Dean’s apprehension. 

“Okay.” Dean submitted, quickly pecking Castiel on the lips before getting up from the bed, throwing on some boxers and leaving the room. 

It wasn't until he was closing the bedroom door behind him that Dean realised he’d just kissed Castiel goodbye like they were boyfriends or something. 

Way to go, Dean. Scare the dude off before anything had properly started. 

Anyway, one problem at a time, he thought as he rounded the corner to find Sam pacing the length of the living room. 

“So…” Dean began, awkwardly. 

“I can’t believe you, Dean.” Sam said, angrily. “Did you not think of my career at all? Of all the people to go home with at that party, you went home with my boss?” 

Hang on..

“Boss?” Dean asked, “I thought that Michael dude was your boss?!” Dean said, confused as hell. 

Sam ran his hands through his hair in a frustrated manner. “I’m an intern, Dean. Practically everyone in the damn company is my boss. And Castiel? He’s the boss.”

Dean paled. “What?”

Sam sighed. “He runs the whole damn thing! Didn’t you see the news a couple months ago? His dad died and left the whole firm solely to Castiel. It created a big stink because his brothers, including Michael Novak, didn’t get a look in. They’ve been contesting the will for months now.”

Dean slumped onto the couch. He couldn’t believe it. Castiel had lied to him? Well, maybe not lied, just didn’t tell the whole truth. 

Sam saw Dean's mood suddenly turn and frowned. “You really didn’t know?” 

Dean silently shook his head. 

“I’m sure he has his reasons for not saying anything.” Sam tried to reassure his brother. 

Dean waved it off. “Don’t worry about it.” He said. “Yeah, I really like the guy, but once he realises who he shacked up with, he’s not gonna hang around.” He shrugged, accepting the situation for what it was. 

There was no way someone like Castiel, with that amount of wealth and riches, would be interested when he understood that Dean was a grown man who still lived with his little because they couldn’t afford much else right now. 

“Why don’t you let him decide that for himself?” Sam asked, pulling Dean from his negative thoughts. “All I know is, I’ve only met Castiel a handful of times but he’s only one of the Novak brothers that has ever tried to even learn my name.” 

Dean was torn. This was such a big thing for Castiel to neglect to mention. 

“Man, I don’t know. This only started because he was hiding from an ex at the party.” Dean explained. “And now I say it out loud, it sounds like a lie. God, I’m so stupid.” He dropped his head into his hands. 

“Damnit, Dean!” Don’t you ever watch anything on TV other than Doctor Sexy?” 

Huh? Dean shot his brother a confused squint. 

Sam shook his head in exasperation. “Even before their dad dying and the inheritance fiasco, the Novak brothers have always been sort of minor celebrities - comes with the money I guess.” Sam explained. “All I know is that he did have what the media called a ‘messy break up’ with a guy who worked for the company. And he was definitely at the party last night.” 

Dean sighed. He didn’t know what to think. 

“Look, Dean. You clearly like this guy already. He’s literally in your room waiting for you. Go talk to him.” 

Dean nodded and stood up, taking a determined breath. 

Sam gave him a supportive pat on the back. 

Just before he left the room, Dean turned back to his brother. “Are we good?”

Sam smiled. “Yeah, man, we’re good.”

Dean nodded and left. 

When he re-entered his room, Castiel was still sitting in Dean’s bed, picking at a thread in the covers. He looked up at the sound of the door clicking shut. 

“How did it go?” Castiel asked, patting the space next to himself, silently asking Dean to join him again. 

Dean sat on the bed, but he didn’t get back under the covers next to Castiel. He still wasn’t sure what to do. “It’s okay. We smoothed everything out.” Dean nodded. “Found out some stuff about you though.”

Castiel nodded in understanding. 

“Why didn’t you tell me you were the boss? My brother’s boss?!” Dean asked, pleading for an explanation. 

“I wanted to come up to you. I’d already seen you from across the room earlier and when I finally gathered the courage to come up to you, you were complaining about my party and clearly had no idea who I was.” Castiel explained. 

Dean flushed. “Sorry about that.”

“Don’t be sorry, Dean.” Castiel reached over to take Dean’s hand in both of his. “It was refreshing. With everything that has been going on recently, it was nice to have a break from that. And then my ex-boyfriend was coming towards us. And, well, you know the rest…” Castiel trailed off. 

“The douchebag who everyone seems to know about except me.” Dean added. “He sounds like a son of a bitch.” 

Castiel hummed in agreement. “That’s an understatement.” He muttered. “I found out Bart was sleeping with someone else a few months ago and I ended it immediately.” Castiel paused at Dean’s whispered ‘bastard’. “However, when my father died, he tried crawling back. He was probably after my new wealth and position in the company. I, of course, rejected him. But, Bart is the kind of person who doesn’t take no for an answer.” 

Dean scowled. He may have only just found out the diner details, but he wouldn’t hesitate to punch that dick in the face if he ever saw him. 

Taking in Castiel’s downtrodden look, Dean sighed. “I understand all of that Cas. But you heard me last night. You run the show and you seem like a decent guy but how can you have hard working interns like Sam and not pay them a cent? While you sit on a literal throne of money?” 

Dean looked down at his lap. He wasn’t sure he was going to like whatever Castiel had to say. 

“Dean,” Castiel lifted Dean’s chin to make the man look at him, “I completely agree with everything you said. That’s one of the reasons my father left everything to me.” Castiel explained. “He knew I had new ideas for the company. He knew it was only a matter of time before he had to hand it over to his sons. So he left it all to me on the sole condition that I go ahead with the changes that I wanted to implement.” 

Dean let out a breath and smiled. Okay, this sounded good. “What, uh, kinda stuff are you changing?” 

“Firstly, we’re going to be taking on a lot more pro bono cases. We are sitting on a throne of money, as you say,” Dean blushed, “and it’s time we actually did something good with it.” 

Dean nodded. Now Castiel mentioned it, he remembered Sam saying something about that when he’d first joined Novak & Sons.

“And,” Castiel continued, “though it hasn’t been announced to the public or even the employees themselves, interns will be getting a competitive rate of pay. You’re right. They do work hard for us and they deserve to be properly credited for it.” 

Dean certainly hadn’t expected that. He’d expected Cas to say that it was out of his hands, or just simply that’s how things worked there. 

“Now, can you please say something? I’m worried I’ve ruined this before it could even begin.” Castiel asked, shyly.

Dean smiled softly. “As long as you don’t mind slumming it with someone like me, I only have one more question.” Castiel nodded. 

“Can I kiss you?”

Dean would give anything to never see that smile leave Cas’ face. 

Instead of answering, Castiel pulled Dean towards him by the shoulder. The smile didn’t leave his face as Dean pressed a long, sweet kiss to his lips. 

“I hope you’re ready,” Castiel said later after they’d parted for breath, “making out with the boss last night would have made quite a spectacle.” 

Dean made a noise of indifference just as Sam shouted from the living room. “Woah, dude! You’re on the news making out with Castiel!” 

“Told you.” Castiel said, triumphantly. 

Dean just laughed and pulled Castiel back in for another deep kiss. 

*  *  * 

They still had a few issues to iron out before they embarked on a relationship, but in the end those issues seemed like small bumps in the road and it was a smooth ride after that. 

Despite his brother’s relationship with the boss, Sam was treated no differently to anyone else. It was important to Castiel to make it clear that any achievements Sam had were entirely down to Sam himself and he had not been handed anything under family privileges. 

And Sam’s hard work paid off. Within a few years, Novak & Sons had another major overhaul and became Winchester & Novak. (Castiel’s brothers had had something to say about, but as he’d been doing for years until that point, he just ignored them.)

Though, it was only a few months after the changes that Dean asked Castiel how pissed off his brothers would be if it was changed again to Winchester & Winchester. Castiel had just laughed and let Dean place the ring on his finger. 

(Turns out, his brothers were extremely pissed off. Oh well.) 

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A/N: I hope you enjoyed it Daria! It ended up being longer than I expected but I’m quite happy with how it turned out.

If you liked what you saw, REBLOG! and consider reserving a prompt from my ‘30 Destiel Prompts’ challenge, or just send me your own prompt you’d like me to fill!

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