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castielific · 4 years ago

Text

Title: Fancy and the tramp

Story status: Complete, 8 chapters

Rating: Explicit

Tags: Dean/Castiel, Alternate Universe, Fake boyfriends, pretend relationship, homeless!Dean, rich!Cas, family, angst with a happy ending, temporary breakup, getting back together, coming out, past!homophobia, self esteem issues, Dean Winchester has a sexuality crisis, first time, homelessness, bed sharing, pining

Sex tags: anal sex, switching, bottom!Cas, bottom!Dean, first time, frottage, marking, blowjob, fingering, barebacking

Special warning: Contrary to what the title may presage, there are no spaghettis in this story.

Summary:

"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 fake boyfriend. What a weird day.

Link to AO3

Chapter 1 under the cut:

************

"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...

You can read the rest on AO3

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