A/N: Hey folks! I haven't published anything in five-ever, so howdy to those of you who remember me! Welcome to an EXTREMELY ill-advised new fic that will probably be super long and pretty angsty but then everyone will hug and crowds will cheer and the kids will make enough money to save the skate park from demolition and Lady and Tramp will have four puppies, three girls and one boy, and the boy one will look *exactly* like his rascally father.

Okay, so I'm exaggerating. But you get my drift.

I'm in my last year of law school, about to start my last quarter ever, and I am in the throes of finals but for some unknowable reason I decided to start writing this story. It's loosely inspired by the movie Arthur, but it ended up being preeetty different. Basically, the premise is that John Winchester was a gajillionaire who died and left all his money to his sons. Sam is pursuing a career in politics while Dean is pursuing a career in doing absolutely nothing with his life except drink and sleep around. With Dean's behavior getting more and more out of control and Sam's campaign for Congress approaching, Sam hires a ~*~ mysterious guy ~*~ to basically be Dean's nanny and keep him in check. Spoiler alert: IT'S CAS! And things go from there. You'll see. This is a Dean/Cas story, but I feel in many ways it is as much about Sam and Dean's relationship and them figuring out how to get back to brotherhood. I wanted to play with their dynamic in an AU setting where they have very different lives than in canon. I've also messed with Cas' life a bit, and that influences his personality - but again, you'll see. No more insider scoop! I've said too much already!

I also want to mention that this was originally two chapters, but the first section was pretty short and felt incomplete as a first installment. You'll see where the chapter break would have been, and I just want you to see that and appreciate that I GAVE YOU MORE.

Thank you for clicking, and I hope you enjoy the chapter! If you do, please review. If you review, I promise I will send you Jensen Ackles' personal phone number and a list of all the people you could pretend to be for at least 5 minutes of conversation before he would figure it out.* Enjoy!

*Author does not have ability to fulfill this promise. Author apologizes for her lack of celebrity connections.

In a king sized bed, in an enormous dark room, with the daylight shut out by thick red and gold brocade curtains and the scent of citrus and sweat still lingering in the air, Dean snores.

His phone rings.

Dean snorts awake. He reaches out to grab his phone and his hand lands on the face of a passed-out supermodel, who groans in her sleep and rolls over, dragging the gold satin sheets with her. He fumbles his way over her and grabs his phone, only to have the model on his other side sit up and try to snatch it from him. "Turn it off!" she whines, all bedhead and smeared makeup.

"I'm trying!" he growls. He manages to unlock the screen and answer the call. He scowls and holds it to his throbbing head, then answers groggily, "911, what's your emergency?"

"Where are you?" Sam snaps. "Did you forget about the meeting?"

"Board of trustees?" Dean rubs his eyes. "That's not until 2."

"It's 2:17, Dean."

"Sheeeiiiit." Dean looks to the woman on his left, then to woman on his right. "Guess I'm not gonna make it, then."

"Dean! These people are in charge of your money!"

"I got my best brother there to look out for me!" Dean replies breezily. "Sides, you're better at the money stuff than me, Sammy."

"It's Sam."

"Just make sure that plenty of my assets are available, alright? I ran out of tequila yesterday – well, technically, the three nearest liquor stores ran out – so I'll be sending Jeff out for a supply run today."

He can almost hear Sam's frown. "Dean."

"It was a party! I was hosting! It's not Fashion Week every day. Jeez, unclench a little, Sammy."

"It's Sam."

"Anyway, I gotta go, I gotta piss like a racehorse –"

"This is it. I'm hiring you a handler."

Dean freezes. "What? Sam, I am way too old for that shit."

"Apparently not!" Sam's voice is firm, resolute. "You've been blowing me off left and right, and my campaign manager has been pressuring me to do this for months already. You're getting a handler."

"You can't just – just decide that!" Dean argues. "I'm an adult, I say who is or is not in charge of me!"

"Well, right now, I'm downtown with board of trustees, and you're not. So you can either accept a handler and do exactly what he says, or I can make a stunning, eloquent speech about all the reasons your distributions should be cut back for the foreseeable future."

Dean squeezes his eyes shut. "Sam. Please. Come on. I – I can do better."

Sam pauses.

"Fine," he finally says. "You have a week to show me you can be an adult. One week. You need to grow up, Dean."

"Peachy," Dean barks, and he hangs up.

He throws the phone into the nearby ice bucket, which is now just full of melted water. "Bitch," he mutters.

The woman on his right rubs his shoulder. "Hey baby," she says soothingly, "let's have some breakfast."

"Alright," Dean sighs. "But not until I get a drink."

….

Dean wanders around the mansion in his boxers and a smoking jacket with a bottle of whiskey in his hand. He stop every so often to admire some artwork and take a swig. "Don't remember buying that one," he mumbles several times. He runs into his head chef Jeff in the kitchen, and directs him to make breakfast for the girls and anyone else who might be sleeping it off around the estate.

He grabs a cigar from the foyer and makes his way down out to the back lawn. The afternoon sun sears brightly into his eyes and pricks at his skin; he winces and squints. He pats his pocket for his phone so he can call Louise and have her bring his sunglasses, and then remembers what he did to his phone. "Mistakes," he mutters. "Mistakes were made." He stumbles back inside.

He plays videogames for a couple of hours.

He gives a tour of the menagerie and introduces the girls to his tigers. "I tried playing Eye of the Tiger for them once," he tells them. "They were not fans."

One of the girls wants to screw again, and he gladly obliges her. He takes her down to the theater room and tells the kid at the projector to run Rocky Horror Picture Show again, and they fuck to the Time Warp, which is pretty awesome.

He finishes his bottle of whiskey. Allie brings him a Bloody Mary, because she knows it's the only way he'll eat any vegetables. She also brings him a new phone.

He finishes his Bloody Mary and takes a bath with three more models he found upstairs in the library. He's a little too drunk for sex now, but he makes a valiant attempt. The girls coo and reassure him. He hops out of the bath and throws on a blue terry bathrobe. "Time for lunch!" he shouts, pulling a bottle of gin out of his bathroom liquor cabinet.

Lunch is burgers and steak fries ala Jeff. The models glare at him enviously as he wolfs down his burger, and ask the server if they can just have salad. He grins with a mouth full of half-chewed beef.

After lunch, he lays on the sofa and watches reruns of A-Team with a beer in his hand. The girls lounge around him in various states of undress.

"I'm bored," he announces.

"Karaoke?" one model suggests.

"Let's go swimming!" another pipes up. "Where's your pool?"

Dean sits up, and smiles broadly at the would-be swimmer. "My pool? Babe, I've got a jet. My pool is the ocean." His smile falters. "I mean, okay, I've also got a pool, but… you get my point."

So they fly to Dean's island just off the coast.

They swim and eat barbecue and drink champagne and sun themselves on the beach and until it gets dark, and then they fly back to the estate. Several of the girls leave, and as they make their goodbyes, Louise slips discreet folds of hundred dollar bills into their hands as party favors, just as instructed. Dean pretends not to notice.

"Let's partaaaay!" he hollers to the remaining girls.

They all pour shots down their throats and pop pills and snort lines of coke off his mirrored bedroom table, and Dean is so high and drunk and horny all at once that for a moment he thinks he might actually be happy.

Then he hears it.

This is it.

You have a week to show me you can be an adult. One week.

The memory plays in his head without warning. Sam's voice, dripping with disgust. You need to grow up, Dean.

One of the girls, a redhead, paws at his crotch and licks the side of his neck, and the sensation sends a slick of nausea down the back of his throat.

"I need some air," Dean mumbles. The room tilts and swirls around him.

Sam's voice, dripping with disgust. Grow up.

He walks down the hall and the girls trail after him, laughing and chattering. The laughter is bubbling and contagious, a reflex, a hiccup, a mirror, stimulus response stimulus response and it boils up inside of Dean until he is giggling and giggling and giggling and the sides of his stomach beg him to stop.

Allie sees him and knows where he's going. She tries to tell him he can't. He shoves her off of him, shoves her so hard she falls to the ground. "You're fired!" he declares. The cascade of his own laughter rings in his ears. Grow up.

He makes it to the garage before anyone else catches him. Grow up.

He fumbles with the keys, trying sluggishly to slide them into the lock. Grow up.

Four girls squeeze into the convertible. Grow up.

He peels down the front gravel drive, pedal to the floor, roof down, girls screaming in delight, wind in his hair, laughing so hard it hurts, so hard he's wheezing, so hard his throat burns, lights and landmarks streaking by him so quickly they are smears in his vision, a blur, his head buzzing and his heart thumping in his white-knuckle clenched hands, and he doesn't need a week, doesn't need Sam, can't shake that voice in his head grow up you fuck-up you fuck-up you worthless piece of shit, and he sucks in his breath to keep it all in, gasping, and he whizzes by the other cars and he chokes and he starts sobbing, sobbing, and he closes his eyes –

...

...

...

...

Sam Winchester sits across from Castiel, leafing through his application. The young politician is everything Castiel expected – crisp, warm but formal, eager to gladhand. His hair is parted to the side and combed back in a way that suggests John F. Kennedy, and even in his brother's home his tie is knotted snugly against his buttoned collar. The room, too, is much what Castiel expected; the parlor is a tasteful pastel green, with finely upholstered mahogany chairs and matching tea table. All of the pieces look brand new. Sam's doing, most likely.

"I really appreciate you coming out here," Sam says. "Zach had only great things to say about you."

Castiel says nothing.

Sam looks up from the papers. "You have quite an impressive resume, Castiel."

"Thank you," Castiel says.

"Can I ask –" Sam hesitates. "Castiel, you're overqualified. This position is for – well, you'd be a glorified babysitter. Why do you want to take this job?"

Castiel clasps his hands. "I'm between projects right now. I like to keep busy."

Sam nods hesitantly. "I see…"

"You're also offering seven times the salary I normally make," Castiel adds.

Sam chuckles and stacks the papers together. "Oh, when you meet him, you'll see why. Dean is…. He's kind of a handful."

Castiel cocks his head slightly, unpacking the phrase in his mind. "If you could describe your brother in one word," he says, "what would it be?"

Sam looks surprised, then considers. "I'd say…." His mouth twists, and he rakes his hand through his hair. "Well, to be perfectly honest, I'd say… self-absorbed."

Castiel stands up. "Thank you. When will I hear back from you?"

Sam stands up quickly. "Whoa, whoa, wait, don't you want to meet Dean before you go?"

Castiel purses his lips. "If you think I should."

Sam steps closer and claps him on the back. "Believe me, you should know what you're getting into."

…

The estate is large, and the parlor is far from their destination. On the way, Sam talks.

"I don't know how much you know about Dean's situation," he begins. "I'm guessing you've done your research, but… I'll give you a quick rundown from the inside. You heard about the crash?"

Castiel nods.

Sam's jaw tightens. "Thank God no one was seriously hurt. It was Dean's first DUI, so he only had a day in jail. And he had to complete an alcohol treatment program to ever hope to ever get his license back. He had to wear one of those SCRAM bracelets that measures alcohol intake, so he's definitely been dry these past three months, but…" Sam glances sidelong at Castiel. "He finished the program yesterday, and they took it off. So I'm not sure how long he'll be sober." He scratches the back of his neck. "But who knows. Maybe…" He trails off, his eyes growing distant.

Then he blinks and coughs self-consciously. He walks a little faster.

Castiel surveys the high-ceilinged foyer as they pass through, peering up the velvet-carpeted horseshoe staircase towards the dark bedroom hallways. "What was your father like?"

Sam looks taken aback, and starts walking up the stairs. "Our dad? He was… just about everything Time Magazine said he was. He started as a college dropout working out of his garage. He formed the company just before I was born, and I was only in second grade when they went public. He was a millionaire overnight, a billionaire pretty quickly after that, and the company exploded. Dad was brilliant, but more than that – he was incredibly driven. He worked eighty hours a week and never let up." Sam huffs a sarcastic laugh. "And that's exactly what killed him! He could never stop going. He never listened to us."

They reach the top of the stairs. Sam turns to Castiel. "Why do you ask?"

"I always ask. Knowing information about the family background helps me to understand the client," Castiel explains.

Sam frowns. "But you didn't even want to meet Dean."

Castiel stares at him evenly. "You are the client, Sam."

Sam blinks. "What?"

"You are considering hiring me," Castiel says. "You are the person I must satisfy. It is important that I understand your goals and expectations."

"My goals –" Sam makes a noise of frustration. "Look, my only goals are that Dean doesn't kill himself or kill somebody else. I'd like to keep him out of the headlines if possible, at least until after the election, but that's incidental to keeping him safe. And if someone could get him to give a damn about something, anything, I'd be over the moon, but I've been trying for six years and nothing's worked so far." His nostrils flare, and his fists are tight at his sides. "I know what it looks like, but I'm not hiring someone for me, Castiel. I'm hiring someone for Dean."

The first surprise of the day. "I understand," Castiel replies, and he revises his mental assessment of Sam. "But then why did you wait so long to look for someone? It's been three months since the crash."

A flush rises on Sam's cheeks. "I, uh, I didn't wait. I've hired… four people so far. Couldn't get any of them to stick. Zach gave me your name when I told him how much trouble I was having."

"Why did they leave?"

Sam exhales. "I'm not exactly sure. Dean is annoying, but at the salary I'm offering – I grew up with the guy, he's not that annoying. I track his finances and I know he didn't pay them off, but I think he might have blackmailed them. He's pretty good at hacking into email accounts, and everybody has their dirt." He gives Castiel a calculating look. "He'll probably try the same thing with you. Got any skeletons you need to keep buried?"

Castiel gazes back at him evenly. "I don't think he'll find much."

Sam holds his gaze for a long moment, and then turns to lead him down the hall. "I think Dean's in the music room…"

The door to the music room is large and black. "It's soundproofed, so… brace yourself," Sam warns.

He opens the door.

The wall of sound hits Castiel in the pit of his stomach, thumping in his bones and vibrating through his chest. Instruments are scattered throughout the room – grand piano, cello, pipe organ – and in the back is a small stage, where a five-man band is plugged in and playing classic driving energetic rock music. Drums, synthesizer, electric guitar, electric bass, all dressed in black. Castiel recognizes the song as "Juke Box Hero" by Foreigner, and recognizes the man next to the guitarist, holding the microphone stand close in one hand and singing at the top of his lungs.

His sleeveless black shirt accentuates his tanned, muscular arms; acid washed jeans, bare feet, and his gelled-up hair complete the costume. He has dressed for the part. Dean leans into the mic and belts the second verse. "In a town without a name/ in a heavy downpour/ thought he passed his own shadow/ by the backstage door!"

Sam and Castiel approach the stage. "Dean!" Sam shouts. "Dean! Stop the music!"

Dean sees them, and yanks the microphone out of its stand. The band is perfectly in tune, and the music pounds relentlessly through the amplifiers. "Like a trip through the past!" he screams into the mic. "To that day in the rain! And that ONE guitar!" He locks eyes with Castiel, and winks. "Made his whole life change…"

A strange thrill courses through Castiel, and the hairs on his arms stand up.

Unexpected.

"Now he needs to keep rockin', he just can't stop!" Dean points to Sam and bangs his head to the beat. "Gotta keep on rockin', that boy has got to stay on top!" He jumps in the air in time to the chorus. "And be a JUKE! BOX! HEROOOOOO! GOT STARS IN HIS EYES!"

"Dean!" Sam yells. "I don't have all day!"

"JUKE! BOX! HEROOOOOO!"

"Dean!"

"JUKE! BOX! HEROOOOOO!"

Sam walks up to the large speakers and yanks the plug out of the wall.

The band clatters to a stop, and Dean shoves the mike back in the stand. "Whoa, whoa, whoa!" he yells, jumping off the stage. "This is sensitive equipment, Sam!"

Sam narrows his eyes. "Yeah, I think you can afford to replace it."

Dean wipes the sweat from his brow with his forearm and glares at Sam as he catches his breath.

The tension between the two brothers is palpable. They stand five feet apart, and the air between them almost ripples with antagonism. Dean lifts his chin slightly, puffing up his chest, and then sways a little where he stands.

"Have you been drinking?" Sam asks sharply.

Dean shrugs.

Sam's mouth is a thin-pressed angry line, and his eyes shine bright and breaking.

Dean turns to Castiel and smirks. "Who's number five?"

"I am Castiel," Castiel answers.

Dean puts his hand to his chest with a theatrical flourish. "I am Dean."

"I know."

He looks Castiel up and down, and then looks at Sam as though suppressing a laugh. Then he coughs into his fist and frowns mock-seriously at Castiel. "So you're vying for the prestigious job of Dean Winchester's butler?"

"Not a butler," Sam cuts in.

"Bodyguard?" Dean suggests.

Sam snorts. "Seriously?"

"Personal assistant," Dean amends.

Sam sighs. "Sure."

"I am," Castiel answers.

Dean claps his hands and rubs them together. "Alright then. I have some questions for you. Do you like piña coladas?"

"No."

"Getting caught in the rain?"

"… No."

"Are you into yoga?"

Castiel frowns. "I fail to see how that is relevant to the job description."

"Ahhh, I'm so sorry, the answer we were looking for was 'not into yoga,'" Dean replies brightly. "Buh-bye, have a nice life, and don't forget to steal something on your way out!" He spins on his heel and goes to heave himself back on the stage.

"Wait." Castiel turns to Sam. "Is it alright if I speak to Dean alone?"

Dean stops and looks back over his shoulder.

Sam stares at Dean and puts his hands in his pockets. "I… suppose."

Castiel turns back to Dean. "Can we talk for a moment?"

Dean sighs and slides down from the stage. "Fiiiiiiiine."

…

The bedroom is large and cluttered. Castiel can tell that Dean has refused to let anyone tidy it. Magazines, DVDs, and video games are stacked on every surface; every piece of furniture has a teetering pile of gadgets or snack cakes or model cars balanced on it precariously. A mountain of clothing sits next to his closet door. Dean collapses into a bean bag chair and lays with his head thrown back, staring at the ceiling, refusing to look at Castiel. "What'd you wanna ask me?"

Castiel looks around at the room, cataloging its contents. "If you could describe yourself in one word, what would it be?"

Dean lifts his head up and smiles sardonically. "Adorable."

"What was your father like?"

He lays his head back again. "Busy."

"Is there anything you think I should know before I take this job?"

Dean lays silent for a long moment.

His adam's apple bobs along his outstretched neck.

"It was my first DUI," he says. "Wasn't the first time I've driven drunk. Not by a long shot." He shuts his eyes.

Castiel slowly steps closer, watching the way Dean's body tenses with every step. "Anything else?"

"I'll make your life hell." His voice is low and hoarse. "I will. And I'll laugh while I do, because I've got nothing goddamn better to do than fuck with you and drag you down into the slime and filth and watch you suffocate in it."

"Is that a threat?"

Dean's eyes stay shut. "It's a promise."

Castiel stands next to Dean and looks down at him, leaning directly over him, and then says his next words carefully and cleanly, like the glinting edge of a heavy knife. "Do you know who I am?"

Dean's eyes snap open.

"You are a man of incredible importance, Dean Winchester. You were born with great purpose into a world of opportunity." He doesn't waver in his gaze, doesn't flinch. "Until your father's death six years ago, you were poised to fulfill every hope, every expectation, every legacy given to you at birth, and instead you have chosen to live like this. To wallow in meaningless hedonism."

Dean's fingers dig into the bean bag chair.

"But the people I work for know that you still have the potential to shape the course of history. They sent me here to show you how, because that is what I do." He leans in closer and growls through his teeth. "Do you think I am impressed by your childish tantrums? Do you think that by screwing socialites and snorting coke you can shock me with your depravity? Dean, you have the power to build and destroy entire nations, and you are making model cars in your bedroom. You have not even begun to imagine what it would take to shock me." He bends down even closer, putting his hand to the right of Dean's head and bracing himself on the bean bag chair, breathing in Dean's sour whiskey breath, watching his pupils expand and contract. "You want to make my life hell? I welcome you to try." He drops his voice to a harsh whisper. "But if you want to break me, Dean Winchester, you are going to have to think. Big."

Dean stares up at him, and breathes, "Who are you?"

"My name is Castiel," he answers, "and I'm the man who's going to save your life."

Then he pulls back, stands up, and buttons his suit jacket. He walks out of the bedroom and closes the door behind him.

Dean remains frozen in place in his bean bag chair.

He doesn't get up for awhile.

…

"Thank you again for coming out," Sam says, leading Castiel to the door. "I'll get in touch in a couple of days and let you know, but honestly, I'm pretty sure that –"

Sam's phone rings. He pulls it out of his pocket and frowns; it's Dean calling. "Sorry, let me just get this real quick." He answers the call.

"Sam?" Dean asks, loud and frantic. "You still with that Castiel guy?"

"Yes," Sam answers. "Why?"

"Sam, Sammy, please, please do not hire him," he pleads. "The guy is a lunatic, I'm serious, he's fucking batshit crazy! Does he even have a last name?! Sam, he cornered me in my room and said he's working for the motherfucking Illuminati or some shit and then he threatened me –"

"Did you threaten him first?"

Silence.

"Goodbye, Dean." Sam hangs up. He turns back to Castiel.

Castiel's mouth turns up at the corners in the barest hint of a smile.

Sam slides his phone into his pocket and beams. "So, when can you start?"