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Roll With It

Summary:

For two years, Dean’s been slaving away beneath his boss – many label him a secretary, but he fucking hates that and feels like it only applies to someone wearing a pencil skirt, so he insists on his title of Executive Assistant. And for what? In the vain hope that one day he’ll manage to become an editor for Sandover Publishing, and that he’ll see the manuscript that he’s slaved over since college finally realized in print.

That’s the dream, anyway.

Right now, he’s fucking late.

Dean wants to be an editor. Castiel just wants to stay in the country.
‘The Proposal’ – as you’ve never seen it before.

Notes:

Shoutout to Makenna for ideas, beta-reading and just generally making sure this is perfect.

If all goes well, this should be a long fic. Updates will hopefully be somewhere between weekly or fortnightly.

Tags will be added as we go.

Hold onto your hats.

ETA: this fic now has art by the absolutely incredible Migglangelus!

Chapter 1

Notes:

(See the end of the chapter for notes.)

Chapter Text

Dean knows that his job is a necessary evil. For someone wanting to make their way up the corporate ladder to a position actually worth anything inside this stupid publishing company, they have to do the hard yards first.

It doesn’t mean he has to like it.

For two years, he’s been slaving away beneath his boss – many label him a secretary, but he fucking hates that and feels like it only applies to someone wearing a pencil skirt, so he insists on his title of Executive Assistant. And for what? In the vain hope that one day he’ll manage to become an editor for Sandover Publishing, and that he’ll see the manuscript that he’s slaved over since college finally realized in print.

That’s the dream, anyway.

Right now, he’s fucking late.

He’s running at full tilt through the New York traffic, mentally and occasionally verbally cursing out the frayed wires that had left his alarm clock blank and silent this morning as his tie flies out behind him. His briefcase smacks into the side of a newsstand as he takes a sharp corner and he barely has time to call out an apology before he’s pelting down the footpath again. Some people get out of his way, because no one wants to tangle with a crazy-looking man at ass-o’clock in the morning, but some need a little more encouragement. Dean is finally able to elbow his way to the coffee shop by the offices.

He pushes his way past the line, ignoring the grumblings and side-eyed glares he receives – he deals with much worse shit from his boss on a daily basis – and flashes a relieved look at the barista. Kaycie? Kaylee? He can’t fuckin’ remember, just pours the sugar on thick as he takes the two cups from her and sends a flirtatious smile her way. “Thanks, sweetheart, you’re a lifesaver,” he tells her before he’s off again, careful not to knock the coffee cups as he ducks out of the shop. In the state he’s in right now, coffee is more important than gold. Even if he’s taken to drinking the shitty unsweetened soy stuff that his boss favours, it’s better than nothing, and Dean can’t wait until he can finally get behind his desk and down his whole cup before his boss arrives.

No one bothers him in the elevator – everyone knows him, recognizes the fact that he’s carrying two coffee cups and shoots him a sympathetic smile – and he makes it to his floor with a minute to spare.

Which is why it stands to reason that, because the universe apparently has a cruel vendetta against a small town boy from Kansas who does not deserve this kind of treatment, he smacks into Andy from Marketing four paces out of the elevator.

His boss’s coffee splatters against his shirt, and Dean can only spare a second to stare dismally down at the spreading stain and think why me? before he’s whirling on Andy.

“Give me your shirt,” he growls, grabbing Andy by the collar and pulling him through to Dean’s own small office adjacent to that of his boss. He’s already stripping off his jacket and tie as he goes, because fucking hell there are not enough seconds in a minute, and he definitely turns some heads as he passes through the maze of cubicles.

Right now, he doesn’t have time to care. Twenty seven seconds later, Andy is scurrying out of his office wearing a coffee-stained white shirt, and Dean is shrugging his jacket on over a shirt slightly too small for him when his computer beeps.

It’s here.

Dean sucks in a sharp breath and scrambles to make himself presentable, because he’s not a fucking amateur and usually he’s more prepared than this. He can’t say the same for a few of his newer coworkers, who scurry out of Novak’s way like scared mice as the man appears out of the elevator, crossing the floor in long strides with his tan trench coat flaring out behind him. He watches from the doorway of his office as the rest of the poor souls on this floor attempt to look as though they had actually been working before Novak walked in, instead of standing around gossiping and sharing stories from the weekend. Dean barely gets a moment to find the situation amusing in a twisted kind of way before Novak is at the door to their offices, his expression surly as ever.

Dean reluctantly hands over the only remaining coffee, resigning himself to the shitty brew kept in the staff breakroom. It may taste like ass, but he’s desperate and he will not survive without it.

“Morning, sir,” Dean tells Novak in the most upbeat tone he can muster – he’s kissed ass to climb the ranks for two years, he’s not about to stop now – and follows his boss into his office.

“I’ve got manuscripts for you to look over and approve from Jeffords, I’ve moved your lunch meeting from 1 to 12:30, you need to call Mr. Devereaux to follow up on the media appearances,” Dean reels off as he sets piles of paperwork down on Novak’s desk, placing a handful of memos down on the desk in front of his boss and grabbing the sheaf of papers that have been neatly stacked in the ‘OUT’ box. “Hammersly from the Printing department wants your final opinion on one of the new series, and…” He rubs a hand across his stubbled jaw, then drops it, hoping Novak won’t notice that he didn’t shave this morning. What was that last thing? If he’d had his coffee this morning, he’d remember, and he glares bitterly at the cup in Novak’s hand. That is, of course, until he and Novak simultaneously spy the scrawled message on the side of the coffee cup, and Dean goes very still.

Novak peers at it, brows drawn into a frown.

“Who is Katie, and why is her number written on my coffee cup, offering a ‘good time’?” He draws finger quotes in the air with his free hand, and Dean blushes deeply. Time to come clean.

“That, uh. That may have been my cup. I may have spilled yours.”

Novak fixes him with a withering look, and it’s only two years of working under this impossible man that gives Dean the mental backbone not to shrink under his stare. His boss takes an experimental sip, then raises an eyebrow at Dean.

“You don’t seem like the kind of man to drink an unsweetened soy latte.”

Dean simply shrugs his shoulders, because yes, he fucking hates the stuff with a vengeance, but it’s even more pathetic to admit that he’s taken to drinking his coffee in the same style as his boss just in case this exact situation occurs.

Novak eyes him for a long moment, quite obviously not buying Dean’s bullshit, but eventually he returns his attention to the neat stacks of paper on his desk and sips at his coffee. Dean watches bitterly, craving caffeine in any shape or form and resigning himself to the breakroom brew as he sorts the papers from the ‘OUT’ box and retreats to the desk just outside of Novak’s office that he calls home. If anyone wants to get to Novak, they have to go through Dean first – which also means that Dean is the number one source of intel when it comes to the boss’s movements.

The dragon is in his cave, he types into the office chat, leaving the subsequent replies from his coworkers to cheer him up a little as he sits down and begins to sort through the outgoing paperwork. A few minutes later, Andy pops his head around the corner to Dean’s office, eyeing Novak’s closed office door with trepidation. “Dude.” He pouts, tugging at Dean’s coffee-stained shirt with distaste. “Am I getting a clean shirt any time soon, or am I stuck in this for the rest of the day? If Novak sees me, I’m fucked, man.”

That explains the numerous fearful glances he’s been shooting the closed office door.

“Here,” Dean sighs, digging into his pocket for the company credit card that he uses to run Novak’s errands. No one will notice one small purchase. “Go buy yourself a cheap shirt. And could you get me a coffee, while you’re at it?” By this point, Dean’s craving the stuff. He holds the card out to Andy, who scampers across the threshold to take it from his outstretched fingers.

The office door swings open.

Again – cruel universe, small town boy from Kansas, Dean doesn’t why it’s continuing to fuck him over. This day could not get worse.

Andy meekly takes the card from Dean’s hand and does his best to surreptitiously push it into his pocket – not that that will help them now. Novak’s surely already taken stock of the situation.

Andy backs away, arms folded over his middle to try and hide the coffee stain (it’s not working, the thing’s giant) and gaze fixed on a point behind Dean, features twisted in fear.

Dean slowly spins in his chair and meets Novak’s impassive gaze. Sometimes he swears that the guy may as well be made of marble, considering the truly minute range of emotion he displays. It’s really quite impressive, but at this point, he has no idea what the man is thinking.

Novak’s gaze fixes on Dean, then slowly tracks over to Andy, his face still expressionless. Dean is starting to sweat now, with absolutely no idea of how Novak is going to react.

His boss looks down at the latte still in his hand, then back up to Dean. “Hmm,” he muses, and raises an eyebrow at Dean. Instead of tearing them each a new one, however, he simply says, “Dean, please reschedule my meetings for tomorrow, I need to meet with Bracknell at three.”

And he disappears back into his office, the door closing behind him.

Andy giggles hysterically, and Dean wants to echo the sentiment. You never know what you’re going to get with Novak. He could have just as easily fired Andy, and severely disciplined Dean (who is a little less expendable, but not by much. It helps that at this point he can basically preempt each of Novak’s movements and is the only person who will put up with the guy).

“Shirt and coffee,” Dean reminds Andy, who just looks relieved to be alive. He seems to snap out of whatever shocked daze he was in. “Dude, I nearly got eaten by the dragon,” he breathes, and then he’s disappearing out the door of Dean’s office as fast as his legs will take him, not wanting to hang around lest Novak return.

Days like this, Dean wishes he could do the same.

Instead, he puts his head down and gets back to work. When Andy returns fifteen minutes later wearing a clean shirt, Dean downs the proffered coffee in one go.

He works steadily for the next hour or so, up until he hears the soft swish of Novak’s office door opening. Dean straightens up and glances over his shoulder at his boss, eyebrow raised.

Novak is frowning down at a memo in his hand, and his blue eyes look troubled when his gaze meets Dean’s. This can’t be good. “It seems that we have an overflow of manuscripts and paperwork to attend to. I know you’d requested leave for the weekend, but I require you to remain here in order to assist with sorting and cataloguing the apparently untouched excess. I hope that won’t be a problem.”

Dean’s stomach sinks. That leave had been requested for weeks – months, even. And now, just days before he’s set to head home, to have it pulled out from under him?

His chair slides back across the carpeted floor as Dean stands, turning to face his boss. “Sir, it’s, uh, it’s actually my little brother’s graduation this weekend, so I-“ Novak is already breezing past him, and it’s evident that he has no intentions of actually listening to Dean’s plea. Dean can’t believe his shitty life. “It’s fine, I’ll just miss it. You’re actually saving me from a weekend of misery anyway,” he bites out, his voice dripping with sarcasm.

Novak disappears around the corner and Dean swears, slapping his palm on the desk and slumping back down into his chair. He just can’t catch a break. He’s been looking forward to the big celebration for so long, knowing that it’s one of the few times he’s going to be able to get out of New York this year to spend time with his family. Now, he’s not even going to get to see his family, let alone be around for Sam’s big day.

His mom’s going to kill him.

Lunchtime finds Dean hunched over his work phone, doodling idly on his memo pad as he’s berated by his mother.

“I know, I know, okay? Tell Sammy I’m sorry, okay, what- mom, what do you want me to tell you? He’s making me work the weekend. No, I’m not- no, listen, I’ve worked too hard for this promotion to throw it all away, okay? I’m sure that dad is pissed, but-“ At that point, Dean sees Novak out of the corner of his eye, almost at the door to his office. He smoothly changes tack, straightening up and shoving his drawings out of sight. “-we take all of our submissions around here very seriously. We’ll get back to you as soon as we can.” He slaps the phone down onto its holder, effectively ending the conversation and carefully avoiding Novak’s gaze.

Novak frowns suspiciously at him from the doorway. “Was that your family?”

For someone who usually has all the social grace of a very obtuse brick, sometimes his boss is irritatingly astute. Dean sighs. “Yes.”

Dean figures that Andy must have put something in his coffee as payback for earlier when he sees the corner of Novak’s mouth curl up just slightly. “Did they tell you to quit?”

“Every single day,” Dean replies without missing a beat, swivelling back to his computer and tapping on the space bar to bring it out of sleep mode.

Novak nods, though it seems to be more to himself than anything else. “I’m meeting Morgan and Sharpe upstairs. It seems that you forgot to inform me of that this morning.” Dean is pinned under a stern look. So that’s the thing he hadn’t been able to remember.

“Come get me in ten minutes, we have a lot of work to do.” And of course, he’s gone before Dean can even reply, disappearing out of view and leaving Dean to drop his forehead down on the desk, praying to whoever the fuck is listening that his promotion is coming soon.

rings

At twenty-nine years of age, Castiel is immensely proud of what he has achieved. To be the editor in chief for Sandover Publishing, one of the youngest to ever hold that position in the history of publication companies? It’s certainly impressive.

He knows that he may have sacrificed some aspects of his life to ensure such a magnitude of success in his career, but they’re not sacrifices that he minds or even notices. So far, he’s done fine without a partner, or even without close friends. His work is more important than any of that – his achievements, his success, the growing influence of Sandover Publishing. Books and numbers make sense. People do not – which is why he has no idea as to the reason behind his meeting with Luke Morgan and Michael Sharpe. His results are impeccable, and while he doesn’t understand the intricacies of day-to-day interaction, over the years he’s gotten very good at manipulating his clients into complying with his goals and wishes. After his hugely successful trip to London to close a difficult client and smooth over some ruffled feathers, he should be one of the bosses’ favourites – so why has he been called up to their office?

His employees scurry across the office before him, scrambling to get out of his way, and he doesn’t blame them. He’s stalking over to the elevators, trench coat snapping out behind him, and he must have a face like thunder. The two people inside the elevator see him coming and almost trip over each other trying to vacate the space, and Castiel pays them no attention as he steps inside and jabs at the button for the right floor. May as well get this over with – usually he’s pretty good at being able to preempt whatever is coming his way, but with this… he has no idea. Once he’s alone in the seclusion of the elevator as it pulls him several floors up, he sighs and runs a hand through his unruly mop of hair. In the mirror, he can see it stick up, and tries in vain to pat it back down before the meeting. There are bags under his eyes, he realizes. Worse than normal.

Not much he can do about that, though. The work around here won’t complete itself. The elevator gives a soft ding to signal his arrival, and he squares his shoulders, stepping out and making his way over to his bosses’ office. Castiel raps twice on the ornate wooden door, and then he’s pushing it open, raising an eyebrow at the two men who glance up at him. “Luke, Michael,” he greets them, nodding woodenly as he pushes the door shut behind himself. “Why have I been called up here?”

Castiel has never been one to beat around the bush.

Luke and Michael exchange a glance, communicating with each other with a simple look in the easy way shared by business partners and co-owners. Michael stands from his desk and wanders over to Luke’s, leaning one hip against the edge and pushing his hands into the pockets of his slacks.

“Castiel,” he begins, and Castiel can’t quite decipher the expressions on their faces. If Dean was here, surely he’d know what was going on – the man is much better with people than he is. But Castiel can hold his own, so he straightens his spine and waits for Michael to continue. “First of all, congratulations on managing to close Ms Talbot on your trip to London. Her addition to Sandover will be a huge asset.”

Castiel blinks. That had not been what he was expecting. A little confused, he simply responds by inclining his head. It’s evident that that’s not all Michael has to say, however, from the way that his mouth twists. The man casts a helpless glance at Luke, who straightens up and folds his hands. Luke has always been the better of them at breaking bad news – Castiel knows this, and his stomach sinks.

“Unfortunately, Castiel, your trip to London has also put you, and us, in a difficult position. I’m sure that you’re aware that you applied to have your visa renewed. A condition of that is that you are not allowed to leave the country.”

Castiel frowns – it had been a business trip, born of the need to secure this client before she could run to another publishing company, and it’s now provided them with a secure foothold in Britain. He opens his mouth to explain this, but only manages to get out a, “Sir, I-” before Luke holds up a hand. Castiel snaps his mouth shut, bristling slightly.

“I know, Castiel. But the fact of the matter is, you broke the rules. As such…” He sighs, shakes his head momentarily. “Your visa has been denied.”

The room spins on its axis – or at least, Castiel swears it does. Denied? For a second, he can’t breathe. He can’t go back home, not when he’s built himself such a good life and career here. He reaches out to steady himself on the back of the chair facing Luke’s desk, blue eyes wide and mouth hanging open. So that was why Michael hadn’t been able to tell him. This will shatter Castiel’s world, and the company will lose their best employee, their editor in chief. The room spins, and there is a very real chance that he’s going to vomit right in front of his bosses.

Luke looks sympathetic, but he continues on. “The fact remains, Castiel, is that even if your visa is eventually renewed, you’ll have to leave the country for at least a year. There’s really no way around it – you simply can’t stay here without a work visa. We’ll be promoting Zachariah Adler to your position in your absence.”

Castiel doesn’t flinch, but it’s a near thing, and his expression fixes itself into a dark scowl. Adler is a scumbag who’s been trying to undermine Castiel for almost a year now, gunning for his job as the only other person in the company who could possibly occupy the position. Now, to have it handed to him so easily because of Castiel’s blunder? He opens his mouth – to protest, argue, beg, he’s not sure. And he’ll never know what may have come out of his mouth, because at that moment, there is a sharp knock on the door.

Dean’s head appears out from behind it, and as the sunlight streaming through the huge windows lining Luke and Michael’s office lands on his face and illuminates those green eyes, Castiel has a brilliant idea.

Dean’s lips are moving, but Castiel isn’t listening to a word he’s saying, his mind too busy formulating the plan. Yes, yes. This could work. Gay marriage is legal, so that isn’t a problem. Dean is the right age, if a few years younger, and not unattractive. Besides, he’s here, which means that it doesn’t look like Castiel is making excuses or grasping at straws. As long as Dean just goes with it. This could be his ticket to staying in America.

Dean blinks at him, and Castiel realizes he’s been staring when he ventures a, “Sir?” He shakes his head to clear it, then gestures for Dean to join them inside the office. While he attempts a smile, it’s clear from Dean’s expression that the result is not a success, and he quickly lets it fall as his assistant joins him in front of Luke and Michael. It’s evident that he’s uncomfortable from the way he shifts his weight and surreptitiously tugs at the shirt that is one size too small, unsure of how to act around the co-owners of Sandover Publishing. It probably also doesn’t help that he has no idea why he’s here.

Dean will be fine – all he has to do is roll with it.

“Michael, Luke,” he begins, resting a hand on Dean’s shoulder. It’s a miscalculated gesture, since Dean is an inch or two taller than him, but he’s committed now. “We didn’t want to share the news for fear of upsetting the balance inside the company, but I feel we now must.”

Castiel may not understand socializing, but manipulation is what he’s good at.

“Dean and I are engaged.”

Beside him, Dean freezes, and Castiel tightens his grip on the man’s shoulder ever so slightly as a warning not to fuck this up.

Blindsided by the information, Michael and Luke look between the two of them in unison, mouths hanging open. It takes them a few moments to process this before Michael manages to get out any words at all. “Mr Winchester? Is this true?”

It seems that in the two years of having Dean as his assistant, Castiel has managed to train him well, because there’s only a beat of hesitation before Dean replies with a, “Yes.”

...yes

Dean may not know what’s going on, but Castiel likes to think that he trusts his boss enough to follow along in blind faith. Plus, Dean has always been eager to please, even if he grumbles about it when he thinks Castiel isn’t within earshot.

Luke and Michael don’t seem to know what to make of this. All Luke can manage is a stuttered, “Congratulations?” and Michael seems too shocked to investigate any further, seemingly stuck on the fact that their male editor in chief is engaged to his male assistant. Several long moments of awkward silence pass, in which Castiel is not sure what to say, and he can feel Dean’s gaze burning into the side of his face. Eventually, Michael seems to snap out of his daze somewhat, still looking a little baffled by this turn of events.

“Well, uh… Then, Castiel, make sure you get all your paperwork done as soon as possible, and… Well, congratulations, I guess. Just keep workplace relations at a professional level.” Michael’s face has taken on a slight red colour, and Castiel nods. “Thank you, Luke, Michael.” With the meeting over, he lets go of Dean’s shoulder and turns to exit the office, Dean hot on his heels.

As soon as they’re out in the hall, Dean whirls on him and, once he’s made sure there’s no one else around, tears into Castiel. “’Scuse my language, boss, but what the fuck was that? Since when are we engaged? Why are we engaged? Hell, I didn’t even know you were into dudes!” Dean’s eyes are wide and he’s tugging compulsively at his tie like he does when he’s stressed, as if having it tight around his neck makes him anxious.

Castiel may not understand socializing, but he’s picked up a habit or two of his assistant’s over the years. He scrubs a hand over his face, suddenly exhausted by this whole ordeal. Hopefully it won’t get too long to get the paperwork sorted and everything straightened out.

“I apologize for surprising you with that,” he tells Dean, who’s now staring at him with hands on hips, his aggressive pose practically demanding an explanation. “It was a necessity. My application for a work visa has been declined, and my only option for remaining in the country and keeping my job is a successful application for a spousal visa. You were available and nearby – to my knowledge, you rarely date, if at all – and your status as my assistant makes any hypothetical relationship between us more plausible.”

Dean is still staring at him, slackjawed, and Castiel fights the urge to roll his eyes. It’s evident that this is going to take a while to sink in.

“But… I… what… I’m not going to marry you, dude! You can’t make me!”

Castiel has had enough of this. No one is around to see him fist a hand in the front of Dean’s shirt and haul him a short distance down the hall and around the corner, where they definitely won’t be interrupted. When he lets Dean go, the man rocks back and lets his shoulders lean back against the wall, his eyes wide and cheeks a little flushed. The sight of his tongue darting out to wet his lips draws Castiel’s attention for a moment, but he quickly snaps himself out of it.

“Listen, Dean. If I’m deported, where do you think that leaves you? Adler will take my job, and he hates both of us. You’ll be tossed to the curb without so much as a backwards glance, and the last two years will all be for naught.” Castiel runs a hand through his hair and squeezes his eyes closed for a second. He needs this to work, damn it. “If you agree to this, we can break it off and get a divorce as soon as I get my spousal visa, I promise. It’s all for pretend.”

He can see the gears working behind Dean’s eyes, and for a second he regrets teaching his assistant so well when he counters with, “If I agree to this, I want a promotion. I want to be an editor, capisce?”

Begrudgingly, Castiel nods, and he notices that the corners of Dean’s mouth tilt up just slightly at his small victory over his boss. “Fine. We’ll go to the USCIS tomorrow and get all this straightened out. Nine in the morning, don’t be late. Understand?” Dean nods, still looking shell-shocked by the whole situation. Castiel doesn’t have time to ease him through it. He has work to do. With a sharp, curt nod of his own, he turns on his heel and strides off down the corridor, towards the elevators.

What a mess.

Notes:

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