Actions

Work Header

You Looked at Me and Somehow Saw Good

Summary:

“Sure, Castiel is the big guy here. But his older brother is the big-big guy. He’s the chief executive officer. Castiel is only one station below him, so he’s the one who gets hit with the brunt of the heavy hitting work and mingles more with us commoners when the job calls for it. Hardly anybody ever sees his brother.”

Before Adam could get a word in, Becky piped back up.

“Yeah, his name’s Michael, I think. I’ve never seen him before, but I hear that’s sort of a good thing. Apparently he’s a real hardass and kind of a dick. But what do you expect from a rich CEO that never leaves his office? Is it true that another one of Novak’s assistants ran out crying yesterday?”

----------

Adam started his new job at NovakOn as Castiel Novak's personal assistant. It's boring and a little dull, but it pays well. Unfortunately, his social life is practically nonexistent and the only people he does talk to, his brothers Sam and Dean, hardly give him the time of day.

Going through the motions of life without expecting much, Adam's world gets turned upside down when he is transferred from Castiel to his older brother Michael, the infamous and very feared CEO of NovakOn.

Notes:

Hi!

The world needs more Michael/Adam Milligan multi chapter fics, okay?

>> Also, there are some serious themes in this story. I will put any serious trigger warnings in the chapter notes as needed but this won't be needed until much later in the fic!

 

I made a pintrest board for this fic if interested :)

(See the end of the work for more notes.)

Chapter Text

“It’s not a tough job. You just have to show up on time and not be an idiot.” Dean told him on his first day. It felt so long ago now.

Somehow, his older brother had managed to convince his boss, Castiel Novak, to take Adam on as an assistant despite his lack of experience. So, naturally he had been practically shaking the entire way to the massive skyscraper they called headquarters and praying to every deity out there that he didn’t make a complete fool of himself the first day.

Castiel was surprisingly kind, if not also a bit stern. It was no wonder why so many enjoyed working under him. Despite his rough exterior and apparent lack of casual people skills, the man was more than fair most of the time. And while he expected good work and a solid work ethic from his employees, he was never needlessly cruel like many bosses could be.

Adam had found this much out fairly quickly, mostly from his older brother who was attached to Castiel at the hip, apparently. But, also through the interactions Adam had with Castiel himself as his assistant. He didn’t actually do anything too terribly difficult, and it could be anything from grabbing the man a cup of coffee from the breakroom or printing out some documents he needed.

It was boring and begrudgingly monotonous, but it was work.

Besides, being the right hand of the big boss himself had its perks. Adam was typically with Castiel, which in turn meant he was also often with Dean, in the nicer parts of the building which saved him from the humdrum of the office cubicles a few floors down. Not all were saved from such a fate, like his other older brother Sam who got stuck in the small legal area of the corporation with little more than a desk and computer.

Overall, though, working for the somewhat famous Castiel Novak was better than he expected it to be by a long shot.

The pay wasn’t too bad either, all things considered. It sure beat his last job as a barista!

Unfortunately, it also meant that each day passed with little to tell about it, and the only real space besides the high end offices he frequented either with or on behalf of Castiel that Adam could really talk to anyone was the breakroom.

It was there, however, that office gossip blossomed like a flower that couldn’t get enough of this dog-eat-dog capitalistic paradise.

“Is it true that another one of Novak’s assistants ran out crying yesterday?” A woman, Adam was pretty sure her name was Becky, not so subtly stage whispered to her table companion.

Normally he wasn’t one to jump into conversations, especially ones that almost always turned out to be untrue. This time though Adam couldn’t help but laugh a little, causing both women to stop and stare at him.

He froze and cleared his throat, pouring himself a fresh cup of coffee from the machine before he sat down.

“Sorry, I, uh…I’m Mr. Novak’s assistant, and I’m pretty sure I’d remember if I ran out of the office crying. Which I didn’t.” He clarified quickly.

The other girl, Adam didn’t actually remember her name, scoffed and rolled her eyes. “Not you. You work for Castiel, right? We’re talking about the other Mr. Novak. The big guy himself.”

“Uhh…” Adam just stared at her and blinked. “Isn’t, uh…isn’t Castiel the ‘big guy’?”

He had been here for months by now and he was pretty sure Castiel was the one who ran the place. Everyone that Adam knew of reported to him, listened to him, and wanted to stay on his good side. He had also never heard of another Mr. Novak, as each and every time Adam came across something with that name he handed it over to Castiel without a second thought and had never been corrected on it.

Miss No Name smirked.

“Sure, Castiel is the big guy here. But his older brother is the big-big guy. He’s the chief executive officer. Castiel is only one station below him, so he’s the one who gets hit with the brunt of the heavy hitting work and mingles more with us commoners when the job calls for it. Hardly anybody ever sees his brother.”

Before Adam could get a word in, Becky piped back up.

“Yeah, his name’s Michael, I think. I’ve never seen him before, but I hear that’s sort of a good thing. Apparently he’s a real hardass and kind of a dick. But what do you expect from a rich CEO that never leaves his office?” She was strangely cheery for what she was saying, but Adam didn’t comment.

“He has an office here?” He asked instead.

“Top floor.” The lady said, pointing up towards the ceiling. “The whole thing is his space, apparently. Only certain people are allowed up there. I’m pretty sure if anybody that isn’t authorized sneaks up there, Michael actually throws them out of the window and watches them splat on the ground.”

Adam shivered.

He had no idea there was even an office right above his head this entire time. Castiel’s office and those of his closest employees were all situated on the second to last floor. Really, this entire time Adam had just kind of assumed the only thing on the very top floor was storage and old holiday decorations waiting to be brought out once a year.

Apparently that assumption had been wrong.

“Aw, why do you look so gloomy all of a sudden, kid? You work for Castiel, so you don’t really gotta worry about his brother eating you alive or anything. I mean, at least probably not.” Ms. No Name grinned toothily and laughed as Adam grabbed his coffee and swiftly left the breakroom.

 

A couple days later, Adam found himself at lunch with both of his older brothers. It was rare that they could all actually have a day off together anymore, and even rarer that they used those days to get together. Sam and Dean were both notoriously busy at their own jobs, and Adam worked a solid 40 hours minimum, if he was lucky. More often than not he got stuck at the office doing overtime.

“Have you guys ever heard of a Michael Novak that works on the top floor?”

Both brothers stopped and stared at him, and not for the first time since discovering he had two half-brothers, Adam wished the ground would open up and swallow him whole.

“Uh,” Sam had stopped with an abomination of a veggie burger halfway to his mouth. “Yeah. He’s the CEO of NovakOn. Why?”

Oh. So apparently Adam was the only person in the universe who didn’t know that already.

“I don’t know. I just heard some people talking about him in the breakroom a few days ago and didn’t really know much about him. Thought I’d ask, since I’ve never seen the guy.” He shrugged.

It was the truth, even if he was a little more curious than he let on. Could a guy really be as bad as everyone said? Well, probably. Adam suspected Michael was a spoiled rich kid that grew up with everything he could possibly want and, as an adult, expected everything handed to him on a silver platter. Though Castiel didn’t act that way, the way people spoke of the two brothers was enough to know they weren’t similar at all.

Dean was the first one to scrunch up his nose and scowl. “What’s there to know? The guy’s a major dick.”

“You’ve met him?”

“Yeah, sure, a few times. He’s a jerk. I still can’t believe Cas is related to him, they’re nothing alike.” Dean grumbled before plopping a fry in his mouth.

“That’s not totally true from what I’ve heard. I’ve never spoken to Michael, but I’ve seen him at company functions once or twice. He’s really quiet, as far as I can tell. So is Cas.” Sam pointed out.

“The guy’s quiet ‘cause he only talks to people who lick his boots or can afford to be charged his rate by the hour.” Dean pointed a fry at Sam across the table and squinted. “Cas is quiet, but he’s not all high and mighty, ‘better than thou’ and all that bullshit.”

“Geez, Dean. Since when do you have it out for the CEO so bad?” Adam asked with a roll of his eyes. It wasn’t rare for his oldest brother to rant about whatever was on his mind, but he hadn’t said a word about Michael before. Now, suddenly, it was like Dean was an expert on just how big of a douchebag he was.

“Hey. I had to work for the guy a few times over the years to help out Cas when he couldn’t go up to his office himself. Each and every one of those times? I wanted to rip my hair out or jump from the window to my untimely demise just to get away from his dickbaggery.” Dean grunted.

“Wow, Dean. Just wow.” Sam sighed and shook his head.

Adam though snorted. He was sure Dean was right anyway. The chances of Michael being anything other than the most stuck up trust fund baby in existence was near nonexistent.

“So, are you the one who started that rumor that one of Michael’s assistants jumped out of his office window? Or was pushed, whatever it was.” Adam asked.

At that, Dean leaned in over his plate of burger and fries with a devious grin on his face. “Rumors all gotta start somewhere, kiddo.”

Adam laughed and decided that if he could continue ignoring the fact Michael existed at work, he would be just fine.

 

The following morning, Adam woke and got ready for work in his small but cozy apartment.

He lived alone for the first time in his life thanks to the fair pay Castiel gave him for being his assistant, not to mention the quarterly and holiday bonuses that didn’t hurt either. His place might not be big, but it was his and he was damn proud of it.

The other biggest plus of having his own place meant that he wasn’t sharing with Sam and Dean anymore. He loved his older brothers, sure, but he didn’t always love living with them either. No matter how welcomed they said he was, there was that air of hesitancy thick and sticky whenever he walked through their house.

He knew why, of course. He was the bastard son. The secret their father kept that didn’t get revealed until after the old man died, leaving his two favorite sons and the one he rarely visited to accidentally find each other after the funeral. Finding out you had a secret sibling as will and testaments were read was a major blow, after all.

Dean had reacted the worst to finding out John had a secret son and woman he visited for years. Sam had at least tried to be polite, but even at nineteen Adam had seen the way the revelation had shocked him too. Eventually, both brothers mellowed out and the awkwardness faded enough that, when his mother died and left him alone not long after John’s passing, Dean and Sam willingly brought Adam, who had nowhere else to go, into their home. But even then he felt like an inconvenience, a parasite, leeching in on the lives of his half-brothers and interrupting their well established normal.

Now, a few years later, Adam was old enough and made enough to go out on his own. Neither Sam or Dean had tried to stop him other than asking him if he was really sure, but when it was all said and done, he was certain his brothers were glad it was just the two of them again. Just the way it had always been, before he came crashing into their lives and unrooted everything they thought they knew about their dad.

The lingering guilt of that never quite left him, even after all the times Sam tried to tell him it wasn’t his fault. Still, somehow, living alone in his tiny apartment felt less lonely than when he lived with Sam and Dean.

Another perk of being the assistant of one Mr. Castiel Novak was that Adam had the luxury of stopping almost every morning at a local coffee shop only a couple blocks away from the office. There, he ordered not only his own favorite drink of the day, but also Castiel’s, who insisted that Adam be reimbursed for his efforts and ensured that was reflected on his paychecks every period.

“Thanks.” He chirped as the barista handed over his receipt and he stepped towards the end of the counter to wait for his drinks.

It was a pretty small place, made only smaller by the amount of people that crammed their way inside and took up every seat and stool in the building, and even the few outside too. Good thing he wasn’t planning on staying, he had to get going if he didn’t want to be late.

To his side, a handful of other people waited for their drinks too. One in particular caught his eyes, and maybe he stared a little too long for what would be socially acceptable, but he wouldn’t admit that.

But who could blame him? The guy a few feet from him was tall and despite the fact he was wearing a suit and long coat, Adam could tell the guy was strong. It was a body type that sort of reminded him of Dean, all power and strength without being obnoxiously bulky. Not to mention that his jaw was just as impressive, and a hint of blonde stubble threatened to peek through with a combed back, professional hairdo to match. It was the sort of well kept kind of face that Adam wouldn’t mind wrapping his legs around. But who was paying attention to that? He couldn’t be that much older than Adam, maybe in his mid to late thirties.

And those eyes, fuck. They might’ve been the bluest things he’d ever seen, and that was saying something considering the guy he worked for had an impressive set of blue eyes himself.

Oh wait, his eyes.

Oh fuck, he was looking back at him.

The instant he realized he got caught staring, Adam averted his gaze and glanced back at the small area the barista was hastily putting orders and calling names. He tried not to combust right on the spot from pure embarrassment and instead focused on watching the employee behind the counter work.

He couldn’t tell if the hot guy was still looking at him or if he had glanced away the second he intimidated Adam into averting his gaze, but either way he tried not to think about it.

“Michael!” The barista called as she plopped down a large cup and warmed muffin onto the counter before skittering away to continue working on the rush of people’s orders.

Hot guy -- Michael, it turns out -- stepped forward to snatch his drink and food without a word. He did, nicely enough, pull out his wallet and plop a few pristine bills into the tip jar at the end of the counter for the miserable underpaid workers though.

Adam tried not to be too obvious as he watched him as he move down the counter slightly towards the packets of cream and sugar. At least this way his back was towards him, so he took in his fill of impressive back and firm posture. Seriously, was the guy a soldier or something? The rigid way he stood, Adam was certain he should be commanding armies or something.

Eventually, or probably in actuality only a few moments later, Mr. Hot Guy aka Michael grabbed his drink and muffin, and walked off without sparing another glance in his direction.

Thank god, really. Adam wasn’t sure he could afford to be that embarrassed twice this early in the morning if he got caught staring again.

He turned back towards the counter to wait for his own name to be called when he spotted something sitting off to the side. A wallet.

“Ah, shit. Hey!” He called, raising a hand and trying to grab the guy’s attention but, unsurprisingly, he watched the dude named Michael slip out the front door and onto the sidewalk without even pausing. “Dammit.” He cursed and turned back to the wallet.

It only took him a couple seconds to make up his mind. He snatched the wallet off the counter and, after a real quick glance at the photo of the ID to confirm it was the right guy’s, Adam took off towards the door.

Once he busted his way out of the coffee shop, he spotted the familiar cut of warm blonde a few paces ahead, walking down the sidewalk.

“Hey! Hey, wait! Michael!” He called out, and this time got a reaction.

Mr. Hot Guy stopped and turned, obviously curious as to who on earth was screaming his name on the sidewalk at exactly 7:48 am. Adam couldn’t bother to feel embarrassed about it though as he ran up to him and thrusted the leather wallet into the man’s chest as he panted. Fuck, he needed to work out more.

“You forgot your wallet.” He explained between breaths, letting go as soon as Michael had his hands on it. “Ya left it on the counter back there. I happened to see it next to the tip jar and stuff. Lucky you I saw it and not somebody who would’ve taken it. You never know, people are kinda crazy.” He let out a breathless laugh.

Unnervingly, Michael simply raised an eyebrow and stared at him. If Adam didn’t know better, he would’ve thought the guy was studying him like he was trying to figure something out.

Instead of speaking, he opened his wallet and offered over two hundred dollar bills.

“Uhh, what are you doing, dude? I don’t want your cash. If I wanted to rob you I wouldn’t have given your wallet back in the first place.” Adam took a step back and held up his hands as if that could placate the entire weird situation.

Michael’s eyebrow shot impossibly higher. “You don’t want compensation for your efforts?”

Oh fuck, Adam could melt. What a voice. All deep and rough around the edges. He should have known, even his voice spoke of strength and no doubt commanded anyone around him to listen. Hot on the outside and a sexy voice? Now he was certain the universe was just taunting him.

“No, not really. I was just trying to give you your stuff back, man. I do need to get back though, I’m still waiting for my and my boss’s coffee and I don’t really have that much time before work. So…” He glanced at his phone and a new wave of anxiety flooded him. It was 7:52. He had eight minutes to get their coffee and get to the top of a fucking sky scraper. “Fuck! Alright, nice to meet you and all that, man, but I gotta go. See ya around!” He called over his shoulder, already half running back to the coffee shop to snag the two cups already waiting for him on the counter.

When he rushed out of the shop and down the street towards HQ again, Michael was already gone.

 

Adam made it only a few minutes past eight, panting and trying to catch his breath even after the long ride from the elevator. Running in dress pants, a button down, and a sweater in warm morning weather didn’t do much to help in that department either.

“Ah, Adam. Good morning.” Castiel greeted once Adam had entered his office and promptly placed his usual coffee order on the desk beside him.

“Good morning. Sorry I’m a little late. I uh, had a little problem at the coffee shop this morning.” He admitted. He didn’t want to make excuses, and he knew that for as nice as Castiel was, he wasn’t one to accept any lies. But he wasn’t lying, and he hoped that came across as true enough with the coffee shaped peace maker he handed over.

“Oh, were you? It’s no problem, these things happen. You aren’t typically late, and I can’t really fault you for being so if the coffee shop held you up when I am the one requesting you go there for me every morning, hm?” Castiel grinned politely from behind his coffee cup and took a long sip.

Adam released a breath he hadn’t realized he’d been holding. “Thank you, sir. I’ll get right to work then.”

“Oh, before you go. I do need to talk to you before you leave this afternoon. Now, you aren’t in trouble. In fact, I think you will be making even more money than you are now. But…let’s save it. Just come see me before you leave tonight, okay?” Castiel offered a reassuring smile, but it was tight. Something not quite right in the way he looked at him.

“Of course, Mr. Novak. I’ll speak to you this afternoon.” He assured, then he quickly scurried away.

The rest of his shift passed in a somewhat awkward fog. It felt as if he was awaiting the proverbial chopping block, like the end of this shift was going to be the end of his entire career. Or rather, if one could call being the personal assistant to a rich guy a career.

But call it whatever you wanted, he didn’t want to lose this job. It might be boring but it paid well and he was finally feeling like the ground had stopped being swept out from under him. He should’ve known better than to think that was going to last. Nothing good ever lasted that long as far as he was concerned.

Eight hours passed in a sludge and when his work was finished and it was time to go, his heart weighed like iron in his chest. He stared at Mr. Novak’s door with a keen sense of dread. He wanted to run, just say he forgot, but he knew that wouldn’t really do anything to help him. If he was going to be fired then he was going to be fired, there was no point in putting off the inevitable.

So, he sighed and knocked on the pristine wooden door, then let himself in when he heard his boss invite him.

“Hello, Mr. Novak. I’m here to talk?”

Castiel smiled and motioned towards the seat opposite his desk. “Yes, of course. I hope your day went well. I have something I’d like to talk to you about. Now, as I mentioned earlier, you aren’t in any trouble. However, something has come up and I’m afraid your position is being moved.”

Adam blinked. “Moved, sir?”

For the first time since he’d known him, Castiel actually looked a little sheepish.

“Ah, yes. I’m not sure if you heard, but our CEO’s former assistant unfortunately had to quit. My brother, however, is desperately in need of a hardworking hand. I don’t trust many with such an important task, and I’m afraid he trusts even fewer with it. You, however, have proven to be even better than I imagined when I hired you on. I’ve truly been impressed by your work since you arrived.” Castiel grinned.

Adam tried to take the compliment, he really did. He was pleased to know his boss thought so highly of him, but the looming uncertainty overshadowed everything else.

“I appreciate that, sir. But…what does that have to do with my job being moved?”

“Oh! Of course, I apologize.” Castiel sighed and rubbed a hand over the dark stubble on his chin. Dean was right, he was a good looking man. “Well, I suppose I should just lay it all out. My brother, our CEO, needs a new assistant that I know is capable of handling the job and he needs it effective immediately. Over the past weeks he had become aware of the work you’re doing, mostly, I admit, from my own praise. However, now that he is without an assistant of his own, the CEO is requesting your immediate transfer to his office. Of course your salary will be increased to accommodate the change as well, but that paperwork can be finalized tomorrow.” When he was finished, Castiel clasped his hands together on his oversized desk and waited patiently.

The thing was though that Adam was pretty sure he was short circuiting inside.

He was being moved to work under Michael? The same Michael that was known for pushing his assistants too far? Making them cry and quit?

“W-What about the work I do here? Who will take over for me?” For some reason that was the only question that could leave his mouth at the moment.

“Hannah can handle some of the workload until I find a replacement.” Castiel explained, looking almost regretful.

Maybe he was, though Adam didn’t know if it was towards himself or Hannah, Castiel’s private secretary. Or maybe he was mourning the fact he was having to give away his assistant and would have to train someone else at the job soon.

Whatever the reason was, Adam knew Castiel really didn’t have a say in the manner. He may be the ‘big-guy’ around, but there was still someone even higher than him and orders were orders.

“Sure, but…um…is it true that his last assistant ran out crying?” He dared to venture, though he wasn’t entirely sure he wanted to answer. If he was going to be forced to work for the guy though, he wanted to be as prepared as possible, even if that meant expecting the worst of the worst.

“Oh, erm…” Castiel hesitated a few moments, until he eventually sighed and ran a hand through his hair. “Technically? Yes, she did. I thought for certain I had picked a good one for him this time but she apparently had a more difficult time with Michael than I anticipated. He’s grown tired of going through so many ‘unreliable help’.” Castiel honest to god used air quotes! “Hence, why he believes you may prove to be a good fit for him. Since you’ve done so well under me and the pressures of this office for the last several months, Michael is convinced you are the best suited candidate for his assistant position. Though I don’t really want to give you up, he made it clear that the change was not optional.”

Now that made something bristle in Adam and his cheeks felt hot. Not optional? Like hell! Rich or not, he wasn’t going to just be tossed around.

“But I signed a contract for your assistant position. He can’t just tell me to move. What if I say no?”

Castiel somehow looked even more uncomfortable than he did ten seconds ago. “Well, actually, he can. It is a policy in all employee contracts, the CEO has the power to terminate or alter any current or future positions as he deems necessary. And as for saying no, well…you could, but doing so would cost you your job. Like I said, he does have the power to terminate or alter positions of individuals, regardless of what that position is. Failure to adhere to the desired changes results in immediate termination.”

Adam couldn’t help but gawk at the man in front of him like he was crazy. Really? Michael could just toss someone aside and say “thank you, next” and be done with it? Where was the regard for the employees’ feelings or their needs outside of the job?

Then again, did Adam seriously expect Richy McRichRich to give a shit about that?

“So it’s go work for him or get fired?” He asked.

Castiel nodded solemnly. “I apologize for the inconvenience, Adam. I do wish I could keep you here, you’ve done a fantastic job as my assistant. But…I’m afraid my hands are tied.”

For what it was worth, Adam believed him.

“Alright…fine. When do I start?”

“Ah, first thing in the morning. You can come to my office here like you typically would and I can escort you up to my brother’s office to introduce you. I’m sure having someone there you know will help ease the transition, a little bit.” Castiel smiled warmly.

Yeah, he was probably right. Castiel was his boss but he was still a decent person. The fact he was offering to hand deliver Adam and bring him some comfort in the process was a testament to that. As if all the gushing his older brother did over the man wasn’t enough.

“Right. Then I will see you tomorrow, Mr. Novak.” He offered as he stood up.

He felt numb. He vaguely recalled saying his goodbyes to Castiel and riding down the elevator. Then he was pretty sure he could remember getting on the bus and walking into his quiet apartment, then eventually into bed. But even as he lay there, staring unseeingly up at his ceiling, none of it felt real.

Just when he thought things could stay comfortable for once, it all came crashing down again.