#ceo!dean

Dean glances down at each packet. He snorts and tosses the first one into the metal garbage bin beside his desk. Sam frowns.

“What was wrong with that one?”

“He’s a dude. Don’t you think we’ve got enough of a sausage fest going on around here?” Dean says, gesturing wide at the multi-floor building that makes up HunterCorp. His father’s enterprise, distilled down to two sons who, on their best day, have very different opinions on what makes for a good executive assistant.

Sam utters a longsuffering sigh.

“Man or woman, you need a real assistant, Dean. Someone competent enough to deal with your demanding schedule and…personality.”

“What’s wrong with my personality?”

“And I need you to have an assistant so I can focus on my real job. You know, running the entire Legal department.”

Dean rolls his eyes. “I know how to do my job, okay? I think I’ve picked up the slack pretty damn well since Dad died.”

Sam pauses, acknowledging that with a nod, and a heavier note.

“Yeah. You have.”

“So while I’m throwing money away hiring for a wholly unnecessary assistant, who I’m gonna have to tolerate looking at every day, I might as well be looking at somebody hot,” Dean says.

Another exhale leaves Sam’s body, along with the brief buoyant feeling of admiration for his brother.

And now we’re back where the neanderthals live. 

Sam gets a text from Reception that has his pocket buzzing. After he checks the message, he nods to himself. Here we go.

“All right. The first one is on her way up now, so do me a favor and get yourself together,” he says. “For example, it’s a little early for the booze, don’t you think? It’s 10:00 a.m.”

Dean pauses. The crystal decanter in his hand is halfway to pouring his first fifth of whiskey.

Second breakfast, if you will.

He gives his brother a flat look, one that’s accusing him of being an eternal wet blanket. But he begrudgingly concedes the point and puts both the decanter and the tumbler in a cabinet under his desk.

Classy. Sam rolls his eyes.

A knock at the door stops him from commenting out loud.

Clearing his throat, he walks over to let you in.

“Hi, Sam…and Mr. Winchester,” you say, shaking hands with the slightly taller brother. Then you turn to Dean Winchester, CEO of HunterCorp. He stands and leaves his desk to greet you.

In the time it takes him to cross the room, he takes you in within the breadth of a few seconds. More than the professional pantsuit and your pretty face, he notices your bright smile, the slight bout of nerves in the way you shake his hand. He finds himself smiling back.

“Uh, hi,” he says eloquently. “Call me Dean. Can we get ya some water, coffee, iced tea…”

He doesn’t even think they have iced tea, but he’s willing to make Sam go and find some.

“No, thank you. I’m fine,” you reply.

“Okay, then. Just, uh, take a seat.” He gestures to the open seat in front of his desk before he returns to his own plush leather chair. It squeaks as he swivels back in place. He shares a nod with Sam, who heads out of the office. The door closes behind him.

Dean glances down at the list of questions Sam prepared for him to ask each candidate, a sheet of paper that lies over your resume. He brushes the questions aside and focuses on the information printed under your name.

His brows raise in interest. “You graduated from Stanford University like my brainiac brother?”

The sound of your light laugh draws his gaze from the page, up to your face.

“Yeah, we were actually friends. It’s just been…a while,” you say, clearing your throat a little.

Dean inclines his head. His understanding grows along with his suspicion as he reads.

“Look at that, a Marketing major. Looks like you had a couple of promising internships too.”

“In college, yes.”

“And you were a Communications Specialist at Ashland for…eight months in 2021?”

“Yes, that’s right.” Again, you nod, smoothing a non-existent wrinkle in your pants. Your gaze falls away from his.

This time, Dean thinks you know full well what he’s getting at when he sets down your resume.

“That was five years ago,” he says. “You haven’t worked in five years since getting out of college?”

“It’s a bit complicated,” you admit, though you sit a little straighter. “I gave birth to my daughter, Emma, in November of 2021. My ex…was not supportive. My mother was also having some heath issues, so I moved back home to help my father take care of her. They took care of me too.”

Your fingers flex and interlace together in your lap. Dean notices the subtle fidget, but otherwise you’re calm and professional as you admit to something so personal. He can respect that you didn’t try to bullshit him.

“Hmm. Complicated,” he nods, then hesitates. “How’s your mom doing now?”

Your lips tug, but not at a smile. “She passed away a few weeks ago.”

Dean dims further as he inhales deeply. “I’m sorry.”

You give a tight nod, your throat swallowing.

“Look, since you’ve been honest with me, I’m gonna be real with you,” he says. “I run a company of 300 employees, 20 departments, 10 floors. I work 60-hour weeks minimum. I meet with department heads, shareholders, business partners and prospective clients on the daily—the kind of schedule that would make your head spin. I know you’ve done what you had to do, but I’m not sure you’re ready for a job like this. And that’s besides the fact that I’m not convinced I even need an assistant who’s probably just going to slow me down by sticking her nose into my process and asking questions I don’t have the damn time to answer.”

You tighten up at that, understandably taken aback. Your lips purse, but instead of tossing him a fuck you then and walking out, like he half expects, you sit with his words. You think it through, and you give him exactly what he doesn’t expect. 

“I may not have been clocking into an office for the past few years, but I haven’t been a stranger to hard work, Mr. Winchester. I’ve done nothing but fulfill the role of an assistant,” you say, and your gaze never leaves his when you say it. “Appointments, calls, messages, emails, paperwork, finances, data reports, coffee, power lunches, drycleaning—whatever you need, however quickly you need it, I can get it and I can make it happen. If there’s someone you can rely on, it’s a single mother who knows how to get shit done.”

Dean understands now. He understands the pain hidden in your eyes, and the too-tight set of your shoulders that hold the weight of responsibility. Urgency. A hint of desperation.

You need this job, maybe a little too much.

He should let you down gently. You’re not the kind of girl he’s looking for.

But whenever his mind and his gut are in conflict, he usually heeds his gut. That’s worked out well for him so far.

So he shrugs, and he stands up, holding out his hand to you across the desk.

“Like I said, call me Dean.”

Two Weeks

He groans into the ceramic mug at the first sip. Jesus Christ, you make a good fucking cup of coffee. That’s not even in the top five of the talents you possess, as it pertains to his business and your ability to learn quickly, talk minimally, and begin to anticipate his needs.

You dress nice, you’re always on time, and hell, you smell good too. Like body lotion and just the right amount of perfume. Obviously he can’t comment on any of these things, unless he wants a visit from Meg in HR. But it doesn’t stop him from noticing you, his heart thumping whenever you come in close to show him a document or ask him a question about a report.

Instead of rolling his eyes or snapping that you should have someone who’s not running this entire company explain it to you—like he did the last assistant who didn’t even survive three days—Dean finds an ounce of patience to spare for you.

He sits there and explains the difference between an M1911 handgun and a shotgun, and why the background checks take two months for one model and a few weeks for the other one is just a difference of state law, not HunterCorp’s manufacturing techniques.

Sam is rather fucking gloaty about it too—mainly at the fact that his top candidate made it through Dean’s initial hiring plans.

“Admit it, she’s good,” Sam says later in the day, while the two of them eat lunch together in his office. You just had it delivered ten minutes ago, still piping hot.

“She’s all right, for being your little college friend.” Dean slurps his lo mien and casts his brother some side-eye. “Is that all she was, or did you two occasionally sneak off for a little rec room break on the side?”

Sam gives him a flat look. “No, I was with Jess by then.”

“Just asking.” Dean shrugs. Secretly, he’s pleased. “You know anything about the ex-boyfriend, Father of the Year?”

Sam snorts in derision. “Some asshole in Sales while she was at Ashland. From what I heard, they were dating for six months or so, and she got pregnant. He, uh, tried to get her to end it.”

Dean frowns, and actually pauses eating to raise his head.

“She told you that?” he asks.

Sam holds back on answering for a suspicious moment, his eyes shifting down at his food.

“Made a couple calls to some contacts I have over there,” he says.

Spies, in other words. Dean nods in understanding. His brother’s always been the smart one. That’s what everyone used to say, including their father.

Two Months

You’re not sure if you should do it.

You have a sensitive report in your hand, fresh off the printer. You really think Dean should see it before he gets any deeper into his negotiations with Roman Enterprises, but he’s meeting with them right now in the big conference room, with Dick Roman himself, as well as the rest of his sales and legal representatives.

This isn’t the first meeting Sam and Dean have undergone with the company; Roman Enterprises been courting HunterCorp into a partnership on a new product, but this could be the day that makes the big swinging dicks in the room shake hands (even if that little visual almost makes you snort).

Dean’s never expressly warned you about entering a meeting uninvited, but it’s still nerve wracking as you stand outside the door. You can hear familiar voices, including the nasally tone of Alastair, the one who gives you the creeps whenever he slithers through the office and gives you a “charming” once-over.

But you also hear Dean. His voice is deep and smooth and confident. It gives you the little confidence boost you need to twist the knob and push the door open.

Just as you predicted, with a sinking feeling, all eyes turn to you when you enter the conference room. Sam and Dean and their lead sales manager, Cas, look over at you in varying degrees of surprise (Cas with disapproval). Dick Roman remains impassive, if slightly amused when you squeak out an, “I’m sorry.”

It’s Alastair’s gaze you feel on your profile when you quickly make your way around the large conference room table and over to Dean. You lean over to hand him the paperwork.

His lips purse when he notices the line of Alistair’s gaze—on your ass.

Dean then frowns at you, and your express delivery.

“What’s this? You think it could’ve waited?” he asks in a low whisper.

“Look,” you whisper back, pointing to the section you starred. It’s a report that Roman Enterprises failed to disclose about their product, a double-chambered gun that can store silver rounds and witch-killing bullets as well as salt rounds: the perfect gun for a hunter.

The problem is the safety and performance report. The one Dean has up on his laptop doesn’t match the one now physically in his hands—the one that says two out of three units of this gun fail to chamber correctly on reloading, resulting in a backfire on the user.

Dean’s brows furrow. “Where did you get this?”

“Is something wrong?” Dick asks. He straightens in his seat, his demeanor a fraction sharper.

Dean glances up at him, then at Sam and Cas, who wear similar looks of confusion. Sam raises his brows expectantly.

“Sorry, one moment,” Dean says to the room, before redirecting his attention to you.

You’re all too aware of being the rabbit caught in the proverbial trap in this room of nearly all men, but you rest a hand on the table and lean in near his ear.

“Their weapons analyst sent this to me,” you explain. “He almost got his hand blown off. Said they didn’t want to go back to the drawing board and waste time when they had us as a prospective distributor.”

Dean blinks in surprise. A fucking whistleblower just outed his own company, but he supposes he can’t blame the guy. If he had half a hand, he’d sue everybody.

“Okay, thank you,” Dean tells you.

It sounds like a dismissal, and truth be told, you’re ready to get the hell of this room. You make a quick escape and shut the door carefully behind you.

Dean watches you leave, but then he collects the report you gave him and passes it along to Sam, with a pointed look that says read it now. Sam doesn’t need the prompting. He shares it with Cas, and they both eventually come to the same frowning conclusions as Dean.

“You gonna fill us in on what that little skirt just gave you that has all of you so fucking sour?” Alastair remarks.

It makes Dean bristle. “That’s my assistant. Have some fucking respect.”

Dick shoots his associate a warning look, as well as a placating hand before he folds both of his on the table.

“Apologies. I’d like to move forward here. How about we discuss oversees shipping—”

“No, I don’t think that’s necessary,” Dean says. He shares a look with Sam. He’s disappointed, but he nods in agreement all the same.

Dick’s head tilts. His fake-ass smile twitches at the corners. “Excuse me?” 

Dean closes his laptop and slides your report across the table.

“We deal with all kinds, but there’s nothing I hate more than a liar,” he says. “Cas will see you guys out to your line of Teslas out front.”

You’re sitting at your desk, stress-eating with a snack bag of popcorn while you answer emails, even though your mind is racing as you imagine what might be going on in that conference room.

You perk up in your seat when the door swings open, and the entire team of Roman Enterprises files out with steam practically coming out of Dick’s ears. You’re more than happy to see the back of Alastair. Cas follows them closely, while Sam and Dean are the last ones lingering outside the door.

They speak for a moment there in the hall, though you’re too far to hear what they’re saying. Dean eventually rubs a hand over his stubble-covered cheeks and jawline as he heads toward his office, and toward you. He gives you a wry look when he steps through the glass doors of the reception area, squeezing your shoulder as he passes by.

“Good job, sweetheart.”

That’s all he says as he disappears back into his office. You can’t help the warm blush blooming across your cheeks, but you do get up to follow him.

“Um, Dean…”

He turns to you as the door of his office closes behind you. You fold your hands in front of you, an almost contrite expression across your face.

“I’m sorry. That just cost you a lot of money, didn’t it?” you ask.

Dean shakes his head. “Don’t be sorry. What you saved me is one bitch of a headache, and probably millions in legal fees. So thank you.”

You smile, making him smile in return.

“Okay, um, would you mind if I leave just a few minutes early today?” you ask. “My father usually picks up my daughter after school, but he has a doctor’s appointment. I can come back after she’s settled.”

Dean frowns. “What time does she usually get out of school?”

“Three. She’s in kindergarten.”

He considers it for a moment. “You know, we have a daycare. Cas brings his kids here too.”

You do know that, all too well. Cas is married to Meg in HR, and they have two, very odd twin daughters. You think they’re stealing ink from the printer and using it for “ink blot tests.” You didn’t know that eight-year-olds knew what those were.

“We do. But I, uh…I can’t afford it,” you admit, with some embarrassment. You’re still helping your dad pay off your mom’s medical bills, and even her funeral. It’s not easy to afford to live and provide for a child, but it seems like it’s almost as expensive to die.

Dean taps his fingers on his desk. He shrugs and rounds his desk to sit down in his comfortable chair.

“How much does it cost?” he asks.

“$500 a month. I’m already trying to get her into a private school…”

Dean does the math in his head, easy. Then he sends a quick text to Meg in HR.

“Well, now you can afford it. I’m gonna raise your annual salary by $10K,” he says. “That should cover the tax deductions and extra gas mileage.”

Your mouth falls open in shock. It closes, then opens again before you’re able to make words pass through them.

“Um, w…what?” you ask.

Dean leans back in his chair and smiles. It isn’t often he gets you flustered.

“Consider it an early Christmas bonus,” he says.

You laugh, slightly breathless still in wonder. “It’s the middle of July.”

Again, Dean shrugs. “Just say thank you.”

You bite your lip in amusement, but you nod. Your gaze on him is sincere, and a little shiny with emotion. Your daughter’s definitely getting into private school now.

“Thank you,” you say.

Dean watches you walk out of his office, along with that brief look over your shoulder before you close the door. His smile fades.

“Fuck,” he mutters.

He sits up in his chair and goes for that stash of whiskey under his desk. If he wasn’t already an alcoholic, you sure were on your way to making him one.

Three Months

Dean blows out a sigh, then rubs his eyes at the strain of just how long he’s stared at a screen and tried to make these goddamn numbers work.

The building is probably empty by now. Even his brother left two hours ago to go home and have dinner with Jess. Dean’s reluctant to go home to his empty apartment. So here he sits, the workaholic that he is, as the sun fades behind other buildings and casts his apartment into darker shades. He switches on the desk lamp.

A knock on the door kicks his thoughts out of alignment, like an old engine sparking out, into crispy defeat.

“Yeah,” he calls out without looking up. He does though, when you come into view.

“Hey, I’m heading out,” you say.

He can see you’re ready to go, packed up and on your way downstairs to pick Emma up from daycare. He still hasn’t met the kid. He’s surprised himself with the idea that he wants to, though he’s never asked. Never wanted to intrude on your life outside of work. Never wanted to get too close to it.

You’re a single mother living with your father, and that’s complicated enough. You don’t need a man like Dean upsetting the delicate balance. And he doesn’t think he can give a woman like you what you need…besides the fact that you’re his employee.

“All right. Make sure Benny keeps an eye on you heading to your car. It’s getting late,” he says.

“Not that late,” you say with a smile. Though you’re a bit concerned when you step further into his office. “When do you typically head home?”

“Uh, around eight or nine, usually.”

“That’s pretty late. You don’t have anyone waiting on you?”

“Not unless you count the beers in the fridge,” he remarks, sending off another email to a sales rep to get his ass in gear if they’re going to make quota for Quarter 3.

By the time Dean looks up, he sees your small frown. Concern.

It rubs him the wrong way (or maybe the right one), so he clears his throat and waves you over to his computer, opening up a tab he was looking at earlier.

“Hey, do me a favor. Tell me what you think of these. I have to go to some tech expo this weekend with Sam,” he says.

You look over his shoulder at the rows of ties on the screen.

“Well, first of all, don’t get them off Amazon. Go to a men’s store,” you say with a short laugh. “Second, what color is the suit?”

“Uh, just black,” he says in amusement.

You hum in contemplation. The man does look good in his usual slacks and nice buttoned-down shirts, but picturing him in a full suit and tie is an enticing image.

“This burgundy one looks nice. Or the blue one with the pattern,” you suggest.

“You don’t think it’s too loud?”

“No, I think it would look nice with a black dress shirt. Or hey, a black vest with a white dress shirt underneath.” 

“A vest?” Dean intones.

“Yeah, with your shoulders, you’ll look really sharp when you pair it with the suit jacket,” you say.

“My shoulders, huh? What about ‘em?” he asks in amusement, verging on the edge of flirtatious, before he realizes what he’s doing.

You both pause then.

You eventually find something approaching a respectable response, if not really a professional one.

“Just…you have a strong frame for a suit. I’m sure whatever you pick will look good,” you say. Though you turn away to grab your purse from where you left it leaning against his desk on the floor. Your face is blushing hot all the while. “Um, have a good night. I’ll see you tomorrow.”

“Yeah, you too,” he nods, clearing his throat. He tries not to watch you leave, but he can’t help himself. The natural sway of your hips is too hard to ignore, as is the way you walk away from him on those heels.

Once the door is firmly shut, he tips his head back against his chair and groans. He hates himself for hoping, even fantasizing, that one day you’ll come back and straddle him on this goddamn chair and fuck him with those heels still on.

He bangs the back of his head repeatedly against the chair, as if that could rid him of his pig-like thoughts.

Fuck. Me.

Four Months

Dean steps into his office after four hours of solid back-to-back meetings. If he had to sit through even five more minutes of Crowley’s condescending ass explain 15 subsections of a contract, as if Dean didn’t know how to fucking read, then he was going to throw his laptop into the nearest window.

He expects to find the quiet refuge of his office, and very quickly his stash of Angel’s Envy. What he gets is a kid sitting in his chair, eating his Doritos. She doesn’t look older than five or six, swinging her little legs as she swivels in his nice leather chair.

The sight is so dumbfounding that Dean stops not two steps through the doorway, his hand still lingering on the doorknob. He frowns.

“Hey,” he says. Not in a nice way. In a who the hell are you way.

“Hi!” The kid smiles and waves at him with fingers coated in Cool Ranch Dorito dust.

Dean’s head tilts. “Uh, hi.”

“You said that,” she says.

His lips twitch upward. He points at her, and the chair she’s sitting in.

“That’s my seat,” he says, with some censure in his voice. “You wanna get down?”

She blinks and pauses, realizing she might be in trouble.

“Sorry.” She slides down carefully without letting go of her snack. She wears a private school uniform: a plaid skirt, navy polo, and a matching headband. Her pink Peppa Pig sneakers give away her personality though. It matches her backpack, which boasts a Minnie Mouse keychain and a princess sticker of Belle in her yellow ballgown.

“What’s your name?” he asks.

“Emma,” she replies.

Dean’s brows raise high in recognition, then they furrow.

“Interesting. Where’s your mom?”

“She had to talk to Miss Nancy, so she told me to stay here.”

Miss Nancy. Gotta be the daycare lady, Dean thinks.

“Here? As in, my office?” he asks in suspicion. “Or did your mom tell you to hang out at her desk?”

Emma guiltily glances down at her feet instead of at him, like Sammy did when he was four, and didn’t want to admit he broke their dad’s watch.

Here, it looks like Emma got bored and wanted to go into the big mysterious room. She continues eating her Doritos.

Dean can’t help but smile. “Did you find those in my desk drawer?”

She blinks up at him with the face. Like when Sam got caught looking through their dad’s old collection of baseball cards with peanut butter and jelly stains on his hands. That puppy dog look had Dean taking the fall—and the week-long grounding.

Emma tentatively offers him her snack. “Want one?”

The look on her face tells him that she’d rather not share, but it’s a clever little manipulation with those big doe eyes. Girls learn quick, don’t they?

Dean shakes his head and pulls out a nearby guest chair after setting down his laptop on the desk.

“It’s okay. You can sit here if you want,” he says.

The chair is a little high, so she reaches for the edge of his desk to help her. Dean offers her his hand instead. She’s happy to settle her little Dorito grime-covered hand in his and have him help her into the chair.

“Thank you,” she says, with that cute little voice. He almost laughs.

“You’re welcome,” he says. You’re definitely going to owe him for this one.

Dean sits at his desk and contemplates just what the hell he’s going to do with this kid for the next few minutes. At least, he hopes it’s just a few minutes. Does he need reinforcements? Should he call Sam up here? Cas?

“Are you and Mommy friends?” Emma asks.

Dean considers her question with a quirk of his head.

“Yeah, I guess you could say that. I work with your mom.”

“She said you’re her boss.”

“You know who I am?”

“Yeah. Your face is on her phone when you call,” Emma says. When she finishes the chips, he can tell she’s looking for a garbage can. He takes the empty bag from her and tosses it in the small bin under his desk. He wishes he could pour himself a much needed adult drink, but he thinks you’d have something to say about that later.

He settles on the bottles of water you keep putting in his other drawer. He grabs one for the kid, and even opens the cap for her, like he used to do for Sam when they were little.

“Uh, how was school?” Dean asks. Because what else do you ask a kindergartner?

She shrugs. “Okay.”

Fair enough, he thinks. He never liked school much, but he has to keep this conversation going somehow.

“Just okay?” he asks.

“Yeah. I don’t like math, but Music was fun. We’re learning how to play the recorder. Oh! And I drew Peppa after school. Wanna see?” she says, pointing at her backpack.

Dean raises a brow, but he grabs her backpack off the floor and hands it to her. She unzips it and rifles through her notebooks and her modest collection of crayons. She then pulls out her prized drawing to show him. It looks more like a ball of pink squiggles to him. But he looks harder, and he can see the eyes and the mouth and the nose are close enough to the character on her sneakers.

“Hey, that’s pretty good,” he indulges her, earning her shy smile.

“Thank you,” she says. But her face soon falls. “I wanted to draw her yellow crown, but a boy took my crayon and broke it.”

“Aw, that sucks,” Dean says. Though a smile threatens his lips at the little angry pout on her face. “What did you do when he wouldn’t give it back?”

“I just pushed his arm and he fell and cried,” she says.

Dean blinks in surprise. “Oh.”

Yikes. No wonder you had to go back and talk to Miss Nancy.

“But I didn’t mean to! He was mean to me first,” Emma argues.

Dean shakes his head in amusement, once again tempted to laugh.

“Well, you know, you should never put your hands on somebody. You wouldn’t want him to hit you, right?” he reasons.

The girl considers it, still with that little pout, but she nods begrudgingly.

“See? But if that kid messes with you again, you come tell me, okay? I’ll set him straight, man to man,” Dean says.

She starts to smile again. “Promise?”

“I promise. Let’s shake on it,” he says, giving her his hand. She puts her much smaller one in his, and they shake on it like adults.

“Emma?” your voice calls from outside the office in worry. The door is still open, so you catch sight of your daughter just as Dean tells you to come over. Your eyes grow wide with embarrassment as you realize where Emma ended up. You hasten inside his office.

“What are you doing in here?” you ask her sternly, taking her hand and leading her off the chair. “You were supposed to be doing your homework at my desk. Dean, I’m so sorry. I didn’t think it would take so long.”

“It’s all right,” he says.

You still look a bit mortified and apologetic.

“Seriously, it’s okay. She’s a good kid,” Dean says. You smile, if a bit wryly as you caress her head.

“Well, she wasn’t on her best behavior today, so we’re going to sort that out tonight. But thank you for watching her.”

Dean sends you off with a raised hand, though it turns into a small wave when Emma looks back at him with a sneaking smile.

He chuckles and shakes his head. Kids. Jesus.

She looks just like you.

Five Months

The insistent ring and vibration of your cell phone disturbs your deeply rooted slumber. You slap at the device charging on your nightstand and nearly yank out the cord in attempt to bring the screen to your eyeballs.

Once your bleary vision adjusts to the brightness, you growl in annoyance.

Still, you answer the call.

“Dean. Jesus Christ, it’s three in the morning.”

“I just need your opinion on the new crossbow flame throwers.”

Your sigh can probably be heard across the Atlantic Ocean.

“It’s fine, but it would make more sense on a gun, right? Half gun, half flame thrower.”

“That’s what I said! But Cas says we need to diversify—”

“Dean. Three. In the morning. Go to sleep and let me get back to dreaming about Pedro Pascal as a gladiator, feeding me grapes as his queen.”

“…You like Latin guys, huh?”

You groan and turn your face fully into your pillow.

“Sleeping now. I’ll see you in five hours.”

Six Months

“Look! Emma got first place in the Spelling Bee.”

You pass Dean your phone while he scrapes the pickled onions off his burger and onto your plate. In turn, you give him the pickle wedge off your plate. By now you know that he’s a veritable bottomless pit when it comes to food in general, except for the fact that he doesn’t like pickled onions, and doesn’t trust sushi.

He smiles as he scrolls through the pictures of your daughter’s kindergarten class.

“Clearly taking after her mom in the smarts department. Though you didn’t have to do her like that with those Pippi Longstocking braids,” he remarks.

You scoff in amusement. “Oh, come on, they’re not that bad. It’s not like she’s got a wire hanger in there. She’s just going through a frizzy phase. No matter what products I use, I can’t seem to tame that hair.”

Dean chomps his burger. You’ve reminded him at least 30 times, but he still talks with his mouth full.

“Looks like she’s trying to land a plane,” he says.

You snort, shaking your head. You shove his arm lightly and go back to eating, while Dean takes another look at the pictures.

He sees a lot of you in that little girl. She’s got your eyes, your smile, but she probably has her dad’s hair, his chin. Dean hopes that’s all the girl’s going to get from that fucking deadbeat, biologically speaking. From what you’ve told Dean, all that guy is good for is sending monthly wire payments. After you got your raise, he even tried taking you to court to get his child support reduced.

“Did you want kids—you know, before? Was that even on your radar?” Dean asks.

He doesn’t know what possesses him, but he asks.

You hum in contemplation. “Honestly, it wasn’t. I was focused on my career.”

You wipe your mouth as the thought settles in.

“I thought I’d do it right, you know? Work hard, achieve my goals, find a husband who wanted the same things I did, then build a life, and a family. I always thought I was smarter than a broken condom in the back of his goddamn Lexus,” you say, your tone bordering on disgust at the end. You shake your head and sip your iced tea.

Dean quirks his head. “Well, we’ve all been thrown a few curveballs in life. What matters is how you take it. And I’d say you’ve got the better end of the deal. You get Emma, a good job, the best boss in the world…”

You shoot him a knowing smile.

Dean smirks, but he’s still serious.

“And that guy, all he gets is a life without his kid, and without the woman who could’ve given him a family,” he says. “Sounds like a fucking chump to me.”

He continues eating, but you’re not sure if he realizes how that just tilted your entire axis. It makes you look at him differently, the warmth of admiration in your chest, and something deeper coiling in your belly, stirring up something unexpected.

You stare at him long enough that his brows furrow.

“What? Got something in my teeth?” he asks. 

Your face relaxes, your lips tugging at a smile.

“Yeah, ground beef. Can you please swallow before you talk?”

“This is how I am, sweetheart. Don’t try to change me,” Dean says, taking another massive bite. Oily ketchup dangles from the bun and threatens to stain one of his nicer buttoned-down shirts.

You roll your eyes. “Wouldn’t dream of it.”

You stick a napkin in his collar, just in time for the ketchup drip.

Seven Months

You and Sam have lunch together every Wednesday. It started out as a way to reconnect with your old friend, but it’s often devolved into an hourly venting session about his brother’s many idiosyncrasies, how he’s driving you both fucking crazy, and how to best manage the man’s schedule, as well as steer him away from any half-cocked decisions that could cause a PR disaster.

Like the time he accidentally asked a reporter at a charity benefit why albacore tuna was becoming an endangered species.

“I mean, come on. They’ve literally got fish on the menu tonight. Maybe if you people stopped eating so much damn sushi with your avocado toast, we wouldn’t need this bougie dinner party. $5,000 a plate? Give me a fucking break.”

The fact that he slept with her that night still didn’t save him from the article she published later that week, complete with direct quotes. She had a good goddamn memory.

Today though, your weekly lunch with Sam is less about quasi-therapy, and more about celebrating the fact that Jess is pregnant. You’re even helping her and her sister plan the baby shower.

“Any advice? Just, you know, about parenting in general,” Sam asks. For once, he seems less his normal confident self, and a little more sheepish. It’s sweet, even endearing.

You smile. “God, I don’t know. I’ve been winging it from the beginning. Just…be present, as much as you can. Jess is going to need you to show the hell up, without being asked, without being nagged. You’re the rock she’ll need to lean on, even when she thinks she can do it all while you’re here trying to show up for the job. Especially when the baby’s born. If you’re not covered in three layers of bodily fluids, then you’re not doing it right.”

He laughs a little. “Noted.”

Your mind veers into other directions as you finish up your sandwich and crumple up the foil wrapper. Most predictably, along the road that leads back to Dean.

“Dean doesn’t seem to be the family man type,” you remark. “More married to his work, but…he’s been really good with Emma every time I’ve brought her up to visit the office.”

“Doesn’t surprise me. He basically half raised me after Mom died. More than half, actually. Dad was always working,” Sam says.

“What about relationships?” you ask.

It earns you a certain look from Sam. You’ve come to learn that both Winchester brothers are incredibly sharp, just in different ways. Dean knows how to read people. He’s a good judge of character, and it makes him a shark in the board room, the kind of man that can take in the information his department heads serve him and make swift decisions that often pan out well for HunterCorp.

Sam is perceptive in an almost clinical way, analytical and methodical. He’s the one who can read the data and find the one thing that’s missing. He can anticipate problems before they start, and when it comes to people, Sam often catches the little things, tells and underlying motivations. It gives you away before you’ve even realized it.

“Well, Dean’s been pretty predictable when it comes to women, even before Dad passed,” Sam says.

And it’s true. Dean’s never seen the same woman more than a week at a time. You know this, because you’ve seen the “consolation gifts” he sends them. A Tiffany bracelet. An Apple Watch. Gucci sunglasses. The perfect gift that tells a girl she won’t need to stick around for breakfast.

“But to his credit, he’s up front with them,” Sam says, drawing your gaze. “They know what not to expect.”

Your lips quirk. “Sounds so transactional…and lonely.”

“Yeah,” Sam nods, “but I get it. He took a lot onto his shoulders when Dad died. Right now, Dean’s more focused on making sure we survive than on what he might want. To be honest, I doubt he’s even thought about what that is.”

For some reason, that hits you behind the ribs in a quiet, sharp strike. In your mind, you can’t help but see the familiar tense set of Dean’s shoulders hunched at his desk, eyes glued to his computer while an evening sun sets behind his head.

Even in that big office overlooking the entire city scape, he never has time to admire the view.

Eight Months

It’s your mistake.

Your fingers brush Dean’s for half a second too long when you give him a stack of purchase orders to sign. His eyes meet yours. You point out the new way you’ve color-coded the departments for each PO.

Your heel wobbles on your pivot, an uneven floorboard. Suddenly it’s his hand closing around your wrist and the other wrapping around your waist, giving you stability. Your eyes meet his, heated breaths in between.

A thank you falls from your lips, drawing Dean’s attention there.

But he lets you go.

You walk away, pretending you don’t know his eyes are following you.

You bite your lip against a smile.

One Year

“Seriously, which one?”

“Jesus, Dean. Green! I already told you.”

“No need to get snippy. I just want your opinion.”

“You always want my opinion. That’s why I already laid out the green one for you.”

“But I like the black one.”

“You always wear the black one. The black one says politician. The green one says you’re the boss, but you’re approachable.”

“I don’t want to be approachable. That’s how I get stuck in a 45-minute fucking conversation in the break room with Garth about his side hustle YouTube sock puppet show. That shit was deeply uncomfortable. I just wanted my damn coffee.”

“You know, you could also cut back on the caffeine and the booze while we’re on the subject.”

“Oh, what are you, my mother?”

“You tell me. I’m the one dressing you right now.”

You work the collar dark green suit jacket over his shoulder and smooth down the wrinkles. You firmly ignore how his gaze roams your face, and lower still. You want to pretend you haven’t noticed these signs, all while you try to stop yourself from giving any yourself.

“There, looks good,” you say. Though you make the mistake of meeting his eyes.

He grins. One of those grins that makes you want to grab his face, either mushing it into his seventeen mugs of coffee, or kissing him fucking stupid. You’ve been restraining the latter urge by a tenuous thread for several months now, mostly because you sicken yourself.

He’s your fucking boss. It’s unprofessional. You’ve already been down this road once in your life, and—

“You okay?” he asks.

Suddenly you realize how close he is. You can feel the warmth of his body, you can smell his cologne, and he sounds so sincere in his concern, briefly touching your arm.

You nod, knowing you should create some distance between you and him. Somehow you can’t force yourself to take that one small step back.

Instead, you reach for his tie. “Remember, you’re meeting Frank Devereau and his wife tonight, and Charlie Bradbury. She’s the brains behind the project, so you’ll want to talk to her about the details, how the program works, and how we can incorporate it into our existing tech.”

Dean hums in agreement, but in truth, his attention is on your nimble hands as you work on his tie. You slide the knot up to settle snugly, but not too tight against his throat. You allow your hands to slide down his chest while you admire your handiwork with satisfaction, but your small smile fades. Your mouth goes dry as your gaze travels back up to his, lingering on his parted mouth.

His hands slowly come to hold you by your arms, making your heart tap a syncopated beat.

“Does that look mean you want me to kiss you, or am I just seeing things?” he says at last.

Your eyes widen. You bite the inside of your lip, nervous energy fluttering through you, even as everything within you would like to scream a resounding yes.

“We can’t…shouldn’t,” you say, in a quieter voice. His office door is closed, but it’s not locked. There are far better reasons than that though, and you struggle to remind yourself of each and every one of them.

Dean steals your focus, however. His eyes seem greener than usual, probably because of the jacket. You picked it with that in mind.

“In this case, shouldn’t isn’t a moral argument,” he says. “It’s society’s rules. I don’t know about you, sweetheart, but I’ve never much cared about what people who don’t matter think about me.”

Your brows begin to knit together. “Who matters to you? Because my daughter and my father. They matter to me.”

“Being with me doesn’t hurt them,” he argues, a little peeved at the implication that it would; that he would hurt them, or you.

“Being with you?” you ask in shock.

Dean’s mouth opens, but he hesitates, like what he just said surprises even himself. His lips quirk at a smile.

“I know you, uh, probably think I’m not capable of something like that,” he asks.

“I mean, it is surprising,” you admit airily. Your cheeks warm in a blush. “You could have anyone, Dean…and you have.”

He chuckles dryly. “All right, fair enough. But other than Sam, who gets me better than you? Who else is gonna handle this, the pressure of my life and everything that goes with it…better than you?”

Your eyes widen. A softer smile threatens your lips, because you realize then that he’s actually serious.

About you?

Of course, that’s when your very real, rational doubt creeps in.

“People are going to talk,” you point out. “That’s why shouldn’t always matters. And you and me? Jesus, Dean, this is the oldest cliché in the fucking book.”

His hands move down to your waist, squeezing gently. Enticingly.

“Then we’ll be discreet,” he says, with one of his crooked grins. You shake your head, but you start to smile too. You allow him to pull you back in, figuratively and literally as he bows his head closer to yours.

“You really think you can pull that off?” you ask.

“Sweetheart, with the right motivation, we can pull off anything,” he says, half whispering them on your lips as he captures them with his own.

It’s slow and laced with a curling heat that licks tingles down your spine, just like his hand moving to the small of your back, pressing you into him. Your body betrays you then, with a moan in your throat and your own hands traveling up his arms, over his shoulders, cupping the back of his neck.

The graze of your nails at his nape makes him shiver and groan as he licks into your mouth, holds you tighter. You feel the press of his growing arousal against your belly.

Your good sense knocks at the door of lust and yearning, reminding you that you’re making all the same mistakes again. This isn’t a man you can trust—not with this. But Dean’s lips are hard to ignore, covered in the remnants of your lipstick as he kisses his way along your jaw and down your neck, where he sucks and nips just hard enough to make you gasp his name and writhe against him. He squeezes your ass and smiles against your skin.

“So fucking beautiful, you know that? Even the little sounds you make when I touch you. I wanna find out what that pretty voice sounds like when you come,” he says, in a voice dripped in whiskey and wicked promises.

Jesus. Your heart flutters. You haven’t been touched like this in so very long. You haven’t felt desired like this in…

“How long have you been thinking about that?” you ask, a little breathlessly. He continues his exploration, his lips blazing a sensuous trail down the column of your throat, along the line of your collar bone, and between the rise and fall your breasts. He slides open the buttons of your blouse with a practiced hand, his eyes drinking in the sight of your lace bra.

“Since the day you started wearing these sexy fucking heels,” he says, dragging his hand up your thigh, over your skirt, in a way that raises goosebumps on your arms. But he hesitates. His eyes ask a question as they meet yours.

“You need to tell me what you want though,” Dean says, more seriously than you expected. “You want me to touch you?”

Your heart feels like it’s beating in your throat, but you nod, biting your lip.

“Kiss me, touch me, make me fucking come,” you say. “But first, you need to lock that door.”

A crooked grin spreads across Dean’s face. He steals another kiss before he does exactly that—he crosses the room and locks that fucking door. You lean against his desk for a breather, but you realize that half this shit needs to go. You move stacks of files to the side, the coasters you put for his mugs of coffee along with the empty cups themselves. You push his double-screen monitors forward, giving Dean just the angle he needs to hold you from behind and start laying more tantalizing kisses along your neck.

You sigh and help him with the zipper of your skirt while he works on the bra clasp. The straps loosen down your arms, and he flings the bra away so he can get a handful each of your breasts. You moan and rest your head against his as he begins to squeeze and tease, gently twisting your nipples between his fingers. He leaves open-mouthed kisses against your jaw, sucking at your pulse point.

When his hand moves further down and slips behind the waistband of your skirt and panties, he feels your pulse flutter and trip along with your gasp. His fingers dip between your folds and find the slick mess of your arousal.

“Goddamn, baby. Soaked for me already,” he teases.

You don’t need to see his face to know that smug smirk is plastered across it. You reach back and tug sharply on his hair.

“You can gloat, or you can fuck me,” you retort.

He chuckles and kisses your temple. “Don’t you worry. You’re gonna have to bite down on my belt to keep from screaming in a minute.”

His hand that never left your breast begins to strum the hardened, sensitive nub, at the same time his other hand finds your clit. You shudder against him at that first touch, that perfect moment when you realize he knows exactly what he’s doing as he learns your body. He circles your clit slowly, but with a delicious pressure until it swells under his fingertips.

Then his long fingers dip down into your needy channel, making you whimper as you hold onto him and the desk for stability. His fingers pump smooth strokes inside you, almost as deep as he plans to fuck you with his cock.

He knows he has you when his fingers curl and brush deliberately against that perfect spot inside your inner walls. Your thighs begin to shake, your breaths labored, your hips bucking against his hand in a quiet plea.

Your orgasm rolls swift and steady against his fingers. Your pussy flutters around his hand, and he groans along with you.

“Good girl. Can’t wait to feel that squeeze around my cock,” he says, a filthy whisper in your ear.

You laugh a little, nodding in agreement. You turn around to help him with his belt.

“Yeah, right now. Want you inside me before we run out of time. You have to meet Sam downstairs soon.”

It’s another work event Dean can’t get himself out of, even if the networking opportunities are good for the company.

“You should come with me,” he says, grinning at the way you slide his jacket off his shoulders, but you toss it as carefully as you can across the nearest chair. You just had it drycleaned this morning.

“What?” you laugh. “Dean, you don’t need me there. I’m just an assistant—”

“No,” Dean says, stilling your movements when his hand cups your cheek. Your lashes raise as you look up at him, finding him serious again. His gaze roams your face, his thumb brushing your lower lip. “If it ain’t fucking obvious, you’re more.”

Your mouth falls open, but you’re not sure what’s going to spill out. Dean doesn’t give you time to figure it out, or even let himself settle into his own admission.

He just kisses you, hard and thorough, knocking any more doubts out of your mind, and any deeper thoughts out of his.

He grabs you up by your hips and seats you on his desk, rattling the surface. Your arms wrap around his shoulders on reflex. You feel the muscles flexing under his dress shirt—a crisp black. You help him yank up your skirt and kick off your panties, though they get tangled around your ankle. His slacks and boxer briefs end up coiled around his knees, just far enough to give him room and leverage to slide into your heat.

You both moan at the feeling of him settling snug inside, bottoming out, his almost bruising grip on your ass. Your thighs are wrapped almost as tightly around his waist as he lays you out more fully on the desk. It’s probably harder to do it this way, instead of him just bending you over the hard mahogany. But you’re glad you get to see his face, get to run your fingers through his hair and share his breaths while he fucks you in a slow-rolling rhythm.

It’s more intimate. It feels like it means something, especially when he once again cradles your cheek and brushes wild strands of hair away from your face. Especially when he kisses you deep enough to taste the Almond Joy you snacked on earlier.

You kiss him back just as fervently, as if this will be the first and the last time. You have no idea what happens after today, and you know that probably makes you a fucking idiot. It could lead to the end of your second chance at a career, but you want to trust this. You want to trust the steadiness in Dean’s hands and the look in his eyes.

So you give into what you want, sitting up to lay nipping kissing along his prickly cheek and neck, sucking your own marks against his skin. The way he groans and shudders and fucks you harder—it makes you feel powerful.

“Lean back, sweetheart,” he grits out. “Touch yourself for me.”

You manage to follow his lead, shakily laying back down and letting your hand drift back down your body, finding your clit. Dean watches you play with yourself, his fingers flexing against your hip. You feel him so deep, so good, that the coil of pleasure in your lower belly begins to tighten in earnest.

He’s only satisfied when you have to smother your own mouth against a cry, your hips snapping up to meet his as your release finally hits. Another few ragged strokes, and he spills into you as well.

“Fuck,” he groans into your neck, catching his breath. That was awesome.

But then, his eyes widen. “Christ, forgot a condom.”

“I’m on birth control.” You breathe out a laugh as you soothe him, caressing his shoulders.

He blinks, then he relaxes, chuckling faintly.

“Guess you just make me lose my head,” he says.

“It’s okay. I’ve gotten used to doing the thinking for you,” you tease, biting your lip.

Dean stares down at you, brows raised, yet amused at your cheek.

“Hmm, I’m gonna remember that one. Might have to punish you tomorrow,” he remarks.

You smirk, though a blush burns down your neck at the idea, and the depths of his voice.

He withdraws from you with a quiet moan, then helps you up with a steading grip on your arms when he feels that you’re still a bit shaky. After pulling up his pants, he finds the paper towels you keep handy in one of his desk drawers for the cleanup.

“Seriously, come with me tonight. I’m sure you’ve got a nice dress. If not, I’ll buy you one on the way,” he says, as you two start to pull your clothes back on. And in your case, find your bra.

“Dean, I need to take Emma home,” you say.

You pause with your fingers poised on his dark green jacket, ready to smooth down any wrinkles. The color matches his slacks perfectly. His hair is a bit messy, but overall, he looks edible and professional at the same time. He’s ready to shmooze with the heads of conglomerates and Silicon Valley tycoons and the politicians they own.

But you know you’re not a part of that world.

“Maybe next time,” you say, though you don’t really mean it. Your hand falls.

Dean nods, but he catches your hand before you walk away from him. He slowly winds you back in and kisses you thoroughly enough to make your knees buckle, just a little.

You’re still not sure if he meant what he said about wanting to be with you, or if this is just something he’ll change his mind about in the morning after a few glasses of whiskey.

You definitely think about more than just the road ahead while on your way home, Emma’s chatter filling the car. For once, you can’t say you’re fully paying attention.

Your fingers keep touching the memory lingering on your lips.

AN: 😘❤️‍🔥 How'd you like the slow build? lol Did Dean's earnest appeal surprise you there at the end? He's been a pretty successful play boy up until now, but he's really going to prove himself in Part 3 of our adventure, set shortly after Pratt Fall.

Next Time in Nothing by Halves:

Dean finds a guest spot in front of the school. The old Impala rumbles to a stop there, and he climbs out, grabbing the bouquet resting in his passenger seat.

His keys jangle in his other hand as he makes his way to the front office to check in, just like you told him to in your texted instructions. The nice ladies there give him a guest badge that he slaps on his chest, over his dress shirt, and they tell him how to get to the theater. He feels awkward and out of place walking down the halls of this school alone, but you had to take Emma over there early before the show. 

The hell am I doing here?

He has to fucking wonder.

But he promised you. He promised the kid. So he’s here.

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“What?” there’s a screeching sound behind you and then, you feel something bump into your bicycle. “Ah! Help!!” you end up on the street, crying out in pain as your neighbor screams in terror.

“OH NO! Someone, call an ambulance. This rude man just ran Y/N over,” Mrs. Babcock clutches her hands to her chest, crying bitterly as you slowly try to get up.

“Sonofabitch! Don’t you have eyes girl? Who drives like a maniac on a street with a bicycle,” he looks at your bicycle bucket, huffing. “What the fuck!”

“Ouch,” you whine as the man easily picks you up in bridal style to place you on the sidewalk. “My flowers! No!” You cry as the lilac and peonies lie on the street. “We need to save them!”

“Flowers?” the man grunts. “Your bicycle is damaged; your knees are bleeding and you almost got killed in a car accident, but you care about some flowers?”

“They are beautiful and smell good,” he looks down at you, laughing as fat tears roll down your cheeks. “Please save them, Sir.”

“Sheesh, sweetheart. Are you sure you didn’t hit your head? Did the helmet a poor job and your brain got damaged?” he cockily asks, furrowing his brows as you try to get back up. “No! You will sit there and lemme call an ambulance. I don’t want you to sue me.”

“Sue you?” confused you look up at the stranger. “I only wanna check on my new bicycle and flowers. It was an accident, right? You didn’t run me over on purpose.” You shrug as the man pinches the bridge of his nose.

“Sit over there and let me call help. I will check on your knees in a second,” he stomps toward his car to open the trunk. “Where is the fucking first aid kit.”

“I got one at home,” you try to be helpful. “I can fix this easily. I fell off my bicycle more than once. Sir? Did you hear me?”

“Sammy, you need to bring an ambulance and swing your ass over here. I kinda bumped into a biker,” the man grumbles into his phone. “No, not a biker. A girl on a bicycle, Sammy.” He makes a face as you hobble toward your bicycle to pick up the flowers. “Girl, stop with the flowers.”

“I need to pick them up and put them in a vase,” you smile while picking the last flower up. “Look, the peonies and lilac are fine.” You always look on the bright side. Your knees are still hurting but your flowers made it out alive.

“Girl, what?” the alpha huffs as you carefully place the flowers on the hood of his car. “What are you doing?”

“I need to pick my bike up, too,” making quick work you crouch down to check on your bicycle. “Hmm…looks like my taillight got damaged. Everything else looks good.”

“You shouldn’t even move,” this time he picks the bike up to carry it toward his car. “We will wait for the ambulance and my brother.”

“Why? I’m fine,” he’s close to losing his patience as you look up at him with doe eyes. “See, my dress isn’t even dirty.”

“Yeah, it’s torn, sweetheart,” you giggle as he seems to be more worried about you than you are yourself. “Look, I’ll pay for the dress and your bicycle. That’s all.”

“Don’t worry,” patting his chest you smile up at him, “I can fix my bicycle and the dress. No problem. You can drive home now.”

“Do you want to sue me? Do you think I’m stupid?” you are still smiling when the alpha starts to throw insults at you. “Did you do this on purpose? You want to make fast cash, huh?”

“Young man, you ran poor Y/N over,” your neighbor tuts. “It wasn’t her fault you are rowdy, Sir.”

“It’s alright, Mrs. Babcock,” you softly coo. “He only tries to protect his money and reputation. Just look at him.” You look the man up and down. “His suit, the perfectly manicured fingernails, his car. This man is rich and believes he can buy everyone and anything.”

“Now she shows her claws,” he smirks as you turn around to hobble toward his car. You pick the flowers up and slowly walk toward your bicycle to put the flowers back inside the bicycle bucket. “Where do you think you are going, girl?”

“Home,” your neighbor laughs as you slowly push your bike along the sidewalk. “You should do the same.”

“What? I—” he throws his hands up as you leave him behind, not looking back. “Where is she going, ma’am?”

“Oh, Y/N lives down the street. She’s a nice one. A bit crazy, but we all love her,” Mrs. Babcock says. “She’s not the kind of girl lusting over money and shiny things.”

“Miss, please open the door,” you reluctantly open the door, as a tall alpha stands in front of your door. “Hi, my name is Sam Winchester. My brother Dean ran you over with his car. He wanted me to check on you.”

“I’m fine,” you point at the band-aids on your forehead and knees. “I don’t want his money. I’ve got all I want here.”

“Please just let my friend check on you. Dean is worried about you,” Sam points at a young brunette omega. “That’s Alex. She’s a nurse.”

“Do I have to,” you whine as the alpha running you over shoves his brother aside. “Hey, what are you doing?” He makes his way toward you to look you all over. His large hand cups your cheek to tilt your head. “What?”

“Dean, calm down. She doesn’t want to sue you,” the other alpha sighs while placing his hand on his brother’s shoulder. “Let me handle this.”

“I gotta be sure she won’t—” you whimper as Dean leans closer to eye the band-aid on your forehead warily. “Hello Kitty?” He smirks. “How does your head feel? What about your knees?”

“I told you, I’m fine,” you shove against his chest. “Can you not put your stink all over me?” Dean grumbles as you scrunch up your nose. “You stink like bourbon and leather.”

“You don’t like my scent, sweetheart?” he almost looks offended. “I do not stink. It’s called scent. And you forgot sandalwood. Take another whiff.”

“Dean, we came here for a reason, not for you to flirt with her,” Sam interjects. “Dean!!”

“What?” Dean snaps back, growling at his brother. “Do your job and let Alex check on her. I don’t have time to come here again. I got a meeting with the members of the board.”

“Well, then you shouldn’t have run a girl over in your free time,” you chuckle at the taller alpha’s attitude. “Miss, please let us in before my brother loses his mind here.”

“Come in,” opening the door wider, walking with it you let Sam, Alex, and the grumpy alpha mumbling curses under his breath, in. “Do you want some homemade lemonade and a slice of pie?”

“Pie?” Dean walks a little faster as you make your way toward your kitchen. “Wait, your kitchen is pink?” he chokes on air. “There are flowers on every surface too.”

“I like pink, and flowers,” you open one of the cabinets to get four glasses out. “Do you want some pie too?”

“Pie for me,” Sam chuckles as his brother eagerly takes the offered plate with pie. “I love me some pie.”

“And look,” Alex laughs as Dean already shoves pie into his mouth, “there are flowers on her glasses too.”

“She loves flowers,” chewing audibly Dean sits on one of your kitchen chairs, snickering as none of the chairs matches. “This is like some crazy drug-induced dream. Green, yellow, and blue chairs mixed with a pink kitchen. Flowers everywhere you look.”

“Hey, I love my furniture,” you glare at Dean. “You’re not nice.”

While Alex checks on your forehead and knees, Dean happily munches your pie. He looks around your kitchen, smiling to himself as there are flowers on the tiles, too. 

“How is she?” Sam asks. “Do we need to call an ambulance or bring her to a doctor?”

“She cleaned the cuts and put a band-aid on her injuries. There is nothing I can do,” Alex takes a large sip of your homemade lemonade. “We should leave her alone now.”

“I can buy her a new bicycle,” Dean offers. He looks at his now empty plate, licking his lips. “Do you want a newer model?”

“I like mine,” the alpha watches you clean the table, always aware you could change your mind and sue him. “It’s perfect and—”

“Pink,” he shakes his head. “You are a strange omega.” You frown at his words. “Pink everywhere. Flowers. Hello Kitty.”

“I like it. If you would excuse me now, I got things to do.”

“Buy more flowers or pink stuff?” Dean gets up from his chair to follow you out of your kitchen. “I bet you got pink pillows and sheets, too.” You whine. “Oh, I’d kill to see them.”

“You’re not a nice alpha,” you point out. “I didn’t comment on your boring black suit, black shoes, and black car. I kept my mouth shut. Why don’t you leave me alone?”

“It’s a classic car,” he growls low in his throat, causing you to take a step back. “A 1967er Chevy Impala. She’s my Baby! You don’t make fun of my Baby!”

“But you can make fun of everything I own?” you cock your head. “I like flowers, pink and fluffy things. What’s the problem?”

“Fluffy things too,” the alpha smirks. His eyes drop to the colorful turtle slippers on your feet. “Man, you’ve got an odd taste.”

“I like them. Turtles are cute,” you sniffle now. “Why do you make fun of everything? You make me feel bad about myself and my taste. I don’t like you.”

“Dean, can you just not make her cry,” Sam watches his brother cup your cheek. “Dean, we should go now.”

“No, I want to see her pink pillows.”

“I won’t show you my pillows,” you wipe your eyes. “Go. Keep your money and your opinion to yourself and leave me alone.”

“Those slippers,” dropping his eyes back to your feet Dean smirks, “where did you get them?”

“Why?” you carefully try. “Do you want to tell the shop owner you hate them?”

“No. They just look very warm and comfy. I get cold easily and—” he grunts as you wrap your hand around his wrist to lead him upstairs. “Where are we going, girl?”

“Y/N,” you correct while guiding Dean toward your hobby room. “I make them.”

“You make what?”

“The slippers. I make them and other stuff,” he follows you inside your hobby room, nodding as you point at the sewing machine in the corner. “It’s a hobby.”

“A hobby, hmm…I see,” Dean looks around the room filled with shelves full of printed fabrics, wool, plushies, and yes, more crazy slippers. “You got Scooby Doo ones too.”

“My favorite,” hands on your hips you glare at Dean. “I dare you to make fun of Scooby.”

“I love him,” Dean drinks the room in, smiling to himself. “He’s my favorite, too.”

“Where is Dean?” Alex impatiently glances at her watch. “It’s almost two hours since we left the house. What takes him so long?”

“I think he has a thing for that cute omega,” Sam laughs as he looks down at his phone. “He just wrote me that Y/N will measure his feet to make a pair of slippers for him. Scooby Doo ones.”

“Only Dean manages to run a girl over and win her heart,” the brunette groans. “Can we go now? I don’t want to watch the poor omega fall for your brother.”

“That tickles,” Dean whines as you try to measure his feet. “Why do you have to do this. Can’t you just make them?”

“Patience, Dean,” looking up at Dean you knit your brows together. “You need to learn to relax and take a deep breath sometimes.”

“You’re something else,” he watches you make quick work while Dean doesn’t know why his heart beats a little too fast close to you. “Why do you do this for me?”

“If you like Scooby Doo, you’ll get a pair of slippers. No problem.”

“How about I pay you for it?”

“I don’t want your money, Dean,” you pat his knee. “You can’t buy my slippers for money. They are a gift.”

“You’re too good for this world. Maybe you need someone protecting you from this world so you can keep on being the nice person you are,” licking his lips Dean watches you sit next to him. “How about we go for dinner tonight?”

“How about ice cream this afternoon?”

“I got a meeting,” he says.

“Skip the meeting and go for ice cream,” Dean chuckles as you hold out your hand. “Come on, live a little.”

“Live a little,” the alpha takes your hand, feeling his heart flutter. “I think they will survive not having me around for yet another meeting…”

>> Part 2

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Castiel licks his suddenly dry lips. “Hi,” he says, then remembers that this is the man who is worth billions and who has power over his literal job (and therefore his living situation and eating situation). “I’m, uh, from IT? There was a problem?” 

Mr. Smith blinks at him for a long moment, and Castiel wonders how he could have possibly screwed up so soon. Then he gathers himself and gestures towards his computer. “Yeah. I got here first thing, and it won’t turn on.” Castiel chances a surreptitious look to make sure it’s plugged in and comes back with inconclusive results. “Think you can do something about that, Steve?” 

Heat floods Castiel’s cheeks. He hadn’t really looked this morning when he grabbed at his nametag (he hadn’t really looked when he grabbed for a shirt, a fact of which he is almost painfully aware of now that he’s standing in front of Mr. Smith), and of course he’d grabbed the joke. 

“Castiel,” he mumbles, and immediately regrets it. What does it matter that Mr. Smith knows his name? He’s never going to see the man again, so really why does it matter? (He wants to hear that lovely, deep, gruff voice say his name, his full name. Just once.)

“Your nametag says Steve.” Castiel knows the look that’s starting to spread over Mr. Smith’s face. It’s the one that he’s seen all of his life, the one that says Uh-oh, now I’ve gotten myself into a conversation with this freak, how can I best extract myself from this situation. It hurts, much more than it should, to see Mr. Smith start to look that way. 

“It was a joke,” Castiel mumbles. Warmth spreads down his neck, sparking a nervous little sweat. “My name is apparently difficult for people, so they gave me this tag to make things easier.” 

Mr. Smith’s mouth purses. “Well, that’s a douchey thing for whoever to do. Cas-tee-ell.” He lingers over the tee, rolling it on the tip of his tongue, and goosebumps prickle on Castiel’s arms. “It’s a mouthful, but it’s not hard.” 

A different kind of warmth suffuses through Castiel. It starts at the center of his chest and slowly spreads outward, like the eggnog that he had last Christmas at the company party. It’s tingly at the edges. 

“Well, that’s not what everyone else thinks,” Castiel says, to try and diffuse the heat flooding through his body. 

“Yeah, well, nobody thinks how I think.” Mr. Smith keeps his eyes focused on Castiel’s face. There’s something intense in his eyes, and for once, Castiel finds himself on the uncomfortable end of a staring contest. “‘S why they gave me the gig in the first place. ‘Innovative ideas’ or something like that.” He chuckles, and there’s something bitter in the sound. “I don’t think they realized that I have maybe one good idea every couple of years.” 

“I don’t think that’s true,” Castiel blurts, before he can stop himself. He has no real basis of comparison for his statement; he knows next to nothing about Mr. Smith. “I just mean,” he stammers, “that if you start doubting yourself, then you’ll never know what you can do.” 

The advice rings as hollow coming from his mouth as it did coming from the mouths of every advisor and guidance counselor he ever had. Mr. Smith’s mouth twists in a sardonic little smile. “Supposed to breathe new life into this company, and I can’t even get the damn computer going.” 

“Oh!” Suddenly remembering the reason he’s in this dream of an office, Castiel moves forward. “I can probably help with that.” 

He steps in close to Mr. Smith (too close if his sudden blush and recoil are any indication) and fiddles with the mouse and monitor. The screen remains dark, which Castiel is almost glad to see. At the very least, it tells him that Mr. Smith isn’t an idiot. He follows the cords and finds that at the very least, the computer is plugged in. He kneels under the desk, sorting through the various tangle. 

“Ok, the person who put this together is an idiot,” he murmurs, tugging at a cord. 

“I put it together.” 

A cold spike of fear jolts through Castiel. Why, why, why does he always speak without thinking? Why can’t he be like a normal person, who had a modicum of tact, why can’t he manage to hold it together in a conversation long enough to interact like a regular person? Why is he such a disaster of a person? 

He bashes his head on the top of the desk as he scrambles out from underneath it. He glances up at Mr. Smith (tries not to concentrate on the visual aspects of this particular scene: him, on his knees underneath the desk, Mr. Smith, on his chair, looking down at him with a smoothly amused expression). “I’m sorry,” he says, hopefully in a garbled amalgamation of the English language. “I didn’t mean to...”

“Calm down, Cas, it was just a joke.” Mr. Smith’s face turns apologetic. “Apparently not a funny one.” 

Relief floods through Castiel, at odds with the throbbing pain in his head. “I just meant...the person who set up the computer did it wrong. The wires are shorted out.” He rubs at the back of his head as he glances back down. “It’s a simple fix, shouldn’t take me more than five minutes.”

“Oh.” Mr. Smith’s mouth (Castiel really shouldn’t be staring at Mr. Smith’s mouth so much, has Mr. Smith noticed how much Castiel has been staring at his mouth? Is Mr. Smith aware that he has a mouth which is very stare-worthy?) drops in a frown. “So quick?” 

“Well like I said,” Castiel grunts as he shimmies back under the desk, “it’s a quick fix once you realize what you’re doing. The person who set this up was probably just trying to go too fast and made a mistake. Or something. Who knows.” He doesn’t want to throw a member of his department under the bus, but he doesn’t want to lie to Mr. Smith either. 

“No, I just mean...” Mr. Smith taps his fingers against the desk. “Listen, do you want a cup of coffee or something?” He gestures towards the gleaming coffee machine on the counter. 

“I don’t know.” Castiel stops working and pokes his head out from under the desk. “I don’t want to be late.” 

Mr. Smith laughs. The sound is round and rich. It fills the room and sends little sparks of delight dancing down to his fingertips. “Who’s going to narc on you? You think you’re going to get in trouble with the boss?” 

“I mean...I guess...” Castiel can’t help but smile at Mr. Smith. 

“Come on, Cas. Give me a break here. Have a cup of coffee.” 

“I’m really glad you got the job,” comes tumbling out of Castiel’s mouth. Which is bad enough, but then comes, “You’re much better looking than Mr. Adler.” 

A dreadful silence hangs over the room. Castiel hopes his words will fade, but they linger between them like skywriting, scrawled in neon. His brain decides to come back online now, with thousands of worst-case scenarios. 

Mr. Smith fires him for sexual harassment. 

Mr. Smith presses charges against him. 

Mr. Smith ensures that Castiel Novak never gets a job anywhere in the industry ever again. 

Castiel ends up homeless and alone, ridiculed by everyone, and has to move in with Gabriel, possibly ending up working as a production assistant in Gabriel’s porn company. 

Then Mr. Smith laughs. It’s not a mean sound; it’s delighted. He pinches at the bridge of his nose, still laughing. Even after the sound fades, his shoulders still shake with mirth. When he opens his eyes, Castiel thinks there are actual tears in them. 

“I mean, that’s a pretty low bar to set, but I’m glad that I made it over.” Mr. Smith chuckles. He’s still laughing as he makes his way to the coffeemaker. He pushes a few buttons, then leans against the counter. “Stay for coffee, Cas. Please,” he adds as an afterthought. 

Castiel thinks of his tiny cubicle, crowded together with dozens of other small boxes, in a stifling environment screaming with the sounds of computers and copiers. He thinks of Mr. Smith’s smile, the strange kindness in him, the thoughtfulness with which he said his name. 

“I can stay for coffee, Mr. Smith.”

Mr. Smith turns around, one eyebrow raising at the formality. “Call me Dean,” he says. 

Castiel turns the name over in his head several times. It’s simple, direct, yet oddly complicated. It suits the man in front of him. 

“Hello, Dean.” 

Sam drove you toward your condo. “So, how long do you think he’ll be in the meeting?” you asked. Your boyfriend hadn’t been able to pick you up himself because he was in an investors meeting for your company, which he was CEO for and you were a low-level manager for.

“Uh, he said it was gonna be late. It’s a working dinner kinda thing.”

You frowned. You hadn’t seen Dean outside of webcam conversations in six months, not since you were promoted and sent to New York to train for your new position. “I guess I’ll get to see him after.”

“Yeah, it won’t be long.” You smiled at him. Sam was a good guy. A good brother to Dean. Maybe one day he’d be your brother, too. You took your bag to your bedroom and hugged Sam before sending him on his way for the night. “Wanna have lunch tomorrow?” he asked as he headed out. You nodded and promised to call him in the morning.

You unpacked your bag, putting your clothes back in the closet, putting your toiletries back in the ensuite bathroom, setting your shoes on the rack by the door. Then you sat on the bed, waiting for Dean. After about twenty minutes, you got bored, anxious about seeing him after so many months, so you slipped back into your shoes and grabbed your keys. It was a short drive to the office, especially at 8pm when the streets weren’t packed.

“Hey, welcome back, Y/n!” Thomas, the guard at the front desk greeted as you walked in. “How was the Big Apple?”

“It was great! I got to see some awesome shows and they have real museums there. It was great,” you reiterated, before heading for the elevators. “I’m gonna go up and say ‘hi’ to Dean...try not to interrupt his meeting too much.”

“Meeting?” Thomas asked, eyebrows coming together.

“The...the meeting with the investors for the new product.”

“Um...sure,” he responded, confusion on his face. 

His confusion confused you, but you weren’t gonna stick around to question it. You hadn’t seen your boyfriend in months. You were so excited to see him. You rode the elevator to the executive floor and headed for the conference room...the empty conference room. In fact, the whole floor seemed empty. Where the hell was Dean?

You walked down the hall to the big office, the one with ‘DEAN WINCHESTER, CHIEF EXECUTIVE OFFICER’ on the door. The small desk parked outside the office was empty too, his assistant gone for the night. Or...not. Her purse was sitting next to her computer keyboard.

You bit your thumbnail as your mind jumped to a conclusion. A horrible conclusion. Thomas was confused because there was no meeting. That’s why there was no one in the conference room. No meeting, no people there but Dean and his assistant, Nicoletta. You set your ear against the door, trying to listen to what was happening in the only office on the floor with the lights on. You couldn’t hear anything, Dean’s office door was a thick oak, so you slowly twisted the knob and pushed it open.

The sound slipped through immediately, a punch in your gut as you heard the telltale sounds of grunts and heavy breathing...tiny moans. “Fuck, Nicki, you feel so fuckin’ good. Such a tight little pussy,” Dean’s voice hit your ears and you slapped your hand over your mouth to hold in a pained gasp.

“Gonna miss this?” the sultry voice of Dean’s assistant asked.

“Oh, baby, we’re not stoppin’ just ‘cause she’s back.” Your jaw dropped behind your hand at his words. “Find another--fuck just like that--trainin’ program to send ‘er to.”

You let go of the doorknob and turned away, running for the elevators at the end of the hallway. He sent you away on purpose?! You were completely overwhelmed by tears by the time the elevator hit the lobby. You ran full-speed for the parking lot and ignored Thomas calling after you. You were glad for the mostly-empty streets because your driving was erratic to say the least.

You ran into your bedroom and grabbed your suitcase, running through the closet to grab all of the clothes you just put in their places. You’d stay in a hotel. You’d find another job. You’d...break down in the middle of packing, thinking about the way he came up to you at the Christmas party three years ago, how you’d assumed he was talking to the woman beside you when he said ‘hi, what’s your name?’. You were so stupid to think he might want to be with you, marry you, have a life with you.

“No time for this,” you whispered, wiping at your stinging eyes and continuing to pack. 

You were pushing down on the overstuffed suitcase, trying to get it to zip, when the security system beeped to let you know the front door had opened. “Baby! I’m home!” Dean called out as you got the zipper done. No way to get past him without a confrontation now. You heard his keys hit the table in the entryway. “Y/n, where are you?” You sat at the end of the bed and waited for him to get around to the bedroom. His lips pursed when his eyes fell on you sitting there with a suitcase and tear-drenched face. “What’s--what’s wrong, Y/n?”

“I got bored waiting for you,” you said quietly. Your eyes were on his stylish leather shoes as he stepped closer. “So, I went to the office to interrupt your meeting with a hello kiss.” He stopped his forward movement. "Imagine my surprise when the only meeting I found was a meeting between you and your assistant's genitals."

"Y/n, I…"

"You sent me away...right after you hired her. Why didn't you just tell me you were done with me?" you asked, still not looking up at him.

There was a moment of silence before he said, "Because I'm not."

"Tell that to Nicoletta," you whispered.

"I have. I remind her damn-near every day that I'm in love with you, Y/n." You scoffed and he dropped to his knees in front of you, trying to get you to look at him. “Look at me.”

“I can’t,” you whispered, shaking your head. “How could you do that if you love me?” 

He sighed and leaned back, sitting on his heels. “I...I needed a break. Be-because I do love you. I love your heart and your brains and your personality and your smile. I love the way my family loves you...but I...I don’t love your body.” Your eyes snapped up to his. He looked apologetic as he bit his bottom lip. “I’m sorry. I looked past it for years, imagined Scarlett Johansson while we were in bed, did the best I could to focus on your face because you’ve got a gorgeous face, but...when Nicoletta walked in to interview for the job, in that bodycon dress...I…”

Your lip trembled as you stood and grabbed your suitcase. Dean popped up, standing tall and in your way. “Don’t do this. Don’t leave. We can talk this out, please!”

“You needed a break. A six month break. Six months to...get Nicoletta out of your system?” you guessed, looking at your feet.

“Yeah. Exactly,” he exclaimed, happy that you seemed to understand. He grabbed your chin and made you look into his eyes, but he didn’t see understanding in your eyes, just depression.

“Well, now you don’t have to worry about that.” You twisted your head to get him to release your face. “You’ll have my resignation letter in the morning and I’ll send a moving service for the rest of my things.”

You pushed past him and walked toward the front. “Don’t do this,” he called after you. “Please. Give me a chance to-”

“I gave you one,” you responded, stopping in the middle of the living room. You didn’t look back. “I had faith in you, Dean. I had so much faith in you that I didn’t even consider that you might hate the most visible part of me so much that you would cheat on me...that you would send me across the country specifically so that you would have the opportunity to fuck around. You had the chance to be a good man. You did this. Not me.”

You swallowed to help the knot in your throat as you walked out of your condo for the last time.

~~~~~~~~~~~~~~~~~~~~~

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