𝑺𝑬𝑹𝑨𝑷𝑯𝑰𝑵𝑬 •𐙚₊˚ @seraphinxxa - Tumblr Blog

Mutual Engagement

Pairing: CEO!Dean Winchester x Assistant!Reader

Summary: Let’s take it back to Day 1. Here's how you got the job at HunterCorp as Dean Winchester’s Executive Assistant, how you kept it, and the day your professionalism with him finally broke.

AN: Ready for more Boss Man Dean? insert Chandler Bing gif (Friends fans will know lol) This of course is in the same world as Pratt Fall, but it spans the year building up to that moment.

Posted on Patreon: June 19, 2026 | Word Count: 9.6K

Tags & Warnings: 18+ | Single mother!reader, ft. a deadbeat dad, mutual pining, Dean’s dirty thoughts, office shenanigans and smut (v. fingering, penetrative sex – yes, on the desk)

Series Masterlist ➤ Dean Winchester Masterlist

“No,” Sam says, snatching the resume out of his brother’s hand.

“Aw, come on,” Dean says. He swivels in his leather chair but doesn’t bother getting out of it.

Sam levees him with an exasperated look. “This girl spelled ‘assistant’ with three Cs and a Y.”

“She’s funny,” Dean shrugs, once again taking a look at the applicant’s profile on his computer. In his opinion, her pouty lips and dewy young face speak for themselves. “And smokin’ fucking hot.”

“She’s illiterate,” Sam deadpans. He sorts through the resumes he printed off and hands his brother three strong candidates that he picked himself.

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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