"Driver picks the music..."

All of these stories follow the main series above and are listed in chronological reading order (not the order I wrote them in, but how they should be read).

(❤️‍🔥 = smut)

In the Dark You and Ben have tackled the insurmountable together, but no one said the recovery would be easy.

Checkerboard You’re not a supe. You’re breakable. Soldier Boy sometimes forgets that.

Wanderlust Your wandering hands are keeping Ben up at night.

A Simple Touch Annie still has reservations about Ben, and you dating him for that matter…until she sees it.

Love Actually ❤️‍🔥 - [MINI SERIES] Ben gets in late on Christmas Eve with a Grinch-like attitude, but you’re determined to force some holiday cheer into his system. At least, you hope you can, before he meets the rest of your dysfunctional family on Christmas Day.

⟡ Series Complete ⟡

Wake Me Up ❤️‍🔥 - [MINI SERIES] A few weeks after you and Ben celebrate your first Christmas together, he is returning from another mission with the Supe Affairs team. When he discovers that you’ve been taken, he’ll do whatever it takes to find you. And then, to help you heal.

⟡ Series Complete ⟡

Exposure Therapy ❤️‍🔥 You’ve tried dealing with it the “healthy way,” like talking it out with a therapist. But what you’re really hoping is for Ben to fuck it out of you.

Strong As Blood ❤️‍🔥 After you accidentally break through a solid wood table, you know there’s something wrong with you. You begin to have your suspicions, but can you keep it from Ben long enough to find out? 

(In other words: This is the story of how you and Ben discover that you’re pregnant.)

Part 1 || Part 2 - Complete

Sleigh Ride Yet again, you convince Ben to indulge you in a new Christmas tradition.

Until Morning A quiet moment between you, Ben, and your newborn daughter.

This One's For You Late one night, finding no other recourse, Ben sings to his infant daughter to help her sleep.

Lesson Learned ❤️‍🔥 There’s only so much teasing Ben is willing to take. He has no choice but to punish you. (Sequel to This One's For You)

Green ❤️‍🔥 Ben spends the day alone with his daughter, to varying degrees of success. When you get home, it prompts a serious conversation.

Calculated Risks You and Ben argue about your commitment to being a working mom. When a rogue supe gets loose at Supe Affairs, mayhem ensues, putting not only your life at risk, but your daughter’s as well.

I've Got You ❤️‍🔥 Being pregnant with a supe’s baby isn’t easy, even the second time around. The good news is your husband is all too willing to help you relieve a certain craving.

Imagines:

Getting jealous. ❤️‍🔥💚 Ben needs new clothes, but the shop girls think your boyfriend is fair game.

Ben’s reaction to his girlfriend on her period.❣️ How he takes care of you.

Ben loses you. 💔 Includes a “twist” ending…

Talk to Me 💞 In the wake of his vivid nightmare, you confront Ben about his fears and get him to open up. [Sequel to “Ben loses you.”]

Headcanons:

Inspiration behind the Part 17 plot twist. It has to do with my love of Smallville. (Spoilers for BMD Part 17.)

How many kids would you and Ben have? The answer is...

Ben's reaction to his daughter Lila's first crush (vs. his son's). The double standard here is ridiculous!

How Ben would react when Lila gets a boyfriend (or girlfriend). Dad!Ben is pretty much what you'd expect...

How Ben reacts when his daughter (Lila) is dating an asshole. He sees an unfortunately "kindred" spirit.

What if Lila caught Ben on a bad day? Featuring reactions from young!Lila and teen!Lila.

What (BMD) Soldier Boy/Ben Would Say to His Younger Self Ben has the opportunity to meet his counterpart from the 1980s. What advice would he offer?

Imagine Soldier Boy (Ben) "Sliding Up" to You in the Club Despite what you might think, he's got moves...

Domestic headcanons with Ben After you get through the wall of bravado, you can expect...

Moodboard below created by @chernayawidow:

"But you move me, baby. All my livin time..."

Moodboard below created by @spnbabe67:

"A fight for love and glory, a case of do or die..."

Did you like this series? If you'd like to keep supporting me as I continue the BMD-verse, you can:

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Soldier Boy Masterlist

Main Masterlist

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

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Dean Winchester Series List

Dean Winchester Masterlist

Main Masterlist

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

You rose to your feet and slipped your flip-flops back on, glancing down at your clothes. It wasn’t like you were dressed for company, but it was too late to worry about it now. You tried to see who was behind the wheel, but the sun glinting off the windshield made that impossible, so you shrugged and went down the steps to greet whoever was driving. When he climbed out of the car, your mouth dropped open, and you stopped in your tracks for a second.

You could have sworn the temperature just rose another 20 degrees. This man was a whole other level of hot. Drool-inducing, panty-melting, fantasy-inspiring hot - tall, lean, bow-legged, broad-shouldered, and gorgeous. As you forced yourself to close your mouth, he swore, talking to the car.

“Son-of-a-bitch! Come on, Baby, we’re almost home.” The frown between his brows (even that was attractive) smoothed out a bit as he saw you approaching (once you recovered your ability to walk). “Hey, sorry about that. I guess this heat is too much even for my Baby today.”

“I can see that!”

He turned to raise the hood, steam surrounding him as he propped it in place, and you swore you could hear porn music playing in the background as you stared at his biceps. You stifled a groan at the play of muscle underneath his grey t-shirt, which was rapidly growing darker with sweat in the heat and clinging to his back. “I’d better let her cool off.”

“I can hook up the hose so you can put some water in the radiator after it sits for a bit.” You were sounding far less wilted than you had felt before he got out of that car, that was for sure.

He smiled, and your heart did a somersault in your chest. “That would be awesome, thanks.” He followed you around to the side of the house, and you shut off the water to your flowers, then reached to unscrew the sprinkler hose. It had apparently welded itself to the spigot – you couldn’t get it to budge. You bent over, struggling to force the stubborn coupling to loosen up, but it was hopeless. You turned, frustrated, and your unexpected visitor’s eyes traveled quickly back up to your face as his tongue swept over his lips. “I – uh… Here, let me give it a try.”

He stepped forward to deal with the stubborn fitting, and you blushed at your thoughts. Had he been staring at your ass? Speaking of… Your eyes were currently glued on his backside as he finally managed to unscrew the sprinkler hose. You shook your head to break the spell and rushed over to grab the regular hose from its storage on the side of the house, handing it to him without meeting his eyes. You had to calm your hormones before you made a total ass of yourself over this guy.

“I have some iced tea in the house – or would you rather have a beer?”

He straightened up after hooking up the hose, turning to grin at you and sending another flood of those pesky hormones flooding into your bloodstream. “A beer sounds great, thanks. And my name’s Dean, by the way. Dean Winchester.”

You smiled back at him as you introduced yourself, then went up the steps and into the house to fetch a couple of cold beers from your fridge. Of course, you stood with your head inside of it for a couple of minutes first, thinking about the way you could feel his eyes following you as you had walked away from him. And you had thought this stay-at-home vacation was going to be boring.

You headed back outside, and Dean walked back towards you from where he had dragged the hose over near his car. You couldn’t stop staring at that bow-legged stride, the denim of his jeans hugging those strong thighs, and you dropped down to sit on the steps to mask your agitation. He plopped down beside you, gratefully taking the beer you offered. “Thanks - nothing like an ice cold beer when it’s hot as hell out,” he said grinning over at you. You agreed, watching as he tipped his bottle and took a long pull. You followed suit quickly, because otherwise you were going to moan out loud at the sight of his perfect lips on the rim of the bottle, the tip of his tongue touching the opening before he drank. There were several very filthy thoughts battling for space in your head, and you could feel your pulse beating between your thighs.

“Soooo,” you started, a little too loudly, but you quickly caught yourself and adjusted your volume. “I heard you say you were almost home – where are you from?”

“My brother and I live a couple miles south of Lebanon.”

“I guess we’re almost neighbors, then,” you said, inwardly cringing at your lack of small talk skills.

Dean gave you a crooked smile, nodding his head. “Yeah, I guess we are. So if I come knocking at your door to borrow a cup of sugar, you got me covered?”

You smiled. “Any time.”

He picked at the label on his bottle, shooting a sideways glance your way with a sly quirk of his lips. “As long as your boyfriend isn’t the jealous type.” You laughed softly, and he nudged your shoulder with his. “What, too subtle?”

“No boyfriend. Just an ex-husband, but that’s old news.” You met his green-eyed gaze, which had your breath catching in your chest for a moment. “How about you?”

“Nope, completely free.” A warm smile slowly spread across his face, making your stomach do a little flip. “So far.” He winked, so quickly that you weren’t completely sure you hadn’t imagined it, and then drained the rest of his beer and rose to his feet. “Let’s see if I can bring Baby back to life, huh?”

You went to the side of the house and waited for his shout, then turned on the water. You waited for him to call out again to shut it back off, then walked back around the house as he slid behind the wheel. You heard him turn the key with a ‘Come on, Baby!’ and then a ‘That’s my girl!’ when the engine roared to life. You were trying to stifle your smile when he shut the engine off and climbed back out, but he just grinned back at you before turning around to put the hood down.

He headed back your way, wiping his hands on the tail of his t-shirt. “If you’re not in a hurry, you could come inside and cool off before you head home, have another beer.” You shrugged as if it was no big deal, but you were holding your breath as you waited for his reply.

“Yeah, thanks. Lead the way.” You smiled and turned to go up the steps, Dean right behind you. You both let out a relieved sigh at the cool air in the house compared to the sauna-like atmosphere outside. “Damn, does that feel good,” he said as you kicked off your flip-flops. He bent to untie his boots, but you stopped him.

“You don’t have to do that, really.” He glanced up to see that you were sincere, gave a little nod in acknowledgment, and followed you into the kitchen.

You went to the fridge, grabbed a couple more beers, and handed him one, turning to lean against the island as you opened yours. Dean settled against the counter top across from you, flipping his lid into the trash with perfect aim, then tilting his head back to take several swallows as you lost yourself in the sight.

His t-shirt was stuck to his body, his nipples showing through the damp cotton of his shirt. You stared at his throat as he drank, watching with bated breath as a bead of sweat trickled from his hairline all the way down his neck. He licked his lips as he set his bottle down beside him, his eyes moving from your parted lips to your breasts as they rose and fell with your rapidly increasing breathing. Your heart was beginning to pound, and you took your bottom lip between your teeth for a second before you spoke, your voice breathless. “So, do you wanna…”

“Hell, yeah,” he growled out before you could finish, and then he was on you before you could blink. You reached back blindly, your beer thankfully settling in an upright position as he pinned you against the island and took your lips in a ravenous kiss, all tongues and teeth and hunger. He had both hands on your ass, kneading and squeezing as your fingers clawed at his back, and you could feel him rapidly growing hard as he pressed closer.

He finally broke the kiss, barely parting from you and still nibbling at your lips as he spoke. “I’ve got some condoms in my bag in the trunk.”

You shook your head, kissing him again and making him moan as you sucked the tip of his tongue. “Down the hall, nightstand, top drawer,” you managed before he flashed a grin, giving your left cheek one more squeeze before he rushed away to follow your directions.

Dean was back before you finished taking a swallow of your beer. He took the bottle from your hand, turning to set it next to his on the opposite counter top. “Might need some room,” he said as he moved close again, putting his hands on your waist and boosting you up to the top of the island. He slipped his fingers up under the hem of your shirt, looking into your eyes. “Can I?”

You nodded, holding his gaze as he slowly peeled your tank top up, then over your head. He tossed it behind him without taking his eyes from your breasts. “Your turn,” you said softly, giving his shirt a tug, and he pulled it off in one quick move, then moved in close. You wrapped your legs around him, pulling him snug between your thighs as you ran your fingertips over his chest, tracing the pattern of his tattoo.

He put a hand on your knee, moving it up slowly until his fingers slipped under the frayed hem of your cutoffs. “I should tell you, these Daisy Dukes have been making me crazy,” he rumbled, making you shiver as he traced a line forward and along the crease of your thigh. He leaned down to kiss you as he worked your zipper open, and you moaned into his mouth as he shoved his hand into your panties, his strong fingers gliding through your slick folds as he hummed against your lips.

“Well, I should tell you I’ve been wet for you since you first climbed out of that car,” you said, your voice raspy with arousal. His lips curved into a sexy smirk, and you leaned back on your elbows to lift up a little as he pulled your shorts and panties down, letting them fall to the floor.

He pulled you back up against his chest, kissing you again as he slipped a finger up inside you, stroking, searching until you squirmed with a little whimper. You felt him smile against your lips, and then he added another finger, rubbing firm circles over your clit with his thumb as he brushed his fingertips repeatedly over your sweet spot.

Dean rested his forehead on yours as you raised you hips to chase his thrusts. It felt amazing, but at the moment there was only one thing you wanted. You clutched desperately at the waistband of his jeans, popping the button free and jerking the zipper down. He grunted as you gave his erection a squeeze, then tugged at his jeans until he pulled his fingers from you, a low chuckle in his throat. “Okay, okay, I get it,” he managed to say as you looked up at him with a coy smile, and he shoved his pants down, your eyes widening a little at the sight of him. He rolled the condom on and moved in close again, rubbing his sheathed cock through your slick pussy.

“Dean….” you whined softly at the friction on your swollen clit, and he leaned close, whispering in your ear.

“Shhhh, sweetheart, I got you.” He reached down, guiding his cock to your entrance and pushing forward as you clutched at the back of his neck. You chased his lips, kissing him desperately as he worked his way inside you with short strokes until he was buried deep, your hips rising to meet him. Every sensitive nerve inside you was singing, your body trembling at being filled to the limit.

You were panting as you pulled back from the kiss, and Dean put a hand to your face, brushing your damp hair back from your forehead, his green eyes warm as he gazed into yours. “You doing ok?”

You leaned into his touch with a euphoric little smile, then nodded. “I’m good. Really good.” He flashed a quick grin before giving you a gentle kiss, letting his hand drift down to cup your breast. “Could be better,” you mumbled against his lips, giggling as he drew back and looked down at you with a cocked eyebrow, a sparkle in his eyes.

“Oh, yeah?”

You reached down to squeeze his ass – his very firm, pert ass – and leaned up to whisper in his ear. “Fuck me, Dean.”

He didn’t make you wait. He braced one hand on your hip and wrapped an arm around you to hold you close as he began to rut into you, staying deep inside you at first, then pulling out farther and driving back into you faster and harder. Your thighs tightened around him, your hips bucking into his thrusts as your fingers dug into the muscle of his back, his skin slick with sweat. Moans of pleasure and grunts of effort filled the air as you began to clench and pulse around his cock, and you arched your back and cried out as you came undone.

“Fuck, sweetheart,” Dean swore softly as he lost control, his cock throbbing inside you as your orgasm sent him over the edge with you. You strained against him, whimpering at the intensity of the sensations washing through you, finally slumping with your face against his chest, a shudder making you clench around his still-pulsing length. He leaned forward, slightly trembling, holding you tight with one arm as he braced a hand on the counter, his chest heaving beneath your cheek as he slowly came down from his high.

He rested his head on top of yours, his warm breath stirring your hair. “You’re fucking incredible,” he breathed, raising back up as you moved to look up at him.

“Pretty incredible yourself,” you responded with a languid smile. “I haven’t felt this good in – well, ever.” His eyes searched yours as he bent close to kiss you, sending a wave of warmth through you.

“You know, I could kiss you for hours. Possibly days.”

He laughed softly, his fingers trailing along your jaw. “Well, maybe we’ll work on that. But I should probably take care of…” He glanced down pointedly at where you were still joined, and you smiled.

“Oh – yeah – I guess so.” You held your breath as he pulled himself free, then put his hands on your waist and helped you down off the island. He smiled down at you, his eyes scanning over your body with a naughty smirk as he let out a soft ‘Mmm-mmm.’

“I’ll be back,” he said, hitching his pants up, and you stared as he walked away from you, heading to the bathroom. You collapsed back against the counter, blowing out a breath in aroused appreciation. You had just had sex with a complete stranger who was hot enough to fuel your fantasies for many, many years into the future – and you were pretty sure you weren’t finished with him yet. In fact, you were sure of it. So you stood up straight and headed for the bathroom, in all your naked glory, with a big smile on your face.

When he opened the door, you were standing there waiting. His eyes widened a little, his smile slowly growing as you peered up at him with a flirty expression. “I need a shower. And you’re welcome to join.” You pushed your way by him, letting your breasts brush against his arm on the way by, grinning to yourself as you heard him chuckle.

You reached in and turned on the water to let it warm up, and Dean watched you with appreciation, pulling his lip between his teeth. “I – uh – have some clean clothes out in the car. I’ll be right back.”

You shot him a sidelong glance with a smile as you stepped into the shower, sliding the glass door shut behind you. He let out a low whistle before he rushed to the front door, heading for the car to get his duffle bag and pulling out his phone to call his brother. “Sammy? Yeah, had a little car trouble, I won’t be home until tomorrow sometime. Nah, nothing serious. Yep, later.”

Sometime tomorrow. Next day at the latest. He smirked to himself as he closed the trunk, patting the Impala’s roof on the way by as he headed back to the house. “I owe you, Baby.”

Three weeks later:

You sat on the porch swing, a cold beer in hand as you relaxed after a long week of work. The weather had finally cooled off, and it was pleasant on the porch, a light breeze stirring your hair. You reached for your phone as it rang, smiling as you looked at the screen. “Hello,” you said, a smile in your voice.

“Hey, there – it’s me, your neighbor.”

“Hi, neighbor,” you laughed. “What’s up?”

“Well – as it turns out, I’m completely out of sugar.”

“Completely, huh?”

“Absolutely. Totally out. I could really, really use some sugar right now.” His voice was already sending vibrations through you that made you want to tell him to get in the car now. “And you know I’ve got a sweet tooth that just won’t quit. I need sugar, sweetheart.”

You laughed as you heard Sam’s voice in the background, threatening to throw up if Dean didn’t stop. “Well, you know you’re always welcome to come over for sugar if you need it, Dean.”

“I knew I could count on you. You’re the best neighbor ever. And we can fire up the grill, I’ll make my world-famous burgers, how’s that sound?”

“Sounds amazing. And I’ll handle dessert.”

He growled into his phone, making you laugh again. “Yeah, you will. Mmmmmm. I’ll be there in half an hour.”

You sighed happily as you hung up, swinging lazily with a smile on your face. Maybe you should put on those Daisy Dukes again.

Without panties, of course.

Tag List #1:

 @saenalife    @deanscarlett    @jensensgotyoudean    @jinkieswouldyoulookatthis    @deansdirtylittlesecretsblog 

   @geeklibrarian    @leatherwhiskeycoffeeplaid      @mrswhozeewhatsis    @littlegreenplasticsoldier    @sleep-silent-angel  

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        @savingapplepie-eatingthings    @kittenofdoomage    @masked-maiden42    @lean-mean-deanwinchester    @ericuhlorain  

  @undecided-garden    @ceeceewinchester    @typicalweirdbookworm          @callmesweetheartifyoumeanit    @youtoldalie 

   @tanithlowisabamf-blog    @deandoesthingstome    @jxackles    @nerdwholikesword    @soivebuiltupaworldofmagic  

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

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@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

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@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

I think what helps is that Dean has interacted with Emma a fair bit by the time we get to this moment, so the transition of him playing a more prominent role in Emma's life while dating reader is more or less smooth. 💓

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

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Dean Winchester Series List

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Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

Tag List Form || Fic Library Blog -> (follow + turn on notifications)

Join My Patreon ⟡ Get early access to new stories, bonus content, and first looks at upcoming stories. Top-tier patrons can even send me requests!

Dean Winchester Series List

Dean Winchester Masterlist

Main Masterlist

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

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Dean Winchester Series List

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Main Masterlist

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

Tag List Form || Fic Library Blog -> (follow + turn on notifications)

Join My Patreon ⟡ Get early access to new stories, bonus content, and first looks at upcoming stories. Top-tier patrons can even send me requests!

Dean Winchester Series List

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Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

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Dean Winchester Series List

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Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

Tag List Form || Fic Library Blog -> (follow + turn on notifications)

Join My Patreon ⟡ Get early access to new stories, bonus content, and first looks at upcoming stories. Top-tier patrons can even send me requests!

Dean Winchester Series List

Dean Winchester Masterlist

Main Masterlist

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

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Dean Winchester Series List

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Main Masterlist

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

Tag List Form || Fic Library Blog -> (follow + turn on notifications)

Join My Patreon ⟡ Get early access to new stories, bonus content, and first looks at upcoming stories. Top-tier patrons can even send me requests!

Dean Winchester Series List

Dean Winchester Masterlist

Main Masterlist

Dean Winchester Tag List (Part 1):

@luci-in-trenchcoats @waynes-multiverse @lamentationsofalonelypotato @chevroletdean @deans-spinster-witch

@jollyhunter @bettystonewell @supernotnatural2005 @roseblue373 @rizlowwritessortof

@wvffles @lyarr24 @ladysparkles78 @spnfamily-j2 @pieandmonsters

@hobby27 @kazsrm67 @foxyjwls007 @mostlymarvelgirl @jensensswthrt

@winchestergirl2 @spnbabe67 @stoneyggirl2 @my-stories-vault @this-is-me19

@tofics @artemys-ackles @mrsjenniferwinchester @charmed-asylum @flawlesslyspellbound

@k-slla @jackles010378 @deanbrainrotwritings @alwaystiredandconfused @rachiem4-blog

@leigh70 @aylacavebear @midnightmadwoman @twinkleinadiamondsky @kmc1989

@siampie @masked-lost-girl @suckitands33 @cheynovak @spnaquakindgdom

@mimaria420 @megara0224 @globetrotter28 @illicithallways @castielscaplan

He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.

His smile is almost involuntary when you notice him, your eyes brightening.

“Hey,” you say, “I um, wasn’t sure you would come.”

Dean kisses your cheek, lingering there at the scent of your perfume.

“Mmm, you smell nice,” he whispers.

You try to temper your smile, but it’s no use.

“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.

“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.

That crooked grin of his should come with a warning label.

You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.

He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.

“Nick Vaught,” he supplies.

Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.

“Dean Winchester,” he offers, along with his hand to shake.

Nick quirks a brow and points at Dean in recognition.

“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.

“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”

One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.

“Should we go in, find our seats?” he asks you. You start to nod, but—

“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”

You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.

“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.

“Right, right. So you’re fucking,” Nick says flatly.

It earns him a frowning look from another parent walking into the theater.

You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”

Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.

“Come on. You don’t owe him an explanation,” he says in your ear.

“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”

“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.

Nick’s lips press together in annoyance.

You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.

“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”

You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.

“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.

“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”

“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”

Dean pauses. “Wait, what?”

“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.

Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.

“Are you the brave soul who’s been dating my daughter?” he asks.

Dean shakes his hand firmly. “That would be me.”

The other man eyes him for a moment, seizing him up. After a moment, he nods.

“Good. You know you’ve got a gem on your hands.”

Dean gives you a sly smile. “Oh, I know very well.”

A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.

It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.

You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.

“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”

“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”

You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.

So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.

Your father watches out of the corner of his eye with a smile of his own.

While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.

After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.

“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.

“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.

“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.

You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.

“Well, you’ve got some more people who came to see you—”

“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.

He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.

Emma’s face brightens. “Daddy!”

She hugs his waist. He holds her back, petting her hair.

“You saw me?” she asks hopefully.

“Of course, honey. You did a great job.”

“What was your favorite part?” she asks.

Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.

“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”

“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.

“What? She’s never stayed over with me before. Tonight’s a special night,” he says.

“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.

“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”

Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.

He looks down at his daughter and gives her an apologetic look.

“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”

“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.

“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”

His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.

But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.

“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.

Her eyes go wide as she accepts them. “Whoa, there’s so many.”

You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.

You squeeze Emma’s shoulders. “What do you say?”

“Thank you,” Emma says, swaying a little with her pretty roses.

Dean laughs and playfully thumbs at her cheek. “You’re welcome.”

She giggles.

Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”

“Food sounds good to me,” your father says.  

“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.

“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”

You bite your lip. “You sure?”

“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”

He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.

“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”

“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.

You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.

Two Years Later

Dean scans the very detailed document on his laptop with a critical eye.

“Okay, Yale graduate. MBA. Internships, the works. Strong start.”

Kevin Tran, the latest candidate, pushes up his glasses.

“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”

Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.

“What do you think, sweetheart?” Dean asks.

He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.

You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.

“Let’s start with internships.”

AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘

I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!

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