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Picture perfect
Characters: Dean Smith (Winchester) x Y/N Wesson Female character
Summary: Request by @radioactivatedspider
Y/N has been to nervous to introduces Dean, her white-collar boyfriend, to her blue-collar family. especially her tough, skeptical father, John. Despite John’s initial disapproval, especially over Dean’s office job and the company hybrid he drives. Will Dean convince the man he really loves his daughter?
Warnings: none
English is not my first language
*Please do not copy my work, reblog/comments/likes are appreciated*
The scent of rosemary and garlic filled the apartment as Y/N stirred the pot on the stove, humming softly to herself. She felt Dean’s arms slide around her waist, his warmth pressing against her back, and she smiled, leaning into him. His hold was comforting, grounding—a reminder of the life they’d built together. A simple, good life.
“Hey,” she greeted him, a soft smile spreading across her face as she stirred the pan.
“Hey yourself.” He nuzzled into her neck, inhaling the scent of her shampoo mixed with the warm aroma of dinner. But there was something… off in the way his fingers drummed lightly against her hips, and when she turned, the usual spark in his green eyes was shadowed by something darker.
"Dean? What’s going on?" She tilted her head, reaching up to trace his jawline with her thumb.
Dean hesitated, looking away briefly, then sighed, his shoulders slumping slightly. “I, uh… I ran into someone today. At work.”
“Oh?” She raised an eyebrow, not quite following.
“Your brother.”
The wooden spoon nearly slipped from her fingers. She stared at him, wide-eyed. "You… you met Sam? I thought he worked on a whole different level of the building?" Her voice faltered, an unexpected spike of nerves twisting in her chest.
Dean gave her a gentle squeeze, as though to reassure her, but there was still something there, a question in his eyes that he hadn’t voiced yet. “Yeah, I met him in the elevator. Really freakishly tall guy, long hair?"
“That sounds like Sam,” she muttered, half to herself.
"Y/N…" Dean said, voice lower, more serious. “He didn’t seem to know about us. About me, have you told your family yet?”
She felt her cheeks warm, a mixture of guilt and embarrassment flooding through her. She'd been so careful about when to introduce Dean to her family, and especially to Sam. Her relationship with her brother had always been complicated, and with Sam’s intense, almost otherworldly nature… she didn’t want to scare Dean away before he really got to know her. “Look, Sam can be… weird,” she began, twisting her fingers together. “He’s, uh, had strange dreams since we were kids. Sometimes they… get a little intense.”
Dean nodded slowly, trying to absorb her words, but there was still that questioning look in his eyes. “Yeah, tell me about it. He mentioned seeing me in a dream of his. That's kinds of… freaky.”
Y/N grimaced, wrinkling her nose. “That’s exactly what I mean, Dean. He can be… different.”
Dean watched her, eyes softening, then gave a small chuckle, the tension in his shoulders easing as he pulled her back into his arms. “Well, freaky brother or not, you’re worth it,” he murmured, pressing a kiss to her temple. He held her there for a moment, close and steady, the kind of embrace that reminded her of everything she loved about him.
But then he pulled back, studying her face. “Wouldn’t it be time I meet the rest of your family? I mean, I'm waiting for a year, you met my family. Maybe next week for your birthday?”
She bit her lip, looking down. Dean had been so understanding, so patient with her hesitation. But there was no more hiding him, not anymore. Meeting her family, even Sam, was the next step—an intimidating one, but one that she wanted to take with him. “Alright,” she whispered, a small smile tugging at her lips. “Let’s set it up.”
Dean’s face lit up, a spark of warmth that melted away the last of her nerves. “Now that’s the spirit,” he said, leaning down to kiss her, soft and slow, and this time, all the doubt and shadows disappeared.
--
A week passed
Y/N smoothed down her dress, nerves prickling under her skin as she paced in Dean’s immaculate penthouse. The place gleamed with polished surfaces and minimalistic, modern decor—everything so distinctly Dean. It was his sanctuary, where he found comfort in clean lines and structured spaces, a far cry from the cluttered, noisy house she grew up in. She couldn’t help but fidget with the hem of her dress, glancing at the door every few seconds.
Dean walked over, a soft smile on his face, and put a reassuring hand on her shoulder. “Hey. It’s going to be fine. Really.”
She looked up at him, grateful for his steady presence but unable to shake the flutter of anxiety in her chest. “You don’t know my dad,” she muttered, shaking her head.
Dean chuckled, adjusting the cuff of his tailored shirt. “Come on, how bad can he be?”
She opened her mouth to answer, but before she could, there was a sharp knock on the door. She jumped slightly, shooting Dean an apologetic look as she stepped toward the door. “Ready?” he whispered.
“Ready as I’ll ever be,” she whispered back.
As she opened the door, her mother stepped in first, all warmth and enthusiasm. Mary wrapped Y/N in a tight hug, murmuring how good it was to see her. Y/N relaxed, if only slightly, under her mother’s affectionate smile.
When she turned to introduce Dean, she found her father eyeing the penthouse’s high ceilings and spotless decor with a skeptical frown, his lips twitching as he glanced at Dean’s suit. He hadn’t even made it inside before he’d looked at the hybrid in the driveway, scoffing loudly. “A real man drives a car with power, not… one of those electric gizmos,” he’d muttered, not quietly enough for anyone to miss.
Mary shot her husband a quick look before smiling at Dean, stepping forward to pull him into a warm hug. “Dean, it’s lovely to meet you. Welcome to the family.”
“Thank you, Mrs. Wesson,” he said, smiling as he hugged her back. “It’s really great to finally meet you both.”
John stepped forward, his eyes sweeping up and down Dean’s suit before offering a firm handshake. “So, you’re the guy my daughter’s been dating.”
Dean met his gaze with that calm, even look Y/N had always admired, shaking his hand without a flicker of hesitation. “That’s right. I’d like to think we’ve built something pretty special together.” He glanced at her, and she couldn’t help but blush.
Mary stepped in with a soft smile, "I think what John means is that we had hoped to meet you before Y/N decided to move in with you."
John huffed, his expression unreadable as he glanced around the sleek living room. “Well, good to know you’re treating her right, I suppose. But I gotta ask… what’s it like working in an office all day, dressed up like that?” He gestured to Dean’s crisp light blue shirt and red matching tie, giving a small smirk as he added, “Not sure I’d have it in me to do… sales or whatever all day. Must be real tough work.”
Y/N swallowed, looking to Dean, hoping he wouldn’t take it the wrong way. But Dean just smiled, his voice cool and unruffled. “It’s definitely different, I’ll give you that. But I’d like to think I work just as hard as anyone else. Besides, your daughter here—she’s the real backbone of my team.” He shot her a warm look, and she relaxed, grateful that he took her dad’s roughness in stride.
“Right,” John said, his eyes narrowing slightly as he studied them both. “Dating your assistant, huh? I thought they called that ‘dipping the pen in company ink’ or something like that.”
Y/N felt her face flush, heat prickling her cheeks. “Dad…” she said softly, her voice carrying an edge of warning. Dean tried to ignore it and shook Sam's hand who looked already apologetic.
Mary stepped in, trying to defuse the tension. “Oh, don’t mind John. You know how he is, rough around the edges.” She cast a fond but exasperated glance at her husband before reaching out to touch Y/N’s arm. “I can see you’re happy here, sweetheart. And that’s all that matters to your father and me.”
Dean squeezed Y/N’s shoulder gently, and her heart lifted at the calm strength in his gaze. “Well,” he said, guiding them all toward the dining area, “I’ve got some drinks ready. Why don’t we settle in?”
As they gathered around the sleek dining table, John gave one last gruff comment about the expense of Dean’s crystal glassware, muttering about “people with more money than sense.” But even he couldn’t hold back a small chuckle when Dean smiled and raised his own glass, not taking any of the jabs to heart.
--
In the kitchen, Y/N took a steadying breath as she placed the dessert plates on a tray, trying to push down the last of her nerves. Meeting her parents had gone better than she expected, but her father’s comments still lingered, tugging at insecurities she thought she’d left behind. Sam stepped quietly into the kitchen, leaning against the counter with a small, understanding smile.
"You okay, sis?" he asked, his voice soft.
Y/N sighed, brushing her hair back. “I forgot how… protective Dad can be,” she admitted, a weary smile touching her lips. “I swear, every time I bring someone home, it’s like he’s ready to chase them out with a wrench.”
Sam chuckled, shaking his head. “Yeah, you know how he is. No one’s ever good enough for his little princess.”
Rolling her eyes, Y/N scooped a spoon into the chocolate mousse, carefully decorating each dessert with a little whipped cream. She stole a glance at Sam. “What about you? What do you think of Dean?”
Sam’s face softened, his gaze warm and steady as he stepped closer, pulling her into a comforting hug. “I think he’s perfect for you, Y/N. I mean it,” he said, a quiet conviction in his voice. “He’s a good guy, and… I know he’ll make you happy. Anyone can see that.”
She pulled back just enough to look at him, a playful grin tugging at her lips. “Oh, did you see that in a dream?” she teased, nudging him lightly.
Sam smirked but didn’t say anything, glancing over his shoulder with a knowing look. His silence, that cryptic expression, made her pause, and for a fleeting moment, she wondered if maybe… just maybe, he had.
“Alright,” she laughed, feeling the tension in her shoulders ease. “Just don’t go scaring him off with any ‘visions,’ okay?”
He chuckled, shrugging. “I think Dean can handle it. He handled Dad pretty well, didn’t he?”
She let out a soft sigh of relief, smiling to herself. “Yeah… he really did.”
As she turned to carry the dessert out, Sam squeezed her shoulder, his eyes gentle but filled with a quiet reassurance. “You made the right choice, Y/N. Don’t doubt that.”
With one last grateful smile, she headed back to the dining room, feeling lighter and more certain than ever. Dean was waiting, his eyes lighting up as she placed the tray on the table, and when she settled back beside him, he reached over, his fingers lacing with hers in that familiar, comforting way. And in that simple touch, she knew—this was exactly where she was meant to be.
Caught up in the warmth and relief of the moment, Y/N leaned over and pressed her lips to Dean’s, a spontaneous gesture that said everything words couldn’t. She felt him smile into the kiss, his hand sliding to her back, steady and sure. When she pulled away, her cheeks flushed as she caught her father’s expression—a mix of surprise and mild horror, like he’d just seen a dead rat. Mary, on the other hand, beamed, her eyes crinkling with quiet approval.
“Oh, that’s right, babe,” Y/N said with a sly grin, squeezing Dean’s hand. “Why don’t you show Dad the garage?”
Dean raised an eyebrow, his hand trailing down to give her a quick pinch that made her squeak. He smirked, then turned to the group with a polite smile. “If you’ll follow me, I’ve got something I think you’ll want to see.”
They all followed Dean through the hall toward the garage, John looking dubious until Dean flicked on the lights, illuminating a sleek, polished 1967 Chevy Impala. The black paint shone under the fluorescent lights, every detail restored to perfection.
John’s eyes went wide as he walked around the car, taking in the flawless curves, the gleaming chrome, and the clear care put into every inch.
Dean, looking more relaxed than he had all evening, ran a hand along the hood, almost reverent. “The hybrid—that’s the company car. But this beauty? She’s mine. Been working on her for years.”
John’s skeptical gaze softened, replaced with an approving gleam. He reached out, brushing his hand over the hood before turning to Dean. He studied him for a moment, a grin beginning to crack through his otherwise stoic expression. “Now this is a real car,” he said, voice gruff but warm. He extended his hand, and Dean accepted it, their grips firm. John nodded, his face more serious but filled with respect.
“Welcome to the family, son.”
Dean nodded, holding the handshake a moment longer, and Y/N’s heart swelled as she saw the respect reflected in her dad’s eyes. Mary smiling at Y/N, who looked back with happy disbelief.
Later, as they saw her parents off and the door finally clicked shut, Dean wrapped an arm around her waist, drawing her close with a satisfied smile. “Guess that went better than we thought,” he murmured, his voice a soft rumble against her hair.
She laughed, leaning into him, her heart still racing. “Better than I could’ve dreamed.” She looked up at him, her eyes filled with gratitude and love. “Thank you, Dean.”
He chuckled, brushing a thumb along her cheek. “Well, I’d go through a hundred more awkward dinners just to keep you, baby.”
--
Taglist:
@jackles010378 @libby99hb @winchesterwild78
@suckitands33 @mostlymarvelgirl @deans-baby-momma
@ancles @tulipsvanilla @thesilmarillionblog
@jays-bonnie-on-the-side @kr804573 @kamisobsessed
@hobby27 @globetrotter28 @kindollss
@muhahaha303 @shadysoulangel @lyarr24
@spxideyver @impala67rollingthroughtown
@panickedbitch @deansimpalababy
#fanfic#jensen ackles#x reader#jensen fucking ackles#fluff#dean winchester#spn#supernatural dean#deanwinchester#dean#sam and dean#sam winchester
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this shot is quite literally insane dude I could write a whole essay about it. The director was like “Oh hey guys let’s do a close up on their hands to emphasize the importance of this gesture (as if making someone a mixtape isn’t already romantic enough), their fingers just inches apart to show have close but yet far away they are, that they share these little moments of intimacy but the weight of the unspoken feelings lingers heavy in the air oh and yeah let’s also make it look like the god damn fucking Michelangelo painting.. but nothing to see here.”
#supernatural#deanwinchester#castiel#spn#destiel#the brainrot is real#deancas#going insane#this keeps me up at night#jensen ackles#misha collins#these dudes are gay#mixtape
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A little Dean doodle | ref
[More art, wips, and sketches on my Patreon 💖]
#dean winchester#supernatural#spn fanart#artists on tumblr#spn#spn art#dean#becauseofthebowties#spncreatorsdaily#deancaskiss#seraphcastiel#userjactingjoices#rambleoncas#angelscas#emeraldcas#deanwinchester#my-art#Fanart
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Waiting for paint to dry...so here is Dean silenced by the Empty. Mars lumograph black + watercolour. To be added or removed from tag list, please let me know :)
@naughtystiel
@malicmalic
@fivefeetfangirl
@letmeblued
@castielsprostate
@dean-you-assbutt-cas-loves-you
@casdeans-pie
@pattywinchester
@bogwitchatrois
@bloodydeanwinchester
@beregond35
@horrorcas
@charlottemanchmal
@strawlessandbraless
@blue-eyed-cutiepatootie
@thefailcollection
@disabled-dean
@squirrelsarecool
@hauntedpearl
@markofcastiel
@butch--dean
@rennerator
@sailorsally
@xofemeraldstars
@forkinthegarbagedisposal
@happilyfeatherafter
@universalcas
@riverwithoutbanks-art
@shutupjaff
@magnificent-winged-beast
@sanndh
@mrs-padalecki2341
@archervale
@idontexistbutwhodoes
@eeveestoneson
@reader-meg
@integer-0verflow
@missingmoonflowers
@seeingthestarsmakesmedream
@sini5terxwalru5
@shipsawayandusuallygay
@famouskidangel
@justjayisfine0
@examishbookwyrm
@ididit-allofit-foryou
#spn fanart#deanwinchester#the empty#dreamtb#supernatural#artists on tumblr#horror#despair#supernatural art#spn#traditional art#dean winchester art
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this parallel is truly insane.
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❤️❤️ THIS ❤️❤️😤🙏
#dean winchester#castiel supernatural#supernatural fandom#spn#supernatural#castiel#destiel#destiehellers#destiew#destiel meme#destiel my beloved#human cas#castiel x dean#deancas#casdean#cas deserved better#twitter meme#twitter screenshot#dean supernatural#dean x castiel#dean#castiel novak#cas spn#cas screenshots#deanwinchester#castiel spn#destiel meta#human castiel#cockles#jenmish
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#Gifs from sunglassesmish#the last one idk i couldn't find the source#Destiel#castiel and dean#cas and dean#dean and cas#dean and castiel#castiel#castiel novak#dean#deanwinchester#dean winchester#Cas#Cass
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Dean Winchester in every episode | S01E01 | Pilot/Woman in white
#spndaily#spnedit#supernaturaledit#deanwinchesteredit#deanwinchester#spn#Dean in every episode#my gif
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Tried another method of rendering but i just keep losing against my brain overthinking/overdoing all that jazz.
So, I lost my patience during the rendering of the clothes especially... thus i didn't finish that.
And you didn't notice it, clear? 😉 Ref pic:
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and though i burn, how could i fall
when i am lifted by every word you say to me?
#supernatural#destiel#deancas#art#castiel#digital illustration#digital art#deanwinchester#dean#spn#hozier
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Unspoken Feelings
Summary: What started as simple, comforting snuggles between friends gradually deepens into something more
It started as something simple, something innocent. Just a couple of friends seeking comfort in each other after a particularly rough hunt. You and Dean had always been close—there was an unspoken bond between you, forged through countless battles, late-night heart-to-hearts, and a mutual understanding of the life you both led.
The first time it happened, you didn’t think much of it. You were both sitting on the couch in the bunker’s library, exhausted and battered from the latest hunt. The adrenaline had worn off, leaving behind the aches and bruises, both physical and emotional. You’d been talking about nothing in particular, just letting the words fill the space, when you suddenly found yourself leaning against Dean, your head resting on his shoulder.
To your surprise, Dean didn’t pull away. Instead, he wrapped an arm around you, pulling you a little closer, his hand resting comfortably on your arm. It was a simple, platonic gesture, one that felt natural, even necessary in that moment. The comfort of his presence, the steady rhythm of his breathing, it all made you feel safe, grounded.
“Rough night,” you murmured, your voice muffled against his shoulder.
Dean chuckled softly, the sound rumbling through his chest. “You can say that again.”
You didn’t say anything else, and neither did he. The silence between you was comfortable, familiar. You stayed like that for a while, just leaning on each other, taking solace in the fact that, for the moment, you were both okay. It was just a quiet, comforting moment shared between two friends who had seen more than their fair share of darkness.
After that night, it became a sort of unspoken tradition. Whenever the world felt too heavy, whenever the hunts took too much out of you, you’d find yourself sitting next to Dean, letting your head rest on his shoulder, his arm draped casually around you. Sometimes you’d talk, sometimes you’d just sit in silence, but the snuggles became a constant—a small, quiet escape from the chaos of your lives.
Over time, those moments became more frequent. It wasn’t just after hunts anymore. Sometimes, you’d be watching a movie, and you’d find yourself leaning into him, or you’d be sitting at the kitchen table, and he’d rest his hand on your back, just a simple touch that made you feel connected, understood.
You didn’t think much of it at first. It was just Dean—Dean who always had your back, who always knew what you needed, even before you did. But as the weeks went by, you started to notice the little things. The way your heart would skip a beat when his hand brushed against yours, the way your breath would hitch when he pulled you closer during one of your late-night snuggles, the way you found yourself craving his touch more and more.
It was confusing, this shift in your feelings, but you didn’t let yourself dwell on it. After all, it was just Dean. Your friend, your hunting partner, the one person you could always count on. And yet, something had changed. The snuggles that had once been purely platonic were beginning to feel like something more, something deeper.
You started to notice that Dean was different too. He held you a little tighter, his hand lingering on your arm or your back a little longer than before. His touches were softer, more deliberate, like he was savoring the contact. There were moments when you’d catch him looking at you, his green eyes filled with something that made your heart race, but he’d always look away before you could figure out what it was.
One night, after a particularly stressful day, you found yourself in Dean’s room. You hadn’t planned on going there, but when you passed by his door and saw the light on, your feet had carried you inside before you could think twice about it.
Dean was sitting on the edge of his bed, his shoulders slumped, clearly exhausted. He looked up when you walked in, a small, tired smile tugging at the corners of his mouth. “Can’t sleep either, huh?”
You shook your head, feeling a wave of warmth and affection for him wash over you. “No. Mind won’t shut off.”
Dean patted the space beside him, and you didn’t hesitate to sit down next to him, the familiar comfort of his presence already easing some of the tension in your chest.
Without a word, he wrapped an arm around you, pulling you close, and you rested your head against his shoulder, feeling the steady rise and fall of his breathing beneath your cheek. The quiet settled over you both, and for a while, you just sat there, letting the silence do the talking.
But tonight, something felt different. The way Dean’s hand was resting on your back, the way his thumb was gently tracing patterns on your skin—it felt more intimate, more intentional than it had before. Your heart started to race, and you couldn’t help but wonder if he was feeling it too, if he’d noticed the shift between you.
“Dean,” you whispered, your voice barely audible in the stillness of the room.
“Yeah?” he replied, his voice just as soft, almost hesitant.
You hesitated, unsure of how to put what you were feeling into words. “Do you ever… do you ever think about us? About what this is?”
Dean was quiet for a moment, and you could feel his breath hitch slightly, like he was trying to figure out how to respond. Finally, he spoke, his voice low, almost vulnerable. “Yeah, I do. More than I probably should.”
You lifted your head to look at him, your heart pounding in your chest. His expression was serious, his green eyes searching yours like he was looking for something, anything, to tell him what you were thinking.
“What if…” you began, your voice trembling slightly. “What if this is something more? What if it’s not just… comfort?”
Dean’s gaze softened, and he reached up to cup your cheek, his thumb brushing gently over your skin. “I think… I think maybe it’s always been something more,” he admitted, his voice rough with emotion. “I just didn’t want to mess things up by saying it out loud.”
Your breath caught in your throat, and you felt a rush of warmth spread through you at his words. All the little moments, the touches, the way he held you close—it all made sense now.
“So, what do we do now?” you asked, your voice barely more than a whisper.
Dean’s thumb continued to stroke your cheek, his touch so tender it made your heart ache. “We figure it out,” he said softly. “Together. One step at a time. If… if that’s what you want.”
You nodded, leaning into his touch, your eyes never leaving his. “It is, Dean. It really is.”
A slow, relieved smile spread across his face, and he leaned in, pressing his forehead against yours. “Good,” he murmured. “Because I’m all in, Y/N. I want this, with you.”
And with that, the distance between you disappeared. Dean’s lips met yours in a gentle, lingering kiss that was filled with all the emotions you’d both been holding back for so long. It was soft, tentative, but it spoke of promises and possibilities, of something real and deep and lasting.
When you finally pulled back, you were both breathless, your foreheads still resting together, the world outside fading away.
“So, I guess our snuggles aren’t so platonic anymore,” you teased, a smile tugging at your lips.
Dean chuckled softly, his thumb brushing over your lips. “No, I guess not. But I’m okay with that.”
“Me too,” you whispered, your heart full as you wrapped your arms around him, pulling him close once more.
And as you settled back into his embrace, the line between friendship and something more blurred completely, leaving behind only the warmth of his arms around you, the steady beat of his heart beneath your cheek, and the certainty that whatever came next, you’d face it together.
Taglist: @roseblue373 @jc-winchester @hobby27 @mishreem
#DeanWinchester#Supernatural#DeanxReader#ComfortFic#ReaderInsert#SupernaturalFic#FluffAndAngst#EmotionalSupport#Fanfiction#SamAndDean#SupernaturalFamily#DeanWinchesterImagine#ImpalaAdventures#deanwinchesterxreader#supernatural dean#dean winchester#deanwinchesterblurb#dean winchester x reader#dean winchester fic#dean winchester fluff#deanwinchesterfluff#sam and dean#dean x you#dean x reader#spn#sam winchester#supernatural fic
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Between Power and Freedom
Part 2
Characters: Dean Winchester x Y/N Shurley Female character
Summary: Y/N, the ambitious daughter of a powerful CEO, grapples with her father's choices, while she secretly takes a job with Dean Winchester, the rugged CEO of a rival company. Sparks fly between Y/N and Dean as they navigate their growing attraction amid corporate rivalry and family pressure.
Warnings: This story will contain parts that are 18+!
English is not my first language
*Please do not copy my work, reblog/comments/likes are appreciated*
Dean stormed out of the venue, his fists clenched so tightly his knuckles were white. The cool night air hit him as he strode towards the old Chevy Impala parked in the lot, his first car. It didn’t matter that he was the CEO of Winchester Industries now or that he could afford the most luxurious cars on the market; the Impala was a part of him, just like the memories of his sister, Charlie. He could never part with either.
Sam followed closely behind, watching his brother’s tense shoulders and the way Dean’s jaw was locked, clearly trying to keep his anger in check. He knew how much it took for Dean not to turn around and hit Chuck Novak right in the face.
“Don’t let him get to you like that,” Sam said softly, hoping to calm his brother down.
Dean spun around, his eyes burning with fury. “I can’t help it, Sammy. He needs to keep our sister’s name out of his greasy mouth!” He kicked the tire of the Impala, the frustration boiling over. “He’s a snake, you know that. He poked me right where it hurts, and he knows it.”
Sam ran a hand through his hair, exhaling slowly. “I know, Dean. Trust me, I do. But you know as well as I do that punching Chuck would only lead to more trouble—legal issues, court dates, all the crap we don’t need. We’d be playing right into his hands.”
Dean’s shoulders slumped slightly, and he leaned against the Impala, rubbing the back of his neck. “You’re right. God, you’re right,” he muttered. “But that doesn’t make me want to hit him any less.”
Sam leaned against the car beside him, thinking. There had to be a better way to deal with Chuck. As much as they both hated it, they had to think strategically.
Dean was silent for a few moments, staring off into the distance. Then suddenly, he straightened up, a sly grin creeping across his face. “Why don’t we hit him where it really hurts?” he said, a glint of mischief in his eyes.
Sam raised an eyebrow, unsure of where Dean was going with this. “What do you mean?”
Dean’s grin widened. “His daughter, Y/N. You saw her tonight, didn’t you? She looked miserable. Unhappy with her job, stuck under his thumb.” He paused, looking at Sam. “Chuck’s grooming her for something, probably to marry that slimy bastard Gabriel, and you know how he is. But if we steal her away from him? Offer her a job, something where she can get out from under Chuck’s control… that’ll drive him insane.”
Sam frowned, trying to follow Dean’s line of thought. “Dean, Y/N’s… well, overqualified for any position we have right now. The only opening we’ve got is in accounting, and with her degree, she could easily be in a management role. I doubt she’d be interested.”
Dean waved it off. “Doesn’t matter. Offer it to her anyway. Give her an out, let her make the decision. It’s not just about the job, Sam—it’s about giving her a way to break free. She’s stuck in Chuck’s world, just like we were stuck in Dad’s, but if she sees there’s another option… she might take it. And when she does? That’ll hurt Chuck more than any punch ever could.”
Sam looked thoughtful for a moment, weighing the idea. “You really think she’ll go for it?”
Dean nodded, his face serious now. “She’s smart, Sam. She’s not like her old man. She’s looking for something more, something that isn’t tied to Chuck’s empire. And even if it’s just a small accounting job to start, it’s a step toward something bigger.”
Sam sighed, seeing the determination in his brother’s eyes. Dean was set on this, and in a way, he had a point. If Y/N was as trapped as she seemed, offering her a lifeline could be the one thing that pulled her away from her father’s grip.
“Alright,” Sam finally agreed. “I’ll reach out to her. Schedule a meeting, see if she’s interested.”
Dean clapped his brother on the shoulder, his grin returning. “That’s my boy. Set it up ASAP. The sooner we get her away from Chuck, the better.”
Sam chuckled, shaking his head. “You always have a plan, don’t you?”
Dean smirked, pushing himself off the Impala. “I don’t just have a plan, Sammy. I have a mission.” He looked back at the event hall, his eyes narrowing slightly. “Chuck has been on top for too long, playing people like pieces on a chessboard. But not this time. This time, we’re flipping the game on him.”
With that, Dean opened the door to the Impala, sliding into the driver’s seat, the engine roaring to life as he revved it. Sam climbed in beside him, already pulling out his phone to make a note to contact Y/N.
As they pulled out of the parking lot, Dean’s focus was sharp. The night had been rough, but now, he had a plan. And this time, Chuck wasn’t going to see it coming.
--
The next morning, I was buried in my desk work at Shurley Enterprises when my phone buzzed. I glanced at the screen, a number I didn’t recognize. Figuring it was some client or a follow-up from the event last night, I answered, my tone neutral.
“Hello?”
“Y/N, it’s Sam Winchester,” the voice on the other end said, calm and familiar. My brow furrowed in confusion. Why would Sam be calling me?
“Uh, hi Sam,” I replied, not quite sure where this was going.
“I wanted to follow up on something,” he began, his tone kind but serious. “Dean and I were talking last night, and we wanted to offer you a position at Winchester Industries. I thought this might be an opportunity for you.”
At first, I bristled, my defenses kicking in. “What? You want me to leave my dad’s company? I’m not some pawn you can use to get back at him.”
“No, Y/N,” Sam said quickly, and I could hear the sincerity in his voice. “This isn’t about that. I… I know what it’s like to work under a father who has plans for you that don’t exactly match what you want. To feel like your life isn’t your own.”
There was a soft pause. “Dean and I had to take over the family business after our dad passed, but before that, it felt like we were on his path, not ours. I get it if you feel trapped.”
I was silent for a moment. He was right, that was exactly how I felt—like my life wasn’t my own, like I was just living out my father’s plans. Sam’s words hit closer to home than I’d like to admit, and for a second, I considered the idea of escaping Shurley Enterprises. So, I agreed to meet him for coffee during lunch to discuss the opportunity.
We met at an old café not too far from my office, a quaint little place with mismatched chairs and the smell of freshly ground coffee beans. When I arrived, I spotted Sam immediately. He was sitting by the window, looking much more casual than the sharp suit he wore at last night’s event.
He wore a jeans—expensive ones, I could tell—and a simple polo shirt. Yet, even in casual clothes, there was an air of professionalism about him.
As soon as he saw me, Sam stood up and smiled warmly, greeting me with a kiss on the cheek. It caught me off guard, but in a surprisingly pleasant way.
“Hey,” he said, pulling out the chair for me.
“Hey,” I replied, sitting down. I could feel the tension ease as we started talking, like we were already old friends. Sam had a way of making conversation feel natural, even though just yesterday we had been strangers. We talked about the event, about small things, about the café itself, but I knew why we were really here.
After a while, Sam steered the conversation back to business. “So, about that job offer… We could really use someone like you at Winchester Industries. The position I have right now is in accounting. I know it’s not much, but Bobby, our current accounting manager, is close to retiring. When that happens, the position is yours if you’re interested.”
I took a deep breath, mulling over his words. Sam wasn’t lying. He wasn’t offering me a glamorous, high-powered role. But he was offering me an escape, a chance to build something for myself, away from my father’s control. Still, the thought of leaving Chuck, despite everything, wasn’t something I could just do on a whim.
“I… I appreciate the offer, Sam. I really do,” I said slowly, my voice soft but firm. “But I can’t just leave my dad’s company like that. He might be difficult, but he’s still my father. And Shurley Enterprises—it’s my family’s legacy.”
Sam nodded, his expression understanding. “I get it, Y/N. Family’s complicated. I won’t pressure you. But, if you ever decide you want something different, something that’s yours, the door’s open.”
He reached into his pocket and pulled out a business card, sliding it across the table toward me. “Here’s my number. If you change your mind, or if you ever just need to talk, give me a call.”
I picked up the card, turning it over in my fingers. It was a simple gesture, but somehow, it felt like more. It was a reminder that I had options, that I wasn’t as trapped as I thought.
“Thank you, Sam,” I said, smiling at him.
“Of course,” he replied, smiling back, his eyes warm and genuine. For a moment, I thought about what it would be like to work for someone like Sam. Someone who listened, who understood. But I wasn’t ready to make that leap just yet.
We finished our coffee, the conversation drifting back to lighter topics. And when we finally parted ways, I walked back to Novak Enterprises with Sam’s card tucked securely in my purse, knowing that no matter what happened, I had a choice.
And maybe, one day soon, I’d make it.
--
When I got home that night, I could feel something was off the moment I stepped through the door. The lights were on, and there was the faint smell of whiskey lingering in the air. My heart skipped a beat as I realized my dad had let himself into my apartment.
“Dad?” I called, already knowing the answer. He was standing in the living room, his arms crossed, his face flushed with anger. I hadn’t even had time to put my bag down before he was glaring at me, his posture radiating fury.
“What are you doing here?” I asked, trying to keep my voice steady, though my stomach churned. I had never seen him this mad before—not at me, at least.
“I heard,” he began, his voice sharp and accusatory, “that you had a date with a Winchester today.”
My heart sank. He knew. How did he know?
“No, Dad, it wasn’t a date. Sam invited me for lunch, but it’s not what you think,” I said quickly, stepping forward, trying to explain before things escalated. But it was no use. I could see the storm in his eyes, and I knew there was no reasoning with him.
“What I think” he spat, taking a step closer to me, “is that you should be spending more time thinking about our business. And about Gabriel. Not having lunch with the competition.”
I sighed, my eyes dropping to the floor. It was always the same with him—business, control, and Gabriel. The suffocating expectations that were becoming unbearable. But before I could say anything, he roughly grabbed my chin, forcing me to look up at him.
“Why did you meet with Sam Winchester?” he demanded, his voice low and dangerous. “What did he want?”
“T-to offer me a job,” I stammered, feeling the heat rise in my cheeks from his grip. My heart raced, and I could see the moment the words hit him. His eyes widened in shock, but what came next caught me completely off guard.
“And what did you say?” he asked, his voice almost too calm, but I knew better. It was the calm before the storm.
“I declined,” I whispered, my voice trembling. I barely had time to process what was happening before his hand lashed out and struck my cheek, hard enough to sting and send me stumbling back a step.
“Are you stupid?!” he yelled, his face contorting with rage. “Do you even understand what you’ve done? You could’ve accepted! Worked for them! Do you have any idea what an opportunity that was? We could’ve torn them apart from the inside out, you stupid child!”
My vision blurred, both from the hit and the words. He didn’t care about me—he never did. He only saw me as a tool, a way to further his ambitions. And for the first time, the weight of it crashed down on me. He would never see me as his daughter. He would never love me for me.
Without thinking, I reached for my phone, my hands trembling. I could feel my dad watching me, his breath heavy, his eyes still full of anger.
I dialed Sam’s number.
“Y/N?” he answered after a couple of rings, his voice filled with concern. “Are you okay?”
“I’ll take the job,” I said, my voice shaking but determined. I swallowed hard, glancing at my father, whose expression turned from shock to cold fury. “I’ll take the job, Sam.”
There was a brief pause on the other end, then Sam’s voice softened. “Alright. We’ll make the arrangements.”
I hung up the phone and put it back in my pocket. My dad’s face twisted, "Good girl."
--
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#fanfic#jensen ackles#x reader#jensen fucking ackles#fluff#dean winchester#spn#smut#supernatural dean#deanwinchester#dean#sam and dean#sam winchester
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I burned so long so quiet
You must have wondered if I loved you back
I did,
I did,
I do.
#supernatural#deanwinchester#castiel#destiel#destiel canon#jensen ackles#misha collins#spn#spnfandom#deancas
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Men's
[HQ download and drawing process on my Patreon here!]
#dean winchester#spn fanart#spn art#supernatural#spn#artists on tumblr#art#becauseofthebowties#deancaskiss#userjactingjoices#spncreatorsdaily#seraphcastiel#rambleoncas#angelscas#theroadsofararchive#deanwinchester#emeraldcas#my-art#Fanart
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Taking a break from my commission with a Destiel pencil sketch :) Taglist, please ask to be added or removed :)
@naughtystiel
@malicmalic
@fivefeetfangirl
@letmeblued
@castielsprostate
@dean-you-assbutt-cas-loves-you
@casdeans-pie
@pattywinchester
@bogwitchatrois
@bloodydeanwinchester
@beregond35
@horrorcas
@charlottemanchmal
@strawlessandbraless
@blue-eyed-cutiepatootie
@thefailcollection
@disabled-dean
@squirrelsarecool
@hauntedpearl
@markofcastiel
@butch--dean
@rennerator
@sailorsally
@xofemeraldstars
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@happilyfeatherafter
@universalcas
@riverwithoutbanks-art
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@magnificent-winged-beast
@sanndh
@mrs-padalecki2341
#destiel art#pencil sketch#supernatural fanart#spn fan art#deanwinchester#castiel#traditional art#artists on tumblr#destiel
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Hi everyone! Nice to see you all!
Sorry for a long time without posts!
In good timing, I finally finished this Destiel comission for @fanficwritergwen, based on her beautiful fic Centerfold! Thanks for your patience waiting, while I was stuck in too much work and personal issues!
LINK to the fic
Also, in a good moment to wish Happy Valentine’s Day! And happy anniversary to them!
My hugs!
#supernatural#castiel#deanandcas#destielfanart#destiel#fanart#deanwinchester#spn fanart#spn fanfic#destiel fanfic
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