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wearywinchester · 3 years ago

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Been Loving You

Dean Winchester x Reader

Summary: After never having the nerve to tell each other how you feel, an opportunity presents itself even if it takes a little work.

Requested by Anonymous: Hi! Since your requests are on. Can you write a fluff/angst dean and reader fic, they both have feelings for each other and they're too insecure to admit it. And dean flirts with another girl and introduces her to the reader, reader acts like she's fine but then cries??

Word Count: 4k

Warnings: angst, flirting, mild heartbreak, jealousy, arguing, little bit of swearing, fluff, kissing

July, 2005

The day was breezy and warm, the clouds having lessened the heat that came with being in the midst of the summer season. Even if the clouds did nothing to stave off the effect of the sun you’d like to believe it actually had been, and you refused to think otherwise or else you just might break another sweat. You were tucked away in the middle of Bobby’s property amongst a lot full of cars ranging from totaled to rusty to salvageable should he feel like getting his hands dirty that day. He didn’t.

But one person that did was Dean Winchester.

You stood with your arms crossed over your chest, staring out over the dozens of car roofs, each one holding their own story as to just how it was they got there in the first place.

“Wrench,” Dean called out at some point, an instruction you only half heard. It was growing increasingly obvious that your mind was elsewhere, that your attention was directed at the puffy gray clouds in the distance. He’d noticed, peeking his head around the Impala from where’d he’d been working under the hood for an amount of time you lost track of. “Sweetheart, wrench.”

You turned your head at the nickname, a brief look of confusion crossing your face before you realized what it was he’d said. You rolled your eyes at the look on his face, one that softened to a smile as you handed over the wrench grasped in your hand. He took it with a shake of his head and a laugh not quiet enough for you to miss, and you breathed out a sigh.

“You’re a terrible helper, you know,” he jests, voice muffled from where he stood.

“Pretty sure I didn’t ask to help you, De,” you say, leaning back against an old truck.

“Too bad,” he says, flashing you a smile all while you furrowed your brows and pursed your lips at his words.

“Why not have Sam help you? I’m sure he knows more about cars than me.”

You heard him laugh again, head shaking at your assumption that Sam had any form of a clue on how to fix a car, let alone Dean’s car. The thought of Sam under a hood had him chuckling, the idea all too humorous. He pulled back to look at you. “First of all, he definitely wouldn’t. Second of all…”

He trails off, looking at you with a half smirk on his lips.

“What?” You inquire, amused curiosity in your tone.

“Sammy’s just not you,” he shrugs, a glimmer in his eyes as he leans back over the engine.

Your smile falls for just a moment as your heart skips a beat, that very smile returning once you realize just what it was that he had said. He’s just not you. You turned away and looked over your shoulder, a pitiful attempt to hide the way you couldn’t stifle your smile, your cheeks burning at what it was that could mean. Maybe it meant something and maybe it didn’t. But either way it’d surely be stuck on your mind for a ridiculous amount of time.

But soon your attention turns back to the very person that it’s always been on, and you were bound to be teased if he’d caught you staring but the thought didn’t sound quite so bad at that moment. In your defense, it was hard not to think about much else other than the way his brows furrow when he’s stumped on just what he wants to fix next, or the way his cheeks flushed ever so lightly under the sun, his freckles all the more prominent across the bridge of his nose. Smudges of grease had stained his t-shirt, painted across his knuckles and smeared on his forehead each and every time he’d wiped the sweat off with the back of his hand.

Maybe it was that, or maybe it was the way his necklace had dangled down and swung there until he finally got irritated enough to tuck it in his shirt with a mumble of a swear and a clench of his jaw. That was something, though—no matter how frustrated repairing this beloved car of his made him, no matter how much he huffed and puffed and tossed his tools down with a bit more force than necessary. It was the way his anger seemed to melt each time he’d looked at you, the corner of his mouth quirking up in a smile before he turned to try again with a better attitude.

Yeah, that was it.

You hadn’t realized just how distracted you’d been until you felt a hand on your cheek, calloused and warm, and when you looked up your eyes met the taunting green gaze of the older Winchester staring down at you. Your breath caught in your throat as the pad of his thumb brushed along your cheek, cheeks that burned under his palm and the way he’d been gazing had your heart pounding in your chest. Racing until you saw the familiar quirk pulling at his lips.

“Got a little somethin’ on your face,” he says, smiling an all too knowing smile.

You roll your eyes, turning away from him with a huff as you begin to walk away. “I’m eating the last slice of pie for that.”

You heard the metallic clink of a tool leave his hand and hit the ground, “no—no you’re not! That has my name on it and you know it.”

You shake your head as you quicken your pace, a smile on your lips as the butterflies in your stomach remain.

October, 2005

You stood in the small, one person bathroom, back to the mirror as you leaned against the small porcelain sink. The tears were already rimming your eyes as you stood there, having been at that same restaurant for forty-five minutes waiting for your date to show up even though you knew it’d been a bust after you’d waited the first fifteen minutes. You were miserable and embarrassed, and this was the exact reason you didn’t like going on dates in the first place.

Your hand was shaky as you pressed Dean’s name, holding your phone up to your ear as it rang all but two times.

He’d make a joke when he answered the phone, something you more than expected by that point each and every time you called him, especially when he knew you were on a date with a guy he’d been poking fun at the whole ride to the restaurant until he’d dropped you off. You couldn’t blame him, maybe you could, but that was just in his nature and there was no changing that.

“Was brown eyes that boring?”

His laugh sounded on the other end, lighthearted and upbeat in a way that had a soft huff leaving your lips as you rolled your eyes at his words.

“Dean,” you grumble, letting your eyes fall closed for a moment.

“Oh, come on. You know I’m not wrong. I just—”

“Dean.”

The simple use of his name that time had effectively cut him and his teasing short, leaving a beat of silence as you swallowed thickly now that you had his full attention. You didn’t even need to see him to be able to picture just what kind of expression he’d been wearing at the moment.

“Can you come pick me up?”

You hated how fragile your voice sounded, something you immediately cover up as you clear your throat in a pitiful attempt to distract him from it. You knew it wouldn’t but it was worth the effort anyway, anything to ease the fact that it must have been obvious that you were hurting.

It’d been all of ten minutes before the rumble of an engine came into earshot as you sat on the curb that bordered the restaurant, gathering more than a few stares of people showing up with their dates in tow. You knew it must have been obvious what you were moping about. The headlights were near blinding as he pulled up next to you, and you were on your feet in an instant as you sulked to the car and slumped in your rightful seat. Your misery was more than evident to him as he sat in the parking lot for a minute much to your dismay.

“Are you okay?” He asks, louder than he meant to be as he gave you a once over.

“Peachy.”

He rolls his eyes. “Are you hurt?”

“Just my ego,” you mumble with a huff, though you soften at the concern sounding in his voice. “‘M fine, Dean.”

His jaw tensed as he looked at you, lingering on the glimmer on your cheeks from the fresh tears you’d tried to wipe away. At the way your bottom lip quivered in a way that was all too telling that you weren’t peachy, you couldn’t be farther from it.

He hadn’t even wanted you to go on that date in the first place, jealousy having simmered in the pit of his stomach since the moment you told him about it. He didn’t even need to see the guy to know he wasn’t good enough for you, that he was up to no good. He hated the tone of your voice when you called him, he hated that he was right. Not that he thought he was good enough for you, not even remotely did he think that, but when you told him about brown eyes, he wanted to be selfish and have you to himself for the night. He wanted to be the one to take you out on that date.

“He’s a dick,” he said quietly, anger woven around his words as he looked at you. “And he damn sure doesn’t deserve you.”

You looked down at your lap, picking at the loose string of your dress. “Can we please go?”

He looked at you as you went and looked out of the window, jaw clenching even tighter as he gave you one more glance. He put the car in drive without another word, tires squealing as he sped out of the parking lot, headed back towards the motel.

March, 2006

The sticks cracked beneath two pairs of muddied boots, the sound near deafening in contrast to the silence amongst the woods you and Dean had found yourself in. It wouldn’t have been quite so bad if you knew where you’d been going even just a little bit, and it wouldn’t have been quite so bad if the sun wasn’t dipping lower and lower into the sky. Not to mention the fact that Dean was simmering in his own anger, and you were fairly certain that you were the cause. In fact, you knew you were.

The light rain that sprinkled over you ever so slightly through the trees hadn’t done very much to work in your favor, though you don’t think anything could at this point. Especially not the scrape grazing your cheek.

“Would you quit huffing? We’ll find a way out of here,” you finally say, nearly smacking into his back when he stops in front of you.

“Right, because we’re totally not stuck in the middle of freakin’ nowhere. If it weren’t for you we’d be out of here by now,” he snaps, brows furrowed deeply as he looks down at you.

“Oh, so this is my fault now?”

He laughed then, humorless as he looked away and shook his head, running his tongue along the inside of his cheek. You knew he was dangerously close to snapping, more than he already did, but even then you couldn’t find it in yourself to tread lightly.

“If I recall correctly, it was your brilliant plan to go and run off and chase a werewolf all by yourself in the woods. You went and got yourself hurt and you nearly got yourself killed. That seems a lot to me like how we got into this mess, doesn’t it, Y/n?”

“Dean—”

“You’re lucky you only came out of there with a scrape on your cheek and a busted lip.”

Your brows knit together and your fists clench, nearly on the verge of tears with how frustrated you’d been at the green eyed Winchester fuming in front of you. “Why are you so mad? I’m here aren’t I?”

He looked as if you’d asked the most ridiculous question he’s ever heard in his life. “Mad? Why am I so mad? You went out there today like you’re invincible. I’m angry because I—”

He cut himself short then, shaking his head as he looked away from you. Those three words were so close on the tip of his tongue he nearly made a fool of himself, his heart pounding and a huff puffing through flared nostrils as you nearly watched him unravel in front of you. The crease between your brows deepens as you watch his inner turmoil, fists relaxing at your sides.

“Forget it,” he says, just as frustrated as he plays it off and looks down at you just briefly. His jaw clenches once more before he hikes his bags up further in his shoulder, grabbing your hand and turning his back to you. “Can’t have you getting lost on me again.”

You roll your eyes but not once did you pull your hand from his.

July, 2006

Your eyes rolled for what had to be the millionth time that night as you slumped further down in your seat, your eyes lingering on the older Winchester and the girl he’d been flirting with at the bar counter for the last half an hour. Sam had caught on to the source of your misery not long after it began, but between the pout you tried so desperately to hide and the way it started right around the time his brother started talking to the pretty girl serving drinks just a few feet away, it wasn’t hard to figure out.

“Am I boring you?” Sam jests, closing the book of notes and newspaper clippings he’d been working from for the next hunt. Your gaze lifts from the table to meet his gaze, unamused by his teasing. “You know, instead of sulking, you could tell him how you feel.”

You snort as you sit up in your seat, dragging your hand down your face. “Sam, that might be the stupidest idea you’ve ever had.”

“Oh, come on. Would it be so bad?”

One glance over your shoulder had your stomach churning and twisting in knots, your gaze moving back to the brunette with the bad ideas. “Yes Sam, it would be terrible.”

The more you sat at that table the less you wanted to be there, the music having grown far too loud for your liking as a headache began to form. This wasn’t the first or the second time you’d been to this bar, it was the third because Dean had eyes for the beautiful bartender. Your food was nearly completely untouched and your drink the same, though you were starting to think it might be a good idea to go ahead and down it but there wasn’t nearly enough time to do that and get another argument in with Sam before that ever familiar voice got your attention.

“Everyone,” he starts, smiling ear to ear as his arm wrapped around her. “I’d like you to meet Julie.”

His grin was beaming as she laughed into his neck, whispering something in his ear that you surely didn’t want to know. Sam’s smile in your direction was as empathetic as ever, your heart sinking down to your stomach as you swirl your straw in your drink. The room was rapidly becoming more suffocating and stuffy, the commotion near nauseating as the pressure behind your eyes deepened. You couldn’t be there another moment.

“I’m feeling a little tired, I—I think I’m gonna go,” you say as you swallow down the lump in your throat, sudden as you rise from your seat and grab your bag.

The smile on Dean’s face fell slightly, brows furrowing. “You okay?”

“‘M fine,” you say, offering a smile as you brush past the pair in favor of making your way to the door.

The outside air, though not very much cooler than the bar, felt better on your skin as you clutched the strap of your bag. The tears that welled in your eyes wasted no time in spilling over your cheeks now that you were alone, lip quivering pitifully as the hurt in your heart seeped out in waves and made your tears fall faster. They rolled down your heated cheeks and raced along the length of your neck, gathering on the collar of your shirt one after another.

Falling in love with your best friend doesn’t seem so bad until it breaks your heart.

September, 2006

Of all the people to be trapped in a storm with, Dean Winchester isn’t one you’d wanted it to be. The rain had been coming down so hard you could barely see the Impala parked outside the motel room. The wind whipping around had cut the power, effectively stealing your chances of busying yourself with some tv to take your mind off of anything other than the man you shared a room with.

Locking yourself in the bathroom would certainly be an option you’d weighed over more than once in your mind, but the thought of sitting alone in a small room with absolutely no source of light hadn’t been something that enticing to you. The only light in the motel room was the frequent flash of lightning and Dean’s flashlight before the batteries died.

“When’s this storm supposed to die down?” He asked from his bed, getting up to peek out through the blinds.

“Why? You late for a date with Julie?”

It’s quiet for a few moments, the blinds snapping back once he lets go of them and you could feel his stare on you as you looked up at the ceiling from your spot on your bed. Your jaw clenched as another flash of lightning illuminated the room, a booming crack of thunder soon to follow it. You were just waiting for what he had to say.

“What’s that supposed to mean?” There it was.

“I think it’s pretty clear,” you say, tone as witty as it’d been for the last who-knows-how-long.

“We broke up a month ago, Y/n. ‘M surprised you don’t already know that. You know, since you’re the know it all of the friendship.”

You roll your eyes even though he can’t see you, a huff falling past your lips. “Quit it, Dean.”

“What is your problem, Y/n? You’ve been actin’ funny for weeks and it’s driving me crazy. You’re taking every chance you get to get away from me,” he says, anger woven around his every word as his voice raises over the thunder.

“I can’t exactly do that right now,” you say, rolling over on your side as you avoid his question and turn your back to him instead.

You heard him laugh to himself, one void of humor as the springs of his mattress squeak under his weight as he sat down. Your jaw tenses once more as you huff through your nose, loud enough for him to hear as you tried your best to make yourself comfortable for the night.

The emotions clouding your mind were bound to boil over at some point before the night is over now that you’d been stuck with the source of your heartache and you weren’t sure if you’d rather stay or walk through the downpour coming down outside. The more you thought on it, the more you thought better of it despite how tempting it may have been.

The simple sight of him had tugged at your heart, making you think of just how foolish it was to fall for your best friend, or perhaps even more so that you hadn’t told him before. You couldn’t get Sam’s words out of your head no matter how hard you tried. If Sam of all people thinks you should have then maybe it wouldn’t have been a bad idea to put your heart on the line. Maybe you should’ve said it, you certainly had plenty of opportunities to do it. But it didn’t matter anymore, not really, your heart was heavy and your mind was heavier as you sulked and moped in your own misery.

You pushed away your own best friend and it was time you’d never get back, all because you had feelings you couldn’t swallow down. But they were always there, and now they’d gone and boiled over.

“You wanna know why it didn’t work out between us?” He asks, sudden as his question cuts through the quiet in the room save for the ongoing storm. You don’t say a word, laying still as your gaze is fixed on the wall and your back remains to him. You don’t know what he could possibly say or what it was supposed to make you feel but you couldn’t find it in yourself to press for an answer. If he told you, fine, but if he didn’t—

“It didn’t work because she wasn’t you.”

You stilled even more if that was possible, your heart skipping more than a few beats as your brows furrow. You were utterly baffled, unsure if you’d even heard him correctly or if it was some dream you’d been having that you were bound to wake up from. Your movement was sudden as you sat up and turned around, the faint bit of light illuminating the expression you held.

“What?”

He sat across from you on the edge of his bed, brows knit together in the dim lighting. He laughed softly as he looked at his hands, shaking his head. He stood to his feet and ran his hands through his hair, pacing a bit before he stood still.

“You’re my best friend, Y/n. You’re a pain in the ass, sure, but you’re my best friend,” he starts, your lips pursing as he cracked a smile. “I don’t know how I didn’t see it lately, I really don’t. But I’ve been lovin’ you since I was sixteen and it took me ten years and a month full of you ignoring me to see it. She’s not you, Y/n.”

“Why didn’t you tell me?”

He laughed softly, rubbing his face and releasing a sigh.

“Because, my life isn’t exactly a chick flick where the guy gets the girl of his dreams, is it, sweetheart? It’s more of a tragic Lifetime movie where the guy’s best friend falls for someone else,” he says, the corner of his mouth quirking up as he looked at his feet.

You swallowed thickly as you looked at him, cheeks burning and stomach filled with butterflies that raged in your stomach. You were at a loss for words as you sat there, starting to wonder for the second time that night if what you were hearing was a dream. Dean Winchester, your best friend, the one you’d spend the better part of ten years pining after, was in love with you. You couldn’t grasp that thought. Not that you had much time to before he spoke up.

“Sweetheart, please say something. I know you’re mad at me but right now I’m starting to feel a little bit like a complete idiot and I—”

Before he could finish you’d already stood to your feet and grabbed the collar to his leather jacket, your lips on his without second thought. It took him by surprise for just a moment before his hands settled on your face, his smile pressing into your lips. You pulled away for just a second, his lips lingering over yours in hopes you wouldn’t stray too far. You wouldn’t, just enough for you to say one more thing.

“You are an idiot.”

He huffed out a soft laugh as his breath brushed warmly against your lips, hands dropping from your face in favor of pulling you closer before he dipped down and kissed you again.

—

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