Dean Winchester One Shots

By Deans-Gardian-Angel

108 0 0

A compilation of all my Dean Winchester oneshots More

Define Love
Piggy Back Ride
Halloween Special

You're Still My Favourite Star

48 0 0
By Deans-Gardian-Angel



The pranks had escalated. She feared for her life at this point. Maybe the glitter was a step too far. He had given her a three-second count down and she took advantage, running as fast as she could as she shrieked for Dean to save her. Naturally, Dean pulled out his gun and took a stance to protect her. Ready to kill whatever was coming after her, he spots her smiling from ear to ear. She practically jumped into his arms as she giggled. Dean couldn't help but smile. He'd had a crush — that's what he chooses to call it because if he admitted to loving her he wouldn't know how to act around her — on her since the day they had met. He had only grown fonder of her the longer she stayed with the Winchester's. She clung to him as he chuckled holding her against himself, smiling wildly.

"What's going on?"

She turned her head and noticed Sam marching over to them, a dangerous smirk on his face, pacified by the glitter on his eyelashes and lips. She faced Dean and in a teasing matter proceeded to explain.

"Dean I don't have much time. I threw a glitter bomb at Sam and now he's gonna kill me you have to save me, Dean, we have to get outta here."

He looked over at Sammy only to laugh before she hit his chest.

"We have to go now!"

"Oh gosh you're right we gotta go now. Y/N he's gonna kill you lets go." He kept up the life or death act as he took her hand and pulled her towards the car before both consecutively hopping into Baby and driving off, leaving Sam in the rear view mirror, arms in the sky.

Y/N and Dean laughed for a solid five minutes before Y/N stopped abruptly.

"Wait, Dean, we ditched Sam he's gonna be ultra pissed!"

"Nah he'll be fine he's probably just gonna hot-wire a car and drive back to the motel."

"Guess that means we can't go back to the motel then huh. If Sammy's there. Might die."

Dean chuckled and side-eyed her as he drove. She looked up at him through her eyelashes. There was glitter on her cheek, probably from the process of making the glitter bomb. With her sitting in his passenger seat, her hair a little wild from running, a smile decorating her face, and her left leg tucked up under the other, hands between them, she faced him. In that moment Dean felt a surge of confidence, acting more like his cocky self he is around other girls. Generally, he's more shy around her, taken aback by her confidence and goofiness.

"I guess you right sweetheart, can't go back there now that Sammy is gonna get you. That leaves you and me and Baby. Where we going." A smirk adorned his face, accompanied by a wink he sends her way making her smile wider.

"Stop at the next pullout big boy. I want to show you something." Dean nearly choked on her reply. Not only because of the words she used but because of the way she said it. A hushed sexual voice really, that affected Dean more than he'd care to admit. In a split second, she's herself again, giddy and energetic, a stark contrast to the sensual act she pulled mere moments ago.

"Do I even want to know"

"Of course you do. We're stopping at the next pull out so I can show you something you rarely get to see. Or at least I think you rarely get to see it."

"Do I get a hint?"

"Absolutely." She paused before finishing "Not."

She laughed at her own joke and pats a hand on his chest in a reassuring manner.

"Oh come on Dean it's nothing bad. And nothing you haven't seen before. Just not often. And that was funny. Relax a little. Just 'cause our job is heartbreaking and difficult doesn't mean we can't enjoy the time we have when we aren't on a case. You gotta learn to relax. Take a breath. Smile a little. You've got an excellent smile, Dean. Use it once in a while." She was tickling him to get him to smile and it had worked despite his better efforts. She was the one person who could put him in a carefree mood and it scared him. Terrified him to no end that a single human being could make him that happy. But she did and she didn't even have to try. All she had to do is look in his direction, call his name from down the hall, nudge him in passing, wish him goodnight on her way to bed. His life had an incredibly bright light that bounced around, was loud, and unconventional with her temperament. More commonly described as a child, Y/N didn't care about anything or anyone's opinion, simply chose to be unconditionally happy. Dean had fallen into an easy pattern with her. She was the one he'd go to with his nightmares and dark thoughts. The one he'd ask to join him on a supply runs just for some company or a drive down an empty road for some space. Essentially, she was the one he had an un-discussed relationship with. Little did she know Dean had been dating her in his head since they met. 'She has a boyfriend', that is if you asked Dean for her number or name at a bar.

"There! Right there, Dean! Stop right there!"

He chuckled pointing at the spot she'd chosen.

"That's not even a pullout!"

"Yeah but it's perfect just pull over Dean no ones around!"

He did as he was told putting Baby in park on a gravel patch in the middle of the open interstate.

"Okay, now what." He asked, pulling the keys out of the ignition and carelessly chucking them onto the dash. Dean threw his arm over the bench and turned to her, eyebrows raised in a questioning manner. She didn't say anything, opting for action rather than explanation as she hopped out of the sleek impala. When Dean didn't follow she dipped her head back in the passenger door with a wavering bitch face.

"Get your ass out here. Oh and turn the music back on."

Dean grew a crooked grin and huffed out a laugh before reigniting the stereo and getting out of the car himself.

Y/N was staring up at the sky, eyes shimmering with moonlight and a smile laid softy upon her lips.

"Look." She told him, holding out her hand to him blindly, which he eagerly took. She glanced at him quickly as he approached her.

"Up."

And so he did. Just as she said, what he was now gazing upon was nothing he hadn't seen before, though he was only now realizing how much he'd missed them. She hadn't let go of his hand and he hadn't, by any means, suggested she do so. After a minute or so he'd walked back a smidge breaking Y/Ns focus from the night sky and bringing it to him. She watched as he sat on the hood of his esteemed Baby and invited her over with a glance, or rather a nod to the spot next to him. She graciously accepted, sitting closer to him than he'd expected, resting her head on his shoulder. Dean tugged her closer, putting his arm around her and pulling her back so that both of them were comfortably leaning against the windshield looking up.

"Is this what you wanted to show me."

"Is this not enough. What'd you think I was gonna show you?" She asked with a smirk, looking up at him. Dean didn't answer, instead smirking in return.

"Dean Winchester, you didn't!?"

Deans smirk grew to a laugh as he pulled her closer kissing her forehead.

"Of course not sweetheart. No, I thought you were finally gonna show me how you got your beard to look like that 'cause I mean mine is nowhere near as nice as yours." He touched her chin.

"Hey! I don't have a beard!" She giggled profusely, but he had settled down, watching her laugh for as long as he could.

"No, but you've got some glitter on that pretty face of yours." He said as he touched her nose.

"Oh ya I was saving it for later," She replied sarcastically "you want some? Here."

She gathered the glitter from her cheek and smeared it on Deans in a warrior fashion.

"'We want a touchdown, We want a touchdown!'." she giggled again making Dean's heart melt for the 78th time in 2 hours.

"There now we're matching. Only yours is cooler." She had painted the glitter on his cheekbones as though he was watching the local unicorns win a football game.

She looked him in the eyes trying to gauge his reaction to her youthful behaviour, only to be met by stunningly green eyes that bore into her soul, a gentle smile on his face as he watched her intently. He hadn't noticed he'd been staring and she didn't say anything to deter him. Alternatively, in the heat of the moment, one may say, Y/N leaned over him and placed a tender kiss on his waiting lips. She hadn't planned this by any means, though she had dreamt of it quite literally. He was her superhero fantasy in a way, or at least that's how she would describe him. She had never dared allow herself to imagine Dean Winchester kissing back at all let alone in the tentative fashion that was the heaven she currently found herself in. His strong hand cradled her delicate features as he kissed her in return. Before he even had the chance to comprehend the situation she had pulled away and gotten off the hood of the car.

"Oh, gosh, Dean I'm so sorry I just, I don't even know what that was, I'm so sorry I really didn't mean to I promise." She turned to him gracefully touching her lips where his lay mere moments ago. Dean was unsure what to say. He wanted to tell her it was okay. More than okay. He wanted to beg her to do it again. But she had promised him she hadn't meant it leaving him to waver in his confidence. Maybe she really hadn't meant it. Maybe she felt pity for him. Dean closed his eyes in sadness and anger. Running his hand through his tousled hair he said the only thing he could,

"It's fine sweetheart, really."

"So I haven't gone and ruined our friendship in one fell swoop." Y/N was breathing heavily desperate to fix what she believed she had nearly lost with a single stupid action.

Dean could feel his heart tighten in his chest, his eyes grew watery as he struggled to get his next words out.

"No, we're just fine, don't you worry about that."

There was a pause before Y/N spoke hoping to alleviate the tension.

"Maybe we should just head back, hey Dean? Sam's probably wondering where we went anyway."

'Stay with me. Be with me. Kiss me again, but this time don't pull away, don't apologize. Let me hold you again. Let's look at the stars together and you can point out all your favourite while I watch your eyes scan over the sky. And then when you turn to me asking what my favourite star is, I'll tell you I'm holding it. Tell you my favourite star is the brightest one I've ever seen, tell you that you are my favourite star, my favourite good morning my favourite goodnight. Favourite smile, laugh, voice, hug, hand to hold.'

Instead, he turned back to the car and got in without a word. If only he could bring the words in his head to the tip of his tongue. If only he could tell her the truth. Y/N knew they were going to have to talk about it but she feared the outcome of the conversation. Expecting Dean to never want to speak with her again. She had ruined the only relationship she had ever truly cared about.

The drive back we sparse of noise, save for the Zeppelin tape playing quietly on the stereo. Neither had dared make a sudden movement such as to turn off the tape, both relishing in the lack of conversation. Y/N had stolen a few glances at Dean noticing his big glossy eyes, wanting to explain herself and apologize once more, but refrained from doing so. It hurt her to see him this way though she didn't understand. When they arrived at the motel, Dean parked Baby in front of their shared room, cutting off the engine. Neither one nor the other moved from their spot in Baby's upholstery. Dean sat with his hands in lap staring down at them, too afraid to look Y/N in the eyes fearing that if he did he'd lose control; either kiss her without hesitation or break down and cry all the tears he'd been holding back. Both options were ones he'd like to avoid, and so without a word, he began to reach for the door handle just as she spoke.

"Dean, I'm really sorry, can we just forget about it please?"

"Would you stop apologizing!" He'd scared her, he could see it now as he'd turned to her with his outburst. Y/N had slumped down in her seat leaning against the door, arms over her body in hopes of shrinking and sheltering herself. Dean's rage and unanticipated movement had shaken loose the tears that had been desperately clinging to his eyes. Sam opened the door to the motel emerging in his PJs no longer covered in glitter. The minor distraction had allowed for Y/N to slip out of the car and past Sam into the room.

"Dean? What happen, did I cock-block you." Sam was laughing at the situation missing the tension between his brother and the girl he knew Dean had loved since she had burst her way into their life. "I heard the car pull up but no one came in so I came out to check and—" Dean didn't answer his little brother, shoving passed him into the room after locking Baby up for the night.

The rest of the evening was filled with questioning glances from Sam and in return; angry and sad one from Dean and Y/N respectively. Dean took the couch mostly because he had already fallen asleep on it as had Y/N on the bed. When Sam was sure his brother was lost in his slumber, he proceeded to wake the girl that lay on the bed across from him. As she stirred he whispered at her pulling her from rest.

"Y/N? Wake up. We need to talk."

Those words startled her awake, calling for Dean, thinking he was the one waking her to tell her that she couldn't stay with them any longer.

"It just me Y/N relax. What happened to you guys, you ran off like a pair of giddy kids and came back the complete opposite. Explain."
"Sam, really, nothing happened. It was a stupid little mistake, I wasn't thinking and made a mistake. It was an accident and now Dean is thoroughly pissed with me. I've tried apologizing but he yelled at me not to, so there isn't much else to do. Tomorrow he's gonna tell me to leave and I will. I don't want more conflict than I've already conjured."

"Okay first off; you're both children, I don't know what you did but considering no ones dead or injured he'll get over it. Secondly; he's not kicking you out 'cause if he does I'm going with, just to prove how stupid he's being, so that won't happen, you don't have to worry about that. And thirdly; would you just tell me what you did so I can better assess the situation?"

"I kissed him. We were looking a the stars and I — I looked at him and he was smiling at me and he looked happy and the feeling of him being happy in that situation, with me in his arms just the two of us, not a soul to be seen, it was overwhelming and I leaned over and kissed him without even thinking of how he might not want me to. About how we're friends and I could ruin everything we have. I immediately jump off and apologized though, I thought I could still save that sliver of friendship I hadn't destroyed but I was too late."

Sam was chuckling as he hung his head shaking it.

"Sam it's not funny. I can't lose him, I can't lose either of you."

"He is such an idiot. Y/N was it spur of the moment, or have you liked him for a while. I wasn't just a one-time thing was it."

"That's not the point Sam, I sacred him and ruined everything..."

"Scared him; yes, but he's afraid of flying so that's nothing special, ruined everything? Never, at least not with a kiss. And... that is the point, isn't it, you like him that why you kissed him... I'll talk to him"

"No! You can't! If you do he'll know I told you and that would just make it worse. Like I'd rather talk to his brother than him."

"Don't worry Y/N, I'll just ask him what happened I won't mention anything you told me. Promise. Go back to sleep, we can deal with this in the morning."

With that, she laid her head on her pillow and did her best to drift back into the sleep she had been pulled from.

When Y/N awoke the next morning, Sam was only just putting on his running shoes. She glanced at the clock and groaned in response to the early hour.

"Morning Y/N."

"Morning Sam." She replied as she flopped back onto the bed. "You going for a run?"

"Yeah, should be back before he wakes up so..." He nodded in his brothers direction, huffing out a laugh at the uncomfortable-looking position Dean lay in.

"I'll be fine Sam, don't rush."

Sam only nodded in acknowledgment waving at her as he closed the door behind him. Y/N took the morning slowly, inching out of the bed as quietly as she could to prevent waking the sleeping body. Y/N strode over to the coffee machine and set it up, turning it on only to jump and the loud noise it made. Her heart was racing as she bent over, bracing herself on her knees doing her best to calm her breathing. She instantly remembered Dean and looked over to see him tucking his gun back into his folded pants on the coffee table next to him.

"Sorry, Dean..."

"I told you to stop apologizing." He sat on the couch rubbing the sleep from his eyes, sniffling a little. He glanced at the clock groaning at the early hour. If she hadn't had just been startled she would laugh at the similarity of their actions which in turn would have made Dean happy because when she's happy, he's happy. But she didn't.

"I was saying sorry for waking you up, not the k— not last night."

"Right. Sorry..." Dean looked around the room noticing his brother wasn't around to be a buffer. "Sammy go for his run?"

"Yeah, left maybe ten, fifteen minutes ago?"

"Great." Y/N could only hear his word in a sarcastic tone making her think the worst. Dean got up as Y/N finished up making the coffee, making his way to the bathroom. He passed her in only his underwear and shirt, such were his PJs, jeans under his arm, running his hand over her shoulder and back, a customary occurrence with the two of them, though she had been on edge ever since the kiss, making her flinched under his touch. It didn't go unnoticed as he looked at her. She opened her mouth to apologize again but before she could get the words out he snickers with a hand dismissing her 'sorry' as he walked away. Dean entered the bathroom looking himself in the mirror momentarily. Cursing himself under his breath. He put on his pants and went to reach for the cups that were usually supplied at a motel only to remember that they had been placed by the coffee machine outside. When Dean opened the door he hadn't expected to see her crying at the table with her cup of coffee, in fact, this was the first time he had ever seen her cry. She was always happy, always smiling or laughing, and most often both. It broke through the shell he had built up by trying to ignore her. Instantly, Dean rushed over and called for her, kneeling down next to her chair.

"Hey! Y/N, what's wrong? What happened? Are you hurt?" As if Sams timing had a grudge against the eldest brother, the long-haired goon walked it all hot and sweaty from his run. Noticing Y/N right away his first reaction was to blame his brother given what Y/N had told him the night before.

"Dean, what did you do to her!?"

"What did 'I' do to her!?" He got up, facing his brother, his hand still on Y/N shoulder as she watched the brothers interaction. "Why do I always, always get the blame!" With that Dean grabbed his jacket his keys and his boots, walking out without even putting them on. Seconds later the sound of Baby turning over engulfed their ears followed by burning rubber, then silence. Y/N got up and followed Deans actions grabbing her jacket and boots though she put hers on before marching out to god knows where.

"Man those two better talk to each other before I rat 'em both out." Sam mumbled to himself before taking a shower and a coffee.

~~~~~~~~~~

Dean drove and drove and drove for hours trying to work out a way to tell her, trying to work out her reaction to his confession. At the rate they were at now it seemed as though he was bound to lose her whether he spoke to her or not. He figured he was better off explaining himself and his reaction and lose her, then ironically driving her away with the fear of losing her. That was it, he had decided, he was going to go back to the motel and tell Sam to go for a walk so he could talk to her. With a plan in mind, he returned to the parking spot he was pulling out of earlier that day and making his way to the door dividing him from his future.

Meanwhile, Y/N walked. She hadn't stopped, not realizing how long she had been walking until she lifted her head as her feet grew tired. She wasn't far from the edge of town, no far off from where she had stupidly kissed him the night before. She laughed at her self conscious that had lead her here. She'd be at the spot in just under an hour had she kept walking but she was tired and rightfully so. Y/N spotted a bench in the park off the interstate and took a seat leaning her head back as she watched the sunset over the valley of kids on the playground. She'd had plenty of time to think between shops she'd stopped in to either look around and take her mind off things or find something to eat. She had established in her mind that whether she or Sam liked it, it was inevitable that she would be kicked out, if not she'd leave on her own. Y/N no longer wanted for Dean to be mad at her and so that was what she would do. She would move on, she had come to terms with that. But she wouldn't leave without explaining herself to him first. She didn't want to leave him in the dark anymore. As she pulled out her phone to call them for a lift — she wasn't the biggest fan of walking back right now — she noticed the 13 missed calls from both Sam and Dean. Guilt washed over her but before she had the chance to call them back she heard the familiar purr of Baby's engine. Y/N lifter her gaze from her phone to the tired and puffy eyes hanging out the window of the '67 chevy. With one arm out the window he gestured for her to come over and she did. As she approached the car she held up her phone.

"Sorry, I was so in my head that I—"

"Y/N. Stop. Stop apologizing." This time he wasn't angry "Just stop apologizing and get in. We need to talk." Dean was smiling shyly but his words had confirmed her notion. With shaky hands and a nearly defining pulse, she opened the passenger door and got in.

"When I got back to the motel, Sammy asked me if you were with me and I panicked. We tried calling you but you wouldn't pick up so I had Sammy track your phone." Dean answered her unvoiced question as he pulled away from the curb, driving out of town.

"Where are you going the motels behind us."

"I told you; we need to talk."

"Yeah, but..." she didn't want to argue with him more than she already had and so she turned back towards the open road he'd started on.

He drove until he reached the gravel patch they had stopped at less than 24 hours ago.

"Dean I—"

"Wait just, Y/N I have to tell you something and I—"

"I need to go first, Dean. Please." Dean nodded bracing his heart for the worst as they faced each other. It took her a minute to find the words, licking her lips when she would try to talk only to bite it back along with the words. Dean waited patiently because deep down he knew, or so he thought, how this would end, and the longer he had with her, even in the silence they sat in, was better than the anticipated ending.

"Dean, I'm sorry—"

"Sweetheart I already told you—"

"No, Dean just let me finish please I have to say this and if I don't it's just gonna eat away at me and I don't want that." Her eyes were squeezed closed half expecting another outburst half expecting herself to implode.

"Okay."

"Dean Winchester, I'm sorry for kissing you and making a mess of things. I know I shouldn't have done it, I know I should have thought before I did anything stupid but evidently, I didn't. It was impulsive. It just felt right in the moment with you looking at me, holding me against your warm body in the cold air I— you looked happy and part of me wanted to believe that I was the reason for the smile on your face and that same part of me was the one that made me kiss you. I wish I could say it was an accident but, honestly Dean, I've been dreaming about that kiss since about a week after we meet. I'm sorry I flinched after you touched my shoulder this morning. I just had it in my head that you were mad at me and I was already on edge Dean, it wasn't 'cause it was you. I was crying this morning because I thought you were going to kick me out and I really didn't want that because you and Sammy are all I have." Y/N was on the brink of crying for the second time today and she moved to exit the car abruptly. Dean followed her out just as fast, wanting to console her but also to tell she has nothing to worry about. "I'm sorry I messed things up and I understand if you want me to leave. In fact, if I had been smart enough when leaving the motel after you this morning, I'd have brought my bag with me." Her body shook as her tears blurred her vision of the man that stood in front of her. Had she been able to see him clearly she would have noticed his broken demeanour and the hurting expression on his face but alas.

"Are you done?" She could hear him choke back a sob and she looked up wiping her tears away with her sleeve as he did the same the one tear he let slip. All she did was nod.

"My turn then. I wasn't the one to pull away from that kiss Y/N you were. You're the one who freaked out right away. And then you went on saying you didn't mean to. You know how that made me feel? Like you pitied me. Like I wasn't someone you'd actually kiss. You were right though, you were the reason I was happy Y/N, you're always the reason I'm happy. I wanted to tell you there and then that I love you that I wanted you to kiss me again but you — you were too concerned with saving our friendship. And I was too concerned about my own pride to tell you those things only to get rejected by the only one I've ever genuinely care about." He looked down to his feet which he'd now focused on in between small glances at her or their surroundings, no longer able to hold her gaze. He knew he had to look at her now though. If anything was going to happen, it had to be initiated with eye contact. When he finally laid his eyes on her all he wanted to do was hold her, wipe her tears away, tell her everything was going to be okay. But he couldn't, not this time, because this time he was the reason she'd been crying, though she'd stopped, and he knew that.

"You love me?" Accentuating her words as she pointed to Dean and then herself, hand still visibly shaking. He didn't dare break eye contact as he nodded his reply and she nodded in return, processing his admission. She sniffled a little more wiping more at her eyes still nodding slightly unsure of how to proceed.

"You love me." She said again and this time Dean laughed out a 'yeah' also wiping away the remainder of his tears.

"Okay, so Dean here's the deal," he looked at her with fear in his eyes still expecting rejection "I'm gonna kiss you again because I really want to and not because I pity you because you're someone I want to kiss. And this time I'm not gonna pull away and apologize. Okay?" He nodded again and with shaky legs Y/N stepped forward and grabbed onto his collar pulling him closer. She placed her lips on his as her heart raced out of control. Dean kissed back instantaneously but took a few seconds to get his hand to move around her waist. The kiss wasn't greedy or rushed rather desirous and mindful. Dean practically stumbled back taking her with him until his legs hit the car they had piled out of. Dean sat on the hood breaking the kiss to both catch his breath and to hold her closer, enveloping her in his embrace. He sat there hugging her closely as long as he could only pulling away a smidge to look her in the eyes to answer her question.

"You okay?" His eyes were on hers as he nodded.

"I'm sorry I made you cry. You never cry you're always happy and then I come along and make you cry." He brushed his thumb over her cheek as he whispered to her. She chuckled at him.

"You think I'm always happy?"

"Every time I see you you're grinning from ear to ear." He tucked some loose locks behind her ear.

"Dean, I'm 'grinning ear to ear' when I see you. I'm not always happy. Sure I may be more optimistic than some but I'm hardly always happy. You're the one who makes me happy. I'm happy when you're around."

"Really?!"

"Don't sound so surprised Dean." But he was surprised. Never could he imagine being the reason for someone else's happiness. He looked at her and blushed.

"You're blushing." She smiled at him gracing his cheek with her delicate touch. Dean dropped his head to her shoulder in an effort to hid it and laughed into her jacket. Y/N pushed him back against the car and hopped up next to him leaning against him the same way she had the night before. Y/N looked back up to the sky and once again Dean watched her. She turned in his grip and looked at him, the same look on his face, smile and all, as the night before.

"You look happy."

"It's because of you."

This time when she leaned over him and finally made contact she could feel him kiss back. Last time she had been too caught up in her own actions to register his response but this time she knew. This time she didn't spring off him, didn't apologize. She would tell him later that night that she loved him in return but for the time being, she cozied up into his body as they both look up at the sky. She pointed a few out, earning a chuckle here and there for her explanation and reasons she like those particular ones. Just as Dean played it out in his head the night before she turned to him. But what she said wasn't what his mind had conjured up for him.

"But at the end of the day, you're still my favourite star, Dean Winchester."

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