Come hell or high water. | Dean Winchester x Reader
Summary: Looming over the Winchesters and [Y/N] is the war between heaven and hell. Dean will ultimately be faced with a choice he’d never be able to make. What will happen?
This will be a multi-part story, not necessarily set in a specific season but around 4-5 (verging on 6 at this point) would be the best fit.
Pairing: Dean Winchester x Reader
Warnings: Supernatural level violence, the rest is pure fluff this go-round.
Mentions: Sam Winchester, Bobby Singer, John Winchester, Lucifer
Here’s Part VI if you haven’t read.
They were just about to enter an abandoned building. Sam, Dean and [Y/N] were on a hunt. It was pretty run of the mill, just a couple of vampires. It wasn’t a large nest—just three or four. All three of them had exited the impala and walked around to the trunk. Dean had opened it up and pulled out three machetes. One was handed to Sam, one to [Y/N] and one for himself to keep. “Alright, let’s just get in and get out. I’m not trying to linger here too long. We got plans and all.” Dean spoke with a smile to [Y/N]. She looked towards him and smiled brightly. It was [Y/N]’s birthday. Sam chuckled softly shaking his head. “Yeah. We. Don’t rush straight to all the couple stuff and you inevitably making me wanna hurl.” Sam butted in, chuckling softly. “All night long.” Dean teased him, [Y/N] couldn’t help but to laugh. Gently pushing down the trunk of Baby, the eldest Winchester would take a gentle breath. “Alright c’mon you two—let’s just get this over with.” [Y/N] spoke before leading the trio towards the abandoned building. All three of them had done this more times than they could count. It was something that became so routine they could almost do it with their eyes closed. After taking a deep breath the group began making their way towards the door. Once inside they remained hush-hush, using hand signals to communicate, much like cops—it had been a running joke at this point. Sam went down the whole way to the basement, Dean took the middle floor and [Y/N] took the top floor.
Sam had found one vamp in the basement, successfully killing it without much fuss. [Y/N] found one on the top floor and it was pretty much the same experience: an easy kill. Almost like it was too easy. Sam didn’t hear much from the floor above, which had been a little strange. He began to head up slowly, just in case there was something going on so he’d be closer. She’d thought a similar thought from above and was headed down—if she was done there’s no way Dean wouldn’t be, this feeling intensified when she entered the little corridor to see Sam coming up from his floor. [Y/N] had a sinking feeling. “You done?” She whispered, her eyes gazing towards Sam and they were betraying her feelings easily. “Yeah. You also feeling like something is..” He was trailing off so she’d nodded and picked his sentence back up. “Weird? Yeah. Almost like this was..” she trailed off this time and it was the younger Winchester who picked the sentence up. “Too easy?” [Y/N] nodded her head. They’d been standing there for at least a minute or two and still there was no noise, no sign of Dean anywhere. Now she was feeling incredibly uneasy. “I say we go in, he can yell if things are fine but there’s no way we’d be done and he’s not.” Her voice betrayed how stressed she was, which to the brothers was an indication that there was something wrong. Sam nodded and slowly, they both pushed the doors open and made their way inside the main portion of the second floor. They’d taken a mere few steps inside when both of them heard Dean groan in pain. It made her heart began to race as both her and Sam began to rush toward the sound. It was still possible it was a small miscalculation but they both knew that was highly unlikely.
However they didn’t want to move too quickly and spook the vamp into doing something drastic. So they moved as they always would in these situations despite everything inside of [Y/N] telling her to run. After what seemed like years they rounded the corner and saw Dean struggling to fend off three vampires—this wasn’t making any sense. Both Sam and [Y/N] ran over gripping their machetes tightly. Sam took the one on the left and [Y/N] took the one on the right. Luckily it caught them off guard and that left just one for Dean to handle. How did they calculate things so incorrectly? She felt a little better when she caught Dean up and fighting in her peripheral vision. Sam was the first to finish off the vamp he was fighting, slicing its head clean off with a swift motion. [Y/N] was the next to do so, ducking an attempt by the vampire to grab her and quickly recovering to slice its head off from behind. Odds had swung in their favor but she still felt a lingering feeling of dread. It didn’t take long to figure out why, the second she turned around she saw Dean swinging his machete, but the vampire knocked it from his hand with a strong kick to his arm. Both Sam and [Y/N] began moving from the opposite directions towards Dean, but what happened next was unexpected—after ducking from a punch thrown by the oldest Winchester, the vampire grabbed his fallen machete. Just as his brother and his girlfriend had reached where he was, the unthinkable happened and in the blink of an eye the vampire buried Dean’s own machete into his chest. [Y/N] screamed his name and ran for Dean dropping her machete in the process, Sam doing the same but keeping his in hand because he knew that she was in distress. She’d reached the eldest Winchester before he’d even fully realized what happened. Hands pressing against his chest to stop the bleeding though she knew deep down that it couldn’t be stopped. Sam with the added rage came in swinging, quickly decapitating the vamp. [Y/N]’s eyes clouded with tears but she kept blinking them away.
Dean was coughing, gasping for air while his hand reached for hers. Sam had rushed over and knelt down beside Dean on the floor. Seeing his brother joining them, Dean grabbed onto his arm and slowly began to speak. “Take.. take care of her Sammy.” He uttered, his voice weak. Sam’s eyes filled with tears but he nodded slowly. “I will, Dean.” He spoke lowly. Both brothers’ gazes moved to [Y/N] and Sam grew quiet, just holding his brother’s arm. “Sweetheart..” Dean coughed and gripped her hand tighter, getting her attention fully. “I’m sorry I ruined your birthday.” He sputtered, making her cry even more. “You didn’t..” she lied, sobbing out her words. “I love you,” he coughed, voice getting more hoarse the more he spoke. “I need you.. to-to watch after Sammy.” She felt like a knife was being driven into her heart. “I know, I will baby. I’ll keep an eye on him..” She sobbed every word, holding back enough so it wouldn’t mess with her words. “I love you too Dean.” It was then that the grip he had on both his brother and his girlfriend began to lessen and lessen until both arms went entirely limp.
She gasped, sitting up in a panic. [Y/N] was short of breath as she tried to figure out where she was—looking around and seeing familiar walls. Cheap art bought at yard sales. She knew because she’d bought it for Bobby to make his house more ‘homey’. He hated it but he’d never outwardly tell her that. It was then that she relaxed just a little, she was okay… she turned to the side to see.. an empty bed? Oh god.. was that a memory? Where was Dean? She began to hyperventilate a little as she threw the comforter off of her body. Pushing herself up to her feet she began to feel panicked. “Dean..?” She whispered out, scared of the answers that waited further into Bobby’s house. “Dean!” She yelled out, moving into the short hallway and down towards the stairs. She began running down the stairs and yelling Dean’s name. Every instinct in her body being set off, but just as she got to the bottom of the stairs she saw Dean looking worried and jogging to her. “Dean!” She exclaimed, throwing her arms around him and squeezing like he’d disappear if she let go. “I’m here baby, I’m right here.” His voice was low and gentle, he’d wrapped his arms around her and held just as tightly onto her as she was to him. Maybe more. “It was just a nightmare, shhh. I got you, you hear me? You’re safe. I’m safe.” He kept repeating those words over and over, holding onto her and rocking her gently. Sam and Bobby looked over with sympathy—the three of them had been in the kitchen while Dean was making her breakfast. He’d dropped the skillet onto the burner when he’d heard her frantically yelling his name. Bobby had quickly grabbed it to both spare the work Dean put in and to prevent his house from catching fire. Sam had sprung up but when he heard Dean soothing [Y/N] he kept back and gave them a minute to themselves.
She’d been silently sobbing in Dean’s arms as he soothed her, it took about ten minutes but he finally managed to calm [Y/N] down. “It’s okay, baby. Don’t worry.” He spoke with his face buried in her hair. “I’m sorry, I’m sorry..” she whispered a couple more times before really hearing what her boyfriend was saying and for the next few minutes there was silence. “Hey, I made you some breakfast. You hungry?” He asked softly to which she nodded. “Yeah, yeah.. thank you.” She replied, but her tone was soft—almost.. small. It made them all sad, hearing the woman they knew and loved sounding so.. broken. Dean kept his arm around her shoulders as they slowly waked towards the kitchen. Sam and Bobby tried their best to not look sombrely at her but it was impossible. She’d only been back for less than twenty-four hours. “Hi.” She spoke seeing Sam and Bobby standing there. “Hi kiddo.” Bobby spoke, hints of emotion in his voice. Slowly [Y/N] pulled away from Dean and walked to the man that had Ben one of her prominent father figures since her own had died. “I missed you.” She spoke softly and it could be heard when Bobby sniffled. “I missed you too kid.” He wrapped his arms around her gently and she did the same. They stood there hugging for a minute or two before she gently pulled back. Now she turned, giving her full attention to Sam. He’d been tearing up seeing [Y/N] and Bobby but the tears slowly fell now that she was looking at him. She laughed softly, which felt out of place but it was the kind of laugh that occurred when you’d done something that seemed impossible. She quickly walked towards Sam and wrapped her arms around him. “I missed you so much, [Y/N/N].” He’d spoke softly while gently while they hugged. She gave him a firm squeeze, almost like she was still questioning whether this was real or not. “I missed you too, Sammy—so much.” Her voice was gentle and they lingered for a moment or so before pulling back.
Just like the opposite ends of a magnet [Y/N] found herself moving immediately back to Dean. Which he welcomed with open arms—physically and mentally. After a year and a half he’d missed having her in his arms. He’d missed the way her skin felt, the way she smelled and the way that she brought peace to his soul. Sam and Bobby were happy to have [Y/N] back of course, but they were also happy to see Dean at ease and smiling for the first time in a year and a half. Slowly they both exited the kitchen to give them some time to talk. When Dean had gotten her back to the house the night before, she was exhausted and laid down and slept immediately. She sat down at the table, so Dean began to dish up the eggs and bacon he’d made for her. He’d also made her toast, just the way she liked it. [Y/N] smiled at him but the light didn’t quite reach her eyes. After all of the food was on the plate, he’d set it down in front of her and immediately sat in the chair next to her. “Thank you.” She spoke, the tone of voice still soft and sad. He watched her as she picked at the food, taking small bites of the eggs. There was a silence that hovered over the couple for a little bit, before Dean took a deep breath in. “You uh.. you wanna tell me what had you so scared?” He asked in a gentle tone, not wanting to push her into anything. She gulped a little harshly. Dean knew how much he was shut off for a couple days after he’d returned from hell and she’d been so patient with him, he wanted to offer her the same courtesy. “You don’t have to explain if you don’t want to though.” [Y/N]’s gaze fell to the table and she began to pick at the eggs again. Silence filled the air in Bobby’s kitchen, for minutes on end. Dean opened his mouth, about to say something, but she finally spoke. “It was.. it was one of the things Lucifer made me live in.” She replied finally, her voice was shaking a little bit. [Y/N] didn’t know whether she should even continue but.. she knew that Dean deserved the truth. She always asked him for it when these situations were reversed, so she needed to practice what she preached.
Dean swallowed hard, he should’ve known that’s what it was—he still had nightmares about his own experience. What was worse in this sense, was that he saw the absolute fear in his girlfriend’s eyes when she came flying down the stairs. It was a look he’d seen a few times and that scared him for what she was about to explain. [Y/N]’s voice still sounded so small, but she continued to speak. “It was my birthday, you, Sam and I were on a hunt. Just a quick one, we thought. Clearing a couple stray vamps and being done for.. whatever we had planned for my birthday.” Dean’s heart broke, hearing that she’d been made to believe, likely more than once, that something horrific happened on her birthday. Lucifer was a prick, always trying to take the deepest jabs at people. [Y/N] took another deep breath, trying to keep her voice steady. He reached out apprehensively to lay his hand atop her own, supporting her without speaking as he didn’t want to interrupt. “It was a three story building, we split floors because we knew there was maximum three or four vamps. You know, just a quick stop and nothing more. Sam and I cleared our floors, we’d met on the staircase and both of us were confused.” She laughed in a sort of dry fashion. “You’d never be the last one done, usually you were the first.” Dean could feel her shaking a little and gently squeezed her hand. “We knew something was wrong from that fact alone, so we moved into your floor and started looking around. We.. miscalculated, three extra vamps were there somehow..” she trailed off and she felt sick to her stomach. Dean knew the feeling she had, he could read her face and her body language and gently pulled the fork from her hand and placed it onto the table—he quickly brought their hands together and intertwined their fingers. “I’m right here sweetheart. I know it must be so hard, but it wasn’t real and I’m right here.” He spoke in such a soft tone that it made her feel more emotional. [Y/N] felt the tears welling up in her eyes but she tried to just blink them away. Firmly she squeezed Dean’s hand, making sure he was indeed right there with her and that further broke his heart.
“Sam and I rushed over, each tackling one of the vamps and you’d been fine, you were fine when I looked at you and then it happened so fast..” she squeezed his hand a little harder, as if to ground herself in the reality of this moment. “He knocked the machete out of your hand by kicking your arm, you tried to land a punch but he ducked and then..” she felt the tears falling onto her cheeks. It was in this moment that she finally looked up, gazing into the green eyes of her boyfriend. It made his heart ache in his chest but he just wanted to let her get it out, however long that took he didn’t care. He was there for her, just like he’d always been there for her and just like she’d always been there for him. “..while you were standing back up the vamp grabbed your machete and.. and..” more tears fell from her [Y/E/C] eyes and Dean just wanted to wrap his arms around her and never let go. “…he buried the machete in your chest and I panicked, dropped my machete and ran for you. Sam ran too but managed to keep his weapon and kill the bastard. You grabbed my hand and then grabbed Sam’s arm..” Again she squeezed Dean’s hand, keeping herself grounded. “You made him promise to take care of me, you apologized for ruining my birthday and asked me to keep an eye on him. You told me you loved me and when I said it to you.. you let go.” Dean’s heart was truly broken hearing how [Y/N]’s words towards the end turning into sobs. “That’s when you woke up—you came running down the stairs because I wasn’t in bed with you.” He spoke softly. She nodded, looking back down at the table. “I thought it-.. it was a recollection dream and that you were really gone.” After she’d finished speaking Dean got up from his chair and quickly wrapped his arms around her body. She melted into his embrace and sobbed for a few minutes. He just kept repeating himself, “You’re okay”, “I’ve got you”, all the usual phrases just to remind her that he was very much alive. This lasted for a couple minutes before they’d separated and she sat back down, finally eating the breakfast that Dean had made for her—he kept by her, sitting back down in the chair where he’d been a little bit before. Once she was finished, Dean gave her hand a gentle squeeze. “If you can handle it, I wanna take you back to your.. place.“ His voice was unsure, but she nodded. “Yeah, yeah.. I wanna go.” Dean clearly had something he wanted to show her and that was enough for her to be okay with going.
A few hours later at [Y/N]’s place..
Dean held tightly onto [Y/N]’s hand as they walked through the gate. It was a gate that looked handcrafted, he’d stopped when he noticed that she was looking at it. “Bobby made it, Sammy did the flowers in the spaces.” He spoke softly, leaning into her and looking up at the gate. “Sunflowers, my favorite.” She spoke with a genuine sense of appreciation and love, moving her gaze over to Dean. His eyes were shining with emotion but mostly with love. They began to move into the main area of the place, where the coffin had been buried. It was surrounded with more sunflowers, some fake and some real. It made her feel a sense of warmth that she hadn’t felt in so long. Dean noticed this and it caused a smile to slowly spread across his lips. Alongside the flowers she noticed some signs, they looked hand painted and featured lyrics from some of her favorite songs. [Y/N] gently pulled Dean towards one of them, smiling as she read the lyric. All we are is dust in the wind. It was one of her favorite songs. He squeezed her hand which drew her from her thoughts. “I used to sit here and play it, over and over again until I was almost tired of Kansas.” There was a sad edge to his voice, but he didn’t need to be sad now. “Remember that day, jeez, we’d known each other about two weeks at that point.” He began explaining. “We were driving to help my dad with a poltergeist case in Memphis.” [Y/N]’s face lit up when she recalled the day, but he continued to speak. “We were listening to music and I was about to change the tape—“ she cut him off affectionately. “..but I made you leave it because ‘Dust In The Wind’ came on and you groaned initially.” She spoke with a gentle chuckle after. “I did, yeah. I’m glad I listened, cause looking over at you in the passenger seat.. sun shining on you through the windshield, singing that damn song—that was the moment I really fell in love with you.” Dean’s voice held so much emotion and she fully turned to look at him. [Y/E/C] eyes brimming with tears. “You never told me that.” She whispered, her heart soaring. He squeezed her hand again while taking her other one into his free hand. There was a comfortable silence that surrounded them for a minute or two, but he wasn’t done. “I wanna read you something.” He spoke up, finally breaking that bit of silence. This gained more interest from [Y/N] and so she nodded. “Okay.” Dean wore a smile but she could tell he was feeling a bit nervous. Slowly he lead her towards the hole in the ground where she’d emerged from less than a day ago. He released his grip on both of her hands and moved toward the hole. Grabbing a shovel, he began to dig—just enough to widen the hole. Once he’d finished with that he tossed the shovel up into the grass. Slowly he bent down, grabbing two things from what was left of the coffin. One thing he slipped into the pocket of his coat and the other he kept in hand, pulling himself back up to the level ground. Dean walked back over to where [Y/N] stood with an envelope in hand, which she could see hand her name on the outside. “I wrote this the day after.. everything. I buried it with one of your favorite dresses, because they were two things that connected us.” He spoke, ripping the envelope open and pulling out a letter. Again she felt tears in her eyes, but she stayed quiet as she still sensed his nervousness. Dean cleared his throat before beginning to read.
“[Y/N/N], I will never have the words to explain how much you made my life better. You know I’m not good with saying how I feel, though I’ve gotten better at it thanks to you. I’ve been sitting here lost in every moment we shared, regretting that I never said ‘I love you’ as much as I should’ve. It was so hard for me to say it, not because I didn’t love you but because everything I’ve loved or held close.. they’ve left, or they’ve died and now.. you sacrificed yourself to spare me from making an impossible choice—but you also saved Sam from having to endure so much pain and torture and I.. I am in so much pain and yet it just made me love you more. I’ve spent so long taking care of Sammy, I never knew what it was like to be taken care of, not until I met you. Up until the last moment.. you put me and my needs above your own. God you’re.. you were.. so selfless. You always told me that perfect didn’t exist but I saw it every time I looked in your eyes. I woke up today hit with the weight of not having you next to me, your hair not sprawled across my face and in my mouth, no warmth where the brightest bit of sunshine usually laid. I was also hit with all the things I’ve never said to you, like, driving down the road to Memphis and watching you singing along to Kansas, that was the moment I fell in love with you. I never told you that dad told me he knew I was gonna spend the rest of my life trying to keep up with you. He told me that I looked at you the way he looked at Mom and that bastard didn’t like many people.
I never got to tell you how you made vanilla and lavender my favorite smells, it just smells like you. When we had to be apart I actually used to swipe your perfume and spray it on my shirts so I had a piece of you with me. Sam made fun of me for it when he found out but I never cared. I slept last night holding onto one of your shirts for that same reason. God, sweetheart I don’t know how I’m gonna do this—I can’t live without you. You’ve been my anchor and the beacon of light in my sea. You’ve got me writing mushy crap and feeling every bit of it. [Y/N] you got under my skin in the best way and I feel so empty without you here. Sam and I, we’re gonna get you back. I don’t know how, I don’t care how long it takes, we’re gonna get you back and I’m gonna say all of this and maybe more.
Another thing I never told you, when I got myself nabbed by that djinn, my dream world was that damned apple pie life I always told myself I never wanted. You knew that much, but what I never told you was.. that next week, I went and bought you a ring. I didn’t know when or where, but I was gonna give us just a little bit of that apple pie life. I kept it hidden at Bobby’s so you wouldn’t find it. Baby I was so scared to ask you that question and as I’m sitting here without you.. it’s the one thing I wish I’d asked the most. It doesn’t matter when, or where, or any of that. When I get you back, I’m gonna ask you and we’re gonna get that slice of heaven. I love you, [Y/N/N].”
She’d been standing there, listening to him read this letter and feeling so many emotions swirling inside of her mind. However that wasn’t the end of this—slowly Dean got down on one knee and pulled out a small velvet box. “I hope you never question if you’re loved, cause if you do it means I’m failin’ and I’d be disgusted with myself. [Y/N] [Y/M/N] [Y/L/N].. will you marry me?” His voice was the shakiest she’d ever heard it in all the years she’d known him. Tears flowing from both of their eyes as she nodded profusely—smiling and lunging forward into his arms. “Yes, yes of course I’ll marry you Dean!” His arms wrapped around her and held her as tightly as he could to his chest. “Alright let me put the damn ring on you.” He muttered with a chuckle. She pulled back and gave Dean her hand, watching as he removed the diamond ring from the box and slid it onto her ring finger. It was a simple ring and the most beautiful thing she’d ever seen. Once it was settled on her finger, he gently pushed himself back up to his feet. [Y/N] admired the ring before she flung herself into Dean’s arms again, their lips crashing into one another’s with a surge of emotions—love, joy, hope. For the first time in a year and a half, things were finally looking up.
AUTHOR’S NOTE: Hii everyone! I am SO sorry for the long wait! I had wicked writer’s block and had to combat a slew of other things but I hope you enjoy the chapter! This story will be drawing to a close soon, I’m debating if I wanna do one more part and an epilogue or a few more parts. I appreciate everyone’s love and support on the story! 🤍
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