Dean x Reader
Request by @ShotThrewTheHot, Reader and Dean have a history but after the day Sam jumped into the cage Dean made a decision that completely broke her. Two years later a chance run in leads to Deans second chance, but after learning Y/N doesn't exactly work alone he tries to confront her, but in the end only heartbreak is revealed...
Warning: super angsty, not exactly a fluffy shot
Feeling the warm blood drip down between your fingers as you held tightly to the man in front of you a small part of you flinched but knew you had no choice but to continue. The demon possessing him had long ago killed off the human after taking control of his body.
"I'm gonna ask you one more time, where is it? I'm not a patient person, and things can get a lot worse for you the longer you make me wait."
Fear flooded the demons eyes as he finally nodded franticly, "Okay okay fine! I only had it for like two days before I sold it. Demon out in New Mexico named Franklin gave me a good deal to take it off my hands."
Pulling him closer to your face you let the knife slip a little deeper into his skin making him wince, "How do I know your telling the truth?"
Wincing the demon rolled his eyes, "You really think I'd keep something like that around for long with Crowley on my tail? Please I'm not that stupid, now you gonna let me go? I told you everything I know."
Leaning back you contemplated it for a moment before meeting the demons eyes once more, "No."
Sliding the knife fully into his chest you watched as the bright orange light flickered under his skin before going dark. Pulling the knife free as you stood up you again felt that flinch of regret. You didn't have long to think about it however before you felt movement in the room behind you.
Quickly turning and throwing the knife you were surprised to see Dean Winchester shift just in time to miss the blade as it buried itself in the wall behind him. Turning quickly with wide eyes he let out a deep breath. "Damn Y/N, I see not much has changed, although I think your aim is better."
As the shock of seeing Dean lessened you quickly composed yourself, "yeah well I've had plenty of time to practice. Your looking a little worn down Dean, tough year?"
Walking forward you forced yourself to keep your cool demeanor as you moved past him to grab your knife. Pulling it free you quickly walked towards the door, "Love to stay and chat but I've got work to do. See ya around Dean."
"Y/N wait! Please I um, its really good to see you." Turning slightly as you reached the doorway you saw the man you'd known for years, the man you'd stupidly fallen in love with, looking back as though he'd found a long lost treasure.
"Wish I could say the same Dean, go home to your girlfriend."
Turning and leaving before he could give a response you quickly walked towards your motorcycle. Straddling the seat and pulling the helmet on you saw Dean come out of the building looking as though you'd kicked his puppy. Starting the bike and swinging the back tire around you raced away, leaving behind a dead demon and the man who broke your heart.
"I'm telling you Sammy somethings different. You should have seen her with that demon, she tortured him before killing him."
Watching his brother pace back and forth across the stained carpet of their motel room Sam couldn't help but notice how uneasy Dean seemed.
"Dean she killed a demon, she's a hunter, whats so different about that?"
Stopping midway across the room Dean stopped and turned back to his brother, "I don't know man, by the time I got there all I know is she was asking him about some object he sold. This wasn't just a hunt she's looking for something, something even the demon was afraid to hold onto. Its dangerous to hunt alone man, what if gets herself killed?"
Rubbing his hand across his face Sam let out a deep breath, "Shes been on her own for almost two years Dean, it sounds like she's doing fine. Besides it doesn't sound like she was happy to see you, what makes you think following her to New Mexico is gonna help anything?"
"I don't know Sam okay! All I know is seeing her tonight, I don't know man I just need to know shes okay. Are you coming with me or not?"
Realizing he was fighting a losing battle Sam stood up and moved to pack up his weapons and books. "Yeah I'm in."
Smiling slightly Dean nodded before moving toward his own bed, "Alright we gotta get going, shes got a good head start on us so..."
"This isn't gonna win her back you know."
Sams words caused Dean to freeze as he held his bag in one hand and a rolled up shirt in the other. Clearing his throat as he threw the shirt into the bag the oldest Winchester never looked up. "I know that."
"Dean it's been two years, we've never been able to find her before and it sounds like this time was just pure luck. I just, I don't want you to get your hopes up. After what happened..."
"Don't," Sam looked up to see Dean giving him a hard stare. "Just, don't Sam. I know I screwed up, I just need to know that she's okay."
Five minutes later both men were in the impala as it sped down the road, Dean immediately blasted the radio hoping to ignore his racing thoughts. He screwed up royally, at the time it seemed like his only choice. One he made out of heartbreak and regretted deeply ever since.
As your bike raced down the dark back roads your mind wouldn't shut up. Images and memories of hunting with Sam and Dean played on repeat as each mile passed. Tears threatened to fall but knowing how bad of an idea it was to ride and cry you quickly managed to calm down the urge. You were on a mission, now was not the time to skip down memory lane, especially after seeing Dean. The fresh feeling of hurt stung your chest as another memory flooded your mind, one that haunted you for the past two years.
"No Dean your not going without me! I'm going with you whether you like it or not!"
"Damnit Y/N just listen to me for once! They already took Sam away I'm not gonna let them take you too. Just stay here! I'm gonna go get Sam back no matter what it takes and I don't need you there distracting me!"
Shaking your head in frustration you tried once more to get through to the stubborn man in front of you. Following him around as he filled a duffle bag with weapons from Baby's trunk you knew there was a good chance this would all end bloody.
"Dean you can't tell me what to do! Besides I wouldn't be a distraction I can help! You can't take them on alone!"
Slamming down the bag Dean turned around to face you, for a moment you were stunned at the depth of emotion on his face. Stepping forward he stopped only inches from you before lifting both hands to cup your face. "Listen to me Y/N, I need to be entirely focused on getting Sam back, if your there then a part of me will only want to make sure your safe."
Opening your mouth to protest Dean shook his head, "No listen to me damnit, you and Sam mean everything to me and I can't lose you both. Please," the pleading look in his eyes made you freeze where you were. "Please sweetheart I just need to know that your here and safe so I can do what needs to be done."
Meeting his eyes you swallowed the lump of emotion in your throat, you and Dean had danced around a relationship for the past year of hunting together. Moments of forehead kisses and shared beds in motels followed by goofy movie marathons never felt as real as the look in his eyes right now.
Bringing your hands up to wrap around his wrists you nodded once, "Okay Dean."
Relief filled his eyes and tension seemed to leave his shoulders at your reply. Leaning forward he pressed his lips to yours for a brief moment before turning and closing the trunk. Walking quickly toward the drivers door Dean wasted no time in climbing inside and bringing the engine to life. Backing up a few feet his gaze once more landed on you as he put the impala into drive.
As your eyes met his you brought your fingertips to your still tingling lips, no words were needed as he turned his gaze ahead and sped off to save his brother. Watching the car disappear you silently prayed to whoever was listening that Dean and Sam would both come out of this alive. Making your way back to Bobby's afterward you waited patiently for a phone call, a text, anything.
Pacing the dusty floor you felt as though you might explode from worrying so much. As the day turned darker and night approached you somehow knew that something had gone horribly wrong. They should have called by now. Continuing to wear a hole in the floor you froze mid-step, something had caught your attention. Listening harder you realized there were footsteps coming towards the front door.
Moving towards the hall and pulling your gun from your waist you waited patiently. A moment later the door opened to reveal a beaten down Bobby. Sighing in relief you quickly moved forward, "Bobby, damn it's good to see you what happened?"
Lifting his eyes to meet yours you froze once more as you noticed tears filled the old mans eyes. "Sam he, he managed to take over from Lucifer."
Confusion set in as dread began to fill your stomach, "That's good right? You guys managed to get rid of Lucifer, right?"
Turning and walking towards the kitchen Bobby moved towards the small table before sinking down into the chair. "Sam jumped into the pit Y/N. He grabbed onto Adam, and then the son of a bitch jumped."
Tears filled your eyes as realization set in. Sam was now locked in the cage with Lucifer and Michael, what he must be going through you couldn't even begin to, eyes widening you looked up, "Dean, Bobby where's Dean?"
Looking up to meet your eyes you thought you saw guilt, "He couldn't take it, he's um, he's gone Y/N."
The breath seemed to leave your body as Bobbys words set in, feeling as though the world was caving in around you the only thing you remembered after that was Bobby saying your name before everything went black.
After that night you spent weeks trying to get in touch with Dean, eventually you realized he had turned off his phone and you felt the betrayal settle into your heart even deeper. You believed he just needed time to deal with losing Sam but after the sixth week you knew something was wrong. It only took you four days to track him down, what you found completely broke the last pieces of your already fragile heart. Pulling to a stop a few doors down from the address you tried taking a deep breath as you eyed the familiar suburban house.
You'd been here with Sam and Dean before when he'd insisted on stopping by to see one of his old one night stands. Getting out of the car you took two steps forward before stopping, the front door opened to reveal Lisa and Ben walking towards her car. Ben ran forward and jumped into the backseat as she seemed to dig through her purse to find her keys.
A familiar voice called out from the house causing both you and Lisa to look toward the front door. Dean emerged shutting the door behind him, smiling wide as he walked towards her you felt as though you were going to be sick. Never before had you felt such heartache or betrayal as you watched him catch up to her and kiss her as he wrapped both arms around her waist.
Seemingly frozen to the spot you could only watch as Lisa and Ben left in her car while Dean watched them pull away before walking to what seemed to be a work truck. Turning around and walking back to your car you tried to fight back the tears as you opened the door. Somewhere in the background you thought you heard your name being called but all you could think about was getting away from this place.
Starting the engine you quickly pulled into the road and sped away, looking in your rearview mirror the last thing you saw was Dean running into the road and watching as you drove away.
In the three months after that day you spent every waking moment hunting, Bobby called to check on you but other than that you never worried about anyone other than yourself. One night he called to let you know Sam had made it back from the cage, remembering the younger Winchester you'd felt a rush of relief to know he was okay. Aside from that night you were always angry at the world, and you took that anger out on any monsters you could find. One night during a seemingly routine demon hunt you'd been ambushed and knocked out. Waking up tied to a chair with a splitting headache your anger came out full force as you growled in frustration.
"Well now, I must say I really am impressed by this new version of you my dear."
Turning your head towards the voice you immediately rolled your eyes, "Crowley, what the hell do you want."
Moving to stand in front of you Crowley simply pulled his hand from his coat pocket and snapped his fingers. Instantly the ropes binding you were gone, "Just want to have a chat."
Rubbing your wrists as you stood up you shot him a bitch face, "Ever heard of a phone?"
Shaking his head Crowley held up his hand, "You've been on a bit of a rampage lately darling, didn't want to take any chances. I told the boys to go easy on you but someone got a little excited. Don't worry he's been dealt with accordingly."
Walking around the room you realized you were in a motel room a lot like the one you were currently staying in. Seeming to read your thoughts Crowley moved to push the curtain aside on the one window in the room. "Same motel, just a different room. Seeing as you've covered yours in traps and such I felt this was a better environment to, negotiate."
Turning around and meeting his eyes you crossed your arms over your chest, "Negotiate what?"
Smiling as he stuck both hands back into the deep pockets of his black coat Crowley met your eyes, "The beginning of a beautiful friendship."
That had been almost a year and a half ago, since then Crowley provided you with plenty of leads on monters to kill in exchange for your help from time to time weeding out unloyal demons. That is what led to your current situation, a powerful object had been taken from hell and brought topside. According to him this supposed object held some major mojo and he didn't want it falling into the wrong hands.
Personally you didn't really care what it was or what it could do, you just wanted to hunt. Once you'd reached New Mexico tracking down the demon you were looking for proved to be easier than you thought. Not many wanted to piss off Crowley's new pet, they all knew how ruthless you'd become. The last demon snitched so fast you didn't even have time to threaten him. Apparently this Franklin guy was holed up in a bar outside of a small town.
Walking inside the run down building you immediately wrinkled your nose at the stale smell of beer and BO. For it to be a Friday night the crowd was rather small. Aside from the three women sitting at a table loudly complaining about another woman they all knew you noticed five men crowded around the pool table as another man sat in the booth beside it watching the crowd. Seeing you his lips rose into a smile and he raised his glass. Rolling your eyes and walking towards the bar you took a seat at the end with your back to the bathrooms.
Two whiskeys later you'd discovered not only was the man in the booth your guy, but three of the five playing pool were his lackeys. The two poor saps they'd just hustled in pool got up and left in a huff after losing their money. As they walked out two more men walked in, downing the last of your drink you motioned once more to the bartender and waited.
Feeling someone slide into the seat beside you your eyes rose to see Sam and Dean both looking at you. Shock covered your face for a brief moment before you quickly recovered. Taking the new drink from the bartender you quickly looked around to see if the demons were suspicious. To your annoyance the biggest one was leaning down whispering something to Franklin.
"Damnit what are you guys doing here? You need to leave, right now."
Frowning slightly Dean shook his head, "Look Y/N we just wanna talk, please."
Looking over and reluctantly meeting his eyes you instantly felt that wave of hurt wash over you again as you looked into the familiar deep green. Opening your mouth to reply you noticed from the corner of your eye that Franklin had stood up and began moving towards the door followed by his companions.
"Shit, I've got to go." Throwing money down on the bar you quickly jumped up before running to the door and following the men into the parking lot.
"Hey Franklin, where you going in such a hurry?"
The men stopped and turned around at your voice, moving forward the demon sneered as he eyed you, "I suppose your Crowley's pet hunter. I should have known he'd be too much of a coward to confront me on his own."
Shaking your head and grinning you pulled out your angel blade and flipped it around into a position against your arm, "Nah, I volunteered, taking out scum like you is the whole reason I get up in the morning."
Hearing familiar heavy footsteps behind you only swayed your attention for a moment, internally cursing you readied your stance for the inevitable.
Looking behind you to see both brothers step forward Franklin seemed to grow nervous but put on a false bravado anyway. "Well now, I suppose the king of hell has the whole set now. How does it feel working for the very thing you've hunted all your life?"
Both brothers shared a look before looking at you, feeling their eyes you simply muttered, "later."
Lifting your head and taking a few steps forward you smiled, 'Well boys? Don't wanna keep a lady waiting do ya?" Immediately two of the three guards ran forward, moving quickly you took two steps before lifting your right leg and kicking the first one hard in the chest. As he flew backward you immediately turned and began fighting off the second one.
Pulling out their own knives both brothers quickly dove into the fight. Each man took on a demon as you killed your first. Running past them and towards Franklin you were caught off guard as an invisible force picked you up and rammed you hard into a parked car. Glass shattered and you felt the air leave your lungs as you fell onto the hard ground head first.
"Y/N!"
Ignoring the pain and the spots clouding your vision you stood up before facing Franklin. "You know how this is gonna end, give it to me and I'll tell Crowley you cooperated." Holding out your hand you saw the demons eyes flash from you to the brothers as they both killed their demons and moved towards you.
"Fine! Here take it, it's not worth the trouble anyways." Reaching into his jacket pocket he threw what seemed to be a small jewel at you. Catching it easily you pocketed the prize before turning to leave, "Good choice, oh and by the way," pulling up the blade in your hand you quickly threw it as hard as you could into his chest. Surprise covered his face as he flashed orange and fell to the ground.
Feeling the adrenaline in your system begin to fade you winced slightly, reaching up to feel your head you noticed how cut up your arm was and could feel warm blood trickling down your neck. Walking toward the demon you could feel both brothers staring at you. "You guys shouldn't be here, I told you to leave."
"Were you gonna take on all four of them by yourself?" Sams voice caused you to pause, you'd missed the younger brother so much. The concern in his voice now only caused your guilt at not reaching out to him to grow. Pulling your blade free and wiping it off you turned around. "Wouldn't be the first time."
Sams face seemed sad as realization set in, you used to be his best friend, he could tell how much you were hurting. Opening his mouth to reply you held up a hand, "Look if we're really gonna do this then let's at least get out of here. I need a shower."
Twenty minutes later you sat at the small table in your motel room stitching up the cuts on your arm as Sam sat across from you and Dean paced the room. Feeling the tension get worse by the second you knew there was no way to avoid the elephant in the room.
"So thanks for the help tonight but you should know this doesn't mean I'm coming back."
From across the room you saw Dean stop pacing and turn towards you. Looking up at Sam you saw him give you a sad look, he always knew how to read you like one of his books. "Can I help with the cut on your head?"
Giving him a small smile you nodded and moved so he could get behind you. Feeling him push against the sensitive area you winced slightly but otherwise kept your eyes forward. Unfortunately this led to being face to face with Dean. From the look on his face you really couldn't tell what he was thinking. On one hand he seemed angry but at the edges he seemed sad too. For a moment as your eyes met you wanted to go to him but quickly squashed the feeling. You didn't matter to him, not really.
"How the hell are you connected to Crowley, what are you his errand girl now?"
Squinting sharply at Dean you gave him your best bitch face, "My business with Crowley doesn't involve you Dean so back off. So what if I do a job for him, at least I get to kill demons."
Throwing up his arms and pacing again you couldn't help but roll your eyes as Dean began muttering to himself. Finally turning back to you he threw an arm up towards the door. "And tonight? Y/N you were gonna take on four demons, four! Alone! What the hell were you thinking?"
Feeling Sam finish the last stitch you quickly stood up and took a few steps toward Dean. He actually had the sense to step back as he registered the anger on your face. "I was thinking that I had it handled! It was never suppose to go down like that Dean I had a plan dammit! One you and Sam ruined the moment you decided to follow me! In case its escaped your attention let me be clear about something, I don't want you here Dean. You decided a long time ago to leave so this is me honoring your wish. Go home to Lisa and leave me alone."
Walking towards your bag on the closest bed you angrily began throwing your stuff into it. Moving to stand beside you Dean took a deep breath. "Look Y/N I, I just don't want you to get hurt. You can't trust Crowley he's..."
Zipping up your bag and throwing it over your shoulder you turned to glare at Dean, "Yeah well thanks to you I don't trust anybody anymore."
Moving to step around him you huffed in frustration as he moved to block your path. Crossing your arms and keeping your eyes downcast you noticed from the corner of your eye that Sam was no longer in the room. Holding his hands out to the side in surrender Dean tried once more. He knew he was dangerously close to getting his ass kicked but it wasn't like he didn't deserve it. Ever since Sam came and got him he'd wondered about what happened to you. Hell, if he was being honest he'd thought about you for longer than that.
"Y/N, the day Sam, the day I lost my brother I didn't know what to do. I felt empty, like everything good had been taken from me. I was tired, I was so damn tired of losing everybody that I didn't even think before I took off. I just wanted out, I didn't want anything to do with hunting or a reminder about what I'd lost. I was hurting, I'm sorry sweetheart, I should never have just abandoned you the way I did. You have to believe me I never meant to hurt you."
Feeling tears build up as he spoke you shook your head once to fight them off, looking up at Deans face you felt a new wave of emotions flood your body but fought as hard as you could to control it. "You kissed me, made me believe you cared about me. Then drove off into the sunset like some damn hero in a movie only you didn't come back. I waited for almost two days to find out what happened. Did you know Bobby had to tell me you left?
Did you ever even for one second consider calling me yourself or even coming back? You act like you had no other options Dean but I was there! I loved you damnit and I would have done anything it took to make you happy! I know how much Sam means to you, after what happened if you had come back I would have held you and told you it was all gonna be okay and that I'd be there to help you through it!"
You could see guilt eating its way through Deans eyes but held up your hand as he opened his mouth. "If you wanted out Dean I would have went with you. Don't give me that bullshit of not wanting a reminder because somewhere deep down you know I'm right. You chose to leave me behind. After everything we'd been through together, you chose her. Where the hell does she think you are now huh?"
Clearing his throat Dean met your eyes, "It didn't work out, I tried, I really tried but it just didn't work out. Cas he um, he wiped their memories."
Feeling your anger simmer slightly at his confession you looked away for a moment, "I'm sorry I know that must have been hard. But it doesn't change anything Dean." Moving around him and walking towards the bathroom you began throwing everything you needed into your bag.
Hearing his footsteps close in you began to feel cornered in the small space.
"Y/N I never meant to make you feel like you didn't matter to me. You did, hell you still do. That day you came to see me, I should have ran after you but I just, I couldn't." The warmth of his hand wrapping around your arm made you freeze as you stood by the sink. "Please, I don't know what's going on between you and Crowley, and I don't know what its been like for you since I left but, I want to make it up to you. Please sweetheart don't keep hunting alone, I'd never forgive myself if something happened to you."
Feeling the first few tears begin to fall you turned around and lifted the bag to your shoulder. Meeting Deans eyes you simply stared into the green orbs remembering all the good times you used to have. Closing your eyes you felt guilt eat at you as the next words left your lips.
"Something already happened to me Dean, and it was your fault."
Feeling tears fall faster down your face you took in a long breath. "I can't come back Dean. It's not enough, I wish it was but it's not. I'm not saying this to hurt you, Chuck only knows why but I still love you. But I can't go back to being there when you feel lonely and sitting around waiting for you to leave again. I wish you and Sam the best but I just can't do it, I'm sorry."
Grabbing your bag you quickly moved past him and back into the room. Knowing you were about to lose any control you had you quickly grabbed your jacket before heading out the door. Frozen in shock Dean could only stand there and listen as you told Sam goodbye before hopping onto your bike. Hearing you kickstart the motor he suddenly turned and ran for the door, he was just in time to see you turn and ride down the road, this time you were the one that left.
Okay so I am so sorry for the major angst, I wasn't sure where to take this at first but I felt like something like this just couldn't necessarily end with a happy make up scene. I may revisit this shot later but for now I'm leaving it as a sad shot. I hope you still liked it!