Dean Winchester X Reader - Blog Posts

SPN OC X OC

hi hope you are all doing well and staying safe!! Just a quick post featuring two of my oc’s one who is bobby signers daughter and Hecate (as in the greek goddess) and the other who is the son of zeus. very much a percy jacksonxsupernatural story

Summary: Dean meets his ex’s new boyfriend

warning: akward, fluffy

Sergio Diablo (oc) son of zeus

Mila Singer (oc) daughter of hecate

 “Good morning meu amor (my love)” Sergio mumbled still half asleep. I humed and reached out to grab him not ready to accept having to leave the bed. I pushed my body against his, my breasts running along his chest as he pulled me closer his hand squeezing my ass. I pressed my lips to his collar bone feeling his body tense up. 

 The front door clicked open as someone entered the house, loud footsteps echoed as they stomped up the stairs. Sergio seemed unfazed by the noises I assumed because he knew what ever they where they probably wont be able to kill him. I created a shield around the two of us to at least have something separating us from them. 

 “I knew you wouldn’t be up yet-” I regconsided the voice as soon as i heard it. Dean Winchester.

"Dean! WHat the hell!" I yelled pulling the sheet up to cover my chest. Sam shuffled in awkwardly and quickly turned leaving the room once he saw me and Sergio in bed.

"What am I doing!?" Dean exclaimed "Who the hell is this?"

"You let yourself into my house I think I have every right to have whoever I want in MY home" Sergio kept his eyes on Dean who seemed to not feel uncomfortable around my naked body.

"Dean let’s give them a minute " Sam said reaching in the room to grab his older brother by the arm yanking him out awkwardly shuting the bedroom door.

The realisation that my current boyfriend had just met my ex hit me as I cringed. The bed groaned as Sergio say up fully, his face unreadable.

"Baby, I-I’m so sorry I really didn’t-" The sound of Sergio’s laugh muffled my apology. "Are you ok, I just didn’t think this would be your reaction"

"Mila it’s fine" he said between laughs "I think he was in the worse position, I mean he wasn’t the one in bed with you"

"I’m sorry I should get dressed it might be about my dad" I stood up from the bed leaving the sheet standing naked infront of him. He leaned back against the headboard toned chest on display, smirking he ran his eyes across my body sending shivers down my spine. A blush spread across my cheeks, as I began pulling on my clothes. "Are you seriously going to stay there?"

"Would you like me to go introduce myself to your ex?" He asked smirking, I huffed in response pulling a hoodie on.

"Wait there" I said hands on the door "do you want to stay for breakfast?"

"Of course meu amor"

I stepped outside of my room shutting the door behind me breathing in to prepare for the oncoming storm of Dean Winchester.

please tell me if you liked it because i am obsessed with these two atm and would love to right more on them. 

Dating Dean Winchester Would Include:

Warnings- There is mention of an injury (no real description though), some arguments (none of them violent), and a one-night stand is mentioned as well. Apart from that, it shouldn’t upset anyone.

- You and Dean met while you both were researching for a hunt disguised as FBI agents. - You two were both super confused at first before figuring out the other was a hunter. - After some arguing between you and the Winchesters, it became clear that you’re all too stubborn to leave so you may as well work together. - Your stubbornness causes you to clash with Dean. Sam mostly rolled his eyes in the background while you two fought. - This tension soon led to a one-night stand. - You all continue to bicker after this. - Sam storms away and leaves you two alone to research and sort through your issues. - While researching, you and Dean get to know each other. - This leads you to realize that he isn’t quite as mean and cocky as he would have others believe. - He discovers that you’re quite an accepting and open person actually and don’t like to pick fights. - You go over how you got into hunting and that causes you to realize just how similar the two of you are. - Sam returns, satisfied that you two are getting along now. - Later, during the hunt, Dean gets injured. - This leads to you flirting with him to try to keep him conscious long enough to get him somewhere safe enough to treat his wound. - Your talk with him escalates and you promise him a date when he heals, thinking that he wouldn’t remember. - After the hunt is resolved and Dean is patched up, he asks about that date. - And so, your relationship began. - He is super protective of you. It can get really irritating sometimes. - Really. It’s to the point where he tries to convince you to stop hunting and live in the bunker 24/7. - You but sing loudly to his classic rock music together. - He lets you drive his car sometimes. - You two trust each other a lot. - He’s huge on PDA. Anything from hand-holding to make-out sessions is okay for him in public. - You both love to cuddle. - You both alternate who is the big spoon and who is the little spoon. - Whenever you have a nightmare, he’ll just take you in his arms and listen to what happened in your dream. He’ll then reassure you and offer extra training time to try to prevent whatever happened from occurring. - When he has a nightmare, you do the same. - You lessen his insecurity by reminding him how important, intelligent, resourceful, heroic, loyal, and loved he is. - You’re both super proud of each other and constantly trying to one up each other’s supportiveness. - For example: You’ll mentioned how he cut off those vamps’ heads in one clean blow and he’ll counter with mentioning how artful your decapitation was of that alpha you all had encountered. - If you get injured in any way during a hunt by someone, he’ll step up training with you and go over the situation again and again. - Even after you have gotten it right six times over and are 100% confident in your ability to avoid the scenario. You eventually have to call Sam in to let Dean know that it’s okay now. - So many ‘I love you’s. - You bake him a lot of pies. - Particularly after arguments. - Speaking of arguments, they’re frequent and often involve some yelling. - They never escalate beyond that though as you both love each other very much. - You two make up very shortly after your arguments as you both love each other too much to stay away. - You become BFFs with Sam, Cas, Crowley, Charlie, and Kevin. - Dean and you still flirt a lot with each other and sometimes will say cheesy pickup lines to make the other laugh. - You love it when he cooks. - He loves it when you cook. - You both cook and bake together super often. - This usually involves some level of food fights and other immature but immensely fun activities. - You both love each other to pieces and are happy to have found a balance between an “apple pie life” and hunting.

DISCLAIMER- I do not own Supernatural or any of its characters referenced in this post. You own you. Please don’t sue me.

Being a part of Team Free Will would include:

WARNING- There is one curse word in this. -Living and traveling alongside the Winchesters. - Whenever Sam and Dean get into stupid arguments or begin to act childish, you're the voice of reason. - You are BFFs with Cas. - Sam and Dean are like your brothers. - No one is allowed to flirt with you or they will have to deal with the boys. - You're a total badass. - You also are incredibly knowledgeable on reasonably obscure monsters. - The whole "There ain't no me if there ain't no you" deal is extended to you. - Having to explain various human body processes to Cas. - Cas trying to understand periods is especially hilarious. - Singing along to the classic rock that is so often blared in the Impala. - Whenever you have the chance, you bake a really lovely pie. Be it pecan, apple, cherry, or otherwise. - This pretty much makes you Dean's favorite person. - Pretty much 90% of your wardrobe is flannels now. - You have the best aim with a firearm. It's seriously impressive. - Cas and you watch Netflix together. - Getting an anti-possession tattoo. - Cas carving sigils into your ribs. - You're Castiel's favorite because of how patient you are with him grasping human concepts. - When you die, you definitely come back because you are just as incapable of staying dead as the boys. - You cut your hair short so that it is more efficient and less of a liability in combat. - This leads to Dean giving Sam more trouble over his longer hair. -You actually are quite close with Death as you recognize the importance of order in an otherwise chaotic world. - You actually remember to prioritize human life and often remind the Winchester's to keep in touch with their humanity. - You're really the best hunter due to this and they know it. DISCLAIMER- I do not own Supernatural or Netflix. The quote is not mine; it is from Supernatural. You are you. Nothing is mine; please don't sue me.

Red Wings {d.w.}

Warnings: 18+ MDNI!! Period sex, descriptions of blood, slight blood kink, pet names, unprotected sex (wrap it unless that's what you want!) Also, I know 'Red Wings' refers to oral sex, but I've only ever known it to be from penetration--so it's penetration in this. (if i missed anything please let me know. also let me know if this is fucked and if i should delete). Word count: 2k

A/N: Any feedback is appreciated, especially on this one. Feel free to be brutally honest. Happy reading, hopefully!

—

It’s no surprise that Dean doesn’t mind cleaning up period blood. It’s a part of his job description for hell's sake. And he’s damn good at getting deep stains out of your underwear, or on occasion where you bleed through your pads and stain the sheets during the night. He’s more than happy to help during your vulnerable days. In fact, he loves it. Loves taking care of his sweet girl. 

Dean has been through numerous types of pain, but he will never know what it’s like for his body to attack itself. Doesn’t understand the breast tenderness where even a loose shirt hurts to have on. Cramps so debilitating that you can’t even stand–that move to your back, to your vagina, and sometimes it zaps your damned asshole. The iron deficiency that gives you headaches and makes you so tired and weak. Sometimes the pain lasts for hours without a break. 

He keeps begging you to get checked for endometriosis–and has been secretly doing his research because it makes him feel useless that he can’t soothe the pain. You’re stubborn though and don’t listen to him. 

The cramps aren’t the worst tonight but they’re bad enough that you keep wiggling around and aren’t able to fall asleep. You’ve noticed recently that Dean sleeps lighter when you’re on your period–he’s more intune with you and your body. Always ready to make sure you’re okay. He’s groggy when he turns over and drapes an arm over your waist. His hand slips under your shirt and goes to your stomach, the warmth acts as a heating pad. Then he starts massaging gently, going from one side to the other, then pushing down towards your uterus. Once he’s done that for a couple rounds, the massage gets deeper, and that’s when you let out a throaty groan.

The pressure that is placed on your stomach actually helps relieve the cramping. 

“Feel good, baby?” Dean mumbles, his warm breath tickles your ear.

“Yes…really good,” You exhale. “How’d you know to do this?”

“Found a video on youtube. Hate knowing how much it hurts you. Had to figure something out for my girl.”

“Fuuuck.” The release is too good to be true.

Dean leaned over your shoulder, kissing your forehead, then your cheek–still massaging. “You, um…you know what else I came across that could help your cramps?”

“Hmm?”

“I read,” he pauses to kiss your shoulder, “that period sex helps release endorphins or whatever and acts as a natural painkiller. Would you–would you want to try…?”

You never entertained the idea of having period sex. It was messy and the clean up would be a nuisance. Also, Dean already had to deal with washing blood from his own hands from the job, plus whenever you bled through clothes and periodically on the sheets. Even if you insisted on cleaning everything yourself, he’d make it his responsibility. You didn’t want to burden him or trigger a trauma response with how heavy your flow could get.

Admittedly, his willingness to do anything for your aching body was turning you on. It was something the two of you have never done. With anyone.

“Let’s try it. But we’re stopping if—“

“If your cramps get worse. Of course, sweetheart.” You saw him wink at you in the dimly lit room and your core heated up. He could read your mind so effortlessly.

Dean gives you a gentle kiss on the lips before getting up and walking out of the room. Coming back a minute later with a dark towel. 

“Lift your hips up fr’me.”

You follow his instruction and he slides the towel underneath you. And when you settle back down he pulls both your underwear and sweatpants off. You remove your tank top while Dean takes off his boxers. His cock springs out of them–you didn’t even realize he was hard in the first place. Your clit pulses at the sight. He eyes you–taking in your beautiful bare body as he begins stroking himself. A small groan leaves his plump lips while he climbs on the bed, positioning his legs on either side of you. 

Dean remains straddling you, pumping his dick slowly–you watch his precum building on his tip, threatening to leak down his shaft at any moment. With his other hand he finds your clit. You can’t help but to jerk back, not being used to him touching you during this time of the month.

His voice sweet and slow like honey, “It’s okay baby. Blood won’t hurt me none.” 

A small croak of approval emits itself from your throat while you shake your head in agreement. Replacing his large fingers over your small sensitive bud, he presses down slightly and moves side to side. Just how you like it. Concern sits at the forefront of your mind about your blood spilling out at any moment. But with every moment that passes while Dean touches you–while you watch him touch himself–is another moment that eases the thought of the clean up that has to happen later. You eventually lay back down, resting your head on your pillow, elevated just enough so you’re still able to watch. 

“That’s my girl. Just relax.” He stops pleasuring himself and drops himself over you with his free hand, and leans down planting a kiss on your lips. He pulls away and brushes his lips against yours, “You ready? I need to hear you speak this time.”

“I’m good, I’m okay.” You say as you brush your fingers along the side of his jaw, a little smile blooming on Dean's face. “Go slow at first?”

His eyes narrow at you, taking his fingers off your clit to find himself, gradually guiding his length into your bloody cunt–moaning, “Always,” once he feels how much warmer you are. 

You can’t describe it, but having him in you definitely feels like ecstacy. Every pump was almost overstimulating, the slickness turning you on. The fact that he was in you raw, had your mind spinning in circles. Your walls gripping him as tightly as possible, and your body begging him to keep going. Desperate cries escaped your pretty little mouth. Wrapping your legs around his back so he had no choice but to keep going–whispering quietly, “Don’t stop”, repeatedly in his ear. 

How was sex this blissful? Maybe because you’re more sensitive? Or hornier than usual? Which was hard to believe, it’s virtually impossible because you always wanted him to fuck you senseless. But this was different. You wanted Dean so fervently. The feeling is almost primal…

“Fuuck,” Dean grunted as he pumped his dick into you, “Baby…you feel so good. So warm.” 

His head bobbed down like he couldn’t hold it up anymore, so you held him in your hands–making him look into your lustful eyes. He was breaking already. When he’s close his nose scrunches, his bottom lip quivers, and his eyebrows knot up. He’s mouthing, “I’m close.”

“No–”

“Shit, am I hurting you?” Dean immediately halts his actions, taking himself out of you and sits you up, “I’m sorry. I–we can stop...”

When you giggle, Dean can’t hide his confusion. He’s so adorable when he’s concerned. “I’m fine, my love.” You place a tender kiss on the hand that had made its way to your cheek, “Just didn’t want you cumming yet. I wanna be on top.”

“Don’t scare me like that.” He glares at you as he takes your place on the towel. 

You look at his pelvis before you climb on top of him, and there’s a decent amount of blood coating his dick and thighs. A part of you is guilty for bloodying him up, but the devilish side of you loves the sight. It’s not other people’s or monsters' body fluid on your partner, but it’s your own. No violence caused this—well besides your uterus hating you, but that’s not the point. The point is that he will do anything to make you feel like you’re on cloud nine. Even if it means staining his skin red.

A loud animalistic moan came from Dean once you slipped his cock in you. Grinding your hips slowly at first to really savor the moment, to take in the beautiful man beneath you. His hands gripping your love handles guiding your movements. Small whines leave you as he makes you speed up, making you grasp onto his hips. 

At this point everything is getting you so riled up and you can’t help it. Any insecurity has left you. There was blood that had smeared on Dean’s stomach, most likely from the hand that grabbed his member, and that was the final straw for your self control. Dean noticed the sinister look in your eyes.

“You like seeing that don’t you? Your blood all over me?” He asks behind gritted teeth, pounding your wet and bloody cunt, “Fuck me baby.”

And that’s exactly what you do. You lay yourself into the crook of Dean’s neck and bounce on his hard length. The sound of his skin slapping against yours drives you mad, involuntary cries escape from both of you.

He’s pulling your hair with one hand and gripping your ass with the other, “That’s it, pretty girl,” he slaps your bottom, whispering in your ear, “can feel you tightening around my dick.” Dean then pushes you up slightly, lifts his head up finding one of your breasts, and starts flicking his tongue against your nipple. The hand that leaned you upwards is now kneading your tit.

That was your weakness—him playing with your nipples. They’ve always been sensitive and are the reason for most of your orgasms, which is where you were heading. Fast. Dean’s taken over again. He’s humming into your breast as he takes it in his mouth, and his hips are bucking into yours at an ungodly speed. Your stomach is twisting at the stimulation, your body is shaking. There’s no strength left to support yourself, you begin to sway. Dean eventually guiding you to rest onto him.

“Dean, I’m…I’m cumming.”

“Yeah, angel. Can feel you throbbing. God…” He lets out a sharp exhale, eyes rolling back–he’s so close to spilling into you. Reaching down to pull himself out of your pussy–but you refuse, needing him in every way imaginable. Pulling his hand away from where you two were connected, “I–I can’t hold it. Baby, please!” 

“Cum in me.”

“Wha–”

You grind as fast as you’re able to.

 “You heard me,” seductively exaggerating your next words, “Cum. In. Me.”

“Oh fuuck, yeah–yeah…” Dean howls your name as he releases his load into your swollen hole, the heat from his climax flowing through you. The euphoria that was clouding your judgement slowly wearing off. Breaths are evening out, while you still slowly move yourself up and down–milking little spasms out of Dean until he begs for you to stop.

“Dirty girl, having me cum in you. Didn’t expect you’d like period sex this much.” A huge grin spreads across his face, love in his eyes, “How’s the pain?”

You say as you cup his face with one hand, returning the happiness, “Gone.”

“Good. Also didn’t expect you to get turned on by having your blood covering me.”

“I’m sorry…”

“Don’t be, it’s hot. C’mere.” Grabbing you by the nape of your neck, he pulls you into a soft, sensual kiss. “I felt so close to you, watching how turned on you got. How wild you looked, made me want to give you my children.”

“Well, you did. Technically.” You smirk. A look of defeat washed over him, he was serious. His demeanor makes you compose your humor, “Well, this is a good start then.” 

There’s that adorable smile and those cute crows feet that crinkle around his eyes.

“Let’s wait a little while though, I have a feeling you’re gunna want me to fuck you while you’re on your period more often.” 

“Mmh, how’d you know?”

“Honey, you gave me my first set of red wings and you got so hot and bothered by it. I know you, know what you want.” He gets off the bed and yanks you into his arms, “Let’s get you cleaned up.”

—

tags! @aylacavebear @daylighted @ambiguous-avery @deans-spinster-witch (if you want to be untagged, there's no judgement!)

The Taste of Us {d.w.}

A/N: This is me losing my smut virginity. Be gentle with me plz!!! Tell me if it’s any good or not.

Warning: semi-public sex?? oral: m & f receiving, pet names, teeth kink?? (if I missed something let me know!!) MDNI 18+ Word count: 1.8k

—

It’s a hot summer night in the Middle of Nowhere, Tennessee. The crickets are chirping, lightning bugs are illuminating the sparsely lit backroads, and the sweet gentle hum of a 1967 Chevy Impala is making its way to your ears. 

You're working the nightshift at a roadside diner that probably loses money staying open twenty-four hours a day, and definitely isn’t paying you enough. There’s only two more hours left of your shift before the next employee shows up. That’s when he comes in, a boy roughly around your age–and he’s unbelievably charming. Rare around these parts.

When the door to the diner closes, you can feel the thick, humid air push towards you. And almost immediately you feel the wind get knocked out of you by the sight of this stranger. Sandy hair, freshly shaven, eyes that could blend into the dense forest surrounding the restaurant; he wore an interesting frog-like necklace? You couldn’t really tell what it was–and what seems to be a wedding ring on one of his pointer fingers. 

He sat away from where you had propped yourself against the counter. You sauntered over there after minutes of painful silence. 

“Long night?”

Dean only lifted his eyes to look at you and gave a weak smile. Comparing his features to the forest is effortless to you. Eyes like the pines, dark circles would blend in with the dirt after it rains, every scar that litters his face resembles the places where lightning hits. His beauty is tragic and unfathomable. 

“Not anymore.” His voice was warmer than how he looked. Seduction covered his eyes like the clouds in the sky.

“Ah, yeah. I bet.” You roll your eyes sarcastically. Tapping your pen against your small notebook, “What can I get ya, darlin’?”

Dean can’t get enough of your accent, he really had to play this right in order not to walk out of here with a raging hard on. He couldn’t imagine waltzing in here again with that kind of embarrassment following him around.

“What’s your name?”

You’ve had more than enough men coming in here looking at you like you’re an object to them. Their smiles that lead to empty, crazy eyes that give you goose-pimples all over. Every. Single. Time. But him? His voice was as sweet as the tea you poured yourself earlier. Dean never breaks eye contact, making you blush. So you told him.

“Such a beautiful name, sweetheart.” He winks at you, then grins as he lowers his head to browse the menu. “Could I have…you?”

If he didn’t look at you like you were the only star in the sky, you definitely would’ve said no. But holy hell, that twinkle in his eyes made you wetter than the spring brings rain. And his teeth. He could sink those canines right into your thighs…

You must’ve been staring too long. He raised his eyebrows and a curious yet defeated expression flooded his features. Mouthing a small “okay” then began to actually look at the menu. 

Shit. Shit. Shit.

“I—I’m sorry. I’m used to old geezers hittin’ on me. Not a fine man like yourself.” Shyness takes over you. You start to tremble from how nervous you are, and the tips of your ears turn even redder.

“No need to be sorry, pretty girl.” He stands up from the stool, leaning so far forward that you can smell a faint hint of Irish Springs on his skin. Mere inches separate your face from his. Dean whispers seductively, “This place usually busy at night?” 

As soon as you shake your head no, he gently places his hand on your cheek, chuckling at how warm it is, then pulling you into the most intimate kiss that has ever touched your lips. It takes you a second to reciprocate before moving at the same tempo. 

God, it’s been forever since you’ve had human contact like this. The two of you synced up so well together, like you’ve done this before. He was too good. So. Good. A small moan escapes from your mouth. 

“Get on the counter fr’ me.”

You obey his command. You pulled yourself up and sat on your shins. The dress you had on rode upwards.

“Sit down and put your feet on the edge.” A light order as his hands trail up and down your exposed thighs.

“Would a please hurt ya, sweet cheeks?”

He teases you back and drawls out, “Pleeaase?”

Again, you do as he says. You just can’t help it, everything about him is alluring. Slowly making your way to the position he wants you at. The two of you don’t break eye contact. Not a fuck would be given by either of you if someone walked in.

He hikes your dress up, smiling at how wide-spread your legs are for him. A serious look washed over him right before he pulled your panties down. A sudden realization. 

“Is this okay?”

How much hotter can he get? You thought.

“What’s your name?”

“Huh? My name? It–it’s Dean…”

“Dean, honey–anything you do to me is more than okay.” You lean back onto your elbows, smirking.

He proceeds with his actions. Placing tender kisses down one thigh, stopping so–so close to your most sensitive area. Then skipping over it to kiss up the other thigh. As if he had read your mind from earlier–when he gets to a meatier part of your leg, Dean sinks his incisors into you and takes your skin between them. Delicately sucking, marking you as his. That’s when you finally begin to relax.

A couple love marks later, without warning, he slides his tongue in you. His warmth makes you jump and squeal–you’ve always been sensitive and ticklish down there, especially if it’s been a while. 

An animalistic grunt comes out of Dean's mouth, into your pussy. You can feel his grin widen against your pelvic bone while his tongue flicks inside you. When you look down at him he’s already staring–desperate for more of what he heard, he moves up to your clit. Massaging it in a side-to-side motion. He sees your eyes roll back and he immediately plunges two of his thick fingers into your slick entrance. Another gasp slips out of you. 

His “come-hither” was perfect—hitting your spot just right. His mouth already knew how to please you. But it was his eyes that made you come undone. Pulling your head back up, you find that Dean had never stopped looking at you.

“You’re so delicious, baby. Fuuck. Could do this all night.”

Tension was building within you. Every muscle was convulsing, one of your legs slipped off of the counter. Dean quickly placed it back up with his free hand.

“That’s it–cum for me.”

You’ve never experienced an orgasm quite like this one. Your swollen clit was throbbing, sending electricity throughout your body. Your walls pulsating around Dean’s fingers–your thick milky cum coated them as he pulled them out of you. He spread them apart and leisurely slipped his digits in his mouth. A delicious sound came from his throat, eyes closing as he savored your taste.

Where did this man come from? Who the fuck cares, you were grateful.

“C’mon, sugar. Your turn.” You pointed to the booth behind him. “Move that table to the side and take a seat.”

That drove him crazy–you taking over. Wanting to pleasure him. It wasn’t often that women told him what to do during sex, but he is more than willing to submit to you. 

“Yes ma’am,” he said with a hint of southern twang. 

The table made a loud shriek as Dean pushed it, making you look behind your shoulder–expecting someone to come from the back of the diner with concern. No one came. You looked out of the window to make sure the parking lot and road were empty. Nothing was out there. Shifting your focus back to Dean, you notice sweat glistening on his forehead. Eyes tracking your every movement. You walk up to him and climb onto his lap, sitting on his hardened length.

“That fucking smile of yours is gunna be the death of me.” You murmur against his ear, and can see the hair on his neck stand up.

His cock wavering in his jeans, trying to find a way to your cunt as you rock your hips and suckle on small areas of his neck. One of his arms wraps around your waist, pulling you in closer while the other wraps around your throat and guides your face towards his. Lips connecting, mouths opening–the taste of your cum still lingers on his tongue. The hand he had on the small of your back reaches for the button on his jeans, but you had other plans.

Jerking away from him, wagging your finger no, then sliding off him to sit on your knees. Glancing up at this devilish man before you, with sex in your eyes. Undoing his jeans for him, he lifts up his lower half to make it easier for you to take them off. His cock springs up. Pre-cum covering his enlarged tip. Your hand making its way to him, spreading his arousal down his shaft in steady, unhurried movements. Dean placed his large palms right under your ears, tugging you towards him. 

“Ask for me, if you want my mouth so badly.”

“Please, sweetheart.”

“What do you want, pretty boy?” You asked, resting your chin on your hand, lightly brushing your lips on his sensitive head.

“Want yr’ mouth around me. Please?” 

The desperation leaking out of him was ecstasy for you. Giving in, you wrap your mouth around his girth. He’s so big. Plunging his dick so far down your throat that you gag on it. Spit dripping down his balls and your chin. In your peripheral vision you see his mouth ajar. It was almost undetectable, but he let out a tiny gasp. 

Removing him from your mouth you beg, “Lemme hear you, Dean…”

Then he lets out the most beautiful moan, making your pussy drip all over again. He grabs the back of your neck and his cock at the same time–ushering himself into you. Desire radiating from him as you lock eyes. Continuing to suck and hum against him, working your hand in circular motions in stride with your mouth. Faster and faster as he begins to buck his hips. 

“Oh fuck, I’m–I’m cumming, baby. Take me out…”

Refusing to listen to him, you don’t stop using the mouth God gave you. The guttural roar that filled the room was your only indicator that he wasn’t in control anymore. His cum shooting to the back of your throat. Dean grabbed the edges of the booth so tightly from you overstimulating him, then he finally took in a sharp breath. Removing his cock from you, you get up and straddle him again. Leaning in to kiss him but he withdraws. A questioning look that reads, did you swallow?

You only nod, then stick your tongue out.

“Good girl.”

Giving you a sensual kiss, slipping his tongue over yours.

“I taste so good in your mouth.”

—

tags! @aylacavebear @daylighted @ambiguous-avery @deans-spinster-witch (if you want to be untagged, there's no judgment!)

MASTERLIST For…

Dean Winchester-

- coming soon… (this request is in the making, if you’d like me to start working on more I’d be more than glad!☺️)

- coming soon…

- coming soon…

- coming soon..

-coming soon…

- coming soon…

For the people that just find Dean Winchester so so handsome like the gorgeous man he is, would y’all be interested in submitting requests for writings? I’m desperate I need to write ab him😭

Would anyone read DeanWinchester fics?

A Fate You Can’t Escape

Summary: Hungry and alone in the bunker the reader decides to take the Impala into town for a quick trip to get dinner. But things don’t go as planned and the reader tries her hardest to escape the consequences of her actions before the brothers return from their hunt. But as things go from bad to worse the reader begins to discover that some times you can’t escape your fate.

Pairing: Dean x Reader

Word Count: 8,900

Warnings: Car Accidents

You were laying on the couch in the Dean cave watching some new show on Netflix when your stomach just started rumbling. You tried to ignore the grumbling, but it got to the point that you couldn’t anymore. If you didn’t eat something soon you were gonna be sick.

You groaned, you knew there was practically no food in the kitchen. There might have been a slice of bread, but that wasn’t gonna hold you over. Neither Sam or Dean were home, Garth had picked them up for help with a case in the area and they promised to pick up supplies and grocery’s on their way back. The problem was you expect them back two hours ago and you hadn’t heard from them.

You could wait for them, but you had no idea when they were going to be back and even if you manage to wait for them then you would have to wait till dinner was cooked.

Another violent grumble in your stomach told you that you weren’t going to be able to wait and decided to go into town yourself and pick up some food.

Although that brought up another problem. Your car was still out of commission after the last hunt you took it on. The impala was still in the garage, as Garth had picked the boys up, but Dean rarely lets you drive it, hell Sam barely gets the chance. You knew that Dean would not be happy if found out you took his baby, especially without asking first.

There were course several other cars in the garage, but half of them weren’t in working order having sat so long uncared for. Dean has been fixing them up in his free time, as a hobby and way to clear his head. But lately, we’ve been so busy with back to back hunts we’ve hardly had any downtime. And the ones Dean has managed to fix up were stick shift and you had no idea how to drive them.

Without any other option, you headed to Dean’s room to get the keys to the impala. You thought about texting him, but he would probably make up some excuse and tell you they were on their way back now and just to wait for them. Of course, that’s what he said the last time you talked and yet they still weren’t here. You figured that as long as you didn’t linger around, you’d be able to get the food and come back before them.

“Pizza for Y/N.” You said to the man behind the counter, he nodded his head and went back to fetch it.

Y/N, that’s a pretty name.” Said the elderly woman standing at the counter waiting for her order.

You gave her a short, but polite smile, “Thanks.”

“It’s so pretty, and it really fits you.” She stepped closer to you, closer than you would have liked, but you fought to hide your discomfort as she was just being a sweet old lady.

“And your hair. It’s so pretty!” She said reaching out as if she was going to run her hand through it. You immediately stepped back only for her to follow. You didn’t want to be rude but she beginning to make you uncomfortable.

You turned away from her staring back at the kitchen hoping your food would come out soon as you kept a watch on her from over your shoulder. Your feeling of uneasiness grew even more when she began asking you questions you were and where you lived. You made up a lie about just passing through town but then her questions only grew.

“Alright pizza and wings combo.” The man said setting the food down on the counter. You let out a sigh of relief and quickly paid for your food and rushed out of the restaurant.

The interaction left you feeling uneasy and you had this unshakable feeling in the pit of your stomach. You sat in the impala for a few seconds to makethe sure she didn’t follow you out and you even drove around the block a couple of times in hopes to settle that uneasiness.

After circling two blocks and another grumble of your stomach that reminded you how hungry you were, you got back on the main road and headed out of town.

You were driving out of town faster than the posted limit because you wanted to get back and dig into ‘your food. You weren’t concerned about speeding as it was a clear evening, no one was around, and Dean always drove at least fifteen over the limit.

You were about two miles out of town, coming across ‘Bendman’s Curve’ as the locals referred to it due to something that happened years ago. The curve was sharp and you slowed down to a more manageable speed, you were probably still driving a little faster than officials would have liked, but you have driven it many times and knew you would be fine at this speed.

That was until you were halfway through the curve and saw a water tank had tipped over and was laying on the side of the road. That wasn’t the problem though, the problem was the tank burst and was currently spilling all over the road. Between the angle of the curve and the water on the road, it was too much. The tires began to spin out and skid and the next thing you know you had last control of the front wheels. As a result, the impala was sliding across the road and despite all your efforts you could not regain control of the car.

Before you knew it the impala came to an abrupt stop as it crashed into the guardrail.

You pull your pounding head up from where it had collided with the steering wheel and as you brushed a loose strand of hair behind your ear, you felt something wet. Blood. A look in the rearview mirror showed a large gash on your forehead.

You weren’t worried about that though. Despite the fact that everything was blurry and how light-headed you were feeling, you pushed past that feeling and climbed out of the impala.

Standing up was a mistake though, and if it wasn’t for the fact you were leaning against the impala you would have fallen to the ground. You slowly pushed yourself upright and made your way around the impala.

You inspected the area you crashed into. The front fender had taken the brute of the impact, causing the siding to cave in. The headlight had popped out too.

You were overwelmed with emotion. Dean was gonna kill you.

This car was his most valued possession. It’s the only thing he’s ever known since the age of four. He took care of his car, more than anyone else would. He washed and waxed it on a set schedule, he was constatly under the hood making sure everything was running just as it should be. The impala was more than just a car, it was a safe place he could take shelter from the monsters when he was a kid, it was a warm sight to see as John came back to pick him up from whatever motel he had dumped him at. It was the first car he learned how to drive and the first and only car he owned. She was his baby and the only home he has ever known. Even now that they have found the bunker and a constant place to rest their heads, the impala was truly where both boys felt at home, especially Dean.

Dean hardly ever lets Sam drive her, and the only time he’s ever let you drive her was because he got hurt on a hunt and Sam wasn’t around, and even then you had to plead with him that he couldn’t drive in the state he was in.

What were you thinking taking Baby without even asking Dean? He would have been mad, no not mad furious if he got home before you and found out you took her out for a ‘joyride’. But now, after he gets a look at her, mad wouldn’t even come close to the rage he will be feeling.

God how could you be so stupid, taking the impala was stupid enough but you knew how much Dean loves her, you should have taken extra care of her, you shouldn’t have been driving so fast, you should have watched the road more carefully for hazards.

You brought your hands up to head, ‘What did I do? What did I do?’ Kept repeating in your head. ‘If only I had driven slower, or if I left the restaurant right away instead of driving mindlessly around the block, or maybe if I waited longer.’

What you wouldn’t do to fix this.

Suddenly the pain in your head grew immensely. You felt dizzy and light-headed, and you went to grab your phone and call for help, but before you got a chance darkness overtook you.

You groaned as you opened your eyes. Your back and neck hurt from the position you were in so as carefully as you could you moved to sit up. It took you a few moments to clear the fogginess in your brain and get your eyes to focus, You were unsure of where you were.

As became more alert, you found yourself sitting in the impala, the ache in your neck and back due to the fact you had been hunched over the steering wheel. You began to remember what had happened, Bendman’s curve, the water truck, and the accident.

But the strange thing was you were no longer there. You vaguely remember passing out at the scene of the accident but now you find yourself waking up in a different place. Normally that wouldn’t be such a unnatural thing somebody found you, and called for help. But if that happened you be waking up in a hospital or even an ambulance. Or if Sam and Dean had found you, you’d find yourself waking up in the familiar sight of the garage in the bunker.

But that’s not where you found yourself. The blinding neon lights flashing in front of you put you back at the restaurant. How you got back here though, you weren’t sure.

You climbed out of the impala and made your way around to the front and were astonished to find baby’s front was unblemished. Her fender was shiny and pristine just like she was the day she rolled off the line. Dean really did a fine job taking care of her.

A fact that only made you feel more guilty for taking her without permission. You weren’t sure why or how you had such a vivid dream, but you were thankful for it. You had foresight of what could happen and you knew what to avoid.

You climbed back into baby and started her up. This time you wasted no time and got on the road. You drove her carefully, making sure to follow the speed limit and keeping your eyes moving for unexpected hazards in or around the road.

When you made it back to Bendman’s curve you were relieved to find the road clear and the water truck no where to be seen. Not willing to take any chances you slowed down below the curve’s speed limit. This curve was named after a tragic accident after all. You made it through the worst of the curve and you began to gently accelerate out of the curve.

You saw the black pickup truck driving towards you in the other lane. You watched it carefully and even moved over toward the side of the road when you thought it was going to crossover into your lane. When it readjusted its position in the center of the left lane you began to move back over. As you approached it closer you continued to watch it, though everything seemed fine.

Until it wasn’t.

Just as you were about to pass the truck, it crossed over into your lane and there was nothing you could do to avoid the head on collision. The impala came to a sudden and violent stop as it collided with the pickup truck.

Ringing. That’s all you could hear as your mind worked through the haze. All you felt was pain, excruciating pain. There was a deep pounding in your head, your chest ached due to the fact you had been jolten into the dashboard, and your legs had been pinned and crushed.

You were having a hard time focusing on anything other than the pain radiating throughout your whole body. You tried hard to concentrate and make your eyes work but your vision was fuzzy and disoriented. You could hear muffled voices, but you couldn’t make out what was being said.

Sacred and worried you began to wiggle and try to turn in the direction that voices were coming from. Which you soon found was a mistake as the pain doubled. You froze where you were, the position painful and uncomfortable but moving proved to be worse.

God, why is this happening to you!? You had a warning, and you took every precaution to make sure the ‘dream’ you had didn’t come to fruition but now not only did it happen but it was worse than predicted.

Forget the rage Dean would have towards you for taking his baby. He was going to kill you for destroying her.

“Miss, can you hear me!” A fuzzy voice was shouting at you. You couldn’t focus on it as you having a hard enough breathing right now.

After a couple more minutes you found that the pain had lessened in intensity, but you knew that wasn’t a good thing. Combined with the fact that your eyes felt extremely heavy and you found it a struggle to keep them open, you knew you wouldn’t have long if you didn’t receive medical attention soon.

Many regrets flashed through your mind. Not taking more time for yourself. Not living your life to its full potential. Not taking chances. Your mind showed you images of the green-eyed man who had captured your heart. He didn’t know about the crush you had on him and now he never will.

“Stay awake,” a voice commanded. But as much as you wanted to you couldn’t follow the demand. Not being able to fight anymore, your eyes slipped closed and the muffled voices around became silent.

You woke with a start, taking in the surroundings around you. You were confused trying to remember what happened. You remembered bits and pieces. You somewhat remembered the crash and you vividly remember the pain.

But your body felt fine now. You even sat up and took stock of your body looking for injuries and moving around feeling for any sort of pain. There was a creak in your neck from the way you had been hunched over the steering wheel, but other than that you were fine.

Baby herself was unharmed as well. Her once caved in dashboard was in perfect condition, the windshield was no longer a spiderweb of broken glass, and her frame was no longer bent out of shape.

You were back in front of the pizza parlor, after having just picked up your food. You were confused as to what was happening. Twice now you had been in an accident, or at least your thought you had, but then you woke up right back here.

Did you fall asleep? Was it all just a dream? But if it was just a dream, why do you fall asleep? You had been perfectly alert before picking up your food and now you’re passing out behind the wheel of baby? It just didn’t make sense.

Something was off, you could feel it in your gut. But yet you were always known to have vivid and wild dreams, it why you had a hard time believing that monsters were out there when you first attacked by one. You couldn’t have been sure that it wasn’t just your crazy imagination.

One thing was for sure though, you weren’t going to solve anything sitting here in the parking lot and the grumbling in your stomach reminded you how famished you were. Whatever was happening or more likely not happening, you could figure it out back at the bunker with the boys. Speaking of the boys you knew you need to get home before they did or rather when Dean did and spotted a Baby sized whole in the garage.

So ignoring everything that just happened, every confused thought you had, you got back on the road heading home. Your cleared your mind of everything that was happening and made getting home your first priority. Nothing else mattered. If something was going on, well it should stop when you were in the protective walls of the bunker, and if not well then you worked it out in the safety of the bunker with the boys while you chowed down on your food.

But your urgency to get home was less because of the strange things you thought you were experiencing and more due to the fact you wanted to get home before Dean. Real or not, twice now you had experienced deep regret about taking his car without even asking. You could imagine how angry he would be at you, for not only taking her but letting her get damaged on your watch. You didn’t want to feel that way again. You didn’t want to see the anger that would cross his face, anger which you caused. You didn’t want see his heartbroken stare as he took in the damage of not only his precious car but his home and his whole world. You would never forgive yourself for causing him such pain and you would never be able to get his hurt expression out of your head. It would haunt you in your dreams, even now just imagining it had left you shaken. The only way to make sure that didn’t happen was to get home before he could notice she was gone.

So you drove home, ignoring everything else happening in town, your only focus was on the two lanes ahead of you. The closer you got to home the more tension you felt lifted from you, you were going to make it. Everything was as it should be but as you approached Bendman’s Curve this nagging feeling in your gut grew. It was so much that just before entering the curve you pulled over to the side of the road.

You sat there trying to compose yourself. You felt silly sitting here, too afraid to move forward. You felt like a coward, but for the life of you, you could not make yourself precede forward.

Another rumble of your stomach reminded you of how hungry you were. You glanced over at your food sitting on the passenger seat. You wanted nothing more than to go home and dig into it, yet still, you couldn’t force youself to move. The thought briefly crossed your mind about eating here in the car, but you quickly dismissed the idea. Dean had a strict rule about eating in his baby. He let snacks and other small things go on long road trips, but never were you allowed to eat meals in his car, he strictly forbid it. Not willing to risk leaving a mess for Dean to find you chose just to wait until you got home, you be lucky enough if you got Baby home before he noticed, you weren’t willing to take the chance of committing two offenses.

You were lost in your own thoughts when suddenly a black truck came zipping out of the curve. Your eyes widen in shock as it drove past you, close enough that it almost hit you, in fact, if you hadn’t been parked on the side of the road they would have definitely hit you head on as the truck had crossed over into your lane.

You sat there, heart racing with adrenaline at the near miss you just had until the dream you had woken from came flashing back to your mind. That was the same truck that had plowed you down in your dream, from its color, to its make and model, to even the mud stains lining the driver’s side of the vehicle. Something was happening, any doubts you had that it was just a fluke, your imagination, or some crazy coincidence were gone. If you hadn’t felt some uneasiness in your gut that made you pull over you would have sure been flattened under the dashboard as the result of the collision.

You remember Sam briefly telling you about the vision or rather premonitions he used to get years ago. Could that be what was happening to you? It was the only reasonable explanation you could come up with, but then again it didn’t make sense. Sam’s premonitions were caused by the demon blood yellow eyes had given him as a baby. You weren’t one of ‘Azazel’s children’, you had been born five years prior so why was this all happening to you? And why now? You had gone your entire life without any of this happening, so what’s causing it now?

Now the urgency to get back to the bunker was even stronger. If those truly had been visions and they depicted you getting in a car wreck on your way home, then you were in trouble. You still had seven miles left, curse the bunker for being located so far from town, and just because you manage to nearly miss the accident a few minutes ago didn’t mean more couldn’t be along the way, there were a lot of idiot drivers after all.

In fact, the reoccurring theme in visions seems to make that pretty obvious. You avoid the first accident by taking a different route, you missed the second by pulling over at the right moment, two accidents was more than just a coincidence, there will be another.

You let out a frustrated yell when you opened your eyes. Once more you were back at the pizza parlor, this time a loose beam under the bridge slipped as the impala rolled over it. There was nothing you could do as the road slipped away right under your wheels and you went crashing into the watery grave below.

That was the seven time you had tried to make it home, each time a new problem rose up preventing you from completing the trek home. You felt stuck like there was nothing you could do. No matter how safe you drove, you never made it back. Some careless driver or unforeseen circumstances always won.

You had even tried to drive a completely different route home. One that would have taken you far longer to get home and risked the boys beating you home, but at the time you felt it was a safer option than the usual route, given that you died on it six times already.

It didn’t matter want you did or didn’t do, you always crashed, you never make home, and you always ended up right back here to due all over again.

Though you have noticed that no matter how long you took the loop never faltered. Every time you woke up, you woke at the same time, each time, 6:23. At first it had been a blessing it meant that you still had time to beat them home but as the loop continued your looked at the number with disdain. You were trapped in an unless cycle.

The only thing you haven’t tried was waiting the hour out. You hated doing it as you wanted more than anything to beat the boys home, a fact you don’t even know why was so important anymore given everything going on.

You still had no idea what was going on. Was your loop tied to the hour? Was it some sort of bad luck on the roads? Who knows? But right now your only option was to stay off of the road. Maybe when the hour passes this will be all over. Maybe once it gets later the amount of people on the road will dwindle down and you would have fewer hazards to worry about when you try once again to go home.

You still wanted to beat the boys home, but this was the only card you had left at the moment. You decided you rather take the chance of Dean finding out you took Baby without asking and the anger that would result than the rage he would feel when you crashed her. Plus you had expected the boys nearly two and a half hours ago. You’re not sure what has delayed them but maybe it might take them even longer to get back and you could still beat them home. Right?

You walked into the restaurant and found an open table and dug into your food. You had to hold back a moan after the first bite of the pizza. God, it was so good! It almost made you forget all of your regrets.

You’ve had pizza before, but never one quiet like this. It was cheesy, but not overpowering and the sauce was thick and rich, the best consistency, which prevents the crust from becoming soggy, an issue you had with a lot of pizza places. Since you moved into town with the boys it quickly became your favorite and you honestly hated getting pizza anywhere else now.

You took your time enjoying every bite of your food, to savoring it, and too waste time. When you finished you had time to kill and you check for a message from Sam or Dean. There was nothing and you were conflicted as to if that was good or bad. The lack of communication could be from whatever was holding them up or if they had made it back Dean could be waiting until you got home to unleash his fury. You weren’t sure if you wanted them to text you, to let you know that they were home, or for Sam to give you a heads up that Dean wasn’t happy.

As you stared down mindlessly at your phone willing the time to pass faster. You had twenty more minutes to wait before you could back on the road. As you waited you glanced around the restaurant for the old woman from earlier. She was nowhere to be found which made you chuckle in an annoyed way.

All of this started because of her. She neglect the curiosity of personal space and just overall creeped you out. All because of that interaction you drove around town in circles in fear that she was following you. You wondered if you hadn’t wasted time, if you had gone straight home would you still be stuck in the situation you were now?

As the seconds ticked by of the last minute of the hour, you watched in anxious anticipation. You squeezed your eyes shut at the last second in fear of what might happen when the hour went passed. You kept your eyes closed for a few moments. When you opened your eyes would you see the dashboard of the impala or the booth you had been sitting in?

You expected to feel something when the hour mark passed. A whoosh as you transport through space and time, dizziness as you reset in the loop, pain, anything at all.

After several moments of nothing you slowly pride your eyes open. Relief flooded over as you opened your eyes to find yourself still in the pizza parlor. You looked at the time 7:25. You broke the loop.

Not wasting another second you ran out the door and back to the impala, not even bothering to clean up garbage as you raced out the door. You’d feel guilty about it later, but right now nothing mattered but getting back to the bunker, hopefully, before the Winchesters did.

You ran across the parking lot and into the driver’s seat. You moved so quickly you even fumbled trying to put the key in the ignition. When you finally got it baby roared to life, a sound that would always bring a smile to your face, maybe you like Dean in that sense.

Despite your rush to get home, you had not forgotten about everything you have gone through. How could you, it had become a curse upon you, a fate that you couldn’t escape. Until now.

You made sure the path was clear and pulled out of the spot you parked in and then drove off towards the road. There was a car approaching fast, though it looked like you would have just enough time to pull out. But given your history today, that was not a chance you were willing to take, so you waited the extra seven seconds till the car passed. You pulled out the parking lot and made it a little down the road before you came to a stop at the traffic light. Once it was green you proceed ahead heading home.

However, in the corner of your eye, you saw it. A car coming from the opposite direction who thought they could make it running the red. There was nothing you could do to react, nothing you could do to stop the collision that was about the happened.

You were shaken in the impala as the car collided with the driver’s side of the car. The impala was pushed off the road and onto a nearby sidewalk.

Your head had made a violent impact with the window when the car smashed into you. Your head was ringing and your vision was blurry, a feeling you were becoming all too familiar with.

You let out a long and exasperated sign. You couldn’t do this anymore. Thirty accidents. Thirty failed attempts to get home. No matter what you did the outcome was always the same. You had reach your breaking point. You had no ideas left and were out of hope. What was the point to keep trying when nothing changed?

You sat at the scene of your latest accident, the impala’s front had been pushed over to the side of the road while the back end remained in the road. Some idiot had rammed into her from behind.

This accident was different from the rest. Taking stock of your body you couldn’t see or feel anything wrong. All of the previous crashes were serve enough that you had been injured in the impact. You weren’t sure if you died each time or if the loop had reset when you passed out. But this time you were completely alert.

You were confused and unsure of what you should do now. You had never lasted this long after the accident. All you knew was that you couldn’t do this anymore and not wanting to waste another second of whatever time you had left, you pull your phone out of your back pocket. While anyone else would be calling the police or their insurance representatives when placed in a situation like this, there was only one person you wanted to talk to.

The ringing seemed to go and on. You didn’t know what you were going to do if you couldn’t get a hold of him. The constant reliving of the same event was one thing but for that loop to change and you couldn’t get a hold of the one person who could help you out. Well, that felt like a fate worst than death. One thing you knew for certain was that you could not take this anymore.

“Hello. Y/N you there?”

You hadn’t even realized he picked up, you had been too lost in your thoughts. “DEAN!” You shouted.

“Hey sorry, we’re late we ran into some trouble on the way back. I’ll explain it all when we get back.”

They weren’t even home yet. God that hurt. Despite all your wishing that you could beat them home now you wished he was home, so he come and help you out of the hole you seemed to be lost in.

“Dean I need help.” You said urgently, emotion overtaking you. There was no doubt Dean could hear the distress in your voice.

“Woah Y/N what happened?”

“I….I…I” You were now gasping as you tried to explain what you have been through.

“Y/N take a breath. Slow Down.” He ordered. “I need you to calm down so you can tell me what happened.” Someone how your body had responded to him and you took several deep breaths feeling your heart steady a bit. “Good, good girl, now what’s going on?”

“I didn’t know where you were and I got hungry, so I took the impala..” You paused waiting for his reaction. A sharp inhale, a grunt of anger, or something. Yet there was nothing he had either reacted in his facial expression knowing you wouldn’t be able to see or he was hiding his reactions as he didn’t want to upset you further than you were right now. “I just went to the pizza parlor, but now I can’t get home.”

“You can’t get home?” Dean interrupted you sounded slightly annoyed but then were quick to hide it.

“No like I literally can’t. I’ve tried at least thirty times. Something always stops me. Every time I get hit or run over and then I wake up right back at the restaurant. Dean, I don’t know what to do.”

“Alright Y/N calm down where are you now?”

“Highway 42 just passed the fallen barn. Dean, I’m so sorry.” You said crying. “I never dreamed that any of this would happen when I took your car. I should have never done it, taking her without asking, I really don’t know what I was thinking.”

“Calm down Y/N, it’s gonna be alright. Are you okay, are you hurt?”

You looked over yourself once more, “No I don’t think so they hit the back this time.”

“Okay stay right where you are. We’re on our way just stay there.”

It was roughly an hour later when you saw Garth’s beat up car pull up. Dean was quick to jump out of the car and run over to the impala. The rest of the emotion you had managed to hold back came flooding out as soon as you saw him.

You expected him to run to the back to see the damage that occur in the collision, the damage that you caused. But he didn’t, instead, he ran to where you were leaning against the hood. You looked down as he approached. “Are you okay?”

“I…I’m f… fine,” You crooked out. “I wasn’t hurt.” You weren’t able to look him in the eyes too ashamed of what you’d done and afraid to see the look on his face, the anger and the hatred that you were sure had to be there. “Dean I’m so so sorry. I know that nothing I will ever do will be able to change what I’ve done, the damage I’ve caused. And I know you probably never be able to forgive me, but I just need you to know that I truly am sorry.” You cried.

“Y/N sweetheart look at me.” He spoke in a gentle voice. And that nickname he used, you knew it meant nothing, he’s used it all the time on victims he came across. But your heart couldn’t help but flutter in response.

Dean put his finger under your chin and gently lifted your eyes to meet his. “I’m not worried about that. I’m more concerned with how you are.”

“Dean you haven’t even see it yet, the damage that …that I caused.” Another tear slipped down your cheek.

“All that can wait. Whatever is damage can be replaced. You can’t.” Dean brushed the tear from your cheek and tucked a strand of hair that had fallen in your face behind your ear. You watched his eyes furrow at you when he did.

“That’s bleeding a lot Y/N.” He brought his hand up to your forehead and touched the gash on your head and you winced in response. “Why didn’t you say something?”

You looked at your reflection in the windshield of the impala. “I didn’t know, I honestly didn’t even feel it.” You confessed. Dean led you back to the driver’s seat and sat you down and then he moved to the back of the impala. You tried to get a look at his face, to see his reaction once he saw the damage, but you couldn’t get see from where you sat.

Dean pride open the trunk of the implala and return to you with the first aid kit. He began to fuss over your wound, cleaning the area and preparing to bandage it. “Dean really I’m fine.” You said trying to stop his hands and moving your head away.

Dean was persistent though and his one hand easily caught both of yours and held them out of his way while he continued to work. “Y/N that was a lot of blood.”

“You know how head wounds are, they’re overdramatic. Really I feel fine.”

“Nevertheless let me take care of you.”

Dean was finishing placing the bandage on your head when Sam came walking over. “How are you feeling Y/N?”

“Just peachy.” You said with a slight sigh.

He gave you a sympathetic look. “Mr. Davis over there takes full responsibility for the crash,” He must have flashed his badge and had been handling the scene. “He said he leaned down to grab his phone which had fallen and wasn’t watching the road.”

This was a fact you had already known as you had talked to the man after you got off the phone with Dean. Dean had yet to show any anger or any inclination that he was upset about the accident, until now that was. You watch Dean’s eyes narrow as Sam spoke then he closed his eyes and took several deep breaths. You could see the rage bubbling below the surface, but when he opened his eyes again all you saw was concern for you.”

“I called Garth at the motel, he’s on his way with a tow truck as she’s not gonna anywhere and I figured you’d rather fix her up yourself.”

Dean nodded his head in response. “Yeah, I saw that too. Back left wheel popped.”

“Dean I’m sor…”

“Shhh Y/N”, Dean said placing a gentle hand on your cheek. “The damage is not that bad. Sidings dented in on the back side and the tire popped on impact with the truck. But that’s nothing I can’t fix. I’m just glad you called me when you needed help.

Sam knelt down next to Dean, “Speaking of Y/N what’s going on?”

You ran anxious fingers through your hair, “I’m not sure I decided I wanted food and went to the pizzeria, got back on the roa to head back and I got into an accident. I passed out only to wake back outside the pizza parlor to do it all again.”

You went on to tell them everything you have been through, every accident, everything you saw and felt on your countless attempts to get home. Sam and Dean nodded their head as you explained everything and when you finished they paused thinking it over.

“And how did you break the cycle?” Sam asked.

You shook your head. “I didn’t. I don’t know what happened I still may reset now.”

Dean looked at his watch and shook his head. “It’s been over an hour since the crash I think if you were gonna reset it would have happened already.”

“So why didn’t I?”

“You said you passed out after each accident right?”

“Yeah, due to the trauma I endured during each crash. I never made it past five minutes afterwards.”

Dean nodded his head in response. “So every time you’ve lost consciousness the loop has reset.” Sam finished Dean’s thoughts.

Dean frowned, “Which means you still could reset if you fall asleep.”

His words made your eyes widen and send a shiver down your spine in fear.

“It’s alright Y/N. We’re gonna figure this out.” Sam said placing a comforting hand on your shoulder. “Can you try and recall anything that you encounter that was strange or out of the ordinary?”

“You mean besides getting into thirty crashes in a row?” You deadpanned, You shook your head, “I don’t know all I really did was drive. I would go different ways or at different times in hopes I could get back, but it never worked.”

Sam and Dean’s faces mirror each other as they puzzled over what could be the cause of your endless cycle.

“Though there was this woman.” You said as you remembered how this truly started.

“What woman?” Dean asked.

“When I was waiting for the food there was this older woman at the counter waiting for hers as well. She started making causal conversation with me but then she started creeping me out.”

“What did she do?” Sam inquired.

“Nothing really. I mean there was the whole neglecting the curiosity of personnel space thing, but is more of the feeling I got. She left me uneasy and for a moment I thought she was following me, so I drove in circles around town trying to lose the tail I thought I had.”

“And then what happened?”

“Once I thought I shook her I got back on the main road to head back to the bunker and then I got into my first accident.”

“Did she say anything unusual?” Dean asked. You furrowed your brow, “You know like something that might lead to our kind of work. Chanting, spells, or anything?”

You shook your head, “Not that I know of. She tried to touch me, but I stepped back.”

“Touch you? How?” Dean asked voice slightly raising.

“She compliment my hair and then tried to run her fingers through it.” Sam and Dean shared a look communicating wordlessly. “Guys, what is it?”

Dean brought his hands out to you, “May I?” He asked as he reached for your jacket.

You nodded your head in response. Dean began running his hands up and down your coat. What he was searching for you weren’t sure, but he left no trace unturned as he scanned your sleeves and your pockets.

When he reached in your left pocket his hand stilled. You watched him pull out a small brown bag wrapped closed with leather. A hex bag.

You couldn’t believe you had no idea it was there. All this time you had been carrying it around with you and you hadn’t even felt it. Nor had you felt the woman place it in your pocket, but I guess that was the whole point.

Dean quickly took at his lighter and burned the bag into ashes effectively ending its cruel spell. You felt relief flow over you as you watched it burn. It was over. It was finally over.

“Damn witches.” You mumbled in embarrassment. You were nowhere near the level of expertise that Sam and Dean were but you still felt like should have figured it out sooner.

“Yeah, they are tricky bastards.” Dean said sharing a knowing glance with Sam.

“What do you mean?”

“The reason we were late, was because of witches they put a border spell around the town and we couldn’t leave until we broke the spell.”

“What’s that have to do with any of this.”

“We caught one of the witches. Their coven order then to do whatever possible to distract us.”

“Distract not kill? Doesn’t that seem strange?”

“That was exactly our thought.” Sam said. “And it looks like you got the same hit. I think it’s got something to do with Rowena, she was acting very strange the last time we ran into her and whatever she working on she clearly doesn’t want us getting wind.”

“Yup, but that’s something we can figure out later. For now, you need to rest.”

“Dean I told you I feel fine.”

“Sure you do, but head injuries are nothing to mess with. You may feel fine now because of a delayed reaction. Plus we don’t know what kind of trauma that might linger after thirty head injuries.”

Later that night

After getting back to the bunker you reheated your food, it was a miracle it was only slightly shaken in the crash. It would have really been a letdown if you endured all that for nothing. You ate with the boys and talked over the day’s events.

Once you were done you were feeling stuffed and tired so you laid down to take a nap

When you woke though you didn’t feel well rested instead there was a throbbing in your skull. You glanced at the clock seeing it was just after midnight. Not feeling like you would be able to sleep you decide to eat or research or whatever, you would decided on the way.

However, when you walked out of the room and started making your way down the hall you heard a clanging noise and despite the ache in your head, you followed the sound.

It led you to the garage where you found Dean working away on his baby. “How’s it coming?” You asked announcing your presence.

Dean stopped what he was doing and turned around to face you. “She’s coming along.” He said placing his tools down. In truth, she was looking better. Dean had already replaced her wheel and he was working on smoothing out her surface.

Despite his success though you still felt guilty. “Dean.” You said your voice changing as the emotion came back.

Dean looked back at you, “Y/N, don’t.”

“Dean,” You repeated, “I know I’ve said it before but I’m so sorry.”

“I know Y/N. I’m not angry at you.” He admitted.

Your eyes widen in shock, “How? I know I don’t need to tell you this, but she’s more than just a car Dean. She’s been the one constant thing in your life. She’s protected you and looked after you more than anyone else ever has. She is where your heart is, where your home is, and where you are truly the happiest. And I knew that. I don’t know why I thought I could just borrow her, especially without even running it past you.”

Dean rested his hands against the impala and leaned on her, “Why did you.”

You brushed your hand through your hair, “ I don’t know. I guess it was because I never get to drive her and I thought it would be a short trip. I guess I was feeling a little rebellious. I’ve told you about the girl I used to be, shy, innocent, and always following my mother’s orders. I guess I just saw it as a chance to break a rule without consequence and without you knowing. Though if I would have known what would happen I would have just starved until you guys got back.”

“You could’ve asked Y/N.” He said in a genuine tone.

“Oh come on Dean. Are you seriously trying to tell me you wouldn’t have made up some excuse for me not to? You hardly let me drive her as it is or Sam for that matter.”

Dean smirked as he thought it over, “I suppose you got a point there. How are you doing?”

“Okay.”

“No lasting effects from the multitude of head bashing?”

“Nope.” You lied. In truth, your headache was starting to grow in intensity so much so that the light was starting to bother you. “You know it’s funny all that I went through, after every crash and I reset back in front of the restaurant and all I could think was I got a second chance to fix this. To get her home before you figured out I took her and get her back safely. If I just called you after the third, fourth, hell even the fifth crash, I could have saved myself a lot of time and pain. I was focused on trying to escape the hand fate dealt me I missed what was really happening.”

Dean let out a small chuckle, “Yeah I guess so. Do you remember it all?”

“Yeah, it wasn’t like your endless loop with the trickster. I remember all the pain I went through and every last minute thought that crossed my mind as the end drew near.”

“Like what?”

“Oh um, just you know the usual stuff.” You said sheepishly. “Stuff I didn’t do, things I didn’t say, and that sort of thing. Love not shared.” You added softly at the end.

Judging by the way Dean’s eyes lit up though he seems to have heard you. He came to your side. “You know I was so worried when you called me tonight. You sounded so worried, so frightened. I didn’t like that. I didn’t like not being there for you.”

“I’m sorry. I was just so afraid I was gonna reset and I didn’t know what else to do.”

“Don’t be. I’m glad that you called me when you needed help. And for the future Y/N, I don’t want you ever to be afraid of calling me when you need help because you’re afraid of how I’m gonna react. If you need help, I’m there. We could work out whatever else later.”

“Thanks, Dean.” You said a warm feeling settling in your chest. “I really appreciate that.”

Dean hummed in response, “So this unfounded love. Anyone I know?” He asked.

You felt your cheeks heat up as the blush rose to them. You wanted to lie as you were ashamed to admit your feelings. You’ve had a crush on him for three years now and every time you tried to confess your feelings it’s as if you’re hit with laryngitis.

But based on the way Dean was looking at you, with the knowing smirk, you knew he would see through your lie. “Just someone who I love very much. He takes care of me in so many ways. Looks out for me and helps me out even when I don’t know it or think I need it. He makes me feel loved and special and makes me believe that there is good in life. He makes my heart flutter with his endearing pet names and his touch is so gentle and sweet.” You looked away from him choosing instead to look past him at baby where he had been fixing her. “I know he doesn’t reciprocate those feelings in the way that I do, but that’s okay because to be loved by him, even as a friend is more than I can ever ask for.”

Dean followed your glance back at his car. “You know you were right she does mean a lot to me. And don’t get me wrong I would kill anyone who tired to take her from me, but there’s one thing you got wrong.” You looked back at him. “Baby is not where my heart lies. My heart lies with the woman who stole it. She’s a dream I never thought I’d get and I cherish every moment I have with her. Whether we’re laughing at cheesy old movies or singing along to the music on the road. I would love more than anything to take her as mine and spend the rest of my life with her.” Dean said grabbing your hands in his own and leaning in for a kiss.

You weren’t sure if this was real, a dream, or a crazy hallucination brought forth by your aching head but either way, you weren’t gonna let this moment pass by. You closed the gap between the two of you as you mapped out his mouth with yours. You only parted when the need for air forced you to and you pull your lips back with a big smile on your face.

Dean had a matching smile of his own and the two of you stood there in each other’s arms happy as can be. Dean stared into your eyes lovestruck for several moments until suddenly his expression changed as his brow raised, “How’s the head Y/N?” He asked amused.

“Good.”

His brow raises further with a smirk on his lips. “Really so you wouldn’t mind if I got back to work pounding out this siding?”

“Actually..” You began before Dean interrupted you.

“Your head hurts doesn’t it?”

“How did you know?”

“I recognize the sign of a concussion Y/N and your dilated pupils and droopy eyelids are a clear giveaway. Why didn’t you say something sooner.”

“I didn’t think it was anything more than a small headache.”

Dean gave you a bitchface, “With all the head trauma you’ve had today?”

“Not hold on we don’t know that the last twenty-nine have lasting side effects seeing as I reset after each one?” You counter.

Dean shook his head smiling. “Come on.” He said taking your hand and leading you back into the bunker. “We’re getting you some Advil and getting you back to bed.”

“Only if you stay with me.”

“Always sweetheart.” He said while placing a kiss on your temple.