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6lostgirl6 · 3 months

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Yandere Alphabet - Demon!Dean Winchester

TW: Toxic Relationship, Possessive Behavior, Controlling Behavior, Hints of Physical Abuse, Hints of Verbal Abuse, Kidnapping, Mentions of Murder, Isolation And Spanking As Punishment, Cursing, Manipulation. A/N: Please inform me if I did not tag something correctly. Please know the difference between fictional and reality. While fictional, these types of relationships are extremely toxic, especially in real-life. If your relationship is showcasing these toxic behaviors, please seek help from someone to get out safely. Reblogs are heavily appreciated!!

Affection: How do they show their love and affection? How intense would it get?

He’s a physical lover, and he doesn’t give two fucks about PDA. He’ll kiss and touch you whenever and wherever he likes. He always gives you heated, passionate kisses while grasping all over your body and pressing you up against him. When he’s really affected, he’ll growl while kissing you, and his eyes will flash black on occasion.

Blood: How messy are they willing to get when it comes to their darling?

Very messy. Demon Dean, at this point, is a malevolent being and will resort to more grotesque methods when it comes to his darling. Even if it means killing innocent people who look at you the wrong way or dare touch you, well, try. He’ll break the person’s bones before they even lay a finger on you.

Cruelty: How would they treat their darling once abducted? Would they mock them?

Depending on how you react to the situation, his treatment of you varies. If you behave, he'll treat you good by his definition. However, if you react badly, he's going to not react well. Yes, he’ll mock you, because we need to remember that he may love you, but that doesn't change his nature. He has a cruel sense of humor.

Darling: Aside from abduction, would they do anything against their darling’s will?

He’ll make you come with him on his killing sprees. You’re not a fan of blood; that’s too bad. You’ll just have to get used to it, because that’s all you’re ever going to see besides him. Blood and carnage.

Exposed: How much of their heart do they bare to their darling? How vulnerable are they when it comes to their darling?

Demon Dean still has some of his old traits from when he was human. He doesn't like expressing his emotions until he trusts you enough. Which would take a long time. However, when he finally trusts you, he’ll be more open about his feelings for you. He still keeps things close to his chest, though he might never speak with you about it.

Fight: How would they feel if their darling fought back?

Oh, he’s pissed.

Game: Is this a game to them? How much would they enjoy watching their darling try to escape?

No, your relationship isn't a game to him. But getting you to fall in love with him will be like a game, and he'll triumph. It’s only a matter of time. Demon Dean wouldn't like seeing you try to escape; it would automatically anger him. He’ll lash out at you.

Hell: What would be their darling’s worst experience with them?

Your worst experience with him would be your fights with him. He's scary when he’s angry, especially when it's towards you. He’ll practically scream in your face and manhandle you. Another thing would be him forcing you to see his killing sprees. He doesn't trust you enough to leave you on your own, so you'll have to witness his brutality.

Ideals: What kind of future do they have in mind for/with their darling?

When it comes to your future with him, you’re stuck with him, and not even death would separate you. He’ll secretly try to uncover a way to turn you into a demon. You'll be isolated from hunters; demons wouldn't dare approach you. He’s the only thing you’ll ever need; nobody else can help you.

Jealousy: Do they get jealous? Do they lash out or find a way to cope?

Extremely, however, it’s not because he’s insecure; you simply belong to him and are completely off-limits. Coping, what’s that? He’s going to lash out in a violent way at the person attempting to flirt with you. He left people bloodied to a pulp on the floor before, and he has done worse.

Kisses: How do they act around or with their darling?

It’s discrete, but he’s a little softer around you, and he would let you get away with small things that he wouldn’t tolerate if it were another person. As a demon, he’s not afraid to show you how deep his love runs for you. He’s clingy and always has a hand grabbing you somewhere. He’s very possessive, and he tends to keep you to himself.

Love letters: How would they go about courting or approaching their darling?

When it comes to demon dean, there is no time for courting or lightly approaching you about his feelings. When he kidnapped you, there were no romantic gestures or heartfelt confessions; you simply belonged to him, and you need to get used to it.

Mask: Are their true colors drastically different from the way they act around everyone else?

Of course, Dean treats you differently compared to others. He’s less rough around the edge, and he does try to control his temper better around you. You’re his, and he doesn’t mistreat what belongs to him.

Naughty: How would they punish their darling?

Depending on what you do, however, he'll simply tie you to the bedpost and keep you there until you learn your lesson. He would never intentionally hurt you, but he will force you over your lap and smack your ass until you’re begging for forgiveness. Trust me, he wouldn’t make it fun for you.

Oppression: How many rights would they take away from their darling?

The better question is: how many rights would he allow you to have? All you need to do around him is eat, sleep, and look pretty for him. Misbehave, and you’re going to be chained to the bed again.

Patience: How patient are they with their darling?

He will have zero patience with you, so you better behave for your own sake. He's not afraid of punishing you, however he sees fit, because you didn’t listen to him or try to escape. Therefore, try not to upset him too much.

Quit: If their darling dies, leaves, or successfully escapes, would they ever be able to move on?

No, he would never move on. If you died or were killed, his rampage would be talked about in Hell for centuries. If you manage to escape, it won’t last long. He’s going to get you back, whatever it takes, so enjoy the freedom while it lasts.

Regret: Would they ever feel guilty about abducting their darling? Would they ever let their darling go?

Ha! Hell no. However, after being cured, he will feel horrible for how he treated you. He’ll feel ashamed that his darker feelings for you were brought to light. He really does love you, but the demonic side of him has horrible ways of showing it.

Stigma: What brought about this side of them (childhood, curiosity, etc)?

His transformation into a demon allowed his yandere tendencies to be brought to the surface. He doesn’t have to hold back his urges anymore, and why would he want to?

Tears: How do they feel about seeing their darling scream, cry, and/or isolate themselves?

Of course he doesn’t like it; he prefers you being obedient and rather docile. He would never admit this, but he would want you to be happy with him, even as a demon. If you try avoiding him, he’ll keep bugging you and forcing you to talk to him. He lacks patience, so your screams and cries will only make him angrier the longer you keep having tantrums.

Unique: Would they do anything different from the classic yandere?

Demon Dean would never hurt you intentionally, especially by abusing you to make you cooperate. Sure, when he lashes out, there may be a few accidents, but that’s all they are. Accidents.

Vice: What weakness can their darling exploit in order to escape?

There are two things you could use: his killing urges and/or feeding into his ego. If you want to play the waiting game, you would have to gain his trust enough to allow you to be out of his sight. Simply pretending to love him won’t be enough because he’ll see right through you. When he goes on his killing sprees, leaving you behind for once will be your chance and only chance to escape. You better protect yourself; he will find you.

Wit’s end: Would they ever hurt their darling?

No matter how much he cares about you, he will hurt your feelings at times, especially when he flirts with other women in front of you. When he’s extremely angry or has the itching need to kill something, you need to stay out of his way. He will lash out at you with hurtful words and potential bruises.

Xoanon: How much would they revere or worship their darling? To what length would they go to win their darling over?

Demon Dean cares about you despite who he is, and he doesn’t like upsetting you. You’re not much fun with tears in your eyes. As a demon, you’re the only one that makes him feel things—feelings he used to hide within when he was human. Anyway, he would go to the ultimate length to win you over. He’s not going to beg on his knees for your love, but he’ll show you how much he worships you in his own way. You want him to kill someone and bring you their head? He'll do it.

Yearn: How long do they pine after their darling before they snap?

After Dean became a demon and left with Crowley, he didn’t take you with him at the time, no matter how much he wanted to. However, you’ve never left his thoughts, no matter how much he tried to drink your sweet voice away. You haunted him for months until he finally snapped and came after you.

Zenith: Would they ever break their darling?

If Dean was never cured or you never managed a way to escape from him, he’ll find a way to break you and make you depend solely on him. Make you finally see that he is the only thing that would kill to keep you safe. One way or another, he’ll make you fall for him.

Taglist: Comment to be added/removed!!

@prettywhenibleed @britany1997 @rottent33th @slaasherslut @huntressandlioness1 @wraith-posts @schizonephilim

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zepskies · 4 months

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DEAN WINCHESTER IMAGINES

Stories are Dean Winchester x Reader unless otherwise noted. These imagines include reader requests, headcanons, and one-shots from other story verses.

(**Notes 18+ only and/or smut)

You are Dean's one exception. 💚 In which Sam's in love with his brother's girl. (How Dean reacts.)

Sam crosses the line. ✨ You're dating Dean. Sam secretly loves you. He finally sees his chance with you after he's hit by a witch's spell. - [Sequel to You are Dean's one exception.]

⭐ Bonus: The conversation between you and Dean after you "find out" about Sam's feelings.

Reuniting with Dean.** 🩵 Dean returns from Purgatory. Will either of you be the same?

Texting Dean when he's on a hunt.📱 Sometimes he likes your teasing...other times he doesn't.

Dean gives you an impossible choice. 🫢 In which Dean is in love with his brother's girl.

Choosing Him 💞 You’re forced to make a decision between Sam and Dean. - [Sequel to Dean gives you an impossible choice. Contains both Sam and Dean endings.]

Say It Right 💜 You ask Dean for the truth: "Do you love me?"

Headcanon: Personality types Castiel, Sam, and Dean would be attracted to. ⭐

Vintage Collection** 📖 You and Dean discuss (argue about) his favorite magazine, Busty Asian Beauties.

Headcanon:** How Dean Winchester, Beau Arlen, and Soldier Boy (Ben) would react to seeing your breast reduction scars. ❤️‍🩹

Headcanon: How Dean Winchester, Beau Arlen, and Soldier Boy (Ben) would make up for pissing you off. 😤

Dean reads you wrong. 🤔 He likes you. The thing is, he thinks you might like Sam...

Headcanon: How Dean Winchester, Beau Arlen, and Soldier Boy (Ben) would react to you teasing him under the table. 😉

Headcanon: How Dean Winchester, Beau Arlen, and Soldier Boy (Ben) would react to you getting "morning" sickness during pregnancy. 🤢

Dean Winchester Masterlist

Supernatural Masterlist

Main Masterlist

✍️ Writer Support:

Have you enjoyed my Dean stories?

If you'd like to keep supporting me as I continue writing, here's a way to keep me caffeinated: Ko-Fi Me ☕

💌 Get Notified:

Follow @zepskieswrites (with notifications on) to get notified every time I drop a new story.

#Dean Winchester Imagines #Dean Winchester Masterlist #dean winchester #dean winchester x reader #dean x reader #dean x you #dean winchester x you #spn #supernatural #dean winchester smut #reader requests #dean winchester x female reader #dean winchester fanfiction #dean winchester x plus sized!reader #dean winchester x latina!reader #dean winchester x plus size!reader #dean winchester headcanons #zepskies writes

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shelbgrey · 9 months

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Dating Dean Winchester Headcanons:

Paring: Dean winchester x Singer!Reader

Summary: just some headcanons about Dean dating Bobby Singer's niece. -NSFW content warring.

A/n: the winner of the latest poll, there will be a new one up next week. I was so excited and suprised on how many people did the poll, my first one only had six and the latest one had over 100.

❤️Mood board ❤️MasterList

Being Dean's girlfriend isn't always easy, but you get through it. So let's talk about it.

There was always something between you guys, but with your choice of life there was always something in the way.

You two practically grew up together, with Bobby being your uncle and John being his father you two were always around each other.

I think Dean also had a slight fear of Bobby, you were his niece and your practly his daughter.

Bobby wasn't clueless, he saw the way you two looked at each other. He wanted to kick Dean's teeth out, he's extremely over protective. Bobby also knew if anyone would keep you safe it wold be Dean.

“I know you'll take care of her”

On a side note, Bobby refuse to call you 'idjit'

The last thing he's said before he died was, “take care of my girl.. You idjits”

Anyway, Even if you two kept denying it or if your just clueless, everyone would know.

Other than Sam and Cas, your the only one he 100% trusts you. He'd trusts you with his life and your his partner in crime.

What makes your relationship stronger is that you started off as best friends and allies.

You always thought you were losing him, he would always have one night stands and there was Lisa. Of course they ment nothing to him, he just thought he'd never be good enough for you.

He thought you deserved better. “I'm not what you need...you deserve better”

That was the first time you opened your heart out to him, but he put his walls up. The he pretended like nothing happened... Until you went on one particularly hard hunt.

Everything was happing so fast thst neither one of you remember that night. There was blood everywhere and Dean did everything he could to save you, Castile healed you and Dean confessed something he's been wanting to since he was 18.

“I love you... Please don't leave me, I can't lose you”

Since everything moves fast in your lives you both decided to take things slow. Dispite his rugged appearance he's nothing but a gentleman to you.

He's extremely over protective of you, to the point hunts with him got annoying.

“I'm not some damsley in distress, Dean!”

He knows what a badass you are and he knows you can hold your own, but he can't help but be your shield.

That's really the only times you fight, your both very reckless and laugh in the face of danger. You guys stress each other out on hunts.

But, lets get to the good stuff now.

Your the only other person who can drive the impala, you'd rather just have him driving with you setting with him.

You guys love the same music, so your always singing on the top of your longs to old rock songs. Your guys song is Angel Eyes by The Jeff Healey Band.

You always have to be sleeping next to each other to get a goods night rest, even when you weren't together you two shared a bed in the old motels.

Dean refuses to sleep unless you have fallen asleep first, he just needs to know your okay before he can have a good night sleep.

You bake the best pies in his opinion and Sam loves your homemade salsa.

When you guys moved into the bunker you guys made great use of the kitchen, Sam loves your guys cooking.

Speaking of Sam, he's one of your best friends. Cas is your first, but you and Sam have a long history together. You were even the first one to hear he got accepted into college.

We know Cas is like the Winchesters gardian angel, well Gabriel is yours.

About three years into yours and Dean's relationship you broke up, it was around the time Sam went to hell and you guys just pushed each other away.

Gabe knew you guys loved each other, so he worked really hard to get you back together. He did succeed.

You guys might argue about the little things, but he always know how to make them better.

You guys just like staying in and watching movies or Scooby-Doo. You guys love cuddling up in the Dean cave and just ignore the world for a few hours.

He loves cuddles, if your in bed or on the couch he needs to be holding you. He loves it when he's laying in bed and your lying on top of his chest.

He also loves it when you hold him, maybe after a rough hunt he'll love just rest his head on your chest while you play with his hair.

You love just being in his arms, there's no feeling better than that. He loves snaking his arms around you and resting his chin on your head because he just really needs to being close to you.

He's really just a big ol' teddy bear.

He's a rough kisser, he's way taller than you so usually he hold your chin between his fingers and lift for head up to kiss you.

There's a lot of neck and forehead kisses being handed out by this man. He loves wrapping his arms around you from behind and just trail soft kisses down your neck.

He also loves it when you kiss his forehead. It just a small, loving gesture he absolutely loves.

If your cold you'll steal his flannels or his jackets, he had this black and red flannel that he now only sees if your wearing it.

when ever your busy doing research Dean always deliver a tiny kiss on your forehead. He'd just be walking by and he'll give you a quick kiss just to make you blush.

He's good a making you blush, he thinks it's adorable.

Trust is a big part of your relationship, you both had opened up about the abuse your fathers and dumped on you. That was the reason Bobby took you in, he could bare you being in the type of environment he grew up in.

With that Dean made a promise to never hurt or scare you. He refuses to lay a hurtful hand on you. It'll break his heart if you flinch away from him during an argument.

As much as you love Dean, demon Dean scares the hell out of you. The demon knew this and used it to his advantage. He Dean went back to normal he could barely look into your eyes. He blamed himself for the bruises around your neck the demon caused.

“I promised you I'd never hurt you... I'm so sorry” he said. “it's not your fault”

On a more positive side... You guys have lots of nicknames. You call him Deano or bub and he calls you just about anything but your actual name, Sweetheart is your favorite.

And with FBI names, you take a different approach. While he uses rock aliases you use actor or fictional names.

“agent Sweets, really?” he said playfully. “What? I like the show Bones”

Your like a mother to Claire, she loves you so much and your the only person she trusts other than Jody and the boys.

Speaking of Jody, she took you under her wing immediately. You never had a mother growing up so it was a relief to have her in your life.

You become a mother to Jack too, and your relationship hit a really bumpy road during that time. You hated how Dean treated Jack and it always turned into a fight.

“if you touch him, I swear to God, Dean!”

Den didn't want to be like his father and after awhile Dean's shell broke and he started to grow a soft spot for him, after your lives calmed down you both did end up adopting Jack.

But to legally do that you had to get married. You both wanted to get married so bad, but with your lives you never got the chance.

You weren't gonna get a white wedding, you knew that and Dean thought the Cort house wasn't good enough. So you got married in the church of Elvis in Las Vegas.

NSFW headcanons:

Dean prefers being on top and being the one in control.

He'll mark your thighs with his teeth and biting hard enough to leave a light bruise.

Loves eating you out,your legs around his head. He loves your legs in general and loves leaving kisses on the insides of your thighs. He'd rather pleasure you for hours than receive.

Hair pulling, he loves feeling your fingers in his hair or he'll tangel his fingers in yours and tug on it when he's getting head or about ready to cum.

Bondeg kink, ropes, his ties, belts, he'll tie you up with anything if your comfortable with it.

definitely a fan of overstimulation, he loves the way that your body twitches and you whimper from his touch.

car sex! All the way. loves to take you in the back of the impala, loving the way the windows fog up and the small area gets loud with the noises you make.

He's a soft/mean Dom, it just depends on his mood. But no matter what he always makes sure your comfortable. He loves to take control in the bed but would never push you.

He would really get off on marking you up. He didn’t think he would, as it wasn’t something he thought too much about but when he did it there was no turning back.

He definitely has a Praise kink too, he loves making you feel loved and appreciated. He love how he can easily make you blush. “your so Beautiful”

“you feel so amazing Sweetheart”

He loves hearing you moan. If you try to hold back or even muffle them when it's unnecessary, he'd put an end to it. “don't hold back, let me hear your voice”

He has big chocking kink, he won't be too rough about but he loves wrapping his fingers around your neck and feeling your pulse when he's ramming into you.

This man is amazing when it comes to aftercare. He knows exactly what you need. After your both cleaned up, he'll pull you to his chest to cuddle.

#Dean winchester #Supernatural #Dean winchester x reader #Dean winchester x Singer!reader #Supernatural headcanons #Dean winchester headcanons #Dean winchester imagines #Jensen Ackles x reader #Bobby Singer x reader #Bobby Singer headcanons #Jensen Ackles

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graceloveswolves · 7 months

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i feel like this is such an odd request but could you do dean winchester headcanons with a fem!reader whos obsessed with anything flavored cinnamon? like cinnamon candy, lollipops, cinnamon tea (yes its a thing) anything from cinnamon gummy bears to cinnamon coffee? this is so weird but i love cinnamon 🤍

I LOVE CINNAMON AND I AM CURRENTLY DRINKING CINNAMON TEA WHILE READING THIS HAHAHA!!

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Dean Winchester Feeding Into Your Cinnamon Addiction Would Include…..

———————————-

- Buying you any candies that have cinnamon in them

- it being a little game for him, every time you stop at a gas station he tries to find a cinnamon candy you haven’t tried yet

- whenever you are mad at him, or he doesn’t come back from a hunt on time, he will come back with a box full of cinnamon treats

- him trying to get you to do the cinnamon challenge

- one time he found this cinnamon whiskey neither of you have ever seen before

- neither of you to this day remember that night

- he woke up with his face on the toilet bowl

- you woke up in the shower next to the toilet

- Sam had a bunch of photos of you guys for blackmail

- the kitchen has a drawer full of all kinds of cinnamon flavored teas

- the Impala has a little candy bag full of cinnamon candies for the road trips you take

- Sam once sat on your cinnamon candies that were in the front seat of the Impala

- melted all over his jeans 👖

- Dean and you were laughing for ages, and got a picture back for blackmail

- him and you playing guess that candy during road trips

- he personally likes red hots the best

- one time you and Sam told Dean to try this piece of “cinnamon chocolate”, it was actually ghost reaper pepper chocolate.

- and of course it was while you guys were on the road

- he pulled over to the nearest gas station and drank 3 bottles of water in the store, without even paying for them

- one time you tried to give him head after eating a bunch of cinnamon candy…

- he had to take a cold shower and scrubbed the hell out of his pee pee

- you guys making cinnamon rock candies during Christmas

- making cinnamon apple spice for him and you

- the bunker always smelling like cinnamon

- him buying you cinnamon candles, wax melts, wall plugs

- one time you bought one of those cinnamon broomsticks for decoration

- then came home to find him sweeping the bunker with it

- Sam bickering with him “DeAn! ThAts NoT wHaT iTs FoR!”

- when you don’t go on hunting trips with him he buys cinnamon air fresheners to feel closer to you since it reminds him of you

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lokischickadee · 15 days

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Found on Pinterest!

#dean winchester #dean winchester smut #dean winchester headcanon #dean winchester fanfiction #dean winchester x reader #dean winchester x you #dean winchester fluff #dean winchester headcanons #dean winchester imagine #supernatural x reader

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dingo-ate-my-hot-lettuce-crazy · 1 year

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THIS IS BASED OFF A TIKTOK I SAW BUT IMAGINE THIS IF YOU WERE THE BOYS’ YOUNGER SIBLING

Dean: Hey kiddo, how was school?

Y/n: it was good i met a boy today!

Dean: …

Sam: …

Dean: oh yeah? what uhh what was this boy’s name?

Y/n: his name was michael and he told me he likes me!

Dean & Sam *panic*: …

Y/n: we held hands and everything!

Dean & Sam: *look to each other* YOU HELD HANDS???!?!?!??

Y/n: yeah :D

Dean: oh no, oh my god, Sam..you know what we have to do…

Sam: agreed.

Dean & Sam: *grab Y/n and carry them to the sink, and stick their hands under the faucet*

Dean: SANITIZE! SANITIZE!

Y/n: *uncontrollable laugher* no! it was only for like five minutes!

Sam: Five whole minutes!!!! This calls for the holy water…

Y/n: *dying laughter with hands still under running water*

RAHARAHARAHARAHARAH im feral for this hc

#supernatural #dean winchester #dean #spn #dean headcanons #dean winchester headcanons #dean winchester x reader #dean x sister!reader #dean winchester headcanon #winsister #winsister imagine #sam #sammy #sam winchester #spn imagine #spn incorrect quotes #incorrect supernatural quotes #sam x sister!reader #spn sister reader

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bitchinfawkseh · 8 months

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Dean Winchester X F!Reader NSFW Headcanons

A/N: mmmmmhM I start school tomorrow kms. Some of these are pretty general and work for M or F soooo yes.

• really, REALLY wants u to sit on his face like all the fckn time

• comes up behind u, presses his hard dick against your ass and gropes your tits when you're alone

• stuffs his hand in your panties and plays with you a lot, especially during traffic jams, and you're both stuff in Baby

• begrudgingly comes with you to buy underwear and lingerie because he knows you'll show him how it looks on ya at home

• LOVES it when you put on lipstick and then make out with him and kiss all over his face and neck bc of the marks it leaves

• too many pregnancy scares bc of how often u fuck

• lots of quick desperate quickies in diner bathrooms and such (works whether ur M or F)

• when you give him the look and put your hair in a ponytail or smth he IMMEDIATELY is hard

• eats your pussy like it's his last meal

• idk bruh he just likes to eat pussy

• likes to fuck u in front of mirrors so he can see you come apart

• lemme tell ya he takes TASETFUL nudes none of that holding the dick, dawgs out crap

•really likes the way ur hair smells so sometimes he'll just come up, hug you from behind and start smelling it and kissing your neck

• very odd ig?? But it immediately gets him in the mood when he watches you like in your element. Like doing the thing your best at

• his favorite bra of yours is his hands. Def a boob guy

• just likes how soft and squishy they are, doesn't matter if you're flat or they big asf.

• picks your nail colour and then later that night probs takes pics as you give him a handie (with permission ofc) likes how pretty your hands look

• hand fetish bro

• roleplayyyyyyy

• can either fuck you so sweet and lovingly or hard and rough with no mercy

•depends on the day 🥰

• LOVES it when you wear his shirt and nothing else not even panties. He'll take you right then and there

• the type to rip your tights or fishnets out of desperation before fucking

#dean winchester x you #dean winchester headcanons #dean winchester #dean winchester x female!reader #dean winchester fanfiction #dean winchester smut

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were-all-idjits-here · 6 months

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How do you think the Winchester dynamic would change if they had another sibling that was the youngest? I’m particularly curious how you think Sam would treat them and stuff!

Thanks for the ask anon!

I'm the oldest with only one younger sibling, so I don't have much experience with three kids/middle child dynamic. The idea of Sam suffering from that "overlooked middle child" trope breaks my heart for him, but he seems to be the type who doesn't mind avoiding the spotlight, so I'm not sure he'd really mind. I think if they had a youngest sibling who was a different gender than them, he wouldn't suffer from that as much since he'd still be considered the youngest boy. But either way, I don't really think it would affect how Sam treats them.

I think both brothers would be very "no one's allowed to pick on my sibling but me" attitude, and both would be very protective over a younger sibling. There would be a lot of teasing, but also a lot of love, too. I think if their youngest sibling was very fem, they'd be even more protective since a lot of hunters (and the world at large) unfortunately can be a bit sexist and disrespectful, especially of fem hunters.

As far as how the dynamic between the two of them would change, I think Dean would obviously still be protective over Sam as well, but would have less of a "Sammy is baby" mentality and delegate some of the protect the youngest tasks to him. I feel like Dean would be aware of the forgotten middle child trope as well as do his best to make sure he never made Sam feel unimportant or left out, but would slip up from time to time. When that does happen, I think Sam would be more frustrated with Dean than anything else since he's empathetic enough to realize it wasn't the youngest's fault and would work really hard to not take it out on them. But if he ever did, he would do whatever it took to make it up to them while Sam and Dean worked out ways to make sure it didn't become a pattern.

#sam winchester #supernatural #dean winchester #winchester sibling #winchester sibling reader #sam winchester x reader #dean winchester x reader #supernatural headcanons #spn headcanons #spn #sam winchester headcanons #dean winchester headcanons #winchester sibling headcanons #sam winchester x sibling!reader #dean winchester x sibling!reader

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bralesscommie · 7 months

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Listen to me. Listen. I know you want to hear my Dean Winchester headcanons

This man has bpd

He plays a persona all the time, pretending to be an oh so masc het man

He has ADHD

Is bisexual. Maybe even vaguely gay

Has cried to Cas in the Dean Cave on late night talks (couldn't look Cas in the eyes for days)

Has trouble with food. Traumatized by not having food as a child, so he'll eat whenever he has the chance

Absolutely adores romcoms and silly little shows (see: dr sexy)

#dean winchester #dean #spn #supernatural #dean winchester headcanons #dean winchester hc #spn headcanons #bpd dean winchester #adhd dean winchester

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5sospenguinqueen · 28 days

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(Dean rolls over in his sleep and knees Y/N in the ribs)

Y/N: Ow. You kneed me.

Dean: (mostly asleep) Yeah, I do need you.

Y/N: (voice cracking) OkAy

#supernatural #supernatural incorrect quotes #supernatural imagine #supernatural drabble #supernatural headcanon #supernatural prompt #supernatural one shot #supernatural funny #supernatural fluff #supernatural dean #dean winchester imagine #dean winchester drabble #dean winchester headcanons #dean winchester x reader #dean winchester fluff #dating dean winchester would include

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spookyysinsanity · 21 days

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once cass says he loves sam and dean, (mary, jack, all of them too) in season 12/13, he says it so much. sam and dean don’t often or really ever say ‘i love you,’ but cass does. he constantly pledges his loyalty to the winchesters and professes his love for them. it always gets me when he referee to them as “the people i love,” because he’s so blatant. he doesn’t hesitate to say it. ever.

idk this always just makes me so sad??? who knows!

#supernatural #spn #dean winchester #destiel #dean and sam #sam winchester #castiel #cass and dean #supernatural headcanon #dean winchester headcanons #sam winchester headcanon #castiel headcanon #mary winchester #team free will #sobbing #he loves them so much

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6lostgirl6 · 3 months

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Dean Winchester Masterlist

🩸 = Smut/18+ Themes 🩸

Fics:

Headcanons:

Yandere Alphabet - Demon!Dean

Dean As Your Boyfriend HCs - Coming Soon!

Imagines/Scenarios:

#dean winchester masterlist #dean winchester #michael dean #demon dean #dean winchester x reader #dean winchester x you #dean winchester x y/n #yandere dean winchester #yandere dean winchester x reader #dean winchester fanfiction #dean winchester fanfic #dean winchester headcanons #dean winchester imagines #supernatural #supernatural fandom #supernatural fanfic #spn #spn fic

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shelbgrey · 9 months

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Being in a love triangle with Dean and Cas

Paring: Dean winchester x reader x Castile (not destile!)

Summary: headcanons about an angel and a hunter fall in love with you.

A/n: this won the newest voting thing :)

MasterList

“They're both in love with her” Sam sighed.

“my money is on Dean” Bobby said drinking his beer.

Okay... So, get ready for every single thing to be a contest. they're both extremely stubborn and even the simplest of things will be turned into a competition of who can do it better, even if Cas doesn't understand.

Since Cas is clueless about most human actions, he usually tries to copy Dean but ends up doing it in a more goofy or messed up way.

Cas wasn't supposed to fall in love with you, he's your Gardian Angel and the rules in heaven are pretty strict. He couldn't help but fall in love with your compassion and goofy personality.

You and Dean had always been on and off, he deeply cares about you and would even say he loves you, but with you both being hunters he's always afraid to lose you or he thinks he's not good enough.

Cas didn't know how to handle the feeling he's never had to deal with, every time he'd see Dean put his arm on you or flirt with you, cas would feel his fist clinch and he'd get so angry.

“I don't know what's wrong with me, my chest is heaving and... I just feel so pissed” Cas said to Sam one day.

“your either jealous or...” Sam stoped. “your not in love with y/n, are you?”

Cas didn't know, but he realized his change in adatued and thoughts. As your Gardian Angel he'd would often go with you to protect you beacuse that was his job, now he would literally push Dean to the side to go on a hunt with you.

Remember when I said you and Dean would often be off and on again? Well Cass has seen two break-ups, and this would be the only time he'd put his feelings aside. He's your best friend and he dose know when you need a shoulder to cry on.

Anyway, Dean would catch on quickly, he cares about Cas but he cares about you more. So challenge accepted.

He wasn't gonna lose you to a baby in a trench coat.

Dean is often very forward and flirty, you were used to his complements and dirty jokes. But when he realized he could use you to Cas he'd turn up the flirting to 100%, which would often make you uncomfortable... You weren't used to him acting like that.

But underneath all the flirting, he's genuine and what he's saying is true.

Suprisenly Cas would become very charming. He wears his heart on his sleeve. He loves he can easily express himself around you and learn about human life without being judged.

I also think Cas is good at knowing when to pump the brakes if he ever steps a line or goes too far. Dean sometimes doesn't and sometimes he forgets that he doesn't need to use the same tactics he used to use bar girls.

If you get hurt Cas will warp his coat around you and heal you up, if it's really bad Cas and Dean will literally start arguing.

One time it got so bad you probably wouldn't still be in this damn triangle if Sam didn't take you to the hospital.

That's when they realized that they really need to put their differences aside, it wasn't just about them, it was about you too.

“she means everything to me... I want her to be happy” Dean says to Sam. “and what if she's chooses Cas?”

“she won't... Just because he's her guardian angel doesn't mean he can make her happy”

Dean was so scared to lose you while Cass just didn't know how to express himself, there been many opportunities for Cas but he'd always chicken out.

What you hated most about this whole situation is that Cas and Dean were turning on each other. You knew they were best friends and you couldn't help but think this, no girl is worth losing your best friend over.

As it went on you got more and more attention, you didn't want that. Then Sam and Bobby's secret poll only grew more bets as time went on.

Jack was so confused, he saw you as a mom and Cas as his dad. So he really just wants you two to be together. He watched the parent trap and used some of the tactics, Sam gently told him to stay out of it.

If Dean would make you a mix tape, Cas would find an even more romantic gesture. During the time you and Dean did date he learned that you were a simple girl and didn't like fancy stuff.

Cas would go to Sam or Jody for advice. Sam would suggest flowers, expensive places while Jody would remind him to just be himself and remember the stuff your actually interested in.

He's been your Gardian Angel for years, so he knows your likes and dislikes. He was so happy when he found a copy of a novel you've been surching for, he loved the feeling of you wrapping your arms around him and cheering that you finally got the book.

“thank you Cas, your the best!”

Gabriel, who liked to stir the pot in the situation was on cas' side. He would sometimes mess somthing up for one of them or just watch one of their planes fail. This was a better love story than twilight in his opinion.

One day Cas found a ring in Dean's room, it's literally not what you guys think. Dean was his mom's and he just wanted to look at it.

Cas watched enough movies with you and thought it was an engagement ring. He felt his heart pounded, he also relized he's watched way too much TV with you. He remembered watching Grey's anatomy with you, he remembered you crying with Mark Sloan died and gave his 'if you love someone' speach.

“I wish I could experience that... A guy not caring about the consequences and just expressing he loves someone” you told him way back when.

That's when he had enough, he didn't care if Dean was there or not he's was gonna tell you. “I love you y/n... I love everything about you, even things I don't understand... I still love”

He told you to think everything through. As much as he loved you, he didn't want you making any hasty decisions or let what he said cloud your mind.

A couple of days later, Dean came to you with the same heart filled love speach after a rough hunt. “I love you... I know I don't show it much or express it, but belive me when I say your the best thing that's ever happened to me”

You had so much to think about and during that time you never felt so overwhelmed, your heart would always pound when you thought about them.

You spent almost three nights just laying awake in bed thinking about them, there was logic and there was reason.

The logical choice would be Dean, you could grow old with him and have a family. After Jack, Cas was terrified to have children with a human. Just because Dean was haman didn't make it a logical choice, but you guys been through so much. There been many night you guys spent patching up wounded parts of your bodies or cleaning up blood after a hunt.

Logically, Cas would be safer. Castile can protect you and heal you with just a brush of his thumb. Just because he was clueless doesn't mean he didn't know how to make a woman's heart pound in the best way possible. Cas knew your deepest fears and kept secrets for years, he knew everything about you.

Positive reasons would bring up the way Dean would make you laugh. Or how he could make you smile no matter how mad you were.

You though about how warm his bear hugs were and how good he smelled.

Dean was a worrior and he would take a bullet for you. You were always his main priority and you never felt that with someone before him.

Even if he didn't know how to interact with humans, he knew how to take care of you. He knew when you need to talk or need a hug. He would catch on to your Quirks, like how you'll nibble on your lip when your doing research or reading.

He'd notice the little wrinks on your forehead when your mad or laughing. He'd know all your different smiles and the meanings of them.

You love whem you hug him you'd feel his wings wrap around you.

What you might not know is Cas would give up immortality for you, he'd become human if it meant spending What humans thought forever was.

“I don't know what to do Sammy” you sighed.

“stop using your brain, what dose your heart say?” he asked. “you'll know the right decision when the time comes”

The next day you took a deep breath and walked down the bunker hallway, Cas and Dean's were right across from each other. Dean's door was beaten up and had band stickers on it. Cas was newer and had 'Cas' place' carved in it.

If you chose Castile:

If you chose him, you didn't go directly to him. You knew he was the one you just didn't know how to do it. When you finally got the courage, Sam interrupted with a paranormal case.

It was hard, you got whipped around like crazy and thrown through windows, the vengeful spirit wasn't gonna let up.

The spirit through your blade at you and it went straight to the gut. You were already bleeding and weak, so this wasn't helping.

You crumbed in Castile's arms and he started to panic. He used his trench coat to applie presher to your wounds.

“Sam! Dean! Help me!”

You coughed and placed your hand on his cheek making him look at you. His watery blue eyes looked at you with so much panic.

You smiled and pulled him closer to you. “I love you Cas... So much”

“I love you too... Hold still, I got you” he placed his lips on yours while his hands healed all your cuts and bruises.

Side note... You also adopt Jack, he finally had parents and he couldn't be happier.

-a week later...

“Balls! I lost $200” Bobby grumbled, you gave the boys a questioning look.

“you beted on us?” you asked Sam, He shrugged. “hey, at least you got $600 for your honeymoon” Sam joked, you took the notebook with all the bets written down and hit him in the head.

If you chose Dean:

You knocked on his door, he when whipped it open a smile immediately formed on his face. “hey, sweetheart”

“can we talk?” you asked softly. Dean nodded as his heart pounded, he didn't know what to expect.

“if this this about what I sa-”

“I love you” you said cutting him off.

He pulled you to his chest and immediately slammed his lips on yours, he pulled away and rested his forehead on yours. “thank God... I love you too”

#Supernatural #Supernatural headcanons #Dean winchester #Jensen Ackles #Dean winchester headcanons #Castiel #Misha Collins #Castiel x reader #Castiel headcanons #Supernatural imagines #Dean winchester x reader

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