#dating dean winchester headcanons

[allthosepeopleilovetofangirlover]

DATING DEAN WINCHESTER HEADCANONS

Dean is the guy who'd pretend that he's the best in the entire universe, but he'll get nervous if he ever sees someone slightly more attractive than him.

He loves to watch movies with you, even more so if they're of his choice. Cuddling on the couch in the Bunker and watching a movie is his favourite evening activity, and he's constantly looking at your face throughout the movie to see if you like it or not.

Dean doesn't want you to accompany him on hunts, especially if the creature you have to hunt happens to be particularly dangerous, like a vampire or a werewolf.

He'll never try to control you, but he will get insanely protective of you and you have had many arguments based on that.

Arguments that almost always get resolved by angry sex or intense makeout sessions.

But for the ones that don't, you two eventually find your way back to each other.

He'll never admit it, but he loves it when you treat him with affection and give him flowers.

If it wasn't obvious, Dean is touch-starved, and you figure it out very soon into your relationship. You make sure to give him reassuring touches ever so often, especially in the times of stress.

Dean is very grateful for those touches, and keeps reciprocating the gesture, but in a much wilder way.

He is very possessive, and will glare daggers at anyone who stares at you for too long. Men who know him know how dangerous he is, and how well he can fight, so they stay away from you. But the strangers who try to look at you in any way other than respect, Dean will not hesitate to throw punches.

For all his playboy ways, he's extremely loyal to you. Will not even look at any other girl when you're in the picture. You're the only one he wants and needs.

Dean likes to pull pranks on you. They're harmless, obviously. He loves to see that adorable expression on your face when you don't know what's wrong when you're being pranked. Once you realise it however, it doesn't take a lot of time for that expression to go from adorable to angry.

You love to pull pranks on him as well, often teaming up with Sam to teach his older brother a lesson. Sam loves it, and though Dean pretends to be angry and offended, he's laughing on the inside.

Frequent rides in the Impala, especially when it's drizzling and a cool breeze is blowing. He just likes to go on long drives with you, no distance is too long with you by his side.

Dean tells you stories of his childhood, yes, even the bad ones. The good ones to get a good laugh while the bad ones for you to get more acquainted with his reality, to know who he really is.

He had taken a lot, and I mean a LOT of time to open up emotionally, it was extremely difficult for him to not be guarded at all times. But nothing is too difficult when it comes to you.

Now, he opens up to you and talks to you about how he feels, instead of hiding his real emotions behind corny jokes and sarcasm.

Whenever you get mad at him, he immediately gets to know and tries his best to make sure that you aren't mad, the process including more corny jokes but you learned to love them anyway.

Sam loves the way you have a positive effect on his brother, how you calm him down from both anger and stress, how you make him less reckless and more affectionate.

The most important thing however, is the fact that you make him less self-destructive. He takes a lot of care of you, but along with you, he has started to learn how to cherish and love himself as well.

You bring out the best in him, and he brings out the best in you.

You're his yin, and he's your yang. Both of you wouldn't have it any other way.

[5sospenguinqueen]

Y/N: Whenever Dean is about to use the shower after me, I turn the temperature to scalding.

Sam: Why-why would you do that?

Y/N: To make him think I am capable of withstanding that pain. I take normal showers, but I want Dean to be a little scared of me.

Sam: (sighs) You’re both idiots.

Charlie: (in awe) That’s genius.

[spookyysinsanity]

dean winchester x fem!reader dating head canons -nsfw edition

not my gif!!^^

18+ only!!! minors dni!!!!!!!

loves fucking in front of mirrors. he likes to be behind you, holding u up by ur hair or neck and he can see your reflection.

goes craazzzyyyy when you moan his name

likes to pretty much fuck you stupid. like to the point ur shaking, can't walk, only can think of his dick and babbling his name

loves leaving marks on your body. like hickeys EVERYWHERE, on ur neck, chest, thighs, stomach, all of it.

likes it when you have lipstick on and kiss his neck

ONLY if you're ok with it, he loves to choke you. especially if you ask.

has a huge thing where he loves to pleasure you first

eats pussy like a man STARVED

especially if ur on his face he fucks that shit up

he's sososo good with his hands. like goooood. it doesn't matter where they are, in between ur legs, on your boobs, your face, neck, hair, whatever bro wherever he is he's doing a damn good job.

loves to send u dirty texts if you're doing research with him and sam. lovesss to watch you get all hot and bothered

loves to tease and play with you in baby. traffics bad? his hands r down your pants. or it's the other way around and you're sucking his dick

jus loves to fuck in(or on) baby idk bro

loves to come up behind you and press himself against you and start jus groping your ass or tits

also will come up behind you and kiss your neck/jaw and his hands will gently come up under ur shirt and trace your stomach and waist

a/n: ok that's all for now! please like and reblog if you liked it, let me know if u want more!

[archiveofvirtue]

ᝰ.ᐟ BF DEAN WINCHESTER ⸻ head canons

notes / just dean being a lil softie, whole lotta fluff, sfw, definitely gonna be making a nsfw version for this as well though,, cause I know y’all are freaky like that!

ʚ he def knew u had a crush on him long before you two even dated, so he would flirt with random girls to get u jealous cause he thinks it's attractive

ʚ scared to open up to u at first, too anxious that he’d scare u away with all of the things he’s carrying inside of him, but u always reassure dean that you would never leave him

ʚ 100% acts like a big baby, when you two are alone in the motel room, since he wants to feel ur warmth and affection

ʚ always calls u “sweetheart" even in the middle of an argument.. it’s his way of showing affection.. in some way.. and he can't help it

ʚ he is incredibly protective of u, he would always try to shield u from the worst of it, even if it means being a little overbearing at times..

ʚ he loves flirting with u, even after you've been together for a long time.. he would out cheesy one-liners or make playful comments, trying to make u laugh

ʚ if u ever get hurt, emotionally or physically, it would break him.. he has a hard time coping with seeing u in pain, and he’d go to great lengths to make things right

ʚ the type to just grab u and drive off in the impala, no real destination in mind, just enjoying each other's company and the open road

ʚ lets you pick out the music whenever he's driving.. “Excellent song choice, sweetheart."

ʚ he loves listening to u babbling, even if it’s about the most boring things.. he’d just be happy to hear ur sweet voice

ʚ he’d feel so proud while seeing u flipping off random guys that are trying to hit on u

ʚ he is addicted to ur lips, sneaking in little kisses here and there, sometimes even having a hard time stopping, he just loves u so much

ʚ always has his hands on u someway, especially when he is driving, his palm would be on ur thigh ALL the time

something a lil different today !!

feedback and requests are greatly appreciated !!

tags 🏷️ @gibson-g1rl @beausling @nuemanfilms @angelicjackles @sammyluvr @rubyvhs @nxptvn @seasons-of-death @deansenvy @drewsarms @starkeysprincess

[lokigonnakmsforbucky]

Dating Dean Winchester Headcanons <3

No one asked for this, but I am going to write about it anyway because I am THIRSTY for some Dean Winchester...feel free to send me requests for dean or any spn character. I will take a look at those asap. Also, this goes without saying but, minors dni, NSFW WILL be mentioned under. You have been warned :)

Long road trips in the impala, classic rock 24/7. You both would be singing to every single song. While Sam does anything possible to get you both to shut up.

Constant jokes, pranks, and teasing.

You guys would often make bets on what monster you would be hunting, but jokes on you both. Sam was always right.

Dean was a man that loved physical touch, as soon as you give him the A-okay. His hands never leave you... and I mean that.

Forehead kisses, cheek kisses, hand kisses... you get them ALL.

This man loves to hug you, wrapping his arms around your waist and putting his head on your shoulder no matter what you are doing or where you at. He will find a way to hug you somehow.

He loved to show his love for you in any way he could, cooking, rubbing your back, and maybe something else ;) He wanted to let you know how much you mean to him.

Baking pies together <3

Dean was an ASS man, his hand would never leave your ass in public. He would always have his hand on top of it, so everyone in the vicinity would know you were his. Don't worry he would slap it too if anyone was looking.

oh, man if anyone was looking... you were in for a treat.

"He thinks it's okay to keep eyeing you...I'm gonna prove to him your mine."

He would get jealous quick... even over something so small.

Dean is also very protective of you...he would fight, lie or even die for you, and when ANYONE made googly eyes at you. He was ready to show everyone you're his girl.

"What do you say, sweetheart, let's show this fool your mine."

"Please..."

Dean could quickly become a Dom or Sub depending on your mood, his, or the situation.

But, fucking him was a perfect combo of filthy and sweet.

This man would have his head between your legs and his fingers inside, keeping eye contact and making you watch while he fingers you.

"C'mon sweetheart, moan for me... let them all hear how good I make you feel just with my fingers... we haven't even got to the good part yet."

"Please...fuck me, Dean... stop teasing"

"Yes, ma'am"

He could spend the rest of his life making you moan for him.

But, remember when I said he was an ass man? He loves taking you from behind... holding your head back. One hand around your neck, while whispering dirty things into your ears.

"Just like that...moan out loud for me"

He also went crazy when you rode him, thrusting up into you when you went too slow or just watching your face take him.

you + him +impala = dean's in heaven, mainly when you were on top of him.

"Ride me just like that, you're doing so well baby"

He would also ensure that everyone knows that he did it if you can't walk well the next day. Was because of him

He absolutely loves aftercare too.

He would make a bath for the both of you, cook you anything you wanted, and cuddle until you both fell asleep watching any show that made you happy.

When he went out for hunts, he would always think about you. Are you eating enough, are you sleeping well, are you okay? His questions would spin in his head the entire time. For once he wishes monsters didn't exist or took a break so he could spend time with you.

He would call you at LEAST twice a day to check-in on how you were doing.

Dean was absolutely in love with you, to the point that he would rant to Sam on how much he did love you and that he was afraid you would leave one day or that he would not be there to save you.

"But what happens if I can't make it in time or if she leaves?"

"Dean, she can handle herself. Plus, she loves you and if you can't see that you an idiot."

This man was head over heels for you, he would do anything for you and I mean anything for you. He even thought of retiring from the family business and start a life with you.

Maybe some day, he will make that a reality.

[delusional-headcannons]

Winchesters- Dating head cannons

edited it cas cause when I originally made this it was only Sam and Dean but now you have cas also sorry his is a bit wierd but still hope you guys like it :D

Involves- sam, dean and Cas

Warning- a little suggestive, cursing, bad spelling

this is my first time doing this I hope it’s good 😭 and they might not be long I’m sorry sorry I didn’t do cas and others I’m just tired and not sure how it’s going to turn out

Dean-

• He wouldn’t want you out on hunts cause it worries him that you might get hurt

• would totally smack your ass

• wouldn’t give you his last bite of pie but might give you a bite

• you would be a passenger princess

• totally would have an inside jokes to many actually

• calls you sweetheart or princess

• would cuddle and watch movies with you all the time

• very touchy, like hand on thigh while driving or always holding your hand stuff like that

• burrows his face into your neck when you hug

• would ‘try’ and cook for you but then orders take out

• ^ knows your order by heart

• loves ABSOLUTELY LOVES seeing you in his clothes but would pick on you for it

• loves you sitting in his lap (agian he’s touchy)

• it’s hard for him to express his feelings so bare with him

• if you fight he would say things he doesn’t mean then feel bad and eventually apologize

• tells Sam about you all the time even if your right there

• jealous like incredibly jealous

• likes when you play with his hair

• ^ will play with your hair to help you sleep

• very….EXTREMELY protective

• likes to hold you in his chest when you cuddle it makes him feel like he’s protecting you and keeping you safe

• loves every part of you like he will lay on your thighs and your boobs (if you have them) he is obsessed with every part of you

• might not be the best at comforting words but with just hold you when you’re sad

• flirts with you ALL THE TIME

Sam -

• Gives THE BEST Hugs and he knows it

• very comforting, tells you everything will be okay and he’s with you when your sad

• likes when you play with his hair…or pull it ifykyk

• he tells Dean about you even though Dean picks on him for it

• like Dean he also loves seeing you in his clothes

• knows you can handle yourself but still worries about you on hunts

• is scared he might crush you sometimes

• you too research together all the time as a date

• coffee dates all the time

• I can see him buying you flowers while out or your favorite food

• ^ knows what you like and what you order

• remembers little details about you

• would share his food with you but not all of it

• likes to tell you how pretty/handsome/beautiful you look all the time

• loves when you give him compliments he will simply melt

• gets shy sometimes

• tries to flirt but just ends up messing up or getting embarrassed/shy

• likes to talk it out instead of just blowing up on you

• you two figure stuff out fast when together

• gets a little jealous but not as much as Dean

• he tries to be honest with you because he’s scared if not something will happen to you like Jessica

•likes when you lay in his lap like your head on his lap while he dose something, not big on you sitting in his lap but wouldn’t say no to it

• loves spending time with you any chance he gets with you alone he takes it

• you two go running together

• “hey beautiful/handsome”

• you two joke around quite a bit 1 or 2 inside jokes

• protective over you

• head kisses for sure

• tries to get you to eat healthy while on cases

• you two both cuddle while stay up late watching late light tv ESPECIALLY on cases

• loves every part of you (inside and out) but favors your eyes the most

• likes seeing your hand in his and how big it is compared to yours

• This poor baby if he did anything he ask if it was okay cause he doesn't know anything about relationships

• would be scared you will get hurt on hunts and makes sure he goes on every one with you

•most likely love when you play with his hair

• prolly EXTREMELY touch starved

• loves when you show him new stuff he hasn’t done

• picnic dates for sure or walks on the beach/park

• this poor baby probably can’t understand you when you flirt (takes it to literally)

• can not flirt

• if he understood what you meant wouldn’t know what to say

• he doesn’t know how tot explain it but he loves seeing you in his shirts or coats :)

•knows your order but hear just like Sam & Dean

• dose NOT know how to cook

• most likely gets jealous but dosent know what it is or how to explain it

• dose not get inside jokes

• either really bad at communicating or extremely good

• if something happens will ‘pop in’ on you to make sure your okay

• if he has a ‘bad day’ he’ll ’pop in’ on you for a hug or something or to talk and then leave

• loves talking to you (can talk to you for hours)

• loves and hates complements

• kisses on check early on lips unless in private

• can see him showing and telling everything (and I mean everything) about you cause he doesn’t know what not to show

• extremely protective of you

• if you die will go down to hell ( let’s be fr you’d be in hell) and grab you up like he did Dean (or find a way to)

•shows you the honey the bees gave him

• shares honey with you

• loves your boobs (in that sense (if you don’t have them then your chest) there/its just so…perfect to him

•definitely hold your hand and just walks around or you walk him around

• 100% follows you like a lost puppy

• love your eyes they are so beautiful and perfect and just he could stare at them forever

• definitely calls you “my love” or something along those lines

[temis-de-leon]

Whose voice I imagine when I see the om! cast speaking:

Part 2: Beel - Dean Winchester (Supernatural)

Specifically 1:20

[downs1de]

what would Sam's dating profile look like. is he a 'long walks on the beach' type?

To be honest? Probably, but it’s because Dean made it for him. He felt bad that his little brother was a virgin in his 20s, and he thought he’d be doing him a favor by taking some candid pictures and creating a profile for him. His description is all over the place, but thankfully, Dean managed not to call him a “nerd” not once!

[nayeliq1]

June 7th, prompt: Stars

The stars were beautiful tonight. Dots of light in a pitch-black sky, no clouds to hide them.

Their fingers were entwined. Remnants of warmth in a tranquil night, no fear to divide them.

Cas had helped create some of those stars, remembered their constellations like the back of his hand.

He turned his head to the side to look at Dean, looking up at his stars.

Dean had a peaceful smile on his face, the silver glow of worlds far away reflected in his eyes. The gentle breeze moved his hair, his bare shoulders relaxed against the hood of his car. Cas' eyes were drawn to the array of freckles scattered there.

Cas had created those too, had arranged them carefully, mimicking the stars he knew so well.

"Hey."

Dean's head had turned, smiling at him.

"Hello, Dean."

"What're you thinking about?"

Stars. Freckles. Beauty. You.

"How much I love you."

And he leaned in, pressing his lips to the starry sky on Dean's shoulder.

For @starcrosseddeancas Dramy Drabbles

[sammyluvr]

SUPERNATURAL M.LIST all works are gender neutral, reblogs + feedback are greatly appreciated !! MINORS AND AGELESS BLOGS DNI WITH MY NSFW CONTENT. YOU WILL IMMEDIATELY BE BLOCKED !!! all nsfw fics are clearly labeled MDNI, this applies to ageless blogs. r for romantic, p for platonic ! ofc all nsfw is romantic !!!

SAM WINCHESTER DRABBLES / ONESHOTS ⟢ something about being close | 9.5K, angst, fluff, r ⟢ makes you wonder | 5.2K, fluff, r ↳ ⟢ part two : now you know | 6.8K, fluff, hurt/comfort ⟢ better than a sight for sore eyes | 1K, suggestive, MDNI ⟢ take my breath away | 13.7K, angst, fluff, hurt/comfort, r ⟢ give and take | 0.7K, fluff, r ⟢ warm brown jacket | 1.3K, fluff, r ⟢ you’d dance with me? | 1.4K, fluff, r ⟢ three seconds | 1.2K, fluff, r ⟢ literary parallels | 3.6K, light angst, fluff, r ↳ ⟢ part two | coming soon … ⟢ this is real, it’s right | 3K, hurt/comfort, r ⟢ my boy only breaks his favorite toys | 10.6K, angst, r ⟢ forget-me-nots | 5.6K, fluff, r ⟢ but daddy i love him | 11.3K, light angst, fluff, r ⟢ some other time |1.1K, fluff, r ⟢ just an observation | 1.3K, fluff, r ⟢ hold me, it’s enough | 1.6K, hurt/comfort, r ⟢ breathe, baby | 4.1K, smut, fluff, MDNI ⟢ only got eyes for you | 2.7K, fluff, r ⟢ dead eyes | 2.4K, hurt/comfort, r ⟢ abstract (psychopomp)| 1.9K, hurt/comfort, angst, r ⟢ love you again| 2K, fluff, hurt/comfort, r ⟢ motel room, 10:00 p.m. | 545, fluff, hurt comfort, r ⟢ book shop, 12:00 p.m.| 515, fluff, r ⟢ motel shower, 12:00 a.m. |629, hurt/comfort, r ⟢ cabin, 3:17 a.m.| 658, hurt/comfort, r ⟢ campus library, 7:00 a.m.| 658, fluff, r ⟢ the impala, 4:00 p.m.| 608, fluff, comfort, p ⟢ in the woods somewhere | coming soon … ⟢ drooling honey | 1.1K, smut, MDNI ⟢ our girl | 1.2K, smut, MDNI, w/jess ⟢ i got you | 4.1K, smut, MDNI ⟢ you can take it | [tfem!sam]. 1.3K, smut, MDNI ⟢ worship you | 1.5K, smut, MDNI ⟢ my hands are yours | 2.8K, hurt/comfort, r ⟢ sweet smile | 1.9K, fluff, r

HEADCANONS ⟢ random boyfriend hcs | 1.6K , fluff, r ⟢ nsfw boyfriend hcs | 1.6K, suggestive/smut, MDNI ⟢ pirate!au | 1.1K, fluff, light angst, r ⟢ with adhd!reader | 0.8K, fluff, r ⟢ with talkative!reader | 0.7K, fluff, r ⟢ fake-dating!au | 1K, fluff, r ⟢ with angel!reader | 2.4K, fluff, r

FAKE TEXTS ⟢ gen z younger sibling | fluff, humor, p

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DEAN WINCHESTER DRABBLES / ONESHOTS ⟢ the language of love isn’t dead | 2.4K, fluff, light angst, r ⟢ flower shop, 11:00 a.m. | 644, fluff, r ⟢ gas station, 3:04 a.m. | 615, hurt/comfort, p

HEADCANONS ⟢ best friend!dean | 1K , fluff, p

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BOTH DRABBLES / ONESHOTS (all platonic) ⟢ sorry won’t cut it (rewrite) | 4.1K, angst, hurt/comfort

HEADCANONS (all separate) … nothing yet !

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RUBY DRABBLES / ONESHOTS ⟢ abandoned church, 5:30 a.m. | 540, fluff, r ⟢ cry for me | 1.2K, smut, MDNI ⟢ lick it better | 1.2K, smut, MDNI, coming soon … ⟢ indulge | 1.2K, fluff, r

HEADCANONS … nothing yet !

౨ৎ

CHARLIE BRADBURY DRABBLES / ONESHOTS ⟢ make you feel so good | 1.K, smut, MDNI

HEADCANONS … nothing yet !

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JO HARVELLE DRABBLES / ONESHOTS ⟢ so pretty | 1.7K, smut, MDNI ⟢ hooked | 1.6K, smut, MDNI

HEADCANONS … nothing yet !

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JESSICA MOORE DRABBLES / ONESHOTS ⟢ our girl | 1.2K, smut, MDNI, w/sam

HEADCANONS … nothing yet !

౨ৎ

© SAMMYLUVR 2024 ALL RIGHTS RESERVED. COPYING, TRANSLATING, AND REPOSTING IS PROHIBITED.

[allthosepeopleilovetofangirlover]

DATING SAM WINCHESTER HEADCANONS

Sam is a complete gentleman. Once you capture his attention, it will be completely fixed on you and he will never even look around at any woman other than you.

That being said, getting his attention is very difficult. He was polite and kind to everyone, so you thought that he didn't want you particularly.

But he did. He liked you more than anyone else, and soon, asked you out.

Sam is the sweetest boyfriend, he'll try his best to know what you like and don't like so that he can make sure that he never makes you uncomfortable.

Hugs and cuddles. He loves it when you keep your head on his shoulder while he's doing research or reading a book. He pretends like he doesn't need affection but deep down, you know he does.

Everyone around Sam treats him like he's a baby, so in the beginning, when you had done that too, Sam had got angry. Very angry.

But as time passed, you saw how talented and capable Sam is, and learned to not underestimate him. Sam fell a bit more in love with you because of that.

Sam is constantly worried about others, including Dean and Bobby, looking at him like he was a freak, like he was inhuman. But you never looked at him like that. For you, he was just Sam. Your Sam.

He takes great pride in the fact that he's tall, and teases you about your height more often than not. You try to tease him back and it eventually ends up in a makeout session.

Sam treats you with great care, but he doesn't underestimate you. He loves and cherishes you while being aware of how strong you are.

He will always make sure that you get enough rest and food. If you're ever upset, he'll try to talk to you and coax the problem out of you. In the sweetest, gentlest way possible.

Whenever he and Dean argue, he always comes to you and talks to you about how he disagrees with most of his family values, and you listen to him patiently, just glad that he doesn't shut himself off like his brother and actually talks about his feelings.

Sam's love language is words of affirmation. He needs to be told how good and kind he is, relying on healthy communication more than anything else. In return, he constantly praises you, showering you with love and appreciation.

Contrary to what most people might believe, Sam is not a boring person. He has different ideas of fun, and though he's not the most joyous or exuberant person around, he's fun to be with. He will make sure that you never get bored in his presence.

That being said, he does get insecure that you might leave him for someone better, someone louder, more enthusiastic, but you convince him with both words and actions that he's the one for you, and you wouldn't even think of leaving him.

He's not the only one who gets insecure, though. Being extraordinarily handsome and cute, many girls and even a couple of guys flirt with him on multiple occasions, even when you're right beside him.

But Sam makes sure to let the world know that he's yours. Many times, to get the point across, he'll kiss you in front of the lot to let them know that you're together.

Sam wants to quit hunting and start a family with you, a quiet, white-fence life, and since it's with him, so do you.

You and Sam are endgame, and both of you are going to make sure that you two stay with each other, forever.

[5sospenguinqueen]

(At the fair)

Sam: So, which ride do you want to go on first?

Y/N: (points at Dean) I want to ride that.

(Dean chokes on his hot dog.)

[mxltifxnd0m]

boyfriend headcanons ⟡ d. winchester

pairings: dean winchester x reader, dean winchester x gn! reader

word count: 1.2K

warnings: no use of 'y/n', fluff, one suggestive comment, a smidge of angst, reader is to be implied as a hunter, lowercase intended

a/n: SURPRISE! i made the dean version of bf headcanons. i stayed up until 3am making this bc my mind had ideas and i didn't want to lose them lol (ik im crazy 😁) also technically my first fic for dean lmao

i hope you all enjoy and please reblog and comment, it really helps out!!

𝘥𝘦𝘢𝘯 𝘸𝘪𝘯𝘤𝘩𝘦𝘴𝘵𝘦𝘳 𝘮𝘢𝘴𝘵𝘦𝘳𝘭𝘪𝘴𝘵

⟡ before dating you:

was super attracted to you before he even said a single word to you 

it was definitely lust at first sight (he wouldn't have minded sleeping with you) 

then you opened your mouth, and he was like, oh man, they're gonna be trouble, aren't they (as if he isn't trouble as well) 

you guys bickered a lot. like A LOT to the point where sam would have to remove himself from the room or get in between you two in order to stop the bickering 

the bickering got so bad that sam had to lock the two of you in the motel room sam and he were sharing and didn't let you guys out until the two of you could have a civil conversation 

you guys eventually stopped bickering out of malice after finding common ground between the two of you 

there was bickering but it read more of an old married couple bantering with one another 

then somehow, you guys became friends, and the physical attraction that dean had to you had morphed into something else and then he realized that he liked you 

he only confessed his feelings when you had a close call with a ghoul and blurted out his feelings to you when patching you up 

⟡ dating dean winchester:

you would describe dating dean as a roller coaster, but like all relationships, it has its ups and downs 

it was hard to have vulnerable conversations with dean without the infamous hunters' helper (alcohol lol)

you guys fought a lot at the beginning of your relationship bc you were fighting tooth and nail to get him to at least try and talk to you 

you soon realized that you would have to take a different approach to it and eventually let him come to you when he needed it 

it took a while, but once he put his walls down and trusted you, it seemed like a weight was lifted off of him when he finally told you a sliver of what was going on in his head 

⟡ soft dean!

now, this is where we get soft! dean 

we all know that dean is secretly a softy at heart, and you see it in the more quiet moments with him

he'll stare at you when the two of you are researching or when you're bustling around the kitchen, prepping and cooking lunch for the three of you 

and without fail, a cute blush will appear on his face, making his freckles pop against the red hue of his cheeks as you catch him staring at you  "what are you looking at?" you asked with a wide smile on your face.  "just you sweetheart." he tries to play off his flustered state with a wink, but you shook your head, knowing he was a bit embarrassed he got caught staring.

speaking about getting flustered, he loves teasing you and trying to get you flustered with fleeting touches, flirty gestures, and outright whispering the filthiest things that he wants to do you during the most inconvenient times, like if you're on a case or researching 

what he didn't take into account when he started it was that you would dish it right back at him

he loves it when you keep him on your toes 

⟡ pet names

OH another thing, PET NAMES  he loves using pet names for you 

we have the usual sweetheart, babe (not baby bc you know you come in a close third after sam and the impala) (he's tried arguing that's not true, but you knew it and understood you came after both of them).

he would def call you honey, beautiful, angel, and some variation of your name/nickname 

if he's in a playful mood, he'd probably call you borderline cringe pet names like pumpkin, sweet cheeks, pookie these are the ones you roll your eyes at since he knows you hate them

⟡ love langauges

now, his love languages, his main ones to give are acts of service, physical affection, and quality time, while the ones he likes to receive are physical touch, words of affirmation, and quality time 

⟡ physical touch

now, physical touch is a given for dean  he's a very tactical man and is a sucker for it 

when he can, he'll always be touching you, holding your hand or resting on your shoulder, thighs pressed together while sitting together eating in a diner booth, cuddling while watching a movie or always being in his arms while sleeping together, making out wherever whenever (his favorite place is obviously in the backseat of baby) 

but there are days when he needs physical affection from you, and you gladly give it to him, and he's a sucker for you when you play with his hair 

PDA, man is shameless with the PDA  he doesn't care he will kiss you no matter what and when he can  he loves you, and even if he's afraid to say it, he'll definitely show it to you 

⟡ acts of service

which brings me to acts of service  dean will do anything for you even if you didn't ask for him to do it  makes breakfast for you almost every morning, gives you his flannel when you're cold (he loves to see you in his clothes), replaces the lightbulb in your lamp when you mentioned it was flickering, taking care of you when you get drunk (he did this even before the two of you started to date and bickered the entire time), but the list goes on and on 

dean just likes to take care of the people he loves (it was practically ingrained into him at a young age) 

⟡ quality time

he also likes spending time with you it doesn't matter if the two of you aren't talking and working on your own tasks; he likes being in your presence (it soothes him)  with how crazy his life is, he loves the mundane things/tasks he does with you

sometimes, he'll go run errands with you, not bc he's bored and wants to avoid research (which is actually the main excuse at times) but, he likes the sense of normalcy it brings him when the two of you are together, and when you spend time with him 

⟡ words of affirmation

now, dean would never admit it to you (or to himself), but he needs to be reassured 

his mind is a dangerous place for him, and he can find himself drowning in his self-deprecating and self-destructive thoughts (these are also the days he needs you the most, and your touch is grounding to him) 

your words act as a lifeboat for him in the chaotic storm that is his mind and calms them down significantly 

he slowly works on his self-esteem and self-worth, but with your help, it's a little easier for him 

⟡ protective

this is a given, but he is SO protective of you 

dean is a fiercely protective person at his core and will do anything and everything to keep the people that he loves safe, and now that includes you 

some arguments were had when dean was being overbearing and flat out refusing to let you go on certain hunts with them bc it was too dangerous. you had to remind him that you were a hunter before you met him and will continue being one until the day you decide to try and retire or die 

he doesn't like it when you hunt alone, and so he always tries to come with you or send sam with you if he's indisposed for some reason 

he's only like this bc he can't lose one of the best things in his life 

[prentissluvr]

fake-dating!au headcanons — sam winchester

cw : gn!reader, fluff, pining!!!, blood mention, kissing, lil bit of swearing, poor editing, 1K words. requested !

prompt : you and sam pretend to be dating for a case.

MOVED BLOGS TO @sammyluvr !! no longer active on this blog! all fics can be found there!

⟢ “you’re too stiff, sam,” you hiss into his ear, leaning in close and making your features look all pleased as you say it, “we have to make this believable.”

⟢ when you pull back, sam looks like he’s trying not to blush, only because you’ve got your arms wrapped around his big upper arm, and you’re whispering things into his ear

⟢ he can feel your breath as you speak, and he thinks it could make him go absolutely crazy

⟢ he’s so flustered, and yet he’s starting to become determined to match your level of dedication, less so to succeed in the hunt, and more so to make you just as flustered as him

⟢ tonight, you pose as a lovesick couple in a decently nice restaurant

⟢ the monster you’re after has been scouting out couples here and preying on the most especially lovey dovey, affectionate couples it can find

⟢ you almost asked to do it with dean; he’s your best friend and you don’t have a massive crush on him like you do with sam

⟢ despite the fact that dean’s a weirdo, it would actually be easier to act the part with him because you’d feel exactly nothing except silly, but he insisted you do it with sam before you could even suggest anything else

⟢ and this close to sam, snuggled up into his side, you feel exactly… well, maybe, everything

⟢ you feel so much that you’d be zero percent surprised if you spontaneously combusted right then and there

⟢ and yet, you’re dedicated to finishing up this case, and you’re learning to enjoy the situation; if you have an excuse to be like this with sam, even just for a night, you’ll take it and make the best of it

⟢ you think you’re doing a grand old job at surviving the close contact, mostly because sam can’t seem to relax for longer than a minute

⟢ but you’re so in tune with him that you feel it the moment his perspective shifts from ‘i don’t know how to act, but i’m trying,’ to ‘i’m trying to induce a heart attack and kill you’

⟢ you’re sure that’s not how he thinks of it, but that’s what it feels like when he finally relaxes into your touch, then loops his arm around your waist and tugs you even closer to him

⟢ he leans close, his lips by your ear as he whispers, “yeah… and it looks like we have competition.”

⟢ you try desperately to keep your face from straying from its carefully constructed lovesick daze, but his breath against your ear makes it more than difficult to keep your composure

⟢ the lovesick look that you have for sam is actually a very natural state of being for you, but normally it comes about when you look at him from afar… 

⟢ or just not when your face is mere inches from his and his arm is solidly draped around your waist

⟢ it takes you a moment to register what sam actually said, and not thinking straight, you turn your head to look at him and ask for an explanation

⟢ you just don’t seem to recall that his face is only inches from yours, so close that your nose brushes against his and you suck in a sharp breath of surprise

⟢ it takes everything in you not to jerk backwards, but you stop yourself by grabbing the lapel of his suit

⟢ “competition?” you repeat, voice coming out quiet and a little raspy

⟢ “yeah,” he whispers back, eyes flicking away from yours for just a moment in the direction of another couple that had just walked into the restaurant

⟢ you glance over; they’re glued to each other’s side, wide smiles and heart eyes to rival anything you’ve seen

⟢ competition is right, which means that you and sam have to step it up, because you’ve spotted the monster already and he’s watching, looking for the best, most affectionate couple to take like he’s been going the past few weeks

⟢ you turn back to sam, looking him in the eyes with a sweet smile, “sam, can i kiss you on the cheek?” you whisper

⟢ “y-yeah, yeah, you can,” he whispers back

⟢ you think your heart could beat out of your chest as you lean closer, then press your lips to his cheek bone

⟢ you linger, then drop your head onto his shoulder and snuggle into him so that he can’t see the look on your face

⟢ whatever’s in your eyes isn’t just an act, and you’re unsure if you can let sam see that

⟢ though maybe it’ll help if the monster can, you’re sure that you look beyond in love at this moment

⟢ sam returns the favor with a kiss to the top of your head and a squeeze to your waist and he’s glad that you can’t see his face either because he looks just as completely and irrevocably in love as you do

⟢ it turns out that the other couple isn’t real competition; the monster clocks that they’re just a short fling, but you two? oh, you love each other and anyone can tell it with ease

⟢ you pretend to be lured out by the monster when he approaches, but the two of you make quick work of him in mere minutes

⟢ it’s the aftermath that’s hard

⟢ it’s the lack of an excuse to be so close to him, the thought of what if i never get to kiss him on the cheek again, what if i never get to kiss him at all? that really gets you

⟢ and now sam knows without a doubt that he goddamn needs you; he’s wondered before but now he knows

⟢ so when he reaches over and wipes away a splatter of blood from your face, you lean into his touch, you step towards him with intent

⟢ he’s not even thinking when his hand lands on your hip, not even when it pulls you closer

⟢ and he almost doesn’t think when he leans in, but he stops just inches away and whispers “fuck, can i kiss you?”

⟢ then your hands are in his hair and your lips are on his, kissing him hard and he’s kissing back with everything in him

⟢ you’re really fucking in love with each other !!!!

[lokigonnakmsforbucky]

Dating Castiel headcanons <3

I got this requested by @via-252<3 I'm pretty excited to do this request and also wanted to just make a point that there will NOT be NSFW as I believe Castiel to be Asexual. If you guys want an NSFW please send me a request and I'll see what I can do. I hope you enjoy it!

Dating Cass was pure heaven ironically, and not just because he was an angel.

It would be truly special.

You and Castiel met through the Winchesters a bit ago, and you two hit it off immediately. Which surprised Dean and Sam.

Castiel at first would come off really shy towards you because you were the first human he ever fell for. To him, that was a big no-no, since he was raised so differently. But, man did he fall for you hard

You would help him learn anything you were able to, since he was very curious of this world and wanted to learn everything he could. Of course, since you don't know everything yourself. When time let you both you guys would often hit the library or take a class to learn things like pottery, art classes, etc.

You would also help Cass understand humans, such as emotions, the importance of a first kiss, and more.

Cass wouldn't really show affection at first, so you would be doing all the hand-holding, or hugging him.

But, once he figured it out he did it ALOT.

He held your hand often, and after everything you guys fight, he holds your hand longer, hugs you longer, afraid that he will lose you.

He would be so cute and awkward during your first kiss with him, scared he might do it wrong.

"So,I just go for it?"

Him being so cauious would make you giggle

"Yes cass, just go for it."

Once you had your first kiss over with, he would often gives you kisses here and there at a random time. But, you would love it.

Castiel would often ask relationship advice from Dean, since Sam wasn't really all on the market.

"So...I just give her all of..."

"Yes, Cass that's what you do."

Castiel didn't always listen to him, thanfully.

Cass is very protective over you. Get a small scratch, he will automatically heal you. Mild headache? Healed. Someone trying to kill you? Dead. No one, or thing will harm you as long as he is here.

Sometimes his powers would get annoying...Like when he uses them to randomly appear out of nowhere.

Like the time you were undressed in your room, finding clothes to put on for a hunt.

"Cass! Can you please learn not to randomly appear in my room?"

"Yeah...uh I'm sorry...I will be waiting outside"

You and Cass had a very cute relationship, no matter the kinks.

Castiel loved you, a lot.

and you loved him.

That's all that mattered.

[shelbgrey]

✨Pookie😏✨Mother Pinecone🥳✨Fellow Simp🤩✨ can I request some lovely shrexy headcanons for the one and only Sammy Winchester😳 I just need some fluff and steamy steamy spicy headcanons please🥹 I’ll pay😉🫴💰💳💵

Dating Sam Winchester Headcanons:

Paring: Sam Winchester X Singer!Reader

Summary: headcanons about Sam dating Bobby Singer's kid. -SMUT warning!

💚MasterList ML2 💚MoodBoard

Between Sam being John's kid and you being Bobby's, you spent a lot of time together as kids.

You were always closer to Sam, you and him bonded over books and you were both the quiet ones.

It was obvious there was something between you two even when you were kids, but you were both completely clueless.

“the only two people who don't know Sam and y/n like each other are Sam and y/n” - Dean

But then he went off to college, you guys talked through letters and Emails for the first few months. Then he met Jes and you guys talked less and less.

Deep down Sam knew he dated Jess just to get over you, but then he felt awful to think that way after she died.

He never would have expected that you'd show up with Dean, telling him John was missing. Sam honestly hated to see the skilled hunter you have become, he always thought you deserved better.

Deep down he knew he stayed for you. College didn't matter much to him anymore and neither did finding his dad. He rekindled his friendship with you and wanted to protect you.

Hell, he would take you away from the hunting life if he could.

Before you knew it the three of you were a trio again. Saving people and hunting things together.

Then before you knew it you and Sam both fell back in to your original, clueless act you had with each other. It pissed Dean off, because he knew you guys liked each other.

Dean also knew neither one of you had the balls to admit your feelings. So he took matters into his own hands.

“Hey, y/n, you busy Saturday night?” Dean asked one night. “no?”

“Sammy, you sure as hell ain't busy” Dean joked, Sam rolled his eyes and sighed. “yeah... I'm not”

“good, because I am... You two go out and have a good time” Dean told you both.

Yeah Dean asked you out on a date for Sam. Both of you had mixed reactions, you didn't know how to proses what what just happened and Sam was just annoyed Dean was getting up in his business. Dean didn't stop you guys from going out.

he is sweet and gentle when he kisses you. The kisses you and him share are always sweet and full of passion. He pours everything into his kisses when his lips are on yours.

He definitely said 'I love you.' he said it after he had to save you from a vampires nest he told you he couldn't lose you and he loves you.

Sam would be the one to encourage you to go on rants or nerd out about things your passionate about. He'll listen beginning to end. If your like: “sorry if I'm talking too much” Sam will say: “no, no, keep going. I'm listening”

Not being stuck in his Tuesday time loop, but helping the best you can.

Sam's Hugs are warm and tight. Since he's so much taller than you he usually picks you up and holds you to his chest as your legs are wrapped around his waist and your arms around his neck holding him tight.

he promised to himself and you that if you were to get hurt by anything and he did mean anything at all, he would kill it. Even the smallest cut or bruse on you, he would freak out and with a gun in his hand, he would go after the very thing that dared to put a wound on you.

Sex with him has always been on the Adventurous side, but he learns your limits quickly and wouldn't do anything to hurt you. But when soulless Sam shows up there's no slowing down.

Even though Soulless Sam is hot one of the things he cares about most is sex and it might seem that's all he wants at the time, but the moment you get hurt the person or thing that hurt you is in a heaping pile of blood and broken bones.

Research dates all the time, you think it's boring as hell but your happy just to he able to spend time with him.

He's a health nut so he's always getting on to you and dean about your eating habits. “you know those things could kill you, right?” Sam asks as he watches you drink a monster energy drink, you'll just shrug him off.

You appreciate his concerns and you do back off on some stuff and let him cook you a healthy meal.

“what is that?” you asked staring at the blender in Discussed. “it's a smoothy, its good for you” he said pouring you a cup. “it's green goop”

✨Forehead kisses✨ he's a giant after all, so it's easier and convenient to just give you a little kiss on the forehead. He also loves it when your setting in his lap and giving him the same treatment.

Matching bracelets. Jack went through a friendship bracelet making phase and you made a couple with him. You and Sam both have one, he refuses to take it off. “you don't have to wear it”

“no, I'm gonna wear it forever. Back off”

You and Sam are literally Jack's parents, you probably end up adopting him at some point.

Never giving up on getting him out of hell, you hated the fact Dean when to live with Lisa. So while he got a girlfriend you were threatening crossroad demons for awnsers.

Making dirty jokes with Dean all the time to annoy Sam.

If Dean pranks Sam, you'll help get back at Dean. One time you convinced Sam to have sex in the impala just to piss Dean off.

Lucifer has the undying love for you and hits on you all the time, it pisses Sam off to no end.

Getting to see Sully first hand because he knew how much Sam ment to you and Sully just really wanted to meet the person that made Sam so happy.

Jody being a mother to you.

He absolutely loves feeling your fingers run through his hair. He'll kill to have his head on your cheat while you play with his hair after a rough hunt.

If your a smut book you get really secretive about and he'll notice quickly. “What you reading?” you blush and hold the book away from him. “nothing”

If he gets a hold of the book and reads a steamy part if the book, he'll probably want to try what he read too.

This man need physical contact a lot. He's a big cuddler and just needs you in his arms, it's a comfort and a protection thing.

He wants to hold your hand all the time too, if your walking around the bunker or a town your hands will be locked together, or sometimes hell just hold your had while doing research.

Communication won't be a problem in your relationship. You both just find it so easy to talk to each other.

But if you get into a fight, your fight loud and mean. There will be the silent treatment.

He's a bed hog so get used to sleeping right on top of him or right up against him because there's no room for personal space when you share a bed, especially if it's a motel bed.

He also hogs blankets.

You have bad sex in the bunker library, do with that information as you will.

You steal his flannels all the time, they're just so big and comfy.

He's good at turning you on😏

NSFW headcanons:

Sammy has a size kink, he loves the fact you are shorter than him. It makes it easier for him to manhandle you and throw you around without even trying.

likes to pretty much fuck you stupid. like to the point your shaking, you only can think of his dick and babbling his name. you probably won't be walking the next morning.

he's ✨skilled✨ with his hands, those big massive hands. it doesn't matter what he's doing with them, in between your legs, your face, around your neck, in your hair, I don't matter he knows what he's doing.

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.

He didn't realize how much he actually liked it untill you started pulling on his hair while he was eating you out. “Damn... Do that again... Please”

Biting, he's loves marking you up. There has been many times you had to cover your neck with makeup, but most of the bite marks are on your thighs.

But he also lives for the moments where it's just sensual and gentle. He secretly loves just holding you and kissing you slowly.

He wants to see if he can he make you scream louder than he did the last time. He loves the noises you make.

He well bend you over the table in the bunker library and take you from behind.

The desk will creak from the force he uses and his large body will presse you hard against the desk.

He loves hearing the moans and gasps coming out of your mouth.

Part of him will want you to be louder, even though he knew you aren't supposed to be sometimes.

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

Sam loves being dominate towards you. Choking you and edging you. “come on, Baby. Cum for me again”

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.

He has a tendency to grip the headboard when he's close to cumming.

“that’s it baby, there you go. takining me so well, honey.”

Sam loves the way his hands look on your body. Even better if you’re smaller than him, he just wants to be touching you all the fucking time.

He love getting head. I feel like he’d like having you on your knees. Plus, feeling your lips around him pushes him closer to cumming in your mouth.

If you’re struggling to take him in or taking long to adjust, he’ll whisper reassurances that you’re doing a good job while rubbing his hands on your back and thighs.

Sam first thought after sex he's always checking on you, making sure it felt good and your not sore. He is very gentle, cleaning you up and giving you anything you need before even thinking of himself.