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shelbgrey · 6 months ago

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✨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.

#Sam Winchester #Sam Winchester X reader #Sam Winchester smut #Sam Winchester Headcanons #Jared padalecki #Jared padalecki x reader #Supernatural #Supernatural x reader #Supernatural headcanons #Sammy #Moose #Dean winchester #Dean winchester x reader #Winchester #Walker

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