────── ⋆⋅☆ DATING DEAN WINCHESTER HEADCANONS
⭑.ᐟI’m obsessed with this… kicked my feet and twirled my hair while writing this..🤭 should I make a part two?
⭑.ᐟDean wouldn’t admit this, but he LOVES being the small spoon when you sleep. He feels protected and in a sense it helps him when he doesn’t want to feel alone, he feels safe. You’re the only one who knows, because Dean doesn’t want other people to see him as weak, or too attached-he has issues with how people view him.
⭑.ᐟhe doesn’t look like it from other people’s point of view but he truly is a sweetheart. Maybe it’s just with you, but he gets really soft. Like he’ll confess things to you at night that he wouldn’t tell anyone else. Whether it’s him being real about his emotions, or telling you embarrassing things that he did as a teenager that still haunt him. He’s so precious actually.
⭑.ᐟDean HATES when other people look at you. Not in a weird jealous and possessive way(only sometimes) but it’s mostly because he thinks he doesn’t deserve you, so whenever someone looks at you, he thinks you could just walk away from him. It’s not because he doesn’t trust you- he does and he knows you wouldn’t do it, but his trust and abandonment issues get the best of him sometimes and he can’t help but think like that.
⭑.ᐟon the other hand, when he does get jealous and possessive, let’s say at a bar on a night out when he feels confident, he gets like really pissed. He goes into starring contest with whoever’s eyeing you to try and intimidate them, and if that doesn’t work he gets vocal. It could be an agressive ‘can I help you?’ Or with a protective hand on your waist, he’d say something like ‘you need something?’. I don’t see him as someone who’s too agressive because he is intimidating so most times he doesn’t need to go too far, they look at him and just walk away cuz they know they have zero fighting chance.
⭑.ᐟokay. So, in bed? Yeah. He’s good. He’s literally Dean Winchester, there’s nothing he can’t do. Too tired? He’s got you, no need to lift a single finger, he’ll take care of you, even if it takes all night. However, because he’s a softie it’s not always rough. Sometimes it’s slow, he tells you he loves you, his pace doesn’t evolve, he does it just the way he knows you like or want it in the moment. When it’s rough, the aftercare is even better. He apologizes or makes sure for HOURS! That you’re okay and that he wasn’t too rough. You assure him it was perfect- but a part of him feels guilty sometimes although he had a great time. He likes slower sex better.
⭑.ᐟHE’S SO BIG OKAY THERE I SAID IT!!!!!!!
⭑.ᐟhe loves holding your hand like if he goes more than an hour without holding your hand or at least touching you in any way shape or form, he loses his mind. It soothes him, the way your thumb caresses the back of his hand, the way his thumb does the same at the back of yours. Sometimes you swear he thinks your hands are one big soccer ball by the way he holds both of your hands in his because he doesn’t wanna let go😭
⭑.ᐟhe loves physical touch but words of affirmation are his favorite. It wasn’t at first because it took him awhile to open up and not feel ashamed for feeling feelings- normal human emotions. But now? Not only does he worship you and lets you know, but he doesn’t go one single day without telling you he loves you, because with that job he knows tomorrow isn’t promised. On his side, he loves being reassured, so he loves giving you words of affirmation but he LOVES getting them. He enjoys feeling wanted and loved because he didn’t have that growing up.
⭑.ᐟhe loves driving around with you. Like at night if he’s bored he’ll just drag you to the impala and drive with no direction just so you can spend time outside of the bunker just the two of you.
⭑.ᐟhe also LOVES stargazing. Sam teases him about it, but he genuinely loves doing that with you. After driving around he’ll find a new spot and you’ll both lay on the impala watching the stars. It can last hours and neither of you mind, sometimes you don’t even talk you just hold each other and that’s enough.
⭑.ᐟhe doesn’t tell you but he hates the fact that you do this job too. If he could shield you from all of it, keep you in the bunker he would. He can’t, obviously- he knows that you do it for the same reasons he does, and it’s important to you, but he always gets this gnarly uncomfortable feeling at the pit of his gut before you go right when you find what the next hunt’s gonna be. You can tell- but you know it’s a touchy subject so you don’t bring it up.
⭑.ᐟsometimes he talks to you when you’re asleep (KILL ME NOW!!!!!!!!) like the first time he told you he loved you, he thought you were asleep- except you weren’t. So the next day you brought it up and you swear you thought he was about to cry of embarrassment. You obviously reassured him and told him you felt the same, so he felt better instantly. But that does kinda haunt him from time to time, he cringes when he thinks about it.
⭑.ᐟpersonally I think Dean loves bear hugs. He loves to hug you however- but bear hugs are his ultimate favorite. He tries not to do it when people are around, he’s not that fond of PDA, except at bars and what not- but when you’re alone he’s like a soft teddy bear, it’s so cute.
⭑.ᐟif you’re sick and beg him to stay away he will have the BEST time choosing movies and snuggling with you. He couldn’t care less about getting sick, he wants to be with you and try to make you feel better.
