#sam headcannons

What do you think Dean would do to celebrate his first anniversary? And maybe you could also do what you think Sam would do to celebrate his first anniversary.

Thank you so much for this idea/request! Sorry this took so long for me to answer! I took a little break from tumblr for a few days, and this idea kind of got lost in the shuffle, but I didn't forget about this!

Also, I love word vomiting thoughts, but I’m trying to get better at making my headcannons a little more structured, so let me know if you guys have any thoughts on that lol

Dean:

Dean has never experienced an anniversary before, so he’s kind of on edge about the whole thing, but it’s you, so of course, he’s going to try his best.

He kisses you awake, whispering to you softly to open your pretty eyes already, before you’re finally fully awake and he can wish you a happy anniversary. 

After that, it’s snuggles and kisses and sweet whispers about how in love with you he is for at least 45. Dean’s not great with words, but he just rambles the entire time, knowing that it doesn’t really matter what he says because you’ll already know.

You guys get ready together, taking your time, and he asks you to wear that favorite dress of his if he wears your favorite shirt, which obviously you can’t say no to. 

Dean then grabs a bunch of stuff and throws it into a duffel before pulling you out to the car. He won’t tell you where you’re going, but that you’ll enjoy it, and to just be patient. On the way there, you stop at a diner and get an order to go, including a celebratory anniversary pie.

Eventually, he brings you to some secluded area off in the middle of nowhere- maybe like a little clearing off a hiking trail or a lookout spot off an empty highway where it’s beautiful and quiet and just you and him.

Dean lays out a blanket he stashed in that duffle earlier and sets out the food, essentially making a little picnic. He even brought a little speaker to softly play music in the background.

You and he eat, talk, and take in the scenery. He gives you a small present, definitely homemade, like a leather bracelet, a mix tape, something like that- personal and something you’ll cherish forever. After that, you guys end up cuddling while lying down on the blanket and cloud gazing for hours while talking. 

Later, Dean takes you home (whether that’s an actual home, a motel room, the bunker, whatever) and before you’re barely in the door, his hands are on you like a man starved for touch. 

That’s when he fucks you over and over and over again. Him on top, you on top, sideways, standing up, his mouth, his hands, his cock, all of it making you come undone multiple times. I’m talking like at least 7 times. 

He makes sure to indulge in every single one of your kinks he can remember in the moment, like he’s trying to prove something- win a competition maybe. You don’t know, and frankly, you’re too fucked out to care. 

But after that, the aftercare is just as heavenly. He cleans you up nice and gently, whispering loving praises and makes sure you drink plenty of water before holding you close, wrapped up in his arms as he makes sure you know exactly where you belong and how much he loves you. 

Sammy:

Oh Sammy, Sammy, Sammy- he’s literally so cute and thoughtful about this!

He definitely wakes up early to prepare for the day, heading out before you wake up so he can bring you breakfast in bed from one of the local diners.

He knows what your favorite flowers are and specifically buys a huge (and extremely overpriced) bouquet of them for you, which he delivers with breakfast.

Then there is most certainly time for cuddles and warm and soft morning sex before the plans he made for the rest of the day.

He would find an activity to do that would suit whatever interests you guys have in common. If you’re a book worm like him, maybe it’s a trip to the all the 2nd hand books stores in a 10 mile radius, if it’s more of the athletic stuff maybe it’s like indoor rock climbing, maybe it’s an old school arcade or an aquarium or museum- it doesn’t really matter as long as it’s something you both can enjoy while spending quality time together. 

Dinner is next, and he picks somewhere nicer than the usual diners you guys stick to- nothing crazy, something still lowkey, but you guys do get a dessert to share. He ends up letting you eat most of it. 

Back at the motel, he’d surprise you with a gift despite the two of you having originally decided on no gifts.

Again, it’s nothing crazy, but it’s something you’ve been mentioning wanting/needing, and shows how much he actually listens to you.

He’s definitely taking the rest of the night to worship you and your body - I’m talking like hours of foreplay. 

I don’t necessarily think Sammy is a sub (okay, maybe switchy but definitely not a pure sub), but I do think he’s a major munch and would spend a lot of time worshipping you like that, especially today of all days.

The main event though is magical when it finally comes because he fucks you like he means it, like this is the last chance he’ll have to have you this way- It’s slow but not at all gentle. It’s deep and passionate and filthy. 

He’s talking your ear off between groans and grunts, telling you how much he loves and appreciates you and your body, and the whole experience is overwhelming in all the best ways.

And after you two finally come down off that high, just to make sure you feel extra loved before it’s time for sleep, you shower together, and he makes sure to do all the work for you, even down to the little shampoo head massage.

-You guys were friends before you started dating

-You asked Sam out

-He nearly shat bricks, he was so shocked and excited

-He tried keeping it from Dean because he was afraid Dean would mess it up, or tell their dad

-Of course Dean ended up finding out when he followed Sam one day

-And he agreed not to tell their dad, because he knew that wouldn't end well

-In fact, Dean helped keep Sam’s secret

-Your first date was a picnic in the woods 

-Whenever you get scared , Sam is there to comfort you

-He didn’t want to tell you about he family business

-He finally did though, when convinced him to talk to you about what was stressing him out

-You were a lot more understanding that he thought you would be

-Which earned you an official stamp of approval from Dean

-Studying together

-Sam sneaking into you room in the middle of the night

-Which surprised you at first because you though Sam was too sweet to be any bit rebellious

-You soon got to know that even Sam could go against the rules sometimes

-Like when he snuck you on a hunt that he and Dean were going on

-Dean was not pleased and you almost got hurt

-Sam felt bad for days afterwards

-Helping each other with homework

-Telling the other kids to back off when they pick on Sam

-Always sticking up for each other

-Meeting each other in the hall at 1:30 every day

-Making Sam tons of foods, because he’s pretty much lived off fast food and canned goods his whole life

-Sam calling you “His cutie”

-You calling Sam “Hunter boy”

-Sam keeping a picture of you in one of his school binders

-Going on movie marathons on rainy days

-Your parents loving him

- I mean, what parent wouldn’t?

-Wanting to meet John when he comes to tow, but Sam refuses

-You’re adamant, but Sam is even more adamant

-And so you never met John, which you were assured was for the better

-Dean being protective over you because he knew how much you mean to Sam

-Sam being protective of you because you mean so much to him

-Sam being the ultimate boyfriend

-Because c’mon Sam would be a great guy

I was thinking a lot about that one Christmas episode (season 3, episode 8) where we see flashbacks of the boys and decided to make a little headcannon about what I would have given the boys if Santa was real and I was, in fact, Santa. Also, for context, I believe Dean is supposed to be like 12, and Sam is supposed to be like 8. (Also, also, I tried to keep this time period accurate, but I wasn’t even born until 1999, so give me a break if this isn’t totally correct lol). And as always, welcome to the I HATE JOHN WINCHESTER FAN CLUB.

Both:

New clothes - I just know John didn’t buy them more than like 3 outfits each, and all of Sam’s were Dean’s hand-me-downs. I’m talking like a new pack of underwear and socks for each, and at least 2 shirts, 2 pants, and a jacket for each boy. Probably a beanie and gloves too, since a lot of their time is spent in the northern part of the US. And also a new pair of sturdy boots.

HYGIENE products. Again, because I know John’s not remembering to do this shit. Both boys get a new toothbrush and their own individual toothpastes, deodorants, and combs. Maybe even their own body washes too, because knowing them, they’d probably hate whatever scent the other one decided to pick.

Comic books and graphic novels.

Bikes so they don’t have to walk to and from school. 

Dean:

A tactical watch, like the kind with a little compass in it, if you know what I mean? It would make him feel like a grown-up for some reason, and he’d love that. 

In the same vein, a utility pocket knife that has all those little flip-out tools.

Those little tech deck finger skateboard toy things? He’d act like it was stupid and childish at first, but then you’d catch him constantly messing with it, learning how to do flips and tricks. 

Cassette tape walk man and a bunch of classic rock cassettes. 

Sam:

Notebook / Journal and lots of pens and pencils. This kid needs an outlet. Let that boy write or draw or whatever he wants; I don’t care, he just needs something to express himself. 

Rubik's Cube. He’d spend hours working on that thing. 

Some kind of action figure? Maybe like transformer, Power Rangers, or Teenage Mutant Ninja Turtles? I think those were all popular around then, so just whichever he would like best. 

His first hunting knife. Dean can teach him how to use it for protection and maybe even wood carving? 

Raspberries

Age: 4 monthsDean smiled toothily at his little brother who was kicking his tiny feet in the air at the sight of Dean. He gurgled softly, hazel eyes already showing big brother adoration. Dean cooed at Sam and leaned down, blowing a small raspberry on the baby tummy. Sam squealed and giggled cutely, kicking his little feet harder.

Age: 4 years“Nooooo Dean go away!” Sam squealed, running around the tiny motel room as his 8-year-old big brother followed at a slower pace.

“C’mon Sammy, it’s tradition!”

“I don't want it!” Sam lied, trying to make his way to the bathroom when Dean managed to scoop him up and toss Sam on the bed. “Nooooooo!”

“Yeeeees~” Dean cooed, lifting up Sam’s Batman t-shirt and blowing a loud wet raspberry on his tummy. “Happy birthday Sammy!”

Age: 8 yearsSam was woken up to scribbling fingers in his armpits and wet raspberries on his neck, making the newly turned 8-year-old shriek with childish laughter.

Age: 16 years“Dean, I am too old for this!” Sam growled, his body tense in a fighting stance. His older brother just grinned cheekily, bowling right into his scrawny brother who hadn't reached a growth spurt yet. “Dean!”

“It’s your birthday Sammy! You get 16 raspberries this year!”

“No! NononOHOH AHAHA DEHEHEAN!”

Age: 21 years“Dehehehean! Stahahap ihihit!” Sam giggled happily, pulling his brother’s dirty blonde hair as he was ambushed in the Impala and subjected to tickle torture in the closed space.

“Nah, I know you love it, Sammy!”

“Ihihit’s SahaHAHAHAM!” He screeched.

“Sammy,” Dean repeated, a sloppy raspberry on his belly button making Sam cackle hysterically.

Age: 35 years oldSam was researching for a way to open a rift and ignoring the world around him. He knew what day it was but much like the year before, he couldn't find himself to care. Not when their mother and Jack were missing and they still hadn't gotten a way to get them back.

On the bright side, they had Gabriel, but the angel was being a pain in the ass as usual. Sam sighed tiredly, glaring at the old clock on the side of the room and seeing it was almost 11 pm. 

He wasn't expecting anything for his birthday, to be honest. He was way past being that selfish, but he sorta wished it was acknowledged. But Dean was in a gruff mood and Sam knew better than to bother him when he was moping. Sam stretched, taking another look at the clock before getting up and heading to his room.

The bunker room now had small bits of his personality laying around and it felt more at ease to call it a home. Just as Sam put his books down on the table, he felt another presence behind him and was surprised to see Dean leaning against the doorframe.

“Dean?”

“I didn't wish you a happy birthday,” Dean said roughly, voice laced with a hint of guilt. “Why didn't you say anything?”

He shouldn't have had to say anything

“I didn’t want to bother you,” Sam shrugged. “I know you were…busy…” drowning in another bottle of scotch.

“Still,” Dean sniffed, obviously reading Sam’s hesitance.

“Uh…sorry.”

Dean walked into the room and lightly sat on the bed, Sam following a second later.

“Do you remember how we used to celebrate your birthday?” Dean asked softly.

Sam chuckled and nodded, despite it being so long ago. “Yeah…”

Dean had a small smile on his lips, obviously caught in memories. Sam but his lip, not wanting to mention he missed it and laid on the bed, hoping Dean got the message. dean glanced at him, eyeing his slim form on the bed before snorting.

“Dork,” He whispered, wasting no time in dipping his head down and blowing raspberry after raspberry on Sam’s already quivering belly.

Dean + Tickle Games