Head canon time!
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.
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