When Sammy is ten, the two of them start the tradition of getting doughnuts when their dad isn't around. Since John Winchester is rarely around, well, that means a lot of early morning dooughnut runs.
The first time, it's because Sammy's craving doughnuts something fierce, and whines and whines until Dean finally gives in. He pretends to be more irritated than he is, of course. Sammy's his little brother, and Dean loves the guy, but it's just not cool to think your family is tolerable, especially baby brothers.
(Even then, family comes first in Dean's book, even ahead of what's cool and what isn't.)
Dean figures that if Sammy's getting his doughnuts, Dean can get some coffee. He's technically not allowed to have coffee, something about it getting him "too damn wired", but he figures that what his dad doesn't know won't hurt him. (And he adds so much milk to it it might as well not be coffee; he'd drink his coffee black since it's more badass but he can't stand the taste.)
They are on their way back to the motel when Sammy decides to try to talk around a doughnut. "I don't think you're allowed to have coffee." Since his words are garbled from the doughnut, Dean's mostly guessing by the tone and suspicious squint that that's what Sammy was attempting to say.
"I am if you're gonna drag me out of bed at the buttcrack of dawn to get you doughnuts." His response produces a giggle from Sammy, which quickly turns to choking. Dean gives him a few thumps on the back, which in turn produces a mess of half-chewed gunk on the sidewalk. "Jeez. See? That's why I told you to wait until we got back to the motel to eat." Sammy scrubs at his mouth with the neck of his t-shirt and makes a grab for the bag, but Dean just elbows him in the ribs and holds it up over his head out of reach. "Dude, what did I just say?"
Sammy hops and jumps and flails around trying to get at the bag, and the image does wonders for Dean's mood. He holds the bag out of reach the rest of the way back to the motel, just because he can and because he knows Sammy well enough to know that he's not really mad.
Sammy's one freakishly-tall ten-year-old, so Dean had better enjoy being taller while he still can.
Another time they go out for doughnuts is about two years later, after they've killed a beastie. John had left them at the local motel and gone on his own hunt, and it turned out that their luck sucked because Dean and Sam had to deal with a Wendigo themselves, and those buggers weren't the easiest things to go up against. (Even years later, Dean couldn't be sure he'd forgiven John for leaving them there and not answering the numbers he left with the boys in case of emergency. What good is emergency contact numbers if you don't respond to them?)
Sammy's sporting a black eye, and Dean's limping a lot, but the two of them got of dead damn lucky and they know it. To celebrate their luck, they get doughnuts again, one of many times over the past two years.
Dean orders a coffee, just like the time they started this tradition, this time not putting anywhere near as much milk in it as he did the first time, having had time for his tastebuds to acclimate to the bitter flavour.
"Coffee's going to stunt your growth." Sammy's gotten better at speaking with doughnut mouth, and it's not that hard for Dean to decipher what his baby brother is saying.
Dean doesn't stop walking and just shrugs. "That's one theory. Another theory is that the caffeine could cause my body to go into hyperdrive and make me even taller."
Sammy gapes at him for a moment, his jaw actually in that "dropped jaw" position. Awesome! "That's not a theory! You just made that up!"
Dean shrugs again. "Isn't that how most theories are created? Someone makes it up, and they start testing it out to see if it might be real? I mean, people used to think the sun revolved around the Earth. How did they come up with that unless one person thought of it?" Dean wasn't the brainiac in the family. That title went undoubtedly to Sammy. But he wasn't stupid, either.
And Dean definitely knew how to argue. He was the arguing master.
"Whatever." Sammy's obviously done with the argument, which only means one thing: Dean totally won.
"Whatever yourself, little brother. Now come on, or I might just eat all your doughnuts myself." Dean started half-limping half-running, and it has the desired reaction. Sammy yelps and chases after Dean, letting his limping big brother win the "race".
Sammy's fourteen another time they go on a doughnut run. He's all legs and feet, gangly and awkward, and he keeps running into things. Dean knows that his days of being the big brother are coming to a close; Sammy hasn't hit his growthspurt yet, but it's only a matter of time. Dean isn't short, he hit 6'0 even before he stopped growing, but everyone who sees Sammy knows he's going to be taller.
This doughnut trip isn't prompted by anything major. Sammy just felt like getting doughnuts, and Dean didn't feel like telling his baby brother no.
Even when Sammy gets taller, Dean will always be the big brother, and they both know it.
This time, they eat their doughnuts in the little bakery, while Dean stretches his flirting muscles with the cute little blonde waitress. Unfortunately, she doesn't take him seriously, because while Dean's flirting with her, Sammy's pretending to puke his doughnuts back up.
Dean grabs the bag of doughnuts and stalks out of the building, Sammy's long legs catching up to him fairly quickly. "You know, little brother, some day, you're going to realize that girls don't have cooties, and you're going to want to hit it off with one. When that day comes, I'm going to get revenge on you so hard, and then remind you of this conversation."
Sammy wrinkles his nose. "Ew. Girls are okay as friends. But they get all kissy-face and that's gross."
"That's what you think now. You'll change your mind. Every guy does. Well, every straight guy does." Dean ruffles Sammy's hair, before Sammy dances out of his reach, the doughnut bag now in his hand.
Sammy shoves a doughnut in his mouth, spraying crumbs when he speaks. "Nuh-uh. Girls are gross, and so is coffee. Why are you still drinking that crap?"
"So I can keep up with you and your massive amount of energy. Enjoy it while it lasts." Dean steals one of Sammy's doughnuts and pops it in his mouth, more to annoy Sammy since he hasn't eaten doughnuts in a few years.
Huh. Maybe the kid is onto something with the doughnut thing. They still aren't as good as pie, though.
Sammy darts away, the paper sack of baked goods clutched to his chest in mock protectiveness. "Mine." Sammy runs off, his long legs carrying him swiftly, and Dean follows, laughing, taking care to not spill his coffee.
Dean can't shake the feeling that maybe, he's gonna start chasing after Sammy a lot more, and in more ways than the physical.
Well, crap, how are you supposed to deny a kid that, when it's his birthday, and that's all he wants?
Dean lucked out on the brother front, and he knows it. He does his best to make Sammy feel like he has a good brother in Dean, too. Some days he succeeds better than others, but this is one day he's determined to succeed.
Sammy's still all floppy hair and big hands and big feet. He's started his growth spurt, and he's already taller than Dean. They can even share clothes, if Dean's willing to roll the cuffs of his jeans up. (Not that they would, Sammy's style and Dean's are two completely different animals. It would be like saying a hippo looks like a giraffe. The only thing Sammy and Dean have in common-style wise is that everything has to be durable.)
Sammy orders coffee, too, this time. Dean just raises an eyebrow. "Aren't you the one who said it would stunt my growth?"
"Why do you think I'm drinking the crap?" Sammy shoots him a look of disbelief, and okay, Dean really should have seen that response coming.
"What's the matter, Sammy? Don't want to be the Jolly Green Giant?" Dean reaches up to ruffle Sammy's hair, but Sammy ducks under and away at the last moment. Sammy's gotten himself some freaky fast reflexes to match those freaky long legs.
Sammy hugs the bag of doughnuts close to his chest as he darts away. "Don't call me Sammy. I'm 16 now. I think I can go by Sam. And hell, no, I don't want to keep growing. I'm 6'3. That's a good height. Anything more might be a hindrance in a fight. I already have a good reach. What more do I need height for?"
Dean shrugs. "Chicks dig tall guys?"
Sammy rolls his eyes. "You get more chicks than I ever will. And I'm okay with that. You're the love 'em and leave 'em guy. One of these days, I'll find a girl and settle down."
No. No, no, no, no, no. That shit isn't going to fly. For Sammy to settle down, that meant he'd be leaving the hunt.
Dean wants his baby brother to be happy. But he wants Sammy to be happy with the family.
Sammy takes off running. "Come on! We're going to be late to the movie!"
Dean wonders how long it'll be before Sammy's running away for good.
Dean pastes a smile on his face. "Congratulations, Sam. You get to bang college chicks on a regular basis, now."
Sammy sighs heavily at him. "So not the point, Dean. You would go for the panty raids. I'm going because I want to be something."
Sammy's already something. Something that fights things most people will never know about, and pee all over themselves if they ever found out.
But Dean knows he can't say that. Not without breaking the dynamic they've had for years.
So Dean simply waves it off. "That's because you have no vision. You're all about the books. Books aren't good company in bed. They're actually pretty lousy company in bed, with those sharp poky corners that cause bruises if you fall asleep on them."
Sammy rolls his eyes at hiim, his hair flopping in his face. "The only times you've fallen asleep on the books is when I've made you help with the research side of things. Can't kill something until you know for sure what you're dealing with and how to actually kill the thing."
Dean knows that Sammy's right.
Hell. If Sammy's not gonna be around, and he's gonna be living it up in California, that means Dean and John are going to have to start researching again. They've gotten used to it being Sammy, because Sammy enjoyed looking into the lore and tracking info down. And Sammy was damn good at it. It made sense for them to divide it up according to their strengths and preferences. Now they're going to have to re-divide the load.
Dean wants to tell Sammy to not leave them. He wants to tell Stanford that they can't have his baby brother. Dean needs Sammy, for more than just research. He needs his brother.
Instead, Dean claps his hand on Sammy's shoulder, maybe a little harder than he means to. "Guess we're going to need to start getting you all your college things.
There are very few things more important to Dean than having his family close by. One of those few things is having his family be safe. The other is having them be happy.
Stanford would make Sammy happy. Dean could make Sammy at Stanford happy.
It's time for Sammy to leave the nest and prove that he can fly, and Dean knows it.
But he would hit on the waitresses, and brag about his little brother to the ones who were offlimits due to age or wedding rings. He'd flip through his wallet and show a picture of Sammy, and tell them about his little brother that was acing courses at Stanford, who'd wind up being an awesome badass lawyer.
Dean would have preferred to have Sammy alongside him for those things. But that actually only served to make Dean prouder of his little brother. Sammy was doing the right thing for himself, getting a good education and choosing his own life. A life that didn't include Hunting, and that meant it didn't, couldn't, include John and Dean.
Dean knew that. He accepted it.
He was proud of Sammy.
Sammy had better be kicking ass at Stanford, though.