Sam and Dean kind of had a rocky relationship with Christmas. Mostly, it was just a matter of their lives being too crazy for them to really have the time for it.
The last time they "celebrated" Christmas, Dean was on the countdown clock to hell and they had just skewered two pagan gods with an evergreen trees. This time, they're smack dab in the middle of the apocalypse, so any sort of acknowledgement of December 25 probably won't go past "a Saturday."
Still, Sam always feels a little guilty, every year that Christmas comes and goes that they don't acknowledge it. Mostly because Dean loves Christmas, even if his brother would never admit to it. Dean played it tough, acted like he couldn't be bothered, but Sam remembers all too well the Dean of his youth, baiting Sam out into the freezing winter nights to walk around and look at all the illuminated decorations, promising a hot meal and a movie of Sam's choice in exchange for the company.
And don't get him started on Christmas movies, which Dean would absorb with gusto on any channel available, claiming the whole time that "there's nothing else on, so might as well."
So yes, Christmas was just one of the many occasions that Sam felt like he let his brother down.
That's why, even in the middle of the goddamn apocalypse, Sam didn't hesitate in the grocery store to take advantage of the 10/$5 sale of Entenmann's mini-pies, grabbing one of every flavor they had, plus a couple extra of the apple, which he knew was Dean's favorite.
"You get lost or something?" Dean asked him when he got back, sitting propped against the headboard, remote in hand, Rudolph the Red-Nosed Reindeershowing on the screen, "How long does it take to pick up toothpaste?"
"I bought some extra stuff, that's all," Sam remarked casually, setting the bags down on the little round table, "Got a problem with that?"
Dean rolled his eyes and shrugged, turning back to the TV, "Your fake credit card, man, go wild."
Sam chuffed at that, extracting the toothpaste, shampoo, deodorant, razors, and new toothbrushes from their plastic bag and throwing a package of each into each of their duffels, sufficiently crossing hygiene products off their to-do list.
He picked up the bag of mini-pies next, tossing them onto Dean's bed as he passed, not looking at his brother as he walked into the bathroom and closed the door.
By the time he had relieved himself and came back into the room, Dean had upended the bag and was sorting through them, looking at each pie with an expression of delight on his face so pure Sam drew up short for a moment.
Dean looked up at him, still smiling, "Dude!This is awesome!"
Sam gave a small laugh, walking to his bed and sitting down.
"Don't say I've never done anything for you," he teased, grinning, and Dean snorted, tearing into an apple pie, just as Sam predicted he would.
"Ah man," Dean sighed, stuffing a huge bite into his mouth and tilting his head back, eyelids fluttering in unsuppressed pleasure.
"You want a moment alone there, Dean?" Sam teased and Dean flipped him off, a look of bliss still in place.
"I love pie," Dean said after he swallowed, opening his eyes to take another huge bite.
"Yeah, I know, Dean," Sam grinned, leaning back with a sigh, propping his head up to watch the TV, Dean comfortably in the corner of his vision, still chowing down.
"Oh, hey, that reminds me," Dean said, swinging his legs over the side of the bed and striding over to his bag, rifling through it, half a pie hanging out of his mouth comically.
Dean made a grunt that sounded a little like "Here!", tossing a paperback in Sam's direction, and Sam caught it, brows furrowed as he read the title.
"James and the Giant Peach?" he asked skeptically, looking at the worn cover.
"Yeah, remember? You were, like 11, or something, and you had this beat up copy you pinched from a library. Dude, I think you read that thing at least once a month, it was crazy. But we left it in a motel in Louisiana, and I never got you a new one. So I saw that at the thrift store the other day, and it made me remember that so," Dean shrugged, settling back down on the bed, and opening his second pie, pumpkin this time, "Thought it would be a laugh. It was 25 cents, I can't really complain, you know?"
Sam flipped through the well-worn pages fondly, stopping here and there to read a passage or two, and smiling as he remembered so many nights with this book, hiding under the covers with a flashlight, or in the back seat of the car. It had been his favorite book, and he had been devastated when he lost it.
"That's... thanks Dean," Sam said quietly, looking over to his brother, and Dean waved him off.
"Nah, nothing. Forget about it," he brushed off casually, but Sam could see he was pleased.
"Ah, good ole Yukon Cornelius," he remarked a moment later, bringing Sam's attention back to the TV, which was still showing Rudolph, "'This fog's as thick as peanut butter!'" Dean quoted with the character and Sam smiled.
"'You mean pea soup,'" Sam supplied next, in time with Herbie the elf and Dean threw him a grin before filling in the next line.
"'You eat what you like, and I'll eat what I like!'"
Dean laughed then, grabbing a lemon pie off the bed and tossing it at his brother.
"Have a pie, bitch," Dean said cheerfully, and Sam smiled, tore open the package before opening his book and starting to read, the sounds of the TV a pleasant noise in the background.
"Merry Christmas to you too, jerk."