The Holidays
The holidays around the Winchesters were never very warm and happy occasions. Seldom were they celebrated, what with John's hunting taking the family from one coast to the other. In fact, there have been times when they celebrated in the car, using a pine air freshener as a tree. Sometimes John wasn't there at all, and it was up to Dean to make Christmas for his little brother.
The first Christmas after Mary's death was the hardest. They were still living in Lawrence, Kansas, and John was just starting to dip his toe into hunting, into finding out what was really out there.
To Dean, Christmas was like reopening an old wound. He couldn't remember much of past Christmases, to be honest, but there was one memory, crystal clear in his mind. It was of Mary, baking Christmas cookies and letting Dean help.
He would put his little toddler hands on the rolling pin and push as hard as he could (which wasn't very hard, really). Then, when the dough was flat, they'd take the cookie cutters and make stars and trees and little men. Dean even insisted they make a tiny baby with the scraps, because even though it couldn't celebrate with them, "the baby inside Mommy is a part of the family too, and deserves its own cookie." Mary just smiled and helped Dean hold the knife to cut out the shape.
The next year, none of that happened. The broken family went to a friend's house for Christmas dinner. Present unwrapping was dull and short. Because, truthfully, John had completely forgotten about Christmas until he heard Dean talking to Sam about Santa Claus.
So, hurriedly, John had scrounged up gifts for the boys. Sam got a squishy toy that crinkled when you squeezed and Dean got a set of toy soldiers. Dean opened Sam's present for him, because, obviously, Sam couldn't. Dean never rolled out cookie dough again and Sam never got to taste his mother's cookies.
But there were times after that when you couldn't tell the Winchester family from a normal one. When Sam was three and Dean was seven, John rented an apartment, bought a little tree, and strung a string of lights. That year, Sam got a stuffed tiger, and Dean, a toy car. And, just for that moment, they could pretend ghosts and demons weren't real, and Santa was.
As the years went on though, holidays became more of a "if we have the time" sort of ordeal.
After Sam left for Stanford, any thoughts of Christmas disappeared, along with John. He'd vanish for a few days, around Christmastime, with no explanation as to where he went. Years later, Dean would come to realize that he went to visit Adam, his half-brother.
Meanwhile, Sam was busy having his first "real" Christmas, with some of his Stanford friends. Eggnog was drunk, gifts were exchanged, stories shared, and Sam drunkenly kissed his friend Jess under the mistletoe. He didn't know it then, but that kiss would spark the best years of his life. Sam, however, would look back and wonder: Could that kiss have sparked much more than love? Could it have lit the flame that killed Jess?
Three years after the fire, Sam and Dean find themselves celebrating in a cheap motel room, because Dean believed it was his last Christmas on Earth.
It wasn't, though, and now Dean sits alone in the Bunker, staring at the Game of Thrones book he was going to give Sammy for Christmas. With Bobby and Kevin dead, Castiel gone, Charlie in Oz, and Sam in the wind, there is no one left to join him. Dean knows he ought to be looking for Sam, but he can't. Not right this second. It's Christmas.
Dean wipes away the tears that are forming in his eyes. Come on, Dean, get it together, he thinks, just because there isn't anyone else around doesn't mean you need to get all weepy.
He stands, downs the rest of his beer, and goes to bed.
Pulling the blankets up to his chin, Dean mutters into the dark:
"Merry Christmas Sammy, wherever you are."