Disclaimer: Don't own Supernatural, I'm just writing for fun.
A/N – Since Sam got to see a different side of Dean, I thought it was only fair to let Dean have his turn.
Dean fought his way through the crowd of people wondering for the tenth time how Sam talked him into this. All of the weapons has been cleaned and stored to Dean's satisfaction. They still had some shopping to do at some local munitions shops for supplies, and Dean wanted to touch base with one of Dad's contacts in the area, but other than that they were ready to go – and the job was a week away. Dean was all for hunting down some local legend; between the displaced native people and the sailors lost in the icy waters of Lake Michigan there was bound to be something to hunt down. But not tonight. Tonight Sam had convinced him to go out for a walk into town.
However, much to his brother's chagrin, Sam had neglected to mention the "Holiday in the Village" activities culminating in the Christmas Eve parade where all the locals gathered to wish Santa good luck on his one-night, globe-trotting adventure. If he didn't have a cup of coffee in each hand, Dean would gladly throttle his little brother. If he could make his way back to where he'd left him.
The crowd was packed on both sides of the street. In spite of the frigid temperatures and biting wind, it looked like all of the local residents of the town of South Haven had come out to get a glimpse of Santa. Bundled in parkas, scarves and hats, the crowd "oohed" and "aahed" at each float and local celebrity. How the cheerleading squad made it all the way down the parade route without suffering severe frostbite or hypothermia was beyond Dean. All he knew was that he was freezing and he was wearing way more clothing than they were.
Taking his eyes off the jailbait cheerleaders, Dean scanned the crowd of people across the street for Sam. The youngest Winchester was fairly easy to spot in a crowd; he usually stood at least a head above the people around him. Just as Dean caught Sam's eye a collective rumble of anticipation rushed through the mass collected on both sides of the street. The sound of applause grew in a deafening wave. A quick glance up the street confirmed that the man in red was on his way. There was no way Dean would be able to fight through the crowd and get across the street before Santa arrived.
With a malicious grin, Dean shrugged his shoulders and with a look indicated that he'd be staying where he was and drinking both cups of coffee in his possession. Sam gave him the "you've got to be kidding me" face. Dean just smirked – payback was a bitch. Sam shook his head and turned to look at the oncoming sled, pointedly ignoring Dean. Dean chuckled and took a deep gulp of the wonderfully pungent coffee.
A disruption in the crowd near Sam got Dean's attention. He was poised in an instant, ready to run across the street in case Sam needed backup. But Sam's body language didn't indicate that he was distressed or in trouble. Rather, Sam leaned over to talk to the woman standing next to him. The woman had her arms full with a little girl - at least Dean assumed it was a girl; it was probably unlikely that the woman would dress a boy in the shockingly bright pink parka that the child in her arms was wearing.
Sam leaned down again, telling the woman something. But this time, he stayed bent over and seemed to be waiting for some kind of answer. The woman seemed to be looking for something in his face. Dean strained trying to make out the conversation, but with the noise of the crowd, he just couldn't make it out. Then, the woman nodded at Sam who straightened up. Immediately he bent back down and lifted a small, blue clad figure over his head and onto his shoulders. Dean relaxed; all of that was just Sammy offering to pick up the lady's other kid since she had her hands full.
The boy, once he got over his surprise at his suddenly improved view, lit up at his new vantage point. Dean could actually read the kid's lips when he dropped his hands onto Sammy's head and exclaimed, "You're tall!" Sam just grinned and took a firm grip on the boy's legs; the kid was so excited he was liable to launch himself off of Sam's shoulders. Dean was fascinated by the tableau because the grin never left Sam's face. Everyone else in the crowd was looking at Santa, but all that Dean could see was Sam.
It struck Dean like a fist to the gut how right it seemed for Sam to be watching a Christmas parade with a family. Even if he wasn't the dad, he could definitely be the uncle. It was so normal, and he was really enjoying himself. He was laughing and waving just like everyone else. And when the boy sitting on his shoulders hugged Sam's face so he could lean over and say something into his ear without falling off, Sam automatically turned toward the boy while keeping him anchored; like he knew what to do. It made Dean wonder if Jess had had any nieces or nephews that Sam played with at family gatherings. Together they both looked up and waved frantically at Santa. When Santa waved back, both the boy and Sam bounced with glee. Even the mom bounced the little girl in her arms until she shrieked with laughter as well.
Suddenly it wasn't the wind that was making Dean feel cold. He felt empty and lost, but not on his own behalf – for Sam. Dean had very few memories of what Christmas had been like before and he clung to them like a drowning man clings to a chunk of driftwood. Sam never had any Christmas memories that included Mom – he didn't have any memories that included Mom; maybe that was why he chased "normal" so hard. It grieved Dean to know that Sam's joy in the holiday came from time spent with random strangers on the sidewalk and not with family.
As Santa moved down the street the buzz of the crowd followed him. Now that the main attraction had passed, no one was willing to stand in the cold for one second more. Seasoned locals quickly dispersed to their homes or one of the restaurants that had stayed open late for the special occasion. Dean watched as Sam flipped the little boy off of his shoulders. The boy was so excited he immediately raised his arms to Sam and demanded to do it again. Sam smiled apologetically at the mom for getting her son so riled up. She shook her head, and though Dean couldn't hear her it was clear she was thanking Sam for helping her out. Sam tried to smile and shrug it off, but Dean could tell how happy he was to be part of their little group, even for just a little while. With the mom urging the son to go, he gave Sam one last hug around the knees. Sam kind of patted him on the top of his parka and made his way across the street to where Dean was standing.
"Please tell me you didn't drink all of the coffee." Sam pleaded. Wordlessly Dean handed the full cup to Sam. Sam cupped it gratefully in his cold hands before taking a drink. Then Sam gave Dean a sidelong glance as though trying to judge his reaction to the evening. "Have I tortured you enough for one night?"
"You have tortured me enough for a lifetime!" Dean retorted. "Please Sam! Elves…reindeer…"
"Cheerleaders…." Sam tossed back.
Dean grinned and started walking. Sam fell into step beside him. "Now if they were college cheerleaders, then I might have been more interested…"
"Sam! Bye Sam! Bye Sam!" a young voice repeated insistently. Over to their left the family Sam had helped out was piling into their car. But while the mom was busy getting the little girl into her car seat, the boy was frantically trying to get Sam's attention.
Sam held his hand up in a wave, and then pointed to the car. "Brian, it's too cold, dude! Get in the car! Listen to your mom!"
"Okay! Bye Sam!"
Though they kept walking, Sam's eyes lingered on the minivan until it pulled out of its spot into traffic.
"Nice family." said Dean.
"Yeah." Sam agreed.
"That's why we do what we do." Dean stated softly unusually serious.
Sam shook his head. "Yeah." He looked at Dean and caught his eye. He nodded again needing no words.
It was about as close to a chick-flick moment as Dean wanted to get. A gust of wind motivated Dean into action. "C'mon! Let's get back to Jensen's before we both freeze to death." Then picking up the pace (and it was hard to set a faster pace than Sam because of his damn long legs) Dean headed back to the motel whistling random bits of Christmas songs that for some reason were stuck in his head.
A/N – Although I did take some liberties with the town of South Haven, I did not make up the name of the motel (Jensen's) - it's an actual place in South Haven. I thought it was serendipitous so I used it :-)