It's your son's first Christmas without you, and with the Winchesters.
Dean glanced at the rearview mirror, eyes meeting Jake's. "So, kid, what do you and your mom do for Christmas?" This was the first year that Jake would be spending Christmas with the Winchesters and Dean wanted to make it special for him, make up for what he hadn't gotten to do while he was growing up.
"Oh, my mom and I make gingerbread cookies!" Jake squealed excitedly. "And-and she makes hot chocolate and we put on our onesie pajamas and watch Rudolph! She reads me a special Christmas story before going to bed and then, then we open presents in the morning! She puts them under-under the tree!"
"Do you and her decorate the tree?" Dean grinned, knowing where to go now. He was about to go to the grocery store with Jake when he had the idea of asking him about Christmas and the traditions that you shared with him.
"Yes!" Jason screeched, clapping his hands. "She-she lets me choose whatever decorations I want and after-after being done, we sit on the couch and mommy sings me Christmas songs!"
"That sounds great, kiddo!" Dean grinned. "What do you say you and I go buy a Christmas tree?"
"Yes!"
"Awesome!" Dean laughed along with Jake, looking forward to the day. Sam had remained behind reading a book, letting Dean have quality time with his son, and Dean was planning on taking advantage of the day to show Jake just how much he had come to love him.
After a few minutes, Dean pulled up to a small lot where pine trees were being sold and parked towards the back of the parking lot. He chuckled as he helped a jumpy, thrilled Jake out of the car and took his hand. "Alright, buddy, choosing the tree will be your responsibility. Are you ready?"
"Yeah!" Jake's tiny fist shot in the air before he was running towards the trees, dragging Dean with him.
It didn't take long for a tree to mesmerize Jake and soon, Dean was thanking one of the employees for helping him haul the pine up on Baby's rooftop. He grimaced at the thought of the branches scratching the paint job, but then Jake clapped his hands excitedly and hugged him, and Dean was convinced that he would do anything to make Jacob happy.
"Alright, next thing we need, kiddo, will be the decorations," Dean announced as he turned the key and the engine roared to life.
"Oh, are we going to those giant Christmas stores?" Jake gasped.
"That's exactly where we're going!" Dean grinned widely.
It was hard to keep track of Jake as he ran around the store, ricocheting from one aisle to another one, squealing at every decoration he saw and begging Dean to take everything he could get his little hands on. Dean sighed, but still felt himself smile as he decided to indulge Jake and agreed to purchase everything possible, even the ugly Christmas sweaters that Jake chose for him, Dean, and Sam to wear.
"Dad, we have to take pictures," Jake turned towards him, voice earnest. "So that we can show mommy when she comes back!"
Dean felt his heart sink, but he concealed his pained expression and nodded at Jake. "Alright, kid, we'll take pictures. Although, you'll have to convince your Uncle Sam."
"I will!" Jake grinned, before tossing in a few more tree decorations.
"Jake, don't you think we have enough things?" Dean chuckled nervously at the full cart.
Jake turned to look at the shopping cart pensively, finger on his chin and eyes squinting as he surveyed what he had chosen. "Yeah, you're right, dad! Let's go," he waved Dean over as he began to walk towards the registers and Dean rolled his eyes. He was reminded of you and how bossy you always were when Dean decided to go shopping with you for whatever reason. Sometimes you would need an outfit to go undercover for a case and you'd drag Dean along with you, leading the way and expecting him to follow. Dean smiled at the memory before focusing on placing all of the Jake's purchases on the conveyor belt.
"Thank you, dad!" Jake leaned up to kiss Dean's cheek as Dean buckled him in. Jake had happily helped Dean in putting the bags in the trunk once they had exited the shop.
"No problem, kid," Dean smiled, pressing a quick peck on Jake's forehead. He climbed into the driver's seat and pulled out of the parking spot. Dean reached towards the dashboard and turned on the radio, raising the volume.
He bopped his head to the music, lips mouthing the lyrics as he tapped his fingers rhythmically on the steering wheel. Jake's squeal made him jump. "Oh, dad, dad!"
"Jesus, kid! Don't scare me like that!" he chastised him.
"Sorry," Jake mumbled before forgetting he had given Dean the scare of his life and clapping his hands enthusiastically. "Mommy sang me that song!"
"Did she now?" Dean raised a brow as he recognized Lynyrd Skynyrd's "Simple Man."
"Yes! She sang it to me whenever I couldn't sleep," Jake said. "Her voice is so pretty!"
"I know," Dean shared a smile with Jake as they met looks through the rearview mirror. "She used to sing all the time to me."