Apple Pie Life... Sort of

~Chapter 1~

"Uncwle Deany, can you tewl me tha stowy 'gain?" Jack, Dean's nephew and Sam's son, asked for the twelfth time.

"Again, bubs?" Dean had told the story of how he and his fiance, Cas, met eleven other times. He'll give it to the boy, it was a pretty funny story, but it was past the boy's bed time, and Sam would kill him if he was the reason for Jack's crankiness at the fittings tomorrow. "J, it's time for bed."

"Pweeeease, Deeeeany," Jack gave him the puppy dog eyes he inherited from his father.

"Fine," Dean gave in. "But afterwards, you have to go to bed."

"Scout's Honor," the boy saluted.

"Okay, it was five years ago, senior year," and so Dean told the story of how he embarrassed himself in front of the biggest jock in his high school. And how that turned out to be the best thing to happen to him, because Cas proposed six months ago, and their wedding is in two.

By the time Dean was finished with the story, the little boy was fast asleep in his lap. He quietly chuckled and laid the boy down in his Lightning McQueen bed, kissing his head goodnight.

"Sleep tight, buddy. Don't let the demons bite."

Dean turned on Jack's night light and left the door cracked open. He had just made it down the stairs, when his phone rang. He looked at the caller ID and saw Sammy's name flash across the screen.

"Hey, bro," he answered the phone.

"Hey, Dean," Sam greeted, his tiredness prominent in his voice. "Is Jack asleep?"

"Yep, he finally fell asleep, after telling him the story of how Cas and I met twelve times. Don't know why he likes that story so much."

"Probably because you were embarrassed," Sam joked.

"Nuh uh," Dean shook his head despite his brother not being able to see him. 

"You're right. It's probably because he loves you and Cas so much," Sam's voice went quieter. "Y'all are his only family."

"Sammy, you gotta quit beating yourself up," Dean hated when his brother was like this. "It wasn't your fault." 

You're probably wondering what happened, right?

Well, Sam and his girlfriend, Jess, were young and dumb. Jess ended up pregnant at sixteen, while Sam was seventeen, with Jack. After one of her appointments, she got in a car accident. Luckily Jack wasn't hurt, but Jess didn't make it. Sam beats himself up because he had to cancel last minute. He had a test that would determine where he was placed in his class for graduation, so he couldn't be at the appointment (he was so close to sealing his valedictorian spot). During lunch, he received a call. Jess' car was hit, sending it rolling twice. She went into labor on the way to the hospital. Jack was born in the back of an ambulance. Medics said she told him 'I love you', and flat-lined. They did everything in their power, yet it wasn't enough. After Jess' passing, he made himself believe that if he had gone, she would still be here. Jack would have his mother.

Now he works with their Uncle Bobby and travels to restore old cars. Most of their clientele are banking, so they make good money. But that also means he isn't home for weeks at a time. Luckily, he has a brother that loves babysitting and doesn't have to go to work due to Cas being the CEO of an enterprise. The benefits!

"Whatever," Sam said. "I gotta let you go. I'll be home in time for the fitting. If not, then I'll meet y'all there, m'kay?"

"Alright, we'll see you then," Dean ran his hand down his face.

"Bye, Dean."

"Wait, Sam."

"Yeah?"

"I love you," Dean told his little brother. "And I'm always here."