Disclaimer: I got the original idea from a headcannon I saw on either Pinterest or Tumblr. I don't own the story, only the writing.
Set in no particular timeline. I guess it could be sometime before the Season 13 finale.
"Are we there yet?''
Dean lay his head back in frustration. "Kid, I swear to God—''
"No, we're not there yet, Jack,'' Sam interrupted his brother.
"I told him that five minutes ago,'' muttered Dean.
"Well, when will we get there?''
"Soon,'' said Dean.
"How soon?" Jack pressed on.
"I don't know, uh, three hours? Four?''
Jack slumped back in his seat, disappointed. They'd already been driving in Dean's Impala, Baby, for hours. Jack was restless.
"Just be patient,'' Castiel advised Jack gently. "We'll get there eventually.''
Jack nodded, watching Cass closely. They were crammed together in the back of the Impala, with Dean driving, and Sam in the passenger seat. Jack knew this was how the Winchesters and Castiel usually operated. He didn't know how they could just sit in the car for hours upon hours, listening to music so loud it made Jack's ears hurt. Sam had made Dean turn off the music while ago because he knew Jack didn't like it. That made all the driving more bearable, but it didn't make Jack any less antsy.
"Where are we going?'' Jack suddenly asked, realizing he did not know. Cass had just told him they were going somewhere and he had obediently gotten in the Impala. Hours had passed, and they had not arrived to the somewhere.
"Some little girl got murdered in Tulsa,'' said Dean. "They want us to check it out.''
"Oh.'' Jack turned to look out the window at the drab, flat, landscape. The casual way Dean had explained the case. . . it bothered Jack. Sam and Cass didn't seem to care though. Jack guessed they were used to talking about their morbid investigations in casual ways. Still, Jack wondered about the little girl who had been murdered. How exactly old was little? Younger than him? How had she been killed? Had it hurt? Most likely, he realized, it had. The thought depressed Jack. He wished he was back at the Bunker.
Sam watched him in the rearview mirror. He noticed the young angel's sudden mood change from restless to melancholy. The Winchesters (+Cass) were still not accustomed to having a kid with them. Jack had asked a question and Dean had answered it. Sam didn't hold upsetting Jack against his older brother; Dean simply had not thought about the prospect of murder dismaying Jack. Still, Sam felt bad for the Son of Lucifer. He thought hard for a moment. Then, "Hey, Dean, why don't you pull over a sec?"
Dean shot Sam a side-glance. "You're not going to throw up, are you?"
"No, no, I'm fine,'' said Sam quickly. "I just thought Jack could use some fresh air.''
"Do you want me to roll the windows down?''
"Uh, no, that's not what I meant.''
"I know,'' Dean sighed. And to Sam's surprise, he actually began pulling over.
Jack lifted his head from where he had been resting it against the window. "What are we doing?"
"Get out,'' said Dean, putting Baby in park.
"Are you kicking me out?!" Panic edged Jack's voice.
"No!" Dean, Sam, and Cass all said at the same time. Then they glanced awkwardly at each other.
"We're taking a break,'' Sam quickly explained.
"Oh.'' Relief crossed Jack's face. "Good.''
"We wouldn't kick you out, kid,'' said Dean.
Jack smiled. "I'm glad.''
Dean cleared his throat. "Let's go then,'' he muttered, unstrapping himself.
Jack yanked at his own seatbelt, but it didn't come undone. Castiel leaned over and popped the buckle. "Thanks,'' said Jack brightly. Cass smiled.
Jack was instantly cheerful as soon as he was out of the Impala. He explored the bare plain land for a few minutes, before returning to the car, where Dean, Sam, and Cass were leaning against the fender drinking beer.
Castiel studied the young angel. His rapid mood swings puzzled Cass. Sam had told him something about how human teenagers were often moody, but Jack didn't qualify as a human teenager. He was more or less a human infant. But he was a teen angel. Cass knew very little about teens and children. But he and the Winchesters had previously agreed the Jack had the innocence, mindset, and softness —and occasional whining— of a toddler.
"Thank you for stopping,'' said Jack politely.
"I think we all needed a break,'' said Dean, taking a swig of his beer. Cass smiled to himself. Dean and Jack's relationship was a turbulent one, but Cass knew, whether Dean would admit it or not, the oldest Winchester did care deeply about Jack. He just wasn't as good as showing it as Sam.
Castiel felt a sudden urge to stretch his wings. No cars had passed a long while. They had time. "Come Jack,'' he said, placing his beer on Baby's hood. Jack trotted behind Cass as the older angel put a couple yards' distance between them and the Winchesters.
Dean watched as long shadow-like forms fingered out from Castiel's back, creating large, graceful wings. A moment later, the same happened to Jack. The angels' wings began to flutter, lifting them off the ground. Dean enjoyed watching the rhythmic beat of Cass's and Jack's carry them further from the ground and closer to the clear blue sky.
"Hey, thanks for stopping,'' said Sam.
Dean didn't say anything. Sam noticed. "Something wrong?''
"Nothing's wrong, Sammy.'' And it was true. Well, plenty things were wrong. But the Winchesters were used to wrong. Dean was currently with his brother, and they were safe. They were watching their friends fly around, carefree and happy, and they were also safe. With the Winchesters, with all hunters, something always went wrong. But at the moment, everything was all right.
Thanks for reading! Please review and let me know what you think!