Well, things could be worse.
The last hunt didn't end too smoothly. You were hit with an age-reversal spell by a witch, leaving you with the mind and body of your seven-year-old self. Luckily, it wasn't permanent. After a bit of research, Sam came to the conclusion that the spell would wear off in a week or two. The only problem? There wasn't much that could be done in the meantime.
It was... strange, to see you so innocent. So used to seeing a hardened shell and walls you put up to protect yourself, seeing you happy for once was like a breath of fresh air for Dean. You followed him around like a lost puppy, seemingly taking a liking to him. You'd practically attached yourself to the man's leg as soon as you saw him --- and Sam couldn't help but laugh, much to his brother's chagrin.
Though, things weren't as bad as Dean originally thought they'd be. He was pretty good with kids, and apparently, that included you. You both went out to a diner for some pie, watched a movie, and now, back at the shitty motel room, you were sat on the edge of one of the beds. Dean had shoved a random box into your hands, hoping its contents would keep you occupied even for a moment while he and Sam focused on the next hunt.
All of Dean and Sam's fake IDs were in the old shoebox in your little lap, your small fingers sorting through them, and reading them as best as you could. An idea popped into your head. These would be great to play dress-up with, and you voiced your idea very quickly.
Dean denied almost immediately- no way in hell was he playing dress-up. But, the way your big doe eyes grew glossy, your little chin quivering as you stared up at him, pleadingly, begging with your eyes- damn it!
"Alright, fine!" Dean eventually relented with a sharp sigh. He didn't want to deal with a crying child. He gently grabbed you from under your arms, setting you down on your feet on the motel floor. "What d'you have in mind, kiddo?"