*This has been done forever, but ff is just now letting me post :/ Sorry for the wait!*
Dedicated to my dearest friend Cheyenne, better known as A Darker Heaven and Hell, who let me write out this brilliant idea! Sorry it's so short and possibly too fluffy, but I had fun writing it! All credit goes to Cheyenne for the idea :D
Dean was stretched out on the bed, absently doodling on a piece of hotel stationary while Sam made a supply run. They were on a hunt and out of Hunter's Helper. AKA cheap whiskey. Cas, who'd come to help with the lore, was standing in the corner doing nothing in particular. He was like a statue with the deadpan sense of humor to match. Dean was getting bored just looking at him.
"What are you doing?" the angel asked.
"What is the purpose of that?" Castiel replied with his signature head tilt.
Dean chuckled softly. "I'm bored, so I'm doodling until Sam gets back."
Cas didn't reply, only watched the hunter with curiosity and interest. An idea sprung into Dean's head. He slid over on the bed to make room before pulling a new sheet of paper from the nightstand.
"Come over here, I'll show you."
Castiel hesitated only briefly before coming over and sitting down next to the hunter. He looked at the piece of paper laying next to Dean, the one with the doodles already on it. His blue eyes glittered with fascination as he picked it up and stared at the drawings. Dean didn't even think the doodles could be considered drawings; they seriously sucked.
"Is this you and I?" Cas asked.
Dean ducked his head to cover his slight blush. "Well, um, sorta…yeah."
The doodle was of Dean, Castiel, and the Impala. Nothing really special, just something he'd wanted to draw out for the hell of it. Now he was embarrassed. It had just been for fun, he didn't want Cas thinking he was some kind of weird stalker dude. If anyone was a creepy stalker it was Cas and his constant invasion of Dean's personal space.
"Here, you try," Dean said, handing Castiel his pencil and the book he'd been baring on. "Just draw the first thing that comes to mind. Anything at all."
Castiel immediately set to work. His hand moved easily and fluidly as he intently worked on his new project. Dean leaned back against the headboard and resisted looking over Cas' shoulder as he drew. Despite of Jimmy having been somewhere in his mid thirties when Castiel took him as a vessel, the angel looked adorably childlike.
"How comes it?" Dean asked a little while later.
Castiel examined his worth before smiling too, just a little smile but enough to make Dean smile too. He passed the hunter the doodle, looking happy and proud of his work. The drawing was of Dean and Sam on a cloud in Heaven. They were more like stick figures than people. It kind of reminded Dean of what his drawings had looked like when he was five.
"What do you think?" Castiel asked nervously, clearly hoping for Dean's approval.
Dean forced a smile and wrapped his arm around Cas' shoulders. "It's, uh, awesome. That's a really great doodle you've got there."
Ignoring the odd look they got when Sam walked in, they doodled for hours until Cas finally fell asleep against Dean's shoulder.