Flashing back to Halloween 1993 with the Winchesters. Truth be told, there were a lot of things Dean would rather be doing on the Saturday before Halloween than watching his little brother try to pick a costume for some lame-ass grade school party he wasn't even going to be able to go to.
When the Mask Slips
Truth be told, there were a lot of things Dean would rather be doing on the Saturday of Halloween than watching his little brother try to pick a costume for some lame-ass grade school party he wasn't even going to be able to go to. But Dad was out on a job (there was at least one werewolf out in this town) so someone had to watch Sam and handle the kid's Halloween thing.
Sam raised his head from the bag of costume possibilities he'd bought with the money Dad had given him. "Check it out!"
Dean pulled one of the headphones away from his ear and raised his eyebrows at Sam. "Did you say something?"
Sam sent him a blankly annoyed look and put in the vampire fangs. "Check it out," he repeated, and bared the teeth.
Dean hit the stop button and tried not to think about the fact that the hot blonde from his homeroom had a Halloween party that started in two hours. "No. Sammy. Not cool. Vampire's a stupid costume, anyway. Dracula was a pussy."
"He was not," Sam argued, sitting up straight. "He impaled people."
"Vampires don't impale people. They either kill them by sucking them dry or turn them into other bloodsucking freaks." Having successfully shot that one down, Dean sat back. "Try again."
Sam glared at him, but went into the bag and emerged wearing a skull mask. He only pulled it up when he heard Dean laughing. "What?" he demanded.
Dean shook his head, trying to stop smirking and instead talk. "What's so scary about a skull?" he asked.
"It's the Grim Reaper. I have the rest of the costume," Sam pointed out.
"Let me guess, you've got the Wolfman and Frankenstein in the dollar store bag, too."
Sam looked down at the bag. "Shut up," he said after a moment, shoving the vampire fangs into the bag.
Dean sat up and then went to the end of the bed in order to better see into the bag. "Do you seriously have Frankenstein in there? You're ten. You're short. No way you can pull off Frankenstein."
"Probably better for you anyway," Sam retorted. "Tall, stupid -- "
"Hey," Dean warned. "I'm in high school now."
"Anyway," Sam said pointedly, "There's a ghost in here -- "
"What?" Dean gave him a look when he realized what he meant. "White face paint or something? Makeup's for girls, Sammy."
Sam rolled his eyes, and realized after a second. "You said I should be Ace Frehley!" he protested.
Dean raised a warning finger. "KISS is different."
"No they aren't." Not wanting a slew of 'reasons Sam might want to wear makeup' jokes next, he looked into the bag, and volunteered, "The werewolf isn't bad."
"Oh yeah?" Dean made a grab for the bag, but Sam snatched it away.
Sam stood and grabbed his duffel bag. "I'll show you," he said.
Dean started to laugh, then saw Sam going for the hotel bathroom. "Wait, are you serious?"
Sam just raised his eyebrows and closed the bathroom behind himself.
First Dean checked his watch, then went to the window, checking as best he could where the moon was -- the sun was already down. Dad was probably hunting down and killing the werewolf already, and he'd come back to the hotel room, expecting to see both of his sons there.
Dad's orders. But Angie Preston was hot, and probably wouldn't mind if he showed up in "costume" (a leather jacket and tight jeans was a costume, right?) and kissed her with tongue. Totally the definition of dilemma.
"I told you," Sam said, his argumentative bratty little brother tone on, and Dean turned to look. He cracked a smile first, before he started to laugh.
"No freaking way," Dean managed, sniggering at all of the bad, fake fur covering his brother, the terrible mask, and worst of all, the flannel. "Dude. No."
Sam pulled off the mask. "You're a jerk," he concluded.
"Werewolves don't look like that, and you just look like you really, really want to hit puberty," Dean said honestly.
Sam dropped the mask to his side. "Do you have a better idea?" he asked.
"Yeah." After a moment of thought, Dean tossed him his leather jacket. "Lose the fur. Ripped jeans. Wifebeater. Screw with your hair. Bam, you're a rockstar."
He looked down at the leather jacket. "... But I thought you were going to -- "
"Whatever," Dean dismissed. "Chick's religious, it'll be lame anyway."
Sam nodded after a moment and ducked into the bathroom, leaving Dean to glance up at the full moon.
The house that Sammy's friend's party was at was only a few blocks away from the motel, so he sent him off and froze his balls off all the way back.
Dad was waiting there -- Dean had his hand on his gun until he heard John's voice, and saw him look out of the bathroom, his now-cleaned silver knife in hand. "Thought you'd at least wait for me before you left."
"Just a werewolf," Dean said, and put his gun under the pillow. "No problem. You're already back."
His dad was looking at him in a way he barely recognized; more like before Mom had died than anything since. No disapproval, no trouble, almost grateful. Weird. "Yeah," John said finally. "You mind picking Sammy up?"
He nodded immediately. "Yeah, no problem. Planned on it."
After a moment, John went to the cooler. "You going anywhere tonight?"
"Nothing good. Apple-bobbing and shit. Lame," Dean concluded.
As Dean watched, John brought out a beer, then, instead, two Cokes. "So what'd he wear?" he asked as he handed Dean the second can. "That stupid Wolfman thing?"
Surprised, Dean cracked open the Coke, and then grinned. "Nah," he said casually. "He's cool."