Work Text:
“I look ridiculous.”
You briefly paused your movements, stilling the brush against Castiel’s cheek, and turned your head. Despite your greatest efforts, you couldn’t fight the smile that crept up your lips. Initially, you had planned to reassure Dean, but he was right. He looked absolutely ridiculous.
Jack had insisted to celebrate Halloween.
They picked up on it recently somewhere — everywhere, really. The past few weeks, every shopping trip turned into long explanations as to why pumpkins, candy corn, and decorations were sold everywhere. As a nephilim, familiar only with a hunter’s life, they were having a hard time figuring out human’s customs to begin with. Holidays, they gathered, were rare and special. But Halloween in particular was confusing them greatly. As hunters they fought and killed monsters all year ‘round.
Vampires, werewolves, ghosts, those were all dangerous to humans. So why throw parties themed around them?
“Because it’s fun,” you had simply shrugged. And soon, Jack learned that you were right. It was fun. Dean throwing scary movie nights, Sam bringing in some candy because it was on sale, Castiel carving pumpkins to decorate the bunker with, and you introducing them to the wonderful concept of costumes.
“People dress up as monsters?” they asked with curiosity in their furrowed brows. You nodded enthusiastically, showing them some clips of make-up tutorials. “Can I try?”
The rest was history.
How the hell they managed to convince Dean to sit down and let them experiment with all sorts of colors and glitters was beyond you. Convincing Cas to sit still so you could paint some extra sets of eyes onto his face was surprisingly easy in comparison. He didn’t mind some harmless fun, after all. Especially when it thrilled Jack so much. Plus, his eyes lit up so prettily when you suggested a biblically accurate angel. But Dean? The guy was fighting his very instincts to smack the paint brush away from his scrunched up face, shifting uncomfortably in his chair.
Jack was focused, face stern and eyes flickering back and forth between the tutorial on your phone and their canvas. For their first time face-painting someone, they were doing a fantastic job, really. It was Dean’s antics that made it so difficult.
“If you keep squirming like that, they might poke your eye out,” you chuckled teasingly, the movement of your mouth slightly hindered by the fake fangs you’d stuck to your teeth. “I mean it might save us some fake blood, but…”
Dean threw a glare in your direction, grumbling something under his breath. Luckily for you, he couldn’t curse you when Jack was occupied flicking brush strikes across his lips, mimicking bloodstained teeth. You were beginning to understand why Dean agreed to this. At least he got to choose to be a cool zombie, all bloodied and tough. You made a mental reminder to yourself to tease him about the accuracy — something about how zombies carried more brains in their filled bellies than in their skull.
“Alright, kiddo, ‘s enough,” Dean huffed after a couple more minutes, overstimulated by all the swiping and textures smeared across his skin. He sat up, grabbing his own phone and angling the selfie camera accordingly. Surprise flashed across his green-stained and splattered with red features. “Damn.”
Jack swallowed, blinking at the hunter expectantly.
“This is awesome,” Dean beamed, grin childlike and eyes filled with glee, though he quickly covered up his excitement by clearing his throat. “I mean, good job.”
Filled with pride at the praise, Jack smiled from one ear to another. It stretched the painted teeth on the corners of their lips even further.
After watching The Nightmare Before Christmas with everyone — you thought it was the best movie to introduce someone to the concept of both Halloween and Christmas, two birds with one stone, two holidays with one classic —, Jack insisted to dress up as Tim Burton’s infamous Pumpkin King, their name-twin. It was a simple enough design, so you fulfilled their wish to your best efforts. And they pulled off the Skellington look effortlessly.
You did some finishing touches on Castiel’s makeup, convincing him that it was less about literal accuracy and more about having fun with it. He did insist on getting the multiple rows of eyes on him at least being the right color, though.
“Are you guys about ready?” Sam’s voice echoed through the doorway, the hunter appearing seconds later in its frame. “Popcorn’s getting cold.”
Jack turned to him, scanning him from head to toe. “You’re not dressed up.”
Sam stiffened, crossing his arms in front of his chest. To his assessment — the messy painting palettes, various brushes, and an unholy amount of makeup wipes — he dodged a bullet by offering to prepare the Dean Cave for movie night. It was no secret that he didn’t care much about Halloween, though he did agree to celebrating for Jack’s sake.
“I’m good,” he attempted, his nervous words accompanied by a subtle twitch of his lips.
“It’s not a costume party without a costume, Sam,” you argued with a pout.
“C’mon guys, he looks plenty scary,” Dean teased, grinning at his brother. “What’re you s’pposed to be? L’Oréal model? Rapunzel gone Lumberjack?”
Sam rolled his eyes, but before he had the chance to retort anything, Jack’s eyes lit up, even more so in the hollow illusion of the black eyeshadow. “How about a princess costume?”
While he pinched the bridge of his nose, through which he exhaled deeply, you chuckled softly and decided to cut him some slack. You undid the clasp around your neck, pulling at the strings. Walking up to Sam with red, satin cloak in one hand, and brush in the other, you tilted your head.
“Nobody can escape the festive magic, Sammy,” you giggled, throwing the fabric around his shoulders. First you tied it securely around his neck, then you used it to pull him down a bit.
“Hold still, Dracula,” you mumbled, haphazardly drawing little bats on his cheekbones. Something simple, but effective. Enough to satisfy Jack and not too much to annoy Sam, though the cold paint drying against his skin was already starting to itch slightly.
“There!” you smiled, “Now we’re matching.”
“And ready to party,” Jack chimed in with a joyous nod.