A/n: In celebration of my favorite holiday, I've decided to do a Halloween one! I will be posting this story every Saturday this month.

it's a teen!Chester story so there are no spoilers (unless you aren't aware of the boys' fear).

Thank you to anyone who checks this out.

Thank you LilyBolt and miXiZ for everything.

I don't own Supernatural or its characters

Ch 1

"Sammy. Sammmyyyyy."

Sam's eyes slowly cracked open at the sound of his name. The voice that called to him wasn't his father's or his brother's, in fact, he couldn't recall what it was about it but it sounded foreign and yet familiar at the same time. It took only seconds for the young teen to go from half awake to wide awake. A white face with blood red lips, razor sharp yellowing teeth, and a large red nose stared down at him with terrifying black buttons for eyes. The moment his hazel eyes had opened enough to actually see and his brain started to function, the sight before him sent the boy yelping and crawling as fast as he could backwards with his hands and feet. He ran out of mattress and landed with a thump on the floor between the motel's queen size bed and the wall, trapping the young teen. The face that had startled him was now coming around to fully block his way, causing Sam to back into the corner. He squeezed his eyes shut and whimpered with his body now curled into itself shaking. The clown let out a side-splitting laugh. The voice may not have been one he had recognized, but the sound coming from it now was one he would know anywhere. Sam cracked open an eye and watched as the hideous face was removed and a much less menacing freckled face with green eyes was revealed.

"Dean?" Sam squealed. The older teen was doubled over with his arms around his stomach as he continued to giggle, tears were rolling down his cheeks from his now slits for eyes.

"Oh man, you shoulda seen your face," the older brother said before exploding once again.

"You're a freakin jerk!" Sam snapped.

"Happy Halloween Sammy!" Dean said now back under control, a large childish grin on his face. He put his hand out towards the younger brother, but instead of taking the offered help, Sam used the wall to push himself to his still shaky feet. The whole time his infamous glare never left Dean. "Come on Sam lighten up, it's Halloween."

"So?" Sam retorted.

"So, it's a day for pranks, scaring the shit out of people, good eats, and my personal favorite, hot chicks in sexy costumes" Dean answered still in high spirits. He tossed the mask carelessly onto the younger brother's bed. Sam scrunched up his face and his eyes followed it until it flopped laying so that it's empty button eyes were staring up at the ceiling.

"Whatever," Sam scoffed.

"Don't be a spoil sport just because I got you good. You gotta learn to laugh at yourself a little Sammy." The younger brother climbed back onto his bed, kicked the mask off and onto the floor, and scooted over until he was sitting back to the side he had been sleeping on. He snatched up the book that was laying on his nightstand, and opened it to the page that was dog eared. "Oh no you don't," Dean said walking over and ripping the book from Sam's hands.

"Hey, give it back!" The younger boy yelled jumping to his feet.

"You aren't going to geek your way through this day."

"Give it back Dean!" The younger teen repeated reaching for his book. Dean simply held it out of the smaller boys reach.

"Sorry pipsqueak, I'm older, stronger, and taller than you."

"Dad says he thinks I'm gonna be taller than you when I'm done growing," Sam riposted taking an ego hit to his brother and pretending to have lost interest in his stolen book.

"Pfft yeah right, I'll believe that when I see it," Dean replied in disbelief. "You're the little brother, always have been, always will be."

"Maybe in age, but my height depends on genes," Sam explained with a bored shrug.

"Dad really thinks you'll be taller?" The older boy asked, disappointment edging into his voice. When Dean's arms dropped to his sides, Sam rushed at his big brother and tugged the book from his grip.

"Yep," he said with a small satisfied grin. He threw himself onto his bed and resumed reading.

"Whatever, I'm still always going to be the oldest, which means I'm always going to be right."

"Mhmm," Sam mumbled.

"Come on Sammy, we're hunt free, it's Halloween, let's go out tonight. Have some fun."

Sam peeked above his book at his brother.

"Go, have fun. I'll be here when you get home. Just, don't come back drunk or with a girl," he said returning his eyes to his reading.

"Hey that was one time." Sam once again glanced at his brother. "Ok maybe twice." The younger boy just shook his head and raised his book up higher as though in doing so, Dean would simply disappear. He marched over and snatched up the book once again.

"Dean," Sam warned.

"Listen to me," Dean started now that he had Sam's undivided attention. The younger Winchester crossed his arms over his chest. "There's this haunted house that's only open tonight. I was thinking we could go check it out, maybe hit up a few houses on the way." Sam noticed the hopeful gleam in his brother's eyes and eagerness in his tone.

"Then go," he said.

"You're coming with me," Dean replied.

"I've already told you Dean, I'm not interested. I'm not dressing up, I'm not going trick or treating, and I'm not going to some stupid haunted house. I hate Halloween."

"What? But you use to love it," the older brother countered.

"Yeah well, I guess hunting actual monsters just took the fun from it." Dean's face fell and Sam caught a glimpse of what he recognized as guilt take hold of his brother. He meant what he said, he couldn't stand or understand the holiday anymore, but he also could tell it meant something to Dean. He didn't know why it did, but the point was it did. "Alright fine," Sam huffed. "I'll go with you." He rolled his eyes with his arms remaining crossed and his tone nothing short of uninterested. His brother's face lit up.

"It's called 'All Hallows Scream.' It's a huge house where everything inside is all mechanical, no actors. Should be lame," he smiled.

"Halloween is lame," Sam grumbled.

"Alright, I'm gonna hop in the shower," Dean reported tossing the book to his brother as he passed on his way to the restroom. A mischievous smile spread across his face, unseen by the engrossed sibling. "Hey Sam, think fast!" Dean launched the clown mask at his little brother. Sam deflected it and was on his feet in seconds.

"Dean!" He yelled. The older brother ducked into the bathroom quickly shutting the door and locking it only seconds before Sam slammed his fits into it. Dean's uncontrollable chuckles could be heard only slightly muffled by the thin piece of wood that separated them. "Jerk!"

"Bitch!"