Dean Winchester, captain of the football team, chick-magnet, car-genius, and the most popular guy in school. Not to mention the hottest.

Castiel sighed and walked into Mr. Roman's history class to find Dean sitting in his usual spot, in the back of the room with all of his jock friends, and Lisa Braeden.

Castiel hates Lisa, not because she's a bad person, though. Lisa is captain of the cheerleading team, she's a genius, and she's gorgeous. No one ever has anything bad to say about her because well, Lisa is perfect, without a flaw.

No, Castiel hates Lisa because she's Dean Winchester's girlfriend, not because she's popular, not because she's gorgeous, and definitely not because she's on cheer squad.

Castiel shook his head and sat down in his usual seat, right next to Chuck Shurley. Chuck is Castiel's best friend, they met freshmen year, they were both outcasts so they had decided to be outcasts together.

"Hey Castiel." Chuck says once Castiel sits down.

Castiel turns to face Chuck "Hi, Chuck."

"Hey Castiel" Meg chirps, tapping Castiel on the shoulder. Castiel jumps and turns his head to see a very determined Meg Masters.

Castiel groans "What is it Meg?"

Meg grins "I'm throwing a party this Saturday. You should come"

Castiel narrows his eyes "No."

"Did I mention Dean, the boy you're hopelessly in love with is going to be there?"

Castiel bites his lip "Do you have to talk so loud?"

Meg rolls her eyes "He didn't hear me, so are you coming or not?"

"He's not interested, and he's with Lisa. So, no."

"Lisa is going out of town, to someone's funeral, she'll be gone for a week."

Castiel opens his mouth to speak but Meg cust him off "That gives you plenty of time to get that dick to fall in love with you."

Castiel crosses his arms "Keep your voice down." Castiel hesitates "If I go will you leave me alone?"

"Not a chance." Meg says "See you Saturday."

Right before Castiel can respond Mr. Roman comes into class wearing a devilish smirk "Sorry I'm late, I had some important business to take care of."

Castiel notes everything Mr. Roman had to say. But throughout class Castiel feels like he's being watched.

About 30 minutes in Castiel finally decides to look and see who it is that's watching him, when he turns to look he sees Dean Winchester staring right at him.

When Dean notices Castiel looking back at him he panics and looks elsewhere. Castiel's face flushes and he goes back to taking notes.

#########

After school Castiel has to take a bus home because Gabriel had somewhere important to go and he didn't have time to take Castiel home first.

Castiel rolls his eyes at that, Gabriel is probably at home stuffing his face with the chocolate cake Anna made the night before.

Once Castiel got home he opens the door to find a lazy Gabriel napping on their $3,000 dollar couch.

"Gabriel!" Castiel yells, throwing the nearest pillow at Gabriel

Gabriel groans and snuggles close to the pillow Castiel just threw at him "Thanks for the pillow Cassy."

"Don't call me Cassy!" Castiel snaps, throwing a shoe at Gabriel

"Ow, what the hell Cassy?" Gabriel whines

"That's what you get for not picking me up for school, big brother." Castiel says, strolling into the kitchen. "We need food, make use of yourself and go to the store!" Castiel shouts from the kitchen.

Gabriel groans then ponders for a moment before answering "Fine. I've been meaning to buy more chocolate syrup and licorice anyway."

Castiel sighs and walks into the living room to discover that Gabriel is already gone.

#########

Gabriel strolls into the local market and heads straight to the candy isle

"My babies!" Gabriel nearly shouts

He loads his basket with sweets and decides to go get other food items for the rest of the family. He doesn't want to get yelled at.. again.

When suddenly he hears two familiar voices talking in angry tones. Gabriel can hardly make out what they're saying, he peeks his head out of the candy isle to see the Winchester brothers.

The younger brother looks defeated, he sighs and the older brother storms off to another part of the store.

Gabriel creeps up behind Sam

"Your brother is a douche." He said, grabbing a carton of milk

Sam stiffens but almost immediately relaxes, he turns around to discover Gabriel Milton standing before him, a basket of sweets in one hand and a carton of milk in the other. Gabriel is wearing his signature smirk.

Gabriel is a senior at his and Dean's school, as is Dean. Gabriel's younger brother Castiel is a junior but he takes 12th grade History and Math with Dean.

"Hey kiddo? Ya in there?" Gabriel says, poking Sam.

Sam jumps "Oh s-sorry." He stutters

"You alright, gigantor?" Gabriel asks, a hint of concern in his voice.

Sam bites his lip, he always tried to deny the fact that he had a crush on Gabriel. He barely even knew the guy, all he knew is that the guy loved pranking people, almost as much as he loved sweets.

"Yeah! Yeah I'm, I'm fine." Sam squeakes

"You sure?" Gabriel asks, standing up on his tip toes, putting a reassuring hand on Sam's shoulder.

Sam bites his lip before saying anything "I'm fine, thanks Gabriel."

Gabriel smiles and removes his hand "Alright, I'll see you at school tomorrow, kiddo."

Sam's face flushes, he runs off to find Dean so they could leave.

Gabriel comes back home with two bags of candy and one bag of stuff the others would eat

Castiel sighs "What took you so long?"

"I got distracted." Gabriel answers

"Got distracted with what?" Castiel asks, narrowing his eyes

"Nothing, I just, saw some kid from school at the store. We made conversation, simple as that." Gabriel responds, rolling his eyes.

"Who?" Castiel asks

Gabriel narrows his eyes "Why do you want to know?"

Castiel ponders his answer "I'm just.. curious."

Gabriel sighs "I saw the Winchester brothers, the older one was being a douche and the younger one looked pretty upset about it so I comforted him."

"What?" Castiel says, he almost asks about Dean but decides not too "Wait. You don't comfort anyone."

"There's an exception for moose." Gabriel answers before running upstairs with his candy.

Castiel doesn't know what Gabriel mean't by that, he isn't entirely sure he wants to know either. So he just continues to put the small amount of food Gabriel brought back where they were supposed to go.

Castiel does his homework then heads off to bed. He falls asleep with Dean on his mind, as always.

#########

Okay so, this is the first chapter to my first fanfiction, woo. Sorry if it's kind of sucky, it'll get better. Promise!