Author's Notes- Ok so I re-read Milton's vs Winchesters and decided to do a rewrite and hopefully it will turn out better with the grammar and all that jazz. Same basic concept thought I just switched up a few things. I am in such a writing mood so between this, my Sterek fanfic, and my Original work, I hope to keep my juices flowing. Destial and Sabriel main ships. High School A/U

I don't own Supernatural this is strictly for fun. Parts of me seriously wish I did though.

Chapter One- The Invites

It was a fairly warm afternoon in late October, so the short skirts fluttering by Dean as he lay outside on the bleachers wasn't a shocking or unpleasant surprise. He sits up, yawning, stretching his arms over his head exposing some on his abs to the crowd.

"Think they'll lift their skirts if you lift your shirt Winchester." Dean narrows his eyes looking to the left seeing his friend Jo hop up onto the bleachers. He puts his arms down as she comes over sitting next to him. She looks out over the football field with him as it beings filling up with students from Lawrence High.

"What's happening?" Dean scratches the back of his neck as he watches a couple more people walk by.

"Who man where have you been? Dean my brother from another mother it it's the Wednesday before All hallows eve. Time for our gods and goddesses to pass out the invited to the hedonistic heaven that is the Milton's." Ash says as he plops down behind Dean and Jo flipping his mullet off his shoulder.

"Already?" Dean's voice gruff from nonuse as he reaches into his backpack and pulls out a drink sipping on it. "I didn't think it was so close to that time."

"Time moving too fast for you Deano?" Jo questions taking his drink for herself. Dean just shakes his head and sees his brother coming out from the cafeteria with his girlfriend Jess carrying and extra tray of food.

"Thanks Sammy." Dean takes the tray when his brother gets close enough and Sam narrows his eyes at him but sits on the bottom bleacher with Jess by his side.

The crowd begins to quiet down as the two Milton's still remaining at Lawrence High headed out to the field, since all the others had graduated. There was six of them total but only two under the legal age to being doing half the shit that goes on at their parties.

The Milton's were Lawrence's answer to the Kennedy's or Baldwin's or any pop group put together over the last twenty some odd years. They are rich, athletic, intelligent and extremely good looking, everything that Dean and his group weren't. Some of Dean's group had a couple of those qualities but not all of them.

The oldest two, Michael and Raphael, ran the family business since their father had retired and moved to some island with his new twenty something bride. But this also meant that they wouldn't stop being rich anytime soon. Michael was a shred business man and Raphael his loyal puppy, doing whatever Michael said.

The first of the middle children caused the family great shame and Michael has been trying to rebuild a positive reputation around the town again. Lucifer Nicholas "Nic" Milton was currently in a maximum security prison for the murder of Karen Singer, Marley Singer and attempted murder of Bobby Singer, who were people all very close to the Winchesters. Marley had been like and older sister to Dean and Same, who Nic decided to kill after apparently being rejected too many times, her mother just got in the way. That was over ten years ago.

The youngest three Milton's were also the closest in age, a year or barely a year separating each of them. First was Gabriel who graduated last year but was still floating around the time, claiming he was taking some time off before going to college. He was smarter than any one gave him credit for cause is loud mouth and obsession with sweets are what sticks in people's minds the most.

Then there was the two positioning themselves in the middle of the field surrounded by their followers. Anna, there only girl in the group, was the Queen of the high school with her bitches Meg and Ruby following her everywhere. They were all seniors like Dean and Dean has had to fend off Meg more than one time. And Castiel who stood looking off to the side. Dean didn't know much about Castiel other than the fact that he was in Sam's grade and too smart to still be in high school. Dean watches the tall blonde behind Castiel lean forward, and Jo grumbles something about how creepy she thinks Balthazar is. Dean snickers.

Castiel moves away from the group and over to the side of the road as a white Porsche pulls up to the curve. Dean watches as Lilith, Ruby's other sister gets out and hands the hot off the presses invites to Castiel before kissing his cheek, whispering something then getting back in her car and leaving. Castiel walks back over to Anna and Anna brings handing the invites out.

Dean and his group never got invited and he was ok with it being that way. The only one who was allowed to go was Jo. But that was only because her mother worked as the Milton's cook during the day. She had practically grown up with them but thankfully she had better since to be friends with them at school, or at least that is what Dean thought most the time.

The group of five watch the envelopes get passed out as they eat their lunches. The Milton's are about done as the Outsiders were too busy talking to themselves to realize that Castiel had moved in front of them. He clears his throat, all of them stop talking and look at him. Dean's eyebrows nearly leave his forehead in shock.

"Hear Sam…Jess…" Castiel's voice made Dean question his sexuality. The deep tones went straight threw his veins down to his cock. Sam and Jess timidly take the invites to the party. Jess is gleaming with excitement. "Jo…Anna insists…Ashley."

"Yo dude…its Ash." He takes the invite, Anna only invited Ash because he is Jo's oldest friend and she really wanted Jo to show up at the last Halloween party should would be throwing.

Dean's eyes trace over all the invites in his friend's hands and his lips purses slightly. He looks up feeling Castiel's intense stare upon him. Dean shifts a little as Castiel tilts his head to the side slightly and there was no way that Dean thought it was cute. Nope. The rest of Dean's group finally realized he didn't get and invite. Sam was about to give his back to Castiel when Jess caught his hand glaring down at him daring him to continue.

Sam looks up at Dean apologetically and Dean just shrugs at him sort of letting him know it would be ok. Castiel lifts a brow and smirks. He turns on his heel as sees some random person who got and invite walking by. Castiel reaches out and pulls it out of his hand, the guy goes to get lippy but sees Castiel narrowing his eyes at him. He frowns walking off to mope. Castiel turns around and looks up handing the invite to Dean.

"Anna is going to kill me, but this only seems fair." Dean takes it and looks over at Jo who laughs and then he looks back at Castiel. "You better show up…all over you." Castiel stops looking at Dean's lips and looks at the rest of the group before walking off.

Jo busts out laughing "Looks like the littlest Milton has his eyes on you." Dean jerks his head to his left and glares at her just causing her to laugh more.