Set In AU

The Outcast

The Jock

The Nerd

The Bad Boy

The Beauty

Saturday Detention really couldn't be more cliche then that. 

Or, at least, that was what Charlie Bradbury was thinking as she sat in class, wasting a perfectly good Saturday that she could've been spending updating her fanfiction and bingeing Doctor Who. 

But NO. Stupid teacher had to give her Detention- on a SATURDAY. 

At least she wasn't alone. Charlie, the classified Nerd in this bizarre version of the Breakfast Club, was just one of five people. At the very back corner of the room was Crowley- Well, now that Charlie thought about it, she didn't even know Crowley's last name- our Bad boy. He was texting on his phone, looking like he was making dug deals or something, a smirk on his face. In the opposite corner, sitting on the window sill, was Dean Winchester, the Jock. His Letterman jacket was gone for the day, and replaced with a plain brown leather jacket that made the girls in Charlie's English class swoon. Our outcast for the day was Castiel Novak, the smart kid in Charlie's math class who was definitely challenging her for the Nerd title. But Castiel's family was weird and religious, and Castiel, everyone knew, was gay as Barry Manilow, thus earning him the title of Outcast. And finally, there was Jo Harvelle, the beauty. Oh, Charlie could stare at her all day, and so could nearly every male in the school, Castiel and Dean excluded, of course. Jo and Dean were like brother and sister.

"I expect you all to sit here today, and think about what you've done wrong." Ms. Naomi declared. "If you're here today, you've obviously disgraced your entire generation in some form, and I expect you to correct your ways by the time you leave." Charlie's hand shot up.

"What if we were falsely accused?" She questioned. 

"I wrote your detention slip myself, Ms. Bradbury, and I assure you, you have a lot to think about." The teacher shot back before grabbing her coffee mug and downing it like it was a shot of whiskey. "Not a word out of any of you, understood?"

They nodded. 

Ten minutes later, Charlie was ready to stab herself out of boredom. She glanced around the room. Dean was playing the knife game with a pencil, mouthing the words to some song as he did so. Jo was braiding her hair, looking just as bored as Charlie felt, Castiel was smiling, obviously off in some fantasy world, and Crowley was intently watching Ms. Naomi, until a bright smile crossed over his face. Charlie frowned at him, and turned, only to see Ms. Naomi's head drop onto the desk.

She didn't move again.

"What did you do to her?" Charlie demanded, whipping back around to stare at Crowley.

"Spiked her coffee with all kinds of sleeping meds." Crowley replied. "She'll be out for the rest of the day if we're lucky. Why? You mad, ginger?"

"Mad?" Charlie echoed. "Hell no- I'm disappointed it wasn't poison!" Crowley paused.

"I could arrange that."

"Go on."

"Could we NOT plot a teacher's murder right now?" Castiel asked.

"Why? Would you rather think about how 'you've obviously disgraced your entire generation'?" Dean asked, imitating Ms. Naomi with a scarily accurate impression that made Castiel burst out laughing.

"Well, my mom isn't gonna be here til four," Jo commented. "What do we do now?"

"We become the Breakfast Club." Charlie declared. Dean, Jo, and Castiel gasped.

"Oh my god, I was JUST thinking that." Castiel insisted.

"I LOVE THAT MOVIE!" Jo exploded.

"Don't you forget about me," Dean started singing. "I'll be alone, dancing and you know it baby,"

"Going to take you apart," Castiel continued it. "I'll put us back together at heart, baby. Don't you, forget about me."

"You are all nerds." Crowley announced.

"And PROUD OF IT!" Charlie yelled out. Castiel held out a hand, and she high fived him.

"So...." Jo began. "What'd everyone do to get in here?"

"You spill first, beautiful." Charlie insisted. Jo smiled.

"I spray painted the pentagram in the cafeteria." She announced.

"I knew it was you!" Dean proclaimed.

"Yeah, thanks, the devil worship really helps business." Crowley agreed.

"You work with Satan?" Castiel questioned.

"Why? You gonna crucify me, religious boy?"

"No, I wanna know who's the cutest hot gay dude down there." 

"Probably Steve. He's cool." Crowley offered. 

"Steve, huh?" Castiel wondered. "I'll ask him out in eighty years when we're both down there."

"What about you, goody-two shoes?" Dean asked. "Why are you here?" Castiel sighed.

"I was late to class."

"That it?"

"I was thirty minutes late, and I showed up covered in fake blood. My teacher didn't appreciate the Carrie cosplay." Dean laughed. "What about you, handsome?" Dean winked at him briefly.

"My kid brother pulled a prank on the principal, and I took the blame." 

"How come?" Dean shrugged.

"Better me in here then him." He insisted. "Saturday detentions go on your permanent record, and Sammy definitely doesn't need that."

"So you're taking the punishment, even though you did nothing, and your brother gets off Scot-free?" Charlie questioned.

"Hey- I never said he got off free." Dean commented. "I made him get a haircut." Jo gasped.

"NO!" She cried out. "Not Sam's hair!" Dean laughed evilly. 

"What about you, Satan's secretary?" Jo asked. Crowley shrugged.

"Nothing." He commented. "I just show up, be me, and they slap me in here. I'm constantly punished for nothing."

"Preach." Castiel muttered. "What about you, Charlie?" The redhead rolled her eyes.

"I am completely innocent." She declared. She pointed at the unconscious Ms. Naomi. "But this bitch is homophobic, and I knew it, so I screamed 'JOHN AND SHERLOCK ARE GAY AS FUCK' in her class at the top of my lungs, and she gave me detention."

"That is the best thing I have heard all week." Dean declared.

"John and Sherlock are SO gay though," Jo agreed.

"I dunno," Castiel insisted. "I kinda like Sherlock and Irene Adler- but only in the Robert Downey Jr. movies."

"I love those movies." Dean commented.

"Nu uh." Jo insisted. "Bendypole Snickersnatch or nothing."

"Are you even speaking English?" Crowley demanded.

"No, we're speaking Sherlock." Charlie offered. "Do you not watch it?"

"No." They all gasped and Crowley rolled his eyes.

"Whatever- how about we do something that's ACTUALLY interesting?" he insisted.

"Like what?"

"How about......Truth or Dare?"

"YES." Dean exploded. 

"Okay, weirdo." Crowley offered. "Truth or Dare?"

"Dare!" Dean proclaimed. 

"I dare you to drag Ms. Naomi down the hall and lock her in the janitor's closet."

"Done." Dean walked over to the desk and examined the teacher, trying to figure out the best way to move her.

"She's a bitch." Charlie insisted. "Make it painful." Dean shrugged and shoved the teacher out of her chair, grabbed her by the feet, and dragged her down the hall, dumping her unceremoniously in the Janitor's closet and shutting the door.

"Done!" He repeated. "Now, let's see.......Jo, truth or dare?"

"Truth." Jo offered. "I don't trust you." Dean thought for a moment.

"Is it true you like girls and guys?" He asked. Jo glared at him.

"Could ask you the same question." She shot back.

"Gotta answer it, Jo." 

"Fine. Yes, but I prefer girls." Behind Jo's back, Charlie was silently singing angelic music, looking like she had just won the lottery. The boys fought back laughs.

"Castiel, Truth or Dare?" Jo asked.

"Um.....Truth?" Castiel guessed.

"Is it true that your family hates you for being gay?" 

"Jo," Dean offered, sending her a look that clearly read 'not cool'. Castiel shrugged.

"Yes," He admitted. "But some of my brothers don't mind. Luci's got a boyfriend, so he doesn't care, Balthazar doesn't give a shit about anything other then his hatred for Celine Dion, and Gabriel is the only one who I'd say still cares about me." 

"Well, at least you've got someone in your corner." Dean insisted, smiling at him. Castiel smiled back shyly, and the game continued.

An hour later, the stakes had been raised, due to intense boredom. Having discovered a ship to sail, Charlie grinned wickedly.

"Dean, Truth or Dare?" 

"Dare," Dean said obviously. He never picked Truth.

"I dare you," Charlie smirked. "To kiss Castiel." Dean's eyes widened, mortified. Castiel looked like a deer in headlights.

"Um..." The outcast started to say.

"Oh don't be a wimp," Crowley crowed. "It's just a kiss."

"Kiss, kiss, kisssssss," Jo whisper chanted. 

Dean glanced over at Castiel, who shrugged.

"It's up to you," He offered, clearly not minding if Dean should choose to kiss him. Dean fidgeted slightly, then finally sighed.

"Screw it. I'm too gay not too." He admitted before turning, grabbing Castiel by the collar, and pressing their lips together as he shut his eyes. Castiel's eyes nearly popped out of his head, but then they slowly closed as he kissed Dean back.

They broke apart a moment later, and Charlie whistled as Jo howled like a wolf. Even Crowley was smirking. 

"Not bad, Cas," Dean whispered. Castiel's face went bright red and he bit his lip slightly, embarrassed, yet pleased.

"Your turn, Dean." Jo reminded him.

"Oh yeah, uh..... Crowley! Truth or Dare?"

"Dare." The king of hell insisted.

"I dare you to find us another game before this one gets too damn weird." A few minutes later, Crowley appeared with a Monopoly game set.

"Oh, here come the childhood flashbacks." Castiel muttered. "Everybody wants the damn Boardwalk."

"I remember playing this game with my sister." Charlie recalled.

"You have a sister?" Jo asked.

"I did." Charlie replied. "Until we played this game."

"Oh, this is nothing." Dean declared. "I once got knocked unconscious after playing Sorry with my brother."

"Sorry is the game meant to destroy friendships and families, Dean." Castiel told him. "You only play it with your enemies."

Nonetheless, they set up the Monopoly board, deeming Crowley, for some unknown reason, the banker. Dean called dibs on the car, naturally, and Charlie called the top hat.

"What?" She questioned. "I like fun hats."

"I WANT THE DOG!" Jo declared.

"No way!" Cas insisted. "I'm always the dog!"

"Not this time." Jo and Castiel locked eyes, and a moment later, they were fighting in the back of the room as Crowley dealt out the money, and Dean and Charlie organized the rest of the cards.

Deafeated, because Jo Harvelle will kick your ass, Castiel settled for the thimble, and the game began.

Three hours later, Crowley had six hotels and owned the Boardwalk.

"What, did you sell your soul to win a board game?" Charlie commented. Crowley laughed at that a bit too long in her opinion. 

Dean wasn't far behind Crowley, though, and he was in control of St. Charles place, which had a hotel, just as Cas landed on it with a groan.

"PAy up, Cas." He declared. 

"No fair!" Cas insisted. "I just lost $600 to Jo- I don't have the money for St. Charles!"

"Well, you should've thought of that before you rolled a six." Castiel counted out all the money he had, but he was still over a hundred dollars short.

"I'm bankrupt." He proclaimed. 

"Not so fast." Dean insisted. "Let's make a deal."

"I'm listening," 

"You can keep your money if you......" Dean smirked. "Take off your shirt." Cas's jaw dropped, and Charlie gasped.

"Strip Monopoly." Jo commented. "Me likey." 

"Things just got interesting." Charlie commented. "Off with the garment, Castiel!" Rolling his eyes, Castiel took off his shirt, ditching it on the floor behind them. Dean's eyes raked over the boy's bare chest, but said nothing as the game continued.

"$500 or your bra." Jo declared as Charlie landed on her space. Charlie smirked, sharing a devilish look with Jo.... And then she handed over the cash. Jo groaned. "Such a tease." She commented.

"$250 or two socks and a shoe." Charlie announced. Dean forked over the clothes, not wanting to part with his hard earned money.

"That snazzy tie, or a grand." Jo proclaimed. Crowley threw the tie at her, and Jo quickly ties it around Charlie's head like a bandanna.

"50 bucks, Dean," Castiel insisted. He blushed. "Or you could just give me your pants." He waited for the cash. Dean was loaded in monopoly money- $50 would be nothing to him. And yet-

Dean shrugged out of his pants, stripped down to his underwear. Charlie was shirtless, but, to Jo's dismay, still wearing all of her underwear. Jo was in a T-shirt, having lost her own pants and her bra- which was now owned by Charlie. Crowley was  down to a tank top and his black pants, being the person most willing to just hand over the money instead of stripping. Cas, to Dean's delight, was just one roll away from potentially losing his pants, rendering him just as bare as Dean.

"This is the best game of Monopoly I've ever played." Charlie insisted.

"No duh." Cas rolled, and Dean smiled slyly. 

"I demand your trousers, Cas." He declared.

"Or.....?" Cas asked tentatively.

"Or two thousand dollars." Castiel sighed. He didn't have that cash.

"No laughing." He ordered, which of course, meant that Charlie, Crowley, and Jo burst out laughing the second that Castiel dropped his pants, revealing TARDIS themed underwear.

Dean held back his laughter, focusing on the view of a nearly naked Castiel instead.

It wasn't until his own turn that Dean snapped back to the real world.

"$800 or strip nude." Charlie said evilly. Castiel's eyes widened.

"Oh NO. I don't want to see that!" Jo cried out. "Make him do something else!"

"Alright, Charlie agreed. "Dean- pay up, or..... Do Seven minutes in Heaven with Castiel." Dean glanced over, and Cas shrugged.

"I'm in if you are." He offered. "But this counts for my turn too."

"Deal." Charlie agreed. So Cas and Dean left the room, very aware that they were wandering the halls of their school in nothing but their underwear.

They stopped in one of the other classrooms, Dean locking the door behind them in case Charlie were weird enough to sneak in and take pictures of them or something.

Castiel blushed wildly as Dean stepped toward him, until he was pushed up against one of the tables.

"You know," Dean commented. "Your underwear's pretty awesome." Cas's face went even redder, but Dean distracted him by locking their lips together.

Meanwhile, it was Jo's turn to decide whether she wanted to lose her underwear, or remove her shirt and let Charlie and Crowley see everything.

"I'll offer you a third deal," Crowley declared, being nice for the first and last time in his life. "Strip, Pay, or do seven minutes in heaven with Charlie."

"You've got my vote for King of Hell 2020." Charlie proclaimed, grabbing Jo's hand and dragging her out of the room. Crowley rolled his eyes, alone with the board.

He took everyone's money, and started folding it.

Because the King of Hell knows origami, okay?

Seven minutes passed, and neither Dean and Cas nor Charlie and Jo had returned. Crowley knew better then to try and find them. So he put away the Monopoly board, knowing they'd never finish the game, and he sat on a desk, his new crown made of money firmly placed on his head as he started hacking into everyone else's phones.

As Crowley pulled up all of their contact info, let's just say a pair of Doctor Who themed underwear dropped to the floor, its owner sprawled out on a table, currently distracted by Dean Winchester's lips, amongst other things.

Charlie and Jo returned an hour later, only to find Crowley laying leisurely on the desks, crown on his head, a drink in his hand.

"Where did you-" Charlie started. 

"A king has his ways." He declared. "Oh, and all of our numbers are in everyone's phone by the way, and I took the liberty of starting a group chat."

"Does that mean you'll still keep in touch will us after today?" Jo asked. The thought had occurred to her- and to Charlie as well. No matter how great a day you had with someone, there was always the possibility of everyone resuming their old ways come Monday morning.

Crowley shrugged at them.

"Let's just say that a King needs subjects." Crowley offered. "And you two wouldn't make bad ones." 

"Aw, he loves us!" Jo declared.

"What? No-" Crowley's arguments were quickly cut off as Jo and Charlie wrapped him in a hug.

"....Dean?" Cas asked, his fingers tracing circles on the jock's chest.

"Yeah?" Dean asked, occupied as he played with Cas's hair.

"Are...... Are we even going to talk to each other on Monday?" Dean frowned, looking at him.

"Why wouldn't we?" Cas scoffed.

"Well, I mean- I'm the kid that nobody likes, and you're basically the most popular guy in the entire school. To be seen with me would destroy your entire reputation."

"Cas..... If being with you destroys my reputation, then I don't want it in the first place." Dean offered. "Hell, I've had more fun with you, Charlie, Jo, and Crowley today then I've had all year with anyone else that's considered popular." Castiel smiled.

"So....You'll still talk to me?" Dean grinned. 

"Of course. And," He hesitated. "If... If you'd let me, I mean.... I'd love to take you out sometime."

"On like a date?"

"Yeah." Castiel smiled broadly.

"I'd love that." 

"Good." Dean smirked. "What are you doing next Saturday?"

"Well, if you want, I can be right here."

"I can see it now- Saturday Detention hookups."

"How scandalous." Dean grinned.

"You know, the others are probably wondering where we are."

"Oh, I'm pretty sure they know exactly where we are and why."

"Still- we should probably head back and retrieve out clothes before they throw them out a window or something."

"Good point." 

"WELL, if it isn't the lovebirds!" Charlie declared as Dean and Castiel walked sheepishly into the room.

"Crowley hacked all of our phones by the way," Jo added as they picked up their clothes. Dean and Castiel froze.

"Oh, please tel me you didn't go through my internet search history." Dean whispered.

"That was the first place I went on everyone's phone." Crowley declared. "Some lovely websites on there, Winchester." Dean grimaced.

"So- we're all totally eating lunch together on Monday, right?" Charlie asked. "We could be the Lunch Club!"

"I'm in." Castiel agreed.

"Me too." Dean insisted, smiling at Cas.

"Definitely." Jo nodded.

"Ugh, fine, you peasants." Crowley declared. 

Four O'clock had arrived without them realizing it, and the group gathered up the rest of their belongings and headed for the school's entrance.

"Here," Dean offered, handing Cas his leather jacket. "You keep it."

"But it's yours-" Castiel started. Dean shook his head.

"I wanna see you rock it on Monday."

"It will kill half the girls in school if they see me with your jacket."

"Good." 

"We should have a sleepover." Jo insisted. "Binge Sherlock and Doctor Who."

"Definitely." Charlie grinned. "Oh! And we need to cosplay together."

"DUH."

"I need a better crown." Crowley commented as the monopoly paper one started to fall apart.

"We'll bring you a real, plastic one on Monday," Dean assured him. "Just don't steal anymore souls."

"But that's my job!"

They all laughed, and headed back to their individual homes, smiling for the rest of the day.

But later that night, as they all lay away in their beds, Charlie, Castiel, Jo, Dean, and Crowley couldn't help but feel like they had forgotten something.

"HELLO?!!?" Ms. Naomi's voice echoed through the empty school. "YOU KIDS ARE SO DEAD WHEN I GET OUT OF HERE!"