This is super old and unfinished (and may never be finished just to warn you) but it was a really strong Ouran/SPN headcanon i had. Enjoy :)
"This place has four libraries; you'd think one would be quiet." The boy huffed, exasperated at the behaviours of his classmates. All he'd wanted was to find a quiet room to study and even after visiting all four libraries, had no luck. Finals were approaching and there was no way he'd let himself fall behind. He trudged up towering stairs, slouching in his scruffy uniform.
As he walked along the hallway around the back of the school, he found himself gazing out onto the ornate courtyard in thought. "How're things in heaven, Mom? I can't believe it's been ten years already," he asked wistfully approaching a set of broad doors at the end of the corridor. "I'm beginning to think rich kids only come to school to have a good time." He raked his hand through lengthy, chocolate locks in exasperation before reading the sign above the door. "An abandoned music room, the only place I guess I'll be able to study in peace and quiet." As his hand pushed the door, he peered inside nervously in case there was anyone else inside.
"Welcome to the Host Club," multiple voices chorused as rose petals fluttered around the group of strangely handsome guys. What did he get himself into?
.
Only those with excellent social standing and those from filthy rich families are lucky enough to spend their time here at the elite private school: Angel Academy. The Angel Host Club is where the school's handsomest boys with too much time on their hands entertain young ladies who also have way too much time on their hands. Just think of it as Angel Academy's elegant playground for the super-rich and beautiful.
.
"This is a host club?" He groped for the door handle out of embarrassment, scrambling desperately to leave as he pressed himself against the door.
"It's a boy!" They seemed so surprised to be visited by a boy.
"Ezekiel, Samandriel. I believe this young man is in the same class as you, isn't he?" This member had an evidently British accent as he asked the two to his left.
"Yeah but he's shy. He doesn't act very sociably so we don't know much about him." They both replied in sync, raising their hands to emphasize their not knowing. A smirk stretched across his face.
"Well that wasn't very polite," he turned to look at the newcomer who was frozen at the door in embarrassment. "Welcome to the Angel Host Club, Mr Honour Student."
"What?" The guy in the centre leapt out of his seat, staring intently at the scruffy teen that was watching the exchange. "You must be Sam Winchester!" At that the boy resumed tugging at the doorknob, desperate the escape this creepy den of debauchery. Continuing to stare, the short guy continued with his revelation. "You're the exceptional Honour Student we've heard about!"
Sam Immediately stopped, whipping his head around to face the other student, towering over him with his sasquatch-like height.
"How did you know my name?"
"Why, you're infamous. It's not every day that a commoner gains entrance into our academy," the British guy explained causing Sam to shudder at the use of the word 'Commoner'. "You must have an audacious nerve to work hard enough to fight your way into this school as an honour student, Mr Winchester." Again, Sam shuddered at the term 'Audacious' before composing himself slightly.
"Well, thank you. I guess…"
"You're Welcome!" The flamboyant teen who had stared at Sam before interjected. "You're a hero to other poor people, Winchester! You've shown the world that even a poor person can excel at an elite private academy," he explained nobly, using over-exaggerated arm gestures and wrapping an arm as best he could around Sam's shoulder. Shuffling away uncomfortably, Sam scurried to the other side of the room, away from this crazy man. "It must be hard for you to constantly be looked down upon by others."
"I think you're taking this poor thing too far," Sam responded, visibly irritated by the overzealous boy who continued his speech as if Sam hadn't said a thing.
"…Spurned, neglected, but that doesn't matter anymore. Long live the poor! We welcome you, poor man, to our world of beauty!" He emphasised the last word with a sprinkle of even more rose petals which caused Sam to shuffle back towards the door in aggravation. He was not going to stay here another minute!
"Hey, Sammy! You must be like a superhero or something! That's so cool!" A surprisingly short figure pushed himself to the front, tugging on Sam's sleeves.
"I'm not a hero, I'm an honour student," he complained before something clicked in his mind. "Who're you calling Sammy?" Sam was now shaking in annoyance at this clown factory.
"I never would've imagined a famous scholar would be so openly gay," The teen from earlier speculated causing Sam to stare over his shoulder at the boy.
"Openly what?"
"So tell me what kind of guys you're into," He gestured at the guys behind him. "Do you like the strong-silent type? The boy-Lolita? How about the mischievous type? Or the cool type?" Sam began to mumble nervously, backing away from the crazy guy.
"I was just looking for a quiet place to study!" A hand reached for Sam's cheek as the teen leant his face closer.
"Or maybe, a guy like me. What do you say?" Sam suddenly tugged himself back, launching into the display behind him before a loud smash sound resonated through the room. All he could do was stand there in shock as shards of porcelain spread across the floor. The twins Ezekiel and Samandriel (the ones the short guy had gestured to as the mischievous types) leant towards Sam, trying to be as intimidating as possible.
"We were going to feature that vintage renaissance vase at an upcoming school auction!" The one to the left moaned.
"Oh now you've done it, commoner, the bidding on that thing was supposed to start around eight million bucks!" Panic flooded through Sam's body as the realization hit him that he suddenly owed these guys eight million dollars.
"I'm going to have to pay you back…" The nervous edge to Sam's voice was increasingly audible.
"With what money? You can't even afford the proper school uniform!" The two once again spoke in unison.
"What's with that grubby outfit you've got on anyway?" One fell silent at this point as the British guy picked up a piece of shattered vase, examining it carefully.
"Well? What do you think we should do, Gabriel?" He stared at the teen who slumped himself into the throne he was sitting on when Sam had entered causing him to shudder at the sudden change in the leader- Gabriel's demeanour.
"There's a famous saying, Mr Winchester," he pointed at Sam for emphasis before continuing. "When in Rome, do as the Romans do. Since you have no money, you can pay with your body," he paused, eyeing Sam seriously. "That means starting today; you are the Host Club's dog!"
Sam froze at that sentence, staring upwards. "I don't think I can handle this, Mom," he whispered. "I've been captured by a bunch of boys who are calling themselves a Host Club!"