Because Chester's last name begins with a W, he gets the honor of showing the new kid, Sam Winchester, around the school. Sam seems all right, as far as new kids go. He doesn't talk all that much about himself, just that his family moves around a lot, and does this school have a library? Chester concludes that the new kid is a nerdy military brat.
It's the beginning of the school year, August has just faded away, along with the last of the heat. Sam is interesting for about a week or two, until something else happens and everybody loses interest and just accepts him as part of the class. Sam himself seems to be more than okay with being left alone. And so he is, until Colby High's resident bully, Roy Anderson, decides to actually grace them with his presence. He's probably out of stolen lunch money, Chester thinks.
Roy sets his sights on the new kid, no surprise there. Sam does his best to ignore him, just shoves past the bully when he demands lunch money and spews threats about toilets and “you better watch your back Winchester!” Honestly, Chester is impressed. Not many people have the guts to stand up to the unofficial king of the school. Kevin Jones, a senior, just like Roy, did stand up to him once. It didn't end well for him. He changed schools two weeks later.
Despite the fact that everybody knows that Roy Anderson is a grade a bully, no one does anything about it. Not the headmaster, not the teachers, not the students. Roy Anderson Senior, Roy's dad, is, unfortunately in Chester's opinion, the town's mayor. He does a whole lot of good for the town, but did a shit job in raising his son. Chester's mom shakes her head every time the Andersons arises in conversation. It is a well known fact that Roy's mother left when he was just a baby. Ran away with one of Anderson senior's staff members. It was a scandal that shook the whole town and the gossip lasted for weeks, even years.
The way Chester sees it, it sucks to be left by someone who is supposed to love you unconditionally, but you can't use the fact that you were abandoned as a reason to behave like a dick. Not that he'd actually ever tell Roy this to his face. He's not suicidal.
But Sam apparently is. The boy continues to ignore Roy's attempts at taking his lunch money day after day, and Roy, understanding that some of his loyal subjects (IE the terrified students of the school) aren't in fact loyal, declares war. Which basically means going after anyone who shows even the slightest hint of kindness towards Sam Winchester. After making sure that no one will come to the new kid's help, he goes after Sam himself. Chester only sees the aftermath of it, because he'd gone home directly after school that day, to help his mother with the grocery shopping and had left Sam on his own in the library. According to the rumor mill the next day, Roy and his goons had found Sam there, reading as the school closed down and most of the students had gone home. They had grabbed him, five against one, and dragged him to the toilets, where they proceeded to repeatedly give him swirlies. After destroying whatever books had been in his bag and the bag itself, the gang had ripped off his clothes and duct taped him to the flagpole out in the school yard. Basically, they had done every cliché that had ever featured in a high school movie. So much for originality, right?
The rumor mill got a little vague as to what had happened after the bullies had left Sam there by the flagpole. Sarah, who sits next to Chester in English, said that she'd heard from Adam that Sam simply had waited until his tormentors left and then cut himself free. With what, exactly, no one seemed to know. His lab partner Cheryl swore up and down that she had seen two guys – one of them Sam – when she had been on her way home from her friend Lizzie's house. Apparently the guy who wasn't Sam had cut Sam down from the flagpole and then hit him over the head. Unfortunately Cheryl hadn't gotten a good look at the other guy, as it had been quite dark at that point, but she was certain it wasn't one of Roy's lap dogs.
Sam, to the surprise of almost everyone, but especially Roy, shows up just as the bell rings for the last time the next morning. He doesn't look terrible, Chester wouldn't say, but something is definitely off. The only indicator that something happened is the black eye Sam is sporting and the fact that he carries a green plastic bag instead of his usual bag. Apparently he'd gone back to get his books, what were left of them anyway, because as he sits down bedside Chester he grabs his math book from the bag. It's dirty and torn in several places, missing pages, but Sam seems to have at least made an effort gluing the book back together.
“Hey, you alright?” Chester whispers, when their teacher turns his back for a moment.
“Yeah, sure,” Sam tries to smile, but it turns into more of a grimace.
“I...We'll talk later, okay?” Sam returns his attention to the teacher, who's explaining something. What, Chester has no idea.
As it turns out, later turns into much, much later. The never kind of later. Apparently Roy and his idiot followers found out that Sam Winchester didn't get the message and actually dared to show his face at school. Big mistake on Sam's part. They have just left math class, are about to split up to go to geography and chemistry respectively, when Roy corners them by a vending machine. The rest of his gang forms a half circle around them, and Chester just knows that this is going to end badly. The rest of the students in the corridor all freeze, like someone's stopped time. You can practically hear the chants of “Fight! Fight!” in the air. Chester swallows and takes a step back. Maybe Roy won't actually go after him, just Sam. His plan was to spend the rest of his high school years until Roy left under the guy's radar. Good job on that one, Chester. You deserve a pat on the back. Not.
Chester's been so lost in his own thoughts about how his life is now ending, that he doesn't notice that Sam has begun to talk.
“... won't be happy if you beat me up.”
“Why should I care your boyfriend won't be happy? Where is he, by the way? I've never seen your boyfriend,” Roy is getting all up in Sam's space now, forcing Sam backwards until his back hits the vending machine.
“He doesn't go here.”
“I bet he doesn't even exist,” Roy says.
”What's his name, then?”
”Dean,” Sam looks like he just realized he should've probably kept his mouth shut, but it's to late now.
“So this Dean is gonna be mad if we beat you up?” Roy asks and Sam nods.
“Did you hear that, guys?” Roy turns to the students standing around in the corridor “the fag's imaginary boyfriend is gonna be mad. I'm so scared I think I just peed my pants,” Roy turns back to Sam, draws his fist back, and punches Sam in the face, once.
“What are you looking at?” He looks at Chester before walking away, his crew following him like little lap dogs.
“Why did you do that?” Chester sits down on the floor, next to where Sam is leaning against the wall.
“Tell 'em you have a boyfriend.”
“I don't know. Just slipped out.”
“You know they're gonna find out there's no boyfriend,” Chester looks at Sam, who just shakes his head.
“I'll figure it out. Trust me.”
Chester doesn't understand how in the world, Sam is ever going to figure this out.
Of course, the subject the rest of the day is Sam's supposed boyfriend. Cheryl tells anybody who will listen that the guy who cut Sam down from the flagpole is his boyfriend. She swears they kissed, even though she forgot to mention that little piece of information the first time she told her story. Chester asks Sam, just to be sure, and Sam scoffs “No,” so that answers that question. The rest of the week is full of gossip and rumors about the boyfriend. Sam himself just shrugs and tells his new found group of friends that “you'll meet him someday.” Apparently having a boyfriend boosts Sam's popularity to new heights, even with the threat of Roy hanging over his head. Who knew. Chester has got to find himself a girlfriend. Stat.
Over a week later, Chester is just coming through the doors after yet another school day has reached its end. He's one of the first out of the doors, and he intends to get home as quickly as possible. He told Sam this, urging him to do the same. Chester has a feeling things are gonna get ugly soon. Roy and his gang spent the whole of lunch staring at Sam, like they couldn't wait to rip him apart. Sam did a good enough job of ignoring them, but when he disappeared for a short while between classes Chester almost feels his heart come up through his throat. Which is just ridiculous. Sam had just smiled when he got back from wherever he was, telling Chester everything was alright. Chester didn't really believe him, which leads him to where he is now, on the stairs outside the school. Chester's just about to say goodbye to Cheryl, when a shadow falls over him.
“Hey kid, mind telling me where I can find Roy Anderson and his buddies?” Chester looks up, cursing his short stature for the ten thousandth time, only to find himself looking at a really pretty face. A really pretty male face, to be more exact.
“Um...Yeah, sure,” Chester hears himself squeak, “They are probably waiting for gym class to end, so I'd try by the locker rooms,” The stranger, an older guy wearing an even older leather jacket, gives an unimpressed look at Chester's rambling.
“Why are they waiting for it to end? Why not just leave?”
“They're not the ones having gym, I think they...” Chester trails off, thinking it may not be the best idea to tell a stranger that his friend is about to be beat up, whilst he, Chester himself, was going home to save his own skin. Kind of hard to win the best friend of the year award if he admitted to such a shitty act.
“Walk me there, will you?” The older, sort of dangerous looking, guy says and starts walking the way Chester pointed out. He doesn't even wait, just expects Chester to follow him. Chester does, because he apparently has no survival instinct whatsoever. For some reason, the rest of the school seems to have the same idea. Everybody they pass stop what they're doing to watch the stranger stalk by and Chester running after him. It would be kind of hilarious if it was anyone expect Chester himself. He should've just said no and gone home when he had the chance.
When they've almost reached the locker rooms Chester spots Roy and his gang standing around someone outside of it. He knows it's Sam in the middle of that circle and it feels like everything stops. Chester the coward left his friend to the wolfs, his brain informs him. The stranger starts running, coming to a stop just before he runs straight into Roy.
“You Roy?” he asks, and Roy turns to him, obviously surprised that someone would dare interrupt him.
“Yes, and you would be?” It's clear to Chester and everybody else that the stranger made a serious mistake, but it's too late to stop him now. The circle around Sam has come apart a little during the interruption, and Chester can see Sam laying on the floor, holding his stomach, face screwed up in pain.
“Who I am? Don't you worry your little toad brain 'bout that. What matters here is you leave my b...oyfriend alone,” the stranger says. He kneels down next to Sam, checking on him. Roy's buddies are too dumbfounded to even react.
“His boyfriend?” Roy asks, “Where did he find you? The corner between Main and Jefferson?” Chester gasps. Main and Jefferson is the local hotspot for prostitutes and the like. The guy, the boyfriend, whoever he is, obviously knows this as well, because Chester can see him stiffen at the mention of the streets.
“You calling me a whore?” The boyfriend stands up again, his full height towering over Roy.
“So what if I am?” Roy says and Chester can see that this is throwing the boy off. He's used to getting his way no matter what and all of a sudden he's getting two no's in a row. There aren't many people who have stood up to Roy Anderson, and the few who have backed down quickly enough. And now, both Sam and his boyfriend have made it quite clear that they aren't going to let Roy walk all over them. That must hurt Chester thinks with glee. It's awesome to see Roy's ego brought down a peg or two.
“I'm not a whore, you...” the boyfriend begins, looking like he wants to rip Roy a new one. He's interrupted by Sam, who's begun to get off the floor, seemingly in a lot of pain. The boyfriend obviously decides that Sam is more important than some bully because he crouches down on the floor to help the younger boy up, grabbing his arms. By doing so, he turns his back on Roy, who takes advantage of the moment and aims a kick at the guy's head. The guy, in turn, let's out a sound of surprise, and loses his balance, landing face first on the floor. Roy grins, let's out a laugh, and turns to the ever growing crowd behind them as if this means he won. Then Chester blinks, and then the guy is standing behind Roy, holding a big ass knife in his hand. Uh oh. Roy seems to understand that something's not right by the way the crowd is not cheering, but instead lets out a collective gasp of horror. He turns around, sees the knife, and promptly loses all the color in his face.
The scene before him is not one Chester ever thought he'd see. Roy's buddies have all abandoned him, standing as far away from their leader as they dare. Roy himself is slowly backing away from the scary guy with a knife, who's looking like he's about ten seconds away from murdering someone with said knife. And then there's Sam, who, whilst still sitting on the cold floor, reaches out and pokes once at the back of his boyfriend's leg. The guy sighs, looking annoyed. He puts the knife in his pockets, seemingly turning his attention towards Sam. And then, in about less than a second, he turns right back around and punches Roy square in the face. Roy, who was clearly not expecting getting hit in the face falls backwards and lands on his ass. Why he wasn't expecting to get hit is a mystery to Chester, but oh well. Sam's boyfriend takes another swing, this time knocking Roy down so that he's laying on the cold stone floor, nose bleeding. The guy crouches down next to him, grabs Roy by the hair, holding his head up.
“The only reason you're even alive is because Sammy's too kind for his own good, I hope you understand that. You ever even look at him again, I promise you I'll come back. And I will make your insides become your outsides, got it?” He spits on the floor next to Roy's head.
It's two days after the big fight when Sam finally shows his face at school again. Everything is exactly as it was before, except the fact that Roy isn't around, and his gang keeps to themselves now, doing surprisingly good without their leader. Sam's bombarded with questions about his mysterious boyfriend, as is expected. Chester admits that he's curious, and tells Sam that if anybody should know anything about the boyfriend, it should be him, considering they're such good friends. Sam just grins and tells him;
“We broke up. Turns out neither of us were all that into incest.”