AN: This is my first ever Supernatural story, and I wrote this instead of sleeping. It's going to be a work in progress, but I don't know how many chapters I'll write. Hope you guys like it! Let me know. :)


What. The. Fuck.

Dean stared hard at the F at the top of his paper, scrubbing his face with exasperation. Shit. He knew he hadn't written a masterpiece, hell, he almost forgot to write the damn thing between hanging out with Lisa and football practice.

But an F?

He was certain he had at least scraped a C- out of it, even in his haste to finish it. He may not be the world's best student, but Dean Winchester could fucking write. It wasn't his fault that he was exhausted. His dad had been gone for weeks, and he had been precariously balancing his time between football, girlfriend, and Sammy.

He hadn't even eaten dinner the night before, barely managing to feed Sam before passing out on the couch with his shoes still on. He had jolted awake at about 5 am, noting that his little brother had covered him up with a blanket before he had gone up to bed. He had smiled and shook his head before getting up to start his day, opting to let the kid sleep in a little longer than usual in return for the blanket.

F.

Dean sighed, finally tearing his eyes from the grade to the much more terrifying "See me after class". He swallowed a wave of anxiety, his mind flashing to his coach's threat to "kick his ass back to Kansas" if he didn't get his grades up.

Great. Not only was he now failing English, but now he had to stay after class to discuss his failing grade, which would make him late for practice.

He was so screwed.

The period crept on longer than was strictly necessary, and Dean glanced anxiously at the clock, dreading the sound of the bell signaling the end of class. Despite his glare, the hands ticked on until his classmates began to shuffle out around him. He only had a moment to collect himself before he heard the scrape of a chair being turned around and the clearing of a throat.

"Mr. Winchester."

Dean's ears tinged with red at the mention of his surname. Now he was really screwed.

He dragged his eyes up from the paper tainted with red pen marks, his bright green eyes meeting clear blue, "M-Mr. Novak."

Castiel Novak was much younger than most of the faculty in this school district, but he took his job very seriously. Students often snickered at his seemingly self-imposed dress code of a button-down white shirt, black slacks, and blue tie, not to mention the fucking trench coat that he kept folded on his desk until the end of class.

Despite their teasing, Mr. Novak was an unspoken favorite in the eyes of his students. He had the ability to take even the driest material, and bring it to life for his students, engaging even the most stubborn minds. He always greeted his students with a smile, clapping them on the back with warm enthusiasm after a well-presented report or answer.

He did not use last names. Ever.

"Mr. Winchester, I'm sorry to have to keep you, but we need to discuss this," he sighed, tapping the paper with obvious disappointment.

Dean sheepishly ducked his head, staring at the grade with enough intensity to set fire to the evidence that he failed, remaining silent.

"Dean," Castiel began with hesitation, "I really don't understand how things have gotten to this point. You do realize that I will have to contact Coach Singer and inform him that you are now failing my class?"

Dean swallowed hard, still refusing to make eye contact.

Dad is going to kill me, he thought with a twist in his gut.

He chose to ignore that particular train of thought for the moment, realizing that his instructor was still waiting for an answer. He cleared his throat, trying to sound more confident than he felt, "Y-yeah. I know." He could feel the other's eyes on him, his body tensing at the uncomfortable attention. He hated being stared at.

He jumped as he felt a hand suddenly appear on his shoulder, banging his knee off the desk when he flinched, "Shit! I mean-uh, ouch?" He grumbled, rubbing at the tender spot on his knee.

Castiel immediately withdrew his hand in concern, "Christ, Dean! Are you alright? I didn't mean to scare you." He furrowed his brows, managing to gaze even more intensely at the teenager before him.

Damn it, Cas. "Yeah, I'm alright," he said gruffly, wincing as be continued to clutch his knee, waiting for the pain to pass. "I uh, just wasn't expecting that is all."

Giving Dean a once over to assess for any further damage, he sat back in his chair, satisfied. "My apologies, Dean." He offered his palms up in peace, and then allowed them to fall back to his thighs where they had been resting before.

Dean's eyes involuntarily tracked the movement, quickly glancing away as he realized that he was glancing at a dude's thighs. What the fuck?

Castiel regarded him in silence for a moment before leaning forward in his chair once more, "Dean... You know that you can talk to me about anything, right?"

Dean's head snapped up in surprise, suspicion clouding his face momentarily before nodding in agreement. "Yeah, I know. It's just that there's nothing to tell."

And even if there were, he still wouldn't tell him.

"It's just that," Castiel began carefully, "this isn't like you, Dean." He tapped the paper once more, as if Dean needed another reminder of his failures.

Dean shrugged, looking down at the worn spot in his jeans, refusing to meet the piercing blue eyes of his teacher. "Things have just been kinda crazy lately with football and everything. Coach thinks we have a shot at the playoffs this year, so he's been pushing us harder."

"I get that, Dean. But don't you realize that your schoolwork is important, too? I'm sure you've heard the 'back up plan' speech before, so I'll spare you, but do you really want to jeopardize your future?"

Dean felt the sting in his gut, shuffling his feet as he stared dejectedly at the floor. Of course he knew how important it was, that's why he always made sure that Sammy's work was done before he even considered thinking about his own. That kid was going places. He sighed, hanging his head in shame, "No, sir."

Castiel snorted, "Damn it, Dean. You know how I feel about being called sir. It reminds me of my ridiculous brother." Castiel's brother taught the business courses, and as far as Dean was concerned, Michael Novak was a pompous prick.

"Right. Yeah. Sorry," he muttered, rubbing the back of his neck. He glanced up at the clock, heart dropping as he realized he was already ten minutes late for practice. He should be dressed and on the field right now. Shit.

Cas followed Dean's gaze toward the clock, shifting his attention back to the matter at hand. "Well, Dean. I don't see how a student that possesses collegiate-level writing capabilities suddenly goes from leading the class to failing, but seeing as you're fine, we need to talk about what comes next," Cas adds, throwing air quotes around 'fine'.

Dean shifts his attention back to the man in front of him, icy dread ripping through his gut in anticipation of what came next. Please don't say it. Please.

"Normally, in a situation like this, you would be kicked off the football team and placed on academic probation," he began, leaning back in his chair to watch his student. "However, seeing as you are more than capable of passing this class, I'm willing to make an exception."

Dean's jaw dropped, staring up at his instructor in confusion, "A-an exception? What do you mean?"

Castiel rolled his eyes, "I mean that I'm going to give you a second chance to pull your grade up, Dean. Here's the deal. I will provide you with a set of alternate assignments that you will have to complete in addition to your regular coursework."

"Wait, like extra credit," Dean asked incredulously. More work to do? How was that going to solve his problems?

Castiel considered this for a moment, then nodded in agreement, "In short, yes. The difference is that these will be required, Dean. If you do not complete these assignments and do well on them, I will have no choice but to fail you."

Dean's heart sank in despair, there was no fucking way he was going to be able to accomplish extra work on top of his already overdrawn schedule. "What... what do I have to do?"

"Your assignments will be due every Monday. You and I will meet after class every Thursday to discuss your progress," Castiel stated with a matter of fact smile.

Every Thursday? Thursdays were the days he spent with Lisa since he didn't have practice. She was going to be pissed.

Castiel must have noticed his internal struggle because he snapped his fingers, pulling Dean from his thoughts.

"I mean it, Dean. This is non-negotiable. Please don't make me be the bad guy here," Castiel sighed in frustration. "You are capable of so much more, and frankly I think you need to pull your head out of your ass to see it."

Dean snorted, taken aback by the comment from the usually calm and collected Castiel Novak, "You sound like Coach."

Castiel rolled his eyes once more, smirking, "Good. Maybe now you'll get it through that thick skull of yours." He stood, shaking the tension from his limbs before turning toward his own desk to retrieve another paper.

"This is your first assignment, Dean. It should be an easy week for you seeing as you're only reading Chapter 7 in class. I expect you to knock this out of the park, Winchester."

It was Dean's turn to roll his eyes, chuckling as he accepted the paper from the other man, "Dude, that's baseball. Not football."

Castiel waved his hand dismissively, "Same difference, Dean. It's all the same. A big fuss over a ball and much more sweating than is strictly necessary." He shuddered in horror at the thought of having to be in a situation like that, opting to surround himself with literature and art instead.

Dean recoiled as though he had been slapped, trying to wrap his head around the audacity of this guy that just compared football to those long-haired douchebags in their stupid pants.

Pulling himself together, he sputtered, "The same? Dude. There is no freaking way. Have you ever even seen a football game?"

Castiel shook his head and shrugged, "Not necessary. I prefer to surround myself with the arts. Besides, I was never really a fan of... physical activity."

He wrinkled his nose, thinking back to all the times he had puked while attempting to run the mile in gym class. Don't get him wrong, he was fit, and he had a decent build of muscle as a result of his frequent hikes. He preferred to read when surrounded by nature.

Dean stared at him taken aback by his complete and utter lack of experience in the best thing in the world, "Are- Are you serious? Dude, you've gotta come to a game. You can cheer us on, show your school spirit and all that jazz."

Castiel scoffed, sweeping the rest of his belongings into his bag before realizing that his student was looking at him with utter sincerity.

He sighed, gesturing to the door for Dean to exit the room, "I'll tell you what, Dean. You make a real effort and pass this class, and I'll try to make an effort to come to one of the games."

Dean grinned in triumph, stepping into the hall before glancing back at his instructor, "You're on." With one last smirk, Dean was off, hustling to get to what Cas could only assume was practice.

Cas sighed, flipping the light switch off in his classroom before heading toward the parking lot. "Damn it, Cas," he grumbled to his reflection in the rear-view mirror, "what did you just get yourself into now?"