Author's Note: Can you believe it's been almost a year since this story was created? And it's still getting more and more popular with every installment? The concept is mind-boggling when I think about it-that people are willing to put up with my procrastinating, writing errors, and painfully slow plot (though I do have to admit, your anguished Destiel cries are going to be answered in the next few chapters or so...)-and this story has turned into a stunning work of art because of dedicated readers like you. Thank you for the support. It means more than you could ever imagine.

Monday morning came sooner than expected, but Dean couldn't find it in himself to complain. Mostly because that particular Monday morning guaranteed a whole afternoon spent with the ever puzzling Castiel Novak, but Dean chose not to dwell on that fact (and how it made his stomach erupt in gay butterflies) for the sake of his stubborn denial.

Honestly, with everything going on and distracting him, he would've completely forgotten about his detention if his mother hadn't come in his bedroom early that morning and woke him up to tell him that she'd cooked breakfast (side note: his mom was awesome).

"You leavin' soon?" Dean asked with a mouthful of omelet, not bothering to care about "manners" and shit because seriously, his mom had raised him enough to become immune to his faulty habits.

Though despite this reasonable justification, Mary still gave him the evil-eye at his impoliteness before she answered, "One of the workers couldn't come in today, so I picked up another shift."

"Their loss, your gain, right?" Dean said with a crooked grin. Mary rolled her eyes, trying to hide her smile by lifting up her cup of coffee and taking a hesitant sip.

"Wait, if you're leaving early," Dean began with a furrowed brow, "Who's takin' Sammy to school?"

"John has the day off today. He'll take him."

Dean snorted, "That'll be an interesting morning." Lately, all Dad and Sam had done together was fight like rattlesnakes. Sure, it was comical at times, but mostly it was just annoying as hell.

Mary sighed and picked at her last piece of bacon, "It's just a phase, Dean. Sam will grow out of it soon."

Dean arched an eyebrow, "How come I didn't go through that phase?"

Mary scoffed, "Dean, you worship the ground your father walks on. Not even your earlier angsty teenage years could get you to resent the man."

Dean shrugged in a silent form of agreement before he glanced at the clock and rose to his feet, "I gotta go, Mom. I'm almost late." With a quick peck on her cheek, Dean gathered up his things and bolted out of the door, walking towards the Impala.

When he was barreling down the street with the radio cranked to the max, Dean tried to convince himself he didn't spend the whole ride glancing at the sidewalk in a subconscious effort to look out for a familiar sighting of a trench coat.

(side not: He failed miserably).

When Dean entered Mr. Shurely's classroom and saw Castiel sitting at his desk with a slight smile on his lips, all tension he didn't know was there immediately evaporated. Smiling somewhat sheepishly, he plopped into the seat next to him, "Hey, Cas."

"Good morning, Dean," Castiel greeted politely, "I hope you slept well?"

Dean chuckled, "As good as I can with a mattress made of rock."

Castiel cocked his head, "I would hope your parents wouldn't force you to sleep on hard stone."

Dean scoffed, "No, Cas, they aren't sadists."

He shrugged, "Just making sure."

Dean smiled as he felt his gaze unwillingly drift to Castiel's tangled, tousled mess of hair, "Dude, do you even try to tame that beast?" Cas blushed faintly as his hands immediately went to his hand, wiry fingers threading through the bush of dark follicles in an effort to flatten the mass out when in reality all he did was make it worse.

Dean smirked and rolled his eyes, leaning over and batting Cas' fumbling hands away, "Here, let me." Cas gave him a skeptical look, which Dean so boldly responded by adding arrogantly, "Hey, trust me, I'm an expert at curing the fatal bed-head." Cas rolled his eyes but didn't openly protest, so Dean took the opportunity to tentatively thread his calloused fingers through the boy's hair.

At first, he was startled at how soft it was. Compared to Dean's cropped haircut and Sam's mop of hair, Cas' was like stroking a newborn kitten. But eventually, he overcame his shock, digging his fingers further into the surface. As he came to discover, the sensation of sliding the longer strands between his fingertips was actually a soothing activity and for a minute, Dean forgot what he was even doing in the first place. Clearing his throat, he shifted in his seat and started smoothing the hair out, his rough hands careful and gentle on the precious surface. In the back of his mind, he thought to himself how the silky strands reminded him of feathers. Feathers, he repeated to himself as his hand caressed the mop of hair, fitting for an angel. He lingered longer than necessary when the job was done, and even with a few minutes of crafting with his expert fingers, Cas' ruffled hair only improved a little.

"There, that helped some." Dean breathed out, not moving away but instead just marveling his handiwork, "Not barber shop worthy, but I think I did alright." When he lowered his gaze, he found himself staring into Castiel's eyes, the pupils so big that there was only a thin ring of blue left surrounding the black orbs.

Dean took in a sharp breath and immediately leaned away, putting a reasonable space between them before Cas—or himself, for that matter—got any ideas. He scratched the back of his neck and said, "So, uh...is that sketch you got of me done yet?"

Taking the hint, Cas released the rigor in his body and looked away, nodding as he replied plainly, "Yes, but I'd like to start another one…if you'd let me, that is."

Dean grinned and cocked an eyebrow, "Will I be able to see one this time?"

A corner of Cas' mouth twitched, "It's in the spectrum of debate."

Dean rolled his eyes, "Okay, I'm just going to pretend I know what that means."

Cas shrugged, "That's what I usually do when you make a quizzical pop culture reference."

He laughed, "Dude, I hate you break it to you, but your 'pretending' skills need a little work. Maybe don't tilt your head as much or look at me like I'm the stupidest person in the world."

"I will take those notes to heart," Cas huffed, getting out a fresh piece of paper quietly for a moment before adding seriously, "And I don't believe you're the stupidest person in the world. Trust me, there are many more deserving candidates for the title than yourself."

"Thanks, Cas." Dean scoffed before arching an eyebrow, "So, do you want me to strike a provocative pose this time?" All movement ceased in Castiel's body except his head, which snapped in Dean's direction to show the boy's shocked and terrified expression.

Dean smirked, "I'll take that as a no then. No biggie, I'll just sit here all studious and shit." He propped his head on an elbow and pulled the straightest face he could muster under the hilarity of the situation, "Like this?"

Cas snorted, "I would prefer a more natural pose."

"Okay," Dean leaned back in his seat, stretching his feet out on the desk in front of him and letting his head fall back, "This way I can catch some sleep when you're playing Michelangelo."

Cas didn't answer and Dean cracked an eye open, "You okay, Partner?"

He only received a glimpse of Castiel's glazed expression before the boy immediately flattened it into a straight face, his head bobbing in a nod as he cleared his throat, "Yes, that's suitable."

Dean gave him a thumbs up and closed his eyes again, letting out a sigh as all tension and coherence left his system. He'd stayed up late last night hanging out with Jo and Ash at the Roadhouse while his mother worked, and he was exhausted.

Dean fell asleep to the melodic sound of Castiel's pencil scratching against paper.

He was awoken by the shrill bell, snapping his head up in alertness and almost falling out of his chair. For a second, he was disoriented and confused, but then he recalled the earlier events of the morning and relaxed. He glanced over and saw Castiel's pencil and paper absent, but the boy was just staring at him with intent and something else on his mastered expression.

Dean cocked an eyebrow, "You been staring at me long?"

Cas shrugged, "For the last thirty minutes or so."

Dean let out a light laugh as he stood to his feet and ruffled Castiel's hair without much thought, destroying his hard work (though he had to admit, he liked it tousled like that anyway), "You're so weird, Cas."

Cas cocked his head, "Is that a good thing?"

"Hell yea, it's good." Dean told him with a grin, joining Cas as they walked out of Mr. Shurely's classroom, "Other people, they're either just really freaking boring or completely nuts. You're neither."

Castiel glanced at the ground, a smile blooming on his mouth despite his obvious attempt to push it down, "Thank you, Dean. You, too."

Dean huffed, "No way, Man. I'm barely a blimp on the map compared to you."

"I wouldn't count on that." Cas muttered, and Dean opened his mouth to assert his statement when Benny's southern drawl made its untimely appearance.

"Hey, Dean," His friend greeted with a smile, smacking Dean on the back, "What are you doin' here so early? Usually, you're not even up by this time."

"I've been sentenced to unjust detention by the Wicked Bitch of West." Dean informed him with a glumness he didn't really feel.

Benny rolled his eyes, "How tragic. I bet you were framed too, right?"

Dean winked, "Always, Dude." Benny let out a chuckle, and Dean turned to introduce him to Castiel only to find the trench-coated boy gone, somehow slipping away and fading into the background in just that short amount of time.

"Who are you lookin' for?" Benny asked, causing Dean to glance over back at him.

"My friend, Cas." Dean answered, sweeping the crowded area fruitlessly again just to make see if he'd missed him or something.

"Cas...as in Castiel?" Benny said, eyebrows shooting upward, "You mean the kid you humiliated at lunch the first day?"

Dean sighed, rolling his eyes, "Yeah, yeah. I was an asshole, but we're friends now."

Benny raised an eyebrow, "Just what have you been up to these last few days, Brother?"

Dean let out a light chuckle, rolling his eyes as he replied, "Complicated shit, Benny, that's what."

Benny didn't laugh but instead just leaned in, saying lowly in his ear, "Dean, Alastair's lookin' at you. I don't know what you did and I don't care, but he's pissed. Like, royally. It's probably best for you to lie low for a little while."

"I'm not afraid of that dick." Dean proclaimed sternly, though there was a tight pit in his stomach that said otherwise.

"I'd be, if I were you," Benny said, pulling away to gaze at him evenly, "Just be careful, Dean. Don't need you spendin' senior year in the hospital."

Dean sighed and rolled his eyes, "Yeah, yeah. Come on, we better get to Mr. Henricksen's so the ass can't find another way to send me to Naomi's lair."

"She's a principal, Dean," Benny reminded him in an exasperated voice, though there was humor sparkling in his eyes, "Not an evil mad scientist."

Dean raised a warning finger at him, "One day, she's going to slice all of us open and put grasshoppers in our livers, and you'll look back on this day and regret not believing me when you had the chance."

Benny arched an eyebrow, "Grasshoppers, huh? I'm more of a beetle person myself."

Dean chuckled, "C'mon, Jackass, let's get to class."

"So Clarence, what's up with the sunshine demeanor?" Meg asked him as they walked together down the bustling hallway, crinkling her nose in disgust as she added, "This whole happiness aura you got goin' on is really dimming my usual 'fuck the world and all who inhabit it' attitude."

Cas let a corner of his mouth twist upward in amusement as he said soberly, "My apologies, Meg. I would hate to diminish your perpetual destructive view of the universe."

Meg grinned at him as she pinched his cheek teasingly, "It's fine, Feathers. I'm sure you can repay me for it somehow." She punctuated her innuendo with a suggestive wink, and if he hadn't known her or her whole-hearted devotion to Balthazar for the last three and half years, he would've believed she was serious about her offer.

But fortunately, he did have the privilege of knowing her for that duration of time, and he only replied with an exasperated eye roll and a half-hearted reply, "Yes, I bet."

"Just say the word, Angel Cakes, and I'll be all over you like Balthazar on a Broadway performance of Jersey Boys." Meg told him with a smirk, a slight twinkle in her eyes when she mentioned her boyfriend.

Castiel scoffed at her claim but nevertheless allowed a calming silence settled over them. All the while, Cas couldn't help but silently debate whether or not he should reveal a certain person's disturbance the day he was out with Dean. Meg wouldn't be pleased to know how or why Crowley found him, and he was certain she would go straight to Balthazar with this newly required knowledge even if he told her not to.

And while he wished his two protégées would mind their own business when it came to that part of his life, Cas wasn't able to hold back any sort of secret from them. Not after all the inconveniences he pushed upon them over the years of their mutual friendship.

So when they reached his homeroom and Meg started to depart to go to her own, he gripped the crook of her elbow and pulled her to a stop, blurting out lowly before he could change his mind, "I saw Crowley this weekend when I was with Dean."

He felt tension seize her body as she met his gaze, her beautiful brown eyes widening in fury and fear, "What did he want?"

"What do you think?" He responded sarcastically as he let go of her.

Meg's jaw locked in place as her eyes narrowed, "You don't think he'd actually—"

"I don't know," Cas answered stoically as he glanced around nervously, not wanting her to finish the implied train of thought so publicly, "I mean, I'd like to believe he wouldn't, but you know Crowley. He can be...surprising when desperate circumstances arise."

Meg bit the inside of her cheek as her hands clenched into fists, "I swear to God, if he screws you over, I'll reach down his throat and rip his—"

"I know, Meg. Trust me, I know." Castiel said softly, sighing in despair, "Now you have to get to class. You know how Naomi has it out for you." Yet again because of me, he thought about adding but decided against it.

"I'm not afraid of that bitch," Meg assured him confidently as she patted his cheek in farewell, "Bye, Fly Boy. I'll make sure to give Balthazar a long, passionate kiss for both of us."

"Goodbye Meg." He said with much exasperation at her last sentence before turning away and entering the classroom, causing his female friend to fall out of his line of sight. Mr. Roman was too busy on his computer to comment on his unusual arrival time (he's usually much earlier than just a few minutes before the bell rings), so Cas took the rare occurrence as a gift from God as he slid into his seat.

"Hey, Castiel." An oddly familiar yet unrecognizable female voice greeted as he saw a flash of red hair out of the corner of his eye. For one irrational second, he thought it was Anna and felt a lurch in his stomach at the very notion of her presence. But obviously, he would've recognized her voice right off the bat, so who—

"You know, this whole 'greeting' concept is supposed to be a two-way street." Charlie Bradbury teased as she plopped down in the seat next to him, clearing away Castiel's confusion.

"Charlie," He began awkwardly with a formal nod as he outstretched his hand, "It's a pleasure to see you again."

Charlie smiled at his open palm but instead of grasping it to give him the proper handshake he was expecting, she just high-fived his hand, saying soberly, "Good to see you too, Dreamboat. Tell me, have you made any more men and women swoon with your almighty hotness?" Her grin widened as she rolled her eyes and added, "Besides Dean, of course."

Castiel cocked his head in confusion at her, registering her words but unable to make sense of them, "I, uh...Not to my knowledge, I suppose."

Charlie chuckled, her smile still remaining so perpetual and sincere that it unnerved him, "You're adorable, Blue Eyes. Anybody ever tell you that?"

"A few times," Cas admitted in an even tone, Gabriel's beaming image crossing his mind, and he immediately shut down his train of thought before Anna's face could inevitably appear, "Though some of them were more sincere than others." Before Charlie could comment, he stared at her intently and asked bluntly, "So what is it you wish to speak to me about? Something regarding Dean, I presume?"

At his cold change of pitch, her brow furrowed as she responded quizzically, "Just wanted to talk, Cas. Since you're gonna be spending more time with Dean-o, I thought we could be friends. In fact," A smile suddenly found the way to her lips, and Cas wondered if the girl could ever keep a straight face for a long period of time, "You and me got a lot in common."

Cas arched an eyebrow, interested in her claim despite his better judgment, "How so?"

"Well, we're both batting for the same team, we both have a killer fashion sense," She motioned to his suit and baggy trench coat and her own...colorful attire, "We love our exasperating Dean-o with all our hearts, we're a little too weird for society's standards..."

"…and we are both pining for people we cannot have." Castiel finished, intending to only innocently add to her list, but instantly recognizing his mistake when he saw Charlie's eyes widen and her grip on her pencil tighten.

She looked almost comically like a deer in headlights as she stared incredulously at him, "What are you—"

"Do you deny your romantic longing for Jo Harvelle?" He asked with a curious tilt of the head, puzzled at Charlie's shock of his obvious observation.

"Jo and I are just friends," Charlie told him sternly if not with an undertone of bitterness, "That's how it always has been, and that's all it will ever be."

"The same with me and Dean," Cas agreed softly, glancing down at his hands that had subconsciously clung together in a desperate grip without his permission, "We are the same in some aspects, Charlene. Especially that one."

He only looked back up at Charlie's hollow burst of low laughter, seeing an eerie mixture of certainty and jealousy in her expression as she replied, "That's where you're wrong, Cas. You—you had Dean the moment you said hello, Me—" She cut off and glanced away, "Not even years of patience and understanding can give me my Princess Peach."

Before he could think better of it, Castiel put a hand over hers, saying quietly and meaningfully, "Are you sure about that?"

Charlie smiled as she glanced back at him, but there was no mirth or amusement about it, "Not everyone can have a happy-ever-after, Dude. Especially not on the first try."

A stab of hurt and empathy pierced his heart, but before Cas could withdraw his hand and reply, Charlie gripped his hand and stared at him intently, all angst about Jo and unrequited love cleared away from her face (though most certainly not from her heart) as another protective gleam shined in her eyes, "Look, Dean is one of my best friends in the history of ever. And I'd rather forget to save my Pokémon game after winning a gym battle than see him get hurt..."

"I don't understand the reference." Cas told her in a mumble, but she ignored his lack of understanding.

"You won't hurt him, right?" Charlie pressed, her gaze searching his face for confirmation.

"I would never hurt Dean in any shape or form," Cas said without hesitation, not understanding why he had to say such an obvious statement, "Even if it meant destroying myself in the process."

His answer seemed to suffice because Charlie smiled and nodded her approval, releasing his hand and leaning back in her chair, her posture relaxing, "You're a cool dude, Cas. I oughta take you LARPing sometime."

"Larp?" He repeated slowly, "Is that another reference?"

Charlie stared scandalously at him like some sort of trust was violated, "You mean you've spent time with Dean on at least three different occasions, and he hasn't mention one of his fondest passions?"

"Fondest passion?" Cas repeated with a slight grin, getting out his notebook on Dean for English and readying his pencil, looking back at Charlie with a mischievous glint in his challenging gaze, "Tell me more." He knew by Charlie's sudden devilish grin that he'd hit the Holy Grail.

First period flew by quicker than it normally did, and it was all thanks to his new friend, Charlie Bradbury. For once, Mr. Roman had an ounce of pity in that black hole residing his chest masquerading as a main artery and allowed his students to complete their unnecessarily long and complicated assignment with a partner. Now normally, Cas would shrink into himself and complete it on his own, and he was prepared to do so. But apparently, Charlie meant what she said about being friends because the moment the teacher finished his announcement, Charlie connected her desk with his in one fluid motion.

"What do you have next?" Charlie asked as they walked out of the classroom after the period ended.

"AP World History."

Charlie chuckled, "Lucky. The teacher there rocks. I'm stuck with freaking Mr. Gaines. I swear, I think him and Mr. Roman will eat me before this year is over with."

Cas scoffed, "They're educators, Charlie. Not Leviathan."

"Who says they can't be both?" Charlie mocks before she slaps him on the back and walks the opposite way towards her next class, "Anyway, see you at lunch, Cas." The certainty in her voice made a hesitant smile rise his face—

"I see you're making new friends."

And Castiel's smile dropped along with his stomach.

"I am," He agreed in a monotone voice, turning around to face the familiar voice's owner, "What do you want, Anna?"

Anna smiled weakly but it dimmed back into a frown immediately under Castiel's precise, critical gaze, "I just wanted to talk. And obviously you aren't going to talk with Dean around..."

"Your next class is on the other side of the building, and you only have three minutes to get there," He reminded her coldly, looking away from her, "Are you really wasting time you don't have to participate in a pointless exchange of words with me?"

"You memorized my schedule?" Was the only thing she said in response, smugness and hope brewing in her tone.

"Just to avoid you." Cas lied stiffly, not meeting her gaze for fear she'd see through his statement, that she'd realized he still cared for her. At least somewhat.

He heard Anna exhale deeply, "Cas...how long is this going to go on? I know what happened wasn't the greatest, but you can't just isolate me from your life forever. I just," She took a step forward, the sincerity in her voice practically dripping onto the floor beneath their feet, "I want things to go back to normal, Cas. Don't you?"

"It's too late to pretend that everything's okay, Anna," Castiel told her quietly, glancing back over at her with steel blue eyes, "You don't have a pencil for this kind of situation. You can't just erase the past with a few strokes of your wrist and then rewrite your mistakes. Life isn't like that."

Anna looked down to the floor, "I didn't think it would go that way, Cas. Honest. Please...you know I would never do anything that I thought would put you in harm's way," She glanced up and took a few more steps forward, close enough to hover her hand over his cheek, "You're my baby brother, Cas. I love you."

"Love doesn't always have a positive impact," Cas told her numbly, though he didn't pull away when he felt her hand ghost against his skin, "It can lead to hate, and destruction, and abuse, and death...professing your affection for someone doesn't make your previous errors bleed away."

"But it helps the wounds fade." She whispered, her dangling hand coming forward to thread through his unresponsive fingers, "Look, why don't we just get out of here after school and eat at that shitty diner you love? We can talk about anything you want: life, death, oblivion..." A corner of her mouth tugged upward, "Just like old times."

Nostalgia washed over him like a tidal wave, enough to make his legs quiver upon impact. Memories flashed before his eyes: Gabriel scooping Anna up into a tight bear hug and spinning her around, Cas reading "Peter Pan" aloud as Anna laid her head on his shoulder, Gabriel kissing him on the cheek just for the sake of watching his little brother squirm...he missed those days, when he knew he could trust Anna enough with all his secrets. Of course, that time was over now, but perhaps it could start again...

"I can't," Cas stated as he pulled himself out of Anna's soft grasp, suddenly recalling his arrangement with Dean, "I'm busy after school today. Dean and I—"

"'Dean and I'?" Anna cut him off with a hollow laugh, all tenderness in her face evaporating as a cruel form of bitterness twisted her beautiful features, "You make it sound like you two are a couple. But that's what you want, isn't it? For Dean to come in with his deceiving smiles and 'sincere' promises, and take you away from it all. Like he's some sort of freaking hero or something. Well guess what, Cas?" She took a step away from him, her breath uneven and voice wobbling with emotion, "He hasn't been there for you like I have. He hasn't loved you as deeply or as long as I have. This twisted version of Dean Winchester is a fantasy. Don't you get that? Or will it take a few weeks before he gets bored with you and throws you away with the rest of his broken toys?"

Anger gripped Castiel's heart with its sharp talons, the perplex emotions of fury and sorrow chasing away any sort of reasoning and coherent thought. Fury was one of Castiel's weaknesses, and Anna knew that. She knew everything about him. Everything. And that was the problem. This was why they were broken like this. Why Anna was resulting to the only remaining option to make Castiel regard her with something other than indifference. She was never one to take rejection well, and this was one of her many downfalls. But he thought he meant more to her than that, than to treat him like a pawn in his own life like everyone else did. Obviously, he was wrong. He was always wrong. Naomi was right about that flaw, along with his many others.

Grinding his teeth to the point of agony, he took a step forward and caught Anna by the wrist, jerking her forward until she was flush against him. Her body stilled under the contact, and Cas took the rare opportunity of silence to lean down and whisper acidly in her ear, "I may not end up with a happy ever after with Dean, but I sure as hell won't have one with you."

He released her like he'd been burned, not caring at the several of students that had stopped what they were doing to watch the scene unfold, to observe with their judgmental minds and cruel stares that had haunted Cas his whole life.

Anna was still watching him with angry, sad eyes, but it didn't matter to him anymore. He turned away and walked towards his next class, ignoring how his heart received another hairline fracture at the bitter reminder that his relationship with his sister was burnt to ashes with the match lit by Anna's ignorance and Castiel's refusal to grant her forgiveness.

Author's Note: This chapter is short, but that's because a lot of the action was saved for next one. And I'd like to inform that we'll see more of Crowley next time and finally find out more regarding his and Castiel's...difficult relationship. And can you believe this story is already halfway finished?

I'm planning on finishing and posting the next chapter on the very day this story's first chapter was posted, so some encourage (as in reviews, pms, favorites, follows) will be greatly appreciated.