Chapter One: In The Shadow of An Winchester

High school can be obnoxious. It can be even worse when you're just a simple angel on a mission from heaven to watch some snarky teen who can't stand school. Dean couldn't focus, never stopped chasing tail, and had to eat fifteen times a day. And Cas was told this guy could save the world.

Author's Notes: Well, first SPN only fic. Be gentle. Please be patient. I work overnights, so my schedule is a little whack.

Warnings: AU-ish, Wings!, OOC, Daddy(ish)!Dean, Foul Language, High School, and guy on guy (eventually).

Disclaimer: I do not own the characters of Supernatural. I do hope to one day own your souls so I may force you into loving my writing and reviewing. For now, I love you silently.

Chapter One: In The Shadow of An Winchester

Dean was never one to hit the books. He not once dressed out for gym. He couldn't remember a time he wasn't late for class. He'd been in detention more than his actual classes. But, high school was just high school. He didn't have his heart in it. He wasn't interested. It felt like a damn waste of time. Then there was Sammy, his little brother.

Nerd to the core and bookworm through and through. As soon as Sam worked those pleading puppy eyes on Dean to continue to go to school, he caved. He would never admit to anyone that's why he hadn't dropped out yet. He could never say that he stayed in school for his kid brother. He could lie and say he did it for his dad – that usually rested good with him. But he really couldn't help but to think how chick-flick it was to have the amazing older brother hang around to save the sweet dorky brother.

He even started school a week late to prove a point no one noticed. For some reason or another, it had looked like they were sticking around this town for awhile. John, his dad, seemed content enough leaving them for longer periods of time. Their Uncle Bobby (no relation) was damn determined to keep them in school and give them an off chance at a semi-not-very-normal life. Dean would rather be off hunting with his father. Hunting all things supernatural, not wildlife. He wasn't that cruel.

Again, Sam pulled the big goo-goo eyes and the sweet little brother card. He asked Dean if they could go back to school. If they could stay around here for a little while. If they could be their father's eyes, ears and occasionally the researcher mouth; pretend to be normal. Not forever, Sammy knew that was impossible. Long enough to know what it was like. Their dad was off on a big job, too. John had even called Bobby to watch over the boys, which meant he wasn't sure when he was getting back. Dean thought he could stay in a motel away from Bobby to hopefully halt his overbearing instincts.

So, Dean caved – again. He left most of his weapons at the motel. He only took a revolver, some holy water, spare bullets, two knives, salt and some rope. Just in case, of course. Sam knew what was in Dean's bag the moment his brother strolled into the school three periods in and ran into him in the hallway. Dean wouldn't have brought a bag otherwise. No way. Just his jacket and a cocky smile.

"Hey Sammy."

Sam gave Dean a bitchy look, causing the older brother to roll his eyes. "It's school Dean. There's a schedule you know."

Dean smiled at the hiss that came out of his little brother. "I know that, but-"

"But nothing Dean." Sam sighed, sounding like he just lost all hope. "You promised me we could pretend to be normal. I hate when you break your promises."

It had felt like someone kicked Dean in the chest while making Dean kick a puppy. With Sam's sad tone, disappointed eyes and the words that came out of his mouth. The kid knew how to work anyone over. If Dean didn't feel like a complete jackass, he'd have been proud. The kid would win an Emmy one day.

Dean sighed in an exasperated fashion. "It was a just in case thing, Sammy. I'll put them in the car, okay? But that is as far away as they get. Pretending is fine, but we can't let our guard down."

"Did you bring the car, or did you walk?"

"I brought the car. " Dean said in a no-duh fashion.

Sam nodded, which made Dean smile. "It's blue."

"I know." Sam growled innocently.

"I'll leave them in the trunk, okay?"

Sam gave his brother a weak smile and Dean's heart clenched a little. He never wanted his baby brother to have a life like this. Not constantly worrying about what was hiding under his bed and lurking in the shadows. Not with the intense knowledge that it was real and not a hefty imagination. He wished his little brother wasn't secretly relieved that Dean brought protection. He didn't want to see the light in his eyes knowing there were weapons around to keep him safe. He just wanted the kid to plaster on a bitch face and whine.

The older brother ruffled Sam's messy hair and gave him one of his sure smiles. Sam smiled back halfheartedly at him. Dean turned on his heel to head towards the car when Sam stopped him.

"Dean!"

"Yeah?" He asked, turning.

"Only salt and water." Sam said, his face slowly morphing into his bitch-face. "If something else falls out of your pocket we're screwed."

"One time!" Dean protested.

"Because of a girl!"

"One. Time." He stressed.

But with the power of full on bitch-face and cute eyes, Dean tossed his hands in the air and started back outside to the car. Sam stayed in place for a few more moments, watching Dean walk out to the car and making sure he didn't sneak back in. When he was mostly sure he could sort of trust Dean to not bring too many weapons inside, he turned to blend with the other students on their way to class.

The parking lot was nearly deserted. Everyone was inside. A few stray seniors here and there were slowly making their way inside, but nothing very noticeable. All seemed in a haze without a care. Dean could have shot his gun and no one would have known.

Except the one other guy.

There was another teen – had to be Dean's age. He looked like the timid type, somehow. Might have been the lone-standing thing. Not to mention, he looked lost as hell. He was staring up at the sky, arms hung in defeat. He was draped in a tan trench coat – far too big for him. His hair looked freshly played with; all distressed and messy. Dean couldn't see his face, just that he was standing there staring at the sky without a move. Dean let his eyes do a once over before reaching into his bag and grabbing the salt. Just in case. You never knew when your last name was Winchester.

He turned to the trunk of the car, dug the keys in the slot and popped it open. He grabbed the holy water and stuffed it in his pocket with his salt. His hand hesitated over a knife before he had a mental flash of Sam. Big pleading eyes, desperate for one taste of normal. Dean cursed under his breath and was thankful no one was around to witness him caving to his little brother. Again. Like usual when Sam got teary-eyed.

He slammed the trunk shut and sighed, turning on his heel with defeated slouching shoulders. Of course when he popped his head up and went to take a step forward, he was more than startled by a pair of large blue eyes looking at him imploringly.

"Hel-"

That was about all the other kid got out before every little sense of Dean's kicked into overdrive. New place, new face, and someone willing to invade his space. He swung his fist without hesitation this time around. More alert, more aware, and ready for a throw down.

What he was not ready for was this kid.

The punch he threw was blocked. The teen opened his mouth to say something, but Dean wasn't wasting seconds anymore. He swung with his other hand, hoping this fake would help. But when he re-swung his right hand he was in for a surprise. His wrist was grabbed and it was grabbed hard. He was spun on the spot, and which way, he wouldn't knew if he replayed the scene five hundred times.

There was a twist, a grab, another block and a hell of a lot of grunting in effort on his end. But not a blink of an eye later Dean found he was choking himself with his own arms. The teen in front of him had both wrists in his grasp, had crossed Dean's arms and shoved them against his neck.

For one long and horrible second Dean thought this was how he was about to start some stint at a high school. The kid that got beat up in the parking lot. The loser who lost to the small kid in the coat. He could sadly imagine Sam trying to stick up for his tough older brother and failing miserably. Then he imagined a new shitty high school for Sam because Dean was a would-be boxer without a thought process.

The next second though, the fierce grip was gone.

Dean was no longer leaning back over the end of the car but slouching forward in the new free space he was given. He rubbed his wrists and gently touched his throat.
Of course, the only way Dean Winchester could possibly meet someone and have a lasting impression was this. Today was the day.

"I apologize if I've caused you harm."

Dean looked at the teen questionably and smartly replied. "Uh..."

"I am pleased to make your acquaintance. I am Castiel."

"Uh..."

Castiel held out his hand. Slowly, with unsure vibes and searching eyes, Dean took his hand in a quick gesture. "I'm Dean?"

"So you're not going to hurt him?"

Dean snapped his head around to find Sam there, looking a bit nervous but his hands behind his back. Dean wasn't sure what his little brother was hiding, but was damn sure it would have ended this Castiel kid real quick.

"I had no intention of hurting him, I was simply trying to introduce myself."

"When you get into someone's face like that, especially without announcing yourself, people get defensive." Sam announced.

"I apologize once more."

"What's up with the way you talk? You're sure proper for a teenager." Dean noted.

He had a nice, white dress shirt on, a crisp blue tie and pressed slacks. The trench coat was a little off, but Dean wasn't going to pick out every awkward detail of this guy. He didn't have enough time in his life.

"I am not from around here." Castiel replied instantly.

"Obviously." The brothers said in unison.

"I'm Sam." He stepped forward and stuck out his hand for Castiel. "I'm Dean's little brother."

"He's trying to kill my reputation already." Dean sighed, pinching the bridge of his nose.

"Is this your first day?" Sam asked, shaking his hand lightly and releasing. He instinctively backed up to stand next to his brother.

"Yes. I just arrived."

"Did you drive?" Dean asked, looking around the lot.

Castiel shook his head. "I was dropped here."

"Dropped off? Is that what you mean?" Dean asked, eyeing Castiel oddly.

"Yes?"

Sam looked up to Dean who had an eyebrow raised. Sam gave Dean his best pleading eye look. Of course, his brother who just supported every damn charity decided he wanted to help the new weird kid. Go figure.

"Fine." He muttered. "Alright, um, Cas...let's get you inside and find your schedule. Sound good?"

"It does sound like an idea I would approve of. I agree to it."

Dean looked at his little brother. Half glare, half confused. Sam smiled at Dean and walked next to the new kid, leading the way. Dean knew his little brother smelled the nerd in Castiel a mile away.

Then Dean caught a glimpse of the huge knife his brother had now sheathed and tucked in his pants. Only being an Winchester, where the sight of your little brother hiding a giant knife, would warm your heart.

Only being an Winchester would give you the luck of dog shit.

He didn't have time to point out to Sam that it wasn't normal for kids his age to carry knives, after of course, having just gone on about being normal. He only had a chance to give Sam a knowing look and to receive and eye roll in return. Then, it just got worse after that. Dean of course landed in his first class with a companion. This new, awkward as hell, same fucking schedule companion.

It didn't help his little brother walked them to their first class. No, not at all. It was a little nice that the girls thought that was cute and adorable. It also got on his nerves his little 'helpful' brother was going to be there when class ended to show him and Castiel to their next class. Dean was sure the administrator gave them the same schedules after she watched Dean eye Castiel with loss, confusion and helplessness. It had to have been silent payback for him missing out on a week. Or he was just paranoid or trying to find a good excuse, because for no damn reason, was unacceptable.

He waited for some divine sign that God hated him or something, but instead Castiel stood at the front of the class with Dean, staring at him unwavering. His crystal blue eyes were a bit unsettling. Only made worse by the staring, of course.

"There are two free seats in the back." The teacher said simply, after a quick introduction. "I'll ask you two to stay after class so I can get you the things you need to get caught up."

Dean was tempted to tell him to save his breath, but he had just had his attention pulled away by the sound of giggling chicks.

As luck would have it, those free seats were surrounded by low cut tops, tight jeans and cleavage.

As Winchester luck would have it, those two free seats were side by fucking side.

So while Dean tried to flirt his way through this horrible period of History, his new seat mate had begun to make it nearly impossible. Because when the girl he was hitting on turned and her giggling died instantly. Dean had been pretty sure he was about to seal the deal and meet this chick in the janitors closet.

"Lets just, you know...talk about it later. When your friend isn't around."

Dean dropped his jaw and turned to look at Castiel. His face passive and genuinely curious. His eyes were searching and wondering. The dude looked like a grade-A creep of a serial killer.

He began to rub at his temples and muttered under his breath.

"This is going to suck."

In a way, he wanted it to suck. He did.

After meeting the girl in fifth period with pretty lips, he really wanted it to suck. The girl in seventh with the rack to end all. The chick he passed in the hallway with jeans too tight and an ass so shapely it should have been illegal. But, he was not going to get lucky or be lucky today. Today was his day from hell. In the form of a curious and awkward teen who wouldn't part from Dean's side. Usually if Dean so decided to shoo his brother away, he relented after a little while. Dean paid for it later, sure, usually having to give in to all of Sammy's ideas for the day.

But thirty minutes alone with a girl was worth it. The only downfall was Castiel. He didn't seem to get any of the notions Dean sent his way about fucking off. Leaving him alone. Shoo-fly, don't bother me. Nothing. He never budged. With that, Sam got some sort of new found confidence. It was like he had some type of admiration for this new kid who was annoying the living shit out of his older brother. Or maybe if Castiel wasn't being hurried away, Sam had an excuse to stick around too.

Dean was outnumbered. In the worst fucking possible way.

If it wasn't the sheer fact that Castiel wouldn't leave when Dean was trying to chat up a girl, it was usually the intense staring with his large blue eyes that had the girls call for rain-checks. Just as Dean was about to rip the kid a new asshole, Sam would appear out of nowhere to talk to his brother about anything. He couldn't escape. Until one moment where he took the opportunity as it was.

The end of the school day.

Dean and Sam got into their car that was borrowed from Bobby, Castiel standing on the outside of the drivers door. Sam got Dean to roll the window down even though Dean bitched at him under his breath.

"Do you have a ride, Castiel?" Sam asked innocently. Dean thought about strangling him. Innocently.

"I do not need a ride, Sam." Castiel assured in his own way.

"Oh..." Sam sounded disheartened and Dean figured it was because Cas was like his new buddy. Not to mention Sammy's heart was enormous. "Well, uh, be safe going home."

Castiel gave a small nod. "You as well Sam. And Dean."

Dean gave an awkward smile and rolled the window up while Sam waved in a friendly manner although he was still frowning in worry.

"He'll be fine Sammy, he isn't a lost puppy." Dean said in a sigh, starting the car and heading towards the motel.

They drove off leaving Dean to man his radio and for Sam to turn in his seat and glace behind him. He frowned. Castiel was already gone. The only thing that lingered in his spot was a black feather. Sam shrugged as he turned around. Maybe, he figured, Castiel got distracted by a raven.

Instead of worrying, he just turned his attention back to his older brother, busting out his puppy eyes.

"Dean? When can we ditch the motel and stay at Bobby's?"

Just what Dean needed. Uncle Bobby breathing down his neck about school work. But Dean made the mistake of turning to glance at his little brother. Those big pleading eyes that wrapped him around his little brother's finger. He sighed.

"We'll go tonight..."

Sam whooped in his seat, rolling his window down to stick his head out like an excited dog. Dean didn't even tell him to get back in the car. He just picked up the speed a little and tried not to crash from laughing after Sammy swallowed a bug.