Hey, so I know I have other ongoing stories at the moment, but this one popped in my head when I was looking through older stories I've written. I decided I wanted to redo my Boarding School Hell one, but this time in the Supernatural universe. It has substantially changed to make the change in Dean's character a lot more realistic. So, I really hope you enjoy it.

Disclaimer: I don't own Supernatural. I'm just writing this for fun.

Chapter 1

Dean Winchester looked up at the school as he climbed out of his dad's jeep. It was large, too large for his liking. And it definitely looked like it was old. Way old. The 17-year-old Winchester didn't really know what to make of it but he didn't like it.

Just one more year, Dean thought to himself. That's all he had to do was one more year. He should have been in Lawrence High School, but he just had to get expelled. It wasn't even his fault. The fight that got him expelled was Michael Jenning's fault. He started it. Dean just finished it. Okay, so the captain of the basketball team had ended up in hospital, but still. It served him right.

If Dean hadn't been on his last warning, it would have been a bit easier. And if Dean hadn't already been expelled from three different schools, it might have been a little different.

God only knew how his parents had gotten him into this school, or how they were going to afford it. No public school wanted to touch him for his senior year. He'd ended up at St. Benedict's Boarding School for Boys. Of course, it was a Catholic school, and it just had to be an all boys one. Did his parents really have to throw both at him? But he knew whose suggestion it had really been. His dad's friend Ellen had connections that helped him get in, despite his track record at not staying out of trouble.

Dean let out a sigh as he felt his dad's hand on his shoulder.

"Please, do not get expelled from this school, Dean." John pleaded with his eldest son as mary Winchester climbed out of the car. Luckily, little brother Sammy had remained at home. Dean didn't want to see the kid watch him get packed off to a boarding school.

"You'll make new friends quickly, Dean. You always do." Mary smiled, as she placed a caring hand on his face. Dean couldn't help but roll his eyes. That wasn't what he was worried about.

"You realize that people have been here for three years already. I'm gonna be here for one. Why did you think this was a good idea?"

"Well, if you hadn't gotten yourself explained from your last school, you wouldn't be in this position, would you?" Mary glared at her son and started walking towards the school. Dean looked over at his dad, a glare in his green eyes. John shook his head with a look that said he would talk to Mary later.

Mary had been livid hearing that Dean had put another boy in the hospital. John, on the other hand, let the marine show through. While he pretended to be angry, he was secretly proud of his son after he heard the whole story. The Jennings boy had been asking for a beating for some time and happened to hurt one of Dean's best friends, who happened to be the daughter of his friend Ellen. Of course Dean was going to defend Jo's honor. It just led to the 18-year-old being put in hospital.

Dean did had to admit that he was lucky. Michael's parents could have pressed charges, but they decided against it as long as Dean was kicked straight out of school. The downside for Dean was it was towards the end of his junior year. He was going to miss football practice, junior prom and a hell of a lot of school. Of course, John and Mary decided against him missing out of school and he was assigned a tutor. Not that it helped. Uncle Bobby Singer wasn't much of a tutor, but he was good fun and understanding.

But now Dean was back in school. Part of him looked forward to it. It would be good to play sports again and good to hang out with friends. But he'd rather be at home with his friends from school. He was going to miss the fun and games with Jo, Ash and even Bela.

Students were walking towards the boarding school with bags. The only upside to today was everyone was starting for the new school year. Right now, he didn't stand out like the new kid. The one who would only be there for a year before going off to college—was he even going to go to college? That wasn't something he'd really given a thought.

Right now, he had to get through high school. He had to manage the year without getting suspended or expelled. That wasn't going to be easy. Trouble had a habit of finding him.

Dean grabbed his two bags while John grabbed a box and they followed Mary into the school. His new room was his port of call. Then he could at least get rid of his parents and get on with settling into his school.

As they walked through the corridors, Dean couldn't help be feel like eyes were on him. Despite being the first day of school, he was clearly the new kid. The boys that he walked past looked like they were at least juniors, so they'd know the faces of the seniors. Dean remembered hearing that the school only had around 100 students per year. It would be easy to remember those in the older years.

Finally, he got to his room. 6C hung on the wall with two names underneath.

C. Novak

D. Winchester

Novak. That was the name of his new roommate. And based on the sound coming from the room, his roommate didn't have the best taste in music. All he could hear was noise. It reminded him of the stoner music from his last high school. God, he hated that music.

Mary pushed the door open and Dean could see a fairly tall guy sitting on the window ledge, writing in something. Great, he writes in a diary too, Dean rolled his eyes. This was going to be one hell of a year.

"Hello!" The boy looked up, and Dean couldn't help but raise his eyebrows. The boy's eyes were an intense bright shade of blue. Dean had never seen anything like them, "I am Castiel."

The boy—Castiel—placed his notebook on a nearby desk and held out his hand for Mary to shake. She smiled softly, introducing herself, quickly followed by John. Dean instantly felt subconscious. This boy didn't have his parents here. He needed to get rid of his.

"Okay, Mom, Dad. You can go now," Dean made it clear they weren't wanted.

"You'll be okay, sweetie," Mary smiled and kissed Dean on his forehead, "We'll pick you up at Christmas."

Mary had tears in her eyes as she hugged her eldest son. The eldest Winchester brother couldn't help but roll his eyes with a soft smile.

"You know, anyone would think I chose to come here with you crying. You sent me here, remember?"

"Well, if you didn't get yourself expelled..." Mary started, but was then conscious about the other boy in the room. Dean glanced over at his new roommate to see Castiel's blue eyes widen. Damn, they were really blue, "Never mind. Please just stay out of trouble, Dean. I'm begging you this time."

Dean rolled his green eyes, again, but nodded his head, "I'll stay outta trouble, Mom. Scout's honor."

"You weren't a scout, Dean." John glared at his son, but pulled Mary out of the door.

Finally, his parents were gone and it was time to meet his new roommate properly. He turned to the dark-haired boy, musing over how messy his hair was.

"I hope you don't mind. I chose this bed." Castiel pointed towards the suitcase that sat on the bed. Dean shrugged his shoulders. He didn't really care where he slept, as long as he was able to get some sleep.

Dean started to unpack his bags, but could feel eyes on him. Out of the corner of his eye, he could see Castiel watching him.

"So, you were expelled," Cas—yeah, now it was Cas—spoke in a low voice, "Why were you expelled?"

"One too many fights." Dean laughed at the question. The last thing he wanted was to make his roommate uncomfortable. As the two went back to unpacking, Dean couldn't help but want to know more about this kid, "So, your parents already gone back home?"

"My mom died when I was 14," Castiel explained with a frown, "My dad left when I was a baby. My older brother took me in, but I get back home to here on my own."

"Oh God!" Dean exclaimed, kicking himself for his laid back attitude, "I am so sorry. I didn't mean to...I'm sorry...it was insensitive..."

"It's okay, Dean," Cas smiled softly, "I deal with it well. My brother helped. And it is not like you knew before you asked. It would make sense that you would want to know about my family."

Dean felt like he could breathe again, but he made a mental note to watch what he asked—to anyone he met. He had no idea why people were in this school. For him it wasn't his choice, for others it could have been a means to escape.

Before Dean could ask any more questions, a knock at the door interrupted them. Before either teenagers could answer the door, it opened and a medium-height, brown-haired boy poked his head around.

"Yo! Novak! How was your summer?" The boy walked into the room and completely ignored Dean. Dean just got back on with packing, listening into the conversation. He did smile when he saw Cas' blue eyes lighten up.

"Good. How was yours, Speedy?"

Dean couldn't help but smirk as the newcomer rattled off everything about his summer vacation. It turned out that the brown-haired boy had finally gotten with a girl called Mandy, and Dean couldn't help but laugh. The guy sounded just like him.

"This the new guy?" Speedy now asked, pointing over at Dean.

"Oh, I forgot my manners. Yes, this is Dean," Castiel introduced Dean and then motioned towards the third boy, "This is Cole Speed."

"Most people call me Speedy," Cole replied with a smile, holding out his hand for Dean to shake, "So, you're the fresh blood."

"I guess I would be." Dean nodded, resenting the fact that he was going to be known as the new guy. There would be around 100 freshman, but he'd been known as the new guy—the fresh blood.

"Cool," Speedy grinned, "So, how come you've got here in your senior year? I'm guessing you're a senior if you're sharing a room with Novak."

"I'm a senior," Dean nodded with a smile, "I was expelled from my last school. A friend of my dad's just happens to know the principal."

Speedy grinned and wiggled his eyebrows. Dean clenched his jaw, preferring not to think of Ellen Harvelle doing the dirty with anyone. She was not like that—and she'd beat any guy who tried it on her. But Speedy didn't know, so Dean was going to give him a free pass. Just this once.

"What you get expelled for?"

"One too many fights." Dean kept the reply short. Not only was he still a little pissed at the insinuation from this brunette guy, he was also trying to get away from people finding out what he'd really done. He didn't need a reputation, at least right now. Speedy just shrugged his shoulders and turned back to Castiel.

"So, how are you and Meg?"

Castiel frowned at the mention of the girl's name and Dean felt a little uncomfortable being here for this conversation. The two were clearly good friends, and Dean felt like an intruder for being here.

"We broke up again," Castiel finally answered, "I broke it off last night."

"You got some before you broke it off, right?"

"Of course." Castiel said it as if Speedy was an idiot. Dean couldn't believe the conversation. He had prim, proper school boys in his head when his mom and dad told him all about the place. He never expected them to have similar conversations to his time at home.

"So, do you have a girlfriend back home?" Dean realized the two boys were not looking at him. This Speedy guy was way too nosey.

"Not as of..." Dean checked his watch, "five hours ago." He and Lisa—could he really call her a girlfriend—had decided to call it off while Dean was in school. They'd be friends and that was about it. But then, really they were just friends with benefits. Dean Winchester didn't do relationships. He liked to have choices.

"Never ever leave home without getting laid a few nights before you get here," Speedy advised him, "You'll be gagging for it while you're in here. This place is worse than jail, unless you're gay. You're not gay, are you?"

Would that be a problem? Dean questioned, but shook his head. No he wasn't gay, but he had friends who were. He had no problem with those who battered for the other team, but it seemed this school and Speedy did.

"Who else is back?" Castiel now broke up the conversation after putting the last of his clothes in his drawers.

"Benny is," Speedy nodded, "And I think Teapot is back."

"Teapot?" Dean just had to check that he heard that name right.

"Yeah, erm, long story about that nickname." Speedy laughed.

As Castiel and his friend left the room, Dean hung back. He wasn't sure whether he was welcome, and didn't exactly want to push his presence.

"You coming, Winchester?" Speedy now called out, "You can meet the gang. Well, some of it."

It turned out that Dean really had no choice. The two teenagers were waiting for him to follow them down the hallway and into one of the other rooms. Dean couldn't help but glance at the door to see the names B. Laffite and C. Speed on the door.

"Castiel, it's good to see you, brother," a shorter, blonde-haired boy smiled, hugging Castiel in a friendly way. His eyes then looked at Dean, "Hi. Name's Benny. You must be the new blood."

"Yeah, seems I've picked up that nickname," Dean nodded his head, "Dean."

"Well, it's good to meet you, Dean," Benny smiled, making Dean feel right at home, "Take a seat. Everyone will end up in here soon enough. They always do."

"Party central." Speedy grinned, sitting on his own bed, while Dean sat on one of the desk chairs. Castiel sat on Benny's bed up by the pillow, while Benny laid across the bottom on his stomach. While the three friends chatted about their summer and asked Dean the odd question, more students joined them.

Dean was soon introduced to "the gang." It was a small gang. James 'Teapot' Bane was the only other senior to join them. There were three juniors, who Dean didn't quite get the names of. He'd worry about that at a later date.

"So, do you play any sports?" Benny now asked Dean with genuine interest.

"I played football at my old school," Dean admitted, "Used to play baseball as a kid."

"You gonna try out for the team?" Teapot now asked, with a questionable glare. Dean suddenly felt self-conscious and rubbed the back of his neck.

"Maybe."

"Watch yourself," Benny suggested, "They're not the friendliest of guys, brother." Dean wasn't sure how to take that warning, but he wasn't going to push it. He was sure he'd find out over the next week.

"Dean'll be able to handle himself," Speedy laughed, "He got expelled for fighting at his old school."

"Really!" one of the juniors asked with a laugh. Dean was sure the guy was called Garth, but he couldn't be sure. He was skinny as a twig and he would call him Twiggy in his head, "How many fights?"

"Enough," Dean shrugged his shoulders, "Not the first time either." They were pulling the story out of him. With enough questions that Dean couldn't avoid, he finally told them about the guy that he'd put in the hospital. While most laughed, Dean couldn't help but see Castiel look at him with shock in his blue eyes, and was there a hint of fear? This was why he didn't want to tell his story. He really didn't need a reputation like this.

"Hey, anyone been down to the hut yet?" a red-haired junior asked, jumping up to his feet, "I heard they were going to put a lock on the door."

"They threaten to do that every year," Benny laughed, climbing off his bed but then turned to look at Dean, "You smoke, brother?"

"Supposed to have quit," Dean shrugged his shoulders. He'd promised Jo that he would quit smoking, but what was the harm in doing it sociably at school? Like she'd find out, "Why?"

"That's what we do in the hut." Castiel told Dean and then followed his friends out of the house. Dean laughed once, realizing that his promise to stay out of trouble was clearly being broken. He should have the middle name Trouble!

Dean just followed his potential new friends through the wood to a small cabin that looked like it had seen better days. Actually, Dean couldn't help but think a gust of wind would blow this thing over. How old was it?

On the way down, Cas had explained that it was the old changing hut for the soccer team before the team was disbanded. The hut had fallen into disrepair and the soccer pitch was overgrown. But it was the perfect spot for the boys to go smoking, even if it was out of bounds and well against school rules.

Dean could see that it had been out of use for some time. The look of it screamed no longer in use. As they stepped into the hut, Dean started to worry about his safety. It was dark, musty and smelled of damp.

"You've had your tetanus job, right?" Castiel now asked with a laugh, before pulling out a packet of cigarettes and sitting down against one of the walls. Dean looked around before sitting near his new roommate, looking around at the boys lighting up. Cas offered Dean a smoke, but he refused. He had promised Jo, after all, "You'll take it back up in a few weeks. Trust me."

Dean smiled weakly, before looking around at the place again. He couldn't help but think of the stern look his mother would be giving him right now. Not an hour ago had he promised her to stay out of trouble. Now he was in a rundown hut that was technically out of bounds with friends who were breaking one of the rules. He was screwed if he was caught.

"So, boyfriend or girlfriend back home?" The third junior that he was sure being called Tommy.

"Tommy asks that because he's gay." Speedy laughed. So, they didn't have a problem with gays. That made Dean feel a little more at ease—not that he was gay, but because he didn't want to spend a year with homophobes.

"I had a girlfriend," Dean answered the question, "I'm straight."

"I'm sure I could change that," Tommy winked, make Dean feel a little uncomfortable. Benny rolled his eyes, telling the junior to shut his pie-hole and then apologized for the boy, "Hey, eventually people change in this place. Look at Cas. He said he was straight when we first met him."

Dean looked over at his roommate, who was turning a shade of pink. He wasn't sure how to take that comment, sure that he'd heard Speedy ask about a girl called Meg earlier on.

"Oh yeah, did Meg ever find out about what you did?" Speedy now asked, laughing at his friend. So, there was a girl called Meg.

"No, and she never will." Castiel warned his friend.

"You two break up again?" Benny now asked and smirked at his friend, "It's about time, brother. She was...well..."

"She was what I needed at the time," Cas confirmed, looking at Dean out of the corner of his blue eyes, "Can we talk about something else?"

"Well, I guess you don't need to worry about relieving that frustration," Teapot now smirked, looking between Castiel and Tommy. Both of them rolled their eyes, and then Teapot glanced at Dean, "Sorry, dude. Don't mean to make you feel uncomfortable."

The group decided to change the topic of conversation after that, deciding that Dean needed to know all about the school. More importantly, they needed to know about the guys not to hang around with, and it seemed like most of the football team was on that list. Like that was going to stop him. He was only going to be here for a year, he'd didn't care about making too many enemies. He wanted to have fun in his senior year.

So, it's just an introduction to someof the characters. I'd love to hear what you think. Just to let you know that I am taking this story slow. It is eventually a Castiel/Dean story, but I want the change to be realistic.