AN - I've been meaning to write a new story for a while, and then one fine day this idea popped into my head. After all, Serena never talks about boarding school, so I figured I'd give her a reason why.
I hope you like this story. Read, Review, Enjoy.
- Marina
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Chapter One - Welcome To Cheshire Academy
Serena Van Der Woodsen did not like boarding school. In fact she didn't like school in general, but boarding school somehow felt different then just school. Boarding school was more strict. It had more rules for her to break. More preppy, stuck up douche bags for her to put up with. More annoying teachers who for some strange reason wanted to teach her things she thought she'd never use in her life. To Serena school was just pointless. She knew she had to go so that she could open doors for her future but whenever she thought about the future she didn't see any of the things she was forced to learn in school. She pictured herself living in some tropical island, surrounded by hot lifeguards and drinking cosmos like there's no tomorrow. So of course in Serena's head, if you didn't learn to make cocktails in school than what was the point of her learning anything at all?
So when Serena got out of the cab that had driven her from the train station to Cheshire Academy, she knew she would never like boarding schools. As she flicked her long golden hair and lay her mystical, navy blue eyes upon the red brick building she was almost certain that she'd get expelled before the end of the semester. She was going to try not to though, for the sake of her mother, and not going home. Serena had begged and pleaded for her mother to send her to boarding school. She never admitted why though. She couldn't. If her mother found out what happened the night of the Shepherd wedding Serena was sure that Lily would never look at her daughter again. So Serena made her mother go through all the trouble of calling a bunch of schools and finding one that would actually take her. It was a tough job but Lily was good friends with the headmistress of a very nice little boarding school in Connecticut. It was co-educational, which Serena thought was a very nice touch. Her mother had warned Serena to obey all the rules because if she got kicked out of this school no other school would ever take her, so it was either behave or she could kiss her trust fund goodbye. And Serena could never give up her money.
As she walked down the halls of Cheshire Academy all she could think was how much she missed Constance. All the students who she walked past here gave her judging looks. She was the new girl, she should expect this. At least in Constance when people looked at her she knew that it was either because of admiration or just because they'd read about another fake scandal on Gossip Girl. The one thing Serena knew she would never miss. Although she was sure that even if she was gone, the rumors about her would continue, at least for a little while longer. She didn't care though. She knew that a life without Gossip Girl would be so much simpler. This was probably the only upside about boarding school.
Serena finally reached the room she had been assigned. On the door of the room there was the numbers 629 painted in gold. The numbers were painted in gold in all the doors but Serena couldn't help but think this one had been redone a few times. She had a feeling that whoever else lived in this room was probably a perfectionist who had requested the numbers to be done up every once in a while. Serena hated perfectionists. They drove her insane. So dull and perfect. She didn't understand why they tried so hard. But then again she never had to work for anything in her life so she wouldn't have any idea what it was like.
She entered the bedroom and looked around. It was large and pretty clean. There were a few fashion magazines scattered on a small table beside the door. To her right there was a wardrobe. It had golden designs on it, painted with the same gold paint at the door. Beside the unnecessarily fancy wardrobe was a large mirror with a bunch of light bulbs on the edges. It was like on of those mirrors you saw backstage at shows. The mirror was attached to a small wooden desk with items of make up taking up every little bit of space it had.
To Serena's left were bunk beds. The top on had a bunch of teddies on it so Serena assumed some one had already taken that bed. She threw her bag onto the bottom bunk and looked around the room a little more. At the back of the room there was a double bed. It was done up with some expensive looking purple sheets. Serena thought the perfectionist must sleep here. It had a small pot of lavenders beside her bed. They were very strong smelling. If the girl wasn't a perfectionist Serena would have thought that she was trying to quit smoking or something. She knew her life would be tough living with this person. It would take a while for them to adapt to each other's way of living. To be honest the only perfectionist Serena had ever liked was Blair. Her best friend Blair. The best friend she had betrayed and then run out on without any explanation. Serena was certain she'd be going to hell. She didn't care. What's done is done, and Blair was stubborn. It was no use trying to make up for it when she knew Blair would hate her forever. It was better if Blair hated her for running away rather then for sleeping with her boyfriend. Besides, this way Serena saved Nate's ass as well.
Her thoughts were interrupted when the two other occupants of room 629 entered.
One was a short girl who gave off such a cute vibe that Serena wanted to hug her tightly and give her a cookie. She had a very sleek black bob that framed her face perfectly. Her eyes were a golden amber color that twinkled with innocence. Serena knew everyone's first thought of her must be virgin. She had perfect sized B-Cup boobs. Yes B-Cup wasn't that big but it wasn't that small either. Serena had an idea that guys lusted for this girl. She had a perfect figure except for her slightly large ass but Serena doubted anyone ever noticed anyway. She knew that if Chuck was here he'd be all over the poor girl.
As for the other girl who had entered, Chuck wouldn't have thrown a second glance. The girl was pretty, but not pretty enough for the playboys standards. She had light brown hair that was slightly frizzy. It was easy to tell that this girl had straightened it way too much. She had piercing hazel eyes that scared Serena a little bit. She was also short but not as short as the cute girl beside her. She was quite skinny but not exactly unhealthy. She's more slender then skinny, Serena thought, if that even makes any sense. This girl obviously didn't get as much attention, probably mostly because of her slight lack of boobs. She also had a very strong smell of lavender. She must have been the smoke-quitting perfectionist.
"Who are you?" The perfectionist asked.
"Serena Van Der Woodsen. I'm you new roommate" Serena answered.
"What new roommate?" The perfectionist asked with a confused expression.
"The one from New York. The headmistress' friend's daughter. She told us about this" The cute one informed her.
"Hi I'm Daisy" The cutie introduced herself. Of course the cute girl was named after a flower, Serena thought. Daisy gave her a warm, welcoming smile that showed almost all her perfectly straight, pearly white teeth. Serena shook her hand politely and then looked at Daisy's companion waiting for an introduction.
"I'm Rhonda" she said sticking out a hand for Serena to shake. She shook her hand. It was cold, and she had a very manly handshake. Serena couldn't help but feel awkward so she just smiled nervously at Rhonda.
"Would you like us to help you get settled?" Daisy asked kindly, earning her some death stares from Rhonda.
"Oh no, it's okay" Serena insisted. She didn't know them well enough to let them go through her stuff just yet.
"Oh, that's okay. I guess we'll see you at dinner then" Daisy said and she and Rhonda left the room. When the door closed Serena could hear Rhonda's muffled complains about helping the new girl. She just rolled her eyes. No one was ever welcoming these days.
She zipped open her bag and started taking out her clothes, book and make-up and trying to find space in the room to put them. She eventually found an empty cupboard above the fancy wardrobe. She figured neither of the girls ever used it since they were both so short, or maybe it was just Serena who was too tall for her own good, but then again, she was wearing five-inch Manolo's.
She put all of her stuff in any place she could fit them until she reached the last few things in her suitcase. All that was left were pictures of her family and friends and the school uniform for this damned boarding school. She put the pictures on the windowsill of the window beside the bunk beds. As she looked at the pictures she couldn't help but feel lonely. One was of her and Eric years ago when she was only seven years old and he was about five. She missed her brother so much. She felt bad for leaving him all on his own with their distant mother but she couldn't stay. Not after everything that had happened with Pete and Georgie.
The other picture was of her, Nate, Blair and Chuck at her mother's latest wedding. Nate was wearing a gray Armani suit that suited him perfectly. It matched well with his dreamy green eyes and his gorgeous lop-sided grin. He had his arm around Blair. Her chestnut colored hair was back in a ponytail that was simple yet elegant at the same time. She was wearing a blue dress with little sequenced patterns on it, every time Serena saw it it reminded her of the sea. The couple were smiling happily together while Serena stood beside them in a gorgeous golden gown. Her golden hair was a long curly mess but it looked perfect on her. She was smiling her angelic smile and from the look on her face anyone who looked at the picture and knew Serena well could tell that she was tipsy. Beside Serena stood Chuck Bass. He was wearing some expensive black tux that showed a subtle handsomeness about him. He was giving his usual smirk. He had one arm inappropriately around Serena's waist, although she was probably too tipsy to tell, and his other arm was holding a flute of champagne. His dark eyes had a menacing sparkle in them.
Every time Serena looked at the picture she always felt the familiarity of their friendship. The four of them had know each other for so long. They were most definitely her best friends. But now looking at it she felt a little lonely. She missed all of them. Blair was her best friend and Serena didn't even get to say goodbye so it was sad. Nate was always there for her, so loyal. And even Chuck had his moments. It was hard for her to think that she wouldn't be seeing them everyday just like she used to.
Serena gave a long lonely sigh and stuffed her suitcase under the bed. She didn't want to go to dinner and gain more stares from people she didn't know. She didn't want to have to put up with Daisy's perfect smile and Rhonda's lavender smell. So instead she just got into her pajamas and crawled under the covers of her bed. It felt cold and unfamiliar and the covers were itchy and uncomfortable. She hated this. She hated boarding school. But she couldn't go back. So she turned the lights off and went to sleep.
---
When Serena woke up that morning for a split second she didn't know where she was. Then she remembered that she was in boarding school because she slept with her best friends boyfriend, killed a guy and then ran away to Connecticut from all her problems. These were going to be Serena's first few thoughts every morning for the next few weeks, she just didn't know it yet.
She sat up in her small bed and looked around. Rhonda wasn't sleeping soundly in the double bed in front of her. In fact her bed was perfectly done up. Serena looked around the room for her cellphone to check the time. She could easily have looked at a clock but she was so used to this little morning ritual. It's what she had been doing her whole life. This usually made her late for school but at this moment she kind of lived in her school, so technically she wouldn't be wasting any time trying to hail a cab. She eventually found the pink, slide-up phone. The time was 9:20 am. Serena thought hard trying to remember what time her classes were supposed to start. 9:00 she remembered. Crap! She pulled her uniform from off a chair she'd laid it out on and put it on as fast as she could. She put her hair up in a messy bun since she didn't get a chance to shower. She put on her make-up, grabbed her books and rushed out to her first class.
It took a while for her to find the correct classroom but she did it eventually. When she entered she could feel the eyes of thirty boys and girls turn to look at her. She looked around at the teacher to see if he was mad or not. He didn't seem so. He looked like on of those easy-going teachers who Serena could charm her way out of trouble with.
He was in his early thirties. He had jet black hair and the brightest silver eyes Serena had ever seen. The eyes were framed with some designer glasses. He was tanned, tall and muscular and Serena knew that if she ever met him at a club, and she didn't know who he was, she'd totally sleep with him.
"Can I help you?" The TILF asked Serena with a clear low voice.
"Um...Yeah. I'm sort of new here. And I might have overslept a little" Serena said.
"Don't worry about it. You're only half an hour late" He said to her with a joking smile.
"Sorry. I'm not really a morning person" She said to him.
"Neither am I, but we learn to live with it. Now why don't you tell me your name and take a seat over there" he said pointing to an empty chair beside Rhonda.
"Serena Van Der Woodsen" Serena said as she walked up to the seat. She could feel everyone's eyes following her, except she had a feeling that all the guys' eyes were more focused on the fact that her skirt was a little too small on her.
"Well Miss Van Der Woodsen, welcome to Cheshire Academy. My name is Mr Powers" Mr Powers introduced. "And before you interrupted I was just telling my class how some of them really needed to learn to use their commas, because for some reason, I am teaching grammatically inept sophomores."
Half the class laughed a little at Mr Powers' insult to the dafter half of the class.
Serena had a feeling she'd like this teacher. Not only was he super hot but he had a sense of humor. She could tell that she could become his favorite in no time. All of a sudden she had the urge to call Blair and tell her about the TILF, but then she remembered that if she and Blair were talking, she wouldn't be in this stupid boarding school anyway.
So Serena tried to forget about her best friend by trying to strike a conversation with her new one. She turned to Rhonda who was sitting beside her and whispered sarcastically "Thanks for waking me up."
"You're new. We didn't feel it was our place. Besides we didn't think anyone could sleep all through breakfast and the first twenty minutes of class as well" Rhonda said snootily.
Suddenly Serena remembered breakfast. She realized just how hungry she was.
"What time's breakfast?" She asked Rhonda.
"8:40" Rhonda answered. At that moment Serena's stomach gave a little groan earning her a few looks from the students around her. Once everyone had turned away and focused their attention back on Mr Powers, Serena turned back to Rhonda.
"Well next time, wake me!"
"Whatever you want princess" was Rhonda's snarky reply. Serena sat back on the red plastic chair and sighed. She was really really going to hate it here.
---
That afternoon at lunch time Serena couldn't help but feel empty. Daisy was nice enough to invite her to sit with her and Rhonda, but Rhonda was reluctant. In the end Daisy's kindness won and Serena sat with the two girls. She wasn't very keen on eating though. Yes she was starving but she just couldn't get a bite of the lasagna that the cafeteria was serving. All she could think of was how Blair must be feeling, eating her usual yogurt with those bitches from Constance. She could almost see poor Blair sitting on the steps of the Met listening to Penelope's theory of where Serena ran off to and why. Serena's daydream didn't go unnoticed though.
"Serena, are you okay?" Daisy asked. Serena just shook the loneliness off.
"Yeah, I'm fine. Just a little homesick" Serena said.
"Aw don't worry. It goes away eventually" Daisy reassured her. Serena just sighed lightly. She noticed the people around her all staring at her as if she was some freak show.
"Why is everyone looking at me?" Serena asked. She knew she was the new girl but even at Constance she didn't get this much attention, and Constance had Gossip Girl!
"They're not looking at you, they're looking at me" Rhonda said taking a small forkful of lasagna.
"Rhonda's like the most popular girl in Cheshire" Daisy explained. Serena almost laughed. Rhonda gave out such a nasty vibe that she thought it hard to believe. But then again Blair was queen back at Constance and she could be a real bitch sometimes.
"I wouldn't blame them for staring at you though. I mean you're totally gorgeous" Daisy said to Serena. This made Serena a little uncomfortable. She'd been complimented on her beauty before but it had never been so straight forward. She just ignored it and looked around the room to see if she could spot anyone interesting.
Eventually she caught sight of a handsome boy two tables away from them. He had short dark brown hair, almost the same color as Blair's. And his eyes were the most unique thing Serena had ever seen. One was a clear icy blue color while the other was a sort of tropical green color. Serena thought he was quite beautiful, but in a manly way. He was certainly one of the most handsome guys she'd ever laid eyes on.
She couldn't help but notice that his multicolored eyes were staring at her. But not like all the other people stared at her. They were almost staring into her. They weren't judging her, they were dying to learn more. He gave Serena a small smile and Serena couldn't help but smile back. She still felt a little uncomfortable with him looking at her like that though. She couldn't understand why anyone would be so interested in her.
"I have to go" Serena said feeling a little awkward. She got up and walked away from her two roommates. Rhonda seemed disgusted that she'd left her tray but Serena couldn't care less. She was never the type of girl to clean up her mess anyway. She walked out to the hall where there were only a few students to stare at her judgmentally. And took out her cellphone. She decided that the unfamiliarity was what was causing all this awkwardness so she would do something that reminded her a little bit of home. So she clicked onto Gossip Girl and read the latest posts. They were all about her leaving. They had some theories, some rumors sent in by tippers and some little bit about how Serena's closest friends were reacting to her sudden absence. Sure it was all pointless rumors that Serena knew weren't true but it still gave her a little taste of New York. Giving out another lonely sigh, Serena got out of the gossip blogger's site and put her phone back into her pocket.
When she looked up again she saw the multicolor eyed boy walking towards her. Once he'd finally reached her she asked him the very thing she was wondering since she had spotted him.
"Why do you keep looking at me?"
"You seem interesting" He answered.
"You don't even know me" Serena said.
"That's why I used the word seem" he wittily shot back at her. Serena smiled. He reminded her of Chuck in a weird way. He was handsome like Chuck and witty as well. Although Serena got the feeling that he wasn't nearly as pervy. That was a good thing though. Serena had always said to herself that if Chuck was less of a womanizer she wouldn't mind sleeping with him, that is if they weren't such close friends either.
"I'm Serena" She introduced herself.
"Derek" Derek replied.
"Why do I seem interesting to you?" Serena asked. She figured if that's why he was staring that must be why everyone else was. That way she could make her interesting-ness go away and get them all to stop.
"Well first of all, you're new. Second, you don't look like you want to be here, you just have to" Derek listed.
"Maybe you're right. Maybe I don't want to be here" Serena said.
"Then why are you? You look like the type of girl who could talk herself out of just about anything" He said. Serena blushed a little at his compliment.
"I can but I kind of need to be here" Serena said.
"Why is that?" Derek asked.
"I'm afraid I don't know you well enough to answer that" Serena said giving him a sly smile.
"In that case why don't we get to know each other a little better?" He asked smoothly. Yep. Definitely a non-pervy Chuck, Serena thought to herself. She would have said yes if she didn't think she was way too messed up to date anyone.
"We shouldn't. You'll call, I'll be off sleeping with some other random guy at a club. It wouldn't end well" Serena spoke her thoughts.
"In that case why don't we just start off as friends" Derek said. Serena smiled. He was very hot. Even his voice was hot, if that was even possible.
"Alright" Serena said flirtatiously, "But only because you're so persistent."
She began to walk away. He watched her go. Staring at her perfect ass.
"So I'll see you around then, Serena my friend" He stated more than asked.
"I guess, Derek my friend" Serena replied and walked back to her room.
---
The rest of the classes that day had been the same as all the classes at Constance. The teachers would get angry at Serena for the simplest things and she would answer back rudely as usual. They'd threaten to throw her in detention and she just wouldn't bother with her work out of spite. It was nice for her to know that some things just would never change.
After all her classes were over, instead of sitting herself down and doing her homework like her roommates, Serena rooted through her clothes for a short party dress. She decided that since she was already sick of this place, she'd sneak out of her room, grab a cab to the nearest club and get herself so drunk that she'd forget her own name. It was easy to do, almost like a habit to Serena since she'd done it so many times before in New York. The only difference was that this time Georgina wasn't there to get her started and Blair wasn't there to get her home safely. This obviously meant that she'd have to drink less then usual but Serena decided she could live with that. She pulled out piles and piles of her clothes throwing all of them on her bed into a big messy mound of designer wear. Daisy seemed to think it was quite an amusing sight while Rhonda was secretly hoping that Serena would just stop and clean everything up. Eventually Serena found a navy blue dress the exact same color as her eyes. It fit her curves perfectly. It was in fact one of her favorite dresses. She remembered Blair had gotten it for her, for her last birthday.
She got out of her skimpy school uniform and put the dress on. She straightened her hair and redid her make-up. She put on some expensive sequenced blue heels took one last look at the mirror before Rhonda finally asked her what she was getting dressed up for.
"I'm going clubbing" Serena answered as if it was the most obvious thing in the world.
"We're not allowed leave the school after eight" Daisy informed her.
"Eight, seriously? I thought this was a school not a convent" Serena said getting some money from her wallet.
"It's a very strict rule you know" Rhonda warned her.
"I'll be fine. I've done this a million times before" Serena assured her.
"We're not waking you up if you have a hang over" Rhonda said.
"I can live with that" Serena said. Nothing could stop her from partying. It was all she had, a change of school didn't mean a change of lifestyle. Right?
"If you get caught we'll get in trouble for letting you go" Rhonda said.
"Then come with me. Might as well do the crime if you're going to do the time" Serena said smiling at the two girls. Daisy looked at Rhonda hopefully but Rhonda was having none of it.
"Look you're new here so you don't understand, but if you go down we're not saving your ass. And you can be certain that we're not going down with you" Rhonda said jumping off her bed and coming almost face to face with Serena. The height difference made it so she was more face to neck with her instead.
"I'm going out, and you won't stop me" Serena said coldly. Then she gave Rhonda a bitchy smile and walked out of the room.
At the club Serena did the usual. She drank anything any guy offered her and made out with loads of men who were a lot older then they looked and most definitely married. It was a ritual Serena had done many times before. Only this time Georgina wasn't getting drunk by her side, Blair wasn't giving them disapproving glances from afar while Nate stood beside her laughing and Chuck wasn't off somewhere sweet-talking some whore to a stall in the bathroom. This time it was just Serena Van Der Woodsen. A lonely blond bombshell from Manhattan. It was almost pathetic.
After hours of drinking martini after another, sticking her tongue down other people's husband's throats and acting like the dumb skanky blond everyone assumed she was, Serena got out of the club, grabbed a cab back to the school and went home. When she got there most of the lights were off except for a in few rooms. She realized the front doors of the building were locked and she hadn't really made a plan B since she never really needed one in the past, so instead she looked for any open window she could find. She eventually found one on her floor. She took off her heels and climbed up the red bricks since there was a decent amount of space between them, enough to put your toes in. She eventually reached the open window. She threw her heels in first and then climbed in herself. She fell straight on the floor seeing as the window was a little higher then she expected but nobody heard because the floor was lined with fancy looking maroon carpet that muffled her fall. It didn't help that she was way to drunk to see anything clearly. In the midst of her drunken sneaking she didn't notice the boy who was watching her, and had saw her sneak in.
"Serena?" Derek asked. Serena stood up. Her long blond hair was in a frizzy, sticky mess from all the drinks spilt on her. Her make-up was smudged and running. One of the straps of her dress was hanging loosely off her shoulder. Derek couldn't help but think that she looked perfect even in her imperfections.
"Hello my friend" She said in a drunken stupor and then giggled sweetly.
"Where have you been?" He asked giving her another look up and down.
"Partying" She answered. Not even trying to hide it.
"You obviously don't belong here" He said more to himself then to Serena. She giggled again.
"You remind me of my friend Chuck" She said for no proper reason. She was drunk, she didn't need a reason.
"Lucky Chuck" Derek said. Serena gave him one last smile before she started to stumble to her room. She brushed past him but then stopped.
"What are you doing out here?" Serena asked him with an interrogating look.
"Needed to use the bathroom" Derek said simply.
"Isn't there one in your room?" She asked. She was trying to sound serious with her interrogation but she was way to drunk to keep up the act.
"Broken" Derek answered. Serena just shrugged and turned to walk away again.
"Why did you come to Cheshire?" Derek asked suddenly. Serena stopped in her tracks and turned to look at him again.
"Because I needed to escape" She answered him simply.
"Escape from what?" Derek asked curiously.
"Myself" She said. Then she gave him a mysterious smile and walked back to her room. He just watched the blond beauty go. She wasn't like most girls he had met but he had a feeling that was a good thing.
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Coming up... Serena shows Derek her wild side. Rhonda plots to get rid of her and Mr Powers agrees to do the exact opposite.
