Ok so this is my first fanfic. I've centered it around Chuck and Blair, but there's also some Ca/J, N/S, and D/V. I've changed a lot of the backround story. Rufus married Lilly when Dan and Serena were 14. Jenny is only one year younger then Dan. Carter is the same age as Chuck. Georgina goes to Chapin with Poppy and Gabriel. Blair's dad is straight and a polititian, and the rest is explained. This first chapter is just to set-up the story so it might be a little boring. Hope you enjoy!

Chapter 1

He got off the airplane at nine in the morning on a relatively hot August day. He already had downed three scotches on the Bass Family jet when he was greeted by his processional. He had been at bordering school in Zurich for the past three years, only visiting his home at the Upper East Side on select holidays and breaks. But his father had taken a new wife and in that had decided to reunite his family by having Chuck return to New York for his senior year. He hadn't expected his father to show up to greet him. They barely spoke and he knew his return was not out of the love in his father's heart but because he wished to impress his new trophy wife with his compassionate family-oriented side. Though he hadn't kept a close relationship with his father he had kept ones with his friends. He, Nate, Carter and more recently Dan Humphrey had traveled the world together partying it up on weekends and breaks because honestly who was going to stop them? Carter's parents were never in town, Nate's were to caught up in their deteriorating marriage to notice and Dan's father was to swept up in gallivanting around town with Lilly Van der Woodsen who insisted on giving the children "freedom"' to make their own choices and live their own lives. A crock of shit, if you asked Chuck, she was just to wrapped up in self-medicating and social events to be involved and Rufus didn't seem to put up a fight.

So that was who waited for him at his limo. He had known Carter and Nate his whole life.

Carter had light brown hair and dark blue eyes. He and Chuck had rivaled each other since middle school to see who could gain the most conquests. Carter was competitive and sometimes a mean drunk, but they never judged one another's actions though Chuck would never be in the position to. Carter however had grownup with somewhat loving and supportive parents, atleast until he was old enough to take care of himself, so he didn't come with all the baggage and commitment issues Chuck did. He from time to time dabbled in monogamy. The one thing that really banded the boys was their view of life's priorities. They both only cared about two things, money and the pleasure money brought them and boy did it bring them a good time. Since they were thirteen they drank like fishes and did any and all drugs they saw. Girls were the same. If they saw it and they wanted it they got it. At fourteen they were picking up models and socialites at nightclubs though they had lost their purity a few years before.

Nate on the contrary was a "good" boy. He was a Van der Bilt with an impeccable reputation though he was far from innocent. Nate was perpetually stoned though he hid it well. And though he wasn't as much of a lothario as Chuck or Carter, his sandy blonde hair and baby blue eyes had every girl at school dreaming of being his girlfriend and he had learned to use that to his advantage often leaving broken hearts in his path.

Dan was new to the group. He had dark brown hair and amber colored eyes that reflected his often-somber moods. His father had married into old money in the form of Lillian Van der Woodsen when Dan was fourteen. He had since risen to the elite with the Van der Woodsen name behind him, and friends like Nate and Carter. Nate and he were on the soccer team together and Carter just came with being friends with Nate much like Chuck did. He tended to be a little holier than though but that was over-looked due to his sharp wit that entertained Carter and Chuck.

So here they were his best friends and really his family at this point that welcomed him back to the Upper East Side.

Carter was the first to speak, "Welcome home my good man it will be fun to have so real competition in this place." He said with a smirk giving Chuck a pat on the back.

"No doubt Nathaniel has been a disappointment in that regard" Chuck laughed.

"I do fine just ask the girls on the met steps" Nate said defending his honor.

"You have slept with all of them" Dan sighed, "Well except one" he finished a smirk dancing on his lips for a second before transforming back into his always sullen expression.

Chuck noticed Nate pout at that statement and Carter suppress a chuckle for what he didn't quite grasp.

Carter quickly brought the conversation back to his earlier point.

"Nate you make everyone of your liaisons into girlfriends that doesn't count you cant date them before and after. Hit and quit has always been my motto" he declared.

"How poetic." Dan scoffed.

"Hey you've had girlfriends before." Nate argued.

"Yes, but in the end I always came to my sense and ended it. You turn every one-night stand into a two month relationship." He summarized.

"Well I' m back and I plan to pick where I left off, I think it was blondes" Chuck smirked inciting a laugh from Carter and Nate and a quick smile from Dan.

"God knows red-heads have never done you well," Nate laughed.

Chuck bristled, "Oh, please don't bring her up. She still calls me the psychopath. And don't act all superior, you've all been there, even you Humphrey." Chuck accused.

"I was drunk and." Dan began but was quickly cut off by Carter.

"And heartbroken over your new money, former Williamsburg girlfriend god we know." He now directed his statements to Chuck, "If you think he's depressing now you should have been here during the two weeks they were broken up. He wrote a poem about her where he rhythmed the word love with the word dove. Pathetic." The last word was sneered at Dan.

"Whatever Vanessa liked it." Dan said defensively.

"Well mediocrity loves mediocrity." Carter jeered.

"Hey!" Dan snapped.

"I'm just saying stick to fiction, poetry's not your strong point. And well as for Vanessa, she used to live in Brooklyn before her mom wrote that book." Carter said.

"I used to live in Brooklyn" Dan yelled.

"I'm aware." Was all Carter said before dismissing Dan with a wave of his hand ending the conversation.

"Well now that your guys' little argument has passed I would like to go home. School starts in two days which means running into Georgina starts in two days and I look forward to trying to avoid her all year."

"Don't be so sure. Your father has asked us to take you to his brunch soirée this fine morning to reintroduce you to the upper crust." Carter said in an exasperated breath rolling his eyes at the last part.

"Already with the schmoozing, dear old dad hasn't lost his touch. Very well, I'd say I'm sufficiently buzzed enough to survive this." He said.

Attention all upper-east siders the prodigal son returns. My sources say Chuck Bass just landed in town and he's staying. Boys guard your girlfriends and girls you know exactly what to guard because if you thought King Carter was bad just wait for what our dark knight has in store. When Chuck Bass is involved all bets are off, I just can't wait to see which girl falls for his charms first. I wonder how our resident queen will like this new edition to her kingdom. Word is the two haven't even met. Good luck Queen B.

You know you love me

Xoxo

Gossip Girl

The Boys arrived in style making their entrance into the ballroom of the Palace. Every upper class girl from Constance and boy from St. Judes was in attendance and almost all chatter stopped as they put down their phones seeing the man enter they had just read about. Chuck made his way through the room surveying his classmates, the girls more than anything. As he looked he found a large group of girls sitting at a table, only four girls stood out above the rest.

The first one that caught his eye was a wafer thin bleach blonde bombshell. She had ivory skin and long hair that was straight with sharp angles to it that hung down to her waist framing her soft face that contained ice blue eyes shrouded in black eye shadow and mascara. She wore a short black dress and a somber expression, which immediately told him this, was Dan's little sister Jenny he'd heard about. She had been thrown into the Upper East Side party scene at thirteen with no previous experience. She lost her virginity freshman year to a drug dealer named Damien that got her hooked on coke. Even then she clawed her way up the social ladder trying to overcome her Little J from Brooklyn reputation. Even after rehab at the Ofstroff she succeeded. To be in the in-crowd she so desperately wanted, she had to fight for the approval of one girl. She knew she could never replace the bubbly blonde at the Queen B's right hand but the left hand that was a whole other story. She finally ousted Penelope from her position at the queen Bees third in-comand and took her spot. But her power struggle with Penelope, her drug abuse and her toxic relationship to Damien had robbed the once naïve girl of her innocence. Her once hopeful eyes were now replaced with sharp icy ones that saw now good only the cold reality a sixteen-year-old girl shouldn't know.

The second was a girl he knew all to well from his early party days. Serena. Serena was sunshine captured in a human form. Her long golden hair hung in loose curls and her big green eyes sparkled with optimism and happiness that not even the Upper East Side could wash away. She wore a somewhat promiscuous gold dress that showed off her long tan legs. Serena wasn't characterized as a slut though her reputation often led to that description, though no one ever said it aloud. She'd started sleeping around in the eighth grade when mommy dearest went off to Singapore with husband number three. But something about Serena made it impossible to call her such a name. She was too sweet, to happy to ever insult.

The third he recognized from photos on Dan's phone. She had caramel colored skin, long black hair that had with soft waves through out it. She had warm coffee colored eyes and was talking animatedly with Serena. This must be Vanessa, Dan's on and off girlfriend for over a year. It astounded Chuck that she was sitting at the elite girl table. She was after all knew money, but Serena had taken an instant liking to her as did Jenny though she was not as vocal about it in fear of falling out of favor with the Queen Bee who bounced back and forth between indifference and disdain for Vanessa.

It was then that his eyes fell on the most beautiful of the girls. She'd had her back turned to him this whole time while she talked to a petite blonde he knew he'd slept with named Hailey or something. When she turned around he stopped breathing for a moment. Her Chestnut curls hung in perfect ringlets just past her shoulders pulled away from her face by a blue headband to reveal her eyes, her big liquid chocolate doe-eyes framed by long thick lashes. His eyes next took in her full pouty red lips and then her petite figure that was concealed by a white lace dress. Thigh it was quite modest it couldn't hide her full chest and dainty hips that led to her small but perfect ass and then down to her slender legs porcelain white like the rest or her body. She was breath taking. Absolute perfection if he ever saw it. How did he not know her? Surely even he would remember a beauty like her, he had to find out who she was. He had to have her. He went to approach her when suddenly someone grabbed his arm and whipped him around.

He came face to face with his worst nightmare. Georgina Sparks. The girl stood there smiling at him like they were on good terms.

"Hey Chuck I've been looking for you." She purred. "You keep missing my calls I was starting to think you were avoiding me"

'Your very perceptive." Was all he could muster up in his annoyance?

"Oh come on don't be like that. Your back in town I thought we could have some fun." She whispered seductively.

"From what I here you've had a whole lot of fun with out me, even with Humphrey." Chuck said with a pointed look. His patience was growing thin and if she didn't quit it he was going to explode at her.

"Well I had to keep myself busy somehow your never here," she lent in for the next part, "I've missed you."

"Well I haven't missed you." He barked not in the mood for this game.

"You always act like this, but in the end you always come back. Oh come on we had such a good time in Venice back in June." She stated.

"A good time I remember is me sleeping with your friend Poppy and you throwing an ashtray at my head and setting my limo on fire. What part of the last part was a good time?" Chuck almost yelled, straining to keep his voice under control.

"Fine if your going to be like that then I'll go entertain myself elsewhere." With that she pushed past him and stormed off.

When Chuck turned back the perfect brunette was across the room talking to a large group of people.

'Who was she?' he thought.

Chuck approached Nate who was standing in the corner with a glass of orange juice.

"Nathaniel, do you know that girl?" Chuck asked quietly pointing to the intoxicatingly beautiful girl across the room. Nate smirked at him.

"Don't even go there its not gonna happen." He chuckled.

"What are you talking about, I'm Chuck Bass." Chuck was shocked by Nathaniel's statement.

"Look I dated Blair for a couple months sophomore year, and she is so not your type."

"Hot girl is my type she fits the description perfectly."

"Well than your not hers. Her parents are super elitist old money. The blood does get much bluer than the Waldorfs and they keep her under lock and key, for good reason. Every guy and school has tried to hit that even yours truly and Carter. She's a no go."

"A little protective eh Nathanial. Do you still have a thing for her?"

"No we broke up over a year ago we're just friends. But trust me you don't have a shot. Almost no one does. Her uptight mom picks who she dates and the formerly banished playboy of the upper east side doesn't fit the bill."

"Well you dated her"

"I'm a Van der Bilt. Look her dad's a politician that means image means everything and having his only daughter linked to you… not exactly good press. My family is like the Kennedy's but without all the scandals and untimely deaths. That's the only reason her mom pushed for us to be together so much."

"Ugh... you being ridiculous. If you still like her cause she dumped your ass just tell me. I'll back off"

"Its not that really. I broke up with her anyways… well sort of." Nste muttered the last art under his breath, but Chuck still heard it.

Chuck raised his eyebrow at that.

"Ok you're not gonna get this I don't really get it. I broke it off but only because I was pretty sure she wanted to dump me."

"That makes no sense."

"Its like she wanted to dump me, but she was almost to polite to do it and to afraid of what her parents would say if she dumped a Van der Bilt. We were just better off as friends. And that's what we are so don't mess with her ok." Nate pleaded.

"That is the stupidest thing I have ever heard." Chuck laughed, "Are you retarded?"

"Shut up. Just leave her alone she's not like the girls you sleep with. She's completely different from anyone I've ever met. She's even going to set me up with Serena who I really like. And if you try to sleep with Blair, only two possible scenarios unfold. You succeed, drop her, she hates you and me for being your friend. And Makes Serena hates me. Or two she turns you down thinks you're a perv and a jerk, thinks I'm a jerk by association tells Serena I'm a jerk and once again Serena hates me. Don't ruin everyone's life over your hormones." Nate reprimanded.

"I think you're over estimating one girls control over another."

"You don't know Blair, she's the queen of Constance. I've seen her blackball a girl at school just for showing up to a party in the same dress. Serena and her are best friends. Just don't ok."

Chuck just kept staring at the doe-eyed beauty. For split second their eyes locked and he felt his breath hitch in his throat. Nate caught his look at the brunette.

'Seriously pick some one else. Penelope's hot and Kati's kinda cool."

"Been there done 'em both last year on winter break." He said staring intently at the beautiful creature before him as he replied. It was at that moment the girl he had been fixated on started walking toward him.