Author's Note: Hello guys! This is my first story, and I would love any feedback you're willing to give. Enjoy:)

He wasn't supposed to feel this way about her.

Chuck Bass was notorious in many categories. He was a well-known player and an even better-known schemer; yes, Gossip Girl had taken his name, swirled it in a whirlwind of (mostly true) epic stories, and made him a legend.

Chuck Bass was no saint.

Girls were playthings to him, and he often tossed them aside like old rag dolls when they were no longer of use. He had a legacy, that was certain, but a stained one.

There was only one one girl in the Upper East Side, hell, most likely the world, that was a worthy match in devious intellect. Blair Waldorf was as infamous as he, and her calculating mind and undeniable charm were an object of envy even to him. Unfortunately, that evil mind was forever hidden under a designer headband and a coordinated outfit; no, a girl like that wasn't needed. He begrudgingly teamed up with her on schemes more often than desired, and though he'd never admit it, the pair had agendas and plans that meshed all too well.

All of the logistics aside, Chuck Bass was a good friend.

Blair was his best friend's girlfriend of forever, and he knew that Nate had always had a sliver of apprehension when it came to the duo uniting. Chuck was notorious, and not the type of guy that you would want around your already-unpredictable partner. As an admirable friend, he kept his distance.

That's why seeing her on the stage, down to her slip, was so unexpected. Even more so was how much he found himself enjoying it.

Perhaps the most surprising of all was the fact that she was next to him, in his limo, boyfriendless and vulnerable. God, Nate could be an idiot. Having a girl next to him was not new, but normally at this point there would be a different kind of silence. For the first time in Chuck's life, he didn't know what to say.

"Thanks for the ride home," she said quietly, breaking the thick tension that hovered in the air.

A million replies raced through his mind, but he tried to keep Nate at the front. "You were... amazing up there." God, he needed his voice to be friendly and not full of pent up want and need and hunger, but he knew that he had failed as soon as the words escaped his lips.

She maintained eye contact, her heavy- lidded stare sending him close to bursting. With every inch closer that she slid, he felt the intensity strengthening, and thoughts of his best friend were gone.

Before Chuck knew what was happening, her lips brushed his, and he didn't have the strength to pull away. They clawed at each other, tongues meshing as well as their plans had one hazy day ago, but he needed to know. "Are you sure?"

Chuck hated himself for asking, for opening up the possibility for the ever so rational girl in front of him to change her mind. But he would have hated himself more if he hadn't, he reasoned. He needed to know that she was sure.

In response, she pulled herself on top of him once more, tugging at his suit jacket. He placed his hands on her waist, pulling her closer. She was sure. He knew. And so did he. This time, it was different.

Author's Note: I hope you liked this (short) prologue. Future chapters will be much longer, and sometimes it'll be from Blair's POV. Feedback is much appreciated! Thanks for reading!