Disclaimer- I don't own any of the Gossip Girl characters.

Playing By the Rules

"But it's time to face the truth, I will never be with you."

-James Blunt, You're Beautiful

He knew that someone like him could never be with someone like her. He'd known it when he saw how Blair looked at Nate. He'd known it since fifth grade, when Nate had finally gathered up his courage and had asked Blair out. He was constantly reminded when Blairs' so-called-friends would gush of how 'perfect' Nate and Blair were together. It had taken awhile but he had learned to accept it. He found it a mere fact of life, such as the fact that Georgina Sparks is the devil reincarnate. He figured that they'd be the perfect couple, the couple that lasts through high-school and college, gets married, and has one big happy family. That's why he was dumbstruck when Blair came to Victorla at eleven thirty, and announcing that she had supposedly broken up with Mr. Perfect himself.

He'd never planned to sleep with her. He really hadn't; as much as everyone wanted to think that it was all a part of one elaborate scheme, it wasn't. He'd never admit it but it killed him whenever he saw her get hurt. Chuck would inwardly cringe whenever Nate would forget one of his an Blairs' anniversary or not have enough time to come to one of Blairs' mothers' brunches with her; Chuck would be stuck cleaning up his mess. Chuck would be stuck with Serena, both of them yelling and banging the door to make Blair come out of the bathroom. Then he and Serena would clean Blair up, make her look presentable to Dorota and Eleanor, and take shifts being on 'Blair Duty' where they'd make sure that she wouldn't make any sudden breaks for the bathroom. Then Blair would fall asleep in Serenas' arms, having just watched Breakfast at Tiffany's in bed and eaten her favorite get-well soup. What killed him was that the next day she'd be back to her normal self, doing a little bit of retail shopping, having her face plastered on Gossip Girl, and putting on her perfect smile, acting as if nothing had ever happened. Apparently she was a good enough actress, because Nate nor the rest of the world ever noticed that something had gone wrong.

He would never admit it, but he was scared when he heard that Serena was really buying that pregnancy test for Blair. He didn't-no couldn't be a father. He knew what kind of a father he would turn out to be and he'd be damned if he let some poor kid live through that. He, and nearly half of the Upper East Siders, knew what it was like to wake up, see your parents for maybe a minute before they left for work, to go to school, and to get home only to find that your parents are working late and then attending some fundraising gala. He knew what that type of life was like, and he'd be damned if he let some poor kid go through that. He was relieved when he found out that Blair wasn't pregnant. He was glad that no future-Bass would endure the same treachery that he had for all those years. But, although he wouldn't admit it, he was also glad that Blair wouldn't have to go through that. He knew what Yale meant to her, and it would kill him to see her give it up.

When Blair texted him, asking him to meet her on the roof of that godforsaken 'art exhibit' in Brooklyn he gave his signature smirk; for, after many months of teasing and taunting, he, Chuck Bass, had won the game. He made a few calls, downed the rest of his scotch, and boarded his helicopter, directed the somewhat confused helicopter pilot to Brooklyn, and was there in just short of a half an hour. Once she asked 'why everything has to be a game' he knew that things would only go downhill from there. Once she stormed away from him, he wondered why he had ever gotten his hopes up. After about a minute or so of just standing on the roof, taking in everything that had just occurred, he started down the stairs. As he was making his way down the stairs one of the least expected, and wanted, people he wanted to talk to hollered to him. He brushed off the elder of the Humphrey siblings and continued his descent. After Dan told him what he had done, Chuck was livid. He gave Cabbage Patch one of the hardest and iciest glares he had, and started for Blair's house.

When he told Blair that he'd, more or less, rather wait and have a real relationship he'd meant it. He'd known since the moment he met her that, eventually, they'd be together. He'd waited so long, and he used whatever self-restraint that he had in him, and told her that he'd rather wait. He'd rather wait so he wouldn't blow it; so he wouldn't blow his one and only chance with the Blair Waldorf; so he wouldn't blow his chance at friendship with her, like Serena had (well temporarily); so he wouldn't blow his chance at love with her, like Nate had. Blair Waldorf was one-of-a-kind and he'd be damned if he missed his chance. Everyone had always thought, as a mere tacit rule, that Blair would end up with Nate and that Chuck would be a replica of his father. They simply couldn't fathom that Chuck Bass would ever be with Blair Waldorf. Chuck had once regarded these assumptions, let them be and leave them as may; but everyone knows that Chuck Bass was never one to play by the rules.

A/N- Hoped you liked the story! I actually have been working on this one for awhile, you know maybe five minutes every week or so, and finally I just finished it up today! Thanks for reading! Please tell be what you thought of it and click the little blue button!