A/N: Ok so I've noticed that in a lot of stories people have the perspective that Chuck was kind of in love with Blair since like way before the show started, but I've never really bought into that idea. I think it was more something that just kind of came out of nowhere for him just like it did for her. So I just randomly came up with this and wrote it really quick so I'm sorry if it is pretty awful. Any reviews would be wonderful!
Chuck had never really been a part of the Non-Judging Breakfast Club. Well, he was, but at the same time he wasn't. Serena a Blair both saw him as a disgusting, immature pervert who just came along with Nate. While they accepted that he was a part of the group, as an extension of Nate, they would never go so far as to call him a friend.
Sure, he was there with Nate and Blair when Serena was in a drunken/drugged state or when the group would be together at some fundraiser luncheon. But at these little get-togethers Chuck was still on his own. When they would meet up, he would make some disparaging comment about Blair's virginity and then he would move on to use some sleazy pick-up line on Serena. Both girls would then scoff at him and remark at how disgusting he was as Nate would crack a small smile. He would then just drift off to the side with a scotch and observe the other three interacting, making the occasional leering comment, but for the most part remaining silent.
Things began to change though when Serena left after the Sheppard wedding.
Blair had always been a bitch. She was the ice queen to Serena's sweet lovable princess. But after Serena left, she took her scheming to a whole new level. She was determined to remain on top at Constance and she was constantly coming up with plots to bring down whoever tried to get in her way. Without Serena there to use her niceness to keep the hatred to a minimum, Blair soon found herself facing many more enemies than she had ever had before. And because Nate was being distant (which was a contributing factor to her desire to be on top) and therefore little help in her plotting, Blair turned to the one person she knew who was a bigger bitch than she was. The one person who could take down anyone, anywhere, at anytime. The one person who could come up with ruthless plots just as quickly as she needed them.
They bonded in that year that Serena was gone. Nate was busy brooding over the loss of his blond crush and Chuck and Blair united over their mutual love of scheming, plotting, and gossiping. He helped her rise to her Queen B status and she provided the companionship he had been missing since Nate had become so Emo.
It's not like they were great friends or anything. Blair needed someone to help her conquer Constance and Chuck was always one to enjoy bringing bitches down. It was only once they started plotting together that they realized the clever banter they could only really keep going with each other. In each other they found the only person who could match their intelligence and wit (two things both of their best friends were lacking).
When Serena returned, nothing changed. Chuck still made snarky comments about Blair's virginity. He even tried his best to get Nate to finally 'seal the deal.' Sometimes, he thought he wanted Blair to lose it more than Nate did. She just had this look about her that screamed sex goddess hidden under that her innocent virgin exterior and it was just begging for someone to finally fuck her and provide that release. This is exactly why Chuck pushed Nate so much to have sex with his girlfriend, so she would finally get some and lose that look which held a certain appeal for Chuck, though he would never admit it out loud.
Chuck also still made blatant lewd attempts at getting with Serena, even though she had become the latest target for him and Blair. Even as Chuck was trying to hook up with her, he was still plotting with Blair for ways to bring Serena down. His discovery of her Ostroff Center visit and the planning he did with Blair to use it against her played out like the dozens of schemes they had planned and pulled off in the previous year.
But Blair and Serena reconciled. Even after Blair did her best to destroy Serena's future. They became best friends once again. This didn't affect Chuck in the slightest. He may have been slightly baffled by this turn of events, but it didn't really change anything. When Blair had a some sort of plot to execute, she still turned to Chuck, because even though she had her best friend back, she still needed to protect her position as Queen, and let's face it, Serena was still way to nice to be of any help in any sort of plot for social destruction.
To Chuck's dismay, Nate still had not done the deed with Blair, causing Blair to still have the "Please Fuck Me Now" look about her. It was very difficult for Chuck to be around her when she always looked like that. He had to constantly remind himself that she was strictly off limits, even for one good fuck. Even if she and Nate broke up, he had claimed her first; she would always be Nate's. Even exes are off limits to best friends. So Chuck just kept hoping for Nate and her to get it on so she would lose the appeal she had when she was the virgin queen who was just begging for sex.
When Chuck put together his proposal for Victrola, it was only logical that he would run it by Blair first. She was one of two people that he actually considered a friend and even he knew that if he were to show the club to Nate, his response would be something along the lines of "Wow man this is really cool." Chuck knew that he would get a much more honest (and detailed) reaction from Blair. So when she said she was impressed, and proud, he was much more confident that his father would go for the proposal.
Later that night, when Blair showed up at the club saying that she and Nate had broken up, he was surprised that it had happened that night, but not surprised that it had happened. He had figured they were heading for splitsville for a while, considering Nate's obvious crush on Serena and Blair's obvious need to be fucked despite Nate's continuing reluctance.
When she got up on stage and danced, Chuck felt his self-control breaking. The sex goddess he had always known was hidden under the surface was finally showing herself and he wanted to be the one to finally free her. But he couldn't. He just couldn't. She was Nate's. Even if they broke up, she was still the ex. She was off limits. Forever.
As she danced, Chuck couldn't tear his eyes away from her. He looked at her with such adoration and want and desire. But in his mind he just kept repeating his mantra. She was off limits. She was Nate's. Off limits. Nate's.
With those thoughts in mind, he was able to hold himself together. But once they were alone together in his limo, with her scent surrounding him and her body just an arm length away; it was harder than ever to hold himself back.
Off limits. Nate's. OFF LIMITS.
When she softly uttered that one simple sentence: "Thanks for the lift home," he couldn't stop himself from letting just one of his thoughts slip out.
"You were… amazing up there"
But revealing that one thought led to everything he wanted and everything he had been trying to prevent. He had never been one to practice self-control in his life, so this whole evening had been extremely difficult for him and considering all the things that were running through his mind, that was one of the tamest things he could let slip.
After he spoke, Blair slid across the seat, came up right beside him, and kissed him. She kissed him. Damn this woman. She was going to kill him.
NATE'S NATE'S NATE'S
With his very last strand of self-control, Chuck managed to break the kiss and choke out just one question. Two words: "You sure?" And when she answered by crashing her lips back to his, that last strand snapped and Chuck was gone. Any thought of Nate vanished completely from his mind. He was finally able to fuck the virgin queen and release the sex goddess Blair Waldorf had hidden inside her for so long. He thought that once she lost that 'virgin needing to be fucked' air she would lose her appeal. So imagine his shock when he realized that her appeal only increased once she had been thoroughly ravished by him. Only him.