A/N: So this is my first ever fanfiction. I'm not much of a writer, but any feedback at all would be great! Thanks!
Chuck was standing outside of the school, smoking before class, while waiting for his best friend, who was late like always. After a few more minutes of waiting Nate appeared at his friends side, a tired look on his face. Chuck put out his cigarette as he and Nate began to walk towards the school.
"So, Nathaniel, why the long face? You said that you had plans last night, so what, did the Captain force you to sit through another of his business meetings." Chuck said with an air of nonchalance and a humorous attitude.
"No, it wasn't that. Um, Blair and I had our first date last night." Nate said almost reluctantly.
"And it didn't go too well I see. What happened, did you not get any? I mean you guys have liked each other for forever I'd be surprised if you didn't," Chuck said, attempting to keep the conversation on the upbeat side, he'd been having a good day and he didn't want it to be interrupted by Nate's constant Blair problems.
"Haha very funny. It wasn't like that, some people actually want to wait until High School starts to even begin thinking about that."
"That's a pity. Take it from someone with two years of experience, you're missing out," Chuck countered, he loved reminding people of the fact that he'd lost his virginity in 6th grade.
"Well Blair and I want to take it slow. Anyway that wasn't even the problem," Nate grumbled after getting pulled off track by Chuck again.
"Oh please, do tell all about this date with your precious Blair," Chuck drawled out, if Nate was going to insist on telling him might as well get it done with quick.
"Well, it actually wasn't that bad," then why are you telling me this, thought Chuck. "It was just really…awkward," Nate ended lamely, leaving out one small detail.
"What else?" Chuck said, reading his friend perfectly.
"Don't tell Blair, because I really do like her and I don't want her to think anything of this, but all during our date I couldn't stop thinking about…"
"Nate!!!!!!! Come over here I need to ask you a question!" shouted Serena from all the way across the courtyard. Nate and Chuck had finally arrived at school. Nate immediately rushed off to answer Serena's call. Could you be anymore obvious Nathaniel, Chuck thought as he saw Nate fawning over Serena. He chuckled under his breath at Nate's obvious feelings for Serena, but at the same time he couldn't help feeling sorry for Blair and how little she knew.
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After only a few minutes of sitting by himself, after Nate ran off after his blond counterpart, Chuck felt the presence of another female beside him. He turned his head to see, as he expected, Blair staring at Nate and Serena with an indiscernible look on her face. When she felt his gaze on her face she turned towards him.
"I need your help with something," she said cutting right to the chase.
"What? More advice on getting your boy toys affection, or do you want to know what he thinks after your little rendezvous last night?" Chuck said mockingly.
"That wasn't what I was going to ask, but since you seem so eager to talk about it…tell me what Nate said about our date," Blair's voiced changed drastically from sweet and innocent to demanding and controlling. Her eyes were firm, but underneath Chuck saw a glint of something else.
"Well…" Chuck began, trying to decide between being truthful or just flat-out lying to her.
The longer Chuck waited to construct his answer the farther Blair's face fell, until her carefully composed mask had faded away leaving only the vulnerable 14 year old girl underneath.
The minute Chuck saw this he immediately answered, "He loved it. He went on and on about how amazing you are and how he can't wait to go out again. It was actually very annoying, not something I want to hear this early in the morning. I was lucky that I kept my breakfast down," Chuck answered with a face of complete sincerity.
"Why'd you have to wait so long to say that? Do you like playing with people's emotions? You're so annoying! Nate must be delusional to hang out with you so much. But now that I'm officially his girlfriend we'll be spending all of our time together, just the two of us," Blair said, quickly covering up her moment of weakness.
"Please, you must be delusional to think that he likes you more than he likes me. Why else would he tell me stuff that he would never tell you. Oh, and I forgot to tell you how disappointed Nate was that you two didn't have sex last night. I mean come on Blair, you've liked him since you were 5, and you couldn't put out on your first date? If you're worried about your performance I'm always here if you want to practice," Chuck said, his voice getting low and seductive. He leaned toward Blair with his signature smirk in place.
"You're disgusting. Not everybody wants to have sex before high school, because some people want it to be special. Not everybody wants to go around saying, 'I lost my virginity when I was 12 to a certified psycho who I've avoided ever since that day," Blair finished with a satisfied smirk on her face, while she watched Chuck stiffen, she'd finally gotten to him.
"I thought I told you not to talk about that bitch ever again. We had an agreement," Chuck hissed at her, a furious expression on his face.
"We do, and that will be the last time I say anything about it as long as you start behaving yourself. Since you are Nate's best friend it is mandatory for us to deal with each other, so no more revolting remarks," Blair continued not intimidated at all by Chuck's death glare. "Anyway, I actually came over here for another reason than to be harassed by you. What do you know about Isabelle Smith?" Blair said taking out folder with a girl's picture and a pile of papers.
"She's rich, her family just moved here from California, and she's already dated half of the boys lacrosse team. Why?" Chuck fired off, a grin already forming when he realized why Blair had come to him.
"Oh nothing, I've just heard from a very reliable source that Nate is her next target."
"Don't tell me you're afraid that this girl will steal Nathaniel away from you. Please Blair, she's got nothing on you."
"I know. I'm just making sure," Blair trailed off, trying to hide the smile that appeared on her face at Chuck's words.
"Well, don't worry. I'll take care of her for you," Chuck said grabbing the file from Blair.
With a satisfied smile and a quick, thank you, Blair ran off. Leaving Chuck alone. Why he continues to do these things for Blair he'll never know. I mean it's not like he liked her or anything. In fact if it weren't for Nate liking her since forever he probably wouldn't think twice about Blair Waldorf. But after all those years together how could they not be friends, Blair only liked to pretend that she was revolted by Chuck, but whenever it came to scheming she would run directly to Chuck. And he began to do the same with her, in fact he began to take such joy in her happiness that he was willing to do anything for her. And if that is keeping all other women away from Nate, and Nate's sights on Blair, so be it. Isabelle Smith would be easy enough, but Chuck wasn't so sure that a certain blonde best friend would be as easy.
