Disclaimer: I do not own in part or whole the characters depicted in this fictional story.

Please Review/Comment and I Might Post More. FYI, I have a total of 60 chapters ready to go if I feel that there is enough interest.

01 Nate Makes a New Friend

Nathaniel "Nate" Archibald stared blankly at the paper before him. He had a little over fifteen minutes to complete his Latin test and he barely managed to answer the first few questions. For a dead language, it was certainly giving Nate a run for his money. Nate was never the model student, so failing this test wouldn't surprise anyone who knew him. What might surprise people was the reason he couldn't focus. Nate was considering dumping his girlfriend, Blair Waldorf.

Nate and Blair had been dating for over a year now and had been friends for much longer than that. They both grew up on the Upper East Side in Manhattan and their parents were long time friends (or enemies depending on the day of the week). He liked Blair. She was short, with dark brown hair and piercing brown eyes. She was smart and was on the committee for every social event worth going to. And, oh yeah, she was hot! Arguably, Nate could see no reason any guy wouldn't want to be with her. Yet he was torn.

Blair had always been there. She was always nice to him while they were growing up. She genuinely seemed to like him. As they entered high school, though, Nate noticed that she changed. She seemed more confident and more focused. This only intensified when their friend, Serena van der Woodsen, mysteriously disappeared for boarding school the previous summer. Shortly after Serena left, Blair started warming up to him. Nate figured this was because Blair was intimidated by Serena. Nate smiled: Serena van der Woodsen.

Serena was the most beautiful woman Nate had ever seen. She had sunny yellow hair, soft blue eyes and a laugh that made his heart melt. She looked great no matter what she wore, a trait which earned many nasty stabs at her from her peers. Nate was mostly infatuated with Serena because she was wild and free. Serena did what she wanted when she wanted to. Rumours also stated that she did who she wanted when she wanted, but Nate never believed them. Serena was perfect. Of course, the night they'd spent together the week before she left created the tiniest ounce of doubt in his mind.

It was just over a year ago, last July in fact, when Nate last saw Serena. He was at home that night watching an old spaghetti western when Serena texted him. She was bored and lonely and wanted to see him. Now, Nate would never have denied her, but he and Blair had been spending a lot of time together. Although they weren't dating, he got the impression that she would not have approved. Still, Nate had just smoked some pot and felt that company would be nice. He just wouldn't tell Blair.

When Serena said she was bored, Nate assumed she was home alone. He had no idea she had been out drinking by herself. She showed up extremely drunk and climbed into Nate's bed as they watched his movie. At one point, her hand made its way on to his inner thigh. Normally, this would have made Nate nervous, but the pot had mellowed him out and he thought nothing of it. Soon, Serena was massaging his thigh, giggling softly to herself. Nate definitely noticed this and he could feel his penis swelling in his pants. Serena laughed.

"So, I take it you don't mind, then?" she asked playfully.

He chuckled to himself.

"My little friend sure doesn't," he commented, "Did I say little? I didn't mean little-little. I mean, I don't-"

"I know what you meant," she assured him as she climbed on top and straddled him.

He watched in awe as she slowly removed her silky, black dress. It seemed to melt away revealing nothing but her creamy skin. Nate looked at her breasts, barely concealed by a black bra. They weren't huge and they weren't tiny. They were perfect. He brought his hand up and massaged the left one. It felt sensational. Serena smiled at him. She pulled his shirt up and over his head. She stared down at his chest.

Nate was insecure about many things, but his body was not one of them. He knew he was in great shape. All the girls at school constantly stared at him, he saw it. He even saw a few guys notice. It made him feel good. It made him feel better that Serena was no exception; she was definitely pleased by his physique. She leaned in and kissed him. He undid her bra while she did this. She sat back upright and let it fall off. Nate carelessly tossed it aside. There was no doubt about it: she had a look of desire in her eyes.

"Before we go any further, I have a question to ask and I want an honest answer," she insisted.

Nate swallowed hard and nodded, his breathing heavy.

"Have you ever been with a girl before?"

He searched her eyes for a hint as to why she was asking. She smiled her flawless smile and he abandoned his search.

"No," he answered finally, "Is that-"

"It's fine," she assured him, "Don't worry. I'll make sure you enjoy your first time."

And she did. It was amazing.

Nate looked up. He had only five minutes left. No point in trying now. Ugh, who gives a test two weeks into the first semester of school? Out of the corner of his eyes, he noticed his best friend, Chuck Bass, watching him intently. Chuck was wearing the expression he wore when he was interrogating someone. Nate hated when Chuck did that. Wasn't he allowed to have a life outside of Chuck Bass? Nate looked around the room. The class was nearly over. Chuck would hand in the test, track Nate down and force him to talk. And this was Chuck Bass; no one ever refused Chuck Bass. Nate needed a distraction. He had Algebra next, another class with Chuck. He noticed a thin, pale boy with messy brown hair and a thin scruff forming. It occurred to Nate that this boy was also in his Algebra class. It also occurred to Nate that this was also another class which he was failing, but he didn't care. He had a plan.

The bell rang. Nate jumped out of his chair and handed in his test. He immediately walked over to the scruffy boy.

"Hi, did we have any homework for Algebra?" he asked lamely.

The boy looked up at him. He seemed confused for a moment.

"No," he answered, "But we did have some reading to do."

"Oh, really?" Nate asked, feeling Chuck's eyes burning a hole in the back of his head.

"Let me guess, you didn't do the reading?" the boy asked in a tone Nate couldn't decipher.

"No..."

The boy sighed.

"Well, if you promise to walk fast, I'll give you a brief summary of it," the boy offered.

Nate smiled and nodded. Perfect.

"I would greatly appreciate it. By the way, I'm Nate."

The boy stared at him briefly.

"Let me guess: you don't know who I am?"

Nate blushed and looked away.

"It's okay, no one here seems to know who I am, even though I've been in your class for over three years," the boy commented.

"No, I know who you are," Nate insisted, "I just can't remember your name."

The boy laughed as they entered the hall and began walking.

"You don't know my name, so don't pretend you do."

"No, I just... I'm so sorry."

"It's fine, Nate," the boy assured him, "My name is Dan Humphrey."

"Nice to meet you, Dan. So, about that reading..."