Disclaimer: I do not own Gossip Girl nor the song Heartless by Kanye West. Because if I did, I would be hella rich right now :P First chapter is RATED M. Don't read if you don't like sex scenes.

Author's Note: So I changed the prologue. This takes place after Season Two's "The Wrath of Con". Figured this one would be better. It's my first time to write a sex scene and a fan fic so do let me know what you think, please? I love your reviews. Thank you. :)

XOXO

Prologue: He Makes Good Girls Go Bad

To say that Chuck Bass is lonely is definitely an understatement. And as he sat on his thousand dollar chair with a glass of scotch in one hand, the feeling of loneliness couldn't have been more evident. Not that he was alone by any chance; a girl was currently sleeping soundly on his bed. Unfortunately, she wasn't the girl he wanted to be with at the moment or possibly, forever. To him, she was just another nameless girl who made his night a little more bearable.

As soon as the high from having sex was gone though, Chuck found the same feeling of loneliness creeping back. It scared him of course, to be alone, and to have anyone know that he actually felt lonely. Come on, Chuck Bass, lonely?

What's worse than having people know he's lonely? It's being vulnerable in front of others. Not even in front of step-sisters. For Chuck, being vulnerable equals to being weak. Blair was the only person he had let in. But due to the events that happened earlier, he couldn't help it. And he was just that – vulnerable in front of Serena. As he basked in the quietness of the early morning, he kept on thinking about the conversation he had with Serena.

"Chuck, why did you just do that?" she asked.

"Because I love her and I can't make her happy." He replied and that was that. No other explanation.

It was hard to imagine that just a few hours ago, he let Blair Waldorf walk out of his life. It's what he wanted, right? To push her away. To do what's best for her. It was a noble thing to do, especially for Chuck Bass.

But boy did it hurt. It hurt so bad that he had to practically shove the tears back into his eyes from falling down. Men didn't cry. Especially not Chuck Bass. But Chuck knew it was time to move on. So he sucked it up and did what he thought was best to cure his broken heart. He partied. To justify it, he thought of another excuse. It was supposed to be just a business affair: he bought back Victrola and wanted to see how the place was doing. It was his first big business decision after his father died and he wanted to make sure it was a good choice.

The moment he stepped in the club, though, he knew that it was a bad idea. It was right there on the stage that he saw Blair in a different light. The events that happened after.. well, that was the start of something. His life turned upside down after the limo ride with Blair. Suddenly life wasn't just this big sexfest with anything fuckable. It had meaning, it had excitement. He was looking forward to actually getting up in the morning and seeing her: seeing her smile, hearing her laugh. He found himself having feelings he never knew existed in him. A soft side, even. Chuck Bass realized that he wasn't this heartless beast he thought he was.

All of a sudden, the memories came flashing back that it was driving him insane. He almost left, but quickly decided against it. He was stronger than that, he shouldn't let Blair control him or how he lives his life. Especially now that she's gone.

As he made his way to the VIP area, that's when he saw her. She looked out of place in Victrola, like a little child in rehab. Yet she looked as though she belonged there. She had an innocent aura that was impossible to miss, with her wide almond shaped black eyes. But her lips contradicted that. It was painted with a very bright and sultry red.

At first she reminded him of Blair, but then again, he thinks that way with every woman he meets. He didn't get to see her that much, though. For a moment, their eyes seemed to have met – until the club bouncers shooed her away. She bumped into him, and they thought she was trying to attack him. They quickly whisked him away before he could even talk to her.

But as luck would have it, he saw her again. Drinking alcohol in plastic cups of all things. That was the moment he decided to make her the conquest of the night. It didn't help that she looked very hot in that outfit of hers, even though her body was something he normally wouldn't go for. She was chubby and overweight, but he was impressed at her boldness to wear such a daring thing. Her attitude definitely added to the turn on.

So he came up to her, got drunk, took her home. One thing led to another, and the next thing he knows, it was all over. He found it comforting at first, not having to sleep alone, but quickly regretted it. She isn't the one he wants next to him. She isn't the one he wants to see the minute he wakes up.

But she isn't Blair.

It was three o'clock in the morning already, and he was looking intently at the girl sprawled on his bed. He had long forgotten her name already and he was wondering why the hell he did he sleep with her in the first place.

And then he remembered. Because she isn't Blair. She was the opposite even. Too much of a goody two shoes that he wondered why she was even in the club. That made it easy for him to decide to sleep with her, thinking that he could do it without thinking of Blair.

But he was wrong, the whole time they were fucking, he was thinking of Blair. Pretended it was her that he was doing. He almost groaned Blair's name in ecstasy at some point even.

He finished his scotch and decided to go back to bed but it was impossible to sleep. The scotch was making his body hot all over, and thoughts of Blair weren't helping either. Again, he looked at the naked girl in his bed and decided that he was going to fuck her for the third time that night. He might as well have his fun while she's here. At least pretend it was Blair sleeping over and wanting him.

The girls back was turned to him, so he kissed her neck while feeling her large breasts. It was another factor that drawn him to her, he was always a sucker for breasts. He played with her nipples gently at first and then kissed her neck some more. She awoke with a gasp as Chuck's hands moved to caress her pussy. She was hesitant at first, perhaps because the effects of the alcohol were wearing off, but still didn't stop him when he inserted a finger inside her.

He was getting harder and harder already as he kissed her lips. The girl was faced him and he sucked and bit her erect nipples violently. Her moans started to get louder, and Chuck found himself getting more turned on. So she liked it rough, he thought.

He was overcome with lust already, and the intoxicating smell of sex and alcohol filled the room. He climbed on top of her and did something he normally didn't do. He looked at her hard. His piercing brown eyes illuminated by the moonlight from the Manhattan skyline view in his room. The setting couldn't have been more romantic, if only they were actually making love as opposed to just sex. Then he kissed her, a soft sweet kiss on the lips that made the girl smile. It was a nice contrast from the way he roughly handled her nipples, she thought. He kissed her again, harder this time. It was a deep, passionate kiss that surprised even Chuck. A kiss that literally left them gasping for air. After a few more kisses, he couldn't take it anymore and got ready to enter her.

"You ready?" he asked, still gazing at the girl. She merely nodded.

He didn't know what was wrong with him, he wanted to fuck her so badly. Mostly to forget Blair, to distract himself. And yet every time he closes his eyes a mental image of Blair lying down, naked, was all he could see. But he was still a man with needs, with or without Blair. In the end, he gave in to his horniness.

He entered her in one quick, violent motion and groaned. She was tight, and it was driving him insane. He pulled out slowly and entered her quickly again. This time it was her turn to moan, and he felt her tighten her grip his shoulders more tightly.

He pounded her hard until he couldn't take it anymore. He came so intensely that he almost passed out. Their tangled, sweaty bodies still one, as they panted and tried to catch their breath. He rolled off her and readjusted his pillow, to his surprise, the girl curled up to him and lay on his arm. He looked at her and kissed her, gently this time. She quickly fell asleep as he stroked her hair. He kissed her forehead and closed his eyes.

The last thing he remembered before he fell asleep was Blair Waldorf. The only person he really wants to spend the rest of his nights, mornings, and everything in between with.