A/N: I wrote this a really long time ago and just decided to submit it. I almost turned it into multi chapter, but I haven't been inspired in a while so I don't think that's going to happen. This is based off an idea I had when I was watching the pilot when Blair and Serena are in a bar, Blair leaves, and Chuck comes in the exact same direction. I was just writing this as though they crossed paths. I haven't seen anything else like that in the show, so this will probably be the only one I write unless anyone else has any other suggestions. This takes place in the pilot episode after Blair and Serena become friends again for the first time. It also sort of explains why Chuck forced himself on Serena.

Summary: Chuck took one of her curls and started gently stroking it down her face. He hoped she thought that this was just one of his games, and not that he was getting excited. Very excited.

Disclaimer: I don't own GG, this whole idea came from the first episode.

Chuck didn't notice her at first. Of course. He was too busy with his arms wrapped around some faceless girls for the night. Not like Blair cared. She was with Nate. But Chuck had done her a favor. Several favors, in fact. If a year ago someone had told Blair that Chuck could be comforting, she would have laughed in their faces. Chuck Bass comforting? The player of the city? Please.

But Blair had been completely alone. Her mother was mentally absent, her father physically. So was her best friend, Serena. Nate was… she didn't even know. But Chuck was weirdly there, like he actually wanted to be.

It made sense. His best friend was sort of gone too. All they had was each other. And Blair had actually appreciated it when Chuck had picked her off the bathroom floor which she had been incapacitated on, and took her to the safety of his limo. She had some pretty bad months for awhile, but he was there for her, every time. And that was more than she could say for Nate.

Blair had found that she and Chuck were weirdly alike. They could banter back and forth and they both had the strange fondness for scheming and manipulation. Chuck was her only friend, her best friend when Serena wasn't there.

Chuck was there when she had found out that her father had left. No word from Serena. So he just picked her up and put her back together again. Blair had no idea why. Maybe it was just some obligation for Nate. But there were sometimes when he had looked into her eyes that it seemed it was more than obligation.

Chuck helped her when she relapsed again. He told her that she was perfect just the way she was. She didn't have to be insecure and Nate was an idiot for not realizing it. It was a strange conversation to have but Blair was buzzed anyway. She could have imagined it.

So it didn't make sense to her when she felt the distinct emotion of jealousy when she saw him with those stick thin blonde's with no brains. Maybe it had something to do with the blonde part.

Blair held her head high and was getting ready to pass him. She was going to see Nate. She shouldn't be preoccupied with his best friend, even if she was writing it off as just friendly jealousy. That's what she told herself when she saw them with him. She was just so used to him caring for her that it was strange to see him "caring" for other girls. Like it mattered. But she didn't see it coming when he broke away and called her attention.

Chuck didn't see her at first. Yes, it was surprising because she lit up a room. There was no one like her in the world. He was used to have these awkward and sinful feelings about her. He'd always had them for her, even though she was with his best friend. He wrote it off as she was just hot so he wanted her.

But his feelings intensified when it turned out that she needed him. She was totally alone, and in a way, so was he. His best friend had turned into a head case because the "love of his life" had run off to boarding school. Wasn't the love of his life supposed to be the girl who was crumpled on the bathroom floor in the club that night, drunk beyond her wits?

She was suffering and Nate hadn't even bothered to notice. Figures. But Chuck was convinced if he had a chance to get with Blair, he would absolutely take it. He assured himself that if he was with her just for one night, these stupid feelings would go away.

So Chuck let the instincitve thoughts about how Nate didn't deserve her and how she was the most perfect thing that had ever walked into his life fly right by him. He would never let his emotions be ensnared by a woman. He just assured himself that it was hormones that made him speak to her that way and react to her that way. Chuck Bass didn't have feelings. And he most certainly never fell in love.

Not that he even knew what that meant. He had never said it, he had never felt it, and from the heartbreak that was coming to Blair, he most certainly never wanted it. He never told her about Serena and Nate, but that didn't mean he desperately didn't want to.

She deserved better. But she didn't have to know that. The only times he had divulged this information was when she was so hammered she could barely hold up her head. When she had to lean it against his shoulder on the limo ride home.

Chuck just put on his signature smirk of indifference and pretended that she was just a scheming friend. That was one of the things that captivated him about her. But there were other times when he called her beautiful, that her intoxicated eyes suddenly became clear and appraised him for it.

He did not like how it made him feel. Like he was important enough, or deserved what he could have had when she was that gone. But he never did. And whenever he saw her now with Nate, or superiorly down-casting her "friends", he always wondered why.

No, he wasn't going to outright tell Blair that Nate had taken Serena when Blair was the one waiting for him. But that didn't mean he didn't want to. That didn't mean he wasn't going to set traps, hint at the reality that Blair was very quick to catch on, but too "in love" to really listen. No, he was a good friend.

Blair was vaguely aware of Chuck peeling himself away from his skank(s). He didn't give them much as a backward glance. Blair didn't give him one either. Chuck strode confidently to her side, keeping her stride.

He was such a player, but it didn't matter to Blair. She wasn't dating him.

Chuck loved the way she held her head up, pretending she didn't notice he was there. She most definitely noticed. And he most definitely noticed the new outfit and sweet fragrance she wore to impress Nate. Nate would never notice. But Chuck did, and he did not know the hell why. But he pursued it anyway. Hit on now, contemplate later. That was his motto.

Blair could inhale his signature musk from here. She used to find it offensive, too overpowering. The first time she noticed it she almost gagged. Now, she supposed she was desensitized to it. She thought it smelled amazing. Yeah, like she would ever tell him that.

"Marching off to your deflowerment, Waldorf?" his seductive breath crashed into her ear. Why did he have to talk so quietly that he was practically in your ear? He was right next to her, couldn't he talk normally? And she knew he was using his trademark "seductive voice" that he thought worked so well.

Chuck watched Blair pause slightly in The Palace. His face was an inch from hers, he was gazing at her profile. She still did not meet his gaze.

He could be so heinous, sometimes. Blair didn't know why she put up with it. Yes she did. Because he understood her and he used that power over her all the time.

"Not that its any of your business--," Blair finally snapped into his slanting, dark, exotic eyes. She hated how she knew exactly how he could put charm on women. It was his eyes and his voice. The way he was looking at her now was how he bedded countless socialites. Blair just didn't know why he bothered to use it on her. He knew she was untouchable. And she used that to her advantage as well.

"Ah, Nathaniel has finally decided to grow a pair," Chuck smirked. Yeah, he had encouraged Nate to finally give Blair what she wanted, but that didn't mean he had alternative agendas. She would soon realize that Nate never loved her. And Chuck had no idea why he wanted to wait for that day. Blair was just a girl. The only girl he was friends with. And his best friend's girl, to be exact. Stupid emotions. They complicated things.

Her dark, glinting eyes scowled at him. Her scent was overwhelming him by now. He hated how he couldn't have her. He hated it more that he couldn't reign in his damn thoughts.

Blair just jutted out her chin stubbornly and continued to glare. Chuck's smirk widened. He knew the reason she wasn't responding in their banter was because she didn't have one. No one was impervious to his stare. Not even Blair Waldorf.

"A drink?" he offered, "to celebrate becoming a woman." Chuck wasn't an emotional person, and he knew it. This was how he talked to her; how they talked to each other. She responded to his dark thoughts because in reality, she had a darkness in her too; a darkness that she didn't let anyone see... except him.

Blair practically gagged, still wondering why she was actually friends with the pig. She heard a chuckle escape his lips. He was enjoying this.

"I'm actually going to be late," Blair reasoned. She didn't like giving into Chuck like this. He was actually entertaining company, but if she said yes immediately, he could use it against her.

"He's not going anywhere," Chuck soothed, using his velvet voice. Would she notice that he was trying hard to get her stay a while with him? She was finally giving herself to Nate. Chuck didn't really want to sabotage Nate, but he wanted to soak her up as much as he could before she would ride gallantly into the sunset with her white knight. She never noticed the Black Knight that cared more about her than her actual boyfriend.

Chuck slept around, but at least it wasn't with her best friend. Serena would be a good one night screw, but she never had the captivation that Blair held over him.

Blair stared into his eyes.

"Fine," she snapped. Yeah, she gave in, but she wasn't going to be pleasant about it. Chuck was surprised. He never dreamed that she would actually have a drink with him when Nate was waiting. Not that Nate cared about anything except his precious golden goddess. He couldn't help but be cocky about it. It was his nature.

Chuck lead her to the bar, the one where he and the skanks had been seated on, the one in a different room than Serena.

Chuck ordered for her. He knew her so well. Blair found it strange how Nate didn't even know her favorite food. Chuck reveled in it.

"So?" Blair demanded sharply. Nate might wait, but what would he think that she was sort of blowing him off for his best friend. Even though she was there with him, he could see she was on edge. He would have to make this quick.

"I see we're in a chipper mood," Chuck smiled. Blair rolled her eyes. "I guess the pressures of sex are not lost on Blair Waldorf." He doubted that Blair wouldn't go to Nate after their encounter, but that didn't mean he wasn't going to tease her about it. It was one of his favorite pastimes.

"The only pressure of sex that you enjoy is the one you're gonna whip out at the Kiss on the Lips party. On the roof," Blair retaliated.

Chuck smirked. It was like she had read his mind. He loved when she got like this. She knew him so well and she was the only one who could banter with him like that.

"Ah, you know me well. I do have a fondness for roofs," Chuck took a drink.

"So this is what you brought me here for?" Blair asked. "More barbed banter? Don't you have some skanks you have attending to?" Blair didn't know why she was sniping at him like this. She hoped he hadn't noticed.

Chuck smiled, seeing his opening.

"Speaking if skanks," Chuck drawled, "isn't there a certain Nathaniel that needs attending to?"

"What are you saying?" Blair quipped. "Your lumping me in that category of slutiness?" Chuck wished she knew. Then he wouldn't have to resort to this sort of thing. Then she would see how Nate really didn't love her. Chuck put on an innocent face

"I would never, lover," he leaned in and stroked her cheek. Gross.

Blair was used to Chuck always being attentive like this. It was normal for him. He was a perv, but Blair never really thought of how it was strange. It was just Chuck. But it was certain that she wouldn't have anyone else touching her like this. Maybe it was strange that she was here with the best friend instead of the boyfriend, when it was Nate who was supposed to be touching her. But then again, this was Chuck.

Chuck loved the feel of her skin underneath his fingers. He couldn't help but think what other things of hers he wanted to feel beneath him.

Damn. He had to stop thinking those thoughts.

"I was merely implying that Nate is an eligible bachelor. He has many options. Many close to home," Chuck wished desperately that she would catch on. But she was hung up on something else in his sentence.

"Yeah," Blair said blatantly, "me." Chuck wished that she would just get wise. "And 'eligible bachelor'. Please, Bass." Yeah, Nate was hot, she got it. And she just… wasn't in the same league. She was fat and mediocre. She was lucky she had gotten him in the first place. Chuck leaned into her.

"I love it when you beg me." Blair pretended not to hear. Not usually a tactic she used, but she did throw him a sparing glance.

Chuck backed off. That was his effort for the day. He was done (for tonight) trying to clue Blair in on her own love life. He would concentrate on more pressing matters. Like how Blair was completely unaware how short her skirt was, no matter what sort of tights she put beneath them.

"Just an observation," he went back to the previous conversation. But Blair could tell that Chuck was done trashing Nate. Which was strange. They were best friends. What was with the "subtle" trying to give Nate a bad name? Whatever. Chuck was weird when he wanted to be.

"Now that the business is out of the way," Chuck took another mouthful of scotch. Blair raised her eyebrows. She should have anticipated this, having a drink with Chuck Bass, but sometimes she was just blind like that. This was the sort of tone he used when picking up girls. He used it on her as a joke. But most times she was just intrigued how Chuck could hold her attention with just one look. Or maybe she wanted it secretly. If she did, she never admitted it to herself. "May I say how ravishing you look this evening, Miss Waldorf?"

Blair wanted to choke back a laugh. Next to Serena, she couldn't even contemplate what she looked like. She knew this was Chuck's way of a friendly come-on.

"May I say how pervy you are this evening, Mr. Bass?" she smiled superiorly up at him.

"Blair, if this is your idea of coming on to me, may I offer a few suggestions… in the coat closet?" Blair couldn't help but laugh. It was weird, but no one could make her laugh like Chuck Bass could. He knew her dark sense of humor. No one else saw that.

She looked down at her martini, surprised that it was empty. How had she drank this much without even noticing?

Chuck loved the sound of her laugh. There was no sound in the world like it. He saw her glancing down at her drink, her eyebrow furrowing.

"Do you want another?" he watched as Blair glanced up at him, her smile back in place.

"No thanks, Bass. I have to get going, anyway."

"Are you sure?" Chuck asked. Blair eyed him strangely. He chose to be a gentleman at the strangest of times. She knew for a fact that Chuck rarely cared about what other people wanted. That phrase just struck her as odd. She knew she had to address this strange new revelation later.

Chuck wasn't being desperate, asking her, in so many ways, not to leave. He wanted to see at least one of her reactions before she left. He let his hand slide up her leg, inching further towards going up the hem of her skirt.

"We could always go back to that coat closet route that I suggested," Chuck's breath was crashing in her ear again, his body very close to hers. Blair closed her eyes. She didn't know what it was, but Chuck had away of making any coherent thoughts flee from her mind. But Nate did come back. Her logic said that he was waiting. But her mind said something else too.

Blair couldn't help but think how Nate hadn't made her feel this may in such a long time.

Chuck took one of her curls and started gently stroking it down her face. He hoped she thought that this was just one of his games, and not that he was getting excited. Very excited.

He was surprised that she hadn't knocked away his hands by now. Anyone who was passing would have thought they were seriously about to get it on. Yeah, he wished.

Blair felt him stroke her hair gently. She wished to God that she wasn't enjoying this so much. She just reminded herself of her perfect boyfriend, and not his skeezy friend. But she could play him too. Blair's eyes fluttered open and saw his hypnotic stare on her. He thought he was the only one who could play games.

Chuck saw a flicker in her eyes an realized that the moment was over. In a moment she would force him to back off and she would be on her way. He saw it in her eyes. Her cool, calculating eyes. He felt like he was drowning in them.

Blair crossed her leg over the one his hand was one, knocking it away. In the same motion as she flicked her hair back.

Chuck inhaled the scent that wafted out of her hair as she flipped it. Was this woman telepathic? Did she know exactly what she could do to him? Her cool eyes observed him for a second. He just let his smirk cross his face. He thought he saw something like relief in her eyes. She was relieved that this was just the game they played. If only she knew.

"Nice try, Bass," she said fake sweetly, "but maybe… " Blair didn't catch the change in Chuck's eyes. She thought it was just lust, because he had made it clear what he would love to do to her had he ever gotten the chance.

"...Never," she finished with a smirk of her own. With that she left down the money for her drink and flounced off. At least there was that. Chuck raised his confident expression up to see a backwards smirk of her own.

It was then that Chuck Bass realized that Blair Waldorf was his perfect match in every way. She had completely pulled him in just to reject him. Genius. He couldn't help but admire her for it, even if she was going off to his best friend.

Chuck stood up and lay down his own money and started scouting the next room. It was a small chance that Blair would ever even want him, but all the same, his hopes were crushed when she left. He needed something, and he needed it now. Blair did things to him that made him want instant gratification.

That's when he saw Serena Van der Woodsen drinking down a martini in his own father's hotel. He had completely forgotten about the other blondes he had abandoned at the other bar. Serena had been with Nate and it looked good enough. He pushed through a crowd of people with a simple "move… please." He owned the place, and everyone knew it. He walked right up to Serena, knowing what he wanted.

She would never know that she was just a filler. A filler after rejection that would happen again. It was the game they played, the come ons. He sat right at the bar with the blonde and he smirked. Even if she wasn't what his emotions begged for, she would do his body justice. She would never know who he was really thinking about the entire time.