A/N: Just a small S1 Chair fic inspired by blackmail of Mad Men. As it should be. I'm thinking I might do another chapter with Vanessa blackmailing Blair as well, but I'm not sure yet.

Summary: When you threaten someone in this manner, you should be aware of the fact if your information is powerful enough to make them do what you want, what else can it make them do?

Disclaimer: Quote belongs to Mad Men. The rest belongs to my beloved GG.

When you threaten someone in this manner, you should be aware of the fact if your information is powerful enough to make them do what you want, what else can it make them do?

-Don Draper

-1.12, Nixon vs. Kennedy

There were many times that Blair had used blackmail to her advantage. She never thought twice about it. It was something that she just did to get what she wanted. She never thought twice about that smirking lecher by her side who encouraged her all the way. Who reveled in her bad behavior and who very well groaned in pleasure at it.

She should have known better. She should have known that she was just begging for it to result into something like this. Because it was the New Year '08 and there that Chuck Bass-tard stood, fresh from Monaco and doing the one thing he was better at than her.

She should have known.


He was smirking at her and even in her prideful proclamation, she knew that he had won anyway.

"No," he repeated to himself. "I don't think that's the right answer, Waldorf."

"Right," Blair repeated. "Are you really going to turn this into an ethical debate?"

"You and I are not ethical," Chuck said, pulling at her uniform tie so she would be closer to him as he spoke lowly to her in the courtyard. "That's the point, isn't it? You and I are not ethical because you did something worthy of blackmail and I am someone who would use blackmail without a moment's hesitation. It surprises me that you haven't figured that out."

"That you would try to do this to me?" Blair asked.

"That we are two of a kind," Chuck answered. "And you're stupid to want to get back with Nathaniel anyway."

"I never said-"

"Please," he snorted. "Cotillion? After you abandoned me on the dance floor? Up in a suite? Ring a bell?"

"I slept with him," Blair rolled her eyes. "But I also slept with you. It doesn't mean it's a foundation for a meaningful relationship."

She knew that one would strike a nerve and his grip tightened on her tie as he pulled her even closer.

"You're practically panting at the prospect of making him your boytoy again," Chuck sneered. "And it's not going to happen. Not if you want him to know what transpired between us many times. And how much you liked it. I wouldn't even bother trying to deny it because your body is incapable of lying to me. I know it too well and have taught it too much."

"Like you're God's gift or something," Blair said, slapping his hands away from her.

"You certainly thought so," he said, his eyes dipping at her Catholic school uniform.


"Why does it even matter to you?" she asked. "You never cared about me anyway."

There wasn't any way he could respond to that without compromising himself. He settled for just glowering at her.

"I'm supposed to be with Nate."

Like she could ever fool him.

"Fate is telling me differently."

"Like you believe in any of that," she scoffed.

"And you do?" he asked. "You and Nate are destined to be together? If Fate didn't favor me and my cause, it wouldn't have given me hours of pleasure at your hands in addition to this tasty blackmail. If you were supposed to be with Nate, you'd be with Nate."

"You're not letting me," Blair said in frustration.

"Then I guess you're not supposed to be with Nate, then" Chuck smirked victoriously.

"I hate you."

"No you don't," Chuck said with almost a genuine smile. "We're too alike. You just hate that you don't hate me. Quite the opposite. You can't force yourself to feel for Nate, princess. Not after what we had."

"Don't pretend that you feel anything for me except fleeting interest," Blair spat. "You wouldn't have attempted to ruin me if you had."

"I didn't—"

He realized what he almost said at her probing gaze. He couldn't show his cards too quickly. Not yet, at least. He had to know he could get her to drop this disgusted act before he did anything too impulsive.

Then again, he thrived on it. And making her squirm. He liked that too.

"Maybe," he reasoned, his hand gripping her waist against him as she wriggled against him, trying to free herself. "But I don't like him thinking that he was the first one to remove that chastity belt of yours. And in a hotel room no less. No, that honor goes to me and my limo."

"How dare-"

He cut her off with a hot kiss to her mouth before releasing her.

"Until we meet again, princess," he said pleasantly before abandoning her staring off at him.


She hated when he was right. Always, always right. How he reveled in his own reverence in the field of social destruction. How he knew they were the same. And how he seemed to know that she still...

She still did.

It was this epiphany that flourished as she stood in the middle of that party. How he could claim that he liked her in the back of his limo but would flirt with some freshman slut who probably crashed the party to begin with.

She hated him.

It was the one thing she hadn't lied about. She really did hate him. She just didn't know how it was possible to feel the opposite emotion for the same person at the same time. It wasn't flattering. Feeling his eyes on her as she downed the rest of her drink wasn't flattering. And when she felt herself walking right up to him definitely wasn't flattering.

She cut right between the two and the girl spilled her drink all over herself. With a fake apologetic smile, she passed the two of them.


The fact was that she didn't feel sorry at all. And she knew that she didn't sound it either. All she felt was his eyes boring into her back and the slight tinge of satisfaction at an impulsion that she would regret.

"I knew it."

His voice was dark and she knew that he would follow her into one of the upstairs bedrooms. Not even a second after he closed the door behind them, her hand flew out of nowhere and he was holding the side of his face in shock. But he was smiling at her and she was forced to hit him again.

And again.

"Whoa, slow down there, lover," he cautioned.

"You're disgusting."

"And you're in love with me," he said with self assurance.

"What is wrong with you?" she asked. "You're blackmailing me. Do you even have any idea what you're doing?"

"You just said it," he pointed out. "I'm blackmailing you."

"If that information is so powerful to make me bend to your will, what else do you think it will do?"

"The side of my face is giving me a couple of ideas," he answered rubbing his jaw.

"How could you?" she asked, pushing against his chest emotionally. And suddenly he was paying very much attention. "I trusted you."

"Yeah, and I trusted you not to go screw my best friend."

"Why?" she asked. "I screwed his."

He was looking at her and she was so flustered and so angry and so beautiful, he couldn't help himself. She could be so acutely evil that he just had to love her.

"Your face has the most beautiful glow when you're vengeful."

She couldn't help but gape at him. He thought she was beautiful. He favored her for all of the things that pushed people away.

"You're a jerk," was all she could think of to say. She knew that he expected her vivacity to kick in again because he caught her wrists before they could do any more damage. And suddenly she was forced on top of the dresser and he was kissing her again, pinning her wrists to the wall.

He forced his way between her legs but they had somehow wrapped themselves around him so he couldn't seem that violent. He pressed himself against her so intimately and excitedly that she realized exactly what was happening. And how it couldn't.

She couldn't let herself get that deep into him. For a moment, she was sure that she had loved him. And she was a fool. She was a fool because no one loved Chuck Bass. No one had been stupid enough to even think that they may have had feelings for him either. They just graced his bed and left before he had a chance to kick them out.

She was stupid. She let him take her virginity. She let herself love him. And that was why Nate was so important. Because it wasn't supposed to be like this. It wasn't supposed to hurt so good.

She had absolutely not control over her body. Her hands were restrained and her legs were crossed around him that when he started moving against her with pleased noises at the back of his throat, she knew that she was in trouble.

She wanted to squirm away but it just made him cling harder. She unhooked her legs and quickly kicked him away. He stumbled, seeing her pull down her dress and pass him.

"I told you, Waldorf," he informed her. "Your body can't lie to me. It loves me too much. Soon your brain will catch up."

"You think you can corner me?" Blair demanded.

"I know it gets you hot," he shrugged, motioning towards the room. "Exhibit A."

"I am going to ruin you, Chuck Bass," she vowed before taking her leave

"I can't wait," he grinned, feeling even more excited at the prospect of her vibrancy as she slammed the door behind her.

It was some moments before he sauntered out of the room before running right into Nathaniel Archibald. What he hated about the whole situation was that Nate was his best friend. And he hated it because right now, he really hated that best friend. With so much jealousy he was surprised he hadn't lashed out physically, even if it was beneath him.

Nate stopped before him and laughed.

"Who's the girl?"

"What?" Chuck asked in confusion. He turned towards the mirror in the hallway to see Blair's lipstick smeared on his face and collar.

"She seems..." Nate said, "enthused."

"She likes pretending that she doesn't want me," Chuck grinned. "That's going to change."

He was sure of it.