Breaking Every Rule

Disclaimer: Of course, I do not own Gossip Girl.


Chapter One: Teach Me

Sure, Chuck knew that on some level he loved his father; after all, he had spent the majority of his life trying to gain the man's approval. Of course, that hadn't happened yet. But sometimes…at times like right now, Chuck didn't care about impressing Bart, and he had to bite his tongue so hard to keep himself from telling him how he really felt that, on some occasions, Chuck swore that he bleed. He needed to get away…to get out of this house before he did something that he would regret – like putting that five-carat diamond ring down the sink drain and turning on the garbage disposal.

"I'm going out." Chuck announced as he passed by his father and placed the ring box that he had stumbled upon down on his desk. "Congratulations."

As Chuck sat in his limo, he mentally went over who he could call to kill the time. Normally, Nate would be the sensible option, because they could just go up to his suite and get high. That's what he loved about his best friend – they never forced each other to talk, it came naturally with the pot, and Chuck could get his problems out of his system while Nate just sat there, staring into the blank abyss. And it worked for them…at least most of the time. But Nate had enough of his own shit going on, everything was so fucked up with the Captain and Chuck didn't really want to intrude.

But as soon as he started going through his address book, he realized that the answer was so incredibly obvious. Blair. Ever since they were little, Chuck and Blair had always been there for each other. Of course, no one ever knew about this. Neither of them would dare tell a soul that Chuck Bass and Blair Waldorf were secretly best friends. That they knew each others deepest and darkest secrets, and weren't afraid of the other using it against them, because no matter how manipulative the two of them may be, they would never intentionally hurt each other.

Intentionally. That was the key word. It had been a five days they last saw each other at seventeenth birthday party. And Chuck had wanted to call, desperately, but he was too afraid to hear what she had to say. He assumed that, whatever she would tell him, wouldn't be good, because he woke up to an empty bed the next morning. He fucked up. He should have had more self control, because, the truth was, as much as he had always wanted Blair, having her wasn't worth losing her friendship, and Chuck was pretty sure that, after taking advantage of her in her time of need, she would never forgive him.

However, Chuck decided to push those thoughts out of his mind, and maybe, just maybe he was wrong.


Chuck confusedly walked into her empty room – Dorota had told her that Blair was up here, so why was—


Chuck heard her call from the bathroom. He recognized that voice. It was just as raspy and was last with the same amount of regret as it was when he found out about her little…condition. It probably had something to do with the fact that Mr. Waldorf wasn't downstairs. Slowly, Chuck opened the door and found her leaning back against the bathroom wall. It must have been a while ago, because the rancid smell had almost dissipated, and Blair's hair was wet, which meant she already took a shower. "Hey," Chuck said as he approached her.

Blair stiffened at the sound of his voice and quickly wiped away the remnants of tears. "It's not what you think." Maybe she could admit this to Serena…but not to Chuck. Not after everything.

"Really?" Chuck raised an eyebrow as he took a seat next to her. "What do I think, Blair?"

She rolled her eyes at him – who the hell gave him the right to be so smug? "You think I…that I made myself do it." Blair paused and then took a deep breath before looking at him for the first time since they last slept together five days ago. "But I didn't. It wasn't on purpose…you have to believe me."

Chuck nodded and then brushed the tears that she wasn't able to hide anymore from under her eyes. "I believe you."

"No you don't." she stated, forcing out a laugh. "It's just that I felt sick."

"Because your Dad's not here?" he asked, bringing up what he assumed to be the reason for her relapse.

To both of their surprise, Blair leaned her head against his shoulder, "That and other things."

"Start with this." He told her, "Why isn't he here?"

Blair scoffed, "Eleanor told him not to come. She told him I was so mad at him for leaving that I didn't want to see him," Chuck nodded and Blair kept going. "And then Serena and I got in a fight. She knows about us. Apparently the brilliant Chuck Bass doesn't have the common sense to lock the door before seducing someone." Chuck couldn't help but let out a little laugh at her sarcasm, which prompted Blair to as well. "Anyway…she just…said some stuff. And I got mad and threw the whole thing with her and Nate back in her face. I'm not a slut. She can't just treat me like I'm a whore."

"Are you kidding?" Chuck asked with a raised eyebrow, "You, Blair Waldorf, who only lost her virginity last week and who has had sex twice in her life think that you're a slut because Serena, the girl who has probably slept with the same, if not more, people than I have tells you that you are? She's a hypocrite."

Laughing, Blair said, "Well, now you're making me sound like an idiot, Bass. I know I'm not a slut, I just hate that she thinks that she has the right to treat me like one. But you're right, she is being a hypocrite."

Chuck smirked, "I know I'm right." With that said, he stood up and held his hand out to her. "Come on…it smells like vomit."

"Fuck you," Blair spat, but took his hand anyway. "It does not! I cleaned…Lysoled…Fabrized…showered."

"Blair," Chuck said with a laugh as they both took a seat on her bed, "I was kidding. It's fine…plus," he paused, "it's not like it's the first time I've caught you in this kind of situation."

She didn't really know how to respond to him, so she just rolled her eyes and allowed the exhaustion to take over and lied down on her bed. Chuck smiled at the sight of her and, in a spur of the moment decision, decided to lay down with her, pulling her into his chest. After a few moments, Chuck let out a huge sigh and finally spoke. "I found a ring." Blair looked up at him with a raised eyebrow and Chuck just shrugged, "Bart's going to propose to Lily."

"Oh." Blair responding, leaving them in a comfortable silence for a few moments before she spoke again, "But your dad has remarried before."

"It's different." Chuck started. "Yeah; he's married random twenty-five-year-old gold-diggers who I knew didn't mean anything. Lily is his age and already has kids and her own money. My dad may be have been married since…the incident." No one ever referred to Chuck's mothers death as what it really was. People very rarely discussed Evelyn Bass, but when they did, her demise was always referred to as the 'accident' or 'incident' or 'unfortunate event'. "But I've never had a step mom. I don't want one."

Blair suddenly rolled over so that she was lying directly on top of him and started nibbling at his ear, stopping for a moment to whisper, "No one is asking you to replace her." A smirk formed on her face as she looked into his eyes and jokingly added, "And who knows? Maybe having a woman influence in the house will teach you some manners."

Raising a suggestive eyebrow, Chuck flipped them over so he was on top of her and said, "I'd rather you teach me," he paused. "My good manners can be rewarded with sexual favors; and as for the bad ones…I'll let you get creative."

"Oh really?" Blair asked incredulously as she kissed him and wrapped her leg around his waist.

Chuck then let his hand travel down her thigh, and, for some reason that was completely beyond him, Chuck forgot about their little game of wits and pulled away, looking into her eyes with a serious face. "You are so beautiful," he stated and then started nibbling on her neck. "Do you even know what you do to me?"

"Hmm?" she asked, while letting out a small moan.

He concentrated on the nape of her neck – his very own kryptonite – as he answered her question. "You make me…" he paused, unable to think of a way to describe the affect she had on him, "You make me…I don't even know. My stomach is still fluttering."

"Mine too," was all Blair could manage. It was beyond her why those words, not only made sense to her, but why they made her feel so much more wanted, desired, and cared about than anything Nate had ever said to her. But she still couldn't help but remember that this was Chuck Bass, and he did not belong in her bed, kissing her lips, caressing her bare thigh with one hand and bringing the other up her dress, slowly making his way up to her breast.

Even though she knew all of this, even though she knew she would probably end up getting hurt, Blair could not help but be drawn to him…no, she wasn't drawn to him – she needed him. She needed his strong hands on her body and she needed to hear the sound of his voice whispering in her ear. She needed him to look at her like she was the most beautiful person in the world, like she was the only person who mattered.

Chuck, who was clearly enjoying this as much as she was, looked into her eyes as he retracted his hand from her breast and brought it to the zipper, pausing a moment to kiss her lips and, as always, wait for her approval. After she nodded, Chuck slowly unzipped her dress, but was careful not to stare at her body. Instead, he was transfixed on her eyes. Chuck smirked when she shivered from his touch, "Cold?" Blair shook her head, but he disregarded her response. "Body heat, Blair. I'll warm you up."

"Really?" Blair asked, incredulously. "In that case, I think you have way to many clothes on." She momentarily overpowered him and flipped them both over, so she was now on top of him, straddling his waist. Blair started to unbutton his shirt, eventually growing impatient and tore his off, causing buttons to go flying all over the place.

After getting Chuck in his boxers, he sat up and unhooked her bra. "You know," Chuck started as caressed her body, "There's a lot I have to teach you, Blair. A lot you have yet to…experience."

All of the sudden, Blair became painfully aware of the fact that he had so much more experience than she did, he was her first, and Blair didn't even know if she was good. So she had to learn. She had to learn because he couldn't get bored with her. "Teach me, Chuck," she whispered and nibbled on his ear. "Please. Just teach me. Now."

Chuck stared at her for a moment in absolute awe – he really hadn't expected her to say that, he expected her to roll her eyes and brush off her comment, but her response blew him away. The truth was, Blair didn't really need to learn anything – she was already the best he'd ever had. What he really meant was that he needed to expose her to different things. Expand her horizon, which was exactly what he was going to do.