Chapter 2

The Penthouse in the Empire Hotel was dark. Only one light shone. It was the light above the pool table. Blair took of her coat and slowly hung it on the coat rack next to the elevator door. She wanted to just get this night over with but she found herself frozen in the entryway. She wrapped her arms around her body. Was the penthouse always this cold? Blair felt a shiver run down her spine and goose bumps appeared all over her body. She felt her stomach turn.

"You can do this." She thought to herself. "You can do this for Chuck."

Just then she heard his voice. "Ah so you did come after all." Blair kept silent.

"Well don't just stand there. Come in. Sit down." He told her. "I mean that is if our deal is still good."

Blair took a deep breath in and started walking toward the pool table her bright gold dress dragging on the floor behind her. She had loved the dress when she saw it at the store earlier that day. But after finding out that Jack wanted her to wear it for him tonight, she despised the dress and she would be throwing it in the trash as soon as the night was over.

When she got to the pool table, Jack was standing there in a suit smirking.

"That dress looks stunning….I'm sure it will look even better off than it does on."

Blair fought the urge to vomit all over him right then and there. She swallowed as she slapped down a contract on the pool table.

"Before we continue with the evening, I need you to sign this."

He scoffed. "What you don't trust me dear?"

Blair just gave him a withering stare.

"Fine" Jack Laughed. "I'll sign your little contract, Princess."

"And Chuck can never know." She whispered in a very serious yet worried tone.

"Now do you think I am the kind of man who kisses and tells?" he asked her grinning from ear to ear.

Jack started walking toward her. Blair's heart raced with fear in anticipation of what they would do together that night. But she kept her face composed and business like. She was not going to pretend she liked what was about to take place. She would not give Jack the satisfaction. Plus she was sure she couldn't even fake like she wanted him even if she tired. Jack stopped in front of her. He took her hand and gave it a kiss. He then moved her hand to his crotch where she could feel him already hard. She felt his wetness on her hand when she touched his buldge. Blair started shivering again. She continued to keep her face still and straight.

"I'm ready for you." He whispered in her ear before he started kissing down her neck.

With one of his hands he unzipped his pants and released his cock. Blair closed her eyes and concentrated on her breathing. He then took both of her hands in his and placed them around his erected penis. Blair opened her eyes trying not to look at him. But she failed. She locked eyes with his. His eyes were hungry with lust for her as he moved her hands back and forth around his cock.

Blair awoke in a panic. She shot up into a sitting position and stared dry heaving.

"Blair!" She heard Chuck's worried voice next to her but it was as if he was in the distance. The only thing she could see was Jack's lustful eyes and his sickening grin.

"Blair!" Chuck addressed her again. This time putting both hands on her to try to get her to calm down.

Blair fought out of his grasp.

"NO!" she screamed. "Don't touch me!"

"Blair it's me!" Chuck told her in a soft voice. "It's me."

Blair's breathing slowed as she realized where she was. She was in her room at her mother's house. She was with Chuck. Her heavy breathing stopped and a few tears ran down her face. She looked down and quickly wiped them off her face.

She turned to face him. Her face was still pale with fear and her eyes were still wet.

Chuck looked at her. Realizing what she must have been dreaming about. He tried to reach out and stroke her face, but Blair pulled away. She was embarrassed, even more embarrassed than she was about her drunken night in Brooklyn. But more than that she remembered it was him who put her in the position to have that nightmare in the first place. She jumped off of the the bed and stood on her floor, her arms hugging her body.

"Blair what is it? What's wrong?" he asked her genuinely worried.

"You need to go home Chuck." She told him.

"Blair…"

"Just go please!" Her voice was insistent but also worrisome.

Chuck stood up and walked over to her on the other side of the bed. He tried to touch her but she pulled away from him. Anger was in her eyes. Chuck took his hand and ruffled his hair. He felt awful. He wanted so badly to help her feel better but he knew that he was at fault for at least some of her pain and for whatever reason what she was dreaming about reminded her of that. He started to come toward her again. This time she just stood there. The expression on Blair's face told Chuck that she was very close to breaking. He put his hand on her arm that she was using to hug herself. She was shivering slightly.

"Do you want to talk about it?" He asked her.

Blair shook her head. "Just leave. Please." She told him more insistently.

"But is there something I can…."

"I DON'T WANT YOU HERE! LEAVE!" Blair yelled in his face.

Chuck froze for a second, shocked. He was extremely concerned for Blair but he didn't want to push things. Chuck felt like the fact that she even let him stay with her for another day was a victory in and of itself. He was going to respect her wishes. He walked over to the bedroom door and opened it to leave.

"I'm Sorry." He whispered to her before he left.

Chuck walked down Blair's hallway and down the stairs. He waited till he got into the elevator and then he couldn't hold it in any longer. Tears were rolling down his face. He pushed the emergency button to stall the elevator. He wiped the tears away with the back of his hand. He couldn't let anyone see him like this. No one but Blair could make him feel like this. He felt a tightening pain inside his chest. He felt utterly hopeless. He was now positive something awful must have happened to Blair that night and there was nothing he could do to take back that deal he made with Jack. There wasn't anything he could do to fix what happened to her. She was forever changed by this. And he just wanted his Blair back. He wanted to see her smile more than anything in the world. He decided he'd better get out of the elevator before people started wondering why it was not working. He pulled the emergency button out and the elevator began to work again.

When Chuck got to his penthouse in the Empire Hotel that afternoon he had 2 messages on his answering machine. He pushed the button to hear his best friend Nate's voice.

"Hey man I guess you are out. Any how we saw this blast about Blair on Gossip Girl and I know you are busy partying with all your lady friends and what not but if you could please check and make sure she is ok since Serena and I are out of the country….yeah that'd be great. And I still have no clue why you two even broke up in the first place…we'll talk when we get home I guess. Bye."

The next message was from Serena, Chuck's step sister and Nate's girlfriend.

"Chuck. I know Nate called you already but I was just checking up on you. Did you get the blast about Blair? Please tell me you talked to her and she's ok? I don't know what's going on with you too but I know you still love each other…it would be nice if you guys worked things out before we get back…take care Chuck."

Chuck wasn't sure what he should do about his friends. He was sure he didn't want to tell them the truth, not the whole truth anyway. He also knew that the chances of Blair and him "working things out" soon were…well slim to none. He buried his face in his hands and took a seat on his couch. Just then his phone started ringing. Chuck got a flutter feeling in his chest thinking it could be Blair. He looked at the caller I.D. It was Nate. Chuck took a deep breath before he answered.

"Nathaniel! How is your trip going?"

"Hey Man, um it's going good. We are coming home tonight. We wanted to know if you wanted to go to my grandfather's county house to hang out? Like old times. Grandfather offered and I thought why the hell not you know…we used to go there just the four of us all the time remember?"

Chuck didn't answer him. He was thinking about how they, Chuck, Nate, Serena, and Blair, used to go to that country house to get away from the city in the beginning of their teen years. The house used to be like a home away from home for the four friends. Chuck knew what Nate was trying to do. He wanted all four of them to go up there like old times hoping that Chuck and Blair would make amends while they were up there. Nate didn't know how awful and complex the details of their break up were. If he knew Chuck was pretty sure he would have a black eye and no friends. Even Nate, who had been Chuck's best friend since kindergarten, wouldn't tolerate him if he knew what an idiot Chuck had been that night. Nate and Blair used to date. And even though Nate realized he and Serena were a better fit a few years ago, Nate was still very protective of Blair. He loved her like a sister. Serena, who had been Blair's best friend since they were in diapers, probably brought up the idea of a night away at the country house and begged Nate to call Chuck and ask.

"Hey Man…you still there…" Chuck heard Nate's voice through the phone.

"hmm? Yeah….that sounds….great." He answered. Chuck couldn't sound less enthusiastic about the idea if he tried.

"Great, man! Well we will meet you up there at around 8:00 tonight! See ya there!" Nate said quickly.

"Nate…" Chuck said before Nate had a chance to hang up the phone.

Nate sighed on the other end like he already knew what Chuck was about to say. "Yeah?"

"Did you invite Blair…?" He asked his friend already knowing the answer he was going to hear.

Nate paused for a second, and then started to answer. "Well…I mean yeah…I know you two are going through something but Blair is a part of our group regardless. So I couldn't just not invite her, know what I mean?"

"Yeah, I know what you mean." Chuck answered him. "See you guys at eight then."

Nate didn't say anything, he just hung up. Probably didn't want to give Chuck a chance to find a way out of going. Nate and Serena thought they were being sneaky, but when it came to things like them trying to bring him and Blair back together, the two of them always made things way too obvious. His friends were nice but they were not the most creative people on the planet.

Chuck looked at the clock on his phone. He still had a few more hours before he had to head to the Vanderbilt Country House. He decided this would be the perfect opportunity to shower and change, maybe even get a little rest before he saw Blair again. He got a nervous twinge inside his chest just thinking about seeing her again today. The image of her pale frightened face flashed in his mind. She'd looked at Chuck that morning almost as if he were a stranger. His chest started to ache with regret. He stood up and rushed into his room, trying to ignore the feelings going on inside of him. He took all of his clothes off as quickly as possible and headed for his shower.

When the water was at the perfect temperature he stepped inside and began to rinse himself off. The warm water felt so good. It also made him tired. He closed his eyes in the shower trying to remember the last time he had been to the Vanderbilt country house. He really couldn't remember the last time he had been there. The only time that was sticking out in his mind at the moment was the first time the four of them had gone up there when they were thirteen. Nate, Serena, and Blair had lied to their parents claiming that Nate's grandfather would be there and he invited them to stay over. Chuck didn't have to say anything to anyone. He just went. His father was never around to talk to and the help at the Palace Hotel, where he lived, never questioned where he was headed.

It was a Saturday night in early February that the four 8th graders found themselves alone at the Vanderbilt country Mansion. When Chuck stepped inside the house he noticed his three friends to the left in the living room Serena and Nate were sitting on the floor looking at an old baby album of Nate. Serena was laughing hysterically. Nate just looked embarrassed. Serena appeared to be already drunk. Nate's baby pictures were not as funny as she was making them out to be. But Serena was flirting. She was one of those people that always flirted without realizing it.

Chuck looked over to the couch and he saw Blair sitting there. She was tiny and pale but her cheeks were rosy and she wore red lipstick. She looked like a China Doll. Blair was never one of those model like Barbie girls. But she was always beautiful. Her problem at the moment, which she spoke of often, was that Serena was taller than her and had bigger breasts. Blair had just begun to develop and Chuck noticed the exact day she came into school and had two small buds poking out of her chest. He practically got hard just thinking about that day. She was wearing a white blouse and a see through bra. Chuck was of course always turned on by any breasts, but when they first start to grow, for whatever reason that always put the girl on the top of his "to fuck" list. Unfortunately for him Blair couldn't have been less interested in Chuck in that way. She made it very clear to Chuck that it was Nate she wanted. That didn't stop Chuck from wanting to fuck her. In fact it actually almost made it more exciting for him. Chuck had lots of girls throwing themselves at him. Blair was not only closed to the idea of being with him, but she acted repulsed by the very thought of being with Chuck. That turned Chuck on. It was like a game to him. And Blair had no idea she was playing it.

Blair was frustrated that night, he could tell. Her legs were crossed, her arms were folded, and she was staring at Serena like she was going to rip her head off. The two girls were best friends, but they were also each other's biggest competition. They were currently competing for Nate. They had been competing for Nate since the 1st grade when he was dared to kiss them both on the same day on the playground. Chuck knew this because he was the one who dared Nate to kiss them. Chuck had promised that if he gave Blair and Serena both a kiss on the lips that day, he would give Nate his pop rocks. At the time Nate would do anything for pop rocks. Chuck just got a laugh out of watching the girl's faces when Nate planted one on them, especially Blair's face. Chuck was sitting next to her during free time one day and he noticed she was writing Nate's name in her pink little notebook, with little hearts drawn all over every inch of the paper where his name wasn't. Chuck thought about stealing the notebook from her and publicly humiliating Blair by handing the notebook to Nate right there in the middle of class. But he later decided that daring Nate to kiss them both and watching them get all giddy about it was a more fun idea. Plus he was hoping the girls would fight over Nate. Chuck was bored at the time and wanted some entertainment. If he had known the girls would fight till the day they both died to win over Nate, Chuck never would have dared Nate to kiss them in the first place.

"Hey you're here!" Nate noticed Chuck standing in the door way and got up to walk over to him.

"Thank God you are here, man." Nate whispered to Chuck when he got to him. "They are both driving me insane. You know you can't leave me alone with the two of them for very long."

Nate wasn't completely blind. He could tell both Blair and Serena liked him. He was flattered of course. Most of the time, Nate loved the attention. But he way they competed for his affections could be overwhelming for Nate at times. That is where Chuck would come in handy. He would distract one of them so Nate would have a chance to breathe.

"Calm Down Nathaniel. I'm here. The party has begun." Chuck exclaimed loud enough for the whole room to hear him.

Chuck walked into the living room and sat down on an old leather arm chair next to the couch were Blair was sitting. He smirked in her direction. She rolled her eyes at him and went back to staring at Serena who was still laughing like an idiot at the photo album. Nate sat down next to Serena and grabbed the book from her.

Serena stopped laughing. "Hey! I was looking at your cute little naked baby butt!"

"And on that note…" Nate mumbled as he brought the book out of the room to hide it somewhere safe.

"Booo…" Serena whined as she turned to face Chuck. "Hey Chuck. We missed you in science yesterday."

"You missed at test." Blair spoke to him next. "Remember? It was the one on anatomy."

"Well…I was studying some fascinating anatomy on my own in the back of the library." Chuck answered with a sly smile.

"Gross!" Blair exclaimed, her face disapproving.

Serena just giggled.

Blair sighed and uncrossed her legs she took her small hands and straightened out her navy skirt. Chuck was staring at her again. She was so prim, proper, and uptight. God he enjoyed ruffling her feathers. She was beyond sexy when she was annoyed.

"Well I can see you don't care whether you pass the 8th grade at all do you?" Blair continued to talk to him. "Don't you want to go to high school with us?"

"Actually Mom…" Chuck started and Blair looked offended by his insult. "I have it handled."

"Whatever." She replied irritated.

"Someone is in a pissy mood." Chuck said as he came to sit down next to her on the couch. She scooted away from him.

"I'm bored." Serena chimed in. "I'm gonna go see where Nate ran off to." Serena got up off the floor and practically skipped out of the living room.

"He's probably getting high…" Chuck called after her. "Hey tell him to bring me some when you find him!"

"Sure Chuck!" Serena yelled back. She was already half way up the stairs.

He turned to look at Blair again and his eyes immediately looked down her shirt. Blair noticed what he was doing and with a sigh of annoyance buttoned one of the buttons on her top so he wouldn't be able to see down her shirt so easily.

"Waldorf, you are not fun at all sometimes." He said to her leaning back on the couch.

Blair rolled her eyes "Why because I am not throwing myself all over you like every other girl at our school?"

"Well…yes." Chuck replied. "I mean don't get me wrong. The whole "I'm saving myself" thing works for you. It's even hot at times…but you can't at least let me look?"

"You're disgusting."

"You're hot."

"Shut up Chuck."

"What?"

Blair's face went from annoyed to sad. "If I'm so hot then why is Nate upstairs with Serena right now?"

Oh geez. Chuck thought. Here we go. Somehow Chuck always ended up being the person that gave Blair the confidence she was lacking to keep going after his best friend. Truth was she was gorgeous. But she wasn't as outgoing or forward as Serena. That just wasn't her way. Blair still believed in fairy tales, where the prince made the first move. Nate was her prince in that fairy tale and she was determined to make him the first guy she would give everything too. No matter how many other guys were interested in her. And there were a lot. Chuck could see it when she walked through the courtyard at school. She was like the unattainable goal to every boy at their school. Every guy wanted to bang her, including Chuck. But he didn't just want to bang her once. He wanted to have his way with her over and over and over again. Because underneath that prim and proper princess he was convinced was a tiger. He could see it in her eyes. She was more dirty than she'd let anyone know.

"Blair… can you just forget about Nate for a second?"

"Why? You know I like him." She interrupted him. "What do you think I'm not good enough for him?"

No, that wasn't it at all. If anything Nate was not good enough for her. And that was the problem. Of course Nate noticed how hot Blair was. You'd have to be blind not to notice. Nate, however, had only ever had ditzy cheerleader like girlfriends. Between Serena and Blair he was naturally more attracted to Serena because she was just more like him. Nate was more comfortable with Serena. And if Chuck recalled correctly Nate was also a virgin, like Blair. Only he wasn't proud of it. Chuck had Nate's back when it came to that though. He had every guy on lacrosse believing Nate was almost as much of a player as Chuck was, almost

Chuck hated when Blair got like this with him. He wanted to make her feel better but he was awful at it. Chuck could tell behind the wall that Blair put up when he was around that she actually greatly valued his opinion. Though Chuck could never figure out why that was. He was basically the king of bad decisions. He was raised by nannies for fuck sake.

"Tyler Canon wants to date you." He said in an effort to show her there were more guys out there besides Nate.

"Tyler Canon is a douche bag." She replied.

"All guys are douche bags, Blair." He told her truthfully

"Not Nate." She started again.

"Oh God…" Chuck leaned farther back on the couch and rolled his eyes.

"He's so nice and thoughtful…he always gets me something for Valentines even though we are not dating."

"It's because you whine loudly every year about how you bet no one is going to get you anything." Chuck stated.

"I do not!" Blair said looking offended and caught. "Fine I do whine...a little, but it's still really nice of him to do that for me don't you think?"

"Sure Blair, whatever." Chuck replied standing up and going over to the liquor cabinet. He grabbed a bottle of scotch and sat back down next to her.

"Want some?" he asked as he put the bottle in front of her face.

Blair wrinkled her nose for a moment. But then, to Chuck's surprise she grabbed the bottle from his hand took a big sip. She quickly handed the bottle back to Chuck. She made a sour face but tried turning her head and pretending to cough before he could see her reaction. She failed.

Chuck smiled. "Never had scotch before huh?"

"It's that obvious?" she asked him.

Chuck just laughed at her.
Blair looked annoyed and determined to prove to him that she could drink along with him and do just fine. She grabbed the bottle back from him and took another sip. This time, she managed to keep her face straight.

"Ok Waldorf. Let's see if you can keep up." He smirked at her. His stomach got an excited feeling inside. He ignored it and took another sip, then passed the bottle back to her.

They passed the scotch back and forth until the entire bottle was finished.

By that time Chuck was sitting on the floor staring at his scarf. He was tired but not tired enough to sleep. He could see two of his scarf. He rubbed his eyes. It was still blurry. He looked over at Blair then who was lying on the couch now staring at the ceiling. He smiled because she was also smiling. He felt like he had something to do with it.

'What are you smiling about?" he asked. "Don't use the N word."

She giggled. Chuck laughed back in response. He loved to hear her laugh. It almost never happened.

"I was just thinking…I don't know….I mean I can't tell you. " She laughed all secretively.

"Oh come on." Chuck said. "It can't be that bad. It's you."

Blair sat up and looked at him still all smiles. "It's just that I just realized. When I finally do eventually do it with someone…"

"You mean have sex with someone?" Chuck interrupted her speaking, relieved that she said with someone and not with Nate.

"Yes…." Blair laughed. "I don't think I have…. I mean I know I have never seen one."

"One what?" Chuck asked knowing all too well what she meant, but wanting her to actually say the words.

"You know." Blair stated.

"No actually I don't"

"Chuck…you know…" Blair stopped laughing and her face got serious. She studied him in her drunken state trying to find out whether he was lying to her or not. She couldn't tell.

"You are just trying to make me say it." Blair said to him trying not to laugh. Chuck was enjoying her new giddy attitude far more than he should have been. He could feel himself starting to get hard.

He made sure his scarf was covering that part of him before he spoke again.

"Please Waldorf. Enlighten me on what you are talking about. I'm all ears."

"You know…." Blair's face got all serious. "A…penis." She whispered as soft as she could before she busted out into uncontrollable laughter.

Chuck just smiled at her waiting for her to calm down before he stood up.

When he stood up it was obvious to Blair that something else was also standing.

"I can help you with that if you want." He said to her with a wide grin.

Blair grew silent, and her eyes widened. She grabbed one of the pillows on the couch and started hugging it. She was staring fascinated at Chuck's erection through his pants.

"OK...Hurry." She told him. "Before I change my mind."

"As you wish…" Chuck said as he quickly whipped out his cock exposing it in all of its glory.

Blair just stared at it for a moment then she threw the pillow at his face and burst into more laughter. She laid down on the couch after she finished laughing, trying to recover from her body's reaction to just seeing her best guy friend's penis.

Chuck put it away and sat down on the arm Chair.

"So…" He spoke to her. "What did you think?" Chuck asked hoping she wouldn't be too harsh. He was quite proud of his penis and a negative comment about it from Blair would most likely knock he ego down a notch.

Blair was staring at her nails now. She looked like she was about ready to pass out.

"Is it always that big?" She asked him.

"Only on real men, like me." Chuck answered.

Blair just laughed again. "It was…wow…I can't wait for..." Blair yawned and her eyes shut. She was out.

Chuck grabbed the afghan off the back of his chair and spread it across her petite body. He doubted she would even remember what happened when she woke up. If she remembered any of it she would probably just write it off as a dream anyway.

Chuck watched her as she slept. God she was breathtaking. And he was still very much aroused. He stuck his hand into his pants and quickly relieved himself before him himself passed out on the arm chair.

Chuck could hardly believe how far they had come since the 8th grade. He turned off the shower and made his way out of the bathroom. While out of the shower, he could no longer ignore the fact that he would be seeing her tonight. Not seeing the small thirteen year old girl who he used to tease but the woman that he loved more than anything, who he knew he could not handle losing. Chuck knew that Nate and Serena were trying to bring them back together tonight. And Chuck decided he was going to try his hardest to make that happen. He was going to finally ask Blair what happened with his uncle that night. He was finally going to get some answers and he was going to get Blair back, even if he died trying.