Chapter I

Chuck Bass was what everyone knew as the quintessential, Park Avenue bad boy who often walked on the wild side of life. His father, Bart Bass, owned a series of hotels where Chuck often stayed in any one of the penthouse suites. He was rich, conceited and terribly charming, which were the very things that brought the ladies running to him all the time. A lust-driven individual, he cared about very few things in life: money, sex, alcohol and his best friend Nate Archibald. Although to the rest of the world Chuck appeared as a cynical, morally bankrupt boy who had too much experience for his young age, deep down he was actually a caring, intelligent and deeply passionate individual…an image he would never let anyone see.

Blair Waldorf was a hopeless romantic who idolized Audrey Hepburn. Her sensitive side, however, contrasted with her tendency to be bitchy and controlling. She was rich and used her money and her charm to get whatever she wanted. Every girl wanted to be her and every guy wanted to be with her. But her cool and charming demeanor was often a show she put on for the rest of the world. Deep down, she was an insecure girl who felt pain in her very core…a pain that came from her boyfriend, Nate, sleeping with her best friend, Serena van der Woodsen, months ago. She had managed to forgive them both, but she would never forget.

Their circle of friends was quite small and included Blair's boyfriend Nate, who was also Chuck's best friend, Blair's best friend Serena and her boyfriend Dan Humphrey, who was still trying to fit in with the 'rich kids' for he was from the other side of the river…Brooklyn. After forgiving her boyfriend for cheating on her months ago, Blair desperately tried to get her turbulent relationship with Nate back on track. But he often seemed indifferent to her efforts and paid her very little attention. She had dreamt for years of losing her virginity to Nate, who she had made out to be the perfect boyfriend, in her bedroom with red roses beautiful music playing in the background. But the more she tried setting the mood, the more things would get in the way. Moment interrupted….or fate intervened? Blair wasn't sure anymore, but she was tired of feeling neglected. She craved to feel wanted and desired; feelings that Nate had never invoked in her throughout the lengthy course of their relationship.

Frustrated with the path their 'perfect' relationship had taken, Blair finally mustered up the courage and called him on his behavior. When his response didn't settle well with her, she sighed and asked him if he ever really loved her. She was met by a down-case gaze and silence. His response felt like someone had taken a dagger and plunged it into her heart, all the while twisting it to make the pain hurt more. But at the same time, she felt a form of relief and closure. She had wasted so much of her time on Nate and their one-way relationship that she suddenly felt relief from finally breaking free. Telling him that it was over between them, she got into a cab and didn't look back as she head towards Victrola.

Waiting for her when she arrived was Chuck, who stared absently at the car for a moment, surprised that Nate wasn't accompanying her.

"Where's Nate?" he asked, following her into the club, past the long lineup of people who were waiting to get in.

"I think we just broke up," she said and to Chuck's surprise, she didn't sound miserable or torn.

Instead, she sounded thrilled with the idea…something that shocked Chuck immensely. As they walked inside, Blair noticed how different the club looked from that very morning when she had visited Chuck and gone over his proposal to his father to purchase the place with him. Lights were shining everywhere and the music blared in the background as five showgirls danced on stage to the many cheers of young men crowded down below. Chuck moved her towards his private booth, one that was situated at the very center of the club, directly below the stage but a little far off to give him his viewing pleasure. Sitting down on the booth, she unbuttoned the first few buttons from the collar of the dress her mother had picked out for her and leaned back, grabbing Chuck's glass and taking a sip from his champagne. He simply sat there and watched her for a moment before speaking up.

"What happened?" he finally managed to asked, pouring himself another glass.

"It was simple," she began, turning to face him. "I asked him if he loved me and he didn't reply."

"I'm sorry," he said quietly, the sincerity in his voice surprising her.

"Don't be," she said, shaking the moment away and turning back to the dancers again. "I feel relieved."

Nodding, he finished his glass and went back for another refill. Blair watched him from the corner of her eyes, a small smile appearing on her lips. There was already an empty bottle on the table and the second one was a third unfilled. She wondered how he could consume so much alcohol so easily and be so unaffected by it. As he sat back and took another sip, she realized that he wasn't even the smallest bit drunk. Without realizing it, she turned her face until she was fully staring at him. He turned to face her and she noticed for the first time how deep his eyes were and how penetrating his gaze was. His nose was thin, his chin was arched in a perfect way and his cheek bones brought certain gentleness to his face. He had a handsome face, his body seemed well built and the suits he wore fit his character. His gelled but messy hair added to his seductive image and she realized in that moment how he simply oozed sexiness.

"Blair?" he asked, calling her name for a third time, only this time he finally got her attention.

Shaking her head, she came out of her daze and cleared her throat.

"What?" she asked, facing the dancers, praying that he didn't realize how flushed she was.

"Are you alright?" he asked, his left brow slightly arched up.

"I'm fine," she said, wanting to change the topic as quickly as she could. "You know, I have moves."

Smirking at her words, he sat up and glanced back at her. "Come on, you're ten times hotter than any of those girls."

"I know what you're doing Bass…," she began with a smile and then scoffed, turning to face him. "You don't think I'd do it."

"I know you won't do it," he replied with another of his signature smirks.

Taking his words into consideration, Blair rose to her feet. "Guard my drink."

Before he was able to say anything, she marched up onto the stage and turned her back to the audience. Taking a deep breath, she turned her head to an angle to see if he was watching and when she realized that he was, she slowly unzipped her dress. Chuck was surprised by her sudden bold and daring move, but he found himself sitting on the edge of his seat, his eyes glued on her. Stepping out of her dress, she tossed it aside and stood in nothing but her satin negligee. As she began moving slowly on stage, she twirled her fingers in his direction and smiled when she got a response from Chuck that involved him rising to his feet. As the music continued and the people cheered, Blair slowly moved down onto the stage, her seductive moves drawing a loud applaud from the single young men down below. Chuck simply stared at her with his hands stuffed in his pockets, mesmerized by the petite brunette beauty before him. When the song ended and her dance was done, Blair suddenly began blushing, realizing what she had just done. Grabbing her dress, she pushed past the loud cheers coming from everyone inside the club and rushed towards Chuck, burying her face in his chest in embarrassment.

"Waldorf, there's no need to feel ashamed," he said, pushing her back slightly to look at her face. "You're beautiful and it's time you knew it."

She was surprised by his words…they seemed heartfelt and almost genuine. But this was after all her friend Chuck Bass: the boy who lived for booze and women and nothing more. He then pulled away from her and took her dress in his hands. They both stared down at it and noticed the great tear it had on the side from being trampled on by the crowd below the stage. Feeling suddenly insecure as she stood in her negligee, Blair wrapped her arms around her body and looked to see if anyone was staring at her. Smiling softly, he removed his suit jacket and draped it over her shoulders, his fingers touching hers as he pulled the jacket tight in front of her. She felt a small electric shock when their fingers touched and the feeling it invoked in her shocked Blair, like so many other things had tonight. She looked up at him gratefully and he smiled in reply.

"Come on," he said, finishing his drink and escorting her outside. "I'll take you home. I think you've had enough adventures for one night."

When they reached outside, he led her towards his limousine and opened the door for her. She stared at him, surprised by his kind gestures which made him chuckle lightly.

"What?" he asked nonchalantly. "I may be a conceited jerk, but even I have some manners."

"Sorry," she mumbled, scrambling inside the limo as he got in after her.

After giving Blair's address to his driver, he shut the inner window connecting them with the front seat. Sighing, he looked outside as they drove down the streets. They remained silent for a long time and when she was sure he wasn't looking, Blair fixed her gaze on him and simply stared at the back of his head. She was unsure how long she was in her trance but his words brought her back to reality.

"That's twice," he said, finally facing her.

"What do you mean?" she asked, looking away.

"That's twice you've stared at me tonight," he replied. "Is there something on your mind?"

I feel so attracted to you right now, Blair's mind declared, the thought astonishing her incredibly.

"Do you want me to talk to Nate?" he asked, the name of her former boyfriend making her brows narrow. "Knock some sense into him?"

"No," she whispered, shaking her head.

As Chuck gazed at her, he loved the way she looked in his clothes. The light from the streetlights outside was cast on her face, making her appear even more beautiful than before, if that were even possible. Shaking such thoughts away, he cleared his throat and sat up slightly. Biting her lower lip, she stared ahead of her and he realized that she was debating something in her mind.

"Hey…," he said, gently touching her hand to get her attention, absently caressing her skin.

She flinched at his touch and bit her lower lip more tightly, closing her eyes as if she were in pain. He had felt something when he touched her just then, but he kept his thoughts to himself and frowned at the way she was acting.

"Blair?" he asked.

When she didn't respond or move, he closed the distance between them and whispered her name again, this time in a coarse whisper that sent a chill down her spine. When she opened her eyes, she followed his gaze as he leaned back in the seat. Her eyes held a lusty gaze in them, one that he suddenly became aware of. Before he was able to say anything else, she closed the distance between them and pressed her lips onto his. The simple kiss unlocked so much emotion she had locked away in her for so long, but before she was able to kiss him again, he pulled away from her, his own deep eyes staring into her soul. The strength and heat in his gaze made her somewhat uncomfortable, but she sat frozen. Blaire was sure that he would break into a fit of laughter and ridicule her, but his next words shocked her once more, but not for the last time.

"You were amazing up there," he said which made her smile.

His next words came out in a whisper.

"Are you sure?" he asked softly.

She couldn't help but smile softly at him and pressed her lips on his again. This time, neither pulled away. Their kisses were heated and passionate in ways she had never experienced before with Nate. His hands slowly moved to the jacket and he pulled it off of her, his fingers tracing a line down her arms as he did so. His touch was so gentle that Blair felt herself going mad. Pulling her onto his lap, she buried her hands in his hair as he began kissing up from her shoulders, to her neck and finally back to her lips. She was inexperienced in all of this, especially compared to him, so she let him guide her, trusting her body with him completely. As their kisses deepened, he moved his hands to the straps of her negligee and seductively pulled them down with his fingers, his touches on her skin almost burning her. Before they were able to go any further, the driver pulled to a stop before her condominium. Chuck was the first to break the kiss and he glanced outside the window with a soft sigh. She was unsure why he had pulled away, but when she followed his gaze, she realized the reason. Pulling his face back to hers, she pressed her lips back onto his, her fingers moving to the collar of his shirt.

"Tell him to keep driving," she whispered into his mouth.

He allowed the kissing to go on for another minute before he pulled away from her. For reasons he was unsure of now and would kick himself for later, he pushed her back slightly.

"You should go home," he said.

"What?" she asked, amazed that Chuck Bass was saying these words.

"Blair, you've been waiting for this moment for so long," he began. "Losing your virginity in the back of a limousine is hardly your fantasy."

"But…," she began, but he gently pulled her off of him and sat her down on the seat.

Grabbing his jacket, he draped it over her shoulders once more and began buttoning it for her, his eyes cast on the task at hand as she gazed down at him in confusion. He, Chuck Bass….notorious bad boy, had just said no to a girl. But not any girl…he had said no to Blair. A part of her felt angry and embarrassed at the way he was behaving. She was giving herself to him and he had rejected her. Before she was able to formulate any words, he pulled her face in for a long, private kiss, one that was shared only between lovers or married couples. When he pulled away, he left her lips swollen red and wanting more.

"If you want to be with me like that, I'm all for it," he began, his smirk not lost on the moment. "But you're not ready for this and I don't want you to regret anything."

With that, he opened the door and stepped out, extending his hand to her. She sat amazed by his behavior and all of her resentment towards him from moments ago floated away. Taking his hand, she stepped out of the limousine as he shut the door and faced his driver who was standing outside.

"I'm going to walk her home, I'll be right back," he said before leading her towards the lobby.

It was late and luckily only the bellman and the overnight manager were around. But neither of them looked up as Chuck led her towards the elevator. As they walked in, he touched the small of her back. It was such a simple but intimate move that made Blair face him as they rode the elevator up to her floor. She leaned up and placed a small kiss on his neck, which made him bring his arms around her and pull her body into his. They both inhaled one another's scent deeply and closed their eyes, enjoying their closeness silently. When the elevator sounded and the doors opened, he took her hand and led her to her door. She unlocked and opened the door, stepped inside and turned around to face him.

"I'm not sure what to say," she began, glad that the lights were off and her mother was asleep.

"Don't say anything," he said, leaning in to kiss her once more. "Goodnight."

"Goodnight," she replied with a soft smile as he winked at her and began heading towards the elevator.

Realizing that she was still wearing his jacket, she called out his name.

"Your jacket," she said as he faced her, his left hand in his pants pocket.

"Nah," he replied as the elevator doors opened. "It looks better on you."

As they smiled at one another, he rubbed the nape of his neck and disappeared from her view. She lingered at her door for another moment before locking up and heading towards her bedroom. Once she was inside, she closed her door, tossed the dress and her purse on her chair and sat on her bed. She closed her eyes and sighed, recalling their kisses and the way he had made her feel. With a content smile on her face, she crawled into bed and closed her eyes, hugging the jacket she still wore tightly.