Chapter 1: It's never just one night

Hey guys! This is my chair story, and it's my first gg fanfiction, so please leave comments and follow me for more! Basically, this story takes place in the present, and there's some sort of role reversal. So Chuck is now the society not and perfect one while Blair's the bad girl who won't follow any rules. I'm really excited about this story! I know it won't get lots of response because I'm posting it in 2018, more than ten years after gg started but whatever, there must fill be some die-hard gg fans or there. Love you all!

Chuck Bass waited impatiently at the foot of the stairs for his fiancée. The lavish dinner they were supposed to be hosting had started twenty minutes ago, and she still had shown no sign of coming down any time soon.

"Two more minutes, Chuck! I still need to fix my hair!" She yelled, making him sigh.

"Dorota, please tell the guests that we'll be there in an hour. This is going to take some time." He said, sitting down and looking at his watch as the maid nodded eagerly and hurried off. He slumped into one of the comfy couches in the living room and waited, adjusting his suit. It was so typical of his soon-to-be wife to be late on their own engagement party. Too lost in his thoughts, he barely notices when the elevator door opened and a man confidently walked in.

"Chuck! What are you doing here?" His best friend Nate asked, flopping down next to him and pouring himself a glass of Scotch.

"Waiting for my fiancée. She's still getting ready." He told him bitterly.

"You know, this is the one society dinner I'm actually going to, and the hosts are late!" Nate grumbled, wishing he had just skipped the whole ordeal and gone to his favorite club.

"Look I'm sorry. I'll make it up to you." Chuck said absent-mindedly, still wondering when his fiancée was going to come to grace him with her presence. A devilish grin spread across Nate's face as he thought exactly how Chuck could make it up to him. After all, it was only fair; if he had to attend Chuck's sleep-inducing dinner then Chuck could come with him to a bar or a club for a change.

"Alright. Tonight, you have to go to Victrola with me." He announced, catching his friend's attention. Chuck whirled around and frowned, obviously displeased.

"Absolutely not." He said with a tone of finality that anyone would have respected. But Nathaniel Archibald wasn't just anyone, and he wasn't going down without a fight. All these years, Chuck had been the perfect little boy, attending every horrible society event, having the same girlfriend for as long as he could remember. It was time to show Chuck the darker, but definitely more fun face of the Upper East Side. Soon, he would be married and therefore bound down for life. It was time that he lived a little, had a couple shots and pick up girls from the bar. Yes, Nathaniel wholeheartedly believed his best friend was truly missing out, getting married at the early age of nineteen, and that was why he did not back down.

"Come on, Chuck. You can't continue being Daddy's perfect society princess forever. Learn to let loose, have a bit of fun before you get married to some girl that takes an unhealthy amount of time getting ready." Nate mocked him.

"She is not some girl, and I don't feel like I'm missing out at all. I'm not ready to be stoned all the time, Archibald." He said, anger mounting as he faced his best friend.

"And you don't have to be! One night is what I'm asking, Chuck. Then you can have your happily ever after with your fiancée. You won't regret it, I swear."

Chuck relaxed, thinking hard.

"Alright, I'll consider it." He replied, giving the Archibald a small smile. Nate flashed his friend a wide smile and stood up.

"I'll meet you at the dinner, and I promise not to fall asleep like last time. Your fiancée is ready." He declared, looking up at the pretty girl descending the steps slowly in a flowing, lavender dress, her hair up in a perfect bun. Chuck stood up and admired her, taking her beauty in. He took her dainty, pale hand, and stroked her hair, inhaling her floral scent.

"Breathtaking as always, Eva."

XXX

"Nate was right." Chuck thought to himself as he looked around the table tiredly, watching the old women wearing too much makeup and jewelers exposing scandalous gossip about everyone on the Upper East Side. They thought themselves superior, with their inattentive husbands who worked too much and all had young mistresses they pretended not to know about, and too much time on their hands. They organized these awful events to brag to no end about their secure social status to bring their minds off the fact that their lives have absolutely no meaning whatsoever. And yet, their approval was your ticket to the Upper East Side. If they liked you and your family, your future and your money were secure. If they didn't, then you may as well be banned to the other side of the planet. So that was why Chuck was currently suffering in a hot suit and an itchy tie, pasting on a fake smile and telling everyone how glad he was to be marrying Eva. Nate had given up a while ago and was now smoking outside without a care in the world. How dearly Chuck wished to join him, but he had to stay for Eva. Eva found these women's opinions important, and he could not abandon her, not now, when the wedding was so close. And maybe it was because he was sweating too much, or maybe it was the prospect of the wedding coming so soon but he saw himself and Eva in one of those chairs, talking about their lives and their money. That vision made him so depressed that he sighed out loud, forgetting the people around him.

"Tragic, is it not?" Cece Rhodes told him sympathetically, thinking his sigh was because of something he had just said.

"Right." He said uncomfortably, ignoring Eva's confused frown beside him.

"Ladies, may I just talk to Chuck for a moment?" His fiancée asked gently as the ladies agreed, giving them delighted smiles. He walked with Eva, already expecting her reprimand.

"Chuck, I know it's hard for you, but we have to go through this. You know how important their approval is!" Eva told him, touching his cheek lightly and giving him a small smile, one different than the sparkly one she had been giving the women less than a minute ago. Chuck breathed out and loosened his tie.

"I'm sorry Eva. It won't happen again." He surrendered, ready to back to the table.

"Good." She said before she kissed him lightly and started to slip away.

"But Eva." He called out, making her stop and turn around. "Do you really want us to do this for the rest of our lives? Trying to gain their approval, and then becoming one of them?" His wife-to-be looked shocked for a moment, having never heard her fiancé express such fears. But she just smiled lightly and said:

"Don't worry, Chuck. We'll never become one of them." She walked back to the table, leaving him alone in the hall. Her words didn't reassure him, he realized. How was he supposed to know that he wouldn't become one of them? That he wouldn't be attending these painful dinners for the rest of his life?

"Having doubts?" A familiar voice said next to his ear, startling Chuck.

"It's normal, right? To have doubts before the wedding? I'm just not sure if I want all of this. I love her, but..." he confessed, facing Nate, who merely shrugged.

"I wouldn't know. But what I do know, is that if I don't get you out of here this instant, something bad's going to happen." He smirked. Chuck shook his head, chuckling.

"I can't leave now."

"Yes, you can. Eva will forgive you." Nate told him, leading him to the fancy black limo waiting outside.

"Alright. But just one night." He warmed his best friends who smiled evilly as he thought to himself that it was never "just one night". But there was no need to tell Chuck that. Instead, the two best friends laughed and talked as they were taken driven away.

XXX

"You're completely sure about this, right?" Chuck asked Nate as they stepped out of the limo and started walking towards the club. Chuck looked around and shivered, he has never been in this part of town before, and even if he would never admit it, he was a bit nervous. What if he hated it? What if he got rejected by everyone? Truth to be told, the closest idea of partying he had ever experienced was people's birthdays in high school, and even then, Eva and he had always left nice and early before the real drama started.

"Yes, you'll love it. Now stop asking me questions." Answered a slightly irritated Nate as he made his way down the streets lazily, knowing the place by heart.

"But do you have the invitations?" Chuck worried, not seeing Nate carry anything except his wallet. Nate turned around incredulously and laughed aloud, realizing his friend was serious.

"You can't ask questions like that to everyone in the club, or it'll be clear you've never partied in your entire life. There are no invitations, Chuck. You just have to hang with the right people. They approached the club, and Chuck looked at it in wonder. It was in full swing at this time, and the lights were shining, music was blaring loudly as people went in and out in different states. He spotted a dancer wearing a long coat that she quickly took off once in the club. Her revealing dress and her fishnet tights made Chuck stare but he came back to his senses, quickly, mostly due to Nate's snickers behind him.

"It's like you've never seen a woman before," Nate whispered. Chuck said nothing but frowned. He had seen Eva plenty of times, and they were sleeping together. That was all he needed. The two boys entered the club moved up to the front, where they could see the dancers up close. Chuck's eyes widened, he had never seen so many people dancing, drinking, talking before in one room. The balls that he had been to barely served alcohol and were fairly quiet, and now he was being plunged into a new world full of guilty pleasures.

"I'm gonna go get us drinks," Nate called out to a barely moving Chuck. He stiffly nodded and sat down, watching not only the dancers but everyone. To his surprise, he recognized a few people from school, people he would have never expected to be at a place like this. Then again, he was the last person he could think of to be in the middle of a burlesque club, as Nate called it. As much as he enjoyed the music and the dancers, he felt slightly uncomfortable being seen in a place like this, and all he wanted was to go home, to go back to Eva and forget this whole ordeal. But Chuck gritted his teeth and told himself that everybody was able to do it, so he stayed. Nate came back quickly with shots and sat down next to Chuck, eyeing the dancers with obvious pleasure.

"Shots?" Asked Chuck, getting more nervous. He had never done shots before, and he wanted to try now.

"You're nervous. This will make it go away." Nate said simply, gulping down a drink and beckoning a stranger. Chuck hesitantly took a small glass and took a sip, almost repulsed. It burned through his stomach, and he gagged.

"Honestly. How do you not know how to do shots?" a female voice said from behind him. Chuck's insides squirmed with embarrassment as he turned around and saw a familiar blonde he could not put a name.

"Jenny! Good to see you here!" Nate greeted her, an affectionate smile growing on his face.

"You're Chuck Bass. You probably don't know me, we're not it the same years in school." She said, smiling.

"No, I remember seeing you," Chuck said slowly.

"So what are you of all people doing here? Aren't you supposed to be at a dinner or something?" She taunted, smirking.

"Just helped him escape, actually. It's his first time in a club, so he doesn't really know what he's doing yet." Nate laughed at the memory of Chuck sipping and gagging on the shots.

"That was pretty clear. You're supposed to do them in one go. Like this." Jenny took a glass and tipped the liquid into her mouth, gulping it down in one go before slamming it back in the table. Nate cheered as he took a shot too. Feeling nervous, but not wanting to be left out, Chuck quickly took a glass and shoved the alcohol down his mouth, trying to ignore the burn.

"Hey, you're getting the hang of it," Jenny told him before turning back to Nate.

"Blair got us a private room again, do you wanna come?" She asked, pointing at a door in the corner. Nate hesitated, looking back at the dancer he had been eyeing.

"Will there be Serena?" He inquired hopefully as Jenny rolled her eyes. The names rung a bell in Chuck's head as he remembered Serena Van der Woodsen, the beautiful party girl Nate loved to have fun with. He strained to remember who this Blair was, but could not, and tuned back in the conversation.

"Is Chuck invited?" Nate tried and failed to ask discreetly. Jenny shrugged and said:

"I'm not sure, you'll just have to find out."

This sentence made Chuck gulp, nothing would be more humiliating than to be rejected at the door. Nevertheless, he followed Nate and Jenny to the door. Jenny knocked and it opened, revealing a bulky bodyguard who smiled at Nate and Jenny.

"Glad you could make it." He told Nate, opening the door for him and Jenny. Then he spotted Chuck and frowned.

"Who is he?" He asked Nate.

"I'm Chuck Bass," Chuck said, annoyed that they were speaking of him as if he weren't there.

"I'm not sure, you're not a regular... Blair's parties are quite exclusive..." he hesitated.

"Do I pay you to stand around and wonder if someone is invited or not? The whole point of the list I gave you was to know without having to ask me! Either he's on the list, either he isn't." a voice snapped loudly.

"I'm very sorry." the bodyguard apologized.

"Whatever. I'll take care of this." the voice said again, pushing him aside and showing herself. Chuck's jaw dropped as he saw her, and his mind went racing. She was the most beautiful girl he had ever seen, and yet beautiful sounded plain when you put it on her. She had luscious dark curls and a sharp face. She was wearing a short leather dress, and her long legs are spilling out. And yet, it wasn't just her astonishing beauty that made her so insanely attractive. It was her determined expression, her aura felt dark and mysterious. For a moment, Chuck forgot how to breathe.

"Chuck Bass. Never thought I'd see you here." She drawled, looking at him up and down, her lip curling into a dark smile.

"That's me." He choked out.

"Don't you have a daddy and a girlfriend to run back to?" She asked him, an eyebrow raised.

"Fiancée, actually. And I don't need to run back to anyone." He corrected her quietly.

"Alright, well it's always nice seeing someone new here. Breaking innocence is what I know best." She said a dangerous smile on her face.

"What innocence?" Chuck said, giving her a smile. He caught her off guard for a second, but she soon composed herself and smiled audaciously.

"Welcome to Victrola, Charles." She smirked, letting him in, and walking away. The conversation left Chuck out of breath and amazed. He stood there, not moving, for what could have been seconds, or could've been days. Around him, people were taking drugs, playing poker, drinking and making out. Finally, Nate came up to him, handing him yet a glass of alcohol, happy that he had been let in.

"Alright, I'll tell you who everyone is. The blonde is Serena." He said wistfully, pointing at the bubbly blonde girl surrounded by drooling men.

"The brunette over there is Georgina. She's a bit crazy, so it's better not to talk to her, even though she's not." Nate gestures to a tall girl with sharp features.

"This is Vanessa. She's great." He pointed to a small dark headed girl who was playing poker. And so the introductions continued, and soon Chuck could pour a name on everyone in the room. All except one. The amazing girl he who had greeted him at the door was lazily drinking alcohol, talking to a few guys around her, sometimes smiling slightly, but never laughing, much unlike Serena, whose tinkling laugh you could hear from the other side of the room. And he could still not name her. Would she always remain a mystery to him?

"The girl on the right, wearing the leather dress. Who is she?" Chuck managed. Nate intercepted his look of awe and grimaced.

"That's Blair Waldorf. She's the most powerful person in this room, and you definitely to do not want to get on her bad side. Trust me, she's beautiful, but she's too dark, too mysterious. People think they know her, but no one actually does. She's a real piece of work, and she's not worth it. Don't get involved with her, Chuck, only bad things will happen to you." Nate told him. The words had no effect on Chuck as he continued staring blatantly.

"I'm going to talk to her. Blair Waldorf." He said, appreciating how even the name sounded. Nate sighed but did not stop him. Chuck walked across the room, keeping his eyes on her as he approached her and the people surrounding her. His insides flipped as he saw her up close again, and the feeling almost made him forget his own name. She was quietly talking to Carter Baizen and a few men he didn't know well, holding a cigarette close to her mouth a puffing our white air. She turned her head toward him.

"Bass." She greeted him.

"Waldorf." He breathed, delighted she remembered his name.

"This is Daniel Humphrey and Carter Baizen. Surely you've heard of them." She introduces him quietly as he tore his eyes off her and turned to face the two men. Daniel's hair was curly and all over the place, and he was one of the few not wearing a suit in the room. At first, he didn't see it, but looking closer, Chuck could see the striking family resemblance between him and his obviously younger sister, Jenny. Carter had an arm wrapped around Blair and was quite drunk, his words were slightly slurred and his expression being all over the place. Yet, he looked at Chuck straight in the eyes, and brought himself closer to her, depositing a slobbery kiss on her mouth. Chuck watched the whole spectacle aghast. The sight of Carter kissing Blair made him squirm and have a strange burning feeling the back of his throat. Suddenly, he wished Carter could burst into flames that very second and disappear from his life, from Blair forever.

"I'm her boyfriend." He said slowly, a drunken grin appearing on his face as he attempted again to kiss Blair, this time in her neck. However, she looked cold and irritated, and slapped his hand away, ice in her eyes.

"You aren't anything to me, Carter. You're drunk, your breath smells terrible and that kiss was mediocre at the very best. You should go." She snapped angrily, not making a move. Carter took a minute to let her words sink in, and then slunk away, sorely disappointed. Daniel just smirked and ran his hands through his hair, as if he was used to this scene. He spotted his sister and excited himself, leaving Chuck and Blair alone. Chuck's breathing sped up at the fact that they were women together and that she was going to talk to him. He immediately reprimanded himself after, telling himself he had a beautiful fiancée at home, and that if he didn't leave, things were quickly going to get out of hand, if they hadn't already. But his feet remained rooted to their spot, making him unable to move, unable to look at anything but her.

"Sorry about that. He does that a lot, especially when he's drunk. You mustn't judge him yet, he can be quite pleasant when sober." Blair addressed him, taking a long drag from her cigarette, discreetly smiling.

"Maybe you should keep him away from alcohol then," Chuck said quietly, taking a risk and sitting down on the sofa next to Blair. His leg accidentally brushed against hers, and every bone in his body shook at her warm touch, craving more. He had never felt this way before, not even with Eva. While he silently suffered as every part of him reacted to her touch, she remained indifferent, her expression unreadable.

"Maybe." She agreed. That was all they said to each other for the night, instead they looked at other people, or he listened to the conversation she would have with the guests that came to her. This was, Chuck reflected, one of the best nights of his life. How could he have refused all of Nate's offers and pleas, calling him a party animal when he could have met her sooner? To think that if he had refused to come here tonight, he wouldn't have been sitting close to her, their legs brushing together, his heart soaring. Chuck discovered she had many admirers and followers, she was deemed as the ruler of all these vents, people came to her for help, for advice, for anything really. He was surprised to see that she chatted amicably with Serena Van der Woodsen for a while, then being so different but so close. But his favorite moments were the ones where they were alone, when they had an unspoken connection, he was sure she could feel it. He had never felt more tortured, yet more content in his lifetime.

XXX

Around the early hours of the morning, Chuck realized he should have gone home hours ago to comfort his fiancée whom he had left at a dinner and get ready for a brunch with all the notable families of the Upper East Side, yet he had no wish to go. All he wanted was to stay here forever, to enjoy her presence for the rest of time. However, people were leaving, and Nate clearly wanted to go home too.

"I should get going." He strangled out, looking at her, desperately hoping that she would care, that she would be saddened by this information. But she betrayed no emotion, instead, she looked up at him and said:

"Goodbye Bass. I'll see you around."

Chuck's insides twisted as he walked off, trying to make sense of those words. To see her again, he would need to go to another party, and that could be in days. He didn't know if he could days without seeing her, without hearing her beautiful voice. Without even trying, she has grown his entire life of balance, and now he was left with several broken pieces that did not fit together. He could not list after her with a wedding in less than a month, yet he didn't think he could survive without her. Glancing one last time to her, he wondered if would ever see her again.

Alright, that's it for now! I'll post the next chapter soon if this one gets a lot of response! Don't hesitate to tell me what you think or give me any advice!