Welcome to the story, upper east siders. I know Gossip Girl went off the air almost 10 years ago (how is that actually possible? I feel old), but I started watching it again over the last few weeks and I wanted to write a story about one of my favorite couples: Chuck and Blair. C.H.A.I.R. These two made the entire show for me, without them, I never would have watched it until the very end. I'm currently watching season 3 and loving their relationship together, which gave me an idea for a story. I know no one will probably read this since the show has been off the air for almost 10 years so, I am basically writing this just because I had the idea and figured why not. It'll probably end up being 10-15 chapters, but we'll see. After I finish the original Gossip Girl, I am going to start watching the new one and write about that if there's a couple in there I end up shipping. I do not own Gossip Girl: this story is simply fiction with fictional characters, I owe my story inspiration to Gossip Girl and the writers of the show.
Backstory: Blair, Chuck, Nate, Serena, Dan, etc., are all 18 and starting their senior year of high school. I'm starting the story in senior year for a reason. Chuck & Blair haven't slept together…yet. Blair and Nate are dating, Dan and Serena are dating, Chuck is being his usual womanizing self. Nate and Serena still slept together like in the show. Blair's mom hasn't married Cyrus yet. This story is heavily Blair/Chuck, rated M for obvious reasons, and will also have mentions/scenes of other character as well to keep things interesting.
Welcome back, Upper East Siders. It has been a long, hot summer. School may have been out all summer, but my inbox has remained in. Let's skip to the good stuff, shall we? James96 sends us this: "Spotted at grand central station, Queen B and Golden Boy Nate Archibald, hand-in-hand as they return from their summer in the Hampton's." Is it true, did our Queen and Golden Boy spend a whole summer shacked up in the Hampton's? I guess we're going to find out. The end to this summer just got a whole lot hotter.
Nate embraced Blair in his arms one last time before saying goodbye. He kissed her neck and took in her sweet scent, she smelled like fresh air. All the time spent at the beach over the last few weeks had them both smelling like fresh air and salt water. "I had so much fun this summer with you sweetie" Blair said as she broke their embrace suddenly. He looked down at her and smiled. Her curls framed her face perfectly as she smiled back at him.
"Me too" Nate said and held her hands. "I'll see you tomorrow, I have to go home and do a lot of laundry before school starts tomorrow" He laughed and sighed.
"I'll see you tomorrow" She kissed him and said goodbye.
She watched him get into his limo and smiled as she watched the car drive away, waving bye to Nate. She suddenly felt exhausted and was ready to lay down in her own bed.
The elevator ride upstairs to the penthouse was short and peaceful, finally Blair was alone. This summer had been a lot of fun with Nate, Serena, Eric, and even Dan. They spent the entire summer in the Hampton's. Lounging by the pool, drinking at night, laughing, and lots of shopping. Things finally felt like they were falling into place, after Blair and Serena's falling out due to Serena having sex with her boyfriend. Blair still cringed at the thought of it. Her thoughts were cut short when the elevator door suddenly opened and there stood her mother and Cyrus. Gross. Cyrus was always there, always lurking, and annoying her.
"Mother, Cyrus" She smiled and hugged her mother. Cyrus also joined in on their hug.
"How was your summer darling? You look like you had a lot of sun" Her mother smiled as they walked into the living room.
"It was…fun. It was a lot of fun" Blair smiled at her mother and Cyrus.
"Not too much fun I hope" Cyrus spoke. "Stayed out of trouble I imagine" He said as he looked at Eleanor at nodded his head.
"Always" Blair faked a smile at Cyrus and her mother. Who did he think he was, her father? He would never replace daddy, he couldn't, Cyrus was far too annoying. Just as I'm starting to be able to tolerate Cyrus, he becomes annoying again.
"How is Nate? Serena?" Eleanor asked while Cyrus stood close to her with his arm around her back. "I heard from Nate's mother over the summer that you two were getting quite serious, and even talking marriage" She said with raised eyebrows and a questioning look on her face.
If only you knew how he had sex with my best friend, Blair thought to herself. She still couldn't get over it, she didn't know if she ever could. Nate had come clean and told her that him and Serena had hooked up before she went off to boarding school. Even though it had been four or five months since Blair found out, it felt like just yesterday. She felt a pang of hurt in her heart at the thought.
"Serena is good, she spent her summer wrapped up in Dan Humphrey's arms" Blair scoffed at the thought of Dan Humphrey. He was always there, lurking around. Always making jokes or being sarcastic, which Blair couldn't stand. She still didn't know why Serena was with him, he was a loser in her eyes. "Me and Nate are good as well, but I don't think we'll be getting married anytime soon" Blair let her eyes wander as she spoke to her mother. I can't even forgive him yet.
"Well, that's too bad to hear. Maybe you should talk about it sometime with him, I mean you are eighteen years old now, and you're going into your senior year. Which reminds me, I had your uniform dry cleaned and it's upstairs on your bed. Along with some new shoes which I think you'll approve of" Eleanor smiled at Blair and then down at Cyrus.
"Thanks" Blair smiled at her mother and Cyrus who took a seat on the couch together. Cyrus was smiling at Eleanor and then leaned in for a kiss on the cheek.
Gross.
"I'm going to head upstairs, I have a lot to get done and school starts tomorrow" Blair smiled and headed towards the stairs.
"Uh, ok. See you later" Eleanor said cooly. "Dorota is out at the store picking up groceries for dinner, she'll be back a bit later" She stated as Blair headed up the stairs.
Blair opened the door to her room and smiled at her view. I missed my bed, my wardrobe, my bathrobe, she thought and smiled to herself.
She set down her bag by her closet and hopped into her bed. She fell backwards onto the bed, and immediately felt comforted by her soft mattress and comforter. It felt good to finally be home.
What am I going to do about Nate? Will I truly ever be able to forgive him for sleeping with my best friend? I don't even know anymore. I spent the entire summer with my boyfriend, and we still haven't had sex, not even once. I'm not sure I even want to, with him.
Queen B is going into senior year as a virgin. Blair cringed at the thought.
Blair walked confidently into the courtyard of Constance Billard with her head held high. Senior year is going to be the best year yet.
She immediately saw Serena, sitting down at one of the tables with Dan sitting right beside her. If he was any closer he'd be sitting on her lap. Blair rolled her eyes before walking over to them.
"B!" Serena yelled happily and started waving when she saw Blair approaching them at the table. She got up from where she was sitting and embraced Blair in a hug.
"Senior year" Blair raised her eyebrows and smiled as their hug ended. She looked up at her best friend who had the same smile on her face as Blair.
"Senior year" Serena repeated back and smiled at Blair. Serena took a seat back next to Dan and kissed him on the lips.
"Where is everyone?" Blair looked around the courtyard as she asked Serena. "It's so empty this morning" She noticed.
She saw a few girls who she didn't associate with sitting at a table in the middle of the courtyard. A few of the stoners smoking in the corner of the courtyard, glaring at students who passed by them.
Blair the noticed Chuck Bass smoking in the group of stoners in the corner of the courtyard. He was blowing smoke out of his mouth and nose and smirking at the girls who were sitting in the middle of the courtyard. Freshman girls. They giggled amongst each other and smiled at Chuck Bass, who couldn't keep his eyes off of them.
Chuck Bass, always womanizing it seemed. Blair rarely saw him without a woman hanging all over him, or him hanging all over a woman.
But eyeing freshman? Really? He is disgusting. What a bass-hole, Blair thought to herself.
"Well, you're always early everywhere you go Blair" Serena said and smiled. Dan had his arm around her shoulders and was nestled closely to her.
"True" Blair smirked and took a seat at the table.
"Where's Nate?" Dan suddenly asked. "I'm surprised he's not here with you right now" He questioned.
"I don't know where he is" Blair shrugged. "I haven't heard from him since he dropped me off at home last night."
Blair suddenly realized she hadn't heard from Nate since yesterday, not even a good morning phone call or text. She glanced down at her phone and looked at the time. 7:45. Class started in just 15 minutes, the first class of senior year, and she hadn't even heard from him.
"Is everything ok B?" Serena placed her hand on Blair's arm and asked.
Blair looked up at Serena and smiled at the gesture. No, the fact that my boyfriend slept with you is not ok. How will it ever be ok? We were supposed to be each other's firsts, first love, first kiss, first time…and now that's all down the drain. She thought to herself.
"Yeah, everything is fine" Blair smiled again quickly at Dan and Serena. "He just overslept this morning I'm sure" She said reassuringly.
Just when Blair was starting to feel unsure about everything, Nate, their summer together, the fact that he cheated on her with her best friend, her thoughts were quickly interrupted when she noticed a familiar somebody walking towards their table. Chuck Bass.
Chuck Bass. Someone she considered a friend, I guess. Although nowadays, their friendship was questionable. Chuck was always seen around school or basically anywhere with a different girl on his arm. When he didn't have his arm around some random woman's shoulders or his hand on their ass, he was scheming. Always scheming.
Blair loved to scheme…it was something she often hated to admit out loud, especially to Nate. Being right in the center of drama, or starting drama, was one of Blair's guilty pleasures. Serena knew it, Chuck knew it, hell, even Dan knew it…but Nate chose to ignore that side of Blair.
The question of being Chuck's friend wasn't even a question 4 years ago, at the start of high school, freshman year.
Blair pulled out her round hand-held mirror and flipped it open, checking her lips and eyes, ensuring her makeup was absolutely perfect for the first day of school. Freshman year, where it all begins. This is the year, the very best year of my life, the year where I will rule Constance Billard St. Jude's. By the end of this year, everyone will know my name. Blair smirked to herself and closed her mirror, placing it back in her bag.
She walked confidently up the steps, smiling as she spotted her best friend, Serena van der Woodsen. She hurriedly ran up the steps calling out for her best friend.
"S!" Blair shouted and waved in Serena's direction.
"B!" Serena smiled and waved at Blair.
Serena was a flawless blonde, Blair had never seen someone as pretty as Serena. And it was effortless on her end. Serena didn't even have to try, she was just pretty. Blair always envied that, but she never let it show.
"I can't believe today is the day, the start of the best year of our lives S" Blair smiled and embraced Serena in a hug.
Serena squealed in excitement, clearly just as excited as Blair about the first day of school.
"I can't wait to see Nate in the courtyard later" Blair pursed her lips and smiled, just the thought of Nate brought her so much joy.
Serena giggled and rolled her eyes.
"If you start making out in the courtyard on the first day of freshman year I'm going to be sick" Serena joked.
Blair and Serena walked arm-in-arm through the doors of Constance Billard, never feeling more confident then they did in this very moment.
Although the day started off perfectly, during her first class Blair couldn't help but think back to the events of last night, the awful, most horrible thing she ever witnessed. Her father, Harold Waldorf, kissing the male model her mother had hired, Roman Garrel. The kiss didn't last more then 5 seconds, but it still horrified Blair in this very moment, just as it did last night. Her father, daddy, the person she loved most in her life. She loved her mom but, Blair and her dad always had a special bond from the time Blair was a little girl. The thought of her dad being anything but faithful to her mother horrified her. Mom and daddy always had the perfect marriage, they were so in love…or so I thought. I guess daddy is in love with that gross, short, middle-aged man with the foreign accent. Roman.
Blair felt so stressed from what she witnessed last night, she couldn't stop eating this morning before school. Dorota had made her a special breakfast for the first day of freshman year, and Blair had indulged. She ate the entire plate of pastries, which was at least 15 in total.
Was she supposed to tell her mother what she saw? I mean, what was there to tell? Daddy kissing Roman in the kitchen and then holding his hand right after. What did that even mean? Would they get a divorce? Would I now come from a broken home?
Blair sighed to herself and tried to focus her attention back on her English teacher who was reviewing the syllabus for the semester.
The bell finally rang and Blair was relieved, class was dismissed. Her first class of freshman year and Blair could hardly focus. All she could focus on was what was happening in her life, this was not how the first day of freshman year was supposed to be.
She rushed out of the doors leading to the courtyard, looking around for Nate, but she didn't see him. I guess he was still in class. Blair turned around and waited for Serena to come through the doors, but she never did. She saw Penelope come through the doors instead.
Blair crossed her arms over her chest and let out a lengthy sigh when she saw Penelope approaching her, along with two of her friends who Blair didn't recognize.
"Hi Blair" Penelope smiled fakely, and her friends joined in with the ever-so-fake smiles.
"Hi" Blair smiled fakely back.
Penelope had been bragging in front of Blair's mother about how she had the highest grade in the class, and Blair didn't. This was so embarrassing to Blair, since she was a perfectionist and strived to be the very best at whatever she did. She couldn't quite find it in herself to forgive Penelope over the summer for being such a braggy-bitch.
"Want to eat lunch with us on the steps?" Penelope asked while holding three bags of food in her hands. "The met steps, by the way" She smirked.
"No, I'm waiting for Nate" Blair shook her head no and pursed her lips.
She wouldn't be caught dead eating with Penelope and her friends, especially after how she had embarrassed Blair just a few months prior.
"I am hungry though" Blair said and snatched the bags of lunch from Penelope's hand. "You read my mind, Penelope. Guess that's why you were head of our class, mind reader and the smartest student in the 8th grade" Blair smirked and held the lunch bags on her lap.
"Bitch" Penelope rolled her eyes and walked away from Blair.
This year was going to be interesting, Blair thought.
She sighed and looked down at the bags of lunch in her lap. Looking around the courtyard once more and still not seeing Serena or Nate, she felt alone. And annoyed. Also, a bit hungry.
Blair started eating the first sandwich in the bag, then the second, and then the third. She felt so stressed and just couldn't help herself from indulging, again.
Just as she was finishing the last bite of the sandwich she felt someone tap her shoulder.
"Blair" Chuck said as he tapped on her shoulder.
"You scared me" She almost choked on the last bite of her sandwich and turned around to face Chuck.
"You ok?" He genuinely asked and sat down next to her on the bench at the table.
"Yeah" She half smiled. "No…"
"What happened?" He asked. "Did Nate forget to bring you flowers on your first day?"
"It's not that" Blair thought about what had happened last night, which had upset her more then anything ever had.
"Well, then what is it?" Chuck asked. He seemed genuinely curious as to what was bothering her.
"It's my dad" Blair sighed and looked Chuck right in the eyes. "Last night I was getting a glass of water before bed and I caught my dad kissing-"
"A stripper?" He laughed.
"No, Chuck!" She rolled her eyes. "Roman…the male model my mother recently hired"
"Really? Didn't see that one coming. I thought you were going to say you caught him kissing some stripper or prostitute" He looked surprised.
"Of course you would, you always think everyone is with strippers or prostitutes, but everyone is not you Chuck" She rolled her eyes at him.
"Yeah, there is only one Chuck Bass" He smirked.
"I feel sick just thinking about it. My poor mother…I don't know how she will react. I don't know if I should tell her, I mean maybe I don't know what I saw. It was late, and I was tired after a long day lounging by the pool with Serena. I don't even know what Serena will think about this" Blair said quietly, thinking about how Serena would react when she told her.
"You haven't told Serena? I feel special" Chuck caught Blair's eye and smiled. That smile. Every time Chuck smiled, his eyes turned 50 shades darker and had a unique sparkle to them. He really did have nice eyes.
"I have to go" Blair said as she suddenly stood up from the bench. Her mind was racing, she had 100 different thoughts running through her head. She had no control over the situation with her father, and no control over what would happen if her mother found out. They would probably get divorced. Blair would have two homes instead of one, and they would never be a family again. She hated feeling like she didn't have control, Blair lived for control.
She noticed Chuck looked surprised when she suddenly stood up and left, but she didn't care. She wanted to be alone. She wanted to feel in control, to know what was going to happen, to ensure her parents stay together no matter what. She didn't know what to do.
She started walking towards the girls bathroom, thinking about refreshing her makeup and her hair.
Blair walked down the hallway, her mind still racing. She didn't even notice who was standing right in front of her when she suddenly bumped into Serena, knocking the books out of her hand.
"B!" Serena squealed, excited to see her best friend even though they had just literally collided in the hallway. She wasn't even phased by the books which had just been knocked to the ground.
Blair picked them up and handed them back to Serena.
"S" She forced a smile.
Serena didn't even notice her forced smile, which she was grateful for. Blair just wanted to be alone and gather herself.
"How's the first day? I just got out of History, it was boring" Serena said as she took the books from Blair's hands.
"Boring also, I had English and I felt like it lasted 3 hours" Blair rolled her eyes. "I have Math next, so I'll see you then" She said and started walking towards the bathroom once again.
"B!" Serena called after her, but Blair wasn't in the mood to talk, not even to her best friend.
Where the hell was Nate? She hadn't even seen him all day. She thought about what Chuck said about Nate not bringing her flowers…and he was right. She hadn't even said hi to Nate yet. The one day she needed him most…he was no where to be found.
Blair opened the door to the bathroom and made her way to the mirror. She fixed her hair and let out a loud sigh. I hate this. I hate knowing this about daddy and Roman, and not sure what to do with the information. Eating all those pastries this morning helped, strangely. And those three sandwiches in the courtyard.
My mother would freak out if she knew I had eaten all this today…she would say something along the lines of "haven't you had enough?" Blair cringed at the thought of what her mother would say to her right now.
She glanced at herself in the mirror, her blouse looking tight against her bloated stomach. She suddenly felt disgusted with herself, a feeling she had never felt before. Sure she never felt drop dead gorgeous like she imagined Serena did, but she felt pretty, hot, and attractive usually. Looking at herself in the mirror, she didn't recognize herself. She felt out-of-control, not only of herself but also the situation with her father.
Blair needed to control something, and there was only one thing she could think of, controlling herself in that very moment. The only thing she could control.
She turned around and headed for one of the bathroom stalls, she suddenly knew what she was going to do. She shut the stall door behind her, not even bothering to lock it.
Blair was going to make herself sick, and feel in control of herself again.
Blair had never considered making herself throw up before, but with everything going on in her life, there didn't seem to be any other solution to making herself feel better. It's not like Nate was there to comfort her in her time of need.
She had heard plenty of her mother's models making themselves throw up in the bathroom stalls at the fashion shows, and she and Serena had stated how horrible that must be. But here Blair was…about to do the horrible thing she thought she'd never do.
Before she knew it, she was kneeling on the bathroom floor of Constance Billard with her fingers halfway down her throat and her head hanging over the toilet, throwing up her entire breakfast and lunch.
She had heard the bathroom door open right before she made herself sick, but completely ignored it. Assuming it was a random student she didn't know, and didn't care to know.
But it wasn't, it was someone she knew.
"Blair?" Chuck said loudly, for the entire bathroom to hear. "I followed you in here because you didn't seem well and suddenly left during our conversation in the courtyard"
He sounded almost concerned for her well-being. Did Chuck Bass actually wonder if she was ok? Because she wasn't.
She flushed the toilet and opened the stall to find Chuck Bass standing right outside of it.
"I'm fine" Blair lied and headed towards the sink to wash her hands.
She looked at herself in the mirror, she was no longer bloated. But now her hair looked messier then when she first came into the bathroom.
She barely held in a gasp and shock filled her entire body when she noticed some vomit was on her blouse.
Her face didn't hide her shock, and Chuck immediately noticed what she was staring at.
"Are you sick?" He questioned.
"No, I'm fine. Like I said, I'm ok" She wet a paper towel and started wiping the vomit off of her shirt. "If anyone finds out you're in here, in the girls bathroom, you're going to be in trouble" She glanced up at him in the reflection of the mirror.
Chuck and Blair had been friends since they were children, basically best friends. They weren't as close as Serena and Blair, but they were still close. Even though Chuck was seen as the biggest womanizer in the 8th grade, this didn't stop Blair from being his friend all throughout the 8th grade.
Chuck started walking towards Blair and stopped right behind her, nearly touching her.
He knew she was lying.
"I…" Blair's voice trailed off, not able to finish her sentence. What have I done? What have I just done to myself? Blair started to question everything once again.
"I know you're lying Blair, you're not ok. You forget I know you and when you are being truthful or telling a lie, you're a bad liar" He said with a small laugh. "You forget who helped you steal Georgina's lipstick in the 7th grade and put it in Nate's bag, to make him look bad when he forgot to call you on your birthday"
Blair remembered the scheming her and Chuck had done to get back at Nate for totally forgetting her birthday that year. She smiled at the memory and decided to tell Chuck what was going on.
"I made myself sick, I made myself throw up" Blair suddenly stated as she turned around to face Chuck.
"What do you mean?" He questioned.
"I had heard the models doing it at my mother's fashion shows, me and Serena had heard them. Making themselves throw up in the bathroom, to be thin and to feel pretty" Blair couldn't believe what was coming out of her mouth, what she was telling Chuck. "I feel like I have no control over my life right now Chuck, no control at all. My father is kissing Roman, and I don't even know what that means. What if my parents get divorced? I have no control over that, and I hate feeling like that. I just wanted to have control over something in my life, even just for a few minutes. So I went into the bathroom stall and made myself throw up, just like the models at my mother's fashion show do" Blair finally finished what she had to say. She felt ashamed for admitting what she had just done out loud.
"Blair…" Chuck didn't even know what to say to her in that moment, he was surprised. For once in his life, Chuck Bass was speechless.
"You don't have to say anything, actually don't say anything, please. Don't ever mention this to Serena, or Nate. Please" Blair was practically begging.
"I won't tell anyone. It's our little secret" He said with a serious look on his face. She had never seen Chuck with such a serious look on his face.
She suddenly reached out and wrapped her arms around his neck, embracing him in a warm hug. She never felt so disgusting, upset, and confused in her entire life. Her world was crumbling around her, and she didn't know what to do to fix it. She was falling apart. And the only thing that felt right in that moment, was Chuck. So she reached out for him and held on for dear life.
She felt his hands wrap around her body and he embraced her in the warmest hug she had ever experienced. She thought Nate's hugs were warm, but she was wrong.
She felt safe and present in Chuck's arms, and she hadn't felt that way all day. She was so grateful for him.
After hugging for what felt like 10 minutes, she felt Chuck suddenly pull away.
There they were, standing in the girls bathroom at Constance Billard, face to face with one another. Chuck and Blair. Blair and Chuck. The first day of freshman year, the first day of the best year of her life. And look where she was…standing in front of Chuck Bass who now knew her biggest secret. She started to feel vulnerable.
Suddenly he leaned in, and kissed her. Right on the mouth. Not on the cheek, or the hand, but right on the mouth.
His lips touched hers ever so softly, and they lingered there for a few moments before he pulled away.
"I'm here for you Blair, you don't have to go through this alone" He looked her right in the eyes and smiled.
Blair was suddenly interrupted from her thoughts and memories of freshman year when Chuck Bass was standing right in front of her saying her name.
"Waldorf" Chuck said with a smirk on his face.