I do not own Gossip Girl or My Fair Lady.

Blair sat on the corner eating her sandwich and watching the nightly call girls. She was waiting for the bus to come to take her to her small apartment in Brooklyn. Her friend Serena came sat with her. Blair had just gotten off of work at the small diner not far from the corner. She didn't make much money but she was saving to go to Yale, she dreamed of being a successful business woman. She was working to take care of her mother who was suffering from dementia. She'd just finished high school and just wanted to go to college to make something of herself.
Serena was also poor but she worked on the corner to get by. She had a rough childhood with many step fathers and an absent mother. Lily Van Der Woodsen left her daughter and her son Eric Van Der Woodsen alone with her many husbands and they would abuse the children instead of actually watch them.

Blair and Serena were best friends and helped each other whenever they could. Blair wanted to be powerful and Serena wanted to be famous. They were going to help each other get to where they wanted to be. Blair had just finished her sandwich as Serena told her about one of her clients that was very rich and cute, whom she like a lot, when a sleek black limo pulled up in front of them.

Chuck and Nate where riding around looking of entertainment for the night. It had been a long day and they needed to unwind. Chuck had to get the board of Bass Industries after they found out about Eva. She was the closest thing to a girlfriend Chuck Bass ever had, and the board was happy until the scandal broke out that she was a prostitute.

Nate and the Spectator were behind on the news of the Upper East Side. He would've been the first to report about Eva being a prostitute but he and Chuck have been best friends since they were children, he couldn't do that to him. So he was the second to report the news after having Chuck's blessing but that wasn't enough to get him more readers. He had the inside exclusives of Chuck Bass' live and famous parties but with Chuck's wild partying ways being frowned upon by the board they were becoming less and less. He need a miracle to happen like Chuck Bass having a girlfriend.

They were pulling up on the corner where Nate's favorite girl Serena worked, Nate had a crush on her but he was so busy with the Spectator that he didn't have time for a girl friend and he wasn't sure if Serena liked him back. She was a prostitute but he knew of her hard life and how she was struggling. He would pay her double and buy her gifts and things she needed. Nate was more than happy to be seeing Serena tonight, he was going to ask her to stay the weekend. He noticed that Serena was talking to a brunette girl and turned to Chuck. "Hey man, Serena has a friend. She's not blonde but I'm sure she'll do for the night."

Chuck looked at the brunette that Nate was referring to. She was about five foot five, had chocolate-brown curls that hung to the middle of her back. She was dressed in a pink polo shirt and a blue skirt, it wasn't anything slutty but it made Chuck hard just looking at her. She had her face turned away from them talking to Serena but Chuck was anxious to she Serena's mystery friend's face.

Serena noticed that limo right away. "Oh look that's him right there. It looks like he has Chuck with him tonight."

"Who's Chuck?" Blair asked.

"Nate's best friend."

Just then the window rolled down and both girls turned to the limo. Nate called out to Serena, "Hey beautiful."

She smiled brightly, "Hey yourself handsome. What's on the menu for tonight?"

"Well I was actually thinking we'd get lost this weekend, I had a very hard day at the office today."

"Sure thing Natey." Serena grabbed Blair and pulled her into the limo before she could even protect.

Serena jump into the seat next to Nate and kissed him, like they were just a regular couple. Nate was the only one allowed to kiss her. Blair however landed face first into someone's lap. Her mouth came into full contact with what she could only assume was someone's cock and from what Serena told her earlier she guessed it belonged to Chuck.

Blair looked up to meet a shocked Chuck's face. He quickly masked his emotions though and looked down at Blair. She was beautiful, her lips were ruby and pouty. Chuck just wanted to kiss them. Her eyes were big and brown, he got lost into them. She looked like a porcelain doll.
Chuck snapped out of his observing to pull Blair up off her knees of the limo floor and on to the seat next to him. "Well that's quite the first impression", he said with his signature smirk. "I'm Chuck -"

As soon as he smirked Blair knew she knew him. He was always in the newspapers for his womanizing ways and wild parties, and because of his billion dollar company. He was a powerful man who just took it for granted. He was a play boy. Blair took this opportunity to tell him just what an ass he was was. "Bass", she finished for him. "I know exactly who you are."

"Oh do you now, I'm not surprised. I am very well-known." He smiled.

"You're known for sleeping around, boozing, and doing other debauchery."

"What's wrong with that?" Chuck asked genuinely curious. Nate and Serena were just looking at their friends with amused looks on their faces.

"What's wrong with that?! You have the potential to be much more powerful than you are but you choose to waste your money and influence on nonsense!"

"Says the hooker."

"I am not a hooker!"

"Then please enlighten me. What is it that you do?"

Blair looked down at her lap while Serena looked away and Nate and Chuck looked at her. "I'm a waitress", she said quietly. Nate busted into laughter while Blair lifted her head high holding back the tears. Chuck then noticed the name tag on her shirt. "Well Blair, I'm sure bringing people their food and cleaning tables really qualifies you to give me advice on how to be a powerful and respectable man."

Just then Nate had an idea. "Wait a minute, Chuck she's right."

Chuck glared at his friend, "What do you mean she's right Nathaniel? She has no idea what she's talking about.

"Chuck the board told you the exact same thing."

"Okay they did, but so what?"

"Blair can help you."

"The only way the waitress can help me is on her knees or in my kitchen." He turned to Blair, "Which would you prefer?"

Blair turned bright red, "Neither! I want nothing to do with you, you Basstard. I may just be a waitress but I'm smarter than you and if given the chance I'd be just as powerful as you if not more."

Nate shook his head and put his face in his hands. "Chuck would you just please be nice."

"I play nice, in the bedroom... sometimes."

"You're a heinous man, you're going to lose your Empire and have nothing" Blair said to Chuck.

Chuck turned to her with a hard look, "What are you even doing here? If you aren't going to get me off you can get out of my limo!"

"Fine!" Blair screamed.

Serena looked to Nate with a pleading look, "Nate stop him please, she's my best friend. Don't let him kick her out on the street."

Nate looked to his best friend with a sigh, "Chuck man look, she could help the both of us."

"How could she possibly help us Nathaniel? Please elaborate."

"Okay just hear me out on this." Nate took a deep breath. "You need to impress the board and improve your ways right?"

"Yes Nathaniel, I'm aware of this. Get to the point."

"Well the point is having a girlfriend would do that."

Chuck glared at Nate, "I'm Chuck Bass, I don't do girlfriends! Even if I did why would I choose a waitress?"

"You have enough money and power to turn her into a powerful business woman. A woman who the board members would love to see you with."

Chuck looked at Blair, who was watching them and hanging on to their conversation. "Why would I want to tie myself down exactly?"

"Because from the way things are looking you're going to lose Bass Industries and if that happens you won't have much money to party with."

Chuck thought about that, he knew Nate was right. Serena who was quiet the whole time turned to Nate and asked, "How does this help you?

Chuck looked at Nate and waited for an answer too. "Well the personal details of Chuck Bass' personal life will have all of Manhattan reading the Spectator. Chuck Bass with a girlfriend, no one will see it coming."

"Does that mean that we can be together if this goes well?" Serena asked hopefully.

Nate smiled, she actually wanted to be with him. "Yes, if things go well and as I hope it will Serena I would love for you to be my girlfriend."

Chuck looked between his friend and Serena and he looked down to his lap. They were in love, and they needed him to put his womanizing aside to be together. He loved Nate like a brother and would do anything for him, and if that meant having a girlfriend he'd do it. Especially since it would be helping him in the process.

Chuck looked at Blair who was looking at Nate and Serena. She wanted someone to look at her that way. She wanted to be in love like her friend was. There were a lot of things she wanted. Blair wanted to sleep in a big bed and lay on someone's chest while they played with her hair. She wanted to eat macarons before bed while he drank a glass of scotch. She wanted to have a closet full of clothes, jewelry, shoes, and purses. She wanted a powerful man to hold her at night and make her feel safe. She wanted to fix someone's tie in the morning before they headed to the office. There was just so much she wanted, but it all seemed like a dream. She was just a waitress barely getting by but if pretending to be an asshole's girlfriend would give her friend the chance she needed to be with the man she loved, she'd do it.

She looked at Chuck to see him looking at her. "Well I'm willing to do this if you are, but there must be some rules."

"Rules?" Chuck looked to Nate and Serena and sighed, "Fine rules."

"I want to go to Yale, and I'm going to need somewhere for my mother to stay."

"Yale, fine. That'll look good with the board. As for your mother, I own a hotel she can stay at the Empire everything on me."

"Where will I stay?" Blair asked quietly.

"You'll stay with me of course. If you're going to be my girlfriend you're going to have to be groomed and taught my lifestyle."

"I have to stay close to my mother, she's sick and she doesn't have anyone else."

Chuck sighed and rolled his eyes, "She can stay with us in the penthouse there are plenty of rooms, and since you won't be working anymore I'll pay for anything your mother needs."

Blair smiled at this. Eleanor would have everything she needed and Blair will be attending Yale. "One more question for the night."

Chuck waited for the question. Blair went on, "Will I have my own room?"

Chuck laughed. "Blair dear", he said in a mocking way "you will be staying in the master bed room with me."

Blair looked down and told herself she could do this. Serena's happiness, her dreams, and her mother's security rested on this.

"Fine but I won't sleep with you."

"I'm your boyfriend, you will but I promise you that you'll want it before we make hot passionate love."

Blair scoffed, "Okay take me home now."

Chuck pressed the button for the speaker to Arthur. "Arthur let's bring Mr. Archibald and his guest home then we're going to go to Ms. Blair's and collect her mother and a few things."

"Yes sir", Arthur replied faithfully.

Blair looked at him questionably, "Why tonight, it's late?"

"We're going to get started as soon as possible, we have a lot to cover before you meet the board or go off to Yale."

Blair just nodded and sat back. Serena and Nate looked excited as the limo dropped them off at Nate's. Blair was feeling nervous about being alone with Chuck, especially since they just met. Blair told Arthur her address and they were off to her apartment building.

Chuck just sat quietly looking out the window the whole ride. When they finally arrived he finally spoke. "Please be quick, I'm rather tired. Just pack clothes for tonight and tomorrow and I'll send someone over to get the rest of your things tomorrow."

"That won't be necessary, I'll just get my mother."

"Fine, that would be best. You can go shopping for you and your mother tomorrow morning while I'm at the office. Just go get her, and I'll call and have one of the guest bedrooms set up for her and have a nurse to come and sit with her if that's necessary..."

"Thank you but she has a nurse already."

Blair got out of the limo and went up to her apartment. She greeted the nurse, "Hey sorry I'm late but something important came up. I'd like to talk to you about that."

"It's no problem Miss Blair", her mother's nurse Dorota answered.

"Dorota my mother and I are going to be moving and I'd like to know if you'd work with her there."

"Of course Miss Blair, Miss Eleanor is good to watch."

"Thank you Dorota, but could you do me a favor and help me get my mother into the limo downstairs?"

Dorota looked confused, "Limo? Why you take Miss Eleanor in middle of night?" Her mother's nurse, who was like a second mother to her, raised her eyebrow in a questioning manner.

"Dorota I really don't have time to explain but I'm taking my mother somewhere nice."

"I know you're up to something and I find out."

"Okay well you can find out at a later time, just help me get my mother downstairs and in to the limo."

Dorota dropped it for now and helped Blair get the angry Eleanor into the limo. Chuck looked amused as Eleanor fought with her daughter and the nurse for having her out in her night-gown and robe. Once they were in the limo Chuck rolled down the window and spoke to Dorota.

"Hello I'm Charles Bass, Blair's boyfriend" Chuck looked to Blair "I'll be taking Blair and her mother to live with me at the Empire and I'd appreciate if you'd come to watch over her dear mother. I'd pay you double your salary now of course."

Dorota looked at Chuck suspiciously, "I don't know."

"I promise you..." Chuck waited for a name.

"Dorota."

"Dorota, Blair and her mother are in great hands. I'll make sure they are both well taken care of. You can see to that yourself."

"I be there 7 am sharp."

"Okay, well I leave for the office at 6 so I'll have Blair call you up or tell security you're coming. Thank you for accepting my offer." Chuck kissed the back of Dorota's hand.

Dorota smiled at Chuck then at Blair. "Bye Miss Blair, Mister Chuck." Then she turned and walked away.

Chuck rolled the window up once they saw that Dorota was safely in her car. Chuck then turned to Eleanor who was sound asleep. "What's wrong with her?"

"Dementia", Blair said sadly.

Chuck just nodded and took off his coat and draped it over Eleanor. Blair looked down into her lap and blushed, "Thank you."

"You're welcome Blair, it's the least I can do. You're my girlfriend now, it's my job to keep you safe and take care of you. Pretend or not, now let's go home."

They drove to the Empire in silence. When they pulled up to the hotel Blair was in awe.