A/N: Thanks for clicking to read my new story; please review and comment! This is completely just based on the characters and has nothing to do with the show but I hope you still like/read it. I'm still continuing Once Upon a Second Chance (currently re-editing the next chapter) and Lost memories (re-writing the next chapter). I thought I would take a break and write a short story about this one since I got the idea from a friend.
Chapter One:
Everyday was a boring day for Chuck. He hated going to Yale but he humored his father anyways. People have repeatedly told him that he was very lucky or very fortunate to represent such a prestigious school but in fact he could care less. He was a trust fund kid and that just meant that when the time was right everything would be handed to him on a silver platter.
For the first time he was sitting in Business Economics. After skipping the first class, he received a letter that if he failed to attend anymore classes he wouldn't be able to graduate this year which he sorely needs. So here he was, waiting for class to start. Chuck already signed the classroom attendance sheet at the front of the class. The girls were whispering as they saw him and Chuck leaned back as he waited for class to begin.
"Excuse me, are you Chuck Bass?" the girl next to him asked.
Chuck gave his infamous smile and said "yes I am, and who do I have the pleasure of talking to?"
The girl giggled and blushed as she stumbled on her words.
"I'm.." she began saying.
Suddenly the door opened and the teacher walked in. She swiftly moved down to the front and placed her Lady Dior bag on her chair. Everyone opened their notebooks and was ready to take notes except for Chuck Bass. The girl next to him slid over a folded piece of paper. Chuck opened the paper and read the name "Anna". There wasn't a reason for him to write after that.
Through the whole lecture he didn't write a single word down. It was boring and he knew he wouldn't need to take notes. The teacher noticed his leaned back personality and tried to ignore him anyways. Time went by quickly and soon the class was over. She dismissed the class as she went to pack up her things.
"Is this your first time in this class?" Anna asked.
"Yeah" Chuck said he walked up the stairs to reach the door.
"Did you enjoy it?" she asked.
Chuck didn't really like these kind of small talk conversations. He knew that she was trying to get to know him but she didn't really interest him but he still played along and answered her question.
"It was boring" Chuck said.
"Sorry to have bore you then" the teacher said behind him.
"But you know maybe if you attended class it wouldn't have been as boring" she continued.
Chuck turned around to face her and that's when he noticed how young she really was. It surprised him that Yale would hire someone so young. The other teachers that he had were all old almost his father's age.
"You should keep it interesting next time" Chuck said with a smirk.
"And how would I do that?" she asked.
"I can think of several ways" Chuck said with his devious look as he looked down.
The teacher didn't flinch but instead gave a smirk.
"It won't be as effective as you think. It'll make your head spin so much you'll wish it would stop" she said before walking past him.
Chuck watched as she walked into the crowd. He was intrigued at her response. It was the first time a girl have talked back to him like that. Anna continued to walk with him until she noticed he was leaving the campus.
"Are you not going to your next class?" she asked.
"No, I'm going home for the day" Chuck said as he raised his hand.
Chuck and Nate were at the hottest club in New Haven right now. It would have taken a regular person at least an hour to get into the club but Chuck had special privileges. Money talks in this industry and it was easy to pay the bouncers off. They were by the bar getting a couple of drinks to start the night off.
"How was your class today?" Nate asked.
"It was fine, my teacher was interesting" Chuck said.
"How come?" Nate asked.
"I don't really know how to put it" Chuck said as he drank a shot of tequila.
Across the bar stood a blonde that caught Nate's attention. Chuck looked over and nudged for his friend to go talk to her. Nate was drank another shot and wasn't sure if he should.
"I'm not sure" Nate said.
"Come on where's the Archibald spirit?" Chuck asked.
Nate laughed and drank another shot. He took a deep breath and went to talk to the blonde. Two more shots came and Chuck paid for them. There was a tap on the shoulder and he turned around to see Anna. He handed her the other shot and she gladly took it. They were at a booth doing shots together when Nate came back with the blonde.
"Hey Chuck, this is Serena" Nate said as he introduced his friend.
"Chuck Bass" he said as he lifted a shot in the air.
"Oh, this is Anna" he said.
Anna nodded her head as she poured another shot for the four of them when Nate and Serena sat down. Serena and Nate were getting cozy talking to each other while Anna was leaning on Chuck. He went to the bar to get more drinks when he bumped into the brunette that was in front of him. The girl turned around to look at him and was shocked to see Chuck.
"Great" she mumbled.
"Didn't think they let teachers in here" he said with a smirk as he looked at her tight red dress.
He had to admit she was doing the dress a favor by wearing it.
"For your information, I'm not that old" she said.
Anna came up behind him and grabbed onto his arm. She looked over his shoulder and noticed the teacher standing before her.
"Ms. Waldorf! It's surprising to see you at a club" Anna said with a smile.
"Ms. Waldorf?" Chuck questioned.
"Don't tell me you don't even know your own teacher's name" she said raising her right eyebrow.
"It caught me off guard" Chuck said.
"Right" Ms. Waldorf said.
"Are you two dating?" she asked.
Anna shook her head.
"No we just accidentally met" Anna said.
"Why don't you go back to the booth? I'll be over with our drinks" Chuck said to Anna.
Anna nodded and walked back to the booth.
"So what's your first name Waldorf?" Chuck asked.
She laughed and shook her head.
"Getting down to business as usual Chuck?" she asked.
"What do you mean?" Chuck asked.
"Please, everyone at Yale...no the Upper East Side knows about Chuck Bass. You sure work fast. Isn't one girl enough?" she asked.
Chuck leaned in close to her ear and said "I love that attitude of yours."
"Even if you don't tell me your name, I'll eventually find out" Chuck said.
"It's not that hard" she said with a smirk.
The drinks she ordered finally came and she walked off with them. Chuck watched as she disappeared in the crowd before he ordered his. By the time he came back, Serena was sitting on Nate's lap, and Anna was sitting with her arms crossed.
"Here" Chuck said as he passed along a glass of whiskey.
"Thanks" she said with a smile
Anna ended coming home with Chuck that night. They did it several times but it didn't mean much to Chuck. It was something he needed like drinking water or eating food. He needed some skin contact after drinking so much. But something Waldorf said kept ringing his head that night: "You sure work fast".
