So here's a new story. This one's a bit ambitious. I started writing it because I wanted to see Rory in some more racy situations. Something I think everyone enjoys. My goal is to see a different kind of Rory while still maintaining her character. A basic summary is the following: Chilton Academy is a very prestigious private school in a secluded location. Everyone from the show goes there, whether they are the elite class or scholarship students. Rory struggles to fit in, but finds herself on a rollercoaster ride through the world of old America wealth. Any hookups are possible. Let me know what you'd like to see.

This is just an introduction to the story. Not too exiting, but it holds the promise of oh so much more!! Enjoy and Review!

Chapter 1

Rory watched as her mother's jeep drove away leaving her to fend for herself in a foreign territory that she was born into. Chilton Academy. The words were engraved in the stone above the archway that led to the entrance of the school's main building. Chilton Academy was the best of the best so far as private schools were concerned and it was going to be Rory's home for the next two years. It attracted some of the biggest family names in America. It was a world that until recently Rory had never been apart of, but was suddenly finding herself in a whole different kind of ocean; one made out of money. She really didn't enjoy being out of her element. She sighed and headed back into the building.

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All the students had their own rooms. It's customary for this type of school to have some sort of roommate system. That's how they show it in the movies, right? Wrong. Completely wrong. Rich kids insist on having their own rooms. How could they be asked to share a space containing all their belongings? It would be far too intrusive. Besides, the amount of closet space that would be needed is unimaginable. But it created the dilemma of meeting people. Rory finally rolled over and pushed herself off her bed. It was finally late enough for her to go to dinner. She vaguely remembered the location of the dining hall from the tour earlier that day. No one on that tour had heard much of what the guide said. Between her mother whispering all kinds of naughty comments in her ear and Emily Gilmore casting disapproving looks upon both of them. Which in the end only makes them laugh harder.

She could hear the noise of hundreds of teenagers coming from the other side of the large mahogany door. She pushed the door open and was instantly overwhelmed with delightful aromas. Had the guide mentioned anything about five star food? Rory tried to blend in, but as a silence fell over the hall she suddenly felt awkward. Staring at her were hundreds of students dressed in black robes. How many times can the tour be blamed? Dining robes were an age-old tradition popular in old money schools like Chilton. In the new age, however, students had rallied it down to Sunday night dinners only. Apparently Rory had forgotten what day it was. This definitely can't be blamed on the tour. She looked down at her plain jeans and black t-shirt remembering when she had been worried about meeting people. And then it happened. It came from the back of the room. A single whistle followed by stifled giggling. She was so humiliated. Rory focused her eyes on her shoes trying to hide the redness of her face as she picked up a plate at the buffet.

Rory chose a completely random table in the entire dining hall. Grabbing a chair at the end of a table where a couple students had cleared out. She sat down and pulled out her book. As she was about to take a bite Rory was interrupted.

"Are you lost?" It came from the cold high-pitched voice of Paris Gellar, also known as la crème de la crème. Rory looked up and the blonde sitting a few chairs down was staring directly at her. Her eyes held a heat that said they were ready to burn.

"I'm sorry I wasn't aware…"

"It's obviously not the only thing you weren't aware of," the girl interrupted, slowly looking Rory up and down sneering at her outfit. "We have a tradition here. It would be appreciated if you could remember that next week."

"Oh, leave her alone Paris. We all know it's a silly mundane tradition that we agree to partake in to appease our parents, because if we didn't there would be nothing to distinguish Chilton from imposter nouveau riche schools." Rory looked to the boy sitting across from Paris. He wasn't tall, dark, and handsome, but he was certainly a blonde brooding bombshell. "You must be the infamous Rory Gilmore," he continued. "I'm Logan Huntzburger. My parents told me about you. They're friends with you're grandparents."

After hearing the name the other few kids sitting at the table had turned to stare at Rory.

"Yea, I am," she replied. "It's nice to meet you. I wasn't aware that I was infamous."

"Daughter of Lorelei Gilmore. A name only heard in whispers for the last sixteen years amongst our social group," explained Logan. He stood from the table and the others followed suit. "I guess we'll see you around Gilmore."

"Hopefully not too soon," said Paris getting the last word in. They left the table and Rory's eyes followed the group as they left from the room. Other students were sure to move out of their not wanting to come into a confrontation with them. Was this the world her mother had run away from? They had been expecting Rory, but she had not known any of their names. For the first time in her life Rory silently cursed her mother for not providing her with proper preparation. She had no idea how to fit in with these kind of people.

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The next morning Rory found herself rushing to get ready after sleeping through her alarm. Twice. Thankfully during the week the students were required to wear uniforms, simplifying the entire morning process of getting ready. She ran across courtyard after courtyard finally making it to the school building. The hallways were nearly empty by the time she arrived. Suddenly Rory, tripped dropping the books she was holding. She bent down to pick them up annoyed that she was going to be even more late.

"Now that is a lovely ass. And one I have not yet seen," said Finn with his thick accent. Rory became very aware of her position and she slowly came back up to standing completely flustered. "My lady," he said falling to one knee before her. "I would willingly be your slave. To do with as you wish. Or to let me do to you what I wish," he brought her hand to his mouth laying one soft chaste kiss on it.

Rory stood there stunned into place from the over dramatic declarations by the Australian guy in front of her. Tristan Dugrey, the blonde boy he was accompanied by, was doing all that he could to not laugh. Rory felt something moist against her finger and she looked down at the boy on his knee shocked to see his lips wrapped around one of her fingers. She quickly pulled her hand away stumbling backwards, almost falling over her own feet. This only caused the blonde to laugh harder, almost mockingly.

"Sorry Finn, looks like she's a Mary," said Tristan as his laughter quieted.

"Excuse me?" Rory said assertively addressing Tristan.

He took a step towards her, "I said you're a Mary," he repeated with smirk that some how extended from ear to ear.

"Well I guess you really wouldn't know that," Rory mumbled angrily.

He closed the remaining space between them. Licking his lips, Tristan looked down at her, "if you want to prove me wrong right now," he said in a low voice moving his head closer to hers, "I'll let you." The words lingered and played along her skin. The promise they held teased her ears so sweetly. Rory could feel his breath warm on her face as alarm bells went off in her head and she quickly stepped away from him regaining her personal space and composure.

"I have nothing to prove to you," she said.

"If you say so, Mary."

"Rory."

"What?"

"My name is Rory. Not Mary."

"And what a lovely name it is. Much better than Mary if you ask me," interjected Finn.

"Well no one asked you," said Tristan never breaking eye contact with the brunette before him. Rory only narrowed her eyes starring back at him. Tristan finally broke the silence, "lets go Finn. We need to get something eat before class." And with that the two boys left Rory alone.

Rory let out a breath she had not been aware she was holding. As she did her stomach simultaneously did somersaults and her skin was burning. For the first time Rory wondered how she was going to survive school. It was always something she had excelled at, but this was a whole different kind of school and she wasn't sure she was ready. It had only been two days and Rory had already experienced two confrontations. That's two more than the rest of her life. Rory had come face to face with her mother's world. It felt like being thrown into the middle of a violent storm. It was unpredictable, unfriendly, and inescapable.

So there you have it. I will be introducing more of everyone's (not so) favorite characters. Let me know what you want to see happen. I always need the feedback.

See you soon,

Amy