Title: First Time

Author: Gilmoregirl7878

A/N: ANOTHER story. I know, but I couldn't help it. I'm completely stuck with my other stories, so I had this idea swimming around and decided to go for it. As per usual, I warn you that the first couple chapters will be short. But they will get longer.

THINGS YOU NEED TO KNOW BEFORE READING:

1. Rory is in her Senior year.

2. Everything with Dean and Jess happened, but Jess and Rory started dating during the summer, after the wedding because Rory didn't go to Washington D.C. with Paris.

3. Rory is kinda innocent, just not as much as the Show, during the beginning of the story, but that will change. Trust me. Haha

I think that's all you need to know right now, I might add a couple more at the bottom of the page if I think of more.

Enjoy, and tell me what you think!

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Rory Gilmore was lonely.

Her Mother, and best friend since the day she was born had just left to go back to Connecticut.

Leaving her in California, to live at boarding school.

Getting into West Coast Preparatory Boarding School was a once in a life time chance. After many long talks with Lorelai, she decided to go and try it, even if it was just for a semester or two.

You should have seen how mad Paris was at her when she told her she couldn't be Vice President.

So, here she was, across the country away from all the people she knew and loved, her mother having just left to catch her flight back to Hartford.

This was a first.

She decided to push all of those thoughts out her head and get unpacked, she first got dressed into comfier clothes, choosing her boxer shorts and halter, not used to such a different climate.

She set up her computer so she could listen to her music while she unpacked. After she had put her seats on her bed, hung up some of her posters, and was now putting her clothes away.

She had her music very loud and could barely hear anything else, she was trying to drown out all insecurities and fears about starting a new school and having live there, too. What if her roommate was like the bitchy girls at Chilton or worse? What if she failed?

Jess.

The music helped stop those thoughts temperately.

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Tristan walked into Stephanie's dorm room, looking for her. School had just officially ended and he was supposed to meet her here because they were going to go out tonight, Friday night.

When he entered he immediately heard Hands Down by Dashboard Confessionals. He thought, at first it was Steph blaring her music, but it was coming from the wrong room, plus Steph tended to listen to more hip hop artists, like 50 Cent.

He looked into the other dorm bedroom next to Stephanies', and saw a very beautiful girl slightly dancing to the music that was playing and unpacking, it looked like.

She was defiantly Steph's new roommate that she was expecting, and she most defiantly wasn't from California.

She had elegant pale complexion, something that most West Coaster's didn't have. She was defiantly beautiful, and she hadn't even turned around for him to know that.

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Rory was absorbed with her own thoughts she didn't realize that there was a very good looking blonde watching her, when she did, she jumped and froze, causing the blonde to smirk at her.

She walked over to her computer and turned down her music, when she turned around to face the blonde, she blushed to see that he was checking her out from behind, and was being blatant about it.

"Can I help you?"

Tristan leaned up against the doorway, smirked, and looked her up and down again.

"Maybe.." He said suggestively.

"I mean, what are you doing here, in my room." Rory asked rolling her eyes.

"Well, I'm Tristan, Tristan DuGrey." Tristan said, walking over closer to her, causing her to take a step back when he came a little to close.

"I'm Rory Gilmore."

"I've heard of you before. You're from Connecticut, right?" Tristan asked.

"Yea..."

"So am I. I've met your Grandparents, Richard and..." Tristan trailed off trying to remember Emily's name.

"Emily." Rory supplied.

"Yea, Emily. They had this party and I was forced to go with my parents one time during the summer. I don't remember seeing you though, and I defiantly think I would remember you." Tristan suggested, giving her his oh-so-charming smile.

"I haven't gone to a lot of their parties." Rory said, not wanting to elaborate.

"Why not? I thought little rich society gi-

"I'm NOT a rich society girl!" Rory declared.

"You're a Gilmore." Tristan just said, for that explained everything.

"So? You don't know anything about me." Rory challenged, causing Tristan to look at her surprised. He was about to say something when Steph walked in.

"Hi! I'm Stephanie! You can call me Steph though, you're Rory, right?" Steph said perkily. Walking past Tristan and hugging Rory, talking fast and excitedly.

"Yea, I'm Rory, I guess I'm your roommate now." Rory said smiling at the perky girl.

"Oh, Tristan. What are you doing here?" Stephanie said, just noticing him.

"Meeting Ms. Gilmore here." Tristan said, not taking his eyes off Rory.

"Well, now you did, so you can go now, I want to have some girl talk with Rory to get to know her and we can't have that with you here. Even though you take about an hour to take a shower." Steph told him pushing him out of the dorm room.

"Bye Mary!" Tristan called before the door shut behind him.

"Oh god, he called you Mary." Steph groaned.

"We just met, it's okay if he calls me by the wrong name." Rory said confused.

"No. You don't know Tristan. He's my cousin, unfortunately." Steph joked, really being very close to him like brother and sister.

"Oh, what did he mean then?" Rory asked innocently.

"It means he thinks you innocent, like the virgin Mary." Steph explained.

"I'm not..."Rory trailed off seeing Steph's disbelieving face. "Okay, so maybe I am a little."

"See, there's more to it though, It means that you, are his newest conquest. Welcome to California." Steph told her, smirking.

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A/N: Wow, kinda long for the first chapter. Usually its like half the length of this. So, You all can probably guess the pairing by now, but I'm not sure. That was Tristan just being...well Tristan. I really liked this chapter, I have some great ideas for this story, so I'll probably be updating it frequently, if you guys like it. Do you like it?

Anyways, I just wanna have a poll and see what you guys think the pairing should be. I might not do what you all want, but I'll take it into consideration. BUT before you vote, please just do this one thing. When you're voting, please think not just who your favorite guy is, but ALSO who you think would be the best pairing for this story.

A. Tristan.

B. Logan.

C. Finn.

Please don't but a D and a different person, just those three.

Anyways, Hope you liked it, I did. Please review and tell me what you think!