Disclaimer: I don't own anything

Summary: Rory's "First" kiss . Jess lands himself in prison?

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(Rory is 15 and is 6 months away from turning 16)

"Rory, he's here!!!" Lorelai's voice echoed throughout the Gilmore household. Rory walked out of her room, looking beautiful. She wore a pinkish dress with a pink sweater over the top. "My baby's goin on her first date tonight! I feel so OLD!" She covered her face.

"But you still look good!" Rory said trying to brighten her mother's fake hurt spirits.

"Why thank ya!" There was a knock at the door. "I'll get it!! OO, wait! Go upstairs and I'll call you to come down after he comes inside, ok?" Lorelai said pushing Rory up the stairs.

"Mom, this isn't my prom for goodness sakes!"

"Yeah yeah, GO!" Rory walked up the stairs and Lorelai opened the door. "Dean." She greeted as she led him inside and into the living room. "I'll get Rory." She called up the stairs. "RORY!!!" Rory came down the stairs slowly, trying to make it dramatic.

"Wow, you look....nice." Dean said. He didn't have much of an imagination as you can tell. *The only word he could think of was 'nice'.* Rory winced.

"Thank you..." She slipped on her coat, said goodbye to her mother and walked out to Dean's car.

AFTER THE DATE

"I had a great time, Rory." He held her hand as they walked up to her porch.

"Yeah, me too." She didn't really mean it, she was just trying to be polite. Before she could do anything, his lips were on hers with a smothering kiss. She gently backed away.

"Goodnight, Dean." She walked inside and caught her mother looking out the window. "Mom." Lorelai looked up quickly and pretended to be looking for something by the window.

"Danget, I can't find it-Rory!" She pretended to just notice her.

"Mom, you don't have to fake it. I saw you spying on us." Lorelai smiled innocently and then the smile faded quickly.

"All right fine, you caught me....YOU GOT YOUR FIRST KISS!!!!" She squealed. Rory looked down... "What? Was it bad?"

"Mom, that wasn't my first kiss." She stared at her daughter in complete horrific shock.

"WHAT! You've been kissed before and you haven't told mommy about it? Bad Rory!" She scolded.

"I DID tell you about it, mom. Luke's nephew gave me my first kiss." She smiled, just remembering the little boy.

"Well that wasn't a real first kiss! When you get your first kiss, you feel something...like deep down in your gut...that's your first REAL kiss..." Rory nodded quietly and went off to her room. She laid down on her bed, remembering the feeling that she had deep within her gut when Jess kissed her. It was crazy she still thought about him. It was insane for that matter, considering it had been nine years ago...but she could never seem to like a guy because every time she would start to like someone, she would think of Jess. How crazy and twisted is that?

*I wonder what he's doing right now.....*

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Jess sometimes thought about Rory, but not much because he was constantly dealing with his mother's behavior.

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"Jess, where are you going?"

"Out. I'll be back around one." He walked out the door and slammed it shut. His sweet sixteenth birthday hadn't been an entire failure, considering his mother got drunk at his so-called party.

"We have guests!" Liz yelled after him, completely drunk. He shook his head. He hated this, she did this last year. She invited all of her friends and three of his "friends" (who he didn't really know that well) and got completely drunk. She must really hate him. Which wasn't exactly true, but she had no idea how to be a real mother, which pretty much sucked for Jess.

His best friend, Kyle, was throwing him a party down at an abandoned warehouse. He knocked on the large door and it slid open. "Jess!" Kyle yelled over the music and patted his friend on the back. "I told you this would be the biggest party of the year!!" Jess looked around at all these people. He didn't know hardly any of them. They just thought this was a regular party, not a birthday party. Oh well, it was better than being at his own house.

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After most of the people had left, a group of guys came up to Jess and Kyle. Jess recognized these guys, they were the guys he had always wanted to hang out with. They seemed really cool and they were about three or four years older than him. "Happy Birthday, Jess." The 'leader', Tommy, said. "You guys want to hang out with us tonight?" Jess looked at Kyle who had a big smile on his face. The two nodded there heads, trying not to seem too excited. They left the building and got into one of their cars. "Ya know, we always thought you guys were pretty cool for your age. We decided that we're gonna initiate you fellas." The two boys nodded and kind of looked at each other. This could be interesting.

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"Tommy! NO!!!" Jess yelled running towards Tommy and knocking the gun out of his hands. But he was too late, the clerk was laying on the ground, blood spilling from his wound. Tommy and the guys had taken him and Kyle to rob a drug store. Tommy had promised no one would get hurt.....but he lied....the guys tried to drag Jess out of the store, but he couldn't just leave the guy laying there. "We can't just leave!" He yelled, trying so desperately hard to help this man.

"Jess, let's go!" The clerk had pushed a button behind the counter that had automatically called the cops and that was what caused Tommy to shoot him. "Jess!" Kyle yelled. The police came and took the whole group away, including Jess and Kyle. The way the group figured it, Jess was the one who landed them in jail and from then on he wasn't treated very well and unnfortunately, they all shared the same cell.

An officer had finally come and told them that Tommy was the only one that was going to have to stay for the trial because he was the one who shot the guy. Friends and parents paid the kid's bail and the rest of the group left and as they walked out, Tommy reached through the bars and grabbed Jess by the shirt. "You won't get away with this. I'm gonna kill you." Jess pulled away quickly and left, shaken.

There stood Liz outside. "Hey." She reached out and hugged him.

"Don't you ever do that again, do you hear me!" He pulled away and nodded. She wasn't going to punish him...because she really didn't know how to.

A FEW WEEKS LATER

Jess hadn't seen Kyle in awhile and went to find him. He searched everywhere he thought his friend would be. He finally found him....he was hanging out with the guys he had been in prison with. "Kyle!" Kyle rolled his eyes and came over to Jess.

"What do you want?" He asked coldly.

"Kyle, why are still haging out with them? They got us put in jail!" He yelled.

"No, Jess. YOU did! They like haging out with me, Jess! Do you know the last time that someone actually liked hanging out with me?"

"I liked hanging out with you!"

"But you were a dork, Jess! You were the only person that would let me hang out with you!" He yelled.

"I'm not a dork anymore, Kyle."

"Just because you got rid of your stutter and those retarded glasses, doesn't mean that you're not a dork anymore! Just stay away from Jess." He walked off and left Jess. They were obviously not as good of friends as Jess thought they were. He didn't consider himself "dorky" anymore....he thought he was doing a lot better....getting rid of the whole stuttering thing and the big glasses. He guessed he was wrong.

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After that, Jess fell in with the wrong group, and he really couldn't have cared less. He used to be careful of who he hung out with, but now he didn't give it a second thought. He started smoking and drinking selling drugs. He was always paranoid and watched his back, afraid that Tommy was still out to get him for getting him put in jail. He had started all of this crap and then sometime later began to want to get out of all of this... but there was no one that could save from himself...or, so he thought.

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A/N: I'm very unsure about this chapter, I think I kind of rushed it...possibly, but I'm still working on that. But please bear with me! I don't know if this is the chapter that you guys wanted, but I thought that maybe you guys should have a look into what he was getting into before he gets moved to Stars Hollow. Anyway- I'm loving the reviews! Please keep on reviewing!!! thanks!!