Undercover Love

By: RoxyRoo

Disclaimer: I own nothing.

Summary: It was Officer Tristan Dugrey's first undercover mission. To uncover the drug lord of private school Chilton. Nothing was going to get in his way of completing this mission... Trory AU

AN: I changed my mind, Rory is 17 in this story. Tristan is still 22.

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Chapter Three

Tristan stared out at the kids from his perch against his locker, as they hustled around grabbing books for the first class of the morning, chatting with friends, finishing last minute homework, ect. It was already Friday. He had been attending Chilton for a week now, yet was no where closer than when he first started to finding the culprit.

In his quest to find loners, he found there were not really any in the school. Everyone seemed to have their own group that they kept to. Being a prep school that wore uniforms, it was not like he could tell which kids were the bad seeds by how the kids dressed. Usually trench coats, were a dead give away to bad guys in movies. But here at Chilton, it was against their dress codes. Everyone dressed the same.

He found out pretty much everyone at the school was rich. He found it interesting that Rory Gilmore was not rich though, yet attended Chilton. From his investigating from his hack of school files in his off hours, he found that it was her grandparents who were paying for her to attend Chilton, as her mother was an inn keeper. She sort of fitted into the loner type. Sure, she hung out with the rich kids like Huntzberger, but at lunch even though she sat with them, she seemed in her own world with her books. He could not help but watch her during class occasionally. He even got in trouble in one of the classes for finding her ear so interesting, as one of the teachers said. This had caused her to turn beet red and to avoid him since.

He found her intriguing. Rory Gilmore was the exact type of girl that Tristan Dugrey always sought after. Quiet, innocent, smart. He had to keep reminding himself that she was only 17, so she is jail bait. Plus he could not get mess up while on a mission. It would be unprofessional of him.

The party was tonight, which he was hoping would help give him some more leads. It was being thrown by Albert Duncan, who seemed to be a bit of a trouble maker along with his sidekick Devin Bowman. Both of which were two on Tristan's radar.

As the bell rang, Tristan sighed, pushing himself off of the locker to head to his first class.

-

Tristan rested his head on his hand, as the English teacher passed back the assignment the class turned in the day before. He barely glanced at the failing grade on the paper, before turning his attention back to the picture he was drawing in his notebook.

He had already graduated from high school, so he saw no need to bother doing anything extra in the classes. His time when he was not in class was not going to be wasted on homework, at least schoolwork, that he did not need to do in the first place.

-

"Class," Mr. McLean said, after he finished passing out all of the papers. "This next assignment, I am going to pair you off in two's. It is your senior year. Some of these kids in your class, you might have known since kindergarten, yet never bothered to really know. I have been observing you all this last week, and will be teaming you off with people I feel you know the least about. What will you be doing? You will be getting to know each other. You are to learn everything about the person you are teamed up with,
then write a paper on them."

Mr. McLean paused to make sure the class was with him. "It's up to you and your partner for when you decide to get together. This will be worth 50 percent of your grade. Now, for the pairs," he glanced down at his paper, before calling out names. "Harper and Kellar, Dills and Welch, Gellar and Mueller."

Rory bit her lip. Paris and Brad. That should be interesting. She glanced around the room, wondering who the teacher would pair her with. Her gaze landed on Tristan the next row over, back a bit. Her eyes narrowed. She better not be paired with him. She had a clear view of his paper, and a very clear view of the grade on it. She turned back to the front, as the teacher went on with the names. It was obvious that he was a slacker. He always seemed to be doodling in his notebook during class.

"Marche and Travis, and our last pair Dugrey and Gilmore."

Rory's head snapped up at the sound of her last name. She turned around to see Tristan also looking up, he smirked at her, as she narrowed her eyes in a glare.

"Class dismissed," Mr. McLean said, as the bell rang.

Rory quickly gathered up her books. She looked up to see Tristan leaving the room, and quickly rushed after him.

"Tristan, wait!"

Tristan paused out in the hall, looking down at her, with a raised eyebrow. "Yeah?"

Rory narrowed her eyes, at his careless attitude. "Look, I need a good grade on this assignment, and I'm not going to let some slacker who would rather live off his daddy's money all his life keep me from my chance of going to Harvard."

"Slacker?" Tristan asked in an insulted voice. If she only knew, he was the farthest thing from a slacker. Straight A's all through high school. Valedictorian. Honor student all the way.

Rory grabbed his paper from him, holding it up for him to see. "Slacker," she repeated, as he smirked. "Now we're going to plan a time to get together. You want to do this tonight?"

"Can't," Tristan said. "It's Friday night. I'm going to a party."

Rory rolled her eyes. "Of course."

Tristan smirked at her. "You're not going?"

Rory shrugged her shoulders. "Don't know yet."

"Look, tomorrow is Saturday, so why don't we get together then, that way we have all day for this project," Tristan offered. Even though he had vowed not to do any homework through this mission, he knew he could not just let her fail on account that he was not a real student.

"Alright," Rory said, nodding her head. "Where at?"

"My place isn't good," Tristan immediately said. There was no way that he wanted her to see his apartment that was obvious only one person lived in it. "How about yours?"

"I live in Stars Hollow," Rory said. "About thirty minutes from here. We could meet at Luke's."

"Luke's?" Tristan asked with a raised eyebrow. A boyfriend?

"Luke's Diner, best coffee in the world," Rory said.

Tristan nodded his head. "Alright, works for me. Meet you at 10:00 am?"

Rory raised an eyebrow in surprise. "Are you going to be awake enough after the party to meet that early?"

Tristan shrugged, as he turned to walk off. "Hey, I thought you said that this place has the best coffee..."

Rory could not help the small smile, as he walked away. She was just glad his back was to her to not catch it.

-

Rory sighed, as she parked her mother's jeep down the street from the party. The block was already filled with cars. Stepping out, she could hear the music pounding. She shook her head. She did not even want to be here. She was only here for one reason.

Paris.

Paris just had to beg her to come. Ruining her plans of curling up with a book for the evening. She tried to use the fact that she had Friday night dinner, however her mother just had to say that she would have her date for the night pick her up at the grandparents so Rory could have the jeep for the night.

She sighed, starting on the trek to the house. She hated Chilton parties. It was just the same people she saw every day at school. She was not a party person. But neither was Paris, whose mother forced her to come to these events. She needed someone to stand around with, being bored.

Once inside the house, the music just became worst.

"Love!"

Rory turned around.

"Finn!"

"So I see Paris talked you into coming, ehh?" Finn asked, wrapping an arm around Rory, his other hand holding a cup that Rory was sure was not lemonade.

Rory rolled her eyes. "Speaking of which, have you seen her anywhere?"

"Nope, don't think the doll is here yet," Finn said as he led her through the house.

"Great," Rory muttered.

"What? Don't want to spend some time with Finn?" he pouted.

Rory rolled her eyes. "You know I love hanging with you. Never a dull moment..."

"Good, now spank me," Finn said, as he bent over.

Rory's eyes became large. "Finn!"

"Oh come on Rory! I'm trying to make that red head over there jealous," Finn motioned in the direction with his head.

"Finn, were you just using me?" Rory asked, acting insulted.

"Never darling... but Louise refused to make out with me..."

Rory's jaw dropped. "So what, I'm your second choice?"

"No!" Finn said, violently shaking his head, spilling some of his drink. "I just found you before Madeline!"

Rory rolled her eyes, before walking away.

"Rory!" Finn cried as he trailed after her. "You're suppose to be making her jealous, not making it look like we're having a lover's spat!"

Rory could not help the smile on her face as she continued walking away from Finn. She had just caught sight of Paris.

"Hey, Paris," Rory said, as she reached her. She looked behind her to find that she had already lost Finn with his short attention span.

"Hey," Paris said, spinning around.

"I thought you would have been here earlier, with how your mom is."

"I was taking a piss," Paris said as they went over to the refreshment table, each grabbing a bottle of water.

"Well, just to warn you, watch out for Finn," Rory said as she twisted the lid off.

"Now what is he up to?" Paris asked with a roll of her eyes.

"Trying to make some red head jealous... He asked Louise to make out with him... And me to spank him."

"Did either of you?" Paris asked with a smirk.

"No!"

"I'll kick his ass, if he wants me too," Paris said with a sly grin. Rory grinned back, as they walked to the back porch.

"I think he knows better than to ask you, after last time..." Rory laughed.

"Look at him now," Paris pointed out where he was on his hands and knees begging Madeline who looked like she was seriously considering it.

"Oomph!" Rory said as she ran into someone, strong arms reaching out to steady her. "I'm sorry, I wasn't looking where-" She looked up startled to see blue eyes looking down at her. "I was going."

"No sweat," Tristan said with a smirk. "Thought you weren't coming?"

"No, just wasn't sure if I was going to," Rory said, folding her arms in front of her. "I'm just here to keep Paris company."

"At a party?" Tristan chuckled. As he followed both of them outside.

Paris rolled his eyes. "Is there a reason for you to be following us?"

"Blunt person, huh?" Tristan asked amused.

"It's called stalking," Paris said in an annoyed voice.

"Anyways," Tristan said, trying to change the subject. "Have either of you seen Bowman or Duncan?"

"What would you want with those losers?" Paris asked.

Tristan shrugged his shoulders. "Just need to find them about something."

"I think I saw them heading upstairs earlier with a few other people," Rory said.

Tristan nodded his head. "Thanks, nice chatting with you Paris, see you tomorrow Rory" he winked at her as he walked away.

"Thinks he's God's gift to woman," Paris mumbled, as Rory felt her cheeks tinge pink.

-

Tristan shook his head as he went up the steps two at a time, wanting to rid Rory Gilmore out of his head. It was bad enough that he had to spend all day tomorrow with her, but for her to show up at the party that was important for him to be completely focused on his job? Not just that, but to literally run into him? He really wished that he had not been paired with her in class. This assignment was just going to make it so much harder on him.

He sighed, as he reached the top of the stairs. He went to the first door, to listen to see if there was anyone in there. He was getting ready to move onto the next door, as it suddenly opened, Bowman, Duncan, and a few other people came tumbling out of it.

"Thanks man," a blonde boy said to Duncan, as he handed him some money. Him and his friends then turned to go downstairs.

"No prob," Duncan said as he leaned against the wall. "There's more where that came from."

"Hey," Tristan said, as the other group was leaving. "Great party."

"Thanks," Duncan said as he went back into his room. He shoved his dresser drawer shut, shut the light off, locking the door, before him and Bowman headed downstairs.

Once they were downstairs all the way, Tristan looked around to see if anyone was watching, before pulling a lock picking kit from his pocket. He quickly picked the lock open, before slipping into the room.

He could not believe his luck. Had he actually found his culprits this early into the case? Could he get out of high school?

He left the light off, so no one would be able to see him from outside. He pulled a small flashlight from his pocket, shining it around the room. He shined it towards the dresser Duncan had been into, before pulling the drawer open.

Several comic books laid in it.

"What the," Tristan grumbled, sifting through the drawer. He stuck the flashlight in his mouth, as he took all the contents from the drawer out, finding nothing but comics books in it. He even open the books, to see if anything would fall out. No luck.

He put everything back into the drawer, hoping that it was how he found it. He did a quick look through the room, to see if he could find anything else in the room. Maybe it was a different drawer. Or under his bed.

"Shit," Tristan grumbled running a hand through his hair, before he finally left the room. This was going to be much harder than he expected...

-

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AN: I'm back... I know, I've been gone for awhile... I'm sorry! Just been super busy... Plus not quite in the mood to write... Still super busy, but was in the mood to write today!

I answered a bunch of the questions on this story in my blog awhile ago. You'll have to scroll down several messages ago to see them though. Incase you didn't catch my AN at the top of the page, I changed Rory's age to be 17. Tristan is still 22.

Anyways, hope you all enjoy, and hopefully I'll be able to keep this writing mood for awhile... Thank you for all of the reviews for the last chapter! I could not believe how many came in for it! You guys are so awesome!