Title: Rory's Boy

Author: Michaelover101

Summery: Tristan's friend comes to visit and some surprising feelings arise. Based on the song Jessie's Girl by Rick Springfield. Trory

Rating: M

Disclaimer: not mine

Beta: Flynn

Jessie is a friend, yeah

I know he's been a good friend of mine

But lately something's changed

That ain'y hard to define

Jessie's got himself a girlfriend

And I want to make her mine

Chapter 1: Meeting James

"So his name is…" Rory asked as Tristan drove towards the airport.

"James," Tristan repeated for the umpteenth time.

"And you know him how?"

"We went to elementary school together," Tristan reminded her. "I swear I told you all of this."

"No, you didn't," Rory said crossing her arms over her chest, glaring slightly at her boyfriend. "You told me last week as I was knocking on my grandmother's door that we were picking up your best friend at the airport, and just as I was about to ask you about it, my grandmother just happened to open the door distracting me like you wanted. You then proceeded to avoid my questions spending the rest of the week talking to said friend," she ranted.

"You're jealous," Tristan laughed, obviously amused by the situation.

"No!" Rory responded quickly.

"Yeah, you are! You're jealous that I'm going to be sharing our first summer together with my best friend. A best friend you just happened to not know about."

"You're crazy!" She said rolling her eyes. "You know I'm not that petty, Tristan. I'm just feeling a bit left out that you haven't told me about your best friend. You know all about Lane."

"Yeah, because she hangs out with us ninety percent of the time."

"That still doesn't give you an excuse to not tell me about James."

Tristan rolled his eyes as he started looking for a spot to park in the crowded airport. Knowing Rory, she'd forgive him for not telling her about James then hold it over his head for the rest of their lives.

Every summer his best friend James returned to Hartford to spend the vacation with his father during which he and Tristan would inevitably hang out.

Since he and Rory had gotten together in their sophomore year of Yale, when a chance meeting at the campus pub had them reconnecting, they had never had a summer together. Either she was traveling with her mom for some mother daughter bonding, like her sophomore, junior and senior year of Yale or he was off working for his dad, like his sophomore and senior year of Yale along with the summers after that.

While he was traveling, Rory would spend the entire summer with her mother, saying that it was hard enough saying goodbye to him at the airport, she couldn't stand the thought of seeing him every day before he left and then not. And in that way summers apart were a bit easier on him.

Though he usually came back the last few weeks of August, she would refuse to leave Stars Hollow until it was absolutely necessary. They saw each other and talked on the phone more, and she would visit the apartment sporadically, but staying in Stars Hollow. In which Tristan would invite James over until he headed back to California the first week of September, the same week Rory pulled herself away from her mom and came home to the apartment they shared, the apartment James had shared with him those last few weeks of his stay.

The only difference this summer was that James was staying at the apartment for 3 months instead of 3 weeks because his father's new wife was getting the house renovated and they were currently living at the Waldorf-Austria in New York.

"I met James in the second grade," Tristan started getting out of the car at the same time Rory did. He locked the car stuffing his keys into the loose jeans and took her hand as they crossed the street. "We were inseparable, always got in trouble together, joint birthdays since the days were close together, all that stuff. But his parents split in the seventh grade. His mom got custody and his dad got holidays. So he stayed in California, but still spends holidays down here, including summer."

"In which you guys hang out."

"Right," Tristan nodded.

"And how is it I never heard of him? I mean… five years, Tristan. Wait, when I come home in September and the apartment reeks of beer and you say you had the guys over, was it really just James?"

Tristan winced. "I wasn't exactly lying, I did have the guys over, but James just stayed there. And you were always with your mom so I didn't see the big deal. The topic of James just never came up."

"Yeah, because I didn't know he existed!"

"Well, when you put it that way it makes it sound like I've been hiding him!"

"Because you have."

Tristan paused and looked at his irate girlfriend who seemed to be avoiding eye contact. "Look, I'm sorry I never told you about James. I don't know why I didn't, I just decided not to. I never meant for this to hurt you and fight about. But if it makes you feel better, I told him a lot of good stuff about you."

Rory sighed and looked at him. "What gate number?"

"Really? That easy?" Tristan asked shocked.

"That easy," she nodded.

Tristan smiled, leaning down and kissing her before mumbling "Gate 12."

Rory smiled. "Which is over there," she said pulling away from him, but keeping her hand in his and dragging him towards the gate.

XxxxxxxX

The plastic of the leather seats burnt his arms as the Connecticut sun hit the airport windows, making the air conditioning the airport had worthless. He was overheated and uncomfortable in the jeans and polo shirt he had decided to wear. And it hadn't helped that he'd been stuck between a heavyset man who'd been sweating profusely and a young mother with her crying baby son who seemed to feel the heat from 20,000 feet.

Every year he always seemed to forget about just how bad Connecticut summers were compared to the fresh-aired heat of California. Yet the summers in Hartford had been the best times of his life. It was the perfect weather for water balloon fights and nightly pool dips at the neighbors'.

Through the dark lenses of his sunglasses he spotted his best friend being dragged into the terminal by a girl about their age. He recognized her from the photos Tristan had sent at Christmas every year. Joint Christmas cards. He'd laughed at the first one, never thinking Tristan would be that serious about a girl but four years later the cards kept coming and it was the same girl. The exact girl that was pulling his best friend's arm out of the socket.

Her long brown hair was swept up in a messy bun as if she'd just grabbed it in the haste of leaving their home. Her milky skin seemed to be unmarred by the rays of sun, still pale in complexion, but healthy. Her arms were the same pure white, dressed in a pink tank top and her long legs clad in a pair of Daisy Duke shorts.

He'd once told Tristan that he was jealous of him for finding a girl that beautiful and who matched his love with her own. It was then that Tristan had admitted that it was her eyes that had attracted him to her in the first place. And as they neared, James saw exactly what he meant. Pictures didn't do those eyes justice. Big and blue so indescribable he could see how they could attract anyone's attention.

He had no problem admitting that when Tristan had told him about her he'd fallen in love with the idea of her. Intelligent, witty, family-oriented, faithful, loyal, best friend and from what Tristan had told him, an excellent lover. What was there not to love? But he had to wonder that if seeing her in the flesh would change his opinion of her. Was she as perfect for his best friend as Tristan claimed?

He unstuck himself from the plastic seat when he noticed they couldn't find him. He walked over, a smile gracing his features.

He was attractive, with his lean body that told the world that not only did he work out but he took good care of his body. He was tanned from his days surfing in the California Ocean; his blonde hair was now flecked with brown because of all the time he spent in the sun.

He had dark brown eyes that showed every single one of his emotions to a person who looked close enough. And a nose that he happened to hate. It'd been broken by Tristan when they were eight and again in football his junior year, so that it had a bump on the bridge and he thought it too long for his face.

"Tris," he greeted as he got closer.

Tristan laughed and pulled him into a hug which James returned with a laugh of his own. They let go only holding each other's forearms as they looked each other over, as they did every year.

"You look the same," James nodded.

"So do you. A bit darker from last time, but the same," Tristan nodded as well as they let go of each other.

"It's the beach bunnies, man," James laughed running a hand through his hair. "Like a moth to a flame you know."

Tristan 'ahh' understanding but laughed. "Oh, this is Rory," he said pulling her forward from her spot a few feet away where she'd been observing them.

"Ah, the long-time girlfriend. I've heard a lot about you. It's great to finally meet you."

She smiled and shook his outstretched hand. "It's nice to meet you as well. Though I've heard nothing about you."

"Really?" James asked surprised as he looked over at his best friend who looked a bit sheepish.

"You just never came up in conversation is all."

James frowned as they made their way out of the terminal and towards baggage claim. "You mean, when you guys met there was no basic 'get to know you' conversation and the topic of best friends never came up once in the five years you've been together?"

"Thank you!" Rory exclaimed.

"See, now this is making me feel bad!" Tristan groaned as they grabbed James's bags. He shouldered one while James grabbed the other. When Rory tried to help, they both subtly waved off her attempts.

"Good!" Rory said reaching into Tristan's pocket and grabbing the keys. "Serves you right for leaving things like this out. I deserve to know you have a best friend. I mean next you're going to tell me you have a kid."

"Wait, you haven't told her about Kimmy?" James asked seriously.

"What?!" Rory asked wide-eyed.

"He'd kidding!" Tristan said quickly, glaring at a laughing James as Rory quickened her step. "Mar! He's kidding!" They walked into the parking lot, Rory striding in front of them leading them to the car. "Thanks, man, I may be sleeping on the couch tonight."

James laughed. "She'll get over it… Right?" He asked, not quite sure just how easygoing Tristan's girlfriend was.

"Yeah, don't worry about it," Tristan waved off, then asked. "So are you ready to stay with us?"

"Yeah, I mean if you're still offering. I don't want to impose or anything."

"You've used the guest room before, man."

"Yeah, but never with your girl around."

Tristan shrugged as he threw the bags into the trunk Rory had opened. "It's the same, only with sounds coming from the other room late at night."

"Oh jeez," James winced as he got into the backseat.

"Hey, we are a healthy 25-year-old couple with needs," Tristan laughed as Rory hit his arm.

"Tristan!"

"What? It's true!"

"Ignore him," Rory said turning in her seat to face James. "You know, if you don't have any plans for this weekend, you're welcome to join us in Stars Hollow. It's Tristan's first summer down there."

"Stars Hollow?" James asked, not knowing the little town that she spoke of.

"It's about half an hour south of Hartford," she explained. "Really small town. We have a Start of Summer Festival and there's a massive water balloon fight to kick it off. Pisses Taylor off to no end."

"Taylor?"

"He's like their mayor," Tristan explained. "I'm telling you, this town is crazier than the old lady Brackett down the street."

James shivered at the old lady's name, causing Rory to frown confused as they made their way to the apartment she and Tristan shared. "Old lady Brackett?"

"She was this old lady that lived down the street from us when we were kids. Rich, widowed, hated kids since she had none of her own. Though we think she would have hated them even if they were hers. Anyway, every year in the summer kids used to throw water balloons at her windows and porch." James explained.

"And at Halloween we'd throw rotten eggs at her."

"At her house you mean," Rory corrected.

"Yeah sure, babe," Tristan laughed

Rory gasped looking at the two laughing men. "You're horrible!"

"No, it was crazy. She'd come out of her house chasing us all off her property in nothing but a skirt, her old white bra and ratty pink slippers with her broom. Grossest thing you'd ever see as a 10-year-old boy."

"Craziest too," Tristan laughed. Rory sat comfortable in her seat as Tristan and James recounted stories of their youth and the trouble they would get in.

She was hurt that Tristan had hidden such a huge part of his life from her. James seemed to know everything about Tristan vividly from the seventh grade down, a time Tristan barely revisited because of his dislike for his parents.

For the longest time Rory had thought that Derek, his old college roommate, had been his best friend. She'd remembered him from Chilton and remembered seeing him and Tristan hang out a lot during those few years of high school.

Tristan had explained that he'd met Derek in middle school and on, and were really great friends. But she'd never heard him use the word 'best' in front of it. Not until that night in front of her grandmother's door. She'd been so surprised to hear the 'best' in front of the 'friend' and annoyed that he refused to answer anything about James.

But watching them interact, finishing each other's thoughts, trailing off and laughing, already knowing the ending of the story, she knew why Tristan hadn't told her about James. He had been keeping the best part of his childhood to himself and was just now sharing it with her. And that's what made her smile.

She reached out and grabbed his hand that was resting on the stick shift. "You guys make a cute couple," she teased as Tristan parked next to her silver Audi.

"What?" Tristan asked shutting off the car.

Rory nodded. "The way you guys can read each other's thoughts, it's cute, very schmoopy. I don't even think we're at that stage yet, Tristan," she giggled as she got out of the car.

Tristan frowned over at James who was smirking. "So would that make you the girl in this relationship?" James laughed.

Tristan's frown turned into a glare as they both got out of the car, James chuckling as he helped Tristan unload the car as Tristan scowled. They followed Rory into the building, then to the elevators.

"So you've known Tristan a long time?" She asked as the elevator took them to the 14th floor where their apartment was.

James nodded. "Close to 20 years."

"So you've got stories?"

James laughed. "Oh yeah, lots of them."

"Oh come on," Tristan groaned as they walked down the hall to the apartment.

"Tristan refuses to revisit his past with me. Says that all that matters is that he isn't the same high school boy I once knew and what happened in the past stays in the past." She rolled her yes. "Of course that didn't seem to apply when I told him everything that happened in my past."

"Well, in elementary school," James started as they dropped his bags at the door and Rory led them to the kitchen, handing them each a water bottle as she settled herself on the counter top. Tristan walked over and settled himself between her legs, her hands dropping around his neck and chin resting on top of his head. "Tristan was believed to be a saint, but we were the ones that pulled most of the pranks at that school. Tristan's signature was the stink bomb, of course."

"Oh gross!" Rory groaned. "That was you at Chilton?!"

Tristan laughed but nodded. "Guilty."

Rory shook her head but laughed. "I think it's funny. I just wish you would have avoided putting them in the girls' bathroom. We used to go in there just as the bomb went off. My uniforms never completely got that smell off. My grandmother had to buy me four news ones. And of course my mother took that opportunity to make the hem higher each time."

"Exactly," Tristan smirked, causing Rory to hit his arm.

"Genius," James laughed as he launched into more stories of Tristan and his past with Tristan groaning the entire way or adding his own details of the account.

XxxxxxxxxxxxxX

A.N.:This was written for Build a Fic summer challenge, but I got carried away and ended up written a loooong one shot, so after talking to the Ickles I decided it was better to post this as a multi-chapter. Plus time didn't allow me to make the changes that I would have made to get it upon Build a Fic. So I hope you guys enjoy it!

Kassandra