I started this close to three years ago(maybe four) as a challenge in an exchange I now lno onger remember the name of. It's still not done, but here's the first part.

Rating: R/NC17

Things to Include:

An encounter with Mrs. Kim

An Argument about the merits of blue v. pink cotton candy

Asshat/Lwewd! Tristan

Smut

A broken car windshield

Things NOT to Include:

A Stars Hollow event of any kind

Any reference to military school

Wimp!Rory or Tender!Tristan

Marriage or Proposals

Happy Writing

This just was not Rory's summer. Just as everything looked like it would be going well, it all came crashing down. Nothing could salvage this summer.

First, there was the whole Dean Fiasco. She definitely thought of that in all capital letters in her head. It had its own category on the Incredibly Stupid Shit in my Life list she had composed for herself. Like she was telling her mom after the confrontation with Lindsay and her mother, she had decided to remove herself from the situation and she was sticking to that decision. She still couldn't believe how that the whole incident went down. Not how she imagined it, that's for sure; not at all. She just couldn't seem to remember why she thought Dean was perfect. Finally, she just had to chalk it up to Tanna's painful reminder of how alone she had been all year. Who else was to make her feel safer than Dean? Boring, predictable, safe, Dean.

Rory had been home from her trip to Europe with Emily for a few days. She just wanted to relax and spend the next two weeks at home with her mom and friends before heading back to Yale. She had just headed for the door to go meet Lorelai at Luke's for lunch when she heard her cell phone ringing in her room. Turning back into the house and grabbing her phone off the desk, she saw that it was Emily calling.

"Hi, Grandma," Rory answered her phone, walking back out of her room, headed towards the door.

"Rory, wonderful, I was hoping I could catch you," said Emily.

"Yeah, I was just leaving for lunch. Did you need something?" asked Rory.

"Well, I've been supervising the unpacking from our little trip and I believe some of your stuff got mixed in with mine," said Emily. "You would think that the concierge would have sent someone who could tell the difference between my clothes and a twenty-year old's, but apparently that is just too much to ask of a hotel these days."

"Oh, tell me you have my yellow rubber ducky pajamas," said Rory. "I've been looking all over for them."

"Yes, those and a few other articles of clothing," Emily replied. "I also have some souvenirs here for you. And I took the camera in to have some pictures printed for you."

"Well, thank you, Grandma," said Rory. "I can come by later this week or I can just get them when I come to dinner this Friday."

"Really, Rory. That is not necessary," said Emily. "An old friend of Richard's had stopped by with his grandson. I believe he went to Chilton with you. He said he could run them out to you; give you two a chance to catch up."

"Grandma, really, you don't need to go to the trouble." Rory continued out of the house and down the street, waving as she passed Maury and Babette.

"Nonsense, Rory. He's already on his way and I was just calling to let you know he'd be there shortly," said Emily. "I have to go now, tea with some of the girls. I'll see you on Friday."

"Grandma, wait," said Rory. "Who is it bringing me my stuff?"

But she was too late. Emily had already disconnected, leaving Rory to wonder just what her grandmother was up to by sending someone she probably didn't know at Chilton to Stars Hollow. It was just like Emily to try and set her up with some rich kid from the society set. Lord knows she had to put up with it all summer.

Walking past Mrs. Kim handing out fliers for the next Bible study group and into Luke's, Rory forgot about the mystery guy showing up as soon as Lorelai started gesturing wildly for her to join her for a cup of coffee at the counter.

"Mom, seriously, I'm not even five minutes late. How many cups of coffee have you had?"

"Kid, how many times do I have to tell you, it doesn't matter how many cups I drink, I'm still gonna need more."

"True. Someday I will have to remember that. We should really just hook you up to a funnel, a new invention, the coffee-bong," Rory said, sitting at the counter on the stool next to Lorelai. "Luke, can I have an order of cheesy fries and some coffee, please?" ?."

"Sure thing," Luke replied. "It should just be a couple of minutes."

Rory was listening to Lorelai go on about Michel and Sookie arguing over Michel's diet, or rather lack thereof, when, out of the corner of her eye, she noticed a bit of a commotion outside. Someone had parked a big SUV type thing vehicle outside the diner and it appeared as though the driver had been accosted by Mrs. Kim as he attempted to enter Luke's. He looked strangely familiar to Rory and she remembered that Emily would be sending someone to the Hollow with her things.

Rory rushed outside, grabbing the guy's arm and pulling him away from Mrs. Kim who had been haranguing Rory's caller with a lecture on greed, and how his appearance was definitely required at the next church meeting to atone for his sins.

"I am so sorry that Emily sent you here," Rory rushed out.

"Ma'am, I fail to see how my vehicle causes a need for me to atone for my sins," said the mystery man as Rory pulled him back to his vehicle. This gave Rory cause to pause and take a closer look at the man she was attempting to force into the SUV.

"Yeah, Mrs. Kim, I'm sure he has many, many other sins, which should be atoned for before greed," said Rory, a look of recognition crossing her face. "Right, Tristan?"

"Aww, you do remember me," he replied, a slight smirk gracing his features. "I have some things for you."

"Yeah, yeah, I know. I just spoke with Grandma."

"Well, get in," Tristan told Rory, gesturing to his vehicle.

"Why on earth would I get in a car with you?" she asked.

"Well, apparently you left your panties at your grandparents," Tristan said, smirking as he approached the other door of the vehicle. "I guess I could just whip them out here and give them to you in front of, who was it, Mrs. Kim? We could get into another discussion about sins of mine, and possibly yours, since I'm just returning some rather personal belongings."

"Oh, God," Rory said, eyes wide, crossing to the other side of the vehicle. "You better not even dare."

"C'mon, Rory," he said, his smirk getting bigger, turning to her as she got in the passenger seat. "We can give this quiet little town quite the show."

"No thanks, I have been enough of a spectacle around here the last couple of days. I really don't need your help in that department," said Rory, now facing him. "Can I please just have my stuff?"

"I'm doing terrific, Rory. Really nice of you to inquire about my health and general well being and all, seeing as how this is the first time we've seen each other in almost three years," Tristan said, a hurt look quickly crossing his face.

"I'm sorry, Tristan," said Rory, hands twisting in her lap. "I shouldn't take my crappy summer out on you."

"I'll say," he replied, leaning towards her a bit. "What the hell did you do that meant you had to go to Europe with Emily for the summer? Cause that must have been some kind of flaming hell for anyone involved."

Rory and Tristan both jumped as his windshield suddenly shattered. Rory's head snapped around and through the broken windshield she saw Lindsay standing off to the side of the vehicle and a brick, having bounced off the windshield, now in the middle of the Escalade's hood.

"What the hell?" shouted Tristan, reaching for the door handle.

Rory grabbed at his shirt, holding him back from exiting the vehicle. "Stop, I will handle this."

"What do you mean, you'll handle this? Some crazy chick just threw a brick at my fucking truck!" Tristan said, looking at Rory as if she had been the one to lose her mind.

"And it has absolutely nothing to do with you, so I will handle it," Rory told him, getting out of the SUV herself. She shut the door behind her, aware of the gathering crowd as it started to surround her, the Escalade, and Lindsay. She really wished Lindsay had chosen another time and place for a confrontation. Hell, showing up for Friday night dinner would have been better than this.

Rory approached Lindsay, now wary of getting too close.

Lindsay was huddled into herself. "How can you stand yourself?" she sobbed. "You ruined my marriage not even two months ago and now you've moved onto another guy! What did I ever do to you?"

"Hey!" shouted Rory, now pissed about the entire situation. "Dean and I were never about you!" she lashed out. "It was always just the two of us. So before you start laying all the blame at my feet, you need to realize that it only happened because he told me that the two of you were over. And he's not a new guy; I've known him as long as I've known Dean."

"So, what," sniveled Lindsay, "you just go back and forth between these guys, playing them off one another?"

"No," Rory said back. "I haven't even seen him in years, so back off. He has absolutely nothing to do with this."

Rory witnessed that Lindsay was really struggling with herself. The crowd was watching in earnest, as was Tristan. This was definitely one of the more interesting things to happen in Stars Hollow. Rory got a bit closer to Lindsay and lowered her voice so that the remainder of their conversation would remain between them.

"Look, I'm sorry," said Rory. "I know that doesn't make this better and it doesn't make the hurt go away. I don't think anything can. But I only know what I did and my reasons for doing so. You'll have to ask Dean about his side of it. I only know that he said you guys weren't working, that he wasn't happy, and that your marriage was over. I wrote to him after I left and told him that I wasn't going to do anything about it because you two need to work yourselves out."

As Rory was talking to Lindsay, Luke had dispersed of the crowd and Lindsay's mom was approaching the two girls on the side of the street. She started to say something to Rory, when Lindsay stopped her.

"Mom, no…just, no," she said in a halting tone. "Let's just go home."

As Lindsay and her mom turned to go Lorelai walked up to Rory.

"What just happened, kid?" she asked. "And who's the hottie in the truck? Seriously, Mommy needs to know."

"Grandma sent him with some of my things. I went to Chilton with him," she replied, only half-answering Lorelai. "I'm just gonna take care of this. I can explain more later."

"Okay," Lorelai said, trying to shrug off her concern over Rory and the latest confrontation. "But I want details and lots of them when you get back." Lorelai gave Rory a quick hug and turned to go back to the diner, leaving Rory to face a smirking Tristan.

"Well, well, well. It seems my Mary, isn't such a Mary anymore."

Rory climbed back into the vehicle, glaring at Tristan.

"Quit being an ass. No, I am not a Mary anymore and I was never yours."

"Challenging me already? I like it more and more."

"You would."

"You know, for being the one responsible for the damage to my ride, you could at least try to be a bit nicer."

"Shit." Rory leaned her head over her lap. Not looking at him, she said, "I'm sorry about your windshield, Tristan. I never meant for anyone else to get caught in this whole mess. Head down the street and we can get Gypsy to look at it."

"I highly doubt any mechanic in this town is going to have a windshield for any kind of Cadillac, never mind a custom one. Seriously, can anyone here even afford a luxury vehicle?"

"More than you would think, actually. We just choose not to flaunt our wealth," she said turning back towards him, tucking away a stray bit of hair.

"Too busy flaunting other things, I take it?."

"Shut up," came her succinct reply. "Just start the damn car and go to Gypsy's. I will have her order you a damn windshield and either you can take my car while it is on order or I will take you home.. Either way, please, just shut up," Rory's statement ended in a whisper.

Tristan just looked at her for a moment and started the SUV. The short drive to Gypsy's was made in silence. Rory was lost in her thoughts and Tristan was equally lost, wondering exactly what happened in the last three years that changed Rory so much. He was determined to find out what caused this … and to see exactly how much she had changed.

"Hey, why don't hang out at my place for a while?" Tristan said. "There's something I want to show you."

"Tristan, I don't know how many times I have to tell you, I don't want to see your penis," Rory replied with a straight face.

Tristan broke out into a large grin. "That's not what I wanted to show you. But if you ask real nice …"

She smacked him on the arm, efficiently breaking the tension that had passed between them during the walk from Gypsy's to Rory's driveway.

"Seriously, come over for a bit," said Tristan, moving to get in her car. "There probably isn't anyone there and we can actually catch up, maybe make that attempt to be friends."

Rory got into the driver's seat and started the car, making her way into Hartford. "So, you never answered me, what are you doing back?"

Tristan looked over at Rory as she kept her eyes on the highway. "I'm doing what almost all kids our age do. I'm getting ready to go to college."

"So, Mary isn't a Mary anymore," Tristan said, breaking the silence that had over taken the car after his comment about school.

"You said that already," Rory said, still refusing to look at him as they approached the DuGrey mansion.

"And you never answered me," Tristan smirked, turning in the passenger seat to face Rory instead of the scenery around them. "Well?"

"Tristan, stop, okay?. Just drop it."

"No, seriously. It had to be bag boy?"

"Tristan."

"Let me guess," he said, leaning in toward her. "Perfect night, made for love, romantic candlelight, soft music playing in the back ground as he…"

"Shut up, Tristan," Rory bit out.

"Of course, if I read that scene correctly, he's married now and that made you the other woman so I guess it really couldn't have been all that romantic."

"Listen, Tristan," Rory snapped, whipping into the driveway he had indicated to her. "You have no idea what my life has been like. You've been gone for well over two, probably closer to three, years and no matter what, I fail to see how my rather lackluster initiation into sex is any of your damn business."

She parked the car next to a fountain in the center of the circular driveway.

"Lackluster, huh?" Tristan was trying to peer into her eyes, but she had her face kind of downward, trying to hide from his prying eyes. "What, old Deany-boy couldn't do it for you? 'Cuz you make it sound like he was a bit of a dud in the sack."

"Shit," Rory muttered to herself, still trying to hide behind what was left of her hair.

"Now, see, if it had been me, it would have been a whole other story," Tristan said, smile still on his face, waving his hands around a bit.

"Yes, Tristan. You really turn me on. You're astounding wit does it for me," Rory came back with in a dry tone.

"I always thought so." That damned grin turned back into a smirk with this. He leaned in closer, the idea of personal space quickly becoming a foreign concept as far as he was concerned, not to mention completely unnecessary.

"So how about it? Come inside and I'll…" he whispered in her ear at this point, his voice low and gritty, causing her to shiver.

"You'll what?" she snapped back, struggling to regain a sense of composure, trying to get back some of her personal space. "Astound me in a heated debate over which flavor lip gloss you prefer? Still can't decide between blue cotton candy and pink cotton candy? Flip a coin already, either way, its cotton candy."

Tristan didn't back off in the slightest; he now had her pinned between her seat and the steering wheel, the door at her back. He fixed his gaze on her lips as she spouted off about cotton candy flavored lip gloss, of all things. "Really, Rory, if I was going to be debating over blue versus pink cotton candy, it wouldn't be flavored lip gloss. Edible panties, now that could be a heated debate."

He grabbed her hands from her lap now, and pinned them above her head, resting her wrists against the headrest. He leaned in and started to nibble and lick along her collar bone.

"Edible panties, are you serious?" Rory got out, struggling to keep breathing.

"Yeah, can't you see it? You, me, my bed, me naked, you in a sticky sweet pair of panties with me bent between your legs, sucking and licking the cotton candy flavor from your flesh."

"Tristan," Rory managed to get out. "Get off."

"I'm trying to. I'm trying to get you off, too. Now, I can't see you in pink panties, a little too girly for you. Blue, however. Blue cotton candy panties would be great, bring out the color of your eyes and the rosiness of all this skin."

Rory was still having trouble breathing. She pressed against the back of her seat, Tristan leaning over her, one knee between her legs, he can feel the heat rolling off her center. He started to gently rub his knee into her as he described the scene to her, imagining what she would look like, naked except for a bright blue pair of candy panties against his darker blue sheets.

"I think Dean-o didn't do it right. I think what you need right now is a nice long hard fuck."

This shocked Rory out of her complacency.

"Why is this any of your business? Why do you even care?"Rory shot at him. "How is my first sexual experience any concern to you?"

"What sexual experience? It sounds like you were barely even a part of losing your virginity, Tristan replied. " You need to accept the idea that there is nothing wrong with enjoying sex. Nothing dirty about it and nothing to hide or be ashamed of. Sex is meant to be enjoyed and I think I want to be the one to show you that."

Rory followed Tristan into the house and up the stairs in silence.. When she saw that she had followed him into his bedroom, she stopped him and said, "Tristan, I told you I didn't want to see your penis."

"And I told you, maybe later, if you ask nicely," came his reply as he continued through another door in the room. "Come in here, take a seat."

Rory walked through the door and saw that the room had a rather large, comfortable couch in front of a large flat screen TV and coffee table. She sat down on the couch, crossed her ankles and propped them on the coffee table. "I could die here," she sighed, spreading her arms across the back of the sofa.

She watched as he got out a DVD and went to answer a knock at the door. He let a maid in carrying a try of food and beverages and had her set it on the coffee table. He shut the door behind the maid and put the DVD in before heading over to make himself at home on the sofa next to Rory.

"So, what exactly are we gonna watch?" Rory asked, starting to get a little curious about what Tristan wanted to show her.

"Well, I thought we could start with soft porn and then work are way up to the more hardcore stuff later," he replied. He tugged at Rory's arm, pulling her across his lap so that she was lying down. He moved so that he was propped up on one elbow, half over her and she was flat on her back.

"Seriously, Tristan, what is going on?" she asked.

"Seriously, Rory, I wasn't joking," came his response.

"What?, Nno. No way," Rory said as she began to struggle to get off the sofa. Tristan just laughed, splayed his free hand over her stomach and threw his leg over hers, pinning her to the sofa.

"Calm down, Rory. I told you after the comment you made about your rather lackluster initiation into sex, it wasn't done right. So we're going to do it right."

"Tristan, this is such a bad idea."

"Shush, you. Just watch the movie. I'm just gonna lay her beside you and play."

"What?!? No. I'm not going to watch some movie, while you 'play'."

"Yes, you are. Just watch the movie and ignore me."

"Tristan."

"Rory."

"Ugh, fine. What am I watching? And don't say porn," she asked, as she turned her head to watch the movie on the screen.

"Who cares, just watch it," he said, grinning a little as he started to just lightly rub her stomach, movie her tank top up a bit, out of his way. Rory was watching what appeared to be a couple returning from a dinner date play out on the screen and Tristan began to nibble on her neck and unfastened her jeans. Rory tries to protest again, but only half heartedly. Tristan removes her top, surprised that she isn't wearing a bra. Rory senses his surprise and looks at him and shrugs. "Built in bra, it's too hot for under wire."

"Did I say anything? Watch your movie." Rory turns back to the screen, but isn't really seeing the couple begin to undress on screen.