Literati in Kyle's Parents' Bedroom

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Rory's first time with Jess at Kyle's party. Gilmore Girls.
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This is a fixer for Gilmore Girls episode "Keg! Max!" (3.19), more specifically to what happened (or didn't happen) in Kyle's parents' bedroom. Literati smut. Just something I needed to get out of my system. I don't own Gilmore Girls nor the original dialogue, but there are just a few lines of that in here.

All characters are 18 or older at the time of this scene.

---

Rory could tell something was up with Jess from the moment she'd met up with him to go to Kyle's party that night. He'd been quieter than usual, less up for their intelligent banter, only really speaking when someone directly asked him something. All she could think of it was that perhaps he was tired.

He had been working a lot recently, though he'd never gone to great lengths to explain what he was working for. She knew it was his way of ensuring he had some kind of a future, that he wouldn't be stuck working at the diner and living with Luke for the rest of his life. But he never really dared to dream much, at least not in so many words.

But Jess was the classical night owl, Rory knew that. He didn't tire that easily - and the realization left Rory without a decent explanation.

Helping the band setup had been less fun than Rory had expected. It was like waiting for something great, something exciting to happen, but it just wasn't happening, and it was only making Rory feel worse about dragging Jess over to Kyle's. It was her first party, the unsupervised kind. And no matter what happened, she was kind of excited to be there.

She wasn't really sure what to expect. All she had to go on was everything she'd seeing Freaks and Geeks, 10 Things I Hate About You and American Pie - and those hardly qualified as documentaries.

Clearly Jess thought they'd arrived too early, which was uncool on so many levels and he wasn't shy about expressing it. This just made Rory feel worse, but she tried to put on a brave face.

Jess knew how to party, he'd done this before. He looked cool, his essence was cool. He knew how to arrive fashionably late, something Rory had never known how to do. She was always too eager. Hell, Jess knew how to install a keg - he was so beyond anyone at that party. He was a city boy, unlike the rest of them.

To bury all that insecurity, Rory had just tried to reason with him and pretend that being early and letting things play out as they were happening was cool, but she could tell he wasn't convinced. At least she desperately hoped that was all it was.

He'd even begged her to just leave with him, but she'd convince him to stay a little longer. Her kisses seemed to pause any unhappiness for a minute or two and persuade him to do a lot of things. Not all things though - he didn't exactly share a lot of what he was thinking.

"There you are!" Rory exclaimed with relief, having found him after looking all over the house for him for at least twenty minutes by now. Jess was sitting in an empty bedroom, having clearly found a comfortable space to hide out. That certainly was like him - all that was missing from this picture was him having at least one light on and having a book in his hand. There was no book, no light either.

"Hey," Jess replied, straightening himself in the dark green armchair by the window.

"I've been looking all over you," she said, worriedly.

"Just got tired of everything down there," he replied, briefly.

Rory closed the door behind her. Clearly he didn't want to be around people, and feeling a little guilty for having convinced him to stay as long as she had, she figured she could at the very least give him that private space. Maybe she could just keep him company? She really wasn't about to force him to go back down there.

Rory walked across the room and Jess got up from the armchair. The prospect of being alone with him wasn't half bad now that the band had performed and Rory had done her duty as Lane's personal fanclub.

Making out with him was quickly becoming one of her favourite hobbies, each time losing herself a little more in him. She was definitely thinking about it becoming something more. And the fact that they were at a keg party, upstairs in a random bedroom - the thought of spending some alone time, getting lost in him again, and perhaps cheering him up in the process, actually kind of had that rite of passage sound to it, even if it was a bit of a cliche.

"Are we allowed to be up here? I mean, Kyle was kind of discouraging it," Rory worried, glancing around the room a little. The room was nice, a little too pink and flowery to her taste, but at least it didn't smell excessively of some overbearing perfume, like some bedrooms did.

She was always such a good girl, so sweet and innocent - it was almost annoyingly cute - Jess thought. He was nothing like that.

"When you have a party, you get what you get," Jess sighed.

He certainly had more experience with parties. It was also the reason why he's specifically avoided throwing them, not that he had a place to hold one these days. Nothing like Kyle had, not by a long shot, and being in this house - where everything was so polished, so white-picket fence, two point five kids and all that crap. Pictures of this facade of a happy family, that's what he chose to believe it was at least, it really wasn't doing his self image any favors either. In fact, it was only making him feel worse about himself.

"Yeah, I guess," Rory exhaled.

Rory extended her hand to stroke his cheek, seeing him miserable like that. Jess just barely grazed her palm with his lips, appreciating the caring gesture.

"Sad boy, what's wrong?" Rory inquired, in a sweet tone.

"You were looking forward to this party, what happened?" she continued worriedly.

"Nothing," Jess grunted, barely audibly, but Rory could tell it wasn't nothing.

"Something did," Rory noted.

She was sick of pretending there was nothing. He was always like this - just shutting her out. She had her own suspicions by now. She knew more than she'd let on, but she didn't want to just bust him on it either. She knew that his reasons for not speaking were not that he had anything against her - he just didn't dare to, he didn't know how to.

"Come on, tell me," she urged. She had to try at least.

But before he had really a moment to actually take in what she'd said, he kissed her. He was kissing her with more than just lust. It was about appreciation, feeling like she was the only person in the world that he wanted to be around. He... he loved her, but he was nowhere near putting that into words.

But knowing what a disappointment he was, how he didn't measure up to her in any logical way - he was kissing her almost like it might be the last time he got a chance to do it.

While he'd sat in that room alone, a lot of very dark scenarios had gone through his head. He'd thought about leaving before Luke found out, he'd thought about begging Luke to give him another chance, but he was pretty sure that wasn't happening. He'd thought about putting up with her mom, but that just would drive him insane, he knew that. He'd thought about his father - maybe that was his way out?

Jimmy had wanted to talk to him after all, surely he wouldn't have come all that way just like that if he hadn't really meant something by it. But all those dark scenarios would end this chemistry that he was feeling in their kiss, this right here. This thought terrified him. The thought of leaving, leaving her, felt like cutting off a limb. This was the only place he wanted to be right now, even if it turned out to be the last time.

"You're not tired of me, are you?" she continued, feeling insecure. What else could it be if he hid it from her that badly.

Maybe she was too inexperienced for him? Maybe... she didn't do enough?

She knew he wanted to do things with her, sexual things... she knew there was a lot with what Jess had been holding back with her.

That deep kiss that followed certainly didn't feel like he was sick of her.

"That's a pretty good answer," Rory replied.

They just stood there, holding each other, foreheads resting against each other.

Soon that tension formed into another kiss, each one deeper than the latter. Kissing him was addictive, it was the best drug she had ever known.

She was getting lost in him, and it only felt natural to follow his lead as they made the few steps towards the bed to lay down. It felt incredible to feel his weight on her - his moves felt so strong and masculine, making her feel desired. Definitely a good answer.

"Please talk to me, Jess," she murmured, breaking their all-consuming kiss reluctantly. She really didn't want him to stop, but she had to - she had to get him to talk.

Jess' lips demanded another kiss, as if being determined to avoid saying a word.

"Jess, wait...," Rory said, raising her voice now.

"Jeez," Jess pulled away from her, and stood up.

She'd already felt his erection against her thigh, she knew she'd gotten his hopes up - it wasn't the first time, and she felt horrible for being such a tease. She really didn't want to stop, she needed him to know that. But she needed to know what was wrong - right now it just didn't feel healthy, him bottling things up again.

"Jess, just listen, okay?" Rory said, taking his hand, trying to calm him.

He was almost about to pull his handback, maybe even just storm out, feeling frustrated. It wasn't about her, he'd never force himself on her, but the whole thing - everything he tried to do he failed, he couldn't even get her to want to

be with him.

But it was her touch, along with those bright blue eyes, visible thanks to the streetlight, that stopped him.

"Ah..," he exhaled, and sank back down on the bed, burying his face in his palms. He didn't like anyone else.

Where was he going to go?

"Jess, I'm not saying 'no'...I wasn't pushing you away because I didn't want

you. I want us to go further than this..," she began, assuringly, stroking the nape of his neck.

That was certainly something Jess hadn't expected to hear from her. He almost felt that he didn't deserve to hear it.

"Then what?" he let out a huff, not understanding why she'd stopped him then.

Rory climbed onto her knees on the bed, and took his head into her hands, looking into his eyes. She could tell it was hard for him to look at her.

"Jess, being intimate with someone, it's not just about taking off one's clothes..," Rory explained, resorting to something she'd read somewhere. "I don't want my first time to be just about getting it over with in Kyle's parents' bedroom. I can tell you are bothered by something. I know you're hiding something from me and I just need you to know that whatever it is... you can tell me," Rory said, caressing his neck and hair.

Rory took a deep breath, looking for the right words.

"Have I ever not tried to help? Have I not supported you? I know I may not get everything you've been through...I know talking is not what you're used to doing, I get it's not as easy for you.. Just please try, Jess -just...," she said, pleadingly, leaning her forehead against his temple. "Please," she begged.

"I don't deserve you, Rory...," Jess exhaled, closing his eyes and looking down, knowing that if she opened them she'd see his tears. "You're so smart, so beautiful. You're graduating from Chilton, top of your class. You're going to Yale... You'll be surrounded by all these intelligent, wealthy people all of your life, people that have everything together...," he continued.

"You're smart too...," Rory assured. "I prefer your brain to most of those in Chilton...probably Yale too," she tried to lighten the mood a little, mostly due to hesitance.

Her heart was beating fast within her, adrenaline rushing - this all sounded too much like a break up not that she'd been through many in her lifetime.

"I'm not graduating, Rory," Jess let the scandalous secret slip from his lips, unable to look at her. He knew she'd be so disappointed in him, she'd know he'd lied to her.

But Rory just didn't say anything right then. She had asked him if he was going to school, and he had assured her he was. Clearly that hadn't been the case. However, it was no news to her that he didn't like the place - but she knew he was smart, but surely there was a limit to how much attitude and slacking principal Atherton would take.

"I'm being held back, I can't even take you to prom. I'm sorry... Luke's going to kick me out the minute he finds out... I am a loser, Rory. Everyone was right - I am no good for you!" Jess said, and Rory could tell now that he was in tears. The darkness hid it well, but his cheeks glistened enough for her to tell.

Rory could tell from the way his muscles tensed up, wanting to raise - perhaps walk out. Instead of letting him, she clinged to his neck. It was perhaps not the way to do it, but she was determined to physically stop him from leaving the room. She was terrified that if she let him leave now, that'd be the last she'd hear from him.

"I don't care about the prom, Jess. I care about you," she whispered to his ear, deciding to not scold him for lying. And pulling back just a little, she let the real bomb drop - "I love you," she said.

At that sentiment Jess' hands just went around her more firmly, holding her as tightly as he could. If nothing else,he would have this moment. He would feel her love for him. For once in his life.

"You don't need to say it back. I just needed to say it," she assured, knowing too well the internal battle he must've been having. She'd been in that position before.

"Everything else - we'll figure it out. The world doesn't end...," she began to explain, already thinking practically about night school options and how she was going to get him back on track.

Jess didn't allow her to finish however - a bruising kiss interrupted her, his tongue demancing access. She certainly didn't hesitate to return that kiss - she really was in no rush to hear it back, that kiss making up for at least a part of it.

The kiss broke with both of them panting, the surprise having passed in the matter of seconds.

"I...," Jess began, wanting to say something. He was so close to letting him know how much he felt for her, how much he cared, how much he needed her. How grateful he was to her, for forgiving him, for understanding, for saying just what he'd needed to hear, but also how undeserving he was of all of that, but the words just wouldn't come.

"Shh..," Rory held a finger to his lips. She knew he wasn't ready.

She knew what he was ready for, however, and after feeling like she'd broken down that invisible barrier between them - all she wanted to do was make him feel better.

Rory looked at him, staring straight into his beautiful dark eyes.

The next minute she climbed to straddle him across his lap, arms going around his neck, and by kissing his lips at the same moment she wasn't giving him any opportunity to object - not that he was objecting.

She wanted to allow him this night to forget himself, forget himself in her, just like she just wanted to be there for him and make him feel better. She hadn't planned on telling him she loved him - there always had been that barrier - but now that that was done, and she'd made herself vulnerable in front of him - going all the way really felt like way less than what she'd said.

Rory melted as his body was no longer tense and began to caress her waist, thighs and ass, his hands slipping under her t-shirt to feel her.

She took the lead, letting her own jacket fall to the floor, not breaking the feverish kiss.

"We don't have to do this here..," Jess managed to whisper. He thought more of her than doing this quickly in someone else's bedroom with the fear of getting caught. But then again they really didn't have a better place at hand. Even his car was gone, stolen, and that certainly was worse than this room.

"I don't care where...," she hummed.

"Lock the door then," he suggested. He didn't want to hurry this. After being as amazing as she'd been that night, she deserved the best he could offer.

"Right," Rory giggled, her lips already red from the bruising kisses. She climbed off of him, and shakily made her way to the door, feeling the nervousness grow. Thank god, the door actually had a lock.

Jess wanted to ask her again if she was sure about this, but surely her voluntarily locking the door, and returning to straddle him was answer enough.

"You're so beautiful, Rory," Jess said, letting the tension linger.

Rory still struggled to take a compliment and instead buried her face in his neck, and tasted his slightly salty skin. Jess took a whiff of her scent, her silky smooth hair feeling so incredible against his lips.

Rory urged him to shed his jacket, allowing her fingers to trace his lean muscles she'd already discovered during their numerous less promising make-out sessions. It had all really just been foreplay for this.

Jess wasn't believing this - the night had started so bad, and now this ravishing, innocent creature wanted to give her virtue to him, if he were to speak in such ancient terms, but he was in no condition to argue - she was the only good thing in his life.

One shirt after the other was removed, exposing the porcelain skin on her chest that moved as she breathed heavily. Her bra was white, or perhaps pinkish - impossible to tell in this light, but it had a lace edge, making her look incredibly sexy. While he hadn't seen much of her underwear so far, he'd seen enough to know this was something new.

She'd really thought of this, hadn't she?

Jess let his back fall to the bed, pulling Rory, who let out a slight yelp at the move, along with him, making her giggle lightly. Rory, beginning to feel nervous, snapped her bra open before he had a chance to even try, wanting to hurry things along a little. She didn't know how long this was supposed to take. She didn't want to make him wait, she didn't want to do it wrong.

It was then as she lay there hovering on top of him, having thrown the bra off to the side, her breast brushing against his chest, she felt for the first time her nipples growing hard as pebbles at that gentle brush against his chest, linking directly to her arousal. She didn't know what it'd be like - all she knew was that she wanted to feel him more, she wanted him to let her feel all of him.

Instead of hurrying things up, Jess bent his neck and urged Rory to lean forward a little, taking her nipple into his mouth. Rory gasped at that sensation, having never felt his hot mouth against something so sensitive. Little did she know...

Rory wasn't sure how long she would be able to take this, her need for his touch below waist was growing stronger by the second, and after gathering her courage she let her hesitant hand trail down his chest and abdomen and onto his crotch, over his jeans - but still. She'd always been too careful and afraid to touch him there deliberately, usually sticking to grinding against him, unsure if she was ready to take things further.

"That feels so good, Rory," he hummed, and took her other nipple into his mouth.

"Ah...," Rory reacted, the feeling taking her by surprise again, allowing herself to be a little bit more vocal.

Jess' hands looked for her belt buckle, only then realizing there was a key hanging from it.

"What the..?" he asked, wondering what was up with that.

"Oh that," Rory said, having completely forgotten about that. It had been her mother's trick for storing a key at a party. For a moment that brought her mom to her mind, which was definitely an idea she wanted to shed. Instead of dwelling on it, desperate to not let the imaginary judgement of her mother stop her, she quickly unbuckled her belt, taking the key away, and placed it into Jess' jeans pocket.

Jess unbuttoned her pants, liberating her, while reaching up to kiss her on the lips again.

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