A/N: This chapter was not edited by a Beta, so there's probably gonna be lots of errors.

Chapter 3

The next morning Rory slowly blinked awake. She felt really cozy and warm, a bit sore but not too much. When she lifted her head up she saw she was lying on top of Jess, who was still asleep, his arms wrapped protectively around her. Her heart fluttered in happiness, and she smiled studying his face in his sleep. He looked so beautiful, relaxed, and peaceful. His lashes were long and dark. He had a few brown freckles on the side of his face and under his chin. There was also light stubble forming already. The sight made her giddy. He was always clean shaven in school, and she never got too close to his face to study the freckles and other little bits that made him unique. She also noticed his nose bridge was a tiny bit crooked, and she wondered if he broke it sometime in the past. His ears were uneven and she caught herself finding all of these little things endearing and cute. She could easily see herself falling in love with him.

That thought made the blood in her veins run still. Love? She had sex with this guy last night. She lost her virginity to this guy last night. Oh God… The more she thought about it, the more panicked she felt. How is it going to be from now on? She's never seen Jess dating anyone. What if he didn't date at all? What could she possibly offer him? She was a Mary, after all. How is she supposed to act when he wakes up? What if he was disgusted with her and pushed her away? Or maybe he would act like nothing happened, and just leave whistling on his way out, having deflowered the last virgin in Chilton.

She wanted to talk about this with someone. She needed to talk this through with her mom. Oh no, mom! Rory and Lorelai never even had 'the talk'. Of course, Rory knew all about the need of using protection, she knew that even having sex once can cause serious repercussions if you're not careful. Her entire existence was proof of that. But while she was dating Dean, sex was not even on the horizon, yet Lorelai had a fully fledged freak out when Rory accidentally fell asleep on a bean bag with Dean at Miss Patty's. It took a lot to convince her mom that nothing happened, and Lorelai made her promise that Rory would talk to her before taking such an important step in her intimate life. Rory has promised her mom she would. And now, she was lying on top of a guy who wasn't even her boyfriend, after having sex with him at some slumber party thrown by her slutty classmate that she didn't even want to attend in the first place.

Rory was one step away of having a full blown panic attack. Everything went not according to plan. Everything was wrong! What was she thinking last night? Could that be the effect of alcohol Tristin put in her drink? But then again, Rory didn't feel drunk. Still it surprised her how easily she gave in to Jess's advances and how good it felt being with him. She was daydreaming about kissing him after they started working together, but losing her virginity to him at Louise's house seemed like a step too far from those innocent fantasies. Rory tensed up, she didn't know what to do, but she couldn't bear to wake up and see him walk away, looking at her like nothing ever happened, like she was just another one of his conquests that didn't mean anything. Just because he didn't brag about it in school doesn't mean he didn't have meaningless sex.

Rory carefully disentangled herself from his arms and stood up, locating her slippers. She tiptoed as quietly as possible and left the library closing the door behind her.

When Jess woke up he knew he was alone. There was no weight of Rory's body on his chest, and even though she covered him back with a blanket when she left, he still felt cold. He had a tiny glimmer of hope that maybe, just maybe she woke up early and decided to read somewhere in the corner, they were in the library after all. But his stomach sank at the realization his wishful thinking did not bring her here. She was gone. For some reason it made him feel really lonely. He was kind of hoping to wake up with her and see how she looks like in the morning, all sleepy and cute. No such luck. He rubbed his face in frustration chasing the remnants of sleep away and stood up to leave. He sneaked into Louise's room and located his overnight bag quickly. She was naked lying on top of the guy from Chilton football team, or was it lacrosse? Jess wasn't sure since he wasn't on any of the teams. He got a pang of jealousy of the guy. At least he gets to wake up next to his girl. Jess grabbed his stuff, changed in the hallway and left while the house was still quiet.

He wanted to call her as soon as he got home, but he wasn't sure what he could say. So he hadn't, but he'd stayed at home just in case she calls. She didn't.

On Monday morning he arrived to school in hopes of talking to her there. When he was closing his locker and was just about to head to class he saw her in the opposite end of the corridor. She looked up at him and froze, her eyes wide in panic. She quickly turned around and ran away. He wanted to run after her, but Tristin was standing leaning onto his locker on the other side of the hall watching their interaction. If the guy asked, Jess could always lie that she probably felt awkward after she kissed him on a dare. But Tristin was actually pretty shrewd, so he would probably know it wasn't the case. Jess closed his locker's door and headed into opposite direction towards his first class. He decided to catch up with her later. They still had their project to finish after all. But he didn't see her for the rest of the day, she wasn't in the cafeteria at lunch, and he didn't see her in the halls. She was late for the only class they shared that day, and when the bell rang she was the first one out the door. He wanted to chase after her, but unfortunately Mr. Sherman asked him to stay for a minute to talk about his latest grade. Jess cursed inwardly.

The next two days went by the same way as Monday. He couldn't find her anywhere, and only saw the glimpses of her in the hallways. He started to worry. He thought she enjoyed what they did. He made sure she had an orgasm. It couldn't be that bad, could it? Did she regret the whole thing even happened? She probably did. He didn't want it to be this way. He needed to talk to her about what happened. He was even desperate enough to call her house. Unfortunately, her mom picked up.

"This is Gilmore mansion," the woman chirped.

"Uhh… hi. Can I talk to Rory?... Please." He added for good measure.

"Rory's not home, but I can get a message. Who's asking for her?" Lorelai was surprised to hear a boy on the other end of the line asking for her daughter. That didn't happen since Rory's break up with Dean. But Rory hasn't mentioned any other guy at all. What was that all about?

"It's Jess… We work on a project together. For biology class. In Chilton. She was supposed to give me her notes today, but apparently she forgot. So can you please tell her to call me back? This grade is really important." He made his voice sound as friendly and concerned as he could. The lie rolled off easily from his tongue. He figured he had to be in this woman's good graces if he wanted a chance with her daughter.

"Oh, okay, I'll tell her you called." Lorelai tried to remember if Rory ever mentioned this Jess guy before.

"Thanks. Have a good one." Jess responded.

"You too. Bye." As soon as Lorelai hung up, Rory busted through the door with Lane laughing about something.

"Hey sweets. I have a message for you." Rory looked up at her mother in confusion. "Someone named Jess called. Apparently you didn't give him the notes for your biology project or whatever."

Rory froze on the spot, eyes went wide. No way would he get to the point of actually calling her to her house. Lorelai saw the reaction on her baby's face and furrowed her eyebrows. "Are you alright, hon?"

"Oh God, I can't believe I forgot to give him the notes!" Rory hoped she could successfully conceal her panic over him calling her in the first place, by pretending to be a forgetful project partner.

"You can always give him those tomorrow. He asked you to call him back." Lorelai had a feeling there was something else entirely going on, but she couldn't call Rory out on it with Lane being there.

"I will, thanks mom!" Rory then turned around and gave Lane the look to follow her into her room.

When the door was carefully closed and the music put on to muffle their conversation Rory looked at Lane and her expression went full on panicking.

"Alright, what's going on?" Her friend tugged on her arms to seat down on the bed.

"Lane… I did something really stupid… well, maybe not stupid, but I don't know, something big, huge even, I don't know what to do…" Rory started rambling again, and Lane had to shake her by the shoulders to get her attention.

"Rory, calm down, breathe. What did you do?"

"I had sex." Rory whispered glancing over her shoulder to the door to make sure Lorelai wasn't listening.

"You what?" Lane exclaimed.

"Shh!" Rory waved her hands at her.

"Sorry, you what?" Lane repeated quieter.

"Remember the slumber party I told you about? The one Louise forced me to go, that I didn't want to go to? Well, guess what, I was right in my desire not to attend that particular event. She invited boys as well." Lane's mouth dropped opened and she couldn't let a word out shocked.

"Exactly! What kind of all girls slumber party is that? Apparently the lame one judging by Louise's standards, so she invited guys from our class. And Tristin was there and…"

"No!" Lane interrupted her story. "Please tell me you did not have sex with Tristin?"

"What? No! Ew." Rory made a disgusted face. "It was… it was… Jess…" Rory already told Lane about Jess, about his teasing, and about the project, and about actually getting to know him, and developing a crush on him. She didn't even tell her mom about it. For some reason she thought Lorelai would not take it well, knowing her daughter fell for one of Tristin's friends. Hence Lane was the only one who was in on all the details.

"How did you manage to go from just working on a project together to actually losing your virginity to him?" the Korean girl asked incredulously.

"Well… what happened was…" and Rory went into full rant mode relaying all the events of the party to her friend, from kissing Jess on a dare, to how he found her in the library, to the kissing and exploring and sex itself. Of course she left a lot of the details out, blushing furiously the entire time, and she also didn't want to overwhelm her friend, who's never even been kissed yet. They now seemed like worlds apart. Lane was listening to her with rapt attention, drinking in everything.

"Wow…" was her only reaction when Rory finished.

"Exactly… I don't know what to do… I've been avoiding him since the party, but now he called, and I obviously can't avoid him anymore. But I don't know what to say…" Rory sighed. "Plus, I have to tell my mom about it somehow, and that's the whole other thing. You know how freaky she gets with any sex related topic. She doesn't want me to get pregnant at sixteen like she did, so, me telling her I had sex would probably have an effect of an atomic bomb!"

"But you said you were safe, right? So, there's nothing to worry about?"

"Yes, we used a condom, and I counted the days of my menstrual cycle when I got home, I was already out of the ovulation time frame. The condom didn't break; at least I didn't think it did, so hopefully I have nothing to worry about. But still… you know my mom…"

"Yeah, I do…" Lane trailed off deep in thought. "Well, for what it's worth, I think you still need to talk to him. While you're freaking out here, he's obviously concerned. I mean he did call your home number."

"Maybe he was just worried about the project. He is on a scholarship after all." Rory tried to rationalize Jess's action, not daring to believe he might actually care about her.

"And that makes a pretty valid excuse for you to talk to him. You can't be the reason he loses his tuition. Bad karma points and all that." Lane said matter-of-factly.

"Yeah, you're right. I'm gonna talk to him tomorrow, I guess…."

~XXX~

The next day at school Rory didn't see Jess for the first half of the day. She even started suspecting he might be avoiding her after she didn't call him back last night. But she quickly dismissed that thought. And truth be told, she still didn't know what to say to him and how to act around him, so not seeing him allowed her some time to collect herself. She was held back by a teacher after her last class was finished, so when she came out of the classroom and headed for the lockers to put her stuff away, the hall was almost empty. Except for one person.

Jess was waiting for her near her locker. She had a choice to just turn around and walk out the building, but she realized they had to talk, however unpleasant it might be. She can't run forever. She slowly approached him.

"Hi," her voice came out like a squeak and she cleared her throat.

"Hey," he said back, his face neutral. "We need to talk." She averted her eyes to floor at that.

"I'm almost done with my part of the project, you don't have to worry about it, I'm gonna-" he interrupted her rambling by suddenly saying "What the fuck, Rory?" She flinched and looked up at him. The storm was brewing behind his eyes, he was mad. She didn't expect him to be this angry.

"What do you mean?" she snapped.

"I mean exactly what I said. What the fuck? Why did you ignore me like that?"

"I didn't ignore-"

"The fuck you didn't! We had sex and then you run away from me the second you see me, you don't call me back, you don't call me yourself. What's happening, Rory?" His voice rising. She looked around making sure nobody heard him.

"Would you keep it down? I don't want the entire school to know that now I am another notch on your bedpost!" She hissed. He looked hurt at that.

"Is that what you think about what happened between us?" She didn't say anything back and just shuffled her feet awkwardly. "It wasn't like that for me." He said, his voice quiet, face grim.

"It wasn't?" She looked up at him to see if he was serious or not.

"No! God, I wouldn't go through with it, if I didn't like you! I may act like an asshole at times, but I'm not a complete jerk. I wouldn't take a girl's virginity like that just for the kicks. Is that really how you think of me? That I would be that guy?" The sheer sincerity and hurt on his face made her feel guilty she insinuated that in the first place. "I thought we were friends." He trailed off, suddenly tired.

"We are! I mean… are we? I'd like us to be…" She bit on her lip anxiously. She did not expect this conversation to go this way. She thought that maybe he would ask her to forget anything ever happen and just move on.

"Well, I don't want us to be friends." Her heart sank at those words. She felt the prickles of tears and blinked rapidly a few times to will them away. "I want us to be more than friends." He put his finger under her chin to make her look at him. "Would you like that?"

Her eyes widened at his question. What was happening? Was Jess Mariano asking her out?

"I… I… what?" She stammered.

"Rory…" He just couldn't help himself, he leaned in and kissed her softly. It surprised him how much he missed her these past few days. It wasn't a lie that he thought they were becoming friends. They saw each other every day in school, and he liked their interactions, he liked sharing things with her during their study sessions, and after what happened at Louise's party, he couldn't imagine just not being around Rory. He wanted to ask her out even before the party, but now that they actually slept together, it seemed so natural and obvious to him, so the fact that she completely ignored him afterwards hurt immensely. She stood there frozen in place while he pressed his lips to hers. But when he licked her bottom lip lightly, it spurred her into action and she responded with fervor. She felt his arms wrapping around her waist pulling her closer to his solid body. When they broke apart, he pressed his forehead to hers, eyes closed, breathing labored.

"You have no idea how awful it was to wake up to you being gone." He finally said. "Why did you leave?"

"I… I freaked out, I guess… I mean… I didn't even want to go that party in the first place. I didn't plan on playing that stupid game, much less having sex for the first time. So when I woke up, I guess the realization just dawned on me and I didn't know what to do. I'm sorry if I upset you."

"I was pretty upset."

"You were?"

"Oh yeah, because I didn't get a chance to do this…" he leaned down and planted an open-mouthed kiss on her pulse point. "Or this…" he went up and sucked her earlobe in between his lips. She let out a tiny whimper. "Rory, I want you to know that you're not just another notch on my belt, don't ever think that. Okay?" He said completely serious.

"Then how… why did you… what?..." Rory didn't even know herself what she wanted to ask him.

"Truth be told, I wanted to ask you out for a while now, but I figured I'd wait till we finish with the project. That way if you didn't want to go out with me, it wouldn't be awkward, because we wouldn't have to work together anymore. I didn't want you to say yes just because we were still paired up together, and you felt guilty for saying no." He was gently stroking her back, his eyes were warm, he wasn't angry anymore. "So, when you kissed me first for a dare, and then in the library, I just couldn't help myself. Of course I didn't expect to actually have sex with you, but it was a really nice bonus." He smirked at her, and she blushed averting her gaze, the topic still making her uncomfortable. "But now that we've done it, I kinda wanna do that all the time." He leaned in and captured her lips in another passionate kiss.

"Hey… we haven't even been on a date yet, and you already have such requests. That wouldn't do, mister." She chided playfully.

"Okay then, let's go on a date. Does tomorrow sound good?"

"Uh, wait, tomorrow is Friday. No, I can't on Friday." She made a face. He lifted a questioning brow at her. "I have dinner with my grandparents every Friday. That's how my tuition here is paid for. My mom's not rich, but my grandparents are. My mom asked them to help pay for Chilton, and my grandma blackmailed her into having weekly dinners." She realized she was rambling again and stopped.

"Huh," was all he said.

"So… maybe Saturday?" She looked at him with a hopeful expression.

"Yeah, okay. My shift ends at 4, so how about we meet at 5 pm at the bus station? Can you come to Hartford? I'm gonna take you back, and by take you I mean get on the bus with you, since I'm still saving for a car." Rory knew that Jess wasn't coming from the rich and elite family, so not having a car was natural. She admired him for working at his father's diner 'Dante's Inferno' to save the money, so that he would be able to call this car his own when he finally bought it.

"Okay, great!" she beamed at him.

"Great. But just because we're gonna have a date, doesn't stop me from wanting to do this," he kissed her again and expertly maneuvered her around and pressed her back against the lockers.

"Jess…" she whispered softly in protest. "We can't keep doing that here, someone might see."

"You're right. The things I'm planning to do with you don't require an audience. C'mon." He pulled her by the hand down the corridor, and soon they were inside the school library. It was deserted since the majority of the students already left after classes were over. The librarian had some hearing problems, so she didn't hear when the door opened and they came inside. He closed the door carefully behind them, and tugged her towards the farther end of the library. She followed him with no objections. Finally they stopped at the very private nook with a small round table and a few chairs. It was surrounded by bookshelves and judging by the layer of dust on those, it hasn't been used very often. When they stopped he turned to her and attacked her lips immediately. But Rory was not having it.

"Are you serious? In the library?" she gave him an incredulous stare. "Is that, like, your make out spot? How many girls did you bring here?" Something changed in his eyes, they became hard again.

"Rory, I already told you this thing between us, it's not just a chase, a game or whatever. I've never brought any girls here. This is actually my reading spot. I hide here when I don't wanna see anyone. This corner is so rarely used, I'm probably the only one who knows about it at this point."

"Then why did you bring me here?"

"Because the first time we did it also happened in the library." He smirked. "I thought you'd appreciate the beauty of this moment. Plus, what I want to do to you kinda requires a surface where you can sit on."

"What do you mean?" Rory's breathing hitched.

"You have no idea how sweet you taste, do you, Rory?" he made her step back until her butt hit the edge of the table. Then he put his hands underneath her skirt, the Chilton plaid formal skirt of the appropriate length, the skirt that covered something he longed for ever since he tasted her. When he reached her underwear, he slid it down in one smooth motion that left her speechless. She didn't know what to expect. He leaned and whispered into her ear. "I've been dreaming about it ever since that night at the party. I literally see dreams about you every night when I fall asleep." His voice low and husky filled with desire. He lifted her up easily and set her down on the table. Then he grabbed one of the chairs and set it the way he would be between her legs when he sat down on it. She was watching his actions mesmerized. All of his movements were so graceful, so masculine. It made her pussy throb. Her underwear was currently tucked in his pocket, and she was sitting on the table in the school library without any panties on. He took her hips and pulled her closer to him, gently urging her to lie down. She propped her upper body on her elbows to be able to see what's going on.

"Even though the librarian is like a thousand years old and probably won't hear a thing, but still, try to keep quiet. We are in the library, after all." He gave her a wicked smirk before diving right in between her legs. He bunched up her skirt and moved her legs to wrap around his neck. The very first lick made him growl lowly in between her legs. "Fuck, you're perfect, Rory." He started off with teasing her entrance with the tip of his tongue, tasting her, lapping at her, not able to get enough. If she hasn't been avoiding him, they could've been doing this every day. No one ever went to this part of the library, they were safe here. The very idea of being able to eat her out, to taste her whenever he wanted sent all of the blood to his crotch. She was writhing on the table, whining and whimpering softly, thank god she wasn't a screamer. When he went up to her clit though, the whimpers turned into small moans, she fell back on the table, and eyes closed in pleasure. He kept working on her pussy until she couldn't take it anymore. She clamped her mouth with her palm to muffle her final moan as she came.

When he pulled away, his face was glistening with her fluids. He looked very satisfied, smug even. She opened her eyes to look at him, dazed. When he leaned down to kiss her, she pulled him closer eagerly tasting herself on his tongue. For some reason she found that super arousing.

"I wanna do this every day, taste you every single day." He whispered hotly in her ear, she shivered. "You're so sweet, so delicious, fuck, Rory… I wanna fuck you so badly." His erection was pressing into her core and she was way too sated to care at this point.

"Do you have a condom?"

"Yeah."

"Then what are you waiting for?" She smirked at him, her face so naughty, in that moment nobody would even think about calling her Mary.

He wrapped his cock into latex protection and positioned himself at her entrance.

"Are you ready?" he asked just in case, she nodded in response. And he went inside. She was all wet and relaxed after her first orgasm, so his cock slid in with ease. The stretching sensation was so pleasant for the both of them they moaned in unison. He stilled for a moment letting them both get used to the feeling. Ever since they've done it at the party, having sex with her was the only thing he could think about. She was so deliciously tight it took him a moment to regain his composure. He did not want to cum too early like the first time. Thankfully, he was on top now, so it gave him more freedom to control the process and change tactics when it was too overwhelming for him. He leaned back and held her close grabbing one of her hips. He placed the other hand on her pubis and pressed his thumb to her clit. He accompanied his thrusts with rhythmic circles he rubbed against her clit and soon the sounds she was making were more desperate, more pleasurable, it looked like she was getting close. He kept fucking her relentlessly, increasing the pressure on her clit, and soon she tightened around him and orgasmed with a muffled cry, her walls spasming around him. He made a few deep and hard thrusts and came himself.

After a moment he pulled out to dispose the condom. There were no trashcans anywhere near them, so he just tied the condom and hid it in his backpack. Rory was still lying on the table trying to catch her breath. Her body felt like jello after two orgasms in a row. He turned back to look at her and couldn't help a happy crooked smile. He was proud of himself for holding on long enough to make her cum. She had that pink glow about her that made her look so pretty, he couldn't fight the urge to come closer and scoop her into his arms to kiss her hard. She responded lazily, still relaxed after sex.

"Just so you know, I'm keeping your panties as a souvenir." He murmured against her lips. She gasped in indignation.

"Jess! There's no way I'm going home without my underwear! How am I gonna sit on the bus the entire time?"

"With your legs crossed, obviously." Came his cheeky reply.

"Jerk!" She slapped him lightly on the chest.

"You like it," he winked at her. "C'mon, the library is gonna close soon. And you have a bus to catch, Miss Flasher." She slapped him again, he just laughed at her.

They fixed their clothes and headed out of the library holding hands.

He was walking her to the bus stop. Jess lived in Hartford in a walking distance from Chilton, so he needed to head the other way from the bus stop, but he wanted to prolong their moments together.

"Jess?" She asked, her voice timid, gaze lowered.

"Hmm?" He thought she acted weird. Was there something wrong again? He could really do without another freak out. But at least he was there and awake this time to stop it from escalating.

"Does it mean we're dating? As in, boyfriend and girlfriend."

"Do you want to?" He gave her a side glance.

"Yeah…" She responded.

"Then we're dating." He shrugged like it was no big deal.

"Really?"

"Yeah. Now hop on the bus, girlfriend." He smirked at her, and she blushed that pretty shade of pink again. As she turned to step into the bus he called after her. "Don't forget to cross your legs."

She gave him a withering stare, and he mimed the arrow in his heart, which made her giggle. He leaned in to kiss her softly on the lips.

"See you tomorrow… Boyfriend." She said, her eyes playful and happy.

"Beat it," he gave her a soft look before turning around and heading towards his place with a spring in his step. He put his hands in his pockets out of habit, and smirked at the feel of cotton of Rory's panties under his fingers. Correction, his girlfriend's panties. He definitely did not regret going to that party. Not one bit.

A/N: Well, this is it. This story was basically an excuse for writing some shameless literati smut, since it felt like I've read everything lemony there is to read, and it's still wasn't enough. Thank you for all the lovely reviews, thank you for those who followed the story and added it to your favourites. You might as well leave a review telling me why you did that *hint hint, nudge nudge*

I was actually surprised this story got any reads at all, since it's been forever since the show aired. So, I also thank those silent readers who spent their precious time on this piece of writing.

My literati phase isn't over yet, so hopefully I will see you in the next one.

~Roxy x