A/N: BTW, the Letters to Cleo song in the end of The Middle was "Co-Pilot" from "Go!" I love that CD!…much tripyness…Anyhoo, here it is….my first lemon-type. I think I'll rate it NC-17 to be safe. Eh, I hope my mom's not reading this…

**********

Ready or Not

"Mom?" Rory asked hesitantly one night. It had been months since she'd first come to her decision, but she had yet to come up with the courage to talk to her mother about it.

Lorelai stopped the tape halfway through the credits and turned to her daughter. "Yeah?"

"How did you know you were ready? For…sex?"

Lorelai blinked a few times before answering. "Huh. I've honestly expected this little conversation for a while now. Ever since you started going with Jess. My, he's a patient fellow. It's been more than a year."

"Mom," Rory sighed, feeling herself beginning to blush. "Please, just answer my question."

"Well, I'm not sure I was ready, my first time. I'm pretty sure I was just rebelling, although I'm just looking back on it. I don't know: maybe when you have enough confidence in yourself and the other person to know that it won't make things weird, but better. Maybe when you are proud to be giving yourself to another person. I don't know, it's probably different for everyone." Lorelai reached for Rory's hand. "Do you think you are?"

Rory sighed, and thought over her relationship. She'd grown used to wanting Jess, to wanting to kiss him, to touch him, to feel his hands over her. And his hands had been most places on her: their make-out sessions—for lack of a better term—had been pretty hot-and-heavy for the last few months but always stopped short of anything that could be termed a sexual act.

And she knew what it was like to sleep next to him, in a bed, without a lot of her clothes. And he'd never pushed her past her limits. In fact, he seemed to know her limits almost more than she did, always stopping a millisecond before her feelings of discomfort registered.

"Yes," she said. "I am. But…how do I approach it?"

"I don't know, hon," Lorelai said. "That's between you and Jess. You will be safe, right? Protection, all that? Do you want to go onto birth control?"

"Maybe," Rory said, wrinkling her nose in thought. "I don't know. But…what if I'm…inadequate?"

Lorelai choked back a laugh. "I don't mean to laugh, hon," she said when Rory looked at her, slightly hurt. "Really. It's not a funny thing. But you are my daughter. And beyond that, I've seen the way Jess looks at you. There's no way there's going to be anything inadequate about it."

"He's really sweet," Rory said quietly. "He hides it well, most of the time. But he is sweet. And considerate. You were right when you said he was shy."

"Witness me gloating like I said I would," Lorelai said, fluffing her hair and smiling.

"I know, I know," Rory said. She flopped into her mother's lap and felt her mom's hand start to comb through her hair. "I do know, mom. It's just…Jess is so confident. He's so smart and sure of himself; how could he be shy? I still don't get it."

"There's no telling what makes people shy. Some are just naturally reserved, and slow to open up to people. And to tell you the truth, most that do open up quickly don't open up very much: it's usually shallow relationships they share. Not always, I fully admit."

"Thanks, mom," Rory said. She looked at her watch. "I better get to sleep. Hell."

"Ah," Lorelai said. "But second-half-of-senior-year Hell. You'll be out of here and moving into the Harvard dorms before you can even say 'Valedictorian!'"

"If Paris doesn't kill me first," Rory groaned. "She wants Valedictorian so bad I'm actually afraid for my life."

"After all this, she's still Paris, isn't she?"

"She'll always be Paris," Rory said. "Goodnight." She kissed her mother and went off to her room.

Lorelai grabbed a pillow and hugged it as she fell into a lying position on the couch. *Oh, god,* she thought. *Rory is going to be having sex soon. With Jess. Is this how mom felt? Blech, I don't think I like it. Rory is my best friend, and I'm going to encourage her through this.* She sighed and put the pillow under her head. *I think I'll take the Scarlet defense and think about this some other time.*

That decided, she climbed the stairs to bed.

**********

Her usual day at school completed, Rory got off the bus and walked to Luke's. She went in and exchanged pleasantries with everyone then went up to Jess behind the counter. He'd graduated the year before—not just barely, thanks to Rory's incentives—and had begun working at the diner full time.

"Hey," Rory said, dropping her school bag and smiling broadly at him.

"Hey," he said back. "So, Paris didn't maim you today? Impressive."

Since the night the three had spent at Rory's house almost two years ago, the three had gotten together at least every once in a while to discuss books, and had become as close to friends as they could. "I think she wanted to a couple times," Rory said. "There were numerous announcements about early purchase of caps and gowns, with special emphasis on the special robes for honor roll and such."

"Ooh," Jess said sympathetically. "Bet that was fun. What shade of purple did she turn?"

"I think it was degree ten, although it was pretty close to a thirteen."

"Impressive."

"So, where's my coffee?" Rory demanded.

"Coming right up as soon as it brews. I poured the last cup right before you probably stepped off the bus."

"Punk," she muttered under her breath.

"Hmm, yes," Jess agreed, and went to attend to his job. While he worked, Rory finished her homework. The two worked side-by-side, helping each other when the need arose. Many tourists watching could only admire the near-perfect balance the two had in their relationship.

After Lorelai got off work, she came in and sat next to Rory. "Jeez," she said. "Think you're taking up enough space here?" She shoved a few papers into a pile and then put them under one of Rory's textbooks.

"I'm not," Rory said. "Really. And I'm almost done. I just need to finish this Physics homework, and then I'm free for the rest of the night." A few minutes later, she closed the textbook with finality. "So, what are you and Luke doing tonight?" she asked Lorelai.

"I don't know," she answered. "Where is he, anyway?" she asked Jess.

"I think he's showing an apartment."

"Really?" Lorelai rolled her eyes towards the ceiling, obviously trying to see through it into the apartments. "Wow. Cool. So, more money, huh? Wonder what I can do with that?" She rubbed her hands together greedily.

"You look like a praying mantis," Jess observed. When Lorelai glared at him, he smiled. "But only in the fact that you're doing the hand thing. Otherwise there's absolutely no resemblance." He gave her his best innocent face, which Rory had coached him on.

"Hmm," Lorelai said, putting her hands around her coffee mug. "I think I'll forgive you this time. But watch your step."

"Got it," Jess said, looking down at his feet as he walked out into the diner proper to take an order.

"Literalist," Lorelai muttered and sipped her coffee. She looked at Rory, who was watching her boyfriend work and smiling. "So, think of anything yet?"

Rory blanched and looked at her mother. "No," she said. She of course knew exactly what her mother was talking about, but wasn't going to say anything specific in the diner. "I don't know. I mean, do I just blurt it out, or should I work up to it slowly?"

"Can you…um, show him…rather than tell him?"

Rory blushed slightly. "I could, but that could backfire. If I don't say it explicitly, he might resent himself…or something else stupid like that. No, I've got to tell him. Maybe I should write a speech."

"Maybe you should just tell him tonight."

"Yeah," Rory said. "Maybe."

**********

That night, Luke and Lorelai went out as usual, and Rory and Jess stayed in, also as usual. "Reading or movie?" Jess asked, settling into a comfortable position, waiting for her to join him.

"Talking," Rory said. One of Jess' eyebrows raised, and he sat up.

"Okay," he said hesitantly. "Let's see. You're kind of pale, you didn't eat much tonight, you've been nervous all day…I'm stumped. What's wrong?"

"I've come to a decision, recently," Rory began, and then chided herself for sounding far too formal. She sat down and took his hand. She examined the fingers closely while she said softly, "I'm ready."

His other hand reached up and tilted her face to his. His eyes bored into hers, making her feel utterly exposed. But she felt no shame, no embarrassment. Only anticipation. "Rory," Jess breathed, understanding perfectly. "Are you sure? I want no doubts in your mind."

"Yes, I'm sure," Rory said. She leaned forward and kissed him. "Positively sure. I want to make love to you."

He hugged her tightly, pulling her onto his lap. He kissed her lightly. "It'll be so good," he murmured into her ear. His hands slid down her back caressing her tenderly.

"I know it will," Rory said.

"When do you want to do it?" he asked, trying not to sound too eager.

"Um, what's wrong with now?"

Jess smiled. "If you were any other girl, nothing. But I love you, and you deserve candlelight, flowers, and a bigger bed than this. I aim to give you that."

"What about you?"

"What about me?"

"What do you need?"

"Only you." He kissed her, deeply, intensely. "You're all I need."

"Jess," Rory said, her hand stroking his cheek. "I don't need all that. It can be saved for another time."

"But—"

"Do you know what it means to me, that you were wanting those things? For me, and for you?" She smiled at him. "It's incredible. You've got such a tough-guy exterior, and inside, you're as mushy as Sleepless in Seattle."

"Now, there's no need to get rude about it," Jess huffed. But he subsided when Rory kissed him. They stayed in the embrace for a long time.

Finally, Rory stood, and stepped away from the bed. She closed the door, then stood facing Jess on the bed. He was looking at her in confusion, but his eyes widened when she began unbuttoning her shirt. "Rory," Jess said.

"You have condoms?" she asked.

"Yeah," he said. Then he blushed. "Not that I was, you know, expecting this, or anything. It's just the whole, Boy Scout 'be prepared' thing. I didn't carry anything around just because we're going out. I mean—"

"Jess," Rory interrupted gently. "Be quiet. You've seen most of me before," she said, slowly sliding her shirt off her shoulders. She wore no bra, and Jess sighed as he always did at her beauty. And he knew that no one but him had seen this beauty without her clothes. She unbuttoned her jeans first, then slowly slid the zipper down. The flaps parted, and she pushed the jeans past her hips slowly, until gravity pulled them to the floor.

"Rory," Jess breathed. "Oh, god, you're so…"

"Shh," she said, stepping towards him. He now perched on the edge of the bed, and she slowly straddled him. He kissed her between her breasts, and she sighed. Then she pushed him gently back, until she could begin on his shirt. His fingers lightly glided over the skin of her back, causing her to shiver. They moved up to her shoulders, and began combing through her hair.

Suddenly, she bent until she could place a kiss on his bare shoulders. "Lie back," she murmured. He had no choice but to do as she said. He lay on his back, unable to take his eyes off Rory. She looked like some sort of mythical creature, a sprite, or fairy. "Nymph" had such bad connotations now, but he wanted to call her that. She was willowy, tall, and beautiful. And his.

Her mouth moved all over him, from his bellybutton to his neck, where she placed a few kisses. "Rory," he said, his voice hoarse. He felt as if his vocal chords were singed and had trouble forming words.

"Hmm?"

"You're driving me crazy," he said.

She chuckled against his skin, and smiled. "I know. I think it's about time, don't you? I don't understand how you've been so patient," she continued. She slid until she was straddling his legs. She reached for the waistband of his pants, and before he could protest had the buttons undone.

She was flushed, and he didn't think it was from embarrassment. She had a look in her eye he'd never seen before, and couldn't identify. His pants slid from his hips with only slight difficulty, and soon Rory was inching down the elastic of his briefs.

"Rory," Jess said. But she ignored him. He was naked to her gaze, and he fought bashfulness. She took hold of him, very firmly, yet still gentle, and he groaned, loudly.

"Rory," he said again, sharply enough that she looked up, her adventurous smile fading.

"I didn't hurt you, did I?"

"No," he said. "You're just killing me. Come here." He pulled her up until she lay next to him. He pulled her into a gentle kiss, which heated until neither could breathe. They pulled apart, panting slightly for air, and Jess looked her up and down. "I'm thinking we're a little uneven here," he said. "Your turn to lie back." She agreeably did so.

He moved down, and removed her remaining undergarment. Then he began to kiss her body, causing her to arch her back and make small, satisfied noises. He began at her neck, one of his favorite parts of her, and began inching his way down. He suckled her breasts, gently at first, then with rising intensity as she began to writhe under him.

"Jess!" Rory cried, running her hands through his hair. "What are you doing to me?" she demanded breathlessly.

"The exact same thing you do to me," he answered. He kissed downward, over her stomach, and below. This was uncharted territory for him: with the other girl, they'd never indulged in anything resembling foreplay. Slowly he learned her, kissed her, touched her, until he heard her gasping for breath. Then he felt her whole body tighten and arch, and he knew he'd given her an orgasm.

He moved up to lay next to her, watching her as she lay a bit dazed from the pleasure. "God," she moaned. "I didn't know anything could be like that. Jess, I love you," she murmured, and pulled him to her for a kiss.

"I love you, too, Rory. Now, hold on a minute." He got off his bed and rooted around in one of his drawers. He came out with a box of condoms, and removed one. He couldn't keep the smile off his face as he looked at her, lying on his bed, looking utterly satisfied. "I've had fantasies that weren't nearly as tempting as this," he told her bluntly. Now she blushed.

"Really?" she asked. "You've fantasized about this?"

"Often," he said. He moved next to her, and opened the condom. When he moved to put it on himself, Rory said, "Can I do it?"

Jess stifled a groan. "Sure," he said. He barely survived the process. "You know," he said when she was done. He pushed her gently to her back, and moved on top of her. "This might hurt you."

"I know," Rory said. "It's supposed to hurt, mostly, your first time." She leaned up and kissed him, pulling him down until he pressed against her.

He gently pushed himself inside of her. He felt Rory gasp, but she held his mouth to hers as he intruded further. She made a small protesting sound, but didn't let him move away.

Slowly, she became acclimated to him, and they began moving in tandem, building to a peak together.

**********

He lay half on top of her, both of them gasping for breath and clinging to each other. "I love you," Rory murmured, and placed a kiss on his shoulder.

"I love you," he said. He mustered the strength to turn over, and they immediately curled together. Rory absently let her fingers walk over his chest.

"I love touching you," she said, watching her own fingers move over his lightly tanned skin. "I love talking to you."

"So what are you going to do when you go to Harvard?" Jess was always slightly worried about that time. He didn't look forward to it. "I mean, you're going to be living in the dorms, hours from here, and meeting all these college guys."

"And I'm guessing that you're smarter than all of them," Rory said. "I wish you would apply to Boston College, or something. Then we could go to school together." She looked away from his face. "Or live together."

"But what would I do?" he asked rhetorically.

"You'd be going to college."

"Not likely. I can't afford any college. No one in my family has the money for it, much less me. All I know, Rory, is basic appliance repair, diner-running, and books." He got a glimmer of an idea just then, but let it stew at the back of his mind.

"You're smart enough to do anything you want," Rory scolded him.

"Let's talk about this some other time, okay?" Jess said desperately. "I'm sorry I brought it up, mea culpa, mea culpa. Why don't we just lie here in the contentment of afterglow?"

"All right," Rory agreed, smiling, and pulling him closer.