Chapter Text
Rory heard a light tap on her window and stood up from her desk, stretching tired muscles to open the window for Jess. She pushed the frame up and looked outside to find her boyfriend standing there with a to-go cup of coffee from Luke's.
"Hey," he said giving the coffee to her.
"Bless you!" She took it gratefully, gulping hungrily.
"You didn't come by the diner after school, thought you might need some fuel."
"Yeah, I had to study. I have this stupid history test tomorrow," Rory groaned.
"When do you think you're gonna be done with it?"
"About ten, maybe?" He nodded in response.
"I'll leave you to it then," he gave her a small smile and almost turned to leave, when she tugged on his arm, and pressed her lips to his in a brief kiss.
"Thank you for the coffee, you're my hero."
"No problem."
~xxx~
A little after ten Rory stood up from her chair, every vertebra creaking in protest from being in the same position for too long. She was just putting her books and notepads away when she heard a tap on her window once again. She smiled to herself and went to open it for the second time that night.
"Hey, how's your studying going?" Jess asked intertwining his fingers with hers through the frame.
"I just finished. Wanna come in for a bit?"
"Where's your mom?"
"She's staying at Alex's tonight."
"Huh," he smirked at that piece of information. Coming here was a right choice after all. He snuck inside with the grace of a cat, closing the window behind him. Rory plopped on her back across the bed.
"I'm exhausted, all those dates and names, I have no idea how I'm gonna remember it all tomorrow, so much cramming with only one cup of coffee is an impossible task." She whined. Jess came to lie next to her, taking her hand in his.
"I know a great way to help you relax," he started.
"Which is?" She turned to look at him.
"Orgasm," he smirked.
She gulped nervously. She let him touch her boobs through her clothes for the first time a few weeks ago, and since then Jess was dropping hints about doing something more, but she still wasn't ready to have sex with him. She didn't want to offend him, but didn't want to go all the way either. It was quite a predicament.
"Uhh... I'm not... You know..."
"I know. You don't have to have sex to get an orgasm, you know?" He turned to look at her only to catch her turning away from him, her cheeks flaming red.
"Oh..." She didn't know how to react to that. What did he expect?
"It's okay if you're not ready for that either," he squeezed her fingers tighter in reassurance.
A long pause followed. Jess seemed relaxed, enjoying just being next to her, while Rory's thoughts were racing a mile a minute. Was she ready for anything sexual at all? It sounded kind of enticing. Scary, but enticing nonetheless. And her mom wasn't going to be home till morning. But she had a test tomorrow, so she couldn't be late for school. She didn't want the repeat of her first year with that meltdown about a Shakespear test. Then again, it wasn't awfully late yet, and she could use some relaxation.... She squeezed Jess's fingers to get his attention, and asked.
"What else can we do for... You know, uh, orgasm?" She could see his smirk out of the corner of her eye. She still didn't dare to look at him directly, too embarrassed and shy about the whole conversation.
"Remember how I touched your breasts the other day? I can touch you like that down there too. Over the clothes. If you want."
"Okay," she whispered after a moment of hesitation. She felt him move to hover above her. They locked eyes before he pressed a soft kiss to her lips, coaxing her to relax. The very next second her instincts kicked in and she lost herself in the kiss, like she always did with him.
They were making out for a bit until she felt his palm covering her breast gently. He started massaging it, kneading and rolling her nipple between his deft fingers. She moaned into his mouth. She wasn't wearing a bra underneath her sweatshirt, so she could feel everything. Encouraged by her reactions he went to kiss and suck on the sensitive skin of her neck. His hand never leaving her chest, alternating between her soft mounds. Rory was clutching at his back, threading fingers through his hair, pulling his head closer to her neck. She loved it when he kissed her neck. Then slowly his hand started travelling lower until it came to the juncture between her legs. She pressed them together, losing focus for a second.
He looked up at her. "May I?" She nodded shakily and relaxed her thighs. His palm landed on her pubic bone and just settled there, his fingers between her legs, applying pressure and heat to the most intimate spot even through her sweatpants. His eyes went completely dark, contrasting to his usual hazel shade. Her lips parted in anticipation, and he started rubbing her softly, careful not to scare her with overwhelming sensations. It felt weird in a way that she never let anyone do that to her, but she still didn't quite understand what she was supposed to be feeling. And then.... He found her clit and everything changed. She gasped suddenly at the shock of feeling like an electric current went through her limbs.
Jess focused on that spot he found, and started rubbing her there in circles, increasing the pressure some. Her eyes closed and she was washed with pleasure she's never felt before. He kept caressing her methodically, tirelessly until her breathing got shallow and with one final moan, she climaxed in front of him.
"There you go," he whispered pressing a soft kiss to her forehead, extracting his hand from between her legs slowly.
Rory was lying there with her eyes closed, breathing erratic, her mind completely blank of all the thoughts and concerns. She blindly reached for him, and he intertwined their fingers one more time. Watching her was such a treat. Looking at her pale cheeks gaining color, and then shining bright pink with arousal, her lips parting, her tongue darting out to lick them, her chest rising and falling, nipples hard, poking through the fabric. She was a vision. And he was pretty sure he just gave her the first ever orgasm of her life.