Rory steps off her bus from Chilton and enters Luke's diner.
"Hey Rory," Luke greets her.
"Hey Luke, is Jess around?"
"Umm… he isn't back from school yet, I don't know where he is. Sorry."
"No, that's fine. I need to talk to you about something."
"Sure, what?"
"Well, Jess was telling me that his teacher is going to talk to you about him attending Chilton next semester."
"Wow, that's great, I never thought Jess would get into Chilton."
"He's really smart and I think he'd really like it. We have this "shadowing" program at school, and it's for people interested in attending the school." Rory drops a form down on the counter for Luke to look at. "So he would follow me around all day to all my classes and see what it's like. I just need you to sign and the principal of Stars Hollow to allow Jess to take the day off."
"Ok, Rory. This sounds good. It's worth a try. I'll give this back to you tomorrow and then he can come with you in two days. Do you want to tell Jess or surprise him the morning of?"
Rory and Luke look at each other and simultaneously said, "Surprise him."
----------
Two Days LaterRory gets up extra early and dresses in her uniform and her saddle shoes and wakes her mom up and tells her to meet her at Luke's.
Rory enters the diner and she and Luke smile at one another, Jess is going to Chilton today. "Can I go up?" Rory asks.
"Yeah, go right ahead." Luke responds, eager for the news to be broken to his nephew.
Rory cautiously approaches the door; she places her hand on the doorknob, but decides to knock. No answer. She opens the door slowly and peeks inside to see Jess cuddled up with his blanket wrapped around him asleep on his bed.
His window is open and Rory begins to shiver because of the cold air entering and encircling her in the apartment.
Rory approaches Jess, leans on his arm and says, "Jess, wake up! I'm cold."
Jess opens his eyes to see Rory's beautiful face, not a bad sight to wake up to. He avoids asking why she is up there or anything to make her uncomfortable or make her want to leave. He is happy she is there, for whatever reason, and he is just going to enjoy it.
"Well, I can't really help you. I'm perfectly fine." Jess explains.
"That's because you have a blanket on."
"Well, hop in." Jess scoots over and holds up his blanket giving Rory a perfect spot to lie down.
Rory would never consider getting in bed with Jess, when she is still with Dean. But she is so cold! She gets in bed and pulls the blanket tight around her. Jess feels her shivering and hugs her tightly and rubs her arms to warm her up.
"Rory?"
"Yes?"
"You're in my bed."
"Yes I am."
"Not that I'm complaining, but is there any reason?"
"Yes there is."
"Are you going to tell me what it is?"
"Not just yet, go get ready."
"Ok, whatever you say Rory."
Jess slips out of bed from the other side and makes his way to the bathroom to shower. Jess is wearing just plaid pajama bottoms, quite obviously without underwear of any sort because his pants are hanging down past where his boxers would start. Not that Rory minded… wait, she should mind. Why is she looking at Jess's cute, tight ass and hard, ripped abs? Oh God. Just stop. Rory's with Dean. Dean is her boyfriend. She loves Dean. She needs to keep reminding herself of that. But why is she is Jess's bed?
She smells the pillow she is resting on. Mmm, Jess. He smells as yummy as he looks. Damn it Rory! Stop it! She probably should just exit the room, yeah, leave. Ok, Rory, that requires movement. Move.
Jess just then walks out of the bathroom with wet hair falling and dripping onto his face and down his already wet chest. He just has a towel wrapped around his waist. Rory can't help but glance at him standing by his dresser picking out his outfit for the day.
Jess pulls out a pair of jeans. Rory loves the way he looks in them so she finds it hard to ask him to change into something other than jeans. The dress code at Chilton for people "shadowing" does not allow jeans.
"Jess, do you think you could wear your cords today?"
"…Sure, any reason why?"
"Uh…" Not wanting to spill the secret, "because I think you look hot in them." Rory lets it out and then blushes furiously and pulls the blanket over her face. Why did that have to come out? Why was that the only reason she could come up with? Maybe because it's true…
When Rory pulls the blanket down, Jess is grinning as wide as she's ever seen.
"Ok, cords it is." Jess pulls out a pair of boxers and his gray corduroy pants and a black button down shirt. He takes it all into the bathroom and in a minute returns in the clothes.
He stands in front of the mirror and is about to do his hair when Rory interrupts herself watching him with fascination and says, "stop," as she is standing up and walking over to him.
"What?" Jess pauses and asks her.
"I want to do it."
"Huh?"
"Can I do your hair? I've always wanted to do your hair. Can I do it?"
"Sure Rory." Jess hands her a tub of a pomade greasy mess, with a huge smirk on his face.
She takes a glob onto her hand and puts it into Jess's hair. She is standing face to face with Jess and she is focusing on his hair as she is repeatedly running her fingers through his sexy hair. She is surprised at how sensual this feels, but now she needs to finish doing it because she has already started.
Jess is completely aroused watching Rory this close to him. He could look up at her face, which he loves, or down at her breasts, which are also a nice sight.
She finishes doing his hair and takes a step back. She smiles at her work and goes to wash her hands.
Jess throws on some shoes and Rory and Jess walk down stairs to the dinner side by side.
"You want to get some breakfast?" Jess asks Rory.
"Sure, let's get two coffees and two doughnuts to go. We can eat them on the bus."
"What? See that Rory?" he points, "That's my school, across the street. No buses."
"Nope, not today. See this? This is a form saying that you're coming with me to Chilton today, and see that," she points, "that's the bus stop we're going to go wait at until the bus comes to take us to my school, and your school for the day."
Jess reads the form and tries to hold in a smile. He shouldn't be happy about this, but he is.
They say goodbye to Lorelai and Luke and get their breakfast to go and wait and sit at the bus stop and eat in silence.
"I hope you're not mad about Luke and I planning this behind your back."
"You mean getting me out of a day of that boring school I attend? And forcing me to spend the whole day with you? Yeah, I think I'll let it slide this time." Jess says with a smirk. "So I get to follow you around all day?"
"Yep, you get to be my shadow."
"Man, I'm lucky." Jess mutters, low enough for Rory to hear and know that she wasn't supposed to.
A/N: Yes, shadowing is a real thing. I shadowed my friend to her Catholic private school, and that's where I got the idea for this fiction, I thought it would be the perfect opportunity to throw Jess and Rory together. I hope you're enjoying this. I have nothing planned; I just surprise myself as I write. So, any suggestions would be very much appreciated!