Multi-Fandom Fanfiction Compilation SMUT 18+⚠️

Jess Mariano(Gilmore Girls)

Swimsuit model (Y/N) (L/N) is new to the Stars Hollow community. She just moved from the Bronx after her divorce from Yankees pitcher, Jackson Winslow. She's met a few people including Jess Mariano. Both are quite smitten with each other. This particular morning, Jess comes by to surprise Y/N with breakfast from Luke's Diner. However, she's on her morning jog. When she returns, she sees Jess on her front porch & pulls out her headphones.
"Morning", he smiles.
"Hey. Morning. What's this?"
"Breakfast", he says holding up the food.
"Aww. Thanks. That's so sweet." They walk into her house & head into the kitchen.

He passes her a coffee. She takes a sip & closes her eyes.
"Mmm. So good", she says. He chuckles. He brought over some bagels & cream cheese.
"I need to ask you something."
"Okay. What is it?", she asks spreading cream cheese multi-grain on her bagel.
"There's a movie night tonight in the town square. Do you want to be my date?"
"Movie night, huh? Sounds awesome. I'd love to be your date."
"Cool. I'll pick you up say, around six?"
"Sounds great." They chat for a bit while finishing their breakfast.
"Thanks for the food. It was exactly what I needed."
"You're welcome", he says getting up.
"Well, I better go. The gazette doesn't write itself." She walks him to the door.
"See you tonight", he says.
"See ya." They kiss quickly then Jess leaves.

She heads to her bathroom & takes a shower. After a quick shower, she sends a slightly risqué photo to Jess when she gets out to dry off. Once she gets dressed, Jess sends her a text back.

"Seriously? You're killing me here. I'm trying to work." Another texts pops up. "So hot. Instant boner. Shit, now I'm distracted."

She giggles out loud as she reads the texts but doesn't write back. She heads to her bedroom & catches up on a few episodes of Real Housewives of Atlanta. Four episodes in & she eventually falls asleep. Y/N wakes up a couple of hours later. She gets up, puts on some music & searches through her closet to find an outfit. She finds a black sundress & a pair of white sandals. She does a few loads of laundry to kill some time. Around 5pm, Y/N starts to get ready. She styles her hair in a top bun & puts on very little makeup. She looks at herself in the full length mirror in the bathroom as she puts her dress & sandals on. She goes downstairs to the living room to wait for Jess. She grabs a book & begins reading. Halfway through the third chapter, there's a knock on the door.
"Come in", she says loudly. Jess opens the door & walks in.
"Hey", Jess says closing the door.
"Hey. In the living room." She puts the book down as he enters with a serious look on his face.

"I'm mad at you."
"Why?"
"You know why."
"Frustrated?"
"You have no idea." She giggles, grabs his hand & they leave. Once, they arrive Jess introduces Y/N to his uncle Luke & his wife, Lorelei. Lorelei introduces her to her daughter, Rory.
"It's nice to meet all of you."
"So what bring you to Stars Hollow, Y/N?", Rory asks.

"Change of scenery after my divorce." They all find their seats. Jess & Y/N sit near the tree. Jess goes to get popcorn & sodas. When he comes back, the movie starts & they cuddle up. His hand rests on her thigh as they share the popcorn.
"You look so hot", she whispers. He smiles & whispers back.
"So do you."

More than halfway through the movie, Y/N teases Jess a bit. She places her hand on the back of his head, kisses his cheek, his jawline & down to his neck. He tries to concentrate on the movie.
"Wanna get out of here?", she whispers, kissing his earlobe. Without responding, he gets up & grabs her hand. They walk back to her place. Once they enter her house, he kisses her, closing the door with his foot.

"Bedroom", he says. She grabs his hand & leads him to the bedroom upstairs. Once they step in, they rush to take off their clothes. She gets on the bed, smirking at him. He crawls onto the bed, kissing up her leg to her lips. Her nails grip his back as his hands get lost in her hair. He flips onto his back. She continues to kiss him then proceeds down his body.

She takes his semi-hard cock in her mouth. He moans, feeling her tongue swirl up & down. Soon, her mouth slides him in & out. She does this quickly before pulling away. She strokes him while her tongue explodes his sac.
"Oh..." His moans grow louder until she lets go & shoves her down his cock again.

She pulls away shortly thereafter. His tongue darts out. Wanting to taste her. She stands above his head & lowers herself onto his face. His tongue pushes into her tight pussy, lightly stretching it. She rests her hands on his upper thighs as she starts riding his face. She finds a steady rhthym but she keeps riding his tongue. Loving the way his growing beard feels on her thighs. She moans his name as she reaches climax. Upon hearing that, his tongue rapidly tastes her.

Her mouth is wrapped around his cock now. Both eager to please one another. After what feels like forever, she pulls away & slowly inserts him in. Both moan as he feels her tight walls stretch over his cock.
"Oh my god...", she moans.
"God....damn", he says.

With her feet are planted into the mattress, she begins riding him. She bites her lip as she eyes him. His hands travel up her waist. He sits up & wraps his arm around her back as she continues. They're nose to nose, moaning loudly. He kisses her & bites her lip. She falls back & he climbs on top of her. He enters her & she moans louder as he rapidly thrusts into her.

"Don't stop....."
"Don't plan on it", he moans in her ear. He pulls out & turns her to her side. He slowly thrusts into her. She pushes her hips into him as he grips her. They both move together. She turns her head to kiss him as he circles her clit with his fingertips. She drapes her leg over his, allowing him more access to her clit.

She moans against his mouth as his tongue keeps teasing hers.
"Oh god...I'm cumming", she yells.
"Cum hard for me." He kisses her as she cums once more. He orgasms soon after her. They pull apart, breathing heavily.
"Holy crap", she says.
"That was so amazing", he replies. They clean up & snuggle under the sheets.
"I don't ever have sex on the first date", he says.
"Me either. But I'm glad I broke that rule with you."
"I agree. You're amazing." She kisses him.

"So are you." They lay together for a bit before putting on a movie. Jess spends the night & they fuck once more.