#gilmore girls imagine

[iwritefandomimagines]

TREEHOUSE — JESS MARIANO

masterlist

pairing: jess mariano x reader

description: you’d be lying if you said you didn’t enjoy jess’ flirty teasing. he’d be lying if he said that you didn’t make him uncharacteristically mushy.

warnings: swearing n fluff!!!, that’s all folks

author’s note: ok so i caved and started rewatching GG already — i had this idea and had to run with it! let me know what u think x

“Wow Y/N, we have got to stop bumping into each other like this!”

You looked up, rolling your eyes at the smirking boy before you as you placed down your book, “Oh yes,” you quipped sarcastically, “Such a shock to see you at your uncle’s diner that you live above and work at. Bonus points for you literally choosing to come over to my table, by the way. Usually you save our tantalising small talk for when I come to the counter for a drink.”

This only emboldened his smirk, and he glanced back to see Luke quirking his brow at his usual game — he always distracted himself from helping out by busying himself with talking to you.

In seconds he’d sat himself down in the empty chair opposite you, leaning on your closed book and staring so intently into your eyes you felt your heartbeat quicken immensely.

“What do you want, Mariano?”

“Ouch, last name?” he pouted, “And here I thought we were friends.”

Your heart was racing at how close to you he seemed to be, but his assertion of your supposed ‘friendship’ dulled this a little.

It infuriated you that he spent so much time flirting, and then every other moment acting like his having any romantic interest in you was a ridiculous suggestion.

“Friends, hm?”

In all the time he’d been loitering around, lending you books, stealing your books, making you coffee and all-round just finding any reason to be near you, Jess had never been certain his attraction to you was reciprocated either.

You’d started out shy, unsure of why the hell he seemed so struck with talking to you when he appeared so disdainful of everyone else in Stars Hollow.

And then you’d warmed to him, you’d opened up, you’d spent evenings as the only two people in Luke’s — just talking for hours on end — only to the next day seem distant again.

He’d tried to reassure himself that you did like him too, and that you were just shy, but something always stopped him from passing the boundaries of friendship beyond flirtatious remarks.

“Am I being relegated to an acquaintance?” he placed a hand over his heart and screwed up his face like he was going to cry, before relaxing it and smirking once more, “Or is your inquisitive tone your way of hinting at your undying love for me?”

“Shut up,” you shoved his arm gently, watching him feign a gasp, “You’re a pain in the ass, you know that right?”

Jess scooted his chair even closer to the table, “I totally thought that was your favourite quality of mine. My mistake!”

You didn’t reply for a moment, challenging him with eye contact and feeling your chest tighten at the way he seemed to match the intensity.

“What’re you doing tonight?”

This was new — he normally just hinted at caring what you were up to, nudged for you to give away whether you were seeing anyone, and danced around flirting just enough that he could deny it if you called him out on it.

You gestured to the book he’d made himself comfortable on, “A riveting night of draining your establishment of coffee ‘til you close, finishing this book and then probably either starting another or binging some shitty tv.”

It was only now that he looked at the book he was leaning on, clocking that it was Ham on Rye and he was the one who’d lent it to you when you’d expressed a desire to read more Bukowski.

“How’re you finding it?”

“Oh, and apparently starting the Jess and Y/N book club,” you teased, “Yeah, I’m enjoying. Thank you again for letting me borrow it.”

He smiled, “Anytime. Want me to leave you alone ‘til you’re done with it?”

You pondered his question for a moment. You didn’t want him to go anywhere, but weren’t quite sure if you should suppress your eagerness for his company.

“No, no,” you bit your lip, “Its alright. Does—,” you almost asked if Luke needed him, in the hopes that he’d say no and you could ask him if he wanted to get out of there. Almost.

“Does… what?”

“Nothing, never mind,” you shook your head, blushing crimson at how closely he watched your every move, “Its quiet in here tonight.”

He shrugged, “I was hoping you’d ask if I wanted to get out of here, because Luke definitely doesn’t need me when it’s this dead.”

You smirked, “Is this you asking me to get out of here?”

“Maybe.”

“Cool.”

“Cool?”

“Yes, Jess, cool. Let’s go somewhere else,” you grinned, pulling your book from beneath his elbow slowly and watching him roll his eyes at your teasing smile as you did so, “I was going to ask that. Didn’t want to seem too eager and boost your ego.”

He feigned insult again, “Ego? What ego?!”

He rose to his feet as you packed your book into your bag, gesturing that he was going to go and tell Luke he was leaving and quickly sauntering over to the counter, where you just about overheard Luke mumble, “Finally asked then?”

That made your stomach swarm with butterflies — this was really happening.

All this time, and things were finally progressing.

Jess briefly disappeared behind the counter, before re-emerging with his jacket and opening the door to the diner for you to lead the way out.

“Where’d ya wanna go?” you asked, your voice quiet as you suddenly felt anxious about being so close to him.

Your feelings for Jess had been growing steadily for so long now, bubbling under the surface, and now you finally had an inkling he actually liked you too you didn’t know what to do with yourself.

He shrugged again, looking down at his feet with his hands stuffed in his pockets as he ambled through Stars Hollow at your side.

“We can just walk,” you hummed, “Or we can go to mine. I’ve, uh, got a treehouse out back that my dad built when I was a kid. Or not if that’s a really fucking lame suggestion.”

He kicked a stone at his feet, “No, that sounds good. Totally lame. But good.”

That pleased you enough to elicit a small hum from your lips, and you found yourself walking a little closer to him as you led the way to your house, “Good. Follow me then.”

When you arrived at your house it was empty as ever — the reason you spent so much time at Luke’s was the rarity of company at your own home given your parents’ busy work lives.

You grabbed a few drinks from the fridge, some snacks from the cupboard, and then led the way out back to the treehouse, which was lit with fairy lights and adorned inside with band posters and shelves of books.

“I’ll give it to you, Y/N, it’s less lame than expected,” Jess nudged your side as you crawled in and slumped down on the mattress in the corner of the room, scoffing at him, “I feel honoured to have the Jess Mariano’s approval.”

“Should I feel privileged to be up here?” he licked his lips, eyes glancing over at the torn “NO BOYS ALLOWED” sign discarded at the edge of the tree house too, “Or does the sad state of the sign suggest I’m one of many exceptions?”

You rolled your eyes, “If you’re jealous that other boys may have been up here, you can just say that, Jess. But you should feel privileged because you’re the first. In fact, I can’t believe I didn’t even think twice about bringing you up here.”

He seemed to like that, his eyes glimmering as they darted between your lips and your eyes repeatedly while he found the words to respond.

“I’d say that means you like me, Y/N,” his voice was barely above a whisper as he spoke, and your close proximity left you shuddering as his breath fanned over your face, “Can’t say I blame you.”

His shit-eating grin made you roll your eyes for the millionth time tonight, “Here I was about to say maybe you were right. Thanks for snapping me out of it, shithead. I don’t like you nearly as much as you like yourself, huh.”

He just stared at you for a moment, eyes still twinkling and his breathing jagged.

“Funny, except I don’t think that’s true,” his head dipped to kiss you now, capturing your lips at first tentatively and then with increasing pressure as you kissed back.

He pulled back for a second, half smirking and half dazed, “Yep, I’d say you definitely like me.”

“Says the one who initiated the kiss,” you challenged, “And has been flirting with me incessantly since, like, the moment we met.”

He raised his eyebrow, “Oh is that so?”

“Are you denying it?”

“Oh no, I’ve definitely been flirting,” he licked his lips once more, desperate to kiss you again but trying to refrain for now, “It’s just funny that you’re only calling me out on it now.”

You gently shoved him and poked out your tongue, “I can kick you out of my treehouse whenever I want, you know.”

He only leaned closer again, “But you’re not gonna, are you?”

Jesus Christ you’d not been prepared for the palpitations in your chest right now. Your heart thrummed against your rib cage, drunk on the feelings that had only gotten stronger tonight.

“It’s your lucky day.”

You kissed him again, and the arm he wasn’t propped up on scooped around your waist to pull you closer and deepen the kiss, “Yeah, I guess it is.”

You stayed like this for god knows how long, joking around in between kisses and getting more and more comfortable in each other’s company, until he sat up abruptly and furrowed his brows.

“What’s wrong? Filled your kiss quota for the night and ready to leave or something?” you smiled, tongue in cheek, and he chuckled.

“Oh no, never. Just figured as much as I’d like to just kiss you, we should probably talk,” it was unlike Jess to look as nervous as he did right now.

In the time that had passed this evening, you’d grown comfortable enough to help him out a little here.

“I really like you, Jess.”

He wasn’t expecting that — you could tell from his wide eyes and open mouth, which he swiftly shut when he realised he was slack-jawed and silent.

He reached out to take your hand in his, fingers twiddling with yours, “You do? That’s, uh, good. ‘Cause I really like you too, Y/N.”

You couldn’t help the little joyous giggle that escaped your lips, and he couldn’t help the warmth that spread through him at the sound of it, “D’you want to stay over tonight? We can sleep in here?”

He kissed your nose, relaxing back into his reclined position again, “If you’re sure… I’d like that.”

“‘Mm, c’mon then,“ you cuddled in a little closer to him, suddenly overcome with tiredness from the evenings events, “…’m sleepy.”

He smiled, a broader smile than he was sure he’d ever smiled before, happy you were finally this close to him. He dipped his head to kiss your forehead, interlocking your hands as you got comfortable on his chest.

“G’night beautiful,” he whispered, and you could hear his heart thrumming in his chest. You couldn’t believe you’d found this side of Jess Mariano. And you weren’t going to get over that joy any time soon.

“Night Jess,” you hummed, already half asleep, “You better be here when I wake up.”

“Oh I will, Y/N, I’m not going anywhere.”

———

ahhHhHhh i hope you enjoyed this !!! please feel free to make some requests if you’d like, or just let me know what you think! i’ve been in such a writer’s block funk lately — but hopefully i’m back now!

here is my masterlist if you’d like to read more of my works!

[bealovesmarauders]

Heyyy! You said you were writing for Gilmore Girls, are you writing for Jess? If so, could you please write headcanons for him or anything you want to write really. If you don’t want it its okay ofc💕

grumpy x sunshine / jess mariano

⋆ ࣪.      ⁺⑅     ⋰˚     *.ﾟ    .˳⁺⁎˚     ˚⁎⁺˳ .    ༺ ˖

jess mariano x reader (headcanons)

wc: 700

a/n: thank you so much for requesting!! yes i do write for jess!! one of my fave bfs other than james potter and gilbert blythe. they’re all so<33  i’m absolutely obsessed with the grumpy x sunshine trope rn and jess with that seems perfect so that’s what im gonna write about if thats ok!!

⋆ ࣪.      ⁺⑅     ⋰˚     *.ﾟ    .˳⁺⁎˚     ˚⁎⁺˳ .    ༺ ˖

jess has always been the bad boy of stars hollow since he moved. that is a fact. and when he meets you it completely throws him off because how can someone be so happy and sweet, and so beautiful at the same time?

obviously he’s not known for being optimistic… so when you meet him while working at luke’s, you try to make it your personal mission to have jess smile at least once a shift

luke thinks it’s great that you two have to work together because jess badly needs a good influence, and you’ve known luke since you were young so you’re completely and entirely trusted with the shop when luke goes fishing and whatever

jess is astounded

and then the way you treat the customers

even kirk likes you- he thinks you’re a wonderful break from whatever the hell luke’s attitude is

you’ve memorized everyone’s regular orders and never fail to serve someone without a smile on your face

at first it kinda pissed jess off tbh because he thinks it’s an act and not genuine

but as he gets to know you better he realizes that you’re just a really lovely sunshiney person no matter what, and hey, maybe you’re rubbing off on him a bit after all

one time he leaves his book at the counter while he’s on a break and you run up to the apartment to give it to him, even though there’s a backlog of customers

“you forgot your book downstairs”

he kind of stares at you, a smile creeping up 

“thanks”

“you’re welcome”

more awkward pauses

“you should really use a bookmark, you know, it’s bad for the pages if you bend them like that”

“you read?”

“yeah. you should really start a new book, though. that one had a super unsatisfying ending”

“oh yeah?”

that’s when everything changes for him

the next shift he comes to work on your day off and you’ve left him a small package beside the coffee machine with his name in cursive on it

it’s a book

your handwriting is inside the front cover with a little note to him

‘for jess, this is my favorite book, don’t bend the pages please :)’

and then there’s a homemade bookmark

from then on you guys start trading books 

and he starts smiling at you more

you guys get closer and more attached, working perfectly in sync at the diner- you’ll have the fries done at the same time he’s grilled a burger, so that everything stays warm for the customers

jess also starts doing more little things for you: wiping down the counter, helping clean up so you can go home earlier, giving you all the tips in the tip jar even though technically he deserves half

until one day you come into work late, eyes rimmed with red, furiously blinking tears away

he’s never seen you like this, so obviously he has to fix it

because you’re y/n l/n. you’re the sunshine of stars hollow

lorelai and rory are there, and so he asks lorelai to help man the coffee 

jess takes you upstairs to his room, away from prying eyes, and asks you what’s wrong, cause he can tell

you just burst into tears

“hey hey hey, you’re okay, what’s wrong?”

cue protective jess.

through the tears you tell him how you’re overwhelmed with school, homework, the pressure to get into a good university, and how you feel like you’re supposed to handle it all by yourself

jess knows it’s not the time for wisecracks

so he wipes away the tears from your cheeks and listens as you talk

when you’ve calmed down, you hug him as a thank you

jess has never really been hugged before. luke and his mom aren’t very affectionate, especially physically

when you finally pull away, his touch lingers

and you kiss him on the cheek very quickly

that’s when jess knows you’re the one

you’ll always be his sunshine, even through both of your worst moments

and he knows he’s going to spend the rest of his life with you, and devote his days to hearing you laugh

but that’s a story for another time

i hope you like this!! thanks so much for requesting, sorry if this got a bit long or if it’s not what you're looking for. likes and reblogs are appreciated! <33

[amorchai]

OMG IM IN LOVE WITH UR JESS MARIANO FICCS!! can i request a jess mariano x reader? the reader is a naturally loud and bubbly person. reader is talking to jess abt something they're excited abt, but realize that theyve been talking the entire time and jess hasnt said anything, reader automatically shuts down and stops themselves bc they're always told that theyre too loud and talk to much. i need the comfort fics😢😢 <3

jess assures you when you're insecure.

pairings: jess mariano x reader

words: 466

warning(s): insecurity ( r thinks they talk too much )

you had been mid-rant, jess fresh on break with a tea towel over his shoulder and hair tousled from the aftermath of mid-afternoon rush in luke’s café. when you had entered, the chaos of people leaving, jess breathed a sigh of relief and his uncle granted him his break.

you were talking about your long day at college – filled with dramatic students and unsympathetic professors, jess was sitting across from you, head perched on his palm staring at you.

“… i didn’t do one of the readings because i used that time to see you instead, god forbid i have a social life because he didn’t care… he just looked right at me and said that i should’ve known the answer.”

jess quirks a smile, a simple ‘how was your day?’ turning into a ramble that he didn’t dare interrupt. he knew you were interested in him, you just needed to offload and then you’d ask how his day was – even though his was significantly more boring than yours.

“anyways, i met paris for a bit during our free periods – she drove down and we grabbed some lunch. so that made me feel better, oh they had the best black coffee! paris loved it! i should take you sometime-”

you take notice into how jess is staring at you, your energy yields as you take it for boredom rather than admiration, the relationship was still fairly new in your defence.

“i would love that, baby,” jess replies.

your eyebrows furrow, your finger that previously runs across jess’ free palm stops. jess matches your expression, hand cupping yours with a small, “what’s just happened?” confused by the sudden silence and change of energy.

“no, sorry, was just rambling. i haven’t even asked you how your day was…” you trail off, looking down to your hands to avoid eye contact in case you might cry. jess tries to meet your gaze, head lobbing down, “it’s okay, i like listening to you talk.”

you look at him, eyes wide and confused, “you do?” jess’ heart throbs in his chest, unsure if you’ve been called out on being talkative or upbeat before, but a topic he’ll bring up another time. “’course, baby.”

your biting your lip anxiously, the need to kiss him very much sitting in your heart, if only you weren’t in the company of small-town eyes – babette sitting across the room. “how was your day?” you ask jess, smiling happily when he takes both your hands in his.

“alright, kirk saying this, dean annoying the living the hell outta me. but tell me more about the café. we could go on friday after your college class, yeah?”

you couldn’t help following your heart in leaning over and kissing jess, even if it was only for a few seconds.

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amorchai © ─ all rights reserved. no reposting/translating/copying will be tolerated.

[ilyasorokinn]

“HOLDING HANDS UNDER THE TABLE” prompt with jess mariano please and thank u 🫶

SPOIL

this is the first thing i've ever written for jess, so i you enjoy besties <3 also, i am a lorelei and rory stan, so if you aren't or want to say anything mean, say it to a wall.

"holding hands under the table." (from this prompt list)

when you and jess got together, you wanted to keep it on the dl. well, he wanted to keep it on the dl. although you weren’t best friends with rory gilmore, you were kind of friends and he didn’t want to create any animosity between you, so you decided to not tell anyone about it.

before school, you would meet in the back parking lot where no one ever was. jess brought a surprise pastry to share and a cup of hot chocolate while you brought a new book.

"on the menu today, vanilla scones with lemon icing."

"ooh, luke's getting fancy." you teased.

"i'm pretty sure he bought them."

"then disregard what i said."

"and what book did you bring today?"

"kirk told me i had amazing taste when i bought the book."

"kirk told you that? why would kirk be working at the bookstore?"

"who knows? i've learned to stop questioning kirk." you handed it over to him.

"really?" you shrugged, "i am not reading this."

"oh, you're boring. come on, it's a good book." you insisted. he opened his mouth to argue when the bell rang, "are you actually going to come to class today?"

"i don't know, i kind of like hearing you recite everything back to me." you playfully shoved his head and grabbed your stuff, "i'm kidding. we'll see. i have some stuff to do before."

"what could you possibly be doing right now?"

"stuff." he responded, "i'll see you later. promise i'll be there."

"you better." he leaned down and kissed your forehead before he was on his way, "i'm holding you to it, mariano." he gave you a thumbs up.

true to his word, jess walked into class as if he hadn't missed the majority if the day, "you know, when you said you had some stuff to do, i didn't think it would take all day."

"you'll be happy to know i got you something." he produced a flower he had definitely picked from the garden on the way to school.

"awh, that's sweet." you cooed, "how much do we owe taylor for it?"

"he won't even know it's missing." jess rolled his eyes, leaning back in his chair then grabbing your hand and holding it in his lap under the table, "i got you something else too, but that'll have to wait till later."

"ooh."

"not like that." he rolled his eyes, "a cd."

"cd? jess mariano, you are spoiling me." you smiled.

"anything to see you smile." he gave you a sarcastic smile.

taylor's 2.5k celly!

[sourcherryandsprinkles]

Could you do 30. ‘‘Each of my thoughts about you are improper.’‘ with Jess Mariano 😄

I haven’t written for Jess in so long. Hopefully this is good🤞

—

The smell of his pine aftershave lingered on you after you left his apartment, making you wish you were still tangled in the sheets with him. Soon, you'll be graduating and this back and forth driving to see Jess will come to an end.

You hadn't told anyone yet, but once college will be over, you'll be moving to Philadelphia and getting an apartment with Jess. His roommates had kindly offered you to stay with them, but you felt uncomfortable moving in with Matthew and Chris. They were very nice guys, you just wanted privacy.

‘’I don't want you to go,’’ Jess said against your shoulder, half-asleep.

It was Sunday and he knew what was coming.

You rubbed his back, his skin golden from the sun coming through the window, wishing Sundays weren’t a thing. Long distance relationship sucked.

‘’Can’t you stay until lunch? We could get breakfast at the café on 2nd street?’’

‘’The pancake place?’’

Jess hummed and began kissing your neck to make himself extra convincing.

Unfortunately, you had to decline. You had to go over your English paper for Monday one last time and finish your article for the Daily News. You had also promised Rory you would get coffee with her in the afternoon.

‘’Or we can stay in bed and…’’ His hand glided under the covers and down your body and slipped underneath your sleeping shorts, making you swallow a moan when his finger brushed over your clothed clit. 

Maybe coffee with Rory could be reported. She would understand, right?

You bucked your hips into Jess’s touch, asking for more. 

‘’So, is this a yes for the bed?’’ he asked, cocking an eyebrow.

You hit his arm. ‘’You’re such a horn-dog.’’

‘‘I can't help it. Each of my thoughts about you are improper.’‘ His lips crashed over yours and his fingers pulled aside your underwear.

—

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[oh-thats-what-it-is]

Jess Mariano SMUT: The best friend and the boyfriend.

POV: Your best friend Rory always gets what she wants as the town’s golden girl. Well, you have had enough and its time you get what you want.

WARNINGS: 18+ (minors dni); cheating; rory slander; lorelai slander; p in v intercourse; dirty talk; unprotected sex; light choking - i think that is it

AUTHOR’S NOTE: wasn’t enough jess smut for me on here. Wanna fix that! first time writing anything so please be gentle. 2k+ words

You’re at Luke’s diner trying to get some work done before your exam tomorrow. The wetness inbetween your legs was proving a great distraction to the task at hand. You had to muster every ounce of concentration to listen to what Lane and Rory were saying. The three of you were finishing up your group project for school. You had all been friends for years, but recently you had found it hard to be yourself around them.

The reason for that, was standing behind the counter, serving customers with a surly look and a quippy comment if he spoke at all. Jess.

The whole town knew about him and Rory. How could they not? Stars’ Hollows’ golden girl drew attention wherever she went. Her and Dean’s romance had been the talk of the town - the stuff of young love! And she could do no wrong. Even after she dragged Dean through hell and back with her indecisiveness before ultimately bringing him to breaking point - people still loved her.

And hey - you did too. She was your best friend. But you couldn't help but roll your eyes at the way the town fawned over her. Even though it had been happening your whole lives. Rory and her busybody, try-hard mother were the apple of the town’s eyes. And you were used to it.

But you had been surprised that Jess had fallen for it. When he arrived in town, a sullen and brooding figure, you had immediately felt drawn to him. You could sense his angst. You could feel it vibrating off of him. And lets not pretend like he wasn’t a total smokeshow. He looked like a man.

If only Lorelai and Luke weren’t so close. Then you might have gotten your chance. But as fate had it, and as it always seemed to, Rory got in there first. Lorelai invited Luke and Jess over for a welcome dinner, and he instantly became smitten with Rory’s mild manner. It only took a matter of months - and a breaking of one Dean Forrestor’s heart - until they became an item.

At first it was all rosy. Rory wouldn’t shut up about it. But you could tell. Something wasn’t quite right. Two months passed and Rory would go red every time Jess was brought up, or came to sit with your group at lunch. You asked Rory - genuinely as a friend. She would just mumble and divert the subject. Lane also pressed, but there was no budging Miss Gilmore.

It was only a month ago when you cottoned on to what the problem was. You had been wearing jeans that hugged your ass, and a top that teased just enough of your cleavage to make anyone blush. You bumped into Jess in the hallway at school. As in, physically bumped into him, as he came around the corner. He grabbed onto you out of instinct to apologise.

“Oh hi Y/N. What are you….” His eyes trailed down to your chest. You didn’t notice at first. You thought he was dazed by the surprise interaction.

“Just on my way to Spanish. Señora Castilla is making us do a book report - I’m doing 100 years of Solitude.”

“Hmm” he responded. “That’s one of my favourites. Magical realism, love, scandal - “

And then you clock. His eyes are on your tits. His hand is still on you. On the small of your back.

This man is hungry. He hasn’t been laid or anything of the sort in a while. Or at least since he has been with Rory. Jess wants you. You avert your gaze.

“Jess. I have to go.”

He moved his hand lower, testing the waters. You don’t remove it. You inhaled, trying to retain your morals. You remind yourself: We’re in the middle of the hallway. At school. He is Rory’s boyfriend. Rory is my best friend.

You repeated these over and over to yourself like a mantra, willing yourself to move. After what seems like an eternity, he whispers in your ear: “My car. 10 minutes,” and sauntered away.

And that was how it began. A whole month of some of the steamiest makeout sessions, hottest sex, and best orgasms of your life. Did the secrecy turn you on? Maybe. Did you feel bad for Rory? Perhaps. But were those moments with Jess worth it? Absolutely.

You had to be careful. Not just to avoid Rory and Lane. But Luke couldn’t know either. If he did, he would have gone straight to Lorelai and it would have been a whole thing. It wasn’t worth it. So the two of you would sneak in quickies in his car, behind Miss Patty’s studio, in the AV room at school etc.

But Luke was out tonight. Doing something for Lorelai probably. Who knows. Jess had suggested the two of you take advantage of the situation. He had recently acquired his own room at Luke’s, ever since his uncle had knocked a hole in the wall for him. It wasn’t much, but you couldn’t wait to share a bed with him, and take your sweet time worshipping his body.

“Okay Y/N, we’re off. You coming?” Asked Lane.

“Nah, I have a bunch more work to do for my college application. I will see you both tomorrow?”

Rory went over to give Jess a kiss goodbye. You couldn’t help but smirk as you saw him looking at you as she kissed his cheek. The two girls waved goodbye and left the cafe.

The minute they left, Jess pounced on your table. He summoned Cesar to take over his shift and close up.

“Cmon baby” he whispered, taking care not make it look obvious to the other customers what was going on.

You and Jess went up the stairs silently but quickly. The minute you reached the top flight and opened the door into the living quarters, Jess slammed the door shut and pressed you against it.

“Do you know how bad you are? Sitting right next to my girlfriend and giving me those ‘fuck me’ eyes all night? It was all i could do not to take you on the table right there.”

His forehead was against yours, his hands cradling your face. All you could see was him. All you could feel was him.

“Such a good boy for restraining yourself,” you cooed, trying lure him into making the first move. Each time you were together, it still felt like new. A game of chicken. Who would break first? Fresh and dangerous, yet familiar and comforting all at once. “It must have been so hard for you” you said, moving your hand towards his crotch. “Show me how much you want me” you dared.

It was too much for him. He growled and leant in to kiss you with everything he had. He was messy and sloppy with need. His teeth clashed against yours. You moaned with need. Your hands wandered to your waist, dipping under your trousers, then your panties. You started playing with your clit and panting his name back into his mouth.

You were still against the door. Jess moved his hands under your shirt, finding the valley of your chest easily as you hadn’t worn a bra today.

“Fuck” he said, breaking the kiss. “You had your tits out all day baby girl? You are such a slut, wanting everyone to notice.”

Before you could begin to formulate a reply, his mouth was on your left nipple. You sighed as he sucking with such fervour. Just as you got used to the sensation enough to say something witty to him, he bit down hard. You yelped - this was a new move from him. He obviously felt emboldened by the new setting, being in his own territory and out of a car.

Jess went to your right nipple, sucking and making the most obscene slurping noise and his hand went to your other tit. It was too much. It felt too good. You started playing with your clit with even more until he finally noticed.

“That’s my job Y/N. Its not like you to be so selfish!“ he scolded. He grabbed both your wrists and pressed himself into you, letting you feel his bulge. You whimpered at the loss of your fingers inside your wet cunt and pouted at him. He brought your fingers to your mouth.

“Suck” he said, with a devious glint in his eyes. Like a fucking wet wipe, you did as he said. You were embarrassed at first, but didn’t care. You would do anything he said at this point.

When he was satisfied you had fully cleaned your fingers, he took them out your mouth and kissed you hard and hungrily on the lips.

You saw you opportunity to the turn the tables, to take power. “Jess?” You asked innocently.

“Hmm?” He responded, trailing kisses down your neck.

“The whole point of tonight is that we have a bed for once. Let’s make the most of it.” You pushed him off you and took his hand. You walked past the door to his bedroom. He stopped you and looked at you confused.

“Oh Jess. I don’t wanna be fucked in your single bed. I want to feel all of you” you whispered in his ear, guiding him to Luke’s room and king-sized bed.

His eyes widened with realisation and need. Was this a bad idea? Almost certainly. Did he care? At this point, not even wild horses could stop him from having you. He would do anything you said. And he had to admit, there was something hot about doing it somewhere he shouldn’t.

You pushed Jess onto Luke’s bed, unzipped his jeans and pulled down his boxers. His cock sprung up immediately. It was red, throbbing and angry. You couldn’t help but drool. Jess saw this and smirked. He knew what he did to you. He pulled off his shirt, knowing it would drive you crazy.

You dived onto his cock, unable to wait any longer. You took all of him in his mouth, as he held your head there. His pubic hair tickled your nose. You stayed there for as long as possible, until your eyes watered. You took your head off, wiped your mouth, and then began bobbing up and down slowly.

Jess propped himself up on his elbows, watching you like a hawk. His tongue was sticking out as he concentrated his breathing to stop himself from blowing his load. His dark curls were pressed wet against his forehead as beads of sweat started to roll down his face.

You moved to his balls, gently sucking them into your mouth while your hand moved up and down on his rock hard member. He started moaning and rocked his hips into your hands, desperate for more.

You had him right where you wanted him. You removed yourself from him completely and clambered to sit on top of him. His cock was nestled in your folds. So close to where he wanted to be. So close to where you wanted him to be. But you decided the chase was more fun. You lowered yourself down, so that your tits were pressed against his chest.

You whispered “Can Rory make you feel this way, Jess? Does she drive you wild like I do? Can she make you moan like a bitch the way I can? Has she ever made your cock this hard?” You punctuated each sentence with a nip on his ear.

“Fuck you,” he replied, grabbing your ass and turning you onto your back so that he was on top. He pushed himself into you and started fucking you with no mercy.

Your tits were bouncing with every thrust and you were whimpering with need every time he pulled out. You snaked your arms around his back, pulling him deeper into you. You didn’t want any space between you.

“You’re such a whore Y/N. Fucking your best friend’s boyfriend. I can’t believe it turns you on so much.”

You moaned at this words, unable to deny the appeal of the whole situation.

“Fuck baby, I can feel your cunt clenching around me as i say that! You are a fucking whore Y/N, squeezing me with your greedy pussy. Such a bad fucking girl.” Jess yelps, spanking your ass.

“I am a whore Jessy, your whore, only for you” you cried, embarrassed by your pathetic display. He grinned as you used the nickname you only brought out for him when you were cock drunk beyond belief. You groaned inwardly as you couldn’t believe you had given him the satisfaction of that ego boost.

You were lost completely in Jess. He moved his hand down to your core, adding a finger into your weeping pussy, and using his thumb to toy with your clit. It was bliss.

“Jessy?” You called out.

“Hmm?” He groaned in response.

“I want you to cum inside me” you begged.

His eyes widened as a wild look came over him. Without missing a beat, he swung your legs over his shoulders and bent you in two as he fucked into you harder than before. His hand moved to your throat, gently choking you. You stuck your tongue out like a dog in heat - animalistic and beyond a care as to what was normal.

The bed’s headboard was hitting the wall with every thrust from Jess’ pelvis, sure to cause a suspect dent tomorrow. But neither of you could have given a single fuck as the you both chased your highs. The sound of skin slapping, moans and gasps were obscene.

“Jess, have you seen Luke’s toolbox? We need it and he said it might be - Oh my god!”

You both froze and turned to the door. Lorelai was face to face with you and Jess butt naked on Luke’s bed. Sorry - lets rephrase that. Lorelai walked in on her daughter’s boyfriend and best friend fucking raw on Luke’s bed.

She narrowed her eyes and hissed: “Get the fuck out.”

[urwhorecrux]

⋆ ˚⁀➷ 𝘥𝘢𝘵𝘪𝘯𝘨 𝘫𝘦𝘴𝘴 𝘮𝘢𝘳𝘪𝘢𝘯𝘰: 𝘮𝘰𝘰𝘥𝘣𝘰𝘢𝘳𝘥

— dating jess mariano: long dates, loves showing you what he’s reading and is always interested in your books too, loves silent moments when you two sit there reading or cuddling, always listening to what you have to say no matter what it is.

[rorynightshade]

Icons of Rory Gilmore from Gilmore Girls

🍂📚

reblog if you save

twitter: @ Adropof_Blue

[graysnetwork]

i was watching Gilmore girls at the beginning of the year i think and then i suddenly got the urge to watch again, so i'm finally on the last episode of season 2. Im completely in love with Tristan but at the moment i'm loving jess (i also searched up jess edits on tiktok and i've spoiled things for myself so i will be debating on skipping that one scene)

Also Ik this is not the best but I hope u guys like it

Warnings— none

Summary— Jess is turning into a great student and Luke not lorelai can think of a reason he’s become an amazing kid all of a sudden.

The library

Two full weeks, two full weeks had gone by now and no calls from the school had been made to Luke's phone. This was more concerning than actually getting calls from the school. And another notable thing was that Jess started leaving every day at the same time 6:30 and he'd come back home at 9:30 or even earlier.

Luke was getting suspicious but he didn't exactly know how to bring it up since it was very possible he was cheating on his tests, maybe copying off some one else for work. So he decided he'd mention it another day, and every time that decided day came by he'd put it off again, and again.

the two of them were in the diner, it was surprisingly very quiet, there was only one person which was also surprising and then the person walked out. Jess started cleaning up the table before checking his watch.

6:15

He dropped the towel and rushed upstairs, he came back down with a backpack, had he been hiding that thing?

"where are you goin?" Luke asked, finally looking up from the counter “somewhere.” “what do you have in there?” “some things” he shrugged and opened the door, before he could even get one foot out the door he could hear Luke’s heavy steps get closer to him, he turned around again.

“What do you have in there” Luke said again, “why do you wanna know, it’s nothing important” Jess rolled his eyes and checked his watch again.

6:20

“I’ve never even seen you come outside with a backpack, and I need to know if you’re stealing things again” Luke gave him an annoyed stare, Jess unzipped the the bag and showed the books in his backpacks.

“Oh” Luke muttered, and looked over to the side “happy? Cause I need to get going” he zipped the bag up again. “where have you been going?” Luke sighed, it was time he got the truth.

“why do you wanna know?” Jess rolled his eyes again, “because I gotta know these things” another sigh came out of Luke, and Jess mumbled something. It took a good few minutes to get him to admit.

“I’m goin to the library”

He said it quietly but at least it was coherent.

———

“You’re late” you smiled as Jess sat down in front of you, “I know, I’m sorry, Luke wouldn’t let me go until I told him where I was going and what I was bringing” he smiled back at you and took out his books. “well, you’re here now, that’s what matters to me, now what’s today? math?” You smiled again and the two of you started opening your books.

“Today is math day” jess nodded and started reading your math notes.

———

“Jess, in the library? Is he meeting behind it and doing something?” Lorelai drank her coffee, “I didn’t think about that” Luke said as he gave her a doughnut.

The moment very quickly ended when Jess came in and quickly went upstairs without saying a word, Luke and Lorelai could hear the thud from Jess’s backpack hitting the floor.

Jess came back down and grabbed a doughnut; pink icing. Very weird to the two adults in the diner. Unknowing to them the only reason he grabbed it was because you swore that the pink icing on the doughnuts taste different.

———

“So anything new and interesting happening?” You asked as you and Jess walked around after studying, it was the quickest you’ve ever studied but that was because it was English, all jess had to do was read and write some answers.

“no, but, if you call getting a new shipments for the diner interesting, than yes, there something new happening” he smiled at you, “sounds very interesting” you smiled back at him.

“what about you?” Jess turned to you again “what about me? Nothing” you shrugged “cmon there’s gotta be something that’s happened so far this week” Jess said, “there’s nothing, nothings happened, and im 100 percent sure nothings gonna happen” you smiled again at him.

He wrapped his arm around your shoulder and smiled “how about I give you something to look forward to then since you’re free” Jess’s brows perked up, “really? how?” your hand reached up and grabbed his that was on your shoulder.

“how bout you, me, and chinese food, and we can do it on, Friday? You said your parents are leaving on Friday right?” He smiled as you two got closer to Luke’s diner.

“yeah, my parents are going on Friday.. that sounds like a plan” you smiled “it’s a date” he smiled. “Cmon I’ll walk you home” he walked past the diner “thanks Jess” you wrapped your arm around his waist as the two of you continued you way down the street.

-

“Did I see that right?” Lorelai’s eyes were wide and her brows were furrowed, “wow” Luke said, it was the only thing that could be uttered at the moment as they had just seen; You and Jess walking together.

“That must be why he’s going to the library so much! y/n’s always at the library!” Her mouth hung open in shock, it was silent for a few moments “y’know what, this is good” like said as he nodded while drinking his coffee.

“This is good?” She looked at him confused, “yes, he’s doing good in school, and it seems like he really likes y/n, as long as he isn’t hurting her, or doing bad things than I’m happy about this” Luke smiled “I guess this is good..” Lorelai smiled back at him.

———

[blueathens]

Idk if I'm doing this right but can you write something with Jess Mariano just being really cute and soft? Submissive isn't the right word but just how you'd think he'd be when he's really comfortable with someone and they're playing with his hair or something.

My Soft Boy

Summary: In which Jess only likes Y/n playing with his hair.

A/N: Okay so I did this as a headcanon instead! I hope you don't mind!

Masterlist//Main Masterlist//Agape Masterlist

It should be known that Jess hates anyone touching his hair

Like no one but him can touch that hair of his

He styles it to perfection

But somewhere down the line, you came along

And it made him rethink it all

Apparently you had been working at Luke's Diner for a long time, and Jess has been surprised he hasn't seen you around in the few weeks he has been there

But then he finds out that you were on holiday

First time he had thoughts about you playing with his hair was before the two of you got together

It was a boring day at the diner

A Tuesday

Hardly any customers

And the two of you (now quite good friends) were playing cards, sat on either side of the counter

And there was a moment where Jess just focuses on your hands

Watching as your fingers fiddle with your own hair

And it brought a weird sensation to Jess and gave him that sudden craving of wanting your hand in his hair

He knew that you knew about his hatred for people touching his hair when you saw one of his dates/hook-ups try touching his hair and him telling her to "get off."

She stormed out the diner and he stormed off upstairs

Stating that he needed to wash his hair now

He came back down with wet hair in his face to continue his shift

And very cautiously you moved to stand in front of him to move a few strands of hair out from his eyes

He didn't tell you to 'get off' like you thought he would

Instead a soft smile appeared on his face and eyes fluttered as the smallest of touches

A few weeks after that, Jess found you reading a book under a tree

He came over to you - completely tired from school (he actually attended because of knowing you would be there)

And without any words he just sat down next to you

And laid his head down on your lap

Guided one of your hands away from your book to his hair

Closed his eyes

And smiled softly when he felt your hand very softly playing with his hair

He never fell asleep so quickly - and he never felt so calm before either with your hand in his hair

He was just falling in love with his best friend - and he knew after today he would have to tell you his feelings

(Especially if he wanted you to continue playing with his hair)

Writing Rule||Character List||Navigation||Masterlist

[chiefdirector]

Hospital Hallways | Luke Danes | Gilmore Girls

GIF by livelovecaliforniadreams

no.16: hospitals

It was no secret that Luke hated hospitals. Everything from the sterile lighting, the smell of antiseptic in the corridors, to the constant hustle and bustle admits the calm. Not to mention the constant rotation of diseases and dying patients.

On a normal day, he could think of a million and one places that he would rather be but today he couldn't think of a single solitary reason to be anywhere else.

(Y/N) had fallen outside the diner. Black ice. Luke had seen it happen; he had rushed out to help her up but quickly found that she couldn't stand by herself. Her leg was broken, he knew that as much which meant a trip to the ER. Luke had offered to drive her, but it was only on the drive up did he realise what that entailed: being stuck in a hospital waiting room.

Luke went though, and he stayed in the waiting room as they examined her leg. He waited even though he hated nothing more than hospitals because there was nothing else he loved more than (Y/N).

He had loved her from a distance for a while. She came into the diner more and more, reciprocating Luke's flirting although he was convinced that hers were only friendly. He watched her from a distance, he didn't allow himself to get involved. She deserved something better than him, something better than what he could give her.

So he resigned himself to be her shoulder to cry on, to be there when she needed a friend. If he couldn't be anything more, Luke was happy to be the man to take her to the hospital when she broke her leg.

Masterlist | Whumptober Masterlist

@ailesswhumptober

[iwritefandomimagines]

ROMANTIC GESTURE — JESS MARIANO

masterlist

pairing: jess mariano x reader

description: jess wasn’t going to buy your easter basket and risk the embarrassment of his potentially unrequited feelings. so instead, he pays kirk to buy it so he can steal you away.

warnings: bit of swearing, bit of fluff, jess mariano i love u

author’s note: jess mariano stop appearing in my dreams challenge! anyway, hope you all enjoy. this has been in the drafts for ages and i finaaally finished it.

You were perched opposite Rory at Luke’s, on the edge of your seat as you tapped your feet anxiously and leaned on your basket.

“Nobody’s going to buy my basket,” you huffed, “You’re so lucky you’ve got Dean to like, 100% make sure yours gets bought.”

Rory rolled her eyes, “You’re being dramatic, Y/N. The town loves you. Just because you’ve been here less time, doesn’t mean nobody will buy your basket. Hey, maybe stalker over there will buy it.”

Rory was blissfully unaware that despite pretending to be distracted by wiping down the counter, Jess’ ears were practically pricked up like a dog listening.

“Stop calling him that, Rory,” you shook your head, cheeks burning as you looked over at him and he briefly looked up and caught your eye, “He’s my friend. And he said he wasn’t participating, which I assume means no buying as well as no making.”

“Whatever you say, Y/N. But we’d better head over there.”

You nodded, following her down to where Taylor Doose was already stood yelling at the town to hand their baskets in with haste and get ready to begin bidding on them.

Jess was lurking just out of sight, deciding what his best approach was for buying your basket and getting to have lunch with you as a result.

He spotted Kirk meandering over, a lightbulb moment sparking in his head as he dashed over to his side, “Kirk. I need you to do me a favour.”

“Jess Mariano needs a favour from me?”

“Yes— I need you to buy Y/N’s basket for me and then give it to me,” his hands were stuffed in his pockets as he sighed out his request, and Kirk eyed him inquisitively.

“What’s in this for me? And why can’t you buy it yourself?”

Jess huffed, “I’ll pay you 20 dollars. I can’t buy it myself because I told them I wasn’t going to be free to. I’ll be back at the diner, bring me the basket when you’ve got it and I’ll go and meet them with it. It’s a surprise then.”

“Oh,” Kirk stared blankly for a moment, “A romantic gesture. Got it. The whole town have been wondering when you’d finally get together. I’ll tell Taylo—,”

Jess took a step forward, hands flying from his pockets, “Don’t say a word! Just— we’re friends. I’m being a nice friend and buying Y’N’s basket.”

“What if I want to buy Y/N’s basket? I’m her friend.”

“Why would you want it?”

“Because— I don’t know. But I might.”

“Just take your $20 and buy me the basket, and I’ll give you what you paid for it after, Kirk,” he pulled $20 from his wallet and handed it over, “Or I’m telling Luke.”

With that, Kirk nodded and scurried over to complete his ‘mission’.

—

Kirk came rushing into the diner out of breath, basket in his hands and his face bright red, “I got it! I got Y/N’s basket. I paid $120 because a love rival of yours wanted it too, according to Ms Patty, so it was difficult. But I got it.”

“$120? I don’t have—,” he rethought it as he saw you headed for the diner, “Fine.”

He pulled his remaining cash from his wallet, handed it over to Kirk as he took the basket from him, and then wrote Luke a note explaining why he was about to take cash from the register and replace it with savings he had stashed upstairs when he next went up.

You entered the diner alone, no Rory this time, and Jess was relieved. He knew she didn’t like him, so he was happy to have time alone with you.

“Oh, so Mr Too Cool for the Easter basket bid wanted a basket after all and just got Kirk to do the work for him?” you teased, propping yourself up on the counter as you tried to suppress the giant smile forming as a result of his gesture.

“Well, time-honoured town traditions aren’t really my thing,” he shrugged nonchalantly, just a hint of a smile tugging at his lips, “But you’re good at this kind of thing. I thought it’d be nice.”

You placed your hand on top of where his rested on the counter, “Oh wow, are you ill? Is Luke ill? Am I ill and entirely unaware? Jess Mariano— doing something because you thought it’d be nice…”

He shook his head with a laugh, “C’mon, I can be nice!”

“Oh sure. You’ll have to show me this apparent nice Jess now when we go and eat the miserable contents of this basket,” you sing-songed, aware that your hand was still on top of his. You grabbed it, giving it a light tug to urge him to get away to join you now.

“Hm, not sure you deserve it if you’re going to tease me,” he pouted, following you out of the diner anyway as you swung the basket in your hands and skipped along, “Fine. Well let me choose where we go to eat then.”

“Sure. I just wonder where you’ll take me,” you teased, watching a smirk grace his face as he shook his head, “Gee golly I sure hope there’s a bridge involved.”

You’d wandered past him sat on that bridge many a time and it had once been your reading spot instead.

Jess scoffed at your mocking, “It’s quiet, can you blame me? I’ve already had Kirk telling the whole town about my supposed romantic gesture.”

You narrowed your eyes, briefly feeling a pang in your chest at the implied denial that there was anything romantic about him buying the basket.

“So this wasn’t your way of confessing your undying love for me?” you paced your palm to your chest in feigned dismay, “What’s your motive, then? Are you luring me out there to kill me?”

“You’re a pain in the ass, Y/N,” Jess rolled his eyes, “Can we just go?”

“No denial. Wow, I’m gonna die at Jess Mariano’s hands, and the last thing I’ll have eaten will be my miserable cheese sandwiches,” you gasped.

Jess led the way out through the town, clocking that all eyes were on you both, “Bold of you to assume I’d let you live that long. Think I’d get the job done quick enough to eat the sandwiches myself. I am pretty hungry.”

“Well unfortunately for you I put up a good fight when I’m hungry,” you nudged him, “And you’re supposed to be being nice, huh?”

Jess nudged you back, “You accused me of plotting to kill you!”

You just hummed, swinging the basket as you walked at his side and finally reached the bridge. You sat yourself down, waiting for him to follow suit as you immediately began unpacking.

“Wow, someone’s eager.”

“You just spent $120 to eat sandwiches with me Mariano,” you laughed, “You haven’t got a leg to stand on talking to me today.”

Jess shrugged, conceding as he looked into the basket while you pulled out it’s contents, “Pretty good.”

You handed him a sandwich with a small smile, taking one of your own and unwrapping it to take a bite, “In all seriousness, why did you actually bid on my basket?”

Your voice was small, and it warmed Jess’ heart to see you nervous to hear his answer.

“I just thought it’d be nice,” he shrugged, but you could see in the way his eyes lingered on you, as they so often did, that he was being honest now.

You smiled, “It is nice. I’m glad. Rory’s always got something to say when we talk at Luke’s, it’s nice to have time to talk alone.”

Jess quirked his brow with a smirk, “To talk alone? Are you sure it’s not you confessing your love for me?”

You scoffed, but the scoff became a small laugh as you looked at your feet where they swung over the edge of the bridge. Had you given the game away with your nervousness? Would it be clear now that you really did like him?

“You know what I mean, asshole,” you chuckled, shrugging, “I like your company.”

He smiled genuinely again, the glimmer in his eyes sending sparks through your body, “I like your company too. Just about the only person in the shithole town whose company I do enjoy.”

“You’re so poetic, Mariano,” you joked, taking another bite of your sandwich and trying to hide your blush, “But I’m glad. I really—yeah, I just like spending time with you.”

There was a brief moment of silence as you both continued eating, swinging your legs practically in sync with each other as you did so.

“Can I be honest?” Jess almost whispered as he finished his sandwich and leaned over to grab a juicebox, “Nice touch by the way.”

You giggled, “Hey, you can’t beat a juicebox. Gimme one, please.”

He handed you one too, and as you pierced the carton with your straw you’d remembered what he said before, “Of course— Of course you can be honest. What is it?”

He gulped, taking one small sip of his drink and then placing it down at his side, “I kinda did this to help me, I dunno, tell you that I liked you. Thought the gesture would… This feels stupid now.”

You bit your lip, trying to process what was currently happening, “It’s not stupid, Jess. I was hoping that was what this was… I mean, who spends $120 on a basket—,”

“Stop reminding me how much money I spent, please,” he interjected with a groan.

“Sorry—,” you smiled, “I didn’t want to get my hopes up and thought maybe it was just you confirming we were friends, but I’ve liked you for ages, Jess.”

He seemed more than pleased with this, a huge smile spreading across his face as you fluttered your lashes at him and smile right back in his direction.

He clenched his jaw, “Really? Rory’s always teasing you so I thought—,”

“How is someone so intelligent simultaneously so dumb?” you teased, shuffling closer to him and pushing the basket back so that you could move close enough that your thighs almost touched, “She teases me because she knows I like you, Jess. It was her who encouraged me to make a stupid basket to see if you’d bid because that would apparently prove you liked me too.”

Jess laughed, “I s’pose it worked out, then. I—I really like you, Y/N. At first I thought it was just because you were the only person here who isn’t— well isn’t always— a pain in the ass. I thought I’d just found a friend, y’know. But that’s not it, I really like you. I don’t wanna be just friends.”

Your heart was racing, and he seemed to have closed the last remaining gap between your sides. You leaned your head on his shoulder with a happy sigh, “I don’t wanna be just friends either.”

His hand moved to rest atop yours where it was placed on your knee, “That’s made the ridiculous amount of money somewhat worth it.”

“Only somewhat, hm?”

“It’ll only be completely worth it when you’re my girlfriend,” you could tell he was shy about saying that, “So yeah, only somewhat.”

“Is this your way of asking me to be your girlfriend, Mariano?” you grinned, heart still thrumming hard against your ribcage as he tilted to look at you.

“It might be,” he smirked, “But only if your answer’s gonna be yes. If not you’ve like, totally got the wrong idea Y/N.”

You leaned up, propping yourself up with your hands on his shoulder, and pressed a small kiss to the corner of his lips.

He smiled against your lips, reciprocating the kiss for a moment, “Is that a yes?”

You laughed, hooking your arm around his and leaning on his shoulder once more, “Yes, Jess. I’d love to be your girlfriend.”

You sat in silence for a moment, enjoying the sound of only the stream of water beneath you and your synchronised heartbeats.

“Those sandwiches sucked, by the way.”

“Oh I know,” you hummed, “I didn’t want to end up eating them with someone else so thought it wasn’t worth making much effort. Hence me hardly packing much.”

“Well now you’ve just got a hungry, broke boyfriend,” as soon as he said the word broke he was once again reminded of the cost of the basket.

“$120 man. Wow, I really do like you.”

———

thanks soooo much for reading! i hope you like this, i really enjoyed writing it <3 let me know if you have any more requests & please let me know what you thought!!!

also — here is my masterlist

[scarlet4rose]

possesive/obsessed jess mariano? where jess is so inlove with the reader that he stalks her and follows her everywhere idk

hmmmm alright, I'll try

---------------------------

obsessed with you, Jess x reader

..༘˚⋆𐙚｡⋆𖦹.✧˚.

° you spent your whole life in Stars Hollow. every day was the same. until the day jess mariano came to town

° you noticed him right away, but he had a bad reputation from the beginning and everyone around you told you to stay away from him. so you did.

° but what you didn't know was that you had caught his eye as much as he had caught yours. and he had no intention of staying away from you.

° every morning you would walk past luke's diner on your way to school. as soon as jess had figured this out, he kept an eye out for you every morning to see when you would walk past the window. he wrote down the time you would usually walk past and would be looking at the clock every few minutes, not being able to concentrate on his work whatsoever.

° he would also voluntarily go to school just to see you there

° he breaks into the school at night and goes through the principal's office looking for your student file and schedule.

° he memorizes your schedule and waits for you after every class. but you just smile at him and continue to ignore him.

° you drive him crazy, but on the outside he tries to remain as cool and unaffected as possible

° one day he sees you kneeling down to a boy after a fight in the schoolyard and worrying about his well-being. his heart stops. he thinks he has a genius idea

° a few days later, he deliberately insults some random boy. he makes sure you're close by and can see everything. he starts a fight with him, but after a while he doesn't fight back at all and lets himself be hit again and again. when it's all over, Jess's face is all bloody and he purposely remains lying on the ground. he waits a bit. and then there you are

° you bend down to him, your face shocked, you put your hand over your mouth. Jess can see your hand shaking. all because of him.

° you help him up and walk him to the school nurse. Jess doesn't even feel that bad, but he still leans on you when he walks just to be closer to you.

° the nurse is taking care of Jess. you're about to leave when Jess starts moaning in pain and is totally exaggerating, at which point the nurse decides to tell you to stay and wants you to take him home.

° you reluctantly agree and stay by his side. Jess makes every effort to keep from smiling.

°when you walk him home, he thanks you every few seconds. when he notices that you blush in response, he continues and showers you with compliments, which you dismiss slightly embarrassed. after all, you're still trying to stay away from him, as everyone around you has been telling you to do.

° you take him up to his room and lay him down on his bed. you look around a bit, then Jess gets his camera, which had been lying on his bedside table, and takes a photo of you out of the blue. you in his room! for him, it's like a dream come true, a moment he has to capture. you're absolutely shocked and set him straight. "Jess, what the hell are you doing?" jess just grins "did you just swear? did I just make miss perfect swear?"

° you get a bit shy: "I'm not as perfect as you think". Jess' heart starts pounding. you're so damn cute to him, he can hardly stand it.

° Jess is running out of excuses to keep you in his room. he makes you get a glass of water. and then some ice. and then a second blanket from the closet. he doesn't want you to leave, but you're starting to feel silly ;) and say you have to go back to school. Jess can't do anything but watch you go.

° the next day he has the photo of you in his room developed and hangs it on his wall

° Luke notices the photo and asks his nephew how he knows 'this girl'. Jess just smiles and says 'this girl' will soon be his girlfriend.

very soon.

------

the end ;)

[amorchai]

thinking about a pining best friend!jess mariano. 

you practically live in your room by your desk with headphones playing soft beats to study for the final exams before graduating from stars hollow high, you practically live on the cosy cottage bungalow alone. too focused on the music and writing notes that you don’t hear jess mariano rattling the window above your bed until you see a figure fall on top of the duvet. 

jess, the pining idiot, just murmurs something and you take your headphones off and he just goofily mutters a, “hey. thought i’d drop by, y’know?” turning to your bookcase and complaining about the sheer number of romance. you promise him ice cream if he shuts up and lets you study for a while. 

jess, who’s scarily in love but has no idea how to express it only connects his thumb and pointer finger across his lips as a mimic of zipping his mouth and throwing away the imaginary key before skimming through your awful friends to lovers book but secretly wishing it could end up like you both. glancing up at you while the desk lamp emits warm glow across your face quite like an angel in the dark room and he wants to kiss you there and then. 

jess, who nods and pats the spot beside him whenever you glance over, coaxing you to cuddle him for a while because he can only bear your company, no one else’s. 

jess, who rolls his eyes but sighs in a nod when you ask to play 'friends' when he won at your distraction to come lay beside him. breathing straggled and uneven when your breath hits his neck and tucks further into his side. 

jess, the infatuated best friend, who watches you sleep and is glad your insomniac self can catch up on a nap in the evening because you’ve been working yourself to death with the upcoming work. chuckling fondly when you wake up and freak at the night sky, thinking you overslept be he assures it’s only been half an hour and there’s still plenty of time. 

jess, who watches you walk back to the desk, sleepy eyes and long cosy cardigan over your frame and asking which of two freezer ice cream flavours he wants can only blurt out, “let’s go on a date,” in return. 

jess, blushing profusely, trying to play it down when you go wide-eyed and look back to your friend, “you. me. date?” and with a casual nod, purse lips to hide his internal freakout, he responds, “well, that is what a date means. is it not?” 

jess, who can only be left in your room bewildered and face beat red, for the first time speechless as one thought runs through his mind, how you said “yes,” straight after. 

[sourcherryandsprinkles]

Jess would so make fun of his girlfriend for drinking pumpkin spice drinks

I miss Jess and Gilmore Girls so much. I need to get the dvds. Streaming sucks when you can't afford it

—

‘’Stop it.’’ You narrowed your eyes at Jess, but he didn’t retreat and continued making fun of you.

‘’I just don’t get why you would put all that pumpkin shit in your coffee. You’re killing the taste of coffee.’’

‘’I’m killing the taste of coffee?!’’ A small humored laugh escaped your lips. ‘’You’re being dramatic.’’

He shook his head, dead serious. ‘’I’m not. This is an abomination.’’ 

You rolled your eyes and added more icing on the chilled cookies. 

It was gray outside, which was the perfect weather to bake cookies and drink coffee. Jess didn’t understand your enthusiasm, but he helped you steal everything you needed from the downstairs kitchen without Luke noticing. He even offered to mix the dough…in exchange that you would not force him to clean the dishes. 

You took a sip of your pumpkin spice latte, ignoring Jess’ grimace, then reached for the cinnamon to sprinkle some on the cookies.  

‘’Do you think Luke would like one?’’ you asked, not really looking at what you were doing. 

Jess shrugged. ‘’Uncle Luke is not much of a fan of cookies. He prefer donuts.’’ 

Although Luke loved a good donut, he didn’t dislike cookies. You had a taste of the bookish themed sugar cookies you baked for Jess’ birthday and said they were really great. 

‘’That’s a lie,’’ you said, giving him a knowing look. ‘’You just want them all for yourself— hey! I’m not finished with the cookies!’’ 

‘’You were with this one.’’ Jess took a bite of the cookie, his mouth immediately burning. He kept chewing and quickly swallowed, his face getting red as he coughed. ‘’Jesus, do you want to kill me with these cookies? Did you put the whole bottle of cinnamon on them?’’ 

You looked down and covered your mouth when seeing the mess of cinnamon, having not realized how much you had sprinkled. ‘’Sorry, I’m just too excited for fall.’’ 

—

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[the-amazing-simp]

Midnight Rain | J.M.

📝 Title: Midnight Rain

📚 Requested: Yes/No

✍ Summary: The story of how you fell in love with Jess Mariano and how second chances exist

🎶: Midnight Rain by Taylor Swift

💌: my first Jess Mariano fic, hope you guys like it!

You never knew what love truly felt like until Jess Mariano walked into your life. 

It was just another typical day, walking into Luke’s diner for your morning dose of caffeine with Rory while her mother went to get a newspaper. 

Then there he was, wearing a metallica t-shirt with red long sleeves, bickering with Luke about his choice of outfit for the day.

“Hello?” Rory waved a hand in front of your face with a teasing smile, “Do you want to sit down or are you just going to stand there?” 

Clearing your throat, you gave the mystery boy one more glance before you nodded, “Yeah, of course we’re sitting down.”

While Rory placed the order, you pulled out your current read and started where you had left off. 

“Emily Dickinson?” A deep voice said as coffee was poured into your cup, “A remarkable poet and woman, or so I’ve heard.” 

Looking up, you see the mysterious boy now standing in front of you, “She is. You’ve read her work?” 

The boy shrugged, “A little here and there.” 

You nodded to the book in your hands, “You can borrow this one if you want, I’m just rereading it anyway.” 

“Really?” He asked, a mischievous smile growing on his lips, “You wouldn’t mind?” 

“Would I be offering if I did?” You countered.

“Touche.” He chuckled as you handed him the book, “Thanks.”

“You’re Luke’s nephew right?” 

“I’d rather be known as Jess. And from what I can deduct, you’re Rory’s friend?” 

“I’d rather be known as Y/N.”

–

“Done.” Jess walked in pace with you as you were on your way to the bookstore. 

“Done with what?” You asked, making him hand you the Emily Dickinson collection of poems you loaned him three days ago.

“The book.” He answered as you took it from him.

“What’s the verdict then?” 

“It was okay, also I did write some thoughts in the margins.” 

Flipping open the book, you were met with his neat handwriting filling up all the empty spaces, “Wow. I thought you said you haven’t read it much?” 

Jess gave a smile, “What is much anyway?” 

“Point taken.” You smiled as he pushed open the door for you.

–

“You seem to be alone today.” Jess noted as he sat in the chair in front of you, “Not here with the rest of your coffee trio?” 

You laughed, closing your book to give him your full attention, “Sadly no. Rory is off tolerating Paris since the latter is freaking out over something and Lorelai is attending to something at the inn.” 

“Pity.” Jess’ signature mischievous smirk in place, “But on the bright side, I guess I’ll have you all to myself.” 

“Oh really?” You giggled. 

Before Jess could give his witty remark, Luke could be heard from behind the counter, “Jess, I do not pay you to flirt with the customers!” 

“First of all, you don’t pay me at all.” Jess stood up, coffee pot in hand, “Second, I only flirt with this particular customer.” 

And before he left your table, he leaned forward and pecked you on the cheek.

You couldn’t control the smile that adorned your lips as the heat crawled its way up to your cheeks.

Oh, but Jess Mariano was far from done, “I’ll pick you up at 8 tomorrow night for our first date?” He calls out as he makes his way to the counter. 

Looking over your shoulder, it kept all of your willpower just to stop yourself from laughing at Luke’s rather shocked expression, “Sounds like a perfect plan.” 

–

“Fine, laugh all you want but no one else can change my mind on the fact that Romeo and Juliet is a complete scam.” Jess said, stabbing his chocolate ice cream with the small spoon the dessert came with.

You were quiet for a moment as you took a bite off your mint chocolate ice cream, making it seem like you were thinking about what he said, “I know right! Rory refuses to hear a word I say on the matter but how stupid can Romeo be to see that Juliet was breathing?”

“It was a sleeping potion, it would be impossible for her to not breathe.” Jess interjected. 

“Yeah, and people have the audacity to call it the greatest love story of all time when the title clearly belongs to ‘The Notebook’.” You said, taking another spoonful of your ice cream.

 “Mhm.” He nodded in agreement, “Alie and Noah beat out Romeo and Juliet anyday.” 

“You know, you’re adorable whenever you talk about books.” Your boyfriend added. 

You swear that your face is 13 shades of red right now, and not because of the summer heat, “So do you.” 

“I’m serious.” 

“I am too.” 

He rolls his eyes with a chuckle, tucking a stray strand of hair behind your ear, “Everything you do is adorable. From the way you would practically scrutinize every single bad decision in a tv show to the way you like to smell newly-bought books before putting it away.”

“Oh, so now we’re pointing out my awful quirks?” You teased.

“Lorelai’s sarcasm is now starting to rub off of you.” Jess mused, “Can I kiss you?” 

“You better. ‘Cause I’ll be so mad if you don’t.” 

–

It was surprising how you didn’t break the door as you ran into the diner.

“Luke, where’s Jess?” You said, hoping that the envelope in your hand wouldn’t be too crumpled with how tight you were holding on to it. 

“In the apar-” He didn’t need to finish his statement as you bounded up the stairs faster than anyone has ever done.

“Looks like somebody’s excited.” Lorelai noted with a smile to which Luke just shrugged.

Immediately jumping into his arms once the door opened, it was a surprise how Jess was still able to keep his balance.

“Woah, someone might’ve got a sugar rush today.” Your boyfriend teased as you started to calm down a little.

“My book is getting published!” Finally brandishing the news you wanted to relay, you held out the envelope to him.

“See? I told you, they’d love you!” Jess grinned, taking the letter out and reading it over.

“I mean it’s nothing permanent yet.” You said, smile still intact, “The book still has to go through a round of edits and all, there’s no contract yet but they’re interested!” 

In his delight, Jess picked you up and spun you around before pecking a kiss to your lips, “C’mon let’s go out.” 

“What for?” You asked, still dizzy yet you weren’t sure if it was from being spun around or being kissed.

“Duh, to celebrate? What else would we go out for?” He then grabbed his coat before pulling you out of the apartment.

–

“Jess, you know it’s not that easy.” You sighed, tired of having to explain this over and over again.

“You’re the one who’s making it complicated.” He argued.

“Jess, the publication firm specifically told me that if I moved out of Stars Hollow then the deal is over. My book won’t get published.” You said, exasperated, “Hence, I cannot move to Philadelphia with you.” 

Jess was getting tired of this discussion too, “Then pull it out! I’m going to be writing my book too, then we can look for a publishing firm together.” 

“And put my dream on hold?” You gave a humorless chuckle, “Let me think about it, oh wait, the answer is practically obvious - I won’t.”

“So you’re going to choose your dreams over me?” 

“Yes Jess, why on earth would you expect me not to?” 

“I don’t know because you love me!”

You scoffed, shaking your head in disbelief, “Just because I love you doesn’t mean I’ll compromise my dreams, my future for you.” 

“I would’ve done that for you.” Jess countered. 

“Then I’m sorry if I can’t say the same.” You could feel your throat tightening with every passing moment, you knew how this would end - and you hated it.

“If that’s the case, then I’m going to Philadelphia with or without you.” He said, packing up the last of his clothes and stuff.

“And I’m not stopping you.” The tears were now freely dripping down your face, like raindrops on a windowsill.

“Fine.” Jess said, not being able to look at you since he hated seeing you cry then without so much as another word he left your apartment, slamming the door on his way out.

–

It’s been years since that fateful day. It took you a while to get over it but as Lorelai said, “Trains barely even wait for you at the station, so why would life?” 

Part of you didn’t regret staying in Stars Hollow, you already had 3 published books to date and was now working on your 4th one. But a part of you would always ask the “what-if?” 

The other night, you saw Jess on the news - proudly promoting the book he had just published. You had forgiven him, after all the time had passed, but you can’t help and wonder about the life you gave away.

“Oh hey, can you go get some coffee to-go? Mom needs me to save her from another one of Ms. Patty’s set-ups.” Rory said, looking up from her pager.

You nodded, “Yeah sure.”

Personally, you could never tire of the ambience that meets you when you walk into Luke’s diner, it’s hardly changed over the years.

“Hello Y/N, let me guess, a cup of coffee?” Luke greeted you with a smile, thankfully still fond of you despite what had happened with his nephew. 

“Three to go actually.” You said, returning the smile. 

“I see some things never really change.” A familiar voice, one you had thought that you would never hear again, reached your ears. 

There he was, standing by the door in all of his glory, as if he never left. 

“Jess.” You said in awe, not noticing that Luke had started tending to other customers - giving you and your old flame some privacy.

“Y/N.” He may have been older, but the same boyish, mischievous smile was there.

Even if you had imagined this day before, every word you had rehearsed was reduced to rubble. You tried to think of something to say, but everything you could ever possibly know in the English language is now gone.

“I see you’re now one of Stars Hollow’s pride and joy.” Jess teased, slowly walking towards you.

“Pride and joy may be a little of an overstatement.” You said, “I see life’s been treating you well too. Loved how you foreshadowed the plot twist.” 

Jess sat down on the bar stool nearest to you, “All of your books were simply impeccable.”

Then with a smile, he pulled a book out of his bag, “Though, I must say, your second one is my favorite.” 

Your heart sank as you braced yourself for the teasing/mocking you get in a few short minutes.

Jess had started to read the synopsis, “He was a montage. A love potion that works in slow motion. He could hardly be described as sunshine but he wanted it comfortable and stayed the same. She was midnight rain, she wanted that pain, would rather chase that fame and all of her changed. Their love was like a postcard of paradise, picture perfect - a guaranteed happy ending. But is anything in life ever guaranteed?”

You sighed, “Jess-” 

“It’s about us isn’t it?” He said, not a trace of any childish humor in his tone.

“If you mean that our relationship served as an inspiration, then yes.” You said. 

“Hm.” Jess contemplated, tracing the small picture of you on the jacket cover, “But they had a happy ending.” 

You shrugged, “A part of me dreamed of getting that ending.” 

“And who says that it's too late for us to have that ending?” He asked, pushing himself off the stool and now standing right in front of you.

You tried not to get your hopes up, “Do you think we could make it work? Pick up where we left it off?”

He reached forward to push the hair out of your eyes, “I mean it won’t always be sunshine and rainbows. We’ll have fights and all but I think that I want to be able to have those fights with you and resolve them with you. Remember when we had that discussion about Romeo and Juliet?”

Furrowing your brows, you didn’t have a clue where this was going, “Yeah?” 

“Alie and Noah may be able to beat out Romeo and Juliet anyday, but I never thought that their story was the greatest one.” Jess said.

“Then who’s?” Your heart was beating faster with every passing second as you had a hint on what the answer was.

“Ours.” 

“But, what about your life in Philadelphia? What about your publishing firm?”

“I can work remotely, then I’ll just go down to Philadelphia if I have to fix something and all. I lost you once, I can’t bear to lose you again.” 

Persistent. One of the many things that made you fall in love with Luke’s nephew in the first place.

Without missing a beat, you grabbed him by the collar of his leather jacket and pressed your lips to his.

“I’m guessing that’s a yes then?” 

“Obviously.” 

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