#jess mariano x y/n

[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!

[thewriterg]

𝐣𝐞𝐬𝐬 𝐦𝐚𝐫𝐢𝐚𝐧𝐨 𝐧𝐬𝐟𝐰 𝐚𝐛𝐜𝐬

pairing(s): jess mariano x gn!reader, collegestudent!jess x collegestudent!reader

summary: you see the title :)

word count: 1.2k

request: if you’re uncomfortable with it you don’t have to but could you write NSFW alphabet with Jess Mariano 🤭

warning(s): smut and language

A/n: —GIFs; @buffysummers— *cracks neck* it’s been a while since I’ve done this but I think I might still got it

Aftercare

Aftercare king

I feel like In his younger years he didn’t really know much about it I mean come on we all knew he was a man whore back than

he would crack you open some water and be on his way before you fell asleep

or fuck you to sleep and leave before you woke up

but he’s gotten better!

gets you a warm rag to wipe you up would run you a bath occasionally but Jess is a little arrogant bitch so he’s not gonna admit that he wants to cuddle with you for a lot of little while 🙄

Body Part

His favorite body part on you is your face even in his younger years jess didn’t base his sole existence off sex he loves to lay a hand on your cheek or kiss your forehead

But In all honesty

Jess is an ass man

There I said it.

His favorite part on himself other than his hair is his hair. he likes when you run your fingers through it and normal time but especially after sex

he’d never say it to your face though it’s Jess come on Y/n 🙄

he’s into hair pulling

pull his hair see what muffled sounds you can get out of him 🙏🏽

because he’s definitely not just going to let it spur out and let you hear them.

bratty jess?

the answer is yes.

Cum

He likes to cum either on your ass or inside you that’s just his preference.

he’s also not against in your mouth when you suck him off

I feel like he’s not really throwing a bitch fit rather you spit or swallow

kiss him and make him taste himself and feels a certain way ;)

but going back to inside you :)

he likes when you clench around him and kinda ground him in a way? Like bringing him back to reality in the best way possible

he’s in love with you either way 🤸🏾‍♀️

Dirty Secret

Jess Mariano is a switch.

Experience

like I said he was a man whore even though it’s behind him now he was a whore.

He has plenty experience on his belt

Also my man is a book reader

You can’t tell me that he hasn’t read smut like let’s be serious for a second

just know that Jess can get around and you’re always gonna finish with him 😊

Favorite Position

Rocking horse and spooning.

Jess is an eye contact person

Just intensely staring at you as he rubs circles on your puffy clit or Keeps running his thumb over your red tip

if you can hold up with his eyes than you might just have him tucked under your thumb

If not than expect him to tease the fuck at out of you and result into shit like fucking you in a mirror forcing you to watch

Goofy

I feel like other than like a sarcastic remark and a couple smirks Jess isn’t really that goofy?

I don’t think Jess is a sunshine/silly character anyways so, there’s that

Hair

He keeps himself trimmed not completely bald but not where to point where he’s uncomfortable or scratching you with it

He doesn’t really care all that much about body hair?

Like it would go like this;

“We can’t, I haven’t shaved.”

“…so?” 🧍🏽🍽️

Intimacy

There’s a lot of things that Jess is but naive however is not one.

when you want to get intimate Jess catches your drift pretty quick

But on a serious not I feel like Jess would like no shit be so sweet sometimes

Like starting up at you as he kiss up your legs to your abdomen and chest

Prepping kissed everywhere kiss rolls, beauty marks, freckles, your back and shoulders, dimples, everything.

Body worship bae

Jack off

He doesn’t do it a lot anymore? He has you and once again he’s never based his whole being off sex intake

but my man is a college student 🙏🏽

and you both have busy schedules so he might have to do what he has to to take his mind off his exam stress

if you catch him!?

please like make him finish in front of you it’d make him so hot and bothered

neither of you would go to class

Kink

Hair pulling; hair pulling is a probably a big key to Jess’s subby side

he is a switch and I’ll die on that hill.

Markings; he’d be a little shit about markings hickeys, hand marks, kiss prints, anything. leave scratches down his back and hickeys one his neck where people can see? he’s fucking whipped and will be back for more when they fade.

Overstimulation.

I rest my case your honor.

Location

your ass or your mouth.

Motivation

When you wear tighter clothes that shows off your figure he loses all sense he has come to have and will shamelessly stare

Also cock warming.

You’re helping him study and he can’t focus? It’s almost like a game

The more flash cards he can go through and get right than the more you move

if he gets more than enough wrong you’ll basically just torture him and sit there as he struggles to hold in his groans

No

Hurting each other other than like a couple smacks on the ass from either parties Jess isn’t into the pain thing at all

Oral

he doesn’t mind a good blowjob

oral fixation go brrr

Place

Risky

Jess is all about the adrenaline he gets off the risky feeling of being caught

Janitors closet type beat

Quickie

Once again y’all are college students

You eat, breathe, and live quickies.

Risk

yes 😈

The amount of places y’all have been in is very questionable

a dressing room 😏

restaurant family bathroom 😝

the janitors closet 🤨

the library 😟

Sext

it’s literally his specialty

“rubbing those pretty legs together thinking about me in the middle of them”

All while your in class

LIEK

sir enough. 🙏🏽

Toys

Not the biggest fan

only toy he was really keen on was something like vibrator underwear

but that’s a story for another day

Unfair

Depending on your personality is rather where you can keep up with Jess or not

because he’s a very big fucking tease

If you can than your best bet is to not let him talk like once you start keep going and he doesn’t have a chance like zero chance

Stare at him dead in his eyes maybe look at lips for a little bit and keep sweet talking him and he’s bending to your will

Volume

you have to really pull the noises out of this one

he’s not letting them slip easy

Wild Card

Once you were giving Jess head he was already overstimulated maybe on his third or forth orgasm and the last one you gave him practically had him unconscious

For the rest of the night he was clinging and whiny wanting you close

That’s been the biggest sun moment you’ve seen in Jess your whole relationship

X ray

6.5 to 7 inches

It gets him around but you’re also not dying splitting in half

Yes

Put your fingers in mouth

Don’t break eye contact as he licks around your digits

you two are at it like fucking rabbits

Zzz

Unless you’ve been at it for a while Jess is usually the one falling asleep after you

he’d run shapes on your hip kiss your forehead when your eyes close and then finally be on his way

[teddypickerry]

Can you do a Jess Mariano blurb where the reader is helping Jess with his homework but he keeps trying to distract her by kissing her lips and neck? 😄 (think of the episode “teach me tonight” but with Jess and the reader dating and he’s kissing her like he kissed Rory in S3 EP10 when they’re walking and kissing)

𝐓𝐄𝐀𝐂𝐇 𝐌𝐄 𝐓𝐎𝐍𝐈𝐆𝐇𝐓 !

pairing! jess mariano x gn reader

warnings! imply of sex (i think that’s it?)

word count! 833

a/n! took me forever ‘m sorry!!! this is also not my best work but back & writing for my boy is good enough for me. <3

the diner was quiet on the particular evening. despite the typical eight o'clock late dinner rush, the door were locked and a red 'closed' sign hung from the blue painted door. the only sound erupting throughout the small former hardware store was the sound of your voice reciting the words from the textbook balanced on your thighs. you were leaned back in your chair, your legs pressed against the table with the book pressed into them. your hair was falling in-front if your face which kept the attention of the boy who sat beside you everytime you pushed it behind your ear.  "and the trail of tears was what year?"

your head bopped up from its current slouched down position as your eyes caught glimpse of the dark haired boy sat beside you. he was leaned on the table, specifically over his book. his head rested on his palm as he held his head up from falling down in boredom.

"is your hair shorter? it looks shorter." your boyfriend was far from an idiot. but in this moment you honestly doubted him. jess was one of the smartest people you'd ever had the privilege of knowing. hell, he was way smarter than you. but here you were sat helping him with history... and geometry, and biology. it wasn't like you were the smartest person in school, but you got your fair share or a's. plus you knew how serious luke was about his nephew passing the twelfth grade. and you'd do anything to get your boyfriend on a good path.

"1828 and 1829." you explained to him simply before continuing onto the next page, him leaning closer to you. it wasn't hard for the smell of cheap cologne, cigarettes, and luke's laundry detergent to catch your attention. especially when you glanced up at your boyfriend's face far too close to your own. "i like it." he mumbled as he lightly pressed his finger to your face, pushing back the strand of hair that fell once more. no matter how long you'd been together, the small touches and glances still made you go mad. "you liked president andrew jackson's racist speech against the cherokee?"

"no," he rolled his eyes at your statement as you tried to diffuse the way he was making you feel on this tuesday evening. "your hair. it's a good length... and you know — i know all about good length."

his comment resulted in a laugh escaping your lips with a smirk growing on his face. jess felt accomplished for making you laugh, especially when you'd just spent half an hour explaining nonsense to him. "okay cmon, back to work." you ordered as he stayed in his exact position. you were about to scold him for not taking this study date seriously. but you lost time when his lips pressed to yours. your eyes immediately shut as your hands cupped his face. he deepened the kiss and leaned over the table to press into you even more. you found yourself getting lost in the kiss that warmed your soul. but before you could be taken by him, you pushed away and pressed your lips together. "jess, we're studying."

"okay we can study," he nodded as he positioned himself back on the chair and balanced a pencil between his fingers. which immediately caught your attention. "i'll start with the inside of your mouth and you can start with mine."

"jess," you hinted with a tone reaching annoyed. he let his smirk grow a bit before glancing around for a moment. "'mkay tell me more about the Indian Removal Act," he shrugged. you gave him a proud smile and muttered a "gladly" before opening the next page and reciting the next paragraph. you were only two and a half sentences in when you felt him move closer to you. and then some more... then some more.

it was when you finished the first paragraph that you felt his dark curls against your jaw as his lips connected with your neck. his arms wrapped around you as he continued to harass your neck with several kisses that would definitely leave a mark. something jess was certainly good at. "jess! we have to study!”

"no, i think you've got this stuff pretty much down." he mumbled as he pulled away for a second before you felt the feeling of his lips reaching your sweet spot. you held in a breath as you found yourself not fighting the feeling for a moment. "you need to learn this stuff if you're going to graduate, jess. please, work with me." you begged as he drew his face away slowly. just enough so that you could face one another. "and after, if you get a b... you might just get something starting with a b.”

the glow on the boy's face suddenly erupted with slightly wider eyes. he simply sat back as he sat his textbook in his lap, leaving only one arm behind your shoulders. "mkay, teach me tonight."

[mystic-writings]

sneak out | jess mariano

PAIRING — jess mariano x fem!gilmore!reader SUMMARY — minutes into your mother’s dinner party, jess suggests you sneak out through your bedroom window - and you can’t help but agree WARNINGS — fluff, jess and reader being ‘troubled’ teens, a bit of angst, reader venting WORD COUNT — 2,322 NOTES — the idea of lorelai having a teen that was just like her is so appealing to me idk why - also would you believe me if i told you i listened to yung gravy while writing the majority of this fic

masterlist | navigation

You weren’t sure which was worse - the dinner your mother was hosting, or the idea that you now had to put up with a whole night of Luke’s strange nephew, whom you’d never met before.

Of course, you loved your family to pieces, and you loved Sookie and Jackson; hell, sometimes you looked at Luke as more of a father than you did your actual dad, but having everyone together for what you knew would be at least a three course meal, under one roof, with Luke’s mysterious nephew from New York, just felt draining.

So, to preserve what little social battery you had left for the day, you decided to spend the time between school and dinner in your room upstairs with a good book and a cd playing from the player that sat on your dresser at a low volume. You had to change the cd twice, first from one of your mothers Bangles cds to a Smiths one, but just as you were enjoying the beginning of David Bowie’s Ziggy Stardust album (and nearly finishing up your book), did you hear the clanging of pots and pans from downstairs, as well as Sookie and Jackson’s lighthearted bickering.

You managed to bury yourself back into your book, one leg crossed loosely over the other outstretched one as you half-sat, half-laid on your bed, being mindful of your shoes so as to not get any dirt on your covers.

From downstairs, Jess was wandering around the Gilmore home as everyone else did whatever they were doing in the kitchen, internally monologuing and half-mocking their decor. He’d met Rory already, and she seemed like a nice enough girl. Enjoyed books. But he had yet to meet the third and final Gilmore girl, who so far had only been mentioned. However, as Jess scanned the various photographs on the mantle, he could hear the faint guitar of Suffragette City emanating from somewhere upstairs.

After peeking down the hallway to make sure no one was watching, Jess smirked and snuck up the stairs, into what was surely off-limits territory for someone like him. Still, he took the stairs two at a time and stealthily, managing to avoid all the places that would creak in a house like this one, despite never stepping foot inside beforehand. He followed the music down the hall, past some more paintings and pictures, to another bedroom. The door was open, and he was able to take a look inside. Posters covered most of the wall, leaving little space to show off the paint beneath them. Bookshelves occupied the wall right beside the door, and similarly to Rory’s room, they looked stuffed to the brim with books.

On the bed, facing him, was the person he assumed to be the final Gilmore girl - Rory’s twin sister. He watched intently, scanning every feature of your focused face as you scanned the final pages of the book you were reading. How your brow furrowed, eyes locked on the ink before you. The way the foot that hung off the edge of the bed was moving to the beat of the song.

Once Jess had decided that he’d been watching you long enough to constitute stalking, and how that was probably extremely creepy, he nudged the door open with a creak and stepped inside, clearing his throat and pulling his lips into a slight smirk. “Hey there, Ziggy.”

At first, you thought that your mother was finally calling you down to dinner, until you heard the unusually male - and entirely unfamiliar - voice come from the body in your doorway. Tucking a receipt into your book to mark your place, you glared over at the boy standing in your room with his hands behind his back, smugness rolling off of him in waves as he admired your room.

“You’re Jess, aren’t you.” Your flat tone seemed to amuse him.

“How nice, you already know my name. I’m flattered.”

You watched him as he walked around your room, over to the window where your desk was, trying to figure him out as he peeled back your curtains. “It’s impossible to not know someone’s name in this town, even someone who’s only been here for 28 hours.”

He chuckled. “Nice one, Ziggy. Now tell me, why aren’t you downstairs with the rest of the freakshow? I mean, they are your family, after all, aren’t they?”

You pretended to smile, but it came out as more of a grimace. “Sorry to break it to you, Mariano, but I’ve been banned from the freakshow. Apparently having apathy toward any sort of Gilmore humour is forbidden, and they’ve locked me away forever.”

“Aw, so sorry to hear that.” Jess mocked, placing a hand over his heart with an exaggerated pout. “I can’t believe they shunned such a ray of sunshine.” He smirked at your rolled eyes. “No, really, you must be a real treat at parties.”

“Quit it, Mariano. Is there a reason you came up here or did you just want to cause enough trouble to get kicked out of our beloved Stars Hollow? Because if so, you came to the right girl.”

Jess’ brow quirked. “Really?”

“Yeah,” you heaved a dramatic sigh, slipping off your bed to walk over to Jess. “But it’s like… 9pm on a Wednesday. In Stars Hollow. Even if I wanted to cause trouble, and I don’t, because I did enough of that at school today, there’s nothing to do. Everyone’s asleep, and I’m pretty sure our 24-hour mini-mart closed like, half an hour ago.”

Now it was Jess’ turn to roll his eyes. “Your sister said that already. Is there seriously nothing to do here?”

“Nope.” You shrugged, just as a thought came to mind. “Well… there is one thing…” Jess’ eyebrows raised at the prospect of having something fun to do, and you couldn’t help but laugh. “It’s not anything revolutionary, you know.”

“Still, give me something, anything, to get us out of here, Ziggy. I’m begging you. I’m being suffocated by the stale air of suburban life.”

You nodded, tapping your fingers on your thigh. “Fine, I’ll tell you. But you gotta do one thing for me.”

“What is it? I’ll do anything, I swear.”

“Stop calling me Ziggy.” You said. “It’s a stupid nickname, and although I admire the fact that you listen to David Bowie enough to come up with a nickname like that one, I hate it. Call me by my actual name.”

“Well I would, if I knew it.”

“My mother never told you my name?” You asked with a raised brow. “She never shuts up about me and Rory, I’m surprised you never caught it.”

“Apparently, I didn’t. It seems she likes talking about Rory more.” Jess shrugged. “At least, around me she does.” He barely caught the slight sag of your shoulders, the drop in your demeanour, before you picked it back up and smiled.

“Well, Jess. I’m Y/n. Y/n Gilmore.” After a pause, you looked around and snagged a sweater from the chair in the corner of your room. “Now, if you’ll follow me, let’s go have as much fun as we’re able to in Stars Hollow at night.”

Jess waited impatiently behind you as you unlatched the window by your desk and pushed it up, slipping through and holding it open for him. As he clamoured out, you grabbed the rock underneath the window and placed it on the windowsill, lowering the window so you’d still be able to get back in later.

You could still hear the tail end of the album playing as Jess looked around.

“How are we supposed to get down?”

“The trellis, obviously.” You said, carefully making your way across the porch’s roof to the trellis right next to the kitchen window. “Just don’t make much noise, this thing is right next to the kitchen’s window and if we get caught we’re screwed. Follow my lead, and run when you hit the ground, got it?”

“Got it.”

Scaling down the trellis was basically second nature to you, but you made sure to look up every once in a while to make sure Jess was doing okay. He seemed to be, which comforted you somehow. You waited at the bottom for him, making sure to stay out of view of the window to the kitchen and the edge of the porch, which were on either side of the trellis, and could possibly get both you and Jess grounded.

When he landed, he looked at you, and a dish clattered in the kitchen. You both snapped to the window, then back to each other. On instinct, you took his hand and ran toward the woods.

“Where the hell are we going?!” Jess whisper-shouted.

“Relax!” You whisper-shouted back, slowing to a stop as soon as you were hidden in the tree line. “We’re not going into the woods, dumbass. What do you think would’ve happened if we waltzed out in the open in front of the living room window?”

Jess only sighed and nodded, letting go of your hand. He let you lead him through the trees, keeping the light of the house close to you, walking around the garage and past all the cars, waiting until Babette’s house was out of sight until you stepped back onto the road.

The walk was calm and quiet, crickets and the breeze occupying you instead of chatter. After a while, when you were beginning to reach the town centre, Jess spoke up. “So, what now?”

You shrugged. “Not sure. Usually I head to the lake, bring a book, or a cd player and some headphones. I don’t normally bring people with me, you know?”

Jess nodded, lips slightly pursed. The walk continued through the town, passing by shop after shop, all of them closed for the night. You had to admit, you weren’t used to taking walks like these, out in the open. Normally you’d find whichever path kept you out of the possible sight of the townspeople, a habit you developed after Taylor snitched on you to your mother after he caught you walking to the lake by the Inn when you were 12. Still, it was nice, and even if you were caught, you somehow didn’t seem to mind it.

As the buildings were fading again and you knew you were approaching the lake, you checked your watch. 9:27pm. You sighed, and Jess looked at you. Dropping your arm, you shook your head. “Almost 9:30. They definitely have to know something’s up at home. Probably sending out a search party by now.” You told him, before shrugging. “Or, you know, miraculously, they forgot we existed and are eating Sookie’s delicious no-allergen, fourteen course meal as we speak.”

Jess scoffed. “Yeah, right. Luke might not care that much, but Lorelai? She seems like the world’s most protective parent.”

“She is.” You confirmed, sitting on your usual bench, eyes following Jess as he sat next to you. “Trust me, I love her to death, but it gets annoying sometimes.”

“Yeah, well, at least you have a protective mom.” Jess’ hands gripped the edge of the bench, his body hunched forward, making him look small, ready to run at a moment’s notice. “Mine decided I wasn’t worth the effort. Shipped me off to this… circus show without so much as a ‘sayonara, kid.’ You’re lucky.”

You frowned. Everyone knew within the hour of him arriving in Stars Hollow that Jess was a troubled kid, but even troubled kids deserved parents that cared. He was right, though, you were lucky. It just didn’t feel like it.

“I know I’m lucky, Jess, but it’s not all rainbows for me, you know.”

“Oh yeah? How?” He scoffed. “You have the perfect life, Y/n. A mom that cares, a great twin sister - hell, even Luke sings your praises.”

“Luke sings?”

Jess rolled his eyes. “You know what I mean.”

“It’s not like that all the time, Jess.” You sighed. “My ‘great’ twin sister is, apparently, so great that she has all eyes on her at all times. My grandparents are always so proud of her for being so smart and planning this amazing, expensive, studious future - they’re planning on funding it, too, from the sounds of things. I just want to live, you know?” You kicked a rock with your shoe, avoiding Jess’ concerned gaze.

“And my mother seems more concerned about her wellbeing than mine, closer to her than to me. But somehow she wonders why I’m the troubled one. I mean, I act out, I barely go to that stupid prep school because it’s so suffocating, and I got an eyebrow piercing without permission instead of taking a calculus test last month, which I’m just getting out of that punishment. Everyone’s so focused on Rory and how seemingly great she is, I don’t even remember the last time I was appreciated for anything. And don’t even get me started on my dad.”

“Sounds like these freaks don’t know a good person when they see one.” Jess told you. “You seem chill. Adventurous, too. But just because you aren’t appreciated doesn’t mean you aren’t good enough.”

You couldn’t help but smile. “You too, Jess.” The world quieted around you for a moment, stars shining off the rippling waters of the lake. “But we don’t need to be good enough for them. Just good enough for us.”

He smiled, nodding once at you. Again, you appreciated the silence with him, watching the water or the sky. It wouldn’t be long until Luke and your mother found you both, you with your head on his shoulder and one knee bent to your chest, laughing quietly at a joke he told as you continued to get to know one another. But that was later. For now, you simply sat and watched the water, wishing the moment could last for the rest of your lives.

permanent taglist: @just-here-to-escape-from-reality @mazerunnerrose @theboldandthebootyful @miraclesoflove @queen-asteria04 @heliads

jess mariano taglist: open!

taglist form is in my navigation!

[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.”

[scarlet4rose]

Sleepless without you

Jess Mariano x reader

--------------˖⁺‧₊˚♡˚₊‧⁺˖---------------

story: your boyfriend Jess wakes you up in the middle of the night cause he can't fall asleep, he's too busy thinking about you

--------------˖⁺‧₊˚♡˚₊‧⁺˖---------------

It´s 3 am and Jess lies awake in his bed. Every time he closes his eyes, he sees your face before his eyelids. He turns around in bed, but he can't get you out of his mind. Jess sighs, thinking about you all the time without you with him is driving him crazy!

When he dropped you off at your house at 10pm, you said you were super tired, so he didn't want to ask you if he could stay over. So he had decided to go to bed early himself too, but now he couldn't find any sleep no matter what he tried. Dammit! One thing was clear, despite of what he had set out to do he just had to see you!

A few minutes later, he had crept to your house in the dark of night and was now standing in front of your window. He knocks, at first gently, then louder.

"Y/n", he whispers your name and fervently hopes you hear him and have not yet fallen into a deep sleep. After a while he hears noises in your room and you open the window a crack.

"Jess?", your sleepy voice couldn't sound any sweeter to Jess and he starts to grin "Yes, it's me babe, as I live and breathe"

You open the window all the way to let him in and he doesn't let a second pass before he joins you in your room.

"What are you doing here?" you ask confused, "I thought we were both going to bed early?" Jess pulls his left leg through the window and is immediately right in front of you, he puts his hands on your hips and gives you a quick kiss on the cheek. "Change of plans, I guess."

"Oh nooo, Jess, I'm really tired," you sigh.

"Yeah, me too, angel"

"Then why the hell didn't you stay home in bed?"

Jess smiles guiltily and lets out a small chuckle "I couldn't sleep without you. I just... I couldn't help it, I had to come here to see you" Your knees go a little weak and you notice his gaze, which he hasn't yet taken away from you for a mere second.

You sigh again "Alright Jess, then stay, I guess" Jess leans in and kisses you deeply, he pulls away from you and then gives you a second kiss. he really can never get enough of you.

"Thanks, babe, I was hoping you'd say that" he then laughs suppressedly "Without your mercy, I probably would have died of insomnia tonight" you roll your eyes "Oh please! The way I see it, I'm the one now who's gonna die of insomnia tonight instead"

Jess shakes his head as he gently twists your body around so that your back is now pressed against his chest. He slowly walks you back to your bed in the corner of the room. "Nah, no way Y/N. You`re gonna get your sleep, I promise".

Standing in front of the bed, he slowly lowers you onto the mattress and pulls the covers over you before getting in bed himself. He wraps his arms around you and whispers softly "Y/N, angel, I swear I came here just cause I needed to see you. Needed to be with you, alright?" You can't help but smile while you lean back against him "Oh Jess, I guess you`re growing soft. My Jess, my poor Jess..."

Jess frowns slightly "whatever that means. I snuck out and came here to see my girl, that`s not... well- I thought you wanted to get some sleep. You wanna start arguing now?" You grin and turn your head around to kiss your boyfriend on the cheek

"No need to argue, baby, you´re the toughest guy I know, really. well, and...", you can feel his heart beating faster behind you, "and I love you"

Jess presses a kiss on your forehead and hugs you even tighter.

"I love you, too, Y/n"

you snuggel into him and the two of you drift off to sleep.

Good night ˖⁺‧₊˚♡˚₊‧⁺˖

[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.

———

[wasabidottie]

Because you asked for requests. Maybe building gingerbread houses with Jess Mariano? xo

Frosting (Jess Mariano)

a/n: anon!!!!!<3 thank you sm for this request! sorry for how long it took, hope you like it :) and to anyone else with requests ill get to them asap :))

The aroma of gingerbread filled the cozy apartment as you an your boyfriend, Jess Mariano, gathered around the kitchen island, ready to embark on the annual tradition of building gingerbread houses. The table was cluttered with an assortment of candies, icing bags, and, of course, pre-baked gingerbread pieces.

Jess eyed the array of candies with a mischievous glint in his eyes. "You know, half of these are gonna end up in my stomach, right?"

You chuckled, playfully swatting his arm. "Behave, Mariano. We need those for the gingerbread house."

As you both started assembling the houses, the competitive spirit ignited. Jess, surprisingly meticulous with the task, scrutinized the angles of the gingerbread walls, determined to make his house a structural masterpiece.

"This has to be stable," he muttered to himself, holding two pieces together as if inspecting a construction project.

On the other hand, you were more focused on the decorative aspect. Your house was adorned with colorful candies, creating a vibrant, sugary landscape.

"Are you going for a candy wonderland or a gingerbread fortress?" Jess quirked an eyebrow, eying your creation.

You grinned. "Why not both? It's called creativity, Jess."

The banter continued as you both decorated your respective houses. Jess's concentration was evident, but you couldn't resist the occasional candy theft – a sneaky swipe here and there, which he pretended not to notice.

Eventually, the clash of creative visions led to a playful argument about the perfect gingerbread house aesthetic.

"It's like a battle between tradition and chaos," Jess remarked, eyeing your candy-covered masterpiece with a raised eyebrow.

"Tradition with a touch of fun," you countered, adding a gumdrop turret to the roof.

As the gingerbread houses neared completion, Jess couldn't resist any longer. He grabbed a handful of candies and strategically placed them on your creation, breaking into a sly grin.

You gasped in mock horror. "Sabotage! This is war!"

The playful argument escalated into a candy fight, both of you laughing as you exchanged sweet artillery. The kitchen was now a mess of frosting and candies, but it was a mess filled with laughter and shared moments.

Finally, you both stood back, surveying the sugary battlefield. Jess had a triumphant grin, a candy cane sword in hand.

"I win," he declared, a victorious glint in his eyes.

You shook your head, smiling. "Fine, fine. You win this round, but only because I let you."

The banter paused, and Jess looked at you, his eyes softening. Without saying a word, he leaned in and kissed you – a sweet, lingering moment that went beyond the playful argument.

When he pulled away, he wiped a bit of frosting from the corner of your lip. "You had something there."

You smirked, knowing the real reason behind the kiss. "Uh-huh, sure. It was just the frosting."

Jess chuckled, pulling you into a tight hug. "Whatever you say, but don't blame me if I need to inspect for stray candy again."

As you both shared a laugh, the gingerbread houses stood as sweet testaments to a day filled with laughter, love, and a bit of delicious chaos.

[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

[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

[pettydollie]

I have a request if you are interested? :)

A teen!dad jess. He has a best friend from New York (she can have a name or it can be Y/N, you can choose) (they are endgame, jess never had feelings for Rory but she has feelings for Jess, it won't go anywhere) Jess and his best friend have a kid, they co-parent (whether they are dating already or in the future is up to you) Jess gets sent to Stars Hallow, she ends up moving to stars Hallow to, to be close to Jess and so their kid can be with him too (she is emancipated, plus Jess knows she's coming because they keep in contact) if anyone reading this would like to turn this into an actual story, I'm totally down for reading it :) if you choose this request, I look forward to reading it. Thank you!!

hi noonie!! this is my first requests omg wowowow i think this is a great idea! im sorry if its kinda sloppy and not how u wanted! but i hope u enjoyy ! wc: 1.7k also i saw how you said that jess knew she was coming, but whats more fun than a suprise? ;) ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ As your best friend grabbed his bag and walked towards you and your one-year-old son, you forced yourself to keep your composure. You didn't know how you were going to okay without him. You'll still see him when he comes back to visit for holidays and such, but it won't be the same. You didn't want Jess to leave and neither did he, but he had no choice. He walked over to you and S/N. Reaching out for his father, S/N cooed and Jess took him from you. Jess held him preciously like it would be the last time. "Be good for your mom kid." He kissed his head.

He put down S/N into his crib before walking over to you and grabbed both of your hands. "I'm going to call you twice a day. Morning and night, okay? If there's anything you need, I'm there for you." He explained clearly. You nodded your head as you chewed on your lip, unable to form words. You wrapped your arms around his neck in a tight hug. Jess Mariano was your best friend. Having S/N was an accident, but you and Jess both believed that everything happens for a reason, so you kept him. And neither of you regret it. Your relationship is a little odd, but you love him nonetheless. You pulled away and kissed his cheek. "You'll be okay." You whispered, wiping a tear from your cheek. "And so will you, Y/N. You're the strongest person I know." You smiled softly at his words and gave him a picture of the three of you. He grinned and held it tightly. "Don't miss your bus, buddy." You joked. He ruffled your hair and waved goodbye.

A year later, you still feel the same as you did before. You know, the same day the two of you created a child, the same day you gave birth, and the same day he left. And you were panicking. "Oh, S/N, I'm so excited!" You jumped around making S/N giggle. He bounced along with you. "But I'm nervous too. What if he found someone else?" Then you gasped. "What if he cut all of his hair off?" You exaggerated just to see S/N's goofy smile. "This isn't about me though. This is all for you!" You tickled him (ugh, he's so darn cute). You grabbed your luggage, held S/N on your hip, and left the apartment. Stars Hollow was a cute name, you had to admit. You were thrilled to live in a small town! When you arrived, you stepped off the bus and looked around. Just as you imagined, it looked great! But maybe you should’ve told Jess you decided to be spontaneous and move to Connecticut. On the other hand, Jess could be on the verge of dying from boredom, so a surprise is the perfect thing to cheer him up.

“Thoughts, S/N?” You asked, clenching your hand into a fist as a pretend mic to his mouth. Your adorable son stared at you with his gorgeous eyes. Damn he looks just like his mother. Kidding, he’s an exact replica of Jess. Anywho, you accepted his answer and began to explore.

45 minutes later, you realized that you didn’t plan this out well enough like you thought. Even after talking to Jess everyday on the phone for an entire year, you didn’t know where exactly he was located. Fortunately, you took notice that people often went into a cute little diner called “William’s Hardware Store”, so you followed the crowd into the diner a little bit confused because this didn’t look like a hardware store. You walked in and almost immediately, people started turning to look at you. But atleast S/N enjoyed the attention.

You cleared your throat awkwardly and walked over to the stools at the counter and sat next to a girl around your age. You placed S/N in your lap and took in your surroundings. The girl you were sat next to turned around and gave you a bright grin. “Hi! You’re the new girl, aren’t you?” Her voice was sweet like candy (in the best way possible). “That I am! I’m Y/N. And this dude here is S/N.” You grabbed his hand making him give a little wave. She giggled. “Well, it’s nice to meet you, Y/N. And you too, S/N.” She tickled his belly quickly and perked up to you. “I’m Rory!”

You looked to where a boy was coming out of a hidden room and THERE HE WAS IRJAHDJWHS

Thank goodness he didn’t cut all of his hair off. You suddenly felt butterflies in your stomach, which you hated. Rory turned to face where you were looking and scoffed. But he was right out the door as quickly as he came. “Not the best of friends?” You asked, jokingly. “Jess? It's.. kind of weird right now. But yeah, no.” She informed you. You nodded. Weird? Like romantic weird?

“Hey, what can I get you?”

You turned away from Rory and looked in front of you. This looks EXACTLY like who Jess explained to be his uncle, Luke. You remember seeing a sign saying “Luke’s” bellow the hardware store sign. Backwards baseball cap, plaid shirt, scruffy facial hair, this must be him. “This is Luke, Y/N. Luke, Y/N just moved here from.. where?” Rory introduced and then turned to you. “New York.” You replied. “Oh, welcome. What part? My nephew Jess is from New York also.” Luke smiled. “Same as him.” You responded. Rory and Luke looked confused and you felt awkward again. Not the right choice of words.

That was until Luke’s face changed from “what is she talking about?” to “ohhh THAT Y/N!” You're glad you didn't have to explain.

“Y/N! It’s great to meet you! How are you? Is this S/N?” Luke looked below to see S/N’s cute lil chubby face. “Yup, this is him!” You held S/N up higher so Luke could see him better. “Wait you know Jess?” Rory asked. “Father of my kid. It wasn’t planned, but things happen, you know? Anyway, he’s my best friend. We’ve know each other since childhood, actually.” You explained. “Wow, this is amazing! So- so you live here now?” Before you could answer Luke, he rushed up and walked to a phone, dialing a number. “I'm gonna get him to come back right now, don't worry."

“Oh, uh. Well sure, I suppose.” You muttered. “Um, well I have to go home to my mom, but it was great meeting you! See you around!” Rory waved goodbye and left. You mentally smacked yourself on the forehead. You were never good at first impressions, EVER. Just a few seconds after Rory left, the door opened again to reveal a sweaty Jess with a panicked expression. “Where’s the fire? Why’s everyone so calm?” He ran over to Luke. “Here, lemme show you.” Luke placed his hand on Jess’ shoulder and guided him to your seat. You fixed your hair as quickly as possible.

Jess stood and stared. “Wh-What are you doing here?” He brightly smiled. He looked down at S/N, who stared into his eyes. He took him from you and rocked him slowly. “Hey, kid.” Jess kissed S/N’s head. “Hi, Jess.” You spoke shyly.

He then turned his attention back to you. “Hey,” He gazed. You stood up quickly and wrapped your arms around him. Luke took S/N from Jess so he could hug you back fully. “I can’t believe you’re here.” He whispered in your neck. “I missed you.” You told him, pulling away. Although Jess always had trouble expressing his feelings into words, it was a little tense when he didn’t respond back to you.

Luke awkwardly turned to you. “Sorry, Y/N, I gotta get back to work.” He apologized, giving S/N back to you. “It was nice meeting you.” You smiled. He winked and walked back to the kitchen.

"Sooo, how have you been?" You asked, trying to start a conversation while bouncing S/N in your lap. "I've been alright." He put his hands in his pockets and began to speak when a blond chick wrapped her arms around him. "Hey. Where were you? I thought we were gonna go to my place." She prodded. She then turned to face you. "Aw, cute baby."

Of course he had a girlfriend. He was always cool and popular in school, so why wouldn't he be here? You were terribly mistaken to think otherwise. But now you felt a weird pit in your stomach. This was a bad move. You shouldn't have come here. But no, your son needs his father. So, you decide to be brave for S/N.

"Can we do this later?" He mumbled to her. "So you expect me to be okay with this? Ugh, what's the matter with you?" She stormed out of the diner before Jess could respond (not that he wanted to). "Trouble in paradise?" You questioned wholeheartedly. Although you were disappointed, you weren't going let this get in the way of your friendship. He scoffed. "Shane is definitely not my paradise. Look," He got serious for a moment and sat down on a stool next to you. "I'm happy you're here. Really, I am! But you came at a bad time." He told you. "Love triangle?" You joked, thinking back to how Rory said things were weird between them two. "How'd you know?" Jess' eyebrows furrowed. Oh. "Lucky guess." You shrugged. Well, this can't get any better can it? "It was nice seeing you. I should go start unpacking though." You stood up and switched S/N to your other hip. "Listen, let me get things sorted out and I promise I will be with you." He grabbed your hand. "Sorted out? Jess, you shouldn't feel forced to be with me. It's okay, I promise." You tried to reason with him. Why did he make it seem like he had no other option but you? Clearly he has choices.

"No, no. I need to be with you. Remember a few weeks ago when I told you I was gonna go back home?" He asked. You nodded. "That's because I wanted to be with you and my son. But you stopped me and I listened. So, now you're here and I'm gonna be the best damn father I can, alright?" He let go of your hand and ran behind the curtain. All of a sudden, S/N began to cry.

a/n: i'm gonna do a part two dont worryy! im just tired rn but i will try and draft something later tonight and maybe post it tmr xx this was a little hard for me to write since jess would be more mature as a father (atleast i think so) and he wasnt alone like in the show yk? but i had fun nonetheless :)

[teddypickerry]

A teen!dad jess. He has a best friend from New York (she can have a name or it can be Y/N, you can choose) (they are endgame, jess never had feelings for Rory but she has feelings for Jess, it won't go anywhere) Jess and his best friend have a kid, they co-parent (whether they are dating already or in the future is up to you) Jess gets sent to Stars Hallow, she ends up moving to stars Hallow to, to be close to Jess and so their kid can be with him too (she is emancipated, plus Jess knows she's coming because they keep in contact) if anyone reading this would like to turn this into an actual story, I'm totally down for reading it :) if you choose this request, I look forward to reading it. Thank you!!

↯ 𝐂𝐀𝐍 𝐈 𝐆𝐎 𝐖𝐇𝐄𝐑𝐄 𝐘𝐎𝐔 𝐆𝐎?

pairings — teen dad! jess mariano x y/n

warnings — none!! (unedited tho so…)

word count — 2.9k

a/n — i’m not the biggest fan of how this turned out (feels lowk out of character even tho i typically write jess best bc i am him), but i LOVEDDDD this plot. i plan on making a part two if that’s something you guys would want!! also dad! jess is my fav (as you guys know) so to have him be bowie’s dad??? FUCKING LOVEEE.

BEING SENT TO STARS HOLLOW was worse than one would imagine. especially for jess mariano, a kid who'd been taken from his hometown and placed in a small apartment above a diner with an uncle he hardly knows. this would be enough to drive one mad, one could presume. but to make matters worse, he was leaving behind his son.

the moment liz danes found out her sixteen year old son had gotten a girl pregnant, she freaked out. as any mother would do. but liz wasn't just any mother, she was (to put it lightly) a whack-job. so she spiraled when she figured this one out. what happened when liz danes spiraled you may ask? who was there for her? her sane big brother, luke.

the practical idea seemed to be sending jess to the quaint down of stars hollow. a place where liz grew up, where she knew luke would keep an eye on him. where she also knew he couldn't cause any havoc. and his world wouldn't become corrupt like hers, being a teen parent.

the months of the pregnancy was difficult to be away. y/n was just a girl he'd met at a party, he was sick and tired of his mother's new boyfriend's hurtful words. y/n was going through something similar and they decided they'd lean on one another one night. until three weeks later when she called jess asking him to coffee, and surprising him with something much more. y/n was scared, as any pregnant sixteen year old would be. being without jess didn't help her case.

the teenage boy didn't let the separation get to them however. his nights sneaking out were spent at a phone booth in the middle of town, talking to y/n about everything and anything. his breaks at the diner were calling to ask about doctors appointments. sure, she had just been a girl he'd met at a party. but the emotional bond of a baby knitted the two together. they were scared kids, they had no one but one another. so they became much more than kids who once went to a party. they were friends.

when y/n went into labor, jess ran out of school like his life depended on it. hoping into his car and speeding back to new york. luckily making it so he could see his son born just in time. his first time meeting his son was only his fourth time seeing y/n. the fourth of many, many visits. stars hollow became less and less entertaining to him as time went on. especially after coming back almost two weeks after his son was born. the pranks, the stealing, the teasing around with this girl rory... it wasn't anything to him. he missed his son, he missed the woman who had his son. jess mariano wanted to be with his family. because for the first time in his life, he had a family. someone loved him, and he loved someone.

"1984 is the most overrated 'classic' book i've ever read," rory gilmore smiled at jess with a teasing look. now, almost a year after his son's birth, jess mariano was nearing eighteen. his adolescence was coming to an end (although it did when the stick turned pink). the toying around was still very much in his nature. hence the conversation with the good girl in a pink sweater.

"nu uh, it's a classic. you can't just hate on 1984," jess counters while standing behind the diner's countertop. the diner was slow, despite it being around the early afternoon and a sunday. which is why two teenagers were sharing false opinions like it was bible. he didn't like her — he was sure of that. ever since bowie mariano was born (guess who named him), jess's feelings had become aware. the love he felt for his son was prominent in his everyday life. unlike anything he'd ever felt before. it was hard for him to even imagine ever having feelings for someone. not when being a dad was his number one priority.

"you're just saying that," rory laughed at his words once more. her late night talks with her mother about jess seeming to not be recalled. the ones where lorelai stressed to rory what jess was going through as a teen parent, something she knew all too well. especially being away from his kid. in her eyes, he was a christopher who'd left his rory. lorelai didn't exactly want her daughter involved with that. but it was hard to resist when he kept giving rory that james dean look. matched with the leather jacket and the book references.

"when are you going to see bowie?" lorelai asked the teenage boy, attempting to remind her daughter of his priorities. jess didn't see this as a question with ulterior motives. he knew lorelai had a deep understanding of him, whether she'd like to admit it or not. "soon, hopefully."

"is y/n liking her new place?" luke questions genuinely from lorelai's side, being reminded of jess's child's mother who he'd grown fond of. "it's kinda hard to like a place where you're crashing on your friend's sofa bed." jess scoffs, being reminded of his friend's condition. when y/n had first gotten pregnant, jess was aware of the darkness in her home. especially when she freaked out to him one night. the first time they opened up to one another. she was too scared to tell her dad about the baby, knowing he'd hurt her.

less than two years later, y/n was emancipated. working a part-time job in the city. where her friends helped watch bowie when necessary. along with (hesitantly) liz, whenever jess made sure she was sober and had an okay boyfriend. it was a lonely life: just like jess's.

"that poor girl," lorelai commented with a sympathetic look making jess's stomach twist. he hated thinking about the living conditions of his family, he hated thinking of being apart from them. but when he did, he couldn't stop. which is why that night, when luke came upstairs to the apartment after closing, jess stopped him to have a serious conversation. "can i talk to you?"

luke searched his nephew's face for sincerity once he heard those words. curious if this was gonna be a 'steely dan sucks' conversation or an actual serious one. a rare option for the teenage boy. "yeah, what's up?"

there was a deep expression anguished on jess's face as he sat at the table. he was clearly unsure how to put his words, which was prominent in his eyes. "i... i can't be away from bowie anymore. i can't let y/n live in that shithole. they're my responsibility."

luke heard his nephew's words clearly. he agreed with every word, a sigh erupting when he processed the stress his teenage nephew was experiencing over this. "where are you going with this, jess?" the diner owner questioned with a calm tone. he still wanted the best for his nephew. he still wanted him to finish high school and start a worthy life. one he didn't want to be started by running off to new york and working to provide for his family. "i need to be with them one way or another. i can't be away from bowie, i can't do that to my kid. i can't be my dad."

"you're not, kid. you're nothing like jimmy, i'm telling you that right now. you would do anything to be with bowie and that proves you're better than him," luke explained before letting out a sigh and nodding his head. "you're a good guy, jess."

a conversation continued throughout the night until the two finally came to a conclusion. or at least luke did. taking matters into his own hands, he picked up the phone once his nephew hit the pillow. a hushed tone rushing into verses of explanations until it all made sense.

the next morning, jess mariano woke up like any other day. not too long after he woke up he went down to the diner to get started on work. his thanksgiving break had begun, so his monday would be spent annotating a new book for his son in between rush hours. it was when two familiar faces entered the diner that he hardly glanced up, noticing the gilmores immediately. "hey jess, how's it going?"

"well, i'm not bleeding or anything so..." jess shrugged towards the woman while he scribbled in a final note for an older bowie. rory kept her eyes on him while luke handed the two mugs of coffee. he had something in his head, especially when he kept glancing out the window every few seconds. "that's good," lorelai nodded before turning to luke.

"what are you reading now? more jane austen?" rory teased while eyeing the boy and taking a sip of her warm coffee. his eyes didn't dare look up from her while he shut the book, "uh huh." he nodded with a thin lipped smile. rory noticed the children's book in his hands and grinned, "didn't know you were that behind. that makes sense with your book taste though."

"this is bowie's, i'm just writing some stuff in the margins for him for when he learns to read," jess shrugged without noticing the sudden change in demeanor when he mentioned his son. the baby had never been to stars hollow. jess also rarely brought up his son to anyone, especially stars hollow-ers. miss patty and babette already whispered about the rebellion enough as it was. he didn't need to add to it by opening up to people who didn't care about him. "oh... that's sweet," rory forced a smile before sinking down into her seat. she felt shorter.

jess picked up the coffee to begin to refill a few cups throughout the diner. his stance was interrupted once the diner phone began to ring, luke noticed this quickly. it wasn't long before he grabbed the coffee from jess's hand and hardly offered to do refills for him instead. jess knew luke was up to something but hesitantly took the phone call, "luke's."

"nice greeting," a voice echoed on the other side making jess's infamous smirk spread across his face. y/n. "well, i thought i'd ask you to marry me. but i was worried our meat supplier was on the other line," jess teased into the phone while his hand went in his pocket. he subconsciously turned around so his back was to the rest of the diner. wanting to be alone with y/n, as if that was possible through this.

"thought so," y/n hummed with an obvious smile. "hey, bowie's missing his dad."

"is bowie's mom also missing bowie's dad?" jess asked with his typical teasing tone towards his friend. "bowie's mom may be. but she doesn't exactly want to give him the satisfaction of that. bowie's dad is very cocky," y/n says through the phone while luke spots something through the window and smiles.

the sound of the bell was a familiar one. reminding the people in the diner that someone had arrived. jess was so used to it now that he didn't bat an eye typically, but this time he glanced around his shoulder for a moment. his eyes glancing back at the figure stood infront of the door. jess's brown eyes locked on them for a second as he dropped the wired phone and bolted past the counter to them.

stood before his eyes was y/n and bowie. the eleven month old was in her arms with a pacifier between his lips. y/n wore a smile while she placed her phone in her pocket with a free hand. she was engulfed in jess's scent immediately as he threw the two into his arms. cigarettes, cheap cologne, and coffee erupting comfortably into her. "hey, watch out i have a baby."

jess ignored her words, but lightened his grip on her while taking bowie out of her arms to hold him. "bowie, hey..." his voice trailed off as he held onto his son. he was interrupted with emotion by being with his son once again. because as much as fatherhood was something he never wished upon himself, ever desired whatsoever, it had turned into the best thing that ever happened to him.

"hi kid," luke greeted the teenage girl while walking over to give her a side hug. he turned his attention towards jess who was hugging his baby with a grin he hadn't seen in awhile. "i thought about our talk last night, jess. you were right."

jess glanced over at his uncle before looking back at y/n with a smile. which shocked even him, because a smile was not something he'd done while being in stars hollow. "so..." luke's voice trailed off while he gave the floor to y/n. who took it and looked at jess, "i think bowie needs to be with his dad... and his mom."

the group shared a few looks, mixed with confusion and happiness. "i asked lorelai for a favor, y/n and bowie are gonna stay at the inn for a few weeks. until you guys can figure out a place." luke started with a nod. "you're gonna be eighteen in a few months, you're gonna graduate in a few months. i want you to do that, jess. so, i brought you some courage... as cheesy as that sounds."

jess looked between the two for a moment before sharing a nod with his uncle, as if a thank you in their own language.

"hey, i'm lorelai. it's nice to meet you i've heard so much about you. we seem to have a lot in common," lorelai interjected as she walked over and introduced herself to y/n. y/n knew her fair share of scoop of the town. her daily phone calls to jess were hardly just baby talk. she'd spent a lot of them telling him to go out with lorelai's daughter, who seemed good for him. but every-time... something was holding him back. "yeah you too, i'm y/n. thank you for everything, by the way. you really didn't have to let me."

"c'mon we're moms, we help eachother out. we can be like desperate housewives. but with no men," lorelai smiled while giving y/n's hand a squeeze. "oh! this is my bowie, rory."

"hey," y/n greeted with an awkward wave towards the other teenage girl who still seemed in shock by the situation. she forced a smile and waved, "hey."

the dispute was a lot more awkward than y/n could have hoped. but a sense of envy had taken over the both of them as they reflected on past or current relations with jess. an awkwardness that washed away quickly when y/n’s eyes locked back on jess and her son. a favorite sight of hers.

“c’mon,” jess nodded towards y/n while she took the baby out of his arms. he grabbed her bag and placed a free hand on her back, mumbling goodbyes before exiting the diner with his two. the three took the scenic tour towards the inn. bowie cracking a million smiles at the tons of birds in sight. the two teenagers reciprocating the action with shared giggles at the baby’s happiness.

the moment they entered the room, jess sat down with bowie to let y/n unpack a little bit. while the two caught up on unspoken things. “so… that was rory,” y/n says suggestively while unpacking her toiletries in the bathroom. jess was sprawled out on the bed with bowie in his arms, playing superman. he turned to her once she erupted from the bathroom and took a seat beside him. “that was rory.”

“she’s pretty,” y/n nodded with a small smile. in an attempt to be polite about jess’s possible love interest, yet he seemed hardly interested when bowie was around. “i guess,” jess shrugged before holding bowie back up in his arms. “have you asked her out yet?”

“i’m not too focused on that,” jess answered while clearly wanting the conversation to be done. y/n only smiled at the sight of the baby, gently rubbing his back. jess’s eyes locked onto her once more. watching her look at bowie with all the love made his eyes gleam. the way her smile spread with love, only made his heart beat faster happily. “thanks.”

y/n glanced over to him at his word, furrowing her eyebrows gently while she looked into his eyes. “for what?”

“for being here, i guess.” he mumbles while turning back to face bowie and bring him closer to him, the baby resting his head on jess’s chest. y/n smiled at the sight while leaning into the pillow, happily watching the two. “of course.”

so, the two laid back into the bed. smiling at the sight of their baby falling into a comforting sleep. followed by y/n minutes later, at a moment of peace. finally having someone she trusted with her baby so she could peacefully have a break. jess shut his eyes to the sound of the light breaths of both his favorite people. never having felt something so perfect once again in his life.

[thewriterg]

♡︎my baby’s day♡︎

Pairing(s): Jess Mariano x gn!reader, Luke Danes x gn!reader, Rory Gilmore x Jess Mariano, Lorelai Gilmore x Jess Mariano

Summary: Traveling to see your boyfriend in the small town of stars hallow for his special day the towns people couldn’t believe there were two of you —flufftober; day 2–

Word count: 2.3k+

Warning(s): PDA, Fluff, Pet names, Taylor, and like two swear word —aren’t you proud 😊🔪—

A/n: —GIF isn’t mine— Jess is literally my baby Dean Sucks :/

The crisp air hit your face while you stepped off the steps of the metro bus as the burnt orange leaves crunched under your feet with a book bag on your back and a duffel bag in your hand you hadn’t had the best ride to the small town the people were… clingy

You had told three people to piss off and five others to watch where they were stepping your New York accent thick and the towns people found your insults ten times more insulting because you cursed heavy and they could barely pick up what you were saying

You decided to take a cab standing on the curb of the street with your hand up in the air until the yellow street car pulled up in front of you before taking the book bag off your back you slid Into the car your hands deep in the pocket of you leather jacket

“Uhh, Luke’s diner or William’s hardware which ever it is” You spoke to the taxi driver who nodded his head with a bright smile on his face as he tapped his fingers against the steering will and began to hum while you couldn’t help but roll your eyes you began to stare out the window watching the scenery pass by before putting the sunglasses that rested on your forehead over your eyes

It wasn’t long before you arrived at what you assumed to be the towns square you looked at the meter in front of you the read $13.50 and you tossed 15 Dollars onto the man’s arm rest before grabbing your bags and letting yourself out the car as you scoped out your surroundings

As you walked across the street you could feel peoples eyes on you and it couldn’t help but irk your nerve’s slightly in New York you have your good chunk of people but for the most part everyone minded their business and went on with their day it were a school of fish you crossed the street together and then left the pod here you already felt cramped like you were in a can of sardines but you wouldn’t let anything ruin your mood for your baby’s day so you let it slide

“Hey Jess, how you doing today?” Lorelai greeted with a small smile as the teen refilled her coffee mug standing over her table

“Well I’m not bleeding or anything so you know” He responded with a shrug moving to Rory’s side of the table repeating his actions not noticing how the girl looked up at him with dreamy eyes tucking a strand of hair behind her ear before averting her attention away from the boy was the bell ringing in the pretty quiet diner at the time in day

There you stood pushing your sun glasses back on your forehead as you looked around the small diner and if it weren’t for Luke the coffee pot that occupied Jess’s hand would’ve shattered on the floor as he charged toward you full speed picking you up and spinning in a circle while you laughed lightly before he sat you down bringing your face closer to his before your lips smashed together pouring your yearning feelings into each other disguised by a kiss

“What the hell are you doing here?” Jess questioned and couldn’t bother to cover up the bright smile on his face while you chuckled at his anticipation

“I couldn’t miss my baby’s special day could I?” You smirked noticing the small audience you both had before giving them a over exaggerated wave before the towns people quickly looked away engaging in their previous activities

“I come bearing gifts” You stated reaching into your bag passing your boyfriend a black gift bag with dark red tissue paper sticking out of it and you made your way over to the table that Luke stood at handing the man a box that had decent wrapping paper around it with a small bow on its top you stood back watching both of the boys open their gifts Luke being a little more hesitant in opening his own Soon enough Luke had unwrapped the box completely looking at it in shock as his eyes switched from you back to the box

“I don’t know who you are but you are heaven sent you understand” Luke pointed a finger at you running behind the counter dramatically swiping his arm against it’s surface knocking his old toaster to the floor with a loud crash opening the box carefully as he revealed a new toaster that seemingly shined in the light

You chuckled softly before walking towards Jess who lied his gifts across the cleanest part of the counter he came across you had got him about three band T-shirts, an iowa slipknot album, a Barnes a noble gift card, and another copy of Pride of prejudice because his was water damaged and when he told you over the phone that seemed like the icing on the cake of his bad day

Jess wouldn’t have cared if it was just some old copy of the book but you both had went on a date around the city when he was back at home you had walked around the park, went to a pizza cart for lunch, picked out some new records, and then you both went to your favorite Barnes and Noble and picked up the same copy’s of book which you both agreed to pride and prejudice you had took both books home and annotated them for each other to exchange the next day

So when Jess was already having a particularly bad day and tried to lift up his mood with the mix of funny, sweet, and the amusing notes of you raging at a character or the cute little doodles You littered some pages with you could imagine his reaction when his uncle had begged him to help with rush and when he came back to read his book to find one of waiters had spilled coffee all over the paperback

So to see his face light up like a kid on Christmas or a puppy meeting’s it’s new family as he flipped through the pages to see highlighted phrases, small words written in black ink and your hand writing in the margin along the white space, and your doodles scattering different pages what caught his eye most was one of his favorite parts of the book you had wrote his and your initial with a big dark red heart around it

“I love you” Jess had sat his book down before bringing you into another embrace kissing your hairline while for the first time in six months without him you smiled

“I love you more baby” You sighed softly breathing in his his scent of coffee, old books and pine wood laying your head on his shoulder you could at least see half of the towns people peering into the windows blinds

“Are they always like that” You blatantly pointed out to your boyfriend who followed your eyes to at least 30 people staring back at him as he signed heavily

“Would you believe me if I said yes” Jess responded before the both of your attention landed on the ringing bell stormed in a angry Taylor while Jess tried to figure out what the man could be mad about now and as he felt the weight of your head on his shoulder he wondered if you had caused in any havoc

“Taylor what do you want from me” Luke questioned the man not taking his eyes away from toasted he had been setting up and admiring for the last ten minutes

“Well Luke I have you know that you have a great percentage of PDA going on in your store and it is distracting my customers” The man said matter of factly pointed a strong finger at the two of which you barely raised your eyebrows at

“Listen it’s not anyone’s fault your customers are nosey the kids are in love something I’m sure you know all about” Luke sarcastically stated before walking to the back as Taylor called out for him You and Jess both watched in amusement as the man tightened his light tan cardigan before giving you the most disgusted look he could muster before leaving with another ring of the bell

“You wanna get out of here? I’ll show you around town” Jess questioned muttering into your ear as you nodded your head with small sigh that quickly turned into a yawned

“I have to drop my bags of at the inn but after that I’m all yours for the day” You responded reaching to pick up your bags bit before you could grace your fingers over the handle Jess beat you to it

“How about we cuddle, get some takeout, and take a nap instead.. Then I’ll show you around and we can do whatever you want” Jess offered he hadn’t missed you small yawn and Connecticut from New York on the metro was at least four hours and it was early noon so he couldn’t imagine of what ungodly hour you woke up in the morning to be there

“Are you sure Bambi?” You question as you tried to stiffen another yawn while Jess could help but feel heat rush to his face as he tried to brush it away with a chuckle ever since you had found out Jess’s favorite movie was Bambi until he was twelve you hadn’t let him live it down and it became a pet name for your boyfriend In your dictionary

Luke Danes has seen a lot of things in life but his nephew blushing to the bone was a first and as he watched wide eye his mouth slightly agape before Lorelai slightly pushed it back closed with the pad of her finger tips

“Hey Luke we’re heading out”Jess called to his uncle who could just give him a nod and slight wave before he left while Luke continued staring at the spot in the diner where he saw his nephew who wore gory band shirts and has never seen smile unless he was on the phone running up his bill blushed

Like didn’t know who you were but god was he starting to like you

༄༄༄

You were all checked in and Jess sat your luggage in corner of the room before flopping down on the mattress while you chuckled softly sitting the Chinese take out down onto the wooden desk before taking each steaming box and container of food out the plastic ‘thank you’ bag

Not being able to wait you took the disposable chopsticks out the bottom of the bag bringing them down with a harsh impact on the table causing them to stick out of there paper packaging You then begin to crack open the small white container of wonton soup with rice noodles picking up a dumpling with the chopsticks you held in your right hand sighing in content at the taste

You could hear Jess stand from his position residing on the bed before he stood on the side of you opening his own box of chicken fried rice and vegetables

“I don’t know how the hell you eat with those” Jess chuckled lightly as you looked up at him you were in the middle of biting a dumplings and the broth of the soup had made a mini mustache above your top lip

“I don’t know how you can’t” You smirked at the the thought of Jess struggling to bring noodles Into his mouth the last time you both had the food

You hummed alerting Jess before bringing the pair of chopsticks in front of his mouth before he opened relentlessly taking the dumpling from the wooden stick Into his mouth before he did the same with his rice and spoon which you ate without a second thought

You both continue eating and sharing food and as you begin to finish up there’s at least two containers of sweet sesame chicken, broccoli, and rice in result of over ordering you put the container back in the bag they came from and shoved them into the little black mini fridge

Jess began to take of his boots along with his band T-shirt while you did the same revealing a bra|tank top you choose

You and Jess were under the soft bed sheets in no time While Jess lied on your chest you ran your nails through his hair before curling it back to its original state while Jess drew patterns on the side of your hip

You were both asleep In no time bathing in each others embrace

༄༄༄

It was around 11 at night and you and Jess had been out since about three or four he was showing you around town and you both picked up a couple books at the small bookshop

You were now in the park just taking small laps while the gazebo‘s dim fairy lights illuminated the dark empty streets

Jess took a hold of your hand leading up the gazebo’s steps as the two of you sat on the wooden bench you leaned you head against Jess’s shoulders while you both sit in a comfortable silence

“Thank you for coming here.. for me” Jess stated suddenly while you looked up at him with a small gleam of admiration in your eye

“I’ll always be there for you Jess no matter what, I promise ” You Held out your pinky finger as to state just how serious you were before Jess smiled genuinely and wrapping his pinky around yours

The town’s clock tower began to ring alerting that it was 12am you looked up at your boyfriend face with a soft smile

“Happy birthday baby” You rested a hand against Jess’s jaw line bringing him Into a kiss which he deepened

You don’t know how long you both sat there kissing and cuddling on a park bench but deemed your baby’s special day as one for the books

Definitely one for the books.

[mystic-writings]

almost perfect | jess mariano

PAIRING — jess mariano x fem!gilmore!reader

REQUEST — Anon - Where Emily and Richard have a kid a year older than Rory (they had her before Lorelai got pregnant with her) and she’s sent to love with Lorelai around the same the same time jess moves to town? And they meet all cutesy and shit 🤭

SUMMARY — you move to stars hollow to live with your sister, lorelai, and end up falling for the one person who understands you - and the one person your sister doesn't like

WARNINGS — angst, familiy arguments, odd family dynamics, confessions, fluff

WORD COUNT — 3,461

NOTES — this idea has had me in a chokehold fr thank you anon

masterlist | navigation

Moving to a new town and starting your life at a new high school with only two years left before graduation was difficult. But moving into your sister’s town, and going to a school where her daughter was a former student, and everyone already knows who you are, is infinitely worse. 

You supposed that being semi-close to Rory as kids was a good thing, because if it weren’t for knowing her and, by extension, knowing Lane, you’d be wandering these halls completely alone, and doubly more confused. 

Dean and Lane were angels, helping you with every piece of much needed information on what teachers were good or bad, who to avoid at every chance, and where to not sit during lunch. They promised to do their best to help, but Lane’s mother was as strict as a dictator, and Dean often worked after school, so beyond sitting with them in the classes you happened to share, there wasn’t much they could do. 

Still, Rory walked you to the doors before heading off to catch the bus to Chilton, taking extra care to make sure you were okay before leaving. It was nice, the relationship you had with her despite everything. 

Lorelai wasn’t too happy that you were staying at theirs, but she understood why you had to leave your parents behind. Or, more realistically, why you were forced to walk out. It’s why she left them 17 years ago. 

Despite the age gap between you and your sister, Lorelai was all too aware of why you were born. Of how your parents treated the both of you, and the fact that no child should’ve been raised under the Gilmore name. She was never really close with you, considering you were only a few months older than Rory, but you understood. No 16 year old should be raising a kid while her parents are raising a baby themselves. 

But, she was kind enough to open her arms, and redecorate her spare bedroom, to fit you in. She got you a place at Stars Hollow High, settled you in with the townspeople, and did anything in her power to help. 

However, there was no helping the bundle of anxiety in your chest as you headed from your locker to homeroom. The school was small, of course. Not small enough to have a graduating class size of under 70 kids, but small enough that people knew who was attached to your last name. Small enough for people to start asking questions. 

Homeroom itself was fine. Lane and Dean had different homeroom classes, and people whispered when your name was called during attendance, but everything else was fine. The boy you sat next to seemed entirely unbothered by the environment around him, clutching a pen as he wrote in the margins of the book he carried - On The Road, by Jack Kerouac. Rory had lent the book to you not even two weeks ago, and you mentally appraised him for his literary taste. 

Of course, you should’ve known that trouble would’ve found you not long after your first day. 

Between second and third period, you’d been standing at your locker, supposedly the one Rory used to inhabit - and one you’d already decorated with stickers of bands and movie references - switching out your books when three girls approached you. You were already not prepared for any unexpected interactions, but these girls spelled trouble, just from the way they were all blonde, pretty and primped at 9am, in a small town high school. You expected it from the Chilton girls, sure, but not here. 

“You’re Y/n Gilmore, right?” The one in the middle said, her mouth upturned in something like a grimace. 

“Yeah, why?”

“Well we saw you during homeroom and we were wondering,” the girl on the left spoke, her gum popping annoyingly as she chewed on it. “If you’re, like, a Gilmore, does that make you Rory’s sister?”

“Yeah, we didn’t know Rory had a sister.” 

“How come we’ve never seen you before? I mean, you both should’ve gone to the same school, right?”

“Oh, my God, are you not her sister? Or were you just like, in rehab or something?”

“Oh my God, are you a drug addict?”

The girls continued to chirp at you, and among themselves, endlessly thinking up possibilities of how you could be Rory’s sister and still not go to Stars Hollow High until now. You didn’t even know they had that much brain power, let alone that they could jump to that far of a conclusion so fast. 

Suddenly, from behind you, someone spoke. “Why don’t you girls leave her alone, huh?” 

They stopped, almost freakishly in sync, and grimaced at the person behind you. 

“Seriously, Barbie, why don’t you go fix your makeup or something.” He scoffed, stepping up to stand beside you. “And honestly, if she was a tweaker, do you really think she’d even be allowed in the school?”

“I-”

“Just go away,” he complained, and the girl in the middle scoffed. 

“Whatever, Jess. Just trying to get to know the new girl.” She rolled her eyes.

You didn’t stop yourself from looking at the trio in disbelief. “You sure have a funny way of doing it, then. Why don’t you make up rumours about someone else and leave me the hell out of it. Or have you gotten bored of doing it to everyone else?”

It was amusing, watching the shock make their jaws drop before they managed to saunter away. When you turned to look at the boy who helped save you from that awful experience, you found the person who sat next to you in homeroom. 

“Thanks.”

“No problem,” he shrugged, a slight smirk playing on his lips, and you noticed that his hands were shoved in his front pockets. “Trust me, those girls do that to everyone. Y/n, right?”

“That’s me. And you’re Jess.” 

“Yep.” 

You stood silently for a few moments, staring awkwardly at one another. Just as you opened your mouth to speak, the warning bell rang, and the noise level around you picked up as students rushed to their next classes. 

“See you around, Y/n.” And just like that, Jess disappeared into the crowd of students, leaving you to gather your things and head to calculus, one of the few classes you shared with Lane. 

It’s been almost two months since you moved to Stars Hollow, and you found that adjusting was a lot easier than you first thought it would be. Despite having Lane and Dean at your side, you also seemed to be one of the lucky few to catch and retain Jess Mariano’s attention. He was, to everyone else, the loner who barely came to class and had no interest in being in the town in the first place; but he seemed to take a liking to you, the reason for which was still unknown to everyone but him. 

He was quick to become your best friend, and the only person in town who you gave a detailed description of your family background to. Somehow, the rumours that the girls who forced you into conversation never made it outside of their circle, but at some point the truth about your relationship with the Gilmore girls was spread around town, as you assumed would happen at some point. 

Still, no one minded that much, and found that your closeness to Rory and Lorelai meant that you were close to everyone in Stars Hollow. The welcoming warmth and sense of community was something that you had never felt in Hartford. 

Jess, of course, found it annoying, but you liked to tease him about it, and you knew he meant well. No one else seemed to want to care about him like you did, like Luke did. Including Lorelai, who was less than pleased that you chose to befriend him out of all the other supposedly stand-up kids in town. 

It wasn’t uncommon for you to have Jess over while Lorelai and Rory went to Hartford for Friday night dinners. In fact, it was what you had in mind for your plans as you watched the mother-daughter duo scramble around the house to get ready. 

Rory was, as usual, ready to leave exceptionally early, and had bid you a cheerful goodbye as she headed out to the car to wait for her mom, who was marching her way down the stairs while struggling to put in earrings. 

Lorelai caught sight of you on the couch, curled up and channel surfing, and smiled. “So, what are your plans for tonight? Partying hard, I hope. Remember my rule, no bikers and no drugs past 8pm.”

“Funny, Lorelai,” you smiled, craning your neck to look at her as she shoved items from the side table into her purse. “I’ll probably just order in and call Jess. He’s never doing anything on Fridays, and it’s better than being alone all night.” 

Your sister paused in the hallway, fidgeting movements indicating that she was contemplating something. 

“Can I ask you something?”

“Sure, what’s up?”

Lorelai turned fully, and took a few tentative steps toward you. Her iconic awkwardly polite smile stretched across her features, and you looked her up and down. “Why do you hang out with Jess so much? Sweetie, I mean, you’ve gotta see how bad of an influence he is.” 

“He’s not a bad influence, Lor. If anything, I’m being a good influence on him.” You said, sitting up straighter, leaning on the arm of the couch to properly face your sister. “Besides, he’s nice. He just doesn’t like a lot of other people in town.” 

“So you’re trying to tell me that he’s nice to everyone but you?”

“Yes, and I don’t exactly see what’s wrong with that.” 

“Well, hon, I mean, don’t you think that maybe that’s a little, I dunno, odd?” Lorelai suggested, her fluster clearly underlining her tone. 

You shrugged. “I don’t think so, no. He’s my best friend.” 

“Yes, I know that, but-” Lorelai tapped her foot, trying to find the right words to say. “I think you’re spending too much time with him, Y/n, and I just think it’s gonna end up with you getting hurt somehow.” 

“Hurt?” You scoffed. “Lorelai, how in the world would Jess be able to hurt me?”

Lorelai sighed, stepping closer to you. “I think you like him, Y/n. I think you have a crush on him, and I don’t think he likes you back. I just don’t want you to do anything and then end up being heartbroken and losing Jess as a friend.” 

You? Having feelings for Jess? It was something you could barely wrap your mind around. Lorelai’s accusations, even if out of some sort of motherly-type concern, were out of line. There was no way you liked Jess like that, right? And besides, even if you did, she didn’t have the right to try to stop you from doing or not doing anything about it. 

“Why are you so concerned about this all of a sudden?” You asked, furrowing your brow. “I mean, I’ve been hanging out with Jess one on one for a while, it’s not like all of a sudden I’ll catch feelings for him or something.”

“I understand that, but I’m saying that it seems like you caught feelings a while ago, Y/n.” Lorelai said, exasperation clear in the speed at which she was talking. 

You resisted the urge to roll your eyes. Why won’t she just drop it? “I’ve got it handled, Lorelai, please, just leave it be and go to dinner. You’re gonna be late, and you know how much mom hates that. Especially when you’re late.”

Lorelai scoffed. “I have plenty of time before we have to go. Now will you please tell me why you have such an attitude about this? I’m just trying to look out for you. Jess isn’t good for you, and I just want to-” 

“I get that Lorelai but I don’t need you to.” You snapped, swiftly getting to your feet. “I don’t need you to protect me, or look out for my best interest, or be motherly toward me. I get that you’re trying to make up for the fact that you couldn’t protect me as a kid and I ended up getting kicked out or whatever, but you’re not my mother.” Your blood was boiling. You didn’t know why, but it seemed that something within you just… snapped. “I don’t need you, Lorelai.” Your words pierced Lorelai’s heart with every bit of enunciation you placed on them. 

“And it doesn’t matter what kind of influence Jess is on me, because our mother made sure to ruin me beforehand. You of all people should understand that.” 

Lorelai stood, shocked at your outburst. She’d never seen more of herself in someone before, and still, she was heartbroken. Tears brimmed her eyes as she realized that, despite what you just said was more than likely teenage hormones kicking into gear, it was the truth. She tried, as hard as she could, to protect you as a kid. Harder than she tried to get herself out of that house. But she failed, because Rory came first, always. You didn’t need her anymore, not to raise or protect you. 

“You’re right,” Lorelai nodded, clearing her throat before blinking away her tears. “You’re too grown up to need me anymore. I just… wanted to make sure you knew I cared. That I was worried. But you don’t need me, so go ahead and make whatever decisions you want to. It’s not on me.” 

You watched Lorelai turn and walk out of the house, the door rattling the house as it swung shut. And suddenly, the silence pressed in on you, weighted with the realization of what you’d just done. Months of trying desperately to repair your relationship with Lorelai, of further building your relationship with Rory, only to have it torn down in seconds by your stupid teenage denial and anger. 

The weight of your actions came crashing down, and soon you were sitting back on the couch, sobbing into your hands. 

You don’t know how long you spent stuck in that spot until the house rattled again, and Jess was calling out to you, telling you what he forced Luke to make for the both of you to eat during your hangout tonight. 

Jess barely heard you crying on the couch until the food was on the table and he turned to find you there, back to him, curled into yourself as you sobbed. His voice faded instantly, his legs making long, quick strides in order to reach you as fast as he could. Jess’ mind was a flurry of confusion and worry - you sounded fine when he called you an hour ago. 

As soon as you were within reach, Jess’ hand gripped your shoulder, refusing to let himself lose the grasp he had on you even after he manoeuvred himself to sit next to you. He shuffled as close as he could get, and it was those movements that forced your head up from where it rested on your knees, enclosed by your arms wrapping around your legs. 

“Hey,” he said, trying his best to soothe you, but Jess wasn’t one to do that sort of thing often. “What’s wrong?”

“I am,” you croaked, followed by a sniffle and a shaking breath. “I’m so stupid, Jess.” 

Jess’ hand moved down your shoulder, until it squeezed your forearm comfortingly. “No, you’re not. And you’re obviously not okay. Tell me what happened.” 

As soon as the words left his mouth, you shook your head. Telling Jess that you argued with Lorelai over him would just make things worse with her, and telling him it was about your feelings for him would ruin things altogether.

“I can’t.” You said quietly. “It’s nothing you need to worry about, okay, Jess? I was just stupid and it’s my fault, I don’t wanna drag you into this.”

“No, I do have to worry about it, Y/n.” Jess said, his words firm. You could see his brows furrowing, eyes darkening. His emotions were brewing, and you knew you wouldn’t be able to stop it. “You’re my best friend. Hell, you’re my only friend, and I don’t know how you managed to do it, but I care about you. I actually care about someone for once in my life, and it’s you. So tell me what happened, drag me into it, because I… I care.” 

You couldn’t help but chuckle a little bit. Sniffling once again, you moved yourself to wipe some tears from your cheeks and put your hand on top of the hand Jess laid on your forearm. You stared at your hands and soaked in his warmth as you spoke. “It was Lorelai, we fought and-”

“Of course it was,” Jess scoffed.

You rolled your eyes. “Jess, just let me-” 

“No, she always has something to say about- about everything.” He said.

“Let me finish, please.” When Jess didn’t speak again, you continued. “I told her you and I were gonna hang out for the night and she sort of… well, she mentioned a few things and I got angry and we fought. I was an idiot and I yelled at her for trying to be my mother because she didn’t protect me as a kid and it just… it was a disaster.” 

Jess scoffed again, pulling his hand back and scrubbing his face, leaning into the couch. “Of course, she had to say something about you being with me. What, does she think we’re gonna rob a bank as a fun casual activity? I mean, seriously, she’s had it out for me since day one.”

You leaned forward, re-initiating the touch by resting your arm on his shoulder, your hand just barely grazing the back of his neck. “She doesn’t think we’re good for each other. At all. But she’s wrong, I know she is.” 

“Me too,” Jess sighed, looking over at you. 

The silence that filled the space between you, and your stomach was churning. Lorelai’s words came back to you, and as much as you didn’t want her in your head right now, you knew, deep down, that what she’d said about your feelings for Jess were true. 

Before you could stop yourself, you pulled away and the words came tumbling out, awkward and choppy and full of anxiety. “She was right about one thing, though.” 

Again, Jess scoffed an almost playful smirk lifting the corners of his lips. “Oh yeah, and what was that?”

“That I… have feelings for you.” You said, following it with an awkward and bashful smile. It was now or never, you supposed. “I mean, I didn’t even realize it until just now so don’t yell at me for keeping it a secret or something but she is right. You’re the only other person besides her and Rory and Luke that I care about and even then I care more about you than them and all I almost ever think or talk about is you and it sucks and I don’t want to keep it to myself. If you don’t want to be friends anymore I understand because it’s weird to have a friend who has feelings for you, trust me, so you can just leave now if you want-”

Jess’ lips crashing onto your own cut off the breathless ramble you had found yourself in. Your brain nearly completely shut down, complete peace silencing all the anxious thoughts in your head as you closed your eyes. By the time you registered that you needed to kiss back, Jess was pulling away, but you refused to let the moment end. He barely made it inches away before you were chasing his lips, placing a hand on his jaw to guide him back to you. 

The kiss was simple, but it was as if it sparked something within you, and every nerve in your body felt the emotion within you. You never imagined you’d be kissing a guy like Jess. Hell, you never imagined you’d find someone like him, someone so damn near perfect for you, in your lifetime. But you did, and he was kissing you, and you couldn’t give a damn about what anyone else would think when they found out. Because right now, it was just you and Jess, and no one else knew, and things were almost perfect, and that was what was important. 

You’d fix things with Lorelai tomorrow, and you weren’t sure you’d ever truly fix things with your parents; one day you’d try, just not yet. But for right now, all that mattered was yourself and Jess.

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[character---obsessed]

Jess Mariano x reader

Summary: R gets overwhelmed and goes to her favourite boy for comfort

Contents: fluff

Warnings: none

Jess was at the diner, doing his usual half argue half joke with Luke.

“It’s not my fault you’re clinically insane”

“Oh I’m the insane one? Really mr i sleep with banging music on at full blast every damn night”

Lorelei shared an amused look with Rory as they sat in the almost empty diner - just being inhabited with Bébete, Morey and Kirk.

Just as Jess was about to pipe in with another witty comment, the bell on the diner door started ringing. Jess was about to look over his shoulder when he felt a smaller body nuzzle into his side. Shocked, he moved abruptly and was about to shove whoever it was. A whine sounded out and he looked down and saw Y/N. She was clearly distressed, face scrunched up and arms wrapped around her own body tightly. Everybody else in the diner was in shock, waiting for Jess’ next move, including whichever townsfolk had walked in after Y/N had. Much to everyone’s - even Luke’s - surprise, Jess wrapped his arms around her tightly, letting her bury into his chest without moving her arms from their tight position.

“What happened? Hm?” Jess spoke gently and quietly into her ear.

Another small whine came out of her mouth. Jess glanced over his shoulder to Luke before gently steering her to the stairs.

“C’mon,” he guided her up and into his bedroom (otherwise known as the left side of the open apartment) and stood with her in the middle of his section.

All she did was bury back into his chest, standing as close as possible without causing one of them to loose their balance.

“You wanna lay down?”

She nodded.

He gently led her to the bed and laid her down underneath the blanket, taking two extra pillows and slotting them behind her to help her feel comfortable. He pulled - with some struggle - the weighted blanket out from under his bed. He always kept it there ever since he first dealt with her feeling like this. He laid it atop her before laying on the other side of her. He didn’t get all the hoopla about weighted blankets or why she liked them so much, but she did and who was he to deprive her? He let her decide if she wanted cuddles and she made a prompt decision by whining the second he got in until he wrapped his arms around her and pressed her side/front against him while her back was against the pillow wall he built. Pushed against by pillows at her back whilst under a weighted blanket on a relatively cold day all the while behind held by Jess was quick to calm her down. That is before she had a thought she didn’t like and took a big, sudden, jarring breath in and sat up abruptly. Jess however was unfazed as he waited for the moment to pass before he eased her back down and traced circles on her forehead and wrapping one arm around her to keep her close while humming a tune to a song he couldn’t pin.

They stayed like that, wrapped in each others arms as Jess traced circles on Y/N’s forehead for a significant chunk of time. Y/N couldn’t seem to get close enough to Jess, burying her head further into his chest every few minutes before finally calming down and settling in the nook she had made for herself out of his body.

Luke stayed downstairs the entire time, not having a great grasp on whatever was going on in the apartment above but knowing well enough to leave them alone until he knows for certain Jess calmed Y/N down. The entire town by that point was bubbling with gossip about what had happened mere moments ago, all huddled up in Luke’s diner as he rolled his eyes in the corner.

[ribbons111]

Track 12: Sweet Nothing

Jess Mariano

Summary. You visit Stars Hollow to wish Jess a happy birthday.

Warning. fluff.

Everything seemed dark, the town felt ghostly, so late at night that nothing seemed to be alive anymore.

I was freezing, the winter air recklessly hitting my skin.

My legs burned and my head was spinning, I was exusted.

My heels clicked the pavement as I ran on the thick ice.

I sighed heavenly as soon as I noticed the sign, Luke’s Diner.

The diner was most obviously closed but I still turned the cold door handle.

To my surprise, it wasn’t locked.

I quickly pulled myself in, shielding myself from the snow.

I remember Jess explaining how the diner looks like.

‘My room is upstairs’ so, I walked up the stairs and into a hallway.

I knocked on a wooden brown door.

Jess could sleep through an earthquake…

After calling his name a couple of times I walked into his room.

The lights were off and soft snoring could be heard.

I walked towards his bed, crouching down to see his face.

“Happy birthday” I whispered kissing the top of his head lightly.

He looks diffrent from the last time I saw him.

A year changes so much.

“Jess,” I repeated softly a couple of times, shaking his body.

He mumbled something before turning around in his sleep.

“Jess wake up!” I shook him again.

“Stop!” He pushed my hand away, sitting up.

I smiled at the way he looks.

His hair messy, eyes half lidded.

I wonder what he did yesterday to seem so tired for sleep.

“Happy birthday” I whispered again, for him to hear this time.

“What- What are you doing here?” He asked rolling to his side to turn on some source of light.

“I missed you!” I gushed jumping on him causing him to fall on his bed.

He’s so warm, melting into my touch.

He pushed me away to look at my face.

“You look so beautiful” he smiled, stroking his thumb on my cheek.

The air stilled, all I could feel was him, all of him.

His eyes held the whole galaxy.

I kissed him gently.

He kissed me with hunger, longing.

“Your so cold” Jess mumbled into my mouth.

“It’s freezing out” I sighed, pulling him in deeper.

“Think I'm dreaming again” he gasped for air with furrowed brows.