𝑠𝑦𝑑 ୨୧⋆ ˚

Hate.

That’s the word you always use when his name comes up. even if it doesn’t feel quite right anymore.

You hated the way Jess Mariano showed up to Stars Hollow like he owned the place, smirking at everyone, acting like the town was beneath him. You hated how he got away with it. that everyone, from Luke to Lorelai, just sighed and said “That’s Jess.”

But mostly, you hated how you noticed him. How his laugh stuck in your head after he made fun of you at Doose’s. How you caught yourself watching him flip through books at the counter of Luke’s, reading faster than you could process the titles. How he’d look up sometimes and catch you staring, giving you a smirk, like he knew exactly what you were thinking. You told yourself it was disgust.

It wasn’t.

It started with small sarcastic comments when you’d pass each other in town. “You know, you’d be way more likable if you talked less,” you’d mutter.

He’d grin. “So would you.”

Then came the arguments, over everything. Who was smarter, who Luke liked more, whether On the Road was genius or garbage. Half the time, you stormed off leaving him there with his stupid smirk.

Somewhere along the line, the rest of Stars Hollow started noticing. Taylor once sighed, muttering, “Can’t you two argue somewhere else?”

You and Jess just exchanged matching looks because even if you claimed to hate him, it was starting to feel like your thing… plus it was fun to watch Taylor get mad.

It’s late when he shows up at your house. the town long asleep, streetlights faintly shining through your window. You’re sitting cross legged on your bed, trying to finish an essay you’d put off all week, when you hear three knocks, faint, on the glass.

No one ever knocks on your window. That’s how horror movies start, right before the dumb girl dies first. Heart racing, you grab the nearest weapon (a pen, because of course) and inch closer getting ready to scream at who ever was there. When you finally yank the window open, you’re met with a familiar smirk making you groan and open your window. “Do you ever use a door like a normal person? Or are you used to using the windows from all the people you’ve stolen from?”

Jess shakes his head with a small laugh. “That would ruin my reputation.” “You don’t have a good reputation.” “Exactly.” He shrugs, climbing through the window with that careless confidence that makes your stomach twist. “Ew no!” You hit his shoulder, “get out!” You cross your arms and whine as he towers over you. “What do you want?”

“Luke’s losing his mind,” he says, dropping onto the edge of your bed like it’s his own. “Needed a break.” You raise a brow as you watch him “And you came here? Why not bug Rory or—”

He cuts you off, eyes flicking up, dark and sharp. “She’s not the one who drives me insane lately.” Your breath hitches. You hate that it does.

You roll your eyes, sitting back at your vanity, pretending to work on the essay. “You’re unbelievable.”

“Thanks.” “Not a compliment.”

He stands, walks over to your side of the room, too close again. the way he always does when he wants to get a rise out of you. He looks at your papers, your handwriting, the pen spinning nervously in your fingers.

“What’s that?” “An essay. Something you clearly wouldn’t understand.” He leans down, voice low. “Try me.”

You turn to glare at him, and that’s when it hits you. the quiet, the proximity, the look in his eyes that isn’t teasing anymore. It’s heavier, loaded with something you’ve both been avoiding for months. You swallow hard. “Jess-” “Don’t.” He says it softly, like he’s tired of pretending too.

He brushes a strand of hair away from your face, slow, testing you. You can feel the tremor in your chest when his thumb grazes your cheekbone. “Still hate me?” he murmurs. You try to sound strong. “More than ever.”

He smirks, the kind of smile that feels like a challenge. “Good.” And then he kisses you. It’s not gentle, it’s messy. impatient, the kind of kiss that’s been building through every argument, every sharp word, every long glance across Luke’s diner.

You shove him back at first, out of instinct, but he only grins against your mouth and grabs you by the neck, pulling you back in closer. suddenly you’re both stumbling, his hands on your waist, yours tangled in his hair.

The kiss deepens, the sound of your pulse roaring in your ears. He tastes like cigarettes and trouble, exactly like you always imagined but never admitted. When he finally pulls away, his forehead rests against yours. You’re both breathing hard.

He laughs under his breath. “Still think I’m the worst?” You manage to look up into his eyes. “You’re definitely the worst.” He grins. he then tightens his grip on your neck, making you gasp and look up at him.

“Fight me," he murmured against your lips, his voice a low growl. "Prove that you hate me." You struggled, your hands clawing at his shoulders, but he was relentless. He pushed you back against the wall, his body pinning yours, his hands roaming over your legs, rough and demanding. You could feel the heat of his touch through your clothes, the way his fingers traced the curve of your waist, the swell of your hips. You hated it, hated the way your body responded to him, the way your heart pounded in your chest.

"Jess," you gasped. "Stop." He laughed, a dark sound. "You want me to stop?" he asked, his hand slipping under her shorts, his fingers tracing the edge of her panties. “Huh?”

You shake your head, your breath coming in short, sharp gasps. Jess smirked, his eyes dark with desire. "I’m gonna ruin you." he says, his voice low and dangerous. "You want me to show you what you've been missing?" You nodded, your eyes locked with his. "Yes" you whispered.

His hands gripping your thighs, lifting you up and wrapping your legs around his waist. You could feel him, hard and ready, pressing against your core. Jess hungrily continued to kiss you deeply before he tossed you onto the bed.

He stayed standing, staring into your eyes as he unbuckled his jeans, showing the growing tent in his boxers. He smirked as you stared at him and pulled you by your legs to the edge of the bed to be in reach of you. He then practically ripped your sleep shorts off, leaving you exposed to him, making you gasp softly. He pumps his dick twice before gliding it against the wetness of your cunt. “I’m not holding back,” he rasps, almost like a warning.

He pushed into you, a rough, brutal thrust that left you gasping. You clung to him, your nails digging into his shoulders, your body arching against his.

"You're so hot," he growled, his voice a low, possessive rumble. He looks down at you as he fucks you "so much better when your not complaining"

“F-fuck you” You moaned. He chuckled as he watched you. “Already doing it” your head falling back against the mattress, your body on fire. He moved inside you, his thrusts hard and deep, each one sending a wave of pleasure crashing through your body. You could feel him, every inch of him, filling you, claiming you.

"You're so tight," he groaned, his voice ragged. "So fucking tight."

You whimpered, your body trembling as his tip continued to kiss your cervix. "Jess!" you gasped. "I can't..."

He smirked, his eyes dark with triumph. "You can take it" he said, his voice low and dangerous. "Since your so tough."

You cried out, your body convulsing as the orgasm tore through your body. He didn't stop, his thrusts growing harder, more insistent. You could feel him, his body tensing, his breath coming in short, sharp gasps. But then he stopped. He pulled out and flipped you onto your stomach, forcing you to arch your back.

“I said I was gonna ruin you” he groan as he slammed back into you, gripping the swell of your hips. You moan out, gripping the sheets. “J-Jess!”

He slaps your ass and pulls at your hair. “Shh- god..“ he moaned making you clench around him. His body started to tense up again, signaling he’s close again.

his right hand grips your neck, pulling you up, your back now against him as he thrusts into you. All you could do was moan louder, his length hitting a deeper spot in you hard. “Jess!” “Yeah?” He moaned “shit you feel so good…” you moaned in response. You can feel your climax coming again.

“I can’t!” He doesn’t tease you or say something cocky. His hands reaches down your body and starts rubbing your clot making your body slump against his chest. “Oh my god..” you moan. He smiles as he’s brutal pace continues, his high also approaching.

“Come on” he groans, his fingers moving faster as your hips buck. You cried out, your body convulsing as your orgasm tore through you, “Jess! Oh…” You could feel him, his body tensing, his breath coming in short, sharp gasps. Jess moaned as he came, his body shuddering, mouth open as he watched his seed spilling into you.

He pulled out of her, his body keeping the strength to hold them both up. You could feel him all, his heart pounding in his chest, his breath coming in short, sharp gasps. He looked at you, his eyes dark and intense.

"I hate you," you whispered, meeting his eyes. your voice raspy from what had just happened. He smiled and laughed, his eyes never leaving yours. "Good," he said, his voice low and dangerous. "Because I love it when you hate me." You smile back and kiss his lips.

Im so so sorry for the delay you guys! With work and school everything has been hard to keep up with. Hoping the next days won’t be so late. So sorry again!