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Oct 6, 2025

The Line We Crossed

4.5k words

Jake Kiszka x Reader

Summary: A stolen night. A year of silence. And now, they're back where they started– wanting each other too much to stop. They promised not to cross the line. But when feelings simmer for too long, they eventually boil over.

a/n: huge huge huge thank you to @missmirador for this request!!! this is a little late and i'm so sorry for that but it is here!!!! yes, it's the "brother's best friend" trope, and i am 10000% into it!!! yall enjoy, my recs are open!

warnings: angst, yearning, pining, forbidden love, drunken hook up, arguing, SMUT - 18+!!!!, finger sucking, fingering, dirty talk, sex, soft moments

MASTERLIST

You’ve always heard that heartbreak is supposed to be the worst kind of pain– that it cracks you open from the inside, leaves you hollow, aching, changed. And yeah, you’ve felt that, once or twice. But none of it, not the silence after a fight, not the finality of goodbye, comes close to this.

This… yearning.

This quiet, constant pull in your chest every time Jake walks into a room.

Jake, your brother Chris’ best friend. Jake, who strums his guitar like he doesn’t know what he does to you. It's not just a crush. It’s a slow, relentless ache that makes heartbreak look merciful.

Because at least heartbreak has an ending.

A clean cut, a reason to cry, something to bury. But this– this want– is endless. It burns in every second Jake looks at you like he shouldn’t, in the way his voice softens when he says your name, in those lingering silences that stretch just a little too long when it’s just the two of you.

It would almost be easier if he didn’t feel the same. If his eyes didn’t flick to your lips and then away like he’s punishing himself for even thinking about it. But he does feel it– you know he does. And still, he won’t touch you. Because Chris made it clear: you’re off limits. And Jake, being the loyal best friend, the good guy, listens.

So instead of heartbreak, you’re stuck with something crueler– mutual desire that neither of you are allowed to act on. A slow, smoldering kind of torment that makes you wish it had ended, just so you could finally breathe.

And yet, you keep finding yourselves alone. In kitchens, in hallways, in the backseat of cars when Chris runs inside to grab something he forgot. Like the universe hasn’t had enough fun watching you squirm, like it’s still waiting to see if you’ll do it again. If Jake will.

He's sitting across from you, guitar in his lap, strumming mindlessly as he talks with your brother. You both keep stealing glances, sharing secret soft smiles and longing looks.

It makes your heart ache every single time.

You want to yell at your brother. You want to stomp your feet and throw a fit until he gives his blessing.

But you can't– You won't put Jake in that situation.

So you suffer in silence, memories of a drunken night dancing through your mind. Bittersweet memories of the way he held you, phantom whispers of the things he said to you.

It makes it worse.

To know what you're not supposed to. To know what you're missing out on.

You could watch him play for hours. You do, you stick around every time Chris mentions he might be coming over. Any chance of seeing Jake, you take it.

He hasn't crossed any boundaries since that night. And you hate it.

He's a lot more subtle than you are, though. He knows when to look at you, when to sneak a touch. A simple hand on the hip when he slips past you, ‘being a good friend' and fixing your hair, your clothes. Ghosting his fingers along your skin when your brother isn't looking.

The way he looks at you is the worst part. Half awe and half devastation, like you're the one thing that'll destroy him.

Like he isn't destroying you.

—

You think about that night often, cursing yourself for being drunk. Cursing him for being drunk.

The morning after, waking up in his arms. The golden afterglow quickly muted with a single word from him.

He woke up after you, running a hand over his mouth, “Shit.”

Your heart cracked.

“Yeah,” you said, looking away from him, “I know.”

He was regretful, calling it a mistake, rushing to fix the damage when he'd seen the heartbreak clear on your face.

“We were drunk.”

As if that was the reason you gave in to the fight. As if that was the reason he did.

He's watching you right now, you can feel his eyes on you. So bold, with your brother sitting just across from him. They begin talking, something about the next show coming up. Your glass is empty, and you stand to fill it.

“Where are you going?” Chris asks, leaning back against the headrest with his guitar still cradled in his lap.

You hold up your glass in lieu of a response.

“Get me one,” he calls after you.

“No,” you call back, laughing lightly.

You're pouring your drink when you feel a hand at your hip, and lips against your ear, “Excuse me.”

Jake.

He slips past you, fully pressing against you, and you nearly have to set the bottle down. You don't look at him, but your lips turn up in a smile. He did it on purpose, there's plenty of room for him to walk by with no issue.

“What are you doing?” You ask casually, ignoring what he did completely.

“Getting a drink for your brother,” he responds, grabbing a glass from the drying rack. If it bothers him that you didn't react, he doesn't show it.

“I was gonna do that,” you mutter, picking the bottle back up to top off your drink.

“I know,” he responds, leaning against the counter next to you. Close, like he's testing both of your willpower.

You hold your hand out for the glass in Jake's hand, avoiding looking at him. You're just tipsy enough to want to kiss him. He's just tipsy enough to try it.

He hands you the glass without a word, his eyes watching you closely.

It used to make you nervous, how intently he stared, but now you crave it. You want him to want you.

“You look pretty tonight,” he says, just above a whisper.

You feel your cheeks heating, and you feel silly for blushing at such a simple compliment. “Thank you,” you say quietly.

He sighs, the sound matching exactly how you feel.

“You have no idea how bad I just wanna–” He cuts himself off with a subdued, frustrated growl and a shake of his head.

You finally look at him, a challenge of sorts, “Wanna what?”

He just stares at you, his eyes mapping over every part of your face. He sighs again, grabbing the glass he'd gotten for your brother, raising it to you, “Thank you.”

And he's gone. No touches, no smiles, just gone.

You stare at the cabinet in front of you, your heart feeling heavier than before.

—

You're drunk.

And Jake looks so good.

You've hardly looked away from him, and he's hardly looked away from you. You have enough sense about you to look away when your eyes catch for the umpteenth time, but Jake hardly does.

Chris is in his own world, he usually is when he's got his guitar– Or so you thought.

When you lock eyes with him, he's squinting slightly, a perturbed look on his face. You furrow your eyebrows slightly, and he glances over at Jake, then back to you.

Your face drops without you meaning for it to, and it gives him his answer.

You feign confusion, and take a sip from your drink, looking away from him once more.

Shit.

—

You're hungover. Your hair is a mess, you're still wearing part of last night's makeup. You're dressed in an oversized tee– one you'd stolen from Jake months ago– and a ratted pair of cotton sleep shorts.

Jake walks into the room yawning, scratching at his lower tummy, his shirt raised up just enough to make your mouth water.

You give him a smile, and he returns it, running his eyes over you, “Don't you just look fucking beautiful,” he says genuinely.

You snort, taking a sip of your orange juice, “Yeah right.”

He hums as he looks at you, shaking his head, “You're breaking my heart, baby.”

You roll your eyes, pretending you don't secretly enjoy it, even if you don't believe him.

He makes his way to the table where you're sitting, leaning over and pressing a quick kiss to your hair, before he grabs a piece of toast off of your plate.

“Asshole,” you mutter, reaching out to swat at him.

He laughs, taking a bite as he dodges your hand. He makes his way to the coffee pot, grabbing a mug from the cabinet.

He wordlessly makes his way to the table, his mug steaming in his hand. He sits beside you, shooting you a wink when you slide your plate to him.

Chris comes in, looking as if he'd been awake for a while, not a single hair out of place. He pours himself a cup of coffee, turning to face you as he leans against the counter. You take another drink of your orange juice.

The room's awkwardly silent, your brother crosses his arms as he stares between the two of you. You take a sip of your juice once more, staring at him over the rim of your glass.

You glance over at Jake, who's watching Chris closely.

“You fucked my sister.”

You inhale sharply– right through your juice. A sudden fit of coughing overtakes you, orange spraying across the table, some of it catching Jake’s arm.

Jake’s eyes flick to you instantly, concern flashing across his face, but he doesn’t move from where he’s sitting. He just slides a napkin your way without looking, keeping his gaze locked on your brother.

“You okay?” he asks, voice low, steady.

You nod between coughs, embarrassed and trying to recover as quietly as possible.

Only once you’ve settled does he finally glance down, notice the juice on his arm, and wipe it off with the edge of his sleeve– still not breaking eye contact with your brother.

Chris waits patiently, staring back at Jake.

“We aren't–”

“When did it happen?” He interrupts you, staring at you now.

You squirm lightly, glancing at Jake, who's still watching your brother. “Almost a year ago,” you murmur.

He gives an offended, disgusted look to Jake, “I asked one thing from you, Jake.”

Jake sighs, “I know.”

“We were drunk,” you step in, offering to take some of the heat off of Jake.

Chris snorts softly, shaking his head but not looking angry– just a little unsettled. “Drunk or not, I wish you’d told me sooner.” His eyes flick to Jake, then back to you.

Jake lets out a quiet breath, his gaze steady but not confrontational. “I know. I should’ve said something.”

You glance down, feeling the weight of the moment settle around you. “It was almost a year ago,” you say quietly. “I didn’t want to make a big deal out of it.”

Chris leans against the counter, running a hand through his hair. “I’m not mad. I’m just… surprised, and a little grossed out.”

Jake nods.

The room falls silent for a moment, the awkwardness lingering but softer now.

Chris takes a slow sip of his coffee and finally looks at both of you. “Just be straight with me. No secrets.”

You meet his eyes, appreciating the honesty in his voice. “We will.”

Chris nods, exhaling deeply. “Good. Let’s just move forward.”

—

You're awkward.

You've spent the last few years of knowing Jake yearning for him, pining over him, daydreaming of him. And now?

You didn't know what to do with yourself.

You sat away from him on the couch, though you weren't sure if that was for your sake, or Chris’– since he had gagged when he saw Jake kiss the top of your head.

You wouldn't look at him much, almost scared of how intense it would be. A forewarning, like you both knew what was coming tonight from one look at each other.

You kept your eyes on the screen for the whole movie.

And as soon as it ended, you stood, feigning an excuse about a headache, and needing to go to bed. You didn't miss the hint of a frustrated smirk on Jake's lips, a glint in his eye as he wished you a good night.

—

You feel like a creep.

Standing outside the guest bedroom door, considering knocking. You can hear Jake on the other side, strumming softly at his guitar, like he’s trying to be quiet. He and Chris had gone to their rooms an hour after you had, and well, you couldn't sleep.

You fidget with your hands for a second, glaring at the door.

You take a deep breath, grabbing the knob.

You twist it open, slipping into the room as quietly as you had snuck to the door.

Jake pauses his playing, his eyes softening when he sees you. You pull the door shut with a soft click, and lock it behind you.

His eyes stick to the lock for a moment, then go back to you, “What are you doing?” He asks quietly, a cautious air in his curiosity.

You open your mouth to speak, but your nerves get the best of you, and you shut your mouth once again.

He stares at you for a moment longer before he slowly sets his guitar to the side. You press your back against the door as he stands, and you suck your bottom lip into your mouth.

You stay there as he approaches you, slowly, like a predator stalking its prey. He stops just inches away from you, tilting his head slightly. He reaches up, cupping your face in both of his hands, and you nearly melt into his touch.

“Your brother will kill me if he finds you in here,” he says, his voice above a whisper.

“Don't let him find me in here then,” you whisper.

He cracks a grin before he presses his lips to yours. You nearly start crying from relief. It'd been a year since he last dared to touch you like this. He'd touch you of course, subtle moves, things he could get away with. But his lips are working against yours and you could shed happy tears.

Your fingers loop around his wrists, needing something to hold onto, and he steps forward, pressing his body to yours, and pushing you tighter against the door.

He detaches his lips from yours, his hands angling your face up so he can kiss along your throat.

“No marks,” you whisper breathlessly, earning a quiet grumble from him. You huff a breath of a laugh, “He'll kill us both, Jake.”

“Let him try,” he murmurs, pressing one final kiss to your jaw before he pulls back.

He leaves a quick kiss to your lips before he pulls you away from the door. He moves his hands to your hips, turning the two of you around and walking you backward to the bed.

“We don't have to do anything,” he assures you, his hand coming back up to brush a thumb along your cheekbone, “I'm– I'll be happy just having you here.”

You nod, “I know,” you say, reaching out to fidget with one of his necklaces draped across his chest, “But I want to.”

You can feel his heartbeat pick up against your hand, and you almost feel proud, knowing you have as much of an effect on him as he has on you.

He nods slowly, his hands dropping to your waist once again, fiddling with the hem of your shirt. “It's scarier when we're sober,” he says honestly, earning a giggle from you.

“Yeah,” you respond, “It is.” You grab his hand, pushing it under your shirt.

His jaw tightens as his palm settles over your smooth, warm skin. His fingertips dig in lightly before he trails them up, pushing your shirt up along the way. You lift your arms as he lifts your shirt over your head, tossing it aside somewhere on the floor.

He freezes only for a moment, enough to get a good look at you, before his hands and mouth are on your breasts.

It almost catches you off guard, a loud gasp escaping you as his lips attach to your nipple. Your hand tangles in his hair, holding on for dear life as he grabs and nips and licks at your chest.

He wraps an arm around your waist, moving you backwards to lay you down against the mattress. He climbs over you, a knee between your thighs, covering as he gives your breasts his attention.

“Fuck,” you barely breathe the word, your head falling back as he pops off of your breast. Before you can mourn the warmth of his mouth, he's on your other breast, licking and sucking with fervor.

You feel as if you're going to combust, you're wet and aching for attention down there. You wiggle down just enough to press yourself against his knee, letting out a loud moan when he presses it tighter to you.

He pulls off of your chest, shushing you gently as he presses his nose to your cheek, “We gotta be quiet, baby,” he whispers, plucking at your bottom lip with his index finger, “Can you do that for me?”

You nod hesitantly, and he slips his finger past your lips, resting it on your tongue. You wrap your lips around it, lulling your tongue gently. “Fuck, there we go,” he says on a breath.

He uses the hand not in your mouth to grab your hip, moving you tightly against him. You're grateful he eases another finger inside your mouth, it helps keep you somewhat quiet as he grinds you along his knee.

He pushes his fingers in deeper, humming when you fight the gag threatening you. He pulls them out of your mouth suddenly, the same time moving his knee, and you nearly whine. Before you can, he pushes his hand past the waistband of your shorts, past your panties, and presses his fingers against your clit.

“Fuck!” It's quiet when you curse, but still too loud for the dead of the night. He presses his lips to yours quickly, before he gently holds his other hand over your mouth.

Your eyes roll back in your head as he begins rubbing quick circles over your clit. You let out a muffled whine, nodding weakly when he shushes you again.

“Stay quiet, sweet girl,” he whispers, “You can do it.”

You grab his wrist, holding onto it and holding his hand against your mouth in place. He whispers a quiet curse, moving his fingers at your clit down to your weeping entrance.

He pushes them into you with no resistance, giving you a light grin as he curls them up. He looks arrogant, like he's proud that you're as wet as you are. It makes you clench down around his fingers mindlessly.

“So fucking wet,” he murmurs, as if in awe. You nod weakly, rocking your hips in tandem with each thrust of his wrist.

He presses the heel of his palm against your clit, grinding it just right as he fucks his fingers into you.

“Fuck, Jake,” it's still muffled, but he understands your whine.

“What, baby?” He asks teasingly, “Does it feel good?”

You nod with a stifled sob, your legs beginning to quake.

“I know,” he says softly, his fingers fucking into you unrelentingly, “You're about to come already, aren't you?”

You nod again, a tinge of fear appearing at the gleam in his eye. Surely he wouldn't deny you that…

“Please,” you say pathetically, your hand grabbing his other wrist now, as if trying to keep him there.

“I'm gonna let you,” he reassures you with a kiss to your temple, “You're gonna fucking come for me.”

You manage a hushed squeak, his hand still over your mouth. He speeds up his fingers, now practically drilling them into you, hitting that spot inside of you every time.

You hit your end with no warning, a sudden, body jerking climax. Your thighs fight to shut as your entire body twitches. You're grateful he keeps his hand over your mouth, loud cries and broken sobs escaping you as your vision goes white.

You can distantly hear him curse, filthy praises escaping him as you squeeze around his hand.

He gets you through it until you can't stand it, and you're trying to push his hand away from between your quivering thighs.

“Fuck, that was so pretty,” he says, removing his hand from your mouth to capture your lips in a heated kiss.

You grab his hips, tugging at his pants, “Fuck me,” you mutter, your voice strained, “Please, Jake–”

“I'm gonna,” he says, gently grabbing your hands to pull them away.

He grabs you, moving you up on the bed, before he loops his fingers at the waistband of your shorts. He tugs your shorts and underwear down in a quick, smooth motion. And before you can ask, he's undressing himself.

You stare at him in awe, drinking in every bit of skin he bares to you. When your eyes settle on his dick, they widen. You were both drunk enough last time that you both forgot some details, but you can't believe you'd forgotten he was that big.

“Jesus,” you whisper, subconsciously letting your thighs fall open as he moves back over you.

He gives you a wry grin as he leans over the top of you, his thighs resting against yours. “Are you sure about this?” He asks, brushing your hair away from your face.

“I'm sure,” you respond airily, “I want you, Jake.”

He kisses you again, the head of him pressing against your drenched heat, and you rock your hips to try to get him to slip inside.

He smirks against your lips, and in one angle of his hips, he's easing inside of you. Slowly, gently, like he's trying to tease the both of you. You're grateful he's going slow, you needed to adjust to the sheer size of him.

“Fuck,” you both say it at the same time, as he bottoms out, fully sheathed inside of you.

His jaw is tight, the muscles in his arms straining as he rests his forehead against your temple. You can feel your walls pulsing, stretching to try to accommodate the intrusion.

“You–” He cuts himself off with a huff, “Fuck, you feel good.”

“So do you,” you manage to say, your voice slightly whimpery.

He hums, slowly– achingly– pulling out just enough to ease back inside of you. He does it again, before he's slowly repeating it over.

He works up to a steady pace, still gentle, as if he's testing the waters. And it feels so good, it does, it's just that– “Harder, Jake,” you plead softly.

He pauses just a second, before he gives a harsh thrust, fucking into you hard enough that a quiet moan escapes you. You grab at his shoulders when he does it again, and when he begins fucking into you like that, your nails dig into his back.

His finger pressing against your clit, something you weren't expecting, and you couldn't stop the moan that escapes you if you tried. He's quick to shush you again, “C'mon, angel, stay quiet for me.”

You whine, the sound weak and pathetic, “I can't.”

“You can,” he says, “What if your brother hears you, hm? You want him to know what I'm doing to you?”

You shake your head, but at this point, you really don't care. You'd let the whole neighborhood hear how good Jake's giving it to you if it was up to you. Part of you wonders how you didn't get caught a year ago.

He grabs you, leaning over you until your bodies are pressed flush together, and he fucks into you unyieldingly. His hands are holding you tightly, one at your waist, the other underneath you, gripping your shoulder as if keeping you in place.

And then he fucks into you impossibly harder, faster, and his pelvic bone is grinding perfectly against your aching clit.

“I'm gonna come.” It escapes you in one breathless moan, your words slurring together.

He nips at your earlobe, “Give it to me,” he demands, kissing just below your ear, “Let me have it, baby.” You whine his name, and it hits you like a bolt of lightning. “Fuck, that's it–”

Your entire body tightens against his, and if he wasn't holding you down, you would have probably accidentally thrashed away from him. “C'mon, honey,” he grits out, “That's it, fuck Y/n– Good fuckin’ girl, look at you.”

He'd pulled back as it hit you, just enough for him to watch you come for him, and he was watching every bit of it with a hint of a proud smile on his face.

Your entire body jerks, little aftershocks causing you to twitch and squirm as he fucks you all the way through it.

“Fuck,” he breathes the word, “I'm close, baby– Where–”

You grab his hips, pulling him tighter to you, too beat to form a coherent sentence, “Inside.”

His thrusts falter just a bit, stuttering just a bit as he reaches his own orgasm. He curses, a little too loudly, and he nestles his face back into the crook of your neck, biting down hard as he works himself through it. You can barely manage to run your fingers through his hair, your chest heaving as you both come down.

“Fuck.”

It's a broken syllable, uttered quietly by Jake.

You're still mindlessly, weakly, brushing your fingers through his tangled locks, your eyes heavy.

He presses a final kiss to your collarbone, before he pushes himself up, his eyes trailing over your fucked out form. He winces lightly as he pulls out, giving you an apologetic smile at the quiet hiss that escapes you.

He collapses next to you on the mattress, holding an arm out for you to snuggle into his side.

“I gotta clean up,” you whisper, burrowing into him regardless.

He shushes you yet another time, “We'll do it later,” he whispers, his eyes falling shut, “Just lemme love you.”

You grin at that, “Do you?”

“Do I what?” He asks softly.

“Do you love me?” You ask, reaching a hand out to straighten his necklaces out– It'd become a nervous habit for you at this point, you think.

“I do love you,” he answers, eyes still shut. “So much.”

You can't help but grin, “Good,” you pause, pressing a kiss to his arm resting under your head, “I love you too.”

He hums at your words, one of those low, sleepy sounds that rumbles in his chest and makes you feel like the safest place in the world is right here, exactly where you are. His hand finds yours under the blanket, fingers lacing together with the kind of easy, practiced affection that makes your heart ache in the best way.

“I’m serious,” he mumbles, his voice thick with sleep. “You’re stuck with me now. Forever.”

You smile against his shoulder. “Is that a threat or a promise?”

“Both,” he whispers, then adds, “and possibly a legally binding contract. You touched my necklaces, pretty sure that seals it.

You laugh quietly, nose nudging into the side of his neck. “You’re an idiot.”

“Mhm,” he says, voice trailing off as sleep starts to pull him under.

It’s peaceful after that. Warm. Quiet. The kind of perfect silence you only get when you’re held like this– safe and full and a little in love.

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