Jonathan Byers x secretary!reader
Summary — your staying with your mom after college and you end up getting a job as a secretary:)
A/N — the ending is kind if dumb but I saw and edit of Jonathan and Nancy as Lee and Mr grey and I had to write this
Warnings — 18+ mdni, finger!ng, praise k!nk, unprotected p in v, spank!ng, mutual masturba!tion(?), j*b mentioned
You had just moved back in with your mom after college. She’d told you it was fine—that you could stay as long as you needed, no pressure, no deadlines. And for a while, you believed her. You settled back into your old room, surrounded by half-unpacked boxes and familiar posters, falling into a quiet routine that felt almost too comfortable.
But eventually, comfort turned into tension.
It came up over dinner, the way things like that always do—casually, almost accidentally. You were twirling spaghetti around your fork, staring down at your plate, when your mom cleared her throat.
“Honey… don’t you think you should maybe start looking for a job?” she asked, trying to sound gentle.
You glanced up, caught off guard. “A job?” you repeated. “Mom, I thought you didn’t mind me staying here for a while.”
“I don’t,” she said quickly, reaching for her glass. “Really, I don’t. I just think you should have something to keep you busy. Something other than sitting at home reading all day.”
You sighed, already knowing this conversation was inevitable. “Okay, Mom,” you said at last. “I’ll look for a job.”
Her face softened instantly, a relieved smile spreading across it. “Oh, I’m glad, honey. I just want what’s best for you.”
A few days later, you found yourself sitting outside on the front steps, a folded newspaper resting in your lap. You scanned the listings half-heartedly, groaning under your breath at words like experience required and fast-paced environment.
Then something caught your eye.
SECRETARY — printed in bold, all caps.
You paused, rereading the listing more carefully this time. Filing, answering phones, scheduling appointments. It didn’t sound too complicated. Manageable. Safe, even. You nodded to yourself. I could do that, you thought.
A few days after that, resume in hand, you stood in front of the building the address had led you to. Some kind of law firm, judging by the sign out front. You hesitated for a moment, then shrugged and pushed the door open.
Inside, the place was quiet—too quiet. You followed a narrow hallway until you reached a door labeled simply:
You snorted softly. Straight to the point, you thought, before knocking and stepping inside.
A man sat behind the desk, phone pressed to his ear. He glanced up at you briefly, then raised one finger, silently asking you to wait. You nodded and moved farther into the room, sitting down in the chair across from his desk.
As you waited, you let your eyes wander, taking in the stacks of folders, the framed certificates on the wall, the faint smell of coffee lingering in the air. Then your gaze dropped to the nameplate on the desk.
You tilted your head slightly. Hm, you thought. For some reason, the name stuck with you.
He finally hangs up the phone and turns his full attention to you, studying your face for a brief moment. “You’re the one who called last night, right?” he asks. “Um… y/n?”
You nod, shifting slightly in the chair. “Yeah, that’s me,” you say, a small, nervous smile tugging at your lips. “I hope I wasn’t too awkward on the phone.”
Jonathan lets out a quiet chuckle, shaking his head as he leans back in his chair. “No, you were fine,” he says. “Honestly, awkward phone calls are kind of a requirement around here.”
That eases something in your chest. You relax a little, your shoulders dropping as he reaches for the resume you’d set on the edge of his desk earlier. He scans it slowly, eyes moving line by line, nodding to himself now and then.
“So,” he says after a moment, looking back up at you, “you just finished college and moved back home?”
“Yeah,” you admit. “Still figuring out what comes next.”
He hums in understanding. “I get that.” He taps the paper lightly. “This job isn’t glamorous, but it’s steady. Answering phones, organizing files, keeping me from forgetting my own schedule.” A faint smile appears. “Which happens more often than I’d like to admit.”
You smile back despite yourself. “I’m good with organization,” you say. “And reminding people of things.”
“That already puts you ahead,” he replies.
There’s a brief pause, the kind that feels less awkward and more thoughtful. Jonathan glances toward the window, then back at you. “Truth is, I could really use the help. Things have been… busy lately.”
You nod, hopeful but trying not to show it too much. “I’m a quick learner,” you add. “And I’m reliable. If that counts for anything.”
He studies you for another second, then smiles more openly this time. “It does,” he says. “How soon could you start?”
Your heart skips. “Uh—whenever you need me to.”
“Good,” Jonathan says, standing and offering his hand across the desk. “Then welcome aboard.”
You shake his hand, smiling.
Jonathan clears his throat after you shake his hand, already looking a little embarrassed by how formal the moment suddenly feels. “Uh—yeah. I’ll, um… show you around,” he says, moving out from behind the desk a bit too quickly, nearly bumping into the corner.
You follow him down the hallway, noticing how quiet he is—like he’s constantly thinking before he speaks. He gestures to a small desk tucked just outside his office. “This would be yours,” he says. “Phones, emails, files… mostly keeping things from falling apart.”
You smile. “I can do that.”
He nods, relieved. “Good. Because I’m… not great at asking for help.” He hesitates, then adds, “Or delegating. Or—talking, sometimes.”
“That makes two of us,” you say lightly.
Something about that makes him relax. Just a little.
The first few days pass slowly. Jonathan keeps his distance, polite but reserved. He thanks you quietly when you hand him organized files, lingers awkwardly when you remind him about meetings, and avoids eye contact just enough that you can tell he’s painfully aware of you being there.
But you also notice the little things.
How he always brings you coffee without asking, setting it down like it’s no big deal.
How he softens when you laugh.
How he watches you when he thinks you’re not looking—curious, careful, like he’s trying to figure you out without crossing a line.
One afternoon, he comes out of his office rubbing the back of his neck. “Hey, um… y/n?”
“There’s… something I need help with.” He pauses, clearly uncomfortable. “It’s not really in the job description.”
You tilt your head. “Try me.”
He hesitates, then sighs. “I need you to tell me if I’m being… difficult.”
“With clients. Or coworkers. Or—” He trails off, frustration creeping into his voice. “I don’t always realize how I come across.”
You study him for a second, then smile softly. “You’re intense,” you say honestly. “But not in a bad way. Just… very serious.”
He exhales, like you’ve lifted something heavy off his chest. “Okay. I can work with that.”
A few days later, Jonathan calls you into his office. His voice comes through the open doorway, hesitant but deliberate, saying your name like he’s rehearsed it beforehand. He mentions something about a spelling mistake in an email you’d typed up for him, his tone careful, almost apologetic.
When you step inside, he’s standing behind his desk instead of sitting, one hand gripping the edge like he’s bracing himself. He turns the computer screen slightly toward you, pointing out the error—something small, barely noticeable.
“Um… I’m sorry,” you say softly, sheepish heat creeping into your face.
Jonathan doesn’t respond right away. He just keeps looking at you, like he’s trying to figure out what he’s feeling before he lets himself react. The silence stretches, making your nerves buzz. You finally break eye contact and sit down in the chair across from him, fidgeting with your fingers in your lap.
“Will you… come here?” His voice wavers, unsure, like he’s already second-guessing himself.
“Come here,” he repeats more gently, gesturing toward him—not demanding, just inviting.
Your heart pounds. “Um…” You hesitate, searching his face for reassurance. He looks just as nervous as you feel, eyes wide, posture stiff, like he’s afraid you’ll say no.
“…Okay,” you say at last.
You stand slowly and step closer, every movement feeling louder than it should. He shifts in his chair to give you space, hands hovering uncertainly until you sit, carefully, on the edge of his lap. He freezes for half a second, then relaxes just enough to rest his hands at your waist—light, tentative, like he’s asking permission without words.
You stammer out the words, your voice barely above a whisper as you shift uncomfortably on Jonathan Byers' lap, feeling the hard edge of his desk pressing against your thighs. The warmth of his body seeps through your skirt, and the scent of his cologne mixes with the faint musk of arousal hanging in the air of his dimly lit office. "Uh... I can fix the typo... I'm sorry," you manage, your cheeks growing a little hot with embarrassment over the mistake in the report he's been scrutinizing on his computer screen.
Jonathan inhales sharply, his breath hot against your neck as he leans in closer, his broad chest rising and falling against your back. His hands, which had been resting innocently on your waist while pointing out the error, slide downward with deliberate slowness. Strong fingers grip the curve of your ass, squeezing the soft flesh through your skirt, pulling you tighter against the growing bulge in his pants.
The power in his touch sends a shiver up your spine—he's your boss, after all, the one who holds your career in his hands, and now he's claiming more.
"Mr. Byers, I—" you gasp, the words catching in your throat as his grip tightens, kneading your ass cheeks possessively. Your heart races, a mix of nerves and unexpected heat pooling between your legs. He chuckles low in his throat, the sound vibrating through you, and one hand slips under the hem of your skirt, tracing the edge of your panties with a teasing stroke.
"Shh, no need to apologize," he murmurs, his lips brushing your ear, voice laced with authority. "But you'll make it up to me right here. Show me how sorry you really are." His other hand joins the first, both now boldly cupping and spreading your ass, fingers dipping toward the dampening fabric at your core.
You squirm against him, but he holds you firm, his erection pressing insistently against your thigh.
Your breath hitches as Jonathan's fingers hook under the edge of your panties, tugging them aside with a firm yank. The cool office air hits your exposed pussy, making you clench involuntarily, already slick from the forbidden thrill of his dominance.
He spreads your ass cheeks wider, one thick digit circling your tight entrance before pressing in just enough to tease, while his thumb grazes your swollen clit, sending jolts of pleasure through your core.
"That's it," he growls, his voice rough with lust, nipping at your earlobe. "Grind against me…." His free hand snakes up to unbutton your blouse, popping the top few open to reveal the lace of your bra. He shoves it down roughly, palming your breast and pinching the hardening nipple between his fingers, twisting just hard enough to make you whimper.
You rock your hips instinctively, your wet folds sliding against the rigid length straining in his trousers. The friction builds heat low in your belly, and you bite your lip to stifle a moan, aware of the thin walls separating you from the rest of the office. But Jonathan doesn't care—he thrives on the risk, on owning you right here at his desk.
He unzips his pants with a swift motion, freeing his thick cock. It springs out, hot and heavy against your thigh, the veined shaft throbbing with need. Precum beads at the tip, smearing onto your skin as he guides your hand back to wrap around it. "Stroke me," he commands, his breath ragged. "Show your boss how badly you want to keep this job."
Your fingers curl around his girth, pumping slowly at first, feeling him pulse in your grip. He groans, thrusting up into your hand while his fingers plunge deeper into your pussy now, two curling inside you to stroke that sensitive spot that makes your vision blur.
Juices coat his hand as he fucks you with them, the wet sounds obscene in the quiet room.
"Fuck, you're soaked," he mutters, withdrawing his fingers only to bring them to your lips. "Taste yourself. Know what you do to me." You obey, sucking the tangy essence from his digits, your tongue swirling as he watches with dark hunger. Then, without warning, he lifts you slightly, positioning his cock at your entrance. The broad head nudges your folds, parting them as he sinks in an inch, stretching you deliciously.
You cry out softly, but he clamps a hand over your mouth, his eyes locking onto yours in the computer screen's reflection. "Quiet, or I'll bend you over this desk and give you a reason to yell…" The threat only heightens your arousal, and you nod, pushing back to take more of him. He thrusts up hard, burying himself to the hilt in one brutal stroke, filling your pussy completely.
His hips snap rhythmically now, pounding into you from below while you ride him on his lap. Each drive hits deep, his balls slapping against your ass, the desk creaking under the force. Sweat beads on his forehead, his tie askew, but his grip on your hips is ironclad, controlling every bounce. "Cum for me," he demands, his thumb returning to rub furious circles on your clit.
The pressure builds unbearably, your walls fluttering around him as orgasm crashes over you. You shudder, biting down on his palm to muffle your screams, pussy clenching in waves that pull him deeper. Jonathan follows seconds later, grunting as he floods you with hot spurts of cum, marking you from the inside out.
The next day, you come into work and barely say a word to Jonathan.
You keep your head down, busying yourself with emails and paperwork, pretending everything is normal even though your stomach is in knots. Every time you hear his office door open, your shoulders tense. You can’t bring yourself to look at him.
You slept with your boss.
The realization hits you all over again, sharp and embarrassing. What was I thinking? What if he regrets it? What if he thinks you crossed a line? Worse—what if you crossed a line and he decides it’s easier to let you go than deal with the awkwardness?
You exhale slowly through your nose, fingers hovering over the keyboard before forcing yourself to keep typing. An email blurs on the screen as your thoughts spiral.
You risk a glance toward his office.
The door is open, but Jonathan is turned away, focused on a stack of papers. He looks just as tense as you feel—jaw tight, shoulders hunched, like he hasn’t quite figured out how to exist in the same space as you yet.
That somehow makes it worse.
You sigh quietly and turn back to your desk, forcing yourself to finish the email in front of you. Professional. Normal. That’s what you need to be. Even if your heart is still racing and last night lingers uncomfortably in the back of your mind.
A few weeks later, you get called into his office again. “More typos,” he says quietly, almost sheepishly. His eyes flick up at you, but there’s something about the way he says it—gentle, hesitant—that makes your stomach knot.
Ever since… the incident, you’ve been double-checking everything, rereading every email, every memo, every little detail. How could there still be a mistake? You feel your cheeks heat as you step inside, holding your hands together nervously.
You stop by the door, unsure if you should sit or stand, and Jonathan gestures toward you with a small, awkward motion. “Come closer,” he says softly.
You take a tentative step forward, stopping awkwardly near his desk. He stands, moving around so he’s now behind you. You notice how careful his movements are, how quiet the room suddenly feels.
“Put your hands on the desk,” he instructs, his voice low, steady, but with that familiar hesitancy that always makes your pulse quicken. “Palm down.”
You glance at him for a brief moment, then place your hands on the polished surface, fingers spread slightly. It’s not like I want to get in trouble, you tell yourself, heart thudding.
He lingers behind you, close enough that you can feel the warmth radiating from him, but not so close that it’s uncomfortable. His presence is heavy, cautious, and charged in a way that makes your stomach twist.
Then, without warning, his hand comes down—firm but not brutal—smacking against your ass with a sharp crack that echoes in the confined space. The sting blooms instantly through your skirt, a jolt of heat that makes you gasp, your body jerking forward instinctively. “Jonathan—” you start, the word half-protest, half-plea, as one hand twitches to move, to rub the smarting flesh or push away.
But he's quicker, his free hand clamping gently but insistently over yours, pinning it back to the desk. His touch is warm, fingers curling around your wrist with that same hesitant firmness.
“Keep your hands down, just like I said,” he murmurs, his voice low and steady now, the sheepishness fading into something more assured, though the underlying gentleness remains. His breath fans hot against the nape of your neck, and you feel the press of his body inching closer, the tension between you thickening like smoke.
You freeze under his touch, the warmth of his hand on your wrist sending sparks up your arm. The sting from the smack lingers on your ass, a throbbing heat that pulses with each heartbeat, making your thighs clench involuntarily. Jonathan's fingers tighten just a fraction, not enough to hurt, but enough to hold you in place, his thumb brushing lightly over the inside of your wrist as if to soothe the restraint.
“I’m sorry,” he whispers, the words so soft they almost dissolve in the air between you. But he doesn’t pull away. Instead, his other hand hovers near your hip, the heat from his palm radiating through your skirt. You can feel the slight tremor in his touch, that hesitancy that makes everything feel more real, more dangerous. Your breath catches, chest rising and falling quickly, and you wonder if he can hear how ragged it’s become.
He steps closer, his chest brushing against your back now, the fabric of his shirt whispering against your blouse. The contact is light, tentative, but it ignites something deep in your core—a slow burn that spreads from your ass up your spine and down between your legs.
His hand on your wrist slides up your arm, fingers tracing the curve of your elbow before settling on your shoulder. He presses gently, urging you to arch your back a little more, to push your ass out toward him. You comply without thinking, the desk cool under your palms, your nails digging into the wood as anticipation coils tighter in your belly. The room spins slightly, the scent of his cologne mixing with the faint musk of arousal hanging in the air—yours, his, impossible to tell.
Another smack lands, this one sharper, landing on the other cheek with a firm slap that makes your skin tingle and burn. You yelp softly, hips jerking forward, but his hand on your shoulder keeps you steady. “Stay still,” he says, voice firmer now, though that gentle edge lingers like a promise.
His free hand finally makes contact, cupping the curve of your ass through the skirt, squeezing the flesh he just struck. The pressure is soothing and possessive all at once, his fingers kneading slowly, working the sting into a deeper ache.
“Jonathan, please,” you breathe, not sure if you’re begging him to stop or to keep going. Your pussy throbs in response, a slick warmth gathering between your thighs, soaking into your panties. You shift your legs slightly, trying to ease the pressure, but it only makes you more aware of how wet you’re getting, how your body betrays the nervousness twisting in your gut.
He leans in closer, his hips pressing against your ass now, and you feel the hard outline of his cock through his pants—thick, insistent, straining against the fabric. It nestles right between your cheeks, the heat of it making you gasp again.
“You feel that?” he asks, his voice low and rough, laced with that sheepish undertone that makes your heart stutter. “That’s what you do to me. Every time you come in here, every time I see your name on an email... it’s this.”
His hand on your ass slides lower, fingers dipping under the hem of your skirt, brushing the bare skin of your thigh. The touch is electric, tentative at first, as if he’s waiting for you to pull away. But you don’t. You can’t.
Instead, you push back against him, grinding your ass against his cock, feeling it twitch in response. A low groan escapes him, vibrating against your neck, and his fingers venture higher, tracing the edge of your panties.
“Tell me to stop,” he says, almost pleading, his breath hot on your skin. But his fingers hook into the waistband, tugging them down slowly, exposing the damp fabric clinging to your pussy. Cool air hits your wet folds, making you shiver, and you bite your lip to stifle a moan. He pauses, hand stilling, giving you that out, that moment of hesitancy that defines him.
“Don’t,” you whisper, the word slipping out before you can catch it. Your cheeks burn hotter than the smack on your ass, but the relief of saying it floods through you. Jonathan exhales sharply, and then his fingers are there, sliding along your slick slit, parting your lips to find your clit. He circles it slowly, gently, the touch so careful it borders on torture, drawing out a whimper from your throat.
“Good girl,” he murmurs, the praise soft and hesitant, like he’s testing the words. His cock presses harder against you, rocking in a slow rhythm as his fingers work your pussy, dipping inside just enough to coat them in your wetness before returning to your clit. The dual sensation—his hand between your legs, his hips grinding against your ass—builds the pressure fast, your knees weakening, body leaning heavier on the desk.
He smacks your ass again, lighter this time, the sound wetter now with your arousal slicking everything. The sting pushes you closer to the edge, your hips bucking back against his hand, chasing the friction.
“You’re so wet,” he says, voice thick with need, fingers plunging deeper into your pussy now, two of them curling inside you, stroking that spot that makes stars burst behind your eyelids.
You cry out, hands slipping on the desk as pleasure coils tight, ready to snap. Jonathan’s other arm wraps around your waist, holding you up, his chest flush against your back. His lips brush your neck, not quite a kiss, but close enough to make you arch into him. “Come for me,” he whispers, the command gentle, hesitant, but undeniable.
His fingers thrust faster, thumb pressing your clit, and you shatter—pussy clenching around him, waves of heat crashing through you as you gasp his name, body trembling against the desk.
He doesn’t stop, drawing it out until you’re boneless, panting, your ass still pressed to his cock. Slowly, he withdraws his fingers, and kisses you on the cheek.
He moves away from you and slides back into his desk chair, the scrape of its legs against the floor making your stomach twist. You stand, legs trembling, hands smoothing the folds of your skirt as if trying to iron out the nervous energy coiling inside you.
You walk out, fidgeting with your fingers, and make your way back to your desk. Sitting down, you wince and press your palms against the cool surface, trying to shake off the lingering tension.
A few weeks later, you realize that you’ve been talking to Jonathan more than you even notice. The conversations start small—checking over reports, clarifying tasks—but gradually, they stretch into more personal exchanges, subtle jokes and easy smiles that make your day feel a little brighter. You catch yourself looking forward to his presence, the soft hum of the office around you fading into the background whenever he’s near. Even the simplest interactions—a shared laugh over a typo, a glance across the room—leave a warm flutter in your chest that you can’t ignore.
One afternoon, as you’re organizing files at your desk, Jonathan leans against the corner, his usual professional composure softened by something warmer in his eyes. There’s a nervous energy in the way he shifts his weight, the faintest smile tugging at his lips, and you feel your own hands tighten slightly on the papers in front of you.
“Hey…” he starts, shifting uncomfortably, his eyes flicking away for just a second before meeting yours again. “…Would you, uh… want to go out? Maybe for coffee, or… something?” His voice is hesitant, almost a whisper, and he runs a hand through his hair nervously. “I know it might seem like—after everything—I don’t really… care. But, uh… I do. I really like you,” he adds, his words tumbling out a little faster, sheepish but honest.
Your chest tightens, your heart skipping a beat. For a moment, the office seems to vanish, leaving just the two of you in a quiet bubble of anticipation. Then, with a small, shy smile, you finally say, “Sure…”
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