*READ PT 1 -> here!*
after a quite unprofessional favor the night before, u and harry reconcile in the office.
based on this, this, this, this, this, and this. ty perf anons;)
CW: ceo!harry x assistant!reader, age gap, improper work relations, masturbation (m), oral (f), clit overstim, p in v penetration (unprotected), choking, dirty talk, size kink, praise kink, power play, soft pleasure dom, subby reader, just…dirty. raw and filthy.
likes/reblogs sooo appreciated!
WC: 14.8k (im sorry)
Head down. Toe to heel. Find your desk.
The solid clack of your heels against the slick flooring was deafening. The excessive pounding against your chest was even worse.
You barely slept.
It wasn’t for lack of trying. You’d turned over, fluffed your pillow, closed your eyes and forced yourself to breathe slowly like that was somehow going to quiet your brain. Like it would somehow take you out of the life altering decision you just had to partake in.
Because you just really couldn’t have done the right thing and said, hey, maybe we shouldnt fuck over the phone. You know, since I work for you.
But every time things got quiet, your mind just… replayed it. Over and over. Every word, every second, every choice.
Your choices, more specifically. The way you complied without question. The way you took it over the top too—adding your own twinge of sexual grossness that he certainly did not ask of you.
By the time your alarm went off, you were already awake, staring at the ceiling with that same tight feeling in your chest.
Now you’re here. Speed walking through the long-halled building and finally making it to your desk.
You take a quick seat and a giant huff of air once you’re settled, staring up at the clock and dropping your head in your hands.
It was too early.
Embarrassingly early.
Of course you showed up early—what else were you supposed to do? Stroll in at your normal time like nothing happened? As if you hadn’t completely humiliated yourself in front of the one person you’re supposed to be the most put together around?
You smooth your hands over your outfit for what has to be the tenth time, even though there’s nothing wrong with it.
A black skirt. White button up. Maybe a little too tight for your own good, and maybe a few too many buttons unraveled. But it was nowhere out of the realm of what you usually wore. You always had fun with what you had on. You’d like to think it wasn’t for Harry’s benefit, but at this point, how would you know.
Everything is exactly how it should be. How it always is. Neat. Professional. Controlled.
“Okay,” you think out loud, staring at your computer screen without actually seeing anything. “You’re fine. You’re going to act normal. Everything is normal.”
Normal.
Right.
Because acting normal is so easy when your brain keeps helpfully reminding you of the fact that you drenched your own fingers while your mind convinced you it was a dick.
Like literally a dick. Your mind genuinely was tricked into thinking your boss was fucking you in your bed, so much so to where you came quicker than you ever had before.
The tone of his voice. The velvet draw of his laughter. The split second where you realized—too late, I’m fucked.
You squeeze your eyes shut briefly before speaking aloud once more. Just to yourself. There was no one even close to near.
“Maybe it wasn’t actually that bizarre.”
Immediately, your brain disagrees.
“No, very bizarre. Definitely abnormal assistant behavior.”
Your fingers hover over your keyboard, still and frozen in place.
“Okay, so we made a mistake. That’s fine. People make mistakes all the time. It doesn’t mean anything.”
You couldn’t even pretend to be taking yourself seriously. There was no comparable situation to what you two engaged in last night in this world.
He’s your boss.
There are lines. Obvious ones. More importantly, strict career ending ones. And somehow you managed to trip right over one like you had a half a brain and a dick of your own.
You let out a quiet breath and glance towards the door that lead into your office.
Still closed.
The room set up was private. A door that lead to your office, and then a door that was in your office that lead to his.
Creating a horribly unavoidable situation in which he would have to pass by you in order to get to his office.
Probably something that should have been further considered before you begged for his cum.
But, it was early. He wouldn’t be coming in soon. Which just gives you more time to sit here and think.
“Maybe you should say something when he comes in.”
Your stomach immediately twists.
“No, no. That would make it worse. If you bring it up, it becomes a thing. If you don’t bring it up… maybe it just fades away.”
You know, they way all sexual encounters in the workplace end up flying under the radar.
You were kidding yourself.
You tap your pen lightly against the desk, the soft rhythm doing nothing to calm the restless energy under your skin.
You still hadn’t started any work.
“But what if he brings it up?”
That thought lands heavier than the others. That one you can’t escape from.
Your posture straightens instinctively and your face tenses, legs crossing over one another as you sink into your anxiety.
“Then what? Do I apologize? Take accountability? Pretend I don’t know what he’s talking about?”
None of those options feel right. None of them were right. And you were just wasting time now.
You glance at the clock.
Too early.
Again.
Even too early to get his coffee. It’d be ice be the time he arrived.
You exhale through your nose, forcing your shoulders to relax and your brows to release their tension.
“Okay. New plan.”
You sit up a little straighter, folding your hands together like that alone might make you feel more composed.
“You’re going to be professional. Calm. Normal. You’ll greet him the way you always do. You’ll go over his schedule. You’ll do your job.”
You know, the normal thing to do.
“And if he says something…” you pause, your fingers tightening slightly, “you’ll handle it. You always do.”
That part, at least, is true. You are good at your job. You’re organized, reliable, composed…
…or at least, you usually are. Apart from shoving 4 fingers deep inside of you as you nearly snapped your arm backwards.
You also decided it was time to stop talking to yourself. As to not seem so disturbing to anyone who may come in.
Your eyes dart up to the door again.
Still closed.
But not for long.
“Morning.”
The door pressed open smoothly, a tall Harry walking through with a bag slung over his shoulder and a polite smile on his face.
You were dumbfounded. And very clearly not as prepared for the initial greeting as you thought you’d be.
“You’re in early,” he continues, shutting the door softly behind him and staring down at you at your desk.
He was dressed perfectly neat—slick ironed pants and a long sleeved button up that was nicely folded up his forearms.
And, worst of all, a smug grin that was only one thing.
Knowing.
“I—um, yes,” you say, and it comes out a bit more formal than you would’ve liked. So, in typical you-nature, you ramble on, “I just wanted to make sure everything was in order today. I didn’t realize you’d be in early too, I’m sorry. I haven’t gotten your coffee.”
There’s a small pause as he watches you speak. Him standing, you sitting. Your eyes were glossed up at him in an innocently sweet manor, and he breathed out slow at your little apology.
And then he was thinking about you. The way you were so generous to him and wrapped up in the pleasure you had given to yourself.
The sweet noises that slipped through the speaker and swarmed around his pumping fist. He felt his pants tightening at just the thought.
“Everything usually is,” he says, referring to your faux reasoning for coming in early.
It was a simple statement. And somehow, it had your stomach twisting into itself until it was locked in a knot.
“I know,” you say, too insistent, “I just thought I’d get a head start.”
He continues to watch you. Delightfully amused and analyzing your every move. The little tick of your eyelids and the way your thumb scratches against the side of your index finger. The way your eyes struggle to hold their contact with his no matter how firm his gaze is on yours.
It was nothing harsh, nothing critical.
Just…observant. Interested.
Your pulse picks up as the silence stretches over you. You reach for the nearest file on your desk, flipping open to the schedule for today and searching for something to fill the gap.
“Your nine o'clock is confirmed,” you start, “I sent over the updated notes for you early last night.”
A brief mention of the night before. Granted, you sent them over before the call, but the two words had your skin tinged.
“Mm.”
“And your branch clients are scheduled for 12:00,” you continue in a nervous rush. Like if you kept talking it would give you less time to think, “there was a slight change in the afternoon so-”
“You don’t have to rush through it,” he cuts you off, gently reminding you that no, you don’t need to inform him of his entire day within the first minute of seeing him.
Something you’ve also literally never done before. You always update him periodically. When needed.
He hasn’t moved much, still relaxed and still adorned in the smug smile of a man who knows he has a cute young thing wrapped around his finger.
“I’m not rushing,” you say, which would have been more convincing if you didn’t say it so quickly.
The corner of his lips deepen into his smile, lips still held together as his dimple presses further inward.
“Right.”
You loosen the tight grip on the file you were holding as you take a small breath, desperately trying to pull your shit together and enter this normalcy that he’s somehow achieving.
“I can go over your day in more detail later then, if you’d like,” you restart, carefully this time. “Or I can send a revised outline to your email.”
He watches you for a second longer than he should after your sentence wraps up, like he’s weighing something in his head.
Or maybe just taking you in. You weren’t sure. Neither was he.
“That won’t be necessary,” he says, “I trust you’ve handled it.”
And then there was that feeling again. The heat on your cheeks and the ping between your legs that you only felt when he praised your work like this.
He noticed your subtle shift, and it only further spurred on the dark thoughts that had been thudding against his skull since the moment he walked in.
“Of course,” you nod, clamping your thighs tight and suddenly finding it more than difficult to look directly at him.
There’s another pause, and it’s quieter this time around. It almost feels purposeful. Like he’s trying to make you feel deliberately nervous.
You expect him to turn around, walk past you and head right to his office. This would usually be the time he’d do it. He’d stay in there and wouldn’t see you again until his nine o'clock clients arrived.
But he didn’t. He stayed perfectly still and unwavering by your desk.
You didn’t know if he was looking at you, you couldn’t bring yourself to check. You were faced down towards your desk, flipping through random papers and trying to look busy.
You weren’t.
Your eyes flick up again before you can stop them, and you immediately regret it when you catch that same look—calm, steady, and unmistakably knowing. Like he’s taunting you with the memory of your misconduct.
“You’re tense.”
It was matter-of-fact as it rolled off his tongue, as if it was an observation he wasn’t particularly concerned about.
Your breath hitched for just a second.
“I’m not.”
You sounded adorably unconvincing, and he couldn’t help himself when he took just a step closer. Maybe an inch. Maybe two. Nothing to freak out over. But still enough for you to feel sick.
Then, softer, with even more amusement, “You are.”
You don’t try to argue this one. You’re already flustered enough and the lack of awareness of last night is seriously starting to weigh on you.
If he wasn’t going to mention it, you’d prefer him to just leave. Instead of sit here and toy with you.
Even if part (all) of you enjoyed it.
Finally, there’s a shift in the energy as he takes a step back towards his office. Slow and steady as he walks with a hand in his pocket.
Relief flickers over you for just a moment—fragile and prepared to snap the next time you have to interact with him.
And then, it shatters.
“Bring those files in here.”
He said it like it was nothing. Like he’s ever once in his whole life asked you to bring your work inside of his office.
He hasn’t, by the way.
Your hands still for a second, “Right now?”
There’s another beat of silence as he looks at you, taking in your flushed cheeks and your shaky hands and the way your eyes pressed further out of their sockets. Just barely.
He remained calm. Composed and completely unbothered by the fact that your whole nervous system just spiked within a half a second.
“If you’re not too busy,” he adds.
There’s something intentional in the way he says that part. Like he already knows that you’re not busy in the way you’re so desperately pretending to be.
It really was almost sarcastic.
“I’m not busy,” you respond a little too quickly, immediately embarrassed by your haste and cringing when you notice his smirk.
“Good,” he replies.
Just that. One word and a small nod.
He turns and walks into his office like he hasn’t just completely derailed your ability to think straight. His strides slow and long and hands still melded softly in the rich material of his pants.
You follow a moment later, files clutched a little too tightly in your hands, trying to convince yourself this is normal.
Part of you says it is. You are his assistant after all. It’s not totally out of realm for him to ask you to bring him something you’d been working on.
It was slightly abnormal that he needed you to come with it, but for the sake of your soaked panties and your swarming mind you chose to ignore that.
You instinctively shut the door behind you, which you immediately regret. The last thing you wanted was for Harry to fall under the impression that you were seeking privacy with him.
It was too late to go back now.
And Harry was quite pleased with your mindless decision.
“Um,” you clear the cracks from your nervous voice, “I can show you some of what your Milan schedule will be, if you’d like. I’ve started to make confirmations so I have a pretty good idea on how it’ll go.”
He nodded, dropping his bag onto his chair and leaning up against his long desk. You were standing in front of him like you didn’t have a clue of where to go, mouth dry and thoughts dangerous.
“You can mention it, you know,” he ignored your offer, folding his arms as he looked at you.
You froze.
This is precisely why you needed more time to prepare yourself.
“Mention?” You gulp, thick and trembling as you fight away your stress.
It was one of those red hot moments where you could feel the heat rising to your cheeks and just get flooded with thoughts of how red you must look. How stupid you look in front of him and how obviously embarrassed you were.
“Us. Fucking, on the phone.”
As if it was the most mundane thing to have ever happened.
You take a small breath, forcing yourself to stay composed as you break your gaze from his in a quick instinct.
“Um, I think-”
Y/n,” he cuts you off, leaning down to try to catch your wandering gaze, “can’t listen to you if you’re not looking at me.”
You nod quickly, itching your bottom lip with your teeth for a moment before blinking your way to his face. He was pleased to see his request, or demand more like, be granted so easily.
He was also pleased to catch the not-so-subtle gulp of saliva down your throat and the quick clamp of your thighs.
“I think, um, it would be best to not dwell on it, sir. I’m sorry to have violated my professional limits.”
You were proud of that one, actually. Clean. Simple.
All bullshit.
He knew it, too.
He shook his head, in no hurry, as his eyes fell down to you through low lids. Pink lips pressing together in a small line as he uncrossed his arms.
“Wasn’t bringing it up for an apology.”
You swallow harder, shutting your eyes for a moment in a sad attempt to remind yourself of reality. To not get completely and totally wrapped up in the seductive sway of Harry’s voice and the deep vanilla musk that swam around him.
“I value my position here,” you continue, ignoring his insinuation, “and I respect you, Mr. Styles. I guess we should just…move forward as usual.”
And the second his name slung its way up your chest and out of your lips, you had unknowingly put yourself in a game. In his game.
You could see it in the way his eyes darkened and his brows fell into each other, just barely, like your words had turned him to putty.
Another pause. Heavier than before.
Your pulse ticks up, but you hold his gaze, refusing to look away now. You’re sucked into the thrill of the forbiddenness of it all, the way the four small walls seemed to shrink and the room blurred.
Then, slowly, the corner of his mouth lifts again. Deep this time, like he’s finally decided what his next move is.
“You always are very efficient.” He said, as if he was weighing between the options of keeping you as his perfect assistant or further crossing the line.
“I try to be,” you answer softly.
And then he exhales—long, deep and drawn out in an overly dramatized way. Like he had made his decision and accepted his fate.
“You do,” he nods, “and you are. Really, you do such a good job.”
And just like that, your gig was up. You had accepted your fate too.
“Thank you,” you smile, cheeks rosy and eyes falling for a moment in a bashful tick.
He takes another small breath as he settles further back against his desk, practically sitting on it now as his hands are stabilized against the same edge.
“You’re efficient. Organized. You know what I want without having to ask. You never fuss, either,” he continues, shaking his head for just a minute as if overwhelmed with pride.
He watched as you shifted in front of him, tugging against the inside of your cheek and picking at the sides of your fingernails. He could tell you were fighting back a smile, the crowns of your cheeks darkening and flinching for just a moment.
You don’t know what it is; maybe the way he’s looking at you or maybe the way he’s leaned against the desk. But, suddenly, you felt your last wall come down with a sharp ache between your thighs.
“I like to fulfill your needs, sir. I couldn’t fuss.”
The second the words leave your mouth, you both get slammed in the chest with the shift. His smirk deepens, your eyes round.
He doesn’t even attempt to hide his growing erection. And with the way he was leaning against his desk—hands gripping the ledge behind him—it was on full display. Hips jutted out and the thin material of his fine pressed pants tenting upwards.
He was big. You could tell. Anyone with two eyes and half a brain could tell. The shadow on his crotch was deep and the curve of his cock was delicious. So much so that you forgot how long you’d been staring.
But he liked to watch you soak him in. He liked when you lingered where you shouldn’t, wide and a little unfocused like your brain forgot to tell you to look away.
There was this brief, flustered pause where your lips parted like you were about to say something but completely lost it; and it hit him all at once. The desperation.
Your breath catches as you lift your gaze too quickly to be smooth, fingers immediately fidgeting with whatever’s in front of you while a faint warmth creeps up your neck and across your cheeks.
“Is that so?” He mutters with a tilted head.
You nod slowly.
“Yes, sir. I take a lot of pride in what I do. I just…want to make you happy with my work.”
He lets out a barely audible chuckle, not criticizing. Just pleased—shocked even—by the little nervous thing in front of him. So quiet and so polite, clawing at him for just a drop of praise.
“I’m aware,” he nods, “you have me more than pleased, y/n. You’re exceptional.”
You practically whimper at that one.
He notices.
“And you know what else?” He leans off of his desk to stand in front of you, “you’re shameless. You were so good to help me out that way last night…but I think we found a place for your own pleasure too. Is that right?”
He was towered over you, eyes turned into themselves as they landed on your face and darted around it like they couldn’t find a place to stop. Yours were glassed as they peered up at him, soft skin shining and heart thudding.
“Y-Yes. Yes, sir.”
He nods, nose practically touching yours as he slips his hands back into his pockets.
And then there was another silence. But this one was different—it was full. So heavy and laced in the fucked up nature of whatever was brewing in this dimmed office.
There's a flicker of something in his expression that you’ve never really seen before. Not up close like this, anyway. Not quite hesitation, not quite intent, but something that makes your pulse spike anyway.
Like he’s on the edge of doing something he shouldn’t. Like he knows you’d give in immediately if he did it. He knew the ball was in his court.
Your body goes still, caught between reacting and not knowing how to. Your fingers toy with the hem of your little skirt as you stare up at him, waiting—but you weren’t totally sure what for.
And then it stops.
You see it happen in slow motion—the subtle shift, the way his jaw tightens just slightly before he exhales, slow and controlled, like he’s grounding himself. Stopping whatever he was so compelled to do without even starting it.
Whatever the hell that moment was, it disappeared just as quickly as it came.
He steps back, turns, and walks to his desk like nothing happened.
The change is almost jarring.
No—it is jarring. Sickening, really.
One second prior, everything was charged, heavy. You even thought he might just…you know, do it. Throw all professional boundaries out the window and close the gap that was already too small to begin with.
And the next, he’s sitting down, opening the file in front of him, his focus dropping to the pages like that’s all that matters.
Like you didn’t just feel that. Like he didn’t either.
The silence that settles is thick.
You’re still standing where you were, your mind trying to catch up with the sudden shift. Do you leave? Do you say something? Were you supposed to follow him? Was that his way of confirming that yes, this is entirely unprofessional and more than wrong.
You hesitate, shifting your weight slightly, hands hovering like you’re about to move but can’t quite decide how.
Then he looks up.
Not fully— his head stays tilted downwards. Just his eyes lifting from the page to you.
There’s no words, no gesture. Just a brief glance toward the chair across from him, subtle but deliberate.
An expectation. An instruction.
Both things that you strived to obey and both things that he knew you always followed through with.
Your stomach sinks into itself, but you nod slightly, even though he didn’t actually say anything. You move to the chair, sitting down a little more carefully than usual. Like you were scared to make too much noise or to scratch the expensive wood of his desk.
You pull the files you brought in closer, aligning them in front of you like you need the structure, the routine, something to ground yourself.
Because you really did. Your mind was mush and your muscles were jelly.
He’s already working. Flipping through pages, scanning, focused. All things that you usually never saw. This was always on the other side of the door, from your perspective.
You’re more than unsure of his goal here. To work silently across from each other? For what, the whole day? Were you supposed to just stay here until his nine o'clock clients arrived?
There would be no one at your desk to greet them. Were you meant to excuse yourself 15 minutes prior to the meeting? No, that feels rude. He’ll tell you to go. But what if he doesn’t? What if your colleagues scope you out? Is it weird that you’re working here with him?
In an attempt to not, you know, break out in a full blown panic attack, you take a breath and look down at your work.
You follow his lead, opening the next file, forcing your attention onto the words in front of you—even though you’re only aware of everything else but.
The quiet. The space between you. The way it still feels like something unresolved is sitting just beneath the surface.
Neither of you say anything. There’s just the soft sound of paper shifting, the occasional scratch of a pen, the steady rhythm of work filling the room in place of everything that almost happened.
And somehow, that’s worse.
Because now it’s contained.
But very much still there.
“You liked listening to me last night,” he breaks the silence, keeping his gaze on the work in front of him.
Your mouth opens, closes, and opens again.
“Yeah,” you nod, pushing your head down and swallowing your anxiety. As much as you can, anyway.
Which isn’t much.
He smiles at this. How easy it was for you to admit it. Eyes still down at his desk.
“Were you picturing it? Me?” He lifts his stare now, meeting your nervous eyes and watching as they stutter until they land on a place to settle.
He leans back in the chair like he owns the space without trying to, shoulders settling into it with confidence that somehow makes him look even more composed than before. His hands rest loosely in his lap, posture relaxed in a way that feels intentional rather than casual.
Nothing about him is rushed, nothing about him is uncertain. Just steady. Controlled.
And it does nothing to help you think.
Wrong words. All of them feel wrong.
Your fingers press lightly into the edge of the file in front of you, grounding yourself in something physical because your thoughts are doing the opposite of that. The silence stretches just enough to make you aware of it, aware of him watching you wait for yourself to respond.
“You’re overthinking,” he says, calm as ever.
That only makes it worse.
“Sort of.”
He slouched further back into his seat, his grin still tugging upwards and his eyes hanging low. He was truly satisfied at your constant compliance. The way you always admitted your deepest embarrassments just because he asked or pointed them out. It was admirable.
“Do you want to watch?” He asks, low and gritted, as casual as ever.
Not a casual ask, by the way.
And then your gaze drops, along with your stomach, and you notice the subtle shift of his hands on his lap. The way his palms melt flat against himself and rub softly over the tented fabric of his pants.
You gulp, thick and heavy, though nothing really slides down your throat. Your mouth is dry and your head is dizzy, caving into itself as you piece together what could possibly be the correct response to this.
Because if the consequences were eliminated, you’d be practically frothing at the mouth and shouting yes yes yes until his pants are at his ankles and his cock is in his hand.
He knew that part, too.
But there were consequences. And you were both under company time.
So, you decide to land on something that you felt was a solid middle ground.
A nod.
Slow and unsteady and paired with an adorable little smile that Harry couldn’t help but grin at. There’s a quiet confidence in the way he looks at you now, like he can already see everything you’re trying not to show.
And you are showing it.
You don’t mind that he can tell.
Because your nerves are getting harder to hide the longer he just sits there watching you. Your fingers keep fidgeting with the edge of the file, then stopping, then starting again. You try to steady your breathing, but it doesn’t fully cooperate. Every second of silence feels like it’s pulling something out of you. Anticipation, maybe.
Or just the fact that you’re waiting for him to say anything.
“You’re doing it again,” he says finally.
Your breath catches, “Doing what?”
He doesn’t answer right away. Just watches you for a second longer, like he’s deciding how honest he wants to be. Or deciding how he could get you as worked up as possible.
“Thinking too much.”
That makes your chest tighten in a way that’s almost frustrating, because he’s right and you don’t want him to be.
But you really can’t actually be frustrated.
Not when his hand continues to slowly rub against his lap in a mindless fashion, running over the hardened curve of his cock beneath his pants.
“I’m not,” you say quickly, but it comes out softer than you mean.
That faint smirk deepens just a fraction.
“You are,” he repeats, calm and with a small nod.
And somehow that calmness makes you feel even more on edge.
You try to focus on the file again, but it’s useless now. Your attention keeps slipping back to him, like you’re drawn to waiting for the next thing he’ll say. Or the next thing he’ll do.
You can’t possibly keep your eyes away from his wandering hands. The way they glide against himself with no effort at all. The way his hips jut upwards just a hair but enough for you to think about his thrusts.
You can feel it building in you—that mix of nerves and something else you don’t want to name, sitting right under your ribs.
Excited. Anxious. A little overwhelmed by how much he seems to notice without even trying.
He finally leans forward just slightly—not enough to change everything, just enough to make you more aware of him again.
“Relax,” he says, quieter now.
So you do. Well, try anyway. You take a deep breath, a nod, and keep your eyes on his.
You really do feel a bit more at ease. Your face has cooled, your breathing has regulated, your stomach has settled.
And then it snaps.
“Now unbutton your shirt.”
You actually choke on nothing, blinking at him like your brain didn’t process it correctly the first time.
You couldn’t have, right?
“I—what?” you manage, too fast, your voice catching slightly as your breathing returns to its prior erratic rhythm.
He doesn’t react too much to your reaction. Just watches you for a second, completely calm, like he’s observing the exact moment it hit you. He even seems amused. Like you just gave him exactly what he was looking for.
And you did. He loves to watch you get riled up like this. To watch your cheeks flush and your pretty pink lips part. It was honestly endearing.
His palm rubs harder against himself.
“Your shirt,” he nods towards your body, “aren’t you gonna let me see? It’s already too tight, anyway. But you knew that. Didn’t you?”
That’s the part that makes you go quiet.
Because it’s true.
You swallow, suddenly very aware of your hands, your posture, the space between you and the desk like it’s all being measured now.
You nod again, staring down at his working hands as they continue to press against himself.
And then, once you see them drift up to his belt and hear the clack of its metal, you comply.
Your shaky hands reach up to the first button of your shirt as you watch his veined fingers, your breath hitching within your chest and releasing in unsteady exhales.
His stare darkens as he watches you, pulling apart his belt and slipping it out of its hold through his pants.
You hook your fingers around the top button and start to open it, slower than you normally would, like speed alone might make you look more composed.
The button slips for half a second.
Of course it does.
You pause, adjust it carefully, then continue, your focus narrowing down to something very small and very controlled—just the act of opening the first few buttons. Nothing more. Just a view to your rounded cleavage and the dark black lace that lies beneath the fabric.
But you can see him watching. The way his jaw clenched with every new button and the way his nostrils flared outwards with every little movement.
His breathing had changed too. He was unstable, working to undo his button and pull down the zipper of his pants.
To say he was aching was an understatement. His cock was crying in pain and his hands were moving ridiculously slow, but he almost liked it this way. The drawn out nature of the beginning and the way your soft hands began to reveal more and more of your smooth skin.
And by the fifth button, he was thrown in a trance.
Your breasts looked so soft—round and firm and held perfectly in the loose restraint of the lace. Your nipples were hardened as they peeked their way through the black, a perfect bright pink that caught his eye without him even trying.
He goes quiet.
His hands pause their task at his zipper.
Not the normal kind of quiet where he’s just thinking. This is different.
His eyes stay fixed on your chest, an expression on his face that you’ve never seen in all your experience of this job. His brows draw in slightly, not tense, just focused in a way that slows everything else down around him. In a way that made him seem like his walls were crashing.
His lips part a little without him seeming to notice. Just slightly. Like his reaction slips out before he can control it.
You just sit there, chest heaving up and down in nervous breaths and bottom lip bitten between your teeth.
For a second, he doesn’t move at all. It’s like he’s caught.
Not frozen in a bad way, just… completely absorbed. Like the reveal of your perky tits has pulled all of his attention and nothing else is competing anymore.
You watch him, unsure if you should say anything.
His gaze shifts again, slower this time, like he’s making sure he’s really seeing it. Like it doesn’t make sense that it’s real, but it is.
And there’s this quiet breath he lets out, almost disbelieving.
“…shit,” he says under his breath, barely audible.
That alone makes your chest tighten a little.
He leans back slightly in his chair, still staring like his life depended on it.
His hands resume their movement as he tugs his zipper down in a haste, suddenly very desperate to give himself some relief.
His expression stays softened in that same stunned way, eyes a little unfocused now, like his mind is still caught in what he’s been gifted.
“I mean…” he starts, then stops again, shaking his head just slightly like he’s trying to reset himself.
When he finally looks at you, your face, it’s different.
Not distant.
Just honest.
“Do you want to see them?” You gain the courage to ask, voice sweet and ever so soft.
And there’s something in his reaction that makes it clear he needs it more than he’s saying.
You don’t wait for him to respond.
You undo the last of your buttons, quicker this time, before shrugging it off your shoulders and leaving you in the little black bra. Barely there. Already showing it all.
You watch him closely as he shrugs his pants down his thighs, his briefs clung tight against his erection and his eyes shutting in a brief moment of bliss.
And then you reach back, unclasp your bra, and just let it fall. No movement. No effort. You just let it slide down your arms until it pools to wrists and drops to the floor of his office.
He physically recoiled at the sight of your bare breasts ahead of him, a muted whine pressing up through his chest and his eyes turning inward.
“You’re—y/n. Fuck…” he stutters as he tugs on the spandex of his briefs, eyes locked on your perky tits and the way they curved so beautifully beneath themselves.
Of course he’d imagined this countless times. Well, he imagined them countless times. Not quite in this exact scenario. He dreamt of the creamy skin that coated them and the solid bud that rested in the center. He’d even cum to the thought more times than he could count.
But this?
It was unlike anything he’d ever seen or felt before in his life.
And if this was how he felt at just the sight of your tits, he was beginning to think he wouldn’t possibly be able to take it as far as he would want.
His hands mindlessly pull down on his underwear, revealing his cock in a slow tease that you couldn’t help but stare at.
And once you saw it, his erection bare and exposed, you couldn’t help the little gasp that slipped its way through your throat. You weren’t even sure if he heard it, but it was there.
He was long and thick and fucking hard. His cock slapped up onto his lower tummy at its initial release and then swayed slow and teasing as it adjusted to fresh air, glistening in a clear drip of what was to come.
Your chest heaved in an erratic rhythm as you took in his density, staring at it with your mouth agape and your cheeks flushed. It’d been awhile since you’ve been so struck by the sight of a good dick. Since you felt that little stab in your belly just at the sight of a heavy stocky cock.
And then there was his hand. Strong and veined and wrapped slowly around his length along with a drawn out sigh.
“Want you to keep working,” he sighs, “sit straight so I can look at you while I touch myself.”
You pull your eyes away from his cock at the sound of his voice, looking up at him with those big doe eyes and snapping your mouth shut.
So you did.
Well, you try to focus on what he asked of you. To work.
You really do.
Your eyes stay on the file, scanning the same line over and over like it’s going to suddenly make sense if you just look at it long enough—but it doesn’t.
Because every few seconds, your attention slips. Pulls. Drifts right back to the same place you’re trying so hard to ignore.
Him, his ringed hands tugging at his cock, his breaths heavy and his eyes locked to your exposed chest.
You shift slightly in your seat, straightening your posture like that alone might fix your distraction, like looking more composed will somehow make you feel more composed.
It doesn’t.
You drag your eyes back down, forcing yourself to read again, slower this time. Word by word. Intentional. Focused.
It lasts maybe three seconds.
His breaths pick up, heavier this time, and then you hear a sharp spit. He wetted his hand with his saliva before returning his feel, stroking smoother against himself this time with the added lubrication.
Then you feel it again—that awareness sitting right in front of you, impossible to ignore no matter how hard you try. Like your brain keeps circling back without permission.
The wet gush of his hand pumping against himself, lathered in his own spit and paired with the breathy sighs that come from deep in his chest.
You inhale quietly, steadying yourself.
“Focus,” he whispers.
Your fingers tighten slightly around your pen with a gulp as you underline something—anything—just to stay grounded in the task. It doesn’t even matter if it needs to be underlined. You just need something to do.
But even that doesn’t hold.
Your eyes flick up again.
Too quick.
His hand is pumping quicker. You keep your head faced down and your eyes flicked up, just peeking at what you so badly want to stare at.
You shift in your chair again, and this time you re-seat yourself with an accidental extra umph. Your tits shook at the repositioning, just barely but enough for him to notice.
Then you hear it—a groan. Deep and gravelled and gritted in his unprofessional pleasure and the sweet sight of his sweet little assistant’s tits jiggling against themselves. So soft and so full, pretty and unmarked and all for him.
And the second you process the sound that slipped through him, you drop your gaze just as fast, like you can undo it if you move quickly enough.
A heavy warmth creeps up your neck and between your legs, and you press your lips together, exhaling slowly through your nose as you try to pull yourself back into something steady.
You adjust the papers again, unnecessarily, aligning the edges with more care than they need. It gives your hands something to focus on, something precise and controlled.
But your mind isn’t cooperating.
Because you’re still aware.
Still distracted.
Still fighting the pull of looking up again.
You force yourself to stay down this time, eyes locked on the page, even though the words blur slightly at the edges.
You don’t look.
And then there’s that sound again. The low muffled groan of your boss, stroking his cock and bringing himself closer and closer to release. All while looking at you. The way you pretended to do your work, just to please him. The way your hard nipples shrunk into themselves and the way your little fingers froze at the edge of a page.
Your gaze lifts at the noise.
Just for a second.
And that’s all it takes. His eyes leave your chest to meet yours, brows furrowed and lips slightly parted. His chest was swelling and his cheeks were hot, hand pumping quicker as he locked himself to you.
You exhale sharply under your breath, heart thumping, dropping your eyes again and shaking your head just slightly at yourself.
This was just how he looked on the phone last night. This was how his chest stuttered and how his eyes fluttered open and closed. How his hand twisted and tugged at himself until his tip was a bright red, twitching in his hold as his balls tingled beneath him.
You press your pen to the paper again, writing something just to anchor yourself, even if it’s messy, even if it doesn’t fully make sense.
But you’re very aware that you’re losing the fight, little by little, every time your mind drags yourself back.
“Want you to look at me when I cum,” he breathes, “want you to watch my face.”
It really didn’t take much for you to agree. You dropped your pen and swallowed hard, watching his fist fuck down into himself in sloppy motions and strained veins.
His eyes dropped back down to your hanging tits as he brought himself to a close, pumping furiously and strangling his face. He quickly grabbed a tissue off of his desk and placed it right behind his tip, staring down at his own cock for a minute before looking back up at you.
He was so riled up and flustered that you felt faint, desperately squeezing your legs together for some sort of relief as you watched him reach his orgasm.
And with a long, drawn out groan and quick pinch of his eyes, his hand slowed and his body tensed, stilling as he came hard and intense.
It was the most beautiful sight you had ever seen in your life. You were even convinced he forgot you were there for a moment.
But he didn’t. Your being there only spurred his orgasm further, bringing him to new sensitivities that he really had only felt when he was young and naive.
He soaked into his orgasm for as long as he could, basking in the pleasure and pumping his length slow and concentrated. He looked so calm like this, even more than usual and so powerful before you. He had you stuck in his trance and you were in no hurry to get out of it.
As he came down, removing his hand and tugging up his briefs, he looked…breathtaking.
So breathtaking in a way that says he hasn’t quite come down from it yet.
There’s a faint flush across his skin, warmth still lingering from the effort, and his breathing hasn’t fully evened out. Slow, deep inhales that lift his chest before falling again, just slightly heavier than normal. A few strands of hair have come loose, sticking out just enough to show his behavior.
His posture is looser than usual, like some of the tension has been worked out of him but replaced with something quieter. Still there, lingering. There’s a subtle sheen along his skin, not overdone, just enough to catch the light when he moves.
You pick up your bra off of the floor and sling it over your arms as he regulates his breathing, his eyes still closed as you pull it up your shoulders and work at the clasp behind your back.
He drags a hand back through his hair, pushing it away from his face without really thinking about it, exhaling through his nose as he does. It’s not dramatic, not exaggerated—just the natural aftermath of exertion, where everything about him feels a little warmer, a little slower, a little more unguarded than before.
And then he looks at you.
Lazy and a little sleepy with that same smug smirk on his face.
He peers up at the clock that high on his wall before sitting up straighter in his desk, leaning over the wood as he looks at you in a firm glance.
“As much as I would love to play with you some more, my clients will be here soon.”
You frowned. Not on purpose, but it happened.
You know it’s not his fault, and based off of what just happened you know what he was telling you had some truth. But it was never a good feeling to get kicked out of a room after a moment of sexual vulnerability.
“Oh, right,” you nod, grabbing your shirt, “okay. I’ll send them in when they arrive.”
He notices it the second you stand.
That small shift in you—quieter than before, a little more reserved, like you’re pulling yourself back into something safer. Your movements are careful, almost too careful, as you button your shirt and gather your things and turn toward the door.
He watches you go. Not stopping you. Not interrupting.
Just… watching.
Your chest feels tight, like something’s sitting there that you can’t quite shake loose. You replay it immediately—every breath, every pause, every look—like if you go over it enough times, you’ll find the right way to process it.
You straighten a little, forcing your shoulders back, trying to pull yourself into something more controlled, more put together.
“Hey.”
You pause, glancing back over your shoulder.
He hasn’t moved much, still relaxed behind his desk, but there’s something lighter in his expression now. Not as intense.
“Don’t overthink it,” he says for the millionth time today, like he can see exactly what you’re doing.
Your fingers tighten slightly around the handle, and you give a small shake of your head, “I’m not.”
That earns a hint of a smile from his end. It was honestly unfortunate how hard it was for you to lie to him.
“Right,” he replies, not calling you out, but letting you know he sees right through you.
There’s a brief pause, just enough to soften the moment.
“Come back after my meeting wraps up, yeah?” He adds, tone ways, like this was just part of the routine.
It’s not phrased like a command. Not quite a question either.
Just like he already expects you to. Like he thought that was mutually agreed on but wanted to verbalize it in case it wasn’t.
You hesitate for half a second, then nod again, a small smile this time, “Okay.”
“Good.”
The weight in the room lifts—just enough to let you breathe a little easier as you step out and close the door behind you, his voice lingering a second longer than it should.
Good.
-
An hour has gone by.
He was still in his meeting.
You were sat at your desk, flipping through schedules and confirming cars and making reservations. As your day usually went.
But it doesn’t feel like working. Even if it was.
It feels like waiting.
Like every second has suddenly stretched out longer than it should, your thoughts filling all the space in between. You try to look normal—open a file, click through something on your screen, straighten a stack of papers that doesn’t need straightening—but none of it sticks. Your focus slips almost immediately, dragged right back to the same thought.
Come back after my meeting wraps up, yeah?
Your stomach flips and your thighs clench.
You glance at the time.
It should really only be a couple more minutes.
You exhale, leaning back slightly, then forward again a second later because sitting still somehow makes the pain between your legs worse.
Your fingers tap once against your desk before you stop yourself, pressing your hands flat like that might quiet everything going on in your head.
What is he even going to say?
Your brain doesn’t help.
It runs through every possible version of what could come next—some normal, some not—and none of them settle. Each one just makes your chest feel tighter, your thoughts faster, like you’re trying to prepare for something you can’t actually predict.
But every scenario has a happy ending. The promise of his touch and maybe even the treat of his cock.
He’s not gonna fuck you…right?
You don’t believe that.
You whimper to yourself at the thought of him nuzzled inside of you, that long dick you just stared at for so long lodged in deep and crashing into you repeatedly.
You swallow, glancing toward his office without meaning to, then quickly looking away like you’ve been caught doing something.
Your knee bounces once under the desk before you force it still, dragging in a slow breath that doesn’t quite steady you. You try to refocus again—pull up the document, read the first line, then the second—but the words blur together, meaningless.
You’re not here.
Not really.
You’re already halfway back in that office, stuck in the before of it, the waiting part that feels worse than anything else.
Your fingers hover over your keyboard, unmoving.
He’ll be done soon.
You exhale slowly, pressing your lips together as you stare at your screen without seeing it.
“Get it together,” you think out loud.
But your thoughts don’t slow.
If anything, they just keep racing—faster, louder—the closer it gets to the moment you have to stand up and walk back in there.
Voices spill out first, polite goodbyes muffled behind the door, the scrape of chairs, the soft shift of movement in his office. You look up just in time to see the group filing toward his office door.
And then he appears.
He’s already in motion, walking them out himself.
Calm. Composed. Completely in control of the space without needing to announce it. You watch as he shakes each hand in turn, exchanging brief, professional farewells, standing just in the doorway.
There’s something about the way he carries it all so effortlessly that makes you sit a little straighter and rub your legs together without meaning to.
One by one, they step out.
A final nod. A last polite smile. And then they’re gone.
And it’s just you and him.
The room quiets almost immediately after, like it’s exhaling itself.
He doesn’t close the door, he leaves it open.
For a second, he just stands there in the frame of it, glancing back into his office, and then straight to you.
It’s quick. Subtle.
But unmistakably meant for you.
It wasn’t a call, and certainly not a question. It never was with him.
Just a look that says now.
Then he turns and walks back inside. Like there was never any doubt you’d follow.
You hesitate for only a second longer than you should, then push yourself up from your chair, papers forgotten for the moment, and start across the room. Each step feels louder than it should.
By the time you reach the doorway, he’s already inside again, moving toward his desk like he hasn’t even looked back to check.
He doesn’t need to.
You’re there. He knew you’d be.
And as you cross the threshold, you feel that shift again. The quiet pull of the space snapping back into something private, something smaller, something that suddenly feels so wrong and so right.
He glances up just as you enter and watches as you shut the door behind you.
“C’mere,” he gestures, “I need you to summarize these notes for me.”
You nod immediately, trotting over to the desk and standing by the edge as you flip through the scattered writing.
You’ve gotten ridiculously good at reading his hand writing. No matter how sloppy it could get, which was bad sometimes, you had read over it so many times that you could translate in your sleep.
“Ok,” you nod, leaning into the desk a bit, “anything specific you want me to focus on? Or just brief overviews for all.”
“No,” he calls from behind you, “however you want to do it. I trust you.”
You cant ignore the hiss in your stomach at his praise.
You start scanning through his notes, trying to piece together the structure of the meeting from the shorthand he left behind. It’s messy in places—quick, efficient, not meant for anyone but him—so you’re translating as you go, quietly organizing it in your head.
You were good at this. He knew you were. It wouldn’t take you long.
You grab a clean sheet of paper from his desk and write up a quick header, underlining it two times before thinking out loud on how you’ll begin.
“Okay, so the first section is mostly basic overview, I can just trim it down to this middle section,” you start, more to ground yourself than anything else.
You hear him move before you see him.
A step closer behind you.
Then another.
You don’t turn around, letting the moment unravel until he’s close enough that you feel it more than register it. The shift in the air, the space behind you suddenly gone.
He leans in slightly to look at the page over your shoulder.
And then, his hand settles lightly at your lower back.
Not heavy. Not forceful.
But instead, sickeningly sensual. Like the one simple breach of space had broken you completely.
His hand was cold against your back, held so low and practically to the waist of your little black skirt. It was steady too, like it was barely a concern and more like a reflex.
Your breath catches instantly and entire train of thought disappears.
“I-um-” you choke on the word, your voice catching mid sentence like it’s been cut off. He loved to see you this way, and he knew you’d get like this too.
Your fingers tighten slightly on the edge of the paper, your posture going rigid without meaning to. Your mind blanks for half a second—completely empty—before everything rushes back in all at once.
Awareness.
But too much of it.
You’re suddenly hyper aware of everything: how close he is, the cooling shock of his hand through the fabric, the way you can feel his presence right behind you without even looking.
The way his front was inching increasing closer to your back, the front of his thighs grazing against the back of yours accidentally. Or at least you thought it was accidental.
“I was just—gonna go over, um..” you try again, but it comes out uneven, your words stumbling over each other.
You swallow, forcing yourself to look back down at the notes, even though the words blur the second you try to focus on them.
His hand drifts lower, curving over your ass gently.
“Um, the second part was mostly about—about timelines,” you manage, your voice still not fully steady.
Your heart is beating a little too fast now, your thoughts scrambling to catch up while also trying very hard not to drift toward the one thing you’re actively avoiding thinking about.
His hand doesn’t move for a moment. It stays firm over the curvature of your ass, holding solid pressure with his finger tips in a way that almost feels like he’s grabbing it.
And then he shifts lower. So low that he reaches the hem of your short little skirt, pressing his body closer to yours as he stood behind you.
You pause as you wait for him to slip underneath.
But he doesn’t.
Not immediately.
And that somehow makes it worse.
You inhale quietly, trying to steady yourself, forcing your brain back into something functional, “And then they shifted into—uh—budget adjustments,” you continue, a little more quickly now, like speed might help you regain control.
Your hand jots down a sloppy outline of the words you say, helplessly thin to what he had asked if you.
But the effort didn’t matter. It would all be thrown to shit. Because when his fingers slipped low off of your skirt and made contact with the bare skin of your ass, you lost it.
Close enough to where you needed him most that your thoughts won’t fully cooperate.
And you’re very aware that you’re trying to act like it isn’t affecting you at all.
So is he.
But he finds it endearing. You’re cute when you act like you’re stronger than you are. He had to hold back a smile at the way you continued to try and work, to do as he asked because you were sure to never fail him.
“Um, I’ll put any numbers in a chart to the left for you,” you muster out, taking a deep inhale as his fingers continue to drift.
Your back curves inward without thinking about it, pressing your ass out further into his hold and shuttering at the feeling.
And then, with the fabric against his palm, he shrugged it upwards in a smooth motion. All the way up until the loose skirt rested on your waist and your ass was bare and exposed in your little black thong.
You choked.
He goes still for a second behind you.
Not the usual kind of calm stillness, this is heavier, almost reverent, like now you’ve really caught him and there’s no way for him to get out.
“…fuck,” he murmurs, soft and almost absentminded.
You barely have time to process it before you feel the lightest shift—his hand moving, not leaving completely but easing just enough as his focus drifts towards the space between your legs.
His fingertips brush lightly over the fabric of your underwear, slow and careful, like he doesn’t want to disturb it.
It’s not rushed.
Not distracted.
It’s deliberate in a way that feels… different. So intense and slow that it’s suffocating.
His touch grazes over the surface—barely there, almost thoughtful—tracing along a line, then pausing, then moving again like he’s following something only he can see.
“So…soft..” he starts, then trails off, exhaling softly instead.
You were soft. You were young and smooth and everything was just as it should be. It’s been awhile since he felt this gifted. Like you had granted him something that no one could ever deserve.
And then he pressed his middle finger right onto the damp spread of your thong, applying a light pressure and sighing at the wet fabric.
A breath slips out of you before you can stop it.
Soft at first—then it deepens into something heavier, your chest rising and falling in a way you can’t quite control. It’s not loud, but it feels louder than it should in the quiet room.
Your fingers tighten slightly against the desk as the feeling settles in, unexpected and hard to ignore. It moves through you in a quick, subtle wave—enough to make your shoulders tense before they ease again.
“You’ve gotten yourself all wet for me. Good,” he sighs, lips up to your ear as his finger continues to explore the hot area. He slips himself up and down your clothed slit, pressing firm and keeping himself behind you against his desk.
You draw in another breath, sharper this time, like you’re trying to steady yourself, but it only half works.
A faint shudder follows—small, but noticeable—running through you before you can stop it. You straighten almost immediately after, like you can recover from it if you move fast enough, if you just act normal.
You’re acting like you’ve never been touched before in your life. Like this was your first experience being rubbed over the blanket of your thong. It honestly was embarrassing that you were this riled up without him even really touching you.
But then he does. Sudden and seemingly out of nowhere, sliding the thin panties to the side and letting the cold air of the room sting against your needy clit.
Your head falls, arms stabilizing themselves with a bit more effort as your hip bones pressed against the ledge of the desk.
Suddenly, there’s an absence by your ear and by your torso where he once stood.
And before you can process it, you realize where he’d gone.
He was kneeling behind you, slow and teasing until his knees were bent in half and his hands were gripping either side of your waist. You were on full display in front of him, dripping pussy all swollen in front of his face and your body leaned over the desk just barely.
If you weren’t nervous before, now you were completely helpless.
“Relax,” he coos, “let me taste you.”
His hands brace against your upper thighs, steady, like he’s anchoring himself there.
Your breath holds deep in your chest.
He takes his time—too much time—and that’s what throws you off. Nothing rushed, nothing careless. Just slow, deliberate movement, as if he’s completely unbothered by the way the moment stretches.
He was basking in the sight of your pretty pussy in front of him, so tight and puffy and dripping down your thigh in a desperate plea.
He lets out a small breath against you, slow, relaxed, hot.
You feel it more than you hear it, and it hits the space between you in a way that makes your thoughts stumble.
Your body reacts before you can stop it—a small, involuntary shift, your weight moving from one foot to the other like you’re trying to settle and can’t quite manage it.
And then, his tongue presses flat against your throbbing clit so firm that you nearly faint.
Your shoulders drop first, just slightly, like your body doesn’t fully trust it yet.
Then more. A lap around the bud. A subtle press into your hole with the tip of his tongue. A sigh that stems deep from his chest at the sweet taste of you on him after all this time.
Another breath leaves you—longer than it should be, heavier. You really had been holding it in without noticing. Your eyes fall shut, not on purpose, just because it feels easier than keeping them open.
You don’t have to think.
For the first time in what feels like forever, your mind actually… quiets.
He hums into you as he continues to lick you up, sucking on your swollen clit and lathering yourself around him.
Sure you’ve had a man between your legs before. Sure you’ve felt the warm sensation of a tongue slung inside of you and swirling around mindlessly.
But this was different. He’d been down there, on his knees, for nearly three minutes and you were already steeping your way to a release.
The tension on your clit eases, then spreads, unraveling through you in slow waves. It’s almost overwhelming—not in a bad way, just in that finally kind of way, like your body doesn’t know what to do with the absence of the sexual build from the last 12 hours.
A soft moan falls through when he nuzzles his face back and forth into you, groaning against your clit as he licked another run of your honeyed arousal.
You sink into it without realizing, letting yourself go a little more with each passing second. You’ve stopped bracing for something and just decided to accept it.
Everything feels warmer. Looser. Lighter.
And for once, you’re not forcing yourself to stay composed, not pulling yourself together, not fighting your own thoughts.
Instead, you’re just falling completely undone. Quaking against the desk as you fight to hold yourself upright, bending further over without thinking and pressing your ass further into his face.
And he loved it. He’d have your ass and your delicious pussy suffocating around him for days on end. Willingly. If anything, he’d beg.
You sucks harder at your clit, enough to the point where your legs start to wobble and your moans tangle within each other. Your torso leans further into the desk, now halfway bent over as you press your core into his face unknowingly.
“That’s it,” he hums, “Feels good, doesn’t it?”
“Mmm—” is all you can press out, knuckles whitened as you grip the desk and hip bones aching in their pressure against it.
Then, without warning, your hole fills with the sudden stuff of his two thick fingers. Thick and gritty and curling up into you like it was where they always meant to be.
“Ah—fuck!”
And you feel it. His smirk. Curving up against your wet pussy and leaving a trail of egotistical success.
“Hm,” he tuts, “that’s what you needed? My fingers?”
He was having fun now, watching you unravel and fall vulnerable in front of him. He only wished he could see your pretty face, so red and twisted and worked up.
“Y-Yes! God, yes, feels so good, Mr. Styles,” you groan, deep from your chest like it’d been trapped there for longer than you knew.
You don’t know why you call him that. Yes, you always have. But never when his face is shoved deep into your cunt and his fingers are jutting into you remorselessly.
But he likes it. He likes your undying respect and the way you worship him.
He also liked the reminder that this was a bad idea. The thought of someone walking in and seeing his assistant ass out over his desk had him aching in his pants for a second time today.
“Yeah? You gonna cum on my face? Get me soaked?”
It was his way of saying please, fucking suffocate me and drown me in your cum till I choke.
But he had a reputation to uphold.
So he kept that part in.
“Mmm, mhm,” you whine, leaning even further over the desk as your head untwists.
He felt how close you were, measuring the clench of your hole around his fingers and the slight vibration of your thighs that echoed through him.
His thrusts quickened, his lips sucked harder, and you were putty. Melting around him until your tummy bubbled with that familiar heat and your breaths stilled.
“I’m-I’m gonna—”
“Mm, I know, baby,” he hums, “do it.”
And as all of his asks went, it only took you half a second to comply.
You were shaking around his head as your orgasm flooded over you, coming in waves and leaving you frozen in front of him.
Your body stilled, your breaths held, your face reddened.
A light, floaty dizziness rolls through you, harsh and overwhelming. Your limbs feel heavier, but not in a bad way—more like they’ve finally stopped trying so hard to hold you up. There’s a loose, almost weightless quality to them, like you could stay exactly where you are and not move for a long time.
But then he keeps going.
Quicker.
More intense.
“Ah—I’m…” you trail off, twitching at the feeling of his tongue on your clit and the way his lips wrapped around it tighter.
Your body tenses instinctively, like it doesn’t know how to process it yet—your breath catching, your shoulders tightening, your fingers curling slightly as you try to hold steady through it.
It almost hurts.
Not sharp exactly, but overwhelming in a way that makes you pull in on yourself for a second, like you’re bracing against it.
“It’s too much,” you breathe out, twitching around him and falling further into the desk.
He just continues harder.
Your mind stumbles, trying to make sense of it, but there’s no space for clear thoughts. Just sensation, heavy and all at once, pushing past what feels comfortable.
“Breathe,” he sighs into you, “it’s not too much. You like it. Don’t act like you don’t.”
You inhale, a little shaky.
And then, it shifts.
Slowly at first.
That tight, overwhelming edge begins to soften, the intensity spreading out instead of pressing down. Your body starts to give instead of fight it, the tension easing little by little as you realize it’s not something you have to resist.
Your shoulders drop.
Your grip loosens.
The pressure that felt like too much just seconds ago turns into something warmer, something that settles into you instead of against you.
Another breath leaves you, longer this time.
“There we go,” he nods as he presses deeper inside of you, clit stinging and pulsing and swarming over you in new pleasure.
You let out a soft breath, almost a quiet stutter under it, like you don’t even recognize yourself in the moment.
“I’ve… never felt— it feels so good,” you admit, your voice a little lighter now, a little dazed around the edges.
It sounds strange even as you say it.
But it’s true.
You've never had a man bring you to an orgasm as quickly as he did, and you’ve never once had a man continue even after you’ve finished. Pushing you to your limits and watching you adjust based off of his preferences.
You shift slightly, still settling into that lingering warmth, that looseness that hasn’t fully left your body yet.
“I’m—shit,” you add, softer this time, like you’re still trying to process it.
And then you feel it, the rise of your second orgasm coming only within a couple moments from your last. Heavier this time, more intense than anything you’ve ever felt and taking up the whole of your body.
“Feel good? Tell me how I make you feel.”
Your voice drops, quieter, more honest, “so good, Mr. Styles. Thank you, it feels so good.”
He groans into your pussy, drowning in your respect and admiration and the way you were always so grateful for him.
You exhale slowly, sinking into the feeling again, like you’re chasing the last of it, hoping it doesn’t fade too quickly. Your shoulders stay relaxed this time, your body not fighting it anymore, just letting it settle wherever it wants.
“C’mon, you’re right there, give it to me again,” he whispers, licking quicker and curling into that spongy spot that has you spinning around yourself.
And in normal fashion, your mind agrees to his request immediately and your body follows with it. You shatter against him again, tensing and groaning and filling the wide office with the erotic noises of your pleasure.
He didn’t care if you got caught. He was floating with his tongue on you. There wasn’t anything in this world that would stop him from finishing the rest of your orgasm, the noises and the tensing too much for him to deny.
Your stomach falls completely flat over the edge of the desk now, cheek pressed against the wood and ass up high in his face. Your feet struggled to stay grounded as you bent in half, completely losing control of yourself and sinking into it all.
This was what he wanted. He wanted to watch his perfect little thing finally relax. You were always so tense, so eager to please him and always trying your hardest.
And yes, it was his favorite thing, to watch you try for him. Sweat for him until he was more than satisfied.
But this was different—new. You were loose, dropping your walls and showing him vulnerabilities you would’ve never dared to do in front of him.
And when he pulled his thick fingers out and finally removed the suction on your clit, you slipped into a breath of relief.
“Ok?”
“Mhm,” you nod against the desk, “ok.”
He stands from his spot on the floor, running a hand up your back until it lands on your shoulder. His face falls to the side of yours, lips near your ear as he rubs gentle circles onto your skin.
“M’gonna fuck you now,” he whispers, “slow and deep until you beg me for more.”
He flips you gently to your back before he continues.
“And I wanna see your face when I make you cum again.”
He says it so simply it almost passes like any other sentence, but you knew it was coming. Or at least part of you did.
Still, hearing it out loud makes your breath catch just a little. The way he casually lets you know that he’ll be fucking you now. Making you cum for a third time. Your boss, his assistant.
You don’t look at him right away.
Your eyes drop instead, a small, almost automatic reaction, like you suddenly don’t trust yourself to hold his gaze without giving something away. Like you feel it’s almost embarrassing how excited you are.
There’s a warmth rising in your face you can’t stop, spreading slowly, settling into your cheeks.
You nod.
Small at first. Then again, a little more certain.
“Okay,” you say quietly, your voice softer than you meant it to be, still recovering from what he had just put you through.
He smiles when you say it, a real smile, endeared at the sweet nature of your acceptance and the way you laid out on his desk in patience.
And once he gets the urge, he can’t stop himself.
He’s leaning down into you, quick, as if he doesn’t want to give himself time to rethink it, before his lips are on yours. Slow, careful. Like if he kissed you too hard he might just break you.
There’s a pause where you feel it—your own reaction, the way your chest feels a little lighter, a little warmer, like something just settled into place.
Everything felt peaceful for a moment. Like the heavy tension of what had started had faltered for a moment and instead turned into something domestic. Personal.
You bring a hand to the back of his neck without really needing to, just to have something to do, still not quite settling into it yet.
But there’s a faint smile there. Subtle. From both of you, unintentionally.
Like you’re trying to keep it in, but it shows anyway.
And when you finally pull back, it’s quick—just for a second—before you both fall back into each other, that same cohesive mesh, like you don’t need to say anything more.
His lips were soft and full against yours, coated in the residue of your last orgasm but you don’t mind. You tasted him through it. The deep mint, the strong patter of his tongue. It was intoxicating, and by the way he was kissing you back, you could tell he was feeling the same.
The two of you start to strip as you continue the kiss, your fingers working to unbutton your shirt once more and his undoing the buckle of his belt. His pants came next, then his shirt, falling down his arms and joining the others.
He shrugged your skirt down and off your legs, leaving you bare in just your bra which soon came next.
It was hasty, but tasteful. Slightly sloppy but also controlled, how it always was with you two.
And then you were both naked, your back pressed against his desk, his lips on yours and a hand tangled through your hair.
“Please, Harry,” you whispered, the first time you’d called him by his first name since the day you started working for him.
And that did it.
“Oh, y/n,” he kissed you deeper, a hand coming down to grab his own length, “been thinking about this for so long. So good to me, all the time. Want to give you what you deserve.”
You whine, slipping your tongue through his lips as he positions himself deeper between you. Your legs wrapped around his waist, his left hand holding your leg stable as his right works to align himself with you.
And once he presses in, slow, teasing, you freeze.
He was thick. So warm and inviting as he slid into your slick with the precision of a man who cares. Who cares about your pleasure and waits to work off of your reaction.
He was analyzing you as he pressed deeper, listening to little noises and pulling back from your lips for small moments just to glance at your expressions.
You felt so full, overwhelmed in the pressure but reveling in the feeling all the same. He was so thick and ridged inside of you, pressing past the tip and further to his base with every passing second.
“Tell me what you’re feeling, y/n,” he breathes out, “need to know if it feels okay. Don’t wanna hurt you.”
You shake your head immediately.
“No, feels so good, don’t stop, please,” you stuttered through a breath, legs tensing around his waist as your tits melted outwards as you laid on your back.
With that, he bottomed out, hips melding into yours in some smooth motion until you were both groaning out into each other.
He starts slowly, rolling in and of you in a loose rhythm that was contained in the way it should be.
You exhale in a wave of pleasure, shoulders loosening as you sink into it again. It’s not overwhelming like before, just steady, lingering. Full in a way you couldn’t quite describe.
Your thoughts quiet on their own, slipping into the background like they’re no longer needed.
You shift on the desk slightly, more comfortable now, not searching for where to put yourself anymore. Everything feels easier—your breathing, your hands, even the way your mind moves.
“Harry,” you moan, “Feels so good inside of me.”
He was sweating already, overwhelmed in the feeling of his thick cock nuzzled deep inside of your little pussy and not quite knowing how to process it.
“Yeah? You like my cock inside of you? This how it felt last night?”
You shake your head messily, “Mm-mm, no. Never as good as this, no.”
His pace quickened, just barely, but enough to give you a hint into what it could be.
Rough. Sloppy. Aggressive.
And suddenly, you needed it that way.
“Please, harder,” you groan, the words slipping out of you before you can really even think about it.
“Hm?”
“Harder, Harry, please! Fuck me harder, please, I want it,” you were tensing around his cock on purpose, prying for him in any way you could.
“What do you want?” He played, stretching you thin until you were a desperate mess.
He just didn’t expect it to come to him so easily.
“Your cock, please, I want it to hurt,” you yelp, “fuck me harder, Harry, please, I need it!”
He growled, squeezing his eyes shut to hold himself together at your filthy pleads. You were a wreck, already so worked up and he had barely fucked you yet.
Not properly, anyway.
With a huff, he paused his gentle rhythm before grabbing onto your left ankle, throwing it up on his shoulder until it slung there naturally.
You gasped at the shift, the difference stretching you out and letting his cock kiss your insides in a new way from before.
“Mm, f—”
You were cut short at the sudden slam of his hips against yours, rough this time and leaving little space for you to process a thing.
He was harsh and unforgiving as he slammed his way into you, again and again and again and again until you were drunk and dizzy with his dick and your eyes were to the back of your head.
“Oh, Harry! Fuck, yes! Yes! Yes!” You were ridiculously loud, neck strained as you grasped onto nothing in an attempt to steady yourself against the solid surface of his desk.
“Yeah? You like this better? Tell me you like it rough,” he groans, sweat forming on the line of his curls as he ruts into you harder.
“I do, fuck! Feels so good, so deep,” your words sounded like nonsense, thoughts rambling out of you with little to no processing time.
He presses his palm flat against your lower stomach, slapping onto the space where his tip tented the skin of your tummy and groaning at the feeling of him so deep in your insides.
He grabs your hand and places it on your stomach with his, watching as you now also feel his cock jutting in and out of you and pressing up into your skin.
“You feel that? You feel my cock fucking into your belly? S’where it belongs.”
“Mm, yes! Fuck, so good, don’t stop,” you were already close, and he hadn’t even touched your clit.
He wasn’t going to, either.
He wanted to know his dick was what made you cum. Nothing else.
He fucked you harder, deeper, every passing second growing more and more intense and even more aggressive.
You were…in heaven.
You’d dreamt of this for god knows how long. You knew he’d be the man to do it. He was big and strong and fucking you just right and handling you like the little thing you were.
“Tell me how good this dick is,” he spits, shoving himself deep into your cervix.
“It’s—it’s…shit,” you tried, really, you did.
But when he was slamming himself into you the way he was, table rocking and wooden legs squeaking, who could blame you?
And when you thought he’d be patient, let you take your time, you were slapped right out of that thought the moment you felt the chill of his rings around your neck.
His hand had you pinned down, gripping tight against your veins until your face reddened and your throat felt raw in ecstasy.
“Fucking say it,” he grits, “tell me how good it is. Tell me what you want.”
You were spinning above yourself, swarming in the mix of the stretch of your leg over his shoulder and the grip on your throat and the slam of his hips.
“So good! Fuck, your dick is so good Harry I need it. Want it all the time, please, want this cock everyday, all the time.”
You were rambling, but not in the way you did when you were nervous to send over his weekly schedule.
This time was different.
You were rambling like there was no end in sight. Like if you weren’t so distracted by the fuck of his hips than you would continue on and it would never stop. Just raving about how good he felt inside of you and how you wanted it forever and ever.
“Good, baby,” he hummed, “so fucking good to me, you know that? Never let me down, never. You’re perfect, so good for me all the time.”
You whimpered at the praise, his grip tightening against your throat as you struggled to keep your eyes open.
“And now you're taking me so well,” he continued through heavy breaths, “so tight around my big cock, hm? Best pussy I’ve ever felt in my life, you’re fucking unreal.”
And that was it.
He should’ve known it would get you there—how could it not when this is what you lived for? His praise, his words, the reassurance that he was happy with what you brought to him. That you were worth his while.
More than worth his while.
“Harry! I’m—”
“I know,” he quickened his pace, “let it out. Squeeze my cock till it stings, make me cum.”
You screamed, legs clenching and extended up around him and mouth falling open in pure bliss. It was the hardest you’ve ever come in your life, so wrapped up in the moment and pulling from the lack of blood to your head.
His grip on your throat loosened a bit as you came, giving you room to breathe and steady yourself so as to not pace out right on his desk.
Because that would be hard to explain to someone.
He replaced his dick with a thumb on your clit to help you ride it out, not wanting to cut it too close as he was there himself now and wouldn’t risk cumming inside of you.
No matter how badly he wanted to watch his insides drip out of your swollen hole.
“Fuckkk,” you groaned deep as he stroked himself onto your stomach, letting it paint your milky tits and drip down to your belly button in a careless fashion.
You both watched each other's faces—the way you curled and squirmed and tensed at every new dash of a feeling. It was so intense, so wrong, so good in the way that felt like it had to be a dream.
And because you just couldn’t help yourself, as you come down from your last orgasm, you swipe your finger up your stomach until you gather a healthy helping of his cum and press your finger onto your tongue. Lapping up the salty liquid until it hit your throat and you were humming in satisfaction.
He twitched at the act, still stroking himself out and groaning at your fucked up behavior.
You would be the death of him.
He lets grabs your ankle and takes your leg off of his shoulder, sighing as his head drops and he catches his breath.
You follow the same pattern, regulating your breaths and shutting your eyes in an attempt to revive yourself.
You both end up looking at each other at the same time.
There’s a beat—just a second—where it’s quiet.
And then it breaks.
A breathy laugh slips out of you first, soft and loose, like it just falls out without asking permission. He follows right after, the same kind of laugh—easy, unguarded, like neither of you has the energy to hold it in or question it.
It’s not in humor. It’s more in bliss. Like you both just can’t beleive how fucking good you feel and how fucking insane you both are.
It feels a little unreal, like you both just came out of something you weren’t expecting to feel that deeply.
There’s that shared look again.
Tired.
Relieved.
But happy. Really happy.
Your shoulders feel heavy in the best way, like all the tension finally burned off and left nothing behind but this loose, quiet calm. His posture mirrors it, less rigid, more open, like what just happened took something out of both of you, but gave something back too.
You peer up at the clock on his wall before looking back at him.
You exhale, still smiling, softer now.
“Your 12:00 will be here soon. I’ll let them in once you’re ready.”
He lets out another small laugh, shaking his head once like he doesn’t even have the words for it.
And for a second, neither of you tries to fill the silence. Because you don’t have to.
“Mm,” he leans to kiss you for just a quick second, “perfect.”
You shift slightly, exhaling under your breath. Looking at him through his flushed cheeks and his lazy smile. His messy hair and the way his body seems a little less tense than it usually is.
He’s satisfied.
And that thought sits comfortably. Like a box checked. Like something resolved.
Good.
That’s what matters.
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love u all sm! thx for ur patience w this one and I hoped it lived up to the expectations!!
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