“ ᴀssɪsᴛᴀɴᴛ ᴏʀ sʟᴀᴠᴇ? ”
( іmᥲgᥱs ᥒ᥆𝗍 mіᥒᥱ, ᥴrᥱძs 𝗍᥆ ᥆ᥕᥒᥱrs ++ ᥲr𝗍 ᑲᥡ @rіmrі4mm )
— ceo!caitlyn x assistant!reader
Caitlyn Kiramman had a long list of assistants that either quit or were fired within a week, due to her dramatic and draining commands — they all hated how needy the CEO was.
But you? No. You were her new assistant. This time though, you weren't going to make any mistakes and for sure you weren't going to give up. You needed the money! It should be easy, right?
tags: office au, modern setting, caitlyn is kinda a brat, dominant caitlyn, top caitlyn, afab reader, very submissive reader, power play, reader is very pathetic, smut, desk sex, oral sex(r!receiving), dirty talk, slight insulting, biting, men dni and minors dni
(wc: 3,833k)
Caitlyn Kiramman, the CEO of the highest-selling company of all of Piltover. She was known for her knowledge and skills in business and trading, her expertise is what led her to be successful and at the top.
To most eyes, she was seen as a kind and caring woman who wanted nothing more to help the public with her wealth. But to your eyes, and every other employee she's ever had, she was the complete opposite of that.
Instead of being an angel, she was a devil. She had a ‘perfectionist’ mindset which meant everything had to be flawless or you'd be out of the door as soon as you made one tiny mistake. Her employees acted as mere pawns in her game, easy to hire and definitely easy to get rid of.
Yes, it was difficult working under her name as an employee. But, it was harder working as her assistant. Caitlyn Kiramman had a long list of assistants in only a year, and it was known that they've never lasted a week with her — more so, the longest one she's ever had was a month.
Unfortunately for you, you were the next one on that long list. You had just been hired, and you were really happy to know that you achieved such a high role on your first try. Well, that is, until you heard the rumours of dealing with her wrath in the front seat.
There's a reason why all of her assistants quit. Most of them deemed her as too ‘demanding’ and receiving many, many and many commands from their CEO.
Apparently, you were basically a slave under her command. Her commands were so ridiculous, that you've heard rumours of one assistant being forced to give Caitlyn a full body massage one time — that must've been fake, right?
It was terrifying even thinking about it, working as her new assistant. Honestly, you were probably going to deal with the same fate as all of them. To suffer, to be taken advantage of and to be discarded as easily as every assistant she's ever had.
It was her hellhole.
But you had to endure it. You were in debt and the job paid surprisingly well, one paycheck would pay for three months of your rent! The job was simple, anyways. Listen. Or you'd be out in the streets begging for scraps, you needed this job really bad even if it was embarrassing and exhausting.
“I don't assume that I need to inform you about how this job goes, hm?” Caitlyn sat on her office chair, tapping a pen on her temples as she stared at you down. “Yes, Ms. Kiramman.” You bowed slightly, trying to look as composed as you could.
The rumours turned out to be true, she had a glare that looked intimidating as ever — it made your knees go weak and you wanted to apologize for existing. You were quivering in your shoes while you stood directly in front of her, not daring to speak a word until she told you so.
Caitlyn sat still on her chair, working on some files. The rumours all said she was a terrifying, mean woman so you expected someone old and raggy — not a woman in her 20’s.
Even with such a rude personality, you couldn't admit that she was attractive. Navy-blue hair that swayed through the breeze of the aircon, glasses that rested perfectly on her nose, a uniform that clung onto the curves of her body paired with a miniskirt and stockings. She was the definition of Piltovan elegance, you were starstruck and couldn't stop staring at her face.
“I have an appointment today,” She hummed, finally acknowledging your presence with her eyes. “Carry those papers for me, will you?” Her figure stood up, walking to the exit of the huge office before slamming the door shut without waiting for you.
A scoff went past your lips while your gaze drifted to the pile of papers she was talking about, a tall stack of them that you had to carry all by yourself. You sighed, before picking it up one by one and balancing it carefully.
You walked outside of her office, trying your best not to drop any of the important documents. Suddenly, you realized that you didn't even know where Caitlyn was having her meeting! She just… left and assumed that you knew, how rude.
The tower of papers rested on your hands as you saw another employee beside you, drinking a cup of coffee.
“Excuse me, do you know where Ms. Kiramman is having her appointment?” You asked him, one of the papers falling down. Your hands reached for it, bending down and placing it back on the stack clumsily. “In the meeting room, on the left side.” He responded, a cheeky smile on his face.
You thanked him, balancing the papers as you followed his directions. Suddenly, his hand patted your shoulder. "Good luck new assistant, you'll need it!” He winked, snickering while he walked away.
A sigh escaped your lips at his words. Great, you were already being teased on your first day. “Whatever.” You muttered, walking to the meeting room. You couldn't let his words get to you, after all, you were going to survive as Caitlyn Kiramman's assistant — you’ll be the first one to actually make it within a year, well hopefully.
Knock! Knock! You knocked on the door of the meeting room, spotting multiple silhouettes of people through the vague window. “Come in!” A voice shouted out, cheery.
You opened the door to the office, still carrying the stack of papers in your hands, poorly balancing it. “Wonderful timing!” Caitlyn chirped, urging you to place the papers on the table with… politeness?
Her previous intimidating stare was now replaced with a completely different one, a kind and inviting smile. More so, she was very polite to you unlike earlier this morning where she barely acknowledged your presence.
You now realize that this is definitely the reason why many people see Caitlyn as an angelic woman, rather than the terrifying one behind closed doors. It was annoying you at how good she was in playing the ‘good cop’ role, already capturing the group of businessmen’s hearts as they laughed at her jokes.
“Thank you, Y/N.” She grinned, patting your back. “You're dismissed for today.” Her voice was gentle, smiling before drifting her attention back to the group of businessmen.
For the next few days, she's been like this. From being an absolute demanding woman in the office to acting like an angel in meetings. You didn't mind it, it wasn't that bad — you just had to survive a few hours doing her chores before she turned all Ms. Nice Guy on you.
Well, that is until she got comfortable with you. Instead of dismissing you as usual during her meeting, she called you to sit beside her, giving you a towel. “It’s burning up in here.” She declared, staring directly at you.
At that statement, you knew exactly what she was implying. Your gaze averted to the drop of sweat rolling down her forehead, Caitlyn looked over back at you with an expectant expression.
You suppressed a groan about to leave your mouth, before your hands grabbed the towel and started to wipe softly at the sweat formed on her face. She continued talking about business stuff you didn't understand as you gently wiped every inch of her face — even going far enough to wipe the back of her neck.
Then, when you were satisfied, you grabbed a nearby book that wasn't being used and started fanning her. The corners of her mouth perked up ever so slightly, barely noticeable if you weren't paying attention as she darted her eyes to your DIY fan and returned it back to the group of business.
The rest of the meeting, you were restless. Your hands never stopped moving and occasionally you would wipe more sweat off her face, like she was royalty. You were growing tired, considering the fact that you haven't taken a break.
Annoyance tugged at your heart but then your gaze drifted to her lips, forming a divine smile. You knew it was fake, only forcing it onto her face for the business deals and how she was only playing a role to convince the businessmen. But, somehow, she's managed to lure you into her stupid trap.
A faint blush crept up your neck as you were suddenly aware of the actions you were doing, you were really close to her face while you wiped more sweat — taking in how her smile-lines showed when she put on that fake smile, that stupid charming smile that made you flustered. You were basically wiping the sweat off of a Goddess. It was frustrating, everything about her!
From how demanding and petty she can get from how your anger dissolves as soon as she smiles in the meeting room, you were supposed to be pissed at her for treating you so poorly! But.. a part of you liked being commanded, especially if it was Caitlyn doing it.
You were falling exactly into her trap.
For the next few days, she's grown bolder. You've established a routine of immediately clocking in and brewing Caitlyn’s jasmine tea.
Then, you would go to her office to help her in whatever she needed for the morning. Whether it was massaging her shoulders or fixing the wrinkles on her uniform — you swallowed your pride and followed.
It wasn't like last time where you had to survive the morning. No, you were by her side the whole day. Every second she would call you and ask you to do something in front of all the co-workers, it was embarrassing but you needed the money.
More so, since her demands have grown to be bolder, that requires you to be physically closer with her. It drove you mad, whenever you massaged her shoulders as she worked — she intrigued you, huffing in frustration while you soothed her muscles.
Sure, it was tiring doing this. But, you've adapted somehow even if it was really, really humiliating and most of your dignity is probably already gone.
Today, you were starting your ritual of brewing Caitlyn's jasmine tea in the break room, making sure everything was perfect for her taste.
You cut across through the crowd of co-workers, receiving nods of appreciation. Unlike last time where you were being teased, it felt good knowing that you've made it longer than others and that every one sorta’ respected your hustle.
“Ms. Kiramman, may I come in?” You knocked at the intimidating office door that wasn't so intimidating to you anymore. She replied with a faint hum, before you entered the office — taking in her usual position.
The jasmine tea was still hot in the teacup while you strode to stand in front of her working form. Your voice was quiet, trying your best not to distract her while you said, “Good morning, here's your tea Ms. Kiramman.” She nodded in response, a wrinkle seen on her forehead while she focused on her work, not even bothering to glance up at you like usual.
“Make sure it's the right temperature.” She ordered. You did as she said, blowing a soft gust of wind onto the steaming tea — making sure it's just right for her.
After a few seconds of pathetic blowing, you were satisfied. “It’s ready for you, Ms. Kiramman.” You muttered, about to place it on her desk until—
Splash!
Oh no.
Your hand slipped, forcing the tea cup to be tilted and fall onto the floor. Your gaze drifted down, praying that it didn't stain anything until you saw her luxurious boots were stained with a mud of coffee on top — leaking onto the quartz floor.
“I'm so sorry!” You gasped out, your hand coming to cover your mouth in fear. Those boots were probably more expensive than your life time, you were so, so dead and there's no way you're going to get out of debt — only further into debt because you had to pay for her boots! Unless…?
Her expression was filled with anger as a scoff went past her lips, a huge crease formed onto her forehead while her eyes widened, glaring at you with nothing but frustration. She opened her mouth to scold you, until... you knelt down.
You were quick to wipe the coffee stain with your clean, white uniform. It transferred the brown liquid onto yours instead. “You—!” Her protest was cut off when she saw what you were doing, using your own shirt as a tissue. For the first time, Caitlyn Kiramman couldn't form a sentence to save her life, she was astonished at how eager you were to clean your mess.
She scoffed again, before her frown turned into a smirk. Caitlyn made herself comfortable, leaning back on her chair and resting her head on her hand while she smirked at you — observing you like a wealthy person taking advantage of a peasant.
Well, that was basically what was happening right now.
You continued to wipe, and wipe while you were knelt down onto the floor. Your hand rubbed your shirt onto the stain in a circular motion, trying your best to remove the brownish puddle of coffee and if it was even possible, save your job.
It was almost gone, only a faint mud rested on the boots, barely noticeable but you still had to wipe it off — Caitlyn wanted perfection, you were determined to stay all night trying to wipe away the evidence of your clumsiness if you had to with your shirt.
While you continued doing your work, your knees aching from staying knelt down for so long, you felt her fingers tilting your chin up. “Enough.” Caitlyn commanded, her Posh accent compelling.
You were forced to look directly up at her, your neck hurting from arching so much because of her grip. But the view was… something else. One of her legs was crossed over another, the slightly stained boot in the air. Other than that, your position made it so that you could see every curve of her body — your mouth thirsted at the sight. She looked so powerful, especially with you knelt down at her mercy.
“I—I apologize Ms. Kiramman—” Your voice faltered, trying to defend yourself until her grip on your chin tightened. Her fingers squeezing your cheeks, forcing you to stop talking.
“You know your place, don't you?” She smirked, tilting her head while she continued to stare you down like you were a chew toy — her eyes darkening with lust. “I..” You trailed off, trying to speak but her gaze only weakened you.
Caitlyn let go of your chin, crossing her arms and leaning against her office chair but her eyes still remained fixated on yours, forcing you to stay in bound even if she didn't have a hold on you any more.
“You’re the only assistant I've ever had that's been so… obedient.” She raised her eyebrow, humming before she stood up and pushed her office chair away from you, the sound of its wheels rolling filling the tensioned silence.
Her figure crouched down, while you remained knelt down beneath her — Caitlyn still towering over you. Her long, ashen fingers caressed your cheek gently. “You’d do anything I'd ask you, wouldn't you? My little assistant.” She spat, taking a hold of your chin once again, this time it was tighter and filled with possessiveness.
She laughed at you, amusingly tainting her lips. You stuttered, not knowing what to say. Was she angry? Was she cocky? Or was she… turned on at your boot-polishing? Maybe it was all three of those options, you couldn't quite tell as she stood up again — waving her fingers lazily, gesturing for you to get up.
You followed out of instinctiveness, legs immediately getting up at her command. “Get on the desk.” Caitlyn pointed, her voice firm, making her intentions clear. This time, you hesitated — this was wrong, very wrong. Instead of sitting down on her desk, you cleared your throat, receiving a glare of unapproval from her.
“Ms. Kiramman, this is inappropriate…” Your voice was barely above a whisper while you whispered, trying to look not as needy as possible but the pool forming in your panties only continued to drip more at how she looked. “Do you want this or not?” She hissed, crossing her arms while she looked up at your body up and down.
Hesitation tugged at your heart, you wanted to scream 'No' at her because this was vulgar! If people found out that you were hooking up with Caitlyn Kiramman, there'd be horrible consequences, from her side and your side. But… her glare was making it harder to resist, you wanted this, so bad. She’s been nothing but a menace with her charm, indirectly teasing you every time she asks you to do something.
Suddenly, a nod came out of you. At that, you climbed on her desk and sat on the wooden surface — slightly groaning at how cold it was. Caitlyn smirked at that, her hands reaching back for the office chair she dismissed earlier and sitting down on it, hovering near your legs.
Without warning, she found the side of your hips, fingers unzipping your skirt. She dragged your skirt down, tossing it on the floor and her eyes took in your soaked panties — your arousal dripping onto her desk. “So wet for me and I haven't even touched you, pathetic.” Her warm breath ghosted over the fabric of your undergarments, fingers tracing your wetness.
She teased you, touching directly onto your clit through your panties but it wasn't enough to get you off. “Please, Ms. Kiramman.” You groaned out, looking down at her cheeky smirk. “Please what?” She tilted her head, raising her eyebrows.
It was cruel, how she was teasing you like this. “Please.. I need your touch, ma’am.” You cried out, before she hummed at your begging and removed your panties, tossing it onto the wooden desk with your glistening cunt all exposed and on display for her eyes. “Look at you.” She murmured, her breath hitting your slickness.
Now, your legs were sprawled out on the wooden desk, your bottom exposed as your top still remained on — Caitlyn not bothering to remove it as she licked her lips at your spread pussy.
Caitlyn licked your pussy, a moan escaping your lips as you gripped the edges of the desk for leverage. “Fuck.” You sighed while her eyes looked up at you from below, smirking at your reaction. Then, without permission, she shoved her tongue inside your vagina — lapping like a dog, the wet sounds of your arousal filling the room paired with your cries. “Oh!” You moaned out, your eyes shutting closed.
She started at a slow pace, licking while your walls took in her long tongue. This continued, soft moans coming out of your lips until she sucked your clit, the sensation turning your moans into a scream. “Ms. Kiramman!” You shouted out until her hand met your ass sharply, a red hand-print forming onto there.
Tears swelled up in your eyes at her slap, not expecting the harsh action. “Keep it down if you want to keep your job.” A growl vibrated through the inside of her throat, looking up at you with furrowed eyebrows until she caressed the area she slapped — soothing the sting there before she continued her sucking.
Caitlyn varied between sucking and licking. inserting her fingers at some point, stretching you a part as she put another finger and thrusted it in and out while her tongue did her work. “Ah.. Ms. Kiramman…” Your breath was uneven, barely keeping up with how overwhelming her fingers and tongue were.
Then, her fingers curled, hitting that spot at the new angle. “Mmgh, ngh! Ms. Kiramman! Oh, yes yes… please…” Her head bobbed up and down, meeting the pace of her fingers as she abused your g-spot — inserting another finger, stretching you wide open while you were getting closer, and closer to the edge with the dual sensation. “Oh, oh my god! Ms. Kiramman!”
Your walls clenched around her as your moans grew louder, she placed her free hand on your mouth in an attempt to keep you quiet. You bit it lightly, your saliva melting onto her hand while she smirked at how your teeth nipped on her hand — trying your best to keep your moans quiet as you were nearing your peak. “Getting feral are we?” She hummed against your pussy as you continued to use her hand as a gag.
Caitlyn noticed you were close, groaning while she was latched onto your pussy — the vibration humming through your vagina, the pleasure creeping through your spine as you bit down on your hand, muffling a scream. “I'm gonna… can I.. please?” You moaned in between each word, back arching off the table.
“No.” She ordered. “Hold it, until I say so.” Then, her pace increased rapidly — she didn't lick your clit anymore, only sucking it like she was a tornado hauling everything in. Other than that, she put her whole fist inside of you, filling your throbbing pussy as she continued to pound her fingers harder.
“Please, I can't… mmph.. hold it…” You whined, looking down at her with pleading eyes. “You're going to listen like the obedient employee you are..” She barked. It was all too much, you couldn't hold it… the knot building up inside you, your legs shivered at how much she was abusing your hole — you bit her harder this time, closing your eyes as you tried to focus.
“Go.” At her words, you cried out, “Oh my, fuck!” Your moan echoed through the empty room and probably heard through the whole office building but you didn't care, your orgasm crashed down as you rode out the aftershocks, thrusting softly into Caitlyn's face.
She pulled her fingers and mouth away from you, her chin soaked with your slickness. “Clean yourself up, I have a meeting.” At her words, you grabbed a tissue and wiped the evidence of your sex on her face and fixed her disheveled navy-blue hair before she gave a hum of approval — trying to suppress a smirk but the corners of her mouth perked up, betraying her while she fixed her glasses.
You finished cleaning her up, your ass still resting on the wet, wooden desk as you wore your clothes again. The sounds of Caitlyn's heels walking through the exit echoed through the room as you did what she said, cleaning her desk.
She paused her movements.
“This isn't finished.” She declared, her hand resting on the doorknob. “I haven't seen all of you yet.” A smirk formed on her lips before she opened the door, the sound of it slamming echoing through the room. You were left alone, with the faint scent of sex still lingering and a soaked mess to clean up.
a/n: alright so i've been obsessed with office aus and srry if this is rlly bad, i quite literally wrote this while i was on a plane so... i had to hide my screen from the people beside me LOL. but, i will definitely write an epilogue or continuation of this — just something short that shows the aftermath cuz office au caitlyn is soooooo hot bro.
this is also my first smut fic, so ty for reading !!!