I’ll Assist You || ceo!keys x assistant
Summary: After his mind is plagued by his sweet assistant, Keys is struggling to concentrate on his work. Surprisingly he finds that she’s ready assist him with his troubles, in any way.
Content warnings: oral (m & f receiving), p in v sex, dom!Keys, sub!assistant, use of sir, slight degradation, sex at work, spit play, light facefucking, male masturbation (i think that’s it?)
Word count: 4.9k
Based on:
“Now, where you see this graph? This is where the data displays engagement. We rose up on launch day - of course - and - and, uh -“ Keys stopped mid-sentence, looking at the young girl that had scrambled through the glass doors, a stack of coffees carefully balanced on one arm, and a notepad and laptop tucked under her other. She was often on time, but today was different.
While Keys couldn’t figure out what had held her back fifteen minutes of the team meeting, his mind was busy. Suddenly occupied with the smooth curves of her exposed shoulders and the slight peek of chest she didn’t usually show. Her face as soft and beautiful as ever was glowing, a summer hue on her cheeks as she handed out the coffees hurriedly.
“I’m so sorry, Mr Mckey, the lines at the coffee shop were horrific.” She explained sweetly, placing his coffee in front of him and settled with her laptop on the chair next to his. Key’s suddenly couldn’t find any words as he waved his hands in a ‘no worries’ gesture.
“So, uh, the dip - this um, this dip line here is where our blue shirt glitch happened, the uh -“ He stuttered as he watched his assistant chew on the end of her pen, her eyes bright as they looked up at him with deep engagement. He couldn’t hear anything, think about anything let alone take his eyes off her lips until he saw them moving.
“Sorry?” Keys spoke suddenly, startling her. Hushed whispers sounded through the conference room as concern grew for his behaviour.
“I said, are you feeling okay? You don’t seem well. I can send everyone out if you need space, sir.” She spoke kindly, quiet so as not to embarrass her boss. She was thoughtful, gentle with her tone as genuine worry flashed behind her eyes.
“Yeah, I, uh - yeah can you take over? Excuse me everybody.” Walter spoke lowly, nodding his head towards everyone in the conference room as his assistant nodded and stood. As he grabbed his coffee and his bag, her body slid past his slowly. He could almost feel her heartbeat against his chest as his eyes dropped to the line of cleavage in front of him. He felt like a teenage boy, stuffed to the brim with hormones as he looked back up at her face; her eyes had a twinkle to them he hadn’t seen before.
The whole interaction was less than 10 seconds, but it had replayed on his mind all afternoon, his jeans tighter than usual as his brain displayed the image of that silly little glint in her irises. He was thankful for his new desk, the thick mahogany concealing any arousal and any twitch of his aching cock trapped underneath it. Every time her sweet voice sounded through his office phone, reminding him of another meeting, he could feel his cheeks burning; his face warm and pink. What the fuck was happening to him?
He’d called in sick. The week off. He couldn’t take it, the summer heat burning such rays down on the office that his pretty assistant walked in a different dress every day. Slip dresses, floral sundresses, high waisted skirts and low cut tank tops. He couldn’t take the ache of having to tear his eyes away from her body, the constant drinking of water because his throat got dry every time she looked at him when he tried to present statistics to his team; he’d end up in the bathroom from not only over-hydration, but the dire need to palm at his cock in attempts to get it to calm the fuck down so he could work.
So he took time off, sitting on his couch at home and tugging desperately at his cock, watching videos of corny scenarios in which some unqualified guy bent his unsuspecting secretary over a flimsy desk. The first few times, he tried to find videos of women that looked nothing like her. Dollar Tree glasses on the bridge of their noses as they put on a painfully pitchy seductive voice and got on their knees waiting. It got him over the edge, spilling precariously over his fist and often times the coffee table in front of him.
But then came Sunday night. The night before he was due to go back into the office, and his heart kept palpitating at the thought of seeing her again. The thought of her eyes, the way they twinkled with something he couldn’t quite place had his imagination running wild. And so came the usual routine, scrolling through his phone for the perfect video to get off to. But something hit different, his heart beating a million miles an hour as a video popped up as a recommendation.
‘Innocent secretary cums hard on her boss’ desk’. Vanilla title but the thumbnail is what sent voltage to Walter’s cock. A pretty girl looking exactly like his assistant, bar the different coloured eyes and heavy glam makeup, laid back against a desk with her boss’ head between her legs and a pretty floral dress bunched up around her waist. He felt guilt creeping up his spine immediately for how quickly he freed his cock from his pants, the speed at which his thumb clicked the video but he couldn’t stop.
“Mhm, cum all over his tongue like that.” Keys mumbled lowly, his bottom lip tugged between his teeth as his fingers wrapped around his throbbing shaft, stroking so fast he almost couldn’t keep up with himself. After pottering around her boss for a good portion of the video, tending to his every need, the girl in the video was about to come, her hips squirming as her ‘boss’ looked up at her determined to make her a sopping mess. God, what he would give to do that to his naive assistant. Have her writhing against his tongue as he lapped up any drop of arousal she’d give him. He couldn’t even fathom an inch of guilt now, too close to exploding all over his stomach at thought of the taboo relationship he’d formed in his head.
He slept peacefully, until his alarm woke him up at 7, reminding him of who he had to face and the events the night before. Sitting up and unlocking his phone, he closed all his internet tabs and erased his history; taking a cold shower to clear his mind and his conscience. He headed into the office, feeling confident about his day back.
That was until she walked in. White and blue floral dress. Just like the girl in the video. His eyes almost popped out of his head, as his laptop slipped from his hands and clattered to the floor. Her head turned towards the sound, eyes widening as she ran over to help him, dropping to her knees in front of him.
“Are you okay, sir?” She asked breathlessly, as she checked his laptop was okay before passing it up to him. Her eyes bright as usual as she didn’t move from the floor. Walter could barely move, his head too busy with a mixture of attempted professionalism, forming words and the pornographic moans of the girl from the video as he looked down at his assistant. He just nodded as he grabbed his laptop and headed into his office, trying hopelessly to blink away this new image of her. She followed him into his office, concern crossing her face.
“Thank you, that’ll be all, really I’m fine. Can you check what presen-“
“Mr Mckey, what is going on? Have I upset you in some way?” Her voice was gentle as always, as she stood in front of his desk, ignoring his heavy sighs and his face buried in his hands. He couldn’t outright tell her that his presentations had been failing, his mind had been racing, his cock had been fucking leaking at the sheer sight of her walking through the office. She’d go straight to HR. But he wished he could say it. Wished he could tell her how much he wanted to bury his tongue -
“Please, sir. I want to help you. Let me help you.” She spoke again. He’d heard that line somewhere before. The tone, his assistant had perfectly matched the whine. The porn video. No, that would be ridiculous. Unless she was crouched behind his couch last night, she’d have no idea. He dropped his hands away from his face, looking up at her confused.
“What did you say?” Walter spoke, wanting her to repeat herself in case his aroused mind had made it up. But he had it confirmed.
She slunk around his desk, sitting on the edge of it with the same concerned yet kind look on her face. Her eyes boring into his with that glint, yet gentleness that he couldn’t stop thinking about. What was happening? Had he not woken up yet?
“I said, please let me help you. Sir.” She whispered, her hand coming to rest on top of his against the desk. Walter shot up, standing in front of her as he shoved his hands into his pockets; distancing the contact between them.
“Were you in my house last night?” Walter accused, his tone a little angry as he became paranoid. His assistants face changed into surprise, shock across it as she shook her head defensively. Walter’s softened as he regretted the tone he used with her.
“I - I’m sorry - I didn’t mean to - fuck - I’m really sorry -“ He apologised, though stopped in his tracks as her expression changed suddenly.
“Mr McKey, I did something bad. I should be saying sorry.” She mumbled softly, her eyebrows frowned with regret but her lips curled up at both ends. Walter was confused, pushing his glasses up on the bridge of his nose as they fell with the furrowing of his eyebrows.
“What - what is going on? What did you do?” He stuttered out, trying not to focus on the way her legs were slightly spread on his desk.
“I…got worried about you. You were off. Acting weird. Especially in meetings and stats presentations and then you slumped off for a week - no communication and -“ She rambled nervously, waving her hands as she spoke. Walter was growing more and more anxious, slamming a hand down on his desk. She flinched ever so lightly but it was met with a tiny smirk.
“What did you do? Tell me now.” Walter spoke with a harsher tone, not meaning to be intimidating but was quickly getting tired of the dragged out responses he was getting.
“I want to be the girl in the video, Mr McKey.”
Walter felt like he was about to pass out, the room spinning slightly as his heart started to pick up again. There was no way this was real. He was still dreaming, the post-orgasm sleep hitting him differently.
“I don’t - I have literally - just no idea what you’re talking about.” Walter scoffed, running his hands through his hair. His eyes darted over to the window of his office, looking out to see if anyone could somehow see into his mind.
His assistant stood up, fiddling with the tie at the chest of her dress, smiling unfazed by Keys’ clear distress. This silly pining and feigned ignorance wouldn’t go on anymore. Walking towards the door, she ignored his questioning of her actions as she locked it, rolling the blinds down. The other members of staff would just suspect they had a meeting, nothing more. As she turned back around, leaning back against the door, she wondered if this was the right thing to do; her body essentially throbbing with the carnal need she’d developed since the day Walter had hired her.
“I wanted this job because I was underestimated everywhere else. Not only that but the way you stood up to Antwan Hovachelik? Dude was an asshole. You deserve to be here, to be owner of your creation. I admire you, so much. So when you got all weird and seemed unwell, I wanted to check in on you.” She spoke, walking slowly towards Keys’ desk again. He cleared his throat as it began to dry as it instinctively did whenever she looked or spoke to him. Her demeanour had changed slightly, a confidence in her walk that wasn’t there before.
“You - yeah - thank you. I, uh, I took time off to clear my head, that’s all.” Walter muttered, his eyes looking around the room; anywhere but at the sultry gaze she was throwing towards him. He couldn’t believe the way he was caving, he was stuttering, nervous by her.
“I know what’s going on.”
“Do you?” Keys chuckled with a scoff, believing he still had the high ground here.
“You watched porn with a video of a girl who looked similarly like me. I’m guessing it made you come, seeing her submit to her boss like that.” His assistant spoke boldly and bluntly, but with a sickeningly innocent tone to her voice as he almost choked on his own tongue.
“And how the fuck would you know something like that? You’re being - this is highly unprofessional.” Keys spluttered, taking off his glasses and throwing them on his desk.
“Because I hacked into your phone. Before I explain why, I want to apologise first and foremost for in the invasion of privacy. I was truly worried. I was going to see if you’d emailed anyone and explained why you were off, what was going on. But then it flashed up on my screen. Like a screen sharing app if you will.”
Keys’ mouth opened and closed with no sound coming out, his knees feeling heavy as he sat down in his office chair. He was filled with guilt, anxiety, shame but most of all, his cock was aching more than ever.
“It doesn’t take a rocket scientist to deduce what was happening then. Seeing her look like me, wearing clothes similar to how I dress? Bar the fact my eyeballs would fall out if I put that much makeup on them, it was a little too familiar right? Getting fucked by her boss? The taboo, the risk of it all?” She kept going, slowly making her way around the desk again and sitting back in the spot right next to his chair.
Keys sighed heavily, leaning back in his chair and looking up at her finally. He knew now, that this wasn’t a one-way street. It wasn’t as perverted as he thought, because she wanted it too. He could tell by the way the glint returned to her irises as they fell upon the strained outline of his cock in his jeans.
“Aren’t you clever? Such a smart girl after all.” Keys muttered, folding his hands over his lap. “Invading my privacy is worthy of a call to my lawyer.”
Her eyes looked away from his groin for just a moment, fear flashing through them.
“Your concern means a lot however.”
“I really just wanted to- to make sure you were okay, to check in. I didn’t think I’d confirm my own fantasies, nor did I think you’d share the same ones.” She stuttered, and Keys rose an eyebrow and smirked before standing up, between her legs this time; his knee nudging one of hers open slightly.
“No. You just thought you could walk around with your pretty dresses, and your little tank tops, and these stupid fucking eyes and think I’m not going to want you? Then you hack into my personal life and think you’re gonna get off scot-free?” Keys spoke firmer this time, a hint of anger in his voice but it was a facade for the hot arousal coursing through his veins. She was looking up at him with the same innocent look she always did.
“What’re you going to do about it, sir?” She whispered back, hop-skip and jumping over the work boundary they were supposed to have. Walter’s eyes flitted over her face, to her lips, the curve of her cheeks and back to her eyes again before he finally gave in.
Smashing his lips against hers, it was messy. Almost painful the way their mouths rolled against one another, carnal need for each other finally being released. His hands travelled up her sides, one tangling in her hair as he held her mouth to his, the other finding the hem of her dress and bunching it up in his fist.
“Please.” The angelic tone of her voice rang through his ears, echoing and swimming through his bloodstream straight to the head of his cock.
“Just once. This one time and we forget it happened.” She carried on, begging with her eyes as her hands found his belt buckle; unfastening it and pulling the zipper apart wantonly.
Keys nodded, his hand tugging at her hair so her head tilted back. His lips sucked at her neck, careful in marking so the entire office didn’t know he’d fucked his assistant. He let her fumble with the hem of his underwear, while his hands got busy hiking her dress up around her waist. He’d dreamed of this, watched porn of this. And now here she was, with her legs spread against his mahogany and her fingers - oh - her fingers wrapping around his cock.
“I want to be that girl, Mr McKey. Want you to make me yours, even if it’s just this once okay?” She whispered softly and sweetly, her tone mimicking the one that had made him come hard maybe a mere 12 hours before. She stroked him slowly, her thumb swiping over his slit and spreading the copious amounts of pre-come he’d produced at the sight of her.
“You want me to take you on this desk? You liked that video too, didn’t you?” Keys spoke with a hint of condescension, his hips bucking slightly into her touch. He watched as she bit her lip and nodded, bringing her other hand to his cock and using both to stroke him.
“Mhm. Odds are we came at the same time.” She spoke softly, smiling sweetly up at him. Keys almost came there and then, his mind pulsating with the thought of her touching herself to the same video, at the same time.
“Tell me. Tell me what made you come. Was it his tongue? Was it the way he held her head as he fucked her throat? What was it?” Keys mumbled desperately, his hands sliding along the insides of her thighs, pushing them apart as a string of her own arousal stuck between them. He moaned aloud, letting two fingers gather the stickiness along the cotton gusset of her panties.
“Yeah - how - he - fuck, sir, please -“
“Tell me and I’ll make you come just as hard. Use your words.” Keys spoke again, looking up into her eyes this time as he awaited her answer, joining his two fingertips in the side of her panties and pulling them against her thigh. His mouth watered at the sight of her wet cunt, glistening on his desk like a fresh meal.
“How he held her face, you know - made her look at him? When she was coming? And then - fuck -“ Keys slid his fingers inside her, her wetness allowing him in with ease as she moaned sweetly; her eyes fluttering shut as her grip on his cock tightened and stilled for a moment.
“And then what?” Keys continued taunting her, copying her hands and stilling his fingers inside her; though his fingertips were angled upwards against the spongy spot that had her chest falling and rising faster.
“And then he spat.”
“All her mess right back into her mouth. Put her in her place, didn’t he?” Keys whispered, his spare hand leaving her hair and gripping her jaw softly. She nodded up at him, finally clicking into the dynamic Keys had manifested subconsciously. He’d never thought he’d be capable of controlling somebody’s arousal like this, but she was so needy, so pliable. Assisting him, like she’d been hired to do.
“Can I make you come?” Keys asked politely, though there was a slight growl in his voice, the desperation to feel her squeeze down around his fingers almost painful.
“Yes. Please.” She groaned, bucking her hips down onto his fingers. He smiled against her lips, grinding his fingers back into her with a deepening intensity, his other hand keeping a tight grip on her jaw. He wanted to watch her climb that peak, dance on the edge of pleasure. Her sounds were heavenly, but already her pleasured expression was more beautiful than he could ever have imagined.
“I’m close, sir. You’re making me so close.” She whimpered, her hands finally letting go of his cock as she braced herself on the edge of his desk with one and pulled his face closer to hers again with the other. He kissed her messily before pulling his fingers out of her; chuckling lightly at her whine.
Tutting at her teasingly, he pushed her shoulders back so she fell onto her elbows, her eyes widening as she realised what was happening.
“Remind me. Who works for who?” Keys spoke softly, tucking his heel into the leg of his office chair and dragging it closer so he could sit. He pressed kisses to her knees as he pulled them upwards, her heels kicked off as she balanced her feet on the arms of his chair.
“I work for you, sir. I’m yours.” She moaned innocently, eyes threatening to roll back as he pulled her hips closer to the edge of the desk, pulling her panties off entirely and diving straight back into her cunt like a man starved. He didn’t let up, not until she was squirming and writhing on his desk like the girl in the video they’d both watched.
“Mhm. And you’re gonna listen to me and come when I tell you to?” Keys mumbled against her clit, sucking it into his mouth as he looked up at her and waited for the answer. Her eyes squeezed shut now as she tried to pinch off the impending orgasm that was waiting, pulsating inside her. Her boss was eating her pussy on his office desk, quoting the exact video that had got them both off before. She could barely hold it off as she replied.
“Yes sir, I promise I’ll be good. Anything to make you fucking happy ohmygod -“ She rambled messily, as his fingers found their way back inside her; pumping rhythmically at the same time as his tongue against her clit. She wasn’t entirely sure of the promise she’d made, only that she wanted to impress him just as much as she wanted to come on his tongue.
“You can come. Can tell you’re being good already, squeezing my fingers so tight they could break. Make it messy, okay?” Keys moaned, his eyes closing in pleasure as one of her hands came to grip the hair at the front of his head, pulling him in closer somehow.
He was entirely entranced with the taste of her, sweet bitterness on his tongue as he waited for her to tipple over that edge. Her breathing was getting faster, her walls clenching sporadically around his fingers.
“Tell me. Tell me when you’re coming.” Keys mumbled against her skin, tongue rolling over her clit as he sucked it in between his lips again.
“I’m coming sir please, please don’t stop -“ Her whines were making his cock jump up against his stomach as he put everything into pulling her through the waves of ecstasy. Her spasms around his fingers could be felt on his chin as his eyes rolled back into his head, not letting up until she fell back fully on his desk; her calves coming to rest down on his shoulders.
When he finally had the willpower to pull away, leaving gentle kisses to the creases of her hips and thighs, he stood up. His knees felt weak, power and arousal weighing him down as he planted his palms on the desk either side of her.
“You need to be way quieter, you understand me? Whining and whimpering like that? Do you want to get caught with your dress up around your waist?” Keys taunted, dominance rushing through his veins. He was shocked at himself, but the way she responded so eagerly to him pushed the doubt to the side.
“No, sir. I’ll be quiet, I promise.” She whispered, reaching for his cock and holding the head of it against her clit. Keys’ hips stuttered for a moment at the contact, her warmth coating him for a second as he became impatient and pushed inside her. He gripped her jaw again, making her look into his eyes as he watched her feel the stretch. She pulled him in so easily, but she was so compressed around him. So much so, he felt like he couldn’t breathe, but would he stop? Never.
“Sir?” She spoke softly, her jaw opening as he rocked into her carefully. He hummed in response, looking down at how his cock disappeared inside her, before pulling out and moaning at the glisten covering his shaft.
“Can you -“ She whispered shyly, as he looked up at her. She was holding her tongue out, just like the girl in the video. He knew what she wanted. He leaned over her with a smile, their eyes glinting towards each other as he spat directly into her mouth. He felt his cock throbbing inside her as she swallowed him down before kissing him hungrily.
“Can’t fucking take this anymore. You’re too pretty.” Keys rambled, his hand settling on her lower back as he rutted into her quickly. She bit down on her lip, eyelids locked shut tight as she tried to hold back the moans firing from her throat. Her hands fisted at his shirt as he pounded into her with a ferocity he didn’t even know he had in him.
“You’re gonna make me come. You feel too good - I can’t -“ Keys let the dynamic shift as she blinked her eyes open, smirking at him. The way he yearned for her with his body, the way he couldn’t control himself anymore sent a power surge up her spine.
She pushed him away, jumping off the desk and kneeling before him before he had any time to complain about the lack of constriction around his cock. He scoffed in disbelief, fingers immediately tangling in her hair and pulling her mouth onto his length messily.
“Can’t believe this. You on your knees, mouth stuffed full of me. God, you’d do anything for me wouldn’t you?” Keys rambled as he thrust his cock into her throat over and over. She nodded as best she could, sweet little whimpers sounding around his shaft as she let her throat go lax to allow him the speed and depth he needed.
It wasn’t long before his balls were drawing up, threatening to spill into her throat. One look down at her teary eyes, her pretty dress crumpled and her lips tucked around him and he was gone.
Fingers matted into her hair as he held her down on him, cum spilling in pools at the base of her tongue as he tried to groan quietly.
She pulled off after a moment, taking the time to not only swallow his spend, but look up at him with the most sated look Keys had ever seen. She smiled, getting up and fixing her dress before seating herself on the edge of his desk again. Walter stood shocked with his softening cock still out of his pants, running a hand through his own hair as he caught his breath.
“You’re…that was…insanity.” He breathed heavily, tucking himself away and sinking into his office chair. He felt exhausted, but in the best way; eyes looking from her ankles all the way up to her eyes as she seemed not just content but back to her usual self.
“Is there anything else I can do to help you?” She said smoothly, her sweet smile now tainted by Keys’ image of her with his cock between his lips.
“No, you uh, I don’t need anything else.” Keys said almost coldly, trying to process what had just happened and whether or not they should have done it. She nudged his calf with her foot, getting him to look up at her as she smiled.
“Nothing happened, remember? One-off. We both feel better now.” His assistant spoke kindly, leaning her feet down to slide into her heels again as she stood and fixed herself one last time. Picking up some stats sheets that had been pushed to the floor, she corrected them into a pile on Keys’ desk, moving and opening his laptop and putting it in front of him while he just watched with widened eyes at the shift in the room.
“Yeah. Really got it out of our systems-“ Keys was interrupted by a harsh knock at his office door, his heart palpitating at the thought of it being someone that found out about their lustful interaction.
“Oh! That’ll be your 11 o’clock. He’s here about your deputy position.” She spoke softly, pulling up his blinds and unlocking the door.
Walter fell back into his own usual self, clearing his throat and putting his glasses back on, tucking his shirt back into his jeans and trying to shake the last 30 minutes out of his head.
“Thank you.” He said gently, double meaning as he smiled back at her before letting her welcome in the interviewee. As she walked over to the coffee machine opposite his office, he sighed. That hadn’t helped at all. He definitely couldn’t stop thinking about her now.