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gurugirl · 4 months ago

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Assistance Needed | assistant!reader

based on this request (thank you anon! hope you enjoy!)

Summary: Harry finds himself in an awkward position when you walk in on him in his office just as he's in the middle of something quite improper.

Word Count: 3,053

Warning: smut (oral sex), inappropriate relationship, power imbalance (boss/assistant)

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. . .

How could you not know the lacy edge of your bra was peeking out from your lovely white silk top? Eyeglasses pushed up on your head while you leaned over the table and held the pencil between your teeth as you pointed to the paragraph in the document that you felt didn’t belong.

Harry stared down at the contract as you pulled the pencil from your lips to speak, “This looks like it doesn’t belong here. I feel like it was accidentally copied from a different contract altogether but we need to remove it.”

He looked up at your pretty eyes, already on his, and stood with a curt nod, “Yes. I think you’re right, Y/n. Once that’s done, print out enough copies for all the partners and we’ll sign them before the end of the day.”

You smiled at him and he felt his face warm. That’s all it took. Your smile.

But that was a problem because he was your boss. He paid your salary. You worked your ass off and you were the best assistant he’d ever had. You were even catching mistakes his administrative assistants didn’t. Sometimes he felt like you knew him better than his mom did. But that didn’t mean he was allowed to pine after you the way he was.

After closing the door to his office when you walked out he sat in his cushy leather chair and ran his hands into his hair. He couldn’t keep this up. His imagination would get the best of him at times but it’d been too frequent as of late. But part of him wondered why you had started wearing the things you were suddenly.

When you first started on, just over a year ago you always dressed professionally but very conservatively. There was no hint of anything particularly sexy or flirty. So Harry had never really looked at you like he had more recently. He always thought you were cute and smart and he was often surprised by how well you listened.

But then it turned into something like a friendship. He would seek you out for advice or to just chat, maybe even vent when the mood was right. He’d text you randomly midweek in the evening, then eventually he’d find himself shooting you a text on a Saturday afternoon, then a Saturday evening. And one day, when he was thinking about you while he was grocery shopping he realized he didn’t just find you refreshing to be around. Nor was he just simply happy to see you and enjoyed your company. No. He liked you. Liked you, liked you.

It really all blew up in his face, though, when you walked into the office one morning a couple of months ago wearing this dress that had his heart stopping and his tongue sliding out of his mouth (yes, just like a cartoon). He felt like a creep. He already knew he was developing feelings for you on some level but when he got a glimpse of you in something slightly more revealing it was like he was 16 again. It was embarrassing when he had to hide the front of his pants because all it took for you to make him hard was to wear a high heel or a dress that was on the shorter side.

Or wearing a thin white silk shirt tucked into a well-fitted pencil skirt and the tiniest peek of lace.

And he decided to do something he’d never done in his life. It’d be fast. No one would ever know and Harry could talk to you with a clear head and it would keep his boner at bay, at least until he left the office.

Scooting in closer to his desk he unzipped his pants and opened up his drawer to pull out tissues before spitting into his palm and smoothing it down his shaft. The relief was instant. He was swollen and already throbbing in his hand, which is why he knew it’d be fast. He could take his time later on at home, but in that moment, he needed to get off before you walked back into his office with the updated documents.

His breaths got deeper as he dropped his mouth open and closed his eyes and thought about your laugh and the curve of your bottom, your lips…

Pumping himself faster he laid one hand flat on his desk as he softly grunted the closer he got to this end. Another glob of saliva over himself made the glide of his big palm even better and he sighed when he felt his balls tighten and imagined your pretty lips wrapped around him, big, soft eyes looking up at him, the front of your shirt fully unbuttoned so he could get a proper look at the pretty bra he knew you were wearing underneath.

He was almost there when he heard a single knock at his door before it opened. You walked in with a folder and a smile on your face before closing the door behind you.

“I printed out copies for everyone. Michelle confirmed that the paragraph was transferred over from the Cota documents.”

Harry scooted himself into the desk and tried to catch his breath and act normal, hoping you wouldn’t see what he was doing or notice anything was off but he’d been right at the edge and his tip was already leaking as you laid the papers down on his desk. So far, it seemed as though you had no idea.

“Everything okay, Mr. Styles?” You suddenly paused and looked at his face. He seemed on edge.

“Yes. Fine. Thank you. I’ll sign these in a few minutes. Just, uh finishing something here.”

You squinted at him and noticed how flushed he was. How wide his pupils were. How dark his pink lips were. And his erratic behavior was a little odd.

“Are you sure? Is there something I can help you with?”

He looked up at you from his spot in his cushy chair and noticed the flirty grin on your face (was it flirty or was he just losing his mind?). The edge of your mouth quirked up as you slid your gaze downward to the space where the bottom half of his torso was just hidden underneath his desk.

“I don’t think that’s…” he inhaled, trying to calm his ragged breaths and will his erection away.

But instead of you stepping back and heading to his door to leave you cocked your head and sauntered to the side of his desk as if you already knew what he’d been doing and were determined to catch him in the act.

See, you’d been aware of his growing interest in you. And when the texts he’d send you on the weekends turned into flirtatious banter well into the evenings you decided to test out your theory. The first time you wore a dress that was just slightly shorter and tighter than normal with high heels that showed off your legs you realized he was checking you out.

So you did it again and again until you were positive it wasn’t just in your head. He was attracted to you. And it was so wrong of you to feed into it the way you did but it was hard not to enjoy the attention because Harry Styles was quite the specimen. Handsome and tall and witty… he was sexy, you’d always thought so.

And it was quite bold of you to assume anything but that day, you were feeling bold. Everything had been working for you since you woke up. Your outfit was banging (if you did say so yourself), your lipstick was staying put, you’d gotten the perfect amount of sleep, and your coffee order had been exactly to your preference. But what had you feeling extra confident was the double take Harry did when you stepped into his office that morning with his coffee.

“Mr. Styles,” you placed your hand on the edge of his desk and leaned down closer, “Tell me what you need.”

He blinked in surprise and swallowed, “I… what?”

Sliding your hand closer to the edge of the desk where he was you bit your lip as your shirt draped open slightly and you saw his pupils drag over your lacy bra.

You looked down at your cleavage and back up at him, “What? Do you like it?”

You watched him swallow again, a thick lump bobbing in his throat, “Do I like it?” He furrowed his brow and looked from your bra to your eyes, “It’s pretty.”

A grin took over your expression as you looked back down at your shirt, “Want to see more? I don’t mind.”

“I can’t. I’m…” he inhaled a shaky breath and looked down at his lap before pinning his eyes back to yours, “I’m your boss. This is inappropriate.”

You shrugged and pushed yourself back up, “I understand,” and turned to walk out. If he didn’t want to take it further you’d certainly not push it. But you knew he was up to something under his desk and you had a feeling what it was.

“Y/n wait a moment, please.”

You looked back at him and placed your arms over your chest with a soft smile, waiting for him to continue.

“Are you serious that you don’t mind?”

Shaking your head you released your arms, letting them fall to your sides, “I mean… this is embarrassing but I sort of wore this on purpose. Thought you might like it. So if you wanted to see more, well it’s for you anyway.”

“For me…” he repeated your words quietly as he considered his next steps.

“Yes. I’ve been dressing for you. I know I shouldn’t because, like you said, you’re my boss but… I don’t know.”

“I am your boss. But that doesn’t mean I haven’t been thinking about you in ways I shouldn’t be.”

“Like you were doing just before I walked in?”

His jaw clenched and he looked back down at his lap with a nod before turning his gaze back to yours, “I’m sorry.”

“Don’t be. I’m not. I think about you too, you know.”

“Probably not like this.”

“Like what? Were you… Mr. Styles, were you touching yourself under your desk?”

He was like a deer caught in headlights. Eyes wide and scanning as he shifted uncomfortably, “I was. I apologize, I…”

Stepping forward you shook your head, “Don’t apologize. When I asked you if you needed something I hoped you’d let me, you know…” you breathed out a laugh and shrugged.

“You wanted to… help me? Like…” his brows scrunched together as if he couldn’t believe where the conversation was headed.

“Yes. If you wanted. We can pretend nothing happened and I’ll leave right now but I would love to– assist.”

He swallowed again, the gulp sounding in the quiet of his office, “Fuck,” he cursed and looked down at his length. He felt like such a pervert but here you were offering your assistance. When he looked back up at you, you’d already made your way back to his desk, eyes wide and hopeful.

“I can’t ask you to do that, Y/n. I don’t want to take advantage of you in that way.”

“You wouldn’t be taking advantage of me. If anything I’d be taking advantage of you. I’ve been hoping it’d come to this and that you’d need me to help you. Whatever you want. My hand, my mouth…”

Harry couldn’t believe his ears. His pretty assistant was standing there waiting for the word. You wanted it. He knew it would be a big mistake but he nodded despite his better judgment, “Okay. I’m already hard and I was pretty close when you walked in so it won’t take long. I’m not gonna make you use your mouth but if you wanted–“

“I would like to use my mouth if you’re okay with it,” you placed your glasses down and began to round the desk to be closer to him when he moved his chair back and you saw it. Ruddy tip, thick from root to crown, precum pearled at his slit and slowly dripping down the impressive length. It looked heavy. His cock was almost as gorgeous as he was.

“You poor thing,” you knelt down next to his chair and slid your hands up his thighs, “I want to make you feel good, Mr. Styles. Is it okay if I suck you off or would you rather me just use my hand?”

He closed his eyes and leaned his head back into his chair, “Fuck… fuck…” his cock twitched as you moved in, perching yourself between his thighs and waiting for his answer.

“If you want you can use your mouth. It’s up to you. I’m not in the position to be picky really, am I?” He laughed his green eyes on yours again.

You smiled back at him and let your nails scrape over the material of his pants before you allowed yourself the indulgence of wrapping your palm around him and he hissed, his head falling into the back of the chair again, but this time he kept his eyes opened as he watched you.

You licked your lips and smeared his precome down his shaft before fixing yourself on your knees and spitting over his head, “You can come in my mouth too,” you added before dipping down and tonguing at his slit for a taste of what was to come. He smelled clean and neutral. The precome was only slightly salty and bitter.

But the moment you took him in your mouth, lips stretching over his crown he gurgled a moan and placed his palm on the back of your head.

Smooth strokes of your mouth up and down, your tongue cradling the underside of his cock as you sucked and hollowed your cheeks. He was quite girthy and long. You clenched your thighs as you took him deeper, wondering what he’d feel like tucked into your cunt, pressing through your already clenching, slick walls.

“Oh fuck… Y/n… shit…” he let curses fall from his mouth as you lightly gagged around him, your drool starting to make a bit of a mess on his pants, “Fuck me… such a good girl. Oh my god…”

He was delirious. It was just what you wanted; to have him mumbling nonsense and praise and to have him shivering… soon he’d be pouring into your throat.

You bobbed over him, his chair squeaking as he tensed his thighs to keep the bottom from swiveling and you felt pressure on your head as he instinctually attempted to keep you in place with his hand. Your sinuses burned as he rutted up into your mouth, a gagged moan coming from the back of your throat as he throbbed and fucked his tip further back, “My god, Y/n… holy shit, such a good fucking assistant, aren’t you? Gonna take my come down your throat? Yeah?”

You moaned and let your blurry eyes slide up to his face and he groaned when he made eye contact with you. It was dirty and sexy, and completely improper for him to be balls-deep in his assistant's mouth. But fuck it was pretty. You were pretty but with your lips wrapped around him, drool slipping from your mouth and down your chin, and watery eyes blinking up at him, the scene was lewd.

He pulled you up so you could gasp for air, strings of saliva connected to his cock and your lips as you heaved in a breath and he wrapped his palm around your neck and pulled you in, his lips pressing against yours.

You were already slick in your panties but now this was making you dizzy. You moaned and pumped his cock slowly before he whispered against your lips, “You okay still?”

“Yes. So good. Let me finish you off.”

So he released your neck and you immediately encased his cock with your warm mouth again, sucking and bobbing and moaning wetly until he was quivering and thrusting his hips, hand pressed over your head once again as he began to pump hot, sticky cum into your mouth. You gulped him down and curved your tongue along his length as he let out a hoarse groan.

It was sloppy. You’d drooled a lot and you were sure your mascara was running down your cheeks, but you didn’t care. You’d risk being a bit of a mess if you could have him like this. You’d take what you could get of your handsome boss.

Harry moved his hand away from your head and you swallowed the last of him down as you pulled up, letting your tongue lick any missed cum, suckling at his tip before sitting back and looking up at him with a smile.

He was breathing hard as he reached for your face, “Thank you.”

“My pleasure,” you laughed softly and pushed yourself to stand. “Think I need to clean up a little before I step out of here.”

Harry tucked himself back into his pants and laughed, “A little. I like the raccoon look, though.”

You opened up the cabinet next to his desk, the door had a mirror on the inside as you dapped tissues at your eyes, “You only like it because of what it represents,” you grinned. “Anyone else would be confused and worried about me if they saw me like this.”

Harry watched as you cleaned up and noticed you kept squeezing your thighs together, “What about you, Y/n? Need anything?”

You huffed a laugh, still feeling flustered and on the edge of crazy for doing what you just did, “Nothing I can’t take care of myself. Besides, there’s no time right now. You’ve got a conference call in a few minutes and I need to run these documents to the other guys before they leave.”

He stood up, following you to the door and stopping you before you could step out, “Will you come find me before you leave today?”

You bit your lip and nodded, “I always do, don’t I?”

Harry pushed a laugh out through his nose and nodded, “You’re right. You do. See you in a while then?”

You opened the door and smiled at him, “Of course, Mr. Styles.”

. . .

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