Midnight II
Pairing: Assistant!Reader/Boss (Original Characters (no names used))
Content: 2nd POV. Smut (18+ only), age gap (all characters over 18), CEO/assistant, assistant!reader, power imbalance, infidelity, teasing, name calling, masturbating (reader masturbates for her boss)
Days later and still no word from the boss about what happened two nights ago. It was embarrassing to come to work the next day knowing what you had done, how you spread your legs so easily for your boss, but when you came into the office the next morning, your boss had a list of tasks for you like she always does. She barely looks at you, but when she does you see nothing behind those icy eyes.
You weren’t sure what that means, or if it’s even worth it to search for said meaning. She's a woman who's spoken for. Having met her spouse a few times before you know there is no chance in hell that marriage is ending any time soon. That alone is enough to make you force yourself to forget about the other night, but imagining the HR nightmare that would ensue makes your stomach twist and turn. She would probably be spared due to her status within the company, but you on the other hand would not make it out alive. They would throw you to the wolves. Not only would you be out of job, you're certain they would blacklist you from working with many of the major companies that operate in this city. You'd have to go back to waitressing, or worse, moving in with your parents. She would turn her cheek the other way while the office skank got tossed out with yesterday's trash.
Thinking about what could happen to you scared the hell out of you. So much so that you found yourself feeling grateful that she was acting as if nothing happened. It was business as usual and no one would suspect a thing. That night was a mistake and clearly your boss wanted to continue being the professional woman she's been groomed to be.
Until she told you you had to work another late night with her.
She promised to let you clock out early Friday afternoon since you'd be out late and have to be back at work by 8 am. She really didn't tell you what needed to be done, just that she needed you to stay late tonight. And once again you watched everyone leave, the janitors leave, and you were alone with your boss in this big building again. You tried to distract yourself with getting ahead on some paperwork you knew your boss was going to need (and that's what she liked about you the most, you were always a step ahead of her when it mattered the most). Everything felt normal, and there was no tension between the two of you at all. However you could feel your neck getting hot. It felt like you had too many layers on despite the temperature in the room being on the cooler side.
Without saying a word you took off your blazer. Her eyes flashed over to you and she instantly noticed how you had unbuttoned the top two buttons of your shirt. It wasn't like that early so she assumes you must've slipped into the bathroom and made yourself more comfortable. Did that mean you trusted her enough to be able to relax around her?
She didn't mean to stare especially after she internally reprimanded herself for taking advantage of her power over you. When she came in this morning she reminded herself to keep things strictly professional. Yet she made up a reason to stay late with you again. It's not so professional to stare at the exposed skin of your chest. The computer's glow wasn't as flattering as the natural light hitting your skin but you looked so illuminating to her. You wore a necklace with your first initial sitting right in the middle of your chest. She wanted it to dangle in front of her face while you straddled her. She would take the metal between her teeth, disregarding the taste, as a tool to pull you closer to her.
The poise, professional demeanor was beginning to slip through her fingers and she found herself spiraling a little.
"Y/n."
Your name comes out of her mouth before she can process it. It takes you both by surprise. When your eyes meet you feel like you're being electrocuted.
"Come here."
Just as easy is it from her to command you to do something, it's easy for you to listen. You close your laptop and forget about it on the couch in her office. Soon you stand in front of her and you feel like an offering. Her eyes scan over your body before looking up at you. You're taller than her while she sits yet you feel small under her gaze.
"Get on the desk."
She asks and you listen.
Your boss doesn't have to ask you to spread your legs, you're already doing that before you know it. A smile spreads across her face; devious and sincere at the same time. You wore no panties today. In fact you haven't worn panties since she touched you. You told yourself you wanted things to go back to normal, but deep down inside you were waiting for this moment. You would squeeze your legs together in anticipation every time she called your name. You were waiting for the moment your boss decided she wanted more of you.
"No panties little girl?"
No one has ever addressed you like that before and it makes you shiver. The tone of her voice, the look in her eyes, it's all too much for you to handle. You whimper instead of replying to her comment. You're almost ashamed of yourself. However, you go to hide your face, she stops you. She grabs your jaw with the right amount of strength and makes you look at her.
"I leave you alone for a few days and you start acting like a slut," she's practically mocking you and she loves seeing how you squirm and try to avoid her gaze. "Were you hoping for someone to notice and take you to their office? Who were you expecting to see you like this."
"N-No one ma’am."
"Oh, so you just wore no panties because you felt like it?"
You had no answer for her and you were so embarrassed that she was trying to make you give her an answer.
"Or did you wear no panties to have easy access to yourself? You know there was a big rumor about some of the employees masturbating on the clock. It was about three, four years ago, so it was before you were here. You were probably stuck at that shitty waitressing job while working your way through college. It was just a rumor, but there are some people who just can't help it."
Your boss traced a line into the skin of your thigh. She had you reeling without even doing much. You watched her in meetings, speaking to powerful people, and securing deals, you shouldn't be so shocked that her charm is able to work on you too. But you feel like you're under a binding spell.
"Were you touching yourself today, Y/n?"
You shake your head no. You thought about when you saw her this morning, but you were scared of getting caught by her, someone else, or the cameras.
"So you just wore no panties for fun, huh? That's cute."
She stops touching you and you want to cry. She sits back in her chair and reclines a little bit. She just watches you sit on her cherrywood desk. She contemplates whether or not she should just leave you alone and frustrate you, but she's too indulgent.
"Show me how you would touch yourself during work."
You were uncertain, hesitating more tonight than the other night. That moment lingers in your head and you're sad that your boss might not touch you tonight. You have never masturbated for anybody before, not even with past partners. Your cheeks were so hot you thought your skin would catch fire. You lean back and rest on your elbows. As you lay back, your skirt moves up higher on your thighs. The legs your boss loves to stare at begin to spread wider for her. She was grateful for the Spring weather because you stopped wearing your stockings (although she loved seeing your legs in them).
"Fucking gorgeous," she whispers when she gets to drink in the full sight of your pussy. You were dripping wet, messy and turned on for your boss. The way she looks at you makes you stupidly feel special.
It took everything in her not to park herself between your legs and devour your pussy the way it deserves to be. She wanted to feel every inch of your soft flesh and watch you squirm against her tongue. She was hot under the collar, but she knew how to show restraint.
She watched on as you ran your fingers through the folds she wanted to lick so bad. The tension in your body was fading as you began to feel the pleasure hit your body. You wouldn't be able to forget that your boss is right there watching you play with yourself, but you let yourself relax knowing that she was enjoying this.
"Good girl rubbing that pretty pussy for me," she purrs, "play with your clit, honey. I know you want to."
Your fingers move as soon as the words come out of her mouth. You almost cried out when you pressed your two fingers into your clit, but you were able to just let a weak gasp escape. It wasn't satisfying enough for your boss who wanted to hear you scream, but she can understand why you wanted to be quiet. She made a mental note to somehow get her hands on you in her car one day so she can really hear you scream. Right now she just enjoys the show of you playing with yourself.
Usually when you're having a private moment to yourself, you have your blanket strewn everywhere, your phone is in your hand, and you have music softly playing from your player. You enjoy creating a sensual atmosphere as you masturbate to various things that pique your interest. It's hard to slip into that exact headspace without all of those elements coming together, but with the soft glow of your bosses' office, you felt close to replicating that atmosphere.
"Oh my god," you whisper.
She wasn't expecting to hear you get vocal tonight, but once she heard your voice she wanted more.
"Does that feel good baby? Use your words to tell me how it feels."
"It feels good sir."
You could barely speak a complete sentence as you stumble through the syllables. It felt so good to be touching yourself after a day of having lustful thoughts of your boss.
"I want you to play in your pussy. Finger yourself for me, Y/n."
You don't think your fingers have reached as deep inside of you like they did tonight. Of course if she wanted she could slip in her longer, skilled fingers into you, but she enjoyed being able to kick back and watch a pretty girl get herself off for her. Your fingers splashed in your wetness as you pistoned two digits in and out of your.
In and out. In and out. In and out.
Your boss was addicted to the rhythm and she couldn't pull her eyes away. She thought she was going to pass out at the sound of your fingers inside of your wet pussy. You were dripping so much that she could see a few drops on her desk. Normally she was strict about someone potentially fucking up her desk but right now she doesn't give a damn. She wanted to lick up the drops of your arousal off her desk once you were done. If she doesn't get one taste of you tonight somehow she just might die.
"That's so pretty, Y/n. You're so pretty baby."
She was cooing at you, watching how your chest rose and fell rapidly. You were certain you looked a mess after a long day of work, but your boss made you feel like the prettiest girl in the world. She continued to egg you on while you fingered yourself.
"What are you thinking about, girl? Are you thinking about me touching your pretty body and feasting on your cunt until you're shaking? I know you went home and did exactly this the night I touched you. You're going to cum thinking about all the things I'd do to you."
Her words kissed your skin and suffocated you at the same time. You wanted everything she teased you about. You would do anything to feel her soft lips wrap around your clit while she fingered you instead of you doing it yourself. You know a woman like her can make you cum over and over again. You wish you were the lucky woman who got to welcome her home.
"I'm gonna cum!"
Your fingers curl against your g-spot and you begin to see stars. Never did you think you'd have such an intense orgasm in your life in front of your boss. She watched with a satisfied smirk as you shook and squirmed around your fingers. Watching your juices seep out around your fingers was better than closing that deal on the 35 million development.
After working so hard and doing what she needed to do for this company, She deserved a little treat for being so good. That treat coming in the form of her pretty assistant made it even sweeter.