The Assistant!
Synopsis: As Michael’s assistant you decided that it was your duty to help him with whatever he needed, even if he couldn’t muster up the courage to ask.
Content: Mature!Michael, sub!Michael, bratty!Michael (the tiniest bit), dom!reader, p in v, unprotected sex, perv!Michael, overstimulation, handjob, cumshot, cum eating, pet names, no use of y/n, finally a plot (omg we cheered!), smut.
Wc: 3.5k
Maybe it was a little inappropriate to walk into your job with your breast pressed up against your blouse, and maybe your skirt was too short, but you didn’t care. In fact, nobody did, not even your boss, Michael.
He didn’t mind at all; he never mentioned it or said a word to you about your explicit outfits. If it had been anybody else, you would’ve been fired a while ago, but—Michael didn’t seem to care—or did he?
You had no idea that when you’d walk away, his eyes would be glued to your plump butt sitting in your skirt or that when you were close to him his eyes would jump from your chest to your face—he hid it so well you never knew that when he’d touch himself you were the only one in his mind.
It was funny—maybe not to you, but in general because you had such a huge crush on him and it still felt like he barely noticed you. You spent so much money trying to doll yourself up only for Michael to not even blink twice—not even a simple “I like your hair.” You were beginning to feel silly.
It was extremely unethical and inappropriate to flirt with your assistant, though…plus Michael didn’t seem like the type to make a move on one of his employees.
Maybe it was time to move on, maybe actually find someone your age and stop fantasizing over your forty-something-year-old boss.
Or not.
You couldn’t do that; you couldn’t just let go that easily, especially after what happened the other day. Your friends told you you were crazy, but something happened that night when you stepped into Michael’s office with your boobs on full display; the only difference was that there was a cold in the air, making your nipples rock solid against your shirt.
You were getting ready to leave when he called you into his office, and the minute you stepped in—something felt different. Through the familiarity of the space, there was an unknown air bubbling up. Michael, who lay back in his chair, relaxed his expression as soon as his eyes landed on you.
You walked further in, stopping right before his desk, scattered with papers and folders, with a few cups of what seemed to be alcohol to accompany them.
His big brown eyes stuck to you like glue, and you noticed him glance at your breast before landing on your face. You didn’t know whether to write it off or keep it tucked in the back of your mind—Michael was a man after all.
“I need you to do something for me,” he said, sitting up and leaning against the surface of the desk, folding his hands together.
“And that would be?” You stood with your head tilted slightly.
“I need you to come early to let the hvac people in tomorrow morning. I’m not gonna be here; I’ll be in New York.”
You nodded at his words, making a mental check in your mind. Michael, then, got up from his chair and walked over to you, his height reaching taller than yours as you stood at 5’4.
You didn’t know what would happen next, but you stood there waiting for him to say something; however, instead he just stared at you—his eyes locked onto yours for what felt like thirty minutes, but in reality it was more like thirty seconds before he spoke again.
He leaned against the edge of the desk, parting his lips to speak. “You know—you’ve been workin’ for me for a while now, and I haven’t gotten the chance to tell you how much I appreciate your hard work. I mean it’s not an easy job being an assistant to someone like me, and I just wanted to say, thank you. Thank you for staying professional, thank you for your dedication, and thank you for being here—for me.”
You blinked at him, an appreciative smile falling on your face at his words. “Oh wow! Thank you, Michael. I mean I love workin’ here, I’m truly honored, really.”
Michael smiled, leaning up from the desk, beginning to close the space between you two. He opened his arms, pulling you into a warm embrace, his broad shoulders taking you in. You, unprepared, snaked your arms around his waist, lightly squeezing him, feeling his warm body pressed against yours.
He held you a few seconds too long as you felt his large hand rub your lower back. His fingers touched the very little slit of exposed skin on your back, the feathery sensation sending chills up your spine.
You didn’t know what to make of it in that moment, his eyes falling back on you as he sat back down. “Jus’ wanted to say thank you, that’s all. I’ll-uh see you Wednesday.”
“See you Wednesday, Michael.” You noticed the double-take he did once his name left your lips. In all of your time working there, you’ve never called him by his first name; it was always ‘Mr. Jackson’ even though he wanted you to call him ‘Michael’, but you felt that it was too informal and you wanted to maintain your professionalism.
What you didn’t know was that your boss didn’t move from his office chair once you left. He, instead, masturbated over and over, letting your soft voice replay in his mind. The image of your glossy lips parting at the use of his name drove him so crazy that he almost slipped up—he almost let it be known that he’s been attracted to you this entire time.
But you didn’t think anything of it; you just said it because now you felt comfortable doing so. However, after ruminating for days on the whole interaction, you realized that Michael maybe called you into his office for more other than to express his appreciation.
You weren’t crazy; you remembered that morning specifically calling the hvac people, scheduling them to come early, and you already had it set in your mind to come in knowing that Michael wouldn’t be there to let them in—he also knew that, but the thing for you is that you forgot and didn’t remember until you got home that night.
Now that Tuesday has passed and Michael was back in California, things went on like usual—except there was a new behavior coming from him.
He was paying extra close attention to you, something that never happened during the first six months of you working there.
Michael did things for you, not like he was an assistant but more so your boyfriend. He cooked you lunch, listened to your troubles, and even massaged your feet. It surprised you because you were unaware of where it was all coming from.
None of it seemed to be flirtatious, so you didn’t take it that way; you just thought that because of his words to you the other night, maybe he decided to show his appreciation for you. Plus, you didn’t mind it at all, even if you thought he was being platonic.
In his world, he was losing his mind trying to contain himself. Michael didn’t want to make any moves on you because what you didn’t know was that behind that stoic exterior, he was incredibly shy, and he wanted to keep it to himself out of respect for you. He wasn’t aware of your attraction to him because you also knew how to contain yourself and keep things at bay.
Besides your skimpy outfits, Michael thought you liked to dress that way, and he wouldn’t deny enjoying the view of you prancing around in your tight clothes, but it never crossed his mind that it was for him.
The sun had already set by the time you were done helping Michael go over and sign business contracts; now you were downstairs finishing up the leftovers from earlier. After cleaning up, you were getting ready to leave, ascending the steps upstairs to say goodbye and goodnight to your boss.
As you reached the top, you headed in the direction of the bedroom he resided in, and as you got closer to the door, you began hearing faint moans. You paused for a moment, trying to take a minute to actually listen to what you were hearing. Creeping up to the door, the sound grew louder, becoming clear that your name was being said in between moans.
Your eyebrows furrowed at the realization. Michael, your boss, was jacking off to you. You heard the faint wet sounds of his dick pumping himself up and down, and out of your control, it started to turn you on.
Grabbing hold of the doorknob, you slowly cracked it open, careful not to make a peep. You opened it just enough to fully see Michael, sitting at the edge of the bed, still with his clothes on, his pants around his ankles, his head tilted back, and his mouth wide open.
He was loud, so loud that he didn’t even hear you calling out to him. He was in his own world of ecstasy; his eyes were shut tight, his expression completely twisting in bliss.
It wasn’t until you walked in, shutting the door behind you, that Michael jumped. His dark brown eyes landed right on you once they shot open, his hand abruptly halting as he sat up.
“O-oh! I-I’m so sorry! It’s not what it looks like.” His words made you scrunch your nose up as if his dick wasn’t fully out with his hand wrapped around it.
“Really? So you weren’t just playing with yourself before I walked in?” You stepped further inside, walking closer towards him.
Words escaped him; embarrassment washed over him. Michael didn’t know what to say. You saw it in the way his shoulders crouched; he wouldn’t even look up at you.
“I’m sorry, I really am.”
“Why do you keep apologizing? And why did you stop? I didn’t tell you to stop.” Your last words caused him to directly plant his eyes on you, slight confusion etching on his face.
“W-what?”
“I want you to keep goin’ and when you finish, finish on my chest.” You stepped right in front of him and knelt between his legs. You unbuttoned your blouse, revealing the black push-up bra that covered your breast.
Michael was stuck, stunned at most; he didn’t expect this reaction. Your eyes met his as you placed your hands on his inner thighs.
“Don’t be so shy now, you weren’t when you were yelling my name earlier. Have you really been up here for an hour stroking yourself thinkin’ of me?”
“Yes,” his response came out in a whisper, his Adam’s Apple bobbing up and down as he swallowed hard. You noticed a wetness pooling in your underwear; you couldn’t believe it.
“Is this what you do when I’m gone? Beat your dick and fantasize about me like the little perv you are?” You began caressing his thighs, hearing a hiss pour out of him.
“Mhmm, yes, I think about you every night.” His hand moved up and down at the tip, precum oozing out of it.
You tilted your head in wonder, “Oh really? What do you think about?”
His eyes fluttered closed as he picked up the pace, whimpers climbing up to his throat. “I-I think about—y-your lips and how’d the-‘yd look clasped around my dick.”
“How—shit—your breast would feel in my mouth and how warm you’d be as I slid in and out of your pussy.” You watched his head fall back as his breath began to hitch.
“O-oh—I think about your voice—your pretty voice singing my name as you cum a-and how you’d use me as a toy to make yourself cum. Oh-baby, I picture you making me cum over and over until I can’t take anymore—fuck and how you’d make me hold it in until I cry—yes!”
Michael’s peak was reaching him; he pumped himself at a relentless pace, his legs beginning to lightly shake. Meanwhile, you sat there, watching your boss get himself off to all of the fantasies he’s made up about you in his head. It was an extraordinary sight to witness. Your underwear at this point was so soaked you were sure there would be a wet spot, but you were too focused on Michael to even care about how much your pussy dripped at his admissions.
You sensed it coming with the way his body locked up, white liquid shooting out of him and landing directly on your chest. Your hands continued to massage his thighs as he pumped out his orgasm. A hunger awakened inside you as you sat, eager, ready to pounce on him.
Once he calmed down, he opened his eyes, looking straight down at your breast. “Oh Michael, look at the mess you made, now you have to clean it up.” You swiped some of his cum off your chest, bringing your finger to your mouth to taste him.
You stood up and sat next to him, your thigh brushing against his as you leaned in his space, crossing your leg over his; you perked your chest up in his face. “Good boys clean up the messes they make. Are you a good boy, Michael?”
“Yes-yes, I’m a good boy, I’m such a good boy.” He leaned his head down, licking up his cum, starting at your left breast.
He sucked lightly at your skin, bringing his hands to cup the right breast as he switched to the other side. You softly moaned at the feeling, bringing your hand to the back of his head, massaging it with your fingertips.
As soon as he was done, you grabbed his jaw, bringing his lips to yours, tasting the remnants of himself on his tongue. You pulled back slowly, his bottom lip between your teeth, and when it retracted, you noticed Michael’s dick rising again.
“Look at you, so needy. Do you want my help with that?” You watched him nod, his eyes pleading for your touch.
“Yes, can you please, please help me?” He leaned his hands back against the bed, fingers lightly gripping the sheets as you grabbed his tip.
He watched as your manicured hand twisted up and down around his base, leaking at the top. You swiped his precum off his tip with your thumb.
Michael mewled, his grip on the sheets tightening as you began to stroke him at a steady pace. “You were so loud earlier; how come you’re so quiet now?”
You turned your head to look back at Michael, whose moans seemed to be caught in his throat. “Are you holding back on purpose?”
“If you are, it’ll only be a matter of time before I pull those pretty moans out of you.” Your hand squeezed him slightly, whimpers escaping from his lips.
“Do you wanna cum?” You began pumping him at a faster rate. “Mmh-mm, ye-s, please,” his voice coming out little and weak.
“Well you’re not goin’ to if you don’t sing for me, Michael.” You heard him release a breath, a string of moans exiting afterwards.
To witness just how submissive he was boggled your mind. He was so different to the outside world you’d never think he’d be into this. Being the one always in charge probably felt mundane; not having a moment to step off the pedestal and let someone else take the lead seemed to leave him pent up with stress, and you didn’t mind being the reliever of it.
Michael dropped his head back, feeling his orgasm sneak up on him. His expression contorted as you felt his legs shake under you.
“Pick your head up and watch me make you cum.” You eyed him as he found some strength to follow your demand, your eyes catching full sight of the beauty before you.
“O-oh shit, sh-it, please d-don’t stop, baby don’t stop!” Your pace quickened, causing his body to tense up, orgasm washing over him; he thrusted into your hand as white ropes shot out, landing on his shirt and your hand.
Although he expected you to stop, you didn’t. Instead of helping him ride out his high, you continued with your hurried pace as Michael felt the overstimulation settling in.
He had no time to rest; his eyes landed on you, feeling chills run down his spine. “Fuck! I-it’s too much!”
“Oh, but you can take it, baby, I just love the sounds that are comin’ out of that pretty mouth of yours, you wanna know how much I love them?” You grabbed his hand, placing it under your skirt as you uncrossed your legs to give him access to feel your wet pussy.
Michael felt himself about to reach his peak again, his fingers rubbing against you; his mind became clouded. “U-uh gon-na cum again! Oh, it f-feels so good!”
“Yes, be my good boy and give me what I want.” He cried out, falling back against the bed as his body aggressively shook. Thick white liquid came out and landed all over his lap and your hand. Michael whimpered as you slowed down, grabbing at your wrist, his breathing breaking up each time he exhaled.
As he calmed down, you took the time to remove your clothes, leaving you naked, and once Michael opened his eyes, his eyes trailed over your body.
“God, you’re beautiful,” he muttered in a rasped tone, beginning to take off his shirt and remove his pants from his ankles.
“Thank you, baby.” You lightly pushed him back on the bed. “Scoot up.”
“C-can I taste you? God, I wanna taste you so bad.” Michael pleaded as he felt your wet pussy brush up against his dick once you climbed on top of him.
“Don’t worry, we have all night; just wanna feel you inside me first.” You grabbed his dick, wasting no time to insert him inside, and as you slowly sat down, your body quivered at his thickness.
“Fuck, you’re so big. Gonna make my pussy come all over this dick.” You whined out as you began to go up and down, your knees pressing into the bed as you picked up speed.
“Oh yes! U-use me, make me your toy.” Expletives and moans began pouring from Michael’s mouth. His hands grabbed hold of your ass as you rode him.
“Mmm-shit! Michael, you feel so good, oh my God!” Your eyebrows came together as you looked down at him, his expression mirroring yours. Bringing your hands to your breast, you massaged them lightly.
As your walls clenched around him, you felt his peak beginning to reach, causing you to speed up. His large hands gripped you so tight you felt his fingertips digging into your skin, causing you to squeal.
“Mi-Michael, don’t let go yet, not yet.” He looked up at you, face scrunching up in anguish.
“You f-feel so good, squeezing me so t-tight.” His moans grew louder as you kept at your fast pace. The room filled with sounds from both of you, physically and verbally, coupled with the headboard clanking against the wall. You felt him cup your ass, spreading it, making your pussy flutter around his dick.
“O-oh yes! Fu-uck ba-aby I’m gonna cum!” You sank all the way, taking him all in and rocking against him, chasing your orgasm. Your body jerked forward violently.
A broken wail flew out of your throat as your eyes saw black reaching to the back of your head. Your thighs clasped around Michael’s torso, your hands grabbing at the pillows beside him.
You pussy hugged his dick, sending him in a daze as he held in his orgasm. Tears welled and fell down the side of his face, holding onto you for leverage. The pressure was so much that Michael felt himself slipping; he shut his eyes so tight they began to hurt.
“C—can—mmm-baby! Ca-n I cum? Please p-please, p-please,” he sounded like a broken record the way his pleads continuously left his lips. You took a minute to catch your breath, leaving you to pause for a moment, but Michael had other plans as he began picking your hips up. “You’re so fuckin’ needy, Michael, you don’t listen.” You tore his hands away from you. Beginning again, this time at an unforgiving speed, leaving Michael a babbling mess.
“S-sorry—y-you just—oh God! Yo-you’re so perfect! Wann-a-fuck!—stuff you with my love!” You held onto the headboard, the bed squeaking so loud you thought it’d break in half.
“Shit! Michael! I’m so f-fuck! I’m so close!” That knowing feeling bubbled up inside you again; your body tensing up.
“Y-yes! Mmmm-fu-uck! Kee-p goin, doll! Your—uh! Baby! I-I c-can’t ho-ld i-t!.” Michael was so dizzy with pleasure he could barely form coherent words, his cries growing louder with every stroke.
You let go of the headboard and snaked your arms around Michael, bringing him up. “I-I’m—oh, my God! Michael cum with me!”
His warm release spurted up into you, covering your womb; you both began to shake, cries hitting the walls like thunder. Michael’s head fell into your neck as moans pulled from his lips, vibrating against your skin. Your chest rose up and down as your breathing slowed, your pussy quivering as Michael gently pumped into you.
You were so sensitive, knees so weak, you gasped softly as you moved off of Michael’s lap. Falling back against the bed, Michael, who looked at you tiredly with a smirk, opened his mouth.
“Can you sit on my face next?”
