Assistant - otw!Michael Jackson x Reader
Summary: “I was wondering if you needed anything else for the night.”
Warnings: 18+, sub!mike, inexperienced!mike x experienced reader, PRAAIIISEEEEEE so much praise, crying, fluff(ish) ending, everything.. just so much, so many things, chronic desperation and eagerness
“How’s that feel? Good?” You say softly, continuing to grind your hand in an upward motion.
“Mhmm” Michael groans reassuringly. “Feels great.”
His head tilts back slightly as he closes his eyes to take in the feeling of your hands on him.
You smile to yourself proudly, “Good! I can-“
“Actually,” he interjects. “You don’t have to do this, I’m sorry.” he breathes out sharply, letting out a small chuckle. He removes your hand from his shoulder before dropping it completely.
“No, I don’t mind.. really! It’s what I’m here for, Mikey. Anything you need.” You insist.
You’ve been Michael’s personal assistant for about a year now. You were hired just after Off The Wall’s release and have been Michael’s right hand ever since.
The bond you shared was sweet which made it ten times harder for him to feel okay asking you to do things for him, especially unnecessary things like massaging out the knots between his shoulders.
You enjoyed taking care of Michael. Working for him was easy, he was never too hard on you, never too demanding. His shy and gentle nature made it easy for you to stay dedicated to his comfort. Plus, the small crush you had on him made everyday that much more exciting.
“Damn it, Michael…” he whispered to himself once you left the room, his back colliding with the mattress.
He couldn’t believe that he had you in his room with your hands roaming all over his body, wearing his favorite (painfully short) miniskirt and he still couldn’t muster up the courage to make a move on you.
You’re older than he is. He’ll be twenty-two in a few weeks and you just turned twenty-four. The closeness in age encouraged an easy partnership. On the other hand, the small gap made him doubt his chances with you.
A faint knock on the door disrupted his thoughts, “Yeah?” Michael shouted while sitting back up.
“I was just wondering if you needed anything else for the night, I was thinking about heading home if that’s okay.” You called out through the crack of the door.
“Oh! Umm.. no.. no, that’s okay. Thank you! Uh.. drive safe!” He scratches the back of his neck feeling defeated as he hears your footsteps walk down the hall, his window of opportunity shrinking with every step.
Before his brain could catch up to his body, his feet were already in the doorway and your name had already slipped past his lips.
You turned your head to see your handsome boss leaning against the doorframe and motioning you over to him.
“Could you come in.. please?” He asked meekly, looking everywhere but at you.
“Sure, Michael. What’s up?” You asked brightly, walking past him and stepping back into his room.
“Can you uh.. could you, maybe, give me some advice? I don’t want to burden you with my troubles but I’m not sure who else to ask.” He plops back onto his mattress, folding his hands in his lap.
You walk over to him, settling next to him at the edge of the bed and looking at his face intently. “Of course, what is it?”
You’re starting to get a bit nervous. His anxious twitching and fumbling with his fingers made you wonder what he was so worried about.
You place a hand on his knee attempting to calm his nerves and you didn’t miss the way a very faint, almost inaudible, gasp left his throat. “Hey,” you smiled. “It’s okay, you can ask me anything.”
“Well.. um, there’s this girl..” his soft voice trembled slightly into a near whisper. “I really like her, and I’m not sure what to do about it. I’m not very experienced… with women.” He confesses.
The shy admission caused your heart to swell. “Michael..” you huffed out a faint giggle. “That’s okay! You don’t have to be so nervous, girls aren’t as scary as they seem.” You nudge his arm with your elbow playfully.
His frame relaxes slightly as he lifts his head and turns it to you.
“I think you should go for it, Michael. Tell her how you feel. You’re very charming I think she’ll be super flattered.” You reassure, holding gentle eye contact.
His eyes widened. “You think I’m charming?”
The shock on his face made you giggle before nodding a hard yes, “Absolutely. You’re irresistible. Any girl would be lucky to have you. You have nothing to worry about.”
“You’re embarrassing me.” Michael bit back a smile while timidness danced across his cheeks leaving a ruby trail behind.
His adorably red face caused your own to blush. “It’s true, Michael.” You lift your hand to his back and caress the fabric comfortingly, the sudden contact causing him to twitch slightly under your touch. “Like I said, any girl would be lucky to have you.”
“It’s just that.. I’ve never really..” He trails off and exhales sharply.
After a beat of silence your curiosity gets the best of you, “Have you ever even kissed a girl, Michael?”
He clears his throat before answering, “Yeah.. I have. I’ve just never..” He looks back up at you through pleading eyes, hoping you don’t make him say it out loud.
“Oooh..” you nod in understanding, “That’s okay.”
You notice his posture slump defeatedly. You cup his face in your hands, forcing him to look at you. “There’s nothing to be ashamed of, Michael. I actually find that quite endearing…”
The rest of your encouragement drowned out into background noise by the flood of Michael’s thoughts. The feeling of your warm, soft hands caressing his cheeks and you previously telling him you found him irresistible was all that was playing on a loop in his head. Your glossy lips moving just inches from his own wasn’t helping his daze either.
A familiar ache started forming in his lower abdomen feeling the warmth of your face radiating onto his. You’re so close to him and it would be so easy for him to lean in and get everything he’s dreamt about for the past year. His heart thuds in his chest with every stroke of your thumb against his cheek.
You notice his eyes haven’t left your mouth the whole time you were talking and he doesn’t seem to be listening. A smile tugs at the corner of your lips before calling his name, “Michael.”
His eyes snap to yours breaking him from his trance. “I, um..” He bit down on his lower lip as his eyes trail back to yours. “..please.” He whispers, his eyebrows scrunching together slightly.
His soft whimper sent a shiver down your spine. “Please, what, Michael?” You inch closer, almost closing the gap between you completely.
“Please let me kiss you.” He whined.
You sunk your teeth into your bottom lip as a cheeky smile snuck onto your face. You parted your lips to agree but he filled the space before your words could.
He moaned into the kiss immediately. His arm slipped around your waist to pull you against him. The hunger of his movements caused an undeniable ache to throb between your thighs.
Your hands migrated from his face to the back of his neck, your fingers intertwining with his curls.
“I’ve wanted this for so long.” He mumbled against your lips. “Me too.” You confess.
His tongue pushes past your lips and begins exploring the inside of your mouth. You suck lightly at the wet muscle, the sweet taste causing you to squeeze your legs together.
“Mmm.” He hums against your lips. The sensual act caused the bulge in his jeans to push harder against the tight fabric.
You broke the kiss to leave a hot, wet trail from his lips to his jaw and up to his ear. “You taste so good, Michael.” You whispered, flicking your tongue slowly against his earlobe.
A soft cry ripped from his throat at the sensation. You pulled back slightly, just enough to get a glimpse of the large bulge throbbing beneath you. The evidence of his need caused enough saliva to pool in your mouth to force a hard swallow.
You pecked his lips softly but continued your kisses to his other ear, “I’m so wet for you, Mikey.” You whispered tauntingly. You tug at his hair gently, exposing his neck. You place an open-mouthed kiss underneath his jaw, sucking on the sensitive skin before grazing your teeth over it.
He tried to speak but it came out as a broken stutter, “C-can, can I-“ The feeling of your hand snaking up his thigh cut him off.
“Do you wanna feel how wet you make me, baby?” You mumble into his neck.
He nods impatiently, sliding his hand between your thighs. A small giggle escapes your throat at his eagerness. “Be patient, Michael.”
You grabbed his wrist and propped yourself back up side by side with him and draped your leg closest to him over his lap and in between his legs.
He groaned eagerly at the sudden pressure of your thigh resting on top of his bulge and his hips involuntarily bucked up against it. He dug his nails into your inner thigh in anticipation.
You hiked up your tight miniskirt, exposing the wet spot clinging to the crotch of your light pink cotton panties. His hold on your leg tightened at the sight.
“Please..” He begged, his voice laced with pathetic desperation.
You guided his hand slowly down to where you needed him most, letting go right before he reached your warm clothed center to give him full freedom to explore.
His hand impatiently pushed your underwear aside and pressed his long, thick fingers against your bare, wet, aching center.
You threw your head back at the sudden sensation and a loud, restrained moan escaped your lips. “Oh, Michael.”
His head fell in the nook of your neck, panting against you. Desperate whines left his lips as he continued exploring you.
“Oh my god,” he moaned your name in disbelief, “you’re so wet…. I did this to you?” His tone gave away his craving for your reassurance.
“You always do, baby.” You brought your hand to his face, catching his chin and forcing him to look at you before you continue. “Sometimes it’s so bad, as soon as I leave here I have no choice but to touch myself. You make me feel so good, Michael. I imagine you doing exactly this, touching my wet pussy and letting me cum all over your fingers.”
“Oh, mama…” He leaned forward, reconnecting your lips hungrily.
The padding of his middle and ring finger grazed over your throbbing clit causing a loud moan to rip from your throat and into his mouth.
He felt the swollen nub underneath his fingers and began rubbing tight, deliberate circles over it.
You gripped onto his bicep and began grinding your hips against his hand. The overwhelming sensation made it harder and harder for you to kiss him steadily. Your kisses became sloppy and slow. Eventually, your mouth fell open and he continued sucking on your bottom lip.
Your feverish grinding made his head spin. Watching you hump his hand greedily and moan his name was making him only want to please you more.
His hand moved from your dripping center back to your thigh causing you to whine at the loss of friction.
“I need to taste you, please.” He looked up at you, sliding off the bed and settling onto his knees below you.
He kept his eyes on your expression as he kissed up your thigh, “Teach me how to make you feel good.” He breathed into your skin.
“Please.” He begged, his fingers hooking around the hem of your underwear and sliding them down. Once they reached your ankles, he pulled them off and began sucking and licking up your inner calf, desperate to have you in anyway possible.
Your mouth fell open in awe at his desperation. His large hands clutched your inner thighs and spread them further, exposing your glistening, throbbing, needy core to him. He bit down on his lip hungrily at the sight.
“Please, baby.” He whined, tears welling up in his eyes.
You reached down and cupped his cheek, wiping away the tear tickling the corner of his eye.
“Look,” you instructed, bringing his head down, “you see how much I’m throbbing for you, Mikey?” You push your finger between your folds and spread them open, exposing your needy clit. He nods his head eagerly. “Lick me, right there.” Your hips arch forward in anticipation.
He pushes his head between your thighs and licks from your aching hole to the tip of your clit, collecting your arousal on his tongue. Your legs twitch at his soft touch and he moans at your taste. “So sweet.” He whispers to himself.
He pauses and looks up at you before doing it again on his own. He watches intently at the way your expression contorts into pure pleasure at the flick of his tongue.
Your stomach tightens at the overwhelming feeling of his tongue manipulating the most sensitive part of your body. Your hands tangle in his hair as you arch forward, pushing his head down into you more. “Just like that.. good job. Thank you for making me feel so good,” you cry out while grinding slowly against his tongue, “you’re so good at this, baby. Please don’t stop.”
His large hand grips your waist firmly, attempting to hold you in place. Noticing the absence of his other hand, you look down and see him using it to palm at his aching bulge over his jeans.
“M-Michael..” you stuttered out. “Take your pants off.” You instructed.
He looked up at you but he didn’t budge. He kept lapping his tongue at your dripping center. You pushed his head back slightly, his mouth detaching from you with a faint pop, forcing him to focus on your words.
“Stroke your dick for me, Michael. Please, baby? I really, really want to see you stroke your big cock for me. Touch yourself while you lick my pussy, Mikey. Can you do that for me, please?” You whine, your tone dripping with lust.
He stands up immediately, fumbling with his belt and pulling his jeans and boxers down in one swift motion. His dick sprung free from the restrictive denim and he groaned feeling it smack against his lower abdomen.
You watch him in awe as he wraps his large hand around his heavy shaft and strokes himself slowly from base to tip, dangerously close to your face. With your legs still wide open, you begin feeling yourself clench around nothing at the erotic sight.
He bent down, placing a sloppy open-mouthed kiss to your lips. His tongue desperately tasting the inside of your mouth.
He reaches down and pushes two fingers inside you causing you to gasp loudly into the kiss. His massive, elongated fingers stretching you caused you to dig your nails into his forearm and bite down on his lower lip. He curls them inside and moans at the feeling of your weeping pussy sucking him in, “Oh, fuck.” He groans.
He pulls his fingers back out and collects the mixture of your wetness and his saliva leaking out of you onto his fingers and strokes his dick with your evidence of desire.
“Oh, Michael..” you whimper at the erotic sight in front of you.
“Need you on my mouth again.” He whispers, kneeling down and positioning himself between your legs just like before as he begins sucking on your clit relentlessly.
“Please, mama… use my tongue again. Need to watch you.” He moans against your slick core, the vibrations sending waves of pleasure through your stomach and lower half.
“Oh, god. Michael..” You cry out. The feeling of his tongue lap at your clit desperately mixed with the lewd sounds of him pumping himself was almost too much.
Your hands grip onto the back of his head as he sticks his tongue out, begging for you to use it. You arch your hips forward and grind down on his tongue harshly. You both moan at the feeling.
“Oh my- oh- oh god.” You whimper.
He jerks himself faster below you, snaking his hand up the front of your shirt and caressing the soft skin underneath. His fingers grazed against your erect nipple sending chills through your whole body. You internally thank yourself for not wearing a bra today.
The padding of his thumb traced teasing circles over your nipple, causing you to arch your back into his touch. The hot coil in your stomach tightens at the overstimulation of the moment.
Your thighs tremble around his head and your hands tug at his hair at your nearing release, “M-Michael. I’m so close, baby. I’m so close.”
He laps at your core eagerly, desperate to feel you cum on his mouth. “Hmmm…” he hums, wrapping his lips around your clit.
The strong vibration caused you to come undone completely around his tongue. Creamy, slick liquid leaked out of you and onto his tongue. Your hole clenched and pulsated in his mouth as a loud cry ripped from your throat, “I’m cu-.. I’m cumming.. I’m cumming, oh fuck.”
He continued to suck and lick your throbbing center, swallowing every last drop of your cum.
“Mmm.. you look so pretty cumming in my mouth.” He whined against you. “Fuck..” he panted, his dick twitching in his palm, “I’m so close-“
“Not yet, come here.” You instructed. “Put your dick inside me, I wanna feel you.” You curled your finger, motioning him upwards.
You scooted back on the mattress as he climbed over you. He connected your lips in a desperate, hungry kiss. You pulled his shirt over his head and hugged him flush against your body.
He rubbed his dick along your entrance, his head falling between your breasts and a muffled moan escaping his lips. You caressed his head soothingly, “Cum inside me, baby.” You whispered.
He pushed his tip into you, stretching you so wide it almost felt masochistic. “Mama.. oh god,” he panted, “fuck- ahh.. oh my god.” He whimpered into your chest.
He pushed his whole length into you in a slow drag, a satisfied shriek ripping from your throat. “Uh huh.. yes, baby. Just like that. Good boy.” You praised breathlessly.
The tender reassurance made him feel dizzy. He pulled out of you slowly and sharply snapped his hips back into you. You feel warm liquid trickle down your collarbone as he pants into your chest.
You grab his face and the eyes that meet yours are hooded with pleasure and flooded with tears. “You feel so good, mama. You’re so tight.. I can’t take it..” he cries.
Your heart swells with adoration, causing you to pout. “You’re doing such a good job, baby. I’m so proud of you.” You whisper, brushing your lips against his before reconnecting them.
He strokes two more times in you before you feel him begin to twitch inside you. “Oh fuck.. I-I’m, I’m gonna-“ he strains against your mouth.
You inch his face back just barely enough to admire his expression, “That’s it, baby. Good job…” you encourage his release.
He grinds his hips upwards one more time, crying out your name like a prayer. “Mama… mama, it’s so- it feels- thank you, thank you.. oh my god, I’m-” he blurts out with tears streaming down his face as you feel his cum paint the inside of your walls clenching around him. You moan at the feeling of his warm liquid filling you up.
He collapses onto your chest and you both lie there in disbelief, your rapid heartbeats syncing with each other. He catches his breath and begins kissing slow, loving kisses up your neck until he reaches your lips again.
You sink into the tender kiss and wrap your arms around his neck, the kiss becoming lazy and sloppy. “You’re perfect.” He whispers faintly into your mouth.
A timid smile blossoms upon your face at the sweet affection. “You’re making me shy, stop!” You squeal bashfully.
“That is what makes you shy?” He says sarcastically, a loud laugh filling the room.
“Hey!” You light-handedly tap his cheek with a false annoyed expression on your face and he giggles.
“I’m teasing, baby. I’m sorry.” He apologizes, leaning down to place a kiss on the corner of your mouth.
“Mhmm..” you hum with a satisfied smile.
“Will you sleep with me tonight? Please?” He places ticklish kisses on your forehead, “Please?” Then your cheeks, “Please?” Then your chin, and your nose and your eye lids - anywhere he can see.
You giggle pushing him off of you slightly, turning your head away. “Okay! Okay! I will. I promise!”
He nuzzles into your neck as both his arms scoop you up coming between you in the mattress, taking a whiff of your warm scent. “I love you.” He says softly into your skin.
Your heart flutters at the sudden confession. “Your hearts racing.” He whispers, looking up at you.
His doe eyes pull at your heart strings and a soft “I love you too” escapes your lips before your mind can process it.
An adoring smile dances across his face as he plants another tender kiss to your lips.
You chuckle against his mouth when you remember, “so who’s the girl?”
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