﹕ (✿˘͈ᵕ˘͈) ┈ woof.
┊ ♡ ﹒ off the wall era! (｡•̀ᴗ-)✧
┊ ♡ ﹒ summary : michael is a lovesick loser boy and you get off on that. you say jump, and he says how high. why? because you’re pretty, give him attention and you have the pussy he can’t last three minutes in.
┊ ♡ ﹒ byi : smut! 🔞, submissive michael, mentions of face fucking.. but its not you getting your face fucked :), full on intercourse, reader is a D1 dirty talker, michael struggles with premature ejaculation, talks of loss of virginity, age gap (reader in mid to late twenties, michael is twenty one), strong emotional dependency, jealousy, codependent tendencies, idolization/idealization of a partner, insecurity (michael), power imbalance, bossy reader, lovesick michael. “daddy” is used to tease. reader is also a socialite. girl idk! there’s a lot to unpack here.
The roller rink was pulsing with life beneath a haze of colored lights. Purple, blue and red beams chased each other across the polished floor, reflecting off sequined jackets and the mirrored disco balls suspended from the ceiling.
The venue itself smelled of an array of things: hints of red icee and cotton candy, colognes, heavy hairspray and cigarette smoke as music thundered from enormous speakers mounted in the corners, bass vibrating through the walls and floor alike.
The rink was one of Los Angeles’ worst kept secrets. On any given weekend, half the city seemed to pass through its doors, LA personalities, aspiring musicians and even well known ones, actors, and industry kids all looking for a few hours of normalcy beneath the disco lights. Michael had even performed there once or twice over the years, drawing crowds that packed the floor shoulder to shoulder. Tonight though, he was there because it was Friday night, the music was good—or so he says.
He sat perched on the edge of a vinyl booth near the rink, one leg bouncing restlessly beneath the table. At twenty one, he occupied an awkward space between abandoning boyhood and stepping into superstardom. Off the Wall had transformed everything. People stared now. People whispered. Girls gathered the courage to approach him and then dissolved into nervous giggles halfway there. Yet somehow he still looked slightly uncomfortable with the attention, dressed in a fitted button down and dark bell bottoms, curls falling around his face as he watched the skaters glide by.
Across from him sat Bill, who had spent the better part of the evening pretending not to notice Michael checking the entrance every five minutes.
“Gonna wear a hole in the floor if you keep doing that, Joker.”
Michael looked away from the doors immediately. “Doin’ what?”
Bill chuckled. “Keep those feet still.”
Beside them, one of Michael’s managers leaned back with folded arms. “She’s not coming.”
Michael frowned. “Who?”
That earned him three unimpressed stares.
The manager laughed first. “Right. Sure.”
Michael rolled his eyes and reached for his orange juice, hiding a shy smile. “You guys are trouble..” The real truth was embarrassing enough without them making a spectacle of it.
You’d simply mentioned a few days ago that you might stop by the rink on Friday night around eleven. Any accusations that he was waiting for any particular person were completely unfounded. Baseless, even! The fact that he’d arrived early, picked a booth with a clear view of the entrance, and couldn’t seem to stop looking toward the doors was merely an unfortunate series of coincidences. Right? Right.
The music shifted into another song, drawing a fresh wave of skaters onto the floor. Michael watched absentmindedly, fingers drumming against the side of his cup.
Unfortunately for Michael, the second he saw you every carefully constructed fantasy he’d been rehearsing in his head before he went to sleep these past couple nights went poof! Oh, baby had the vision planned out so perfectly too. You would arrive alone, right? Perhaps a little late knowing how you girls were. Your eyes would find him across the rink.. he’d wave you over with a pretty smile, say something clever to make you giggle, something charming to make you blush, and the two of you would spend the whole evening together. Simple! Romantic! And honestly.. the sort of thing that only ever seemed possible in his imagination.
Instead, you arrived wrapped in a world that had nothing to do with him.
You were laughing before you had even fully stepped inside, surrounded by friends who seemed to orbit you as naturally as planets around the sun. One of them hooked an arm through yours. Another leaned close enough to whisper something that sent you into another fit of giggles. You moved through the crowd completely absorbed in your circle, tucked safely inside a bubble of conversation and affection that Michael found himself staring at with an intensity that bordered on painful.
It was ridiculous, really. He knew that. These were your friends. People who loved you. People who had every right to occupy your attention. Yet all he could think about was how easily they had access to you. They could stand beside you without overthinking. They could make you laugh without rehearsing every sentence beforehand. They could touch your arm, lean into your space, steal your attention for entire evenings without their heart threatening to beat itself clean out of their chest. Michael hated the ugly little stab of jealousy the realization inspired but it settled in anyway, impossible to ignore.
The worst part was that you looked so happy. Not even looking for him. Not wondering if he had shown up. Not scanning the room in search of a familiar face. You were perfectly content exactly where you were and that simple fact managed to burst his fantasy more effectively than outright rejection ever could have. It forced him to confront the embarrassing truth that while he had spent the better part of a week thinking about you, you had probably spent the week simply living your life.
His fingers tightened around his cup as he watched you laugh again, your head tilting back beneath the colorful lights. God, you were beautiful. So beautiful it almost felt unfair. There was something doll like about you tonight, something soft and luminous that seemed untouched by the chaos around you. For a moment, Michael forgot entirely about the drink in his hand. Orange juice slipped over the rim and splashed across the table, but he barely noticed. The pounding in his ears had grown so loud that the rest of the rink seemed to fade into the background.
All he could see was you.
And all he could think, with a mixture of longing and frustration that made him feel like an awkward teen instead of twenty one, was that every single person standing between him and you suddenly felt like an obstacle because they were occupying the exact place he wished he was.
The pounding in his ears was so loud he didn’t even hear Bill calling for him. “Michael.”
No response. “Michael.” Still nothing.
“Yeah, that brotha’s starvin’.” Bill says shaking his head, causing the other two in his party to chuckle at how adorably absurd this entire situation was.
The longer he watched, the worse it became.
At first, Michael told himself he was being dramatic. You had only been there a few minutes. There was no reason to assume you wouldn’t acknowledge him eventually. No reason to let his imagination run wild simply because you were occupied talking with your friends.
Yet with every passing moment, his confidence seemed to shrink.
You looked so settled over there. Every now and then another person would stop to greet you, extending the circle around you further. You laughed, listened, smiled, completely absorbed in whatever conversation was unfolding. Meanwhile, Michael remained exactly where he was, nursing a cup of orange juice and feeling increasingly foolish for having spent the entire evening waiting for you.
The ugly little voice in the back of his mind began whispering all the things he hated most.
Maybe you hadn’t come for him. Maybe you’d only mentioned stopping by in passing. Maybe you hadn’t even noticed he was there.
His stomach twisted.
The more he thought about it, the more embarrassed he became. Suddenly every hopeful fantasy he’d entertained over the past week felt very childish. Of course you weren’t looking for him. Why would you be? You had a life, friends, people you genuinely wanted to see. You were a socialite. The world did not stop spinning simply because Michael Jackson happened to have a crush.
Across the table, Bill watched the slow collapse unfold in real time. The slumped shoulders, distant stare, the deepening pout.
“Don’t start.”
Michael frowned. “’M not startin’ anything.” Oh! He has a little funky attitude now.
“Alright now.” Bill warned and Michael looked away.
For a moment, Michael seriously considered leaving the booth altogether. Maybe he’d skate a few laps, find something else to focus on. Anything was preferable to sitting there feeling sorry for himself while you remained blissfully unaware of the emotional catastrophe taking place twenty feet away.
Then it happened.
Your laughter softened as the conversation around you shifted, and for the first time since you'd arrived your attention wandered. Almost absentmindedly, your gaze swept across the rink drifting over the crowd until it landed on him.
Michael forgot how to breathe.
The feeling was instantaneous and overwhelming. One moment he had been sitting there stewing in his wounded pride, thoroughly convinced that you hadn’t noticed him all evening. The next, he found himself trapped beneath the weight of your attention, every insecurity he’d managed to accumulate over the last ten minutes suddenly feeling ridiculous.
Because you had noticed him.
And apparently, you’d noticed him quite a while ago. A smile began to form on your lips, and Michael felt his stomach drop for an entirely different reason.
It wasn’t a grin nor was it playful enough to be teasing or sweet enough to be innocent. It was something far more dangerous than either of those things. A smile touched with amusement and recognition, as though you’d caught sight of something you found particularly endearing. As though the sight of him sitting over there, staring at you from across the rink like a lovesick puppy had confirmed something you’d suspected all along.
Heat climbed his neck and the longer you looked at him, the more certain he became that you’d seen everything.
You’d seen him checking the entrance, seen him watching your group from across the room. Seen the way his mood had visibly soured the longer he convinced himself you weren’t coming over.
The realization should have mortified him. Instead, all it seemed to do was make him feel validated.
God.
You looked beautiful.
The colorful lights flashed across your face as you stood among your friends on the rink, completely at ease in a way Michael had always envied. While he spent half his life overthinking every conversation, every interaction, every glance, you moved through the world so effortlessly confident that made everything look easy. You never seemed concerned with whether people liked you. They just did. You never chased attention because it found you anyway.
And right now, all of that attention was directed at him.
Neither of you looked away as the skaters continued moving around you. Music thundered from the speakers. Laughter echoed throughout the rink.
Yet somehow the space between you felt strangely quiet.
Then you lifted your hand.
Just one finger.
Crooked toward yourself.
Come here.
It felt like a command because it absolutely was, with the confidence of someone who already knew exactly what would happen next. And the truly humiliating part was that you were right.
Michael was on his feet before his brain had fully processed the gesture. His knee struck the edge of the table and all the drinks nearly spilled over as the booth rattled violently.
A chorus of protests erupted behind him as he nearly sent the entire setup crashing to the floor, but Michael barely heard any of it. He was already moving through the crowd, abandoning every ounce of composure he’d spent the evening trying to maintain.
Behind him, Bill watched the scene unfold with the exhausted expression of a man witnessing something both embarrassing and completely predictable.
“Oh, man. That boy is gone.”
Because after all that moping, it had taken exactly one finger to get Michael Jackson moving. Not a greeting or even his name.
Just a look and a simple little come here.
And off he went.
You stood on the other side of the low barricade that separated the rink from the seating area, balanced easily on your own personal skates. Colored lights skimmed across the polished wood beneath your feet, catching on your jewelry every time you moved. Up close, Michael found you even more distracting. You smelled so good.
The journey across the rink had done absolutely nothing to improve his condition. If anything, it had made it worse.
“Hi, Michael.” You tilted your head slightly as you looked at him, your smile lingering at the corners of your mouth.
“Hi.” The response came out embarrassingly quiet.
For all the confidence he’d managed to summon while crossing the room, it deserted him the second he arrived. He was suddenly intensely interested in the floor, the barricade, the wheels on your skates, anything except your eyes.
A soft laugh escaped your lips. “You look nice.”
Before he could respond, your hand rose to straighten his collar. The gesture was casual and like muscle memory, and Michael felt every nerve in his body come alive beneath your touch. Your fingers smoothed the fabric before sliding behind his neck, settling briefly against the nape.
Your acrylics scratched lightly through his curls just enough to send a pleasant shiver down his spine.
You noticed the way his shoulders stiffened and your smile widened. “Miss me?”
Michael swallowed. The honest answer sat so heavily in his chest that he couldn’t think of a clever way around it.
“Yeah..” His voice was barely above a mumble.
You heard him but you pretended like you didn’t just to hear him say it again. “Hm?”
Then he nodded and a little louder, “Yeah.”
Something softened in your expression, satisfaction. You’d suspected that was going to be the answer and you were merely waiting to hear him say it.
“That’s sweet.”
Michael felt his face grow hotter. You, meanwhile, appeared completely unaffected.
“Go get skates.” You ordered
Michael blinked. “Pardon?” He wasn’t listening, he was staring.
”Go get skates.” You gave his shoulder a light push. “You’re not gonna sit over there all night, are you?”
“Oh, right!” Another blink. “Okay.”
You stared at him.
Michael stared back.
A laugh escaped you. “Michael.”
“Yeah?”
”Go.”
He nodded immediately. “Right. Okay.” Then he turned and started walking away to rent some skates for the night.
By the time the night was halfway over, the pattern had become impossible to ignore.
Michael had spent most of the night orbiting you.
Not hovering awkwardly across the room or lingering nearby under the pretense of doing his own thing. Deadass on you. Every time you moved, he ended up moving too. If you skated toward the opposite side of the rink, he followed. If you stopped to talk to someone, he appeared a few feet behind you waiting for you to get done. More than once, you’d looked over your shoulder only to discover him on your heels, wearing the innocent expression of a man who had absolutely no idea how he’d gotten there.
The funniest part was that he never seemed aware he was doing it, but you were no better.
At one point you’d hooked a finger through one of his belt loops and dragged him through a crowd because he kept getting distracted by people stopping to talk to him. Michael hadn’t protested, he was right where he wanted to be and simply allowed himself to be steered wherever you wanted him, weaving obediently between skaters and crowds alike while your friends tried not to laugh. Which by the way? You didn’t like very much, because you should always be the one giggling him out of his underwear.
Then later, there was a point where the music grew too loud and you’d grabbed his jaw to pull his face closer so you could hear him better.
“What?”
You’d tugged him forward. “What’d you say?”
Michael had repeated himself, this time barely three inches from your ear. The poor thing had nearly short circuited.
Now he was standing at the concession counter retrieving the drink you’s sent him to get, and your friends were watching him with poorly concealed amusement.
“Girl,” One of them said, glancing between you and Michael. “He’s been overly going. All night.”
A smile tugged at your mouth. “I know.”
Across the room, Michael accepted the drink from the cashier before immediately turning to look for you. The second he spotted you, he started heading back like clockwork.
You watched him approach, taking in the sight of him weaving through the crowd with such earnest determination that somehow managed to be both charming and ridiculous.
“He’s just as cute in person, right?” you asked.
Your friend barked out a laugh. “He’s cute but what if the shy thing is for appearances?”
You shrugged, not minding her. “I’ve known him for a while through my dad, he’s really like that. I think it’s charming.”
“How old is he again?”
“Twenty one.”
Your friend made a face. “Girl..”
“What?” You laughed. “I’m twenty (number).”
"I don't know— younger guys.. they be lowkey annoying.”
Your gaze drifted back toward Michael. He was almost there now, protecting the drink from being knocked out of his hands while navigating around people.
The sight made something warm settle in your chest.
“Mm.” You tilted your head slightly, she eyes him. “He’s been good to me though..”
Michael finally reached the group and immediately held out the drink you’d asked for and his expression brightened the moment you took it.
Like he’d just accomplished something so important.
You were feeling generous tonight, maybe even a little possessive.
That was the only explanation you could come up with later, because the way the evening had escalated felt almost absurd in retrospect. One moment Michael had been trailing after you everywhere you went, carrying drinks, accepting orders, allowing himself to be tugged through crowds by his ear whenever he drifted too far away from you. The next, you were standing beside him beneath the flashing lights, watching him laugh again at something one of your girlfriends said, and making a decision that surprised even you because usually you were much more.. tactful.
Maybe it was the way he’d spent the entire night looking at you or the fact that he’d never once complained. Maybe it was because every time you called his name, he appeared instantly.
Whatever the reason, you’d found yourself gliding up beside him as the night began winding down. Michael was midway through a conversation with Bill when you hooked a finger through the front of his shirt and pulled him down slightly.
He went without resistance.
Of course he did.
The music was still loud enough that nobody else could hear you as you leaned close, your lips brushing the shell of his ear.
“You’re coming home with me tonight.” You felt him go completely still. “Say bye bye to Bill and your people, ‘kay?”
For a moment, Michael simply stared at the floor and you watched the reaction spread down his neck. When he finally looked at you, there was something dazed in his expression, as though his brain had temporarily stopped functioning.
“Okay.” The answer came so fast you nearly laughed.
Not where?
Not why?
Not even a hesitant really?
Just: “Okay.”
You bit back a smile and wave at Bill as she glides away back to her table and Michael had barely managed three words of explanation before Bill figured it out.
Not that there had been much mystery to solve, the equation practically solved itself.
Bill sighed heavily. “You serious?”
Michael nodded. “Yeah.”
“She askin’ or tellin’?” Bill immediately had his answer when Michael coughed in response.
Michael looked down at the floor and Bill shook his head. “Son, one of these days you’re gonna have to stop jumpin’every time that woman points somewhere.”
Michael’s embarrassment deepened. “I don’t do that.”
The thing was, Bill liked you. You made Michael happy. You were good to him. You looked after him in your own way.
Bill had no objections there. His issue was the complete collapse of Michael’s spine whenever you entered the equation.
The boy had spent all evening following you around like he’d been hired for the job. “You know she already likes you, right?” Bill asked.
Michael blinked. “Huh?”
Bill rubbed his face. “She already likes you.”
Michael stared, the very suggestion seemed impossible to him. “But..”
Bill already knew where this was going. “But what?”
Michael shrugged awkwardly.
“She’s..”
“Pretty?” Michael nodded.
“Successful?” Another nod.
“Older than you?” A smaller nod.
Bill threw his hands in the air. “And?”
Michael didn’t answer, because that was the problem.
Somewhere deep down, Michael still couldn’t understand why someone like you would choose him when you could have anybody. Meanwhile, everyone around him had been forced to watch you practically drag him around a roller rink all evening.
Bill snorted. “Son, if you don’t quit feelin’ sorry for yourself."
Michael frowned. “I’m not..”
Bill laughed. “She got you fetchin’ drinks, carryin’ her stuff, followin’ her around, and lookin’ at her like she hung the moon.”
Michael buried his face in his hands.
You looked over your shoulder at him across the room, probably to see what was taking so long and the second Michael noticed, he straightened.
Bill caught it and a long, exhausted sigh followed.
Then he patted Michael’s shoulder. “Go on. Use protection.”
Michael sputtered. “You’re talkin’ dirty! I’m a gentleman.”
Bill shook his head. “You hopeless.”
The funny thing is Bill didn’t dislike the dynamic. He probably finds it adorable. He just spends a lot of the time trying, and failing, to convince Michael that being loved by a confident woman did not require acting like he’d been personally selected by royalty every single day. Michael, unfortunately, would continue acting exactly like that.
Because he loved bossy women.
You were beautiful—everyone knew that. It wasn’t exactly a revolutionary observation. People noticed when you walked into a room, they turned their heads and stumbled over conversations, found reasons to linger a little longer in your presence.
But Michael’s problem had long since surpassed simple attraction, because your pussy was the closest thing Michael thought he’d ever get to experiencing heaven while he was still on earth.
The thing about Michael was that he was sort of person who experienced affection through proximity. He liked sitting close enough for your shoulders to touch. He liked feeling your weight beside him on a couch. He liked the absent minded ways you occupied space, the little touches that seemed insignificant to everyone else but somehow lingered in his mind for days afterward.
The truth was that he never quite got used to you, even more so because you were the one to take his virginity.
Some people eventually acclimated to affection, they normalized it and over time, they came to expect it. Michael never seemed capable of doing that. Every act of intimacy, no matter how small, retained its ability to affect him. A hand on the back of his neck. Your fingers smoothing his collar. Your arm looping through his. Tiny gestures that should have become ordinary by now somehow remained extraordinary.
There’s unfortunately just a small part of him still couldn’t believe he was being chosen.
For Michael, intimacy was never something separate from affection. The two were hopelessly intertwined. Physical closeness carried an emotional weight that he couldn’t easily detach from which is why he’s so enamored with you. Where other people might eventually grow accustomed to being loved, Michael seemed determined to remain grateful for it. The familiarity never dulled his appreciation.
You’re no longer just the woman he has a crush on. You’re the person he trusted with something deeply personal. The person who guided him through an experience he had spent years imagining, worrying about, romanticizing, and building up in his head.
The irony is that it probably makes him less focused on sex itself and more focused on you.
Because afterward, what’s left isn’t necessarily the memory of the sex. It’s the memory of your kindness. Your patience. The way you looked at him during. The fact that you wanted him there with you. The feeling of being accepted completely, without performance or expectation.
For someone like Michael, that would be difficult to separate from love. Very difficult.
“Fuck, Michael,” You feel breathless, hands resting on the sides of his abdomen as you wrap your legs around his waist. Michael balances his weight above you, palms spread out on your soft bedding as you pull him closer with each thrust deeper into your pussy. Your pubic bones met with each movement, curly bushes intermingling and creating a friction. “That feel s’good, baby. Can’t believe you’re fuckin’ me this good..”
Michael’s face twists with a cute strain, his eyes squeeze shut so tightly his brows pinch. Every muscle in his body goes rigid as he fights the overwhelming to pump his nut inside of you. He can’t cum now. It’s too early, it’s way too soon. He can’t. He can’t. It’s barely been three minutes! But the filth spilling from your pretty lips in such a nasty tone makes his dick fucking throb and jerk against your tight walls. ”Lovey.. stop—stop.. stop talkin’ for a second..”
You know exactly what you’re doing, but you don’t mind. He’s been very generous with his mouth tonight and you can’t even count the amount of times you used his tongue to get off. Emphasis on you using his tongue, he’s eager to please but he still needs a little guidance. So, usually when he’s between your legs, you’re practically face fucking him. Hands in his curly coils to hold him in place as you roll your clit along his tongue.
Your heavy breasts bounce and sway with each sloppy thrust, jiggling provocatively under his straining chest. You reach up, soft palms cupping his tense cheeks, tenderly stroking his sweaty skin as you whisper.
“Look,” You tilt his face down, forcing him to look directly beneath the two of you—making him watch. “Look at that dick fucking your pussy, daddy.” He lets out a particularly pathetic whine as the nickname, you only use it to tease him but he seems to like it even though.. he’s not really the ”daddy” type. He watches as his slick, latex covered cock pushes relentlessly in and out of your pretty petaled pussy. The smooth wrapper makes his shaft glide effortlessly, pumping in and out as his dark skin contrasts against the lighter colored latex. Fuck, it’s pretty. All six inches of it.
“Who’s pussy is this? Let me know..” You grab his jaw, making him look at you as you gently runs a finger down his bottom lip to watch it pop back into place.
“It’s mine..” He whimpers out.
“Yeah? ’s all yours?” You smile, slipping her ring and middle finger into his mouth.
“Mhm..” He nods, closing his eyes again as he sucks on her fingers.
“Look at me, baby..” You say and he reluctantly does as he’s told. “I love watching you fuck me this good..” You look up at him with those big soft eyes, your expression melting into a breathtaking mix of pure adoration and overwhelming affection. Right now, there’s nothing dirty in your gaze now, only a deep, lovesick tenderness that reciprocates his same feelings for you—and it completely unravels him. Seeing you look at him with such.. love is his absolute undoing, shattering his control instantly.
Michael’s hips start to stutter and falter, his rhythm breaking as he approaches his high. His face contorts with distress, a mixture of pleasure and panic etched into his features.
“Oh—m’god..” He pants, his breath coming in ragged gasps. “Can’t.. that's gonna make me..”
“Make you what, angel face? Cum?” You smile.
“I can’t—I really can’t..” There’s really no warning.
Michael’s body suddenly goes rigid and his hips press deep as he buries himself completely inside you. His muscles tense and twitch as wave after wave of intense pleasure crashes over him, filling the condom with thick ropes of hot, sticky cum.
Michael collapses fully onto you, his strength completely spent as his body trembles uncontrollably. His hips continue to rut instinctively, pathetic little twitches driving his spent cock deeper into your warmth as he rides out the overwhelming aftershocks. His face buries into you shoulder, whimpering softly.
“Sorry.. sorry—felt too good..” There’s always a sense of shame that sits on his chest because since he’s been having sex, he’s been struggling with prematurely finishing. But you always tell him it’s not his fault when he brings it up hours later, his body has never known a woman until relatively recently. It just makes his body notoriously hypersensitive and prone to finishing too soon. It takes some time to build an endurance. But what he lacks in lasting, he makes up for with his refractory period which is seemingly nonexistent.
But that’s a story for a different day.
© michaeldiary. 2026. do not copy, repost, translate, or feed into ai.
