summary | Five years of being his assistant and five years of failed attempts at finding love with your help, but maybe the obvious answer has been there the entire time. Alternatively, you fucked your boss? Uh-oh.
author's note | harry...randy...who knows. i'll change it if needed but given the name tag, this is what i'm sticking with for now. skip the lecture about not writing until the movie is out, this isn't hurting anyone so don't bother me about it, xo. the horny demons always win. i listened to this song i repeat while i wrote, felt fitting.
content warning | 18+ MDNI, power imbalance (boss/assistant), work wife/work husband type beat, mentions of failed dating, being superficial, mentions of sugar daddy things, expensive gifts, reader is a godly assistant with a will stronger than mine, he smokes, they drink, sex while inebriated, he's down so bad, also oral!, tense morning after, open-ended
word count — 4.5k
You knew him better than anyone.
From his breakfast order down to his specific choice of underwear, like you weren’t making the weekly purchases and filling up his rarely used fridge in the apartment that was way out your price range, arranging his schedule down to the minute, booking his flights, packing his bag.
Really, Harry should just marry you.
…it was more of a joke, but you’ve teased him about it once or twice.
He called you his work wife anyways, but in reality, you were just his assistant.
He did trust you with his life, though.
More importantly, his love life.
“Kim flaked,” he tells you over coffee, perched at his kitchen island as you typed away on your laptop, looking up briefly with eyes that begged for him to explain, he does and makes a show about, mimicking a more feminine voice as he relays the message she gave him, “same song and dance—you’re great and fun but I can’t do anything serious right now,”
“Were you nice?” you ask curiously.
Harry rolls his eyes at that, like it was a stupid question to ask. But, eventually he nods.
“Did you ask questions?” you continue, fingers folding over the screen of your laptop to close it.
“Plenty, she works in finance, loves the color blue, wants to travel,” he could go on and on, throwing his hands up in defeat before they slump to his side, “maybe I should try out a real matchmaker—not that you’re bad at it—”
“You think I’m bad at it,” you smile knowingly, “don’t you?”
“No,” you’re unconvinced, “besides—you’re my assistant, I never meant for that type of responsibility to fall on you, you know?”
“I’m doing both of us a favor,” you remind him, “I think…it just takes time.”
And fortunately, all you had was time.
It felt pointless for Harry to spend a chunk of cash to have someone pair him up with the supposed love of his life, though you knew that money wasn’t a problem, you felt a weird responsibility to protect him, unsure how quickly someone would take advantage of his kindness.
“There’s a gala,” you tell him offhandedly, “next week. I already cleared your schedule for it. I think…maybe you should just peruse this time.”
“Peruse?” he chuckles, eyes creasing in amusement, his crow’s feet deepening with the emotion, “You’re a control freak, you sure about that?”
“That’s just mean,” you retort, “you’re paying me anyways—if you didn’t like it you’d fire me.”
He knew you were right, sipping quietly at his coffee in response.
He was frustrating, predictable, and painfully superficial.
Every date was an exercise in appearances—perfectly tailored suits, dinner at the most exclusive places, charm turned up to eleven. And yet, none of it ever stuck. He was overcompensating and you weren’t sure why.
He was a good guy, down to his core, and in the five years you had worked with him there was never a moment you thought he didn’t deserve love, he was perfect. Too perfect.
That was the problem.
“You know, you’re like prime age to be a sugar daddy,” you tease him, knowing how he felt about the topic, “there’s plenty of apps that I can—”
“You’re relentless,” he grumbles, “if you ever did that, I’m firing you on the spot.”
“You wouldn’t,” it was a gentle challenge, smirk flashing across your face as he returned it with fondness, “without me you would crash and burn, Mr. Castillo.”
And he knows it.
–
The gala is a bust.
So, as a bandaid to his wounded ego, you order takeout and keep him company in his big, lavish apartment—it wasn’t the first time, it wouldn’t be the last.
You knew what the issue was, but there was a sinking feeling in your stomach that told you he wouldn’t receive the information well.
It was after every failed date, every expensive dinner.
They saw him at the surface, the charming man with an easy, warm smile.
You saw the man who kicked his shoes off and stripped himself of his suit jacket the second he walked through the door, who couldn’t resist a late-night binge of his newest streaming obsession, someone who insisted on stirring his coffee counterclockwise because it made it taste better, a man would text you pictures of squirrels in the park that he would feed on his way home.
It wasn’t that you were pining over him. You just knew him better than anyone.
“Why are you so dead set on marriage?” you ask him over dinner, turned toward him on the couch as he reaches for the remote to pause the show on screen.
He’s had this conversation before, but he’s never asked you any questions on the matter.
“What’s your opinion on it?” he’s avoiding, clearly, but you’ll bite.
“I don’t date, I’m not interested, signing a piece of paper isn’t going to signify my feelings toward someone if it came down to that,” you admit, “I’m not cynical, marriage is fine, but this stuff takes time,”
“Well, I’m not getting any younger,” Harry gripes, arms reaching over the back of the couch as he mirrors your position.
“Oh, please,” you scoff, “you’re forty-nine.”
“Almost fifty,” he corrects, “I’m ancient.”
“O-kay,” you sigh, “do you want honesty?”
“I’d hope you were being honest with me all the time.”
“No,” you laugh softly, “like…brutal fucking honesty?”
He’s silent, but attentive.
“You keep choosing women who treat you like they’re next getaway vacation and you fall for it every time,” his forehead creases at the words, looking hurt by your words, “I see your bank payments every month, the activity—”
“It’s not like money is an issue,” he defends, causing you to sigh dramatically and fall back against the arm of the couch in faux distress.
“This is impossible,” you groan, staring up at the ceiling before you feel his hand circle around your wrist, tugging gently,
“Okay, I’m listening,” Harry says softly, pulling you upright, “I’m sorry—I am.”
“You want it to work so bad,” you tell him, “I see it—every time you approach someone you put on that smile and it works, but you’re giving so much and yeah, maybe some of them like that, but I’m sure a few would just enjoy a nice dinner here, or something simple. I think you forget to realize that someone can just be interested in you, for you, not for what you are or have,”
It’s profound, the way his face softens at your words, his touch still lingering around your wrist.
You’ve never even considered or entertained the idea that you might find Harry attractive or even attainable—for one, you had signed a contract that agreed to a professional work relationship, as a benefit for both of you, not that he ever had any intention to begin with.
You’ve been with him for so long, it feels, a fresh and young mind to help keep him active and busy, constantly refreshing ideas and helping him not feel like he was stuck, and you were damn good at taking care of him when he’s often tended to neglect himself.
The only thing you know is that he’s never looked at you like that.
Like you could see straight through him, all his flaws on display.
But, that was because you knew all of them.
You knew everything about him, even the worse bits.
His bad habits, his self-inflicting ones, everything that he refused to bring to the surface.
Harry’s fingers still lingered around your wrist, the weight of your words sinking in.
But then, just like he always did, he broke the tension with a huff of laughter and frowns as he brushed you off.
“You just think I’m a sucker, don’t you?”
You shook your head with a faint smile, returning your arm to your lap.
“No—I think you like to see the good in people. So much good that you’re willing to ignore red flags.”
“Jeez,” he chuckled, clutching his stomach like you had physically wounded him, “that hurt.”
You shrugged and reached for the remote to resume the picture on screen, “You’ll survive.”
–
It was your day off—Sunday, the one day.
“Have you seen my cufflinks laying around?” he asked over the video call, “Shit—my tie, too. I can’t find it anywhere. I thought you said you laid it out for me.”
“No, I said I had it hung up and for you to lay it out before you showered,” you correct him, laying tiredly on your couch as you watched him search around frantically, hair damp and his bare shoulders on display, only catching the briefest glimpses of the towel around his waist as he turned the camera around, “Waitwait—go back!”
“There’s no fucking way you saw it,” Harry argues, “I’ve been looking for the last ten minutes—”
“In the pocket of your suit, the tie is there,” you tell him, “and given that you probably tossed the suit on the bed like you always do, the cufflinks are probably somewhere hiding under the blanket,”
He tosses you against the mattress, your screen succumbing to darkness as you wait, some shifting of the sheets before you hear him make a sound before he appears again, cufflinks pinched between his fingers and a look of defeat on his face.
“What would you do without me?” you ask with a cocky grin, finger hovering over the end call button as he shakes his head.
“What was this for again?” Harry asks curiously, laying you down upright as you caught a glimpse of his bare chest as he shrugged the crisp, white button down over his shoulders.
“It’s a charity auction, your favorite,” you chirp, “and you’re flying solo, so—don’t do anything stupid or…crass,”
“If I paid you double a day of work would you go?” Harry asks after a long pause, glancing down at the screen, “Triple?”
“Triple?!” you gawk, “see—you’re insane, this is what I’m talking about,”
He chuckles despite your response, “You’re good at keeping the sharks away,”
There were particular hawking businessmen who made it their mission to hunt Harry down at events and keep him occupied, eager to do business, whatever it may be—you were the unspoken master of redirection, as much as he refused to admit it.
“Can we grab dinner on the way?”
“Burgers?” Harry asks, perking up slightly.
It was a constant go-to for you and him.
You nod through the screen, “Don’t even bother with the tie either, I’ll do it.”
–
“I can’t believe you roped me into this on my day off,” you whisper at his side, earning a half-smirk from him.
The charity auction was as lavish as you’d expected.
Crystal chandeliers, gold accents, and far too much champagne and hors d'oeuvres.
Harry’s hand found the small of your back the moment you arrived, steering you through a sea of designer gowns and tuxedos, feeling uncomfortable in the tight dress and stilettos that you only wore on rare occasions, biting at your heels.
“You’ll survive,” he grins, grabbing you both a glass of champagne and pressing it into your waiting fingers, “I’m gonna…peruse, alright?”
“Don’t say it—that just makes you sound like a creep,” your face scrunches up in disgust as you sip at the alcohol, “just go—go, I’ll…handle everything else.”
The evening passed in a blur of small talk and polite smiles, but somewhere between the endless speeches and bidding wars, you found yourself on the balcony, the cool night air a welcome relief in the stuffy ballroom.
You smell him before you see him, the thick and rich scent of his cologne so familiar you swear you could find him on that alone, turning over your shoulder to see him closing the door quietly, cigarette pack tucked in his palm as he approached with a neutral expression.
“You okay?” you ask, leaning against the railing of the balcony.
Harry sighed, rubbing the back of his neck and then plucking a single cigarette from the box, “Honestly? I’m just tired of it.”
“The auctions? Charity?” you inquire, a small smile tugging at your face.
“All of it.” He looked at you, his gaze lingering as he lit the tobacco, “The events, the dates, searching for—I don’t even fucking know at this point,”
“The offer stands…” you say jokingly, though he knows exactly where this is heading.
“If I wanted a sugar baby I’d find one.”
Your eyes roam over his figure as he puffs at the cigarette, pulling a deep laugh from his chest before you’re pushing him away playfully.
“Let’s go,” he tells you with a deep sigh, stubbing out the end of the cigarette and tucking it away for later, tossing his arm over your shoulder as he readied to guide you through the crowd, always protective in spaces like this, another thing that was special to him.
–
The ride home is quiet, like it always is, both of you sitting in the backseat with the partition up, watching as he looked through his phone with a scowl, occasional typing and sending a message.
Eventually, he looks at you.
“Thank you,” He says with a soft tone, “I know this isn’t your favorite thing to do.”
You tilted your head into the headrest and smiled, crossing one thigh over the other as you worked at your heels to remove them, “Oh, it wasn’t that bad—the free alcohol is always a plus.”
He chuckled at that, silently helping you remove your shoes with a soft squeeze to your foot.
That was normal—but, it forces you to pause.
His natural instinct to help, to touch, to comfort you.
Your brow furrows at the gesture before you shake it away, blaming it on the buzz of alcohol in your system, watching as he continues the gesture with the other foot.
“Having you there makes it bearable, is all,” he explains, looking up at you briefly as he undid the tie around your ankle, “you…calm me, I guess.”
You swallowed. Hard.
The warmth of his words lingering in your chest, in his touch against your ankle, “You’d do the same for me.”
And he would—if you ever needed anything, anything, Harry was there.
“Yeah,” he agreed quietly, “without question.”
The sincerity caught you off guard.
You turned to study him, the familiar slope of his nose, the line of his jaw. There was something about the way he looked tonight—tired, maybe, but softer.
And he keeps looking at you, checking.
The car moved smoothly through the dimly lit streets, the city blurring past in streaks of gold and blues and reds. The hum of the engine was steady, the faint sound of music barely audible from the front, through the glass, the back lit up dimly by the trim of lights on the roof and door.
Harry leaned back, one hand moved against the seat, his other hand dragging slowly over his thigh—restless.
Instinctually, without thinking, you reached for his hand.
It wasn’t purposeful. Just a simple act of absentmindedness.
You’ve done it a hundred times before.
Tugged at his sleeves to fix his cufflinks, brushed lint from his lapel or pants, adjusted the collar of his shirts. Constantly fixed his hair, touching him wasn’t new.
His skin was warm. Not hot, not cold.
You felt the slight twitch of his hand, like he was debating whether to move. Instead, his fingers shifted, just a fraction, enough that the edge of his thumbnail brushed over the inside of your wrist.
The contact was thoughtless, nothing.
But, in the same moment, it felt like everything.
The way his eyes watched the movement, roamed your body like they had before but with a different implication, his eyes half-lidded and relaxed, wondering how much alcohol he had consumed himself—this wasn’t friendly.
And it definitely wasn’t professional.
Harry’s gaze was on you now, your face, as you couldn’t tear your eyes away from his hand.
Then his thumb moved.
Up.
Barely.
A soft drag along your pulse.
It was half a decade of avoidance, defeat in his heart and mind, and fear in your own.
Broken, by the car rolling to a stop outside of Harry’s apartment building.
“We’re here, Mr. Castillo,” the voice of the driver came from the front, a nod of acknowledgement as his hand slipped from yours.
“Oh, hold on,” you were scooting aside to let him out, readied for the next stop as he cocks his head toward the building, “I’ve got something for you—I’ll drive you home, don’t worry,”
“Harry,” you stress, looking down at his hand that waves you toward him, extending out for you to grab, insistently as his fingers wiggle in wait.
Turns out, he wasn’t totally lying.
That something was accompanied by a seven thousand dollar bottle of Leroz Aux Brulees—you knew that because you had purchased it during his trip to France, the supposed city of love.
“I’m going to murder you,” you tell him as he places the bottle on the counter and keeps the closed case of mystery at his side, “hide your body, flee country—I hate surprises, you know that.”
“I think you’ll like this one,” he grins, popping the cork on the bottle and pouring two hefty glasses, eyeing the deep red as it glugged into the glass.
“You know, if you wanted company you could have just asked,” you tell him, “I get it, you’re lonely,”
He knows you’re only teasing but it stings nonetheless, both of you taking a long and heavy sip as his fingers swirl over the velvet casing before he’s pushing it over quickly, tapping it with his fingers, “Open it,” he encourages, eyeing you over the rim.
You place your glass down and pry it open slowly, carefully, like you were deconstructing a bomb, but as the piece inside comes into view you find yourself at a loss for words or thoughts.
Your eyes are wide, staring up at him with parted lips that tingled from the lingering alcohol, knowing you should have cut yourself off at one glass of champagne and refused to come inside, that you should have just went home and enjoyed what little bit of the day you had left to yourself.
Now, you were looking back at a necklace so delicate you were afraid to stare at it too long, embedded with a cluster of diamonds and nearly two years of your rent if you were doing the math correctly in your mind.
Always about the numbers, Harry constantly teased.
“I saw how you looked at it the other day,” he admits, “and I owe you a hell of a lot more, but it…I’m trying to say thank you for…being you,”
“I’m not taking that,” you refuse with a laugh of disbelief, sliding back over to him gently, downing the rest of your wine in one go to forget how fast your heart was beating in your chest.
“You are,” Harry insists, “consider it a bonus—Christmas is in a couple months, too.”
“You know…this is exactly that kind of stuff a sugar da—”
Harry makes a noise, shaking his head.
You bite your lip in thought, ignoring his subtle annoyance at your comment.
It was fucking beautiful, really.
You sigh, using one finger to turn the case back toward you, examining it closely.
Quietly, Harry presses his glass into the counter and rounds the edge toward you, his chest at your shoulder as he reaches for the jewelry, working carefully at the clasp before he’s motioning for you to relax your shoulders.
It wasn’t the stillness of the moment, but his touch, again.
He’s methodical in the way he touches you, dragging his hand around your neck as he fits the necklace into place, his fingertips pressing against the column of your throat in a way that tickles slightly, shifting uncomfortably until you hear the faint click and he breathes behind you, hands resting at your shoulders.
You’re not sure why he hasn’t moved, but you find yourself turning to speak.
“I’m just going to call an uber,” you tell him, “probably shouldn’t drive since we’ve both been drinking,”
“Yeah,” he agrees, but it sounds hollow, his eyes not following you as you move.
You hop from the chair and bend down to grab your shoes, but his hand is curling around your bicep and pulling you up and he’s staring again, the charge of his touch sending a jolt through your body as freeze,
“Come here,” he beckons, too natural.
And you listen.
He’s soft, every part of him. Skin, clothes, hair, lips.
He’s kissing you gently, like you might break, but you can tell he wants more.
Needs more.
“Are you going to regret this tomorrow?” you find yourself asking as he parts from you, licking at his lips as you both take a breath, letting the moment settle.
He shakes his head, “Are you?”
“Maybe,” you answer honestly, “maybe…not—fuck, I don’t know,”
“It doesn’t have to mean anything,” he promises, but you knew that was a lie.
Still, you nod in understanding.
–
He’s so tender with his touch, slipping you out of the dress in the dim light of his room.
Even softer as he guides you to your back and spreads himself on his belly between your legs, fingers interlocked with his at your hips as he buries his nose between your folds, his tongue splitting your cunt open in a sharp gasp that has you throwing your head back. His lips traced a slow, deliberate path down your body, igniting sparks along every inch of your skin.
He kissed along the curve of your thighs, teasing, tasting, until the tension was unbearable and with each flick of his tongue, each gentle suck, it pulled you deeper into a haze of heady desire.
This was reckless, dangerous, but neither of you found the moment to pause and think.
You wonder if things had been building to this for a while—if it was always supposed to happen this way or if he was acting off of greed; lust and companionship, even if just for a night.
You know you can ask him to stop at any point and he would, but even as his tongue brings you to your first orgasm of the night and he’s guiding you to your stomach, reaching blindly into his bedside table for a foil wrapping the crinkles loudly in the silence, you want this.
It was embarrassing how badly you wanted this.
He fucks you slow, too.
It was torturous, his chest flat against your back as he palms his cock and feeds it into you.
You don’t talk, neither does he.
But, his low moans and stuttering breaths speak for him.
If you could see him, you’d know how furrowed his brow would be, a hand sliding over the curve of your ass until he can reach your thigh, beckoning for you to raise it without speaking.
You oblige, the angle of his thrusts changing on a dime.
“I can’t believe you’re real sometimes,” he admits like he’s confessing a sin.
You feel him nod where his forehead is pressed between your shoulder blades as his fist curls into the sheet beside your head.
“Another, gimme another,” he pleads, the fingers on his other hand curling under your neck to life your chin, not expecting to meet his eyes as he leans over you.
The expression on his face so raw it makes you flutter around him, his lips parting in a deep, guttural groan, “I know you can,” he nods hurriedly.
And damn, does the praise work.
Your whimper breaks him, breathing out shakily as you locked eyes when he comes, slow and forceful thrusts until you’re nothing but an exhausted pile of tangled limbs.
“Greedy girl,” he comments through the haze, a weak giggle bubbling from your chest.
He pulls out slowly, a low grunt as he does so.
You’re not sure when you fall asleep, but you wake to a startling amount of weight over your stomach, an arm splayed possessively, the faint outline of a ring as you drag your hand over the limb.
It’s only as your eyes pry open that reality hits you, stumbling out of bed quickly.
No…nononono, where the fuck were your clothes? Jesus.
You stumble around half awake, searching for the silk dress on the floor, feeling accomplished when you find it and hastily redressing yourself as Harry stirs in bed, encouraging you to hurry, to slip out before he can say anything.
Your shoes are already on and you’re reaching for the doorknob when the voice comes, the weight of the necklace that still remained on your neck, two empty glasses of wine on the counter, a night of hasty choices and urgency laid out like a crime scene as his voice rings out from behind you, pleading.
“Don’t—don’t go,” Harry begs, “You don’t have to go,”
So much of this was wrong—it complicated everything.
Your life, your job, your relationship with him.
He can see you slipping, fingers inching toward the knob as he approaches you in a hurry, barefoot and shirtless, the kind of scene you shouldn’t be comforted with, like this was all normal to the both of you.
You’ve seen him like this a thousand times, but not when he’s looking at you so vulnerable, heart tore open and stapled to his chest, beating against your own as his hands splayed out over your cheeks.
“I don’t regret it,” he assures you again, “so please—stay, okay?”
“What changed?” you ask, voice trembling, “Five years, Harry. Five.”
“I’ve been running in circles this entire time,” he admits, “you know it—I know it.”
You had been there the entire time, learning every part of him without judgement, cataloging his flaws and skills, learning how he ticked and what motivated him. You had never quite settled on the ideal person to fit in his life as his partner, it surely wasn’t you.
It couldn’t be you.
“Please, don’t go,” Harry echoed once more.
The sick, cruel joke of it all was that this was your job.
You had nowhere to go. If it was any other morning, you would just be arriving, leaving his breakfast in the kitchen and starting your day.
You nod solemnly, “Of course, Mr. Castillo.”
It was painstaking, forcing the mask back on.
But, you couldn’t deal with this now.
Or ever, even.
Harry looks at you with a confused sadness, thumbs rubbing at your cheekbones before his hands fall to his side.
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