EARNED IT
Part 1 of 2 | Harry Castillo x f!reader
summary: Harry is a man who always needs control. But when you come along, the lines between lust, obsession, and love start to blur, and he gets the urge to let go completely.
contents/warnings: Explicit (18+ MDNI!) - fifty shades of grey vibes, AU, banter, playing hard to get, age gap (nearly 30 years⊠oops), Harry is a playboy, mentions of sex workers, longing, obsession, possessiveness and jealousy, dark romance (??), learning to love, one face slap, angst (i cannot be stopped), some description of reader (long enough hair to put up, sex on legs according to Harry), no uses of y/n. Apologies if I missed anything.
smut tags: m!masturbation, overstimulation, impure day dreams, dirty talk, dubcon (??), unprotected sex, a few ass slaps, rough sex, sex contract, exhibitionism, aftercare (kinda), the red room đ, sex toys
wc: 9600+ (oops)
a/n: my entry for @time-for-my-weekly-spanking 's 2026 kinky challenge (i chose age gap for my husband Harry). biggg thank you to @mcthsman for proofreading and helping me edit this! love you lots đ€ (more notes at the end)
áŻœ part 2 | soundtrack | read on ao3
Harry Castillo is a man of power. He works for the private equity business that his mother started up when she was younger, and he owns the most businesses out of anyone there. Besides his mother of course.Â
The Castillos have never been afraid of money. Hell, they bathe in it every night. Because of this, Harry isnât afraid to spend a pretty penny on a woman. Except he hasnât found someone that actually deserved it.
Sure, heâs had his fair share of women â none that heâs ever been photographed with. A list extending from women heâs worked with to sex workers. But no one has interested him long enough for him to think about any type of future with them. Heâs not necessarily proud of his ways, but itâs a big stress relief for him.
Control is a necessity in all parts of Harryâs life â including in the bedroom. These women willingly submit themselves to please him in whatever way he desires. Of course, Harry still respects them and makes sure theyâre properly taken care of. After all, heâs not a dick. He just thinks with his.Â
Harry is currently on a phone call in his office. Something about a leak that was reported in a recent building he bought. To be honest, he tunes out the man on the other end about halfway into the conversation.
âYeah, Iâll look into it,â he says, exasperated as he waits to end the phone call sooner rather than later.
âOkay. Thank you, Mr. Castillo. Have a goodââ
The manâs voice dies out as Harry puts down the phone, effectively ending the conversation before the man could finish his thought. He slumps back in his chair, running a hand down his face.Â
Crown Castillo has been the busiest and biggest itâs ever been. The annual New Years gala is in a few weeks, and his mother wants him to have a date for it. Harry could get any woman he wants for it, really. But he has been getting tired of that life. He is well into his fifties and coming to terms with the fact that he might end up alone.
Just then, his assistant, Rick, knocks on his door. âCome in,â Harry calls out, sitting up straight in his chair.
The door slowly opens before Rick steps in, âMr. Castillo, thereâs a woman here to see you. Something about the photography at the gala.â
Confusion stretches across Harryâs face before he tells Rick to let her in. He wasnât aware of any meetings with a photographer, but heâd see what they needed.
What Harry doesnât expect is for you to walk in: younger, long hair that went down past your shoulders, soft skin, black blazer, black skirt that stopped at your mid thighs, and the expanse of your legs being covered by sheer stockings.Â
Fuck, youâre a sight.
Standing up, Harry buttons the middle of his suit jacket. âHow can I help you, maâam?â he asks with a small nod.
You wait for his assistant to close the door before you walk up to Harryâs desk. Extending out your hand, you introduce yourself. Your hand is practically swimming in his as he gives you a firm handshake.
âPleasure to meet you,â he says before gesturing for you to sit in one of the chairs across from his desk.
âMy business was called about taking pictures for your upcoming New Years gala. They sent me out to confirm with you. Make sure everything is exactly the way you want; the pictures you want taken of the venue, the people â the food even.â
Harry watches your lips move as you talk, subconsciously licking his own while he takes in your words. He hadnât been aware that there would even be photographers at the gala this year, so this mustâve been his motherâs doing.
He clears his throat, âIâm sorry, but I donât think I was made aware about any of this. You mightâve been looking for my parents, not me.â
You raise an eyebrow, âYour parents?â
âItâs a family business,â he shrugs like itâs nothing. As if Crown Castillo isnât the wealthiest private equity firm in the U.S.
âAh, I see,â you nod slowly, âSo who do I speak to then?â
âWell,â he rounds his desk, moving to stand in front of you, âif you were looking for a âMr. Castilloâ, that would be my father: Emiliano.â
You nod once, taking in the information and correcting the form you brought in. As you build up the courage to ask, you place the end of your pen between your lips, drawing Harryâs gaze towards them once more.
His gaze darkens, hands tightening on the edge of his desk until his knuckles are nearly white.
âDo you mind showing me where your fatherâs office is then?â you finally ask, putting down your pen and meeting his eyes.
Harry would normally tell someone who asked for directions to ask his assistant, but something about you draws him towards you. His body craves a little more time with you, even if itâs just for five more minutes.
âSure. This place is easy to get lost in,â he huffs out something close to a laugh.
He gestures for you to walk in front of him, getting a small whiff of your perfume. Itâs something subtle, sexy and sophisticated, causing his slacks to feel a little tighter and uncomfortable. Harry doesnât think heâs ever been so easily affected by a woman, let alone one he just met.
As he holds the door open for you, he allows his eyes to travel down the back of your body, getting a good view of your ass before he walks in front of you.
âSuch a gentleman,â you tease him lightly as the two of you walk in unison.
Harry feels heat creep up his neck, wondering if you felt his heavy gaze on you or if youâre referring to his manners. âYeah,â he says gruffly before he clears his throat, âIâm not as big of an asshole as they say I am in the press.â
Your brows knit in confusion at that, âThe press?â
He freezes in his tracks, making you stop as well. The stare heâs giving you is almost like heâs trying to figure you out. His eyes are narrowed, mouth slightly agape as he reads you.
Your pulse picks up under his intense stare. Chest rising and falling a bit faster before he speaks. âYou donât⊠know who my family is?â he asks in disbelief.
âAm I supposed to?â
âI⊠guess not,â he says quietly, brushing it off before he continues walking.
You stand there, trying to process what just happened before you trail behind him.Â
âSorry if I offended you, Mr. Castillo, but Iâm not really into the whole⊠business world of things. Iâm sure you and your family have plenty of fame. I just donât know anything about it.â
Immediately you realize how much youâre rambling when Harry doesnât even bat another eye at you. His expression is stoic as he walks, keeping his eyes trained forward. You got a sense that you would ruin this deal if you kept talking, so you stayed quiet for the rest of the walk.
After another minute of walking past the most expensive and busiest people youâve ever seen, the two of you stop in front of an office door that reads: Emiliano Castillo.
âThanks for walking me here,â you murmur once he turns towards you.
Thereâs the faintest hint of a fire burning behind Harryâs eyes. So faint that you arenât even sure if youâre really seeing it.
âGuess Iâll see you soon,â he states, his voice a little rougher than it was before.Â
Youâre not too sure why, but your skin prickles at his tone. Goosebumps spread across your arms as you look up at him.
âSee you soon, Mr. Castillo.â
With that, he walks away, leaving you alone to talk to his father.
Harry Castillo was a man of power, and he was slowly losing it with you. After leaving you, he makes his way to the menâs restroom, locking the door behind himself before he steps into a stall. The heavy ache between his thighs becomes too much, and his erection is noticeable. He needs to do something about it quickly.
The second the sound of him unbuckling his belt echoes within the four walls of the restroom, he knows he is going to regret this. He pulls out his throbbing cock with a small hiss before spitting on his hand and fisting himself.
He works his wrist at a steady pace, tipping his head back in ecstasy as his thoughts drift to you. He imagines hiking up your short skirt and bending you over his desk, or fucking you against the floor-to-ceiling windows in his office.
God, he just knows youâd make the prettiest noises as he fucked you into oblivion. Heâd make sure to drag his cock within the deepest depths of you, making you and your pussy sing.Â
Just the mere thought of it has him thrusting into his hand faster, fucking his fist until he creams all over it. He shudders through his orgasm, vision going a little blurry around the edges, causing him to place a hand on the stall door to keep his balance.Â
Harry doesnât think heâs ever cum like that just from the thought of someone he barely had five minutes of interaction with. No, this is something entirely different, and he isnât completely sure about what it was exactly.Â
After all of that, thereâs one thing Harry knows for sure: Youâre his, whether you know it or not.
Setting up the gala with the coordinator has been⊠eventful. Youâre not even completely sure if he was actually listening to your advice or if he was just staring at your tits. Perhaps the dip of your dress was a little too far down your cleavage, but it isnât your fault that men act like pigs around you.
The venue is beautifully decorated and youâre sure you are going to get some gorgeous shots. Diamonds dangle from the ceiling in forms of chandeliers, reflecting off of the tall walls covered in expensive art. You had an inkling that the Castillos were rich, you just didnât know how rich.
Right at 7PM, guests start to pile in. Women wearing diamonds and gold around their necks, wrists, and fingers. Youâre guaranteed that if you sold this building and the people in it alone, youâd make a lot of money. But you arenât here to think hypothetically, youâre here to do your job, and youâre going to make sure the photographs are up to both your bossâ and Emilianoâs standards.
Guests mingle, drinking punch, eating the appetizers that were set out, some checking out the art, but the Castillos are still nowhere to be found. Itâs nearing 8:30 and Gavin â another photographer â is starting to get antsy.Â
âWeâre supposed to get a shot of them coming in,â Gavin says through his teeth, letting out an exasperated breath.
âTheyâll be here,â you murmur, your eyes focused within the camera lens.
Youâre watching the guests through your camera, always ready for the perfect shots. A happy couple smiling, the camera flashes. Guests looking up at the art, another flash.Â
When one head snaps towards the door, so does your camera, and you donât hesitate to take the shot of the family walking in. The lens whirs as you zoom in on the parents alone, and then the brothers.
Itâs almost automatic when Harry feels a camera on him. His gaze finds you in the crowd after the picture is taken, and you lower the camera just slightly to catch his eyes. His eyes travel down your body before he tips his head slightly towards you. Immediately, you feel your skin heat up.
He is clad in a tailored black suit, broad shoulders stretching out his suit jacket so much that you could hear the fabric begging for mercy from where you stand. A white handkerchief folded neatly in the pocket of his suit jacket, black slacks down his legs.Â
You could already tell he was a big and broad man. Probably manhandling every woman heâs ever been with.Â
âDid you get the shot?â Gavin asks, pulling your attention away from the man across the room.
âI got it,â you nod slowly, taking a few more just for good measure.
Harryâs gaze still hasnât moved from you, and for a brief moment, you wonder if this is how mice feel underneath a microscope. Their little bodies squirming as theyâre being examined and experimented on against their will.
âYou better fucking have,â Gavin states before he walks away from you.
Ignoring his comment, you take more pictures of Anastasia and Emiliano walking up to the small makeshift stage by the speakers. A microphone stand sits idly on it, waiting to be used for announcements.Â
You may not be looking at Harry, but you can still feel his gaze on you. Briefly, you wonder what heâs thinking about, but then his father starts speaking.
âMay I have your attention ladies and gentlemen. It is with great honor that I thank each and every one of you in this room tonight. My wifeâs business would not be as successful as it is without the help of you all. We are extremely grateful for your commitment and dedication to the place we call home: Crown Castillo.
Friends, family, employees â all of you are important and valuable. All of our hands keep this place up and running, and that is what a found family is. I hope we all continue to have each otherâs backs during the years to come. And please⊠enjoy yourselves tonight, and donât forget that all the funds collected tonight are going towards charity.â
Emiliano and Anastasia raise their glasses of champagne before Ana continues, âTo the Crown Castillo family.â
Everyone raises their glasses, repeating her words and going back to mingling. A handful of cameras flash, you and your coworkers getting hundreds of shots for the family and company. The more lively the photo, the better. Youâve learned over the years that these kinds of people appreciate the âvibeâ of the pictures more. If they look united, theyâll love the photos.Â
You lower your camera, checking all of the photos youâve gotten so far before a man walks up to you. âExcuse me,â he says, placing a hand on your bicep to get your attention.Â
You look at his hand before you look up at him, âCan I help you, sir?â
He extends his hand out, introducing himself, âLucas Taylor, Taylored Photography.â
Extending your hand out, you stare at him. Heâs a recruiter, no doubt. With a company name that doesnât even sound familiar to you, and you know all of the photography companies in New York. Emiliano didnât tell you about another photographer being here, so youâre a little confused.
âI must say,â he puts his hands in his pockets, straightening his posture, âthe photos youâve taken thus far are beautiful.â
âHow would you know?â you query, âYou havenât seen them⊠Lucas.â
He chuckles softly at your retort, nodding, âYouâre right.â The heated look heâs giving you isnât very subtle, and it makes you a bit uncomfortable. âI just wanted to tell you how breathtaking you look in that dress, missâŠâ Lucas trails off, trying to get you to tell him your name.
You press your lips into a fine line, getting ready to open your mouth, but Harry steps in next to you, placing a hand on your lower back. âYouâre a little close, arenât you?â
âOh, I,â Lucas stammers, chuckling sheepishly, âI was just complimenting her on her-â
âIâd advise you to leave,â Harry states, his voice cold and calculated as he stares Lucas down.
Harry has a good few inches on Lucas, so he shrinks into his skin, murmuring something under his breath as he walks away. Immediately, you step away from Harry, the warmth of his hand leaving your back and sending a cold shiver up your spine.
âI didnât need saving.â
âReally?â he draws out with a raised eyebrow, putting his hands in his pockets, ââCause it seemed like you were dying to be saved.â
His tease makes you narrow your eyes slightly, âI appreciate the act, but I can handle myself, Mr. Castilloââ
âHarry,â he corrects you, âI think weâre well past the formalities now, donât you think?â
âWhat, because you âsavedâ me?â you retort.
âThatâs exactly why,â the corner of his lips tug up into a small smirk, making you roll your eyes.
âLook, Iâm trying to do my job for your father. So if you donât mind, Iâd like to get back to it now.â
Harry chuckles fondly, watching you raise your camera back up to your eyes. You have a good work ethic, which he admires. But he also wonders if you ever took a break and truly winded down. Thereâs a huge chance that you donât do anything remotely close to what he does to wind down, but he feels the need to push your boundaries.
Throughout the night, his gaze keeps landing on you. Watching you mingle with guests, take pictures, talk to his parents, and sip your own glass of champagne. Thereâs just something so intriguing about you and how you carry yourself. Itâs not surprising that heâs thinking with his dick first, but he feels some sort of pull towards you. Like something within the both of you is calling out to each other.
Itâs been weeks.Â
Harry hasnât been able to get you off his mind. He doesnât think heâs ever fucked his fist as often as he has lately. Heâs done it at least four times today, and heâs painfully hard again, but he canât wrap his hand around his cock without hissing.Â
Youâre taking over his mind, and you havenât even really done anything.Â
Heâs looked up the photography company you work for to see if your number is anywhere on it, but the website only has the ownerâs information on it.Â
Asking his parents would be the easy thing to do, but he doesnât want to raise their suspicions. They already hassle him enough about finding someone to marry, and he doesnât need more of it.
As if the Gods were blessing him, he looks up from his desktop just in time to see you walking by. A black portfolio folder is in your arms as you walk swiftly towards his fatherâs office. Youâre probably here to drop off the pictures, but Harry knows that his parents are out on a lunch date.
Without really thinking it through, he leaves his office, walking past the many cubicles while keeping his eyes trained on you. Youâre on the opposite side and have yet to notice him, but he catches up to you just before you make it to his fatherâs office door.Â
Just as youâre about to knock, Harry slides right in front of you, blocking the door with his broad frame. Your palm meets his chest instead of the door, causing warmth to bloom throughout his entire body.
âHey you,â Harry says, putting his hands in his pockets like he wasnât entirely in your way.
âHi,â you reply tentatively, dropping your hand down to your side. âIs your dad here?â
âNo, heâs out on lunch,â he averts your gaze for a moment, making eye contact with his assistant before he looks back down at you.
âOh, I was told to drop off the pictures here,â you murmur, tucking your hair behind your ear as you take a step back. âIâll just come back laterââ
âI can look at them,â Harry says a little too quickly, clearing his throat and backing off the door, âI mean, this is my firm just as much as it is my parentsâ. Let me look at them.â
âOkay,â you draw out, handing him the portfolio, âYour dad can email me if you guys arenât happy with the photos.â
âIâm sure we will be,â Harry states matter-of-factly, giving you a charming smile as he takes the folder from you. He holds it like itâs something sacred, âWe can get this done now, if you want. Why waste more time on this?â
You ponder his request, biting the inside of your cheek. The instructions your boss gave you were to drop the photos off, get all information if changes needed to be made, get lunch, and come back to edit photos for another company. But with Emiliano gone, Harry is your best option right now.
Reluctantly, you agree, following him to his office. The look he and his assistant share isnât lost on you as he closes the door, drawing the blinds as well, plunging the room in partial darkness as the sun spills in from the floor-to-ceiling windows.
The cool leather quietly squeaks as you sit down across from his desk, watching him sit in his own chair and open the folder. He carefully studies each photo, not saying anything yet, but his dark eyes meet yours every now and then over the photographs.Â
You shift under his heated gaze, crossing your leg over the other and sitting up straighter.Â
Harry smirks faintly at your reaction, knowing heâs got you right where he wants you. âThese look amazing,â he compliments, putting down the photographs to make eye contact with you.
You murmur a small thank you, intertwining your hands in your lap. âIâll send them over to your father this afternoon so you guys can⊠do whatever you please with them.â
âAnd then weâre done?â he asks.
âAnd then weâre done,â you confirm, slowly nodding.
âSo,â Harry starts, standing up to round his desk, âyou wonât be working for my company anymore, right?â he asks, sitting on the edge of his desk â directly in front of you.
You can hear the frantic pulse of your heartbeat thrumming in your ears. Though, you keep it strictly professional.
Harryâs eyes follow your movements as you stand, pressing his palms into his desk and looking at you with his big brown eyes.Â
âThatâs correct,â you confirm, straightening your posture and adjusting your suit jacket. âWe wonât ever have to see each other again, Mr. Castillo.â
âHarry,â he corrects you again, âAnd who said anything about not seeing each other anymore?â
âI did.â
Harry huffs, shaking his head slowly, âYou can be very disobedient. Someone outta teach you a lesson.â
Your eyes narrow by a fraction, taken aback by the sudden statement that came tumbling out of his mouth. âIs that what you tell all the women you sleep with?â
âIââ
âWomen arenât on this earth for menâs pleasure. We are people, and we have feelings,â you scoff.
Suddenly he stands, towering over you with his broad frame. But you donât back down, standing your ground and looking up at him with a defiant look.
âI never told you anything about my sex life,â he states, his voice low.
âAw, did I hit a nerve?â you pout, âI know you didnât. I like to know the people that I work for, and it wasnât that hard to find out about your⊠extracurricular activities, Mr. Castillo. Maybe you should make sure the women that you fuck are more tightlipped than they let onââ
Harryâs hands grip your waist, pulling you flush against the warmth of his body. You can feel his breath fanning over your face, his lips slightly agape as he stares down at you.
âSay one more thing,â he warns, eyes flicking to your lips momentarily. âIâm used to getting what I want, when I want it.â
âThat must get very boring,â you tease with a tilt of your head. âYou want me? Then earn it,â thatâs all you leave it at before you step back from him, heading towards his office door. âTell your father I said thank you for the opportunity,â a small smirk tugs at the corner of your lips, and then youâre gone.
Harry exhales harshly through his nose, running a hand through his curls as heâs left there: wanting you.
You gave him a challenge and he sure as hell isnât going to back down.
Steam from your coffee mug curls around your laptop in lazy tendrils, patrons of the coffee shop chattering amongst themselves. The raised ceilings give the place a more open feel, the hissing of the espresso machines echoing throughout the building.Â
Your friend, Samantha, sits across from you, telling you about her latest hookup. Itâs some guy she met at a party a few months ago. Theyâve been talking back and forth for a while and only recently decided to just bite the bullet and fuck.
She waves her hands around as she speaks, telling you in grave detail about the fun night she had.
âI think I blacked out at some point,â she mentions, prompting you to raise your brows in surprise.
âJesus, Sammy,â you breathe out, astonished by the statement.
As the conversation goes on, she tries to press you into telling her about the last person you worked for.
âHave you heard from Harry?â she casually asks, earning narrowed eyes from you.
âWhy would I have heard from him?â
âBecause,â she draws out, lifting her coffee mug to her lips, âhe definitely wanted to fuck you and you totally shot him down!â
You bite the inside of your cheek, âHeâs just like every other rich asshole, Sam. He thinks he can walk all over people and expect them to polish his Italian shoes with their tongues. I donât need anything like that.â
âSo?â she shrugs, placing her elbows on the wooden table, âI bet he fucks like an animal.â
âSamantha,â you deadpan.
âWhat?â she feigns innocence, âHe is a man that screams dominance in the bedroom. If you wonât get under him, I will.â
Against your will, a fire of possessiveness begins to burn in your gut, prompting you to narrow your eyes at your friend. She continues to talk, oblivious to the uneasiness youâre beginning to feel.
âItâs a crazy feeling being with someone that dominant and kinky,â she pauses, thinking. âOo, maybe he has a sex dungeonââ
âSam,â you shake your head once, âEnough.â
âIâm just saying,â her tone switches to something lighter, âmaybe youâre missing out on whatâs right in front of you.â
âOr maybe I dodged a bullet,â you tilt your head to the side slightly. âHeâs like⊠in his 50s, Sam. You do know that, right?â
She shrugs, âJust because the wrapper is wrinkled, doesnât mean the candy isnât sweet.â
You raise your brows, amusement spreading across your face as you let out an incredulous chuckle. âYou did not just say that. Do I need to take your phone away from you?â
âProbably,â she grimaces, âBut seriously, he wants you. I donât think you should let that go to waste.â
You press your lips into a fine line, hearing the murmurs of the cafe die down. Everyoneâs gazes collectively fall to a single person who walks in, reeking of luxury and money. Like a moth to a flame, Samanthaâs eyes lift as well.
You bite into your toast, the crunch a lot more audible than it should be in a busy cafe in New York.Â
âOh my God,â your friend murmurs, causing you to look up at her.
âWhat?â you ask, putting your hand over your mouth as you chew.
âExpensive looking hottie alert,â she states, nearly making you choke on your food.
You wipe the corner of your mouth, turning to look over your shoulder at whoâs caught everyoneâs attention. The world slows around you, Harryâs dark eyes locking onto yours as his signature smirk pulls at his lips.
âWait, isnât thatââ
âYes, it is,â you cut Sammy off, pulling your bottom lip between your teeth as Harry begins to stalk towards you.
âLadies,â Harry greets, nodding once towards your friend before his gaze locks onto yours. He crouches down to your level, so close that you can feel his breath fanning across your face. âHi,â he murmurs to you, a shit-eating grin plastered across his face.
âHi,â you repeat his words, narrowing your eyes at him. âHow the hell did you find me?â
Harry nods towards Samantha again, âYour friend posts a lot on social media.â
Of course.
âLookââ
âI just wanted to personally invite you to the Crown Castillo Black & White Gala,â he speaks lowly for your ears only. âButâŠâ he trails off, reaching for a manilla envelope from the inside of his suit jacket, âIâd like you to look over something for me.â
âIs it regarding the photos I took?â you ask steadily, not looking away from his deep espresso eyes.Â
His Adam's apple bobs as he swallows, drawing your eyes towards it. âNot necessarily, but it is business.â
You tilt your head to the side, âWhatââ
âJust think about it and have an answer by the night of the gala.â He hands you the envelope, standing up and straightening his suit jacket. âI look forward to doing business with you.â
The second you get to your apartment, the sound of the envelope ripping fills the empty space. You pull out a thick packet of white paper. The title page reads: âTHE COMMENCEMENT DATE BETWEEN THE DOMINANT AND THE SUBMISSIVEâ
âOh, youâve got to be fucking kidding me,â you blurt out immediately.
Your thoughts start to swarm as you glance through the pages, words like sex toys, gags, and whipping sticking out to you.
He wants you to be his sex slave?
Did he listen to a single word you told him in his office?
Your phone buzzes in your pocket and you pull it out without thinking. A new email pops up on your lock screen, Harry Castillo being the obvious name as the sender.
The packet hits your kitchen counter with a sharp thud as you unlock your phone, quickly opening the email he sent.
âGood afternoon, I hope this email finds you well.â
You narrow your eyes at the first line before you continue reading.
âI hope you consider reading over the packet I left with you. Whatever you arenât willing to do, I will accept immediately and set up a meeting to change them. Please read over everything. All I need is your written consent.â
You scoff, placing your phone face down on the counter, hands gripping the edge of it until your knuckles are white. Darkness envelops you when you close your eyes, your breathing picking up as you attempt (and fail) to process whatever the fuck you just read.
Thereâs no way this is real life, right? People donât actually do this outside of movies.
Right?
The thick packet taunts you when you open your eyes, sticking out like a sore thumb in your peripheral vision.Â
As the weeks go by, the contract sits untouched in your nightstand drawer. Harry emails you, but most of the time you donât respond, earning desperate messages from him late at night.Â
You donât know what to think about the situation. Honestly, you thought everything you found out about him were all lies, but this seems pretty fucking real to you.
The night before the gala, you build up the courage to show up at his office. You briskly walk past the security, the packet held tightly against your chest as you reach for the elevator, repeatedly pressing the button for his floor until the doors close.
You exhale in relief once the security guards faces are no longer in view, leaning back against the back wall. Briefly, you look down at the contract again, the word submissive staring back at you.
That isnât who you are. Isnât who you were going to be.
You refused to bend yourself to a manâs will just to please him. It goes against everything you stand for.
The elevator dinging pulls you out of your thoughts, the doors sliding open to reveal his floor. Itâs dark and quiet, nothing like the other times youâve been here. Your heels echo in the space as you step out.Â
Too loud.Â
Too final.
You turn back around to leave but the doors close too quickly, sealing your decision.
A familiar voice calls out your name, you looking over your shoulder to see Harryâs assistant, Rick, walking towards you.
âSorry,â you call for the elevator again before turning around to face him, âI shouldnât have come here. I was just leavingââ
âMr. Castillo will see you now.â
That catches your attention, the doors sliding open behind you and revealing the two security guards. Rick holds up his hand, signaling them away. âWeâre fine here. She has an appointment.â
The men share a look, deciding itâs best not to say anything.
âPlease, right this way, miss,â Rick beckons you to follow him.
You glance back at the two brawly men, figuring that itâs best not to get in the elevator with them since you technically just snuck into the building. Against your better judgement and your body screaming at you not to, you follow Rick to Harryâs office.
Thereâs nobody on the floor. Not even a single janitor in sight. Itâs like a ghost town, or one of those horror movies that start off with a vulnerable woman left alone in an office building. Nine times out of ten, she ends up dead in her car.
Rick knocks on Harryâs closed office door twice before opening it. âHave fun.â
âWait, you arenât staying?â you ask quietly, watching him shake his head.
âI donât work overtime.â With that, he gathers his things and heads back towards the elevator, leaving you alone with a stranger that asked you to be his submissive through a packet of paper.
You walk in slowly, noting that his eyes immediately dart down to your bare legs as he stands. He says your name, nodding in greeting. âIâve been expecting you. Please, shut the door.â
Hesitantly, you close the door behind yourself, feeling like youâre sealing a deal without signing your signature.
âWhy were you expecting me?â you ask, walking deeper into his office. The skyline of New York City gleams behind him, like diamonds against a dark sky.
He shrugs faintly, placing his hands in his pockets. âWomen usually come around to these sorts of things.â
The statement nearly gives you whiplash, your fingers tightening around the contract before you toss it onto his desk with a sharp thwack.
âIs that what you think? That women want to be your little plaything?â
âItâs not about that,â Harry claims, rounding his desk to stand in front of you. âItâs more about⊠testing your limits. Seeing how far youâll go, learning what pleases youââ
You hold out your hand, âIâm gonna stop you right there.â Harry goes quiet, allowing you the space to speak freely, âYou tell me one thing, but the contract says another.â
âSo you read it?â he asks.
âNo, I only read the title page,â you explain. âSex shouldnât be a business deal. A relationship shouldnât be a business deal.â
Harry weighs your words, rolling his tongue over his teeth. âI prefer the term fucking.â
âI didnât ask.â
He chuckles faintly, crossing his arms over his chest and sitting on the edge of his desk. âIf you want to change things in the contractââ
âNo, you donât get it,â you cut him off again, stepping closer, âI didnât want it in the first place. Did our conversation in this very office just fly over your head?â
âNo, it didnât,â he claims, shaking his head slowly, âbut I can tell that you want more from me.â
Harry stands slowly, closing the last bit of space between the two of you until you have to tilt your chin up to look at him directly. A faint smirk tugs at his lips, âWhat is it that you want? Money? Jewelryââ
âYou canât buy me, Harry,â you interrupt him. âI wonât sign your sex contract and I donât want to see your face again.â
He nods once, âYou came to my office at 9PM just to tell me that? Something you couldâve emailed me or told me over the phone.â
You roll your eyes.
âI mean, itâs a little much, donât you think?â he asks.
âNo, youâre right,â you take a slow step back, âGoodbye, Mr. Castillo.â
You turn around, exhaling through your nose as you begin to head for his office door. Before you can get too far, you feel his hand wrap around your wrist, spinning you around until youâre flush against his chest. The collision steals all the air from your lungs, hands instinctively coming up to steady yourself on his biceps.Â
Harryâs breath mingles with yours, one of his hands coming up to cup the nape of your neck before he crashes his lips against yours in a searing kiss.
A sound of surprise leaves you, and without thinking, you push at him just enough to jostle him before your hand flies across his face. Your hand stings from the force of it, causing you to shake off the pain. Harry keeps his head turned to the side for a moment, his gaze dark when he looks back at you.
What you donât expect is for him to spin the both of you around, sending everything on his desk flying before he bends you over it.
âIs this what you wanted, princess?â he rasps, breath hot against your ear as he hikes up your skirt.
âHarryââ a low moan cuts you off when he sucks at your pulse point, the rapid flutter of your heartbeat quivering in between his teeth.
He slips his foot between your legs, kicking them apart before he delivers a harsh smack to your ass. You jolt forward upon impact, a sharp gasp leaving your lips. He soothes the plush skin, rubbing his hand along the red spot thatâs started to bloom from the force of his palm.
âYou have no idea what you do to me,â he murmurs in your ear, the metallic rattle of his belt unbuckling filling the office.Â
âThis is a bad idea,â you weakly protest. Though, you make absolutely no effort to move.
âReally?â he taunts, dropping his slacks and boxers in one go. âYouâre saying one thing⊠but your body is saying another,â he repeats what you said in his own twisted way, peeling your lacy panties to the side.
The cool air hits your slick heat, sending a shiver throughout your body. You know this shouldnât happen. Fuck, you shouldnât have even shown up here tonight. But then he swipes the tip of his cock through your folds, parting them, smearing your slick as well as his precum.Â
His hand is steady on your hip, the other gripping the base of himself as he repeatedly stimulates your clit with his swollen tip until your knees nearly buckle.Â
âFuck,â he breathes, âyouâre so pretty.â
âJust shut up and fuck me,â you quip.
Harry chuckles darkly, shoving himself in, the stretch stealing the air from your lungs as you both moan in unison. He doesnât give you time to adjust to his girth before heâs fucking you raw. The obscene slap of wet skin against each other fills the space of the office, his breathy grunts behind you stirring you on.
Push him back, you repeat in your head over and over again. It feels so right, like the Earthâs axis has finally shifted into place as your slick velvet walls greedily suck him in deeper. But you know this shouldnât be happening â you worked for his family, he left a fucking sex contract with you, and heâs the most cocky son of a bitch youâve ever met.
Not to mention, absolutely infuriating.
But he feels too good, angling his hips to reach parts of you that have never been touched before. Youâll get your fill just this once, you tell yourself, succumbing to the feeling of him splitting you open.
âLook at you,â he purrs, âtaking my cock so well, baby.â Another gasp comes tumbling from your lips when he smacks the supple skin of your ass, watching it ripple with every deep thrust.
The ruthless pace has you mewling, arching your back until your arms are straight forward across the surface of his desk. Harry wraps your hair around his hand, using it to pull your head back and fuck you harder.
âYesyesyes,â you chant, your jaw going slack, the sting of your hair being pulled, an odd but welcome sensation.
Harryâs other hand slides up to your waist, indenting his fingertips into your skin. âIs this how you like it?â he punctuates between thrusts, âI knew youâd be fucking perfect.â
For now, you ignore the comment, too focused on your pending orgasm and the roaring of your blood rushing in your ears. âOhh, fuck,â you slur, feeling every ridge of his cock stimulate your sensitive spots perfectly â like it was made to ruin you specifically.
He groans, gritting his teeth as your walls squeeze his shaft. Without much warning, he hooks his forearm under you, lifting your upper body towards his. His hot breath fans over your ear, deep grunts telling you heâs just as affected as you are.
âYou feel so fucking good,â he growls, tugging at your blouse until your tits spill free. Roughly, he takes one in his warm palm, massaging the soft skin and rolling your peaked nipple between his thumb and forefinger.
You lean your head back on his shoulder, closing your eyes and pulling your bottom lip between your teeth when his hand leaves your waist to wrap around your throat. He squeezes gently, feeling the frantic pulse of your heartbeat under the pads of his fingers.
âHarry,â you whimper, heat pooling low in your abdomen as you near your peak.
âShit,â he hisses, your walls pulsing and squeezing him just right. âYou gonna come for me?â he rasps, slipping his hand between your legs to circle your swollen clit.Â
Your vision goes blurry around the edges, incoherent moans toppling out of your lips as shockwaves spark through your body in fast-rising surges. Blood roars in your ears, your body threatening to double over, but Harry holds you tightly to his heaving chest.
He lets out a ragged groan, bending you back over the desk and pulling out just in time to release his thick, hot, white spurts of cum. He shudders through his orgasm, fucking his fist until he has nothing left to give.
The room stills, both of you breathing heavily from your equally intense climaxes. Your heart pounds in your ears, mind a little hazy and not fully coherent as you lift yourself up, palms pressing into the desk.
Harry pulls up his boxers and slacks, grabbing the box of tissues on his desk to clean up the mess he made.
âDid I hurt you?â he asks quietly when you donât speak, watching you adjust your clothes and hair back into place.
âNo,â you shake your head, turning around to face him, âit was good.â
He hums in acknowledgement, âSo will I see you tomorrow night?â
You open your mouth to speak, but nothing comes out just yet. Honestly, you hadnât thought about whether or not you would go to the gala. What would you even do there besides accompany him and fulfill his⊠needs?
âI havenât made up my mind yet.â
Harry steps closer, closing the distance between the two of you and placing his hands on the desk behind you. This way, you have to tilt your chin up to meet his eyes.
âYou should go,â he murmurs, leaning in to press his plush lips to yours, giving you a tender kiss that you didnât think he was capable of.Â
Despite yourself, warmth blooms in your chest, leaving you wanting more.Â
Everything feels wrong: your heels are too uncomfortable, dress too tight â too long, jewelry too heavy.
You felt completely out of place. This isnât your crowd. Youâre always the one in the back, a professional black dress and pumps on your body, camera in hand while you blend in with the wall.Â
Youâve never been in the sea of people you take pictures of.
The building is 24 stories, drowning in exquisite taste and class â something you definitely missed the lesson on in school. Chandeliers scream money, reflecting off the lights and the diamonds dangling from women's necks.Â
Soft jazz music fills the lobby, creating an alluring atmosphere that eases your nerves for the moment.Â
A worker offers to take your coat, hanging it up with the rest when you give it to him. You feel exposed, anxiety rising once more now that your dress is revealed. It was a black off-the-shoulder dress, the back of it stopping in the middle of your back.Â
Goosebumps sprinkle across your skin, shrinking you into your own warmth as you take cautious steps towards the grand double doors. Your heels clack on the marble floors, echoing in your ears.
Inside, classical music drifts through the air, strangers chatting too loudly and overlapping one another.Â
What the fuck were you doing here?
This isnât your scene and youâre already going against your morals â stepping out of your comfort zone because a man asked you to.
On instinct, you stick close to the back wall, not wanting to draw attention to yourself, but also not wanting to intrude.Â
Neither Harry or his family are anywhere to be seen, tempting you to leave before youâre noticed by anyone.
Servers pass by, not giving you a second glance as you practically hug the wall. One walks by holding glasses of champagne and you donât hesitate to grab one, hoping the fizzy beverage will ease your racing heart.
Itâs just a party, you tell yourself. Hell, not even a party, this could pass as someoneâs fucking wedding reception.
Just before you burrow deeper into your inner turmoil, everyone goes silent â even the music. Someone on a microphone somewhere introduces the Castillo family and everyone claps. You look around for a moment, lost, before you tuck your clutch under your arm and clap along with them; careful of your glass of champagne.
âHappy birthday, Mrs. Castillo!â
âHappy birthday, Ana!â
People begin shouting out, the older woman laughing and wrapping an arm around her husband.
Harry invited you to his motherâs birthday party and acted like it was just another annual gala.
Jesus Christ.
After a while, you manage to make your way to the bar, successfully ignoring Harry to the best of your abilities. You donât move from your spot until he disappears into the crowd and youâre 100% sure he canât see you.
You order a vodka martini, downing it pretty quickly before you pop the olive in your mouth. The sting tingles your throat, causing you to clear it into your hand, ordering another one.
âThere you are,â a familiar voice says behind you, placing his forearms on the counter. âYouâre avoiding me.â
You stand up straighter, rolling a toothpick in between your fingers. âAm I?â you query, tilting your head to the side. âYou donât even know how long Iâveââ
âI noticed you the second I walked in,â Harry cuts you off, rendering you speechless for a second.
He chuckles when you donât respond, another glass being replaced with your empty one. âIs that so hard to believe?â
âA little, yeah,â you murmur, nodding before you sip on your drink.
Harry watches your throat work when you swallow, his mind going to more impure places. âYou wanna get out of here?â
You raise your brows, âIsnât this your momâs party?â you pause, leaning in and lowering your voice. âYâknow, I donât appreciate how you blindsided me with that, by the way. I wouldâve brought a present.â
He chuckles, straightening up and looking down at you. âNow where would the fun be in that?â he asks, pausing before adding, âPlus, you didnât need to. My mom already adores you.â
Surprise flashes across your face before you remember that you worked with her and her husband â not just Harry. âWell, she was lovely to work for,â you murmur.
âSo what do you say?â he asks, leaning in to whisper in your ear, âLetâs go somewhere more private.â
Your skin tingles, not only from his tone of voice, but also from his proximity. In order to keep your sanity, you press your palm against his chest, pushing him just a bit. âJust because we had sex doesnât mean that weâre together now.â
âReally?â he draws out, straightening up and placing his hands in his pockets. âSo youâre not gonna go home with me?â
âI didnât say that.â
The city of New York twinkles below, reflecting in your irises. There hasnât been a time where youâve seen the city like this: so high up and a lot clearer.Â
âYou can see most of the city from here,â you murmur to Harry once he steps behind you, wrapping his arms around your waist and turning you around.
âWouldnât you rather look at me?â he teases, earning an eye roll from you.
âYou do that a lot,â he points out.
âDo what?â
âRoll your eyes at me.â
A small smirk tugs at your lips, âAnd youâve deserved it every single time.â
Harryâs hands tighten on your waist, pulling you flush against the hard planes of his body. âHave you thought about the contract anymore?â
Your expression falters, opening your mouth but nothing comes out. In your hasty escape from his office last night, you completely forgot about the contract. âNo, because I donât have it anymore. Plus, I already told you my answer.â
His eyes narrow by a fraction before he pulls you by your wrist, leading you up the stairs in his penthouse.Â
âHarry,â you try to get him to stop, but he tightens his grip on your wrist.
âI just need you to see,â he states, stopping in front of a locked door and fishing the key out of his pocket.
The lock clicks, your heart races, practically in your throat as he opens the door. Lights slowly turn on, reflecting off of the deep red of the walls. Harry gestures for you to go first, and your breath catches in your throat when you step inside.Â
âOh, my God,â you whisper, your body going rigid, the shock evident on your face.Â
A king-size bed sits in the middle of the room, gold hoops attached to the four bedposts. The walls look like a horrific murder scene, a wine red making everything seem more intense and unnerving.
âThis is my playroom,â Harry announces.
Your eyes are wide, lips agape as you assess the sight in front of you. âYeah, I can see that,â you breathe, âJesus Christ, Harryââ
âBefore you start,â he cuts you off, âjust look around. Nothing in here can harm you, I promise.â
You glance at him sideways before he stands off to the side, giving you free reign to look around. Your eyes dart around the room, trying to figure out what youâre looking at. Hesitantly, you put one foot in front of the other, heels clacking against the hardwood floor.
The wall on your right is lined with various paddles and sensory toys. A rack of items youâve never seen before sits in front of the bed, and without really thinking, you run your fingers through the rough material.
âThatâs called a flogger,â Harry informs you, moving to hover beside you.
You snatch your hand back like youâve been burned, suddenly remembering his reputation and the other women heâs most likely used this stuff on. Crossing your arms over your chest, you move on, examining the various cuffs and gag toys he has.
âSay something,â he murmurs, âPlease.â
You take a deep breath, tilting your head back to look at the ceiling as you muster up the courage to even open your mouth again. Only, you realize that the expanse of the ceiling is covered in a metal grid system. Bondage is the first thing you think of.
You knew he was kinky, you just didnât know how kinky⊠Until now, that is.
What the fuck have you gotten yourself into?
This has never been something youâve been remotely interested in, and now it is right in your face.Â
Finally, you look back at Harry. âYou do this stuff to women?â you ask, even though you already know the answer.
âYes,â he confirms, âbut everyone walks away happy.â
âH-How?â you stammer, some of your willpower returning to your body. âYouâre a sadist.â
âDominant,â Harry corrects you, earning an eye roll from you. âThat right there,â he points at you, âIf you were mine, you wouldnât be able to sit for a week.â
âExcuse me?â you chuckle breathlessly, crossing your arms tighter across your chest. âBy definition, you are a sadist. You get off on peopleâs pain.â
âItâs not that,â he states, a smirk tugging at his lips. âI told you: itâs all about testing limits.â
âWhy?â you shrug, âWhy would you want toâŠâ you gesture towards the dangling whips on the opposite wall, âuse these kinds of things on people?â
âFor pleasure,â he answers like itâs completely obvious.
You shake your head slowly, âYou canât just enjoy regular sex like everyone else?â
When he doesnât answer, you continue. âI donât know what you want from me, but I sure as hell know that this isnât a relationship.â
âI never said anything about a relationship.â
Thatâs what gets you. Your brows knit, an unfamiliar ache settling in your heart. âThen what the fuck are you doing with me?â
Instead of answering, he grabs a silk ribbon from a drawer, walking back over to you. âHold out your wrists,â he instructs.
You glare up at him, and he senses your defiance. âIâm not gonna use them to force you into anything, I promise.â
To make sure he knows you donât want to do this, you continue glaring at him as you slowly hold out both wrists. His signature smirk pulls at his lips, his hands deftly tying the red silk around you. Once tied, he tugs harshly, pulling a gasp from your lips.
âIt doesnât hurt, does it?â
âNo,â you whisper, meeting his eyes. âNo, it doesnât.â
âAll the fear is in your head,â he voices firmly, letting the silk slip from your wrists.
A thought pops into your mind as you drop your hands to your sides. âIf you want to⊠continue having sex with me, then why canât we be together?â
âThis is the only kind of relationship I associate myself with.â
Confusion stretches across your face, your brows furrowing as you try to see through his facade. Heâs telling you one thing, but the way heâs acting is the complete opposite. He almost seems⊠obsessed with you; he hasnât left you alone for months, he tracked you down via Samanthaâs Instagram stories, and now he is trying to force a contract on you to keep you.
To you, it seems like he enjoys the thrill of the chase rather than anything else.
âHow many women have you done this with?â
All you know is what you and your friend could find on the internet, and honestly, it wasnât much. News outlets are very vague when it comes to Harry Castilloâs personal relationships, and it makes you curious.
He tosses the ribbon onto the bed, placing his hands in his pockets. âLetâs not go there right now.â
âWhy not?â you push gently, closing the distance between the two of you, only for him to suddenly take a step back.
Oh, is all you can think as you stare up at him, trying to read between the lines of what heâs not telling you.
âHow many?â you repeat your question earnestly, keeping your place.
Harry rolls his tongue over his teeth, âTwenty.â
âTwenty?â you breathe, all of the air leaving your lungs at once. âChrist, Fabio,â you joke, deflecting the situation.
Your mind swims within multiple questions.
Whoâs to say that there wonât be twenty more after you?
How has his dick not fallen off?
Do you need to get tested?
The two of you fucked raw on his desk. You should definitely get tested.
Harry doesnât laugh at your joke, his face remains serious. âItâs the way I am.â
âWhy?â you ask quietly, almost scared of the answer.
His lips press into a fine line, avoiding your gaze for a moment. Abruptly, he grabs you by your upper arm, leading you out of the room and locking up behind the two of you.Â
In the hallway, you can think clearly, not intimidated by the actual sex dungeon you were just in. You swallow thickly when he turns to face you, he seems steady but his eyes tell you otherwise. Thereâs the smallest hint of vulnerability in them, and itâs gone the moment you notice it.
âBe honest with me,â Harry says, âwhat are you thinking?â
You exhale sharply. What are you supposed to think after being shown that? It is the exact opposite of what you firmly stand on, but he seems set in his own ways.
âI donât know,â you answer honestly, heading for the stairs. âThatâs⊠a lot to take in,â you look over your shoulder, seeing that heâs following a few steps behind you.
âIf you donât want anything to do with me anymore,â he stops at the end of the hallway, looking down at you, âthatâs completely fine.â
You know heâs not fine with it, but you appreciate the statement more than youâd ever let on. âI just,â you start, trying to find the right words as you process what he showed you, âI donât think I can do that: bend to the will of someone else. Thatâs not me.â
He nods slowly, his eyes mimicking a puppy. Itâs almost enough to make you change your mind.
Almost.
âI canât be one of your girls â I wonât.â
part 2
a/n: i couldn't find anything like this so i wrote it myself đ ive genuinely only been thinking about fifty shades since i watched it in december and Harry was the perfect character to write something related to those movies on. this isn't like anything else ive written so im stepping out of my comfort zone a bit here đ but i hope you enjoyed reading it. feedback is much appreciated! (part 2 soon i hope lmao)
áŻœ tags: @missladym1981 , @kirsteng42 , @mcthsman , @petalsinblood , @rosharanfiction , @cherrycokeispunk , @cuteanimalmama , @harriedandharassed , @madpanda75 , @shadowqueen2024 , @picketniffler , @kokoluwie , @reedispunk , @umadirectioner , @katyispunk , @missadangel , @time-for-my-weekly-spanking , @missadangel , @stylesispunk , @milla-frenchy , @gothcsz , @la-vie-est-une-fleur29 , @sunshineflowersandkisses
dividers by @/angeliicide
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