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 😛, 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 🤍 (more notes at the end)
᯽ 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.
The Castillos have never been afraid of money. Hell, they bathe in it every night. Because of this, Harry isn’t afraid to spend a pretty penny on a woman. Except he hasn’t found someone that actually deserved it.
Sure, he’s had his fair share of women — none that he’s ever been photographed with. A list extending from women he’s worked with to sex workers. But no one has interested him long enough for him to think about any type of future with them. He’s not necessarily proud of his ways, but it’s a big stress relief for him.
Control is a necessity in all parts of Harry’s life — 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 they’re properly taken care of. After all, he’s not a dick. He just thinks with his.
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.
“Yeah, I’ll look into it,” he says, exasperated as he waits to end the phone call sooner rather than later.
“Okay. Thank you, Mr. Castillo. Have a good—“
The man’s 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.
Crown Castillo has been the busiest and biggest it’s 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. “Come in,” Harry calls out, sitting up straight in his chair.
The door slowly opens before Rick steps in, “Mr. Castillo, there’s a woman here to see you. Something about the photography at the gala.”
Confusion stretches across Harry’s face before he tells Rick to let her in. He wasn’t aware of any meetings with a photographer, but he’d see what they needed.
What Harry doesn’t 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.
Fuck, you’re a sight.
Standing up, Harry buttons the middle of his suit jacket. “How can I help you, ma’am?” he asks with a small nod.
You wait for his assistant to close the door before you walk up to Harry’s desk. Extending out your hand, you introduce yourself. Your hand is practically swimming in his as he gives you a firm handshake.
“Pleasure to meet you,” he says before gesturing for you to sit in one of the chairs across from his desk.
“My 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 – the food even.”
Harry watches your lips move as you talk, subconsciously licking his own while he takes in your words. He hadn’t been aware that there would even be photographers at the gala this year, so this must’ve been his mother’s doing.
He clears his throat, “I’m sorry, but I don’t think I was made aware about any of this. You might’ve been looking for my parents, not me.”
You raise an eyebrow, “Your parents?”
“It’s a family business,” he shrugs like it’s nothing. As if Crown Castillo isn’t the wealthiest private equity firm in the U.S.
“Ah, I see,” you nod slowly, “So who do I speak to then?”
“Well,” he rounds his desk, moving to stand in front of you, “if you were looking for a ‘Mr. Castillo’, that would be my father: Emiliano.”
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 Harry’s gaze towards them once more.
His gaze darkens, hands tightening on the edge of his desk until his knuckles are nearly white.
“Do you mind showing me where your father’s office is then?” 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 it’s just for five more minutes.
“Sure. This place is easy to get lost in,” 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. It’s something subtle, sexy and sophisticated, causing his slacks to feel a little tighter and uncomfortable. Harry doesn’t think he’s 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.
“Such a gentleman,” 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 you’re referring to his manners. “Yeah,” he says gruffly before he clears his throat, “I’m not as big of an asshole as they say I am in the press.”
Your brows knit in confusion at that, “The press?”
He freezes in his tracks, making you stop as well. The stare he’s giving you is almost like he’s 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. “You don’t… know who my family is?” he asks in disbelief.
“Am I supposed to?”
“I… guess not,” he says quietly, brushing it off before he continues walking.
You stand there, trying to process what just happened before you trail behind him.
“Sorry if I offended you, Mr. Castillo, but I’m not really into the whole… business world of things. I’m sure you and your family have plenty of fame. I just don’t know anything about it.”
Immediately you realize how much you’re rambling when Harry doesn’t 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 you’ve ever seen, the two of you stop in front of an office door that reads: Emiliano Castillo.
“Thanks for walking me here,” you murmur once he turns towards you.
There’s the faintest hint of a fire burning behind Harry’s eyes. So faint that you aren’t even sure if you’re really seeing it.
“Guess I’ll see you soon,” he states, his voice a little rougher than it was before.
You’re not too sure why, but your skin prickles at his tone. Goosebumps spread across your arms as you look up at him.
“See you soon, Mr. Castillo.”
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 men’s 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 you’d make the prettiest noises as he fucked you into oblivion. He’d make sure to drag his cock within the deepest depths of you, making you and your pussy sing.
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.
Harry doesn’t think he’s 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 isn’t completely sure about what it was exactly.
After all of that, there’s one thing Harry knows for sure: You’re his, whether you know it or not.
Setting up the gala with the coordinator has been… eventful. You’re 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 isn’t your fault that men act like pigs around you.
The venue is beautifully decorated and you’re 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 didn’t know how rich.
Right at 7PM, guests start to pile in. Women wearing diamonds and gold around their necks, wrists, and fingers. You’re guaranteed that if you sold this building and the people in it alone, you’d make a lot of money. But you aren’t here to think hypothetically, you’re here to do your job, and you’re going to make sure the photographs are up to both your boss’ and Emiliano’s 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. It’s nearing 8:30 and Gavin — another photographer — is starting to get antsy.
“We’re supposed to get a shot of them coming in,” Gavin says through his teeth, letting out an exasperated breath.
“They’ll be here,” you murmur, your eyes focused within the camera lens.
You’re 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.
When one head snaps towards the door, so does your camera, and you don’t 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.
It’s 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.
You could already tell he was a big and broad man. Probably manhandling every woman he’s ever been with.
“Did you get the shot?” Gavin asks, pulling your attention away from the man across the room.
“I got it,” you nod slowly, taking a few more just for good measure.
Harry’s gaze still hasn’t moved from you, and for a brief moment, you wonder if this is how mice feel underneath a microscope. Their little bodies squirming as they’re being examined and experimented on against their will.
“You better fucking have,” 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.
You may not be looking at Harry, but you can still feel his gaze on you. Briefly, you wonder what he’s thinking about, but then his father starts speaking.
“May 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 wife’s 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 – 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 other’s backs during the years to come. And please… enjoy yourselves tonight, and don’t forget that all the funds collected tonight are going towards charity.”
Emiliano and Anastasia raise their glasses of champagne before Ana continues, “To the Crown Castillo family.”
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. You’ve learned over the years that these kinds of people appreciate the ‘vibe’ of the pictures more. If they look united, they’ll love the photos.
You lower your camera, checking all of the photos you’ve gotten so far before a man walks up to you. “Excuse me,” he says, placing a hand on your bicep to get your attention.
You look at his hand before you look up at him, “Can I help you, sir?”
He extends his hand out, introducing himself, “Lucas Taylor, Taylored Photography.”
Extending your hand out, you stare at him. He’s a recruiter, no doubt. With a company name that doesn’t even sound familiar to you, and you know all of the photography companies in New York. Emiliano didn’t tell you about another photographer being here, so you’re a little confused.
“I must say,” he puts his hands in his pockets, straightening his posture, “the photos you’ve taken thus far are beautiful.”
“How would you know?” you query, “You haven’t seen them… Lucas.”
He chuckles softly at your retort, nodding, “You’re right.” The heated look he’s giving you isn’t very subtle, and it makes you a bit uncomfortable. “I just wanted to tell you how breathtaking you look in that dress, miss…” 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. “You’re a little close, aren’t you?”
“Oh, I,” Lucas stammers, chuckling sheepishly, “I was just complimenting her on her-”
“I’d advise you to leave,” 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.
“I didn’t need saving.”
“Really?” he draws out with a raised eyebrow, putting his hands in his pockets, “‘Cause it seemed like you were dying to be saved.”
His tease makes you narrow your eyes slightly, “I appreciate the act, but I can handle myself, Mr. Castillo—”
“Harry,” he corrects you, “I think we’re well past the formalities now, don’t you think?”
“What, because you ‘saved’ me?” you retort.
“That’s exactly why,” the corner of his lips tug up into a small smirk, making you roll your eyes.
“Look, I’m trying to do my job for your father. So if you don’t mind, I’d like to get back to it now.”
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. There’s a huge chance that you don’t 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. There’s just something so intriguing about you and how you carry yourself. It’s not surprising that he’s 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.
It’s been weeks.
Harry hasn’t been able to get you off his mind. He doesn’t think he’s ever fucked his fist as often as he has lately. He’s done it at least four times today, and he’s painfully hard again, but he can’t wrap his hand around his cock without hissing.
You’re taking over his mind, and you haven’t even really done anything.
He’s looked up the photography company you work for to see if your number is anywhere on it, but the website only has the owner’s information on it.
Asking his parents would be the easy thing to do, but he doesn’t want to raise their suspicions. They already hassle him enough about finding someone to marry, and he doesn’t 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 father’s office. You’re 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. You’re on the opposite side and have yet to notice him, but he catches up to you just before you make it to his father’s office door.
Just as you’re 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.
“Hey you,” Harry says, putting his hands in his pockets like he wasn’t entirely in your way.
“Hi,” you reply tentatively, dropping your hand down to your side. “Is your dad here?”
“No, he’s out on lunch,” he averts your gaze for a moment, making eye contact with his assistant before he looks back down at you.
“Oh, I was told to drop off the pictures here,” you murmur, tucking your hair behind your ear as you take a step back. “I’ll just come back later—”
“I can look at them,” Harry says a little too quickly, clearing his throat and backing off the door, “I mean, this is my firm just as much as it is my parents’. Let me look at them.”
“Okay,” you draw out, handing him the portfolio, “Your dad can email me if you guys aren’t happy with the photos.”
“I’m sure we will be,” Harry states matter-of-factly, giving you a charming smile as he takes the folder from you. He holds it like it’s something sacred, “We can get this done now, if you want. Why waste more time on this?”
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 isn’t 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.
You shift under his heated gaze, crossing your leg over the other and sitting up straighter.
Harry smirks faintly at your reaction, knowing he’s got you right where he wants you. “These look amazing,” he compliments, putting down the photographs to make eye contact with you.
You murmur a small thank you, intertwining your hands in your lap. “I’ll send them over to your father this afternoon so you guys can… do whatever you please with them.”
“And then we’re done?” he asks.
“And then we’re done,” you confirm, slowly nodding.
“So,” Harry starts, standing up to round his desk, “you won’t be working for my company anymore, right?” he asks, sitting on the edge of his desk – directly in front of you.
You can hear the frantic pulse of your heartbeat thrumming in your ears. Though, you keep it strictly professional.
Harry’s eyes follow your movements as you stand, pressing his palms into his desk and looking at you with his big brown eyes.
“That’s correct,” you confirm, straightening your posture and adjusting your suit jacket. “We won’t ever have to see each other again, Mr. Castillo.”
“Harry,” he corrects you again, “And who said anything about not seeing each other anymore?”
“I did.”
Harry huffs, shaking his head slowly, “You can be very disobedient. Someone outta teach you a lesson.”
Your eyes narrow by a fraction, taken aback by the sudden statement that came tumbling out of his mouth. “Is that what you tell all the women you sleep with?”
“I—”
“Women aren’t on this earth for men’s pleasure. We are people, and we have feelings,” you scoff.
Suddenly he stands, towering over you with his broad frame. But you don’t back down, standing your ground and looking up at him with a defiant look.
“I never told you anything about my sex life,” he states, his voice low.
“Aw, did I hit a nerve?” you pout, “I know you didn’t. I like to know the people that I work for, and it wasn’t 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 on—”
Harry’s 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.
“Say one more thing,” he warns, eyes flicking to your lips momentarily. “I’m used to getting what I want, when I want it.”
“That must get very boring,” you tease with a tilt of your head. “You want me? Then earn it,” that’s all you leave it at before you step back from him, heading towards his office door. “Tell your father I said thank you for the opportunity,” a small smirk tugs at the corner of your lips, and then you’re gone.
Harry exhales harshly through his nose, running a hand through his curls as he’s left there: wanting you.
You gave him a challenge and he sure as hell isn’t 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.
Your friend, Samantha, sits across from you, telling you about her latest hookup. It’s some guy she met at a party a few months ago. They’ve 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.
“I think I blacked out at some point,” she mentions, prompting you to raise your brows in surprise.
“Jesus, Sammy,” 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.
“Have you heard from Harry?” she casually asks, earning narrowed eyes from you.
“Why would I have heard from him?”
“Because,” she draws out, lifting her coffee mug to her lips, “he definitely wanted to fuck you and you totally shot him down!”
You bite the inside of your cheek, “He’s 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 don’t need anything like that.”
“So?” she shrugs, placing her elbows on the wooden table, “I bet he fucks like an animal.”
“Samantha,” you deadpan.
“What?” she feigns innocence, “He is a man that screams dominance in the bedroom. If you won’t get under him, I will.”
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 you’re beginning to feel.
“It’s a crazy feeling being with someone that dominant and kinky,” she pauses, thinking. “Oo, maybe he has a sex dungeon—”
“Sam,” you shake your head once, “Enough.”
“I’m just saying,” her tone switches to something lighter, “maybe you’re missing out on what’s right in front of you.”
“Or maybe I dodged a bullet,” you tilt your head to the side slightly. “He’s like… in his 50s, Sam. You do know that, right?”
She shrugs, “Just because the wrapper is wrinkled, doesn’t mean the candy isn’t sweet.”
You raise your brows, amusement spreading across your face as you let out an incredulous chuckle. “You did not just say that. Do I need to take your phone away from you?”
“Probably,” she grimaces, “But seriously, he wants you. I don’t think you should let that go to waste.”
You press your lips into a fine line, hearing the murmurs of the cafe die down. Everyone’s gazes collectively fall to a single person who walks in, reeking of luxury and money. Like a moth to a flame, Samantha’s 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.
“Oh my God,” your friend murmurs, causing you to look up at her.
“What?” you ask, putting your hand over your mouth as you chew.
“Expensive looking hottie alert,” she states, nearly making you choke on your food.
You wipe the corner of your mouth, turning to look over your shoulder at who’s caught everyone’s attention. The world slows around you, Harry’s dark eyes locking onto yours as his signature smirk pulls at his lips.
“Wait, isn’t that—”
“Yes, it is,” you cut Sammy off, pulling your bottom lip between your teeth as Harry begins to stalk towards you.
“Ladies,” 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. “Hi,” he murmurs to you, a shit-eating grin plastered across his face.
“Hi,” you repeat his words, narrowing your eyes at him. “How the hell did you find me?”
Harry nods towards Samantha again, “Your friend posts a lot on social media.”
Of course.
“Look—“
“I just wanted to personally invite you to the Crown Castillo Black & White Gala,” he speaks lowly for your ears only. “But…” he trails off, reaching for a manilla envelope from the inside of his suit jacket, “I’d like you to look over something for me.”
“Is it regarding the photos I took?” you ask steadily, not looking away from his deep espresso eyes.
His Adam's apple bobs as he swallows, drawing your eyes towards it. “Not necessarily, but it is business.”
You tilt your head to the side, “What—”
“Just think about it and have an answer by the night of the gala.” He hands you the envelope, standing up and straightening his suit jacket. “I look forward to doing business with you.”
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: “THE COMMENCEMENT DATE BETWEEN THE DOMINANT AND THE SUBMISSIVE”
“Oh, you’ve got to be fucking kidding me,” 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.
“Good afternoon, I hope this email finds you well.”
You narrow your eyes at the first line before you continue reading.
“I hope you consider reading over the packet I left with you. Whatever you aren’t 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.”
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.
There’s no way this is real life, right? People don’t 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.
As the weeks go by, the contract sits untouched in your nightstand drawer. Harry emails you, but most of the time you don’t respond, earning desperate messages from him late at night.
You don’t 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 isn’t who you are. Isn’t who you were going to be.
You refused to bend yourself to a man’s 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. It’s dark and quiet, nothing like the other times you’ve been here. Your heels echo in the space as you step out.
Too loud.
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 Harry’s assistant, Rick, walking towards you.
“Sorry,” you call for the elevator again before turning around to face him, “I shouldn’t have come here. I was just leaving—”
“Mr. Castillo will see you now.”
That catches your attention, the doors sliding open behind you and revealing the two security guards. Rick holds up his hand, signaling them away. “We’re fine here. She has an appointment.”
The men share a look, deciding it’s best not to say anything.
“Please, right this way, miss,” Rick beckons you to follow him.
You glance back at the two brawly men, figuring that it’s 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 Harry’s office.
There’s nobody on the floor. Not even a single janitor in sight. It’s 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 Harry’s closed office door twice before opening it. “Have fun.”
“Wait, you aren’t staying?” you ask quietly, watching him shake his head.
“I don’t work overtime.” 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. “I’ve been expecting you. Please, shut the door.”
Hesitantly, you close the door behind yourself, feeling like you’re sealing a deal without signing your signature.
“Why were you expecting me?” 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. “Women usually come around to these sorts of things.”
The statement nearly gives you whiplash, your fingers tightening around the contract before you toss it onto his desk with a sharp thwack.
“Is that what you think? That women want to be your little plaything?”
“It’s not about that,” Harry claims, rounding his desk to stand in front of you. “It’s more about… testing your limits. Seeing how far you’ll go, learning what pleases you—”
You hold out your hand, “I’m gonna stop you right there.” Harry goes quiet, allowing you the space to speak freely, “You tell me one thing, but the contract says another.”
“So you read it?” he asks.
“No, I only read the title page,” you explain. “Sex shouldn’t be a business deal. A relationship shouldn’t be a business deal.”
Harry weighs your words, rolling his tongue over his teeth. “I prefer the term fucking.”
“I didn’t ask.”
He chuckles faintly, crossing his arms over his chest and sitting on the edge of his desk. “If you want to change things in the contract—”
“No, you don’t get it,” you cut him off again, stepping closer, “I didn’t want it in the first place. Did our conversation in this very office just fly over your head?”
“No, it didn’t,” he claims, shaking his head slowly, “but I can tell that you want more from me.”
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, “What is it that you want? Money? Jewelry—”
“You can’t buy me, Harry,” you interrupt him. “I won’t sign your sex contract and I don’t want to see your face again.”
He nods once, “You came to my office at 9PM just to tell me that? Something you could’ve emailed me or told me over the phone.”
You roll your eyes.
“I mean, it’s a little much, don’t you think?” he asks.
“No, you’re right,” you take a slow step back, “Goodbye, Mr. Castillo.”
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 you’re flush against his chest. The collision steals all the air from your lungs, hands instinctively coming up to steady yourself on his biceps.
Harry’s 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 don’t expect is for him to spin the both of you around, sending everything on his desk flying before he bends you over it.
“Is this what you wanted, princess?” he rasps, breath hot against your ear as he hikes up your skirt.
“Harry—” 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 that’s started to bloom from the force of his palm.
“You have no idea what you do to me,” he murmurs in your ear, the metallic rattle of his belt unbuckling filling the office.
“This is a bad idea,” you weakly protest. Though, you make absolutely no effort to move.
“Really?” he taunts, dropping his slacks and boxers in one go. “You’re saying one thing… but your body is saying another,” 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 shouldn’t happen. Fuck, you shouldn’t 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.
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.
“Fuck,” he breathes, “you’re so pretty.”
“Just shut up and fuck me,” you quip.
Harry chuckles darkly, shoving himself in, the stretch stealing the air from your lungs as you both moan in unison. He doesn’t give you time to adjust to his girth before he’s 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 Earth’s axis has finally shifted into place as your slick velvet walls greedily suck him in deeper. But you know this shouldn’t be happening – you worked for his family, he left a fucking sex contract with you, and he’s the most cocky son of a bitch you’ve 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. You’ll get your fill just this once, you tell yourself, succumbing to the feeling of him splitting you open.
“Look at you,” he purrs, “taking my cock so well, baby.” 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.
“Yesyesyes,” you chant, your jaw going slack, the sting of your hair being pulled, an odd but welcome sensation.
Harry’s other hand slides up to your waist, indenting his fingertips into your skin. “Is this how you like it?” he punctuates between thrusts, “I knew you’d be fucking perfect.”
For now, you ignore the comment, too focused on your pending orgasm and the roaring of your blood rushing in your ears. “Ohh, fuck,” you slur, feeling every ridge of his cock stimulate your sensitive spots perfectly – 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 he’s just as affected as you are.
“You feel so fucking good,” 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.
“Harry,” you whimper, heat pooling low in your abdomen as you near your peak.
“Shit,” he hisses, your walls pulsing and squeezing him just right. “You gonna come for me?” he rasps, slipping his hand between your legs to circle your swollen clit.
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.
“Did I hurt you?” he asks quietly when you don’t speak, watching you adjust your clothes and hair back into place.
“No,” you shake your head, turning around to face him, “it was good.”
He hums in acknowledgement, “So will I see you tomorrow night?”
You open your mouth to speak, but nothing comes out just yet. Honestly, you hadn’t thought about whether or not you would go to the gala. What would you even do there besides accompany him and fulfill his… needs?
“I haven’t made up my mind yet.”
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.
“You should go,” he murmurs, leaning in to press his plush lips to yours, giving you a tender kiss that you didn’t think he was capable of.
Despite yourself, warmth blooms in your chest, leaving you wanting more.
Everything feels wrong: your heels are too uncomfortable, dress too tight – too long, jewelry too heavy.
You felt completely out of place. This isn’t your crowd. You’re 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.
You’ve never been in the sea of people you take pictures of.
The building is 24 stories, drowning in exquisite taste and class – something you definitely missed the lesson on in school. Chandeliers scream money, reflecting off the lights and the diamonds dangling from women's necks.
Soft jazz music fills the lobby, creating an alluring atmosphere that eases your nerves for the moment.
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.
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.
What the fuck were you doing here?
This isn’t your scene and you’re already going against your morals – 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.
Neither Harry or his family are anywhere to be seen, tempting you to leave before you’re 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 don’t hesitate to grab one, hoping the fizzy beverage will ease your racing heart.
It’s just a party, you tell yourself. Hell, not even a party, this could pass as someone’s fucking wedding reception.
Just before you burrow deeper into your inner turmoil, everyone goes silent – 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.
“Happy birthday, Mrs. Castillo!”
“Happy birthday, Ana!”
People begin shouting out, the older woman laughing and wrapping an arm around her husband.
Harry invited you to his mother’s 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 don’t move from your spot until he disappears into the crowd and you’re 100% sure he can’t 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.
“There you are,” a familiar voice says behind you, placing his forearms on the counter. “You’re avoiding me.”
You stand up straighter, rolling a toothpick in between your fingers. “Am I?” you query, tilting your head to the side. “You don’t even know how long I’ve–”
“I noticed you the second I walked in,” Harry cuts you off, rendering you speechless for a second.
He chuckles when you don’t respond, another glass being replaced with your empty one. “Is that so hard to believe?”
“A little, yeah,” you murmur, nodding before you sip on your drink.
Harry watches your throat work when you swallow, his mind going to more impure places. “You wanna get out of here?”
You raise your brows, “Isn’t this your mom’s party?” you pause, leaning in and lowering your voice. “Y’know, I don’t appreciate how you blindsided me with that, by the way. I would’ve brought a present.”
He chuckles, straightening up and looking down at you. “Now where would the fun be in that?” he asks, pausing before adding, “Plus, you didn’t need to. My mom already adores you.”
Surprise flashes across your face before you remember that you worked with her and her husband – not just Harry. “Well, she was lovely to work for,” you murmur.
“So what do you say?” he asks, leaning in to whisper in your ear, “Let’s go somewhere more private.”
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. “Just because we had sex doesn’t mean that we’re together now.”
“Really?” he draws out, straightening up and placing his hands in his pockets. “So you’re not gonna go home with me?”
“I didn’t say that.”
The city of New York twinkles below, reflecting in your irises. There hasn’t been a time where you’ve seen the city like this: so high up and a lot clearer.
“You can see most of the city from here,” you murmur to Harry once he steps behind you, wrapping his arms around your waist and turning you around.
“Wouldn’t you rather look at me?” he teases, earning an eye roll from you.
“You do that a lot,” he points out.
“Do what?”
“Roll your eyes at me.”
A small smirk tugs at your lips, “And you’ve deserved it every single time.”
Harry’s hands tighten on your waist, pulling you flush against the hard planes of his body. “Have you thought about the contract anymore?”
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. “No, because I don’t have it anymore. Plus, I already told you my answer.”
His eyes narrow by a fraction before he pulls you by your wrist, leading you up the stairs in his penthouse.
“Harry,” you try to get him to stop, but he tightens his grip on your wrist.
“I just need you to see,” 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.
“Oh, my God,” you whisper, your body going rigid, the shock evident on your face.
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.
“This is my playroom,” Harry announces.
Your eyes are wide, lips agape as you assess the sight in front of you. “Yeah, I can see that,” you breathe, “Jesus Christ, Harry–”
“Before you start,” he cuts you off, “just look around. Nothing in here can harm you, I promise.”
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 you’re 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 you’ve never seen before sits in front of the bed, and without really thinking, you run your fingers through the rough material.
“That’s called a flogger,” Harry informs you, moving to hover beside you.
You snatch your hand back like you’ve been burned, suddenly remembering his reputation and the other women he’s most likely used this stuff on. Crossing your arms over your chest, you move on, examining the various cuffs and gag toys he has.
“Say something,” he murmurs, “Please.”
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 didn’t know how kinky… Until now, that is.
What the fuck have you gotten yourself into?
This has never been something you’ve been remotely interested in, and now it is right in your face.
Finally, you look back at Harry. “You do this stuff to women?” you ask, even though you already know the answer.
“Yes,” he confirms, “but everyone walks away happy.”
“H-How?” you stammer, some of your willpower returning to your body. “You’re a sadist.”
“Dominant,” Harry corrects you, earning an eye roll from you. “That right there,” he points at you, “If you were mine, you wouldn’t be able to sit for a week.”
“Excuse me?” you chuckle breathlessly, crossing your arms tighter across your chest. “By definition, you are a sadist. You get off on people’s pain.”
“It’s not that,” he states, a smirk tugging at his lips. “I told you: it’s all about testing limits.”
“Why?” you shrug, “Why would you want to…” you gesture towards the dangling whips on the opposite wall, “use these kinds of things on people?”
“For pleasure,” he answers like it’s completely obvious.
You shake your head slowly, “You can’t just enjoy regular sex like everyone else?”
When he doesn’t answer, you continue. “I don’t know what you want from me, but I sure as hell know that this isn’t a relationship.”
“I never said anything about a relationship.”
That’s what gets you. Your brows knit, an unfamiliar ache settling in your heart. “Then what the fuck are you doing with me?”
Instead of answering, he grabs a silk ribbon from a drawer, walking back over to you. “Hold out your wrists,” he instructs.
You glare up at him, and he senses your defiance. “I’m not gonna use them to force you into anything, I promise.”
To make sure he knows you don’t 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.
“It doesn’t hurt, does it?”
“No,” you whisper, meeting his eyes. “No, it doesn’t.”
“All the fear is in your head,” he voices firmly, letting the silk slip from your wrists.
A thought pops into your mind as you drop your hands to your sides. “If you want to… continue having sex with me, then why can’t we be together?”
“This is the only kind of relationship I associate myself with.”
Confusion stretches across your face, your brows furrowing as you try to see through his facade. He’s telling you one thing, but the way he’s acting is the complete opposite. He almost seems… obsessed with you; he hasn’t left you alone for months, he tracked you down via Samantha’s 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.
“How many women have you done this with?”
All you know is what you and your friend could find on the internet, and honestly, it wasn’t much. News outlets are very vague when it comes to Harry Castillo’s personal relationships, and it makes you curious.
He tosses the ribbon onto the bed, placing his hands in his pockets. “Let’s not go there right now.”
“Why not?” 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 he’s not telling you.
“How many?” you repeat your question earnestly, keeping your place.
Harry rolls his tongue over his teeth, “Twenty.”
“Twenty?” you breathe, all of the air leaving your lungs at once. “Christ, Fabio,” you joke, deflecting the situation.
Your mind swims within multiple questions.
Who’s to say that there won’t 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 doesn’t laugh at your joke, his face remains serious. “It’s the way I am.”
“Why?” 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.
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. There’s the smallest hint of vulnerability in them, and it’s gone the moment you notice it.
“Be honest with me,” Harry says, “what are you thinking?”
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.
“I don’t know,” you answer honestly, heading for the stairs. “That’s… a lot to take in,” you look over your shoulder, seeing that he’s following a few steps behind you.
“If you don’t want anything to do with me anymore,” he stops at the end of the hallway, looking down at you, “that’s completely fine.”
You know he’s not fine with it, but you appreciate the statement more than you’d ever let on. “I just,” you start, trying to find the right words as you process what he showed you, “I don’t think I can do that: bend to the will of someone else. That’s not me.”
He nods slowly, his eyes mimicking a puppy. It’s almost enough to make you change your mind.
Almost.
“I can’t be one of your girls – I won’t.”
part 2
a/n: i couldn't find anything like this so i wrote it myself 🌝 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 😅 but i hope you enjoyed reading it. feedback is much appreciated! (part 2 soon i hope lmao)
᯽ 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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