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*HUSBAND MATERIAL: a harry castillo x reader story.
Three times Harry tried to propose, and the one time he finally did it.
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warnings: mdni, established relationship, reader is afab and goes by she/her, vomiting, allergic reactions, unspecified age gap (harry is late 40s, reader's age is not mentioned apart from being younger), eating/descriptions of food, 3 + 1 trope, wealth gap, alcohol consumption, harry's family being kinda shitty, hospital visits, matching tattoos, no use of y/n, hopefully this makes yall giggle, pure fluff.
word count: 4.4k.
fox says: hi friends, thank you for reading! no smut on this one, sorry! i've never written for harry before so i'm sorry if this feels a little ooc. the picture above is just for aesthetics (i'm so in love with this dress its no joke) and there is no physical description of reader. as always, please let me know how we feel!
also available on archiveofourown.
one: the oysters.
Harry knew he wanted to marry you the day the two of you met. He didn’t know he was falling in love back then, all he knew was that he wanted you more than he’d ever wanted Lucy or any other woman. With her, it had been a pragmatic decision: He needed a wife, she wanted the money— Lucy was beautiful, poised, and would blend in well with his lifestyle. You are the opposite. You’re loud, and you snort when you laugh, and you don’t smile in that vacant, demure way most socialites do. You have a job in which you make no money, but you stay there because you love it so much; you live your life to the fullest, always pushing uptight Harry to his limits, always testing and challenging him. Harry wants to marry you because he wants you. Not because of his image, not because he’s afraid to die alone or because his mother keeps nagging him about heirs but because he simply cannot imagine a single day in which he doesn’t wake up to your messy hair and frowny face.
He decides on a different approach than the one he had with Lucy; he doesn’t take you on a grand vacation but rather a lavish afternoon on a yacht he borrowed from a friend — he mentioned buying one once, and you made so much fun of him that he gave up on it —, with a seventeen course tasting menu that is a trip through your relationship: Bite sized meals from every big step of your relationship, from the first night you’ve slept together, from your first date, from a memorable night in Greece with a kleftiko so good it brought tears to your eyes.
Things go south on the fifth course, when you’re sharing a tray of oysters and caviar canapés that are a memento from a trip to Australia— The two of you had spent just the weekend there, because Harry’s company had a crisis that meant flying back home before the trip was over, but Harry had spent so much time between your legs as an apology that you’d squirted all over his face.
He’d gotten a lung infection from breathing it in that landed him in the hospital for three weeks, but it was still one of the best nights of his entire life.
“God, I love oysters.” You say, a little giggly from the champagne, leaning into his side. “Reminds me of that night in Almonta.”
Harry hums, pretending that night isn’t the sole reason for the platter of oysters in front of you.
“I remember that. Best meal of my life.” He gives you a small, toothy grin when you tilt your head back to look at him. “The oysters were alright, too.”
You cackle, shoulder bumping against his as you stab the shellfish with your fork, carefully unsticking it from its casing before slurping into your mouth; butter drips down your fingers and Harry can’t look away, picturing what they would look like with the diamond ring he has in his pocket.
“Yeah, the tingling isn’t all that fun, though.” You say, casually, wiping your hands clean.
Harry blinks.
“The what?”
“The tingling?” Your statement sounds more like a question, and you frown at him. Something must show on his face because you chuckle, uncomfortable. “You know, the way oysters make your mouth a little numb?”
“Honey, no—” Harry shook his head, pushing the platter away. “That’s— That’s an allergic reaction. How many of those did you eat? Are you breathing okay?”
You frown, looking at the nearly empty platter before shrugging sheepishly. “Uh— More than in Almonta. By a lot. I feel fine, just the tingly mouth and uh— Maybe a little nauseous?”
Harry jumps from his seat, telling you to stay still before he rushes towards the wheelhouse. They don’t have any epipens on board, which seems like a terrible oversight, but the captain immediately starts barking orders, getting the small crew onto some sort of emergency protocol and promising they’ll get the yacht back to shore as quickly as possible.
You’re violently retching in the suite’s bathroom by the time Harry finds you; your skin clammy and cold. He kneels by your side, holding your hair out of the way, breathing through his mouth to keep himself from puking as well. He stays there no matter how many times you try to usher him away, thinking of the vows he’ll make as he wipes sweat away from your forehead— In sickness and in health, even if it makes him want to puke too.
There’s an ambulance waiting for the two of you at the harbor, fully equipped and prepared to handle the allergic reaction that, thankfully, doesn’t seem to affect your breathing or your throat. Harry climbs into the ambulance with you, even as you try to wiggle out of you, telling everyone that you’re fine and that you don’t need a hospital and it takes the paramedic reassuring you that the hospital has a good financial aid for him to realize that you’re concerned about money and not the hospital itself.
It makes him feel like a failure. Here he is, a man with more money and power than anyone deserves, and the most precious thing in his life is worrying about her financial future. He squeezes your calf, heart constricting in his chest. For richer or for poorer.
“Don’t worry about that.” Harry says, low enough that you’re the only one that hears it. “Don’t ever worry about that. I got you, always.”
two: the wonder wheel.
The second time Harry tries to propose, he steers away from seafood. He takes you to Coney Island instead for an afternoon of childish glee at the amusement park: Harry hasn’t been there since Peter’s seventh birthday, and he tells you the story of how his mother’s company was just starting, and how the boys had shared a Nathan’s hot dog because it was the most she could afford— He omits the fact that they both fought over it and that Peter cried all the way home because Harry told him their mother only made his birthday special because it was the day she plucked him out of a dumpster and decided to raise him as her own.
He can’t remember the last time you looked this happy. You’re giggling the entire day, dragging him around the park, outright cackling at him when he drips ice cream on his 800 dollars sweater but your eyes are kind as you try to help him wash it off — it’s cashmere, the whole thing ruined and stretched out where the ice cream had been — and cussing so much as you ring toss that, for a moment, he’s genuinely afraid you might get kicked out of the park before he can propose.
Harry slips the guy manning the ferris wheel twenty dollars so that he stops the ride when the two of you are at the very top, just as the sun starts to set. It’s romantic, even if a little cliché, but Harry thinks you’ll like it. He’s been taught, from a very early age, that the right way to love is through grand shows of romance. The roses and the private dinners and the lavish vacations— Expensive gifts, big and small acts of chivalry that are meant to show someone that you love them; it’s what women want, his brother told him once, even if Harry couldn’t quite grasp the concept of why. He’d done it all with Lucy because he felt like he had to. It was a transaction, and Harry constantly felt the need to prove that he was well-suited for her.
With you, it’s different. He does it because he loves the way your face lights up, how you giggle and bat your lashes at him; how you say it’s silly and that he didn’t have to go out of his way for you but there is still a prep to your step for the rest of the day.
Harry does it to make you happy, and that is an unfamiliar feeling for a man so used to putting himself first.
He’s shaking all over by the time the ferris wheel finally stops. You turn your head this and that way, sitting on the very top of the wheel; it has a beautiful view, he’ll give you that— The sun is just starting to set, falling behind the skyscrapers in the distance, the entire sky taken over by shades of orange and pink.
“I think I can see your apartment from here.” You giggle, pointing to the opposite direction of Tribeca but Harry pays it no mind, because it’s the first time you’ve had your back to him all day, and it’s fucking perfect.
He reaches into his pocket with trembling fingers, grasping the dainty diamond ring he’s been hiding for over a month now; he has a speech prepared, a little story about a boy who never thought he would be worthy of love and the girl that showed up just at the right time but, as he tries to position the ring in the right way, it slips from his sweaty fingers.
Harry curses so loud it makes you jump.
“God— Fucking damn it.” He dives forward, trying to catch it before it hits the ground but instead the ring bumps against his fingers, arching through the air and falling directly through the grates on the cart’s windows.
“What was that?” You scoot forward in your seat, trying to peak through the metal squares. “What did you drop?”
“Nothing.” He says, and it sounds so fake he follows up with: “A penny.”
“A penny?” You raise an eyebrow. “Does the big Mr. Castillo even know what that looks like?”
Harry huffs, rolling his eyes just for good measure— It only lasts for a second, though, before he discreetly starts to peer down below; the view from above isn’t great, but he knows there’s no way he’ll ever get that ring back.
“Harry?” You call out, your voice so sweet when he finally pulls his eyes away from the ground. “Are you okay? You look like you’re going to be sick.”
“I’m okay.” He says, bringing a hand to smooth the little crease between your brows. “It’s alright, just a penny.”
A ‘penny’, worth two hundred and seventy thousand dollars, lost somewhere between colorful carts and wonder wheel fuselage.
By the time the two of you go home, your eyelids are drooping, your head on Harry’s shoulder as his driver brings the two of you back to Tribeca; you’re clutching tightly to the walrus plushie Harry won for you, and he can’t stop thinking about how bright you smiled when he did it. The streetlights reflect on your face, and Harry thinks you might be the most gorgeous thing he’s ever seen.
“Today was very special.” You mumble, voice clouded by sleepiness. “Thank you.”
Harry turns his head, ignoring the insistent vibration of his work phone, and presses a kiss to the top of your head, heart aching with the knowledge of just how more special it could’ve been.
three: the waterfall.
Harry is nothing if not an obstinate man. Where others (his brother included, during one late night phone call) might see the two failed proposals as a sign of the universe that, perhaps, he’s making a mistake, Harry sees it as a challenge. He’s a man that is used to high stakes, that thrives off of the thrill of a risky business deal, a shark in the water that smells blood miles away and goes for it. He’s also the sort of man that gets nervous enough to drop an engagement ring down a ferris wheel (which he really never recovered, just as he presumed), but that’s part of why he loves you so much. You make him human. With you, he’s not Harry Castillo, the business mogul that is known for hostile acquisitions and getting exactly what he wants, when he wants it. With you, he’s just Harry.
After the wonder wheel disaster, Harry takes a different approach. He goes in hard, not with his heart but with his mind, tackling the proposal like he would a difficult client: He starts with the ring, going back to his usual jeweler and designed a custom piece— Not the same as the one he’d lost, because someone would eventually find that ring and he didn’t want a copy of your ring walking around but a brand new one, inspired by several celebrity engagement rings he’d noticed you zoom in on while scrolling through your phone. A gold band, because he knows you always go for the yellow gold when picking out jewelry, twisted and molded in a way that would, eventually, stack perfectly above the wedding band.
The main difference between the two rings, however, is the diamond. They’re both six carats and pear shaped, but this one is lab grown— His mother would go into cardiac arrest if she ever knew, and even his jeweler had raised both eyebrows when he requested it but, two days after the Coney Island fiasco, you’d gotten into a pretty heated argument on an Instagram post’s comment section about the ethics of natural jewels and the consequences that mining them has on the people who are enslaved and exploited for it.
Harry had never thought about that. He had never thought about a lot of things before you— The consequences of his wealth, what that meant for other people around him. It shone a terrible light on all the things he took for granted, forgetting his not-so-fortunate past as the years of more money than he could ever need stacked up on top of each other. And he’s both embarrassed for it and thankful that you came into his life, no matter how much his mother scoffs at your antics.
He had also told himself he wouldn’t do it overseas. He’d planned the trip for Lucy’s proposal, and it felt like a cheap second try but, all things considered, Harry thinks proposing abroad might be the thing that makes it so special. So, after seeing the way you keep swooning at Tiktoks of Phi Phi Island, he takes you to Thailand.
Truth be told, Harry didn’t expect to like the country as much as he does— He’s never been a beach kind of guy, always preferring the bustling of a big city, but there is something about sitting on the silky white sand of Railay Beach watching you dive into the crystal blue waters that almost has him proposing right then and there.
In retrospect, he probably should have; even if he left the ring back at the hotel, maybe he should’ve dropped to his knees when you finally come out of the ocean in your pink bikini, salt water dripping down your chest. At least, like that, he would’ve proposed at all.
You plop down on the beach towel next to him and Harry hands you his half-drunk dragon fruit kiwi smoothie; you lean against him, sticky shoulder bumping against his sunburnt one.
“Don’t think I’d ever get tired of this view.” You say, softly, watching as the blood red sun starts to set.
“I wish we could live here.” He admits in a small voice, tensing as he waits for your reaction— It’s childish but he’s embarrassed of the admission, afraid of what you’d think of his moment of vulnerability even if, logically, he knows you’d never judge him for anything; not like his parents did, at least, who’d mock him relentlessly whenever he was a kid and cried on the way home after a vacation.
“We?”
Harry shrugs, feeling his already reddened face burning even brighter as you shift to stare at him. He keeps his eyes on the ocean, doing his best to pretend he hasn’t just opened his heart to you with a single, small sentence. You press a kiss to his shoulder.
“Me too.”
He waits until almost the end of your trip, when you finally make it all the way up to Tak. For all of Harry’s new-found love for the beach, he’s not a big fan of the forest. Still, he hikes with you all the way to Pha Charoen because he knows that proposing to you in the scenic staircase-shaped waterfall is going to be a thousand times more memorable than the wonder wheel or a borrowed yacht. The private tour guide he hired giggles as Harry wades into the water, cellphone in hand and fully prepared to serve as a photographer during the big moment; you’re in a pretty dress that is short enough so it doesn’t get wet but Harry, for all of his planning, trudges with water soaking into his khakis— He thinks it’ll look bad in the pictures but maybe you won’t care, not with the way you’re smiling so wide, taking in the views of the water that cascades just a few feet away.
The tour guide, Pranee, gives Harry a discreet thumbs up when the two of you are perfectly in frame and then points to the left. “Look, guys! A monkey!”
You immediately turn your back to Harry, searching for the animal that doesn’t exist. He breathes deeply, takes a small step back and kneels.
Harry doesn’t even see it happen. One moment he’s lowering himself on one knee, the other he has both feet in the air, his back scratching against the rock formation as he slides down several steps. He hears you screech and then nothing else other than the roaring of the water as he unwillingly somersaults down the current.
He ends up with seven stitches on his bicep after getting caught in a particularly sharp rock, a twisted ankle and enough muscle pain to show that he is, indeed, nearing fifty years old. The ring somehow stayed in his pocket, thankfully, and you’re now using one of Pranee’s pictures of Harry being ass up face down in the water as your phone’s lockscreen, so he figures it wasn’t all bad.
four: the proposal.
Harry doesn’t give up. He is not the sort of man to give up on anything, especially not something this important. He just… Takes a step back. His recovery from the Thailand trip is slow, slower than it would’ve been a couple of years back, and it brings forth a whole plethora of realizations he has been trying to avoid. His age is the main concern— He feels like his body is starting to break down, his stamina dwindling, injuries taking longer to recover from; his mother starts casually mentioning botox every time they have lunch together, the grays in his hair more prominent every time he looks in the mirror.
Despite that, Harry doesn’t feel old (well, maybe only when it takes him five weeks to stop groaning whenever he stands because of a silly tumble down a waterfall). But then he looks at you, so much younger, still so full of energy and life and he wonders if he’s not selfishly taking away your youth.
So, yes, Harry doesn’t give up. But he does reconsider. He hides the ring in his office and leaves it there for a couple of weeks, choosing instead to spend his time with you without the worry of the perfect proposal— He still wants to marry you, wants to have the pride of knowing you carry his last name, the safety that comes with his money and his status. He wants you on his bed and his house and his car, wants your name next to his at every event. But it dawns on him that he’s not certain if you want that too: He’s been so focused on making sure to keep the proposal a surprise, he doesn’t even consider the possibility of your answer being no.
He decides to just ask you. Not in an actual proposal but more of a conversation, testing the waters to figure out if he can pull out the ring or if he should keep it hidden for another year, but there never seems to be a right time for that— Or maybe he’s scared of the answer, even though Harry would never admit to it.
The question slips out on a Saturday evening while the two of you are having a movie night in the shoebox that you call an apartment, sitting on the couch you stole from a garbage pile on the curb. You’d made Harry carry the damn thing for three blocks even though he promised he’d give you all of the couches in the entire world if it kept you from bringing garbage into your home.
The garbage couch is, perhaps, the most comfortable couch he has ever sat on.
“Would you ever want to get married?” He asks, watching the way your hand full of Skittles freezes halfway to your lips.
“What?” You ask. Despite how good Harry is at reading people, he cannot make sense of the emotion that fleets across your face.
“With me. Would you ever want to get married to me?”
You twist on your side of the couch, your knees drawn to your chest; you’re wearing a pair of sweatpants that you got either from Walmart or Target or whatever other big store Harry hasn’t set foot inside since he was a child, an old t-shirt from his days at Brown University that is ratty and stretched out from age, and a pair of Chanel eye patches.
This is another little thing that Harry loves about you. Here you are, in a stolen couch in sweatpants that might well be from the Dollar Tree, wearing an eye mask that costs over a hundred dollars. Any other person might’ve seen it as hypocrisy, but Harry knows better than that— He understands that you don’t care about boasting luxury, about flaunting his money or spending it on things that you might consider futile. You’re ambivalent but strong-willed, sticking to your morals and what you think is the right thing. Headstrong.
“Are you proposing to me, Harry Castillo?”
“No. Yes.” He pauses, trying to figure out the look on your face when you quirk an eyebrow at him. “Maybe. I mean— I tried three times already, so I figured I might as well just say it, but if you want it to be more romantic I can try again. Fifth time’s the charm or something.”
You throw your legs over his, swinging on the couch until you plop down on his lap, your chest pressed against his, shins bracketing his thighs. Harry’s hands find your waist all on their own, the weight of you a familiar and welcoming feeling.
“I would marry the shit out of you.” You say, fingers running through his hair. “So yes, if this is a proposal, I’m saying yes.”
He kisses you, your teeth clacking against each other as you both smile through the kiss. Harry’s heart thunders inside his chest, so fast he thinks he might go into cardiac arrest— And he’d die a happy man, because the way you press against him and giggle into his mouth brings forth an emotion that he never thought he’d ever truly feel.
Love.
It was true when he told Lucy he’d never been in love before, and at some point he truly thought that would never be in the cards for him, but all along he’d simply been waiting for you. The woman that challenges him, that disrupts his world and pulls him away from the trap of his own mind.
“I love you.” Harry says when he finally pulls back, and he thinks you’ll never understand how much he means it. He kisses your cheek once, twice, thrice. You giggle, folding in on yourself when his mustache brushes against that soft part of your neck where you’re extra ticklish.
“I love you too.” You say, grinning ear to ear. “Wait, what do you mean you tried to propose before?”
Harry groans, head tilting against the back of the garbage couch.
“You don’t even wanna know.”
bonus: the wedding.
The two of you get married in New York City, seven months after Harry finally manages to propose. It was a rocky road, with Harry’s mother trying to take control of the festivities and you slamming your foot down on having the party exactly the way you and Harry wanted it, and he’s never been so attracted to you as he’d been then.
Well, maybe only when you made your way down the aisle. You wore a shiny satin dress that was more champagne than white, figure accentuated by the corset that tied to your back— Harry had missed his portion of the vows, only snapping out of his trance when the officiant called his name twice; you’d laughed, and he’d blushed, and all Harry could think and say was about how lucky he was to have such a powerful, incredible woman by his side. He worships at your altar that night, trying to convey with his body what his words could not: How much he’d kiss the ground you walk on, how he’d never be able — or willing — to find someone that came even close to make him feel the way he does for you.
Your honeymoon is in Thailand. You make the same island hopping you’d done the last time — sans Tak, because Harry wasn’t ready to face that humiliation again — and you end the trip on Railay Beach, in a small seaside bungalow that Harry buys for the two of you. You get matching bamboo tattoos one evening after too many boozy smoothies: Your initials on his left collarbone, his initials on your left ribcage. If anyone asked, getting a matching tattoo with his wife at fifty years old while honeymooning in paradise had never been in the realm of possibility for one Harry Castillo, but he wouldn’t change a thing.
Going back to New York City after a month of good food, beautiful beaches and lovemaking is a sad affair and, once again, Harry is reminded of the ten year old little boy he once was, sitting in his parents private jet or the back of a car, holding back tears because he did not want to go back home. This time it’s just bittersweet, your hand in his as you sit next to each other on the private plane.
“Is it weird that I already want to go back?” You giggle, and Harry smiles, pressing a kiss to the bridge of your nose.
“No, Mrs. Castillo.” He says, savoring the words. “Not weird at all.”
Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
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Joel does math off the top of his head or correctly guesses the right measurements to something and suddenly it’s one of the hottest things you’ve ever seen
Or he does that carpenter thing where he measures, takes a pencil from behind his ear and scribbles the number on the 2x4 he's working on, then throws down a quick equation next to it to factor in the degree of the angle he has to cut it at then holding the pencil between his teeth while he makes the perfect cut
Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
✓ Live Streaming✓ Interactive Chat✓ Private Shows✓ HD Quality✓ Free Actions
Free to watch • No registration required • HD streaming
Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
✓ Live Streaming✓ Interactive Chat✓ Private Shows✓ HD Quality✓ Free Actions
Free to watch • No registration required • HD streaming