summary: you and harry fuck in the shower. you later realize that something has changed.
warnings: 4.8k wc. explicit content. pre-established fwb. handjob. fingering. unprotected p-in-v shower sex. fluffy aftercare. feelings get involved. contains a minor spoiler. no physical description of the reader other than she has hair.
a/n: full disclosure, i haven’t seen materialists (& idk if i ever will bc from what i heard about what happens, watching it will just make me mad lmao). anyway, after seeing this gif and harry edits, something possessed me to write this.
as always, hope you enjoy and feedback would be much appreciated!
Fuck, you need him.
Again.
Badly.
You had stirred awake at the sound of the shower turning on in the private en-suite, your hand brushing across the silk sheets beside you that are still warm. Then, comes the tender, pulsing ache between your thighs, one that sharpens when your memory starts drifting back;
His mouth, his fingers, his hands. Skin on skin, your breaths and moans intertwined like your bodies were, moving as one.
It has only been two, three hours since Harry's cock was buried deep inside you, his voice low and sinful as he whispered the filthiest things into your ear. He made you cum for a third time right there that night, much harder than the previous two (or ever)— and god, it was so intense that you passed out in his arms immediately after.
Now, you lie in an empty bed that’s too big for one person, craving Harry again as if you weren’t satisfied the last time. The truth is, he’s ruined you. He has from the very first moment you started sleeping together. Three months ago, to be precise, when this arrangement—pure hot sex, no strings attached— was agreed upon. You never expected it to leave you this wrecked and wanting more and more.
Harry is charming, handsome. Irresistible, addicting. Like he’s the only thing in the world that could pull you apart and piece you back together under the same touch.
And he’s in the other room. Standing alone, naked under a spray of water. Just several strides away.
Without a second thought, you throw back the covers and roll out of bed. Your bare skin prickles from the chill in the air; your body throbs from the earlier activities, and you almost couldn’t walk a straight path. But you don’t seem to care. Your feet carry you towards the bathroom door left ajar, not wasting any more time.
The warm, humid fog greets you at first. The water pattering softly against the pale white tile masks the noise of your movements as you approach the misted-glass shower stall.
Harry doesn’t notice you immediately, allowing you a few seconds to admire the sight of his broad back and shoulders. The way beads of water glisten and slide across taut muscles that ripple under his skin as he lathers soap unhurriedly all over his body.
Not only does he fuck like a god, but he looks like one, too.
He hums an unfamiliar tune to himself, quiet but rich; smooth and warm like whiskey. It echoes off the walls, the rumbling sound close to a touch you somehow feel even if it didn't land.
Your breath catches somewhere between your lungs and your lips. It's sweet, slow torture— you standing there and not saying a word, not reaching out. You can't tear your eyes away, not that you wanted to. Fuck, no. You're going to savor every second of this, commit each detail of Harry to memory, and tuck it away with all the other dirty ones.
And when you've finally had enough— when the blooming heat in your belly has melted down your restraint— you slip into the shower stall behind Harry, pressing your body gently into his solid back. He doesn't tense up at your unexpected presence. If anything, he relaxes more with you there. Steam envelops you as your hands glide over his slick chest, feeling the thrumming beneath your palm when he chuckles.
"Didn't mean to wake you, baby. You should've stayed in bed, I wasn't going to take too long," Harry says, his hand catching one of yours to bring up to his lips.
In return, you softly kiss the hollow between his shoulder blades. "And lose out on an opportunity to watch you in the shower? No, thank you. Besides, m'not really tired anymore."
"Sure about that?" He wonders, and you can practically hear the smirk in his tone. "Thought I wore you out pretty good earlier."
"Mhmm, you did," you murmur against Harry's back, your hands beginning to drift down his chest, fingers slowly caressing his soft belly, and the thatch of hair there. You almost miss the subtle stutter of his breath, drowned out by the steady cascade above your heads. "But I missed you and this..."
Harry lets out a soft groan when your hand lightly brushes against his cock, which has been stirring with interest from the moment your touch landed upon him. You grin at that, unseen by him, of course. You relish knowing how fast he gets worked up by you, from not doing too much at that either.
"Needy, needy girl," he cooes, thinking he’s in complete control here, just like always. Harry tries to turn around and face you, but you gently push forward, pinning him to the wall.
You keep your body flush against Harry’s to give him no room to move. He doesn’t fight it, though, which is more surprising to you than not. Perhaps he doesn’t make an attempt because your fingers are now wrapped around the girth of his cock, choosing to surrender to baser urges rather than delay relief.
But then again, you know Harry. You know he likes it when you show him what you want. When that bold confidence of yours doesn't shy away from him, acting as though you're worth more than his wealth and yours combined. It's what drew him to you when you first met at some glitzy gala in Manhattan neither of you wanted to attend in the first place. Maybe you taking the lead for a change is turning him on more than he anticipated.
“Fu-uck, baby. That’s it,” Harry grunts, rough and ragged. He leans forward, bracing an arm against the shower tile as you continue pumping his length with long, steady strokes from behind. His hand finds your other resting low at his hip, and he laces his fingers with yours, his grip tightening, grounding— you’re not entirely sure if he was holding back or barely holding on.
Slick from the coated mix of water, soap, and his own arousal, your hand moves up and down Harry’s shaft, hot and heavy, effortlessly. You see the way his head dips down to watch you work him over with such practiced and devastating ease. Every drag of your closed palm, every twist and tug and squeeze, unravels him in a way that he can’t and won’t stop.
Harry’s close. You’re well acquainted with his body at this point to be sure of that. You can feel it with each broken breath pushing past his lips, in the slight shiver beneath his skin, the tight rise and fall of his chest. How his hips jerk into your fist with small, shallow, desperate thrusts, a string of curses and praises muttered low along with your name.
There's something thrilling about having Harry like this, teetering over the edge. You could draw it out, tease him helplessly. Leave him aching, begging, and trembling like he often does to you.
But you didn't come here for that. As much as it lit a hot, dangerous fire within you, you wanted Harry to fuck you. You wanted the throbbing cock in your hand back inside you, to quell the ache that no fingers, mouth, or toys could ever do.
Your rhythm falters, then eventually stills. Harry is quick to react, a sound caught in his throat— half-protest, half plea. He inhales sharply, body tensing when he’s pulled back from the very brink. His head lifts from the tile where he’d rested it, and he glances over his shoulder to meet your hazy eyes.
The heat in his gaze is dark, searing, and hungry, as if he doesn’t at all appreciate the fact that you’ve stopped so abruptly.
“Not gonna finish what you started, baby?” Harry pants, his hand reaching down to drape over your fingers that remain loosely curled around the base of him. He twitches against the softness of your palm. “Didn’t think you could be cruel.”
“Cruel? Never. Well, at least not now anyway,” you reply, placing a kiss on the center of his spine. “I was hoping that you would finish inside me instead.”
“That can be arranged.”
You wring Harry’s cock with one last slow pull, just enough to make him shudder, before letting him slip from your grasp. It’s only then that you take a step back, allowing him space to turn to you.
And when he does, you feel the power shift back to Harry. Something low in your belly coils so tight that it almost hurts. Your eyes drag over him without an ounce of shame— flushed, gorgeous, and hard.
Fuck, Harry is so hard, his tip swollen and a shade or two darker. Just one look at him and your pussy clenches around nothing, begging to be filled. He notices this, notices how your thighs press firmly together from the mere anticipation, your eyes locked in a silent, electric exchange.
Then all at once, Harry’s mouth crashes onto yours, fierce, bruising, and urgent. The force of which nearly causes you to stumble if it hadn’t been for his steady grip settling on your waist. His other hand slides behind your head, angling you perfectly for him to deepen the kiss, his tongue insistent and greedy as it dives past your lips in a hungry sweep.
He doesn’t slow down, not even as he backs you against the cool tile of the wall. The shower stream hits only Harry now, his body shielding you from it, the heat of him replacing the warmth of the water on you.
Harry’s lips break away from yours, dragging them across your cheek, along the line of your jaw. He continues down onto your neck, his mouth moving with a purpose; teeth grazing lightly, nipping and sucking against your tender flesh until it undoubtedly leaves a bloom of color— you feel it, even if you can’t see it.
“So fucking beautiful… and all mine,” Harry rasps, the words meant for you, but just as much for himself.
You see his throat work as he swallows, his large hand skimming up the curve of your waist, thumb brushing gently under the swell of your breast. His heavy-lidded eyes take in every inch of you before him, as if this is the first time he’s ever seen you bare, wet, and wanting— like he’s looking at something so sinfully holy.
“Yours,” you whisper, and hearing it hits Harry like a live wire.
Because suddenly he’s surging forward, his mouth claiming yours again with kisses that are all messy and consuming, that leave you with no room to breathe.
Your head starts to spin, and your knees buckle from the intensity. But Harry's there, trapping you between his chest and the shower wall, keeping you upright, fully flushed against him.
Harry only breaks away from your lips when you arch your back slightly, rolling your hips against his. He lets out a groan, rough and guttural, his breath hot and uneven as it fans over your face. You rock against him once more, and he hisses at the sensation— at the sweet friction he gets from each grind against your pelvis. His warm, glistening precum smears across wherever it can reach.
“Feel that, baby?” Harry husks as your eyes drop to where the rigid line of his cock ruts between the two of you. “That’s all you. You did that. Made me so hard…fuck I can’t even think anymore. I need you— gotta have you."
A hand then comes into view, trailing from your waist to your hip, and then dipping lower and lower until he’s palming your sex, groaning low when he finds the slick mess pooling down there.
“God, you’re soaking wet. Haven't even touched you properly yet. All this from jacking me off, hmm?”
You answer with a breathless whimper when Harry leisurely drags two digits through your slit, gathering your arousal onto his fingers. Your gaze follows as he lifts his hand to his mouth, sliding those fingers covered in a thin sheen of desire between his lips, sucking and savoring the essence that is purely you.
He hums in satisfaction. "You taste so sweet, darling. Wish my legs weren't shot, ‘cause I'd go down on you right here, right now."
A renewed rush of heat spreads under your skin as you’re reminded of how unbelievably good Harry is at eating pussy. It’s earth-shattering each and every time. He listens to your body, knows exactly what to do and when to give it to make you come undone easily. You love it mainly because he’s not just going through the motions like your exes used to. No, not him. Harry will happily bury his face between your legs as if he’s a starved man.
Any and all thoughts in your head dissolve the instant the pad of Harry’s thumb brushes over your clit, sending a jolt straight to you. He holds your gaze, watching the pleasure ripple through your expression. His tongue flicks over his bottom lip to chase the lingering taste of you as he continues the tender assault on your sensitive bundle of nerves that soon has you writhing beneath his touch.
It’s almost embarrassing how quickly he’s gotten you to this point. How he’s not even inside of you yet, and if you let him, you could cum just like this. But you’re so wound up, so desperate to be filled more than anything that you don’t want that. You don’t want to prolong this. You couldn’t wait any longer.
“Want—want more, Harry, shit… fuck me. Please, fuck me,” you plead to him, and he stops, his fingers immediately pulling away, and damn it, is this how it felt for him when you took your hand off his cock just like that?
Harry flashes you a knowing smirk, but he doesn’t leave you hanging for long, though. He kisses you once more, this time unhurried. Softer. Much, much softer now, like he's kissing you simply because he wants to feel your lips on him again, to get his fill of it before his hands rest on your hips, gently coaxing you to turn and face the tiled walls behind you.
“Bend over a little for me, sweetheart. Hands on the wall— good, just like that. That’s my girl.” Harry guides you into a comfortable enough position, his voice thick as he speaks, nearly strained as though it bears the weight of his own arousal. He smooths his hand down the length of your spine, coasting along the curve of your ass where he squeezes the soft skin of it.
You hold your breath believing it might keep you from falling apart due to impatience, waiting for the heavy press of him against your entrance, the raw slide of hard flesh that makes you squirm at the intrusion. And it does. You feel the familiar flare of pressure as something sinks into you— a finger.
Then, another.
Harry couldn’t help himself. How could he when your dripping pussy is staring straight at him? Two of his fingers don’t fill you the same way his cock would, but at least your wishes have been granted somewhat.
Selfishly, you want more. Not this. More.
But when those two, thick digits delve in as far as they would go, it shuts you up long enough to get lost in the sensation. Harry doesn’t rush, and you’re too distracted by his skilled fingers working inside of you to protest. He crooks them just right, just enough that he’s pushing up against that spongy spot of yours that has you keening.
“Wanna make you come on my hand, my darling. Love the way you squeeze my fingers when you do.”
You shake your head deliriously. “On your cock, baby. I need your cock, been needing it so bad ever since I woke up.”
“You sure? We got all the time in the world for that—”
“Fuck me with your cock, Castillo,” you cut Harry off with a near growl, drawing an amused chuckle out of him. “Fuck me right now, or I swear I’ll just find somebody else—”
Your unserious threat is swallowed by the whine escaping you when Harry withdraws his fingers. Before you could recover from the loss, he’s gliding his length between your wet folds, the very tip of his cock nudging your swollen clit. The sudden contact makes you gasp and sway, your footing slips for a second, but his hands on your waist keep you firmly in place.
“Harry, please. Enough—no more teasing.”
“Shhh, it’s alright,” Harry croons, his hips shifting back the slightest, and you know what’s coming next. You’re sure of it this time. “Gonna take care of you now. Need you just as bad. Relax for me, baby.”
You suck in sharp breath, fingers flexing against the wall as the thick head of Harry's length breaches your cunt at last. He eases himself inside of you, inch by inch, so agonizingly slow that it drives you mad. He doesn't do this out of cruelty, but rather with a tenderness, making sure that he doesn't hurt you even if it feels like he's splitting you in half.
“F-Fuck honey, this pussy’s so tight for me,” Harry mutters through gritted teeth when he finally bottoms out, his fingers digging into your hip, allowing a few moments for you to adjust.
The stretch of him, the fullness Harry brings— fuck, it’s everything you’ve been aching for and more. You can’t explain how it’s possible, but somehow he feels even better right now. Maybe it’s from the build-up, the angle he’s got you in, or the way the warm air clings to your damp skin, amplifying every touch, every spark he sets alight within you.
Whatever it is, it has the nerves in your body pulsing to life, like a hot electric current running through your veins.
Harry holds onto your shoulder with one hand, the other splayed across your waist, and he starts to move inside of you. His thrusts are slow at first, deep and deliberate, reaching a depth that has your walls helplessly fluttering around him.
And he feels it, too. You know he does, because his pace picks up, knocking the air out of your lungs. His grip clamps down on you, not so much to maintain your balance this time, but to pull you back onto his cock as he pushes in, as if he couldn't get close enough.
"Fuck—don't stop. Just like that. Please, don't you dare fucking stop," you cry out, voice frayed at the edges. Your mind scatters with each snap of Harry's hips, which seemingly have grown much harder at your words, hitting the sweet spot that he had teased earlier over and over again.
“Never, baby,” he chokes out. “Never gonna stop. Feels too fucking good.”
The noises trapped within the walls are filthy and obscene. There's the wet, rhythmic squelch of Harry's cock driving into; the frantic slap of the front of his thighs against the back of yours. The lewd symphony of your strung-out whines and his deep, throaty groans.
If Harry had neighbors, they would have certainly loathed him. And you. Mostly you, with your loud, unabashed moans from being fucked into oblivion in every room, on every surface of his home.
“M’close, Harry,” you tell him as the burning warmth in your core begins to crescendo towards your peak.
Harry lets out a hiss when your cunt tightens its walls around him, like it's warning him of your fast-approaching climax in case he hadn't heard you the first time. "Keep squeezing me like that darling, and you're gonna make me cum too."
Your legs shake as Harry pounds into you with reckless abandon, his control slipping away as he chases his own release. But he won’t allow himself to fall before you do. He makes sure of that once his fingers land on your delicate clit, rubbing in tight circles, trying to time with his increasingly sloppy thrusts.
Glancing over your shoulder, you arch your spine as much as you can until his chest brushes against your back. Harry nuzzles his face into the crook of your neck, his scruff on his lower jaw scraping roughly against your skin.
“Need you to cum for me—fuck, baby cum now,” he urges, his tone wrecked, his restraint obvious. He’s right there with you on the edge, not letting go. Not yet. He couldn’t, wouldn’t.
But you do. You cum for Harry, the tension in your body snapping and unraveling all at once. You couldn't speak, not that any coherent thoughts were forming in your head. Not when the waves of pleasure come crashing down on you one after another, after another.
You barely hear the strangled groan behind you, nor register the way Harry’s hips stutter against you. Your pussy gushes around his shaft, clenching down on him hard, and that’s all it took. He buries himself to the hilt with a broken sigh of your name, his throbbing cock spilling deep inside of you, filling you up to the very brim.
Stillness passes over you and Harry. The shower is still running overhead, now the only sound in the room along with your tangled, labored breaths. He doesn’t pull out right away, and you’re glad he didn’t.
You allow this connection to remain for a minute or two more, before his softening length slips out without truly meaning to. A warm trickle of his seed slides down the inside of your leg, mixing with the rivulets of water on your skin, and you both share a hum at the sight.
Carefully, you shift your weight and turn, feeling the fresh new ache between your thighs. Harry’s heady eyes are already on you when you face him. His arms move instantly, pulling you flush against him, chest to chest, two hearts slowing down together to a calmer beat.
He kisses you tenderly, sweetly. The heat between you has now softened, like the burn of a fire that has settled into embers. It's moments like this where you look at Harry differently, as if he's not just a man you befriended after crossing paths one night, who, after finishing a bottle of Château Margaux, later became someone you seek out for relief.
Here, he’s… more. You don’t know how much more or why that is, and honestly, you’re terrified that this is currently crossing your mind.
“You okay there?” Harry asks quietly.
Pushing the confusing thought away, you're quick to nod and smile, brushing his wet hair back when it clings to his forehead. "Never better. Although, may I suggest investing in a shower bench? Could be helpful whenever we decide to fool around here."
He laughs lightheartedly. “Don’t worry, it’s already on my to-do list.”
“Good. It baffles me that your bathroom doesn’t already come with it, considering this penthouse cost you $12 million.”
“Why? Does your modest $5 million condo have one?”
“Duh, of course. It’s one of my non-negotiables. Makes shaving a lot easier, among other things.”
Harry shakes his head, eyes crinkling with amusement. “Guess that means we’re showering next at your place then.”
“I wouldn’t say no to that,” you reply with a soft chuckle. “You can see the benefits for yourself. Especially with your uh…”
You trail off, motioning to the healed scars running down the length of each of Harry's legs. He'd hidden them from you at first, choosing to have sex under the sheets, never letting you close enough to notice. But you did by accident some time ago, though you never asked where they were from. He's hesitant to share, still is, but you don't force him. You figure he’ll tell you once he’s ready, if and whenever that may be.
A gentle smile tugs at the corner of Harry’s mouth. “I’ll call up a contractor tomorrow. But for now, why don’t I wash you up before we head to bed?”
“You calling me dirty, Castillo?” You tease as he directs you closer under the spray of water. Undeniably, though, there’s something about the affection in his tone and his offer that has your heart stumbling.
“You are,” Harry smirks, taking his shampoo bottle from the nook and squeezing a generous amount of it into his hand. “You crashed my shower because you woke up horny. Almost got me off with just one hand, then you were begging to get fucked by my cock.”
You moan softly from both his retelling of events and the feeling of his hands in your hair, fingers lathering the shampoo into your scalp. Your eyes flutter shut as he massages your head, swaying just slightly from the motion of his hands.
The scent of cedar wood floods your senses—god, you’re not sure how you’ll make it through the entire day tomorrow smelling like Harry, feeling like you’re still wrapped in him completely.
“You always do this?” You question low, eyes peeking open after thoroughly rinsing the suds out of your hair. “Wreck a girl’s pussy then bathe her gently after?”
Harry reaches for the body wash. “Only you.”
You had half-expected him to give you a witty remark, but what came out of him instead carried a certain tenderness that’s becoming more and more familiar. It leads you to speculate whether he notices that, too.
A new kind of shiver sweeps down your spine as Harry glides his now soapy hands over you. He starts at your shoulders, moving down to your arms, then across your chest. There’s so much care when he circles your breasts, touching them not out of lust, but with something very sincere. Intimate. He later bends down a bit to reach the inside of your thighs, brushing clean the remnants of your mixed release there.
By the time Harry rinses you one last time, your chest aches in a way that has nothing to do with sex, but everything to do with him.
“This feels… oddly domestic.” The words tumble out unintentionally as Harry switches the shower off. You wait too long to take it back, and you can’t explain what you mean by that either.
You might have offended Harry when he doesn't respond right away, just pushes the shower door, and grabs a towel hanging nearby. He spends the stretch of silence drying you off before he bundles the cotton fabric around your body, tucking it at your chest.
Afterwards, he steps out of the stall, reaching for a second towel to quickly pat himself dry. He wraps it low around his hips and shifts back to you, extending a hand out, palm up. His fingers close gently around yours, guiding you forward— out of the warmth and into the cool air that raises goosebumps on your skin.
Then came his voice, much softer than you’re used to. The sound of it twists in your gut. “You didn’t like it?”
“No, I mean— yes. Yeah, I liked it. It was really… nice,” you ramble, struggling to find the right words to say here. But your answer was the truth. “Sorry, just not used to it, that's all.”
“Me neither,” Harry whispers. There’s a flicker of understanding in his warm gaze, and it swirls with something that you couldn’t quite pin a name to, or perhaps you’re simply not ready to. “It felt… nice. Doing that—for you.”
You fall into silence once more, though this time it rests lighter on your shoulders. A smile blossoms across your lips when you notice Harry still staring at you, looking as if you’re not a luxury, but a rarity—the one thing in this world his money can’t buy.
The lines between the two of you are blurred now. At least to you, they were. You wonder at what point it all changed. Or maybe it had been a slow, gradual shift, and it's only begun to catch up to you.
Either way, you and Harry were never meant to be this close. Purely sex, that was the deal. But now…
Now, he’s kissing you again, each brush of his lips demanding nothing more than you can give. You can taste the faintest trace of you on his tongue when he weaves it into your mouth, coaxing a pleased sigh from you that he drinks in without pause.
Then, Harry pulls away for a breath, his forehead resting against yours. You couldn’t remember what you’d been thinking or why it even mattered. Your mind, so noisy several moments ago, has gone blissfully blank.
You know without a doubt that it’s all because of him.
“Is this too much?” Harry asks, the weight of the question hanging in the air.
"No," comes your answer. You say the following words almost as if they hold something fragile. "It's perfectly enough for me."
Soft and slow, you press your lips to Harry’s again—and it would make you the richest woman on earth if you could just stay this way for as long as he’ll keep you close.
series summary: after lucy, harry believed he was destined to be alone. he had given up on his dream to be a father and husband. that is, until he met you who gave him hope for a future he thought was lost.
pairing: harry castillo x fem!reader
series content warning(s): EXPLICIT CONTENT (18+ ONLY MDNI), eventual romance/relationship + smut, slow burn, slight age gap (harry's in late 40s, reader is in early 30s), reader is single mom, two different backgrounds, harry's insanely rich, elements of angst, jealousy, insecurity, happy ending! (don't worry), no use of y/n. each chapter will have its own separate warnings!
a/n: so i know i said i'd take a hiatus from writing, but here i am... with another wip for harry castillo bc i'm still not over this man (and the 20-somethin' mins he was on screen for 💀) anyway, i hope y'all enjoy this. gonna try uploading a new chapter every friday, so stay tuned! <3
SUMMARY: You meet Harry Castillo whilst on the vacation of your dreams and spend the entire summer intertwined in a romance with an expiration date. Come season’s end, you’ll have to decide if you want to return to your old life or pursuit a new one with Harry.
RATING: E.
GENERAL TAGS: No use of y/n (reader has the nickname Sol that is used sparingly), reader is described as being plus-size/curvy/thick, reader is written to be a woman of color (latina) though everyone is encouraged to read, summer romance, love at first sight, he fell first and he fell harder, sugar daddy vibes a little bit, cliché romcom shenanigans, strangers to lovers, the one that got away trope, lying, infidelity (reader is married), angst, implied age gap (harry is fifty and reader is in her mid thirties), smut, alternating povs. More specific tags will be listed per chapter.
P.S. For the sake of keeping the whimsical, summer vibes afloat… we’re going to suspend our disbelief (the conscious choice to ignore plot holes or unrealistic elements simply to enjoy a fictional story) when it comes to travel laws and all that boring stuff, kay?
⊱ ⠀ ⠀ 𝗖𝗛𝗔𝗣𝗧𝗘𝗥 𝗠𝗔𝗦𝗧𝗘𝗥𝗟𝗜𝗦𝗧.
part one: monte-carlo, monaco
part two: lagos, portugal
part three: ibiza, spain
part four: sicily, italy
part five: mykonos, greece
part six: new york city, new york
⊱ ⠀ ⠀ 𝗠𝗜𝗦𝗖𝗘𝗟𝗟𝗔𝗡𝗘𝗢𝗨𝗦.
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#summer affair
moodboard
main graphic credit @/devociones
divider credit @/bronzewasp
I am starting a whole new taglist for this series! If you want to be tagged, feel free to DM me or reply to this post to be added! ☀️
The Arrangement - A Harry Castillo Fanfic Masterlist
She’s the lie he hired. He’s the truth she wasn’t ready for.
After a bitter breakup with Lucy, 50-year-old private equity billionaire, Harry Castillo, isn’t looking for love - he just needs someone beautiful, discreet, and uncomplicated to be on his arm for a high-profile week of events in New York. What he gets is you, an escort, 28 years old, with sharp wit, hidden depth, and zero interest in becoming someone’s fantasy girlfriend off the clock.
But Harry makes you an offer you can’t refuse: a month of luxury, five-star hotels, couture fittings, private jets, and a generous paycheck… in exchange for playing the part of his girlfriend at a string of galas, charity balls, and business dinners.
You aren't some downtrodden dreamer. You are funny, clever, and fiercely independent. You're doing this job to stay in control of your own life - not waiting for a saviour. And Harry isn’t trying to fix anyone; in fact, he’s the one who might be broken, and he doesn’t even realise it.
Warnings: 🔞 NSFW themes (slow burn but oh it burns), smut, Escort x billionaire dynamic, Power imbalance (navigated and explored), Age gap (50m / 28f), Post-breakup emotional damage (on his end), Feminine rage + soft power, Men in suits, emotionally repressed, whiskey as a coping mechanism, Mutual pining (yes, even with a contract), Glamour, deception, and dangerous amounts of eye contact, Contractual arrangements that spiral into genuine affection, Rich people problems + broken people pretending they’re not, Soft power games, Sharp banter + late-night vulnerability, Trust issues + protective instincts
Pretty Woman inspired but make it jaded playlist 🎶
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)
age gap, female reader, contains themes of body image, chapter has not been edited
─────
You were born in the penthouse suite of Lenox Hill Hospital, wrapped in lavender silk instead of muslin.
The first sound you heard was the laugh track of your mother’s favorite 1950s sitcom playing softly in the background as she recovered on morphine.
You grew up in a six-story limestone townhouse off Fifth Avenue, the kind with frescoed ceilings and staircases so wide they made women feel like swans. The house smelled like bergamot and old paper. Always.
Your last name meant something—meant everything—in film. Directors paused when they heard it. Festival organizers offered you rooms. Cinematographers tried not to blink. Your family didn’t just fund films, they curated the atmosphere in which they were watched. Museums asked for your grandfather’s reel collection like relics. Your father’s voice had been immortalized in Criterion commentary tracks. You were born into the lighting. You were born on set.
By the time you were five, you knew what a backlot was.
By ten, you’d learned how to tell when a director was faking their references.
You could cry on cue, not because you were trained—but because crying got you what you wanted. You were always told you looked like your mother, which you hated.
But you knew it was true.
Same feline cheekbones, same bloodless complexion, same way of arching an eyebrow so it felt like an accusation.
Your sister, younger by three years, had always been the darling of brunch tables. You were the one who drew headlines when you spilled wine on a Cannes jury member’s lap and didn’t apologize. You were called “feisty” by Vanity Fair and “difficult” by your aunt’s third husband.
You hadn’t worked a day in your life, not in the way people mean it. You’d attended Columbia briefly, then left because someone on the faculty looked at you wrong. You dated mostly artists—photographers who lived in lofts and sculptors who never returned your YSL coat. Occasionally a screenwriter, someone who claimed he was writing you into something. They never did.
But lately, it had begun to sour.
Parties were too loud. Everyone looked like someone you’d already met. Men your age were either married or trying to get you to invest in something blockchain-related. Your doorman had started to pity you. He looked at you like you were an orchid in the wrong light.
It didn’t help that the world had shifted.
The industry, the city, the people you once dismissed as temporary had begun to stick. There were new families at the Met Gala now, new surnames attached to legacy tables at Polo Bar. You knew the kind of men you wanted. You just hadn’t seen one in a very long time. Not really.
But elsewhere, in a different corner of the city, another life was ticking along with equal weight and silence.
Harry Castillo stood in front of the floor-to-ceiling windows in his penthouse and read a memo he didn’t care about. The building was newer than yours, all glass and good taste. The kind of place where appliances whispered and marble was warm to the touch.
He was tall, broad-shouldered, wearing a slate-gray sweater that looked like it belonged in a film about grief. His hair was dark but threaded with silver, curling at the back of his neck. His eyes were the color of wet earth. There was something old-fashioned about the way he stood—shoulders slightly back, like he was ready to say something difficult but necessary.
Harry was born into money too, though it was newer and quieter than yours.
His mother founded the Castillo Group after taking an inheritance and multiplying it tenfold in under a decade. She built the firm with the kind of discipline normally reserved for surgeons. Harry's father and brother now worked under her. So did he. Not because he had to—but because it was what Castillos did.
Private equity didn’t thrill him, but it made sense.
And Harry liked things that made sense.
He liked structure. He liked the rhythms of quarterly reports and the smell of ink on legal pads. His world ran on spreadsheets and quiet dinners with men who owned things you’d never see.
He had recently ended things with Lucy Mason, a woman who had once been important to him. She was a professional matchmaker—poised, brilliant, and deeply concerned with emotional compatibility indexes.
He’d liked her. He’d tried to love her. But there had always been a small door inside his chest that wouldn’t open for her. Not all the way.
They ended things late at night.
It was civil, almost eerie in its neatness. She told him that if he ever wanted to try her service, he should.
“If you call the office,” she said. “They'll assign someone great for you.”
He nodded and never called. Not yet.
Back uptown, you were barefoot on the heated terrazzo floor of your kitchen, making a mess out of truffle honey and sourdough. Your sister was at the counter, scrolling through her phone like it was her real job. She looked too pleased. You didn’t trust her when she looked pleased.
“You’re not wearing those boots again, are you?” she asked, not looking up. “They’re very…divorcee.”
You ignored her. You’d been feeling unstable lately, a little trapped in the amber of your own life. You’d been googling people you once hated and found out they might have figured something out.
Before you.
You hated how that felt.
Your sister put down her phone. Too deliberately.
“So,” she said. “Promise not to get mad?”
You looked up. “No.”
She beamed. “Okay. Don’t freak out. But I might have filled out a little thing for you.”
You blinked. “What kind of thing.”
“It’s nothing. Just…a profile. For a matchmaking service. Very elite. Very low-profile. Super bespoke.”
You said nothing. You stared at her, hard enough that she briefly flinched.
“I knew you’d react like this,” she groaned. “But come on. You’ve dated everyone in Manhattan who’s not in rehab or under federal investigation. You need a reset. A new algorithm. Let the universe—or a very qualified stranger—take the wheel.”
You turned away, grabbed the spoon, stirred your espresso like it was someone’s fault.
“Please tell me you didn’t use my real name,” you said quietly.
She hesitated.
“I used your middle name,” she said brightly. “That counts, right?”
Outside, the city shuddered to life—cars moving like brushstrokes, old buildings watching from behind limestone brows.
You didn’t know it yet but Harry Castillo would open a drawer that night and find the business card Lucy once left behind. He’d hold it in his hand a little too long.
Today was for disbelief. For the kind of quiet before something tilts. For looking out at the city and wondering—against all logic—if maybe someone was already looking back.
You didn’t go out much that week.
Not in any performative way—no detoxes, no dramatic declarations to your group chat, just a slow unspooling of invitations you didn’t RSVP to.
A dinner at Lucien you skipped.
A gallery opening where someone’s assistant texted, They’re asking if you’re coming.
You weren’t.
You sat barefoot on the windowsill instead, eating cold papaya and watching the fog crawl up like it was trying to forget where it came from.
Your sister had gone quiet. Not in a guilty way—she’d never been wired for guilt—but in that annoying, practiced stillness she slipped into when she was waiting to be proven right. You could feel it in the one word texts. The silence that followed. The smug, hovering dot-dot-dot that never became a message.
You lasted about two weeks like that. Then your mother called.
Lunch, she said. Cipriani, obviously. She didn’t ask if it worked for you. She didn’t need to.
You arrived ten minutes late on principle. She was already seated, already picking mint from her cocktail, already tilting her cheek for a kiss she never quite gave.
Her hair was perfect.
It always was.
Still pulled into a chignon so tight it made her face look slightly unreal. Her scarf—Hermès, naturally—was twisted just so, like she'd stepped out of a 1970s Italian film and never aged past the good lighting.
“I ordered the risotto for the table,” she said. “You look pale.”
“I’m fine.”
“Have you been working out? Your stomach looks soft.”
“I said I’m fine.”
She waved you off, already bored. Her nails tapped her wine glass with deliberate disdain. You knew the rhythm by heart.
She asked how you’d been, and you told her the sanitized version—books you were pretending to read, your new pilates instructor with that Finnish accent, something about how you were considering showing up on dad's set in Los Angeles just to feel something.
She nodded politely through all of it, eyes scanning the room.
Then, as the waiter laid down the salmon, she struck.
“You know,” she said. “There’s nothing wrong with wanting to be chosen.”
You didn’t look up. You kept slicing bread. Slowly. Cleanly.
She kept going, of course.
“I worry you’ve built this little moat around yourself. And for what? So no one can disappoint you? That’s not strength, darling.”
“Are you seriously—”
“And don’t say you’re not lonely. Everyone’s lonely. It’s boring.”
You could feel your jaw set. That was the thing with her. She never said it cruelly. She said it like it was just another fact, like the weather or your blood type. Like cruelty wasn’t personal unless you let it be.
“I didn’t come here for a lecture.”
“No. You came because I asked you to.” She smiled over her wine. “And because no one else did.”
The silence that followed was sour and expensive. The kind that doesn’t get broken by apologies, only by checks and limousines and the distraction of someone else’s scandal.
You got into the back of your car with your stomach a tight little fist. You didn’t cry. Not there, not then. You weren’t that girl.
At first, you thought it was spam. Then you saw your middle name typed like it belonged to someone else. The same photo your sister had forced you to take last year, standing on the terrace in a white dress that had made you feel like a ghost. It was you. You, in some unnervingly accurate bullet points. Preferences. Dealbreakers. Love languages.
You hovered over the trash icon. Didn’t click.
Not yet.
Harry sat in his bedroom in silence.
The penthouse—more glass than walls—was hushed, interrupted only by the occasional hum of temperature regulation or the sigh of traffic five stories down. He liked it that way. Controlled. Calibrated. No echoes of someone else’s taste.
He sat in the reading chair by the window, laptop balanced across his thighs, a page open with the pale gray header: Castillo, H — Matchmaker Profile Review Requested.
Rose—his matchmaker—had told him to look it over. See if anything felt off. “Even the smallest thing,” she’d said, with her clipped precision. “We don’t want anything distorting the signal.”
He didn’t believe in signals. Not really.
Still, he scrolled.
He scanned the words—edited, carefully neutral. No photos. He’d opted out. There were photos of everyone now. He didn’t want that. He liked the idea of someone reading first. Imagining. Filling in the edges wrong.
Then he saw it.
Height: 6’0
He paused.
It was true. Now.
But it wasn’t always.
He shifted in the chair, legs stiff. That familiar ache, dull and ghostlike, stirred beneath his skin.
It had been eight years.
Still, some mornings he swore he could feel the break. The phantom throb of it. The remembering.
He’d been thirty-seven when he did it. His brother had gone first, dragging him into the consultation like it was some secret rite. The doctor spoke with an accent and wore a Rolex that glinted like a challenge.
They broke the bones. Femurs. Tibias. Stretched them millimeter by millimeter over months. Metal rods inside the legs. Physical therapy that made grown men cry.
Four hundred thousand dollars.
Each.
They were lucky.
Rich boys.
They healed in penthouses with private nurses and blackout curtains. Harry read biographies of ruined men while his legs screamed.
He never told anyone. Not even Lucy. Until she found his scars while he was sleeping.
The scars were faint. A pair of pale, wicked lines running along the outside of each leg, like punctuation marks on a story he didn’t talk about. He saw them in the mirror sometimes and thought, What did I gain, really?
Six inches, yes.
But also… something unspoken. Some strange edge. A new way men listened when he spoke. The way women didn’t ask questions, just tilted their heads in approval, as if the air had shifted.
It wasn’t vanity. Not exactly.
It was about scale. About not disappearing in rooms where power stood tall.
Still, seeing it there, written down, made something in his throat tighten.
He shut the laptop and leaned back. The city glowed below him. Red tail lights inching up West Broadway. People moving, choosing, being chosen.
He reached down and rubbed his shin gently, as if to remind himself...this is yours.
You paid for this height.
You earned it in bone.
Meanwhile in another penthouse just a few blocks away...you were lying on your back, staring up at the crown molding, thinking about the things your mother said.
The idea that being chosen was something worth wanting.
You hated that it echoed.
You hated more that it almost sounded true.
Downstairs, your doorman signed for a package. Something sent from an office you’d never heard of. A folder sealed in black. Your name printed in serif.
You wouldn’t see it until morning.
But it was already in the building.
Already waiting.
When you woke, the light in your bedroom was soft and dull, filtered through gauzy curtains your mother had once called tragically optimistic. The air had that filtered morning silence that felt vaguely judgmental, like even your apartment was waiting to see what kind of person you were going to be today.
You padded barefoot across the terrazzo floor, still in last night’s silk camisole, your stomach a soft ache from too much wine or not enough food. You didn’t remember which.
And there it was.
A black envelope.
Just outside your penthouse door. Laid neatly on the marble like it belonged there. No branding. No return address. Only your middle name printed in thin serif font.
You stood there for a moment, coffee-less, suspicious, bare-legged in a building where people wore jewelry to take out the trash.
You thought...spam. PR. A strange flex from a failed suitor.
But then you saw the initials etched lightly on the back seal...R.S.
Your stomach curled slightly.
Your sister. That smug, beautiful demon.
You carried the envelope inside like it was cursed.
At the kitchen island, you made espresso and stared at it like it might blink. Your phone had seven unread messages and none of them mattered. You’d spent too many mornings like this—floating in your own life like it was someone else’s bathwater.
Eventually, you slid your finger under the flap.
Inside a slim folder. Matte cardstock. Minimalist. Heavy enough to feel expensive.
A letter on the front.
Your sister mentioned you were hesitant. I understand hesitation—it can be a sign of intelligence. But I also know a match when I see one. The following is not a pitch, nor a promise. It’s just a possibility.
— Rose
You blinked. That was it. No company logo, no contact info. Just a name and a voice like the inside of a glass of wine—dry, elegant, a little smug.
You flipped the page.
There were bullet points. Controlled, curated, clinical. Every line written like it had been vetted by lawyers and therapists.
Age: 47
Height: 6'0
Marital Status: Never married
Children: None
Occupation: Private Equity (Partner, Family Firm)
Residency: Tribeca
Education: Ivy League (Economics)
Religion: Agnostic
Languages: English, Spanish
Temperament: Observant. Principled.
Emotional Availability: High—when trust is earned.
Love Language: Acts of service.
Looking for: The real thing.
You stared at it.
Private equity. Tribeca. Forty-seven. You groaned.
He sounded like the kind of man who corrected waitstaff and had a framed blueprint of a yacht in his office. The kind of man your mother would politely destroy with a single glance and a casually cruel remark about his tie.
But you kept reading.
There were notes. Margins full of them. From the matchmaker, apparently—this unseen curator pulling invisible strings.
"He listens more than he speaks. But when he speaks, everyone listens."
"Very tactile with people he trusts. Rare, but notable."
"He likes reading before bed. Not out of habit. Out of need."
"Wants children. Not urgently. But honestly."
You felt yourself bristle. Then soften. Then bristle again.
Because you knew men like this didn’t exist. Not really. And if they did, they didn’t submit themselves to algorithms. They didn’t hand over their inner lives to professional matchmakers in New York City. They didn’t wait around for women with baggage and beautifully designed boundaries.
But then—
Then there was the smaller envelope.
Sealed. Black wax. No flourish, just the words...
Only open if interested.
Which, of course, was exactly the kind of thing that made you want to open it.
So you did.
Inside, a deeper profile. Not his answers. Her notes.
No photo. Of course not.
But somehow, without seeing him, the image began to form anyway.
Tall. Broad-shouldered. A man who dressed like he didn’t think about it—because someone else always had. Dark hair, graying in a way that made you think of salt, of restraint, of stories not told too soon. Eyes like wet bark. The kind of brown that held heat, not just color.
There was a line under Romantic Compatibility, written in Rose's careful script...
“He doesn’t flirt. He focuses. Makes you feel like the only room he’s ever stood in is the one you’re in now.”
Your stomach did a thing.
You hated that it did a thing.
You closed the file. Too fast. Like the words could see you, like they knew.
Who was this man?
You’d known hundreds of men. Dated enough to recognize types. Models. Trust fund poets. One devastating poet’s assistant. You could smell performative vulnerability from two rooms away. But this wasn’t that.
This was something else.
Across the city, Rose sipped her espresso in a glass office with zero personal items. She tapped a pen against her tablet and refreshed her inbox.
Harry still hadn’t responded.
She didn’t blame him. He was slower than most. A man who considered decisions like he was building a bridge over water he hadn’t named yet.
So she’d done it herself.
She'd read your sister’s submission, then read between the lines.
Googled you. Googled your grandfather.
Saw the name in festival archives, on lost reels from the sixties. Watched the grainy interview with your mother in a Paris cinema.
Saw the haunted brilliance in your face, the face of a legacy you hadn’t asked for.
She knew then.
She knew.
It wasn’t about wealth or aesthetic parity—it was energy. Containment. Quiet power looking for a counterpart.
So she sent it.
Let the rich girl read. Let the serious man stall.
Let the city do the rest.
Back in your kitchen, you refilled your espresso. Opened the file again. Not because you believed in it. But because something in your chest had begun to hum.
You hadn’t seen his face.
But you couldn’t stop picturing it.
And when you went to bed that night, you didn’t throw away the folder like you had planned to do.
You didn’t talk to your sister about it either.
You just let it sit there, glowing in your building.
A match you hadn’t chosen.
But maybe—
Just maybe—
One that saw you anyway.
The next tine you blinked it had been six days since the envelope.
Time moves fast when you are stressing over a man who doesn't even know you exist.
You hadn’t opened the envelope again. You’d slid it back into the matte folder and tucked the whole thing into the shallow drawer of your vanity—the one usually reserved for lipsticks in limited-edition packaging and love letters you never responded to.
You told yourself it didn’t mean anything, that it was just some expensive exercise in curated loneliness.
Like horoscopes for people with trust funds.
You’d stopped searching the internet.
There were too many men. Too many firms.
Every time you typed “New York private equity, 47, no kids,” the results made you want to burn your laptop. Sleek men in sleeker suits, blinking across LinkedIn headshots like a smug carousel. Half of them looked like the villain in a thriller, the other half like your ex’s father.
None of them looked like him—whoever he was.
And you told yourself you didn’t care.
You were busy, anyway.
Your grandmother had summoned the family.
She did this sometimes. Not for holidays, not for birthdays. Only for matters. The kind that required linen blazers and polite expressions, and the ceremonial silence that came when she mentioned death like it was something chic and inevitable.
Your grandfather had passed five years ago in Italy, holding a cigarette and laughing at a joke you never heard. He’d left behind vaults of film, four ex-lovers at his funeral, and a will that could’ve passed for a screenplay. Your grandmother had been quiet since. Not sad, exactly—just...theatrical in a colder register. As if grief was a role she’d aged out of but still wanted to audition for.
She’d asked the family to meet with a firm. Something about reorganizing trusts. Future-proofing. “Estate things,” your mother had said vaguely while buttering toast with her rings on.
All you heard was...meetings.
So now you had one. A meeting with a private equity firm that sounded like a wine label. It was supposed to be “the best,” of course. It always was.
The name meant nothing to you.
Castillo Group.
Sounded clean. Impersonal. Like a gallery that only sold work in black and white.
You were barely listening when your sister explained the structure of the meeting.
“…and we’re meeting with one of the partners,” she said, scrolling through her phone while icing her jaw. “They assigned us someone directly. It’s serious, apparently. Gran wants to talk about legacy clauses.”
You made a vague sound of acknowledgement and stole a sip of her green juice.
She slapped your hand without looking up.
“Don’t be weird,” she said.
You weren’t weird. You were bored.
The week passed in lacquered hours.
Days filled with pilates, wine, group chats muted indefinitely.
You ignored texts from men you didn’t remember giving your number to.
You wore sunglasses indoors. You bought a vintage Schiaparelli coat you didn’t need. You stared out windows longer than was socially acceptable.
And still—
The man lingered.
The match. Him.
Not directly. Just in flashes. The way someone brushed your wrist on the subway. The way the barista called your name too softly. The memory of Rose’s notes, scribbled like a diary for someone else’s soul.
You didn’t even know his name.
So you stopped thinking about it.
You went to pilates instead.
It was one of those spaces that didn’t call itself a gym—more like a “wellness lab.” All eucalyptus mist and minimalist lighting. The front desk staff were beautiful in that beige, uncanny way, like they’d been grown in a vat labeled Miu Miu campaign.
Your friends were already on the reformers when you arrived.
“Nice of you to join us,” said Inez, legs in straps, gold hoops catching the morning light. “Thought maybe you’d died of aesthetic fatigue.”
You dropped your mat bag dramatically. “I almost did. Someone tried to pitch me a podcast on legacy healing at Dries.”
Sophia snorted and gestured for you to take the spot beside her.
“Guess who’s instructing today,” she whispered, eyes gleaming.
You didn’t have to guess long.
The instructor—Matteo—looked like a poem someone wrote after watching too many Prada ads. Italian. Arms covered in tattoos that didn’t need stories.
You tried not to notice. You failed.
Midway through class, he came over to adjust your form. His hands grazed your hips, featherlight, intentional. He said something low in your ear—“You hold tension here, no?”—and you didn’t even pretend not to smirk.
After class, he caught up with you by the locker rooms. Said your movement was better than anyone in that class. You laughed, genuinely. He asked if you wanted to get a drink sometime.
You paused. Tilted your head. Let the moment breathe.
And then, “You wouldn’t survive my family,” you said, brushing past him with the smile you reserved for temporary men.
Your friends howled when you told them.
“I give it two weeks before you sleep with him,” said Sophia, adjusting her sunglasses.
“Two days,” Inez countered. “Max.”
You shook your head. “He’s a rebound I haven’t even earned yet.”
You didn’t tell them about the envelope. You hadn’t told anyone. Not really. It wasn’t shame—just…a strange refusal to share something you didn’t understand.
The man. The notes. The way they settled under your skin like they belonged there.
Later that evening, your mother texted.
Confirming tomorrow’s appointment. 11 AM. Don’t wear that thing with the fringe.
You didn’t respond.
Instead, you stood by your window, barefoot again, staring down at the city.
Somewhere out there was a man who might’ve been made for you.
And you were about to walk into his building.
Without even knowing it.
The next morning, the light came in soft again—but this time, you were ready for it.
You woke early. Not from an alarm, but from something subtler...the shifting silence of the city beyond your window, the almost imperceptible creak of your building adjusting to the day. There was a feeling in the air, taut and irritable, like silk snagged on a nail.
You didn’t hesitate.
Slipped out of bed, bare feet meeting cold terrazzo, body moving through the motions of your morning like choreography. Coffee first. Then the shower, where steam curled like memory and water hit your back in steady, punishing streams. Your playlist—jazz, something you played when you needed stability.
At your vanity, you moved with purpose.
Silk robe open at the shoulders. Skin dewy from serum. Hair twisted into a low chignon so severe your mother might approve. Your makeup was minimal. A little contour, a matte lip, the faintest shimmer on your cheekbones.
Then the dress.
Vintage Givenchy, the kind of black that absorbs your body. Sleeveless, high-necked, sculpted like you’d been poured into it. It flared just slightly at the hem. You added earrings your grandmother had once described as “impractical for daylight” which of course meant they were perfect.
You checked your reflection only once.
Perfect posture. Unbothered elegance.
Then, you descended.
At the lobby, your driver was already waiting.
Claude had been with your family since before you were born. He'd taught you how to parallel park in Montauk and once threatened paparazzi with a tire iron outside your prep school formal. He didn’t ask questions. He didn’t need to.
You slid into the back seat, legs crossed at the knee, coat draped over one shoulder. He merged onto Fifth with surgical precision.
“Traffic?” you asked.
“Not terrible.”
You nodded. Looked out the window.
Then the camera flashes hit.
Paparazzi. Two of them—lurking just outside the florist’s on 74th, lying in wait like roaches with thousand-dollar lenses. You didn’t flinch. You turned slightly, letting them get your better side.
Later, someone would send you a tabloid screenshot with the headline...Heiress En Route to High-Stakes Family Meeting. Your hair would tried to be recreated on TikTok. Someone in the comments would say you looked like a bitch.
Everything is great.
You arrived fifteen minutes late.
Because of course you did.
Claude pulled up in front of the building, not caring about the no parking sign,
Castillo Group read on the glass. The entrance was flanked by planters so perfectly symmetrical it felt aggressive.
You didn’t wait for the concierge. You just walked in, heels clicking like punctuation, coat draped over your forearm, eyes scanning the marble-and-brushed-brass lobby like it might bore you.
The receptionist blinked.
Everyone blinked.
You were used to that.
You gave your name. She gave a floor number.
“Your family’s already up there.”
Of course they were.
The elevator was silent, mirrored. You caught your own reflection and didn’t look away. You didn’t fidget. You didn’t check your phone. When the doors opened, you walked out like you belonged there.
Upstairs, in a glass-walled conference room designed for bids and negotiations, Harry Castillo was already seated.
He didn’t see you at first. He was focused on your grandmother—who’d arrived ten minutes early and was now seated at the head of the table like a bored monarch.
Your mother was beside her, glancing at her nails like they might betray her. Your sister, chewing invisible gum, scrolling on her phone. Your father, thank God, smiled when Harry greeted him. Warmly, even.
Harry liked your father. Had met him briefly before—quietly magnetic, the kind of man who’d aged into his cynicism with charm.
Harry had learned long ago how to focus on the numbers without being distracted by the jewelry, the veiled insults, the family lore. Your grandmother referred to their fortune like it had been bestowed by Zeus himself.
Then the door opened.
And you entered.
Harry didn’t look up right away. He was mid-sentence, something about generational liquidity and stepped-up basis calculations. Then his eyes lifted.
And the sentence died in his mouth.
You walked in like the room had been built around your arrival. Back straight. Expression unreadable. Not arrogant—just certain.
Black dress. Earrings that shouldn’t have worked, but did. A face that held a thousand stories and dared you to ask for one. You didn’t apologize for being late. You didn’t even pretend to care.
You took the empty seat beside your father.
Harry watched you like a man trying not to be caught watching.
His colleagues—the senior associate, the analyst, even the usually-unflappable estate attorney—reacted like something seismic had shifted. A cough. A fidget. A clearing of the throat.
You didn’t notice.
Or you did—and chose not to respond.
Harry looked down at his notes.
You, he thought, were exactly what Rose had sent. Except he didn’t know that yet. Couldn’t know. Because the sleek black envelope was still unopened. Still sealed. Still sitting in his office under a stack of quarterly earnings reports.
And you?
You barely looked at him.
You were polite. Dismissive. Tired in a way that didn’t show on your face but echoed in the way you crossed your legs. You asked two questions—sharp, surgical. You answered one of your grandmother’s passive-aggressive remarks with a half-smile so lethal the paralegal accidentally knocked over his water glass.
Harry watched it all.
Took it in like a study.
You didn’t look like a woman who needed anything.
Which is why, when you leaned slightly toward your father and murmured something that made him laugh, Harry felt something strange stir behind his ribs.
You were nothing like Lucy.
You were...burnt edges and quiet glamour, the kind of presence that made people straighten their posture without knowing why. The kind of woman who didn’t smile to make others comfortable.
The meeting continued.
You didn’t speak much.
But when you did, it changed the tone.
You challenged who would earn the rights to certain films.
Asked about film archive clauses.
Corrected your mother without blinking.
And when Harry finally did address you—only once, to clarify a section on trust structure—you nodded.
“Understood,” you said.
No smile. No flirtation.
Just clarity.
And still—Harry felt it. That tilt. The quiet shift. The thing that lives in the breath between two people before they ever really speak.
When the meeting ended, your grandmother rose first.
She didn't thank anyone. She didn’t need to. Her rings did the talking.
Your mother followed. Your sister made a quip about the chairs being bad for her hips. Your father lingered, shaking hands, making small talk with the estate attorney about his late father-in-law's cinema.
You were the last to stand.
And Harry—Harry watched you go.
Not in a way anyone would notice. Just a glance. A flicker. But enough to feel something crack inside his well-constructed, well-curated sense of detachment.
He didn’t know your name.
You didn’t know his.
Not yet.
And the black envelope in his office remained untouched.
But the city was shifting.
And the string had already pulled tight.
That night, Harry couldn’t sleep.
He didn’t usually have this problem. His apartment—if it could still be called that—was engineered for silence. Floor-to-ceiling windows, blackout shades, temperature calibrated to lull any insomniac into submission. The kind of place where sound had to ask permission.
But still, he laid there, one arm behind his head, shirt off, the city beyond the glass blinking like a pulse.
You’d been in his head all day.
Since you walked into that conference room like it owed you something. Since you’d crossed your legs and tilted your chin and answered your grandmother like a diplomat with a dagger under her tongue.
He’d barely heard a word of the financial summary after that. The analyst had repeated himself twice.
He’d nodded. Pretended. Said all the right things. But your face had lingered—cool, sculptural, with eyes that didn’t wander. Like you didn’t need the room’s approval. Like the room had already lost its chance to impress you.
Which is exactly why he needed to get you out of his head.
He rose sometime past midnight. The floor was cold against his feet. He poured himself a glass of water and crossed to his office.
The space was minimalist, but not impersonal. Books lined the walls. A single photograph—his brother Peter’s wedding—sat framed in the corner of his desk.
He had been Peter’s best man. Smiling, tailored, solemn in that way that made women say he looked like someone who had stories and the discipline not to tell them.
Peter had married Charlotte—sharp, beautiful, meticulous. A match made by Adore Matchmaking, by Lucy herself. The agency Harry had never believed in.
But Rose...Rose had sent him something weeks ago. Something he hadn’t touched.
He got to his desk slowly. The envelope was still there. Black wax seal. No branding. Just two letters.
R.S.
No flourish. Just intent.
He cracked the seal. Slowly. Like it might burn.
Inside, a folder. Matte. Heavy. Clinical. His name written at the top in neat serif.
Castillo, H. — Match Profile Review
He almost laughed. Almost.
Then he flipped the page.
And saw your photo.
It hit him like a held breath.
You.
You, in a white dress, standing on a terrace that looked vaguely Roman, vaguely imagined. You weren’t smiling. Just watching something beyond the frame, your posture perfect, your mouth slightly parted like you were about to say something.
The city dimmed around him.
He set the photo down, too gently.
The rest came after—your name (middle only, smart), your background, the carefully-worded notes Rose had stitched together like myth.
He read the line about your grandfather and felt it click into place. The film family. The legacy. The reason everyone in the room had sat straighter when your father entered.
But it was you.
It had been you all along.
And you had no idea.
He sank into the leather chair, your photo still resting beside his wrist like something too sacred to touch again.
It felt impossible. Too neat. And yet—
He thought about that moment in the meeting. When your eyes flicked over him once, unreadable. When you barely spoke to him at all.
He’d assumed it was because you were used to men noticing you. That it was nothing.
But now he wondered...was it better that you didn’t know? Or worse?
He rubbed his hand absently along the outside of his thigh. Scar tissue.
The faint ridge where bone had once been broken, slowly stretched, made new.
If you ever saw it—if you ran your fingers down his legs in the dark, tracing those pale punctuation marks—would you recoil? Would you laugh? Would you ask why?
Would he tell you the truth?
That it wasn’t vanity. Not really. That it was something more primitive than that.
Survival.
He closed the folder. Not to hide it. Just to think.
Because suddenly the idea of seeing you again—of meeting you, really meeting you—felt unbearable and inevitable all at once.
He hadn’t believed in fate. Not until now.
He looked out at the city.
Somewhere, not far, you were probably asleep in a bed the size of a country, one arm flung over your eyes, dreaming of nothing because you refused to give the universe the satisfaction.
And he—
He leaned back in his chair, your name like an electric thread running behind his ribs.
He would see you again.
He knew it.
He just didn’t know when.
But he hoped—quietly, selfishly—that it would be soon.
Summary: Your life has always been structured, dependable. You don’t stray, and it’s gifted you affluence. When you rashly decide to go on a blind date and they don’t show, you’re left with another fruitless, lone night of solitary. Until one equally lonely Harry Castillo invites himself to your dinner table and offers you a partnership just maybe worth investing in.
Pairing: Harry Castillo (Materialists) x f!reader
Word Count: 10k
Warnings: 18+ mdni, smut, unprotected piv (don’t be silly, wrap your willy.), oral (f!receiving), pull out and pray, cum eating, praise, wealthy hedge fund manager reader, lucy doesn’t exist/isn’t mentioned, fancy wine drinking, smoking, fluff, so much flirting, the authors limited knowledge of business and chess, no description of reader other than female anatomy and wears a dress/heels, a little easter egg referencing the kitchen scene bc i couldn't help myself
A/N: yes.. i did just post about my current wips.. but then i watched materialists, and came home and immediately wrote (no major spoilers in this). wanted to write something where Harry finds a partner who's also rich and work-oriented. i caved too quick for him and had to. sorry. thanks to anyone who reads <33 dividers by @/saradika-graphics
Masterlist
Blind dates are foolish.
You knew this. You’ve always thought this. Have never been convinced otherwise.
They’re wishes; a hopeful fantasy that two people will somehow be able to run an effective, effortless conversation despite knowing nothing about the other prior. They’re unorganised, variable.
Inconsistent. Nothing in your life is inconsistent.
You wake up at 5:30AM. Have a shower. Do your hair. Face. Slip on business casual clothes. Breakfast paired with a cappuccino with an extra shot of espresso. At work by 7AM. At your desk by 7:30AM. Home by 4:30PM.
Sure, sometimes the schedule can dip and maneuver in the later hours of the night in accordance with your current work load, but the point is- you have a schedule. It’s unwavering, sustained. Perfectly crafted to suit your needs and the straining pressure of your job.
You don’t do foolish acts like going on a blind date that the incompetent Rebecca you sometimes have a decent conversation with who sits at the desk opposite yours coerced you into believing would be enjoyable.
Witless, you think, as you stare blandly towards the empty plate opposite yours, framed by silver cutlery and a flawlessly folded napkin, pressed to delicacy. The third glass from the 2020 bottle of Argiano Toscana clenched between your impeccably manicured nails that tap an insistent, mindless rhythm against the stem. The liquor swirls like a bleeding wound in your glass, swishing up against the edges in crimson waterfalls each time you twirl it. It’s bitter on your tongue. Some blackcurrant and dark cherry bullshit of a far too expensive amalgamation of Merlot and Sauvignon Blanc.
Plus, there’s also the delicate lace-trimmed Stygian black dress curled around your body that flows down to your shin with a slit up along to the thigh, paired with simple but efficient silver heels. It’s not the most comfortable item you’ve ever worn- but it’s nice. Extravagant, if you look at it close enough.
Reckless, you think, glaring across at that empty plate on the opposite side of your two-person table that belongs to a person who hadn’t shown up. Toby, Troy, or something. Someone who apparently worked in luxury Real Estate, but who couldn’t even sell you one night of fulfillment or anything close to it. You had to call three different acquaintances to even acquire this table booking tonight, and this is apparently how gratitude is expressed back for your effort.
The candlelight flickers and illuminates the few tables scattered around the devastatingly wealth-painted Italian restaurant, the light laying across one side of your face like some sort of forlorn, two-faced golem sat isolated in the corner. Each of the other tables are occupied, mostly with couples on some feigned romantic date they paid too much to obtain, murmuring words of faux-affection across the flutter of a gentle flame and small portions of meals that took half of their last pay to afford.
“Were we still waiting on ordering, ma’am?” A voice abruptly chips into your carefully molded self-preservation, drawing your gaze slowly up to the waiter with the unpigmented mesh apron wrapped tight around his waist. You blink, eyes unfocused after glaring sharpened blades into the plate ahead of you like it might magically force a meal and a person to form.
“Yep. Still waiting,” You confirm, a grimace tugging at your features as you watch the waiter hesitate, glancing between you and the empty chair opposite. The situation you’re in is ridiculously obvious, like an open gash starkly revealed to everyone in the establishment.
He nods in understanding anyways, pivoting on polished shoes to leave, when you chip up to him, voiced edged with an indignation you fail to swallow back.
“Mind fetching the bottle?”
The man blinks back over his shoulder, peering down towards the glass in your hand, mapping out which wine bottle he needs to fetch. His brows twitch for just a beat- though you’re not sure if it’s in concern or awe- before he’s offering you a polite smile and dipping his head, whisking back to the kitchen to follow through.
You exhale sharply through your nose like the very breath is strenuous, eyelids fluttering closed before you’re leaning back in your chair. Dragging your gaze across the restaurant, the tungsten lighting- warm, reassuring, meaning to console the guests. Currently, it just makes you feel dreary.
You’re preparing to go on another wistful subconscious rant about the disadvantaged woes of blind dates whilst wondering if your vibrator’s batteries have been charged when a figure does appear. Looming like an assured shadow before lowering down into the seat opposite. Your head reels up to stare rather owlishly towards the newcomer’s sudden appearance. He leans back into the wooden seat like he belongs there, has already marked ground, a suave kind of allure hovering around him that you’re surprised you don’t immediately find smarmy, especially combined with the easy grin that upturns the corner of his lip.
Brown eyes are amongst the first things you notice.
The kind of brown that ensures it peers right into you without missing a beat, cooling the simmering apprehension in your chest like it’s effortless. Then the way he’s dressed. A black mesh top- formal enough for the establishment but not so lavish it’s considered profligate. He has a Roman kind of curve to his nose, full lips with a littering of a mustache that combs out into a stubble. He’s handsome, to say the least. Enough to make your heart stutter in a beat, but you blame it on alarm.
His brow curls upwards in a quirk at you as though expecting you to speak first, breaking you away from your pensive observation, mouth slightly parted like you’re spellbound. This can’t be Troy, Toby, Something. He looks too put together to fit the category of Rebecca’s acquaintances.
“You’re not my blind date sent by Rebecca, are you?” You ask blatantly.
He doesn’t look offended by the question. Rather, he seems amused.
“You’re the Hedge Fund Manager.”
His voice comes as a lower drawl than you expected. You can’t pinpoint the accent, but it’s like a rumble of a lullaby past your ears, twirling in mollifying notes with the gentle lull of the piano chords whisking in the air through the speakers. His residence here within just moments of seeing him is zephyr-like, as though he shifts and changes in accordance to the room he’s stationed in, all whilst commanding it with just the broad capability he clearly holds.
Your face falls slightly at his unforeseen mention of your occupation. You tilt back in your own chair, unsure if you’re trying to build an air of nonchalance or trying to create distance between you and this stranger that isn’t just the polished timber of the table.
“I dabble in that, sure,” You reply candidly, idly cautious. His eyes seem to lighten with satisfaction in the faint sandstone lighting. Like he’s trying to breach the space you created, he leans himself forward, tucking his elbows onto the table.
“You recently funded the last deal I brokered. Luxe Escapes,” He explains coolly. You perked slightly, gaze whisking along him, trying to regard him with a more inquisitive glance, wondering distantly if you had ever communicated with him before. It feels unlikely. You think you would’ve remembered a face like this.
“How were you involved in that?” You question, distantly wondering if you had clashed with him over the deal and that’s why you dismissed his existence following the conflict; act as though it never happened until the complication eventually dissolves itself into ash whilst you’re left with your triumph.
“I was the Sales Executive,” He assures, noting the slight pull of your shoulder blades in anticipation of a tense conversation. You blink, frets smoothed over swiftly.
“You were the Sales Executive?” You echo, giving him a once-over. Truthfully, it’s not difficult at all to imagine him pacing around a vast space of some grey-painted living room, footsteps leaden and quick as he prattles on about why some company or item would be efficient and worthwhile to invest in.
“That’s me,” He confirms, but he doesn’t look exactly supercilious or smug. Definitely not like that hotel branch company of luxury stays that conform the guests into the daydream of ‘escaping reality’ is rapidly becoming worth millions of dollars.
“And you are?”
“Harry.”
You tsk softly, tongue clicking against the roof of your mouth, seemingly unimpressed. Your head tilts, along with your wine glass as you circle it with mindless consideration, tone sardonic. “Harry. Fancy.”
He smirks lopsidedly, fingers flexing where they curl neatly over each other on the table. “Thought it’d sound less formal than saying Harry Castillo outright like this is a business meeting.”
“You’ve only talked about business so far,” You remind him facetiously.
“That’s fair. Let me try again,” He concurs. Then he rolls his thickset shoulders back to fixate his posture, a good-natured smile stretching along his inviting lips. He tilts himself forward, outstretching his hand towards you over the table. “Harry. I saw you sitting here over here alone and thought I’d come join you.”
You pause for just a beat, gaze fluttering to his outstretched hand, then back to him. Brazenly and uncharacteristically, you decide to amuse whatever this is. Leaning forward to meet him, you stick out your arm and take his hand, offering your own name back. His palm curls over yours, practically swallowing the proportions of your hand. It makes your throat tight realising how large he is, taking up the space like a polished, debonair boulder.
“You didn’t think about if I’d tell you to go away?” You hum, squinting towards him in silent challenge, attuned to keeping up this impression of satire he doesn’t seem to mind. His hand is still engulfed over yours- and instead of shaking, he squeezes once, before attentively turning your palm downwards, until he’s holding just your fingers in his grip. He bends down further, dipping his head down to lay an amiable but lingering kiss against your knuckles.
But what sends your heartbeat tripping calamitously in your ear drums is the way he keeps his eyes perched towards you, unwavering and unmoving. Drowning you in a melody of heat that seeps over you like dripping, melted sugar. That subtle flicker of interest swirling within the embrace of coffee-coloured warmth.
“I did. But I just had hope that you wouldn’t,” He rumbles in reply as he lifts back up, tentatively dropping your hand. It hovers sluggishly in the air for a beat too long before you finally regain control of your motor functions and let it fall back to your thigh. You huff a short, disbelieving laugh disguised as an exhale.
“Hope sourced from what?”
He crosses his hands over his lap, head cocking to the side as he considers the question for a moment, a sense of susceptibility murmured through the language of gaze. It’s not exactly pitying, just heartening.
“From the way you look like you could use some company,” He answers sincerely, his eyes flickering over you in an appreciative once-over that doesn’t feel like he’s leering, only valuing like you’re something cherishable. “And, admittedly, in good faith I couldn’t let that dress go to waste. It looks too good on you to do so.”
Jesus, he’s pulling out every move in the game.
Atypical in comparison to your usual indifferent composure, you can feel your cheeks heating, burning your skin. Actually flustered for the first time in what feels like months.
As if your own personal saviour dedicated to assuaging all your needs, the waiter swoops back in with the bottle of wine you requested held in two hands. He pauses for a second as he notices Harry, incredulity flicking through his eyes. But then he sends you a pleased smirk and unscrews the cork of the bottle, refilling your glass with repeated precision.
You murmur a quick gratitude, and the waiter takes the initiative to fill up the wine glass in front of Harry, who nods his own thanks. He plucks it up from the stem, gaze flickering from the rich scarlet liquid as he swirls it before returning back to you as he takes a sip, gaze remaining set on you. You mimic his actions, eyeing him from over the translucent rim, gaining back your conviction.
“Merlot,” He muses as he lowers the liquor from his lips. Your purse your own with amusement.
“You know wine?”
“No. The bottle's label says Merlot,” He says matter-of-factly, mirth ringing in his tone as he gestures off-handedly to the bottle. You blink quickly, that flushed tint coiling back over your skin, which only spurs him on.
“Fancy,” He comments steadily.
You breathe out sharply, lifting the glass back to your mouth to take a quick sip, lifting your shoulders in a careless shrug. “Didn’t think I was going to have any company.”
“I hope I’ll live up to any expectations you had for tonight,” He says, intentions genuine. But he clearly noticed how the table was set up for two when he approached, and yet only holding you.
It’s correctly jarring and disorienting considering your former thoughts on blind dating just a short while ago. Sure, this meeting wasn’t set up between you and Harry- but it was still accepting an offer of company from a stranger you knew nothing about prior, just as you would on a blind date. Harry continues to persuade you into telling him more about yourself, which you tentatively immerse yourself with.
Much to your bewilderment, you don’t entirely despise the conversation that you slip into with him. It’s smooth, undemanding, and light.
You tell him mundane things like what you had for breakfast, how early you usually wake, your pet lizard who lives back at your parent’s home in LA- before dipping into the story of why you were seated alone in this abundantly ornate and elaborate restaurant. Sheepishly laying out the story of how Rebecca had somehow coerced you into going on a blind date with a guy you can’t remember the name of, and how he stood you up. You shield any mortified winces with expressions of contempt, fingers starting up that irritable tapping against the stem of your glass again.
You go back and forth on sharing short, meaningless information about yourselves. Learning how Harry got into sales, explaining he grew up being surrounded by factors of money and influence constantly. He gestures back to a pair sheltered in a side booth, both hunched over the table and murmuring to each other like deadly secrets are being transferred. He elucidates with a grimace about how they’re newly-weds, boisterous and too sickeningly loving, which is what first led him to approach you when he couldn’t stand another second of third-wheeling his own kin and his newfound wife.
“So I guess we were both just feeling a bit lonely tonight,” You evaluate, chin tilting your face sideways slightly, wondering, are you lonely just like me?
“I suppose so.”
“Any thoughts on how to quench loneliness?” You ask, tone coy, one leg lifting to cross over the other. His gaze follows the movement, dropping to the table as though he can see it through the glossy wood.
“You want me to be honest?” He murmurs, eyes returning to your face, your features cast with casual curiosity.
“Of course.”
“I’d like to invite you back to mine tonight,” He admits, unhesitant.
Your moulded expression falters with the outright confession, heart tripping with it.
“You would?” You almost gawk.
“Only if you’re interested,” He assures, mouth thinning slightly as if he mistook your reaction for apathy.
“It’s not that I’m not entirely interested,” You correct, drawing out a soft sigh to collect yourself, propping one of your elbows onto the table. “I’m just.. weighing the pros and cons.”
He gives a slanted grin as you rest your chin on the palm of your hand. “Pros; you won’t be spending the night alone. Cons; you have to deal with repeats of Pink Floyd continuously playing during the car ride.”
You can’t help the gladdened snort that falls from you at the jest. You purse your bottom lip thoughtfully.
“And what do you expect to get in return?” You try to keep your voice methodical.
“Company,” He answers easily, his tone not housing any insistence for you to acquiesce.
You squint towards him, studying and observing. Maybe slightly teasingly, weighing the options over in your head like you’re being faced with a task from your employer.
“It sounds like an investment strategy,” You comment off-handedly.
“More like a mutual agreement.”
You lean back into your chair, hands falling back into your lap, giving a purposeful show of tipping your head to the side again.
“To fuck?” You question crudely. You catch the brief surprise that whisks along his features, but also the way the corner of his mouth twitches in the starts of a smile.
“To not be lonely,” He rectifies.
“Just for a night?” You test, your arms crossing over your middle loosely in a subconscious move of defence.
“Or we could see where it goes after,” He says with that enticing interest painted over his eyes again, with maybe some mingled hope tangled through it.
“After we fuck,” You lift your chin up, humour dour, like the thought of going back to Harry’s doesn’t send adrenaline pulsing through your veins.
He lets himself grin at your bluntness this time around. “Sure.”
“And if I’m thinking about saying no?” You croon, just to scrutinise his reaction, see if this gallant, poised persona of his can stumble.
His jaw clenches in consideration. “How do you usually approach your possible investments?”
You only pause for a beat.
“Like a game of chess.”
“Chess?” He parrots, intrigue evident. You nod.
“Investment is a game of chess. You think about all the strategies you need to win the board over, not just about your next move,” You cerebrate, eyes tipping down to your wine glass, fingertips etching a mindful pattern over it. “Each piece has its own pros and cons, like multiple investments do. If you move a piece in the right direction, it can become a more powerful player. It can grow in importance over time. But, a rash decision can leave you vulnerable and perceptible to attacks, or you can strategise and reach a checkmate. You need to invest foresight before anything else.”
His eyes round towards you as you tatter contemplatively, a deference evident in the solemn features of his gaze.
“So it’s a high-risk, high-reward situation,” He suggests, drawing your attention squarely back to him. A sly, knowing smile pulls at your mouth.
“That’s only considering it is a high reward.”
He doesn’t back down, fishing out a lighthearted jest, willingly taking the extra leap to solidify the blatant idea whisking between you. An idea you both already know was agreed to the moment he complimented your sleek dress earlier. “You could always find out. The customer is offering a first-hand demonstration.”
“Well, I do have to adapt to my opponent’s moves,” You hum wittingly, an easy, unarmed smile replacing your artful coquettishness.
“Is that an agreement we’re coming to?” He questions, optimism lighting his face the same way the candlelight casting along the strong curve of his jaw does.
“A mutual one, yes,” You assent, your stomach fluttering like a rocket preparing for launch, excitement twirling through you in searing ambers now that you’ve concretely settled on your decision.
“My driver can be here in the next ten minutes,” He suggests, brow raising. You agree zealously, smoothing your slightly clammy hands down the front of your dress as you rise to a stand. Harry fetches both his wallet and phone from his pants pocket, swinging a text his brother’s way to let him know he won’t be returning to advise him on how to keep his freshly-made wife appeased, and then calling his driver to your location. Placing a few hefty bills as a tip on the table even though neither of you ordered any food- which you belatedly realise- before he’s turning back to you, guiding you out of the establishment, his hand hovering just above the small of your back, barely grazing his touch along you.
You breathe out sharply as the pair of you move out of the restaurant onto the sidewalk, the New York nighttime traffic bustling, the usual tumultuous honk of a horn and the blinding streak of striking lights second-hand nature to you by now. You lean back against the rust-coloured brick of the building, hooking out a cigarette from the packet you kept stashed in your purse, just a pick-me-up in case Troy, Toby, Something ended up being a mundane bore.
Now you light the end, watching the embers burn as they smear tobacco into your lungs in hopes it’ll cool your anticipation long enough to arrive at Harry’s place first before you accidentally slip up and decide to crash your lips against his now and try to lick that blackcurrant wine right off his tongue against this brick wall.
“Drive shouldn’t be too long. I have a penthouse just up in up-town Manhattan,” Harry explains, peering down at his phone to confirm the driver’s journey to you both, settling next to you. You exhale, the smoke pluming up above you, catching away with the blur of a gentle breeze that’s swiftly turning frigid despite the mellow spring weather.
“You own a penthouse in up-town Manhattan?” You echo with only a tinge of bemusement intertwined.
“That surprising?” He raises a brow with a serene look.
“Not really,” You answer quickly. It wasn’t surprising at all, truthfully. He carried the staunch of his wealth with every step, his frame swallowing up the space he accompanied like he had banked out millions worth of cash just to own it, even somewhere as mundane as a sidewalk. It makes your breath hitch all the more as you watch his sombre eyes flutter down to your lips as they part to allow a plume of whitened smoke to trail up past your nose.
“Good,” He murmurs, gaze flickering back up to meet yours after a moment too long has passed.
You swallow gratingly at the simple way he eases into such a winsome persona, glamour and charisma tailing him constantly. He ushers you forth with a warm hand at the top of your spine as the car arrives, letting you stub out your half-smoked cigarette on the sidewalk before holding the door open for you as you slide into the backseat of the lush vehicle, smiling stiffly towards the driver, nerves growing fretfully in a churn in your lower stomach. Harry settles into the leather seat beside you, addressing the driver deferentially and directing him to upper Manhattan, back home.
As promised, the trip is entirely filled with the pleasant, tranquil lull of Pink Floyd drifting through the speakers, mingled with occasional talk between you and Harry. But for the most part, there’s just an effortless, unworried quiet between you; no demand to appear modish or shrewd- just a mutual understanding of comfortability.
The driver pulls up to the curb not long after, Harry swiftly hopping out of the car and trudging around to help you out. This time around, his hand settles more firmly against the base of your spine, fingers curling slightly as he leads you up to his penthouse with a phlegmatic gait, nodding his chin in polite greeting to the staff you pass. Your face is shrouded with a sanguine expression, heartbeat growing more erratic as you step inside the elevator.
Harry opens the dark-oaked door for you, allowing you to move inside the space first, his hand falling away from your lower back. Just with a first glance, you can tell how sumptuous it is. A wide, inviting hallway that opens out into a lavish living room and curves around to a dining table and kitchen, extensive floor-to-ceiling windows combing the expanse of the far wall. The hallway has two other doors perched at the opposite end, which you suppose lead to the bathroom and bedroom. It has similar lighting to the restaurant, only lit by the oscillating flutter of the city lights outside the windows, casting shadows inside and streams of gentle light, along with the low copper glow of a lamp sitting on the coffee table.
“You want a drink?” Harry asks, trotting through the living room in the direction of a side-bar set up opposite the dining table. You turn your gaze back to him, away from the darkened New York City skyline, a sight that somehow augmented your confidence.
“You don’t want to get straight to the business part of tonight? Close the deal?”
He pauses by the counter littered with liquors, blinking over his shoulder back towards you, a beguiled surprise whisking along his features. He diverts his actions, hand falling away from the wine he had been reaching for, instead turning around to face you. He leans back slightly against the bartop, a brow lifting with a teasing fashion.
“Well, I was hoping to try and charm you a bit first,” He replies steadily, his gaze looking even darker in the subdued lighting, casting over the entire length of you. Your body tenses slightly under the regarding look of cherishing esteem, your blood buzzing alight beneath your skin, anticipation coiling.
You take a step forward to meet him, which prompts him to kick off from the edge of the bar, taking purposeful steps towards here.
“Inviting me here was enough,” You murmur when he’s only a few short footsteps from you, deliberately fluttering your eyelashes and craning your neck up to meet his auburn-painted eyes swallowed by a blazing darkness. The side of his mouth twitches, as if with amusement, before it’s mellowing and darkening into something more decisive, nearly hungry-looking.
“Well, in that case..” He mumbles, more to himself, closing the distance between you. His hands lift to steady themselves on your hips, fingers curling around your frame with a durable finality. Your throat tightens with suspense, hopefulness whisking through you as his head tilts, eyes dropping down towards your lips. But neither of you shy away, your gaze mimicking his and wavering down to the fullness of his mouth that suddenly seems so close.
He leans in, and you mirror the movement, going to meet him- his breath brushes along the skin of your mouth which parts on instinct, eyes dropping to slip closed. His hands flex against your sides, and he pauses, pulling back with just a murmur of dubiety shadowing him.
“Though- you can pull out of this investment at any time, you know,” He reminds you, earnestly searching your gaze. You appreciate the effort to reassure and console you, but you fear your knees might give out beneath you if you have to go back and forth with this bashful, coquettish teasing any longer.
“Okay. Enough with the business metaphors. Just kiss me,” You husk back, one of your hands sliding up to curve around the nape of his neck and bring his face back down to yours. He meets you halfway, your lips meeting in a secure, firm kiss.
Your other hand lifts to balance yourself against his covered chest as his mouth slots over yours. It’s not rushed or heady like you might have expected in this case; but instead slow, deep. Assured. Bounding in a way that makes your lips part when his tongue drags along your bottom lip, coaxing. You acquiesce easily, sighing as his tongue meets yours, tangling in a precise dance that gradually grows more resolute, determined.
You sigh into his mouth as if you’re alleviated as his arms curl around your waist, tightening his hold on you, large hands tracing over the dress painted over your back. You tilt your head to the side to purposefully deepen the kiss, which he easily follows, movements quickly growing more desperate, a heat you thought had become a long-lost friend burning at the base of your spine, looping around in curling tendrils to your belly, warming. Your hand traces up from his neck to the edge of his jaw, then up into his hair- softer than you expected, threading through your fingers like silk.
You tug gently, urging. He sounds a low groan into the kiss, arms pulling you flush with the firmness of his body, the two of you swaying slightly to the side, unbalanced. He grips at your waist and guides you backwards. You stumble slightly in your heels, to which his hands curl tighter around your sides, nearly lifting you from the floor and carrying you backwards. He delicately but hurriedly pushes you back against a small side-table where he placed his keys by the door in the hallway, mouth working more urgently over yours. You respond with equal enthusiasm, a desperation clawing through each of your movements as your ass presses back into the edge of the wood, hips tilting.
He keeps one arm wrapped around your body whilst the other dips down, fingers toying with the edge of your dress where the split ends on your thigh. His fingers tilt beneath the fabric, carefully skimming along the softer skin of your inner thigh, making you keen towards him. He then swiftly grabs at your hips, and hoists you up onto the table.
The sudden action has you gasping with incredulity, lips disconnecting from his. He doesn’t waste a beat of not occupying his mouth, head dipping downwards to attach his lips to your neck. He kisses down the length of your throat, tongue tipping out to drag along your pulse, feeling it flutter frantically beneath the muscle.
He travels down further with open-mouthed kisses, to the exposed line of your collarbone. He curls his lips, sucking a small, blooming mark of purple into the small dip by the bone, his tongue smoothing over it. You should scold him, knowing you’ll have to cover it when you go into work next- but your thoughts are swiftly disoriented as he steps between your legs which part instinctually for him, his body moving flush to yours. You can feel the bulge of his arousal pressing into where your dress begins to hike up.
Need barrels into you harsher than you expected. With hasty fingers, you slide both of your hands down his body to his waist, hands working urgently at his belt. You barely get the buckle undone before his hands are covering yours, fingers dipping down to curl over your wrists and cease your actions.
He tuts, lifting his head from your neck.
“Not yet, honey. Wanna taste you first.”
You go to groan your objection, but it’s quickly swayed and swallowed by his mouth again, laying a prompt yet lingering kiss before he’s nipping at your chin, your jaw, working downwards. He lathes swift, small pecks of his lips over the curve of your chest, before following further down to your middle, his hand returning to your thigh, dragging beneath the hem of your dress beneath the slit, gliding upwards to your inner thigh, right by where you need him most.
He drops down more, his knees crouching down with a slight strain, and you notice the gentle wince that pulls at his face, the angle just not right. The table an inch too tall for him to comfortably try and settle between your thighs without an awkward position of having his body half-hunched and knees bent gracelessly, like some clumsy structure of a tower.
“You don’t have to crouch awkwardly, Castillo,” You inform through a rather breathless laugh, mirthful. Not mocking him, just finding his rushed enthusiasm endearing. You tug gently at his hair, coaxing him back enough for you to slide off the edge of the side-table so you’re pressed back against it again, ass squished against the wood. “I can just lean back on this.”
His eyes flutter up to yours with an inkling of vulnerability that’s quickly replaced with his own amusement as he comfortably settles onto his knees in front of you, now at the precise height to meet you.
“Great point. Underestimated my height,” He rumbles with gaiety, hiking one of your legs up so it’s resting half on the table, whilst looping your calf over his shoulder, opening you up further to him.
His fingers curl over through the fabric through the slit on your thigh, hiking up your dress enough to rumple it around your hips and give himself more access, both of his hands curling around your shins, before sliding up the expanse of your legs to your thighs with a reverent touch, like he’s sculpting a statue from just the rawness of his fingertips. He opens your dress like he’s unveiling a museum artifact, slowly opening the sheen curtains of the hem.
A nearly distraught sound falls from him.
“Jesus,” He breathes, eyes rounding, locked towards your covered core. Wrapped in a delicate black lace. His thumb swipes out to prod and stroke gently over the gusset he finds already damp, making his eyes flutter and his eyes drop with a ravenous look.
Your breath hitches, and his insatiable attention lifts up to you, locking his gaze on yours like an enchanting siren call.
“This was for him?” He mutters, calling back to your blind date who never showed up. He keeps his eyes on your face as he dips forward, pressing a lingering kiss to the inside of your thigh.
“Not anymore,” You reply throatily, fingers carding through his hair, urging. He smiles, nearly smug, boastful. Then lowers his head and presses another kiss to you, this time right against the soaked fabric of your panties, over your soaked folds held beneath. His hands slide higher beneath your dress to your hips to hook his thumbs through the waistband of the lace, dragging your panties down your legs with meticulous slowness. He curls the moist material in his fist after hooking it over your heels, before he’s tucking it into the back pocket of his pants like a secret fantasy hidden away.
His eyes drop down to where you’re now revealed to him, hands returning to your inner thighs, widening the stance, slotting his broad shoulders between them. You hear his breath stumble as he takes in the sight of you; puffy folds drenched with need, clit basically begging for his attention, hole clenching around nothing like it’s already calling him directly to you.
“So pretty, darlin’,” He murmurs, his thumb stroking out to swipe along the edges of your lips, spreading them wider for him. You feel your heart loop around in a scattered carousel as he lowers his face completely between your legs, his tongue flicking out to flatten against your cunt, then smooth upwards in one slow, long line.
You gasp at the wet heat of his tongue, and he responds with a drawling groan, his hand wrapping tight around your thigh. Then he’s lapping more insistently at your dripping slit, collecting your juices on his tongue like it’s the sweet nectar of a maple tree. His mouth lifts, suckling your clit past his lips, his tongue stroking over it in a smoothing motion that makes you twitch, chest arching upwards with a sharp inhale.
His tongue dips down, experimentally sliding inside you, curling to taste the slick right off your fluttering walls, slick pooling on the muscle. The motion has a devastating whimper slipping from your lips, your hand tightening and yanking lightly at his hair. He moans into you, the sound reverberating right up your spine in a quiver and making your hips flex into his mouth, which he only responds to with an eager, nearly debauched slurp, his mouth covering the entirety of your pulsing core like it’s his personal alter.
He licks into you, maneuvering between plunging his tongue in and out of your hole and sucking against that sensitive bundle of nerves that makes your knees threaten to give out. His eyes slip closed with a fervent expression as he suckles against your clit, his hand coiling up from your thigh to work his middle finger into you, your tightness wrapping around the digit as your mouth parts pendulously, body eagerly accepting the stretch of his thick finger.
He begins to dip his finger in and out of you with strenuous slowness, letting you feel each drag of it along your walls, making you drip more shiny slick onto him, drooling down onto his palm. He swipes his tongue out to collect it right from the source, drawing a ragged moan from both of you as he experimentally plunges his tongue into you alongside his finger. The act is followed by an obscene squelch as he licks up your fallen juices, the curve of his nose pressing against your clit.
“Oh, shit, like that-” You puff, chest heaving upwards. You urge him impossibly closer to you with the end of your heel pressing into his shoulder blade. He avidly complies, his finger moving faster inside you, submerging his tongue and twirling it inside you, curling and lapping. Your hips twist as he finger fucks you, but he stills you with one hand against your hip, whilst the other dips down to flatten his palm against your mound, his thumb slicking out and circling tightly over your clit.
You jerk, a whine curdling up past your throat as the tendrils simmer through your pelvis, the triple stimulation of his finger fucking into you repeatedly alongside his tongue catching any of your dribbling slick, and the rub of his thumb over your bundle of nerves making you lean further back against the side-table.
"Tha's it. You gonna come for me?” He asks into your cunt, voice muffled into your skin, sending another shiver up along your spine whilst you nod earnestly, quickly, lips pursing with another impure moan.
He redoubles and amplifies his efforts, sinking his middle finger deeper inside you, fucking it into you with rougher, sharper movements designed to make you uncoil like thread around his digit. His tongue continues to cuff and curl inside you, licking at you. His thumb strokes acute, tight circles around your clit until your thighs are clenching around his head.
Your hips roll down eagerly, impaling yourself further onto his tongue and finger, eyes slipping closed as your rapture tightens through your system, burning up along your spine and lashing over your chest like a smoothing of velvet honey. You’re pushed and diving thirstily down into the looping ravines of bliss, gushing down onto his tongue, your hand fisting in his hair.
He makes a starved sound against you, his tongue eagerly pushing and swiping, drinking down everything you have to offer like it’s something holy, an amalgamation of sweetness and headiness he’s rapidly becoming addicted to.
You wrench at his hair more insistently as he continues his ministrations against you, although slower, savouring each drip of your slick onto his skin and tongue. You whimper as the overstimulation of the flick of his tongue has your hips tilting away, his thumb a steady pressure against your puffy clit. He grins against you, smug, but relents, lifting his face up from between your thighs and peering up towards you with a lopsided smirk, pleased and satisfied.
“Okay?” He asks raspingly, like his lower face isn’t smeared with your release, lips glossy with you. You don’t reply, instead curling both of your hands over his cheeks and practically dragging him back up your body, lifting him up from his sore knees until his mouth is pressing back to yours, fervent, like you’re starved. You lick into his mouth to taste yourself on his tongue, moaning against him.
His nose bumps against yours as the kiss escalates, famished and keen, his hand grabbing at your jaw to direct your face and deepen your movements, his slick middle finger smearing your want against your skin. His other hand grabs at your hip to steer you away from the side-table, leading you backwards to those two doors by the end of the hall, mumbling into your mouth. “Want you in my bed.”
You both stumble slightly, but quickly anchor yourselves, polished leather and the plastic of heels clacking against the linoleum floors. His hand on your jaw drops down to snake behind you and fiddle with the zipper of your dress until it eventually comes loose, dragging it down to the base of your spine. The glossy material slides off your frame, pooling at your ankles. He helps you step out of it, guiding you backwards through the doorway to where you assume is his bedroom, his lips never breaking away from yours.
He kicks off his shoes whilst you wrestle off your heels, dropping down a few short inches as his hands covetously travel over you, melding over your curves like he can’t trace enough of you in the time he has- which is the entire night. He unclasps your bra, discarding it carelessly to the side with a soft clatter, leaving you completely bare for him.
His large hands come to immediately cup your breasts, squeezing carefully, his thumbs swiping over your nipples that quickly pebble under his attention. You whimper softly, pulling your lips from his and pushing your chest up into his hold, head slinging back with a breathy sigh. He takes the initiative, dipping his head down and attacking along the underside of your jaw, his tongue prodding at that sensitive skin behind your ear.
It’s heady, potent, a mix of heavy breaths and mingled want clashing into a nearly violent need. A different kind of greed than that of desire for wealth, desire for love or affection- but instead something rawer. Unbridled, weighty lust.
You barely get a glance around the costly expanse of his bedroom as you’re grabbing at his shoulders, directing him in a pivot until the back of his knees hit the edge of his king-sized mattress. You gently yet imperatively shove him back onto his bed, the silk sheets shifting with his weight as he lands back against them, his arms falling away from you.
He moves further up the pillows as you climb up onto the prodigious bed to join him, thighs framing his waist. His eyes draw up your bare frame towards you, inky black, his pupils swallowing out the brown of his irises almost completely in the soft lighting and in the consummation of his want.
His hands settle around your waist, squeezing as you dip down to press a swift kiss against his lips, your breasts squishing against his chest whilst your fingers slide down and tangle with his half-open belt, looping it finally through the fabric, before flicking it to the side. You nibble at his bottom lip before pulling away and unbuttoning his pants, zipping them down. You slide down briefly to urge and tug the fabric away from his legs, whilst he takes measure to tug his long-sleeved top over his head.
You crawl back over him, legs straddling his hips, your hands dropping to splay over the broad, warmth expanse of his exposed chest, his body left in just his boxers beneath you, an inviting happy trail of darkened brown hair littered above the waistband. Licentiously, you roll your hips down into him, dragging the soaked state of your core over the bulge of his boxers, making his cock twitch beneath the fabric, a groan rumbling from his chest.
“Fuck, honey,” He huffs, head falling back into the pillows, hands gripping your waist as you move against him in a teasing downwards grind, a carefully precise rhythm. “Can’t wait to have that sweet little cunt wrapped around me.”
You bite down against your swollen bottom lip, body straining with arousal, and hook your fingers through the waistband of his boxers, dragging them down his thighs, swiping them off his legs. Your throat tightens. His cock, thick and throbbing, slaps up against his stomach, the tip red and engorged, dripping a bead of translucent pre-come onto his belly, his balls full and heavy between his thighs. He keeps his gaze settled on you as you gawk like a renaissance painting; his eyes needy, dark, hungry. Unrestrained.
You exhale shakily, hand gliding down to curl around the base of him, manicured nails delicately smoothing over the sensitive, soft skin. You give him the smallest pump with your fist loosely clenched, and his cock twitches in your grip, hipbones flexing beneath you.
“Gotta be honest. M’ not gonna last if you tease me like that, baby,” He rasps sincerely, lips spreading with a rugged exhale like he’s struggling to contain himself and this bubbling need threatening to boil over between you. The confession only sends electrified wire sizzling along your veins in the form of arousal, and you nod in acknowledgement quickly, lifting your hips. You squeeze gently at the base of him, angling his cock until it’s nudging against your entrance.
“There you go,” He breathes, exhaling out through his nostrils, whilst you tilt your hips slightly, slowly sinking down onto his thickness. Your mouth dries at the sheer size of him stretching your clenching walls, jaw falling slack as your hips roll, determinedly swaying down until he’s entirely sheathed inside you to the hilt. You both sound a simultaneous groan of thrill, his brows pinched with concentration as he gives you time to adjust, your hips continuing to absently swirl in circles as the prior dull pain swiftly bleeds out into pleasure, hooking into the base of your spine like a hook.
His jaw works in a grating clench when you tighten around him as you slowly lift your hips, as though your body is trying to keep him inside you. You raise until just his tip is notched inside you, before you’re sinking back down. Slow, steady, his cock curving against the deepest part of you, nudging against that soft, sensitive place that makes your eyes roll back into your skull.
You gradually begin to increase the pace, elevating your hips just to drop back down on him, repeatedly stretching yourself over his girth. His gaze hops over you like he doesn’t know where to settle his attention on; your tits bouncing with your steady pace, the slick of his cock as he’s sheathed in and out of your gripping pussy, folds spreading around him, the inviting line of your neck pulsing as your hips roll. He finally settles on your face, captivated in watching the way your eyes twist with bliss, pleasure striking up along your body, your thighs squeezing around his waist.
“Fuck.. look at you,” He pants, his hands curling tighter around your waist, aiding you, guiding your hips into a slightly firmer tempo. “Look like a goddess on top of me. Like a bloody gift sent just for me.”
You whimper, nodding quickly, cunt squeezing around him, egging him on.
“So pretty taking this cock,” He mumbles mindlessly, eyes drawing to watch where you take him again, your inner thighs quivering. Your fingers curl against his chest, nails digging soft, crescent moons into his skin as you heave yourself up, before slamming down harsher, both of you moaning wantonly at the pressure. Your ass begins to slap wetly back onto his thighs as you rise and fall quickly, your back arching each time his cockhead brushes and prods into your G-spot.
“Other guy doesn’t know what he missed out on,” Harry husks, eyes drawing a searing line up your body as if he’s mapping you out, committing you to memory. His hips sway, grinding himself up to meet your repeated dropping motions, rolling himself flush into you each time. He chuckles, the noise strained with pleasure. “I can’t say I’m that sympathetic for him, though.”
His hands smooth further up along your curves, before he’s hiking himself up enough to wrap his arms around your body, your chest arching into his. You buck down into him, his face burying against the crook of your neck, breathing hot and rasped against your skin, your pulse fluttering frantically beneath it, tensing with each shameless moan that crawls out from your throat.
“Get it all to myself, huh?” He mumbles, sucking against that spot he left on your collarbone earlier, darkening it further, the bruise blooming with red and violet, like a stain against your skin you currently wear with unadulterated pride. Your cunt makes a vulgar, moist squelching sound around him as you jerk yourself onto his cock, riding his lap with a lacerating wildness.
“Yes, baby, fuck- like that,” He moans, tilting his head back to peer up at you, his blackened-out eyes shimmering with lust and something bordering on worship. “S’ all for me, yeah?”
“Mhmm- yes, all you,” You agree haplessly, your tits jerking with your body as you bounce on his dick, chasing that twist you already feel pulverising and chewing at the frayed edges of your burning bliss.
His hand dips down between you, the tips of his fingers consciously rubbing sternly over the engorged swell of your sensitive clit that’s peeking out beneath the hood. You jolt at the added stimulation, pace stumbling, and Harry takes the chance to curl his robust arms tighter around your frame, and before you can process his movement, your vision is whirling in a blinded blur as he flips you both, his cock still impaled in you. He lowers you down into the cushiony comfort of the mattress, silk spilling out around your head.
“You’ve had your turn,” He says with a crooked smirk, dipping his head down to bite gently at the edge of your chin. You go to grumble in petulant protest, but he cuts the sound off from the tip of your tongue with an unyielding, borderline harsh thrust into you, silencing you with his cock.
He repeats the action, slower this time, letting you feel the ridge and veins of his length, sliding through your slick, sensitive walls. Grinding down into you, that coarse thatch of curls at the base of him that’s slowly greying rubbing against your swollen clit peeking out from beneath the hood. You sound a rapturous, libidinous moan, head falling back into the pillows and chest arching upwards with a heave.
His hips jerk at the sight, before restraint snaps like a thread untying, the chain unsnapping that shielded the rabid dog to the pillar. He slams into you, hips slapping wetly against yours, cock plunging into you with brisk speed, firm.
“Yeah, you can take it, can’t you baby?” He moans in a gruff rumble, a sheen of sweat tilting over his temple. “So fuckin’ good. Feel so good wrapped around me- better than I imagined.”
You whimper, arms looping beneath his, hands curling over to his back. You dig your nails deeper into his skin than you meant to, leaving dim, red marks down the length of his back. But he doesn’t seem deterred- if anything, it spurs him on to pound into you swifter, relentless.
“So sweet and wet,” He mumbles more to himself than you, fucking you into his mattress. “Dripping all over my cock, aren’t you?”
His hasty, muttered questions are rhetoric, slipping from his lips like the drip of honey, curdling with sweetness. You couldn’t think to answer even if you wanted to anyways, shameless moans pouring from you in tumbling sways of bliss, body sliding up the bed with each jackhammering thrust of his hips.
You squeeze around him, legs loosely splayed wide for him to pummel into you, cunt slick and hot around his throbbing length, your face flushed and hair splaying widely around your head on his pillows. His hands settle on either side of your head, his eyes settling on yours intensely as his hips swing into yours, his eyebrows saddled with focus, dense breaths and groans drawing out of him. His chest shines with a thin line of sweat, his biceps flexing and the veins in his forearms bulging as he bucks himself forward, fucking you ruthlessly.
It’s shameless, a tangle of bodies and limbs that intertwine like second nature, like your frames automatically blend into each other. As if you hadn’t just met tonight, starting as strangers when you were both meant to grovel around in your own solitary. As if you were both molded to be here; with you beneath him, his cock hammering into your pulsating hole.
“Fuck, m’ not gonna last much longer,” He admits, glancing down between you to watch where your abdomen rolls to grind your hips up into his sharp, plunging thrusts. “You gonna come for me, baby?”
Your mouth feels numb, eyes glazed over with the pleasure that curdles along you. But you nod eagerly, nails digging further into his flesh. He pants, using the last of his renowned energy to buck harder into you, chasing you both to those releases burning through your blood, sizzling to an unstoppable height before it captures the pair of you.
His head drops down, forehead pressing to yours, your mingled noises tangling in the heated air between your mouths.
“Go on, honey. Come for me. Let me feel you squeezing me,” He mutters frantically, and his mumbled coaxing that rasps past your ears are the final length that stretches before that release curls around your veins, splashing like liquid ecstasy through you. Your mouth catches open in a noiseless whine, your eyes rolling back into your head.
Your thighs clamp around his waist, cunt tightening around him before spasming, juices slicking over him in streams, dripping down to his balls and smearing each time they slap against the curve of your ass. He sounds a groan that sounds pained, his hips stuttering in their pace as your walls squeeze and flutter like they’re trying to milk him of everything he’s worth.
“Fuck. That’s it, that’s it, so good for me-” He groans jarringly whilst you mewl hopelessly, hips bucking up. His thrusts turn erratic, uncoordinated as he unceremoniously chases his own orgasm, slamming down into you with propelling hips, sinful, the force staggering.
His mouth pinches in effort as your cunt slicks another gush around him, and with a hiss of restraint, he pulls himself out of your wet embrace at the last moment. His hand hastily dipping down to wrap around himself, length soaked and throbbing. He barely pumps himself once before his thighs are locking up, a trembling moan that whisks off into a whimper as the bliss hits him squarely in the gut, and his cock is jumping in his hold, ropes of thick white painting over your stomach in ropes of heat, nearly reaching your breasts.
You squirm, limbs aching, dipping your chin down towards your chest to see where he weakly strokes over his cock to milk out the last of his come, which dribbles down to your mound, warm and smooth and sticky.
For a moment, the only sound in the room is the hoarse panting of your shared breaths as you both reel through the after effects, foreheads still pressed together. Your eyes flutter closed, body sated, a content afterglow burning low through you. You feel him shift above you, dipping his hand down to your stomach.
Slowly, reverently in a way that feels nearly pious, he swipes a thick finger through the layer of his come on your belly, smearing it over your skin and collecting it on the pad of his digit. And then-
He’s carefully lifting it up between your warm bodies to your parted, swollen mouth. His finger taps softly against your bottom lip, coaxing your eyes open to meet his. They’re still dark, inky, but there’s a softer kind of benevolence swimming through them now, tender.
You swipe your tongue out to collect his come from the tip of his finger, letting your jaw fall slack as he guides it into your mouth. You moan softly at the salty taste of him, stifled as you curl your lips around his finger, sucking the essence of his release right from his skin. You hear his breath hitch as he laboriously slides his finger out again, swiping over your bottom lip. A beat passes before he’s dipping down and pressing his mouth to yours, tasting himself on you.
The kiss is delicate, still amorous but with a fondness burning through it. He pulls back, his tongue carefully swiping over his lower lip like he’s relishing the flavour of both of you combined, your need like a physical, potent taste.
He gives you an unhurried, warm smile, before his hefty body is moving from atop you, and he’s dragging himself off the bed with strained, exhausted movements. You exhale shakily into the slightly humid air, your skin gradually cooling as he pads into the connected ensuite. You hear the tap running as the room lulls around you, head drooping to the side, eyelids feeling heavy.
He returns a moment later, crawling to your side. You almost jolt as the warmth of a damp washcloth meets your sensitive skin. He prods it gently over your stomach, cleaning his own release from you, padding it gently against your sore, puffy core. His movements are nothing short of reverent.
He carelessly chucks the rag onto the floor, before he’s maneuvering your body onto your side, settling down behind you, his brawny arm curling around your waist, your arms tucking in front of you. His fingers brush against your wrist as his body presses into yours from behind, broad and assured.
For a while, neither of you speak, simply relishing in the afterglow that drapes over you like a blanket, especially after Harry moves the glossy silk of the sheet over the two of you, the coolness inviting on your warm skin. Consoling, he presses a slow kiss against the curve of your shoulder from behind.
“You know, I’d like to invest further in this, if you’d be so kind as to allow me,” He murmurs into your skin, careful but unhesitant in his decision. There’s a tinge of amusement intertwined with his tone at the inane ridiculousness of the continued jesting metaphors of a business transaction being shared between you.
“What are you offering?” You whisper back into the dull smoothness of his lavish bedroom, a knowing smile lilting up the corner of your lips. You feel his own mouth upturn in a grin against you.
“A second date. If you want it.”
You’re gladdened by the fact he can’t entirely see your face so you can shield the giddy, elated expression that tilts over your expression. Your heart thumping with a vertiginous stutter at the thought of going out on another date with Harry, to share precious time with him again.
Time where you’re both aren’t under the restraints and tensions of your jobs, where you can relish in the taste of each other, the feel of each other, the simpleness of comfort found within tenderness and lasting looks. A time in which you don’t have to be perfect- you can just be.
You tilt your head back, coaxing his face into the crook of your neck, hearing him inhale softly as he breathes you in, the scent of sex and something softer lingering in the air.
“That can definitely be arranged,” You answer, coyness blooming in your voice, but settled with an undeniable soft rawness. His arms tighten gently around you, the both of you ravelled in the other in his large bed, the milk-dipped moon waving somewhere high above the heights of colossal towers that loom like spires, the scintillating but gentle whisk of the city lights peeking into the room, something like nectar settled on the tips of your tongue, saccharine and honeyed, settling into the air like promise.
And now you think; when you return to work, maybe you actually will thank Rebecca for convincing you to go on that blind date.
“But I have infinite tenderness for you. I always will. All my life long.” - Blue Is the Warmest Color (2013)
Comments, reblogs and feedback are so gratefully appreciated! I’m slowly starting a tag list, so if you’d like to be added, let me know.
A DECENT THIEF, A SMITTEN BILLIONAIRE, ONE EMERALD RING, A SIMPLE CON JOB, ONE VERY INCONVENIENT ATTRACTION. SEX, LIES, LARCENY—ALL BEFORE THE SUN COMES UP. EASY PEASY... RIGHT?
-> READ MASTERLIST HERE.
A.N. -> NO SPOILERS TO MATERIALISTS. This is a ROM-COM done right. Inspired by 'Desperado' by Rihanna. And also, a completely different take on Harry's character than the bullshit he had to deal with, he just has so much potential. I had so much fun writing this 🌻 (as in, 18 straight hours of staring at a word doc, burning my corneas and rubbing my hands like an evil fly. haha I'm actually dyingggg)
W.C -> 13k+
C.W -> 18+ MDNI, third person POV, fem reader, thief reader and she's a bad bitch, harry is fucking rich with a big dick that's what, sexual themes, smuuuuuut baby but make it fun :), luxury brand and pop culture references, witty repartee, cat-and-mouse dynamics, romcom everything.
If you think all thieves lurk in shadows wearing black, bless your pedestrian heart—you’ve never seen her steal a thing. And besides, subtlety is overrated. Also, spoiler: she actually preferred furs. Fur, red-bottoms, a little harmless cleavage, and a crimson-lipped grin that says, ‘catch me if you can.’
Now, these businessmen, no matter how adorned from their broad shoulders to their straight cuffs, are exactly what they seem: easy pickings. That is—if you’re content with playing in the minor leagues.
Rookie mistake. You aim for the big leagues, reap the financial rewards, and set your sights on those wearing rings.
The ring is the tell. A man who wears his wealth and dignity on his finger is either married, vain, or a dumbass. Often enough, he’s all three. And a man who wears a ring worth more than your apartment building—and the one next to it? That’s not bait, that’s a goddamn challenge.
And this probably married, definitely vain dumbass made her want to stomp her heels through the marble.
She was supposed to be walking out the door right about now—a smoky, smirking, forgotten memory—with her latest spoils: Tateossian cufflinks, a Chopard Happy Sport, and two crisp hundreds tucked into a Balmain wallet.
She’d earned it. Eeny, meeny, miney, more than endured a full hour and a half of sucky—literally—sloppy neck-kissing and thigh-groping from a receding-hairline gentleman who fancied himself the face of a major hotel chain. Now that face was lying sideways on a lounge table, mouth open, snoring softly into a puddle of $600 Scotch. And she hadn’t even made it past the lobby. Cash on arrival, you could say. Astral forces or coincidence—either way, it had been a full year since Dame Fortune had dropped by her door.
A few touches here, a brush of her wrist there, a shoulder-check, a pat on the cheek—bada-bing-bada-boom—two months’ rent. A dent in the student loans. And a little extra, just for her trouble.
She should’ve called it a night. Then there was this fucking guy.
Mr. Premium-cocktail-without-a-care, lounging like temptation in a custom-cut Ralph Lauren and Zegna shoes. You want to know how much money follows a single glimpse of this man? You start punching in zeroes, and line those fuckers up.
She didn’t lose sight of him even for a second as she quieted her Louboutin soles on the carpet past the velvet curtains into the lobby bar. Here, the ice clinked softer, and the elite laughed quieter. No one poured their own champagne. It was all expensive colognes, curated modesty, and vintage timepieces ticking loud enough to remind her she’d never belong.
And tonight—him.
Seated alone (aw, poor little rich boy), fingers curved around a lowball glass dribbled with condensation. Judging by the burnt orange peel and the blood-toned glint: Negroni. Bold, bitter… how predictable. Almost medieval in its masculinity.
He looked like a statue someone forgot to rope off—half-lit under the frozen-firework chandelier, carved jaw tense, eyes cool and unreadable. His suit, charcoal black, cut so sharp it could split an atom. No tie, studded cufflinks, clean-shaven, but not enough to suggest he was expecting company.
And in a sea of glitz and fakeassery, where every other guest was a fresh Rolex or a hollow trust fund playing dress-up, this one? This man was none of that. There were minnows, jellyfish, the occasional shark... but this motherfucking blue whale was a silent, drifting monolith that out-riched half the Atlantic. And she was ready to cast a wide enough net, even if stitching it for days on end was all it took.
The bartender called him Mister Castillo, the name curling off his tongue, veritable old money dipped in Cuban honey.
She blinked once, then twice.
Castillo. Cast-ee-yo.
Huh. Exciting. Exotic. Never heard of him. And she was very good at knowing people she was supposed to know, which made him even more of a tricky mark.
But then that fucking ring had just made itself her next prize.
Thick, unapologetically gold, crowned with an obscene emerald—the colour of envy, of desire, of high-stakes possession. It whispered legacy, old money, old blood, an item a loving father might hand down to his son. Worn on his right hand, not left—because commitment to women was optional, but commitment to the image was unbreakable.
She hung fire at first, took the long way round the lounge, steps a punctuation for her thoughts, an extra lap through velvet shadows, watching him. Reading him.
Right off the bat, her target was a gorgeous, sun-kissed Grecian god. Late thirties, if she had to guess. Sexiest physique—broad-shouldered, lean in the hips, tall enough to make other men glance sideways. Sinful dark curls, waiting for a manicured hand to tug on them and mess up. A restless ankle tapping to some invisible metronome, presenting an internal tempo she’d kill to sync with. Not a sliver of a smile, just those full, distracted lips, tucked over a neat row of pearl-white teeth.
And what lay between his legs better be a stack of fresh greenbacks or his entire goddamn offshore account, because oy vey—she’d seen her share of oversized Hollywood ego and whispered big dick myths, but she never thought they existed. Jesus, they were real. Sometimes, they walked amongst us, anonymous, brooding solo in a gilded hotel bar.
The results were in: another tired, beautiful, well-endowed man. Bullseye. So what did this one deserve?
A moneyed ingénue? Pass. A spoiled heiress dripping charm? Overdone. A chic art dealer with one too many anecdotes about Venice? Closer, but no.
No, tonight she wanted to be... unmissable. Impenetrable. She would be the dazzling chess piece dropped mid-game, daunted into taking a closer look.
That hadn’t been the case for the last woman who’d approached him in the past three minutes—swiftly intercepted, spun around, and escorted back to her table with stunned, indignant scoffs by a bodyguard stationed less than a yard away, built like a marble column, an earpiece coiled into his collar.
So. Castillo was important. Hot damn.
Maybe a politician or maybe even a crimelord. Honestly, who cared when he looked like that? And for all that—how had she never heard of him? Either way she weighed it, those sons of bitches spilled out of headlines like loose pearls. If he were one of them, she’d have seen the profile, the scandal, the fourth wife in Chanel.
She realised, somewhere between her fifth glance at the back of his neck and the slow burn of hour-old-white-wine in her gut, that she was only dragging this out. For what? A better angle? A cleaner exit?
She wanted him to see her, and not in the metaphorical way poets meant—she wanted his eyes. She wanted the recognition.
And the truth was that the sight of him was turning her into smoke. Thick, ribboning, deliciously absurd smoke. So, she might as well put the fire out herself. Or at least throw more gasoline on it. Whichever worked.
She straightened, traipsing past low-lit booths and lower morals, the air around her reeking of rumoured secrets and the spice of Creed Aventus. Her fur coat dragged the dusk with her, the black silk slip beneath flirted with every bulb overhead, while the slit at her thigh played hide-and-seek with lace and sharp intentions. She was the whole damn production. Flash of leg. Flash of steel.
Upon reaching the bar, she slid into a seat one down from him—close enough to be noticed, distant enough to play disinterest. That sweet spot that begged curiosity without costing power.
The coat slipped off, one less layer between her and the moment, and it had been trained—trained to fall, trained to seduce. But then—
Everything moved in a single blink.
Two shadows, flanking, closing in from either side, en route to check. Earpieces. Fast, trained, and quiet, that always came before a very loud takedown. Her instincts tensed, reflexes flickering: eyes on the back exit, how she could make it there in four seconds flat—
But before she even had to brace, before her pulse spiked, the man—Castillo—lifted a hand. Just a flick. Barely even a gesture.
And the shadows fell back, evaporated, melting into the gold-trimmed corners like good little dogs trained to obey.
She let out a breath she hadn’t meant to hold. Phew, she thought. She really didn’t feel like ending up zip-tied in a body bag tonight.
The good news was, she’d just passed her first test, and he hadn’t even looked at her yet.
Her lips curled minutely. She set her elbows on the bar, angling her body in that curated way, just enough to show off the right curves, the lune of her spine, the shape of her ass—all half-bored, half-bored-with-a-purpose. Every molecule of her screaming, I’m exactly where I’m supposed to be, and isn’t that unfortunate for you.
Now here came the fun part. Playtime.
She flagged the bartender with two fingers and a smile that had gotten her out of far worse.
“Rusty Nail and two shots of tequila, please.” The freshly stolen hundred-dollar bill skimmed across the bar with the grace of a ballerina and the indifference of a bribe.
She smiled at him, lashes batting like the wings of an expensive butterfly. “Keep the change. Thanks, sweetie.”
The bartender blinked. People didn’t usually tip like that unless they were drunk or trying to impress. She was neither.
To her, life was about redistributing wealth—ideally while looking this hot doing it. It didn’t always have to be her wealth, not technically. From the rich, to the clever, to the ones who just seemed like they could use a little extra—she played the part, took the cut, passed it along. Redistribution with flair.
“Ma’am,” the bartender said, voice barely concealing his awe. “Coming right up.”
And then—finally—she turned to her enigma.
He had thawed because now, the gorgeous ice sculpture wore the suggestion of a smirk. A mouth made for terrible decisions curled at the edge as though he knew all her secrets and wasn’t judging. Yet.
Her first instinct? Run. Her second? Double the fuck down. This man, who’d probably grown an empire on poker faces, read hers in under thirty seconds.
“Feeling generous?” he asked.
His voice—good lord—it got under her skin like velvet poured over sandpaper. A silken drawl soaked in wet, hot caramel. The goosebumps on her skin were an obvious giveaway, and her legs crossed unintentionally.
She forced herself to play it casual, leaning her chin into her palm as if she were a woman who had nowhere better to be. “Especially tonight.”
Her drinks arrived, lined up like loyal foot soldiers, and the tequila hit the bar with a theatrical flourish and a pricey wink from the bartender. She dragged her cocktail glass toward her lips, not breaking eye contact, not giving him the pleasure of her full attention, ready to take the first sip when he hit her with—
“Or did old Billings not deserve the hundred as much as the bartender?”
She nearly inhaled the drink. Her brain split in two—half processing the drink’s cost, the other shouting what the actual fuck. But because her reflexes screamed to defend, she swallowed, industriously, the way one would swallow a really sharp insult. Well, she wasn't new to that.
She faced him, properly now, eyes narrowed in amused disbelief.
Oh, he was sharp. Old, but sharp.
Then, as if she weren’t even a threat worth standing for, he rose, unhurried, shoulders rolled beneath his jacket in one fluid ripple. He did the thing men do when they don’t button their coat—deliberately, arrogantly—and walked the three steps to the seat beside her. The shortening distance only crescendoed the goosebumps on her skin.
His knee grazed hers as he sat down beside her, and she felt the contact echo up her spine like a bassline.
He leaned back, turning to her fully, claiming space without apology. She was certain this man had been worshipped before. He obviously wanted to make no fuss with that when he gestured lazily to the nearest shot.
“That for me?”
Goddamn it, he caught her drift. All too familiar with it. Oh, this guy didn’t just play, he collected gilded fucking trophies.
She tilted her head, thoughtful, not giving him the win. “Two hundred.”
His hand paused, brows lifting. “For a shot? Pretty steep ask.”
“Billings didn’t deserve the two hundred bucks.”
His mouth twitched again. “Who are you to decide?”
“You know how it is,” she said airily, fingers brushing her cocktail. “He fumbled the bag. I picked it up. Capitalism, heard of it?”
That earned her a laugh. Deep. Rough. Stupidly attractive. A laugh she would accidentally rote-learn and dream about later when she was in bed with someone else.
He scratched his temple with one slow finger—enough to flash the ring again. That exquisite, infuriating ring. She was no kleptomaniac, but she was reading some signs tonight.
“So,” he said. “You won’t even deny it.”
She smiled with her teeth. Catlike. “What can I say? Sometimes the universe makes executive decisions—and I just follow orders.”
“And who’s pulling your strings?”
“I’m more of a free agent, though I have my own reasons for playing along,” she drawled, popping her lips.
His eyes searched hers for a long moment—more clinical than flirtatious. Then he leaned in, his voice dropping half an octave.
“Now, you’ve got me lined up—what’s your play? Charm me, crush me, or cut me loose?”
Oh. Well. Shit. But what irked her more was that he was expecting her to fold and kneel like some desperate fool. Not a chance in emerald heaven.
The smile slipped from her lips—but only to reassemble, sharper, colder, with twice the wickedness and indifference. She leaned in, just enough for their chests to brush, breathing in the scent that clung to him: bergamot, crisp, fresh like banknotes, tangled with heat and velvet. Maison Francis? Jean Paul Le Castillo?
She couldn't give two shits anymore. What mattered was the truth in his words—he was a mark. Just another mark. You know what would be funny? If his name was ‘Mark.’ Talk about aligned stars.
Rather, her sharp finger traced a soft line down the strong ridge of his nose.
“Oh, honey, all three,” she purred. “You’re my retirement plan.”
If that line rattled him, tipped his balance, he didn’t show it. He just tilted his head a fraction, chewing the inside of his cheek to fight a smirk like she’d just said something cute. Cute, for fuck's sake. That was new. And slightly offensive. If anything, he leaned in a breath closer—her red lips now a whisper from the tip of his nose.
Well. She did always have a thing for brave men with stupid impulses.
“In that case,” he murmured, low enough to be indecent, “you’ll want to give that watch back. I’m not exactly hurting for time.”
Her mental playbook skipped a beat. These moves? These flirtations, the very presence of her? They’d killed with a 99.9% success rate. And yet—
He was the 0.01%. In her life, and in the flesh.
His breath danced against her mouth—warm, spiced, all sin. His eyes, dark as midnight ink, watched her with that unreadable calm that meant he already had an answer to a question she hadn’t asked yet.
She offered her most innocent smile. “Which watch?”
Now that was bait, and she was proud of it. She knew how to pick a mark—but he was starting to feel like a match.
Before she could finish a sip, his hand lifted. First to her chin—just a touch, a direction, a swish of the stunning emerald—then lower, big, soft fingertips drifting along the curve of her neck like he had all the time in the world. It was intimate, yes, but worse—it was confident. A languor that predators used just before they pounced.
And then the other hand moved to her waist. Ah, so that was the game. No sudden grabs or cheap tells. Just proximity, pressure—and gravity pulling her into a choice.
To anyone watching, they probably looked like lovers. Or worse: like a husband and mistress on a regular date night. Which, in this city, was practically tradition.
While her pulse tried to find its way back to a normal rhythm, the smug bastard reached deeper in. Her lips parted, his brows sloped in amusement. He slipped his hand into the folds of her... faux mink—and surfaced with a familiar glint of gold, his knuckles grazing her waist like he’d paid for the privilege.
“This watch,” he murmured, all victorious and amused, lifting the Chopard into view like a magician pulling a rabbit from her cleavage.
Okay, that was a mindless attempt on his part. She didn't show it—she was too experienced for that.
She stuck out her bottom lip, a perfect little faux-pout. “Oh.”
“Didn’t deserve that either?”
She gave a light shrug, eyes flicking to his working jaw. Probably with the restraint of not dragging her to a more private conversation.
“Old Billings spent most of our evening convincing me his Cadillac had reclining seats, that he had a penthouse if I preferred vertical real estate, and—my personal favourite—that his artificial hip could rotate 180 degrees. Figured I need added compensation.”
He wrinkled his nose.
“Yeah,” she said. “I thought so, too.”
There was a beat of loaded silence between them, just long enough for her to decide to play a little dirtier.
“I really, really need you to understand that I…”
And with that, she slipped her ankle up the inside of his pant leg—delicate, methodical, just suggestive enough to distract without giving anything away. She watched it register in his body, the stillness, the knowledge she was still in control. The way his breath faltered for a fraction of a second. The tiniest tension in his thigh.
Then—while he was preoccupied with the very important inches of him she wasn’t touching—she gently pried his hand off her neck and placed a second watch into his palm.
“I thought you meant this watch,” she finished.
He blinked, eyes flicking down to his hand—and then to the beloved watch nestled there. Audemars Piguet. He hiked his sleeve up to reveal his bare wrist. No Audemars Piguet.
His expression flashed. For a heartbeat, genuine surprise cracked the perfect glass mask he wore. And oh, how delicious that was.
Zero fucking clue when she’d taken it. But she had, and it had been laughably too easy.
She turned away before he could collect his scattered little wits, spun back on her stool with feline grace, and plucked up her cocktail. The sip-stirrer spun between her teeth as she smiled into the clinking glass like she hadn’t just pickpocketed a man worth enough to fund a coup.
He exhaled behind her. A low, almost breathless laugh. “Jesus, you keep me on my toes.”
And she kept her eyes on her drink, swirling her glass, smugness curled into her spine. Her heart, however, was thudding. A pleasure so sharp she hadn't felt in months.
He fastened his watch back on with effortless precision, as if the stolen moment hadn’t unnerved him at all. But she’d seen it in his pupils, dilated for just a flicker too long, and in the slight drag of his liquor breath.
“That won’t be the last time tonight, will it?” he asked.
And now, finally, she turned—the game levelling up—letting the full consequence of her grin land like a challenge.
“Depends on whether you plan to undress me. Or just negotiate a better security team.”
A single brow arched. “You really think I’d sleep with a thief?”
She spoke into her straw, “And here I thought you were desperate.”
He angled his head, eyeing her as if she were a puzzle that might explode if solved too quickly. “Hm. Charming.”
“Oh, please,” she said, shaking her head, eyes glittering with mischief. “I’m persuasive. Charming is for people who wear pearls and apologise for orgasming first.”
That startled a laugh out of him, just a soft breath—barely there. But she caught it.
He leaned forward slightly. “So this is your play. You cosy up to men in designer, sweet-talk your way into their wallets, leave them with crushed egos and significantly lighter pockets?”
She traced the rim of her glass with a manicured nail, her gaze not leaving his. “If you’re lucky, that’s all I leave you with.”
He studied her. “And if I’m unlucky?”
She smirked. “You’ll never forget me.”
His tongue pressed into his cheek again. “You’re so certain I won’t turn you in.”
She rolled her eyes. “If you were going to do that, you wouldn’t be sitting this close. You’d be signing forms, talking to Officer Hardass Number Forty-Two, and making a statement about your poor, ravaged emotional trauma.”
He smiled. It was dangerous on him—sharp at the corners. “Oh, I am emotionally traumatised. That watch you nicked off me was one out of the three ever made.”
Be still, my traitorous, beating vagina, she thought. And that magically enhanced third leg of his—was it a limited edition, too? If so, she needed to bring out the big guns.
She tilted her head, slow and feline. “Well, I’d have to console you. Probably by sitting on your face.”
He blinked once. Visibly.
She stirred her drink once, then leaned in, her voice dropping to a whisper like it was just between them and the velvet dark. “Let’s be honest. If you really wanted Billings’ watch back, you would’ve demanded it the second I sat down. Instead, you tested me and played.”
She let that hang.
“Which tells me,” she added, “you’re not here for justice.”
“Definitely not,” he murmured, his voice suddenly hoarser than before.
“Mhm. You’re bored. You want me for the kicks.”
The way she said it, he knew he was already too deep. Her words moved like smoke: evocative, listless, curling around the edges of his constraint. His eyes dipped to her collarbone, her shoulder, her motionless thigh as it crossed over the other, the little peekaboo of the lace stocking catching the amber lights.
“Are we going upstairs,” she asked simply, “or are we having this entire conversation without your hands on my tits?”
Silence. A beat. Then two. She only grinned at him, teeth set on her straw suggestively.
He hung his head for just a moment—as though he needed a second to recalibrate. Or maybe to hide the smirk whittling its way across his mouth. When he looked up again, his dark eyes flashed, a little less amused.
Wordless, he slid one of the shot glasses toward her with two fingers, then reached for the other himself. Deciphering his inclination, they knocked the rims together in a soft clink.
“To boredom,” she cheered.
“And not-so-cheap thrills,” he triumphed.
They tipped them back in sync, the tequila burning down her throat, fast and sharp. She swallowed, licked her lip slowly, watching the way his throat bobbed, the way he adjusted his cufflinks with the grace of someone preparing for battle—not sex.
Then he stood, straightened his already-perfect jacket, tugged once at the hem, and offered his kingly hand to her.
She stood of her own accord, shoulder brushing his as she leaned in to murmur near his ear, breath tracing the line of his jaw. “You better have a penthouse suite waiting,” she murmured. “It’s the least I deserve if I promise not to do anything stupid tonight.”
He gave the barest tilt of his head, eyes burning. “You’re just the prettiest little liar, aren’t you?” A pause. A half-smile. A yearned release. “I was hoping for a more insightful breakfast later.”
Her lip caught between her teeth—just briefly, reflexively. Delightful. Penthouse suite. Hotel breakfast. Her weekend was off to a great start.
His suave grin or lethal gaze didn't break even as he flicked his wrist to gesture to someone behind her.
From the shadows, security materialised once more—clinical gazes, efficient, precise. Two of them, lean and suited, eyes scanning her from habit rather than hostility.
He rifled through the inner pocket of his jacket and snagged a sleek black card—no numbers, just the embedded insignia of something far more exclusive than a Visa. He handed it to the taller guard with a calm, “Her pick. Thanks.”
“Sir,” the guard nodded and spoke into a mic clipped inside his lapel.
The moment flew into surreality—muted commands, invisible systems moving around her. She watched the transaction unfold, the way reality seemed to bend to his will. There was no front desk, no credit hold, and no keycard handed over. Ching, ching, ching—the dollar signs rolled up within the imaginary slot machines in her head.
A final nod from his lackey crew, and it was done. Her eyes twinkled with the beginnings of a grin.
Well, then. That was too damn easy.
Only now did she take his hand, the one with the inordinate emerald ring, feeling the curve of the metal, folding her fingers in, as though it had been her idea all along.
“You always carry that much power on you?” she asked, stepping in beside him as they turned toward the elevators.
“Only when I plan to be stripped of it later,” and he shot her a wink.
Her laugh came, unexpected and soft. And this time, she didn't hide her grin.
As they entered the elevator, the doors whispered shut, and for a brief moment, she knew—this was a checkmate.
Here’s what you really needed to know about first-name-still-unknown Castillo: boy, can he kiss.
The man could kiss as if he were meant to wreck religion. It wasn’t sweet, or even aggressive—it was hunger, six-foot-all-male arched and soldered to her lips with intention, with certainty that he was going to fuck hard tonight. One hand fastened in her hair, the other fumbling behind him for the bedroom door handle as if the whole city were plotting to interrupt them. She barely registered the luxuriant flash of the penthouse behind his broad shoulders: the wet bar gleaming like something out of a Bond set, the marble floors glowing under dimmed designer lighting, the magnanimous kitchen, the terrace doors flung open to reveal Manhattan glittering like an unfurled circuit board.
All of it—opulence, skyline, good sense—blurred at the edges as her resolve melted beneath his wicked mouth. She’d come for a ring and a job, and somehow ended up consumed. And probably... coming, too. Let's see how it goes.
She vaguely recalled thinking, Well, at least security’s off tonight, before he kicked the door shut behind him, and she surged up into him like she’d been waiting all year, tearing that blazer off his shoulders.
At some point—maybe while his hand mapped the grooves of her spine, maybe while his mouth drifted lower in slow worship—he broke the rhythm long enough to mumble against her skin.
“You gotta... tell me... something first.”
“Clean bill of health. IUD’s locked and loaded,” she hummed knowingly, arching into his mouth as it brushed her clavicle. Oh, and god bless the IUD.
He spoke through a mouthful of a kiss. “Appreciate the intel, but I meant to ask if you’re past eighteen.”
She tossed her head back to giggle as his lips moved over her collarbone. “That’s your cutoff? I should be the one calling the cops.”
“It’s called chivalry, sweetheart. A gentleman doesn’t ask a lady her age.”
“Checking ID is where you draw the line, not bringing a potential criminal into your bed.”
“Your words, not mine.”
“And names?” she shot back, lips brushing his jaw.
He smirked against her throat, voice molten. “I like not knowing anything.”
And it struck her—unexpectedly—of course he did. It was great for her, too. Not knowing her made this cleaner. She was all curves, sex, and invitation, faceless by design. No backstory or entanglement. No real name to trace or recall in the morning—just a woman who walked out of a fur coat and into his bed like a loaded question.
She didn’t move as he kissed lower, slower, charting his route down her sternum. Her eyes drifted to the gold trim of the ceiling above them, but her mind was sprinting elsewhere. Letting sex overrule a job? Not her usual MO. It was too messy, came bearing vulnerability. Intimacy, or really world-shattering sex, in her experience, shattered deceit like glassware, and she needed the lie to keep him seeing her as the sleek, unbothered woman who stole his watch and then made him laugh about it.
She didn’t need his guard down. She needed hers up.
And still, she arched into his mouth as though he were the one writing her name in cursive across her skin, still let herself ache for this brief, hot moment she earned with cleverness.
“For the record,” she whispered, breath catching as his hand skimmed beneath the hem of her thigh-high, “I’m well past twenty-one.”
He lifted his head just enough to glance at her, shadows tucked beneath his lashes, and gave a dry, approving smile. “Perfect. I do my best work outside a prison cell.”
There was a joke in there about experience and knowing better, but her throat closed around it. She did know better, and she was still about to make this mistake with goddamn choreography.
Then, without another word, he ducked low, scooped her up in a single agile motion, and threw her over his shoulder like a victorious hunter returning home with his spoils. She shrieked only to be defeated by a laugh in half-lust.
“Down, boy!”
His big hand came down on her ass for a sound slap. “Behave.”
“Oh, hey, kinda loving my view right now,” she called out, swaying upside-down, giving his admittedly perfect ass a firm squeeze.
He didn’t miss a beat. “More than the skyline?”
“More than the view from the Ritz bathtub, baby.”
“High praise. I like that.”
She landed on the bed with a soft, lavish oof, her hair splayed like a halo, silk dress skating up her thighs. Before she could even prop herself on her elbows, he was over her again—mouth returning to hers, fingertips under her hem, tracing the garter, teasing the edge of her panties with that kind of reverence that made her almost forget her exit strategy.
Then, just as he lowered his head between her thighs, her Louboutin heel planted right between his pecs. A gentle nudge of a reminder.
He paused, blinked, looked up from her foot to her suspecting face—brows raised like a schoolboy caught halfway through a particularly delicious crime.
“What’re you doing?”
“I’m...” he tilted his head with exaggerated innocence, “going to make you come on my tongue?”
She pressed her pointed heel in deeper, just to make a point. “Yeah, let’s not skip to the part where I forget your name and my standards.”
His grin spread wider, unfazed, overjoyed even. Smug fucker.
She leaned up on her elbows, her voice syruped with challenge. “I’d rather have you come inside me. With me.”
He let out a low laugh, shaking his head. “Jesus. What is this, male-finagling 101?”
“Call it negotiation. You want a headliner? Play by house rules.”
He crawled forward with a surrendered sigh, mouth brushing her knee on the way up. Rather, he took her ankle—gently—and began to guide it upward, eyes never leaving hers. The slide of her calf along his shoulder was idle, confident, and territorial.
“Something tells me you are the house.”
“Damn right I am,” she muttered, yanking him in by the collar. “And you’re already losing chips.”
By the time her heel rested behind his neck, he was already smiling again. “Trust me, sweetheart, I can afford it.”
His words sent a short-circuit of dysfunctions sparking through her system. Lust, amusement, danger, maybe a little bit of deranged curiosity. Her body felt like a pressure cooker wrapped in silk. She watched him lean in again, kiss slow and deft, like he was tasting victory already.
She curled her fingers in his hair—his freaking curls—and angled him deeper into the lazy kiss. The way it gave under her touch, thick and dark and sinfully plush, felt like the luxury version of every shitty knockoff she’d tolerated before. This was a rich man’s hair. This was what money bought, not the thinning, brittle kind that came with executives and artificial virility—those were all coconut-head kisses: stiff, unyielding, mildly tragic. This was investment-grade.
Her hands flew to his shirt buttons with greedy precision, undoing, untucking, peeling away the crisp cotton. He shrugged the shirt off and let it fall somewhere past the horizon of the room. She couldn’t look anywhere but at him.
This goddamn man was all ridged muscle and splendid heat, a living sculpture carved by a person deeply horny and well-compensated. Her eyes wandered without apology, drinking him in. Shoulders broad enough to make furniture obsolete, that weathered tan etched into skin like he’d been born in a Marlboro ad, and that V-cut—the infamous, fabled V muscle that you would only acquire with months on a BowFlex—was practically rude. It announced, with a golden arrow from Olympus saying, ‘Please direct your gaze below,’ and that was until he reached down, opened his fly and—
“Holy fuck.”
His face dropped to honest concern, searching her from head to toe. “Something wrong?”
She looked back at his eyes and tried, sincerely, to find shame and failed. “Sorry. No, really. Wow, congrats.”
His brow rose, faintly amused. “Thanks.”
She squinted back at the enormity between his legs. That was no big dick. For every twig, there was a trunk. For every soft peach, there was a firm cucumber. And finally, for every tight space that she had in her body, that was the perfect fit.
“Hang on, I’m just... recalibrating my entire worldview,” she breathed.
“Take your time. He is a shower.” He curved his arms around her thighs and dragged her closer, amused. “Now, should I be flattered or concerned?”
She pointed, unabashed. “You’re breaking zoning laws. That should be registered as a private landmark.”
He couldn’t hold back the smirk. “My penis is a landmark?”
She shook her head solemnly. “Seriously, dude, if you try shoving that in my mouth, I’m gonna need a neck brace and dental insurance. It’s not that subtle.”
He huffed, mock-exasperated, dipping back toward her as she bit her lip to contain a laugh. “Well, neither are you. Seriously, dude, why don’t you just walk beside me with a bullhorn tomorrow?”
She grinned. “Touché.”
And she wanted it all.
She wanted him to wreck her perpetually laid-out life in the shape of whorish moans. She wanted the kind of orgasm that felt like a cathedral collapsing, that made her forget what city she was in, what she was wearing, even what she’d meant to acquire tonight—because who gave a shit about emerald rings when your thighs were trembling like this?
He sank to his knees at the edge of the bed, his rough hands oh-so-warm as he found her ankles, coasting upward, willful. Her heels came off one by one with a reverent slide and dropped somewhere with two clicks. He raised a brow at the stockings—black, sheer, goddamn expensive—and made a face like, ‘those stay.’ Smart man.
While his mouth claimed hers again—wide, possessive, coaxing more of her soul out with each pass of tongue—his fingers found the zipper at the base of her spine. He worked it off her like he’d earned the right; he wasn’t just removing fabric, but unveiling a scripture.
The dress fell away, the only flimsy fabric separating them now. Bared, exposed before him.
“Look at you,” he murmured, and then tilted his head skyward, like the ceiling might offer some divine explanation. “Where’ve you been hiding this?”
The smile that bloomed on her lips was ridiculous. “Right where no one bothered to look.”
He was just… devotion, that made her forget every well-earned cynicism she’d armed herself with. That look he gave her—it was like someone seeing the night sky for the first time.
Every woman deserves this at least once: to be gazed at like a divine revelation, especially by this man. Especially by Señor Castillo.
And when he came down between her breasts and buried his face there—kissing, biting, mouthing, trailing warmth over the softness—and she catalogued.
Every graze of his mouth on the swell of her breast became a snapshot, every drag of his stubble a burn she’d wear like jewellery. His lips ghosted along her skin in an obedience, and that made it worse—better. She kept her eyes on the ceiling, needing somewhere to focus on before she melted into goo.
It was becoming harder to separate pleasure from power, and harder still to remember which one she usually wielded.
Her fingers found his cheekbones, traced the topography of him like a blind woman trying to remember a face she wasn’t supposed to fall for. His thin stubble, coarse, dark, scratched and scalded her in the best way.
She’d despised facial hair on men. Always. Until she decided that his goddamn moustache deserved its own novella. Every time it flicked across her nipple, her body jolted like a live wire. It was filthy what that thing's pornographic implications were. Filthy, what she wanted from it.
She stroked the curve of his upper lip with a fingertip, and he caught her hand in his, kissed the pad of her finger, drew it slowly into his mouth. His tongue curled around it, wet and obscene, eyes on hers the entire time. Then he let it go with a pop so lewd, she had to bite her lip to stop a moan.
“You gotta let me taste you, baby,” he rasped. “If your tits taste this good...” His breath ghosted over her skin. “I can’t imagine your sweet pussy.”
She burst into laughter, spirited, ruined. “I did say I’d sit on your face,” she replied, lifting a brow.
He grinned. “Look at me, I’m a man grieving.”
“Hm. Not in the mood anymore.”
His groan was practically theatrical—but his fingers didn’t wait for applause. They slipped between her thighs, bypassing preamble entirely, right past silk and into soaked, desperate heat.
Conversation stopped.
All her clever little barbs, her glib charm, her velvet one-liners lay dead. Obliterated by the first stroke of his fingers inside her. Her brain went static. White-noise pleasure. A hiss of disbelief.
All the sharpness and swagger she’d carried into the suite dimmed under the slow, deliberate pressure of his hand. Precision. Intention. Like he already knew exactly how she’d fall apart.
She tried to say something, anything. Tried to land one last jab. But all she could do was breathe around his long, fantastic fingers—wide-eyed, hands fisted into the pillow behind her, lips parted, staring up at the gold-leaf ceiling like it might explain her undoing. In, out, in, out... then came the thumb.
And then—the fucking ring.
She felt the metal graze her inner thigh, the cool edge of the gold where it pressed to her skin. Sharp contrast to his heat. And then—Jesus fucking Christ—it dragged. Subtle, sluggish, just enough to remind her her prize was there.
That gorgeous, thick emerald, gold band, tasteful, heavy and fuck, so out of place between her legs.
Or maybe not.
Because when he curled his fingers just right and his thumb pressed in deeper—when he let the gold nudge her, roll slightly against her wetness—her whole body arched like a drawn bow.
He felt her react. Any dumbass would've known, he wasn't that special.
His thumb stayed at the ready, steady pressure circling her clit—but the gem, that fucking gem, shifted again. Cool gold and the sharp cut of emerald dragged leisurely through the slick between her folds, catching where she was wettest, where she throbbed for friction. It was intentional. Calculated. A little cruel, to be honest.
Her body jerked, hips twitching, a powerless gasp yanked straight from the base of her spine—high-pitched, fractured. That ring shouldn’t have turned her on or feel owned. But could a material girl help it?
He looked down at her, mouth curved just enough to betray pleasure, but not enough to give her satisfaction.
“Oh, you like that?” he murmured—just wicked enough to feel intimate. “Huh, you like the way my ring feels on you?”
She wanted to say no. Wanted to sneer, to roll her eyes, to make a joke about being allergic to sentiment or emeralds or anything that felt vaguely like trust. Instead, she bit her bottom lip like it might keep her dignity in place, but it really did not, and—
She nodded. Tiny. Shaking. Needy.
So he rewarded her.
He slowed his strokes, so infuriating, so obscene, and let the ring do the work. Rolled the emerald flat against her clit, then angled it up, letting one of the faceted edges skim across her slit, grazing nerves that had no business being teased like that. Precise. Punishing.
And it lit her the fuck up.
She should’ve hated what it meant—that she wanted something so material, so glittering and male. That this thing—a token of wealth, probably from a wife or a mistress long since discarded—was turning her slick and pliant and desperate beneath him.
God, she craved it.
That ring was everything she didn’t get to have. Status. Opulence. Being touched like treasure.
It was proof of power. And right now, she clearly wanted to be fucked by it.
She wanted it pressed deeper. She wanted it shoved into her mouth next, to taste the gold and the salt of her own arousal and watch his eyes go dark with the knowledge that she liked it. That it wasn’t just sex—it was starvation. It was his want and hers.
Tension spiralled hard and fast, gathering in her abdomen. One wrong stroke, one more whisper, and she'd shatter with her slick clinging to it like a goddamn offering.
And still, he was watching her—all darkly pleased. Reading her confession in real time. Every moan, a comma. Every shiver, a pause in the syntax of her unravelling.
This wasn’t a play for the upper hand or a con. It was relinquishing. And maybe, the part that terrified her most—being known.
That, in itself, was a wake-up call.
So she cudgeled the horny out, pushed him off her with her purpose, let him fall back into the pillows, trousers still hanging indecently low on his hips, cock straining upward like it had its own agenda. For a second, he just looked at her—half-dazed, wholly starstruck.
She climbed on top with a panther's grace and rolled her hips. Just once. Just to feel the obscene friction of silk against her bare, wet slit. The contact made her gasp—all unmasked—and his answering groan was deep, surprised, like she’d just given him the ultimate divulgence.
Then, like the devil himself, he brought his fingers—her slick still coating them—to his mouth. Sucked them in with a hum, as if tasting a rare libation, expensive and exclusively his.
“Christ,” he murmured. “You taste like a dream.”
She didn't have it in her to rejoinder. He was distractingly hard beneath her, so hard it was criminal. Big, big, big man. The feel of him even contained through the barrier of his boxers had her knees nearly give out.
“Gonna kill me,” he muttered, voice hoarse, stunned.
Funny, that was her line.
“Good,” she whispered, leaning in until her mouth brushed his. “Then I won’t need to fake my name.”
He laughed, dazed, ravenous, eyes drinking her in. “Ah, what the hell,” he breathed. “What’s your name, sweetheart?”
For half a second, her mind blanked. What was her name? What was any name? She had to have a name ready for him. How was she so unprepared?
Then, she made up her mind: “Eve,” she said, because one, it was cool, two, sweet biblical references, and three, what a fun little palindrome.
He tested the word on that naughty tongue. “Eve. The first woman.”
She tilted her head, gave him a wicked little smile. “Gotta start somewhere,” she murmured—still perched above him, all wit and velvet, more dangerous than that: ease.
She reached between them. Even after staring for three more moments, the sheer size of him—thick, heavy, curved just enough to ruin. Her mouth opened slightly, involuntarily, but she didn’t make a sound. She absorbed it.
She gripped him, slowly, trifling—more an assessment than a stroke. His cock kicked in her palm, already leaking, and his jaw went slack.
“You got a license for this thing, sir?” she purred in a tease, still staring down like she was reading a classified document.
“I was grandfathered in,” he said through gritted teeth. “Now be a good girl and fuck me.”
And for a breath, a single heartbeat, she let herself feel it. Just once.
His hands, strong and solid at her hips, slid up the line of her torso as if to memorise the arch there. He waited for her, no rushing, no seizing the moment to flip her over and take control.
She leaned forward and kissed him at her leisure. And again, and again, just to be sure it wasn’t a fluke. That made her forget where her body ended, and his began. Her fingers curled against his chest, dragging over the soft smattering of dark hair there, nails teasing. His breath hitched.
It was ridiculous how good this felt. Big dick or not, he was fucking fantastic.
And that was the thing. She’d never trusted fantastic feelings; they were distractions. Weak spots. She’d spent ages compartmentalising pleasure like it came with a damn invoice. Oh, this wasn't that. There were no transactions left (except, er, maybe one) or power plays she had to look out for.
This was two people choosing to fuck like they’d never see each other again. And for once, that felt like a relief, not a regret.
She lined him up with a maddening delay, hips angling just right, and when she sank down—Jesus, it was a stretch. Her breath faltered, lips parted. Head tilted back. Hands braced on his chest as she took him—the world churning to liquid around her.
She took him inch by gentle, conscious inch, and the fullness knocked the wind out of her. She paused halfway, chest heaving, stretched to her capacity.
“You okay, beautiful?” he asked, hands steadying her thigh.
“Yeah,” she breathed. “Just… Christ.”
He gave a strained laugh. “I’ve been called worse.”
She braced herself, inhaled, levelled her knees on either side of his hips, and took the rest of him.
All the way down.
The shock of it punched through her, and the moan that followed was nothing like the others—it was scraping, involuntary, from the deepest part of her.
“Omigodomigodomigod,” she chanted, barely.
“Shit,” he growled, “you’re gonna make me come just watching you do that.”
“Baby, you have got to last longer than that,” she managed.
It can't have been a concurrency. It was vulgar, how flawless he fit inside her. How her body opened for him, swallowed him like it had been waiting for this.
The nasty fucking sounds he made—soft curses, a low-throated groan, the broken “Jesus fucking Christ” against her neck—they conducted volts of electricity down her spine.
She rolled her hips once, testing the weight of him, the stretch, the slick pressure as he filled up that fragment of space so deep within her she didn't know needed to be freed.
Their eyes held for a glorious moment, engraved an intrigue between the lines, as their breaths fused in the intensifying silence.
Finally, she moved again—tentatively at first, recalibrating, learning the shape of this body, its responsiveness, its heat. Then purposeful. Hips circling in uneven figure-eights, savouring every drag of him along her walls. The friction, the angle—it was unmistakable. Her clit brushed the hard plane of his pubic bone with each motion, and the sensation throbbed through her with the symphony of the dirtiest choir of angels.
Her hair clung to her skin, damp with sweat. Her thighs trembled. She adjusted again, finely tuned the roll of her hips as though she were a safecracker aligning the final dial. Listening, calculating, cracking open something far more intimate than a vault.
And in those strokes, she realized: man, this fucking was nice.
Disarming enough to take her off guard. Not flowers-and-pillow-talk nice—but it was strange how his eyes never left hers. In the way he breathed through his teeth when she clenched around him.
Nice, for someone like her, felt impossible. She didn’t get this. She got fancy hotel rooms with poor lighting and overpriced minibars. She got transactional glances, pickpocketed her forgettable flings, and sex that didn’t leave bruises but didn’t leave memories either. She got mornings when she slipped out before the sheets cooled, before they could question what her name was.
This gorgeous man under her, with his big wallet and his even bigger cock, sweat-slicked and broad-chested, dark curls matted against the pillow, hands reverent on her hips—this was selfish memory-making. A reward, maybe. A cosmic oversight in her favour. A divine fuck-up.
And god, what a man. She loathed giving him that vestige of power, but really—wow.
She slowed just to look.
There was heat in his gaze, sure—but also awe. He looked at her like she was the miracle, not the other way around. Chest heaving, abs taut, thighs twitching. There was a line of sweat down his temple that she wanted to lick. Insane, disgusting, but wild.
She leaned forward to do just that, and he kissed her sternum like it was instinct, then moved up—mouthing her breast, sucking just hard enough to draw a gasp from her. She ground down in response, shivering as her clit caught again, the rhythm quickening. She was so wet now, slick, soaked, that it felt inevitable, elemental.
His hands tensed. Thighs twitched. His cock gave a small, telling pulse inside her. He was close, no rush, no push, ticking within her, feeling everything.
And still, he watched her. If he blinked, he’d miss it. This version of her—sweating, gasping, taking him deep—was the most honest one yet.
She’d never been seen like this. Not without masks. Not mid-lie. Not mid-fuck. Not without shame, licking at her spine. She liked it, just a little.
“You feel so good,” he groaned. “Fuck, Eve…”
She almost laughed aloud. Even now, even as her orgasm climbed her spine like a fuse about to spark, she wanted to correct him. Not my name. Yet, there was a naked poetry in it.
Eve. The first woman. The original sin. Fitting, wasn’t it? Sometimes, she couldn't comprehend her own genius.
She leaned in, dragged his lip between her teeth, bit gently, then rolled her hips harder, faster. She could feel herself starting to fall apart—release coiling tight in her belly like a loaded spring, every thrust building the tension sharper, sharper. It was happening—her body catching fire from the inside, everything spiralling, tightening.
Then—snap. She went splintering apart.
She came with a sound that drained all the colour from her world. A broken gasp, mouth frozen in a silent scream, stifled into his throat as she folded over him. Her body trembled, thighs clamped in, and she clung so tightly around him like she refused to let go. Riding out her waves.
He wasn’t far behind. As if the very sight of her had nudged him forward. A growl—deep, ragged—tore from his chest, face rigid, power intense, eyes hazed over, and with one sharp, helpless thrust, he came too. “Fuck, fuck, fuck,” he panted, buried deep, twitching inside her as his nails digging into her waist like she was the only thing keeping him tethered to earth.
And then—quietude in the afterglow.
No lies, no scams, no exit plan. Two strangers wrapped around each other in the thick fog of sex, sweat, and softening breath.
Eventually, she lifted her head, curls clinging to her cheek. She looked down at him, and despite everything—the ache in her thighs and the sharp echo of release still ringing in her—she smiled a real one.
He reached up, tucked a lock of hair behind her ear, and gave her a smile so goddamn comforting it shouldn’t have existed in this room.
She huffed a little laugh, diverting her weight to graze his softening cock still buried inside her, she leaned in closer—lips ghosting his ear.
“Nice to meet you, Castillo.”
He let out a sound—half laugh, half groan—as his hand slid down to squeeze her ass.
“Pleasure’s mine, Eve.”
‘Eve’ was luxuriating.
There was no better word for it. Luxuriation at its finest. Stretching every nerve and bone in the wake of that mind-blowing orgasm at three in the goddamn morning, she lay draped in hotel linen like it had been tailored for her personally.
She was starving, of course. Ravenous. But not just for food.
She slid out of bed while the stranger—Mr. Big Wallet, Mr. Bigger Cock, Mr. Goddamn Castillo—was still draped across the mattress like a Renaissance nude. Sprawled and golden under the lamplight, limbs askew, a lean hand tucked under his head, a man who knew no one would ever dare disturb him. The picture of leisure. Post-coital smugness facsimiled into art.
Yeah, she would definitely overlook every stinging pain in her demolished muscles to ride him again, why do you ask?
Eventually, she found the lacquered room service menu on the desk and squinted at it, blinking through the haze of sex and triumph. Her instinct was to scan for the cheapest option—buttered toast, maybe, or the $25 fruit bowl. Years of living in the margins didn’t go away with one good fuck.
A wolfish grin crept onto her face. Or maybe it did.
Soon after, she ordered everything she ever denied herself, engaging in a little harmless flirting to get her way. Pancakes with clotted cream. French-style omelettes, salmon on brioche, truffle hash browns, a mimosa and champagne, because why the fuck not? She threw in a side of bacon and a whole carafe of coffee for good measure. Let her fake name live a little.
While she waited, she made herself at home—because that’s what you do when you’ve stolen a beautiful artefact, and no one’s caught you yet. She slipped into the plush hotel robe (absurdly soft, felt like being hugged by a cloud of money), then padded into the marbled bathroom where Bulgari-branded amenities waited like her personal butler’s blessing.
She washed her hair. Twice. Slathered herself in conditioner that smelled like a yacht moored in Monaco, under a majestic shower that almost aerosol-misted water right into her eyes. Then she filled the bottomless, claw-foot porcelain tub to the brim, lemon scented bubbles spilling over. She slipped in with a sigh that reached down to her childhood.
This was the end of the line. This was the life.
The ease of wealth. The promise of solitary comfort. The luxury of not having to think about consequences for once. People who came from nothing—real nothing—didn’t dream in moderation. They didn’t require stability or modest success.
They wanted everything.
Every millionth thread count, every miniature jam jar, every long-legged man with a wallet fat enough to make the world shut up.
And as she soaked in her expensive bath for the night, legs stretched wide and one arm hung lazily over the tub’s edge, breakfast arrived. She insisted on it being wheeled straight into the bathroom in the other guest room, champagne flutes and silver trays and all, so as to not wake Big Dick Castillo slumbering in the master.
Breakfast in the bath. Her version of communion.
She took one bite of pancake, one sip of mimosa, then paused.
Hang on. She didn’t even know his first name. Who was the rich stranger footing the bill?
The thought struck with the odd gravity of a joke that turns into a riddle. She reached for her phone—miraculously still charged—and typed with wet fingers:
🔎 Castillo New York
Top suggestion: Harry Castillo New York
She chewed her pancake thoughtfully. “Harry Cast-ee-yo.” Then pushed her lips up into a prideful smirk. “Found you.”
As easy as that. A few vague words and his whole history spilled out of the phone. She clicked the first, most recent result:
WMAG Exclusive: The Silent Rise of Harry Castillo, Manhattan’s Phantom Power Player
The layout was glossy and over-designed—grayscale cityscapes, oversized type, the whole corporate-chic fantasy. His photo sat dead center, sat in his corner office, hand templed: tall, broad-shouldered, dark eyes infinite, hair tousled, and that fucking smirk. He looked good enough to eat, sure—but there was something off about the Savile Row suit clinging to that lean, lethal frame. The armour didn’t quite fit the man.
And in the profile, no bold title crowned him. No CEO and/or founder. Nothing that screamed self-made grit or startup savant.
Just: Private Equities. Flat. Unapologetic. Take it or leave it.
She snorted into her mimosa. Finance guy. Not what she had in mind.
Private equity—the burgeoning art of buying dying things and gutting them for sport. She was certain he wasn’t a shark. You see, sharks had a purpose. This man was a collector of leverage. He bought struggling companies, debt, political favours, and maybe the occasional dumb woman who lied and pilfered for a living.
Still, she kept reading. Because curiosity, like appetite, always demanded payment.
“I’m not interested in visibility,” Castillo had told WMAG. “The people who talk loudest are usually the least important. Influence is quieter. And I am always thinking about the long game.”
She rolled her eyes. “Prick.”
Yet, the article hilariously went on, and this interviewer did not back down:
“And what is the best thing about being this wealthy?”
She half-expected some PR-friendly answer. Time with his big, affluent family in Antibes. Philanthropy. The freedom to pursue passions, blah blah superyacht. But Harry, naturally, said this:
“I now own WMAG.”
“...Seriously?”
He grinned at me. “I could.”
A full-bodied, white-collar mic drop. She giggled into a layer of bubbles. Smug bastard.
That was Harry Castillo's real currency—believability. He didn’t have to lie; the proposition would suffice. He let people fill in the blanks, and by the time they realised they’d handed him everything, their signatures were already on the dotted line.
Hard to ignore how he sounded like every other wealthy nihilist out there on Wall Street. That tone he took—unshakable, a little too polished—dripped with discretion. She could hear it in her head now, could imagine him saying it between sips of twelve-year-old scotch at a table only lit by a Baccarat lamp.
“I don’t believe in risk for risk’s sake,” he had continued. “Every move should be precise. You don’t bet on fire. You buy the match factory.”
Wow, bravo. She almost clapped. Amusing poetry, Harvard grad, big dick. The man was god's favourite creation in triplicate. She could hardly wait for the leather-bound memoir.
The more she read, the more outlandish it became. Nothing she was new to. He had holdings in everything—media conglomerates, boutique aerospace startups, a vineyard in France that sold wine exclusively to Michelin-starred chefs. Oh, and a minority stake in a European football club, which was probably just code for laundering money through ticket sales. Ted Lasso would have a field day with this fucker.
She scrolled further down and hit a quote from someone unnamed but very impressed:
“Castillo’s power is that you don’t see him coming. He is the storm with no centre. By the time you realise he’s at the table, he already owns the room.”
She tapped her glass against the tub, grinning. “No shit.”
The man outside, Harry Castillo, resupine on his bed like a Greco-Roman mural, the one she’d just ridden to death into the mattress, wasn’t just some rich man.
He was a whole mechanism. A muted weapon clothed in desire. And suddenly she wasn’t sure if she’d seduced him or if she’d walked directly into a carefully placed snare.
Which, of course, was all the more arousing, interesting, tempting, than alarming.
She set the phone by the ledge, reached for a slice of brioche, and thought idly about what her fake, biblical name had said the night before. Eve. The first woman. The fall of Man.
Well, was that not just perfect, she thought and dunked her bread in hollandaise.
At least she picked the right apple.
Later, she watched the sun rise over Manhattan like it was hers.
Legs curled beneath the robe she hadn’t paid for, mimosa in one hand, toast crumbs on the other. Coi Leray murmured through one AirPod, girl-code gospel about how players wear heels now. She bobbed her head to the beat, eyes closed, face tilted toward the morning light. The breeze off the terrace kissed her bare collarbone. Below, the city stirred, unaware that one of its daughters had momentarily won.
“What you know ‛bout livin’ on the top?” her favourite singer chirped. Damn right, people had no damn clue.
The sky was daubed with watercolour—soft roses and scintillating golds bleeding into the steel blue silhouette of the city. She was soaking in every second of it like heat through her bones, feeling a little more than fortunate that she’d stolen this morning. Or maybe rented it by the hour. Either way, it felt like trespassing in heaven.
It was going to be very, very hard to leave.
She heard the thud-thud-thud of his footsteps before she saw him. Padding out from the bedroom, across the polished floors, through the quiet hush of money well-spent. She didn’t open her eyes.
“Did you pig out on the whole menu without me?”
Not a trace of annoyance in that freshly-fucked voice. Not even mockery. It was a soft exhale of disappointment, as if he’d actually been looking forward to an insightful breakfast of champagne and eggs with her.
She grinned, head turned toward the sun. “Oops.”
A soft, amused chuckle. “Are there leftovers at least?”
“Might be toast,” she hummed, “or a fruit bowl.”
You know, the stuff you could score from a lobby continental if you smiled just right.
Then came the shadow, a dawdling eclipse, as he blocked the sun with his body. She sighed out her blunt nuisance, popped one earbud free, and opened her eyes—
Oh, my fuck.
How exactly was a girl supposed to leave when the man she was meant to swindle was standing there like some water-dappled fantasy come to life?
Shower-warm water trickled from his curls like holy beads, trailing down his throat, over that sickeningly perfect chest. The towel around his hips hung low and loose—threatening virtue, daring gravity. In daylight, he looked even more expensive. Someone had carved him out of dark gold and complacency. Was the sun doing that on purpose, playing him out in slow motion and amber hues of a porn film?
Her eyes dragged over him like fingers. Simply put on this Earth to be appreciated, wasn't he?
The worst part was that he knew exactly what he looked like.
He leaned in, bracing one hand by her head, the other hooking a finger into the delicate strap of her black slip. “Leaving without a kiss?”
She tilted her chin. “I gave you plenty last night.”
“Too bad I’m insatiable,” he murmured—and claimed her.
This special kiss was slower, curled around her throat like silk. Luxurious. Marvis toothpaste and vices. He had nothing left to prove now, just him to taste again. His hand cradled her jaw, thumb brushing just under her lip as if establishing her identity. Ha, good luck with that. While she let herself melt into it, one last time, and her fingers found his damp curls, twining. Tugging. Greedy.
When he finally let go, it was with a kiss to her nose—infuriatingly domestic. Tucking affection between stolen moments.
She patted his chest—twice, lightly, how one might close a book—and moved to slip her stilettos back on from where they waited obediently by the lounger.
“I better hoof it before the cops show up,” she muttered, bending to fasten them back on with still-shaky fingers.
He placed his hands on his hips, the towel still miraculously hitched there with Popeye's knot. “Inexpedient. You know I have security, right?”
“That needs replacing, yes.”
His mouth twitched, but his eyes stayed trained on her. Calculating. Curious. “You don’t do this often.”
She arched a brow, slipping on a heel. “Sex? Or talking to billionaires in towels?”
“You don’t get caught. But you’re not greedy either, you take just enough.”
She gave him her best grin—sharp, blameless. “I’m light-fingered with taste.”
“I know your play now.”
She paused mid-buckle, scoffing. “From a single fuck? Please, you do not.”
He said it, simple and unambiguous—“Oh, no. In fact, I know your type. You only bite when you’re starving.”
The words dropped like a pin in a vault.
And her stomach did that thing again—flipped traitorously, like it forgot what team she was playing for. Even if it showed on her face, she masked it by standing too quickly, balancing all that tension in her calves and those goddamn heels. One foot out the door was always her secret weapon.
“You’ve downgraded in a span of six hours,” he observed, clicking his tongue. “Lifting Chopards to swiping complimentary toiletries.”
But her hand, buried in the folds of her coat, curled tighter around the little Bulgari amenity kit she’d palmed like a lifeline. Conditioner, soap, even the shower cap—luxuries she didn’t demand, but had taken anyway. A permission to remember.
She kept her eyes forward, chin tilted, expression carved from cool marble. Still, her fingers gripped that miniature bottle like it might explain her—or what she refused to say out loud.
The guilt was feather-light. The habit was heavier.
Behind her, he shifted. She could feel the heat of him before she turned—wet curls, water beading off his collarbones, barefoot and beautiful, and still half a head taller.
She pivoted smoothly, letting the smile break across her lips. Blinding, forged in the alleyways of survival.
With a theatrical grace, she reached into her coat and produced the bag and set it down on the nearest lounger like an offering at a goddamn altar.
“I’m sentimental,” she said airily, flipping her hair over the coat. “Didn’t want to take anything I couldn’t fence.”
He raised a brow. “I would’ve bought you a crate full if you said it.”
She snorted. “Then you’d expect a thank-you note. Maybe a handwritten apology for bruising your ego.”
“You think this is about ego?”
She was already walking, all legs and larceny, her heels clicking a decisive farewell toward the suite’s door. “It’s always about ego, honey. Yours, mine, New York’s.”
He let her go, for only a beat before: “So that’s it? You’re leaving me here?”
She didn’t answer.
“Empty-handed?” he added, trying for levity. But there was an edge in it. Uncertain, almost hurt.
That stopped her.
She turned slowly, heel catching the light. Her gaze roamed down his body—shoulders to smirk at the towel and his hands. She let her lips curl with the final review of her appraisal. A pause, then:
“No, Harry. You are.”
He blinked, stunned. Then laughed that deep, throaty laugh—quick, surprised, maybe even impressed.
“Wait... you stalked me?”
She was already halfway through the door, but her voice reached him in a whiff of perfume—soft, sweet, a last kiss goodbye. “I did. I'm largely underwhelmed.”
“Offence largely taken—!”
But the door snapped shut with the crisp punctuation of a woman who’d just stolen back her power.
The hallway waited, quiet and cooled by central air and generational wealth. The marble underfoot gleamed. Her heels made the kind of sound that said: I finally belong here. Or at least—I dare you to say I don’t.
She walked with no urgency, each step a slow, delicious exhale. No alarms or shouting, chock-full with expensive silence that forgave indulgence.
At the elevator, she pressed the button. Waited. Tucked her hands into the silk-lined pockets of the fur coat, not out of cold, but because she liked the feel of the significance of it in her palm. That familiar shape—warm now against her skin.
The big fucking emerald ring.
It was there. A flicker of green fire between her fingers. She wasn’t even sure when she'd slipped it off him. Maybe when he trusted her enough to fall asleep or when he was deep inside her, and her mind had gone static. Maybe it had just… found her. It was fate.
The elevator dinged.
Without missing a beat, she stepped inside. Her reflection caught in the gold-trimmed mirror: hair wild and haloed, eyes glowing with triumph from an utterly bare face. The hotel robe had vanished; now it was the satin slip, the coat, the heels. Chaos in elegance.
And there it was—on her finger.
A perfect, vulgar gleam. Standing there like a question mark that didn’t need answering.
The doors started to close.
But a hand blocked them. Big, firm, wet. A horny reminder of last night.
They hurtled open again—and there her once target was.
Still in the goddamn towel. Dripping. Curls unruly. A single drop of water slid down his chest like it was tracing a signature. Harry’s hand braced the elevator door open, wide and planted, and his breath came just a little too fast for a man who pretended he never chased.
They just stared at each other.
She raised a brow. “Forgot your goodbye monologue?”
His lips curled lazily. “Forgot to ask if you’re free tonight.”
Not that the inquiry stopped her—he just asked as if this were a boardroom, and she was a merger he didn’t want to lose.
Her grin betrayed itself gloriously—and she had to bite her lip to contain the whole thing. The emerald was warm between her fingers now, hidden in the fur lining of her coat. Poor little rich boy didn’t know she’d swiped the emerald off his finger while he was too busy trying to memorise the shape of her name on his tongue. It was already cooling against her skin like a private joke.
“I don’t do second showings,” she said, tilting her head. “I believe in leaving them wanting.”
“No sex,” he replied smoothly. “Just dinner. A civilised meal. Wine optional. Clothes preferred.”
She took a step forward. Her heels whispered across the carpet like a signature. Her palm landed gently on his cheek, thumb trailing down the line of his jaw like she was testing for flaws in the marble.
“Dinner,” she repeated. “While you stare at the cutlery to see what I pocket?”
His mouth twitched, not quite a smile. Those wondrous gears in his head turned where she could see them. “If it makes you feel better, sweetheart, I’ll buy the whole restaurant for one night. Want the chef? You can have them. Kitchen, too.”
She gave a soft snort. “Are you always this desperate to feed your dates?”
He smiled, unapologetic. “I like investing in volatile assets.”
Her eyes narrowed—amused. “And I like playing with over-leveraged men.”
He leaned in slightly, water glinting off his collarbone like jewellery. “Then this should be fun.”
She let her hand drop like a curtain call, but there was a hum beneath the restraint. “I’m not a return on investment.”
“Didn’t say I expected one.”
The elevator pinged—doors trying to slide shut again. He caught it reflexively, fingers splayed, blocking the sensors. He tilted his head knowingly, waiting for her.
She let a soft, exhilarated breath leave her. “Jesus, you’re persistent.”
“I’m intrigued.”
“Dangerous word.”
“Only if you’re worth the damage.” He thinned his eyes. “C'mon, try your luck a little more.”
That made her laugh—head tipped back, shoulders relaxed.
As the impatient elevator doors began to close again, she tapped the emerald glinting between her fingers against the rail once, a sharp clink, like a period at the end of a sentence. She let the metal sing.
A signature. A thief’s version of a calling card.
There was a fascination about them that felt depraved. Poetical. He knew the danger, and that she wasn’t just sharp around the edges—she was serrated. Unreliable. She was halfway to detonation, and still he lingered—like a man who’d light her twice, just to watch the world go up with her.
That was the thing about men like Harry Castillo. Chaos was their muse, especially when it walked like sin and smirked like it knew them.
The doors finally began to slide again with no interference.
“I'll find you, Eve,” Harry promised.
She blew him a kiss with two fingers, let her tongue click in pity. “Poor guy,” she whispered, turning her head the second before the elevator doors kissed closed.
