The Arrangement - A Harry Castillo Fanfic Masterlist
Sheâs the lie he hired. Heâs the truth she wasnât ready for.
After a bitter breakup with Lucy, 50-year-old private equity billionaire, Harry Castillo, isnât 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 someoneâs fantasy girlfriend off the clock.
But Harry makes you an offer you canât 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 isnât trying to fix anyone; in fact, heâs the one who might be broken, and he doesnât even realise it.
Warnings: đ 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 theyâre not, Soft power games, Sharp banter + late-night vulnerability, Trust issues + protective instincts
Pretty Woman inspired but make it jaded playlist đś
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Iâm thinking⌠Harry and you have been a couple for a few years now. Maybe engaged? Somethingâs on your mind but you find it hard to open up to him because heâs been busy and you donât wanna burden him. But then he found out you opened up to a friend and heâs part jealous, part hurt, part concerned, part confused. He then just reassures you on your feelings and your relationship and his role as your man.
The rest of the details, Iâll leave that to you. Smut or not, also up to you. Just thought about it because I need a Harry pick me up!
Together - One Shot, Harry Castillo Fanfic
Warnings : fluff, so sweet your teeth will rot.
The apartment was quiet except for the soft hum of the city outside. You were curled on the sofa with a magazine you hadnât really read, the diamond on your finger glinting every time you turned a page. It shouldâve filled you with nothing but joy, that perfect reminder of the life you were about to start with Harry, but lately it felt heavy.
Every day brought another decision about the wedding. Flowers, menus, seating charts, family politics. It was supposed to be exciting, magical even, but instead it left you tense and drained. Each choice felt like a test you could fail - as if one wrong shade of table linen might disappoint everyone you loved.
Meanwhile Harry was already drowning in late nights, constant calls, impossible meetings that stretched into the early hours. You would watch him loosen his tie after midnight, shoulders heavy, and the last thing you wanted was to pile your own worries on top of his. So you smiled, brushed off the panic, and told yourself you could carry it alone.
But it crept in anyway. The way you picked at your food instead of eating. The way your phone buzzed with another message from the planner and your jaw tightened before you could stop it. The way you lay awake beside him, staring at the ceiling, mind spinning through a carousel of decisions you hadnât made.
Harry noticed. Of course he did. He always noticed. Heâd reach for your hand across the sheets, or tug you gently against his chest, murmuring for you to sleep. Sometimes you managed a soft âIâm fine.â Sometimes you didnât trust your voice at all.
And all the while, the list grew longer.
So youâd vented to Claire. Your best friend of 20 years. Just once. Over coffee, when the weight of the endless lists and the tug-of-war between families had pressed too hard against your ribs.
You hadnât meant to unload - sheâd simply asked how the planning was going, and before you could stop yourself, the words spilled out. How the florist kept sending invoices that didnât match what youâd agreed on. How your mom wanted to invite cousins you barely knew. How the planner acted like linen samples were matters of national security.
Claire had listened, nodding in that steady way she had, her hand resting over yours on the table. âYou know, it doesnât have to be this hard,â sheâd said gently. âHarryâs part of this too. You donât need to do it all by yourself.â
The reminder landed like a pebble in your chest, rippling outward. Youâd brushed it off with a smile, promising youâd figure it out, but later that night the echo of her words followed you into bed.
Because she was right. You didnât want to be the kind of partner who crumbled silently under the weight of things Harry hadnât even been given the chance to carry. But he came home so late, so exhausted, and you hated the thought of being another demand on his time. So you swallowed it back down, even as the pressure built.
When the front door opened earlier than expected, you looked up. Harry stepped in, jacket in hand, tie hanging loose. He looked tired, but when his gaze found you, there was something sharper there.
âHey,â you said softly, closing the magazine.
âHey.â His voice was low, careful. He went through the usual motions - keys on the counter, jacket hung up - but when he came back, two glasses of wine in hand, he didnât sit casually. He sat forward, elbows on his knees, eyes locked on yours.
âI saw Claire today.â
Your stomach dropped. âOh?â
âShe mentioned the wedding. That youâve been overwhelmed.â His tone wasnât cruel, but it was edged. âYou never said anything to me.â
Your throat tightened. âHarry, I didnât mean...â
âYou told her you feel like itâs too much. Like youâre suffocating.â His jaw flexed. âBut not me.â
The hurt in his voice was worse than anger. It was disappointment. You hurried to explain. âYouâve been so busy. Every time I wanted to bring it up, you were buried in work or exhausted. It felt selfish to throw⌠flowers and guest lists on top of that.â
âSelfish,â he repeated, shaking his head. He leaned closer, catching your chin, tilting your face toward him. âSweetheart, this isnât about flowers. This is about us. About building our life together. And you thought I wouldnât want to hear it?â
Your eyes stung. âI didnât want to be another weight on your shoulders.â
His gaze softened, but his grip didnât waver. âYouâre not a weight. Youâre the reason I carry everything else. Donât you get that?â His thumb brushed along your jaw. âI canât stand the thought of someone else being the one you turn to when it should always be me.â
You swallowed. âI just didnât want to make things harder.â
âBaby,â he said gently, âyouâre not capable of that. The only thing that makes things harder is thinking you donât trust me enough to let me in.â
That cracked something open in you. A tear slipped free, and he kissed it away before you could speak. His arms came around you, pulling you into his chest, tucking your head under his chin. For a long while, he just held you. The tension youâd been carrying seemed to melt under his steady hands, the rise and fall of his chest grounding you.
âListen to me,â he murmured against your hair. âThis wedding doesnât mean anything if youâre carrying it all alone. I donât care if itâs flower arrangements or the end of the world. You bring it to me. Always.â
You nodded against his shirt, your voice muffled. âOkay. I promise.â
âGood,â he whispered, kissing the top of your head. âBecause youâre not in this alone. You never will be.â
*****
Later, he scooped you up as if you weighed nothing and carried you to the bathroom. He set you on the counter, turned on the taps, and began running a warm bath. Steam filled the room as he moved around with quiet purpose, sleeves rolled up, tie gone.
When he returned to you, his hands rested on your thighs, his expression softening into something tender. âYouâre going to sit in there and tell me everything thatâs been spinning in that pretty head of yours. Every worry, every detail. And Iâll remind you that none of it is bigger than us.â
You laughed wetly, swiping at your eyes. âYou donât want to hear me debate roses versus peonies.â
âI want to hear everything,â he said simply, brushing your engagement ring with his thumb. âBecause itâs ours. And because youâre mine.â
When he finally settled on the edge of the bath, his presence steady and grounding, his hands reached for yours where they rested on the curve of your stomach. The ring gleamed in the rising steam, catching the soft light.
âYouâre going to be my wife,â he whispered, leaning close, lips brushing your damp hair. âAnd Iâll be damned if you ever think you have to carry any of this alone.â
And in the warmth of his words, for the first time in weeks, you let yourself believe it.
For a while, the only sound was the water and the soft rhythm of his breathing. Then he murmured, lips brushing your damp hair, âAlright. Start talking. Whatâs been eating at you?â
You hesitated, fingers tracing circles on the surface of the water. âEverything feels⌠big. Every decision feels like if I get it wrong, Iâll ruin the day. And everyone has an opinion. My mom wants something formal, your mother keeps hinting about guest lists, the planner keeps sending me mood boards I donât even likeâŚâ You exhaled. âItâs too much.â
Harry kissed the side of your head. âBaby, no oneâs going to remember if the napkins were ivory or cream. Theyâll remember you walking down that aisle. Theyâll remember you saying yes. Thatâs it.â
You smiled faintly. âEasy for you to say. Youâre not being asked to pick between six kinds of roses.â
âThen donât.â His tone was matter-of-fact, but his hand rubbed lazy circles over your arm. âYou pick one you like, and thatâs the end of it. You donât owe anyone else a committee vote.â
âYou donât care what flowers we have?â
âI care that youâre not tearing yourself apart over them,â he said simply. âThough, if you ask meâŚâ His mouth curved in a rare, boyish grin. âPeonies sound like something out of a fairytale. Big, ridiculous, dramatic. Perfect for you.â
You laughed, the sound bubbling out before you could stop it. âYouâre not supposed to be good at this.â
âIâm good at everything when it comes to you,â he said, with enough mock arrogance to make you laugh harder. Then he kissed your temple again, softer this time. âWe could get married in a field with dandelions, and Iâd still think it was the most beautiful day of my life.â
The knot in your chest eased a little more. You leaned back fully, soaking in the comfort of the warm water and Harry beside you. âI just donât want to let you down. I want it to be perfect.â
His arms tightened around you, his voice low and steady. âYou could walk down that aisle barefoot, in jeans, with nothing but me waiting at the end and it would be perfect. Because itâs us. Thatâs all I want.â
Your throat ached at the sincerity in his tone. You learned forward in the water, reaching over the tub to kiss him. He met you halfway, slow and certain, as if sealing the words heâd just given you.
When you pulled back, he rested his forehead against yours. âSo. No more bottling it up. You tell me when somethingâs too heavy. We carry it together.â
âTogether,â you whispered.
His smile was small but sure, the kind that reached his eyes. âThatâs my girl.â
You let the warmth of the water and the steadiness of his arms wash the worry out of you, realizing for the first time in weeks that maybe it really could be simple because you werenât doing it alone.
Warnings: jealousy, tooth rotting fluff, importance of family.
The penthouse had grown too quiet since Harry had gone back to work. Two months with the baby meant exhaustion, of course, but it also meant youâd grown used to his steady presence - the way heâd change a diaper without complaint, or the way heâd whisper goodnight to both you and the baby before drifting off beside you.
Now, mornings were marked by the sound of his tie being knotted, the scrape of leather soles on the floor, his brief kiss on your hair. Then he was gone, and you were left to fill the silence with lullabies and soft rocking.
That afternoon, restless and craving his company, you bundled the baby into her carrier and decided to surprise him at his office before heading to a friendâs for coffee.
The lobby of his office was sleek, filled with people who looked untouched by sleepless nights or milk stains. You smoothed your hair back, adjusting the carrier straps, nerves prickling under your skin. You hadn't been out properly since the birth, so putting on proper clothes and some make up felt like a novelty but also, refreshing.
When the elevator doors slid open onto Harryâs floor, your steps slowed. His voice carried, warm and familiar. You turned the corner.... and saw her.
The new secretary - Nancy, you thought her name was, if memory served you right. She was perched on the edge of his desk, too close, her laughter low and deliberate. A pencil skirt clung to her slim figure, paired with a silk blouse that dipped just enough to suggest she dressed for attention rather than work. Glossy brunette hair fell in loose, calculated waves around her shoulders, the kind of salon-polished style that never moved out of place. Her lips were painted a deep, deliberate red, the shade designed to be noticed, and her manicured hand - nails filed to sharp points - brushed his arm as if it belonged there. She carried herself like someone who knew she was being watched, who enjoyed it, who expected it.
Your breath caught, chest aching as you looked down at your choice of clothes: jeans and an oversized white shirt, worn in the hope they might conceal the gentle swell that remained at your middle.
Before doubt could fester, Harry looked up and everything about him changed. His whole face lit up, eyes softening in an instant. âThereâs my girls,â he murmured, standing so quickly his chair rolled back. He crossed the room in long strides, ignoring Nancy entirely, and pressed a kiss to your temple.
âBrought me the best surprise,â he said, leaning down to brush a finger gently over the babyâs cheek. His grin was boyish, proud. âSheâs getting bigger every day.â
Nancy's expression soured in the corner of your eye, but Harry didnât even look her way. He was too wrapped up in you, in your daughter. And for a while, that was enough to soothe the unease in your chest.
*****
Weeks passed. The baby grew heavier in your arms, her coos filling the apartment with new music. But the unease never fully left.
One afternoon, you dropped by Harryâs office again with your daughter. He hadnât expected you, and you were half a step away from knocking on his door when you froze. Voices carried through the crack.
It was her.
âI donât know how sheâs managed to keep him interested,â Nancy said, tone sharp and dripping with disdain. âShe hasnât even lost the baby weight. Men like Harry donât stay when things change. Heâll get bored sooner or later.â
The words hit like a blow. Your breath stilled in your throat. Tears pricking the corners of your eyes.
You turned, leaving before Harry could see you, your heart pounding with shame and fear. By the time you reached the elevator, hot tears blurred your vision.
At home, the words replayed like poison. She hasnât even lost the baby weight⌠He wonât stay.
That night, Harry kissed your shoulder as he climbed into bed. You tensed. He noticed. Of course he noticed.
âWhatâs wrong?â he murmured, voice low in the dark.
âNothing,â you lied, curling away.
It wasnât until one late night, weeks later, that Harry pressed.
But over the coming weeks, the distance began to grow.
You were in bed, his hand resting on your hip, his mouth trailing slow kisses down your shoulder. But instead of melting into him like you usually did, you stiffened, mind elsewhere.
He stopped, pulling back. âSweetheart,â he said softly, âyouâve been miles away from me for weeks. Tell me whatâs going on.â
You shook your head, but his thumb brushed your cheek, catching the tears you hadnât meant to shed.
"Please baby, I can't do anything to help you if I don't know what's going on in that pretty head of yours."
Harryâs face hardened, but not at you.
âI heard her,â you whispered, voice breaking. âNancy. She said I havenât lost the baby weight. That youâd⌠that youâd leave me. And maybe sheâs right. You deserve someone who...who doesnât look like this, who isnât tired all the time, who isnât....â
âDonât,â he interrupted sharply. Then his tone gentled, his hands cradling your face. âDonât you dare finish that sentence.â
Your lip trembled. He leaned in closer, eyes blazing.
âYou are the love of my life,â he said, every word deliberate. âYou gave me our daughter. You think Iâd trade the most beautiful woman Iâve ever known - the strongest, the bravest - for someone who canât hold a candle to you? Not in a million lifetimes.â
Tears spilled hot down your cheeks.
âHarryâŚâ
âShh,â he whispered.
He kissed you then - not a peck, but a deep, anchoring kiss. His lips moved slowly, coaxing, his tongue teasing the edge of your mouth until you opened for him. The way he kissed you made you feel like you were the only thing he wanted in the world.
When he pulled back, his thumb traced the corner of your lips. âLie back for me.â His voice was a low command, but gentle.
You lay back on the bed, the cool silk sheets whispering against your skin. He untied the sash of your robe slowly, as if unwrapping something precious. The fabric slipped apart and he just⌠looked. His gaze wasnât distant; it was hungry and tender at the same time.
âEvery inch of you is mine,â he murmured, bending to kiss the hollow of your throat. His lips dragged slowly along your collarbone, then down to the curve of your breast. His hand followed, cupping you, thumb brushing your nipple until it hardened. He took it into his mouth, sucking lightly, tongue swirling in lazy circles, making your back arch off the bed.
âHarryâŚâ you gasped, fingers sliding into his hair.
âShh,â he whispered against your skin, moving to the other breast, giving it the same slow, teasing worship. âYouâre perfect. Youâre beautiful. Donât ever doubt it.â
His hand slid down your waist, pausing at the faint marks on your stomach. He bent and pressed kisses there, reverent, his voice rough. âProof you gave me our daughter,â he said. âMost beautiful thing youâve ever done.â
By the time his mouth reached the inside of your thigh, your breathing was shallow. He kissed up one leg, then the other, slow and deliberate, until you were trembling. When he finally touched his tongue to you, it was feather-light at first, teasing, coaxing. He licked a long, slow stroke up your center, then circled gently, again and again, until you moaned softly, hips lifting off the bed.
âLook at me,â he murmured, eyes glinting up at you. âI want to see you.â
You obeyed, meeting his gaze, and the intensity of it made you shudder. He kept his eyes on yours as he licked you again, deeper now, his tongue pressing and flicking, his hands holding your thighs open. Every motion was slow and sure, a rhythm meant to worship, not rush.
When you were trembling under his mouth, on the edge of release, he finally slid up your body again, kissing you deeply so you could taste yourself on his lips. Then he pressed himself against you, hard and ready, but didnât thrust yet - he just rubbed slowly along your slick folds, teasing, until you were whispering his name.
He slid into you slowly, inch by inch, filling you completely. You gasped, nails digging into his back, overwhelmed by the fullness of him. He stayed there, forehead against yours, lips brushing yours, murmuring, âIâm here. Iâm not going anywhere.â
Then he began to move - slow, deep strokes, each one measured, his hips rolling into yours. His hands framed your face, thumbs brushing away the tears on your cheeks. âOnly me,â he whispered between kisses. âAlways me. Youâre perfect. God, you feel so goodâŚâ
You wrapped your legs around his waist, pulling him deeper, meeting each slow thrust. He kissed you again and again, murmuring your name, telling you you were beautiful, his, everything heâd ever wanted.
When you came, it was with a soft cry, your body tightening around him, your breath catching in your throat. He followed moments later, groaning against your neck, holding you close as he pulsed inside you.
He stayed inside you, chest pressed to yours, lips brushing your temple. âDo you believe me now?â he asked softly, his voice rough with emotion.
âYes,â you whispered, tears slipping free. âI believe you.â
He kissed you then, slow and tender. âGood. Because Iâll keep proving it until you never doubt it again.â
He eased out of you gently, but didnât let you go. He gathered you against his chest, one hand stroking your hair, the other tracing circles over your hip. Outside the glass walls, the city sparkled, but here in the dim light of the penthouse, it was just the two of you: his power, his wealth, all meaningless except for this moment, with you in his arms.
*****
The company gala was a world of glitter and polishâgold chandeliers spilling warm light over the marble floor, the hum of strings filling the space, waiters weaving through with trays of champagne. Harry stood at your side like he always did in public: composed, poised, his hand steady at the small of your back. He didnât grip, didnât clingâjust guided, a constant presence that grounded you in the swirl of opulence.
You were smiling at a board memberâs wife when she appeared. Nancy. Her heels clicked against the marble, her posture confident, her smile designed for Harry alone. You stiffened almost instinctively, remembering her words that had haunted you for weeks.
âMr. Castillo,â she said smoothly, ignoring you. Her hand brushed the sleeve of his tuxedo as though she had the right. âAs always, you command the room.â
You waited for Harry to draw back, for irritation to flare. But instead, he simply regarded her. Cool, unreadable. His expression didnât flicker - not warmth, not anger. Just control. âNancy,â he said evenly. âI didnât expect you here tonight. I thought you said work events were not your scene.â
Her eyes flicked to you and back. âWell, I wanted to lend my support. You know, no one speaks about you the way I do - I make sure everyone knows how indispensable you are.â
Something in your chest tightened. The words stung, not because you believed them, but because you remembered too clearly the cruel whispers sheâd aimed at you - that Harry would leave, that you werenât enough anymore. For a moment, you felt the sting of that doubt again.
Harryâs jaw shifted, so subtle only you noticed, but his voice remained calm and clear. âYou seem to be mistaken,â he said, every syllable precise. âYour position was to support my work, not my reputation. And certainly not to spread gossip about my wife.â
The air shifted. People nearby slowed, listening, their conversations fading. You felt the weight of eyes around you, heat creeping into your cheeks. His arm not leaving your waist once.
Nancy faltered, her confidence slipping. âI...I donât know what you mean...â
But Harryâs tone didnât waver. âI will not tolerate disrespect in my company. To my wife, or to my family. You are relieved of your position, effective immediately. Security will escort you out, and your things will be returned in the morning.â
It wasnât loud, it wasnât cruel...it was final. A command delivered with the certainty of a man used to his word being law.
Nancy flushed crimson, her mouth opening, closing, as though she might argue. But one glance at Harryâs steady eyes silenced her. She turned sharply, heels clattering against the marble as she disappeared into the crowd.
You let out a breath you hadnât realized you were holding. Your heart pounded, caught between nerves and a sudden flood of relief. He had done it - in public, with perfect composure. For you. For your little family.
Harry didnât watch her go. Instead, he adjusted his cufflink as if brushing dust from his sleeve, and then he turned back to you. The edges of his mouth softened, a quiet warmth slipping through the controlled façade.
âApologies for the interruption,â he murmured, his voice low, meant only for you. âIt wonât happen again.â
Something in your throat tightened, emotions threatening to spill over. You werenât sure if you wanted to cry or kiss him. Your hand found his arm instinctively, grounding yourself in the man who had just defended you with such calm certainty.
The crowd began to murmur again, the moment already folding back into the night, but you couldnât quite stop staring at him. Not the billionaire, not the untouchable man everyone else sawâbut your husband. The man who had made it absolutely clear, to everyone and to you, that you were not replaceable.
When he offered you his arm again, it was steady, deliberate. He guided you forward as though the interruption had never happened, but his thumb brushed the back of your hand onceâsmall, secret reassurance that was only for you.
The car door shut with a soft thud, sealing the two of you away from the hum of the gala. The city lights blurred past the tinted windows, but all you could feel was the pounding in your chest.
Harry sat beside you, composed as ever, one leg crossed, hand resting easily on his knee. To anyone else, he looked like nothing had happened, like firing a woman in front of half of his company was just another item on his agenda.
But you couldnât stop replaying it. The hush of the crowd. The way heâd spoken, calm but absolute. The way everyone had turned to stare.
Finally, you exhaled, turning toward him. âHarry⌠you didnât have to do that. Not like that. In front of everyone.â Your voice was soft, a little shaky. You meant it - part of you still couldnât believe heâd done it so openly, for you.
His eyes shifted to you, steady and unyielding. âYes, I did.â
You blinked, startled by the firmness in his tone. He reached across, his fingers lacing through yours. His grip wasnât tight, it was grounding, deliberate.
âYou think I shouldâve let it slide?â he asked quietly. âIgnored the way she spoke about you? Pretended it didnât reach me? Thatâs not how I run my company. Thatâs not how I run my life.â
You swallowed, your chest aching. âBut⌠it was public. People will talk.â
âThey were already talking,â he countered smoothly. âShe was talking. Whispering poison where she thought I wouldnât hear. If I corrected her behind closed doors, sheâd still walk out of that room smiling, still believing she could get away with it. This wayâŚâ His thumb brushed the back of your hand, controlled, precise. ââŚshe knows. Everyone knows. No one questions where I stand.â
You bit your lip, tears prickling at your eyes. âBut Harry, you donât have to defend me....â
That broke his composure for just a moment. His jaw set, his eyes sharpening. âI donât have to,â he agreed softly, almost sharply. âI choose to. Always.â
Your throat tightened, and you looked away, overwhelmed. But he shifted closer, his hand leaving yours only to tilt your chin back to him. His voice softened, but the steel remained underneath.
âShe disrespected my wife. The mother of my child. You are the one thing in this world I will never allow to be diminished. Not in whispers. Not in public. Not ever.â
Your breath caught, tears spilling before you could stop them. You whispered, âHarryâŚâ
He leaned in, kissed the corner of your mouth gently - not possession, not spectacle, but assurance. Then he rested his forehead against yours, his voice low enough that only you could hear.
âDonât thank me. Donât tell me I didnât have to. It was necessary. And Iâd do it again tomorrow if I had to.â
The car rolled smoothly through the city, but in that cocoon of quiet, the truth settled into you: he hadnât done it to make a scene. He had done it for you. And not because he had to but because it was his choice. His promise.
âNow, letâs see our little girl before she lets the whole city know sheâs awake."
Thank you @kellyxo1 for this great prompt! I loved writing it and I hope you all loved reading it! đâ¨
Warnings: 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.
The Arrangement Masterlist
An angel's smile is what you sell, you promised me heaven then put me through hell - Bon Jovi.
Youâre not supposed to wait in the lobby.
Technically, you're meant to meet in the car or in the bar or at some anonymous hotel where no one asks for your last name and everyone pretends this is just coincidence. But this clientâs assistant was specific - âHeâll meet you in the penthouse. Not before. Donât be late.â So you took the private elevator like a ghost, let the doorman scan you like contraband, and now youâre perched on the arm of a velvet chair that probably costs more than your entire rent history combined.
You cross your legs slowly, deliberately. The slit in your dress falls open just enough to say yes, I know what Iâm doing, but not enough to look desperate. You learned the balance years ago.
The lobby smells like money. Like eucalyptus, old scotch, and silence. The kind of quiet that comes with wealth so obscene it doesnât need to prove itself anymore. You glance at your reflection in the dark glass of the window: red lips, long lashes, collarbones dusted in shimmer. You look expensive tonight and not just because of the dress.
Then you hear it, the soft chime of the elevator.
You donât stand. You wait.
He steps out like he owns the whole building. Maybe he does. Tailored black tuxedo. Cufflinks that probably have a backstory. Hair slightly mussed, like heâs been running his hands through it in frustration. Not young. Not old. Late forties, maybe. Sharp jaw, tired eyes. Handsome. Odd. They never usually are.
You know men like him or at least, you know the version they show the world.
You watch him clock you in an instant. You can almost feel it: his brain filing you under unexpected, then evaluating, then deciding not to react. He walks past you toward the private bar like you're just another piece of expensive furniture.
âRough night?â you ask, just loud enough to land.
He stops.
Turns back.
He sees you. Not lounging. Not waiting. Posed. Composed. All long legs, a slit of red silk, and confidence that didnât ask for permission. You looked like you belonged in a perfume ad or a scandal - somewhere curated, somewhere sharp.
He registered you in stages.
The dress first - off-the-shoulder, effortless. Then the mouth - painted red, curved like you knew something he didnât. Then the eyes - watching him with the kind of calm that made him feel like he was the one being bought. You were young, late twenties he would pin you at. Not what he was looking for, but for what he was looking for, he wasn't going to be fussy.
And now heâs looking. Really looking. Assessing. You hold his gaze and smile - a half-smile, the kind that says Iâm not nervous, but I am curious.
He doesnât smile back. âThat obvious?â
You shrug, shifting slightly on the chair. âYou look like you just escaped a fundraiser and a firing squad.â
That earns a ghost of a smirk. He steps toward you. âWhich one are you?â
You tilt your head. âExcuse me?â
âThe fundraiser or the firing squad?â
âIâm the intermission,â you say smoothly. Then you uncross your legs and rise, slow, measured. You gave your name.
He watches you like heâs solving a riddle. âYou donât look like one.â
You arch a brow. âAnd what should I look like?â
He doesnât answer. Just gestures toward the bar. âDrink?â
You nod. âIâll have whatever youâre having.â
He pours two fingers of something that probably costs more than your weekly rate and hands it to you without ceremony. No toast. No fake charm.
The glass is heavy in your hand. So is the silence that follows.
âHarry Castillo,â he says eventually. Like it matters. Like you donât already know exactly who he is.
You let the name hang there, then give a small, ironic smile. âNice to meet you, Harry Castillo.â
You donât ask him why he called. You never ask.
But part of you wonders.
Not why he hired you - men like him always want a distraction, a clean slate, something that wonât end up on Page Six. But why now. Why tonight. Why you.
He doesnât make a move. Doesnât leer. Doesnât even pretend to flirt.
He just leans against the bar, whiskey in hand, and says, âDo you want the short version or the long version?â
You take a sip. Let it burn a little. âStart with the short.â
âI need someone on my arm tomorrow night, maybe the month. Galas. Dinners. PR damage control.â
You raise a brow. âA girlfriend experience.â
âA convincing one.â
You swirl the drink, pretending to consider. But you already know your answer.
âHow convincing are we talking?â you ask.
He meets your gaze again. His eyes are dark, but not cold. Just... quiet. Like heâs been through enough not to waste energy.
âYou wear what you want. Say what you want. Just look like you want to be there.â A pause. âAnd donât lie to me.â
You smile at that. âWhat makes you think Iâm a liar?â
He finishes his drink in one measured swallow.
âI donât,â he says.
And for the first time tonight, you think this job might actually be interesting.
You donât usually stay this long. Most clients like to pretend thereâs a rush. They fumble through their introductions, rush the champagne, get to the point. Youâre a service. A transaction. The longer it takes, the more it costs and the more real it starts to feel.
But this one⌠Harry Castillo⌠he doesnât move like a man trying to fill a void. He moves like heâs protecting one.
You lean back against the marble edge of the bar, letting the silence stretch again. Heâs watching you, still and composed, the kind of stillness that comes from years of controlling rooms, markets, people.
âSo,â you say lightly, âyouâre not looking for sex.â
He doesnât flinch. âIâm not looking to lie to myself.â
That earns him a faint smile from you - a real one. Honest. Dry.
âGood start,â you murmur. âBut hereâs the thing - if you want a girlfriend for longer than a night, youâll need more than just heels and a pretty face.â
His brow lifts. âWhat do you charge for personality?â
You tap a finger against your glass. âDouble.â
He almost - almost - smiles.
Then he steps closer, slow and unhurried, setting his empty glass down beside yours. You can smell his cologne now - something woodsy and clean, with a bite underneath.
âIâm not going to sleep with you,â he says calmly, and itâs not an insult. Itâs a statement of terms. âNot unless you want to.â
You tilt your head. âIs that your way of being noble?â
âNo. Itâs my way of not confusing boundaries.â A pause. âMine. Or yours.â
You study him for a beat. Itâs not the first time a manâs drawn a line. But it is the first time you believe one might actually stick to it.
âSo this is what you want?â you ask. âA fake girlfriend. For a month. In public. Private dinners, parties, events.â
âI'll see how you do tomorrow night. Then we can discuss the rest later.â
âYou want me to dress the part. Charm your board. Laugh at your jokes.â
âI donât need you to laugh,â he says. âJust show up.â
You consider him - the directness, the tiredness he doesnât bother hiding, the sliver of something under all that restraint. Loneliness, maybe. Or something older.
âIâll need a wardrobe if we agree to more than one eventâ you say, casual.
âFine.â
âAnd a stylist. Because if weâre playing pretend, Iâm not showing up in knockoff Louboutins.â
He nods once.
You watch him watching you, calculating. Thereâs no desire in his eyes â not the kind youâre used to seeing. Just thought. Just intention.
âAnd no NDA?â you ask softly.
He finally blinks. âYou want one?â
âI want to know if Iâm being hired as a woman⌠or a risk.â
That pauses him. His voice, when it comes, is lower. âI donât think youâre either.â
You take the final sip of your drink, slow, deliberate.
âThen I accept,â you say, and hold out your hand. âFull illusion. Your perfect lie. You'll want me for the month Harry, trust me.â
He doesnât take your hand right away. He studies it, then finally wraps his own around yours. His grip is warm. Firm. Respectful.
And for the first time all night, you both know ... this is going to be a problem.
He didnât walk you out.
That was the first thing he noticed.
He always did. It was polite. Expected. Something drilled into him during years of stiff boarding school manners and clean-cut PR polish. Even when things were messy, especially when they were messy, Harry knew how to end them gracefully.
But you had risen without prompting. Smoothed your dress with one fluid motion. And left.
Just like that.
No hesitation. No extra glance over the shoulder. No âwhat happens next?â â because you already knew. Or because you didnât care.
He wasn't sure which was worse.
The door shut with a soft hiss, and the silence that followed was loud in a way only penthouses could be. He stood where you'd left him, beside the bar, his glass half full, his chest half empty.
You didnât act like someone whoâd been hired. You acted like someone who was choosing, choosing him, choosing this, choosing every word and pause and smirk with the control of someone who didnât need a script to own a scene.
That dress. That voice. Those eyes that didnât ask for permission.
He shouldâve felt in control. He always did.
But the moment you walked in, everything had shifted half a degree to the left. Still manageable. Still clean. But⌠unfamiliar.
And Harry hated unfamiliar.
He leaned forward and braced his hands on the barâs edge, watching the city glitter beneath the windows like it owed him something.
The arrangement was simple. A distraction. A stand-in. A convenient narrative: Look, heâs already moved on. You are younger. Gorgeous. Not a trace of Lucy.
You would do your job. Charm the right people. Smile at the photographers. Let the world believe he was unbothered, untouched, still winning.
And then youâd disappear.
That was the plan.
But he already knew something wasnât clean about it. Not the way you looked at him, not soft, not sultry. Just sharp. Like you saw right through the expensive suit and the cold bourbon and the man who hadnât slept well in three months.
You didnât ask about Lucy.
You didnât try to guess.
But somehow, you knew.
He exhaled, rolled his shoulders back, and reached for the small leather folder Maya had left for him on the counter - your contract, signed and dated. Full discretion. Rates itemized with painful efficiency.
It felt sterile. It was supposed to.
But all Harry could think about was the faint scent of her perfume, something warm, not sweet, still hanging in the air.
And the way you smiled when you said,
âFull illusion. Your perfect lie. You'll want me for the month Harry, trust me."
I couldn't help myself. As I was writing my other fix 'A Getaway Car' I had some ideas that I could put away so here you go! I hope you love this one, it's going to be very sexy! But slow burn! â¨
At 27 years old, you sign up with a high-end agency for your first âsugar babyâ arrangement, you expects rules, paychecks, and professionalism. What you don't expect is Harry Castillo - a handsome, billionaire who has never hired a sugar baby before and has no idea how to act around one.
Tasked with accompanying him on a high-stakes business trip in the Hamptons for a month to secure a high end business deal, you quickly discover that pretending to be his girlfriend in public is harder than you imagined - especially when Harry is like no man you have ever met or been with.
For the first time, you are both learning that closeness can be intoxicating, dangerous, and impossible to ignore .... and that falling for each other might be the riskiest deal of all.
Warnings: Sugar-baby arrangement | Age gap romance | Billionaire/sugar baby dynamic | Fake relationship | Flirtation and romantic tension | Near-kisses | Intimate touching and cuddling | Protective/possessive behavior | Slow-burn romance | Mature themes (smut) | Emotional vulnerability | very intimate scenes | hot and heavy
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Would you consider writing a Drabble where Harry almost forgets their 1. Year wedding anniversary đžđˇđ
Almost Forgotten - A Harry Castillo Drabble
You wake up smiling.
One year.
Today marks your first wedding anniversary with Harry Castillo.
You don't expect a grand gesture. Harry has never been the type to make a spectacle out of his love. His affection has always lived in the quiet moments-the coffee waiting for you every morning before you've even opened your eyes, the absentminded way he reaches for your hand whenever you're close enough, the gentle kiss he presses to your forehead every single time he passes as though he can't help himself.
He remembers how you take your coffee without ever asking. He tucks the blanket back over your shoulders when you fall asleep on the sofa. He pulls you into his lap while answering emails, one arm wrapped securely around your waist, as if keeping you close is second nature.
That's just who Harry is.
So you don't need flowers. You don't need expensive jewellery or a lavish dinner.
You only want one simple sentence.
"Happy anniversary."
"Morning, sweetheart."
The smell of freshly brewed coffee greets you before you're fully awake.
You pad down the hallway in one of Harry's old T-shirts, rubbing the sleep from your eyes as soft morning light spills through the kitchen windows.
Harry is already dressed.
Navy trousers.
White shirt.
The sleeves rolled neatly to his forearms while his tie hangs loose around his neck, waiting to be finished.
His laptop is open on the island, emails covering the screen, his phone vibrating every few seconds beside it.
The second he hears your footsteps, though, he looks up.
His face immediately softens.
"There she is," he murmurs, a smile tugging at his lips.
He doesn't hesitate.
He opens an arm towards you, and you walk straight into it, letting yourself melt against his chest.
His hand settles comfortably at the small of your back, pulling you impossibly closer.
"Morning, sweetheart."
His voice is still rough from sleep. Warm. Comforting.
"Morning," you mumble into his shirt.
He chuckles quietly before pressing an absent-minded kiss to the top of your head.
His thumb strokes absentmindedly across your waist while the two of you stand there for another moment, neither in any rush to move.
Then his phone buzzes again.
The smile slips into a sigh.
"Sorry."
He leans away just enough to glance at the screen before muttering something under his breath.
"They've moved the Zurich meeting forward."
You watch him skim another email, his brow furrowing.
"Today's going to be hectic."
"That bad?"
"Worse."
"Careful," he says softly. "It's hot."
He pinches the bridge of his nose before setting the phone down again. Without needing to ask, he reaches for the mug sitting beside the coffee machin and he slides it into your hands. Exactly the way you like it. Still hot. Still topped with the little sprinkle of cinnamon he insists makes it taste better.
Your heart squeezes.
"What?"
God. He's so thoughtful
You wrap both hands around the mug, watching him straighten his tie in the reflection of the microwave. You wait. Surely now. Maybe he's building up to it. Maybe he's waiting until you've had your first sip of coffee. Maybe...
He glances back over his shoulder.
You blink.
"Hm?"
"Nothing."
"You're staring." A sheepish smile tugs at your lips.
He laughs under his breath.
"C'mere."
"There."
You walk back over and he cups your face in both hands, thumbs brushing gently across your cheeks before leaning down to press another lingering kiss against your forehead.
One. Then another against the bridge of your nose.
"What was that for?"
"Do I need a reason?"
"No..."
"I just wanted to kiss my girl."
"There she is."
Your stomach flips despite yourself. He smiles, satisfied with the blush creeping onto your face.
You laugh quietly.
"Right."
This is Harry. Always so effortlessly affectionate. Always finding tiny excuses to love you out loud. Which somehow makes the silence even louder. Because after all that... He still hasn't said it. He checks the time on his watch.
He grabs his briefcase from beside the door before shrugging into his coat.
"I'll try not to be too late tonight."
"I love you."
You nod and he kisses your forehead one last time.
Then he's gone. You stare at the closed elevator doors. Maybe he's planning a surprise? Maybe he has things lined up?
"I love you too."
He has to be. Harry doesn't forget anything, especially when it comes to you.
*****
By lunchtime, you still haven't heard anything. No text. No call. Nothing. Your phone buzzes.
Running into another meeting. Love you. â Harry
You sigh.
Love you too.
You don't remind him. You shouldn't have to. Has he really forgot? You tap your nails against the back of your phone as you chew your lip wondering if it's all a mistake. If you're overthinking this.
But by late afternoon, the excitement you'd woken up with has turned into quiet disappointment. You even changed out of the black lace Dior dress you'd picked specially for dinner. Your hair slowly falling out of their curls. The dinner you had started to prep had become more of a chore then made out of love.
Maybe he'd simply forgotten.
*****
Harry barely looks up from his laptop as another file lands on his desk.
"Leave it there, thanks."
His personal assistant, Emma, offers a sympathetic smile, placing the folder neatly beside the growing stack of paperwork.
"You've got the Zurich call in ten minutes, legal at eleven, lunch with the board has been pushed to one, and your flight to Geneva has been cancelled."
Harry exhales through his nose.
"Perfect."
"You've also got three contracts waiting for your signature."
He nods absentmindedly, already reading through another email. His assistant hesitates.
"...And one more thing."
"Hm?" Harry flicks down to a piece of paper with some scribbled numbers across it.
"You asked me to remind you if you looked like you were about to forget."
Harry finally glances up.
"What am I forgetting now?"
"Your anniversary."
Silence. For a second, he simply stares at her.
"...What?"
She gives him a small, apologetic smile, hating that she was the one having to remind him.
"Today. It's your first wedding anniversary."
The colour drained from his face.
"No..." Emma just simply nodded.
"1st July 2025."
Harry's stomach drops so violently it almost makes him feel sick. Today's date flashes through his mind.
The coffee. The kiss on your forehead. The way you'd lingered in the kitchen, watching him. The little smile you'd given him every time he'd looked your way.
His chest tightens.
"Oh, God."
He leaned back in his chair, one hand dragging down his face.
"I forgot."
"You did."
"I forgot."
The words sound hollow coming out of his own mouth. He never forgot. Birthdays. Doctor's appointments. Your mother's favourite flowers. The day your dog had died years before you met him because he knew it was always a difficult one. He remembered everything that mattered.
Except this.
He thinks back to this morning. You'd stood there in one of his old shirts. Sleep still clinging to your eyes. Smiling at him. Waiting. You'd been waiting.
The realization makes his chest ache.
"You knew," he mutters to himself. Emma raises an eyebrow.
"Sorry?"
"You were waiting for me to say it." His eyes close briefly. "And I just... walked out."
A heavy silence fills the office. Emma cleared her throat carefully.
"I've already cancelled your two o'clock." Harry brought himself back up into the office.
"You what?"
"I figured this might be more important." For the first time all morning, Harry smiles.
"Thank you."
"Mr Castillo."
"You should probably go." He doesn't argue as he shuts his laptop. Files are shoved into untidy piles - something Harry never does. He grabs his suit jacket from the back of his chair, nearly forgetting his phone before doubling back for it. As he reaches the office door, his Emma calls after him.
"Go to the flower shop on 6th, ask for Lisa, I rang them through this morning."
He lets out a humourless laugh.
"I don't think flowers are going to fix this."
"No." She smiles knowingly. "But they won't hurt." Harry gives her a thankful smile.
Not because he's trying to save the anniversary.
But because somewhere across the city, the woman he loves has spent the entire day believing she'd slipped his mind.
And that thought hurts far more than any forgotten date ever could.
*****
The penthouse is dark when Harry unlocks the front door. Not completely. Just dim enough that the soft glow of a lamp in the living room spills into the hallway. He pauses for a moment, his hand still wrapped around the doorknob. Normally, you'd be waiting for him.
Curled up on the sofa with a book or cooking dinner with music playing softly through the speakers.
Sometimes you'd meet him at the door before he'd even had the chance to set his briefcase down, wrapping your arms around his waist because you'd "missed him for at least nine hours and forty-three minutes."
Tonight... It's quiet.
Painfully quiet.
He steps inside, gently closing the door behind him.His eyes immediately find the dining table. Two untouched place settings. Candles. Burned almost all the way down. The remains of a dinner that's long since gone cold. His chest caves in. You'd planned something.
Of course you had.
A bottle of wine sits unopened between the plates. Your favourite. The one you'd been saving even though Harry insisted he could buy the winery.
Harry shuts his eyes.
"...Jesus."
He runs a hand over his face, guilt twisting tighter in his stomach. You'd spent the day waiting. You'd probably cooked this yourself. Set the table. Lit the candles. Waited for him.
And he'd spent the entire day buried in meetings, blissfully unaware of the date circled on your calendar at home.
He quietly sets the bouquet he'd bought on the kitchen island.
It suddenly feels...small. Pathetic, even. Flowers couldn't erase this. Neither could the red box in his jacket pocket.
He hadn't bought it because he'd forgotten.
He'd bought it months ago, planning to give it to you tonight. He'd imagined the smile on your face. The way you'd throw your arms around his neck.
Instead...
He forgot to say two words. A floorboard creaks upstairs causing Harry to look up. You're home. He takes the stairs two at a time. The bedroom door is slightly open but he knocks softly anyway.
"Sweetheart?"
No answer. He pushes it open. You're sitting against the headboard in one of his hoodies, a book resting open in your lap. You look up and your expression is calm.
Too calm.
"Hi."
That one word almost breaks him.
"Hi."
He steps inside slowly, as though he's afraid you'll ask him to leave. The silence stretches between you. He notices the discarded black Dior dress over one of the chairs.
"I..." Harry starts, before stopping himself.
There aren't enough words. No excuse sounds good enough. Work doesn't matter. Meetings don't matter. Nothing matters more than the woman sitting in front of him. He lets out a shaky breath.
"I'm so sorry."
You lower your eyes to the pages of your book.
"It's okay."
"It's not."
"It is."
"No." His voice cracks slightly. "Please don't tell me it's okay because it isn't." You don't answer.
Harry takes another step. Then another. Until he's standing beside the bed.
"I forgot."
The words are barely audible.
"I know."
"I didn't remember until Emma reminded me this afternoon."
You nod once.
"I figured."
"I kept thinking something felt...off." He laughs bitterly at himself. "When you were looking at me this morning. I knew something wasn't right, and I couldn't work out what it was."
Your throat tightens. Harry kneels in front of you. Actually kneels, like the day he asked you to marry him but this time it was for forgiveness.
His hands find yours, careful, tentative, as though he's waiting for you to pull away. You don't.
"I'm so, so sorry."
His thumbs stroke across your knuckles.
"I've replayed this morning in my head about a hundred times." A tear slips down your cheek before you can stop it.
"You kissed me goodbye."
His face crumples.
"I know."
"You told me you loved me."
"I know."
"You remembered how I take my coffee."
"I know."
"But you forgot our anniversary." The tears are falling freely now.
"I kept thinking..." you whisper, "...that maybe you'd remember in the car. Or someone at work would say something. Then you text and I thought..." Your voice catches. "I thought this is it."
Harry's own eyes shine with tears.
"And then you just..."
You can't finish. His forehead rests against your joined hands.
"I hurt you."
It isn't a question.
"No meeting was important enough for this. No email. No phone call." His voice is thick with emotion. "I made the person I love most in this world feel forgotten."
You squeeze your eyes shut.
"I didn't need presents, Harry."
"I know."
"I just wanted you to remember."
"I know."
He lifts his head, his eyes red.
"I have loved you every single day we've been married. Every single day before that. Forgetting today doesn't change that."
"It doesn't," you agree softly. "But it still hurt."
He nods immediately, not trying to argue or lessen it.
"And you have every right to be angry with me." You look at him for a long moment.
"I'm not angry."
"No?" You shake your head.
"I'm just...sad."
Somehow, that hurts him even more. Because anger would fade. Sadness lingers.
Harry carefully reaches up, brushing away a tear with his thumb.
"I can't undo today," he whispers. "But if you'll let me...I'd like to spend the rest of my life making sure I never make you feel like this again."n
He reaches into his jacket pocket, then pauses. Instead of pulling out the small red box with gold writing, he leaves it there.
Not tonight.
Tonight wasn't about gifts.
It was about making sure you knew you had never, ever been forgotten in his heart even if he'd failed to show it that morning.
Instead, he leans forward and wraps his arms around you, holding you gently, as if trying to mend the hurt he'd caused one heartbeat at a time.
After a moment's hesitation, you wrap your arms around him too.
"I'm an idiot." He whispers into your hair. Despite yourself, you let out a small laugh.
"The biggest one in New York."
"Happy anniversary," he whispers. You smile against his shoulder.
"Took you long enough."
"I know."
"And Harry?"
"Hm?" He said reluctantly pulled away from your warm embrace.
What Happens After Midnight - Harry Castillo Christmas Story Masterlist
A slow-burn, years-long almost-love between you and Harry Castillo - a man who swears men and women canât be friends, and yet somehow becomes yours anyway.
Missed chances. Jealous moments. A New Yearâs kiss that shouldnât have happened. One night you pretend meant nothing. And a confession that changes everything.
Inspired by the ever great festive film, When Harry Met Sally.
Warnings: heartbreak, Angst, Friends to lovers, Enemies to friends to lovers, Mutual pining, jealousy, Miscommunication, One-night stand aftermath, smut, Cursing / strong language, Crying, Alcohol use, Arguments, Breakups / ex getting married, New Yearâs Eve kiss, Hurt/comfort, Denial (lots of denial).
Warnings: đ smut warning. 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.
I don't wanna tip toe and I don't wanna hide, but I don't wanna feed this monstrous fire - Ariana Grande
The first thing you were aware of was warmth.
Not just from the sunlight bleeding through the floor-to-ceiling windows, but from the body beside you â steady, solid, unmistakably Harry.
It took all of three heartbeats for memory to catch up.
The way his hands had gripped your hips last night, his voice rough in your ear, the heat that had drowned out every rational thought until you werenât thinking about contracts or boundaries or anything except him.
Your stomach tightened.
This was never part of the deal. Sex wasnât mentioned, wasnât implied. The contract was about appearances, companionship, playing the part. Not this.
You shifted, the sheet slipping down your skin. Harry stirred, his arm falling away from your waist, and for a moment you thought you could slip out unnoticed. But then his voice came, low and still heavy with sleep.
âMorning.â
You froze, looking over your shoulder at him. His hair was a tousled mess, his jaw shadowed with stubble. He looked unfairly good for a man whoâd barely slept.
âMorning,â you echoed, your voice quieter.
His gaze lingered on you, slow, deliberate, before he pushed himself up to sit against the headboard. The silence between you wasnât uncomfortable exactly - it was charged, thick with all the things neither of you could say.
He rubbed a hand over his face. âAbout last nightâŚâ
Your chest tightened. You couldnât let him finish. âIt canât happen again.â
He stilled, eyes narrowing almost imperceptibly. âI was going to say the same.â But his tone wasnât quite convincing, and he didnât look away immediately.
âGood,â you said, pulling the sheet up over your chest like armor. âIt was⌠not part of what Iâm here for.â
Something flickered in his eyes - annoyance? Regret? You couldnât tell. âRight. Just⌠a lapse in judgment.â
You forced a light shrug. âHappens.â
But the truth was still humming beneath your skin. Last night hadnât felt like a lapse, not for a second. It had felt inevitable.
Harry swung his legs out of bed, standing and reaching for his shirt. âIâll get us some coffee.â His voice was casual, but his shoulders were stiff.
âSure,â you murmured, not trusting yourself to say more.
He glanced at you once more before leaving the bedroom, his expression unreadable. And as the door clicked shut, you were left staring at the empty space beside you, the sheet still warm where heâd been.
You told yourself you were relieved it was over.
But your body, your thoughts, refused to believe you.
*****
Harry woke up before you.
Heâd been awake for a while, actually - lying there in the grey dawn light, staring at the ceiling, replaying every moment of the night before like some kind of masochist.
Heâd never meant for it to happen.
Hell, it shouldnât have happened. The contract was clear: you were there for appearances, to keep him from walking into events alone, to smooth over the edges of his public image. Sex wasnât part of it.
But last night⌠last night heâd stopped caring about the rules.
His gaze drifted sideways to where you slept, hair spilled across the pillow, the sheet tangled low around your hips. His chest tightened. He should have gotten out of bed the second it was over. He should have put that distance back between you before either of you had a chance to think.
Instead, heâd stayed. Heâd watched you fall asleep against him, your breath warm on his chest, and for a dangerous moment, heâd let himself imagine what it would be like if this wasnât temporary.
Now, in the pale light of morning, reality was clawing its way back in. The clock was ticking on your thirty days. He wasnât supposed to want you beyond that - wasnât supposed to want you at all.
You stirred, and his eyes snapped shut for a second. When you turned to look at him, his heart kicked once, hard.
âAbout last nightâŚâ he started, unsure whether to apologise or just pretend it didnât matter.
âIt canât happen again,â you cut in.
The words landed like a punch, though heâd been bracing for them. He forced his jaw to unclench. âI was going to say the same.â
It wasnât entirely a lie. It shouldnât happen again. But the way your skin had felt under his hands, the way youâd said his name - he knew it would haunt him every time you stood beside him from now on.
âRight. Just a lapse in judgment,â he added, hoping it sounded casual.
âHappens.â
He didnât miss the way you clutched the sheet higher, like you needed the barrier. He also didnât miss the part of himself that wanted to pull it away and drag you back under him.
He stood, grabbing his shirt if only to have something to do with his hands. âIâll get us some coffee.â
He looked at you once more before leaving - one last glance he shouldnât have taken. You were staring at the empty space beside you, the same one heâd just vacated, and it made his stomach twist.
In the hallway, he rubbed a hand over his face. He needed to get his head straight. Keep it professional. Go back to how it was.
But deep down, he already knew the truth.
If it happened again, he wouldnât stop it.
*****
Harry had been staring at the same spreadsheet for twenty minutes. The numbers blurred, his mind refusing to click into gear.
It wasnât the deal. Wasnât the shareholdersâ meeting. It was you.
Last night kept looping in his head like some private, torturous reel - the way your breath had hitched when heâd first touched you, the way your nails had scraped against his shoulders when he pushed deeper, the sound you made when you came. That sound alone was enough to make him shift uncomfortably in his chair.
You both agreed it was a one-time thing. An accident. But it didnât feel like an accident. It felt like something heâd been heading toward since the second you had walked into his life. And now that it had happened, he couldnât remember a single good reason why it shouldnât happen again.
Harry loosened his tie, dragging a hand down his face. You looked wrecked in his sheets, hair tangled, lips swollen, the red marks heâd left on your skin blooming like proof. And you smiled, sleepy, content, right before telling him it couldnât happen again.
That smile had gutted him more than the words.
Now, there was another event tonight. Another chance to see you in some dress that made every man in the room look twice, while he stood there pretending he wasnât imagining you underneath him again. Pretending he wasnât counting the hours until he could get you alone.
His phone buzzed with a message from Maya confirming the car for that evening. He should have been thinking about speeches, handshakes, deals.
Instead, Harry was thinking about your mouth. Your hands. The way you gasped his name like it was the only word you knew.
And God help him, he was already planning how to break the rule again.
******
By the time the evening event rolled around, Harry was already wound tight. He told himself to stay cool, stick to the plan, keep it professional.
That resolve shattered the moment he saw you.
You stepped onto the rooftop terrace like you'd been born for it, wrapped in a black silk dress that clung to you in a way that made his mouth dry. The thigh-high slit flashed smooth skin every time you moved, and the delicate straps left your shoulders bare. Your hair was loose, catching the soft breeze, and the city lights behind you only sharpened the effect.
Harryâs drink stilled halfway to his lips.
You were already deep in conversation with one of the hosts, laughter threading effortlessly through your words, one hand resting lightly on the railing as if you had nowhere else to be. To anyone watching, you looked perfectly at ease - unbothered, engaged, sparkling even.
He thought you hadnât noticed him yet. That was his mistake.
Youâd felt him the moment you stepped into the room - not just seen him, but felt the shift in the air, the way your skin prickled in awareness. Your first instinct had been to keep your distance, to slip behind clusters of guests and position yourself as far from him as the space allowed.
Thank God youâd arrived separately tonight. Heâd come straight from work; youâd had the luxury of breathing space, time to rehearse the cool detachment you swore youâd keep.
It wasnât working. Not with him somewhere in this room, dressed in a tux that fit him like a sin, probably with that low, knowing smile he wore whenever he caught you looking.
For Harry, watching you smile at someone else while he was still carrying the feel of your body in his bed from twelve hours ago - it was a test he had no interest in passing.
He closed the distance, keeping his voice low when he reached you.
âYouâre late."
You turned, eyes skimming over him, a faint smile curling your lips, trying to ignore the butterflies in your stomach.
âFashionably.â
âThat dress should be illegal."
Harry always complimented you on your dresses and every time it made you blush, but this time, your weren't blushing you were burning.
Not from embarrassment, but from the way his voice dropped when he said it, low and intimate, meant for you and only you.
It wasnât just the words. It was the way his eyes dragged down the length of you, slow and unapologetic, like he was taking his time unwrapping something he already owned. His gaze lingered at the dip of your neckline before lifting back to meet yours, and this time, you didnât shy away.
Usually, youâd laugh it off. Make a joke. Pretend you werenât secretly thrilled by his approval. But tonight, something in you rebelled. Maybe it was the memory of last night, still sharp in your mind no matter how many times you told yourself it wouldnât happen again. You told him it wouldn't happen again.
You tilted your chin, matching his stare. âYou say that like youâre hoping Iâll take it off.â It was a challenge. That's what you told yourself anyway.
A muscle ticked in his jaw. He hand pressing on your lower back as he leaned close to your ear, his breath tickling your neck. âDonât tempt me. Not here.â
But you could tell he wasnât warning you. He was daring you.
The air between you thickened. People milled past, laughing and clinking glasses, but you didnât hear a thing, not over the pulse of want building in your chest. His compliment wasnât just about the dress. It was a reminder. A provocation. And the heat coiling low in your stomach told you he knew exactly what it was doing to you.
You both mingled. Smiled for cameras. Nodded politely through small talk neither of you heard. But Harry kept catching your eyes across the crowd - long, weighted looks that pulled the air taut between them. And then, like fate wanted to see just how far his control could stretch, he saw you with Leo Price.
Across the room, you smiled, feeling the warmth of the evening settle around you as Leo leaned in, a teasing glint in his eyes.
âQuite the gala tonight, huh?â His voice was smooth, casual, but there was something beneath it, an edge.
You returned the smile, matching his tone. âItâs hard not to be impressed. And you? Always managing to show up in style.â
Leo gave a slow, confident shrug, a sly smile playing at his lips. âOnly when the companyâs worth it.â
Your glance flicked toward Harry, who was watching from across the room. You let your smile deepen. âWell, Iâm glad to be making an impression.â
Leoâs eyes darkened just slightly. âCareful with compliments like that. They tend to lead somewhere⌠interesting.â
You raised an eyebrow, biting back a smirk. âMaybe Iâm in the mood for a little excitement.â It was harmless flirting. Leo was a few years older than you, in your 'age bracket' and frankly, quite harmless and good company in a room full of men and women over 40.
He chuckled softly. âNow thatâs a conversation Iâd like to keep going.â
The flirtation hung between you, light, effortless, but charged with something unspoken, the kind of tension that made every word feel like part of a delicate dance.
You tilted your head slightly, voice casual but edged with genuine curiosity. âDare I ask how the deal is going with Harry and your father?â
Leoâs smile flickered for a moment - just a flash - before he answered smoothly, âItâs moving along. Nothing finalized yet, but weâre close.â
You nodded, folding your hands loosely in front of you. âHarry hasnât said much since that dinner.â
He glanced over, eyes narrowing just a bit. âHarry tends to keep things close to the chest. You know how he is.â
You did. The careful control, the way he guarded his business like it was a secret weapon. But something about Leoâs tone made you wonder if there was more beneath the surface - a tension you couldnât quite place.
âLet me know if I can help,â you said lightly, the offer half business, half something else.
Leoâs grin returned, warm and a little dangerous. âIâll hold you to that.â
The conversation drifted, but the unspoken currents beneath your words lingered - both of you playing your parts, aware of the lines you couldnât cross.
But across the room, Harryâs jaw set. He didnât think.
In three strides he was there, his palm finding the small of your back in a way that looked gentlemanly enough for anyone watching.
âExcuse us.â
Leo blinked, but Harry was already steering you away, the heat of your body under his hand doing nothing to help his temper.
âThat was rude.â you said, trying to keep your tone light as he guided you away, his hand firm but careful, like he was protecting something precious.
âThat was necessary.â
He didnât stop until you were tucked into a shadowed alcove just off the terrace, the muffled hum of the party spilling through the open doors.
âHarry....â
âYouâve been avoiding me.â
You laughed at his words. âIâve been talking to people. Thatâs what one does at a gala.â
âTalking with Price.â
You laughed softly, without looking at him. âYou really have a problem with that, donât you?â
He stepped closer, close enough for the subtle scent of his cologne to reach you, warm, expensive, and maddeningly familiar.
âYouâve been avoiding me⌠because youâre remembering exactly what happened the last time we were alone."
The next thing you felt was the railing at your back and Harryâs body close enough that the heat of him seeped straight through the silk of your dress.
You opened your mouth to answer, but his hand slid to your hip - not pulling, just holding - his thumb brushing over the bare skin exposed by the dressâs low side.
You should have told him to stop. Should have reminded him of the agreement. Of your conversation this morning. But instead, you stayed perfectly still, every nerve in your body screaming at the contact, begging for more.
âWe said...â
âI know what we said.â
His voice was low, controlled, but his grip tightened like he wasnât as composed as he wanted you to believe.
He shifted, pinning you lightly against the railing with nothing more than the angle of his body, his mouth dangerously close to your ear.
âEvery time Iâve looked at you tonight, youâve been biting your lip. And I know exactly why.â
Your pulse thudded so hard you could hear it.
âYouâre imagining things.â you rolled your eyes laughing, knowing he was absolutely right.
âIâm imagining what youâd sound like if I slid my hand up under this dress right now. And I bet you are too.â
His fingertips brushed your bare arm, just enough to make your breath catch before he stepped back, leaving you stranded in the cool air heâd just vacated. You were quick to miss the warmth of his body.
âGo back in there. Smile. Pretend youâre not thinking about me."
*****
You did. You tried. But the heat coiled low in your stomach only grew worse. Every time your eyes found him, leaning in to speak with someone, adjusting his cufflinks, catching you watching, it was like the two of you were the only people in the room.
By dessert, you were done pretending. He saw it in your face when he offered his hand and asked, far too casually,
âShall we get some air?â
The night was warm when you stepped outside, the garden strung with fairy lights, music muffled behind glass. He didnât touch you at first - just stood close enough that your arm brushed his every time you shifted. Then his hand slid to the small of your back, guiding you toward a darker corner where no one could see.
The wall of the building was cool against your spine. His body was hot against the front of yours.
âStill think it was a lapse in judgement?â
When his mouth claimed yours, there was no pretense left - only weeks of denial snapping all at once, the taste of him, the faint rasp of his stubble against your skin as his hands roamed lower. You didnât even notice your clutch hit the ground.
And in that moment, you both knew there was no such thing as one time.
âWe agreed....â you gasped for air as you pressed your hands to his chest lightly.
âWe agreed while you were still breathless in my bed. That was never going to stick.â
His voice was low, rough, the kind of tone that sank under your skin and stayed. You took a step back, but the wall caught you, leaving nowhere to go.
âSomeone could see.â
âThen donât make me give them a reason to look.â
He stepped in, the heat from his body bleeding into yours, one hand braced on the wall by your head, the other slipping around your waist.
âTell me to stop.â
You don't and within seconds he kissed you.
It was nothing like the night before - this was harder, hungrier, the kind of kiss that left no room for air. You gasped, and his tongue swept in, claiming, tasting, daring you to push him away. Instead, your hand curled into his jacket, pulling him closer.
His palm slid down your side, fingertips finding the bare skin high on your thigh where the slit opened. You shivered, your breath breaking against his mouth.
âStill think it was a one-off?â
Harryâs hand stayed on your hip, the heat of it burning through the silk. You could feel the subtle shift of his body, the controlled way he leaned in so his breath grazed your ear.
âYou have no idea how hard it is to keep my hands off you tonight.â
You swallowed, pulse kicking hard against your throat.
His thumb traced a slow line just under the edge of your dress, finding the bare skin of your thigh. The movement was maddening, not rushed, but deliberate, like he wanted you to feel every second of it.
âHarryâŚâ
âSay my name like that again and Iâll forget where we are.â
Your breath hitched when his fingers slid higher, just enough to graze the softest part of your inner thigh. Not quite touching where you needed, but close enough that your body betrayed you, hips tilting forward, breath shallow.
He smirked, his mouth so close to your ear you could feel the curve of it.
"Yeah. Thatâs what I thought.â
Somewhere behind you, the faint hum of voices drifted from the main terrace. But here, in the dim light, it felt like the two of you existed in your own dangerous bubble.
His hand moved higher - not enough for full contact, but enough to make your legs press together instinctively. You hated how much you wanted more.
âHarryâŚâ
âSay it.â
He pressed his mouth to your jaw, your neck, each kiss hotter than the last.
âHarry...someone...â
âDonât care.â
His voice was ragged, like heâd been holding this back since sunrise. The party was only a few feet away, the murmur of conversation and the occasional burst of laughter bleeding into the alcove. Anyone could glance over and see. The thought should have stopped you. It didnât.
Harryâs fingers caught the slit of your dress and eased it further apart, his palm cupping you over the thin scrap of lace youâd put on that morning without thinking of him - though you knew now youâd never wear them without thinking of him again.
âYouâre soaked.â
Your head tipped back against the wall when he pressed his fingers just right, heat and friction sparking low in your belly. His other hand slid up your side, claiming the curve of your breast through the silk.
You bit your lip to keep from making a sound, but Harryâs mouth found your ear.
âDonât be quiet for me.â
He kissed you again, deeper this time, his fingers stroking through the lace until your hips tilted toward him. His knee slid between yours, pinning you, holding you open.
You tugged at his jacket, wanting more, and he pulled back just long enough to shrug it off and toss it aside.
âThis is-â
â-exactly what you want.â
The smirk was there, dangerous and knowing, as he pushed your panties aside and slid two fingers into you. Your breath caught on a sharp, involuntary moan that made his grin widen.
âThatâs it. Just like last night.â
He moved his hand in a slow, deliberate rhythm, his thumb brushing your clit in a way that made your knees threaten to give out. You clutched his shoulders, nails biting through his shirt.
The hum of voices nearby blurred into white noise. The air felt thick, heavy with the scent of him and the taste of his mouth still lingering on your lips.
Your hips began to rock into his touch, chasing that crest, and Harryâs eyes locked on yours like he could feel every pulse of heat building inside you.
âCome for me baby.â
You did - hard, your cry muffled against his shoulder, his fingers drawing it out until you were trembling against him.
"Harry..."
"Come on. Time to go."
You watched him, cool and collected, as he straightened his tie and slipped into his suit jacket â like nothing had shifted between you. Like the heat of your skin still clinging to his fingers didnât exist. Your mouth fell slightly open, caught in the pull of disbelief and something deeper, something you werenât ready to name.
Then, without hesitation, he reached out, his hand closing around yours with firm certainty. The touch was electric, grounding you even as it stirred a quiet fire beneath your skin. He led you toward the exit, each step deliberate, measured, like this was all part of the same choreography.
No words. Just the weight of his hand in yours, a promise unspoken.
Luca was waiting by the car, door already open, his eyes flicking briefly between you and Harry.
You slipped inside the back seat, the city lights blurring past the window as the door clicked shut behind you.
******
The whole car journey was unbearable. The delicate lace of your thong was soaked and damp, sending a subtle heat that you tried to tame by crossing your legs tightly. Your body ached with a delicious ache you werenât ready to admit aloud, but Harry seemed oblivious, his eyes fixed straight ahead on the dark city streets rushing by the windows.
Yet, his hand was still entwined with yours - warm, steady, and grounding - something you werenât quite ready to let go of just yet. That simple connection kept you tethered, even as the silence between you stretched thick with unspoken desire.
You stole a glance at him from the corner of your eye. His jaw was clenched, the tension in his shoulders betraying the calm mask he wore. The way his fingers tightened around yours, just slightly, told you he was feeling it too - that simmering need youâd both agreed to deny but clearly hadnât forgotten.
The car slowed as it pulled up to the penthouse, and your heart jumped.
âWeâre here,â he said softly, voice low.
You swallowed hard, reluctant to leave the warmth of his hand, the heat that still clung to your skin like a whispered promise.
As the car door opened, the cool night air hit you, sharp and sobering. You took a deep breath, knowing the night wasnât over - but that whatever came next would be wrapped in tension, restraint, and all the things you hadnât yet dared to say.
You step out of the car, the soft click of your heels echoing on the polished pavement as you follow Harry inside. The lobby is quiet, the muted hum of the city distant behind the heavy doors. Your skin still tingles from the lingering heat of the ride, but you keep your posture steady, refusing to let him see how rattled you are.
Harry leads the way up the elevator, the air between you charged but unspoken. When the doors slide open onto the penthouse floor, you pause for a moment, catching his eye.
He steps inside first, closing the door softly behind you. The penthouse glows softly under the city lights. You breathe out, steadying yourself.
Harry moves to the window, looking out over the skyline. Then he turns, eyes sharp.
âNo more pretending,â he says quietly. âLast night wasnât just some mistake for me.â
You hold his gaze, cool and steady. âIt wasnât a mistake, Harry. I said it can't happen again. But Iâm not in this for feelings. You know that.â
He takes a step closer, voice low. âThen why canât I stop thinking about it? About you?â
You shrug, trying to not think about the dampness in your thong, desperate to play it cool. âMaybe youâre overthinking it.â
His lips twitch, amused. âOr maybe Iâm the only one here whoâs being honest.â
You raise an eyebrow. âMaybe. But honesty doesnât mean Iâm going to hand over my heart.â
He reaches out, brushing a loose strand of hair from your face. âIâm not asking for your heart. Just a chance.â
You smirk, stepping even closer. âCareful. Youâre getting dangerously close.â
His voice drops to a whisper. âDanger is kind of my thing.â
Just as your lips almost meet, he pulls back slightly, eyes gleaming. âNot yet. I like watching you want me.â
You grin, feeling the challenge, the heat between you crackling like static. You watch as he goes to his bedroom, no further words exchanged.
As you settle into bed, the city lights casting a faint glow through the curtains, your mind replays the night: the tension, the unspoken promises, the delicious tease of almost-touching lips just moments ago.
You tell yourself youâre in control - always in control - but the quiet thrill running beneath your skin tells a different story.
Turning onto your side, you stare out the window, heart pounding slightly faster than usual. The night stretches on, endless and full of possibility. But Harry was forgetting one thing... You were a master of this game, skilled at giving men exactly what they craved - and making a living from it.