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
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I’m thinking… Harry and you have been a couple for a few years now. Maybe engaged? Something’s on your mind but you find it hard to open up to him because he’s been busy and you don’t wanna burden him. But then he found out you opened up to a friend and he’s 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, I’ll 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 hadn’t really read, the diamond on your finger glinting every time you turned a page. It should’ve 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 hadn’t made.
Harry noticed. Of course he did. He always noticed. He’d reach for your hand across the sheets, or tug you gently against his chest, murmuring for you to sleep. Sometimes you managed a soft “I’m fine.” Sometimes you didn’t trust your voice at all.
And all the while, the list grew longer.
So you’d 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 hadn’t meant to unload - she’d simply asked how the planning was going, and before you could stop yourself, the words spilled out. How the florist kept sending invoices that didn’t match what you’d 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. “You know, it doesn’t have to be this hard,” she’d said gently. “Harry’s part of this too. You don’t need to do it all by yourself.”
The reminder landed like a pebble in your chest, rippling outward. You’d brushed it off with a smile, promising you’d figure it out, but later that night the echo of her words followed you into bed.
Because she was right. You didn’t want to be the kind of partner who crumbled silently under the weight of things Harry hadn’t 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.
“Hey,” you said softly, closing the magazine.
“Hey.” 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 didn’t sit casually. He sat forward, elbows on his knees, eyes locked on yours.
“I saw Claire today.”
Your stomach dropped. “Oh?”
“She mentioned the wedding. That you’ve been overwhelmed.” His tone wasn’t cruel, but it was edged. “You never said anything to me.”
Your throat tightened. “Harry, I didn’t mean...”
“You told her you feel like it’s too much. Like you’re suffocating.” His jaw flexed. “But not me.”
The hurt in his voice was worse than anger. It was disappointment. You hurried to explain. “You’ve 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.”
“Selfish,” he repeated, shaking his head. He leaned closer, catching your chin, tilting your face toward him. “Sweetheart, this isn’t about flowers. This is about us. About building our life together. And you thought I wouldn’t want to hear it?”
Your eyes stung. “I didn’t want to be another weight on your shoulders.”
His gaze softened, but his grip didn’t waver. “You’re not a weight. You’re the reason I carry everything else. Don’t you get that?” His thumb brushed along your jaw. “I can’t stand the thought of someone else being the one you turn to when it should always be me.”
You swallowed. “I just didn’t want to make things harder.”
“Baby,” he said gently, “you’re not capable of that. The only thing that makes things harder is thinking you don’t trust me enough to let me in.”
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 you’d been carrying seemed to melt under his steady hands, the rise and fall of his chest grounding you.
“Listen to me,” he murmured against your hair. “This wedding doesn’t mean anything if you’re carrying it all alone. I don’t care if it’s flower arrangements or the end of the world. You bring it to me. Always.”
You nodded against his shirt, your voice muffled. “Okay. I promise.”
“Good,” he whispered, kissing the top of your head. “Because you’re not in this alone. You never will be.”
*****
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. “You’re going to sit in there and tell me everything that’s been spinning in that pretty head of yours. Every worry, every detail. And I’ll remind you that none of it is bigger than us.”
You laughed wetly, swiping at your eyes. “You don’t want to hear me debate roses versus peonies.”
“I want to hear everything,” he said simply, brushing your engagement ring with his thumb. “Because it’s ours. And because you’re mine.”
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.
“You’re going to be my wife,” he whispered, leaning close, lips brushing your damp hair. “And I’ll be damned if you ever think you have to carry any of this alone.”
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, “Alright. Start talking. What’s been eating at you?”
You hesitated, fingers tracing circles on the surface of the water. “Everything feels… big. Every decision feels like if I get it wrong, I’ll 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 don’t even like…” You exhaled. “It’s too much.”
Harry kissed the side of your head. “Baby, no one’s going to remember if the napkins were ivory or cream. They’ll remember you walking down that aisle. They’ll remember you saying yes. That’s it.”
You smiled faintly. “Easy for you to say. You’re not being asked to pick between six kinds of roses.”
“Then don’t.” His tone was matter-of-fact, but his hand rubbed lazy circles over your arm. “You pick one you like, and that’s the end of it. You don’t owe anyone else a committee vote.”
“You don’t care what flowers we have?”
“I care that you’re not tearing yourself apart over them,” he said simply. “Though, if you ask me…” His mouth curved in a rare, boyish grin. “Peonies sound like something out of a fairytale. Big, ridiculous, dramatic. Perfect for you.”
You laughed, the sound bubbling out before you could stop it. “You’re not supposed to be good at this.”
“I’m good at everything when it comes to you,” he said, with enough mock arrogance to make you laugh harder. Then he kissed your temple again, softer this time. “We could get married in a field with dandelions, and I’d still think it was the most beautiful day of my life.”
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. “I just don’t want to let you down. I want it to be perfect.”
His arms tightened around you, his voice low and steady. “You could walk down that aisle barefoot, in jeans, with nothing but me waiting at the end and it would be perfect. Because it’s us. That’s all I want.”
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 he’d just given you.
When you pulled back, he rested his forehead against yours. “So. No more bottling it up. You tell me when something’s too heavy. We carry it together.”
“Together,” you whispered.
His smile was small but sure, the kind that reached his eyes. “That’s my girl.”
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 weren’t 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 you’d grown used to his steady presence - the way he’d change a diaper without complaint, or the way he’d 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 friend’s 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 Harry’s 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. “There’s my girls,” 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.
“Brought me the best surprise,” he said, leaning down to brush a finger gently over the baby’s cheek. His grin was boyish, proud. “She’s getting bigger every day.”
Nancy's expression soured in the corner of your eye, but Harry didn’t 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 Harry’s office again with your daughter. He hadn’t 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.
“I don’t know how she’s managed to keep him interested,” Nancy said, tone sharp and dripping with disdain. “She hasn’t even lost the baby weight. Men like Harry don’t stay when things change. He’ll get bored sooner or later.”
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 hasn’t even lost the baby weight… He won’t stay.
That night, Harry kissed your shoulder as he climbed into bed. You tensed. He noticed. Of course he noticed.
“What’s wrong?” he murmured, voice low in the dark.
“Nothing,” you lied, curling away.
It wasn’t 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. “Sweetheart,” he said softly, “you’ve been miles away from me for weeks. Tell me what’s going on.”
You shook your head, but his thumb brushed your cheek, catching the tears you hadn’t 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."
Harry’s face hardened, but not at you.
“I heard her,” you whispered, voice breaking. “Nancy. She said I haven’t lost the baby weight. That you’d… that you’d leave me. And maybe she’s right. You deserve someone who...who doesn’t look like this, who isn’t tired all the time, who isn’t....”
“Don’t,” he interrupted sharply. Then his tone gentled, his hands cradling your face. “Don’t you dare finish that sentence.”
Your lip trembled. He leaned in closer, eyes blazing.
“You are the love of my life,” he said, every word deliberate. “You gave me our daughter. You think I’d trade the most beautiful woman I’ve ever known - the strongest, the bravest - for someone who can’t hold a candle to you? Not in a million lifetimes.”
Tears spilled hot down your cheeks.
“Harry…”
“Shh,” 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. “Lie back for me.” 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 wasn’t distant; it was hungry and tender at the same time.
“Every inch of you is mine,” 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.
“Harry…” you gasped, fingers sliding into his hair.
“Shh,” he whispered against your skin, moving to the other breast, giving it the same slow, teasing worship. “You’re perfect. You’re beautiful. Don’t ever doubt it.”
His hand slid down your waist, pausing at the faint marks on your stomach. He bent and pressed kisses there, reverent, his voice rough. “Proof you gave me our daughter,” he said. “Most beautiful thing you’ve ever done.”
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.
“Look at me,” he murmured, eyes glinting up at you. “I want to see you.”
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 didn’t 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, “I’m here. I’m not going anywhere.”
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. “Only me,” he whispered between kisses. “Always me. You’re perfect. God, you feel so good…”
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 he’d 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. “Do you believe me now?” he asked softly, his voice rough with emotion.
“Yes,” you whispered, tears slipping free. “I believe you.”
He kissed you then, slow and tender. “Good. Because I’ll keep proving it until you never doubt it again.”
He eased out of you gently, but didn’t 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 polish—gold 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 didn’t grip, didn’t cling—just guided, a constant presence that grounded you in the swirl of opulence.
You were smiling at a board member’s 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.
“Mr. Castillo,” she said smoothly, ignoring you. Her hand brushed the sleeve of his tuxedo as though she had the right. “As always, you command the room.”
You waited for Harry to draw back, for irritation to flare. But instead, he simply regarded her. Cool, unreadable. His expression didn’t flicker - not warmth, not anger. Just control. “Nancy,” he said evenly. “I didn’t expect you here tonight. I thought you said work events were not your scene.”
Her eyes flicked to you and back. “Well, 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.”
Something in your chest tightened. The words stung, not because you believed them, but because you remembered too clearly the cruel whispers she’d aimed at you - that Harry would leave, that you weren’t enough anymore. For a moment, you felt the sting of that doubt again.
Harry’s jaw shifted, so subtle only you noticed, but his voice remained calm and clear. “You seem to be mistaken,” he said, every syllable precise. “Your position was to support my work, not my reputation. And certainly not to spread gossip about my wife.”
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. “I...I don’t know what you mean...”
But Harry’s tone didn’t waver. “I 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.”
It wasn’t loud, it wasn’t 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 Harry’s steady eyes silenced her. She turned sharply, heels clattering against the marble as she disappeared into the crowd.
You let out a breath you hadn’t 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 didn’t 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.
“Apologies for the interruption,” he murmured, his voice low, meant only for you. “It won’t happen again.”
Something in your throat tightened, emotions threatening to spill over. You weren’t 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 couldn’t quite stop staring at him. Not the billionaire, not the untouchable man everyone else saw—but 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 once—small, 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 couldn’t stop replaying it. The hush of the crowd. The way he’d spoken, calm but absolute. The way everyone had turned to stare.
Finally, you exhaled, turning toward him. “Harry… you didn’t have to do that. Not like that. In front of everyone.” Your voice was soft, a little shaky. You meant it - part of you still couldn’t believe he’d done it so openly, for you.
His eyes shifted to you, steady and unyielding. “Yes, I did.”
You blinked, startled by the firmness in his tone. He reached across, his fingers lacing through yours. His grip wasn’t tight, it was grounding, deliberate.
“You think I should’ve let it slide?” he asked quietly. “Ignored the way she spoke about you? Pretended it didn’t reach me? That’s not how I run my company. That’s not how I run my life.”
You swallowed, your chest aching. “But… it was public. People will talk.”
“They were already talking,” he countered smoothly. “She was talking. Whispering poison where she thought I wouldn’t hear. If I corrected her behind closed doors, she’d still walk out of that room smiling, still believing she could get away with it. This way…” His thumb brushed the back of your hand, controlled, precise. “…she knows. Everyone knows. No one questions where I stand.”
You bit your lip, tears prickling at your eyes. “But Harry, you don’t have to defend me....”
That broke his composure for just a moment. His jaw set, his eyes sharpening. “I don’t have to,” he agreed softly, almost sharply. “I choose to. Always.”
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.
“She 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.”
Your breath caught, tears spilling before you could stop them. You whispered, “Harry…”
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.
“Don’t thank me. Don’t tell me I didn’t have to. It was necessary. And I’d do it again tomorrow if I had to.”
The car rolled smoothly through the city, but in that cocoon of quiet, the truth settled into you: he hadn’t 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.
“Now, let’s see our little girl before she lets the whole city know she’s awake."
Thank you @kellyxo1 for this great prompt! I loved writing it and I hope you all loved reading it! 😘✨
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.
You’re 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 client’s assistant was specific - “He’ll meet you in the penthouse. Not before. Don’t be late.” So you took the private elevator like a ghost, let the doorman scan you like contraband, and now you’re 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 I’m 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 doesn’t 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 don’t 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 he’s 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.
“Rough night?” 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 didn’t 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 didn’t. 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 he’s looking. Really looking. Assessing. You hold his gaze and smile - a half-smile, the kind that says I’m not nervous, but I am curious.
He doesn’t smile back. “That obvious?”
You shrug, shifting slightly on the chair. “You look like you just escaped a fundraiser and a firing squad.”
That earns a ghost of a smirk. He steps toward you. “Which one are you?”
You tilt your head. “Excuse me?”
“The fundraiser or the firing squad?”
“I’m the intermission,” you say smoothly. Then you uncross your legs and rise, slow, measured. You gave your name.
He watches you like he’s solving a riddle. “You don’t look like one.”
You arch a brow. “And what should I look like?”
He doesn’t answer. Just gestures toward the bar. “Drink?”
You nod. “I’ll have whatever you’re having.”
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.
“Harry Castillo,” he says eventually. Like it matters. Like you don’t already know exactly who he is.
You let the name hang there, then give a small, ironic smile. “Nice to meet you, Harry Castillo.”
You don’t 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 won’t end up on Page Six. But why now. Why tonight. Why you.
He doesn’t make a move. Doesn’t leer. Doesn’t even pretend to flirt.
He just leans against the bar, whiskey in hand, and says, “Do you want the short version or the long version?”
You take a sip. Let it burn a little. “Start with the short.”
“I need someone on my arm tomorrow night, maybe the month. Galas. Dinners. PR damage control.”
You raise a brow. “A girlfriend experience.”
“A convincing one.”
You swirl the drink, pretending to consider. But you already know your answer.
“How convincing are we talking?” you ask.
He meets your gaze again. His eyes are dark, but not cold. Just... quiet. Like he’s been through enough not to waste energy.
“You wear what you want. Say what you want. Just look like you want to be there.” A pause. “And don’t lie to me.”
You smile at that. “What makes you think I’m a liar?”
He finishes his drink in one measured swallow.
“I don’t,” he says.
And for the first time tonight, you think this job might actually be interesting.
You don’t usually stay this long. Most clients like to pretend there’s a rush. They fumble through their introductions, rush the champagne, get to the point. You’re 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 doesn’t move like a man trying to fill a void. He moves like he’s protecting one.
You lean back against the marble edge of the bar, letting the silence stretch again. He’s watching you, still and composed, the kind of stillness that comes from years of controlling rooms, markets, people.
“So,” you say lightly, “you’re not looking for sex.”
He doesn’t flinch. “I’m not looking to lie to myself.”
That earns him a faint smile from you - a real one. Honest. Dry.
“Good start,” you murmur. “But here’s the thing - if you want a girlfriend for longer than a night, you’ll need more than just heels and a pretty face.”
His brow lifts. “What do you charge for personality?”
You tap a finger against your glass. “Double.”
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.
“I’m not going to sleep with you,” he says calmly, and it’s not an insult. It’s a statement of terms. “Not unless you want to.”
You tilt your head. “Is that your way of being noble?”
“No. It’s my way of not confusing boundaries.” A pause. “Mine. Or yours.”
You study him for a beat. It’s not the first time a man’s drawn a line. But it is the first time you believe one might actually stick to it.
“So this is what you want?” you ask. “A fake girlfriend. For a month. In public. Private dinners, parties, events.”
“I'll see how you do tomorrow night. Then we can discuss the rest later.”
“You want me to dress the part. Charm your board. Laugh at your jokes.”
“I don’t need you to laugh,” he says. “Just show up.”
You consider him - the directness, the tiredness he doesn’t bother hiding, the sliver of something under all that restraint. Loneliness, maybe. Or something older.
“I’ll need a wardrobe if we agree to more than one event” you say, casual.
“Fine.”
“And a stylist. Because if we’re playing pretend, I’m not showing up in knockoff Louboutins.”
He nods once.
You watch him watching you, calculating. There’s no desire in his eyes — not the kind you’re used to seeing. Just thought. Just intention.
“And no NDA?” you ask softly.
He finally blinks. “You want one?”
“I want to know if I’m being hired as a woman… or a risk.”
That pauses him. His voice, when it comes, is lower. “I don’t think you’re either.”
You take the final sip of your drink, slow, deliberate.
“Then I accept,” you say, and hold out your hand. “Full illusion. Your perfect lie. You'll want me for the month Harry, trust me.”
He doesn’t 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 didn’t 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 “what happens next?” — because you already knew. Or because you didn’t 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 didn’t act like someone who’d 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 didn’t need a script to own a scene.
That dress. That voice. Those eyes that didn’t ask for permission.
He should’ve 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 bar’s 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, he’s 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 you’d disappear.
That was the plan.
But he already knew something wasn’t 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 hadn’t slept well in three months.
You didn’t ask about Lucy.
You didn’t 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,
“Full 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! ✨
Summary: Harry Castillo arrives in Wyoming expecting a simple acquisition: buy Willow Creek Ranch and move on to his next deal. Instead, he meets the ranch’s owner - a fiercely independent woman who refuses to sell the land her family has spent generations protecting. Their first meeting is filled with tension, frustration, and an undeniable spark neither of them expected. For Harry, it’s the first deal he can’t easily close. For her, he’s the first man who makes her question everything she thought she knew
Wyoming stretched endlessly beyond the windshield of the rented SUV, a landscape so vast it made Manhattan feel like another planet. Miles of sagebrush rolled into green valleys, broken only by weathered fences and the occasional herd of cattle grazing beneath an impossibly wide sky.
Harry loosened his tie and glanced at the navigation screen.
Seven more miles.
The proposal waiting in the leather briefcase beside him had taken six months to assemble. Market analysis. Environmental surveys. Financial projections. Every page had been scrutinized by lawyers, analysts, and investors.
To Harry, Willow Creek Ranch was an opportunity - the perfect location for an exclusive luxury resort.
By the end of the week, if everything went according to plan, the ranch would belong to him.
His phone vibrated through the console.
"Castillo."
"Ethan, all is well I hope?"
His lawyer. A man who had kept him on his toes and secure for the last 20 years. Ensuring every business deal went through like clock work.
"Ready and waiting to hear if you get this one over the line Harry. Could make you a lot of money - retirement might be closer than you think!"
"I haven't lost one yet."
"You sound confident." Harry's gaze stayed fixed on the gravel road ahead.
"I usually am." He ended the call before another question could follow. Confidence wasn't arrogance. It was preparation. Harry never walked into a negotiation without already knowing the likely outcome.
People had dreams. Businesses had debts. Families had emotions. Eventually, everyone reached a number they couldn't refuse.
The weathered wooden sign appeared beside the road.
WILLOW CREEK RANCH
He slowed the SUV and turned through the open gate. Dust rose behind him in soft clouds as the ranch came into view. It was larger than the photographs had suggested.
A white farmhouse sat at the centre of the property, shaded by towering cottonwoods whose leaves shimmered in the afternoon breeze. Beyond it stood a red barn, its faded paint telling stories of decades of Wyoming winters. Horses grazed peacefully in distant paddocks while mountains towered over the valley like silent guardians.
For reasons Harry couldn't explain, he found himself switching off the engine without immediately reaching for his phone.
The quiet was... unusual.
No sirens. No traffic. No endless hum of Manhattan.
Only birdsong, wind through the trees, and the rhythmic creak of an old porch swing moving gently in the breeze.
He stepped from the vehicle, polished shoes crunching across the gravel.
The silence broke with the sound of hoofbeats.
Harry turned.
A young woman guided a bay mare across the yard with effortless confidence, one hand resting lightly against the horse's neck. The mare matched her pace without resistance, as though following an old friend rather than a command.
She didn't look toward the SUV. Not immediately.
Instead, Harry watched as she secured the horse inside a nearby paddock before latching the gate with practiced ease.
Only then did she glance across the yard. Her eyes settled on him. There was no flicker of recognition. No surprise. No curiosity.
Just a calm, measuring look that lingered for a moment before she started walking in his direction.
Harry had spent years reading people. He knew nervousness. Ambition. Greed. He saw none of those things. But what he did see was the way her wavy hair blew in the gentle breeze, and how her hips moved as she walked. She was already nothing like New York girls. But Harry shook his head as though to remove his distracted theought.
She stopped a few feet away.
"Can I help you?"
Your voice was steady, almost casual, as though men in expensive suits wandered onto the ranch every afternoon.
Harry offered a polite smile.
"Harry Castillo."
You looked at him for a long moment.
"I know."
That gave him pause.
"You do?" He asked raising an eyebrow.
"The whole county's been talking about the billionaire from New York who's trying to buy the ranch." You folded your arms as you looked the stranger up and down. "Figured you'd show up eventually."
Harry studied you for the first time.
You couldn't have been older than your late twenties. Wind had loosened strands of hair from your ponytail, and the sleeves of your plaid shirt were rolled to your elbows. Dust clung to worn cowboy boots that had clearly seen years of work.
Nothing about you seemed staged.
Nothing about you seemed impressed.
And somehow... that intrigued him more than he expected.
“Harry,” he said, extending his hand. You hesitated for only a moment before taking it.
His handshake was firm, confident - the kind of handshake belonging to a man who was used to being listened to. You met it with one of your own, refusing to let him think you were intimidated.
“If Mr. Henderson is around, I’d like to speak with him,” Harry said.
You raised an eyebrow.
“You’re here to see Mr Henderson?” The slight confusion in his expression told you everything you needed to know.
“Yes,” he replied. “He owns this ranch, correct?”
You stared at him for a second before letting out a quiet breath.
“Owned.”
Harry’s brow furrowed.
“My father passed away two years ago. You would’ve thought a big shot buying the ranch would’ve known that.” you snorted.
The words weren’t cruel, but there was enough bite behind them to make him straighten slightly.
For the first time since arriving, Harry Castillo looked caught off guard.
“I apologise. I didn’t-”
“No, you didn’t.” You folded your arms, glancing briefly back toward the sprawling land behind you. “And that’s the problem.”
Harry studied you carefully.
You weren’t angry because he was rich. You weren’t angry because he wanted to buy the place. You were angry because he had looked at Willow Creek Ranch as a business opportunity without understanding what it meant.
“Look,” you continued, “I’ve already given your lawyers my answer.”
Harry’s expression hardened slightly.
“And what answer is that?”
You met his eyes. “Willow Creek Ranch is not for sale.”
The silence that followed was heavier than either of you expected. Harry had walked onto the ranch expecting a negotiation.
A number.
A signature.
A deal.
He hadn’t expected resistance. Well maybe a little.
And he definitely hadn’t expected it to come from the woman standing in front of him, covered in dust and wearing old boots, who had just looked one of New York’s most powerful investors in the eye and told him no.
He looked past you toward the ranch, taking in the wide stretch of land that disappeared into the Wyoming horizon.
“You’re refusing without hearing the updated offer?”
Your expression didn’t change.
“I heard the first one. No doesn't mean no where you're from I'm guessing,” you spat back.
“That was before I came here personally.” You almost smiled.
“And that’s supposed to change my mind?”
Harry paused. Most people were impressed by the fact that he showed up himself. It meant something. His time was valuable. But you just looked at him like he was another person standing on your property.
Not a billionaire.
Not a businessman.
Just a man.
“I’m trying to understand your position,” he said.
“No, you’re trying to understand what number will make me change my mind. And no number exists, so please get off my ranch before I have to force you off.”
His jaw tightened slightly. Because you were right.
“I don’t know you well enough to assume that.”
“You don’t know me at all. This isn't just land to buy at any price you want to throw. My family has owned this land for generations and I will not give it up for some wanna be money grabbing asshole who thinks he can convince me otherwise.”
The statement landed harder than he expected. Because it was true. He had spent weeks reviewing the ranch. Land value. Potential revenue. Development opportunities. But not once had he looked into the people who had spent their lives here. Not once had he wondered why someone would refuse the kind of money most people would dream about.
Harry glanced toward the old farmhouse.
“How long has your family owned this place?”
Your eyes followed his.
“Almost a hundred years.”
“A hundred years.”
You nodded. “My great-grandfather built the original barn by hand. My grandfather expanded the cattle operation. My dad spent his whole life keeping this place alive.” Your voice softened slightly. “And now it’s mine.”
Harry looked back at you.
“You run the entire ranch yourself?”
A small smile appeared.
“Were you expecting someone else?”
It was a simple question. But there was something behind it. A challenge. Harry didn’t answer immediately. Because maybe he had. Maybe some part of him had expected an older man. Someone who looked more like the ranch owner he had pictured in his head. Not a woman in her twenties standing in front of him, protecting a legacy.
“I wasn’t expecting you,” he admitted.
The honesty surprised both of you. Your eyebrows lifted slightly.
“At least that’s the first truthful thing you’ve said.”
Harry almost laughed. Almost.
“You always this difficult?”
“Only when people show up thinking they already know everything.”
“I don’t think I know everything.”
“You came here thinking this was a transaction.”
“It is a transaction.”
“No.” You shook your head. “That’s where you’re wrong. The ranch might be an investment to you. A number on a spreadsheet. But to me, it’s home.”
For a moment, neither of you spoke.
The wind moved across the fields, carrying the sound of horses in the distance.
Harry had sat across from executives who fought harder over millions than you were fighting over hundreds of acres. But this felt different. Because you weren’t trying to win. You were trying to protect something.
His phone buzzed. He glanced down.
A message from his assistant, Sarah.
Need update. Investors waiting.
He ignored it.
Your eyes flickered toward the phone.
“Busy?”
“Usually.”
“Then I won’t keep you.”
The words were polite.
But they were also a dismissal. And Harry wasn’t used to being dismissed.
“You’re really not going to reconsider?”
“No.”
“Not even if the offer increases?”
“No.”
“Everyone has a price.”.
You looked at him for a long moment. If he wasn't careful you would think he was about to get on his knees and start begging. Now what a sight that would make. This man just didn't get it.
“Maybe. But not everything is for sale.”
Harry held your gaze. For some reason, that answer bothered him more than an outright argument would have. Because he believed in deals. He believed everything could be negotiated. And now, standing on a ranch in the middle of Wyoming, he was faced with something he couldn’t put a value on.
You stepped back toward the barn.
“Enjoy your flight back to New York, Mr. Castillo.”
He watched you walk away. Slightly defeated.
Most people would have been relieved to end a difficult negotiation. Harry wasn’t. And he could help but continue to watch you walk away, the small swing in your hip like you had won the war. But it has only just begun.
Looks like he might be staying a little longer in Wyoming....
*******
You stood on the porch, arms folded against the cool Wyoming breeze, watching the black SUV disappear down the gravel drive until it became nothing more than a cloud of dust. Only then did you let out the breath you'd been holding.
"You did the right thing," you whispered to yourself.
So why didn't it feel like it?
You looked across the ranch. The horses grazed peacefully in the lower pasture, the old red barn standing exactly where it had for generations. Everything was as it had been that morning. Except you couldn't stop thinking about the man from New York.
Harry Castillo hadn't argued. He hadn't raised his voice. He hadn't thrown around his wealth or his reputation the way you'd expected. He'd simply looked... disappointed.
That should have made saying no easier. Instead, it made it harder.
The ranch wasn't for sale. It never would be. That should have been the end of it. So why couldn't you stop replaying the conversation?
You'd expected another arrogant businessman in an expensive suit - someone who thought enough money could solve every problem. Harry Castillo certainly looked the part. Tailored navy suit. Polished boots that had clearly never stepped in mud. An impossibly expensive watch that had probably cost more than your truck. But none of that was what lingered in your mind.
It was his face.
Annoyingly so.
Strong jaw dusted with the beginnings of stubble. Dark hair that looked as though he'd run a hand through it one too many times during the drive. Warm brown eyes that had held yours without ever making you feel uncomfortable.
And that smile...
You frowned at yourself.
It wasn't even a full smile. Just the slight lift at one corner of his mouth whenever you challenged him. It had been confident without being cocky.
Infuriatingly attractive.
You groaned, dragging a hand over your face.
"Seriously?"
Of all the men to find attractive... It had to be the billionaire from New York trying to buy your family's ranch.
You shook your head, almost laughing at yourself.
"He probably spends more on coffee in a week than I spend feeding the horses."
The thought should have made him seem ridiculous.
Instead, you found yourself wondering what he'd looked like without the suit jacket. Whether he always rolled his shirt sleeves to his forearms like that. Whether he always smelled faintly of cedarwood and expensive cologne, or if you'd only noticed because he'd been standing closer than either of you had realised.
Your cheeks warmed.
"Oh, for heaven's sake." You turned sharply towards the barn.
He was handsome. Ridiculously handsome.
That didn't change anything.
He was still trying to buy the place your family had spent his life building. Still trying to convince you to sell the only home you'd ever known. Still completely wrong.
...Even if he did have the nicest smile you'd seen in a very long time.
"You coming in?" One of the ranch hands leaned out of the barn, distracting you from your thoughts.
"In a minute."
You turned back towards the mountains, trying to shake the feeling that somehow the conversation wasn't over.
******
Harry drove in silence. The radio remained off. Sarah had already called twice. He ignored both calls.
He replayed the meeting in his head instead. The owner hadn't been who he'd expected.
Young, late twenties at least.
Sharp.
Completely unimpressed by him.
Unlike any woman he has ever met.
Most negotiations followed a familiar pattern. There was resistance, then discussion, then compromise. There had been none of that today.
Just one word.
No.
He found himself smiling despite himself. She'd challenged him and nobody challenged him anymore.
His phone rang again.
"Ethan."
"Please tell me you've got good news."
Harry glanced in the rear-view mirror, the ranch shrinking in the distance.
"Not exactly."
"What happened?" Ethan asked, concern thick in his voice.
"She refused."
"She?" Harry ran a hand through his hair.
"Yes, a stubborn she too. We need to double check everything we have on this ranch, her father passed two years ago. If we haven't picked that up, what else have we missed?" Harry said slightly irritated.
"Leave it with us Harry. So she said no immediately?" The sound of a keyboard tapping in the background echoed in the car.
"Immediately."
There was silence on the other end.
"That's... unusual."
Harry looked back towards the road leading to the ranch. "Very."
"So what's the next step?"
Harry didn't answer immediately. For once, he didn't have a solution ready. That was something that rarely happened. Harry Castillo always had a next move. A backup plan. Another route to take if the first one failed. That was how he had built his career.
Plan A.
Plan B.
Plan C.
He had never needed to think beyond that because people usually said yes eventually. But this time was different.
Willow Creek Ranch wasn't just another acquisition. The numbers were perfect, the opportunity was undeniable, and yet the one person standing in his way wasn't interested in being convinced.
And Harry had no idea what his next move was. Then, slowly, an idea began to form. Not a business strategy. Not another negotiation tactic. Something completely unexpected.
A different approach.
A way to understand the one person who had managed to make him question his usual playbook.
"Do me a favour. Get Sarah to book a table." Harry instructed.
"For...?"
"Grand Teton Lodge."
"The nicest restaurant in town?"
"Yes."
"And who am I booking it for?" Ethan asked, a hint of concern in his voice, wondering where this could possibly be leading too.
Harry smiled faintly. "Me."
Another pause.
"And Miss Henderson?"
"I'll invite her."
Ethan hesitated. "You think she'll come?"
Harry looked out at the Wyoming landscape, the sun starting to set over the mountains. "I honestly don't know."
******
The afternoon slipped by in the way it always did at Willow Creek. A broken gate hinge. A feed delivery that arrived an hour late. Two foals that seemed determined to test everyone's patience.
By the time you finally made it back to the farmhouse, the Wyoming sun had begun to sink behind the mountains, painting the sky in shades of orange and gold.
You kicked your dusty boots off on the porch and reached for the glass of iced tea you'd left on the kitchen counter that morning.
It had gone warm.
You sighed.
"Figures."
Your phone, abandoned beside the sink, began to vibrate across the worktop.
Unknown number.
You frowned.
Most people who needed you either drove up the lane or had your number saved.
You let it ring once.
Twice.
Three times.
Then curiosity got the better of you.
"Hello?"
"Miss Henderson?"
"Speaking." You asked pulling out a beer hidden at the back of the fridge.
"This is Harry Castillo." Shit.
"Mr. Castillo."
"I hope I'm not calling at a bad time." You stared at the cold beer in front of you.
"You are."
There was the faintest hint of laughter in his voice.
"I suspected as much."
"What do you want Mr Castillo?" You asked irritated that you hadn't had a sip of the well warmed drink.
"Harry please and I'd like to invite you to dinner." Your breath caught in your throat causing you to cough.
"Dinner?" You heard right.. right?
"Yes."
You grabbed your beer as you leaned against your kitchen island. "I already told you the ranch isn't for sale."
"I remember."
"So why would I have dinner with you?" You asked hoping he would realise how stupid of a suggestion this was.
"Because I'd like the chance to understand why."
"You can understand it over the phone Mr Castillo. No need to waste a good dinner on that." You smirked as you finally took a swig of the cold beer.
"I don't think I can." That caused you to place the bottle down. "It won't be a negotiation."
You snorted.
"It absolutely will."
"I'll make you a deal." His voice was smooth over the phone as he spoke. Your eyebrow lifted in curiosity.
"A deal?"
"No contracts. No paperwork. No lawyers. Just dinner."
"And the ranch doesn't come up?"
Harry smiled to himself. "I can't promise that."
"I knew it." You rolled your eyes.
"But I can promise I'll listen as much as I talk."
You walked out onto the porch, looking across the fields as the horses wandered towards the lower pasture.
The sensible answer was no. The obvious answer was no. So why were you hesitating?
"You really don't give up, do you?"
"I've never been very good at it." You chuckled at his answer.
"I noticed."
Silence settled between you for a moment. Finally, you sighed.
"One dinner."
Harry's smile widened.
"One dinner."
"If you start waving contracts at me, I'm leaving."
"I wouldn't dream of it."
"No sliding of figures over a bread basket."
"No figures. No bread basket." He agreed.
"And you're paying." You finalised. You could practically feel his smirk through the phone.
"I was planning to."
"Good." You shook your head, smiling again despite yourself. "Seven o'clock."
"I'll pick you up."
"No." You practically shouted down the phone. "Sorry, I mean, I'll meet you there."
He smiled to himself. "You still don't trust me."
"Not even a little."
"I appreciate the honesty."
"Get used to it, Mr. Castillo." He shook his head at the formality of his name.
"I was hoping I might." You both paused, neither of you hung up straight away. Neither of you seemed in a hurry to end the conversation. Eventually, you cleared your throat.
"I'll see you at seven."
"I'll be looking forward to it. I'll send you the details."
The call ended.
You stared at your phone for several moments before placing it back on the counter.
"This is not a date," you muttered to yourself.
From the paddock outside, one of the ranch hands called your name, asking where the spare feed buckets were. You answered automatically, but your mind was elsewhere. On a man from New York with kind brown eyes, an infuriating smile...
You picked up your phone again, your thumb scrolling to one name. You pressed the call button to am immediate answer.
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At 27 years old, you sign up with a high-end agency for your first “sugar baby” 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
Would you consider writing a Drabble where Harry almost forgets their 1. Year wedding anniversary 🍾🌷💗
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. – 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.