The Arrangement - A Harry Castillo Fanfic Masterlist
She’s the lie he hired. He’s the truth she wasn’t ready for.
After a bitter breakup with Lucy, 50-year-old private equity billionaire, Harry Castillo, isn’t looking for love - he just needs someone beautiful, discreet, and uncomplicated to be on his arm for a high-profile week of events in New York. What he gets is you, an escort, 28 years old, with sharp wit, hidden depth, and zero interest in becoming someone’s fantasy girlfriend off the clock.
But Harry makes you an offer you can’t refuse: a month of luxury, five-star hotels, couture fittings, private jets, and a generous paycheck… in exchange for playing the part of his girlfriend at a string of galas, charity balls, and business dinners.
You aren't some downtrodden dreamer. You are funny, clever, and fiercely independent. You're doing this job to stay in control of your own life - not waiting for a saviour. And Harry isn’t trying to fix anyone; in fact, he’s the one who might be broken, and he doesn’t even realise it.
Warnings: 🔞 NSFW themes (slow burn but oh it burns), smut, Escort x billionaire dynamic, Power imbalance (navigated and explored), Age gap (50m / 28f), Post-breakup emotional damage (on his end), Feminine rage + soft power, Men in suits, emotionally repressed, whiskey as a coping mechanism, Mutual pining (yes, even with a contract), Glamour, deception, and dangerous amounts of eye contact, Contractual arrangements that spiral into genuine affection, Rich people problems + broken people pretending they’re not, Soft power games, Sharp banter + late-night vulnerability, Trust issues + protective instincts
Pretty Woman inspired but make it jaded playlist 🎶
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! ✨
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
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 can’t be friends, and yet somehow becomes yours anyway.
Missed chances. Jealous moments. A New Year’s kiss that shouldn’t 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 Year’s Eve kiss, Hurt/comfort, Denial (lots of denial).
Warnings: 🔞 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 — 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 weren’t thinking about contracts or boundaries or anything except him.
Your stomach tightened.
This was never part of the deal. Sex wasn’t mentioned, wasn’t 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.
“Morning.”
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 who’d barely slept.
“Morning,” 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 wasn’t uncomfortable exactly - it was charged, thick with all the things neither of you could say.
He rubbed a hand over his face. “About last night…”
Your chest tightened. You couldn’t let him finish. “It can’t happen again.”
He stilled, eyes narrowing almost imperceptibly. “I was going to say the same.” But his tone wasn’t quite convincing, and he didn’t look away immediately.
“Good,” you said, pulling the sheet up over your chest like armor. “It was… not part of what I’m here for.”
Something flickered in his eyes - annoyance? Regret? You couldn’t tell. “Right. Just… a lapse in judgment.”
You forced a light shrug. “Happens.”
But the truth was still humming beneath your skin. Last night hadn’t 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. “I’ll get us some coffee.” His voice was casual, but his shoulders were stiff.
“Sure,” 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 he’d been.
You told yourself you were relieved it was over.
But your body, your thoughts, refused to believe you.
*****
Harry woke up before you.
He’d 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.
He’d never meant for it to happen.
Hell, it shouldn’t 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 wasn’t part of it.
But last night… last night he’d 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, he’d stayed. He’d watched you fall asleep against him, your breath warm on his chest, and for a dangerous moment, he’d let himself imagine what it would be like if this wasn’t temporary.
Now, in the pale light of morning, reality was clawing its way back in. The clock was ticking on your thirty days. He wasn’t supposed to want you beyond that - wasn’t 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.
“About last night…” he started, unsure whether to apologise or just pretend it didn’t matter.
“It can’t happen again,” you cut in.
The words landed like a punch, though he’d been bracing for them. He forced his jaw to unclench. “I was going to say the same.”
It wasn’t entirely a lie. It shouldn’t happen again. But the way your skin had felt under his hands, the way you’d said his name - he knew it would haunt him every time you stood beside him from now on.
“Right. Just a lapse in judgment,” he added, hoping it sounded casual.
“Happens.”
He didn’t miss the way you clutched the sheet higher, like you needed the barrier. He also didn’t 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. “I’ll get us some coffee.”
He looked at you once more before leaving - one last glance he shouldn’t have taken. You were staring at the empty space beside you, the same one he’d 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 wouldn’t stop it.
*****
Harry had been staring at the same spreadsheet for twenty minutes. The numbers blurred, his mind refusing to click into gear.
It wasn’t the deal. Wasn’t the shareholders’ meeting. It was you.
Last night kept looping in his head like some private, torturous reel - the way your breath had hitched when he’d 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 didn’t feel like an accident. It felt like something he’d been heading toward since the second you had walked into his life. And now that it had happened, he couldn’t remember a single good reason why it shouldn’t 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 he’d left on your skin blooming like proof. And you smiled, sleepy, content, right before telling him it couldn’t 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 wasn’t imagining you underneath him again. Pretending he wasn’t 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.
Harry’s 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 hadn’t noticed him yet. That was his mistake.
You’d 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 you’d arrived separately tonight. He’d come straight from work; you’d had the luxury of breathing space, time to rehearse the cool detachment you swore you’d keep.
It wasn’t 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.
“You’re late."
You turned, eyes skimming over him, a faint smile curling your lips, trying to ignore the butterflies in your stomach.
“Fashionably.”
“That 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 wasn’t 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 didn’t shy away.
Usually, you’d laugh it off. Make a joke. Pretend you weren’t 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 wouldn’t happen again. You told him it wouldn't happen again.
You tilted your chin, matching his stare. “You say that like you’re hoping I’ll take it off.” 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. “Don’t tempt me. Not here.”
But you could tell he wasn’t warning you. He was daring you.
The air between you thickened. People milled past, laughing and clinking glasses, but you didn’t hear a thing, not over the pulse of want building in your chest. His compliment wasn’t 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.
“Quite the gala tonight, huh?” His voice was smooth, casual, but there was something beneath it, an edge.
You returned the smile, matching his tone. “It’s hard not to be impressed. And you? Always managing to show up in style.”
Leo gave a slow, confident shrug, a sly smile playing at his lips. “Only when the company’s worth it.”
Your glance flicked toward Harry, who was watching from across the room. You let your smile deepen. “Well, I’m glad to be making an impression.”
Leo’s eyes darkened just slightly. “Careful with compliments like that. They tend to lead somewhere… interesting.”
You raised an eyebrow, biting back a smirk. “Maybe I’m in the mood for a little excitement.” 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. “Now that’s a conversation I’d like to keep going.”
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. “Dare I ask how the deal is going with Harry and your father?”
Leo’s smile flickered for a moment - just a flash - before he answered smoothly, “It’s moving along. Nothing finalized yet, but we’re close.”
You nodded, folding your hands loosely in front of you. “Harry hasn’t said much since that dinner.”
He glanced over, eyes narrowing just a bit. “Harry tends to keep things close to the chest. You know how he is.”
You did. The careful control, the way he guarded his business like it was a secret weapon. But something about Leo’s tone made you wonder if there was more beneath the surface - a tension you couldn’t quite place.
“Let me know if I can help,” you said lightly, the offer half business, half something else.
Leo’s grin returned, warm and a little dangerous. “I’ll hold you to that.”
The conversation drifted, but the unspoken currents beneath your words lingered - both of you playing your parts, aware of the lines you couldn’t cross.
But across the room, Harry’s jaw set. He didn’t 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.
“Excuse us.”
Leo blinked, but Harry was already steering you away, the heat of your body under his hand doing nothing to help his temper.
“That was rude.” you said, trying to keep your tone light as he guided you away, his hand firm but careful, like he was protecting something precious.
“That was necessary.”
He didn’t stop until you were tucked into a shadowed alcove just off the terrace, the muffled hum of the party spilling through the open doors.
“Harry....”
“You’ve been avoiding me.”
You laughed at his words. “I’ve been talking to people. That’s what one does at a gala.”
“Talking with Price.”
You laughed softly, without looking at him. “You really have a problem with that, don’t you?”
He stepped closer, close enough for the subtle scent of his cologne to reach you, warm, expensive, and maddeningly familiar.
“You’ve been avoiding me… because you’re remembering exactly what happened the last time we were alone."
The next thing you felt was the railing at your back and Harry’s 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 dress’s 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.
“We said...”
“I know what we said.”
His voice was low, controlled, but his grip tightened like he wasn’t 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.
“Every time I’ve looked at you tonight, you’ve been biting your lip. And I know exactly why.”
Your pulse thudded so hard you could hear it.
“You’re imagining things.” you rolled your eyes laughing, knowing he was absolutely right.
“I’m imagining what you’d sound like if I slid my hand up under this dress right now. And I bet you are too.”
His fingertips brushed your bare arm, just enough to make your breath catch before he stepped back, leaving you stranded in the cool air he’d just vacated. You were quick to miss the warmth of his body.
“Go back in there. Smile. Pretend you’re 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,
“Shall we get some air?”
The night was warm when you stepped outside, the garden strung with fairy lights, music muffled behind glass. He didn’t 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.
“Still think it was a lapse in judgement?”
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 didn’t even notice your clutch hit the ground.
And in that moment, you both knew there was no such thing as one time.
“We agreed....” you gasped for air as you pressed your hands to his chest lightly.
“We agreed while you were still breathless in my bed. That was never going to stick.”
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.
“Someone could see.”
“Then don’t make me give them a reason to look.”
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.
“Tell me to stop.”
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.
“Still think it was a one-off?”
Harry’s 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.
“You have no idea how hard it is to keep my hands off you tonight.”
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.
“Harry…”
“Say my name like that again and I’ll forget where we are.”
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. That’s what I thought.”
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.
“Harry…”
“Say it.”
He pressed his mouth to your jaw, your neck, each kiss hotter than the last.
“Harry...someone...”
“Don’t care.”
His voice was ragged, like he’d 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 didn’t.
Harry’s fingers caught the slit of your dress and eased it further apart, his palm cupping you over the thin scrap of lace you’d put on that morning without thinking of him - though you knew now you’d never wear them without thinking of him again.
“You’re soaked.”
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 Harry’s mouth found your ear.
“Don’t be quiet for me.”
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.
“This is-”
“-exactly what you want.”
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.
“That’s it. Just like last night.”
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 Harry’s eyes locked on yours like he could feel every pulse of heat building inside you.
“Come for me baby.”
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 — like nothing had shifted between you. Like the heat of your skin still clinging to his fingers didn’t exist. Your mouth fell slightly open, caught in the pull of disbelief and something deeper, something you weren’t 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 weren’t 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 weren’t 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 you’d both agreed to deny but clearly hadn’t forgotten.
The car slowed as it pulled up to the penthouse, and your heart jumped.
“We’re here,” 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 wasn’t over - but that whatever came next would be wrapped in tension, restraint, and all the things you hadn’t 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.
“No more pretending,” he says quietly. “Last night wasn’t just some mistake for me.”
You hold his gaze, cool and steady. “It wasn’t a mistake, Harry. I said it can't happen again. But I’m not in this for feelings. You know that.”
He takes a step closer, voice low. “Then why can’t I stop thinking about it? About you?”
You shrug, trying to not think about the dampness in your thong, desperate to play it cool. “Maybe you’re overthinking it.”
His lips twitch, amused. “Or maybe I’m the only one here who’s being honest.”
You raise an eyebrow. “Maybe. But honesty doesn’t mean I’m going to hand over my heart.”
He reaches out, brushing a loose strand of hair from your face. “I’m not asking for your heart. Just a chance.”
You smirk, stepping even closer. “Careful. You’re getting dangerously close.”
His voice drops to a whisper. “Danger is kind of my thing.”
Just as your lips almost meet, he pulls back slightly, eyes gleaming. “Not yet. I like watching you want me.”
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 you’re 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.
Warnings: 🔞 smut warning, yes we finally got there. 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.
For you, I would cross the line, I would waste my time, I would lose my mind. They say, "She's gone too far this time" - Taylor Swift
It starts with him knocking gently on your bedroom door.
You’re in the middle of scrolling aimlessly, wearing nothing but a robe and a silk headband you forgot to take off after washing your face. The knock isn’t loud, but it’s deliberate. You know his rhythm by now - that same, composed restraint that somehow makes everything feel more intimate.
You swing the door open halfway. “Yeah?”
Harry leans casually against the frame, one hand in his pocket, the other holding his phone like he was just about to text you instead.
He’s in a black T-shirt and dark trousers, clean-shaven, hair a little damp like he just stepped out of the shower. Unbothered. Effortless. Dangerous.
“You doing anything tonight?” he asks, tone light.
You raise a brow. “Other than existing in your spare room rent-free?”
His mouth twitches. “Thought I’d take you to dinner. If you wanted.”
You blink. “Like… actual dinner?”
“I meant a bar fight and a kebab van,” he deadpans.
You smile, despite yourself. “Where?”
“Somewhere low-lit. Music, good food, no one trying to sell us anything.” He pauses, eyes flicking down to your robe, then back up, pointed but polite. “Thought it might be nice to get out someone where normal for a change. Unless you’ve got plans.”
You hesitate. You don’t. But that’s not the point.
“This is just dinner?” you ask.
He nods. “No pressure. No work. Just you and me.”
You pretend to consider, even though your heart already said yes. “Sure, I can do dinner. ”
******
An hour later, he’s waiting by the door, checking his watch. He’s added a dark blazer over his T-shirt, and changed his shoes. You feel his gaze before he speaks.
The dress you wear is one of the simpler ones from the boutique - elegant, but not flashy. Soft black silk, thin straps, delicate across the collarbone. It sways when you walk. You didn’t choose it to impress him, not really. But part of you wonders if he’ll notice.
You move slowly down the steps. “Is this okay?”
His gaze lifts when he hears your heels, and then pauses. There’s a flicker of something. Appreciation, maybe. Or surprise. You can’t quite read it. He doesn’t say anything, just watches you cross the room with that stillness of his, the kind that always makes you feel slightly breathless, like he sees more than he’s letting on.
“You look...” he begins, then shakes his head slightly, and settles on, “Nice choice.”
You smile faintly. “You picked it.”
He lifts a brow. “I only paid for it.”
But when he opens the door for you and rests his hand at the small of your back to guide you out, it lingers half a second longer than it needs to.
*****
The restaurant is candlelit and quiet, tucked away in a side street near Tribeca. There’s no paparazzi, no flash, no hoards of billionaires and old money. Just polished wood tables, flickering glass votives, and the hum of conversation and jazz guitar.
You’re led to a corner table, partially hidden behind a column. It feels private in a way that’s intentional but not overbearing. Safe.
He lets you sit first. Lets you order first. Doesn’t correct your wine choice, doesn’t dominate the conversation. He just watches you, interested, relaxed, the slightest twitch at the corner of his mouth when you make a dry joke about the bread being better than your ex’s personality.
“I find that’s true of most sourdough,” he murmurs, swirling his wine.
You laugh. It’s easy. Too easy, maybe.
He doesn’t reach for your hand. Doesn’t touch you when the waiter pours wine. But his eyes keep returning to your mouth when you speak, your collarbone when you shift, your knees when you cross them beneath the table.
There’s a comfort in his presence tonight like neither of you are pretending. The conversation is slow and honest. Not about business. Not about image. Not even about the contract.
Just music. Food. People-watching.
At one point he tells you a story about nearly getting expelled from school - something about a stolen Vespa and a fire alarm. His voice is drier than the martini he’s sipping, but there’s a trace of fondness in it. You can picture it: younger Harry, scruffy, sharper around the edges. Still a little dangerous, even back then.
“Were you always like this?” you ask, eyes narrowing slightly as you lean on your elbow.
“Like what?”
“Intense. Observant. Kind of terrifying.” That earns you a slow smile.
“No,” he says simply. “That came later.”
You don’t ask what made it happen.
******
Over the main course, grilled sea bass for you, rare steak for him and the conversation turns unexpectedly light.
You mention how you once tried to learn French and gave up halfway because your tutor was too attractive. He gives you a flat look across his wine glass.
“Is that how it works with you? You get distracted by good bone structure and abandon all ambition?”
You lean back in your chair, unbothered.
“Only when the bone structure’s worth it,” you say, meeting his gaze over the rim of your own glass.
You lift your glass and glance at him over the rim. “Can I ask something?”
His brow rises. “Yeah.”
“What was your ex like?” Harry pauses.
You didn’t mean it to come out that way, so casual but you hold his gaze anyway. He leans back a little, arms resting loosely on the counter behind him.
“Lucy?” he says after a beat. You nod not expecting an answer. Not a real one. But he gives it anyway.
“She was... smart. A strategist. No illusions.” A faint smile flickers at his mouth, more memory than fondness. “We were good on paper.”
“But not in person?” His eyes lift to yours.
“No.”
You don't press. Instead, you say, “I always wonder what people leave behind in breakups. The stuff no one else sees.”
Harry looks at you for a long moment, quiet. Then, finally, he says, “She said I cared more about control than connection. That I didn’t let people close.” A small breath. “And she was right. I liked being needed more than being known.”
You blink. “That’s… honest.” He smiles faintly.
“You asked.”
“I guess I’m just not used to men who talk like that.”
“Like what?”
“Like they’ve thought about it.” Harry shrugs.
“Maybe I’ve had to.” You don't say anything to that. Just take another sip. There’s a heaviness in the air now, not uncomfortable, but weighty. Meaningful. He studies you again.
“What about you?”
“What about me?”
“Anyone serious?” You let out a short laugh.
“God, no. You think men date girls like me?”
His eyes darken a little. “I think they want to.”
You hum, gaze falling to your mug. “Wanting isn’t the same as staying.”
That lands somewhere between you both. Harry doesn’t push further.
By the time dessert is offered, you’re both sitting a little closer. Not touching. But the air between you is warm now. Easy. You shake your head when the waiter appears with the menu.
“Too full.”
“Coffee?” Harry asks, already glancing at the waiter.
You nod. “Always.”
The waiter disappears. Harry leans back slightly in his chair, studying you in that unreadable way he has.
“What?” you ask, suddenly aware of how soft your voice sounds in this place.
“Nothing,” he says. Then: “You’re different when you’re not trying.”
You tilt your head. “You think I’m trying most of the time?”
“I think you’ve had to,” he says. “Tonight... it doesn’t feel like work.”
You don’t say anything for a moment. Just study him. Most men like to see only what you show them, the curated version, the practiced smile, the performance.
Harry, on the other hand, seems to watch for what’s underneath.
It’s disarming. And you don’t know what to do with it.
You wait until the coffees arrives before you ask it, timing it so the clink of spoons and the low hum of conversation soften the edges of the question.
“I've been meaning to ask. Why wasn’t sex in the contract?” you say, casual on the surface, but watching him closely. “Very unusual for a man of your stature to not want a woman in his bed that he is paying for."
Harry pushed back his cup and for a moment, he looks at you as if weighing whether to laugh it off or answer honestly.
“Because I didn’t want that to be what you thought I was buying,” he says at last, his voice low, deliberate. “I wanted your presence, your attention… without you wondering what it might cost you later.”
You tilt your head, a faint smile playing at your lips. “And here I thought you just had saintly self-control.”
The corner of his mouth curves, but his gaze doesn’t waver. “Don’t mistake restraint for disinterest.”
The line lands heavier than you expect, settling between you along with the unspoken things neither of you dares to chase just yet.
******
Outside, the night is warm and quiet.
He offers his jacket when he sees your arms are bare, and you let him drape it over your shoulders. It smells like him, bergamot and something smoky, and it makes your stomach twist in the most inconvenient way.
On the walk back to the car, there’s a moment.
You pause at the curb as Luca pulls up. Harry lingers behind you, and you feel the brush of his hand on your lower back, not possessive, not overt. Just steady.
You glance at him over your shoulder.
“Thanks for dinner. I had a really good time." you murmur.
His voice is quiet. “Any time.”
And the way he says it, soft, sincere, like he means every syllable, makes something inside you flicker dangerously close to wanting.
*****
The car ride is quiet, but not awkward. You rest your head against the window, the city blurring past, your hands folded neatly in your lap. He doesn’t speak, doesn’t try to fill the silence. There’s something in that restraint that makes your chest ache.
When the lift doors open into the penthouse, he lets you step out first. You toe off your heels by the door, your feet aching. He watches you do it.
Usually, this is the part where things turn, where the evening shifts toward the bedroom or the door or some awkward negotiation of roles. But Harry doesn’t move toward you.
The city is quiet beyond the glass, the skyline flickering in reflections across the floor-to-ceiling windows. Inside the penthouse, the air is dim and hushed. The kind of quiet that makes you whisper without knowing why.
You’re barefoot now, wineglass still in hand, standing near the window with the lights behind you. Harry’s across the room, jacket long since discarded, shirt sleeves rolled to the forearms. The top two buttons undone. No tie.
He watches you as you sip.
“You always this quiet after dinner?” you ask softly.
“Only when I’m thinking.”
You glance over your shoulder. “About what?”
He doesn’t answer right away. Just walks over, slow and steady, until he’s standing beside you. Not touching, not even close enough for that but near enough that you can feel the heat of him. The energy, low and humming between you.
He lifts his glass. “That you surprise me,” he says.
You look up at him. His face is unreadable again, except for the faint crease at the edge of his brow, something thoughtful, something unsettled.
“You say that like it’s a bad thing.”
“No,” he says, after a beat. “It’s not.”
A quiet settles. You can feel the air shift.
And then, very slowly, he reaches out, just two fingers, brushing a loose strand of hair away from your cheek. Not possessive. Not practiced. Just… tender.
Your breath catches.
He notices. His hand lingers for a second longer than it should, fingertips grazing your jaw, and your eyes meet his.
There’s a flicker, something unsaid that flickers like a match.
You tilt your face slightly toward his. Not a move. Not an invitation. Just enough that your lips are close now. A breath apart.
He leans in.
You think he’s going to do it.
And for a split second, you want him to.
But he stops.
Right there.
His nose almost brushing yours, his voice low, rougher than before. “If I kiss you right now…”
You wait, heart thudding. “What?”
“I won’t stop there.”
Your pulse stumbles. Silence. You can’t breathe.
And then, he takes a breath, blinks once, and leans back. Withdraws his hand. His jaw tightens.
“I’ll say goodnight,” he murmurs, stepping away. “Before I forget why I shouldn't.”
You’re left alone by the window. Wineglass warm in your hand. Cheeks flushed. Mouth parted.
And it takes longer than you’d like for your heart to settle.
*****
You close the bedroom door behind you with a soft click.
The hallway still echoes with the ghost of his voice -"If I kiss you right now..." and it replays in your head like a song you can’t turn off. That low, deliberate tone. The pause. The way he looked at you like he wanted to break every rule he’d written. And every rule you had created.
You lean against the door and exhale. Your wineglass is still warm in your hand, your fingers loose around the stem.
God, what was that?
You have been with men before. Rich men. Powerful men. Men who expect, who assume, who take. You know how to play the game. Know how to read their body language, when they’re bluffing, when they’re bluffing themselves.
But Harry…
He didn’t touch you like you were his. He didn’t kiss you just because he could.
He pulled back.
I won’t stop there.
The words twist in your stomach. Not fear. Not nerves. Just heat - low and unexpected. You hadn’t even planned to flirt tonight. This wasn’t one of those outings. No show to put on. No flashbulbs, no high-slit dresses, no lipstick like armour.
Just dinner.
You push away from the door and sets the wineglass down on the side table. Shrugs off the black blazer he's given you to wear after dinner. It smells like him now - warm cedar and something deeper, expensive, but not try-hard.
You catche a glimpse of yourself in the mirror across the room. Bare shoulders. Sleep shorts. Hair down.
There’s something disarmed about you tonight.
You don't like it.
No...you do. That’s the problem.
With Harry, you keep losing your balance. One moment your fully in control, smiling sweetly while he watches you from across a crowded room. The next, your standing by a window with his hand on your face and the air thick with something that doesn’t feel transactional at all.
You brush your fingertips over your cheek where he touched you. It’s still warm.
Maybe it was nothing. A moment. Men like him probably collect moments and forget them by morning.
But the way he looked at you...
You shake your head.
This isn’t that kind of story. You don't get caught. You can’t afford to.
You climb into bed, but the sheets feel too cold and your thoughts too loud. Your body still humming from how close he’d been. From how close you'd got to tipping into something dangerous.
From the fact that he could have kissed you - and didn’t.
And that not kissing you somehow felt even more intimate.
*****
You stare at the hallway for a full thirty seconds before moving.
Your bare feet are silent on the polished floors, your heartbeat anything but. The silk of your sleep shorts whispers against your skin, and your arms folded across the oversized blazer you still hasn’t returned. His blazer. Your knuckles brush the edge of the lapel as you walk, stupid how grounding it feels, how steady.
You don't know why you're doing this.
That’s a lie.
You do.
You're not sure what you want, exactly. But it’s definitely not lying awake in a cold bed while your brain replays the sound of his voice and the look in his eyes when he said, "I won’t stop there."
Your hand lifts before you can think too hard. One soft knock.
You nearly walk away right after.
But then you hear the low creak of floorboards, the muffled shift of movement. The door opens slowly, only a little at first. And then fully.
Harry stands there, shirtless, in black drawstring trousers. Barefoot. His hair mussed in a way you have never seen, looser, softer. He blinks once, adjusting to the hallway light, and then looks at you properly.
Still quiet. No surprise. Just him.
“Couldn’t sleep,” you say lightly, your voice smaller than you expected. “Too quiet.”
He looks at her a second longer, not just at her, but into her, like he’s weighing the exact meaning of why she’s here, now, like this.
His gaze lingers on your face, then drops to the blazer. His blazer. His voice, when it comes, is low and rough from sleep. “You want to come in?”
You hesitate. Not because you're unsure but because this is you. The girl who always knows what you're doing. The one who’s paid to be five steps ahead, to own a room, a man, a night. You don't knock on doors. Not unless you're paid too.
But you nod.
He steps aside. You brush past him and into the warmth of his room.
It smells faintly like cedar and laundry and something darker, lived-in. There’s a glass of water by his nightstand, a few papers on the desk in the corner. Everything is neat, except for the tousled bed and the way your presence seems to warp the air around them.
Harry leans against the edge of the windowsill, arms crossed. Watching you. Not like a man sizing up an opportunity. Like someone trying not to cross a line he drew himself.
You turn to him. “Harry.”
“You okay?” he asks, voice still soft, careful.
“I just…” You swallow. “I didn’t want to be alone.”
Something in his expression shifts. Not lust. Not smugness. Just… understanding.
His tone is almost teasing when he says, “I take it you’re not here for a midnight strategy meeting.”
You smile faintly, a flicker of relief easing the tension that had been coiling inside you. "Not unless it involves pillows," you say softly, trying to keep the mood light.
But before you can even catch your breath, he’s already in front of you, the air between you thick with something unspoken.
His eyes darken, sharp and searching. "What are you really here for?"
You feel the weight of that question, more than just words, more than curiosity. It’s a challenge, an invitation, a promise all rolled into one.
You meet his gaze, steady despite the fluttering in your chest.
"I came because I needed to be close," you whisper, voice low. "Close to something real."
His jaw tightens, and for a moment, the guarded man slips away, replaced by someone raw and vulnerable.
Slowly, deliberately, he reaches out, fingers brushing a stray lock of hair behind your ear.
"And now that you’re here," he murmurs, voice husky, "what do you want to do with that?"
The air between you crackles, electric, tense, ready to ignite.
You take a small step closer, heart pounding, breath shallow, and the space between you disappears.
He closes the distance, his breath warm against your skin as his hand cups your cheek, thumb tracing a slow, deliberate path along your jaw. Every nerve in your body ignites under his touch, the tension building with a delicious intensity.
Your eyes flicker shut for a moment, savoring the charged silence between you, before you lean into his palm, needing the reassurance of his touch.
His lips find yours, soft at first, tentative, as if testing the waters. Then the kiss deepens, slow and consuming, like a flame growing steadily, threatening to engulf you both.
Your hands rest against his chest, feeling the steady beat of his heart, matching the rapid rhythm building in your own veins.
When he pulls back just enough to whisper, “Tell me what you want,” his voice is rough, edged with desire and something more vulnerable.
You meet his gaze, breathless but steady. “I want to stop pretending,” you confess, “even if just for tonight.”
He smiles, a slow, genuine curve that lights up his eyes. “You sure?”
"Certain."
His hands explore your body with reverence, tracing every curve and hollow, igniting every nerve ending. The world outside ceases to exist, there’s only this moment, this connection, raw and electric.
As he guides you toward the bed, the anticipation coils tighter, every touch a promise, every glance a silent vow.
When your lips meet again, it’s with the full weight of all the things left unsaid, all the emotions barely held back.
Tonight, you’re no longer just an arrangement. You’re something more.
It’s nothing like you imagined.
It’s more.
Hot. Unsteady. All control gone. His lips are rough with need, one hand cupping your jaw like he needs to feel your shape to believe you are real. You melt into him, fingers fisting the front of his shirt, kissing him back like your whole body’s been waiting for this exact moment.
He groans against your mouth, pulling back just slightly.
“Tell me to stop,” he says hoarsely.
You breathe against his lips. “Don’t you dare.”
His mouth crashes back into yours.
You don’t make it to the bed right away, not at first. Your back finds the wall beside the door, his hand bunching the hem of your shirt as your knee slips between his legs.
The urgency is clumsy, breathless, a collision of desire and hesitation. His mouth finds yours again, rough and demanding, swallowing every gasp you manage to catch. Your hands tangle in his hair, pulling him closer, needing the press of his body against yours.
Slowly, the frenzy begins to ease. His hands trail from your waist to your back, pulling you tighter with a possessive firmness. His lips descend to your neck, teeth grazing lightly before sucking a mark that leaves you shivering. His fingers slip beneath your shirt, fingertips burning trails across your skin, seeking every sensitive spot.
Your breath hitches as his hand finds the curve of your breast, palm heavy and warm. His thumb circles your nipple, coaxing it hard beneath his touch, while his other hand slips lower, brushing against the waistband of your underwear. The friction between your bodies is electric, sending waves of heat pooling deeper.
He presses against you harder now, his length straining urgently, teasing the seam of your underwear. Your hips rock forward instinctively, desperate for more. His hand moves boldly, sliding your panties aside, fingers teasing your wetness through the slick heat that’s already pooled. You let out a low moan, nails digging into his shoulders as he explores you slowly, deliberately.
The wall no longer feels cold, it’s the heat of your bodies clashing that fills the space. His mouth returns to yours, tongue slipping past your lips, claiming you with hunger and tenderness all at once.
When he finally lowers you from the wall, guiding you toward the bed, every touch is charged with intent.
Your hands tremble slightly as you reach for the buttons on your shirt, fingers brushing against his as he helps guide them free. Each button undone feels like a small surrender, a permission granted to the space growing between you. The fabric parts slowly, sliding off your shoulders to reveal the smooth skin beneath, exposed and vulnerable under the dim glow of the room.
He watches you intently, eyes dark and hungry, but there’s a tenderness there too, like he’s memorizing every inch. Your hands trace over his bare chest trying to remember every touch.
His lips follow the bare expanse of your collarbone, kissing a slow, deliberate trail down to your breasts. You arch into him instinctively, hands sliding behind his back to peel his trousers away.
When the fabric falls away, you take a moment to drink in the sight of him, strong, exposed, the curves and lines you’ve been craving now tangible beneath your hands.
He leans in again, lips capturing yours in a kiss that’s deep and slow, filled with reverence and hunger both. Your hands explore his back, tracing the muscles that tense beneath your touch, while his hands roam your curves, mapping the soft planes of your body.
Every moment stretches out, slow and deliberate, as you shed the last of your reservations, piece by piece until there is nothing left but the heat between you, the rhythm of your bodies beginning to move as one.
His fingers slide slowly, teasing your skin as he parts your underwear, the heat between you rising with every inch. You breathe out a soft, shaky sigh, fingers tangling in his hair, pulling him closer.
“God, you’re already so wet,” he murmurs against your inner thigh, voice low and thick with desire.
You arch your back, lips parting as his tongue flicks over your skin, slow and deliberate, drawing a moan you can’t hold back.
“Harry...” you whisper, voice trembling, “Please...”
He looks up at you through dark lashes, eyes burning with need. “Tell me what you want.”
“I want you,” you admit, heart pounding. “I want all of you.”
His smile is a wicked promise as he moves upward, capturing your lips in a deep, hungry kiss. His hands roam your body, fingers tracing every curve, every sensitive spot, making your skin flush.
His fingers slip inside you slowly, carefully, watching your reactions, letting you set the pace.
“Does that feel good?” he asks, voice husky.
You nod, biting your lip to keep from moaning louder. “Yes... more...”
He responds with a steady rhythm, thrusting slow and deep, hands gripping your hips, holding you close.
“Fuck, you’re incredible,” he breathes, voice rough, lost in the moment.
You reach up, tracing the line of his jaw, feeling the heat of his skin under your fingertips. “Don’t stop.”
His fingers part you gently, sliding inside with deliberate care, every inch coaxed in slowly, letting you adjust to the delicious fullness. You bite your lip, a low moan escaping as the stretch melts into steady, exquisite pressure.
“God, you feel so good,” he murmurs against your skin, his voice thick with need. His thumb circles your clit lightly, sending jolts of heat spiraling through your body.
You arch your back, pressing into his touch, breath hitching. “More,” you whisper, fingers tangling in his hair, pulling him closer.
He obliges, curling his fingers inside you, hitting the spots that make your knees tremble. His mouth finds yours in a fierce kiss, tongue swirling, matching the rhythm of his fingers teasing you relentlessly.
His other hand grips your hip, holding you steady as he slides deeper, slower, each movement deliberate, worshipful. “You’re so wet for me,” he groans, voice husky.
You wrap your legs around his waist, pulling him closer, desperate for every inch. His mouth trails down your neck, sucking and biting softly, leaving a trail of fire in his wake.
His fingers flick expertly at your clit, each stroke building the pressure until you’re trembling, gasping beneath him.
“Harry,” you cry, hips bucking, “I’m so close."
He matches your pace, thrusting slowly inside you while his fingers circle your clit, driving you higher and higher.
With a strangled moan, you shatter, waves of pleasure crashing through your body as your muscles clench around him. He holds you through it, steady and sure, before following with a deep groan of his own, filling you completely.
His lips trail down your neck, across your collarbone, until they reach the curve of your breast, kissing and teasing until your breath quickens. Then, slowly, deliberately, his mouth travels lower - down your stomach, across your hipbones - each touch feather-light, sending shivers racing through your skin.
You gasp softly as his warm breath brushes the sensitive skin of your inner thigh, fingers parting you gently, exposing the place that’s already glistening with desire.
"I've got to taste you baby."
His tongue flicks out, tasting you with slow, deliberate strokes that make your whole body tighten with anticipation. He circles your most sensitive spot, teasing the flat of his tongue over your folds, coaxing a low, involuntary moan from deep inside your chest.
“Tell me how you want it,” he murmurs, voice husky and thick with need.
You tremble, hips arching upward. “Slow... and steady,” you whisper, voice barely audible but full of want.
He obeys, tongue swirling in lazy circles, flicking and tracing, his lips sucking softly before moving to nibble gently along your sensitive flesh.
Your fingers grip the sheets as pleasure coils tighter, building with every skilled movement. He slips a finger inside you, matching the rhythm of his tongue, sending shockwaves through your body.
“Jesus Harry,” you moan, voice shaky, “Don’t stop.”
His hands grip your hips, anchoring you, as he intensifies the rhythm - tongue teasing, flicking, pressing just right until you’re gasping and trembling, riding the edge of release.
With a final, deliberate flick, he sends you tumbling over the edge again, your body convulsing with pleasure as he holds you steady, lips soft against your skin.
As you come down from the waves, his eyes find yours, full of warmth and something unspoken, connection, trust, and raw desire.
You trail your fingers along the curve of his hips, your eyes dark with want as you slowly lean down, lips grazing the sensitive skin of his lower stomach. Your breath fans over him, teasing, inviting.
Your tongue flicks out, soft and warm, just as you begin to explore, ready to take him fully into your mouth.
But before you can, his hand presses gently but firmly against the back of your head, stopping you mid-motion.
His eyes meet yours, intense, calm, holding an unspoken command. “Not yet,” he murmurs, voice low and steady.
You pause, breath caught in your throat, heart pounding not from rejection, but from the weight of his control. The way he’s holding you back isn’t denial; it’s something else entirely.
He cups your face, thumb brushing over your cheek with slow tenderness. “I want you. All of you. No rush,” he says, voice thick with need.
You look up at him, a slow smile curling your lips as the tension between you shifts. There’s trust here, in his restraint, in the way he’s telling you that he wants this moment to be right, not rushed.
You lean back just enough to meet his gaze fully, the heat between you simmering, deliciously suspended.
“Okay,” you whisper, voice soft but full of promise.
He pulls you up into a kiss, slow, deep, filled with everything he’s been holding back. His hands travel your body with reverence, reminding you that this night is about more than just urgency.
The unspoken tension lingers, thick and sweet, as you both settle into the slow burn, savoring every breath, every touch, every moment together.
He deepens the kiss, hands sliding from your waist down to your thighs, lifting you effortlessly as his lips never break contact with yours. Your breath hitches, heart pounding wildly against his chest. You press closer, feeling the steady heat radiating from him, every nerve alive with anticipation.
His mouth trails down your jaw to your neck, leaving hot, demanding kisses that make you shiver. Your hands roam his back, memorizing the firm muscles beneath your touch.
When he finally breaks the kiss, his voice is low, thick with desire. “Tonight is about you. Every inch of you.”
You nod, eyes heavy-lidded, your body already aching for more.
He settles you gently onto the bed, lips following your every movement, hands exploring with reverence and urgency. His touch is both commanding and tender, a perfect balance that leaves you breathless.
Slow and deliberate, he takes his time undoing the last barriers between you, every second a promise.
As he finally enters you, the sensation overwhelms every nerve ending, a perfect blend of tenderness and raw, urgent passion that steals your breath. The slow, full stretch gives way to a deep, steady pressure that fills you completely, making your muscles clench instinctively around him.
His hands grip your hips with possessive strength, anchoring you as he sets a deliberate rhythm, thrusting deep and slow, allowing every inch of connection to register, every gasp and shiver to fuel him.
“You feel so fucking good,” he murmurs against your lips, voice rough and low.
Your breath hitches, a soft moan escaping your lips as he begins to pick up the pace, hips rolling with increasing urgency. The slick glide of skin against skin, the slick heat pooling between you, wraps you in a haze of sensation.
He leans down, mouth capturing yours in a fierce kiss, tongue dancing with yours as his hands roam, one trailing down your side, fingers teasing your clit with light, circular strokes that send jolts of pleasure radiating through your body.
“Tell me what you want,” he growls, breath hot against your skin.
You arch into him, gasping against his mouth as the dual sensations overwhelm you, the stretch inside, the teasing outside, building toward a crescendo.
“Faster,” you whisper, voice trembling.
“Fuck, you’re mine,” he groans, his pace growing more demanding, every thrust pushing you closer to the edge.
Your hands clutch his shoulders, nails digging in as your body trembles, hips meeting his in a frantic rhythm. The tension coils tighter, muscles tightening, breath catching in your throat.
With a strangled cry, you shatter, waves of pleasure crashing through your body as your muscles clamp down on him, every nerve on fire.
After a few deep, steady thrusts, he slows, his breath heavy and warm against your neck. You feel his hands on your hips, steadying you, and an unspoken invitation to take the lead.
You shift, sliding your hands down his chest as you rise, your knees pressing on either side of his hips. His eyes darken with desire, watching every movement as you settle onto him, your body molding perfectly against his.
You lean forward, lips brushing his collarbone, then trailing slow kisses along his jawline. His hands roam your back, fingers digging in lightly, grounding you as you begin to move.
You set the pace, slow at first, hips rolling in a seductive rhythm that sends a delicious burn deep inside. You watch his face, mesmerized by the way his eyes close, lips parted, breath catching with every stroke.
“Fuck, you look incredible,” he breathes, voice rough with need.
You smile against his skin, picking up the pace just a little, hips grinding, riding him with a steady, controlled sway that makes his hands tighten on your hips.
“You feel so good wrapped around me like this,” he groans, voice thick.
You lean down to capture his mouth in a fierce kiss, tongue tangling with his as your hips roll faster, each movement igniting a fire that blazes hotter between you.
The world narrows to the slick glide of skin on skin, your bodies moving in perfect harmony, breath mingling, heartbeats racing.
When you finally lean back, resting your hands on his chest, your gaze locks with his, full of heat and promise.
His breath catches, and he groans low in your ear, fingers digging into your hips to keep you steady. “Fuck, I’ve never felt anything like this.”
You lean down, capturing his lips in a fierce kiss, tongues dancing in perfect sync. The taste of him is intoxicating, salty, warm, urgent.
Your body moves with a confidence you didn’t know you had, each grind and roll a statement, a claim. You feel him respond, his hips thrusting up to meet yours, the friction building between you both unbearable.
“Come for me,” he whispers, voice breaking slightly.
Your muscles clench, pleasure spiraling out of control as you ride the wave, moans spilling freely, filling the room. His hands roam your body, every touch sending shivers down your spine.
When the climax finally crashes over you, it’s like fire bursting through every nerve ending, raw, fierce, beautiful. You collapse against him, breathless, your skin slick with sweat.
He follows soon after, his groan deep and guttural as he spills inside you, holding you close, skin slick and glistening in the soft light.
“Stay with me,” he breathes, voice thick.
You collapse into his arms, breathless and sated, the quiet afterglow wrapping around you both like a warm blanket.
