Chapter Eighteen: The Date
Warnings: Escort x billionaire dynamic, Power imbalance (navigated and explored), Age gap (50m / 28f), Post-breakup emotional damage, Feminine rage + soft power, Men in suits, emotionally repressed, whiskey as a coping mechanism, Mutual pining (yes, even with a contract), Glamour.
The wrong place at the right time and I break down, then he's pullin' me in, in a world of boys, he's a gentleman - Taylor Swift
He watched you move around the penthouse, silent and deliberate, picking up your things with a carefulness that reminded him just how guarded you were. Every motion, every glance in his direction, carried caution but also a strange comfort, like you were testing the waters without fully admitting it.
Harry leaned against the kitchen counter, arms crossed loosely, observing you from across the room. The apology had been said, the Richard fallout handled, and yet… the tension lingered. He wasn’t used to someone being this close, this present, and still so carefully distant. He wanted to reach out, to bridge the gap, but he knew patience was the only way forward.
When you mentioned leaving, he felt that familiar knot in his chest but he didn’t push. Instead, he tried to anchor himself in the simplicity of the moment. “You don’t have to go,” he said softly, more as an offer than a command. You hesitated, eyes flicking up to meet his, then back down to your shoes.
And then… you stayed.
Harry didn’t say anything. He didn’t need to. He simply watched as you settled onto the sofa, tucking your legs underneath you, and pulled the blanket over your shoulders. He poured himself a coffee and sat across from you, enjoying the quiet hum of the city below through the floor-to-ceiling windows. The silence wasn’t awkward. It was easy, almost domestic, the kind of unspoken understanding that only came when trust, fragile and new, was being rebuilt.
Every so often, your eyes would meet his, a flicker of acknowledgment passing between you before you looked away. Harry felt his chest tighten in a way that wasn’t desperation but anticipation. Every small smile, every casual stretch of your legs, every sip of coffee you took felt like a silent reassurance that maybe, just maybe, you were letting him back in, careful, but inch by inch.
He leaned back in his chair, letting himself enjoy it. No rush. No expectations. Just you, him, and the quiet rebuilding of something that had been nearly lost.
The night stretched ahead, and Harry silently promised himself he would guard it, nurture it, let it grow, one small moment at a time.
That next morning, you tugged the blanket tighter around your shoulders, standing slowly as the sunlight filtered through the blinds. The penthouse felt quiet, too quiet, and your stomach knotted at the thought of leaving. Harry was perched on the edge of the sofa, coffee in hand, eyes quietly following you.
“I should… I should get going,” you murmured, voice soft. You tried not to meet his gaze, but his presence made it impossible to keep your thoughts straight.
He set his mug down, standing but not moving closer. “You don’t have to go if you don’t want to,” he said carefully. “Stay a little longer. Just… for now.”
You shook your head, managing a small smile. “I really should. I have a client tonight.” The words tasted bitter, even though you said them like any other line of your work. Escorting wasn’t about love or trust, and you needed to keep it that way...for now.
Harry’s expression flickered, that tension in his jaw softening slightly. “Right… work,” he murmured. His voice wasn’t harsh, but you could hear the weight behind it. He clearly didn’t like the thought of you going out into that world, not doing what you do but he didn’t argue. Not right now. Not so soon after he had you back in his penthouse. In his life.
You grabbed your bag and slung it over your shoulder, pausing by the door. “I had a good night,” you said softly, almost as if testing the waters. “Thanks… for everything.”
He gave a small nod, a shadow of a smile tugging at his lips. “Be careful tonight,” he said, and for the first time, it wasn’t just a polite warning, it carried concern, something far more personal than your arrangement had ever allowed.
You paused for a heartbeat, glancing back at him. The way he looked, calm, steady, watching without pressuring you felt that tiny pull in your chest that had made the last month so complicated. But you couldn’t stay, not yet. Not when there were rules, clients, and boundaries you weren’t ready to cross.
You paused at the threshold of the penthouse, your bag slung over your shoulder, your heels clicking softly on the marble floor. Harry’s gaze followed you, steady, expectant, as if he already knew the space you’d need but still couldn’t let you go entirely.
“Text me when you get home,” he said quietly, his voice low but firm, almost pleading. There was a subtle vulnerability there, one that made your chest tighten.
Instead of replying, you leaned in, brushing your lips lightly against his cheek. The gesture was soft, fleeting, but deliberate, a small act of closeness, a reassurance, a way to bridge the distance between you without words.
Harry froze. His eyes widened slightly, surprise flickering across his face. He hadn’t expected it, not this way, not from you, not yet.
You pulled back just enough to give him a teasing, gentle smile, whispering softly, “I will.”
He nodded, still caught off guard, his hand twitching as if he wanted to reach for you again but didn’t. You straightened, adjusted your bag, and turned toward the elevator. Each step echoed in the quiet penthouse, carrying a weight of intimacy, fragile but undeniable, leaving Harry standing there, quietly absorbing the warmth of the unexpected moment.
He wanted to reach for you, to pull you back, to make you stay a little longer - not for sex, not for anything physical but just to exist together in the same space without the past crashing down between them.
He ran a hand through his hair, exhaling slowly. Every small move you made reminded him of what he had risked, what he had lost, and what he still desperately wanted. The cheek-kiss, so innocent, so fleeting was enough to make his chest tighten. Enough to make him realize just how much he liked you, how much he needed your trust again, and how far he was willing to go to earn it.
The apartment suddenly felt too big, too empty without you, and Harry quietly vowed that he wouldn’t let these small, intimate moments slip by unnoticed again. You were here, you were real, no contract, no rules and he wasn’t going to take another chance for granted.
As the doors slid shut, you exhaled, letting the tension in your shoulders loosen slightly. You had survived the night. You had survived him. And yet… even as your mind raced toward work, a small part of you ached at the thought of leaving him behind.
*****
You pushed open the door to your apartment, the familiar quiet wrapping around you after a night that felt anything but ordinary. Last night at Harry’s hadn’t been planned, you’d just ended up there, and somehow it stretched into hours. You talked, you laughed until your stomach hurt, you sprawled across his sofa with cartons of takeout balanced between you. For a moment, it was like slipping back into the days when you still had the contract - routine, simple, just the two of you orbiting each other in your own little world.
But this time, something was different. There was no script, no obligation, no invisible clock ticking down the hours. You weren’t performing, you weren’t earning - you were just there like it has been just before he told Richard your occupation. And that difference, as small as it seemed, felt enormous. For the first time in a long time, you felt untethered. Free.
You closed the door behind you, leaning against it for a beat, as if the weight of the night clung to your shoulders. The apartment was quiet, dimly lit, and yet you still felt the echo of Harry’s voice, his laugh, the way his eyes softened when he told you things he shouldn’t have admitted at all.
You hadn’t expected him to apologize the way he did. Not Harry Castillo - the man who always seemed to be in control, who didn’t bow to anyone. But he had, and not with some throwaway line or half-hearted excuse. He’d sat there, unflinching, and told you he was wrong. Told you he’d been sick with it. Told you that firing Richard was the least he could do after the damage he caused.
And you… you’d listened. You’d let him explain, let him peel himself open in ways you weren’t sure you were ready for. You hadn’t forgiven him outright - not completely but you hadn’t walked away either. That in itself was dangerous.
You padded across the apartment, tossing your bag onto the couch. It felt strange being back here after a night that blurred the lines all over again. Once upon a time, you knew exactly where you stood: you were the escort, he was the client, and there were rules - clear, solid, sharp-edged, until you broke them by sleeping together countless times. But now those rules had been shredded - they didn't exist and your chest ached at the thought of what that meant.
Harry saying the words out loud, admitting to Richard that you were an escort, that was the crack that split everything. It had cost you your contract, cost you your pride and cost you your feelings towards Harry kicking you back into perspective. It was why you’d left in the first place. And yet… he’d stood in front of you last night, stripped of all that arrogance, and told you he’d made a mistake.
You pressed your palms against the counter, closing your eyes.
Freedom, you’d told yourself as you left his place. That’s what this is. No obligations. No money exchanged. And yet the gnawing truth was that freedom didn’t feel light - it felt heavy. Heavy with what you weren’t saying, heavy with the possibility of wanting more than you should. What you tried to let go of in Europe with Katie.
Because if Harry Castillo could admit he was wrong, if he could unravel just enough to let you see the guilt underneath… then what excuse did you have left for keeping him at arm’s length?
You grabbed your phone, your fingers scrolling for his name, a small smile creeping on your lips as you found it. Home safe.
Your phone buzzed in return in quick succession.
Good. I forgot to ask, are you free tomorrow night? Fancy taking my girl out for a long awaited dinner.
Your phone buzzed in your hand, and the words made your chest tighten. My girl. Just hearing him call you that, casual, almost teasing, but with an unmistakable edge of possession, sent a warmth rushing through your cheeks.
You knew he liked you. That had been obvious from the start of the contract, the lingering glances, the subtle touches, the way he always seemed just a second too close. But now, seeing it in black and white, addressed to you, it hit differently. Realer. Harder to ignore. No longer lost in the days counting down.
You paused, fingers hovering over the screen, trying to decide how to reply. Part of you wanted to play it cool, tease him back, keep your walls in place. Another part… wanted to reply immediately, with something soft, inviting, admitting more than you should.
Finally, you typed, careful but teasing: When did I become your girl Mr Castillo?
The three dots appeared, lingered… and then vanished. Your phone buzzed almost immediately:
Since the moment you walked into my life and refused to leave my head.
You rolled your eyes, biting back a laugh. Classic Harry, you thought, half exasperated, half charmed.
You're going to have to earn it then.
His reply was almost instant, confident, teasing:
Consider it a full-time job, and I’m a very dedicated employer.
You smirked at your phone, fingers hovering for a moment. He’s impossible. But you couldn’t help the warmth curling through your chest.
I’ll give you the chance… but don’t mess it up 😉
Before you knew it, his reply came though.
Too late, I never do.
You set your phone down, shaking your head with a grin. Tomorrow night suddenly didn’t feel like just dinner. It felt like him - Harry, always Harry - and you weren’t entirely sure if you were ready for what that meant.
*****
The dinners started small, the kind of evening you thought would feel like any other, except it wasn’t. Harry picked you up in his blacked-out car, the city lights reflecting off the polished panels, and the way he looked at you from the driver’s seat made your stomach flutter in a way you hadn’t expected. Not like when he was your client, or when the contract dictated boundaries - this was different. Free. Careful. Gentle. Attentive.
You tried to resist, every cell in your body screaming that this wasn’t supposed to happen, that you weren’t supposed to let anyone close. And yet, every shared laugh, every brush of his hand against yours over the tablecloth, made it harder to maintain the distance you’d tried so desperately to keep.
At the first restaurant, the lighting was soft, warm, flattering. Harry insisted on sitting across from you, but whenever you reached for your wine glass, his hand would brush against yours. A fleeting touch, almost accidental, but enough to make your pulse quicken.
Later, on a stroll through the quiet streets of the city, he slipped his hand into yours. You stiffened for a moment, surprised by the warmth, the pressure, the subtle assertion that he belonged there with you. You tugged your fingers back, pretending to adjust your coat, but he didn’t pull away. Instead, his grip tightened gently, a soft smile tugging at his lips as he leaned closer, murmuring something low that made your pulse stutter.
A few days later, he took you to an art gallery. You wandered among the sculptures and canvases, his hand finding yours again, this time a little bolder. When you stopped at a particularly striking painting, he reached out to touch the back of your hand, brushing his thumb over your knuckles in a gesture that should have been innocent but wasn’t. You caught his eyes, a mixture of apology and adoration swimming in their depths, and you had to look away, your breath catching.
A few days after that, you went for a quiet dinner at his penthouse, takeout and wine, the city stretched out behind the glass walls. He rested your hand in his while you talked, fingers curling gently around yours. At some point, he leaned forward, pressing a soft, deliberate peck against the back of your hand. You froze, your chest tightening at the boldness, and when you looked up at him, he simply gave you that small, infuriating smirk. You were trying not to fall, trying to remind yourself of boundaries, but every time he did something like that, the walls you’d built around yourself crumbled a little more.
Even simple things, like walking through a park after a late dinner, became charged. He’d take your hand, sometimes weaving your fingers together, sometimes brushing the back of your hand with his lips in a fleeting, possessive gesture. You told yourself you were immune, that it was nothing more than attention, that it didn’t matter but every peck, every squeeze of your hand, every glance that lingered too long, chipped away at your resolve.
A few weeks in and it was undeniable: you were falling. Again and harder.
You were resisting, reminding yourself that you had a life and a job that demanded boundaries, that emotions were dangerous and unnecessary but the way he looked at you across the table, the way his hand always found yours, the way he brushed a stray hair from your face with delicate precision… it was breaking you. And you didn’t hate it. And the more you tried to resist, the more you realized, you were falling, whether you wanted to or not.
Even now, long after the contract had ended, the memory of the nights you’d shared under its shadow lingered in every glance, every touch. It wasn’t just his hand brushing yours at dinner or the way he held your coat for you as you walked, it was the way your body still remembered him, the faint, delicious ache that flared when his thumb traced the back of your hand or when his gaze lingered too long across the table.
On one evening, you found yourselves wandering the quiet streets after a few rooftop drinks. The city lights cast a golden shimmer on the pavements, and for a fleeting moment, you imagined that this could be like before....carefree, intimate, familiar. Harry’s hand found yours again, sliding into yours with that familiar ease. You stiffened, and he paused, his thumb brushing gently over your knuckles.
“You’re tense,” he murmured, low and soft, almost as if he was apologizing before you even realized you’d been holding your breath.
“I’m fine,” you lied, though the faint tremor in your fingers betrayed you.
He smiled faintly, but his eyes flicked down to the subtle shiver that ran through you, and you remembered, those nights when he had touched you under the guise of the contract, when the air between you had thickened and nothing had been off-limits. The memory made your pulse quicken in a way you weren’t ready to admit.
He didn’t overstep now; every touch was measured, careful, teasing, building a slow rhythm of trust. But the ghosts of the past, the stolen kisses, the nights you’d collapsed together, limbs tangled, the unspoken acknowledgment of desire, hovered in every brush of skin against skin, every glance that lingered too long. You tried to remind yourself that this time it was different, that he wasn’t his client-self and you weren’t his escort-self but the pull was there, a magnetic tension that neither of you could fully ignore.
Every measured smile, every teasing touch, every careful handhold was a reminder: you had been there before, you had crossed lines, and now the slow burn of trust and attraction was the hardest, most exhilarating game either of you had ever played.
Even as you walked beside Harry, hand-in-hand through the city streets, laughing softly at some joke he had made, a part of you remained elsewhere. The world outside this quiet bubble of dinners, galleries, and late-night walks still existed, the life you led for money, for independence, for control. You were still an escort. You still took clients, negotiated schedules, and maintained the carefully curated persona that separated your professional self from the girl Harry was slowly trying to see.
Some nights, when you were home alone, the hum of the city outside your window reminded you that your world didn’t pause for love or intimacy. You still had obligations, appointments, clients you couldn’t ignore, and boundaries you had to maintain. You reminded yourself often that Harry’s presence didn’t erase that - you hadn’t promised him exclusivity, hadn’t yet allowed yourself to.
Harry, of course, didn’t know the details of every arrangement. He knew you worked - he had even asked but the specifics, the faces, the intimate nature of your work, remained yours. You carried it silently, a careful line between your life with him and your work life, because you weren’t ready to let either fully define you.
And yet, being with Harry made the contrast sharper. In his presence, every casual touch, every fleeting glance, every handhold carried a weight far heavier than a client appointment ever could. You could feel it in the brush of his thumb over your hand, in the way he held your coat, in the quiet attention he gave you over candlelight dinners. With clients, intimacy was currency, rehearsed, transactional. With Harry, it was unpredictable, vulnerable, messy. And it scared you.
He noticed the subtle shift sometimes - the flicker in your eyes when your phone buzzed unexpectedly, the way your fingers lingered on his hand just a moment too long, almost reluctantly letting go. He didn’t push, not yet. He asked questions gently, watched you, learned the rhythms of your life, accepted the boundaries you still insisted on maintaining. And even though you tried to compartmentalize, clients here, Harry there - the two worlds inevitably bled together. You carried memories of him into the appointments, the feeling of his hand, the sound of his voice, the quiet teasing banter, and it made the work harder, more dangerous for your heart.
Thankfully, you hadn’t yet had a client asking for full intimacy, but deep down, you knew it could come, and the thought left a knot in your stomach - uncertain of how Harry would react, unsure of what he might feel.
Some nights, after a long appointment, you would collapse into your apartment and reach for your phone almost automatically, checking for a message from him. A simple “How was your evening?” or “Home safe?” would make your chest tighten and your pulse race. You weren’t ready to let him in fully - not yet - but those small gestures reminded you that a life beyond the transactional existed, that there could be softness, patience, and genuine desire.
And as much as you tried to keep your worlds separate, Harry’s presence made the lines blur. With him, the slow-building warmth, the pecks, the hand-holding, the teasing glances—they reminded you why it was impossible to ignore your feelings. You were falling again, inch by inch, while the other part of your life remained a careful, professional shield.
******
You had spent the night with Harry, over dinner. The dinner had been a perfect balance of casual and intimate, a private corner table at a small, dimly lit Italian restaurant. Candles flickered between you, casting warm, dancing shadows across the table. The clink of cutlery and quiet hum of conversation from other diners faded into the background as you focused solely on each other.
You started with a shared appetizer, feeding each other pieces of prosciutto-wrapped figs, laughing softly when he got a little too eager.
You laughed softly as Harry slid a piece of prosciutto-wrapped fig across the table toward you. “Careful,” you said, “I might take it all.”
“I dare you,” he replied, smirk tugging at his lips. “I think you’d be generous… with me, maybe.”
You rolled your eyes but felt a flush creep up your neck. “Generous, am I? That’s a bold claim for someone who just tried to steal my last bite.”
“I’m just testing you,” he murmured, leaning in slightly. “To see if you’re worth the trouble.”
“Oh, I’m worth it,” you countered, leaning back but letting your fingers brush his under the table. “Just… depends on how much trouble you’re willing to handle.”
He chuckled, low and throaty, his eyes flicking down to your lips for a heartbeat before returning to your eyes. “I can handle more than you think,” he said quietly. “Maybe too much.”
You felt your pulse quicken. “That’s a dangerous thing to admit.”
“Not as dangerous as you,” he teased back, reaching out under the table to let his fingers graze yours, careful, tentative, but undeniably claiming space. “You have a way of… distracting me.”
“I could say the same about you,” you whispered, leaning closer, letting the brush of your knees against his stir something you couldn’t quite name.
The main course arrived, rich, creamy pasta for you, a perfectly seared fish for him but the food barely touched your attention. Between sips of wine, his hand would brush yours across the table, accidental, or maybe not, and your stomach fluttered with each contact.
Conversation flowed effortlessly: teasing about little city quirks, sharing snippets of past travels, light jokes that made your cheeks ache from smiling. Occasionally, your laughter would soften as he leaned closer, voice dropping just enough that you had to lean in to hear him, your senses tingling at the nearness. Every glance toward your lips, every subtle touch of his fingers against yours, made your heart race, your thoughts tangle.
A waiter appeared with dessert, interrupting the moment, but your laughter lingered as Harry leaned closer, voice low enough for only you to hear. “Promise me one thing,” he said, “that when we get back, you won’t make me wait too long.”
“Depends,” you replied, biting your lip and pretending to study the tiramisu. “Depends how much you think you can handle.” He smirked, eyes glinting with challenge, as you both finished the last bites.
The teasing had turned into something charged, a palpable tension in the air that neither of you could ignore. You felt it in the lingering brush of his hand as he passed the tiramisu, in the way his knee brushed against yours under the table, in the soft warmth of his eyes that seemed to drink you in.
By the time you left the restaurant, it was impossible to deny the pull between you, a silent, thrilling promise of the kiss waiting back at the penthouse. You hoped.
*****
The elevator doors closed behind you, leaving the city noise swallowed by the quiet luxury of Harry’s penthouse. You sighed softly, kicking off your coat, and Harry’s eyes followed your every movement, lingering on the curve of your shoulder, the line of your neck.
“You’re… glowing,” he murmured, voice low, almost a whisper. “That dress… you should’ve warned me.”
You smirked, a little shyly, taking a seat on his sofa, fiddling with the buckles of your fiddly heels. “Warn you? Why? That I might make you lose your composure?”
He stepped closer, slow, deliberate. “Maybe,” he said, as he knelt in front of you, hands warm and steady as he slipped your heels off one by one.. “Or maybe I just like touching you.”
You laughed softly, heart fluttering. “Harry…”
His fingers brushed your ankles, light and teasing, making you shiver. “There,” he said, still kneeling, his eyes scanning you with that familiar intensity. “Much better. You can actually walk without hobbling now.”
“I might get used to this,” you teased, learning a little closer to him.
“Hmm?” he replied, tilting his head. “What do you mean?” “
"You being… attentive,” you said, letting your gaze drop to his lips for just a moment before flicking back up. “Making me feel…” You trailed off, words failing as the heat between you pulsed in the quiet penthouse.
“I like making you feel safe,” he said, voice soft, brushing a strand of hair behind your ear. His thumb lingered along your cheek, tracing the curve gently. “And I like this,” he added, his hand resting lightly around the inside of your knee. “This closeness, even before anything else happens.”
You swallowed, nerves and longing tangling together. “Harry…” you murmured, letting the word hang, tasting it on your lips.
He leaned in, brushing his lips against your temple before resting his forehead against yours. “I’ve missed this,” he admitted quietly. “Missed… you.”
Your breath hitched, and without thinking, you leaned forward, pressing your lips to his. At first it was soft, tentative, like testing the waters of something you weren’t supposed to want so badly. But the second his mouth moved against yours, the restraint started to crumble.
His hand tightened on your knee, thumb pressing into the fabric of your dress, the other sliding up your arm in a slow, deliberate trail that left your skin buzzing. You tilted your head, deepening the kiss, and he responded instantly—tongue brushing yours, breath mingling, the kind of kiss that wasn’t polite or careful but hungry, claiming.
He shifted closer, the heat of his body closing the space between you. One of your hands curled in the lapel of his jacket, pulling him down to you, needing more, while the other skimmed over the strong line of his shoulder. His lips dragged down the corner of your mouth, teasing at the edge of your jaw before returning to capture you again, firmer this time, almost making you dizzy, breathed, rough and low, a warning laced with want.
The sound of your name on his lips sent a shiver straight through you. You kissed him back, desperate for another hit of that fire, but the burn in your chest, the pull in your stomach, scared you as much as it thrilled you.
“Baby…” he breathed, rough and low, a warning laced with want.
So you tore yourself away. Breathless, lips tingling, chest rising and falling too fast.
“I should....” your voice broke, and you swallowed, avoiding the weight of his gaze. “I should stop.”
His hand was still on your knee, thumb tracing idle circles like he wasn’t ready to let go. His eyes searched yours, dark and unreadable, his chest rising as though he was fighting the same war inside himself.
“You don’t have to,” he said softly, almost a plea but he didn’t push. He stayed perfectly still, waiting.
And that was what undid you most of all. God, you didn’t want to stop.
You pulled back slightly, resting your forehead against his, breathing unevenly. “I know,” you murmured. “I just… I missed this too. Just… slow.” He smiled, soft and understanding, pressing a gentle kiss to your temple.
“Slow,” he agreed. “Always.” Then, almost playfully, he slid his hand up your thigh, just resting where your dress finished caressing your thighs. “But don’t think that means I won’t keep teasing you,” he said, lips brushing your ear. “Or touching you.” You shivered, your body already responding, and laughed softly.
“I think I can handle it,” you said, though the flush on your cheeks betrayed your words. He leaned back just slightly, giving you space to breathe but not losing the connection, fingers still lightly tracing your thighs.
“Good,” he murmured. “Because I plan on doing this… all night. And not letting go.” You met his gaze, and for the first time in a long while, you let yourself feel the pull between you fully. Safe, wanted, and utterly caught in Harry Castillo’s orbit and wanting to stay there.
*****
After what felt like hours of lingering kisses and soft touches, the two of you finally eased back, settling into the quiet warmth of the penthouse. You curled up on the sofa, tucking your legs beneath you, the day’s tension melting from your body.
Harry moved to sit beside you, careful not to crowd, but close enough that his presence was a constant, steady heat. He draped a soft throw over your shoulders, his fingers brushing against your arm as he tucked it around you. You let out a long, contented sigh, your head finding the perfect spot against the cushions, the scent of him wrapping around you like a protective shield.
“You okay?” he asked softly, voice low, not demanding, just a gentle murmur meant for you alone.
“I… yeah,” you whispered, voice thick with exhaustion and lingering emotion. “Better than okay.”
He smiled, leaning back slightly, watching you with something unreadable in his gaze, tenderness, longing, and relief all tangled together. “Good,” he said simply, as if that one word could hold everything he felt.
The city lights streamed through the windows, soft and scattered, painting the room in a warm glow. You listened to the faint hum of traffic below, the quiet rhythm of Harry’s breathing beside you, and for the first time in days, your mind was at peace.
“Don’t want to move?” he asked after a moment, his hand brushing your hair back gently.
“No,” you murmured, snuggling slightly into the sofa, letting yourself sink into the comfort he offered. “Not yet.”
He stayed there, still and patient, just his presence enough to fill the quiet spaces. Slowly, your eyes grew heavy, and the warmth of the throw, the steady rhythm of his breathing, and the quiet security of being near him lulled you into a gentle sleep.
Harry didn’t move, didn’t breathe too loudly, just watched over you for a while longer, letting the moment linger. He rested an arm on the back of the sofa, a protective barrier without closing you off, and in that quiet, the two of you existed simply together - no words, no expectations, just trust slowly rebuilding with each heartbeat.
Eventually, your soft, even breaths told him you were completely asleep. He smiled, brushing a strand of hair from your face, and let himself relax into the sofa as well, just a few inches from you, content to simply be near you in the aftermath of everything.
*****
The morning light hit the room just right, warm and golden, glinting off the glass surfaces of the penthouse. You were still curled up under the soft throw on the sofa, hair tangled, skin warm from the night before. Harry hadn’t left your side all morning, kneeling beside you with his hand lightly tracing the curve of your arm, just enough to make you shiver without words.
“You’re still asleep,” he murmured, voice low and husky. His thumb brushed against your jawline, and the air between you felt charged, thick. You stirred, letting your eyes meet his. The way he looked at you, hungry, tender, and protective all at once, made your pulse spike.
“I didn’t want to wake you,” he said, leaning closer. His lips hovered near your temple, soft, teasing, and you felt heat bloom between your thighs at the proximity.
Your fingers found his wrist, tracing the veins, the subtle strength of his hand. “You didn’t have to leave either,” you murmured, voice just above a whisper.
He chuckled softly, low and possessive, brushing a strand of hair from your face. “I’m not going anywhere,” he said, voice thick with intent. His hand slid down to your waist, tracing a slow, deliberate path that made you arch into him instinctively.
Your breath hitched as his other hand cupped your cheek, tilting your face toward his. “You feel… like you’re mine,” he murmured, lips brushing your own lightly, teasing, drawing you closer without fully claiming you yet.
You leaned in, barely, letting your lips ghost over his in a featherlight kiss that made him groan softly. The tension between you, all the nights apart, all the things unsaid, throbbed in the heat radiating from his body.
His hands slid lower, fingers brushing over your hips, tracing, teasing, and you felt every nerve ending on fire. “Do you know what you do to me?” he murmured, voice rough, dragging you closer.
You responded with a shiver, leaning fully into him this time, lips meeting his in a heated, hungry kiss. Tongue teased tongue, teeth grazed lips, and your hands roamed over his chest, feeling the strength beneath the soft fabric of his shirt.
He lifted you slightly, pressing you flush against him, lips and hands claiming, exploring, testing boundaries. Every touch was deliberate, every kiss a mix of reverence and need. But even in the heat, he slowed just enough to let you breathe, to let the tension linger, stretching desire into delicious anticipation.
“You’re… mine,” he breathed into your ear, and you shivered, heart racing. You tilted your head back to kiss him again, deeper, more insistent, letting the want you’d been holding back spill over.
His hands roamed your body with a reverent intensity, teasing under the hem of the throw, over your curves, making you arch into him. You could feel the raw pull between you, the memory of past nights together under the contract flashing through every nerve ending, reminding you of everything, every heated night you’d shared, every time you’d given in.
And even as the heat built, the delicious ache of want rolling between you, you held back, letting the anticipation linger, savoring the slow burn, the power of just being close before letting it ignite fully.
*****
By late afternoon, you’d finally peeled yourself away from the warmth of Harry’s sofa, where you’d dozed against him longer than you’d meant to. A few quiet hours in his penthouse had felt almost indulgent - safe in a way you hadn’t realized you needed. But work didn’t pause for comfort.
In the guest bathroom, you applied fresh lipstick, adjusted the straps of the sleek black dress you’d chosen, and fixed your hair until it fell into glossy waves. The mirror reflected someone elegant, polished, professional. A version of you designed to walk into rooms and disarm men with nothing more than a smile. Still, beneath the careful surface, there was the faintest crease at your temple from where you’d rested against Harry’s shoulder. You caught it in the mirror and hesitated, fingertips brushing the mark as if it betrayed something you hadn’t meant to show.
When you stepped back into the living room, Harry was waiting, leaning against the arm of the sofa where you’d left him. Jacket discarded, his sleeves were rolled neatly to his forearms, his tie loosened just enough to make him look effortlessly undone. But his eyes, sharp, watchful, tracked you the second you entered.
His gaze traveled from your heels up to the dip of your waist, then lingered at your collarbone before meeting your eyes again. It wasn’t the usual appreciative look, though there was no denying the heat behind it. Tonight, there was something else there. Something heavier.
“You look…” His voice trailed, almost as though he had to steady it before continuing. A faint, wry smile tugged at his mouth. “Dangerous.”
You lifted an eyebrow, smoothing invisible creases from your dress. “That’s the point, isn’t it?”
“Depends who it’s for.”
You crossed the room, the click of your heels sharp against the marble floor. “Harry, it’s a dinner. That’s all. No drinks after, no hotel keycards, nothing you should be worried about. An old client, very reserved.” You said it lightly, practiced.
But he didn’t soften. He shifted, straightening off the sofa, sliding his hands into his pockets in a way that made him look composed but not relaxed. His jaw ticked, betraying him.
“I don’t like it,” he said finally, blunt. “I don’t like the idea of you laughing at someone else’s jokes, pretending to listen like they’re the only one in the room. Not when I know what it looks like up close.” His voice dipped on the last words, quieter, meant just for you.
You froze halfway to the door, heart kicking in your chest. He’d said it without thinking, without the careful restraint he usually wrapped around himself.
You turned, one hand on your clutch, the other brushing hair from your face. “Harry,” you said softly, warning and gentle all at once. “It’s work. You know that.”
He studied you for a long beat, eyes flicking over your face like he was trying to memorize it. Finally, he exhaled through his nose, sharp, controlled. “Text me when you’re done. Just so I know you’re alright.”
You tilted your head, lips curving in the smallest smile. “You worry too much.”
His eyes darkened, voice low enough that it barely carried. “Not enough.”
The way he said it made you pause with your hand on the doorknob, your chest tightening in a way that had nothing to do with the client waiting for you and everything to do with the man standing in his shirtsleeves watching you walk away.
You lingered a beat longer than you meant to, caught in the heavy silence between you, before finally opening the door.
“Don’t wait up,” you teased over your shoulder. But it came out softer, weaker, like part of you didn’t want him to listen.
Harry stayed where he was, hands shoved deep into his pockets, watching you pause at the door. For a split second, he thought - hoped - you might turn back, that you’d sigh, drop the clutch on the table, and let him talk you into staying. But you didn’t.
You gave him that half-smile, the one that always cut through his resolve, and then the door clicked open. He saw the faint shimmer of your perfume in the air as you stepped into the hallway, the soft sway of your hair as it caught the light. And then, just like that...you were gone.
The lock slid back into place with a muted thud. Silence followed.
Harry exhaled slowly, the tension in his chest refusing to leave with the air. His eyes stayed fixed on the door like he could will you back through it, like maybe if he stared long enough, you’d realize you didn’t want to go in the first place.
You’d looked too good tonight. Too polished. Too much like the version of yourself that wasn’t his, the version you packaged up and sold to rooms full of strangers. He hated it. Hated that they’d get to sit across from you, watch your lips curve around a smile, lean in like they mattered.
And worse....he hated that he couldn’t stop you.
He dragged a hand over his mouth, then down the back of his neck, pacing once across the living room before dropping heavily into the chair by the window. The city stretched out beneath him, glittering and cold, and he knew you were already moving through it, heels sharp against pavement, disappearing into the night like you always did.
He tried to tell himself it was business. That it had nothing to do with him. That he had no right to feel the way he did. But his jaw was tight, his pulse too quick, and the ghost of your lipstick was still warm on his mouth from the kiss you’d left there hours ago.
He leaned back in the chair, staring at the ceiling, muttering under his breath: “Fuck.”
Because the truth was simple, and it pressed heavier on him than anything else...He didn’t want to share you
Not tonight. Not ever.
*****
You arrived at the sleek, private restaurant, the kind of place where discreet clients preferred to dine. The doorman greeted you politely, and the hostess led you to a corner table, away from prying eyes. Your posture was impeccable, smile poised, the kind that promised charm and elegance without revealing anything personal.
He was already seated when you approached - a tall man, maybe 15 years older than you, with an expensive watch, eyes that calculated everything but didn’t linger too long. “You look… perfect.”
“Thank you,” you replied smoothly, sliding into the chair opposite him. “I hope the evening meets your expectations.”
As the dinner began, you laughed lightly at his jokes, leaned in to discuss his latest business ventures, subtly touched his arm when appropriate, and guided the conversation. Every gesture was calculated, the perfect balance of attention and distance. You sipped your wine, letting the warmth spread through you, but every so often, your thoughts drifted to Harry.
Your phone buzzed in your clutch. Hope the dinner isn’t too boring…
You bit back a smile, typing quickly: It’s fine… but I keep thinking about someone else.
Seconds later, his reply appeared: Is that a hint I should be there instead?
Your lips curved, your pulse quickening. You wanted to respond...Maybe. But you’re not. Yet.
You pressed the phone down, letting out a soft breath. You couldn’t send him more now, discretion was key, even in texts. Instead, you returned to the client, laughing softly at a comment, but your mind replayed Harry’s voice, the curve of his jaw, the way his hand lingered when he touched you.
The client leaned forward slightly. “You’re very attentive tonight. I appreciate it.”
“Of course,” you replied, letting your hand brush lightly against his. The touch was soft, casual, but precise, never crossing any boundaries. “I enjoy making sure my companions have the evening they deserve.”
You moved through the dinner like this, poised, charming, attentive but every gesture, every laugh, was underscored by thoughts of Harry. The way he’d kissed your temple before you left the penthouse, the intensity in his eyes, the promise that he’d be waiting for you.
After dessert, as the client excused himself to take a call, you leaned back, exhaling quietly. The small victories, the smooth conversation, the successful performance - it was all business. Yet your heart thumped in your chest for a completely different reason.
Don’t be long… Harry’s text buzzed again, and you couldn’t help the soft, almost guilty smile that tugged at your lips.
Not long. You’ll be the first thing I think about when I get home.
Good. Be careful.
You tucked your phone away, your thoughts tangled between professionalism and the man who owned your attention in a way no client ever could. The dinner continued, the city lights sparkling outside the window, but your mind was already halfway back at the penthouse, thinking of Harry and how he was going to be the end of you.
*****
The city was quiet as you slipped into your apartment, the soft click of the door echoing faintly in the hall. Your heels were off, tossed carelessly near the entrance, and you leaned against the doorframe for a moment, letting out a slow breath. The client dinner had gone perfectly - charming, smooth, no complications, but your mind wasn’t on the evening. It was on Harry.
Sliding into something softer, more comfortable, you grabbed your phone. Home safe, you typed quickly. Within seconds, your phone buzzed:
Good. Did everything go smoothly?
You bit your lip, smirking, and decided to play a little. You snapped a quick picture, the dim light of your apartment making your hair glow, your lips slightly parted, just enough to tease.
Smooth as silk. But something was missing...
Almost immediately, the reply came:
Is that my imagination or are you trying to get me in trouble?
You chuckled, slipping into your lounge set, the fabric soft against your skin.
Maybe both. Can’t help myself.
A pause, then another text:
I hope you're saving that for me?
You grinned, feeling a flutter of excitement. You leaned back on the sofa, one leg curled beneath you, phone in hand. Another picture, this one a little closer, teasing the curve of your collarbone.
Depends... If you're being good.
I always try to be on my best behavior, but around you, that's pretty damn hard.
Harry replied, and you could practically hear the deep chuckle behind the words.
Good. I like it when your're patient - you typed back, letting the playful tone linger.
The texts flowed easily after that, short bursts of flirtation and tension. Nothing crossed a line yet, but every word, every picture, carried electricity. Harry’s responses were just enough to tease, just enough to make your pulse race.
Come over?
One of his texts eventually asked.
You hesitated, biting your lip.
Not yet. I want you to imagine me for a little longer.
That’s cruel…
Or maybe it’s fun - you teased back, your heart racing as the screen glowed softly in the dark.
For the rest of the evening, the two of you continued this quiet dance, messages pinging back and forth. Each one, a teasing reminder that while you had been professional all night, now it was just you and him, the anticipation building with every text.
And in the back of your mind, you knew the tension was only going to get harder to resist the next time you were finally face-to-face.
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Sorry this has taken a few days I actually found it hard to write this chapter I don't know why... Maybe cos it was a bit filler esque? Who knows!
Also is anyone else obsessed with the new Sabrina Carpenter song Tears? Gives Harry vibes no? 👀
Taglist: @katssecretdiary @pedrosgrogus @bunny-pancake @littlewitchgirly @sesdeuxyeux @notyourlovemonkey @lizzie-cakes @aquanatalie @indiegirlunited @hotmess-x @krystal---meth @karlawithacapitalk @ro-nahime-things @noisynightmarepoetry @readingiskeepingmegoing
