Summer Affair: Part 4 | Harry Castillo x F!Reader/“You” | ~3.9k Word Count
SUMMARY: Your time with Harry in Sicily changes everything.
RATING: E.
TAGS: No use of y/n, reader has the nickname (Sol) that is used sparingly, summer romance is romancing, infidelity (reader is married), reader is a history nerd, reader is described as not being thin, feelings have hit these two hard, Harry is OBSCENELY rich (i’m not even sure if you can do what he did in this chapter but idgaf we ball), smut, light dom/sub vibes, blindfolding, creampie (oops), squirting..., pussy pronouns, fingering, overstimulation, oral (f receiving), Harry loves giving praise, if I forgot to tag anything else please let me know, more tags found on series masterlist.
A/N: phew, guys, this chapter had me all dizzy as i was writing it, omfg! i want to shoutout @ak-vintage for her amazing ezra fic that inspired some of the smut in this chapter, so, thanks ashley! anyways, hope you all enjoy! 🖤 reblogs, comments and likes are always appreciated, thank you for reading!
P.S. series masterlist. read on ao3. header credit to @/devociones.
The sun shines over Taormina as you wander hand in hand through the winding streets, the air fragrant with the faint scent of the nearby Ionian Sea.
Sicily is undeniably your favorite stop on this entire trip. You love the rich, layered history that exists in every corner—from the towering theaters where myths were once brought to life, to the mosaics and courtyards and cathedrals that tell stories of conquest and cultural fusion spanning millennia.
It’s inspiring you more than you anticipated. One thing you love about design in general is being able to pull from the cultures that came before, keeping their art alive and appreciated through the decoration of space. You already know you’re going to be a busy bee the second you make it back to your office.
Harry makes every moment feel impossibly better, transforming the history into something intimate for the two of you.
He arranges exclusive private tours, charming local guides into leading you through parts of the amphitheater where most aren’t usually allowed, then to courtyards filled with blooming bougainvillea, sharing stories of festivals thrown to celebrate gods and goddesses.
Harry walks beside you, listening intently as you marvel at the history and snap photos of everything.
“You light up when you talk about this stuff. I love how passionate you are.”
You bite down on your lip. “Thanks, baby.” You lift your camera up, directing him to stand right where you want him, next to a bust of a Roman general that favors him greatly.
“Riiiight there. Perfect!” You snap the photo, already knowing you’re going to be swooning over how good he looks in his linen outfit, the top unbuttoned enough to showcase his strong chest, the tanned skin teasing you with every glimpse you get.
As you admire a gemstone necklace (that’s way too pricey) in a shop tucked into a narrow alley, Harry leans in close, his fingers tracing lazily across your back, which is exposed from the halter top you’re wearing.
“Get whatever you want. Seeing you indulge, spending my money—it turns me on more than you could possibly imagine.” His voice is a little hoarse, that charming lilt making your thighs tense together.
Your cheeks heat deeply. The way he treats you as if you truly are the rarest treasure amid historic wonders makes you want to mount him right then and there.
This energy leads Harry to sweep you off for a lavish shopping spree in preparation for the special dinner he has planned tonight.
“We’re heading to Selinunte this evening,” he tells you with an excited grin as you stroll towards the boutique.
“It’s about a three-hour drive west across the island. I’ve got something perfect lined up. You’re going to love it. But first, you need the perfect outfit to match the occasion.”
He insists on buying you every and any thing, it seems. The dressing room becomes its own dreamy montage as various articles of clothing and accessories are wheeled in by the associates.
You emerge from behind the curtain in a flowing azure sundress that catches the light beautifully, twirling for Harry’s appreciative gaze.
“Stunning,” he leans back against the small loveseat that’s provided, spreading his thighs wide as he gets himself comfortable for the show you’re putting on.
Next comes a sleek black number that hugs your curves and is extremely short. The tag says it is Versace and you swear it’s the most expensive piece you’ve ever had on your body.
This one makes Harry’s eyes widen, taking in how good your full thighs look. “Turn around,” he orders and you smirk at him, doing so slowly, bending over slightly so he can get a nice view of your ass in the tiny dress, a sliver of your panties tantalizing him.
“You’re getting that one.” He says in such a commanding tone, it makes you wet. “Not for tonight, though, but fuck—you look sexy.”
Satisfied and flustered, you blow him a kiss before disappearing behind the curtain again. He adjusts himself in his shorts, feeling his cock stirring half hard at how gorgeous your body is. No matter what you’re wearing.
Harry loves that you embrace your figure for what it is. You’re thicker, curvier, a lot more to love than his previous partners. Not that it matters to him one bit, but so many women (and men) in his circle focus too much on physical appearance.
He did too, once when he was insecure and his self esteem was at an all time low. However, in order to become the confident man that he is today, he had to learn how to overcome that.
Which he did. It taught him a lot about himself and how much he’s willing to change in order to fit into the box of what everyone else expects of him.
Each time you step out in a different outfit, Harry’s gaze darkens with desire. He pulls you to him between changes, hands sliding greedily over the silk at your waist, stealing fervent kisses.
You can feel how much he wants you right there, his intensity one of the many things about this man that turns you on.
Your back presses against the mirrored wall as his lips trail down your neck, but you laugh breathlessly and gently push him back, teasing, “Harry... behave. You have to keep those hands to yourself until tonight.”
He groans playfully, but respects your words with a wicked smile, planting one final peck at your lips.
“You’re killing me.”
Finally you come out in the showstopper—a deep orange, one shoulder satin dress with blush lace detailing that falls into a softly flared midi hem.
His stomach bottoms out at the sight of you. The hue of the dress compliments your sun kissed skin, hugging your form perfectly, enough skin shown to drive him insane.
“You look…” Harry is at a loss for words, truly.
“Perfect? Gorgeous? Amazing?” You tease, smoothing the fabric down, admiring yourself in the mirror. You look very, very fucking good.
“Took the words right out of my mouth, sweetheart.”
You try not to cringe as the grand total pops up when the associate rings you up, especially since Harry had implored you to also purchase matching jewelry and shoes.
He is totally indifferent about it, however. He just swipes his black American Express card like all of this costs him nothing.
As if it’s not more than the mortgage on the house you own with Joel.
“How on Earth am I supposed to get all these beautiful things back home? My luggage is going to explode.”
Harry shrugs, a charming grin on his lips, carrying all the bags for you as you walk out into the street “I’ll have them shipped straight to your place. Don’t worry about a single thing. What’s the point of all this if I can’t spoil my girl properly?”
This opens the door to a conversation you’ve both been gently circling. As you take a break from shopping at a shaded café terrace overlooking the ancient theater, sipping sweet limoncello, things turn a little serious.
“Sol,” he gets your attention, “what happens when this trip ends? When we leave all this behind and go back to our real lives?”
The weight of his growing feelings is palpable—holding you tight in bed every night, the quiet ways you’ve softened his once rigid need to control every little detail.
“This... us... it’s become so much more than a summer fling. For me, anyway.”
You don’t say anything at first, blinking slowly as you try to figure out what is the best approach to take here. Is this the out you need to finally come clean about your marriage?
You reach across the small table, lacing your fingers with his, feeling the warmth of his palm. “I don’t want to think about it yet,” you whisper honestly, your heart thudding rapidly from all the directions it’s being pulled.
“I want to enjoy every single second here—the beautiful world that surrounds us, the way you make me feel so alive and seen. If I spend it all worrying about the future, I’ll look back and regret not fully living in this moment. And I don’t want any regrets with you, Harry. Not one.”
He isn’t entirely pleased by your answer. You catch the flicker of uncertainty and longing in his gaze. It’s the pull of emotions that have been blooming steadily like the flowers you’ve admired this entire trip.
But he exhales slowly, a small, understanding smile breaking through as he lifts your hand to his lips for a lingering kiss. “You’re right,” he says, his tone softening with genuine resolve. “You’re teaching me that, you know. I’ve spent my life controlling everything… and here you are, showing me how good it feels to just be. It’s a better way. Our way, at least, for this incredible summer.”
Later, as you’re being driven to Selinunte, Harry briefly takes a call with his brother while you nap in his lap, completely wiped from your eventful day.
His voice is low enough to not wake you.
“Yeah... she’s incredible. She’s the most fun I’ve had… ever.” A small smile stretches on his lips as memories of your time together float through his mind.
“I think I’ve found the one—”
“Bullshit.”
“No, I’m serious—this feels different. Europe with her... it’s like everything makes sense.”
“And to think you almost fucked off back to Manhattan after that meeting in Monte-Carlo.”
Harry chuckles with a shake of his head, eyes tracing over your soft features, his free hand gently rubbing at your hip in a soothing gesture that keeps you comfortable and asleep.
“So if you could look into that for me, I’d really appreciate it. The sooner, the better. The more I think about it, the more I’m sure it’s the right thing to do.”
Peter remains silent momentarily, never having seen or heard his brother behave this way before. Harry Castillo is actually in love—he never thought he’d see the day.
That whole thing with Lucy was not love, it was more of Harry realizing what it really was that he was seeking out of a relationship. He understands now that it’s more than just about a partnership. It’s about devotion, vulnerability, allowing yourself to put all of your trust in someone.
“Okay,” his brother answers finally. “I’ll hit you back when I’ve got something.”
“Thanks.”
With that, the call ends and Harry lets out a deep sigh, looking out the window as the sun almost disappears over the horizon.
You get ready for dinner at the villa you’ll be staying in for the rest of your stay in Italy. It’s grand, way too luxurious for just you, Harry and the staff he’s hired—but he had found it absolutely breathtaking and wanted you to stay somewhere unlike anywhere else you’ve been before.
He definitely succeeded in that aspect.
When you finally arrive at the archaeological park later that night, the sight before you steals your breath completely.
Harry has rented out the entire Acropolis of Selinunte just for the two of you. Towering temples stand sentinel against the starlit sky, their honey-colored stones whispering of civilizations long past.
The setup is breathtaking: a private table draped in crisp white linen sits amidst the majestic ruins of the temples, surrounded by hundreds of flickering candles that cast a golden, ethereal glow on the weathered columns.
Moonlight spills across the archaeological site while the gentle rhythm of the waves crashes softly against the nearby shore, creating the most picturesque scene you have ever witnessed.
Even more than your first dinner date with him in Monte-Carlo.
You stand frozen for a moment, eyes wide with disbelief, as Harry takes your hand and leads you forward towards your table.
“This is for you,” he says simply. “If I could give you the whole world, I would.”
Tears prick at the corners of your eyes, blurring the candlelight. No one has ever treated you like this—memorizing every small detail you love, from your fascination with ancient history to your quiet yearning for meaningful gestures.
Not even Joel, with all the years you spent together, ever planned something so grand or romantic. He was simple, never one for sweeping, heartfelt surprises.
Harry does it effortlessly, as naturally as breathing.
The dinner unfolds amazingly. Your server brings course after course of local fare: fresh seafood caught that morning, delicate pasta with wild fennel and sardines, tender lamb prepared with fragrant herbs from the surrounding hills, and crisp wine from a local vineyard that tastes like bottled sunshine.
You talk and laugh between bites, the conversation flowing easily like it always has as the ruins stand watch like spectators of your summer affair.
The candle flames dance in the breeze, casting warm shadows across Harry’s handsome face as he watches you with open adoration.
Towards the end of the meal, as you finish your decadent dessert of ricotta-filled cannoli dusted with pistachios and orange zest, Harry reaches across the table and takes both your hands in his.
“I need to tell you something,” he begins, his tone so vulnerable in the quiet expanse of the site. “I know this is crazy—I’ve only known you for such a short time—but I’m falling in love with you. Deeply. These weeks traveling Europe, seeing the world through your eyes... it’s changed everything for me. You’ve changed me.”
You are not surprised in the slightest. The strong feelings growing in your own chest mirror his words perfectly—the way your heart races whenever he looks at you, the comfort of his touch, the effortless joy you find in his company.
Yet a persistent shadow lingers over this perfect daydream. Pursuing this fully would only complicate everything because of Joel and the life waiting back home that you haven’t fully untangled.
Your husband hasn’t reached out to you since you hung up on him, and while you should be relieved—it also brought a small sense of anxiety nitpicking at the back of your mind.
Now, the thoughts stab at you deeply. But looking at Harry—his brown eyes glowing with sincerity and surrounded by so much beauty—you don’t have the heart to break his in this fantastical moment.
Not after everything he has done for you. How he has made you feel loved like never before.
Instead, you squeeze his hands gently, tears slipping down your cheeks as a soft smile curves your lips.
“Harry... I’m falling for you too,” you whisper, the words dancing on the sea breeze. “Truly. I’m so appreciative of everything you’ve done for me—the gestures, the surprises, the way you spoil me and make me feel like the center of your world. You’re such a generous man with the biggest heart. I’ve never experienced anything like this.”
He leans forward, kissing you tenderly over the table, the taste of sweet cannoli tingling on your lips.
In this moonlit bubble amidst the ancient ruins of Selinunte, your summer romance feels timeless and destined.
You decide then that you will tell him the full truth about your marriage soon.
When you return to the private villa, Harry holds his hands over your eyes as he guides you to the main bedroom.
“No peeking, it’s a surprise.”
“I’m not peeking, I swear!” Though, you do attempt to sneak a look between the gaps of his fingers… to no avail.
Once inside, he drops his hands, and for the second time tonight—you’re left breathless.
Expensive linens drape the oversized four-poster bed, scattered with petals that contrast beautifully against the bedding. Dozens of candles flicker in ornate holders around the room, casting their light across tasteful tapestries.
The large open terrace doors let in the soothing rhythm of the ocean beyond, its breeze blowing against the sheer curtains.
“This is what I had in mind for our first time together,” he murmurs against your neck, wrapping his arms around your waist from behind. “Something slow, beautiful, worthy of you. But someone got a little too eager on the yacht in Lagos... so I haven’t been able to do it properly until now.” He smirks, remembering your frantic encounter on the deck, and you laugh breathlessly as you melt into his embrace.
Clothes fall away in a heated trail toward the bed. His hands roam your body, peeling off the designer dress until you stand naked before him.
“I won’t ever tire of seeing you like this.” He whispers against your lips, grabbing a handful of your ass which makes you shudder as he lays you down on the comfortable mattress.
The foreplay builds languidly and oh so torturously. You kiss like you have all the time in the world, tongues sliding and tangling, breaths shared until you feel like you’re breathing life into the other.
Harry’s large, warm hands caress your curves—squeezing your hips, tracing the dip of your waist, cupping your breasts until your nipples tighten into sensitive peaks.
It feels so fucking amazing. You don’t know what’s better: feeling him touch you like this or seeing how attractive he looks naked. His curls fall over his eyes as his broad figure blankets you entirely, his wide shoulders luring you to leave scratch marks all over them and down his freckled back.
He pauses his affections, lips brushing your ear, his facial hair tickling your skin. “Is it okay if I blindfold you?”
The request sends a fresh rush of arousal straight to your core. You are already beyond horny, your pussy aching and throbbing for him to give her some attention… but the idea of surrendering control to him like this turns you on even more than you thought possible.
“Yes,” you breathe out needily, almost whimpering. “Please, Harry. Do whatever you want.”
Your submission makes a sound rumble in his throat and he squeezes one of your breasts before pulling away, his presence missed the second it is gone.
He uses a soft silk scarf from the nightstand, tying it gently but securely over your eyes. Darkness envelops you, heightening every sensation. You cannot anticipate his next move, and the uncertainty makes your skin prickle with welcomed anticipation.
One moment, his hand glides softly down your stomach, fingertips feather-light. The next, his hot mouth closes around one peaked nipple, sucking hard while his tongue swirls, sending intense jolts of pleasure straight to your clit.
You arch and whimper, fingers threading through his hair.
He continues his exquisite torment, kissing a slow path lower with those full lips of his. His stubble grazes your inner thighs as he settles between your legs. His tongue parts your slick folds, licking along your slit with long strokes that have you gasping.
“Harry, baby…”
He eats your pussy like he’s devoting himself to her, savoring the natural tanginess of you—alternating between broad, flat licks and focused suction on your swollen clit. Two thick fingers slide inside you, curling perfectly against that sensitive spot while his mouth works vehemently.
Your first orgasm crashes over you without warning, thighs trembling around his head as you cry out, slicking his tongue.
Harry pulls back just enough to kiss up your quivering stomach, then claims your mouth in a filthy kiss so you can taste yourself on him.
Then he returns between your legs, devouring you again. Another orgasm builds and shatters through you, then another, until your mind melts into pure euphoric bliss.
All the while, you hear the rhythmic creak of the bed as Harry thrusts his throbbing, leaking cock against the sheets, desperately grinding for friction. He groans against your pussy, clearly on the edge himself, barely holding back from finishing all over the luxurious bedding as he pleasures you.
You babble his name over and over, fingers twisting into his soft hair to keep you from floating out of your body.
His thicker digits are building the pressure up so intensely against your g-spot. You start to feel like you need to relieve yourself.
“H-Harry…” you sob, attempting to push his head away. But he’s so lost in sucking on your clit and fingering you zealously that he’s not really taking notice of your weak efforts.
It’s not like you want him to stop for real, but you’re afraid that if you let go then you’ll just make a giant mess and that would be an embarrassment that would ruin the night.
You definitely don’t want that to happen.
But then he twists his wrist in a specific way and his skilled tongue starts to rapidly lick all over your pussy that you manage to dig your nails into his scalp as you finally squirt all over him, the release shuddering throughout your body while you gush everywhere.
“Oh my fucking god!” You yelp loudly, violently shaking in his hold as he just lets it happen, his fingers being pushed out from your core from how tightly you had squeezed around him, his mouth and facial hair drenched from your release.
By the time he finally pulls away, you are a trembling, blissed-out mess, your body humming with the aftershocks.
Harry removes the blindfold. His face hovers above yours, stare shaded with lust and profound love that steals what little breath you have left. The intensity overwhelms you—tears streak down your heated cheeks as the sensations crest.
He moves in a blur, your eyes too bleary to make out the way he swiftly discards the loose sheet that’s been ruined, then climbs over you.
“H-Harry that was…—I-I made a mess—”
“Shh, mi Sol,” he soothes, cupping your cheek affectionately, thumb brushing away the tears that have slipped from your pretty eyes. He leans in, kissing you deeply, pouring every feeling into it, his tongue sliding into your mouth.
The thick, bulbous head of his cock nudges against your oversensitive entrance and you shiver at the feel of it. With a shared groan, he pushes in inch by inch, stretching your tight, warm cunt around his hard length until he is buried to the root.
What follows is hours of hot, slow, passionate sex that is nothing like the frantic, desperate fucking you have indulged in previously.
This is different. Every thrust is given with dedicated purpose, hips rolling in a sensual rhythm that lets you feel all of him, the protruding underside sliding deliciously against your grip.
You wrap your legs around him, heels digging into his ass as he fills you again and again. Candlelight flickers across your joined bodies, highlighting the sheen of sweat on his muscles, the way your heavy breasts bounce with each measured stroke.
He whispers praises against your throat, kissing up your jaw.
“So perfect.”
“I love how you feel around me.”
“You’re mine. I love you.”
All while you mutter his name like it’s a hymn, moaning nonsense as you lose yourself in the lovemaking.
You come together multiple times, sometimes with him deep inside you, sometimes with his fingers on your clit while he grinds slow circles.
Positions shift languidly: you on top, riding him with lazy rolls of your hips as he watches you with worshipful eyes; him behind you, spooning close as he thrusts deep and kisses your neck.
It feels like you are laying your hearts completely bare, bodies and souls entwined.
Eventually, exhaustion and satisfaction claim you. You fall sound asleep in Harry’s arms, your body curled against his, the sheets tangled around your naked forms and rose petals scattered across the bed.
Harry stays awake a little longer, gently stroking your hair as he watches you.
The depth of his feelings crashes over him overwhelmingly so. In this moment, he knows with absolute certainty that he wants to marry you.
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YOUR HONOR PLS LET THEM GET MARRIED
















