are you lonely? (just like me) || Pretty Woman AU!Harry Castillo (Materialists) x gn!reader
AVAILABLE ON AO3
Part 1
Inspiration: Pretty Woman (1990) + Margaret by Lana Del Rey
Summary: You're a sex worker, living pay check to paycheck. One day, you meet a rich man, who asks for a different kind of companionship.
TWs: sex work mention (vague mostly but it is prevalent), explicit language, loneliness, and whipped man behavior (y'all seen Pretty Woman??).
[[A/N: hello!! Let me clarify a few things! So this is based on a movie literally about a sex worker, so expect a lot of that kind of talk. Not sure about smut yet, but! If I do it'll probably be a separate entity. Mostly because I want to keep the language gender neutral mainly, and smut tends to give some sort of identification to the reader. Otherwise, it'll just be talked about, and maybe some cut to black scenes, we'll see!! Also, I am slow, so it's may not come out fast, but I appreciate any support so :). Enjoy !!]]
It was a pretty run-of-the-mill night for you, the neon city lights and the busy cars. You hadn't found any familiar faces yet, nor anyone to bite at all for the night. Which was an issue for you because rent was due very, very soon, and you needed a biter, just one.
The night faded later and later, and eventually, you got to the point of almost taking off. Sleeping on it, and maybe staying up later another night this week to try and build up more. Which would suck, but-
A sleek, black car smoothed up in front of you.
It was the kind of car that even if you knew nothing about cars, you knew it was expensive. Shiny and the kind that should never been seen out in these streets, especially at this hour. But here it was.
An enigma in your usual schedule, perhaps an enigma for that section of town, actually.
Before you could think much else of it, the window rolled down and instinctively you crouched your head to meet it.
You took pause as soon as it rolled down all the way. Just for a spare second.
It was a man. A man, the kind that screamed power and wealth, something in his shoulders, the flat line of his mouth. With his rectangle jaw and his Roman nose and dark, dark eyes, you knew you'd hit the jackpot. Maybe it'd be one you actually enjoyed-
You slipped into a flirty sort of grin, and leaned against the window, “Feeling a little lonely tonight, honey?”
The man's eyes shifted over your face for a moment and you swear you saw something flashing behind his eyes (something you couldn't quite name). Otherwise, his face stayed relatively flat as he took you in.
“You offering?”
It was a deep sort of rumble, heavy with something and at the same time a tone of indifference. It was nice, very nice to listen to.
It was a typical question, confirmation of who and what you were. No one ever asked outright, especially a man like him who seemed so composed and well, past what you do.
You grin wide, still in that same flirtatious tone, “Anything you want.”
The man nodded (a quick solid motion, with an unshakeable certainty) and unlocked the door. A clear sign to move into the seat, a clear sign of, what you would perceive to be, a very good night.
You scampered in without a second's hesitation.
Just as you got comfortable (the seats were definitely heated), the voice returned.
“Buckle,” it was a low, almost command but not quite.
That request wasn't normal.
It was usually so quick, get in the car, take you to a motel and get it over with. None of them ever thought of you as, well… a human being. Never had that instinct of ‘be safe’, but this one did. You took note of it somewhere in your head, just like you did with all of your clients (mostly for your safety).
He glanced over, gaze flickering over your lap (not lingering for a second, unusual) for the seatbelt, and promptly sped off down the street.
You had many questions on the tip of your tongue (waiting to spill every time you saw his fingers flex around the wheel), more than you usually did. Because he was not like your regular client.
Plenty of clients were wealthy business men with perfect suits and perfect hair. Chasing after something they couldn't ask their wife for, usually.
At the thought, your eyes dropped to his hands on the wheel; his left hand, barren.
Strike one, you thought to yourself.
You pause, thinking, ‘He's too handsome for it to be a lack of options, and he's, assumedly, very wealthy, so he could get a much classier option, probably just going to the bar. So, what-’
“How long are your usual…” he pauses, “-appointments?”
You blink a few times, a little startled by the words. Instinctively, your gaze flicked to him.
He wasn't looking at you, focused and driving through town with a comfortable ease (but somehow a heavy tension set in his shoulders, like maybe the world rested there and he’d gotten used to it).
“3 hours,” you chime, slowly, “-but I can do as long as you need me.”
There's a pause.
“Mmm,” he hummed, a deep gravelly sort of tone that almost made you shiver.
And just like that, it was quiet again.
You took it upon yourself to note the buildings for a few moments. The lights, the architecture, all of it. And when you finally started paying attention, you realized you were in the upscale part of the city. Very, very upscale.
Another weird thing about this man. At least in your line of work.
It was mostly seedy hotels, where they wouldn't been seen. Back alleys even. But you were very much in a part of the city where everyone was seen.
Although, he looked rich enough that maybe it would all be hush-hush anyway-
The man suddenly stopped the car, rolling down the window to speak to a man, a valet probably. Based on this part of town, it's the kind of place that would have a valet.
After a moment, the man's gaze drifted back over to you. His eyes flicked up and down your body, at your outfit. It was a familiar motion, one you'd seen often, but somehow his gaze wasn't as… hungry. At least not what you could tell.
In an instant, he began shedding off his suit jacket within the driver's seat.
You were a little confused until he held it out to you, the fabric heavy with a nice cologne (sweet somewhat) and definitely ironed. Perfect. It was almost surreal to see it hanging between his strong fingers, offered to you-
“Wear it,” he murmured (again, not quite a command, but almost).
Your gaze lingered on it for a spare few extra seconds, a little like you were in an art gallery trying to decipher an abstract piece. Lost. A little in awe.
Slowly, you took the fabric from his hands.
It was soft against your skin, a sort of relieving sensation (how you imagine flowers feel after a rain), and you gently pulled it over your shoulders. It was loose on you, obviously tailored to him, and as it smoothed across your limbs, that cologne smell seemed to swallow you whole. Expensive, but in an effortless way. It smelt like the way champagne bubbles down your throat, smooth but with something dancing along your nose (much like the drink on your tongue).
There was a pause, where again, he seemed to look over you. This time hinging on you a touch slower, a brief flash of something appreciative in his gaze. Yet, somehow, the look isn’t recognizable for nights like these. Something soft in his eyes, even just for a moment; it had been a long time since you’d been gazed at that way.
“Buttons,” the man motioned over the suit jacket, loosely (his voice is still low but there’s a split second of something else in it before it promptly vanishes), “-Button it, please.”
Please, it echoes around in your mind, a word you hadn’t heard in a long time. And you’d never heard it from a man as well-composed, as… powerful as he seemed to be.
Carefully, you begin buttoning up the coat, fingers diligent in their work as you trail up your chest. There’s a strange thought that you’re touching something he has, and it’s somehow pleasing for a spare second.
The man nods again (that solid, certain motion) and speaks, “Thank you.”
Thank you.
You blink a few times, those, again, are words you barely heard in your line of work. Quick and done. No buckle, no please, no thank you-
“You're welcome,” you responded after a while, dumbfounded.
The man flicks over you again, curiously, like he's taking something in. Not objectifying you, tracing your thighs with his gaze or anything you're used to. No. He looks like he's trying to go deeper. Like he can see the human. Which you're not used to, it makes you want to squirm.
Luckily, the man seems to get out of his head, unbuckling his seatbelt. The motion fluid, as he slips his gaze over you.
“Stay.”
You pause, stalling in your motion. Your buckle slips across you, as you had clicked it, the noise of it slipping back into place filling the, now, empty car.
Within a few seconds, your door was open and that same hand (somehow both worn and smooth) was extended to you. Natural, as if it's instinct for the man.
After a few spare moments, you took his hand and slowly stood outside of the car.
In theory, you knew where you were. You'd seen it in quick flashes of taxis, driving through to your own part of town. But getting out and seeing it?
“Wow,” you murmured, gaze hinging on the hotel he had guided you to.
It had beautifully large windows, gold accents and perfectly trimmed plants. Kinda looked like how someone may describe the gates of heaven, shiny, golden and just… beautiful.
You were lost in the opulence, not noticing the odd stares of the guards by the door nor the man's gaze shifting on you. (It was a soft one, like he was uncovering something that was special for the first time in a long time.)
As you got to the doors, you expected to be stopped, at least for a moment. Perhaps like a stare down, a look of ‘are you the type of people we let in?’.
Instead…
There was a murmur from the two men, a greeting, “Mr. Castillo.”
And just like that, they pulled the doors open.
Your jaw dropped, and your eyes widened -the high ceilings, the marble floors, the chandelier, “Holy shit.”
At the curse, a few gazes snap to you. It wasn't a new sort of feeling, especially with your line of work, but even still you felt the urge to correct it.
“Oh, sorry,” you replied, smiling nervously and waving to a few of the people, “-didn't know it was that kinda place.”
“It's not,” the man, Mr. Castillo, interrupted, and there was something new in his tone (something you couldn't label), “-Don't apologize.”
Your gaze flicked over to the side of his face as he guided you through the lobby. His face was still set in an indifferent look, something heavy tugging at his features, and he still wasn't looking at you. And somehow, you ached for him to.
He was odd, this was odd.
You simply moved your gaze back to the place around you, detailing the lavish chairs, and the tall pillars like it was some sort of ancient Greek building. It was the kind of building you could make a point about architecture being art, about the craft of the hands, the delicate details of the design-
“Mr. Castillo,” another person murmured out of a sort of diligent respect. Your gaze snaps to the voice, a pretty woman at the front desk who was looking at you in a sort of envy. And maybe curiosity.
The man barely even reacted, instead, placing a hand on the small of your back and pulling you into the elevator with a casual sort of effort. Like he was almost, inherently, a gentleman. Like it echoed in his bones to be gentle, be caring, touch in appropriate spots, and handle with care.
You can't remember the last time you were handled with care.
He pressed the top button (the penthouse), scanned a keycard, and leaned against the railing on the wall. Quiet. Casual. His hand remaining respectfully on your back, it was a warm reality of your situation.
Words were on the tip of your tongue, but you didn’t want to break this bubble. This gentle sort of touch, this handsome man, this beautiful building. You were afraid you'd wake up in some seedy hotels with groping hands and the dusty smell of mildew.
And then, the doors slid open.
“Wow,” you repeated, in awe for the 3rd time that night.
Large windows, sleek kitchen, dark floors, pristine.
The man gently guided you in, almost a gentle push. As if encouraging you to take a look around, gaze upon the expensive furniture and the beautiful views of the city. Not in a way of arrogance though, more so in satisfying your wonder, your awe. For you.
Slowly, you stepped into the space. Fingers tracing marble countertops, darting across almost silky couches. You'd even tapped some of the fancy lamps, laughing to yourself at the noises.
“Wow,” you laugh again, twirling in place before landing your gaze on the window. The twinkling city below you, the cars rushing by, the other buildings just as tall, if not taller than this one.
“Holy shit,” your jaw dropped, as you approached it -hand up against the window as if you could touch it. Touch the lights of the night outside.
Finally, after a breath, you spun around and looked over the apartment in entirety.
It was beautiful, but…
Still echoed a kind of hollow air. Empty. Like no one even lived here. And then your eyes moved to him, Mr. Castillo, as he laid his keys down in a tiny bowl made for that kind of thing.
There was a moment, and he looked so… tiny in this space. As he navigated it silently, it wasn't a home, not really. And then, you had a sudden realization.
He's lonely. That's why you're here.
There's a breath, and then you speak, kicking yourself back into work mode.
“Where do you want me?”
Mr. Castillo pauses, just for a spare second, not like he's thinking but like he had the sudden realization that he was where he was, that you existed, maybe.
His dark eyes tilted up to you, and something in them suggested a sort of hesitance. Which was not new to you, many men backed out after it got real. After you started asking specifics, after the fabric began to slip off your body-
“Have you eaten?” he speaks, suddenly and still gravelly but no longer as… detached.
You pause in place, “What?”
“You work the corner all night, right?” He hums, untying his tie diligently, “Until you get a… client?”
“I… yes,” you reply slowly, confused.
“It's late, very late, and you finally got one,” he hums, letting the tie hang around his neck, untied, “-safe to say you haven't eaten in a while.”
You purse your lips, unsure how to take the suggestion, “I… No. I haven't eaten since about 3.”
The man nods, picking up his cellphone, and seeming to click through some things, “What do you prefer? Italian? Chinese?”
“Wait, hold on, I'm sorry-” you shake your head, almost like you think you might be in a dream, “-I'm confused. Very confused. Are you… Are you paying me?”
The man seems to take that in for a moment, before answering solidly, “Yes.”
There's a pause.
“-Just not for your typical services.”
You glance over him (sharp jaw, Roman nose, chocolate eyes), “Which means what?”
“Your company,” he says after several, long moments.
“Like my company?” You repeat, tone laced with other implications, “-Sir, you do not have to-”
“Harry,” he corrected, instantly (almost like the word upset him), “-please, call me Harry.”
You pause, eyeing him suspiciously, “Harry,” you correct, before continuing, “-you don’t have to dance around with me. I know what you hired me for. Unless you’re into some sort of roleplay-”
“No,” he interrupts, quickly, and seems to notice it -taking a moment to recenter himself, “No, no, that’s not what I…”
He sighs deeply, lets his head fall (looking at the countertop under his fingers), and runs a hand through his hair -frustrated maybe but you can somehow tell it’s not at you, “I just…”
You can tell he’s hesitant, like the words are stopped at the tip of his tongue. And normally, you would push, but this time, you just waited.
“I need someone…” he starts, slowly, “-around. Not… I don’t need anything from you, just… your presence.”
Your head tilted, softer and curious. Lonely. He’s lonely, but not in the way you’re used to. Not craving the intimacy you’re used to, he wants a different kind, a softer kind. For a moment, you’re not sure what to do -this is new, so, so new.
“Italian sounds good,” you echo out, slipping into a nearby armchair.
If you were unsure of your decision, it lasted only a moment because that heavy tension that had lasted all day eased. A smile, a beautiful, charming smile (light but better than nothing) spread across his face, and a relief melted into his eyes.
His voice was still low, gravelly but there was something lighter there, “I know just the place.”
are you lonely? (just like me) P2 || Pretty Woman AU!Harry Castillo (Materialists) x gn!reader
AVAILABLE ON AO3
Part 1, 2
Inspiration: Pretty Woman (1990) + Margaret by Lana Del Rey
Summary: You're a sex worker, living pay check to paycheck. One day, you meet a rich man, who asks for a different kind of companionship.
TWs: sex work mention (vague mostly but it is prevalent), loneliness, and whipped man behavior (y'all seen Pretty Woman??).
[[A/N: about to go on vacation, so enjoy this chapter :))) The show is Alone, by the way, stupid shit fs. ]]
“Tell me about yourself,” he interrupts the quiet.
The two empty bowls being the only evidence of the food moments before, which were eaten in a new kind of silence. Partially comfortable, partially strange.
You raise an eyebrow, and laugh slightly, “That's not normally part of the deal.”
“Okay,” he hums, eyes lingering on you, “-well, just a normal conversation, then.”
“Okay,” you sigh, thinking for a moment, “-I watched this Survivor-like show once, and they had a season where they did couples. Lamest shit I've ever seen.”
Harry seems to take pause, almost a little shocked by the words. And then he lets out a chuckle, an actual chuckle.
It's warm, like a crackling fire, and deep, low, gravelly. The kind you let out when something surprises you into a laugh. Like you had apparently.
“Doesn't that erase the purpose of the show?” he asks, tilting his head -leaning back in his chair with a new kind of gleam in his eye.
“Yes, exactly, Harry-” you emphasize it, almost with a touch of frustration, “-you get it better than the fucking showrunners-”
Something softens in him at the use of his name, like a foundation creaking, or something shifting into place. He looks at you like he's figuring something out. Like he's been digging around into the Earth in search of the core but found something else. Something new, undiscovered.
And then, he speaks.
“What show is it?”
That led to now, after forcing him to watch some episodes of previous seasons, where you mindlessly watched the one you complained about. You were both relaxed on the couch, that felt nearly like laying on a cloud, a bowl of popcorn between the two of you, and eyes on the large, but not obsessively large, TV. One that didn't hurt to look at, but still one that made your wallet ache looking at it. Which most of this elegant, yet minimalist (you were debating on your opinion about it) apartment did, so you supposed that wasn't special.
“You're right,” Harry agrees, popping a piece of popcorn into his mouth, “-this is shit.”
“I know, right?” you groan, “-And I'm not rooting for a single one of them.”
“Mmm,” he hums, low, and flickers his gaze to you for just a second, “-I kinda like that one.”
You raise an eyebrow, “Really? You like them?”
There's a pause.
“I don't trust your taste.”
And then Harry chuckles again, harder (nearly a laugh) that almost makes your skin tingle with how light and airy it is. How the tension seems to slip off his shoulders, and the crinkles of smile lines make themselves known. And something in you can tell that those don't show up often.
After finishing the season, you both sat in a comfortable silence. Every once in a while, you'd ask an odd question and he'd answer it legitimately like he really cared about what you were saying. It was new, that look. That attention. And yet, you still feel on edge like something will jump out at you, something will change-
“What do you do?” You ask, at this point, fully laying down and looking up at the ceiling (your feet beside his lap), “-For work, I mean.”
Harry seems to pause at that, almost reluctant. But it doesn't seem to be about you, no, it seems to be about talking about his work. Like he wanted to exist in a bubble without it.
“I'm the CEO and founder of an investment company,” he answers, finally.
“CEO and founder,” you repeat, still looking up at the barren ceiling, “-those are some big words for ‘boss’.”
That got a little bit of a chuckle out of him, one you were getting used to throughout the night.
“Sure, you could say that,” he chimes, and although you're not looking at him, you can tell he's smiling, “-Although, I'd argue ‘big boss’ is more accurate.”
You laugh a little at that, playing with a necklace hung around your neck. There's a moment of comfortable silence, one you haven't felt in a while.
“Are you one of those kinds that always work? Or the kind that smooths by barely doing anything?” you speak, curiously.
Harry pauses, once again thinking about it like you were asking his opinion on world hunger (like ever word out of your mouth was important), “Both. Most of my days are filled with meetings.”
You can tell he wants to say more, so you let the silence hang for a moment.
“But,” he adds, slowly, “-they're meetings I don't necessarily have to go to,” he pauses again, “-Not all of them, anyway.”
“Yet, you do,” you reply, simply.
He answers slowly, as if this answer reflects much more than the simple question (it does), “I do.”
There's another silence there, this one more telling. And you take the moment to try and debate how you're going to ask this. If he'll even answer it. It seems a little personal but you can't help your curiosity.
You sit up on your elbows to look at him.
“Why is that?” you offer, gentler (almost saying ‘you don't have to answer it if you don't want to’ without saying it at all).
His gaze is straight ahead on the window that frames the twinkling city. You get a profile of him, and it's a handsome one. The kind they'd carve out of stone, and you once again wonder why he's doing this. Why this man is hiring you because he feels alone. He shouldn't feel alone. So why is he?
He doesn't speak for a while, instead his fingers come to mindlessly fidget with the strap of your shoe. They're the showy, uncomfortable kind that gives you more of a leg up on your job; the kind that your feet ache in every second you stand. His touch though is soft, gentle, as if you're something he'd break if he wasn't careful enough. The touch is… new for you. Or at the very least you haven't been touched so kindly in a long time.
After a long silence, he speaks again, but he doesn't answer your question. Instead, his gaze moves to your shoes -analyzing, not like the heated gaze you're used to.
“How long have you had these on?”
So, not going there yet, you note.
“The whole time I've been out,” you answer.
“They look uncomfortable,” he murmurs, one of his fingers pulling at the straps slightly (maybe to see if they'd made the skin red, left a mark).
You answer again, bluntly, “They are.”
Harry's gaze moves to yours then, and it's soft and sweet -a gleam of something new in them. For a moment, you can't even remember how those eyes had been so detached once.
And then, with careful grace, he began taking them off. His attention focused there now, entirely; his hands were so careful, like he was handling porcelain.
You hadn't been touched like that in so long, so delicately. It almost made a lump in your throat.
“Why do you wear them, then?” He finally spoke, gaze and hands still solidly on the job he'd assigned himself.
“Better for the job,” you answer, a touch shortly (maybe because the mention of your work, or maybe because you felt your heart ache in a way you hadn't let it in a long time under his fingers).
There's a moment, a flicker of hesitation in his eyes at the mention of your job. Not judgemental, no, you could tell that much, but you couldn't tell what it was.
He undoes your shoes in silence after that, that flicker of something fading away, as he pulls one off and then starts on the other. His fingers diligent but careful. So, so very careful.
The silence once again isn't suffocating, or even uncomfortable at all. Even still, you want to say something. To break this carefully crafted intimacy. Because it's new and it's scary-
“How much is your rate?”
You pause, thinking. He's obviously wealthier, you could get more, but you decide to be honest. You think he deserves it.
“100 an hour,” you reply.
There's a pause again, and his fingers halt on your shoe.
It's almost like you've said something wrong. Something like a lie. And for a moment, you're afraid it's too much, but-
His gaze snaps up to you, and he speaks with the most emotion inflicted in his voice all day, “Only 100 dollars an hour?”
Only, echoes through your head.
You pause, pursing your lips, “Yeah. It's… That’s actually pretty high-”
He scoffs, almost angry (but not at you, you can tell), as he repeats it -almost to himself, “100 dollars an hour.”
His fingers go back to working on your shoes, no less gentle. Yet his voice and face stay somewhat frustrated, well, not frustrated, more… indignant. It's a contrast you're not sure you want to unravel yet, but that doesn't make it any less interesting to witness.
Before you can say anything about it though, he speaks.
“I'll pay you a 1000.”
You freeze in place, your eyes darting to his, even though he isn't looking at you, “What?”
“100 dollars an hour is ridiculous for you,” he replies, as if you're a precious commodity, as if he can't fathom putting a label on you at all, “-I'll pay you a 1000.”
You pause, words lost on your tongue.
“Maybe more,” he adds as an afterthought, like he isn't changing your life, “-if you'll let me.”
“What?” You repeat, nearly speechless.
“Come back tomorrow night,” he says, almost like he's not even hearing the words out of your mouth, “-I'll pay you the same.”
You felt like the world wasn't real around you for a moment, like these words, these events really, were all made up in your head. Maybe you were sleeping? Maybe you'd fallen and hit your head because of these stupid shoes? Maybe-
“Tomorrow evening, actually,” he adds on, almost correcting himself, “-can you do 5?”
“5,” you repeat mindlessly.
He continues with ease, almost as if he's piecing it together as it comes, “I want you here for dinner.”
“Dinner,” you repeat again.
“Yes, dinner at 5,” he repeats, confirming -certainly and decisively, “-I'll send a car.”
“To where?” You ask, clearing your throat, almost dizzy with the information.
“Wherever you want,” he pauses, hands still smooth across your skin as he takes off your shoe, “-wherever you are. Doesn't have to be your place.”
You blink a few times.
“Just tell me where you'll be,” he offers, still decisively, but not quite forcefully -’you're in control here’ he assures without saying a word.
You take a moment, watching him as he carefully pulls off your last shoe, “You're serious?”
Harry's gaze turns up to you -something solid, unshakeable in his eyes, “I don’t say things I don't mean,” his fingers linger at your ankle, “-you'll learn that about me.”
Your eyes smooth over him for a spare moment. Now, that's something you'd have to learn to trust. That was the first thing that you were hung up on, the first thing that you couldn't quite believe.
"And I'd like you here for dinner tomorrow," he murmurs again, moving back to taking off your shoe again, "-just like tonight was. Take out and TV. Or whatever you want."
There's a pause.
"As long as you're here."
There's a pause again. This time it's your doing. Your mind racing with a million things, because this in of itself was an opportunity. A great one. A wonderful one. But still something irked at you, something tugging and pulling at your brain: 'He's a man who hired you. You know how these men are.'
But the more you look at him, the more you smooth your eyes over the way he's softly handling you. The way he's pulling shoes off you because they make you uncomfortable.
It's new, it's scary.
And for now, you'll tell yourself that you're doing it for the money. Because you really can't think about the fact that you might be doing it for something else.
"Okay," you speak, low -almost like you don't want him to hear it.
Harry's eyes move up to yours and there's a flash in them, quick and sudden. Gone as soon as you noticed.
He repeats, gently, "Okay."
There's a moment there, where you look at each other. One you're not sure you want to exactly think about too hard.
"Dinner at 5," he confirms, dropping your gaze, "-and, please, wear more comfortable shoes."
(imma be fr I don't know about the movie in its entirety but I am in fact honored to see Pedro Pascal and his Roman nose all up in her face as they make out)
(also some of the serious shit took me out on the real)
