Jack, perched on the edge of his desk, was polishing a compass that hadn't pointed north in years. His eyes, though perpetually shadowed by kohl, were sharp as they watched her. "Lost, my dearie?" he asked, a playful lilt in his voice. "If it's me you're looking for, you've found me."

Elizabeth rolled her eyes, her gaze catching on something half-hidden in the shadows of the room. It was a small, ornate portrait, propped against a stack of charts. She moved closer, drawn by the delicate brushstrokes. The subject was a woman, her hair the color of h/c and her eyes a vibrant, surprising e/c. A small, knowing smile played on her lips. She wore a simple dress, not the finery of a lady, but a practical outfit of a sailor or a rogue.

"Who is she, Jack?" Elizabeth asked, her voice quiet. The portrait held an undeniable power, a certain spark that reminded her of Jack himself.

He stopped polishing his compass, his hand still. The playful mask he wore so easily slipped away, replaced by a flicker of something she couldn't name—nostalgia, sorrow, a distant affection. "An old acquaintance," he mumbled, turning his back to her to place the compass on the desk.

"She's beautiful," Elizabeth said, reaching out to pick up the frame.

A sharp knock on the door made them both jump. Jack’s demeanor immediately shifted back to his familiar, theatrical self. "Enter!" he called out, his voice booming with practiced bravado.

The door swung open, and Will Turner stepped inside. "Jack," he said, his eyes going straight to Elizabeth's hand, which held the portrait. His brow furrowed in curiosity. "Just came to discuss some of the crew organizations. We're running low on hands for the night shift."

Jack's eyes flicked from Will's questioning look to Elizabeth's hand, still holding the portrait. For a moment, a storm of emotions seemed to pass over his face—concern about the ship, a flash of annoyance at the interruption, and something else, something hidden and private, that Elizabeth knew she had just glimpsed in the depths of his soul. He gave Will a lazy salute. "Right then, William. The crew's got a grand plan for us today, it seems. We can discuss my 'acquaintance' later, Elizabeth." He winked, but the light in his eyes had dimmed, and for the first time, Elizabeth saw a glimpse of the man beneath the pirate.

A silence, heavy and thick with unspoken questions, settled over the captain's quarters. Will's eyes, still fixed on the portrait in Elizabeth's hand, narrowed slightly. "You just went quiet, Jack. Who is she?"

Jack’s signature smirk had vanished, replaced by a quiet stillness that was far more unnerving than his usual theatrics. He turned from the desk, running a hand over his face. "Some things, Will, are best left to the tides and the wind," he mumbled, his voice uncharacteristically low.

Elizabeth ignored him, stepping closer to Will. "He said she was an 'old acquaintance.' But look at him, Will. He hasn't looked this… sober since he lost his jar of dirt."

Will took the portrait from her, his gaze sweeping over the delicate features of the woman within the frame. "I've never seen her before," he said, turning it over and then back. "There's no name on it."

Jack let out a long, theatrical sigh, a poor attempt at a distraction. He walked to his cabinet and poured himself a generous measure of rum. "A man is allowed a bit of privacy, isn't he? It's not like I go asking about your little... knick-knacks."

Elizabeth crossed her arms, a determined glint in her eye. "Don't try to change the subject, Jack. You act like she's a ghost."

At the word 'ghost', Jack froze, his hand halfway to his mouth. The playful mask he wore so easily was gone. The shadows in his eyes deepened as he stared at the portrait, a flicker of something raw and private crossing his features. "Some ghosts," he said, his voice barely a whisper, "are more real than the living." He looked up, first at Will, then at Elizabeth, his gaze holding them both in a rare, genuine moment of vulnerability. "Her name is Y/n," he said, the name a soft, almost reverent sound on his lips. "And she was the best part of me."

A profound silence filled the room, broken only by the gentle creak of the ship. Will and Elizabeth exchanged a glance, their earlier curiosity now replaced by a deep and unexpected empathy. This wasn't the Jack they knew—the flamboyant, roguish pirate with a quip for every occasion. This was a man stripped bare, his vulnerability on full display.

Jack took a long pull from his bottle, his eyes fixed on some distant memory. "She was… a tempest, that one. More beautiful than any mermaid, with a spirit wilder than the sea itself. And those eyes of hers, e/c pools of mischief and kindness. She could out-sail, out-fight, and out-drink any man on the crew, myself included. I'd watch her from across the deck, laughing at some joke I’d made, and my chest… it felt like it was going to burst."

He spoke of her with a reverence that was both beautiful and heartbreaking. He told them how he'd chased her, a relentless pursuit across islands and oceans, just to catch a moment of her time. He told them of her favorite songs, the way her laughter sounded like bells, and how she'd always choose adventure over comfort.

"I fell in love with her the moment I saw her," Jack continued, his voice softer now. "But she… she was stubborn. Said she had no place for love in her life. Took me ages, but I won her over. Eventually, she agreed to be mine. We were wed on some forgotten shore, with the ocean as our witness. We were a team, a storm and its calm. We were perfect."

A ghost of a smile touched his lips as he described their life together, the easy companionship, the shared dreams. "We were even going to be three. She was going to have a child," he said, the words catching in his throat.

That's when they noticed it. The past tense. He spoke of her as if she were a memory, a chapter that had closed. The joy that had momentarily lit up his face was now extinguished, replaced by a shadow of unbearable pain.

Jack’s gaze shifted, no longer focused on them, but on something only he could see. His eyes were wide with the horror of a moment replayed a thousand times in his mind. "I saw it happen," he whispered, his voice a raw, jagged sound. "A raid on a port. I was too far away. Just a street's width between us. I was running to her, screaming her name, but the chaos… it was too much."

He stopped, his hand trembling as he brought the bottle to his lips. "I saw him. A rival pirate, a cur I'd crossed years ago. He had a sword, and she was fighting, oh, she was fighting so hard. But he was bigger, faster. I saw the flash of the steel. The sound it made as it went in… I can still hear it. The blade piercing her stomach."

His breath hitched, and a single tear, dark as kohl, traced a path down his cheek. "She stopped fighting. Her eyes found mine across the distance, and I saw her fall. He pulled the sword out of her, and she crumpled to the dirt like a broken doll."

Jack took another shaky swig of rum, the bottle now nearly empty. His hand trembled so violently that he had to set it down on the desk. Elizabeth, her own heart aching with a pain she hadn’t expected to feel for this man, finally broke the silence. "The child, Jack? Was the baby..." Her voice trailed off, unable to complete the dreadful question.

He didn't answer right away. He just stared at the portrait, a single, silent tear tracing a path through the grime and kohl on his face. When he finally spoke, his voice was barely a whisper, a desolate ghost of his usual flamboyant tone. "The child was gone, Elizabeth. They both were. The sword... it went straight through her stomach. Her belly... it was already showing a little bit."

The words were like daggers, each one a testament to the agony he had carried for so long. Jack closed his eyes, a pained grimace twisting his features. He remembered the roundness of her belly, the way she would smile at him when she felt the baby kick. A small, perfect hand, a tiny foot, all gone in an instant.

He sank down onto his desk chair, the bravado completely gone, replaced by a profound and raw grief. The silence in the room was deafening, the only sound the gentle rocking of the ship on the waves and the ragged catch of Jack’s breath. Will and Elizabeth watched him, their own expressions a mixture of shock and profound sadness. They had seen Jack fight monsters, outsmart navies, and cheat death itself, but they had never seen him so utterly, completely broken. It was a side of the captain they never could have imagined, a heart shattered into a million pieces.

Will broke the heavy silence, his voice barely a whisper. "How long ago was this, Jack?"

Jack's eyes, red-rimmed and distant, finally focused on the question. He slowly lifted his left hand, the leather glove still covering it. He pulled it back, revealing a simple silver ring on his fourth finger, tarnished with age and sea salt. It was his wedding band.

"Fifteen years," he said, his voice flat, hollow. "Fifteen years, three months, and a handful of days."

He wasn't just counting the years; he was counting every moment that had passed without her. The grief was a physical weight on him, a silent, unseen burden that he carried beneath his layers of flamboyant scarves and bluster. The pirate captain who had defied Davy Jones and outwitted the British Navy was now just a man mourning the love he had lost.

Elizabeth watched him, her heart aching. The pieces of the puzzle were finally clicking into place. The reckless bravado, the constant running, the way he never stayed in one place for too long—it was all a desperate attempt to outrun a past that was forever nipping at his heels. He wasn't just a pirate searching for treasure; he was a man searching for a way to forget, a way to move on from a pain that had become his constant companion.

He looked at the portrait one last time, a small, sad smile on his lips. "We were supposed to have it all, you know," he said, his voice softer now. "A life on the sea, with a little crew of our own. But the sea... she can be a cruel mistress. She took my love, and she left me with nothing but ghosts."

Will, feeling the weight of the moment, reached out and placed a hand on Jack's shoulder. It was a simple gesture, but one of profound empathy. "I'm so sorry, Jack," he said, the words heavy with genuine sorrow. Elizabeth, too, stood silent, a lump forming in her throat. The man before them wasn't the swaggering pirate they knew, but a widower, a father who had lost his family before they had a chance to begin.

Jack didn't acknowledge Will's hand. He just continued to stare at the portrait, lost in a world of what-ifs. "She's in every sunrise, every storm," he murmured, more to himself than to them. "The way the light hits the water, the way the wind sings through the rigging... I can still feel her laugh in it."

He finally looked at them, and for the first time, Will and Elizabeth saw the depth of the loneliness that had been Jack's true companion all these years. It wasn't just the loss of a wife; it was the loss of his future, the life he had so carefully imagined and planned. The recklessness, the endless quest for the horizon, the flamboyant persona—it wasn't just a mask; it was a distraction, a desperate attempt to fill the gaping hole in his soul.

"I tried," he said, his voice cracking. "I tried to find him. The man who did it. I tore the seas apart. But he was a ghost, too. Just like her."

The silence that followed was different from the one before. It was no longer filled with questions, but with a quiet understanding. They had stumbled upon a part of Jack Sparrow that no one else had ever seen, a secret kept buried beneath layers of rum, sarcasm, and adventure. He had let them into his chamber, and into a chamber of his heart he had long kept locked. And in that moment, in the dim light of his cabin, they saw not just Captain Jack Sparrow, the legendary pirate, but a man who had loved and lost everything, and was still trying to find his way back to shore.

A/N: thank you to everyone who’s been so patient since I’ve started slowing down, and shown appreciation for my work. There’s so much love from me to all of you, I wish I had a better way of showing it 💛 Hope this lives up to expectations!

──────── UNDEFINED TERMS ────────

You met Yolanda Garcia eight months ago.

But this story doesn’t start with her. It’s not about her, at least not yet.

No, it starts with a house. It’s always the house.

It’s the same one you’ve lived in since you were a child. It has the same creaky step (the second one below the landing), the same dent in the hallway from when you fell against the wall too hard when you were running from your dad while playing, and the same kitchen table with the uneven leg your dad swore he’d fix but never quite got around to. Instead, he just stuck a wooden brick underneath it and called it good. Your childhood home has always reflected stability for your family, it was never something you really thought too much about.

Except now it’s all you think about.

The HVAC system went first, right in the middle of winter. The heat stopped overnight, and by the morning the house was freezing cold in that bone-deep way that requires a steaming shower to warm you back up. Your dad spent two days trying to fix it himself before he gave in and called someone. Those two days really sucked.

The number they quoted might as well be impossible, $11,000, but you managed to pay it anyways because you had to. What else were you going to do?

Then the roof started leaking, because when it rains, it pours. It wasn’t bad enough to collapse, but it was a slow, steady drip that stained the ceiling and spreads out a little more every time it rains. At first, your mom set a bucket underneath it for when it dripped to the floor, and then another, until you were forced to stop pretending that was a solution.

That was another bill, but that time you had to take out a loan because there was no way you could afford it, it just wasn’t happening.

And then there was the car. Not yours, you don’t actually have a car of your own, you take the bus. But the family one. The one your mom would use to drive your dad to work, and then go to her first part-time job, then her second, then drive to pick him up, and then drive home. It broke down on the side of the road, in the dark, after a shift your dad couldn’t afford to miss.

That loan wasn’t optional either. 

None of this was, just one thing after another. Every fix turned into a bill, every bill turned into a balance you can’t catch up to, and suddenly the word mortgage started feeling very dangerous. It loomed over your heads like a dark cloud, because suddenly the house wasn’t just your childhood, it was something that could be taken away.

Your dad is working more than full-time. He picks up whatever extra hours he can get. Your mom has two part-time jobs, one in the morning and one in the late afternoon, she’s barely home long enough to sit down before she’s out the door again, or in bed.

And you?

You work retail. 

It’s a job that pays just enough to feel like you’re contributing but not enough to actually make a difference. Long shifts on your feet, customers who treat you like shit, and a manager who schedules you just barely under full-time so they don’t have to give you any benefits.

Your paycheck isn’t yours anymore. It goes straight into groceries, or into whatever bill is most urgent when your paycheck hits. Sometimes it goes into things your parents don’t even ask you for, but you see the way that your mom hesitates at the grocery store, putting things back and doing math in her head. 

So you hand it all over, even when there isn’t much to give.

Dinner is cheap. There are nights when it’s just pasta or canned soup. Once you ate bread with gravy for three days right before payday. You can’t remember the last time you ate out, even fast food. You’ve stopped buying anything that isn’t necessary, and stopped thinking about things you want.

But it’s never enough. That feels like the worst part: you’re doing everything right, everyone is, and it still isn’t enough. 

The house is old. It needs things that cost money that you don’t have. You notice things you never paid attention to before, like the draft near the windows and the way you have to shut the front door just right in order for it to latch. You wonder how long it’ll be before something else breaks. You wonder how much longer you have left before the bank takes it.

The mortgage is past due, way past due. You co-signed on loans with the agreement that those get paid first so that your credit doesn’t go in the toilet before you’ve had the chance to really live. That means sometimes the mortgage gets skipped when there isn’t enough left over. 

It’s at least two months past due on the evening you get desperate.

You’re on Charlie’s couch with your legs tucked under you and a blanket thrown over your lap. The TV is quiet enough to talk over for when you feel like it, but loud enough to hear the dialogue of Law and Order without needing subtitles. The episodes have been playing back-to-back for hours now, the familiar dun dun starting to sound like a broken record.

There’s a bowl of popcorn between you, buttered and salty. You haven’t had popcorn in…god, you don’t even remember how long. You can’t spare the $4 for a box at the grocery store. You don’t say anything about it, but it’s heaven every time you pop a handful into your mouth. 

Charlie notices your desperation over the snack, but she doesn’t say anything about it. 

On-screen, a woman in a skimpy dress is mid-argument, heels loud on the floor as she paces in front of an undercover detective. 

“I told you what my terms were,” she argues. “Five thousand a week, non-negotiable.”

You let out an incredulous laugh, accompanied by a shake of your head. “Yeah, okay.”

Charlie turns to you with a confused look. “What?”

“Five thousand a week?” you repeat, nodding your head toward the screen. “For that? That’s so unrealistic.”

“It’s not that unrealistic,” Charlie says with a shrug of her shoulders.

“You cannot be serious.”

“Totally serious,” she says, reaching for the popcorn bucket. “People really do pay that much.”

“No they don’t.”

“They do,” she insists. “Sugar babies. It’s, like, a whole thing for rich guys.”

You snort. “Yeah, on tv.”

Charlie rolls her eyes. “No, like in real life. There are actual websites.”

You pause mid-reach, fingers barely closed around an absurdly sized fistful of popcorn. “…you’re kidding.”

“I’m not!” She sits up, grabbing her phone from the arm of the couch. “Hold on, I’ll show you.”

“Charlie -”

She’s not listening, tapping away on the screen. “I had a coworker who used one,” she says. “She paid off, like, half her student loans in a year.”

“That’s not real,” you say, even though your voice is losing some of it’s certainty at the conviction in Charlie’s voice.

“It is,” she insists again. “Look.” She turns her phone toward you and you hesitate a little before leaning in to look.

On the screen is exactly what she said would be. Profiles with clean layouts and pictures that don’t include full faces. Bios with words like arrangement and discreet and mutually beneficial in them like it’s no big deal, like this is just something people…do.

You’re dumbfounded. People really have money they can just…throw away because a girl is pretty?

“No way people are making that kind of money just for - for dating someone.”

“It’s not just dating,” Charlie says with a shrug. “It’s like…an arrangement. Like friends with benefits, except the benefits aren’t just sex, you know?”

“I’m just saying, it’s not realistic,” you say quietly.

“Maybe not for everyone.”

The Law and Order episode keeps playing in the background, voices rising and someone winding up arrested, but you’re not really listening to it now. Your eyes keep drifting back to her phone where she’s set it down between you.

Five thousand a week.

You sign up for that website less than six hours later. 

In the dark of your bedroom, when the rest of the house is fast asleep and there’s nobody to catch you in the act. 

You hesitate, because this is where it stops being something you’re just looking at and becomes real. You’re uncomfortable with even just the thought, wondering if this is the right move for you.

Then you think about the house. And then the past due notices sitting on the counter, and about your mom putting things back in the grocery store and your dad on the side of the road.

And you sign up.

You fill in the blank fields asking you for your name, your email, a username. You’re careful not to use anything identifying. And when it asks for photos, you hesitate again. You choose photos that don’t show your face - the same thing you’d seen in profiles when Charlie was showing you them on her phone. Your body, your silhouette, a hint of you instead of anything that could concretely tie you to the photos. It could be anyone, that’s the point. 

Anonymity.

The bio takes you a bit longer. You don’t know what to say at first, so you open another internet tab and type sugar baby profile tips. The internet has more suggestions than your brain does. You skim articles and forums alike, your eyes catching on things like know your worth and define your boundaries. Some articles talk about contracts, like actual contracts. Some mention NDA’s and Terms and Conditions. What’s allowed and what isn’t.

It's more formal than you expected, a semblance of structure, like a real job. You latch onto that thought because it makes you feel less dirty.

You swipe back over to the tab that holds your bio and begin to type, doing your best to sound like someone who knows what they’re doing. Someone that belongs here, even if you’re not actually sure you do.

The first message comes less than an hour after you finish your profile, and you don’t answer it right away. You instead just stare at the notification with an uncomfortable feeling in your stomach. Someone saw you and clicked on your profile and decided that you were worth messaging.

Eventually you open it and then wish you hadn’t.

The next few weeks are a blur of work and sifting through messages. It feels like that’s all you ever do anymore.

It’s not one bad experience, no, it’s a pattern. A steady stream of messages that all begin to look the same the longer you scroll through them.

Some of them are way too blunt. There’s no introduction or conversation, instead just expectations laid out like you’re a product they’re trying to order. Numbers thrown out without context and requests that make your face burn with shame.

Others try to be charming. Those are sometimes worse because they start normal, and you almost start to relax. But then they always start to change, with an underlying assumption that your time and attention and body belong to them already. That the “arrangement” part of this doesn’t need to be discussed because it’s implied. Why else would you be here?

But then there are a few that are normal enough that you try.

The first time you meet someone, it’s for coffee. In a public place, during the day, and you sit across from him for twenty minutes before you realize he’s not listening to a word you’re saying. He talks over you about himself, and it’s clear that you’re just supposed to fall into line with whatever he “usually expects” from arrangements like this.

Your second date (with someone else, because you never saw that asshole again) is even worse. It’s dinner this time, and you naively let yourself think that meant that it would be more serious, but it’s not. 

He’s too comfortable before food even arrives; he sits too close, speaks too low to try and get you to lean in to hear him, acting like you’ve already agreed to things you haven’t even talked about. When you try to steer conversation back to expectation and terms, he laughs at you like you’re being difficult.

He doesn’t offer to pay and you leave before dessert and refuse to let him walk you to the car your dad let you borrow for “work.”

After that, it starts to feel the same: different names but the same conversations.

Eventually the sinking realization hits that this isn’t what you thought it would be. It feels like you’re trying to force something to work that just…doesn’t. You were naïve to think that you could be like that girl on tv.

You don’t even actually like men, and you’re torturing yourself with them just for money. You didn’t delude yourself into thinking that there were women looking for company this way. 

This is just like every other app you’ve ever used, only with higher numbers and worse expectations attached. Like Tinder with money. 

You think about deleting your profile entirely and cutting your losses. This was a bad idea from the start, this isn’t something that works for people like you. Instead, you spend your last few dollars on some wine coolers from the gas station up the street and drink until you’re unconscious in your bed, the first real reprieve from your own thoughts in months.

──────── UNDEFINED TERMS ────────

One morning, you wake to a message sent at 3:07am.

You frown at that, blinking rapidly to rid your eyes of the sleep as you sit up in bed. You get a lot of messages in the middle of the night, that isn’t what has you stunned. It’s the fact that it’s from a woman.

Her profile picture is the only thing you can see next to the New Message notification, and it’s very intentionally cropped. There’s no face, just an angular jaw at the top of the photo, clothing that gives very expensive vibes, and a watch that probably costs more than the mortgage on your house.

It’s enough to make you open the message.

I like your profile. If you’re still looking for an arrangement, I’d be interested in discussing terms.

That’s it. It doesn’t even seem like she’s trying to convince you, like she could take or leave your response. 

You click on her profile, taking note of her username: Dr.G_Consult. 

Like, a real doctor?

You scroll a little further down, past her listed occupation that confirms the title. Her Bio is just as straightforward as her message to you:

Busy professional. Limited availability. Clear expectations. Discretion required. Not interested in emotional entanglement.

Between her tone and her intimidating profession, you feel like you’ve been evaluated without her even seeing you. You wonder if her messaging you at 3am is the result of insomnia or some drunken middle-of-the-night impulse.

Either way, you message her back. And she answers again. 

There’s no small talk or drawn-out conversation. She moves straight into inviting you out to dinner, already with a time and place. 

You understand the implication without her having to say it outright. She doesn’t have the time to waste, and with what she’s offering, you’re expected to meet her where she is.

On the day-of, you take longer to get ready than you have in a very long time. 

You have this dress, a green one that you haven’t worn in years because you haven’t had a reason to. It’s too nice for any events in your real life. It’s fitted and doesn’t match your current situation at all. This dress doesn’t scream overdue bills and $0.29 in your bank account. 

It’s perfect.

You take time doing your hair and makeup. You’re careful about the makeup, stretching out uses because you can’t afford to replace the products yet. You change yourself so drastically that you barely recognize the woman in the mirror. It’s been a long time since you’ve tried this hard.

The ride there is the part you think about too much. Opening the Uber app and selecting the credit card that you only use in case of an emergency.

Just this once, you tell yourself. If this doesn’t work, if it turns out like everything else, you’re done. You’ll delete the profile and forget the whole thing ever happened.

You lean your head back against the seat as the car pulls away from your street, focusing on the passing blur of the streetlights. The city fades from familiarity into something else entirely, something that feels cleaner, more expensive. You can feel it before you even arrive at the restaurant, you can see the way things like different when money is involved.

You smooth your hands over your dress as the car slows to a stop in front of the restaurant. Your heart is beating so hard in your chest that you can feel it, adrenaline setting your nerves on fire as you step out and thank the driver. 

Your heels click against pavement that doesn’t have any cracks or holes. 

The doors to the restaurant are heavy, but that’s okay because it’s the kind of place with a doorman to open them for you. That’s his whole job. 

The inside of the restaurant is muted. Nobody is talking loudly, there are no glasses clinking. It’s polished, like even sound knows better than to draw attention to itself.

It makes you stop just inside the entrance, looking around in wonder. Everyone here looks effortlessly cool, from the waitstaff to the patrons. They wear tailored clothes and look relaxed, and the laughs you hear sound rich, like you’d hear them on a golf course or a yacht somewhere.

And as you catch sight of your reflection in the window as you approach the hostess station, you realize that you don’t look that different. You blend in, you could pass for one of these people. But it doesn’t feel the same because you know what it took just to get you here, you don’t belong the way they do.

“Hello.” The hostess’ voice pulls you out of it.

You snap back to reality, realizing you’ve been standing in front of her for a little too long to be normal.

“Do you have a reservation?”

“Oh -” You start, caught off guard. “Um -” Your mind blanks because what do you even say? Yes, but not under your name. No, but you’re meeting someone. You’re here for a date that’s not really a date. You’re here for something you can’t say out loud with dignity.

“I’m meeting someone,” you say weakly, feeling your cheeks heat. 

“Name?”

You start to give her your name before realizing that’s not what she wants, she’s asking for the name your reservation is under, and you don’t know. You only know her username, it’s not like she’s making the reservation under Dr. G.

“There you are.” A voice behind you undercuts your panic.

You turn around, back toward the front doors, and find a woman standing from the padded benches there. You hadn’t noticed her before, hiding behind you the whole time, stepping in when you’re at your least comfortable.

She wears tailored slacks and a deep green button-down with the sleeves rolled up just enough to expose her forearms. Her dark hair is pulled back with intention, not a strand out of place, but even in the low lighting of the restaurant you can see it’s curly.

You love curls.

You don’t need to have seen pictures of her face to recognize her. Aside from the similar posture, the definition of her jaw is familiar, having been almost the only part of her you’ve seen until now. Her deep brown eyes are beautiful, but not in a way that feels warm. No, she’s not warm at all. She’s intelligent and clinical, even now you feel like you’re being analyzed despite the smile on her face.

She crosses the space between you in a few easy steps, and her hand finds your lower back comfortably as she turns to the hostess. “She’s with me.”

The hostess nods in acknowledgement and she picks up two menu’s from her station before gesturing toward the interior. “Of course,” she says, “right this way.”

You follow the hostess with the smallest nudge of your date’s hand. You’re increasingly aware of how the atmosphere seems to change around you in ways that are subtle enough to miss if you aren’t paying exactly the right attention. But it’s impossible to ignore once you are, everything from the soft dip in conversation as you pass tables to the way everyone except you seems to feel completely at ease here. 

Your date doesn’t look out of place one bit. She walks like the air around her owes her something, like nothing here is unfamiliar or intimidating or even noteworthy, except you. She hasn’t taken her eyes off you the entire time, you can see it out of the corner of your eye.

The hostess leads you to a table that’s set slightly apart from the main flow of the room. It’s positioned in a way that gives you privacy - no doubt a request from your date who’s profile made it very clear she values discretion. 

You’ve barely settled into your seat when the hostess leaves, and you’re suddenly alone with your date.

There’s silence for a moment, the kind that comes from first meetings and is awkward until you’re the first to break it with your name.

“Yolanda,” she introduces in return, leaning back in her chair. It makes you wonder if everything she does will intimidate you like this. “Why don’t we start with you telling me what you’re looking for.”

It’s direct enough that you look around for prying ears before you answer.

“I’m - I’m not very good at this part,” you admit with a sheepish smile.  

That gets you a small, amused smile, breaking the tension of her otherwise-stoic face. “You’ve never done this before,” she says. She’s not asking.

“I’ve talked to people,” you reply. “It just hasn’t gone beyond that yet.”

“Because you don’t know what you want,” Yolanda supplies. “Most people who use that site either don’t know what they want or think they want things that they don’t.”

You watch her carefully, confused on where she’s going with it. “And you know what you want?”

“I know what I don’t want,” she says. “And I can usually tell within the first five minutes whether someone is going to be a problem or not.”

You open your mouth before you can think twice. “Am I a problem?” you ask, and it sounds more curious than defensive to Yolanda.

Her lips curl upward further, more a smirk than a smile now. “Not yet.”

You smile as well and shake your head. “You’re very direct.”

“I have to be,” she says as she raises a hand to flag down a waiter. One - not yours - stops by the table, and she points to something on the wine list. Wordlessly, the waiter nods and disappears. “I’ve done this before,” she says, turning back to you and snapping the wine list shut.

Your hands are folded in your lap and you’re silent as you wait for her to continue.

“A couple of times,” she goes on, tilting her head like she’s gauging your reaction. “Nothing too long-term.”

That piques your curiosity. “Why didn’t they last?” you ask, leaning forward as you brace your elbows on the table.

She’s quiet as she chooses her words, but even in her own pondering, you can tell she’s still assessing you. Like she’s noticed your engagement and is still figuring out what to do with it. 

“…because they couldn’t follow the rules,” she says simply.

The conversation lingers in the wake of the mention of rules. The word sits between you and creates a tension that’s almost awkward as you try to pivot to change the subject.

“You said you’re busy,” you try. “What do you actually do?”

The waiter returns with empty wine glasses and a bottle, uncorking it and pouring you both glasses as Yolanda speaks. 

“I’m a surgeon.” She doesn’t say it with arrogance, but it still comes off cocky.

“Well obviously,” you say with a little huff. “Your profile already said that. I meant what kind?”

Yolanda thumbs the stem of her wine glass, lifting and swirling it. “Trauma.”

You take in her rolled sleeves and steady hands, her controlled posture now making more sense. “That seems like it would suit you.”

She shrugs her shoulders as she takes a sip. “And you?” she asks as she swallows.

“What about me?”

“Have you always been taken care of?”

The question catches you off-guard, but not because it’s confusing. You’re on a sugar baby website, it’s filled with spoiled women who want to be taken care of in exchange for sex. But it’s too direct, too close to home for you to answer realistically.

Because the answer is no. Painfully, and obviously no. 

You think about the house. About your mom counting dollars at the kitchen table to see how far she can stretch your last $10.About how none of this would be happening if things were different. You wouldn’t be here, with her, in this dress, if you had another choice.

You feel disgusting.

And the last thing you’re going to do is hand a stranger something they could use against you.

So you lift your gaze back to hers, smoothing your facial expression into neutrality. “Yeah.” The word comes out steadier than you feel saying it. “For the most part.”

Yolanda hums as you pick up your own wine glass, desperate to play the part. “Then this will be an adjustment.”

Your face crumples in confusion. “Why?”

“Because I don’t allow passiveness,” she replies calmly, still swirling her wine glass. “You don’t just receive from me, you participate.”

It’s an accusation disguised as clarity. Like she’s used to spoiled little girls expecting money in exchange for the bare minimum. Your mind wanders to her past arrangements, wondering what kind of rules they couldn’t follow. 

You take a sip of your wine, almost immediately beginning to feel the pleasant tingling in your toes that accompanies intoxication, and it reminds you that you haven’t eaten all day. You turn your attention to the menu in front of you.

You already know you’re not going to pick something easily. The prices alone make that clear. Even now, sitting here, and even knowing logically that you aren’t the one paying tonight, there’s still a level of discomfort in your chest when your eyes land on the numbers next to each dish. Calculation of money you don’t have that you can’t turn off.

You don’t want to misstep. 

Play your cards right and this could change your life. 

You can only imagine how much money a surgeon makes. Enough to take girls like you out to fancy restaurants on first dates.

You glance up at Yolanda and then back down again at the menu, your fingers resting against the edge of the laminated page as a thought comes to you. A test.

You lift your gaze again. “Will you order for me?”

She stops mid-sip at the question. She returns your gaze, though her eyes narrow a little. “That’s a new one,” she says, her voice edged with curiosity. “What kind of game is this?”

You press your lips together to keep from smiling. “No games. I’d just like your opinion.”

She watches you, trying to figure out if you’re telling the truth, and you can almost see the moment she decides to believe you. “…alright,” she says finally. She sets her own menu aside without looking at it and then leans forward. “Do you have any food allergies?”

“Walnuts,” you say immediately. “No other type of nuts though.”

She nods, taking that in. “What about strong dislikes?”

“No,” you say with a shake of your head. “I’m not picky.”

“Good.”

The waiter returns not long after and Yolanda orders for you both without hesitation, assured as she names dishes you didn’t even look far enough into the menu to consider. She asks one or two questions about preparation before confirming your order.

You watch her, analyzing her level of comfort with total control. You’ve seen enough Greys Anatomy to know that surgeons have a reputation for being control freaks, and Yolanda fits the stereotype from what you’ve seen.

You almost miss the way her attention turns back on you, until she speaks. “You’re overthinking this.”

You let out a small laugh. “I usually am.”

“I can tell.”

There’s no bite to her words. If anything, it sounds…teasing?

Tilting your head, you ask, “Is that a problem?”

Yolanda sucks her teeth and then purses her lips, considering it. “No,” she eventually says. “Not if you learn when to stop.”

You lift a brow. “And this is one of those times?”

“Yeah.”

You ponder that for a moment before taking a deep breath and relaxing your shoulders. You don’t fully slouch, but you’re not as rigid as you were before. 

Food arrives not long after, carried out in measured timing by two servers rather than just by one, your plates set down quietly and without a word from the staff other than the question of anything else needed. 

Your food looks…intimidating. Not in portion, but presentation. A perfectly seared piece of fish rests over a bed of something green and glossy, dotted with small bright elements you can’t name. There’s a citrusy scent, something fresh that you can smell over the richness.

Yolanda notices your stare. “Branzino,” she says like she’s answering a question you didn’t ask. “Lean protein, it’s easy to digest.”

You glance up at her, then back down at the plate. It looks expensive.

“It is.”

Shit, did you say that out loud?

You let out an awkward chuckle as you pick up your fork. “Good to know.”

Hesitating as you take the first bite, you relax fully once you do. It’s good, really good. Clean but not bland, rich without feeling heavy. You take another bite. Across from you, Yolanda is watching your reaction.

“Well?” she asks.

You glance up mid-bite and swallow quickly. “It’s really good,” you admit. “I haven’t eaten anything this healthy in a while.”

“Oh?”

“I’m usually more of a whatever I can find at midnight kind of person,” you say honestly. “I basically live on black coffee.”

There’s a brief pause that you don’t even notice because you’re taking another bite.

“That might have to change.”

You look up from your plate again to find Yolanda casually cutting into her own dish. Her expression is relaxed, but the lift of her eyebrows suggests more sternness than she’s letting on. 

“I can’t have you running on processed junk and caffeine,” she continues, “if this is going to work out between us.”

You blink. “If this -”

She’s watching your reaction with that same critical gaze, and you realize the implication of her words.

She’s interested, even if she hasn’t said it aloud. 

Your mouth curves up at the win. “Are you going to be monitoring everything that goes into my body?”

Yolanda takes a bite of her own food, chewing thoroughly and then swallowing before answering you. “If necessary.”

“And is that something that would be in writing?” you tease with a smile. 

“It probably needs to be,” she says with a returning, teasing lilt. 

You take another bite, the discomfort in your stomach that never seems to go away these days actually easing a little bit for once. 

Taking another sip of her wine, Yolanda sets the glass down carefully and returns her attention to you. “You adapt quickly.”

You’re caught off guard once more by what you assume is a compliment. “I’m trying to keep up,” you admit.

“If you’re unsure about how this works,” she continues, “there’s an easier way to figure it out.”

“How?”

She opts to watch you instead of answering, as if she’s giving you time to realize what she’s suggesting before she actually says it out loud. When you don’t respond, she sighs exaggeratedly, like she’s being dramatic on purpose for the effect. “I don’t usually extend this kind of an offer,” she says. “But it might be useful in your case.”

You shift nervously in your seat. “What kind of offer?”

“A trial,” she says. “An opportunity to see if this is something that actually works for you instead of trying to decide based on a conversation.”

She’s not offering - no way.

Your fingers tighten around your fork and knife. “You mean -”

“Yes.” She didn’t even let you finish the question. The implication is clear. “You’re free to say no, it isn’t a requirement.”

You look down at your plate while your thoughts catch up to you. You don’t do this, you’ve never gone home with someone on the first date, especially someone you don’t know.

And it’s hypocritical to even consider it. You would’ve never gone home with any of the others you’ve met from that godforsaken website. But Yolanda isn’t making you uncomfortable; she isn’t being pushy, or rude, or only talking about herself.

And it doesn’t hurt that she’s devastatingly beautiful.

You glance back up at her and she’s watching you patiently. “What…what would that entail?”

Yolanda has to contain the smirk that threatens to consume her expression. Because she knows now, she has you. You started this date so uncertain and nervous, but now, even though you’re still sitting there with the same hint of anxiety, it’s mixed with something else. Curiosity. A willingness to take the next step even when you don’t fully understand where you’re stepping. And that’s way more fun than confidence.

Because most of the women who sit across from her try too hard. They perform and play up to her ego to get what they want from her. You’re not doing that, at least not that she’s seen. 

Yolanda’s tongue darts out to wet her lips, her smirk deepening when she catches your eyes tracking the movement.

It’s dangerously appealing.

There’s something almost indulgent about you, about the way your uncertainty presents itself, not as a weakness but as untouched, unshapen by this world she’s so familiar with. You’re someone she could teach.

“A test drive.”

When the check comes, she doesn’t even look at you to see if you’ll offer to pay for your own meal. You’re not supposed to, and Yolanda is nothing if not a gentlewoman. She picks it up and slides her card in without even looking at the total. And when the receipt is provided, she again doesn’t look at it, sliding her card back into her wallet, and her wallet back into her bag.

She guides you out of the restaurant with your hand fit snugly in hers, like you could be any other couple, you trailing behind her as she leads the way outside, and when you step out, a black car is already waiting at the curb for you both. 

Yolanda steps forward and opens the back door. “After you.” It’s directive, not chivalrous.

The interior is dim with cool leather beneath your legs. Yolanda follows a second later and shuts the door behind her. You don’t bother asking where you’re going, you already know.

Your dress sits slightly higher on your thighs from the way you slid into the seat, and her hand settles hot on your skin.

She turns her head slowly, leaning in until she’s close enough that you can feel her breath on your neck when she speaks. “You can still change your mind.”

You keep your head straight, looking forward between the front seats and out the windshield, trying desperately to ignore the rapid thud of your heart beating in your chest. Your own fingers curl around Yolanda’s wrist at your thigh, but you don’t pull her away, instead running them lazily over her bare forearms.

“I know,” you whisper.

She leans even closer at that and you can feel the smirk on her mouth as her lips press against your neck, jut under your ear. Goosebumps erupt over your skin and you unconsciously tilt your head a little to give her better access. The hand that was on your thigh closest to her reaches to your other, fingers digging into your skin as she pulls you closer to her, still mouthing at your neck.

You never take your eyes off the road in front of you, and you catch the eye of the driver in the rear view mirror.

Shame fills your gut, curling like steam and igniting your skin as your cheeks flame. Hot, your whole body feels hot, and you’re not sure if it’s the eyes of the driver or Yolanda alternating between kissing and biting the skin on your neck.

The car stops in front of a building that looks like it costs more per square foot than your whole house.

The lobby inside made of polished stone and expensive light fixtures. The doorman nods as you pass him, though it’s directed at Yolanda and definitely not you, and she returns it with the same motion.

The elevator ride up is quiet and she stands beside you without touching you now, her hands at her sides and her gaze forward. If you didn’t know better, you could almost gaslight yourself into thinking the car ride never happened at all and you don’t know this woman. At her floor, she leads the way down the hallway with her keys in hand. 

But the moment you step inside, the tone changes so sharply it almost gives you whiplash. She closes the door, and then she’s on you.

One hand fists the front of your dress right above your navel while the other slams flat against the wall beside your head, caging you in. Her mouth crashes into yours, hot and demanding and all slick tongue. There’s no gentleness to it, which doesn’t surprise you since you can still feel the ghost of her teeth on your neck. Her teeth scrape over your lower lip and you can’t help the little moan that slips out of your mouth and vibrates between you two.

Your hands slide down her button-up, pulling it to untuck from the waistband of her pants and allowing you to reach her skin underneath. Your palms meet warm, smooth skin that stretches tight over lean muscle. And as you breathe through your nose, you can smell the sandalwood cologne that screams expensive.

She breaks away from your mouth and yanks your dress up and over your head in one unexpected motion, and cool air hits your skin as you’re left in nothing but your heels and panties. Then she pulls on her own shirt, not even bothering to undo the buttons, opting instead to yank her shirt off over her head. It exposes the black lace of her bra, so see-through that your mouth waters at the sight of her nipples through the fabric.

The contrast makes your clit throb; she’s barely undressed, still in her bra and slacks and you can already feel the dampening fabric of your panties becoming uncomfortably slick.

Yolanda drops to her knees right there on the hardwood of her entryway, so fluid it steals your breath. Her hands grip your thighs, spreading them wide enough that the cool air hits your soaked cunt and makes you shiver. There are no teasing strokes, no soft kisses up your inner thigh. No, she leans in and drags her tongue flat up your slit in one long and intentional lick. The wet heat of her mouth stuns you, velvet and pressure all at once. You gasp, your hips jerking forward seeking her mouth, but her hold on your thighs pins you to the wall.

Fuck, she’s good. She circles your clit with the flat of her tongue and then sucks it hard between her lips, the suction bordering on painful and pulling a cry from your throat. She lifts one thigh over her shoulder so you’re balanced on one foot, using her for leverage to keep you upright. Two fingers push into you without warning, thick and insistent, curling immediately against the inside of your walls. The stretch burns and you clench around her, the slick sounds of your pleasure filling the entryway as she pumps her fingers quickly in and out of you. 

She doesn’t bother with filthy words to ramp you up. Instead, she works the same way you imagine she performs surgery: with precision and a kind of total domination. You would do anything, say anything, be anything to keep feeling the way she’s making you feel. Her tongue never stops it’s relentless rhythm, flicking and sucking while her free hand holds your hip in an iron grip.

Your thigh trembles against her shoulders. She’s not even looking up to see your reactions, like she knows what she’s doing, knows she’s so good at this that she doesn’t need to check in. And she’s right. The pressure inside you builds fast, coiling tight in your belly until it snaps almost without warning. 

You cum with a loud moan, your pussy fluttering hard around her fingers and a rush of wet heat flooding her tongue. She doesn’t slow down, fucking you through it and drawing it out until your legs threaten to give. Only then does she pull back, licking her glistening mouth with her tongue like it’s nothing more than a reward for a job well done.

She rises, her eyes dark with want but still cool and intimidating, and grabs your wrist. “Bedroom,” she says, her voice rough from effort, and she tugs you after her.

The bedroom is just as precise as the rest of her: silk sheets pulled tight over a king mattress, no decorative pillows and a single lamp casting a yellow glow. 

She shoves you onto the bed on your back and the cool of the silk shocks your overheated skin.

You watch, breath shallow, as she strips the rest of the way: slacks sliding down long, toned legs, bra unhooked and tossed aside. Her body is made out of sharp lines, her nipples are already tight from the cool air. From the nightstand she retrieves a harness and a thick, veined black strip, the silicone both realistic and heavy-looking. She squeezes lube onto it with a wet squelch and then steps into the harness, buckling it around her hips efficiently.

“Hands and knees,” she orders.

You scramble into position, ass up and chest pressed to the mattress, your knees spread wide to make room for her. Anticipation coils in your stomach like a live wire as she climbs over you, one palm smoothing over the curve of your ass before gripping your hip hard. 

The blunt head of the strap nudges your entrance, pausing there before she pushes in. It’s slow at first, splitting you open nice and easy, and you wonder if it’s for your benefit or if Yolanda is simply cherishing the moment. The burn is exquisite, the fullness is overwhelming. When she bottoms out, hips flush against your ass, you let out a shaky sigh. 

She barely gives you time to adjust. She pulls back out slowly and slams in again, setting an immediate and brutal pace. The slap of her hips against your ass echoes obscenely, mixed with the filthy wet sound of the strap driving into your soaked cunt. One hand snakes around your body to rub perfect little circles over your clit while the other fists your hair, yanking your head back enough to arch your spine.

“Take it,” she grows above you. “That’s it, gooood girl.”

The praise lands like gasoline on the fire already raging inside you, but there’s no softness or affection to it - just the satisfaction of watching you fall apart on her cock. The strap nudges against your g-spot perfectly with every thrust, the harness pressing against her own clit and you can feel her hips stutter when it hits just right. You cum again, harder this time, loud moans falling from your tongue as your vision whites out and your cunt spasms against the silicone.

She rides you through it, her pace refusing to falter, until your arms give out and you collapse forward. Only then does she pull out with a wet pop, leaving you empty and throbbing in time with your heartbeat. She flips you over onto your back like you weigh nothing, the strap still jutting from her hips, now slick with your cum.

She unbuckles it fast, leather straps whispering as they fall away, and tosses the toy aside. Then she’s climbing up your body until her thighs bracket your head, the heat of her pussy hovering inches from your mouth. You can smell her, musky and wet from how turned on she’s clearly been the whole time she was fucking you.

“My turn,” she says, rough with restraint as she lowers herself onto your waiting tongue.

You’ve barely had a second to recover from your own orgasm, yet you still dive in without hesitation, eager to return the favor. You lick a broad stripe up her slit, tasting the flood of her arousal. She’s dripping, slick coating your lips and chin as you circle her swollen clit with the tip of your tongue before sucking it into your mouth. She tastes so fucking good, and it’s been so long since you’ve wanted and been wanted in this way.

She grinds down on your tongue roughly, dominance emanating off her despite receiving instead of giving now. You push your tongue inside her, fucking her with it while your hands grip the muscle of her ass, pulling her down harder. She rides your face with the same intensity she fucked you with, her hips rolling in circles to retain some semblance of control, chasing what she wants. Her thighs shake against your ears but she’s nearly silent, only low groans and the occasional sharp gasp escaping her.

She grips your hair so tight it nearly pulls from your head as she cums. It’s sudden and intense, her walls fluttering around your tongue, her essence flooding your mouth as her hips jerk, riding it out on your face before she stills above you.

Her breath comes deep as she climbs off and collapses to your right on the bed. You lie there, your chest heaving and body buzzing with aftershocks, your own thighs still sticky and trembling.

The silence that follows isn’t heavy. For a minute, you can pretend that this was just a regular hook-up, a run-of-the-mill romp with a woman you met at a bar. But as your body catches up, your thoughts lag behind.

Yolanda moves first, rolling onto her side with an arm bent under her head as she stares at the ceiling for a moment like she’s returning to her baseline. Then she turns to you. 

“You should drink some water,” she says with the same commanding edge to her voice that she seems to say everything with. 

A giggle escapes you. “Is that part of the rules too?” you ask, still a little breathless.

“It will be if you don’t do it yourself.”

Oh my god, that almost sounds like humor.

She sits up just a bit as she reaches for her phone, fishing it from the pocket of her slacks from earlier. She taps the bright screen a couple of times before setting it face-down.

A second later, your own phone buzzes and you reach for it without thinking. The screen lights up with a payment notification.

$3,000

What the fuck. What the actual fuck. This has to be a mistake, she couldn’t have meant to -

“Get out of your head.”

Your head snaps up to find Yolanda looking at you, her head propped up on her hand. 

“You thought this was just a trial for me?” she chuckles, almost condescendingly as she runs her free hand along your cheek. “That’s sweet.” She pushes up off the bed fully, standing to get dressed. “We can talk about next steps later.”

And as she moves to leave you alone in the bedroom to retrieve water, she stops in the doorway. “If you still want to.”

She doesn’t look at you when she says it, because she doesn’t have to. Yolanda is an expert at reading the human body, call it a byproduct of her profession that’s practically second nature by now. Call it whatever you want.

She knows she has her hooks in you.

──────── UNDEFINED TERMS ────────

Part III

Terms and Conditions Masterlist

Enjoy this? Check out my Masterlist.

──────── UNDEFINED TERMS ────────

❥ His attempt at being gentle with you. Most likely the morning after an argument.

❥ Is it really a punishment if you’re enjoying it this much?

Bonus SFW

❥ Driving w Sylus in the N109 zone :)

❥ Sends you videos like this & types “Hm, this little kitten reminds me of someone.”