Archive of Our Own

It isn’t the first time you’ve gotten a call like this. Help, Miles always needs help, but today…

Your brother’s voice trembles on the other side of the phone. He sounds more distressed than you think you’ve ever heard him sound before. It makes you pause, this doesn’t feel like his usual calls.

“Hey, hey, what’s wrong?” Your voice is a soothing balm, trying to maintain relaxation. You’ve never heard Miles so riled up before.

“I-I…” He stutters out. “I need you to come get me. I…I messed up, I messed up.” He speaks slowly.

“Send me the address, I’ll be right there.”

“Okay…” He trails off for a moment. “I’ll send it to you, please come quickly. She’s…I’m scared.”

“Don’t worry about a thing.” You reply without thinking much and then hang up. You’ll always help your younger brother. He hasn’t been making the best choices lately. You tried to talk to him about it, but decided, life will have to teach him a lesson.

And, with the way he just sounded, you think it has. You get into your car and put in the address he sent. The keys twist and the engine roars as you start your drive there. He’s at a casino, which leaves a bad taste in your mouth.

Miles has never been the gambling type, but he’s really been up to no good lately. You sigh softly and keep your eyes on the road. “She’s…I’m scared.” You wonder who he was referring to. He definitely sounded disturbed to say the least.

Twenty minutes later, your car rolls to a stop in the parking lot. It’s an upscale casino, bustling with people, but the inside just makes you feel sad. It’s half young, stupid people having fun and the other half are people with sunken eyes, staring at machines and clicking buttons on autopilot. Addiction, not that someone like that would admit to it.

You’ve been here before, but only for a friend’s birthday party a couple years ago. You were all freshly 21 and ready to explore. The experience had been disappointing, none of you won anything, you only drained your wallets.

You enter with your back straight, not wanting to appear too meek even though, usually, you think that you are. You look around for Miles.

When you can’t find him, you decide to just call. He picks up almost immediately, voice shaky. “Hello?” He murmurs into the speaker.

“Hey, I’m here. Where are you?”

“One of the…backrooms…” He pauses, pulling his voice away from the phone. “She’s here, I’ll go get her.” The words aren’t directed at you, they’re for someone else with the distance it brings.

There’s quiet for a few moments, before Miles’s voice is back on the speaker. “Stay there, I’m coming.”

“Okay…” You stay on the phone, looking around for him. After about a minute, you spot him. He looks disheveled. The bridge of his nose is discolored, some dried blood is on the collar of his shirt, and his left eye is swollen- the beginning stages of a bruise.

He got beat up. You move closer to him. Upon closer inspect, you spot that his lip is split too.

“What the hell happened?” You grab his shoulder.

“I messed up!” He squeaks out, unlike his usual self at all. “I…borrowed some money. I thought I was gonna win it back! I fucked up! And now I’m screwed, and I’m sorry, but they said they’re gonna kill me. I-I need your help.” He admits.

Your lips form into a thin line, agitated, but not too much. This isn’t a good situation, but you’d be even more mad at him if he hadn’t called you, if he’d eaten death instead.

“Now…it is what it is. I’ll see what I can do.” You’re not well versed in things of this nature, but you’ll do your best for him. You don’t have much money either, certainly none to spend.

If these people are holding the threat of death, you have to assume he’s wracked up a substantial debt to them.

Miles is quiet as he guides you to the backroom. Behind a wooden, ornate door, there’s three people. Two men flank one woman. They’re all about the same height. The men are dressed the same way - black suits and ties. It only further makes your heart plummet, Miles has gotten involved with bad people.

The woman in the center stands out a bit more. She’s dressed similarly, except she lacks a tie and instead of a white button down, hers is a dark brown color, almost black. 

They look straight out of a movie. If they were wearing fedoras, you’d think this wasn’t real (but it would tie it all together).

“Y/n, I presume.” The woman speaks, voice flat, but it has an edge to it that you can’t quite identify.

“Yes, that’s…me.” You walk forwards, feeling nervous, but trying not to show it.

“Your brother owes us a lot of money.” She says, hand ghosting over her hip, it’s then that you see a gun in a holster when her blazer shifts. You think she meant to show it.

“How much…?”

“Well, it’s up to about $30,000 now.” She says it simply.

Your jaw goes slack. You spare a glance at your brother. “What, uh, how long did it take?”

She hums, tilting her head from side to side. “About…four months.” A smile climbs onto her lips, lines forming.

You clear your throat, anxious. “I see, well…neither of us have that kind of money, so possibly, you could give us some time to come up with it?”

She crosses her arms, tapping her fingers against one of her elbows. “I’ve given him plenty of time. I was told you’d resolve this.”

“I don’t have $30,000.”

“How much do you have?” Fingers ghost over the gun once more, the threat is there, clear.

“I could give…$5,000.”

“Oho, that’ll do. Fork it up, and I’ll afford you…three months to come up with the rest.” 

“How about…four months?”

“Three.”

You back away subconsciously. “Understood.”

She smiles, gleaming. She presses a hand into her pocket and comes up with a pack of cigarettes. You grab Miles’s arm, anxious, but unwilling to leave until you’re directly told to.

The woman extends an offer to you, presenting to crinkled package of tobacco. “Do you smoke?”

“No, no thank you.”

She pulls the offering back. “Name’s Esme, I’ll be keeping an eye on you, now, get lost.”

She doesn’t have to tell you twice, you drag Miles out of there immediately. He shakes like a leaf, petrified. You can’t imagine what they did to him when you weren’t there.

—

Esme…

You pretend like you don’t see her. It’d be hard to forget a face like hers, especially with the situation you find yourself in. You picked up extra hours and an extra job too. Miles is doing the same.

These people mean business, if you can’t fork over that money in two months, you can kiss your normal lives goodbye. One month has passed, and you haven’t made nearly as much as you had hoped.

You're concerned about Miles’s compliance to the plan, scared that he’s out blowing money. Certainly, you should have been able to stow away more than $4,000 last month, right? Though, $30,000…you’d need six months to make that, and that’s not counting the money you need to spend on necessities.

You never have any excess money lying around. Miles doesn’t either, Miles never has enough.

A gloved hand grabs your wrist, stopping you in your tracks. You can’t believe you forgot about her for a moment. She’s dressed nice, but not as intimidating as she was a month ago. Today, she wears a long, fitted skirt and a turtleneck beneath a beige coat.

“Ignoring me?” The question is playful, her face is crinkled slightly, smile lines visible. She doesn’t seem like someone who smiles much, though, from what you’ve seen, she likes to do mocking smiles.

“No…of course not.”

“Sit.”

“I’m…I can’t, I’m working right now.”

She tilts her head slightly, eyes closed in a smile. The expression isn’t friendly. “Sit.” She repeats, and this time, you listen.

Her gray eyes open again, slowly this time. Her black hair is down, perfectly parted in the middle. “How’s the money coming along?”

“It’s, yeah, it’s coming.” You swallow thickly, nervous. You aren’t sure how you’re going to make things work yet. If you don’t, she’ll know in the end.

“It’s kind of you, lending a hand out to your brother like that, but…” She leans in, dark red lips coming close to your ear. “...he’s been at the casino, thinking he can win it back.” She pulls away quickly, eyeing you up and down.

“Has he?” Your tone sparks, anxious and angry.

“Yes.” She affirms, pausing and then waving her hand. “Get a drink with me tonight.”

“I can’t, I have work.”

“Call out, or you’ll certainly regret it.”

You close your eyes for a moment, thinking the words over. When you open them, she already has your phone in her hands. She unlocks it swiftly, pushing it towards your face and then taking it right back.

“Hey-” You reach out, she smacks your hand away, abrasive.

She doesn’t return it until she's done with whatever she’s doing. “There.” She slides the phone across the table. “You have my number, and I have yours. I’ll send you the details.” She eyes you up and down again, and it feels like she’s checking you out. “Wear something nice.”

Then, she’s off, and you watch the enigma that is Esme leave the diner. You feel less scared of her now, for some reason.

—

You don’t wear dresses very much, or not ones like this at least. She told you to dress nice, and the address she sent you was to an upscale restaurant with a bar, not just a bar. You’re glad she sent the address, because you certainly would have underdressed if she hadn’t.

Regardless, your car looks incredibly out of place in the parking lot. You send her a text, telling her that you’re here. She tells you she’s up sitting at the bar.

You enter the building, marveling at the structure, and…she better be paying tonight.

You examine your surroundings as you make your trek up to the bar, you can’t help but feel out of place when you’re somewhere like this.

You find her sitting at the very end of the bar, on the outer seat. There’s a spot next to her open, among many. People seem to come here for the dining experience, not the drinks. She smiles at you, pulling the seat out slightly. It’s not quite enough to fit, but you appreciate the gesture.

“Ah, I’m glad you came.” She takes one of your hands into her own, raising it to her lips and pressing a chaste kiss to your knuckles.

You’re a bit taken aback by the gesture, but you thank her for it anyway. She’s not wearing the same thing she did earlier. Tonight, her outfit is more reminiscent of what she wore on your first meeting.

She places a hand onto your thigh almost immediately, and her intentions become clear to you. You’re not normally so devious, but you feel you ought to use your situation to your advantage.

She squeezes softly, offering you a curt smile. “So then, about your brother…” She trails off. “I believe he’s a lost cause. You should leave him to pay off the debt alone.”

“I can’t do something like that, he’s my brother.” You frown, that isn’t really an option.

“You know,” she shifts closer, body turning to face you. “I see people like him all the time, I deal with them all of the time. They all drag other people in and get them killed or screwed over, you shouldn’t let him do that to you.”

“You’ll have to get the money somehow, even if he dies. Wouldn’t I be on that list anyway?”

She grins, teeth showing, as if she’s been exposed. “I’d make an exception for you.” Drinks are placed down in front of the two of you. She picks her glass up. “I hope you like whiskey.”

You pick yours up too, taking a sip. It burns the back of your throat, but you swallow it anyway.

“I feel you’ve taken a liking to me?” You address what’s been bothering you. Or rather, what you think you’ve noticed.

“I wouldn’t have invited you out if I didn’t like you.” The glass clinks softly as she places it down. “That being said, I have a…proposition for you.”

You subconsciously lean in closer. This is what you had been hoping for. “Tell me more.”

Gray eyes scan you, glinting. “Women like you…they’re…just my type. Entertain me, and I’ll forget about the remaining debt. I won’t ever loan out to Miles again, and I expect you wouldn’t ask me for help with him down the line.”

You nod your head, placing your hand over hers, which is now drifting towards your inner thigh. “Yes, that’s…I’ll agree to that, and I think Miles has learned his lesson.”

“People like that don’t learn.” She’s still smiling. “You should leave him behind while you’re in a position to do so, but I suppose, I don’t care much.”

—

Everything is better with alcohol, you’ve always thought. Esme’s lips slide against yours, hungry and messy, a stark contrast from the strict composure you’ve examined from her up until now. She doesn’t waste any time, pushing you against the wall and pressing her hand onto your crotch, rubbing roughly.

Her eyes pick apart your own, looking for some kind of reaction. The sensations tingle, in a good way, the effects of all the whiskey sparking to even more pleasantries. A soft noise of pleasure leaves your mouth.

She takes it as permission, slipping her hand beneath your dress and into your underwear. Smooth, long fingers caress you.

“Wet already?” She clicks her tongue, smirking at you.

You nod your head, not even feeling embarrassed about it. You think you would if you were sober, but in your current state, you only grind into her hand. 

“Greedy.” She says, but she doesn’t deny you, fingers plunging into you slowly, beginning slow, scissoring motions inside. Your walls flex around her, squeezing her as if not allowing her to leave.

She presses her mouth over yours again. You aren’t sure you can call it a kiss with the way she positively devours your mouth. You lean into her touch, arms wrapping around her neck. It sends electricity through you, sparking a feeling that you chase.

She pulls away from the kiss. “Greedy.” She repeats, adding another finger into your pussy. You whimper, surprised, but quickly melt into it, enjoying the rhythm against you.

Your hips swim against her hand as you stabilize yourself against her. She kisses you repeatedly, fingers thrumming restlessly.

“Ah…” You pant, sensations building. Her fingers pull out, rubbing up and down between your lips and settling on your now swollen clit. “I’m…close.” You breathe out.

You can practically hear the smile in her voice. “Already?”

You nod your head. Her fingers continue, pushing, twisting, and rubbing until you can’t take it anymore. Your muscles twitch, hands tightening on the fabric of her clothes as your thighs tighten on her hand.

You grab onto her as if you’ll die if you don’t, a slew of noises leaving your mouth. Your pussy tingles pleasantly, pleasure spreading down to your legs in a sudden tuft. You cum right on her hand, and she continues moving, helping you ride out your orgasm. You just hold onto her the entire time, by the end of it, your hands are shaking.

You bury your face into the crook of her neck, panting in the aftermath. Your ears ring, room spinning slightly. You don’t know if it’s from all the drinks or from her, possibly, a combination of both.

“Take your clothes off.” The command is quiet and low, murmured against your head.

You don’t say anything, pulling off and complying with her demand. Your dress comes off, then your bra and underwear. She examines you the whole time, watching you undress.

“Get on the bed.”

You follow that command too, sitting down.

Her eyes are half lidded as she stares at you. “Now, watch me, just like how I watched you.”

You nod, observing her almost clinically. The blazer is removed, and she didn’t even wear a shirt beneath it, not that you could even tell earlier. Her breasts are average sized, but even more alluring with the defined abdomen she sports. Her arms bear lean muscle too, you assumed she had some, but seeing it up close is different.

She takes her pants off slowly, unfastening her belt, unbuttoning, unzipping, and then pulling them down, sure to arch her back as she does it. She pauses there, staring at you before taking off the rest; socks and underwear.

Then, Esme’s on top of you, pushing you down against the mattress. Red lips press against yours, and you’re surprised her lipstick is still even on, a dark red, almost brownish color. It seems strange, but it fits her features quite nicely.

She slots a leg between yours, pressing her knee down.

“A-ah,” an involuntary noise leaves you at the feeling. You almost want to ask her to go harder.

“It’s good?” She questions, even though you think it might be rhetoric, you nod your head anyway.

Her hands grab your thigh, lifting it up and angling it as she further slots herself against you, so close her pussy presses against yours. You observe just how wet she is for a moment, and then you feel it, fluids intertwining with your already spilled ones.

She pushes your thigh up higher, you grimace, but only briefly. You think you might be sore from this tomorrow. She pays it no mind, pressing down fully with her weight before beginning to swim her hips against yours.

She moves slowly, shifting several times until she finds the spot that seems to work for the both of you. She knows it’s right because you gasp when she presses against you in just the right spot. You try to keep up with her movements, but she’s just too quick, too strong. You feel the muscle of her thighs against yours, and you can’t deny that you’re impressed.

She continues mostly the same. You quickly discover that she isn’t all that vocal. It’s only indicated by a slight tinge in her expression that she’s close, and further confirmed when her pace quickens. You’re close too, you’d been trying to hold out, but the dam breaks with no warning at all.

You can’t help it, legs convulsing and back arches as you climax for the second time. She slows down for you, aiding you, but the carefulness doesn’t last. She chases her own orgasm after, using you to reach it.

A soft, quiet and deep sound leaves her throat and her pussy twitches against yours, hot liquid spilling, almost dripping directly into you.

She leans down, you twitch, leg at an even more awkward angle now, but you don’t mention it. She presses a kiss to your lips, hips beginning to grind against yours again. You press into her, wanting to tell her it’s starting to ache, but your mouth stays swallowed by hers.

—

You are reminded of your actions in the morning. Esme is coiled around you, arms around your waist and head on top of yours. You don’t move, closing your eyes again.

You don’t want to wake her.

“Good morning.” Esme’s voice greets you. She must have already been awake.

“Good morning.” You repeat back, beginning to rub your eyes.

She kisses the back of your head softly. “Are you still happy with our deal?”

“Yes.”

“I expect you here whenever I need you to be.”

You nod your head. She kisses you again before unwrapping her arms from you. “Face me.” She says sternly.

You roll over to look at her. She’s a bit disheveled, but not as much as you would have expected her to be. Rolling over made you realize how sore you actually are, ouch.

She leans in, closing the distance. Warm lips melt against yours.

“Mine.” She says the word softly. “You belong to me, this might be an arrangement, but it’s exclusive, no sleeping around.”

“Mhm…” You agree.

“Good.” She kisses you again, this time on the forehead. “I have to…work, but you can stay as long as you need, door locks automatically…” She gets up from the bed. You look at her, face flushing slightly.

You can’t believe you slept with someone so attractive.

“I can really…forget about Miles’s debt?”

She actually turns to look at you when you ask, eyes becoming half-lidded. “Yes, I already said that, but that’s not all this is about. I’m quite fond of you.” She’s direct, and well, she has been this entire time.

“Yes, I understand.” You respond quickly, the words feeling a bit unnatural. You still can’t speak to her in a relaxed way (but you did last night).

If she notices, she doesn’t mention it, instead asking another question. “Do you like me?”

You’re honest with your reply. You have an odd feeling Esme’s the type that could see right through you. “I don’t really know you that well, but I wouldn’t say I dislike you.”

She hums. “Sounded like you liked me last night.”

“But of course, you’re good in bed.”

She grins, laughing lightly. “I’ve been told.” She turns back around, heading into the bathroom. “You’ll be head over heels for me by the end of the week.” Then, the door closes behind her and you sigh softly, quickly putting your clothes back on.

—

Miles goes back to his old ways. You hate to admit that Esme was right, but you have to. He gets into trouble with different loan sharks, and you find him at your door, begging for your help.

You ended up having to block his number some time ago. You thought he had a big heart, but now, you aren’t so sure. He’s asked for so much from you, and you’ve spread yourself so thin to try and help.

Tears well up in his eyes, and no matter what you do, he’ll always be your little brother. When he cries, you feel like you’ll cry too.

He tells you his woes, revealing a similar situation to what happened to Esme. She made it clear that you’re not to ask for her help, but it would be so easy…

You shake your head at the thought. “How much?”

His fingers flex as he looks down at the floor. “40,000…”

“40,000?!” You can’t help but grab his shoulders. “You idiot! Why haven’t you learned your lesson?” He was scared out of his mind with Esme, why then, could he not remember that feeling?

“I’m sorry! I’m sorry!” He apologizes. He doesn’t know you’ve been seeing her. He probably must suspect something going on (given the debt’s disappearance), but you haven’t contacted him very much. “Please, I…”

You sigh softly, relenting. “We’ll…figure it out.”

He nods his head, smiling up at you. His arms wrap around you tightly. “Thank you, thank you…”

—

The sound of the slap rings through the room. You gasp in response to the feeling, cheek stinging painfully. 

“What did I tell you?” Esme hisses the question out.

You grit your teeth, tempted to smack her back. “I didn’t ask for your help.”

“You’re a stupid girl.” Her hand grabs your ear. You wince, whining in pain.

“Stop that!” You grab her wrist, but she doesn’t budge.

“I’ll deal with this, and you will not speak to him ever again.” She tosses you onto the bed, climbing on top of you. Things have been a bit rocky with her, if you’re being honest.

Esme demands perfect obedience. She doesn’t like it when you say ‘no,’ she doesn’t like it when you mess up, and she especially doesn’t like it when you hang out with other people. She’s been showing up at your workplace, demanding attention when you’re supposed to be with customers.

Everyone’s too scared to make her leave, so they let it happen. You outright asked your boss to kick her out (of course, while she wasn’t there), and he shook his head frantically, not giving a further conversation.

“I said I’d deal with it.” You repeat. “I didn’t ask for your help.”

“Do you have any idea who he’s messed with this time? They’re not nice like me, they’ll just kill him, and do you know who they’ll come for next?”

“Stop that.”

“They’ll come for you, it won’t end. I will take care of it. I’m on good terms with them, Miles will still have to pay, but not with his life.”

You stay quiet, torn between protecting your pride or letting her help. “You slapped me.” You state instead.

“Yes, I did.” She caresses your cheek gently, planting a soft kiss to it. “Sorry, I…lost my temper.”

“I don’t accept your apology.”

“You’re angry?”

“Yes.”

She continues to caress your cheek softly. “I’ll take care of everything, but it’s not for free.”

“What’s the price this time?”

Her gray eyes look at you intensely, seeming to spin. “Move in with me.”

You’re a bit taken aback, shaking your head. “We’ve only known each other for four months, it’s too early for that.”

She’s quiet, words coming out just above a whisper. “You know that you need me, and I need you too.”

“I’ll…figure it out.”

She clicks her tongue, she seems to do that a lot. “Is that so?” She pulls off of you. “Then try, you’ll come running back to me when you can’t do it.”

You frown, you know it’s true, but your pride stings, hurting. Anger follows, and it’s directed towards her.

But you swallow it down. “I…I need your help.”

She grins, satisfied with your words. “Yes, you do, so, what do you say?”

“I’ll move in with you.”

She returns to you, hands cupping your cheeks and pulling you in for a kiss. You feel so agitated with her right now, so you end it quickly.

“I’m…going home.”

“Ah, you’re so…pent up…” Hands trace yours. “Let me help you.”

“Not right now, Esme.”

She grabs your face this time, pulling you in forcefully. You don’t feel disgusted, just agitated as you hesitantly return the kiss. Something surges in you and you find yourself grabbing her right back.

“There it is.” She smiles, looking smug and satisfied and it pisses you off. She stays on top of you, pressing her thigh between yours, like she always does. Her head tilts slowly, face illuminated by the moon slightly. It makes her look quite pretty, but you suppose, objectively, she is. It seems to soften her hardened look quite nicely in some way.

Her hands grapple with your clothes, tugging them off before removing her own. In that time, you’ve moved to sit up, feeling torn at the current moment.

She moves closer, pulling you onto her lap. Her lips meet yours, and you respond with vigor, feeling your agitation begin to melt away. You shift, locking one of her legs between yours.

“Ah?” She lets out a questioning noise. “I don’t like you on top, but I guess…you can ride me, if you want.”

Something like that feels almost pathetic, but you press down, feeling the bone of her thigh against your pussy. When you lean forwards and press down, the sensation stimulates your clit. “Mhm…”

Esme pulls your face to hers again, mouth peppering hot kisses onto your mouth and descending down to the corner of your jaw. You thrum your hips slowly, moaning softly. It feels nice to not be the one getting used for once.

Esme moves down, mouth biting on the skin of your neck. A noise of complaint leaves you. When she doesn’t stop, you lean down further, doing it right back.

She twitches and laughs, rubbing the back of your head as she seems to find it endearing.

The knot in your stomach begins to untie. You move your hips quicker, feeling more and more at ease. She wraps her arms around you, holding you close. You stop biting her, instead resting your head in the crook of your neck.

It doesn’t take much longer, your legs begin to twitch, pleasured sounds begin to leave your throat. You’re just about there when she decides to slam you backwards onto the bed. She gets on top of you quickly.

You pant, red faced and agitated at being denied. Your legs stop twitching, with nothing to get you there now.

Esme stares down at you. “It’s better with my fingers.” They descend you slowly, and you relax slightly, but it feels like she’s really trying to piss you off.

She inserts two and then three, squelching noises filling the otherwise quiet room. She wraps her mouth around one of your breasts, beginning to suck sharply. Her teeth bite down, drawing a pained gasp from you. The feeling is mixed with pleasure too.

She adds a fourth finger, stretching you. Your walls close down on her, tightening. She presses hard, finding the spongy spot inside. You keel backwards, moaning heartily in enjoyment. You buck your hips slightly, wanting her to pick up the pace.

Her teeth bite down on your nipple harder in response. You whine again, looking off to the side.

Her fingers finally quicken, thrusting and scissoring inside before she pulls them out with a squelch.

Then, she focuses, pressing her middle and ring down onto your clit.

“Please…” The plea leaves your lips.

She finally complies, quickening her pace and rubbing up and down harshly. Your thighs grasp around her hand tightly, not wanting her to stop.

She continues, faster and faster until your back arches and a moan tears from your throat. She pulls her mouth from your breast, pressing it over your open one.

She bucks her hips slightly, hand becoming even more wet with your ejaculation. You hold her instinctively, rocking your hips against her.

Then, you slump backwards, but you still don’t let go. You can’t. She nuzzles her face into the crook of your neck, kissing you softly, repeatedly.

You close your eyes, loosening up as you slip further back, as if boneless.

She notices. “You’re not tired already, are you?” She pulls back, looking at you deeply.

“A…little.”

“You were so agitated, hm? What happened?”

You only shrug in response.

“Do you love me?” Esme questions out of the blue.

“I like you, but I don’t know about that.”

“I’m sure you’ll love me by the end of the week.”

You smile softly, tension dissipating. You remember her saying something like that a while ago, too.

“You’re mine, after all.” She adds, pressing a kiss to your temple. “But, I’m not done with you yet.”