#bailey x reader

Most days, Bailey struggles to decide whether you're an idiot or a masochist.

He’s leaning towards the former, but it wouldn’t take much to sway him towards the latter. That doesn’t make you special on its own, though – no, most of the stupid brats in his orphanage have shit for brains and the survival instincts of pre-splattered roadkill, but you manage to make your peers look like shining pillars of intelligence and caution and all the good, important, necessary traits that you were tragic enough to be born without. If he didn’t know better, he might think that you’re doing it on purpose, that your behavior is just the product of some misplaced cry for attention. You should count yourself lucky that he’s a hell of a lot smarter than you’ll ever be.

He should’ve gotten rid of you the first time you failed to pay your rent. He should’ve, and he tried to – selling you off to the highest bidder, leaving you blindfolded in alleyways and restrained on the edge of town, but like a beaten dog too stupid to acknowledge that its master left it for dead, you always seem to drag yourself back, always bruised, most often bloody, and occasionally soaking wet. More than once, you haven’t made it all the way back, and he’s had to go out of his way to pick up ‘his precious ward’ from the intensive care unit at Harper’s request. He would leave you there, if he thought his reputation would survive giving that freak of a doctor a free lab rat.

 You can’t hold down a job. That part, he can’t entirely blame on you. If going outside is risky, then trying to earn a living is all-but a death sentence in a town like this. He knows you have a few minor gigs, pick up odd jobs every now-and-then around the wealthier neighborhoods, but it’s never more than petty cash, and having to watch you drag yourself through the orphanage halls with torn clothes and that distant, glazed-over look in your eyes almost makes what little rent money you can scrap up not worth it. You’re wary enough to keep your head down in school, so you don’t have a lot of friends, either. Most of your time is spent at home; toiling in your weed-infested garden, trying to pretend you aren’t hiding in your room, and when he lets you, curling up in the smallest, darkest corner of his office – your legs pulled into your chair and your eyes fixed on the floor. He asked, once, why you thought you had to waste your time sulking in his peripheral like some poor, attention-starving kitten. Despite help from the better half of a bottle from his vintage stash, he can still remember your answer.

“I don’t know,” you mumbled, with a smile so delicate, he was almost tempted to see how easily it shattered. “I guess I just feel safe around you.”

He stopped asking for rent, after that.

He tries not to think about you. It’s a constant effort, but he tries the hardest when he’s standing in your doorway hours after midnight, fucking his fist as you pretend to sleep less than a full ten feet away. He still hasn’t made up his mind about the masochist part, but you have to be an idiot. A pretty, empty-headed idiot.

His pretty, empty-headed idiot.

He decides, as he finishes to the sound of your muffled sobbing, that he’ll soak it in while he can. Even if he does his best, even if he keeps his distance, even if you never come to your senses and run far, faraway, he knows he won’t have long left to enjoy this.

“Your body was always mine.”

Synopsis: You owe Bailey, but are short on cash. He takes your virginity as payment.

Contains: afab!gn!reader, anal mention, biting, cervix kiss, deflowering, fingering, masturbation, noncon, oral mention, overstimulation, scratching, purity/virginity kink

Words: 2,159

A/N: Sorry this took so long. It’s been a rough month or so. I wish they would have left us the ability to fuck Bailey at least until they had more lewd content to replace it with. I refuse to acknowledge his canon disinterest in the player.

In a town such as this, where temptations festered in the shadow, it was a miracle you’d preserved your purity for as long as you had. He can’t imagine how you managed, though he supposes your affiliation with the church must have contributed. Fat load of good that did against him, though, didn’t it? It hadn’t been intentional, but he’d gradually accrued your virginities, unraveling your innocence thread by thread.

Once in a moment of weakness, driven by frustration. You’d pestered him all that morning with dumb shit, and in a haze of anger and desire, he overwhelmed you, his hands gripping your body as he bent you over his desk and roughly violated your ass. You fought valiantly, but you were just no match.

"You should be putting out more if you're this tight. What do you think you're good for?"

Once with the intentions to torment that insufferable prick, Avery. You may have been that bastard’s date for the evening, but he was your guardian, and it was about damn time he reminded you both who actually owned you. With the right encouragement—threats against that other brat, Robin—he hadn’t needed to lift a finger for your mouth to get to work. The look on that man’s face as you choked on him was the highlight of his evening, though your inexperienced tongue running alongside his shaft was a contender to be sure.

"Don't get any funny ideas. Just take it."

Once more that same evening without thinking. With all the adrenaline coursing through his body, he hadn’t considered the significance before grabbing your hand and thoughtlessly dragging you off to his car. He hadn’t registered the way your hand tensed against his own until long after he’d dumped you off at the orphanage.

Lastly, by your discretion, too drunk for you to realize the “handsome stranger with kissable lips” was in fact your caretaker coming to collect your dumbass after you’d gone and got yourself roofied. You were lucky it was the day before collection; otherwise, he wouldn’t have bothered. For reasons unknown to even himself, his resolve to remain indifferent crumbled under your clumsy lips, pulling you close to dress your lips with his and turning that chaste brush of lips into a ferocious battle with his tongue. You probably still think it was that haunting freak you barely tolerate who took your first kiss, but he hasn’t forgotten.

"Surprised are you? You'll learn to kiss better soon."

Now, behind the locked door of his office, he finds himself clawing at the remnants of his self-control, trying desperately to ignore the desire that began to bloom since he first pinned you against his desk. He palms at the ache pressing against his trousers, shame creeping along his spine. He should never have let things get as far as they did. There were lines he had resolved not to cross, and yet here he was, hips jerking to the thought of your warm tongue, soft lips, and tight ass.

The thought that you’ve been sauntering around town with that virgin cunt of yours unprotected, purity vulnerable to any prowling perverts, evokes a possessive rage that has no place invading his thoughts.

He sure as fuck shouldn’t be entertaining the thought that you’re only some doors down, just out of reach. The desire to own you in full has him in a chokehold. Growling, he reclines deeper into his swivel chair, impatiently fishing his cock out from his trousers, leaking pre-cum down over angry veins.

Fuck it, just this once.

With a sense of urgency, he gathers himself in his hand, tightening his hold damn near enough to strangle, and begins furiously pumping his hand. It doesn't take too long before he reaches that precipice, jaw and core tightening as he inhales sharply. Warmth spreads over his hand, pace and grip relaxing as he eases himself down from his high.

Releasing a sigh, he reaches across his desk for a tissue. After cleaning himself off and resituating himself into his pants, he glances down at his wristwatch.

12:30 AM

Right, there was still the matter of your debt. Before he could erase you from his thoughts, he had to collect your payment for this week. It was admittedly early, but the day of collection nonetheless, and he could swing by damn well any time he pleased. He steels himself before pushing the door open and striding up the stairs towards your room. The sound of your laughter mingling with that of another orphan—Robin, his mind supplies to his distaste—pulls at his insides like a vice.

The door swings open violently, the force startling the both of you into silence. The sight before him reignits that possessive rage; your hips straddling his with only a pair of panties protecting you from his exposed length. Underneath you, the boy cringes as Bailey's attention rests on him, eyes widening in bewilderment and terror. The air was thick with tension.

“Get out.” He bites out as calmly as he could manage, nails digging into his palms.

Robin casts a rueful glance between the both of you, torn between the desire to shield you and fear. You assure him that you’ll be fine, gesturing towards the door with your chin.

“But—” Robin begins, but is interrupted by Bailey.

“Did I fucking stutter?” he snarls, the animosity seemingly making the air colder and heavier. Quickly worming back into his night shorts, Robin slinks by Bailey while sending one last remorseful glance your way before vanishing down the corridor.

Silence punctuates his departure. Rage simmers below the surface of his skin, threatening to burn him. The sound of shuffling sheets punctures the quiet, instinctually causing him to look your way. Breath catches in his throat, soaking in the sight of your exposed thighs. As you reach for your bottoms, awkwardly twisting your body, he sees what he believes must be that brat's fluids discoloring your underwear. Lips twitching, he’s overcome with the desire to tear it from your body and have it burned.

Had he arrived even an hour later, you’d have surrendered your virginity to that urchin. Struck with violent impulse, he feels the final strand of resolve disintegrate. He stalks forward, his presence overwhelming as he closes the distance between you.

Scrambling back until your back is pressed against the headboard, you glare daggers, demanding to know why he’s here. The slight tremble of your voice reveals the fear underlining that false bravado you’ve taken to wearing. He makes note of your shifting eyes, frantically searching for an escape, and snorts in amusement. There would be no trouble subduing you, especially at this distance. Perhaps you came to this realization yourself, your eyes snapping back to him with a trace of defeat settling onto your features.

“You owe me.” A grimace overtakes your expression. Ah, now this was a first. Of all his orphans, you were one of the few that were consistently prompt with their payments. No wonder you were offering yourself to that brat. Now, no guilt would weigh on his conscience; you owed him and he intended to collect. You had only yourself to blame for whatever happened next.

Gathering your voice, you stamper out a retort, voice raising as you speak. “I-I’m a little short, but I ha-have enough to cover Robin! Do whatever to me; just leave him out of it!"

You nervously extend the bills out, and he snatches them, flicking through the stack to tally the sum. Satisfied with the amount, he stuffs the wad of cash into his pocket before glancing back up to you.

“I know just what to do with you. Don’t worry, I have no interest in that brat joining.” Closing the distance between you, he snatches your ankle and drags you towards him before you can resist.

You yelp as he pounces, quickly pinning your arms above your head and adjusting his grip so he can hold them down with just one hand. He doesn’t give you a moment to react before he snatches your lips with his own, silencing any potential objections. His tongue swipes across your lips, thrusting down your throat—domineering, rough, and speaking of suppressed desire. Pulling back, a string of saliva connects your lips.

“Wh-What was that about...?” You gasp out, greedily sucking in air, nearly suffocated by his intensity.

“You owe me.” He begins, hand drifting down to cup your sex. “And you have something I want.”

Tears gather at the revelation, struggling against his hold. “N-no way! Haven’t you stolen enough from me?”

Snatching your cheeks in his fingers, he clenches as a warning and sneers. “You fucking owe me, so unless you want me knocking on that brat’s door for payment, you’ll do whatever the fuck I tell you.”

You sniffle and sob, but otherwise settle down, realizing you have no other choice but to comply. Watching your eyes for any signs of rebellion, he feels assured you won’t try anything and releases your face and arms. You go limp, defeated. He hooks his finger in your panties, impatiently pulling them off your body before tossing them to the floor. He doesn’t bother to take off your shirt.

Though having seen you exposed before, he can’t help but stare in appreciation at your glistening lips. Swiping his middle and ring finger between your folds, he wastes no time before sinking knuckle deep, aided by your slick.

“Fuck, you’re soaked. That brat do this to you?” He begins pumping his fingers and circling your clit with his thumb, enjoying the crinkle of your nose and eyes as you try to maintain composure. “Or do you actually want this?”

You shake your head and try to say no, but your voice breaks into a whine as he curls his fingers against a sensitive spot. He takes the initiative to attack that spot, pressing a hand against your chest to hold you down when you begin to squirm.

"Just relax. I'll handle everything like always."

Feeling your chest rise faster and walls clenching tighter, he pulls away just as you’re about to reach your high. A whine leaves your throat against your will, feeling betrayed at the loss of his fingers. Without warning, his hands grip your waist, pulling you into him and replacing his fingers with something much thicker. The sudden intrusion steals your breath away and sends you over the edge, vaguely registering the pain through your climax. Perhaps he was just impatient, or maybe he cares some semblance to distract you from the pain of being split open by something so large. Either way, he gives you no time to adjust to his size, fingers digging into your skin and leaving crescent-shaped marks.

His eyes and lips pressed tight, overwhelmed by your tight heat. He’s plucked plenty of virgins, but none had brought him such intense pleasure. Melting into you, he sinks his face into your neck, tongue gliding across your skin and savoring your taste. You shiver as his lips trace your collarbone, the nipping of his teeth forcing sharp breaths from your throat.

It’s subtle, but you can hear his muted groans as his hips snap against yours, hungry and desperate. The sounds of wet, heated sex penetrate the thin walls of your room, sure to be heard by all. He can’t find it in him to care when all he can focus on is how sweetly you massage him, bringing him closer to the precipice of pleasure with each thrust. The crown of his cock kisses your cervix, your back arching from the sensation as your hands and legs wrap around him. Your nails dig into his back as that coil in your stomach tightens, leaving deep scratches in their path.

As you push against his thrusts, his hand slips between your bodies, teasing your clit with fervor. You feel yourself slip over that edge, head snapping back against the bed and calling out his name with eyes twisted shut. Feeling you tighten, he loses composure and begins frantically chasing that high for himself. Sensitive, you whine from overstimulation, softly calling out his name to catch his attention. The sound of your soft voice helplessly calling for him and only him lights his nerves and leaves him helplessly gripping the sheets. He bites down on your shoulder to stiffle a moan, spilling into you. His hips grind into yours as he winds down, hands tenderly gliding across your body.

As he pulls back, hot white pools onto the sheets below. He admires the mess he’s made: your bruised skin, neck raw and glistening, and lips parted as you try to gather your breath. His thumb ghosts over your lips, amused by the dumb look settled on your face. Satisfaction thrums through him, having claimed the last of your purity.

"Your body was always mine. Like your first time."

"Come now, open wide." Bailey's thumb swiped over your lip, smearing his precum all over it. You obediently opened it and darted your tongue out, feeling his head twitching above your warm tongue. He didn't wait for you to open wide enough for his size, forcing his way into you. He could feel your teeth scrapped his cock and he surprisingly enjoyed it.

"Careful with your teeth, you don't wanna lose them right?"

His words seemed to scare you as he felt you open wider. It didn't take him long to use you comfortably, fucking your face and throat like a fleshlight, only giving you split seconds to breathe before he buried his cock deep into your throat, feeling it twitch and gagging you.

At least he had trained you well enough to not have you vomit or gag too much. A toy he molded to his own cock's shape and size. Any holes that he could bury himself into were bound to be ruined by him and you better thank him that he was merciful enough to not tear a new hole into you.

Maybe that wouldn't be a bad idea for when you started to misbehave and defy him, put you back into your rightful place.

His pace was no longer steady and he started to lose his temper, his hand tugging and pulling your hair harder to the point you felt like he might tear your scalp. He was close, damn close.

"Attagirl/boy, gonna feed you dinner. Don't waste a single drop."

God he loved how salacious the noises you made, struggling to accommodate to his size. Not like it would last any longer as he pushed your face into him, pouring his cum into your throat while you simultaneously drink it down. Just before he finished, he pulled back and came into your mouth as well, "Show it to me before you swallow."

And obediently you did. You could taste the aftertaste and to be frank, he tasted way better than anyone you knew, mostly contributed by his healthy diet and way of living you suppose. Anyone would have thought Bailey lived off cigarettes, drugs, and alcohol but Bailey was a healthy man.

And that would his semen taste damn good.

Good enough to make you squirm in impatience, waiting for him to allow you to swallow it as he eyed your mouth. The sight alone made his limp cock grow again.

"Good. Now swallow it."

cw: forced captivity

thinking of yandere bailey ever since experiencing the game night scene (ˉ▽ˉ；)...

"...but the brat belongs to me." wasn't just a statement to get avery off his high-horse, it was fact—every word of it.

originally, he was gonna keep his promise—of letting you go after you've paid off all the debt you've accumulated over the several years you've been under his care but something about you showing up to his apartment with one of his so-called 'buddies', hanging over his arm like some sort of prize kinda rubbed him the wrong way.

...and now, he's thinking of keeping you in the orphanage, your little glass box, forever—like the treasure you are, a treasure he had failed to see the value of till that day.

not out of love, hell, not even out of lust but a possession like no other, a pride of knowing he might be holding the source of desire for many. he doesn't really care about you per say—if you threw yourself on the street, slept with every single breathing creature out there - as long as you returned to him... he's content.

...because without him you wouldn't have had a home to grow up in, wouldn't have gotten the education you needed, wouldn't have been able to make yourself who you were today.

he gave you a purpose.

so why don't you be a good brat and sign the contract... and maybe if you're extra obedient, he'll increase your share of the orphanage's revenue by another two percent.

1)Literally no one even knew Bailey was married OR capable of love and other complex feelings

2)Him being a caretaker is actually what drew her to him cause she was also an orphan and loves children (She’s from out of town, there’s trauma but it’s more of a parentification sorta thing)

3)Despite how he talks about the orphans she feels that deep down he loves them and is just tired(he doesn’t)

4) PC is an office assistant and transferred to this town, works for avery and thats how they first met

5)PC insists on buying the orphans gifts, snacks, and planning party’s “cause they just look so sad :(“ and “Maybe a change of scenery could encourage growth and positivity! :D”

>Bailey always says no, but she does it anyway (He’s pissed but at least she’s using her own money for all this)

6)Btw PC is completely unaware that Bailey has been trafficking orphans for years and if they ever found out there’s gonna be 2 mental breakdowns, PC for obvious reasons and bailey who’s going to lose them forever (possible yandere outcome)

E1

You were Bailey's favorite orphan, the only orphan he actually cared for as if you were his blood and flesh. While the other orphans got stuck with worn-out clothes, he’d get you a new dress whenever you got bored with the ones in your closet. He would spare some time to actually bathe you, do your hair, and sometimes help you with your homework.

There was also a nanny who was specifically assigned to take care of you. It was the same nanny to had breastfed you the first day he took you under his wings, so seeing her face for so long made you mistake her for your mother. Bailey wasn't happy about that when he knew about it. He never got angry around you, lest toward you so it was the first time you were actually terrified of him.

Unlike the other orphans, you were slower when it came to picking up on emotional stuff. Any other kids would have learned to call either Bailey or your nanny “Papa” or “Mama” when they were one year old whereas you were already three when it happened.

You cried for the whole day when he just so much as scolded you, not even close to how he usually berated the others and that left you bedridden from fever. Oh, Bailey was sweating bullets when he heard that you were terribly sick. Aside from the risk of any underlying medical condition that might follow, he kept on muttering about the fear of losing you again.

Bailey wouldn't go to the temple to pray to God. He simply prayed to someone else for your well being.

word count: 952

tags/warnings: virginity loss, power dynamics, reader has a cunt and wears a skirt but no gendered terms are used, dubcon, degradation/name-calling

“Alright, brat,” Bailey sneered, standing up from his desk. “You want it so bad? Bend over. Let me teach you a lesson.”

Your blood ran cold. You had just been teasing, only trying to rile him up and annoy him. But when you looked into Bailey’s eyes, you realized…this had gone too far. 

“W-wait, hold on–” you tried to speak up, but apparently you hadn’t been moving fast enough, because Bailey suddenly moved behind you and forced you to bend over, your face smacking the cold wood of his desk. 

“Too late,” he growled. “Isn’t this what you were asking for?”

With all my DoL stories, I will be changing school to university, and the orphanage will just be an apartment complex with Bailey being your landlord instead of caretaker.

All characters in this one have he/him pronouns and male genitalia.

Reader characteristics not specified

TW - I mean, you read the title what do you expect?