*pokes* oh my god! i really love all of your dol headcanons, the suicidal one admitedly made me cry, it's just that good! :'D not sure if you take request or not, you can ignore this if you aren't, but i'd absolutely would love something related to bailey taking reader's virginity...? his dialogue in canon (before it was removed rip) when he took pc's virginity drive me fucking crazy :)
“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."
Minors Do Not Interact; MDNI
