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Pay the Devil His Dues - A Doflamingo x Reader Fanfic Part 1

Your desperate, starving parents trade you to the ruthless new town Lord, Doflamingo, to cover their taxes.

Smut. 18+. Fem Reader. AU. Age Difference. Size Difference. Dubcon. Innocent Reader. Slightly Rough Sex (will be rougher next chapter). Biting/Marking. Oral Sex. Doffy’s Monstrously Huge Dick.

Dividers by @animatedglittergraphics-n-more and @benkeibear!

Any feedback/comments/reblogs are greatly appreciated!

You vividly remember the day Donquixote Doflamingo arrived in your town. He was the new Lord sent to reign over the locals after the last one was executed for lining his own pockets with money meant for the emperor, Kaido.

The first thing he did was order all the citizens to gather in the town square, where he introduced himself and explained how things were going to be from then on.

“Everyone will pay their taxes,” he said firmly, an unnatural grin on his face. “On time. Every time. And to make it clear just how serious I am, we’re going to have a little show today!”

All the townspeople glanced at each other nervously. Something about this man put everyone on edge. Maybe it was his freakish height. He stood far above every other man there. Or maybe it was the strangely casual state of his attire. He wore the crisp military uniform of the empire in a way no one had ever seen before. The shirt was left unbuttoned and open, displaying his tanned, chiseled torso. The pants hung low on his hips, almost scandalously so, and the long coat was draped loosely over his shoulders.

No, you think it must have been the demonic grin that seemed to be etched onto his otherwise handsome face. It was made more eerie by the blood red lenses of his glasses that completely obscured his eyes.

Doflamingo snapped his fingers and another soldier stepped forward, holding a scroll. The man opened it and called out a name. “William Smith. Step forward please.”

The crowd looked around. The name wasn’t familiar to you, but you certainly didn’t know every person in town. Finally you noticed some sort of commotion taking place several yards away. A man had broken into a run and was fleeing the square.

He didn’t make it very far.

Two soldiers ran after him, tackling him to the ground. He struggled and screamed as they bodily dragged him to Doflamingo, who was standing in the center of the town square, still grinning.

As the soldiers held the man in place, Doflamingo addressed the townsfolk.

“Mr. Smith here failed to pay his taxes the past two months in a row. The last time he did pay, he was a week late and only paid half. So let this be a lesson to all of you!”

So quickly you could barely process what was happening, Doflamingo pulled a large knife from the pocket of his pants and strode over to the now panicking William Smith. While everyone looked on in horror, the new Lord of the town plunged the knife into William’s belly, then ripped it across his abdomen.

Innards began to spill out, guts and organs, still steaming, hitting the ground with a wet “splat”. For a few moments, William just stared down at his own entrails with shock, as if he didn’t believe what he was seeing. Then, he fell forward, landing in the pile of his own guts.

Horrified silence loomed over the crowd as they looked at the now dead body with wide eyes. Until Doflamingo began to laugh.

In the months that passed since then, the town has become poorer and desolate. The people, like your parents, work hard day and night and still have barely enough resources to survive. All the money goes to taxes.

Occasionally someone will not have enough. Depending on how much they still owe, different punishments are handed out with ruthless efficiency.

Not paying the taxes at all results in swift execution. Paying half or less results in public lashings or, in severe cases, the chopping off of a limb. And paying close to the full amount but being a bit short results in the soldiers raiding your home to take anything of value you might have, including livestock and food rations.

It didn’t take long for everyone to figure out Doflamingo is just as corrupt as the last Lord. He’s probably just smarter about it. He accepts trades of things he personally wants, like wine, food, and of course, women.

Generally, it’s the women who voluntarily offer themselves. Some seem to view it as a humiliating but necessary evil they must do to survive or protect their families. But some seem to actually like going to Doflamingo every month.

At first, you couldn’t believe it. He’s a monster who is terrorizing your town. You’ve all witnessed his violence, his brutality. But the more you see of him, from a distance with your mother as your father pays the taxes, the more you understand.

There’s a certain magnetism to Doflamingo, a charisma you can’t help but notice. He’s handsome, well spoken, strong, and has a powerful position in the empire. It’s not that surprising that some women would want to sleep with him.

But you could never do such a thing, primarily because he terrifies you. He is not a man who would show mercy under any circumstances, not even to a frightened girl who has never been touched by a man. The word “gentle” could never apply to him.

There’s also the fact that he would never be interested in you to begin with. He’s never even glanced in your direction. Why would he? You’re an impoverished peasant girl who owns exactly two stained dresses. He’s a wealthy Lord and high ranking soldier.

You’ll probably never even speak to the man.

Tomorrow is the first day of the month, the day taxes are collected. Your parents have been strangely quiet the past few days, whereas they normally fret and complain this time of the month.

Maybe it’s because tomorrow is also your birthday. You’ll finally be of age, an adult. You’ll be able to accept suitors, if anyone is interested, and possibly even marry.

You go to sleep with these thoughts in your head, and end up having a bizarre dream about marrying Doflamingo. It’s both scary and exciting.

The next day your parents don’t even mention your birthday, which is unusual in itself, but they also barely speak to you at all as they prepare to go to the square.

A huge crowd is gathered, most of the men lined up in single file to pay their dues. Ordinarily, most women and children wait on the sidelines, aside from the women who have come to offer themselves in lieu of payment.

To your surprise, your mother lines up with your father and pulls you along with her. What is going on? She isn’t planning to offer herself, is she?!

“Mother, what are you doing?” you ask.

“Shush. We don’t have the money this month. We’re going to try to appeal to his pity.”

Oh no. This will end terribly! Several families have attempted such a thing, but at best it only turns a severe punishment for one into a lesser punishment for many. One man who would have been sentenced to having his arm cut off only had to give up his pinky finger, while his wife and adult son endured public lashings.

Is that what will happen to you? The thought of being tied up in the square and whipped in front of everyone was beyond horrifying. Will that be how Doflamingo will see you for the first time? You can scarcely imagine the humiliation.

As the three of you move along the line, your heart races with worry and your mind clouds with dread. By the time you reach the front, your body is trembling with fright and you’re fighting to hold back tears.

Doflamingo sits in a high backed chair on a raised platform, looking like a king on a throne. One long leg is draped over the arm of the chair and you can see his lean muscles flexing beneath the skin of his abdomen as he talks casually with the other soldiers standing around him.

When he looks up at you and your parents, it’s obvious he notices the new faces. He probably already knows that your father can’t pay and has come to beg for leniency, but he says nothing.

He simply watches and waits for your father to begin his pleas.

To your shock, it is your mother who speaks first. And what she says shocks you even more.

“My Lord, we’ve come to offer a trade,” she says. Then she pulls you forward be the arm. “Our daughter came of age today. We give her to you as payment for our taxes.”

What?! You look at your parents frantically, not believing what you heard. Surely your father would never agree to such a thing! But he’s looking at the ground, avoiding your eyes.

Doflamingo’s face turns slightly toward you as that terrible grin spreads over it. “Oh? And how many months of taxes do you think she’s worth?”

Your mother looks firm and resolute. “Twelve, my Lord.”

Doflamingo stands up and steps closer. Being directly in front of his full height makes you realize just how frighteningly tall he is, and how small and insignificant you are.

All at once he reaches forward and rips your pitiful dress open, tearing it off your body as if it’s made of paper and leaving you in your thin white shift.

You shriek in alarm, curling in on yourself to protect your modesty. Your parents turn their faces away.

“Don’t look away now,” Doflamingo says to them. “You’re the ones who brought this sweet little lamb to be slaughtered.”

You tremble before him, using your arms to shield yourself from his gaze as much as you can. You can’t see his eyes, but you can feel them burning into you.

After a few moments, he says, “Six months.”

Your father looks stunned. “Only six? But my Lord, she is our only daughter…”

Doflamingo returns to his seat. “I’ll make it eight, if she pleases me.” Then his attention shifts back to you. “Today is your birthday?” he asks.

You nod, too afraid to speak.

He laughs. “What cruel parents you have.”

You look back at them. Are they cruel for doing this? Or just desperate and starving? Neither of them will meet your gaze.

The deal finalized, your parents are shooed away and two soldiers drag you in the opposite direction, toward Doflamingo’s base. One of them throws a long military coat over your shoulders, a kindness you didn’t expect. While your shift does cover most of your body, it is by design extremely thin and clinging to your curves. For a young woman to be seen in public this way would be a scandal you could never live down.

When you arrive at the huge house reserved for the Lord of the town, you see mostly soldiers moving about, patrolling, or just taking breaks. A few servants can be spotted doing chores. You’re relieved to see that a few of them are women.

None of the soldiers seem to pay you any mind. No one leers at you or tries to take the coat away. They simply lead you down a hallway and hand you off to some women who are doing laundry. Dozens of military uniforms are folded into near stacks, and three women are scrubbing sheets.

“See that she’s taken care of,” one of the soldiers tells the women, before leaving the room.

The three women look at you in confusion, as if they have no idea why you’re there. Haven’t any other daughters been handed over to Doflamingo before?

One of them, who looks old enough to be your mother, steps forward. “Are you a new servant?” she asks, her eyes clearly drawn to your state of undress beneath the coat.

You begin explaining what happened, but you only get halfway through the story before you start crying. Maybe your parents are cruel after all.

All three women rush forward and hug you. “It’s alright,” one of them is saying, “we’ll look after you!”

“It’s not so bad here,” another offers, clearly trying to console you. “As long as you don’t anger the Lord, he won’t do anything terrible to you.”

The oldest, who looks positively ancient, gives you a grin. “And if he does mistreat you, come tell me! I’ll give him a good whacking!”

The others laugh. “Don’t mention it in front of the Lord, but he’s weak to grandmas!”

You wipe your eyes and try to smile. At least there are nice people here. They help you clean up, bathe, and even give you a dress to wear. The youngest among them, still a good six years older than you by your guess, brought the dress from her own closet. It doesn’t fit perfectly, but well enough, and it’s far nicer than any dress you’ve ever owned.

“There, pretty as a princess,” the motherly one says, looking you over.

You bow your head slightly to show respect. “Thank you, all of you.”

With nothing else to do, you help them with their chores until the end of the day, when the tax collection is over. When Doflamingo walks into the base, flanked by soldiers, he barely gives you a passing glance.

You’re a little disappointed. You’re dressed up for the first time in your life, and some small part of you hoped he would notice.

It’s late in the evening before he calls for you, summoning you to his quarters. Once the soldiers escort you there and leave, Doflamingo stands up from the desk he’d been sitting at. Across it are scrolls and books filled with names and numbers. This must be where he manages the taxes collected.

He walks around the desk to stand in front of you, looming over your far smaller frame.

“I’m going to give you a choice. Consider it a birthday gift,” he adds, that ever present grin widening.

You have to crane your neck to look up at him, but you nod.

“You can stay here and use your body to pay your family’s taxes. It won’t be pleasant. I won’t treat you gently. I’ll wring every drop of value from you,” he says, his voice deep and powerful.

The words are scary, but somehow, deep down, there’s an inexplicable thrill to them.

“Or,” he continues, “you can officially separate yourself from your parents and walk away. Of course you’ll have to pay your own taxes starting next month.”

What? You can just… leave? You hesitate, then ask, “What will happen to my parents if I do that?”

The grin widens again. “They’ll be executed immediately. Not that you should care. They threw you to the wolves and abandoned you.”

The two options dance around in your mind. It’s true your parents betrayed you, but they were facing execution otherwise. And they’re still the people who raised you.

But to stay means to give yourself to a brutal and violent man who terrifies you, to let him do as he pleases with your body. Even if you have been feeling a spark of excitement at the thought of being touched by him, it doesn’t overcome your fear of him.

Doflamingo steps closer, so close you can practically feel him. “Choose,” he says. “I’m not a patient man.”

You stare up at him, seeing the reflection of your wide, frightened eyes in his sunglasses. You know there’s only one choice you can live with.

“I’ll stay,” you say in a shaky voice, your lips quivering.

A low, rumbling laugh emanates from him as he reaches one hand toward you. Reflexively, you flinch. You’ve seen the level of cruelty and violence his hands are capable of. You feel his hand on your head, and it slides down to your neck, then to the front buttons of your dress.

“W-wait!” you cry, and he pauses. “This is a borrowed dress, my Lord,” you say quickly. “One of the women who work here let me wear it. If possible, I’d like to return it to her.”

You glance up, prepared to face his wrath, but instead he’s looking at you with amusement as he withdraws his hand. “If you don’t want it ripped apart, take the dress off yourself,” he says.

“Alright,” you say, reaching up to your buttons with trembling fingers. You unfasten them slowly but steadily, trying to drag this out without making him angry. He returns to his desk and sits on it, watching you as if you’re putting on a show for him.

Once the buttons are undone, you carefully untie the belt at your waist and then slide the dress off your shoulders, letting it fall to the floor before quickly picking it up and holding it in front of you.

The shift given to you is a bit smaller than the one you wore in, showing a little more of your thighs. You stand there holding the dress awkwardly. “Um, where should I…?”

He gestures toward a chair in the corner. “Leave it there.”

You gingerly step over to the chair and gently drape the dress over the back of it, trying to leave it as smooth as possible. When you walk back to your previous spot, in front of Doflamingo, you can feel your face burning.

All this time, you’ve secretly wanted him to look at you, to notice you. Of course you imagined it very differently. In your forbidden daydreams, you pictured him spotting you in the crowd on collection day, and then being so enamored with you that he immediately stopped the collection and stepped into the crowd to approach you. He’d take you back to his base to be his bride, and be so happy with you, so touched by your love, that he’d change his ways and become a kind, noble Lord.

Such childish fantasies.

He steps away from the desk and approaches you again, slowly. His huge hands land on your shoulders, then slide down your arms, pulling the thin straps of your shift with them. As the silky fabric slips down over your breasts, revealing them to the cool air of the room, you close your eyes. It’s too embarrassing to look at him.

The shift continues sliding down, eventually pooling around your feet. You’re completely exposed now, totally bare before a merciless tyrant. You’re afraid, naturally, but you can’t manage to tamp down the electric current running through you, the thrill of finally being perceived by Doflamingo.

You gather your courage and open your eyes, only to see his red glasses leering down at you. Your first instinct is to shrink away, but before you can even have that reaction, he suddenly pulls you to him, your delicate body crashing against his. You can feel his smooth, hard chest, the heat of his skin where his open shirt bares it.

His hand moves to your chin, lifting it up so that your face is tilted skyward. He bends down and kisses you. It’s not the sweet, romantic kiss you daydreamed about. It is rough and dominant, his tongue pressing into your mouth and filling it while his hand holds your face still. It’s suffocating, but the heat of it, the taste of his mouth, is somehow intoxicating.

You’re not sure what to do. You’ve never done anything like this, but be reflex you raise your hands to his toned abdomen and rub across it, relishing the feel of it.

He breaks the kiss and looks down at you, at your hands, then laughs. “Needy little thing, aren’t you?”

You pull them away, shyly dropping them to your sides. Maybe you shouldn’t have been so brazen.

He takes your hands and places them back on his body. “I don’t mind a needy woman,” he says, pulling his shirt off his shoulders. Your eyes roam over him, taking in the absolutely sinful sight. Your hands, carefully and hesitantly, move across his muscled torso.

Seemingly amused by your wandering hands and staring eyes, he unbuttons his pants and pushes them down, giving you more to see and touch. When your eyes fall upon the absolute beast between his thighs, you gasp and draw back a step.

You’ve never seen one up close before, but is it normal for a cock to be the size of your arm? It’s as terrifying as it is mesmerizing. He takes one of your hands and pulls it toward the shocking organ, guiding your fingers to wrap around it as best they can. It’s hot and heavy in your soft grip, and as you watch, it grows and stiffens, like magic.

He sits on his desk, spreading his thighs, and ushers you to your knees before him. You’ve heard enough stories from village women to know what he wants, what he expects of you.

Looking up, you tilt your face to get the angle right, then you hold the massive cock up with both hands. You start by licking it, running your tongue along the underside, hoping you’re doing this right. Then you lick the tip of it, as you would a sweet treat.

His hand appears on your head. “Open your mouth,” he says, and you obey. You feel it slide into your mouth, hitting the back of your throat almost immediately. Your body’s reflex demands you pull away, but his hand is holding you in place. “Breathe through your nose,” he tells you. “Relax your throat.”

You do as he said, trying to will your body to calm down and accept the huge cock in your mouth. It’s not even halfway in, and already you’re choking. He pulls your head back, enough to let you breathe, before pulling it back down. He moves your head slowly, but firmly, establishing a rhythm as well as his complete control.

Doing your best to please him, fighting back your urge to panic, you keep your tongue moving as he continues moving your head. There’s something scary about surrendering control of yourself to someone else, especially someone you’ve seen murder numerous people. But you can’t deny the slick dampness between your thighs. He’s looking at you! He’s paying attention to you!

After a while, he pushes your head down and holds it there. “Don’t spill any,” is the only warning he gives you before a massive load of cum floods your mouth. You swallow it down as fast as you can, barely tasting it before it disappears down your throat.

When finished, he releases you, and you pull away to take several deep breaths. He only gives you a few moments of reprieve before he pulls you up to your feet, not hard enough to hurt but firmly enough to let you know he has little patience.

He stands from the desk, then lifts you onto it, pushing you onto your back and spreading your legs. As shameful as this position is, you still feel a hint of exhilaration when you think about his eyes upon you. His huge hands begin to roam freely over your body, heating every inch of your skin with his touch.

You feel something hard and heavy against your thigh. You look down and see that, surprisingly, he’s already hard again. For a man over twice your age, he sure has plenty of stamina.

Thinking you’re not quite ready to have that monster shoved inside you, you close your eyes again. The next thing you feel is his long fingers between your legs, spreading open your soft folds. They slowly rub over your clit, then his thumb draws circles around it.

Your back arches off the desk as you moan, and you hear him laugh again. At this point you feel too good to be humiliated, so you ignore his amusement. You’re dripping wet as one of his fingers slides inside you. It stings a bit, but it fills you up nicely. When he curls his finger, he touches something deep within you that makes you gasp.

He withdraws his hand and climbs onto the desk, his arms on either side of you, caging you in with his massive frame. You imagine you must look like a tiny mouse to him, gazing up at him with glassy eyes. That terrible grin is still plastered on his face as he reaches down and positions himself at your entrance. It feels like he’s moving in slow motion, letting both the dread and the excitement build.

Then, he pushes in.

He won’t fit. Not without seriously hurting you, but he’s splitting you open regardless. It hurts, and you whimper as you tremble beneath him, trying not to cry or disappoint him. You have to please him to keep your parents alive.

And… there’s that small hidden part of you that wants to please him for your own satisfaction.

He begins moving, and you’re certain he’s no more than halfway in. Maybe he doesn’t want to break his new toy too quickly. His thrusts are slow and shallow at first, then become faster and harsher, making you cry out in both pain and pleasure.

You look up at him, at the reflection of your tear stained face in his glasses, wishing you could cling to him. Would that anger him?

“M-my Lord… May I please…?”

“Hmm? What is it you want?” he asks, never pausing his movements, his cock stirring the deepest parts of you.

You wince at the sting. “May I please… hold you?”

He stops for the briefest moment, seemingly staring at you from behind his sunglasses. Then he grins again. “Do as you please.”

Your hands creep up his shoulders and hook around his neck, holding onto him for dear life as he continues wrecking you.

His tip repeatedly hits that spot. The one that took your breath away, the one that makes you want to feel him even deeper. Soon, you’re shuddering and crying as your first orgasm washes over you. Your arms weaken and fall away from his neck, and in response, he leans down and kisses your throat. You feel his long, wet tongue glide over the tender skin, then, out of nowhere, you feel his teeth bite down. You cry out, your hands instinctively trying to push him away, but you’re powerless against him.

The pain of the bite subsides, and his tongue laps at the wound. It must not have been very deep. Your struggling arms go still.

In the next moment, you feel his cock bulge inside you. Then, as suddenly as he did in your mouth, he spills his entire load in your virgin pussy.

He holds you under him for a few moments more, still gently licking the spot on your neck where he bit, his cock still lodged inside you. Then he pulls away and stands up. He pulls on his clothes, drapes his own military coat over you, and leaves you lying on the desk.

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