Archive of Our Own ^beta

Chapter Text

“Hold the elevator!” Dammit I’m going to be late. Your heels click against the tile floors as you beelined towards the elevator. The doors were about to shut but then you noticed a certain woman on the elevator. “Baby 5! I need you to hold the elevator for me!”

“YOU NEED ME.” The dark haired woman stops the elevator with her foot, giving you the opportunity to get on.

“Thank you Baby 5.” You clutch your chest in a fight to catch your breath as the doors close. “You're a lifesaver.”

“My pleasure .” She smiles with a rosy blush dusting her cheeks. “I mean you did need me after all.”

“I did.” You give her a friendly pat on the back as the elevator starts making its way to the 44th floor. “Take this as my thanks.” You open your lunch box and pull out the doughnut you were going to have for breakfast.

“Thank you.” She beams. “I’ll treasure it forever.”

“You're welcome, but I’d recommend you eat it by noon.” The elevator clicks to your floor and you get off. “Have a good day, don’t work too hard.” You wave the woman off and make your way towards your cubicle.

“Let’s get down to it.” You murmur to yourself as you power your computer up. As soon as the home screen lit up you were met with a billion new email notifications. How wonderful. Scrolling through them you noticed they were mostly asking the golden question of your bosses whereabouts. Last week he left for a business trip to Drum Island and wasn’t due back until this coming Monday. As frustrating as it was to get the repetitive emails, it was thankfully Friday, meaning it was the last day you would have to deal with them.

After spending the good portion of your morning replying to each of the emails, it was finally time for a small break meaning it was also time for your daily task of antagonizing your said boss. Normally you would do what you're about to do in person, but since he wasn’t here you had to resort to other methods. You pull your cell phone out and check your surroundings to make sure you are alone. A smirk forms on your lips seeing no one was around, so you sink down in the office chair and spread your legs before taking a picture of your lacy panties.

Y/N🐇- Sir, do you think these are work appropriate?: Attached image

Doffy🦩- For a slut like you, I think they are more than appropriate.
You weren't surprised by the quick reply, he was probably expecting it considering you’ve sent him something like this everyday that he’s been gone. But you couldn't help it and since today was the last day to get away with this, you decide to take things a step further. You dip your free hand in between your legs, pulling your panties to the side to show him what he was really missing out on.

Y/N🐇- What about this?~ Attached image

Doffy🦩- What a shameful employee I have, seems like I need to teach you a lesson on professionalism.

Y/N🐇- Stop acting like you don’t like it 😉, besides we aren’t exactly “professional” are we sir~

Doffy🦩is typing…..

This rather strange relationship between you and Doflamingo started one year ago when you were offered the job as his personal assistant. The man himself gave you an employee contract/agreement and instructed you to look over it very carefully before accepting. The agreement seemed quite normal at first, mentioning things you were expected to do like, dress appropriately, arrive at work in a timely fashion, etc. But then you got down to the column labeled ‘other duties as assigned'. That's when you knew your job was going to be a lot more than keeping up with his schedule and remembering birthdays.

The list varied from things like, always do what Doflamingo asked, to more intimate things such as making an established safeword with him. The safeword part confused you, but then you stumbled across the list of explicit activities and punishments he was into. The more you read, the more you realized you were being offered a job not only as his PA, but as the man's outlet for his “frustrations” , both work-related and sexual.

At first you were hesitant, thinking did I really go to college just to become my potential boss's plaything? But then again, you couldn’t say you were fully against the idea. The salary was double the amount of a normal PA (for obvious reasons) and the thought of “being under” a man as handsome and powerful as Doflamingo didn’t sound so bad. So in the end you agreed.

To this day you still don’t regret your decision. You truly love both aspects of your job and even though he could be a little bit of a bastard, Doflamingo was still a great boss. Speaking of.. You go to pull up your text messages to see if he replied but stop as your desk phone begins to ring.

“Donquixote Brothers LLC, this is Y/N….. I’m sorry sir, Doflamingo is currently out of office and won’t be back until Monday.” You roll your eyes as the voice on the other line sighs in frustration. “I apologize, but If you give me your name and number I can have him call you-” Your sentence was cut off as static fills your ear. “Are you still there?” Weird? You place the phone back on the receiver and hope the person calls back.

“Fufufu, you know it’s rude to hang up on someone my dear~” The blood in your veins runs cold hearing the familiar laugh and condescending tone of none other than…

“Doffy!?” Turning around in your chair, you come face to face with the smirking blonde who of course was playing with the line of your office phone. So it was his fault..

“Don’t look so surprised Y/N~” You watch his smirk grow wider seeing you were a little more than “surprised” by his sudden arrival. “You made it very clear that you missed me oh so much this week, so I figured I’d come back a little early.” He throws the phone cord down and strides up until he is towering over your sitting form.

“Oh yeah?'' Having him looming over you was a little overwhelming, but you learnt early on that Doffy loves it when you challenge him, so you were going to do just that. “You're one to talk~” Shooting him a smirk of your own, you lean back in the chair acting calm and cool. “I’m starting to think it was you who missed me considering you went out of the way to come back early.”

“Is that so?” You could tell from the veins on his forehead that your comment quite literally struck a nerve. “You were already in trouble for teasing me all week, and now you want to test me even more with your bratty remarks?”

“Yeah I guess so.” You let your legs part a little, giving him a view of your damp underwear. “What are you going to do about it?”

“If you keep running your mouth.” The chair squeaks as his hands come down to your armrests, leaving you completely caged in. “I'd be more than happy to show you what I’ll do about it.” The dangerous tone of his threat sent shivers up and down your spine.

“Well~” You manage to wiggle your chair out of his hold so you can turn back around to the desk. “As fun as that sounds, I don’t think you’ll have any time for that, sir.” You grab the huge stack of paperwork that accumulated in his absence and turn back to him, shoving them into his chest. “Looks like you have your work cut out for you.”

“Is that so my stupid girl?” You squirm in place watching him crumple the papers in his gloved hand. “You don’t know what you just got yourself into.”

“You keep saying that, but you don’t seem to be doing anything about it.”

“You truly are just a glutton for punishment, aren't you?” Your heart rate picks up as his gloves hand wraps around the delicate skin of your neck. “Answer me.”

“Well.” Despite teasing him about his piles of work, It’s been a long and rather lonely week without him, so you're more than ready for whatever he had in mind. “Yes.” The hand not wrapped around your neck caresses up the sensitive skin of your thighs.

“As fun as that sounds fun.” His fingertips had just reached the band of your panties before he pulled away sporting an evil grin. “I don’t think I have time for you today, whore.” A frustrated cry leaves your lips knowing not only did he turn your own words against you, he also planned on leaving you high and dry. “I’m going to be busy, so don’t let anyone disturb me, that includes you.”

“Yes sir.” He walks away without another word leaving you a flushed, embarrassed mess.

~~~~

It was nearing the end of the day and you haven’t seen Doflamingo since your encounter earlier this morning. The fact bummed you out in all honesty, you were hoping he’d break over and pull you into his office, but he unfortunately didn’t. Glancing at the clock you realize it was time to shut your computer down for the day. Your finger had almost reached the power button before an email notification chimes on the screen. Seeing it was from Doffy, you immediately click your email icon to see what it was.

Subject line- Disciplinary action
Y/N,
Due to your recent “behavioral issues”, I will be issuing you a daily punishment beginning this Monday and ending on Friday. If you have any questions or concerns, feel free to find someone who actually cares. (Because I assure you I don’t)
-Donquixote Doflamingo, CEO Donquixote Brothers. LLC
P.S-I hope it was worth it.

“Are you kidding me?” You mumble to yourself seeing the email attachments of all the “evidence” of your said bad behavior (AKA the nudes and sexts you sent him). Not only that, the devious man was making you wait until Monday for any action, that alone was a punishment in your eyes. But then again it did give you something to look forward to next week~

~~~~

~~Monday- Punishment day 1~~

Oddly enough you enjoyed your weekend. The entire time your mind constantly swirled trying to guess in what ways Doflamingo planned to punish you. As you walked into the building your phone buzzed in your pocket.

Doffy🦩- Report to my office first thing this morning.

You didn’t feel the need to respond back considering you were almost there.

“Good morning sir.” You walk into the office and see Doflamingo sitting in his chair sporting a neutral expression.

“I’d tell you the same, but I assure you it’s not going to be good.” The neutral expression disappears and changes into a wicked smirk. “For you at least~ Take your clothes off.”

“Yes sir.” The confidence you felt goes MIA as you start undressing yourself for the man. One by one your articles of clothes hit the office floor until you were fully naked and shaking with anticipation.

“Fufufu~ You seem on edge Y/N.” Doffy stands up from his chair and starts to circle around your nude form. “But I guess I understand considering what I’m about to do to you.” Your body tenses up as his hands find your plush hips, giving them a rough squeeze. “Go over to my side of the desk and get on your hands and knees.”

“Yes sir.” You follow his command and go around his desk before crawling onto the surface. After moving some of his papers and supplies to the side, you anchor the palms of your hand flat against the desk as you bring your hips high in the air.

“Now let's see~” He walks around his desk and sits down in his chair, giving him the perfect view of your bare cunt. “I’m not surprised to see that you're already wet.” The muscles in your thighs shake as something trails up and down your wet slit. “It's practically begging to be filled up” You feel something rubbing at your opening, but you couldn't tell exactly what it was. “Don’t worry, I’ll make sure you're nice and full.”

“Sir wha-” Your words are cut off with a scream as a hand roughly comes down your ass, causing whatever was in your walls to fall out. Despite being in pain, you were curious to see what Doffy had inserted into you, so you lifted your hips up and looked down. No way.. Your cheeks heat up seeing an ink pen that was coated in your arousal laying on the desk. That was in me?

“Fufufu~ Y/N you just gave me an idea.” A large hand laces through your hair and roughly slams your face into the desk. “Listen up.” The pen that had fallen out of your cunt was slid back into you, causing you to moan. “I’m going to stuff your pussy full of these and then I’m going to spank you twenty times.” The thought of being his human pen holder was a little embarrassing, but at the same time it turned you on. “But here's the catch~ If even one of these pens falls out of your useless hole while doing so, I’ll start over.”

“Yes sir.” One by one Doffy shoves your pussy full of the ink pens until you are stretched out.

“My my~” The palm of his hand firmly pressed against the pens, causing them to grind against your g-spot. “You make an excellent pen holder~” He leans over your form and taunts in your ear. “Now let's get to the fun part.” Your walls squeeze around the pens feeling his gloved hands ghost up and down the globes of your ass. “Start counting.”

“One.” You cry out receiving the harsh first slap.

With each hit you found yourself growing wetter and wetter, making keeping the pens in harder.

“Fufufu~ that makes 18, don’t let one of them drop or else I’ll start all the way over~”

“19!” You cry out as desperately clench your walls to keep the pens in place.

“Last one~”

“Wait.” It was too late, before his hand could reach your skin a few of the pens slipped out and landed on the desk below.

“Oh how unfortunate.” You could cry knowing you were going to have to do it all over again. “You were almost done too, looks like we'll have to start over.”

“Sir I’m sorry..” Tears fall down your face as you try to focus on anything beside the searing pain you're experiencing. “I can’t take it anymore.”

“You say that like I care?” He slides the fallen pens back into you. “Start from the top.”

“One!” You cry as his hand meets your tender ass yet again. One after one you began sobbing more and more.

“Twenty!” You cry out the last one as your hands paw at the loose papers on his desk, crushing them in hopes of channeling your pain into the writing. “Thank you sir.” It was finally over and you couldn't be more glad.

“Your welcome~” No longer able to hold your body up, you fall limp against the desk as you try to catch your breath. “I’ll take these back now.” His hand wraps around the bundle of pens before pulling them out. You grit your teeth as Doflamingo pulls your lacy panties back over the abused flesh. “You may leave now.” Slowly you rise up from the desk and fix your skirt. “And before you go, I need you to do something for me.” With a wicked smirk, your boss places a thick stack of papers into your jittery hands. “Be a dear and retype these for me.”

“Okay.” With the stack of papers, you leave the office sniffling and with a limp in your step. “That jerk.” You mumble under your breath knowing he gave you this on purpose, because typing involves using your computer, which involves having to sit down on your sore behind.

After a ten minute stand off with your office chair, you carefully lower yourself onto the cushion below. You bite back a cry as you rest your weight on your backside. I need a ibuprofen, or maybe an entire bottle.
“Bahaha.” Your mind was focused on the literal pain in your ass, you failed to notice the one standing at your desk. “Here’s my department's reports for Doffy.”

“Thanks Trebol.” You reach over to get the papers from his hand and nearly yell feeling the blooming pain in your rear. “I’ll give them to him when he comes back from his meeting.”

“You look like you're in pain bahaha” Hearing him laugh was enough to make you want to knock the guy's lights out. “Did something happen?”

“Yeah, I just fell this morning.” Fell thirty-nine times on Doffy's hand. “I’m fine, thank you for asking.” A fake smile forms on your lips hoping he wouldn't investigate it any further and lucky you, he took the bait.

~~~~

Finally the sweet, sweet time of 4:30 rolls around, meaning you get to go home, meaning you could finally sit down on a glorious frozen bag of vegetables. You waste no time grabbing your lunch box and your purse before heading toward the elevators.

You click on the button and watch as the light slowly makes its way up to your floor. The elevator lands, making a small chime sound. You’ve got to be kidding me. The doors opened to reveal none other than Doflamingo.

“Good, you're still here.” He walks out of the elevators holding his briefcase. “Come with me.”

“Okay?” You internally scream no watching the elevator door to frozen pea freedom close.

You follow him into his office where he asks “Let me see.”

“Let you see what?” You shut the office door behind you and quirk a brow at the man.

“Just turn around.” You were a little confused, but you twirl around on your feet. “Bend over my desk.”

“Doffy wait!” You turn back around in a state of panic. “I don’t-”

“Calm down.” He cuts you off by grabbing your shoulders, forcing you to turn back around. “It’s not what you think.” You feel the fabric of your skirt lift up as he pulls your panties down, revealing the large purple and red handprints welted into your plush skin. “I did quite a number on you~” As prideful as his remark sounds, you also notice the remorseful softness of his fingers caressing over the raised skin. “Lay down.” You walk over to his desk and let your torso fall against the surface.

“So what do you hav-AH.” A yelp escapes your lips from both the shock and discomfort of something cold meeting the skin. You look over your shoulder and see him holding a small bottle. “What is that?”

“Aloe vera gel, it will help bring the swelling down.” His action was confusing, scary even considering he has never done anything like this in the past, but despite that fact, you find yourself purring as his large hands rub the gel into your skin.

“I was always taught never to eat out of the same hand that hits me.”

“That only counts if you don’t like it.” You laugh at his rather blunt reply. “And you, my dear, like it very much.” He states while rubbing the last of the soothing gel in.

“Touché.” But maybe not 39 times. “Thank you, I feel like a new woman.” You try to lift up from his desk ,but a large hand pressing in the middle of your back stops you. “Doffy?”

“Why the rush Y/N?” You tense up feeling his overwhelming presence looming over you. “I’m not done with you quite yet~”

“What?” His hands move down to your sides before lifting you off the desk by your hips. “??” Your hands grab onto the edge of his desk expecting him to roughly bottom out in you, but instead you feel hot breath fanning over your clit.

“I think I’ll indulge myself~” His hands move down to hook around each of your thighs, pressing you even further into his face as his expert tongue begins to eat you out from behind.

“Doffy please~” You beg as drool rolls from your parted lips and onto the desk below. “More.” The way his tongue was lapping and sucking the sensitive pearl had an orgasm building up fast. “It’s s’good I’m gonna.”

“Do what you want.” The vibrations from his deep voice were enough to send you over the edge.

“Doffy!” You cry out his name as his tongue rides you through your orgasm.

“I think I’ve had my fill.” The hold around your thighs releases, causing you to fall against the desk. “Are you alive down there?” To blissed out from the strong orgasm, you answer him with a nod. “Good, I’ll see you tomorrow.”

“But..” You knew better than anyone that Doflamingo was a taker, and if he did give like just now, it was never without something in return. “Don’t you want to.?”

“Trust me I do~” He picks you up from the desk and helps place you on your feet. “But I don’t think you could handle it.” What he said made sense, you doubt your poor butt could handle any more rough “activities”.

“Aww, who knew you could be so sweet and considerate~” Although you sound like you're teasing him, you were dead serious.

“Young lady, you may be speaking too soon.” He smirks, wiping your slick off his chin. “This is just the first day of your punishment after all~” You blush as his hand adjusts the skirt around your hips. “I’ll see you first thing in the morning.”

~~Tuesday- Punishment day 2~~

Just like yesterday, Doflamingo instructed you to come to his office first thing this morning. You knock on his door and receive a malicious “Come in~”

“Have a seat.” He immediately points to one of the chairs in front of his desk. You nod and walk over to sit in the chair. “I have quite the surprise for you today.” He stands up from his desk and makes his way over to your sitting form. A wild smirk forms on his face as he pulls a bundle of red rope from behind his back. “Hold still for me.”

“Don’t you want me naked first?” You question.

“It won’t be necessary.” Your skirt bunches around your hips as he places your thighs on the chair's arms rest. “I’m sure that is disappointing considering how much you love being fully exposed in front of your owner~” His large hands wrap and tie the rope around each side, restraining both of your legs and leaving you spread open. Then his hands wrap the remaining rope around your torso, immobilizing both arms.

“Sir..”

“Since you can’t seem to stay quiet.” You watch as the red satin tie around his neck comes undone. “Say ahh~”

“Ahh.” You part your lips and let his tie enter your mouth like a gag. He then wraps the fabric around your head and ties it in place.

“You are probably wondering what I have planned for you.” He walks back over to his desk and pulls something out of one of the drawers. “Let me show you.” Your eyes widen seeing the magic wand in one hand and a remote controlled egg vibe in the other.

You squirm nervously in the chair as he squats down in front of your restrained form. His gloved fingers hook around the slit of your panties, pulling them to the side. You knew you were already soaked from the mere fact you were tied up and completely vulnerable to the man in front of you.

“Since you seem well and ready~.” He smirks before lubing the vibe with your own arousal. “Let’s put this in here.” The egg nudges against your walls as he slowly presses it into you. He lets your panties snap back in place before he slips the vibrating wand under the band of your panties. “Hmm choices, choices.” You cry into the tie as the wand comes to life against your clit. “I think I like it right here~” He leaves it on the highest setting while your panties keep the wand anchored against your clit. “Oh I almost forgot.” He smirks, holding up the small remote, clicking a button.

“Mhmm.” You wither in the chair as the egg begins to massage your g-spot.

“I bet that feels good.” You nod as Doflamingo sits down in his chair and opens his laptop. “Fufufu~ Let’s see for how long.”

You weren't sure what he meant by that at first, but now after 4 hours of being tied up with both vibrators on their max setting, you figured it out. The punishment was enjoyable at first, feeling the strong buzzing on your clit and the delicious vibrations against your g spot but after two orgasms, things started going downhill. Now your clit was swollen and numb, but you were somehow still cumming.

“Did you cum again?” You nod your head as tears roll down your face. “I do believe that was number 15~” Doffy sat back in his office chair, hands behind his head smiling like the evil bastard he is. “Tell me, does it still feel good?”

“D-ffy.” You look at him with pleading eyes before shaking your head from side to side.

“Don’t look at me like I’m the bad guy.” Doffy gets up from his chair and stalks over to your shuddering form. “In case you’ve forgotten, you brought this on yourself..” He smirks seeing the frustration in your glassy eyes. “You should already know how things work.” The blonde reaches down and places his large hands on both of your thighs. “If you're going to act like a brat..” He presses down on the plush skin, forcing your overstimulated clit to grind even harder against the wand. “I’ll treat you like one.”

You sob as your hips roll in response to your sixteenth, mind numbing orgasm.

“I think you’ve had enough fun for today.” You whimper in relief as the wand and egg both click off. “It’s time to put this slobbering mouth of yours to good use.” Doflamingo pulls his red tie out along with a string of your saliva. He removes the toys and then unties you from the chair before going back to his own. “Crawl.” Your mind was still foggy and your body was sore from being cramped up, but you managed to land on all fours on the floor. “That’s it, come to your owner.”

“Sir.” You look at your reflection in the lens of his glasses as you open your mouth. “Use me.”

“Oh my~” His evil smirk widens, seeing your jaw open wide and ready to serve him. “I didn’t even have to ask.” The salty taste of his pre cum fills your mouth as he roughly pushes his length to the back of your throat. “What a good little slut~”

“Mhm.” You moan around his length as he brutally starts fucking your throat.

“Look at you~” Your eyes meet your reflection once again to see the trails of mascara rolling down your face along with the fresh tears. “Seems like your whore mouth is good for more than bratty comments.”

“Doffy.” Both you and Doflamingo freeze, hearing a knock followed by a voice. “May I come in?”

“Of course.” He shoots you a wicked grin before slamming his cock back into your throat. “Gladius, what a pleasant surprise~, I assume production is running smoothly?”

“Of course.” Footsteps echo in the room as the man walks up to Doffy’s desk. “I was going to get Y/N to schedule us a meeting next week to go over profits, but she has been away from her desk.” Away from mine and under his.
“Yes, I do apologize, I’ve given her a special task this week, so she's been quite…busy.” Saliva rolls down your lips and onto the floor below as Doffy pulls out to release his salty load on your face. “But worry not, I’ll make us sometime.”

“Understood, I’ll see my leave.” You feel relief wash over you as the office door clicks shut.

“You sure look like a mess and it seems you’ve made me one as well” Your cheeks heat up as he looks down at the drool and cum glistening against the black leather of his shoe. “How rude.” His hand threads in your hair before pushing your face against his shoe. “Clean it up.” As embarrassing as it was, the taste of his leather and cum fills your mouth as you lick his shoe. “That’s good enough.” The tight grip in your hair releases, allowing you to come back up.

“Please tell me we're done for the day.” You huff out as you try to wipe the remaining cum off your face. “My body is sore and It feels like T.V static down there.” Numb, very very numb.
“Fufufu is that so?” Doffy laughs as his hands hook under your arms, pulling you up from the floor. “I suppose we can be.” He sits you in front of him on his desk and pulls out a bag of makeup wipes. “ Make yourself presentable, I need you to get to work.”

“Yes sir.” The moist towelette feels good against your face as you wipe away the evidence of your euphoria. “What do you need me to do?”

“Get that meeting with Gladius set up first and-” He leans up in his seat and pulls something out from his back pocket. “Since you missed lunch, go get yourself something”

“Okay?” Your sore jaw nearly hits the floor seeing him holding out his fancy credit card at you. “Thanks, would you like me to bring you anything back?”

“Just a coffee is fine.” You nod and stand up from the desk. “I’m sure you know how I like it?” He smirks as you roll your eyes.

“After a year of dealing with you, of course I do.” You smirk back at him why stretching your worn out muscles. “Jet black, just like your soul~”

“Well this jet black soul just gave you his credit card.”

“True.” You wink at him while holding the card up. “Maybe I should make a few extra stops on the way back~”

“By all means do it.”

“Really?”

“Yes, because if you do I get to punish you even more~”

“I should have figured you’d say something like that.” You pout as you make your way out the door. “Just so you know, I won’t make any extra stops.. But I’m going all out on lunch BYE.” You close the door and run towards the elevators thinking about all the expensive dishes you plan on getting.

~~~~

Doflamingo sat in his office looking at the take out coffee you had brought him earlier when you came back from lunch. On the side of the cup was a note in your hand writing saying “To the okayist boss-From the best personal assistant.”

“I don’t think I will ever understand her.” He takes the paper slip off with your note on it before throwing the empty cup away. Sure, It was just a stupid note written by a stupid girl, but for whatever reason he wanted to keep it. “Or myself for that matter..”

Chapter Text

Wednesday- Punishment Day 3

*This is obviously not going to be my day*. Your misfortunate morning started out not so bright and early thanks to sleeping in over a half hour through your alarm. By the time you got up and scrambled to get ready, the bus that would have taken you straight to work was long gone.

Now here you are, making the rather lengthy commute by foot. But the walk wasn’t necessarily the bad part, but the fact it was absolutely pouring rain and you didn’t have an umbrella, was.

You cringe feeling your drenched clothes cling to your skin as even more water beats down. *At Least it can’t get any worse*. The second the optimistic thought resonated in your mind, the faint sound of your phone's ringtone filled your ears.

*I take that back*… Seeing the caller I.D alone was enough for you to realize it was about to get a lot worse. You glance around the street and find a small overhang in front of a bakery to take cover under as you answer the phone.

“Good mor-”

“Young lady…” The rather unpleasant sounding Doflamingo cuts your greeting off. “Do you have any idea what time it is?”

“Umm..” Considering you’ve been walking through what felt like a tropical storm, the time wasn’t exactly the most important thing to you. “No?”

“No? Well let me catch you up to speed.” *He sounds soooo pissed* “It’s twenty minutes past your scheduled time, so care to tell me why you aren’t here?”

“I accidentally slept through my alarm and....”

“Why the hell is it so loud?” Once again the irritated man cuts you off. “I can barely hear you.”

“I’m sorry sir, it’s storming.” You raise your voice to combat the booming thunder. “I missed the bus, so I have to walk, but I’ll be there as soon as I can!”

“Where are you?”

“I’m..” You glance up at the two name plates adorning the metal post of the traffic light. “At the intersection where redline street and grand line boulevard meet.”

“That’s over five miles away from here!”

“I know, I’ll walk as quickly as I can.”

“No need, just stay put, I’ll be there soon.” The line suddenly goes dead, leaving you stunned by what he just said.

In all honesty you thought the sadistic man would laugh at your misery while getting a kick out of the overall unsavory situation. So knowing that right now, he was going out of his way to come get you, has your mind going blank. You slip your phone back into your pocket and let your back rest against the brick siding of the shop while taking in the odd smell combination of fresh baked pastries and rain.

*I wonder what kind of car he has?* The first image that came to your mind was a pink Volkswagen beetle with the tacky eye lashes on the headlights. Just thinking about him getting into a car that small made you chuckle.

But It didn’t take long for your funny thought to be ruined seeing the s-class mercedes-benz pull up on the side of the street. *I atleast got the color right.* You were about to make a mad dash for the car, but Doflamingo got out of the driver's side with an umbrella in hand.

“Umm..” The sound of his Oxford’s smacking the wet concrete and the unreadable expression on his face causes your lips to curl into a nervous smile. “Hello?”

“Fufufu~ hello to you as well, troublesome little girl.” Doflamingo snickers while walking up to your trembling form. “Or maybe I should call you a drenched mouse?” You roll your eyes as one of his arms wraps around your side, pulling you against him under the umbrella. “Let’s go.” You were a little taken back from his gesture considering he just called you a wet rodent, but you enjoy the brief warmth radiating from his body before he opens the car door.

After helping you in, Doffy walks around to the driver side and gets in. “What’s with that look on your face?” He states while pressing a button on the console, causing the car to roar to life.

“Well..” The leather seat beneath you squeeks as you shift into a comfortable position.“I should have called to let you know I was going to be late...” You already know about today's punishment and you're hoping he doesn't add anything extra on top of it. Especially since you were running on little to no sleep, and adding the rainy day marathon to the equation, you were already both mentally and physically exhausted. “I’m sorry.”

“I’m not worried about it.” The blonde dismisses your concern and takes one hand off the wheel to play with the A/C controls. “But I would like to know why you slept through your alarm?” He angles the vents until they all point at you, sending a burst of hot air to your cold body.

A relaxed smile curls on your lips knowing he was letting you off the hook for being late. “I just had a hard time falling asleep last night.” Doflamingo hums in response, but little did he know it was all thanks to him…

All night you couldn't stop thinking about his recent change in behavior towards you. Doffy has never been one to be “sweet”, but lately he has been, in his own strange way. It was throwing you into a conundrum by making your already complicated feelings toward the man even more so. Part of you was becoming hopeful that maybe he saw you as more than his contracted out “toy”. But the realistic side of you was all too aware of the downhearted truth.

Along with the weird, kinky stuff in the contract you signed on employment, it also stated that Donquixote Doflamingo does not and will not do either love or relationships, meaning the relationship you have as DOM/SUB will not escalate into anything romantic, let alone leave the four walls of his office. And it also meant if for any reason you fell in love with him, you would be fired on the spot. The idea of that happening left a bitter taste lingering on your tongue.

You snap out of your thoughts no longer feeling the gentle rumble of the car beneath your feet. “Wait there.” Doflamingo tucks his keys into his suit pocket and steps out of the parked car before walking around to your door.

“Thanks.” You take his chivalrous hand as he helps you out of the car. “And thanks for coming to get me.”

“You’re welcome~” The neutral expression he wore up until now was replaced by his wicked smile as he cages you against the car. “Now let's go get you out of these~” You gasp, feeling his hands come down to your hips, giving the plush skin a rough squeeze through the damp fabric. “I can’t have my slut catching a cold now, can I?”

˗ˏˋ ♡ ˎˊ˗
Doflamingo brought you into his office and stripped you down, but oddly enough he didn’t start ravaging you right away. Instead you watch him place your clothes in front of an air vent so they would dry. Yet another sweet gesture that you’ll have to add to his baffling behavior list.

“Thanks to you, I’m rather behind on work.” The blonde walks up to you and grabs your jaw, squishing your cheeks together while forcing you to look into the red lens of his glasses. “So I won’t be able to give much attention….. Not that you really deserve it in the first place.” A string of drool rolls down your lips as he releases his hold. “You know what that means, right?” Doffy walks up to his desk and traces his long fingers across the edge, stopping at one of the pointed corners. “You’ll have to keep yourself occupied.” Sporting a smirk, he sat down in his chair and motioned you with his finger.

“Yes sir.” You feel heat blossoming all over your body knowing exactly what he’s wanting you to do. Taking in a deep breath, you walk over to the left corner of the desk that was closest to him. You lift up on the tips of your toes and straddle the desk before bringing your bare pussy down to meet the cold, wooden surface.

“Move.” Doflamingo commands while opening the screen of his laptop.

The desk shakes slightly as you roll your hips back and forth, grazing your clit across its smooth surface. It was so embarrassing, but at the same time you find yourself enjoying it. “Mhm~” You bite down your lip, feeling your juices begin to leak onto the desk below, creating the lube you needed to glide faster.

You glance over at Doflamingo and expect to see him watching your every move, but instead you see his focus was fully on his computer. The fact that you were doing something so lewd in front of him without his attention drove you insane. “Sir~” The whiny moan left your lips as you brought your hands down to anchor against the desk. “Sir, look at me.” You grind down even harder in hopes of gaining his attention, but he disregards your request and continues working.

“Oh fuc~“ The fight for his interest is long forgotten as your clit glides over the rippled details carved on the desk’s edge, causing your pussy to gush. “Mhmm~” The desk squeaks as you rock even faster, focusing your strokes on that one area with the most texture. Beads of sweat begin rolling down your body from the effort you were putting in to reach your high and judging from the pressure in your abdomen, it was about to pay off. “Gonna-”

“Stop.” Doflamingo speaks up, causing your rapid movements to cease. “Stay still until I say you can move.” You let out a frustrated groan and move ever so slightly, earning a harsh slap to your ass. “Stupid whore, what part of staying still do you not understand?”

“I’m sorry sir.” You blink away the tears forming in your eyes. “I won’t do it again.”

“Good.” Doflamingo goes back to working on his computer while you focus on not moving a single muscle.

˗ˏˋ ♡ ˎˊ˗
After being in a stand still for nearly two hours, both the muscles in your arms and legs were cramping up and on the verge of giving out thanks to the awkward position. The climax that you worked so hard to build up had dwindled down to nothing but the gooey slick pooling around your throbbing cunt. You wanted to move so bad, and the occasional jolt of pleasure you got when he’d move something on the desk was making your desire even harder to fight off.

“Look at me.” He finally speaks and you snap your head around to see the reflection of your worn out body in his glasses. “Go.” The second the word left his mouth you begin to move. You hiss with your eyes closed, feeling a sharp pain zap from your thigh to your calf muscle. “Did I say you could close your eyes?”

Your eyes open wide as his large hand meets your rear once more. “No sir, m’ sorry!” You continue to move your hips while keeping your eyes on him. With each movement, the stiffness in your joints nulled down. “Oh fuck-” The lost pleasure comes surging back into your body as you swing your left leg up in the air, exposing your clit more as you desperately bump it against the desk. “Feels s’ good~”

“Seems like I need to buy you a collar...” Doflamingo sneers while leaning back in his chair, enjoying the humiliating show his perfect slut was putting on. “Since you clearly love humping and grinding your cunt on things~”

“Sir..” His jeering words send you dangerously close to the edge. “Can I cum, please?”

“Nope~stop.” Once again both your body and pleasure come to a devastating hault. “Let’s switch things up.” Doflamingo’s arm suddenly hooks around your middle, pulling you into his lap and causing your back to meet the taunt muscles of his abs. “Lookie at what I got~”

Held in front of your face was something any woman with internet access could recognize, the iconic toy rose. Although you’ve never personally used one before, you’ve heard the stories on how this little silicon flower could turn your mind into mush.

“Spread.” The toy rumbles to life in the palm of his hand as you prop your feet on either of his muscular thighs, leaving you exposed and at his mercy. “Try not to squirm too much~” Goosebumps form on your skin as he licks up the side of your neck while his hand brings the toy in between your legs.

“Oh-“ The world around you went black before bursting with aerials of color as the toy sucked your puffy clit up. “Fuc~” From the hair on your head to the main tips of your toes, every fiber and muscle in your body tingle with sheer bliss. “Feels s’ good~” You babble while thrashing around as if you were trying to escape the heaven you’ve found yourself in.

“I should have known my little slut couldn't stay still.” Doflamingo's deep and teasing tone fills your ringing ears as his free arm wraps around your middle. “I guess it’s a good thing I love seeing you squirm~”

“Si-r” With the click of a button your eyes roll into the back of your head feeling both the suction and vibration grow stronger. “To-o much I-i can’t handle it.” Your orgasm was approaching like a bullet train, fast and completely unstoppable. “Gonna-” Tears from the ecstasy roll down your flushed face as liquid pleasure trickles from your cunt and into the floor below. “Cum!” You slam your head against him and lift your hips into the air as your high takes over your body, but just as quickly as it came, it was gone. The man behind your ruined orgasm starts to laugh as you shudder from the feeling of dissatisfaction. "Sir, why?”

“Why you ask?” Doflamingo reaches around and grabs your slack jaw with his large hand. “Is my slut so stupid that she forgot this is a punishment?” You squint your eyes as he bobbles your head from side to side. “But no matter the case you know being a brat won’t get you anywhere~”

“I need more, please~!”

“It’s honestly quite funny hearing that from you, especially since you were practically begging for the complete opposite yesterday.” He brings the toy glossed over in your arousal, back in front of your face. “But if you want it so bad, convince me.”

“Please, please, please.” You could only hope the desperate mantra is enough to get you the satisfaction you so desperately needed. “I want it so bad~”

“Would you look at that?” The toy held in front of your face is replaced by the golden face of Doflamingo’s Rolex. No way. “I guess you did that for nothing.” Your eyes widened seeing it was well over an hour past business hours. “How unfortunate.”

“Doffy.” You weren't ready to give up just yet, so you flip around until you're straddling his lap. “I really want to cum~” You prove your point by rubbing your needy pussy against his clothed erection, earning a deep grunt from the man. “Please, it hurts.”

“Please, it hurts.” He mimics your pathetic tone while throwing you off of his lap and onto the desk. “What a desperate slut you are.” Doflamingo got up from his chair and threw your clothes into your lap. “You know only good girls get my cock.”

“But-“

“Say another word and I’ll take you over my knee right now.” Despite being utterly disappointed, you also didn't want to experience that twice in one week, so you get up from his desk sporting a pout and begin to put your clothes on.

“And you better not touch yourself once you leave here.” Doflamingo adds.

“Fine I won’t.” You groan out and walk towards the door while making some final adjustments to your clothes. “Asshole.”

“What was that?” The grating tone of his voice causes you to freeze in place. “Did I just hear you speak after I clearly told you not to?” Fuck. “Come here, now.”

“Uh-“ I’ll probably regret this. “No.” Without turning around, you throw the door open and run as fast as your heels would allow.

“Get back here!” His yell echoes through the now empty office. I take that back, I already regret this.

Knowing that Doflamingo was inhumanly quick despite his large stature, you run over to one of the empty cubicles and crawl under the desk to hide. His office door slams shut as his heavy footsteps reverberate in the room.

“You sure have a knack of making things harder on yourself~” At this moment, you would have to agree with him. “But I think this little game of cat and mouse will be enjoyable~” You could hear your heart pounding against your chest as his footsteps got closer and closer. “How about this, if you can make it out of the building, you're free to go.”

He’s giving me a chance to escape? Although most people don’t believe this, Doflamingo was a man of his word. If he said he would do something he did, and if he said he wouldn’t, he didn’t (terms and conditions may apply).

“And if you can’t...” You stifle a whimper by cupping your hand over your mouth, seeing that he now stood right in front of the cubicle. “I’ll just say the cat has a few ideas on how to devour its prey~”

Luckily he didn’t notice you and he kept walking. I need a plan. You stay under the desk and strategize your next move. Judging from the direction he went, Doflamingo was most likely heading towards the elevators. Leaving you with only one option of escape, the stairs.

You take your heels off so their clacking sound wouldn't warn him of your position. Carefully and quietly you slide out of your hiding spot and get into a crouched position before making your way through the dim office.*I’ve got this*. You approach the door and take a deep breath before pushing the handle. The door opens, making a rather loud metallic screeching sound, but you quickly get into the stairwell and start your next course of action. Run. Like. Hell.

You made quick work of the first two sets of steps and got halfway down the third before stopping dead in your tracks. *How did he?!* Lurking at the bottom was none other than the self proclaimed “cat”.

“Fufufu~ I’m not surprised, however I am rather disappointed.” His words and the cocky smirk on his face told you he knew this is what you were going to do. “I thought you were going to make catching you fun~” Fear washes over your body seeing his foot come into contact with the first step. “Run.”

You throw your heels down and focus solely on retreat, knowing your ass was literally on the line. Plan A failed thanks to Doffy’s ‘always a step ahead nature, so it was time to bring in Plan B.

You make it back into the office and beeline towards the elevators. “Come on, hurry!” You frantically press the button and watch the light make its way up to your floor. You turn around and briefly look into the dark office. Knowing that at any moment the 10 foot tall man could emerge, pulling you to your doom was enough to make your adrenaline induced anxiety skyrocket. The elevator chimes followed by the doors sliding open and you waste no time getting on.

You click both the 1st floor and the close button, fully expecting his dress shoe to stop it from doing so, but it doesn’t. “I did it!” You smile from ear to ear and soak up the victory as the elevator starts to descend. “As if he could really out smart m-” The words died in your throat as the elevator came to a grinding halt after going down just one floor. Don’t tell me. The small ding that signaled freedom moments ago, now sounds more like a funeral bell. The doors open, showing that your suspicion was correct. You had once again fallen right into his hands.

“Fufufu~Seems like my little mouse took the bait.” The elevator shakes as the smirking man walks in. “There’s nowhere to run now~”

“Wait..” With no hope or options left, your back meets the wall of the elevator. The ferocious, primal aura surrounding his looming figure is a suffocating one you recognize all too well. He was in full sadist mode. “Doffy.” Your knees give out, sending you straight to the elevator floor. “M-sorry.”

“It’s far too late for that~” He declared with a deep, unforgiving tone. “Looks like I need to teach you a lesson on taking responsibility for your actions.” With that his large hand fists in your hair, dragging you out of the elevator and leaving you to crawl behind him.

“Please-“ Tears quickly build up in your eyes and roll down your face from both the stinging pain in your scalp and the throbbing pain in your knee caps. “Hurts-“ Your cries don’t even cause him to falter for a moment.

Any other time a situation like this would have aroused you, but after losing sleep last night and being punished all day, your emotional state was not the best and you most definitely didn’t want to be in any more pain.

“Stand up.” Your body falls limply to the floor as his hand releases from your hair. “If I have to repeat myself, you won’t like what happens.”

“Doffy ple-se.” You sob half formed pleas and try to crawl away, but he retaliates by grabbing your hair once again, pulling you up to your feet. “I can’t-“ The breath is knocked from your lungs as Doffy slams you against a wall.

“You can and you will.” He snarls while bringing both your skirt and underwear down in a single fluid motion. “I’m going to absolutely ruin you.”

“N-” You knew he meant his words so you try to open your mouth to plea once more, but a harsh slap to your rear causes a cry to come out instead.

“You’ve been so bad I think you need a little more than my ‘guiding hand’.” You look over your shoulder and your heart drops seeing the blonde undoing his belt. “This should do~” He folds the belt against itself and rears back. Your vision tunnels and you scream as the belt comes in contact with your irritated skin.

“You're crying so hard after one hit? How pathetic.” His words sting just as much as the thick leather. “But what else should I expect, you are just a useless little mouse after all.”

“W-whisky!” Doflamingo stops the belt just a few inches over your red, welting skin after hearing the established safeword faintly fall from your lips. He takes a step back and you immediately cower away, desperate to get some distance in between you and him.

He’ll be the first to admit there’s nothing quite like having someone trembling and terrified beneath him, especially you. But most of the time there was a twinkle of excitement in your eyes, but right now they were blown wide and filled with true fear.

Doflamingo silently studies you. Your chest was heaving as you fought back hiccups and sobs with distress and pain written all over your face. This was the first time that you’ve used the safeword and he was unsure how to help you. He wasn’t a good comforter and that fact alone is most likely the reason his past PA’s/Subs quit after a few months. But seeing you in such a state made him want to at the very least try.

“Y/N.” Doflamingo held his hand out, as if he were trying to gain a feral dog's trust. “It’s okay, come here.” You hesitate for a moment ,but end up resting your tear soaked cheek against his palm.

“Did you mean it……Am I really useless?” Your broken question made the man realize that you weren't just going through physical pain.

“No.” He answers while brushing a few stray strands of hair behind your head. “But-.” A subtle smile forms on his lips. “You really are just like a mouse.”

“Am I?” Both the dejection and terror fogging your eyes disappears and a smile of your own curls on your lips. “I guess I am adorable and a-“

“Pest~” Doflamingo finishes your sentence with a snicker while you mumble something about him being mean under your breath. “I think it’s time for us to leave my dear.” He bent down to help you bring both your skirt and panties back up your legs. “I’ll drive you home.” With that ,the merciless cat had decided to let you go….at least for now, that is.

🐈⬛˗ˏˋ ♡ ˎˊ˗🐁
“Stop laughing, you jerk!” You glare daggers at the driver of the bubble gum pink car. “It’s your fault I’m having to do this in the first place.” Despite your request to stop, Doflamingo still laughs over the fact you were having to lay sideways in the car seat. “It’s not funny, it really hurts.”

“You poor thing.” You roll your eyes hearing the fake sympathy in his voice. “At Least I was kind enough to nurse you a little.” Before leaving the office, he gave you a rub down once more with the aloe cream, but after what you went through, it only helped a little.

“Hopefully when I have to get a butt transplant you’ll be ‘kind enough’ to pay for it.” The blonde responds to your statement with a smirk while one of his large hands comes to rest on your hip, giving the plush skin a gentle squeeze.

“Y/N, are you in a rush to get home?” His out of the blue and rather odd question caught you off guard.

“Not really…” You didn’t have anything planned besides maybe catching up on some rest. “Why?” You look over at the blonde with a raised brow.

“I need to do some shopping….Care to join?”

“Yes!” You cringe at both the way you answered so quickly and how eccentric you sounded, but who could blame you? The one and only Donquixote Doflamingo just invited you on a shopping trip…This is going to be fun~

˗ˏˋ ♡ ˎˊ˗
“Wow this place is nice.” You whistle in amusement while walking into the shopping mall. It became very obvious to you seeing the amount of luxury stores that this was clearly catered to the rich and elite. “So what kind of shopping are you doing?” You ask while trying to keep up with his large strides.

“I’m picking up a suit and a new pair of cufflinks~” He held his hand up, showing you the skull and crossbone ones he typically wore. “I’m getting rather bored of these.”

˗ˏˋ ♡ ˎˊ˗
“Mr. Donquixote, what a pleasure to see you again.” A gentleman working the tailor shop greets him before turning his attention towards you. “I see you’ve brought Mrs’s. Donquixote with you this time”

“Yes, this is Y/N.” *HUH?!*

You look up at Doflamingo completely confused as to why he agreed. “Oh, sorry!” You were too baffled to notice the man's outreached hand. Awkward.. “It’s nice to meet you!”

“Likewise.” The man pulls away and guides you both to the back of the store. “Your suit is in the private dressing room, please try it on and let me know if I need to make adjustments.”

The tailor leaves and Doflamingo walks into the dressing room. You look around and spot a small cushioned chair. Don't mind if I do~You start to walk towards it, but a hand grabs your shoulder, pulling you back.

“Doffy?” The dressing room door shuts and he turns to you. You’ve seen enough cliche romance movies to know what is about to happen. “What if he hears u-”

“Hold these for me.” He cuts you off by wrapping his pink jacket around your form before sliding the iconic pair glass over your eyes. He then boots you out of the dressing room, leaving you a little bummed out that he didn’t pull you in here for steamy, dressing room sex in the first place. But your job as his personal mannequin wasn’t so bad. In all honesty, you were enjoying the soft feathers and the deep smell of his nautical cologne.

*I bet I look ridiculous.* You walk over to the lobby’s huge mirror and immediately have to hold back laughter. Seeing yourself made you realize that he was most likely the only person who would make the coat look scary, because you looked about as intimidating as a truffula tree.

“Fufufu~” You push his glasses up the bridge of your nose and decide to take things a step further by copying his laugh. “Y/N make me a cup of coffee. Y/N come fix this damn copier. Y/N, help me make this email sound more offensive.” You strike different poses while saying some of the daily things he asks from you.

“Fufufu~” You were too busy goofing around to remember the man you were mocking was in the same vicinity as you. “Has my little accomplice had her fill?” You nod up at the man standing right behind you in the mirror. “Thoughts?” You glance up and down the light gray, pink detailed suit that was hugging his body like a glove. Doflamingo was honestly so handsome you think he would look good in anything, but this suit really brought the “wow” factor.

“I love it….I’d even say it really “suits” you.” You laugh at your own joke, but earn nothing but an eye roll from the dry man. Speaking of eyes.. As cool as his glasses were, you also wish he didn’t wear them as often so you could see the two beautiful crimson orbs that are staring back at you.

“Your work here is done.” Before you could really admire them, he took his glasses from your face and put them back in their rightful spot over his eyes. “I’m going to get changed. '' His voice was much lower than normal and he seemed to be..flustered? “Tell the tailor the suit was to my liking and to have it delivered to my home.”

“Roger that.” You leave the dressing room feeling puzzled by his sudden odd behavior. I wonder what’s up with him?

˗ˏˋ ♡ ˎˊ˗
“Look, Don Doflamingo is here!” Hearing about his arrival, multiple women working in the jewelry store you’ve found yourself in flock to his side, nearly taking you out in the process. “How can we help you?”

“My my~” He smirks down at the women practically hanging onto him. “Aren’t you all eager?” You’d be lying if you didn’t feel a twinge of jealousy right now, especially since you were tossed aside and seemingly forgotten about.

Doffy is obviously in multiple good hands, so you break away to mingle around the store. You looked at all of the sparkling glass cases, but nothing really caught your eye until you saw a lone necklace in a display of its very own. At first it looked like a simple necklace with a big hollow heart charm in the middle, but upon closer inspection, you notice the diamond links of the chain were shaped like hearts as well. That cute detail alone was enough for you to instantly fall in love.

“You have a keen eye!” One of the workers not ogling your boss approaches you from behind the counter. “Would you like to try it on?”

“Please, if that’s okay..” The woman pulls the necklace out of the case and hands it to you. You bring the necklace behind your head and try to pinch the clasp, but can’t get it to go on. Just when you were about to give up and ask the worker for assistance, two large hands from behind helped guide you.

“Oh wow, take a look!” The saleswoman brings a mirror in front of you, revealing both the necklace and the blonde man who helped you into it. “It’s absolutely stunning on you!”

“It is.” You move gently from side to side, admiring the way the jewels shone against your skin. “How much is it?” Hopefully it's a reasonable amoun-

“100,000 berries.”

“100,000!” You repeat back in pure disbelief. Did they steal it from the freaking Titanic? “I love it, but for now I’m going to have to pas-.”

“We’ll take it.” You look up and see Doflamingo reaching over you while holding out his card to the woman.

“Of course Mr. Donquixote.” She takes his card and swipes it before you have a chance to say anything. “Would you like me to bag it up?”

“No need.” Doffy took his card back and slid it into his wallet. “She’ll wear it out.”

“What a lucky girl you are to have such an amazing boyfriend.” The woman smiles at you while placing an empty jewelry box in your hand.

“Oh, I’m n-”

“I’d have to agree~” His arm snakes around your waist, pulling you against his side. “She is very lucky~”

“She’s actually his girlfriend?!” You follow the distressed cries to the group of girls sulking against the counter at the other end of the store. “I thought he was single.” I did too…

Still close to his side, you walk out of the store with a bewildered smile tugging at your lips. Not just because of the fact he bought you the necklace of your dreams. The thing that really made you happy was the fact you and him got mistaken for a couple twice, but he didn’t attempt to correct it either time.

˗ˏˋ ♡ ˎˊ˗
“Are you joking?” Doflamingo’s face scrunches up as he pulls the car up to your apartment complex. “This is where you live?” He scowls at the rundown building. “Surely I pay you enough to afford something better than this?”

“You do pay me very well, but rent in Grand Line City is ridiculous and nice apartments are hard to find, so it’s live here or in a cardboard box.” It’s sad, but true. Plus this was the only apartment that was even relatively close to your work.

“I honestly feel like I’m looking at a cardboard box.” You roll your eyes at his rude comment. “I don’t like it.” That’s obvious.

“You don’t have to like it.” You retort with a yawn while grabbing onto the door handle. “Anyways I better get going.” You look down at the jewel decorating your neck before giving the man who bought it a smile. “Doffy thank you for this, I love it so much.”

“No need to thank me.” He smirks before his finger hooks in the necklace's charm, pulling you towards him. “After all, I did say I was going to buy you a collar~” Heat rushes to your cheeks realizing that this was not only a gift, it was also a mark of Doflamingo’s ownership over you. “Now go get some sleep young lady.”

As happy as you felt in the moment you also knew If things keep going like this, you were going to end up in big trouble. Or maybe you already were, because you know the familiar giddy feeling blooming in your chest could only mean one thing. *I’m falling in love with him.*

˗ˏˋ ♡ ˎˊ˗
Doflamingo parked his car and was getting ready to step out, but noticed something out of the corner of his eyes. “Of course she’d forget this.” He held up your cell phone causing the screen to light up. Out of curiosity Doffy tilts his glasses down to see what you had your background set to.

He wasn't sure what he was expecting, but it definitely wasn’t this. “That little..” On the screen he was laid back in his office chair taking a nap with a business and economics book covering his face, and you were posed right by him with a dorky smile plastering your face.

His eyes roll wondering how many photos of him you’ve taken without his knowledge. But then again, earlier when you were playing in his jacket and glasses, he took a few photos. Just because he found it humorous, no other reason…..Right?

Being the prime age of 41, Doflamingo has had his fair share of women, but he’d be lying if he said you weren't extra special to him. But the part he couldn't wrap his mind around is why you were? Was it the fact you were always yourself around him, was it the way you were never afraid to challenge him? Or maybe it’s because you were just so… you?

His own cell phone begins to ring, pulling him from the troublesome thoughts circulating around you. A devilish, wide smile plasters his face seeing the name flashing on the screen.

🦩“What a pleasant surprise, have you finally decided to take me up on my offer, Crocodile?”

🐊“I won’t say I’ve accepted quite yet, but I have taken it into consideration…. Come over to the casino tomorrow and we’ll talk business.”

🦩“Sounds like a plan~”

🐊“And make sure you bring Y/N with you….. It’s been far too long since I’ve gotten to see my precious intern.”

AN-Part three coming soon 🦩🆚🐊

Chapter Text

Thursday- Punishment Day 4

Thanks to falling asleep right after Doflamingo dropped you off, you woke up early and on the right side of the bed. You started off with a warm shower before making your way to the kitchen for a nice glass of orange juice.

“Hurry up, we have places to be.”

“Right.” WAIT. You slowly turn on the heels of your feet to see none other than Doflamingo sitting at your kitchen island. “??”

“And you need to find a better hiding place for this.” Swirling around his gloved index finger was the spare key you kept under the doormat. So that’s how he got in. “It’s not smart to keep it in such an obvious place, an intruder could break in.”

“You are an intruder.” You mumble under your breath and finish off the last of your orange juice. “I'll finish getting ready, make yourself…. even more at home.”

˗ˏˋ 🦩 ˎˊ˗
Despite being very expressive and very readable, there were many things that made you an enigma to Doflamingo, so he was going to take you up on your offer by exploring your tiny apartment. So these are the things she likes? He found himself confused, but intrigued at the different little knick knacks scattered all around. Maybe one of these days, I’ll figure you out.

“I’m sorry it’s taking me so long.” He turns his attention towards you and sees that you're digging through the cushions of your couch. “I can’t find my phone.”

“I’d say not, considering you left it in my car last night.” The blonde reaches into his coat pocket and pulls out the missing phone. “I was kind enough to charge it for you~”

“Thank you.” Doflamingo places the phone in your outreached hand and watches a panic expression paint your features. “Er-m.. did you see-”

“Did I see what?” He crosses his arms and acts puzzled, but he knows what was on your mind.

“Haha~nothing~” You laugh nervously and place the phone into the pocket of your skirt. “We better go! Like you said, we have places to be~”

˗ˏˋ ♡ ˎˊ˗

The car ride to work was rather peaceful and quiet beside Doflamingo’s occasional, but understandable road rage. But you noticed he has driven past the turn off for work. “Where are we going?”

“I’d say it's a surprise, but you’ll know the second you see that hideous pyramid.” Doffy sneeres.

There was only one building in Grand Line City that could fit his unfavorable description. “Rain Dinners?”

“You’re unfortunately correct.” His index finger rises from the steering wheel, pointing towards the building in the distance.“Me and your dear old boss have a meeting, I’ll need you to take notes for me.”

“Okay.” A sense of nostalgia washes over you seeing the bright, neon lights decorating the building flicker. It’s been a long time…

While finishing up college, you accepted an internship at the Rain Dinners in the casino’s accounting department. You were so nervous at first, but you eventually started excelling, even going as far to plan up a way to more efficiently handle the casino’s revenue. This caught the eye of the owner/CEO, Crocodile, or better known by his alias, Mr. Zero.

He took you under his wing and taught you a lot of skills that you use to this day. A few weeks before you were set to graduate, he even approached you and offered you a job.

With the finish line in sight and a promised job in the company you loved, you were certain the beginning of your career was set in stone. But before you could reach the checkered flag, a feather landed at your feet.

‧₊˚✧[Flashback]✧˚₊‧
You were taking a leisurely walk around the casino, but stopped seeing a small feather laying on the ground. At first you didn’t think anything of it and assumed it had fallen off one of the burlesque show girl’s uniforms, but then again, their feathers were not pink. Weird.

After taking a few more steps, you stumbled across another one. Is there a flamingo on the loose? One by one you followed the mysterious trail of feathers until you ended up in front of the V.I.P elevators where a tall, blonde man stood, tapping his foot on the ground.

Right off the bat, you noticed the fluffy, pink parka adorning the man's shoulders. That explains a lot. Before you could approach the stranger he spoke up as if he already knew of your presence. “I take you're the cute and talented intern that bastard keeps raving about?”

“Perhaps.” You chuckled and held up the collected wad of feathers. “And you must be the runaway flamingo.”

“Perhaps.” The man returned your playful tone and turned around to face you. “I’m Heavenly Demon.”

“I’m Angel.” You took his outreached hand and responded with the alias Crocodile gave you. “Nice to meet you.”

“Likewise~” His large hand engulfed yours as the elevator door opened. “Care to join me?”

“Sure, my break is about over anyway.” You stepped into the elevator, followed by the man. “What floor do you need, Heavenly Demon?” You asked while clicking the button for the revenue department on the 21st floor.

“Whatever floor that insufferable Mr. Zero is on.” The blonde grumbled while leaning up against the elevator wall.

“That would be the 20th floor.” I’m starting to think they don’t like each other. You pressed the button for the floor and walked over to the opposite side.

“Angel…” The blonde hummed, turning his attention towards you. “What’s your real name?”

“I’m..” You stopped yourself midway remembering the strict policy Mr. Zero had on real names. “I can’t tell you, and considering you are using an alias as well, I’m sure you know why…”

“What an obedient girl you are~” A smirk grew on his face as he lifted himself from the elevator wall. “But I will say, he could have picked a better one besides "Angel "." The breath in your throat hitched seeing his large form looming over yours. “In my eyes, “Mouse” would suit you more~”

“R-eally?” The word embarrassingly stumbled from your lips as you met your frazzled expression in the red lens of his strange sunglasses. “Why’s that?”

“Because you're timid~” The smirk on his handsome face widened as he slotted a long leg in between yours. “But something tells me that could change..” Your heart pounded against your chest while your skirt slowly rolled up your legs with his movements. He then swooped down to the corner of your neck, bringing his lips directly against your ear and in a deep whisper- “In the presence of a cat~” The suggestive words and the way his hot breath tickled your sensitive skin had your mind melting, but the racy moment was cut short when the elevator stopped on the 20th floor. “I’ll see you around, little mouse~”

Oh. My. As the doors began to close, you grabbed the metal railing to keep from falling. You took in deep breaths and looked up to catch one last glimpse of him. You’ve never been one to get bewitched easily, especially by a very forward stranger. So it was almost maddening how the charming blonde took a mere ten minutes to get you complete and utterly under his trance. Who was he?

~~~~
It had been two weeks since your encounter with the Heavenly Demon and he managed to plagued your thoughts morning, noon and night. You tried to do some digging around in hopes of finding out who he was, but came up empty handed. I need to quit thinking about him.

In order to clear your mind for the sake of getting work done, you took a break and went down to the casino’s gift shop for some snacks. You grabbed a bag of chips and a drink before running across a small rack of stuffed animals. The fluffy assortment was decorated like your average gambler, with tacky Hawaiian shirts, Margarita glasses and of course a fake wad of cash.

But one of them was different from the rest. It was a small flamingo wearing a pair of sunglasses. You picked it up with your free hand and instantly thought of the pink pile of feathers along with the man they came from. “It’s kinda funny.” You mumbled to yourself taking a closer look at the plush. Although the glasses weren't the exact same as the mans, the vibe however, was. “You remind me of him.”

“Of who?” A deep voice spoke against the shell of your ear, causing you to surge forward, almost knocking over a keychain rack in the process. “We meet again-” A gloved hand held a firm grip on your forearm, keeping you from doing so. “Little mouse~” The second you heard that strange nickname you knew it could only be one person.

“Hello, Heavenly Demon.” As glad as you were to see him again, you were also embarrassed it had to be under these circumstances.“Thank you.” You gave him an appreciative smile as you regained your footing. “I apologize in advance, Mr. Zero isn’t here at the moment.”

“I’m actually not here to see him, I’m here for you.”

“For me!?” He confirms with a smug nod. “Um- why?” You were of course flattered, but it was still a little strange that he would make a special trip just to see you.

“Well I heard you were graduating soon.” He crossed his arms and leaned up against the shop's walls. “And I wanted to ask if you’d taken any jobs into consideration.”

“I am and I have, Mr. Zero has actually offered me a full-time job here.” It was the only job you had been offered and in all reality you had full intentions of taking it, so you didn’t feel the need to job hunt any further. “Why do you ask?”

“Well, I have a vacant position open.” The blonde reached down into his suit pocket. “Take this~” He slid a business card into your blouse pocket before taking the drink, chips and stuffed flamingo from your hand. “Friday at noon.” He turned around and walked up to the cashier. Is he going to?

“Oh you don’t have to-”

“Think of it as an early graduation gift.” Before you could utter another word, both your snacks and the plush were paid for and placed in your hands. “And before I leave.” He leaned down, cupping a large hand around your ear.“I wanted to say Y/N is a beautiful name.” And with the Heavenly Demon left you both confused and curious.

How’d he know my real name? The thought didn’t linger too long remembering he placed a card in your pocket. Upon pulling it out you learnt that his real name was Donquixote Doflamingo. No way! Anyone who lived in Grand Line City would know that name, especially since the man practically owned half of it!

But even with his name being well renowned, very little was known about him from the public eye. You wanted, no, you needed to learn more about the man, so you made plans to meet with the one who knows all.

~~~~
“Excuse me, Mr. Zero” You knocked on his half open office door, gaining his attention. “Can I talk to you?”

“Of course you can.” He waved you in, motioning you to the seat across from him. “What’s on my Angel’s mind?”

“Not so much a what, as it is a who.. Donquixote Doflamingo..” The second you said his name, Crocodile’s eyes widened. “Can you tell me about him?”

The man hesitated at first, but broke his silence with a sigh. “I’ve known him for a long time and I’ll just say his reputation isn’t exactly the best.” Crocodile grimaced while placing a fresh cigar in between his lips. “Why do you ask?”

“I’ll tell you..” You said, giving him a sheepish smile. “But promise you won’t get mad at me?”

“I don’t believe I could ever be mad at you.” Crocodile blew out a puff of smoke while relaxing back in his chair. “Go on Angel.”

“Before I say this, just know I haven’t made any final decisions.” You swallowed the lump in your throat before continuing. “The other day, Mr. Donquixote invited me to his office for an interview, and I think I’ll go.”

“Did he now?” The cigar in his hand almost snapped in half as the man growled. “I’ll admit I’m not exactly thrilled, but I’m also not surprised. You're both a smart and beautiful girl, so I could understand why he’d come after you.” He took one last drag before sitting the cigar in the small ashtray on the desk. “If for some unfortunate reason you take his job, just know whatever happens, you’ll always have a place here.”

“Thank you Mr. Zero.” You felt relieved knowing that to an extent, you had his grace.

‧₊˚✧[Flashback End]✧˚₊‧
As Doflamingo gave the valet his key, you waited in your seat for him to open your door. But before he could, another man beats him to it. “It’s been far too long Angel.” The familiar smell of cigars fills your nostrils as you take the man's outreached hand.

“Hello Mr. Zero, it's good to see you again!” You give him a wide smile as he helps you from the car. “How’s business go-” The words die in your throat and you jump slightly in place hearing the car door slam shut.

“You’re ill mannered as always-” Looking over your shoulder, Crocodile’s pleasant expression turns into one that holds both respect and contempt. “Heavenly Demon.”

“Fufufu~ I wouldn’t know what you're talking about, Mr. Zero.” Doflamingo arms hooks around your shoulder, pulling you to his side. “As much fun as I’m having looking at this geometrical eyesore, I’d like to get this show on the road sometime in the near future.”

“What a pity, I was about to suggest we have a little pleasure before business.” Crocodile shrugs his shoulders and turns around to walk towards the entrance.

“Is that so?” You look up and see the cocky smirk growing on Doffy's lips, that alone lets you know he was intrigued. “What exactly did you have in mind?”

“How does a game of roulette sound, Heavenly Demon?”

˗ˏˋ ♡ ˎˊ˗
This is going to be interesting. You watch the two men take a seat at the roulette table before going to get one of your own, but your boss obviously has a different seating arrangement in mind as he pulls you into his lap. Not that you really mind, in all honesty it was quite nice, but you also realize he’s doing it just to show you off, ultimately treating you like a shiny accessory.

“Place your bets gentlemen.” The game attendee calls out.

Doflamingo places a huge stack of chips on all of the even numbers, while Crocodile lays an equally huge amount on all of the odd numbers.

“Let’s begin.” The host drops a small, white ball on the wheel before turning it counterclockwise.

Considering you’ve worked for both of them, you knew how much Doflamingo and Crocodile liked to gamble. Needless to say they are each experts in the sleight of hand arts, but roulette was a game of pure chance. And with the way they placed their bets, the odds of winning were at a balanced 50/50.

With each spin of the wheel, you kept a mental note of how many times each man has won. Right now, Crocodile’s won 10 times, and Doflamingo has won 11.

“Gentlemen, this will be the last spin.” As the attendee turns the wheel, Crocodile leans over and whispers something in Doflamingo’s ear. You try to make out what they're saying, but can’t, thanks to the loud clacking of the roulette wheel.

“So what do you say?” As Crocodile pulls away grunting those words, the man holding you tenses up. “Don’t tell me your-”

“I’m in.” Doflaimgo spoke up while tightening his arm around you. What’s going on? You feel a bout of anxiety brewing in your chest as the ball slows down once more.

*Click* *Click* *Click* …….

“What will our last winning number be, gentlemen.” The host cheers as the ball comes to its last stop. “21!” Both an odd number and number heavily associated with sin.

“Looks like I win, Heavenly Demon.” You look over at Crocodile who was lighting up a victory cigar. “Today must be my lucky day~” His eyes narrow in on you, giving you a subtle wink. “Let’s go do some business, shall we?” Once again, Doflamingo’s entire body tenses under you. Something’s not right…

˗ˏˋ ♡ ˎˊ˗
As you left the casino floor, the blonde grew eerily quiet with the exception of him popping his jaw or cracking his knuckles, actions he did when he was super, super angry. But it makes sense in a way taking into account he's a sore sport, but losing has never made him act quite this strange.

“I think we’ll conduct our little meeting in the V.I.P conference room.” Crocodile spoke as you stepped into the elevator. “You haven't seen it before, have you Angel?”

“I don’t think so.” You’ve been in almost every room at the Rain Dinners, but the one he’s speaking of was strictly for the elite members. In order to even get to it you need a special card, something you as an intern never had. But you’ve heard rumors that made you curious~

˗ˏˋ ♡ ˎˊ˗
After the short elevator ride you followed behind the two men into the meeting room. At first it was hard to see much due to the only lights illuminating the room being deep hues of indigo and cobalt, but you were quick to learn that this wasn’t just some “meeting room”.

None of the rumors you heard mentioned walls decorated with erotic art, whips, handcuffs and a bunch of other kinky stuff that both scare and excite you. I’m starting to think I’m not just here for notes..

“What do you think, Angel?” Crocodile asks while walking towards the chaise lounge that sat in front of a large, leather sectional. “Quite the “conference room”, wouldn't you say?”

“Yeah..” This is a literal sex dungeon.. help…

“I’m sure you noticed we made a “special bet”.” You nod with a raised brow. “You were that bet.” WHAT?! In your mind you were thinking they had placed a bet on a business deal or something to that extent, but hearing it was you the whole time…. “And since I won, I get to keep you to myself.. for a little while at least.” Crocodile smirks at you while parting his legs, a gesture you knew meant “come here.”

“Wai-!” You couldn't even finish your sentence before blood began to rush to your cheeks. Unlike with Doflamingo, when you were Crocodiles intern, you were just that. Nothing sexual. He really agreed with this? While you try to process the shock you were feeling, you look over at Doflamingo. In the contract he made it very, VERY, clear that no one else could touch you.

“Sir..” You whisper low enough so he was the only one who could hear you. “What do you really want me to do?” You knew he was way too stubborn and prideful to run from a bet. But bet or not, you weren't going to do something that would make him uncomfortable. “If your not th-”

“Shut up.” Doffy rudely cuts you off before walking over to the sectional across from Crocodile. “In case I haven’t told you croco boy, my little whore’s been somewhat of a bad girl here recently~” His snarky attitude comes back to life as one long leg crosses over another. “So don’t feel the need to hold back.” Your feet froze to the floor feeling the icy gaze hidden behind his glasses zero in. “Go on slut, do what you do best~”

You hesitate for a second, feeling uneasy about the situation, but you see the iconic “do it, or there will be hell to pay” look on his features. I guess this is really happening.

With each step, you feel more and more nervous, asking yourself is this really okay? Sure you find Crocodile very attractive, and you did have a teensy tiny crush on him at one point, but something about this feels wrong.

“Angel..” As you step in between his parted legs, his right hand gently grabs one of yours. “Are you okay with this?”

You still don’t know the answer to that, so out of good measure and respect, you turn your head and encounter Doflamingo’s illegible expression. You put yourself into his shoes and immediately feel your stomach drop at the thought of another woman touching him. But with a stern nod of his head, his answer still remained the same.

“Yes, I’m okay with this.” You turn your attention back to the man waiting for your approval.

“Good.” Crocodile gently pulls you further in between his legs. “We can stop at any time, okay?” You nod as his hook starts caressing your side. “And since you call that bastard sir, why don’t you call me what you did that one time~”

That one time? What he said confused at first until you remembered the little slip up you had. Oh..that. To make a long story short, you accidentally addressed him as “Daddy”, and it's now very clear that he took and ran with it. “Okay daddy.”

“That’s a good girl.” Crocodile flesh hand joins in caressing up and down your sides. “My, good girl.” It felt illicit, but hearing the gruff tone of his praise sent pleasant shivers down your spine. It had been far too long since you’ve heard any (considering in Doflamingo’s eyes you were practically always a “bad girl”), you forgot just how much you loved it. “Now let’s take these off.”

His right hand slides down to the zipper at the side of your skirt before finding the small metal clasp, slowly bringing it down until the garment falls onto the shag carpet below. “How cute.” Your thighs squeeze together from feeling him toy with the ribbon decorating the top of your lingerie bottoms. “I think I’ll keep these on you for now, but I want you to take everything else off for me.”

Your unsteady hands come up to the first button on your blouse. One by one you manage to unfasten them but halt halfway down feeling the silky fabric of your panties press up against your clit.. “Mhm~”

“My, what a sweet sound.” Crocodile chuckles as his smooth hook grinds up and down your slit. “Keep going princess.” With guilty pleasure starting to cloud your mind, you struggle, but manage to work off the last few buttons, letting the garment fall down your shoulders. You then bring your hands behind your back to unclasp your bra before taking it off and throwing it down into the small pile on the floor.

“Beautiful.” The man whistles while raking his sharp every over inch of your form. “Absolutely beautiful.” A bashful smile forms on your lips from both hearing and seeing his adoration for you. “Tell me sweet girl?” His hand comes down to his right thigh, patting it a few times. “Are you going to do everything daddy says?”

“Yes daddy~” You husk before obeying his gesture, straddling yourself over his thigh. “I will.” You lower your clothed core until it becomes flush with the taunt muscles under his slacks.

“That’s what I like to hear.” His lips press up against your forehead before he pulls something out of his suit pocket. “Lay forward.”

You follow his instruction and lean until your upper body meets the couch, leaving your lower half still straddled and bent over his leg. The position was making you a little nervous considering you couldn’t see either man let alone what they were doing, not to mention this was a position Doflamingo typically put you in for the sole purpose of spanking. You're really hoping, considering the man holding you has thick rings decorating his fingers, that it's not the case.

You hear a small click as Crocodile's hook slips under the slit of your panties, pulling them to the side. A thick, cold substance comes into contact with your clit, causing your thighs to tremble from the sensation.

“You're squirming that much all over a little lube?” Crocodile's teasing tone sends even more blood pumping to your cheeks. “How precious~” You stifle a moan, feeling the pads of his fingers slowly circle around your clit, delicately massaging the lube into it and the sensitive, surrounding area.

“Are you deaf or something?” For the first time in a while, Doflamingo speaks up, sounding rather annoyed. “The slut needs to be punished, not spoiled.” Right now, you would have to disagree. After dealing with harsh punishments the last three days, you are more than ready to be “spoiled.”

“No, I heard you.” As Crocodile responds, his fingers work down to the wet entrance of your core. “But I have a hard time imagining this sweet princess doing something deserving of a punishment.”

“Mhm..” You groan and wiggle your hips, feeling his fingers rub and tease only the outside before they glide down to do the same to your tight ring of muscles, spreading the mix of your arousal and the lube.

“Is that so?” Doflamingo replies with a scoff. “The “sweet princess” your speak so highly of sent me pictures of her sloppy cunt every two seconds while I was away on business last week, not to mention she’s just a disobedient brat in general.”

“What do you think about all of this, do you really think you deserve more punishment?” His cool hook pats your behind, beckoning you to respond

“No daddy I don’t~” The cushion below you muffles your words as his fingers come back up to circle directly on your clit, giving you the friction you so desperately wanted. “Sir has already been mean enough to me.”

“Mean enough?” You didn’t need to see Doflamingo to know his face was turning blood red at your declaration. “You just wait, little girl, I’ll really show you ‘mean enough.” His threat sends a chill down your spine, but at least for now you are in safe hands.

“And if I do say so myself, she's anything but disobedient and I’ll prove it.” Crocodile pipes in while retracting his fingers, causing you to whine. “Princess, don’t speak or move unless I say so.”

“Okay daddy~”

“Now let's talk business.” Crocodile and Doflamingo begin to talk about partnering up and you lay still as a stone. After a while you got bored of hearing them bicker and found yourself ready to doze off, but before you could drift to sleep you started feeling strange down below…

There was a new tingling sensation on your clit that felt as if someone was petting it with a soft brush. It was pleasant and aroused you even more, but the feeling was beginning to spread down to your entrance and… wait..Your eyes widened realizing it was following the pattern in which Crocodile touched you.

Fuck. It was becoming very clear that the proclaimed ‘lube’ wasn't just that. Oh fuck. You bite down hard on your bottom lip as the tingling sensation turns into a dull burn. FUCK. As the minutes passed, the dull burn turned into a prominent one that made it hard for you to keep still.

You try to focus on something else, but the fire in between your legs is growing hotter and hotter, demanding every ounce of your attention. But just when you thought it couldn’t get any worse, it did.

Oh no.. There was no stopping the twitching muscles in your thighs, it was completely out of your control all thanks to the ticklish, itching sensation spreading from your clit to your ass.

“What did I tell you, Heavenly Demon?” Crocodile's hands come down to the globes of your ass, spreading them to expose your drenched and irritated pussy to the man sitting across. “She’s a good girl.” His leg bounces up slightly, bringing your enraged bundle of nerves so close to the fabric of his pants that it’s taking every ounce of your will not to grind down for the sake of relief.

“Fufufu~ I don’t believe I’ve ever seen her pussy be quite that red and swollen before~” Hearing Doflaimgo’s deep taunt made you hyper aware that he was watching everything. “What was in that little bottle of yours?”

“An aphrodisiac, a strong one at that.” You figured that’s what it was, but you still feel betrayed considering you thought Crocodile was on your side, but then again he and Doflamingo are cut from the same fabric, just in different patterns. “It’s surprising she’s been able to last this long...” His fingers dive back in between your legs to glide up and down your throbbing slit, but quickly pull away before you could get your fix. “I’m sure she’s quite miserable.”

“Please!” You cry out, feeling your mind and body slipping into the rabbit hole of desperation. “I can’t take it anymore!” No longer caring about the repercussions, you grind your clit down on his leg. “Make it go away!”

“Make what go away?” Crocodile “innocently” cooes while grabbing your hips. “We can’t help you if you don’t tell us.”

“The itching!” You wail. “It's so bad, please.”

“And what do you want us to do?” Your eyes roll into the back of your head as Crocodile bounces his leg up and down to bump against your clit. “Use your words.”

“Oh fu..” Your pleasure filled brain can only think of one thing that could satisfy the need in between your legs. “Daddy, Sir.. please fill me up, ‘need your cocks.”

“No, you don’t deserve it.” Doflamingo shot down your request just as quickly as you spoke it. “Unlike someone else, I know how to properly punish brats like you.”

“Sir you don’t understand!” You lift your upper body up from the chaise and grind down even harder on Crocodile’s leg. “See, look at how desperate I am~”

“I honestly don’t care.” Despite the lewd display you were putting on, the blonde's iron fist of punishment still isn't shaken. “You haven’t earned my cock, therefore you're not going to get my cock.” Frustrated tears roll down your face as you slam face first back into the cushions. “Cry all you want, it won’t change anything.”

“I knew you were cruel, but just look at the poor girl.” Crocodile picks you up and moves your body so you're sitting up right in his lap, facing Doflamingo. “Can you really say no to this?” His hook comes under your jaw, helping you keep your limp head up.

Doflamingo sneers seeing that your face perfectly matches the wet, flushed mess in between your legs. You looked like you were on a completely different planet with your tongue lolled out, drool dripping from your lips that were babbling incoherent pleas and then your watery eyes that could barely hold focus.

The sadistic man was absolutely eating the scene up, but as bad as he hates to admit, Crocodile did have a point. You were so pathetic with want, but lucky for you his cock had been straining against his pants for so long, he decides to give in just this once~

“If you want fucked oh~so~ bad, I will.” You sob out a weak ‘thank you’ seeing Doffy approaching you. “I’ve been wanting to stretch your little ass out for awhile now anyways.” His devilish long tongue swipes across his bottom lip as he plays with the zipper on his pants. “But I’m not going to prep you~” Prep or no prep, you didn’t even care, you just needed it. “Open up wide slut~”

“Yes sir.” You barely get the chance to part your lips before Doflamingo pulls his dick out and shoves it to the very back of your throat, causing you to gag around it.

“Since you're taking the back..” The man holding you brings his hand back in between your legs and slowly begins to tease small circles around your clit. “I assume I get to take this pretty pussy?” Crocodile’s hand trails down to your weeping entrance, slowly shoving two fingers in.

“Do what you want, just wrap it up.” Doflamingo scowls at the man while looking down at you, struggling to take his cock with a painfully wide mouth and hollow cheeks. “That’s right little slut, slobber as much as you can~” He balls his hand into your hair and thrusts even harder into your throat. “It's the only lube your going to get~”

“Don’t worry baby, daddy will make sure you're ready.” You tremble with dissatisfaction feeling his thick fingers leave your aching core before they glide down to your rear. “Relax for me.” You breathe through your nose and try your best to not tense up as he slowly works a finger in. “It will feel good, you just need to get used to it.” At first the sensation was strange, but by the time he worked a second finger in, you were starting to feel good. But it just wasn’t enough to satisfy the deep desire, you need much more. “Are you ready?”

“Of course she is.” Doflamingo’s blonde pubes tickle against your nose one last time before he abruptly pulls out with a thick string of your saliva attached to his pretty pink tip. He then rips your panties off and pulls you out of Crocodile's lap by hooking both arms under your knees, bringing your sweat covered back against his clothed abs. “I bet you're wondering how it’s going to fit?” Feeling his saliva coated tip smack against your semi dilated hole made you wonder the same thing. “You know what they say~ His hands tighten around your knees as he adjusts your position. “There's only one way to find out~”

Fuck! Your mouth falls open in a silent scream feeling Doflamingo abruptly slam his entire length into your virgin ass. “S’ big.” Your head falls back onto his chest as you fight to adjust to his size. “S’ good.” Although the pain was very present, so was the pleasure.

“Such a beautiful expression.” Through blurry vision you watch Crocodile pull his cock out. It was both fortunately and unfortunately massive in both length and girth with an up curve that you know is going to absolutely wreck you. “I wonder what it's going to look like when we're done?” He pulls a condom out from his pocket and rolls it on before finding your vacant hole. “Do you think you can handle it?”

“Yes~” You moan out, feeling the tip of his cock stretch your entrance. “I can~” He slowly fills your body's empty space, grazing over your g-spot and finally bottoming out against your cervix. “Oh fu~” Tears roll down your face from the stinging satisfaction of being so full and sandwiched between the two men.

“Look at you, taking us so well.” Crocodile grabs your limp hand and brings it down to the sweaty skin of your stomach so you can feel the way your body’s being split apart by two large cocks. “You’re such a good girl.”

“You’re such a good girl.” Doffy mocks the praise against your ear while dragging his length out of your rear. “You want to know what you really are?” Once again he slams back in, leaving you delightfully breathless. “A cock hungry slut, that’s what.”

“A-h!” You mewl, sending drool trickling from your lips, down to the valley of your breast.

“What a lovely mess you are.” You meet Crocodile's deep, lusty gaze as he licks the stray saliva off of your skin. “Does it feel good?” He slowly pulls out of your front, letting the head of his cock gloss over your pulsing walls.

“Yes, s’good, but I need more.”

And more is what you got.

Both men start fucking into you fast, hard, and in perfect sync, but unlike Crocodile’s precise, strokes, Doflamingo’s had a brutal, animalistic undertone as if he were attacking you. But it felt so damn good. Everything felt so damn good.

You don’t know if it's from the aphrodisiac or just the fact that they were filling you to the very brim, but both sets of your walls felt like one giant sweet spot and with each time their hips snap into you, you were being sent dangerously close to the edge.

You look down and watch your tummy jolt with each of their deep thrusts. Is this heaven or hell? At this point you don't even know. You were teeter tottering on the verge of losing both your consciousness and sanity, the only thing keeping you from doing so are the soft lips praising you on how good of a girl you were being in your right ear, and the sinful, degrading tongue calling you nothing but a dumb, sloppy whore in the left.

“Are you getting close princess?” Crocodile gains your attention by bringing his thumb down to your neglected bundle of nerves, rubbing it in fast circles. “You must be considering how tight you're getting around daddy’s cock~” You shake your head feeling the band in your abdomen ready to snap.

“Sir, daddy~” You lean forward and wrap your arms around Crocodile's neck for stability. “M’ cumming!” The vision behind your eyes turns white as you reach your climax, causing both men to let out a deep groan from the way your holes pulse and constrict around them.

“So tight.” Crocodile hisses against your ear while picking up his pace. “I won’t last much longer.”

“Lucky little whore.” You yelp as Doflamingo pulls you back against him with his sharp teeth biting into the skin of your neck. “I’m going to fill this useless hole of yours up to the brim.”

The men thoroughly fuck you through your high and reach their own by slamming balls deep into your abused holes. For a few minutes neither of them moved, that was until Doflamingo pulled out, taking a thick rope of cum with him.

Crocodile takes you from the blonde’s hold and pulls out gently before carrying you over to the chaise. “You did such a good job Angel.” He lays you down on the soft cushions and starts taking the full condom off of his softening length. “How do you feel?”

“M’ tired.” Along with your drooping eyes, a faint yawn leaves your lips, showing the fatigue you feel. “And thirsty.”

“Let me go get you some water from my office.” He gives your tousled hair a few pats. “I’ll be back shortly.”

˗ˏˋ ♡ ˎˊ˗
That was something... Although you had fun getting turned into a Y/N panini by the two businessmen, it had to be the most intense thing you’ve ever experienced both mentally and physically. It was mind boggling how you went from feeling so complete and full, to now feeling like a hollowed out shell.

Alongside the emptiness was a feeling of shame and guilt. Shame that you enjoyed it and guilt that another man touched you. “Sir.” You look at him while calling out, but he ignores you. “Are you angry with me?” His silence spoke for him. “I’m sorry.” There is nothing you hate more than knowing that Doflamingo was genuinely upset and displeased with you. It gave you a sinking feeling that you could compare to receiving a bad grade on something you worked really hard for. “I’m so sorry.” With tears running down your face, you force yourself to stand up on wobbly legs in order to make your way over to him. “Sir, please-”

“Kneel.” Doflamingo spat while giving you a disappointed frown.

“Yes sir.” Wanting to get back on his goodside, you obey. For a few seconds he just looks at you, but then suddenly cups your cheek in his large hand. You look up at him with a weak smile and nuzzle into his palm, enjoying the comfort you so desperately needed. “Thank you.” With the kindness he has shown you recently, you were expecting him to pull you into arms next, or maybe he would praise you on how good of a job you did. But you should have known better, because the devil doesn't hand out halos, does he?

“So tell me..” Before you have the chance to react, his hand rears back, striking you across the face. “Was that “mean enough” for you?” He mocks your earlier remark with a cold, bitter tone.

“Sir..” Your shaking hand comes up to your throbbing cheek. “I’m sorry for saying that, but I did everything else right, didn’t I? I was good..”

“Good?” The blonde laughs at you while smooshing both of your cheeks together. “Your “daddy” may not know any better, but I do.” His hand comes down the “collar” around your neck, tugging you forward. “You're just a whiny little slut, a messy one at that.” He motions down to the blotches of white falling from your ass and onto the floor below. “Now, I’m going to go grab something to fix that problem ~”He stands up from the couch. “And when I get back, that floor better be clean.”

As he walks over to the toy filled wall, you frantically look around for something, anything to clean the puddle up with, but nothing is in reach. Leaving you with only one choice. Carefully, you bend your upper body down to the floor and loll your tongue out, gathering some of the salty substance on the muscle before swallowing. It was disgusting, humiliating, downright dehumanizing, but you were going to do whatever it takes to get back on his good side.

“Fufufu~” Hearing his laugh coming from right above you, your eyes widen with panic seeing that some of the white liquid is still on the floor. “Despite typically being a useless slut-.” His overwhelming, domineering shadow was cast over you. “You’ve actually made my job a lot easier so to say by already being bent over~”

“A-h.” Feeling something cool and metallic prod at your leaking ring of muscles, your body quivers, almost sending you face first into the floor.

“Would you look at that?” Without warning, the object was shoved in all at once, causing you to wail from the stretch. “I think it suits you perfectly~” Along with the object, something soft was brushing up against your sensitive parts. “Considering your lapping up your master's leftovers right off the floor like the dumb dog you are.” You look in between your legs and see a fuzzy tail.

“No I’m not!” You bite back, and instantly regret it hearing the man tsk.

“You stupid, stupid girl.” Doflamingo instantly retaliates by tugging up on the tail, forcing you up to your knees. “Will you ever learn?” He bends down in front of you, showing off three clamps in the palm of his hand. “Maybe these will help.” To your horror, they had ball weights at the end of them. “Afterall, pain is a quick teacher.”

“N-o.” You shake your head and try to squirm away seeing the two of the clips closer and closer to your nipples. “D-”

“It would seem you don’t like my idea of a lesson~” You tense up, feeling the cool metal brush up against both your areolas. “Too bad~”

“Sto-!” Before you could get the word out, Doffy releases his hold on the clamps, causing them to painfully pinch around your sensitive buds. “Fuck!”

“Watch your tongue.” Once again, his large hand meets your soaked cheek, sending even more tears to pool in your eyes. “Cursing isn’t very professional~ ” His long tongue swipes across his lips and he brings the third clam down in between your legs.

“Wai-!” You panic knowing exactly where the clamp was going. “Doff-“ He releases his hold on the clamp, sending painful shocks to your already stinging clit. “Sir, please, take them off, I’ll be good!” Between the tight pressure and the weighs dragging the buds down, it was painful and not in a sexy, fun way.

“If you keep talking, I’ll put one on your tongue.” The threat shuts you up quickly. “Hmm, I wonder what would happen if we put more of this down here?~” Wait, no.. You see him grab a small bottle and make the horrific guess that it was the stimulant Crocodile used earlier. “Lay down and spread.” He clicks the cap open and pours a goop of it onto his fingers.

Knowing that both your breaking mind and your drained body couldn’t handle feeling that miserable again, you dig your knees into the floor and begin to inch away from him. “Sir please. You can spank me a hundred times or edge me a thousand, just please not that.” This entire time you’ve kept thinking if you could endure this, if you could deal with the pain, maybe he would be sweet to you. But it’s become very apparent, you are not going to get that, not any time soon.

“Is that so?” With each of your pathetic movements, his malicious smile grew wider and wider. “I was going to do all of that anyways~”

Stop. Your chest vibrates from your heart pounding against it, your ears ring from the blood pumping adrenaline and cortisol throughout your body. I can’t do it anymore. But no matter how hard you tried, your lips wouldn’t form words, only hiccups as you became frozen with a panic that left you completely at Doflamingo’s callous mercy. The only thing you could do now was slam your eyes shut as the gel covered fingers inch closer and closer.

Right when all of you hope ran out, the cold floor disappears and is replaced by something warm and strong. “Doflamingo!” You open your eyes and see Crocodile holding your body to his side. The sobs you held come back full force seeing that you were rescued and knowing that you were safe. “It’s okay, I’m here.” Crocodile scoops you up and carries you over to the sectional. “Take deep breaths.” He bends down in front of you and guides you through your panic attack. “That’s it, good girl.” His flesh hand smoothes up and down your calf muscles, helping ground you.

Gradually the pounding against your ribs mellowed out and your erratic breathing finally stabilized. “Thank you.” You rasp out. “I’m okay now.”

“Good, now drink this.” He holds the promised bottle of water up and you gladly downed the entire thing in a few gulps. “I’m going to take these off.” You wince as he removes the three, weighted clamps, but instantly feel relief as blood begins to flow back to the areas. “Want me to take that out too?” He gestures to the tail in between your legs and you nod. “Turn around and bend over for me.” You turn around on the couch and anchor your hands on the back.

“A-h!” You whimper feeling the bulbous head of what you now realize was a butt plug, stretching your sore rear one last time before it’s tossed to the side.

“There we go, all done.” Crocodile helps you back around and drapes you in his pelted fur coat. “Don’t worry, I won’t let him bother you anymore.” He gave you a reassuring smile before turning his attention to the blonde. “What the hell is wrong with you Doflamingo?” His calm demeanor disappears as he moves across the room to pull the blonde up by his suit vest. “Is scaring the poor girl into a panic attack your sick idea of a punishment?” You thought Doflamingo would bite back, but he didn’t. “If you have nothing to say for yourself.” Crocodile’s flesh hand pulls back and forms a fist. “Then maybe this will get you talking.”

The already unbearable tension in the room doubled and the steady heartbeat you worked so hard to achieve was starting to climb back up.“Stop fighting!” Both men tense up hearing you yell out. “I’ve been through enough today, I can’t handle any more.” They share a look with each other before letting go.

“We still have a few things to discuss business wise.” Crocodile grumbles and comes back over to sit down next to you, while Doflamingo sits back down on the chaise. “Let’s wrap this up.”

˗ˏˋ ♡ ˎˊ˗
Once again you found yourself listening to them do more arguing than business. Occasionally you would look at Doflamingo. What is wrong with you? You were now back in your right mind to realize that what just happened, was extremely messed up. To say he took things too far would be an understatement. There have been times like yesterday, where he went a little too far, but this…this was overboard, rock bottom even.

You recall an online article you read when studying up on dom/sub relationships that warned of something called ‘sub dropping”. There is no doubt in your mind, you had just experienced it for the first time and it was horrible and definitely something you never want to experience again.

In all honesty, you should have never got to that point in the first place. As you dom, Doflamingo should have seen the signs and put a stop to it, but he didn’t. For the first time ever, he had fully let you down, to the point you had to seek protection from another man.

A shiver tickles down your spine thinking about what would have happened if Crocodile didn’t rescue you when he did. Not only did he save you from experiencing that devilish lube again, he also calmly pulled you out of a dark place while giving you some of the comfort and aftercare that you so desperately needed. But. You pull the coat around your body and can’t help but wish it was pink and covered in soft feathers.

“Mr. Zero~” The conference room door opens, revealing a woman wearing nothing but a bikini. “I brought the liquor you requested~” In her hands was a large silver tray that had two bottles of amber liquid alongside a few glasses on it. “Heavenly Demon?” Her eyes immediately land on your boss.“It's so good to see you!” She squeals before making her way over to him. “It’s been so long~” She sits the tray down and jumps right into Doflamingo’s lap, making herself nice and cozy. “I missed you.”

What. You blink a few times to make sure you’re seeing what you’re seeing. The. The woman nuzzles her face into his check, smearing her thick make up on his skin. Hell.

“Likewise Cherry.” To your surprise, he welcomes her by hooking an arm around her, pulling her closer against his body. “Care to pour me a drink?”

“Of course~” You watch as she pours him a glass of the liquor. “Anything for my favorite guest.”

You didn’t personally know Cherry when you worked here, but you knew she’s one of Crocodile's errand girls and escorts. And it was quite obvious she and Doflamingo have a past.

“What a good girl you are, Cherry.” Doflamingo copies the praise you received earlier while giving the woman a kiss on the cheek. “Such a good girl~”

“You know how I am, Sir.” She straddles his lap and brings the drink up to his smirking lips. “Always eager to please~”

You couldn’t form a logical thought as jealousy, betrayal and sadness clash with one another in the very pit of your stomach. You chant over and over he’s mine, he’s mine. But you wonder if you even have the right to feel like this?

Although Doflamingo didn’t want anyone else to touch you, in the contract, nothing stated that he couldn't. Either way, seeing the display both upsets and angers you. Would it have been that hard to give you the same comfort and praise as he was giving this floozy?

“Who’s that?” Your coventonus eyes gain the attention of Cherry as she looks at you with both disgust and annoyance written on her face. “She keeps staring, it's freaking me out.” She wraps her arms tighter around the blonde as if she were afraid of you.

“Don’t worry about her, she’s nothing, just my toy.” Nothing? Toy? The harsh words from his lips made your already heavy heart drop. “Maybe if she was a good girl like you, I’d spoil her~.” Your brows furrow as he starts peppering kisses down your neck. Why? “Don’t look at me like that.” His arm wraps tighter around her petite frame as he looks at you from behind his glasses. “It’s not like I belong to you.”

That was the final straw. I’m leaving.

You go to stand up, but a hand on your forearm stops you. “Look at me Y/N.” You blink away the tears threatening to spill and look into Crocodiles eyes. “Are you okay?”

“No..” You shake your head. Far from it. “I’m not..”

“Sweetheart.” He gives you a remorseful look. “What can I do to help you?”

Back me up so I can beat his ass. Is what you want to say, but right now you are tired and still desperately in need of reassurance.“I just want held..” You look up at him with big, watery eyes. “If that’s okay..”

“Of course, come here.” For the second time today, the ever ruthless, uncaring, Doflamingo, drives you into the arms of another man.

“Mr. Zero..”

“Shh, I’ve got you.” You crawl into Crocodile’s lap and silently sob into his neck, taking in the oddly comforting smell of lingering cigar smoke. “It’s okay, let it out.” His hand rubs up down your back, while his hook keeps you in place. “He’s doing that just to hurt you, don’t let him win.”

“I know.” You mutter against your ear. “I just don’t understand why I deserve it.”

“You don’t understand, because you didn’t deserve it in the first place.” He softly replies. “Angel, you’ve been under that jackasses thumb for long enough, you need to-”

“Right there!” Cherry’s high pitched, girly giggles pull you away from the much needed pep talk. “Feels good~” Wait, is he? You lift away from Crocodiles chest and turn to see your worst nightmare was reality.

“Does it now~” Doflamingo had her back against his chest with her bottoms pulled to the side as he fingered her.

The knife in your back digs further into your flesh, to the point It made you nauseous. Cuddling and flirting was one thing, but touching her so intimately with the same hands that touch you.. You may be in the lap of another man yourself, but you would never be so disrespectful to the point you would touch Crocodile like that in front of Doffy.

“Angel.” Crocodile's hand gently turns your attention back to him. “It’s cruel, but that is who he really is.” You were realizing that before he spoke those words. “You’re wasting both your time and potential working under him.” Yeah, I know… “Come back to me. I’ll give you more opportunities and everything that he will not and will never give to you. And~” He winks at you as his hand slides from behind your back. “I can make you feel so good that you’ll forget about his lousy ass.”

“Mr. Zero...” You look up at him with tears stinging at the corners of your eyes. “I understand where you're coming from and I totally agree, but I...” Feeling his hand drop lower and lower, the guilt from earlier comes back. I can’t. You weren’t going to drop down that level of petty. I won’t. “I think-” The air in the room was becoming more and more suffocating. “I need to leave…”

“It’s okay.” You notice a glimmer of defeat in his eyes as he pulls his hand away and down to the pocket on his pants. “The platinum penthouse is vacant.” He spoke low against your ear while placing the penthouse key in your hand. “Stay as long as you need to.”

“Thank you.” You clutch the keycard while giving him one last hug, and, being the only man you felt cared about you, returns it. “I appreciate everything you did for me.”

“Please fuck me sir~” You get up from his lap and try to ignore the woman's wanton moans as you pick up and put your clothes back on. “Want you so bad~”

“Now, now Cherry.” Despite not wanting to, you turn around and see him looming over her with his hand on his zipper. “Be patient~”

Fuck it and fuck him. Your heels hit the floor so hard the sound was almost defining. Before you could think, blink or process, you were already in front of the Chaise, grabbing a fist full of Doflamingo’s suit jacket.“You bastard…” Something deep inside of you conjures enough power to sling him off of the woman and into the floor.

Your legs find either side of his large body before you crouch down.“How dare you, Doflamingo!” Out of anger, you rear your hand back, slapping the man across the cheek. “How dare you…” You lift up from him and come up to the diamond’s around your neck, pulling them off in one fatal tug. “I hope this makes it clear that this “toy” doesn’t belong to you either.. not anymore.”

“Here Cherry, it’s all yours.” You throw the necklace into the confused girl's lap. “He takes his coffee black, he shows only three emotions and I assure you this-” You meet his red lenses with tears rolling down your face. “He will only ever know how to hurt you.”

With that you left the room and the people in it, quiet and speechless.

˗ˏˋ ♡ ˎˊ˗
How ironic. As you key into the penthouse, you see the stinging red spot in the middle of your hand from where you slapped Doflamingo. Of course your attempt to get back at him ended up with you carrying the inflicted pain.

You kick your shoes off and pad over to the luxurious california king bed before letting your tired body be engulfed by it. Why did I fall in love with him? Why lie to yourself any longer, you were never falling in love with him, you’ve been in love with him from the very start. I’m so stupid. You curl into one of the pillows for comfort and think back on the many nights you stayed up imagining what it would be like if you and Doffy became a normal couple. The kind of couple who went on dates, who woke up next to each other, who loved each other.

What was I thinking? As much as you loved being his masochistic sub, before him you were just a normal girl who kicked her feet and giggled at a kissing scene in a movie. You loved the idea of love and you always dreamed of building a cute and meaningful relationship with someone, so you can't understand why you signed that stupid contract. Maybe, despite knowing deep down it never would, you thought you would end up charming him to the point he would fall head over oxfords for you. But you remember there were women before you who must have thought the same thing, and you're sure there will be women after you who will too.

You’ve learnt a disheartening, but valuable lesson today. Being with Donquixote Doflamingo was both excruciating and dementing. One day he gives you hope by calling you his wife and leads you on even more by buying you a pretty necklace, then the next day he puts you back into your place, giving you a harsh wake up call that he will never truly care about you, let alone love you, by pushing you to far and touching another woman right in front of you while reminding you of what you really are.

A toy.. At the end of it all, that's all you were. It’s just as he said, you didn’t own him and you never would in the same way he owns you. Barring you no longer having a “collar”, you were no different than a pet to him, his good obedient pet that no matter how badly he treated, would always come running back to him for more.

Not anymore. Today, you are putting an end to a war that you were doomed to lose from the declaration. And never again. Your white flag goes into the air, ending the confusing, vicious, one sided battle. It’s over…

˗ˏˋ 🦩ˎˊ˗

“Doflamingo I’ve had the unfortunate privilege of knowing you for a long time and I’ve never seen you lose your composure quite like *click* this..”

“I’m actually quite composed, gator boy.” Doflamingo held the man by the collar with one hand, while the other held a gun to his head. “But that will change if you don’t tell me where my little mouse scurried off to.”

“I already told you I don’t know.” Crocodile, despite being held at gunpoint, covers for you. “We’re obviously done here, you should leave.”

“I’m not going anywhere until you tell me where the hell she went.” After Doflamingo got over his initial shock, he ran after you, but your trail ran cold as if you disappeared into thin air. “Answer me or I’ll blow a hole in your head.”

“My answer remains the same.”

“If I find out you're lying….” He pulls his suit jacket to the side, putting the shiny pistol back in place. “Let’s just say I’m pretty confident that I could run a casino.” The blonde removes himself and walks towards the conference room exit.

“Don’t you think it’s about time?” Crocodile spoke up while fixing his disheveled scarf. “To let her go, that is..”

“Care to elaborate on that?” Doflamingo turns around and snarls, feeling angered by the suggestion.

“You know, most of your past PA’s, subs, whatever the hell they are to you, work for me now and they all said the same thing.” Crocodile huffs out while bringing a fresh cigar to his lips. “That you were cruel, heartless, overbearing.”

“What are you getting at?”

“Y/N is a talented, sweet, and bright girl whom you have stuck in your dark web.” A cloud of gray fills the stale air. “So do her a favor, and let her go.”

“You want to know what I think Mr.Zero?” Doflamingo looks over his shoulders and at the figure hazed over by the thick smoke. “You need to take your own advice.”

˗ˏˋ🦩 ˎˊ˗

Doflamingo left the casino and found himself in your apartment. He had a hunch that you wouldn't be here, but he still checked behind every door until he reached your bedroom.

He walked over and sat down on the neatly made bed, picking up the familiar pink flamingo in the process. A pleased smile quirks onto his lips seeing the matted fur, a sign that showed him just how much it meant to you.

The blonde lays the plush back into its rightful place before pulling his phone out. Where are you? On his screen was your bright smile from the picture he took yesterday. But that happy look was long gone and replaced by sadness and anger, all because of him. He will only ever know how to hurt you. Your words shook him and the very firm foundation he stood upon, but after what he just did to you, he could see why you said it.

I’m truely, a bastard. A painfully aware, bastard who realizes that what he did, was fucked up. Why would I do that when I..

Doflamingo never planned on having true, genuine feelings for anyone, but the second he saw you in the reflection of the elevator doors, holding up his fallen feathers as if fate had led you to him, that all changed.

The more he talked to you, the more he learned about you, he found himself becoming more “fond” of you. But he fought that feeling, stringed you into signing the contract and then treated you as if you were just another one of his submissive PA’s. He figured by doing so, he would get over the strange way you made him feel, but as time passed it seemed to get worse and worse.

And now as he sits on your bed, he realizes the iron wall guarding his heart cracked, leaving a small opening that only a mouse could mosy its way into. Damn that girl. He got up from the bed and made his way back to his car. I need to find her.

Doflamingo’s actions were petty, spiteful and very befitting of his cruel title of a man that can only hurt. He knew he pushed you too far yet again, he knew he was a asshole for punishing you so harshly and he knew that right now, you were somewhere alone and hurting, just because he wanted you to feel the same sinking feeling he did when he saw Crocodile touching you and giving you the comfort that he should have.

Do her a favor and let her go.

He knew Crocodile ran a good argument. If he keeps you, would he ever be able to bring you the same joy that you bring him? And most importantly, is he even capable of giving you that four letter word? He takes one last look at your picture on his phone screen and makes up his mind.

“Like hell I will, and like hell I will try.”

˗ˏˋ ♡ ˎˊ˗
You sat on the bed looking out the penthouse windows, admiring the way the evening sun illuminates the endless lines of skyscrapers. I better leave soon, you’ve been telling yourself this for hours, yet you didn’t move.

You’ve been lost in thought, thinking of what comes next. After spending the last year starring in fifty shades of pink with the tall, blonde version of Christian Grey (that crawled out of the deepest, darkest pits of hell), you were at a stand still.

It stings, but you know soon, Doflamingo would have another woman in your spot and his life would go on as if you were never in it. Why am I crying? You hold your palm up and watch the tears collecting on the skin. Was it because of the thought of him replacing you so easily? Maybe, but knowing that your time spent together probably meant so little to him..

It’s funny how determined you are to forget about him, yet here you are with sweet memories of him flooding your mind. Like the time you caught him stocking your desk drawer full of your favorite snacks when he thought no one was around, or the time he gave you a piggyback ride up the horrendous 44 flights of stairs when the elevator was out of order, and your favorite, the time he cheered you up on a bad day by tickling your ear with a pink feather. You’ll remember all the subtle, but nonetheless special things he did. But special or not, he was still cruel.

It will be okay Y/N..You know there is only one Donquixote Doflamingo and you have no doubt that you’ll compare every future partner to him. I just need to get through this. Right now it seems like your whole world is falling apart, but you know soon it will all be for the better. Because without Doflamingo in your life you-

Before you could finish the thought, the hotel room bursts open with a power that sends the decorative wall clock to the ground. You turn around and the very man you were thinking of, stood in the doorway with an eerie, unpredictable aura surrounding him.

“Doflamingo!?” You quickly stand up from the bed. How did he find me?

The melancholic air in the hotel shifts as he slams the door shut, locking it in place. Without uttering a word he took both his suit jacket and glasses off, placing them on the small desk by the entryway. You took a few cautionary steps back, but kept your composure knowing he was just trying to intimidate you.

Don’t let him win. You chant to yourself while he begins making slow, but long strides towards you. You can’t let him win. Once again you find yourself moving back until your body comes in contact with the windows. You were cornered with nowhere to run, but you weren't about to cower, no, you were going to stand tall and hold your ground firmly.

“You smell like cigars.” He spoke up, snarling through clenched teeth.

“You smell like tacky perfume.” Snapping back at him, you hold eye contact with his fierce crimson gaze and take a powerful step forward, showing him you weren’t afraid. “Now care to tell me why the hell you’re here?”

He didn’t answer and the room fell silent as you both stood off against one another in a battle of your hell bent anger vs his pure, unbridled rage.

“Strip, now.” His beautifully dangerous, sharp eyes narrow in on you.

“You have some audacity.” You cross your arms and reply with a blunt “No.”

“Excuse me?” Doflamingo’s hands slam down on the windows, resting on either side of your head.

“Despite what you may believe about yourself, you're still a human with two ears.” Even with the unease swirling in your chest, your words don’t falter. “So surely you heard me say no!”

“Oh I heard you, I just don’t care.” Doflamingo bends down until his hot breath is fanning your face. “Strip.”

“You’ll have to make me!” The fury swimming in his eyes turns feral at your poor wording Oops. “Wait-”

“Is that so?” You gasp as his large hands grab onto your blouse. “You want me to make you?” His long fingers thread into the empty spaces between the buttons.“Then I’ll fucking make you alright.” His brute strength rips the fabric like it were made of paper, sending buttons to scatter across the carpeted floor.

Before you could blink he took your skirt off just as easily, ripping a clean line right down the seam before tearing both your bra and underwear off. You try to bring your arms around your body to cover yourself, but one of his hands traps both of you together, slamming you back against the glass.

“I should take you right here.” He twirls your body around in his hold and presses you against the window, smooshing your breasts against the cool surface. “Show the whole fucking city who you belong to.” His knee comes in between your legs, knocking them apart before he grinds up against your bare core. You mewl as the soft texture of his dress pants slowly drags up and down your sensitive clit. “You must like that idea considering you're practically wetting yourself.” You look down and see the dark blotches where your growing arousal has soaked his pants.

“I was actually thinking about Crocodile before you came in here~”

“Were you now?” Both the lie and your breath get stolen from your lungs, feeling his knee apply even more pressure. “Maybe you should go work for that bastard.”

“Maybe I should!” You swallow a moan and meet his reflection in the glass. “Unlike you, he didn’t treat me like shit before touching another woman right in front of my eyes!” Your venom filled tone caught him off guard, giving you the opportunity to shimmy out and away from his hold. “I don’t know why you even bothered to find me, considering you see me as "nothing" and just a "toy ".”

“Y/N wait.” Upon hearing your words, both his demeanor and tone took a complete turn. “I need you to listen to me.”

“Why should I?” You slam your foot on the ground. “Listening to you has only gotten me hurt today.” You bite your trembling lip. “You know, before Crocodile ever laid a finger on me I was concerned about you…” Despite wanting to stay calm and cool, tears begin to roll down your face.“I put myself in your position and thought about seeing you with another woman and it absolutely crushed me, but you told me to do it and I did it because you are my dom and I trust you.” You wipe away your tears with the back of your hand. “I did everything you asked, but you, being you of course, felt the need to “punish me”.”

“Y/N…”

“Imagine if I slapped you twice, made you lick a gross floor, called you nothing and a toy while sitting in the lap of a stranger before looking into your eyes and saying I don’t belong to you…. It’s not a pretty picture, is it?” Your voice cracks. “I was so vulnerable and I needed you but...” Seeing his blank expression made the dizzying mix of emotions you were feeling come pouring out all at once.“Goddamn you Doflamingo, I hate you, I hate you!” You walk up to him and ball your fists in his button up, channeling your anger into the linen until your knuckles went pale. “I hate you so fucking much that I don’t understand why I love you!”

It's over now. You release his shirt and take a step back, while he looks down at you with shock written all over his face. “Don’t look so surprised, you heard me right…I love you.” You motion over to the door. “That means our contract is broken, so you should just leave..” This is goodbye. You step out of his way, clearing his path, but he doesn't move.

“It’s not broken quite yet.” In one quick motion, you find yourself back against the windows and under Doflamingo’s looming figure. “But tomorrow when we go into the office, it will be, because I’m going to rip it to shreds.” The intense red orbs no longer harbor the look of rage or confusion, instead you see something new. You were unsure what it was exactly, but It was soft and determined. “There’s no point in keeping it if both parties broke it.”

Both parties?? “What are yo..”

“I’m not done, little mouse.” He bends down, making his face level with yours. “I won’t make excuses, just know I am ashamed for both my actions and the fact that I failed you today.” In the time that you’ve spent with him, you’ve never heard his tone be so calm, so sincere. “And you’re not just my “toy”, you never really were.”

“Then what am I, your PA, your sub?” You clench your fist. “Just what exactly do you see right now?”

“You’re all of those things, but more importantly your Y/N.” His hands wipes the stray tears away from your face. “My Y/N.” There was no dark possessiveness laced in his words, they were spoken as a soft matter of fact. “I may not know much about love or romance, but I’m sure you can help me learn.”

“Say it..” You need to hear it, the three words that could clear the confusion clouding your mind. “I need to hear it from you, Donquixote Doflamingo.”

“Using my full name are we?” He smirks, pulling your trembling body closer to him. “I’m very fond of you..”

“Doffy..”

“I think very highly of you.”

“DOFFY!”

“You're not going to give up are you?” He chuckles while bumping his forehead against your own. “I love you Y/N.” In the moment after the confession, where his lips press against yours for the first time, despite the shattered clock still laying on the floor, time truly froze for you. “And for you-” His hands then trail down your sides and come around to pat your butt, singlining you to jump. “I’ll try to be a sweet and gentle lover.”

“I doubt you ripped my clothes off to be “gentle”?” You jump into his arms and cut him off with another kiss while bringing your hands down to free his erection. “What happened to showing this “whole fucking city” who I belong to, hmm?”

And just like that, you caused Doflamingo to completely lose his mind and composure. “My naughty girl.” He purrs against your ear and in one move, bottoms out in your soaked cunt, sending your eyes rolling into the back of your head. “Is that what you want?” His tongue licks up the side of your neck, leaving a trail of goosebumps to follow. “You want me to show you who owns you?”

“Yes!” You cry out as he sets a fervent but belligerent pace. “Oh fu~” Your arms hook around his neck. “S’ good~”

“Tell me something~” Without warning he pulls out and turns you around in his hold to face the window. “Do you think Crocodile could make you do this?” Your mouth gapes as he slams back in, continuing his relentless strokes. It didn’t take long to realize what he was asking. “Look at yourself.” You whimper seeing the reflection of your pussy squirting all over his cock. “My slutty little girl’s making such a mess.” With each of his hard, purposeful thrusts against your sweet spots, you gush even more and watch it trickle down to the window seal. “Now tell me, who do you belong to?”

“You!” You babble out, lost in the euphoria. “I belong to you Doffy!”

“Damn right you do.” He moves you away from the window and slams you down on the bed before slotting in between your legs. “And I’m going to make sure you never forget it.”

Sex with Doflamingo was always passionate and intense, but what you were experiencing right now was on a whole nother level. Your legs are folded against your body and both of his hands are wrapped around your throat, not in a way that choked you, but in a way that kept your eyes locked on his as he fucks you like the merciless, taker of a man he is.

“Did he fill you up like I do?”

“N-o ” You shake your head knowing nothing in this world could truly compare to Doffy's cock. “Oh fuck-” With the new position, it was absolutely rearranging your guts, no, your entire DNA so that it would be the only one to give you pleasure. “M gonna cum ~”

“Yeah?” You frantically nod your head as his thumb comes down to rub fast circles into your clit. “I’m going to fill your pussy up and send a picture to that bastard~”

“You’re wrong sir.” You rasp out meeting his confused expression. “It’s your pussy, I belong to you.”

“Fuck-” His deep voice growls against your ear. “That’s right~” His pace quickens, causing the band your abdomen to reach its breaking point. “My good girl knows her place~”

“Doffy!” You hear the lewd liquid sloshing out of you once more as you cum with his name falling from your swollen lips.

“Fuck Y/N-” Doflamingo follows right behind you with a low hiss of your name, filling you up with his hot, thick release.

“Wait.” He abruptly pulls out and gets up from the bed, causing a confused expression to paint your flushed face. “What are you doing?”

“Don’t worry about what I'm doing, worry about what I’m going to do.” He throws his shirt on the floor followed by his pants and boxers. “My precious girl~” He picks you up from the bed and slams you up against the wall. “I’m going to absolutely ruin you.” With a malicious smirk, he bottoms out into your twitching hole. “Lovingly of course~” He follows up, placing a sweet kiss on your forehead.

Doflamingo fucked you for hours. There wasn’t a surface or square foot of the penthouse without both of your sweat, cum or some form of body fluid tainting it. No matter how many times your perfect pussy tightened around him, no matter how many times he filled you up, he just couldn’t get enough of you. And judging from the bloody nail scratches on his shoulders/back, and the way you were babbling absolute nonsense, was all the proof he needed to know you felt the same.

The blonde moves back to the bed, sitting down with you in his lap. “Watch Y/N.” A large hand guides your gaze to him slowly bringing you back down on his cock.“You look so beautiful being split open by me, don’t you think?”

“Yes.” Your eyes roll into the back of your head. It was unbelievable how even hours later, he was still deliciously stretching you out. “I love it~” You wrap your arms around his neck and smash your lips against his. “S’ good.” You use your last bit of energy to roll your hips in his lap. “Feels s’ good~” With every one of your movements, his head grinds on the spot deep within you that sends stars shooting across your eyes. “Gonna cum again!”

“You’re driving me insane.” Doflamingo grunts while bringing his hands down to your hips, urging you to keep going. “If you keep doing that, I’ll cum.” The sounds of sweaty skin meeting crescendos in the room as you pick up the pace. “Fuck, that’s my girl.” He praises feeling your walls squeezing around him.

“Doffy!” With one last rock of your hips, you reach your climaxes at the same time. “Full~” You utter as he fills you up for what felt like the millionth time, leaving you completely overflowing with his cum. His arms circle around your back, keeping you held snugly against him while you both come back down from your highs.

You bring your head down to rest in the crook of his neck. “I don’t think-” A small whimper leaves your lips feeling him slowly pull out. “I can do it anymore.” It was official, you were truly past your limits.

“Neither can I.” Doflamingo falls back with you on the bed, taking in deep breaths of his own, which was a rare sight considering his otherworldly stamina. “Are you okay?”

“Yeah.” Lifting your head, you give him a lazy smile. “You said you wanted me to teach you how to be romantic?” You come face to face with him, bringing your sweat covered forehead against his. “Well, it would be really romantic if you’d carry me to the bathroom….I really need to pee.”

“Fufufu~ is that so?” With you in his arms, he lifts up from the bed. “You're telling me you still have a drop of liquid in you after all of that?” You blush as he motions to the different areas of the room where he made you fall apart.

“Shut it.”

˗ˏˋ🫧ˎˊ˗

After you finish your business, Doflamingo starts a shower, filling the bathroom full of steam.

“Ahh~” He was nice enough to let you get under the hot stream of water first. “That’s the stuff~”

“Y/N.” You hum, letting the blonde know you were listening. “I should have never made that bet, I should have never punished you nor took my jealousy out on you and I should have never touched that woman.” He places a small, apologetic kiss against your sore cheek. “For all of that and the many distasteful things I’ve brought upon your sweet soul, I’m sorry.”

“Okay gigs up imposter.” You look up at him with a raised brow. “Where is the real Doflamingo?”

“I assure you I’m the real deal.” With a wicked grin, he pulls you from under the shower and slides his hands down your hips before coming around to your butt, giving the supple flesh a warning squeeze . Yup, it’s him. “Shall I prove it to you?”

“No thanks~” You step back under the safety of the running water. “I’m good.”

“Are you sure?” Positive. “I’ll be gentle~”

“You couldn't be gentle if you tried.” You murmur. “In all seriousness, I appreciate you apologizing. But I have to ask…are we..in a relationship..” Although you both fessed up, you were still unsure what this made you.

“Yes.” Doflamingo smiles while grabbing the small bottle of shampoo from the shelf. “We are.” He twirls his finger in the air. “Close your eyes dear.”

You turn around and close your eyes. “So we’ll go on dates?”

“Of course~” His large hands come up to your head before he begins massaging the shampoo into your hair. “I’ll take you anywhere, even the moon, if that's what you wanted.”

“I was thinking something less interstellar, maybe a nice restaurant.” You hum in delight feeling his fingers dance against your scalp. I could get used to this side of him. “Are you going to start introducing me as your girlfriend?”

“I will, that is what you are after all.” Doflamingo guides you under the shower, rinsing the shampoo from your hair. “All done.”

“Doffy.” You step out from under the shower and wrap your arms around him. “I love you.”

“I know~” Smug jerk. “And I love you too.” There we go, much better. “Go ahead and dry off, I’ll be out soon.”

˗ˏˋ🫧ˎˊ˗

“Since he decided to rip my clothes.” After drying off, you pick his button up from the floor. “I’m taking this.” Once again, you find yourself admiring the way his clothes fit you in a mirror. A shirt to him, and a nightgown to me.

“Y/N.” You jump a little, feeling stray drops of water fall from blonde locks and onto the juncture of your neck. “I never want you to take it off again, okay?” In the mirror you see a familiar set of diamonds back in their rightful place adorning your skin.

“I won’t , but what about you?” You tease as he fastens the clasp. “How am I going to lay claim to you?”

“You say that as if you don’t have a few layers of my skin under your nails.” Touche~ “But I guess you didn’t notice.” Notice what? He grabs your hand, twisting it slightly to the side, revealing the small, golden cufflink shaped like a mouse. “Out of all the pairs I could pick out, I got these.” They were extremely cute, but also extremely unlike him. “Because they put me in mind of you.” You were about to “aww” but he cuts you off finishing with a “My little pest~”

“Would it hurt you to be nice to me for once?” You growl before shaking away from him and make you over to the bed to crawl under the duvet. “For that, you can sleep on the wet spot~”

“And you call me the cruel one.” He scoffs. “But I’ll take accountability, considering I caused it~” The lights in the room go out as Doflamingo slots himself next to you, pulling you against his chest. “Goodnight Y/N.”

“Doffy?” With a soft tone, you mumble into his pecs. “You're not going to change your mind…are you?”

“On what?”

As happy as you were in this moment, as much as you didn’t want this fuzzy feeling to go away, you couldn't help but worry knowing how predictable the man was. “Loving me..”

The sorrow filled question and the uncertainty in your tone catches Doflamingo off guard, but he understands why you’d be concerned. He is fully aware of his Y/N quote “Sour Patch Kid.” behavior. But he has never been so certain in his life. He wants you, he has you and that isn’t going to change.

“No, little mouse, I won’t.” A satisfied smile curls on his lips feeling you relax and snuggle closer to him. “Now go to sleep, we still have to work tomorrow.”

ᶻ 𝗓 𐰁

Doflamingo felt your body relax more and more in his hold and finally, you fell asleep. But he on the other hand didn’t want to close his eyes. He felt the need to stay up to make sure that you didn’t vanish from his hold.

He was so worried that he lost you for good today, but seeing your face smashed against his chest with a small line of drool connecting from your lips to his skin, made him very aware that he hadn’t.

“I almost forgot!!” His whole body tense up as you suddenly rise up from his chest with a sense of urgency. “How did you find me??”

Doflamingo blinked at you a few times. What is wrong with her? “Umm, you remember my friend Vergo who works for the police department?”

“Yeah?” You nod in your half asleep state.

“I got him to ping your cell phone.”

“But how did you figure out what room I was in?”

“I had Dellinger hack into the security systems.”

“Oh, makes sense.” And just like that you fell right back asleep on his chest.

“My dear...” He gave your forehead one last kiss before laying back onto the pillows. “You are an odd one.”

˗ˏˋ 𓆌 ˎˊ˗

Pink Jackass- Sent an attachment. As you can see, I’ve made quite the mess, send my condolences to the maid. Also I’m leaving you a bad yelp review~

Crocodile’s eyes blew wide open looking at the picture of you laid out on the hotel bed with thick cum leaking from your swollen pussy and a fucked out expression on your face.

Pink Jackass- Sent an attachment. P.S-Look at how precious your Angel looks in the arms of the Heavenly Demon.

“Dammit.” Crocodile gritted his teeth seeing the second picture of you peacefully asleep at that asshole's side. “I really do loathe that bastard.” He closed his phone and threw it against the desk. “It’s a shame he’s so good with business.” Needlessly said, he got the message loud and clear, you were not and will never be his.

˗ˏˋ Part 4 Coming Soon ˎˊ˗