Since you wore yourself out repeatedly the afternoon before, you slept like a rock and ended up awake and about at 4am. Oh how the tides had turned on how this Sunday was going compared to last week. You took a nice shower that you had hoped would be relaxing, but the idea of getting into clothes that had been gifted to you had gotten your imagination rolling again.

You had once heard Thatch tell Marco that a man only gifts a woman clothes to see them on his floor, and by that logic they had decided to buy you a set of lockpicks for your birthday instead of clothes. But now the jest was bouncing around in your head as you put on the sweats and shirt.

You had to admit you were grateful, of all accessories provided, lingerie wasn't a part of it. You had plenty of your own and given the modest cut of the dress you didn't have to worry about needing anything custom to go along with it. It had taken you a few moments to decide on what underwear to wear – the basics, and assume nothing will happen? Or dress to match and deal with the fallout of having thought ahead if something does happen.

In the end you went with dressed to match, since the idea of something happening and being in your boring underclothes felt more mortifying than anything else. At least if you ended up being teased for matching it would help you lean into things that were already happening.

You stepped outside a few minutes before 8, enjoying the morning air and preferring to watch the world go by vs pacing yourself into a frenzy inside. It was barely a minute later when an, admittedly modest, limousine pulled up to the end of your driveway.

An older gentleman, who looks like he worked out at every available opportunity to be that muscled at that age, steps out from the limo's driver side and approaches you.

"Miss (Y/N), shall I take your bag?" He inquires. His voice didn't have the deep timbre that Doflamingo's did, but there was a layer of long-held authority in it. You doubted his only job was chauffer.

"Yes, please – mister?"

"Just Lao, young miss. The young master suggested that if you insisted on calling me Mr. Lao I should address you as young lady." He adds, and a grin spreads across your face.

"Very well, thank you for coming to get me, Lao." You reply as he puts the small suitcase into the trunk.

"You're quite welcome, Miss (Y/N)." He opens the door for you, and you had the good sense to let him. As you step into the limo, you find you were not alone.

Doflamingo sat along the side in casual enough attire you were almost unable to stop yourself from making a face at the sight of it. He still wore his shades, but the t-shirt fit him in a relaxed way – quite the feat given his broad shoulders. You were surprised to see sweatpants not dissimilar in style from yours, and loafers to finish the look. You noticed he had even downgraded his usual metal watch to one with a leather band.

You couldn't help yourself as you settled in, and quipped. "Do you even own a pair of sneakers?"

"Due to my height, my shoes are all custom-made." He replies smoothly enough.

"That would be a no, then." You smile back at him as Lao gets into the driver's seat.

Doflamingo gives a faint smirk and turns toward the front of the limo. "We are ready, Lao."

"Very well, young master." Comes the reply, and the window separating the driver from the two of you rolls up as the limo rolled into motion.

Taking a better look around the limo, you realize it wasn't overly large, but with enough room that both Doflamingo and you had a comfortable amount of personal space, while not being so separated as to make conversation awkward. The black leather interior was broken by accents of velvet and a deep blood-red wood grain. It was certainly old-time elegant, and not as flashy as you expected.

"I admit, I appreciate you sending over clothes for today. I would've felt uncomfortably under dressed for breakfast if I'd chosen something on my own." You'd poked him a couple times and he hadn't teased in return, so you figured it was only polite to go easy on him. As he said before, today was for your enjoyment.

"I'm glad to hear it put you at ease." He purrs with a smirk. Teasing or not that voice was a sin. "Before we get too far into the day, I did want to ask if you were at all uncomfortable with going to my family's estate. I have alternative plans if you'd rather not, so don't feel pressured."

"Will your family be there?"

"They will."

"I'm okay with it then," you admit. "Being in a place like that and having it empty would be a bit unnerving, but it wouldn't be bad to see your family again." You see him raise an eyebrow and you sigh in mock defeat, pouting and looking away. "I feel a tiny bit guilty for leaving how I did last week."

"I see."

"Miniscule." You reiterate, going quiet for a few minutes before relaxing into the comfortable seats. The low, barely noticeable vibration of the car's wheels as it drove forward were starting to lull you into a nap, and you decide to fight against it.

"So where are we going for breakfast, your estate?"

"No, after some asking around, I was informed of a nice place not far from here that does an exceptionally good job with breakfast, and I thought it would be worth the risk to go there."

It was your turn to raise your eyebrows in surprise. "I... don't mean this nearly as mean as it's gonna sound, but you don't look like the kind of person who risks the unknown, Trouble."

"I assure you; I take plenty of risks." He replies, and you could swear there was almost the tiniest hint of a pout in his voice.

"Oh, I'm sure you take all kinds of risks, Trouble." You laugh. "What I mean is you seem like someone who mitigates risks to make sure any risk you do take still end how you want. Like if you went skydiving you'd pack your own parachute."

Or provide someone with clothes for a day on the town so you knew they'd wear something that matched your style. You thought to yourself, finally realizing all the reasons behind the offered clothes.

"A fair assessment, Miss (Y/N), and one I imagine I cannot deny in this case either."

The limo comes to a stop, and you hear Lao exit from his cab. He opens the door and Doflamingo steps out first, offering his hand as you come out behind him.

"Something like a date, indeed, what a gentleman." You tease, taking his offered hand and stepping out of the limo.

"I did promise." He states.

"You never said 'promise', but you're keeping your word, so I'll appreciate... that..." Your words die on your lips as you realize you are outside Sanji's café. A sign on the door indicates they were closed, but Sanji steps out and greets you.

"The private party has arrived, right this way." He offers cheerfully.

You weren't sure who you needed to kill for this first, Trouble or Sanji. You opened and closed your mouth a couple times trying to find the right words and a chuckle from Doflamingo causes you to turn to him first.

"Worth the..." you stammer, and then bite back what else was on your mind, unsure of if you wanted to say it.

Stomping over to Sanji, you go to snag his cigarette out of his mouth, but he removes it and holds it aloft before you can reach him, smiling all the while. "You could've warned me." You huff.

"My silence was appropriately negotiated." He beams, he was having the time of his life, this romantic idiot. "Besides, (Y/N), I promised."

"Tch." You walk past Sanji and into the café. It was done up a little more than usual, with nothing but a single table in the middle of the, granted, small interior of the café. Normally there weren't more than five tables as it was.

After Doflamingo enters, Sanji closes and locks the door, to make sure that none of his sleepy morning regulars blunder in past Lao accidentally. There are menus waiting for you and Sanji leaves to get coffee before coming back to take your orders. You have been keeping your arms crossed and grumbling in Sanji's general direction since entering the café.

"I hope you're not truly upset, Miss (Y/N)." Doflamingo says as you wait for your meals.

You finally crack a smile and shake your head. "I'm... not. I'm just," you scrunch up your nose a little. "I can't say I dislike surprises, cause good surprises are great, I've just been done in by my own morals is all."

"Might I ask you to elaborate?" He inquires. You could feel him taking in all of this as though he were compiling data for future use.

"For reasons I'm not yet okay with getting into, let's just say I take promises seriously. Someone's word can falter, cause sometimes we agree to something, and it slips our mind. No shame, no foul." You explain. "But promises are another matter. An invocation of honor. I don't promise lightly, and my friends seem to have adapted it."

A moment's silence. "Ah, I see. You expected your long-time friend and boss would give you a warning about my plan."

"I did, until he said he had promised." Your smile is genuine. "I'm not mad. A little salty that I feel like I've fallen into a trap of some sort, but not mad."

"Promise?" Doflamingo prompts, quite the smile on his lips.

Your face goes pink despite your efforts. "Promise."

You have a good meal afterward, filled mostly with small talk about the food. You say the most; rambling on about Sanji's cooking, about how bad you were when you first started helping him, and about how you only absent-mindedly put buttered bread in a toaster one time before you never made that mistake again. It was hard to keep conversation going with Sanji's cooking in front of you, however, and things naturally die down as you finish up your meal.

"I don't know how you do it, Sange," you say, not quite hitting the last syllable of his name. "But I feel perfectly full again. Like if I had one more bite it would be too much."

"Agreed. It was delicious and satisfying." Doflamingo adds. "Well worth the risk."

You almost choke and then laugh. "You really are a smarmy bastard."

"Nonsense," Doflamingo insists, standing up and offering his hand. "Today I'm a perfect gentleman."

"You're a perfect something," you quip taking his hand. It was warm, and expectedly large, and you were reminded of when you shook hands before, as though he wanted to kiss yours instead of shaking it. "Jury's out on what, exactly."

He unlocks the door in a smooth motion and holds it open as you leave the café and go back into the limo. Lao assists you back in again, and this time Doflamingo sits next to you in the same backseat. There was still some space, and he kept his hands to himself, but the proximity was threatening to stir your imagination.

"We're not going far." He states, as though giving an excuse for why he hadn't moved to a different section of seating. "There's a small carnival between here and the estate and I had assumed it would be a good place to walk after breakfast."

"Oh, Binks' carnival," you are doing your best to seem completely unconcerned about the arrangement, you didn't want to scoot away and give the impression he was having an effect on you. "That's not a bad place for a stroll. Especially this early on a Sunday, there won't be many people."

The walk around the carnival grounds was relatively uneventful. Neither of you said a whole lot, but it wasn't uncomfortable. At one of the stands you leaned into the whole 'something like a date' concept, and asked him to buy you something to commemorate the day.

He makes a face. "Something from here?"

"Yes indeed Mr. Money-bags-inc." You flash your best teasing grin. "I want you to pick out some hokey cheap carnival gift. The ordeal will make this more of a proper repayment."

"Oh?"

"Well, I can already tell you're not particularly enjoying the idea of it." You grin. You feel like the Cheshire Cat, except with more sass. Sitting down on a nearby bench, you gesture for him to peruse the stalls, your feet kicking back and forth and the shit-eating grin still plastered on your face.

With a sigh, and a smile, he goes over to the stalls. You had to admit watching him walk away was a bit of a treat, he had an ass that didn't just look good in a suit, and it was a good thing you were already seated or you would've been tempted to smack it. You decide to distract yourself by poking at your phone for a little while, so as to not get caught staring.

You kept your eyes on your surroundings regardless and caught sight of someone you hoped would continue to not notice you. The officer appeared off-duty, which was surprising all on its own, you were pretty sure Agent Smoker only had one setting. But it seemed he was doing some volunteer work, as he was completely without any cigars, and surrounded by a small gaggle of children.

Kudos to him for doing the Big Brother thing and looking like an actual human begin while doing so. You notice Tashigi with him, coming back with two more kids following her, and trays of food for everyone. They disappeared off in a direction you were resolved to avoid, at least for today you didn't want to have to deal with either of them.

Not they were bad or treated you unkindly. Smoker wanted you to go into the force as a linguistics analyst or some other equally boring desk job. Tashigi thought you'd make a good agent if the desk job sounded too boring. Both knew who your biological dad was, and who you considered to be your real father. You imagined they were just trying to keep you out of trouble.

Bit late for that, though.

Doflamingo returns after a few long moments and sits down beside you. He holds out his hand, whatever he had decided on apparently fit inside of it.

"My dear," He says, and you weren't sure if he was playing at the role of A Good Date™, or if the 'something like' had started to fall away into actual date territory.

You put your hand out, palm up, expecting him to put it in your hand, when instead he slips a beaded bracelet around your wrist. The material holding it together was stretchy, the beads were small marble sized orbs of polished wood. For carnie fare, it was surprising good quality, and looked quite elegant.

You smile. "Leave it to you to find the highest quality carnival gift I've ever seen."

"I do my best within the situation." He replies with a chuckle, and you feel a heat in your cheeks rise.

Before you even left the carnival grounds you knew those cheap wooden beads were already more important to you than they should've been. It was a shame there was no way they'd go with the evening gown, and you certainly weren't going to risk them swimming.

You head back to the limo, and while you let Lao open the door, you step back and make a dramatic flourish with your arm, bowing. "Age before beauty, Trouble, I insist."

The cheeky action earns you a small chuckle and Doflamingo gets into the limo first. Your win, you imagine, but he sits in the back-side seat again. If you didn't want to sit beside him, you'd have to step over him. This slick bastard.

You decide to turn your win into a draw, and sit down beside him. He already has one arm draped across the back of the seat, and you opt to sit close enough to be under his arm while not right next to him. Between his reach and your height, it wasn't like you were really super near any part of him.

"Now we're headed to your estate?" You prompt, putting a bit of lift on the word estate as though you were teasing him for being rich.

"Mmm," He agrees as he leans into your teasing. "We're headed to my estate, in my limo, driven by my chauffeur, so that my savoir can swim in my pool and relax before dinner." Oh, when he smoothed out his voice and teased you it was better than you had imagined.

"Savior, huh?" You muse, trying to distract yourself from the effect his proximity and tone were having on you. "I wouldn't go that far. If those SUVs hadn't belonged to your family, it would've been a total botch job on my part."

"And yet the end result has been thus." His seems to pout.

You turn toward him a little, looking up and giving him a crooked smile. "You sound irritated by that. Are you angry someone had to step in and help?"

A frown twists his face for a second, before he was back to his usual expression. "Not even slightly. I feel as though you are undervaluing what you did, and that is unacceptable."

"Oh." You lean back into the seat, heat going to your ears. "Well... my apologies, then." Being told to value yourself by an international underworld mob boss was certainly an experience. "So, uh, tell me about your family. If I'm going to meet more important people, I'd rather not do so cold."

"Very well, my dear."

He spent the rest of the car ride telling you about his family. Names and basic descriptions. you'd met Vergo and Diamante before, and briefly interacted with Dellinger, and Lao was driving the limo. When he spoke about his family there was a kindness in his voice you hadn't expected. He very obviously cared about these people, even if they all worked together for often nefarious reasons, and you were absolutely certain he'd burn and salt the world to protect them if that's what it took.

In the twenty or so minutes of the ride you learned about sixteen members of the family, and some of their more particular quirks. Pica had a unique voice, and he was quite sensitive about it. Giolla's taste in art suited her but it was a bit outside what would be considered typical. When he talked about Dellinger you admitted to having praised his heels. That earned you a smile, before he moved on to Senor Pink. This poor man had been through the ringer, and how he coped could be shocking if you weren't prepared for it.

Aside from Baby being needy, the rest of the family seemed fairly normal. Sugar was the youngest, but she was Monet's baby sister and not the only child at the estate either. While you hadn't met Violet, you had spoken with her, and that covered the immediate family for the most part.

When you arrived at the estate, you had to admit that Doflamingo was in a different class from Pops, it was almost twice the land and building size. Which wasn't too surprising, since the immediate Family of Donquixote was quite a few more top officers than Pop had. You imagine the number of subordinates was a number of people that was a real nightmare to keep organized.

There wasn't a chance to go swimming. You saw the pool, and the gardens, and the dinning room, kitchen, living area, work out room, Sugar's playroom, Dellinger's heel collection, half – if not all – of Giolla's favorite art pieces, and were told about the deep history of some of the estate's older heirlooms by Lao. You had been effectively kidnapped by Doflamingo's family. Not even Doflamingo could save you.

Sugar had immediately decided she liked you and was putting random bow clips in your hair while you painted Dellinger's nails after an hour or so of being dragged around the estate. Sure, some of these people were a little quirky, but you couldn't say that your friends were exactly normal either.

"There you are." Doflamingo's voice was full of amusement. You probably look like a reject store front display with enough unmatched barrettes in your hair to make clacking noises if you moved your head too fast.

"Here I am." You reply, not looking up from what you were doing. "I'm almost finished with Dellinger's nails, give me a moment."

"We still have some time to spare, though I apologize there won't be enough time for you to swim before we need to leave." He didn't sound too apologetic, and you imagine it was because you had been effectively claimed by his family.

"(Y/N) can come over again and swim whenever she wants." Sugar declares. "You weren't only going to visit today, were you?"

"If you're only here for today you can't leave to go to some stupid restaurant." Dellinger adds. "You're going to come back, right, right?"

You finish with Dellinger's nails and smile. "I mean, that's kind of your boss's call."

"Young master, you have to let her come back!" Sugar demands, flashing an impressive pair of puppy dog eyes at Doflamingo.

"Young master pleeeeease?" Dellinger begs, drawing out the long word in a childish whine and trying to imitate Sugar's puppy dog eyes.

You get up and walk toward him. "I feel like you're going to be outvoted if you don't acquiesce." You tease, pointing to the clips in your hair. "I've been adorned with highly valued prize items after all, you might have a rebellion on your hands."

"Rebellion!" Sugar says forcefully.

Dellinger turns to her hurriedly. "No rebellion Sugar! Focus on the prize items!"

"Highly prized (y/n)!" Sugar put her fist in the air.

Your face goes beet red at the unexpected qualifier, and Doflamingo licks the bottom of his lip before his face splits into a devious grin.

"Highly prized, indeed." His voice rumbles quietly, but you weren't sure if the others had heard him. "Miss (Y/N) is allowed to return if she wants to," he says, loudly enough for Sugar and Dellinger to hear. "But we cannot force her, she's not a part of the family."

There was an unspoken yet that drove its way into your brain, and you had the distinct impression of being hunted again. You could feel heat in places that weren't just your face and then shoved your children-inappropriate thoughts back down into the corner of your mind before turning toward Sugar – who has turned her puppy dog eyes on you.

"Since I've been invited, I'll come back." You assure her, taking out some of the clips. "So make sure you keep these safe and you can fancy up my hair again next time, okay?"

Sugar nods happily in response and her and Dellinger start chattering about all the things they could do the next time you visited while they help you remove the rest of the clips. In the few minutes it took them to empty your hair of clips you were certain they'd listed off enough events to ensure you'd be visiting several more times.

Leaving the others behind, the two of you walk down the hallway together. Despite the bustle of the estate, you realize that there wasn't anyone else around. You very quickly became very aware of being alone with him.

"There's been a room and bath prepared for you," Doflamingo begins, "so you can relax and clean up at your leisure before dinner. Lao has already put your luggage in the room for you." He stops in front of a door, opening it and allowing you to step through. "If you need anything, the common room is in that direction," he points, "please don't hesitate to ask."

"Ah, um... thank you." You manage, walking by him into the room you found yourself a full bundle of nerves. You kept expecting, or wanting, him to just reach out and do as he pleased, or maybe as you pleased.

"You're welcome, Miss (Y/N). I had been informed by your talented café boss that you do appreciate space and quiet. After the welcome my family unexpectedly bestowed upon you, I believed this would be an acceptable adjustment to the schedule." He didn't draw nearer, or loom, or do anything ungentlemanly, but you still felt the small hairs on your neck stand on end.

You chuckle a bit as you step further in and appreciate the room. It was luxurious, but not ostentatiously so, and the door leading into the private bath was open. There were several bookcases, seating for people who were visiting, and an impressive four poster bed that was separated slightly from the more common area of the room by drapes and an elegant room divider. There was a TV as well, and a computer – not that you were going to log into someone else's family network during your short stay, but the efficiency of items in the room was appreciable.

"I believe I was correct earlier," you muse, turning toward him with a smile. "You really do mitigate all possible risks, don't you?"

He chuckles. "Such mitigation seems hardly effective recently." He admits, his voice slipping from the near-business tone he'd been using most of the day, into something more akin to a purr.

Oh. Oh I was not wrong. Things had gone from business to interest at the café, and there was no mistaking that interest was fast becoming desire. Assuming it hadn't already gotten there before now, and he was just putting on a solid gentlemanly display this entire day.

"Until later, Miss (Y/N), please relax to your heart's content." He bids you farewell and closes the door.

You gulp, alone in the room, and silently wondering if a fling was even an acceptable possibility at this point. If he was as skilled in other activities as he was in well, in whatever all this was, then it might be impossible to just dip a toe in the proverbial pool.

If the vibe was appropriate during dinner, it wouldn't be a bad idea to brooch the topic. Leaving things unresolved wasn't really your style, and if being blunt scared him off easily, then that would resolve things.

And if it didn't, then, well, that was not something entirely undesired.