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When he was first asked, he wasn't even an official member of the Port Mafia yet.
A blond teen with sunglasses and a sleeveless leather jacket with a fur collar approached him out of nowhere.
“Yo! Name's Albatross, you're the new kid, right?” He'd asked, as though it wasn't already obvious. Mori, who had just been stated as boss of the Port Mafia, was currently too busy to put up with Dazai's annoyingness; he'd allowed Dazai to run rampant and explore the building. The boy in question was currently thinking of aggravating some low-level Mafia grunts into shooting him.
This was one of the few times where Dazai was allowed freedom from Mori's nagging, and he didn't particularly want his precious time to be eaten up by some rambunctious blondie.
“Yes.” He replied curtly.
Albatross grinned like he had just won the lottery, “Well, kid, would you be interested in joining the YoungBloods?”
Dazai raised a brow, “The YoungBloods?” He questioned. Of course, he already knew the Young Bloods, he knew every damn thing that went on in this organization, but this vexatious pleb didn't need to know that.
“Oh, the YoungBloods are basically a peer support group for the Port Mafia's youngest members!” Albatross explained, his voice was unnecessarily loud, matching his loud personality.
“Oh, alright,” Dazai nodded, face blank.
“So do you wanna join?” Albatross asked with a hopeful grin.
“No.”
Albatross stood there for a second, body almost lagging. Dazai took that moment to escape, walking away from him, disappearing before Albatross could snap out of his stupor.
—
The second time he was asked, he still wasn't an official member, but Mori had called him up to his office.
He wrung his knuckle on the door three times, taking Mori's overly cheerful “come in” as his cue to enter. When he pushed open the needlessly big doors, he noticed Mori wasn't the only person in the room.
The man was quite easy to recognize, mostly from his monochrome look. Pianoman turned to face him, a smile latched onto his face. He stood in front of Mori's desk, a bit to the right, expecting someone to stand on his left.
“You called for me, Mori?” Dazai drawled.
Mori twitched at the blatant disrespect Dazai was showing him in front of such a high-ranking member. “Yes, you see, I have a simple question for you.” He paused, Dazai blinked at him before nodding for him to continue, “Would you like to join the YoungBloods?”
Dazai blinked, was this really all Mori wanted to ask? “No,” he replied simply.
Pianoman's smile turned into a small frown as if he was already convinced that Dazai would join their little group. “Why not?” He'd asked, hoping to fix any reasons that the YoungBloods were undesired by the bandaged boy.
“I have no reason to join,” he spoke as if that was fact.
Mori interrupted before Pianoman could reply, “Now now Dazai-kun, I think you should give it more thought.”
He stopped talking, stood up straight, and brought a hand up to his chin to mimic the classic thinking pose. He stood like that for almost a minute.
“No.”
He then promptly left the room.
—
The third time he was asked, he wasn't even in the Port Mafia building! He was sitting at this nice Cafe before someone slid into the seat in front of him.
The handsome man in front of him was, as usual, very recognizable. Lippmann smiled at him kindly, eyes crinkling slightly at the sides in a genuine show of happiness. “You're Dazai Osamu, right?” He asked, voice smooth.
Dazai nodded curtly, already predicting what Lippmann wanted from him. The YoungBloods nagging was starting to annoy him, and usually, he was very patient with annoying things (he had to spend time with Mori almost every day) but he swears if this was another invitation–
“Would you like to join the Flags?” Lippmann smiles, tilting his head slightly. His bangs fell in front of his face and a hand swooped up to tuck them behind his ear.
Now Dazai didn't exactly know what “The Flags” were but he could take a wild guess and say he wouldn't want to join them.
Though, it wouldn't hurt to ask, “What are the Flags?” He asked.
Lippmann smiled kindly, voice light as he explained, “The Flags are the new name of the YoungBloods.”
Dazai had indeed guessed correctly, and answered with his usual “No.”
Lippmann's smile fell into a small frown, looking genuinely hurt by the rejection in a way that made Dazai almost feel bad. “Oh, why not?” The blond-haired man asked.
“I have no reason to,” he replied simply.
“But wouldn't you like to have a group of people you can trust?” He then paused, making sure Dazai was listening, “Friends, even?”
Now that was quite the argument. Dazai himself didn't quite know what it was like to have friends, he was tutored at home so he never went out to meet kids his age. When he was living on the streets, everyone was an enemy so there was no room for friends there either. And in the mafia, he didn't truly like or really know anyone except Mori but he doesn't count.
Maybe it would be better if he had friends….
However, did he want to burden people with his presence more than he already has? One of the reasons he never made an effort to know people was he never wanted to burden anyone with his death. When he ends it all, he wants no connection to the world of the living, and befriending “The Flags” would defeat that purpose.
He looked up at the man in front of him. He had such kind eyes, warm with affection for a boy he didn't truly know. He didn't want someone like him to experience the loss of someone, like Dazai himself has experienced countless times.
“No thank you,” Dazai repeated, despite the slight longing veiled beneath the surface of the black holes he called his eyes. Lippmann's angelic smile dawned his face once again, he nodded in understanding, respecting Dazai's decision before he stood up to leave. A small frown pulled at Dazai's lips as he watched him leave, almost wanting to call out to the man that he changed his mind.
He sat in that cafe for another hour, only ordering a small coffee before he left.
—
The fourth time he was asked, he had just turned 15. He sat in one of the Port Mafia’s clinics, Mori sent him here to check if he’d gained any weight and how the healing from his previous extreme malnutrition was going. Mori would have done it himself if it wasn’t for the fact that he had multiple important meetings back to back for the next week, taking up all his time. Dazai honestly wished that it was Mori who would be poking and prodding him to eat more, he didn’t want some no-name doctor to know what was under his bandages.
He sat in the empty doctor’s office, tensing when he heard the sound of sharp footsteps echoing through the halls accompanied by a slight rolling sound. His eyes trained on the door as the handle turned before being pushed in. Before the doctor even came in, an IV was pushed through the door. A hunched young man walked in behind it, sharp teeth pulled into a tight smile. Hooded grey eyes looked up at Dazai, the man gleaned once he recognized who he was.
“Heh-heh, if it isn’t the one and only Demon Prodigy!” Doc’s scratchy voice rang. Dazai almost flinched at the mention of the new moniker he was given. Doc approached the table at the side, logging into the computer with quick fingers, most likely going off of muscle memory. He almost immediately pulled out a file, squinting his eyes slightly while reading off what was no doubt Dazai’s information. “Fufufufu, Malnutrition?” He said, before rummaging through a draw and pulling out a needle.
He turned back to Dazai, his ever-present creepy smile still on his face, though he most likely didn’t mean to look so horrific at this moment. “A simple blood test should do the trick, Heheheheh, though I’ll also check your blood pressure and weigh you before you go.”
Dazai nodded curtly and Doc rolled his IV beside Dazai, grabbing his right arm and yanking up his sleeve. Dazai winced slightly when he realized Doc was most likely going to ask him to take off the bandages on his arm, though his eyes widened slightly when the man in front of him only slightly nudged one of his bandages aside to see his vein before disinfecting it promptly then sticking the needle in. The syringe was filled quickly, and Doc pulled it out just as quickly, putting a small bandage over the puncture point with a hint of amusement.
He walked back to the table and placed the needle down before turning to Dazai once again. “Could you take off your shirt? Your sleeves won't roll up enough to properly measure your blood pressure.”
Dazai almost wanted to refuse but he knew that wouldn’t go very well for him. He shrugged off the black coat that was perpetually on his shoulders, pulled off his tie, and unbuttoned his dress shirt just enough to pull an arm through. Doc seemingly teleported to his side and wrapped the manometer tightly around his bony arm. The machine squeezed him tightly before stopping, when the machine finally beeped the screen said ‘67’.
The man's creepy smile widened into a full grin, “Fufu, That is concerningly low…” he said, unwrapping the cuff from Dazai's arm. Doc wheeled back over to his desk where he started rapidly typing things in.
Dazai sat there for a full minute, the only sound in the room was the click-clacking of the computer's keys. He felt awkward and out of place, he tried his best to restrain himself from fidgeting slightly but couldn't help it. The silence didn't seem to be stopping anytime soon so he decided to break it himself. “Can I leave now?” He asked almost meekly.
“I still need to weigh you!” Doc creaked, his scratchy voice continuing to grate Dazai's ears. When Doc's skinny little hand grabbed onto Dazai's wrist to pull him towards the scale, he had half a mind to just shoot the doctor. Though as he was dragged towards the scale, he noted how surprisingly gentle. Dazai is unceremoniously left in front of the scale and he got the hint and stepped on the machine. He could feel Doc looming behind him, intently watching the numbers on the screen change until it selected the number 42.
Dazai almost winced at the number, 42kg (93 lbs) was definitely underweight. He knew how annoyingly naggy Mori's going to be when he found this out, and he might let it slip to Randou who would then not stop fussing over Dazai for the next month. It was going to be so hard to kill himself when there were two people constantly checking on you to make you eat.
“Wow! That's only a bit heavier than me!” Doc unnecessarily supplied. “That's actually extremely concerning!” The doctor exclaimed with his ever-present smile still on his face.
“Whatever, can I leave now?” Dazai asked, starting to get irritated with the sickly man.
The man opened his mouth, and Dazai could clearly see he was about to say yes, then he closed it, thought for a second before continuing, “Fufu~ you can leave after I ask you something.”
Dazai almost groaned as he proceeded to ask. “Would you like to–?” and Dazai wanted to bang his head against the wall.
“No, I would not like to join the Flags.” Dazai deadpanned before walking out of the room.
(And as Dazai thought, the next month Dazai was rarely alone. It was just Mori at first, inviting him to have meals together but making sure Dazai had an “acceptable” portion of food. Then when he started getting caught up in meetings, he'd told Randou who almost never left Dazai's side. And while he didn't mind Randou's company, seeing as he's become the closest thing to family (other than Mori) that he's had in a while, It got annoying extremely fast.)
–
Despite Dazai finally becoming an official member of the Port Mafia, there wasn’t a fifth time. Mori had sent him on a wild goose chase trying to find the revived mafia boss which turned out to be Randou’s (They now knew his real name as Arthur Rimbaud) ability. Randou had apparently gained his memories back recently and realized the true power of his ability, and of course, Mori used this new knowledge to make Dazai suffer even more.
During this fruitless first mission he was sent on, he met and recruited the king of the sheep Chuuya Nakahara. Chuuya was the first actual person his age he’d ever talked to longer than a few seconds, and, despite how he’d never admit this out loud, he quite liked Chuuya. Though Chuuya seemed to despise him for being the reason the sheep betrayed him even though Dazai was just doing him a favor.
Since Dazai has officially joined the mafia, Mori has worked him to the bone (not really). He’s been sent on multiple missions ‘just to get a feel of the mafia’, mostly with Randou or Hirotsu, though he’s also been forced to meet and go on missions with a bunch of new people.
For example, right now.
Iceman’s eternal frown greeted him when he looked back at the hitman. Dazai had found out that Iceman was a man of few words, mostly grumbling in response to whatever Dazai said, it was extremely annoying. Iceman himself wasn't that bad to be around, he's been put on missions with much worse.
Iceman interrupted his thoughts by launching to his feet and bringing a shard of glass from the bottle he had just broken to their opponent’s neck. The man was a data broker who was selling information about the Port Mafia's inner workings.
Iceman slit the broker's throat, then he let go and allowed the body to hit the ground. Iceman stepped away from the growing pool of blood, keeping his shoes clean. The grotesque sound of a man choking on his blood echoed through the hallway, the thick carmine liquid that leaked from the wound caused a gory sight that would cause people with even the thickest of skin to look away. Iceman just lit a cigarette and started walking in deeper, Dazai following behind right after.
The two of them were silent throughout their journey to the office. The computer was still on, though signed out. Iceman glanced at Dazai, then jutted his chin towards the computer and Dazai took that as the sign to break into the computer. Dazai slid into the office chair, immediately tugging on the handles of the drawers under the desk. Once realizing they were locked, he turned to Iceman while fishing through his sleeves for his bobby pin.
“Go search the body for something, anything at all,” he commanded, hoping to find something like a wallet that would have information to help figure out the passwords. Iceman grunted in agreement and left the room. Dazai wiggled the Bobby pin into the first drawers. It took around 30 seconds before the soft click of unlocking sounded. He pulled out the drawer slightly so it wouldn't lock again before moving on to the next one. After a few seconds it clicked open as well, he would have continued to the next drawer but there was a combination lock on it.
That was the moment Iceman reentered the room, wallet in hand which he tossed to Dazai. Dazai turned to him, “Could you break this for me?” He asked, gesturing to the lock.
A hammer swung down on the lock, and Dazai genuinely flinched away even though it was not directed at him. The lock shattered and fell to the floor and Iceman sat up into his original stance, dropping the hammer he'd grabbed back to the ground. Dazai looked from the broken lock to the hammer, to Iceman to back to the lock before deciding that this was insane and dug through the drawers. The first two were almost empty apart from snacks, the third though, had a blank notebook which once Dazai opened had lists of passwords inside.
Dazai noticed that a lot of the passwords had a four-digit number at the end and used that to unlock the computer. The files that were sent to clients were written in a code that took him a few seconds to understand before he wrote down the names of those who received the information. He deleted the files before shutting off the computer and standing up.
It took less than 3 minutes.
Iceman whistled in surprise, “You're quite good at this, kid, real smart… you'd do well in torture and interrogation,” Iceman's gruff voice praised. “The Flags don't have a torture specialist yet,”
“I'm not joining the Flags,” Dazai rolled his eyes dismissively and walked through the doorway.
“Wasn't asking you,” Iceman piped from behind him.
—
Chuuya groaned again at the stomping from the party upstairs, mentally cursing Albatross. Dazai, who had broken into his house, looked over at him in amusement. Chuuya rolled his eyes at the half-done mummy and continued to try and beat him in Mario Kart.
Dazai's victorious shout made his ears bleed as he crossed the finish line first. “What the fuck!? Rematch!” He screamed in rage at losing yet again to the brunette. Before Dazai could make his retort, Chuuya's doorbell rang. Chuuya groaned slightly as the room quieted down, the ginger walking in silence to answer the door. There stood Lippmann's kind smile, Pianoman leaning on the wall behind him.
“I'm throwing a party for all the Flags!” Albatross popped up in front of Chuuya, making him jump in surprise. “And you're coming no matter what!” Albatross laughed, before grabbing Chuuya's wrist, “Doc and Iceman are already upstairs!”
“Oi! Wait!” He dug his foot in the ground to stop Albatross from dragging him away. “I have company!”
“Huh?” Albatross commented intelligently, before he, Lippman, and Pianoman nosily looked into Chuuya's apartment. Dazai's head was poking around the corner, sneakily listening to their conversation.
“Oi, shitty Dazai,” Chuuya turned to him with a raised brow. “You coming?”
Dazai looked at him with a raised brow, “did Chuuya's stupid hat make him deaf? He said it was a 'party for the flags’, keywords: for the flags. I am not a flag.”
“Then join, dumbass!” Chuuya retorted as he grabbed Dazai's arm and hauled him out the door and up the stairs to the party.
—