A/N: Random idea that's been bugging me for a long while that finally decided to straighten itself out to be written.

Sorry for inconsistent updating, my Muses are being pretty damn lazy. -_-

Posted this on Tumblr first to check public reaction, so thanks to kichchan on Tumblr for telling me to post this asap because they thought it was amazing, YOU'RE AMAZING.

Warnings: Warnings for prostitution, Prostitution of a Minor, canon-typical violence, Jaded!Naruto, maybe triggers, Time Skips, and other things.

Dark Themed

Law of the Shinobi

Death is a Shinobi's most faithful companion,

Secrets are a Shinobi's lifeblood,

And Trust is a Shinobi's most precious possession.

OoOoO

It was raining.

It always was, whenever the Orphanage Caretakers kicked him out for the night. Didn't want the Demon taking up the space where other, normal orphans could be keeping warm and dry, after all.

Demon.

One day, he'd show them that he wasn't a Demon, a Monster. He was Uzumaki Naruto, and one day, he'd be happy and they would be sad.

Dattebayo.

"Oh my, what have we here?" A woman's voice said, and Naruto turned, blonde, spiky hair falling into his face, shadowing his bright blue eyes as he observed the beautiful woman standing in front of him. She had long black hair that was pinned back in an elegant bun by two expensive-looking black sticks that were tipped in red jewels. She was dressed in a red-and-yellow kimono that was long, but open at the top, exposing her large bosom and the lacy underclothes that held her breasts, barely. She was holding a decorative umbrella and her dark eyes were looking at Naruto from her smooth face, brightly painted lips pursed slightly in thought. Suddenly, her eyes were half-lidded and she was smiling coyly, leaning down towards the five-year-old and offering her soft, pale hand, the nails long and painted red, with tiny yellow flowers painted on.

"How would you like to stay somewhere dry, sweetheart?" She asked, coy smile still in place, and, to Naruto, she looked like an angel sent by Kami himself. Blue eyes wide and startled, he stared at her for a long moment, before hesitantly lifting nervously trembling fingers to cautiously grasp the woman's long digits.

"I'd like that, Neesan," he whispered shyly; she smiled a little wider, just a hint of bright, white teeth beyond blood-colored lips as she gently pulled him under her umbrella, and began to lead him away from the orphanage and deeper into the Redlight District.

"My name is Akemi," she told him airily as they walked. "But you, sweet one, can call me Kaasan."

OoOoO

Naruto wrinkled his nose as Himiwari-Neesan finished adjusting his bright green overalls, his blue shirt underneath smelling clean and faintly of perfume as the off-duty prostitute fussed about him. It was his first day at the Academy, a whole year earlier than everyone else his age, and she wanted him to be as made-up as possible, despite not being from a Clan or higher Civilian family.

"Don't pout, Naru-chan," Sorami-Neesan scolded gently from a few feet away, where she was just getting back from her work, smelling heavily of musk and cigarettes and strangers, carefully washing off her make-up in the only mirror the room had. Naruto immediately shot her a sweet smile, face abruptly a mask of cherubic bliss, and she laughed even as Himiwari-Neesan poked him in the nose with an amused smile.

"A little less teeth, un-squint your eyes a bit," she advised; he immediately obeyed, and his face gentled into a happy, almost-shy-looking visage. "Much better, Naru-chan," the prostitute cooed, kissing his whisker-marked cheek affectionately. "We'll have an actor out of you, yet!"

"Or a Yakuza," Oki-Neesan remarked dryly from where she lounged naked on the bed, watching the proceedings with faint amusement. Himiwari-Neesan just huffed at her, flicking her hand at the other woman with a dismissive air.

"You ready to go, Naru-chan?" she asked instead; the six-year-old immediately dropped his smiling mask, returning to the calm, slightly-frowning face that could usually be found there when he had to do something he found mildly unpleasant, or when he was thinking.

"I guess," he admitted reluctantly, and accepted his special Froggy backpack from Sorami-Neesan, kissing her on the cheek, before padding over to do the same to Oki-Neesan, and finally returning to Himiwari-Neesan and taking her hand. The white-haired prostitute smiled down at the sweet boy their boss had adopted, and gently led him down the hall and out the backdoor, having to pause several times as the other girls (and two men) wished him good day, gave him advise, and offered cheek-kisses for luck. Finally, they were on their way, and Naruto was soon at the Academy, reluctantly letting go of Himiwari-Neesan's hand as she crouched, turning him to face her, pink eyes affectionate and loving as she absently wiped a smudge of lipstick from his temple.

"Remember," she said gently, placing her unadorned hands on his small shoulders. "Don't show too many teeth, when you lie your eyes squint shut, use the proper kanji when spelling your name or everyone will think your name is Fishcake instead of Maelstrom. Don't be afraid to stand up for yourself, but don't make a fool of yourself either. If one of the Sensei's doesn't teach you like the other kids, Akemi-sama and the rest of us will teach you that subject. Don't let anyone talk down to you, but put on a good face when dealing with them. If there's one thing these Shinobi understand, it's restraint and self-control. Revenge is best thought out, planned with prejudice, and implemented when you have a rock-solid alibi." She kissed the blond boy on the shoulder and hugged him close. "Make us proud, Otouto," she murmured, kissing his head again before gently releasing him. "Nishiko will pick you up after Academy, you have a bento in your bag. Now, go on, or you'll be late," she shooed him, and Naruto turned, his smiling mask in place, and trotted into the Academy with a few other children, blending in with the brighter colors and pastels of their clothes, disappearing into the crowd. Himiwari sighed happily, before she left, heading back to The Butterfly Palace. Her shift didn't start for another two hours, and she wanted to nap for a bit, if Oki hadn't stolen the entire bed, that is.

OoOoO

"Try again," Fuyuki told Naruto, his deep voice patient as the almost-seven-year-old practiced throwing Kunai at a board propped up in the alley behind the Palace. The crudely drawn target on it was dotted with splintered holes as the young boy continued to work on his aim, the Genin helping him with what he could remember from his own Academy days, before his Team and Sensei were murdered on mission that had been mislabeled. Instead of joining a new Team, he remained a technical Genin, despite being nearly thirty now, usually doing the higher-paying D-Ranks or substituting on C-Ranks.

"You're still twisting your body too hard, Naruto-kun," the older man said, gently readjusting the boy's grip again. "Remember, smooth and sleek, not rough and rude." Naruto bit back a frustrated noise.

"Hai, Fuyuki-sempai," he replied instead, and went back to work.

OoOoO

"Kaasan, why do you and the Neesan's and the Nissan's do what you do with all those men and women?" Naruto asked on one of the rare occasions Akemi was with him, the two of them cuddling on a futon, the beautiful woman mostly naked as she dragged her long, decorated fingernails through his sunflower-colored locks. She paused for a minute, and then smiled slyly, curling her arm around the little boy until he was nuzzled right between her impressive breasts.

"Do you know what Shinobi do, Naruto?" she asked gently. "What their purpose is?" The seven-year-old frowned slightly.

"Shinobi protect Konoha from invasion, they take missions to better the Village, and they…gather information on other Villages…?" He trailed off questioningly and Akemi smiled gently.

"Very good," she crooned, stroking his face as he smiled sweetly up at her, curiosity and trust shining in his pretty blue eyes. "But do you now how they do all that?" Naruto hesitated; forehead crinkling and smiling lips transforming into a pursed pout as he thought.

"…Jutsu?" He asked; Akemi continued to smile and pet him gently even as she shook her head a bit.

"In certain ways, yes," she told him. "But they also do all that and more, by being cunning and crafty and ruthless. They kill to protect this Village and their Mission. They torture and seduce to get the information on other Villages. They are our pet monsters, our soldiers. To be a Shinobi is to be equally loved and vilified in any Village, some lean more towards one side of the spectrum or the other, but it is the same." Naruto had his eyes locked on hers, hanging on her every word.

"Whores can be the best sort of Shinobi," she told him, sly smile still curling her lush, red-painted lips. "We can seduce our clients into telling us their darkest secret, we can go into places even Shinobi have difficulty, under the guise of being hired. We can even be brutal assassins, if the price is right." Gently, she pressed a blood-colored kiss to his forehead, still smiling that secretive smile. "Secrets are everywhere. Everyone has one and, sometimes, the best way to get them is to let a strange man or woman fondle you and fuck you, or you them. It is worth it in the end, little one." Naruto was wide-eyed with wonder and fascination as she again kissed him. The woman settled down more onto her back, pulling Naruto up to rest between her barred breasts, body laying over her naked stomach and legs straddling her barely-clothed hips. She hummed softly as she stroked a hand down his back, still smiling faintly, eyes closed.

"…Kaasan?" Naruto whispered after several minutes of silence; Akemi hummed to show she heard. "…Will you teach me?" Slowly, she opened her dark eyes and looked down, where Naruto shyly and hopefully peeked up at her from her cleavage; her smile became something dark.

"Of course, Naruto," she replied, leaning her head back and closing her eyes, smile sharp and satisfied. "After all, it's what mothers do."

OoOoO

A poof of smoke, and suddenly a buxom brunet was standing provocatively in front of them, dark blue eyes smoky and half-lidded, plump mouth curved into a come-hither smile. A blue kimono was curling around her curvaceous body, gaping open and showing a large amount of cleavage and stopping only a few inches down her thighs, exposing long, lean legs, smooth and tapering into a pair of small, delicate ankles and feet that were nestled into a pair of blue slippers. A hand slid up her neck, small, thin fingers tipped in dark blue nails as that hand teasingly slipped over her mouth, as if covering her smile coyly.

"Excellent work, Naru-chan!" Himiwari-Neesan praised as she and a handful of other prostitutes looked over the eight-year-olds solid transformation, so much stronger and more potent than the Academy standard Henge, because this literally transformed the user into whatever they were mimicking. Naruto, in the form of what they had been calling "Maiha", gave a soft chuckle and straightened up, dragging her nimble fingers lightly down her body and licking her lips softly.

"It feels nice," he murmured in a soft, husky alto; Himiwari smiled gently at him and stroked one of his whisker-less cheeks affectionately.

"It's perfect," she told him gently. "Akemi-sama will be pleased," she added; making dark blue eyes light up with happiness. "Akimitsu and Hama have both agreed to be the two to teach you tonight, Maiha-chan," the albino continued; and Naruto/Maiha took a deep breath and straightened her shoulders, nodding.

"Lead the way, Himiwari-Neesan," she murmured and the prostitute took her hand and led her to the private room, where the two male prostitutes would teach her everything they could about their profession, in every position and situation they could.

OoOoO

"You Fail!" The instructor shouted, dark glee in his eyes as nine-year-old Naruto failed the Genin Exam; frowning, Naruto slipped out of the room to sit with his classmates. He ignored the jeers graduating students sent him, knowing a majority of them would be right back in the classroom three weeks from now. Unlike them, he was in the know-how, and knew that every Jounin Instructor gave his or her Team a secondary Genin test, to assess their skills in different ways. Team Work, Tracking, Information Gathering, Strategy, and several other topics were spread out, each Team testing in something different in an attempt to get as many decent Shinobi as they could. Sixty-six percent of the graduating class would fail, a depressing number really, but it was normal. Naruto frowned down at his hands as he waited for the bell.

Why couldn't he do that damn Bunshin?

As soon as the bell rang, he was out the door and away from the Academy. When he was absolutely positive he was out of sight, he Transformed into Akina, one of his several different forms, and started leisurely down the road towards The Palace. In this form, he was a tall, lanky green-haired woman with a mole on the left corner of her left eye, those eyes a deep copper color. Today, he wore a pale green Kimono with a yellow obi and gold outlines of leaves swirling around the bottom edges. As she walked down the street, she caught many male gazes and flirted through smiles and hungry looks, sashaying seductively towards the Red Light district. Just before she reached it, a man approached, one of her regulars, Kimihiro Kioshi, a middle-aged merchant who had a wife and three children, a gambling problem, and a bit of an exhibition kink. His favorite food was calamari, he hated mornings, his youngest daughter was joining the Academy in two years, and he didn't have a problem tipping his whores generously if they showed him an extra good time.

"Akina-chan," he greeted with a leer, gray eyes already locked on her breasts, and Akina let her expression morph into a pleased, hungry smile.

"Kioshi-sama," she purred, and curled her arm through his when he offered, gently steering him towards and alley and placing her mouth right at his ear, lips teasingly brushing against it. "How may I please you today?" She purred; he groaned and, once they were safely in the alley, twisted around to pin her against the stone, pressing his groin, and his erection, against her own pelvis and grinding.

"Right here, right now," he growled, already panting slightly in excitement. "How much?" She made a show of fluttering her eyes and tipping her head back, lips parting slightly in "pleasure".

"For you? Three thousand Ryo," she moaned, and he gave a pleased sound, yanking one of her legs up and around his waist, fumbling for the front of his pants.

"Done," he panted eagerly; she nodded and, after a few minutes more of fumbling, he was pressing into her and thrusting. Akina gasped and moaned and curled her legs around him, curling his fingers into the crevices of the bricks, putting on a bit of a show as he pounded into her. Unlike a majority of her clients, in her many different forms, Kioshi wasn't a selfish lover and, by the time he finally came, he had made her come apart three times. After they had both caught their breath, he set her feet back on the ground, and Akina made a point of slipping to her knees and personally cleaning him to show her appreciation. Since that led to more action, when she finally left the alley, Akina had ten thousand ryo in her pocket and a satisfied smirk on her lips. When she reached The Palace, she slipped its entirety into her money-slot, where it would be divided between her, Akemi, and the establishment (as well as a small fee to the local Yakuza for protection).

"Did you pass?" Oki asked nonchalantly as she lounged on a cushion in the Girls Room, where the Neesan's relaxed and awaited a customer.

"Damn thing was rigged," Akina told her with a wrinkle of her nose; Oki spat to the side and sneered, pulling out a cigarette and lighting it up.

"Figures," she grunted and blew a smoke ring, passing one to Akina without a pause. The green-haired prostitute huffed in bitter agreement, lighting up her own cigarette and awaiting her next customer.

It was going to be a long night.

OoOoO

Naruto couldn't help but feel very, very lucky that Akemi-Kaasan had been the one to take him in. Very few shops could turn in away, no matter what form he was wearing. To turn away or overcharge one of Akemi-Kaasan's girls (or her adopted son) was asking to be Black Listed throughout the Red District until you either made amends or were a member of the Yakuza. This meant no one in any of the brothels would play with you or use your shop, and you wouldn't be allowed in any of the gambling houses that were allied with them, which meant you'd be stuck with the lower-end ones where you were more likely to get stabbed and cheated than win anything.

As a result, instead of the orange monstrosity that the clothes-shop would have sold the eleven-year-old Naruto, he was able to get himself some dark gray Shinobi pants, a smoky-gray loose-long-sleeved shirt, and a charcoal vest, which contained decent pockets, while the pants had huge pockets as well. He got black Shinobi boots, and a very dark brown bandanna to hide his hair. Bandages pinned the ends of his pant-legs and sleeves down and hid several packets of emergency items (Blood, Chakra, Soldier, and Caffeine Pills, cauterizing powder, wound-stitching string and needles, and a few generalized antidotes to common poisons and Paralyzers). He got decent Kunai, Shurikan, and Senbon, as well as plenty of Tag papers with Chakra-ink and paintbrush. He had a few Storage Scrolls and plenty of ration bars as well, and all for a decent price.

Later, after he did a few shifts as Maiha and Akina and Washi (one of his few male prostitute forms, a small, teenage-looking redhead with large orange eyes and a dusting of freckles, surprisingly popular with the older men and women), he showed off his new Shinobi gear to his adoptive family, getting many compliments and appreciative catcalls. Akemi smiled and kissed his forehead and told him he looked just like a true Shinobi would, and he couldn't help but swell up with pride before happily stripping off and climbing into the bed he shared with one or more of his Neesans (tonight it was Sorami and Momoko, both of whom were completely naked as well, and who simply curled around him like overly-affectionate squid.).

He had his second Genin Exam in a few days, and didn't want to fail again.

OoOoO

It was rare for a customer to request him by name, but still, it occasionally happened.

"Kiko~" Oki called as she sauntered into the Girls Room; the purple-haired, teenage-looking prostitute looked up, gray eyes curious. "You've a reservation!" Kiko blinked and then smiled at the man who strolled in arrogantly after Oki, leering at her before turning his dark eyes to Kiko.

"Mizuki-sama!" she greeted the assistant Academy instructor with a shy, sweet smile even as she inwardly sneered. Naruto hated the silver-haired bastard, with his fake-kind smiles and sugary sweet encouragement even as he taught Naruto purposefully wrong Taijutsu and marked off his homework as failures when some of the answers were even better than Sasuke's or Kiba's. The Chunin looked up and down her rather childish outfit, made to make her look even younger and more innocent appearing, his leer darkening and edging with a cruelty.

"Come on, Kiko-chan," he purred, offering a hand and the purple-haired prostitute made a show of blushing and shyly taking it, even though she immediately wanted nothing more than to yank it away and wipe it on something to get rid of the slimy feel it gave her. "Let's go play a game, hmm?" And Kiko giggled and followed him into a private room, where he immediately yanked her to the bed, bent her over it, and pulled her dress up, exposing her panty-clad bottom. He caressed it and shushed her when she started to ask him what he wanted to play, before he slowly pulled her panties down, and then proceeded to viciously spank her until she was sobbing and whimpering and deeply bruised.

Only then did he pull back, panting heavily as he ripped at his pants until his cock was free, and forcefully slammed it into her small pussy, chuckling breathlessly at her pained scream, and proceeded to brutally fuck her in several different positions for several hours. Later, as he slammed so deep into her throat that she choked repeatedly, he groaned and huskily mocked her with cruel word, telling her how he wished she were one of his students so he could fuck her on the desk, and maybe he would shove Uzumaki's homework into her cunt and fuck her with it there.

"Maybe I'll do that after I fail him tomorrow," he hissed, tightening his hands viciously into her hair, as he slammed harder, listening to her choke gleefully. "Maybe, maybe I'll do that as I wait for the stupid little shit steals the Scroll for me, before I kill him. Maybe I'll just have to reserve you for that, hmm, cunt? What do you think of that?" He snarled, before forcing her all the way down to the base of his cock, groaning as she choked and gagged and struggled weakly as he came down her throat, eventually letting her up as he slouched backwards onto the bed, smirking as she choked and coughed, gasping for air as her blotchy face slowly returned to normal coloring. He used her hair to pull her up onto the bed with him, and manhandled her over his body, head pinned to his shoulder as he used his other hand to rub his cock against the crease of her ass slowly.

As he started to get hard once again, Naruto silently vowed to get him killed tomorrow, and use his plan against him to the best of his ability.

OoOoO

"You are the Kyuubi no Yoko!" Mizuki shouted, cackling as Iruka shouted in anger.

"Oh, that?" Naruto asked, making a show of cleaning out an ear boredly with his pinky, ignoring the stunned looks that were shot at him. "I learned that years ago, Mizuki-baka. You're a bit late…" He blinked, and then looked up, face sliding into a mocking, foxes smile. "By the way, the ANBU have been here the entire time." As he said this, four black-clad, animal-masked Shinobi appeared, surrounding Mizuki and swiftly capturing him. In a swirl of leaves, the Hokage appeared next to Naruto, countenance severe as the twelve-year-old handed him the scroll without hesitation, foxy smile remaining.

"Well done, Naruto-kun," the old man said seriously, dark eyes watching as his ANBU took the traitor away to be dealt with by Ibiki. "I think, for collecting such information and assisting the ANBU is capturing a traitor, you should be rewarded. Don't you agree, Iruka-kun?" He turned a small smile to the gobsmacked Chunin, who sputtered but quickly agreed, face slowly morphing into a proud look as he pulled off his own headband, and kneeling to tie it around Naruto's head himself.

"I want you to know, that I don't think of you as the fox," the Chunin told him seriously. "At first, I hated you, and sure, you're annoying, you skip classes, you curse too much in class, you make crude comments, and you smoke, but you're not the fox, and you're kind to people. I just wanted you to know that, and that I think of you as more of a little brother than a student, okay?" Naruto took a soft, hitching breath, blue eyes made even brighter with tears, before nodding and hesitantly hugging the instructor, careful of his wounds. Iruka smiled and hugged him back, and the Hokage smiled from where he watched proudly nearby.

"Now, let's go get some ramen, huh? My treat."

"Dattebayo!"

OoOoO

"Tell me about yourselves," Kakashi-sensei told them while they sat on the roof.

"Nani?" Sakura asked; Sasuke and Naruto just stared at the Jounin, eyes twitching slightly.

"You know," the Jounin said simply. "Your likes, dislikes, hobbies, dreams for the future, things like that."

"Why don't you go first, Sensei," Sakura suggested. "So we can have an example!" Kakashi hummed, barely even looking up from his smut book.

"My name's Hatake Kakashi, I like some things and dislike others. My hobbies? …Well, you're too young to hear about those yet, and I don't really have dreams." He smiled at them and Sakura's eye twitched with her teammates. "Your turn, Pinky!" The girl blinked.

"Er, my name is Haruno Sakura, I like…(giggles and glances at Sasuke). I hate Naruto!" She snarled and Naruto rolled his eyes and pointedly pulled out his cigarettes, lighting one up just to rile her further, blue eyes amused. "My hobbies are reading and (giggles and once more glances at Sasuke). And my dreams… (another giggle and Sasuke-glance)." Naruto snorted and Kakashi pointed his book at him.

"You're turn, Smokestack," he ordered; Naruto sarcastically salutes.

"Uzumaki Naruto, call me either, I don't care," he replied easily, and blew a smoke-ring. "I like to smoke but won't on missions, I like to mess with people, and play the occasional prank. I dislike stalkers, bigots, and generally rude people. My hobbies are collecting secrets, and my dream is to rise through the ranks of Shinobi and perhaps one day become Hokage." He flicked his ash and arched a brow at Kakashi.

"Baka, how would you collect secrets?" Sakura sneered; Naruto rolled his eyes.

"Are you a Shinobi or not?" He asked bluntly and sneered faintly back at her before the expression disappeared, leaving behind only his usual calm, and placidly smiling mien.

"You next, Broody," Kakashi announced before a fight could break out.

"Uchiha Sasuke," the boy responded, face blank. "I like to train. I dislike fangirls and idiots. My hobbies are training. My dream… No, my ambition is to kill a certain man." The roof was silent as everyone stared at him, Kakashi's eye twitching, Sakura with the standard "He's so Cool!" expression, and Naruto looking unamused, eyebrow arched.

"…You do know that 'dream' and 'ambition' are synonyms, right?" he deadpanned; Kakashi sighed as Sakura began screeching at the blond, who did nothing but stick a finger in his ear and wiggle it with a bored expression while Sasuke just looked irritated and slightly embarrassed.

"Shut up already," Naruto sighed, giving the pink-haired girl an irritated look. "I don't know why you're bitching about anything, since we're not even a Genin Team yet."

"BAKA, of course we're a Team!" she snapped; Naruto snorted.

"Not until we pass Kakashi-sensei's test," he told her with a small sneer. "Only thirty-three percent of any graduating class passes their Jounin test to become real Genin. The Academy Graduation Exam is made to show who has potential and who needs to return for another year. It's a Jounin Sensei's job to test if we're ready to be a Team." Sakura gaped, and then whipped her head up to stare at Kakashi, something Sasuke did as well. The Jounin was eying Naruto with interest.

"Maa, maa, it's true," he said, before his eye slid half-shut. "It's also supposed to be confidential. Tell me, Naruto-chan, how did you find out about it?" Naruto gave a small shrug and smiled sweetly.

"I told you, my hobby is collecting secrets," he told the Jounin; who stared a few moments longer, before his eye closed in a happy look.

"A good hobby for any Shinobi," he said easily. "Now, tomorrow morning at, say, eight o'clock, we'll meet up at Training Ground Seven for the test. Don't eat anything unless you want to throw it up! Buh-bye~" He chirruped, before he disappeared in a swirl of leaves. Naruto sighed and stood, stretching, before leaving, Sasuke and Sakura ahead of him, with the Pinkette asking the broody Uchiha if he wanted to eat dinner with her.

Naruto's mind had already turned away from them, however, and instead sifted through all the information he had gained over the years about Hatake Kakashi and his Jounin test…

Maybe a little honey would attract the right flies…

OoOoO

A/N: Was originally going to be a One-Shot, but turned into something else (Shrug) reviews are always welcome!