A/N: Its'a me, CrackedLips, back after 10 years for a brand new Naruto fanfiction. Chaos is how I roll baby!

Itachi x OC. Dabbling in some darker themes, some moral ambiguity, some good ol' off-kilter romance. I have no idea who my audience is anymore so please leave whatever feedback you can.

If you're curious about WHSG, feel free to message me. It's an objectively bad story and I'm planning a rewrite, but there's no timeline for that at the moment.

Rated T for now, but I'm going to crisscross that line like an Olympic figure skater so let's just friggin' see.

Prologue

'And thus Eve's heaven was a field of dead apples, and Adam's hell a full stomach.'

"So… you're a bad guy."

The sallow man said nothing, eyes fixed to the wall behind her head.

Shin threw a glance over her shoulder - a purely paranoid gesture. She had yet to recover from an earlier episode wherein a coworker had released hoards of unsanctioned spider-summons into the breakroom. But no spiders here. Just wall. Dirty old wall coated top to bottom with the nastiest stains institutional neglect could buy.

"I meet a lot of bad guys down here. It's fine, I guess," Shin murmured, a faint drip of water the only soundtrack to her voice. "Once in a while somebody from the bingo book rolls through, that's kind of neat. Like meeting a celebrity but they... want to kill you." She drummed her fingers on the table. The poor guy looked stricken. Hardly a breath had crossed his lips for several minutes.

Shin frowned. She wasn't Ibiki for god's sake - one could look at her without bursting into flames. "You don't have to be so tense, you know. I'm not your interrogator, I'm the intern."

This got his attention. It usually did. Jae-Jin hated when she told them, but that prickly slave-driver wasn't here. And she'd dumped Shin's jasmine tea in the sink yesterday, so Jae-Jin could suck it.

"Intern?"

"Yeah. I'm supposed to observe you for ten minutes. Think of me as your last life-line. You can tell me anything you want now, or you can wait till my mentor drags it out of you. You're my fifth try so far." Her face soured at the memories. "You wouldn't guess, but most people opt for the torture bit."

"I didn't do anything wrong."

"Oh," She said lamely. "How'd you get here, then?"

He shifted and put his hands on the table. They were cuffed, dirty. "I… why do they let interns talk to prisoners? Isn't that dangerous?"

"Well, I am a shinobi." He flinched at the word. She shot him a smile. "And my assignments so far have been low-level offenders, civilian spies, things like that. They won't let me at the big-wigs for a while. So you haven't committed any crimes?"

He did not answer this.

Shin leaned back. "You seem like an okay guy to me. I'd like to believe you. Unfortunately, if you weren't a criminal you wouldn't be here."

He smiled a little. It was surprisingly sweet, and Shin found herself melting only a bit. "That's optimistic of you. Do you trust implicitly that everyone who sits on this side of the table is guilty, and everyone on that side is innocent?" He brought his hands together and twiddled his thumbs, voice never rising above a subdued murmur. "You think there's only one truth and you're the one who knows it?"

She nodded. "Yeah, that's what most of them say."

His twiddling continued. "Who?"

"Bad guys."

He looked up. "You're trying to provoke me."

She shrugged, bobbing her head along to the tick of the clock. Five minutes. "I guess. Sometimes it helps separate normal offenders from the ones who are really dangerous. Nobody here is objectively harmless, it's just… true bad guys don't think they're bad guys. They think they're the heroes."

"Being a criminal isn't the same as being a bad person."

"Not always."

He stopped twiddling. "Yes. Not always."

They stared at each other. Was this progress? Jae-Jin said that so long as someone's breathing there's something to be learned from them. Shin didn't feel like this had gone anywhere useful, but decided to take it at face value. She wasn't going to get results - she was too inexperienced, too directionless for that. Her eyes couldn't read every twitch of muscle like Jae-Jin could. Much as she was loathe to admit it, this was probably the best session with a prisoner Shin had had yet.

Well, the most successful, at least. 'Best' was a strong word.

She reached for the folder in her lap and discreetly read the label at the top. "So... Iraku-san. I've only got about three minutes left in here with you. I hate to rush this since you're the first fully-conscious person I've spoken to in months, but if there's anything you want to tell me I think now's the time to do it."

The man's smile dissolved into something distinctly more bitter, his hands sliding from the table with a clatter. "It was nice meeting you, Shin-san." The expression slipped off his face smoothly, like water off oil. "I appreciate your efforts, but there's nothing more I can give you. Good luck with your studies."

Shin studied him as his eyes unfocused, and she was once more overcome with the feeling that this dirty holding cell had just become another person's deathbed. She wished not for the first time that these idiots would just take the easy way out already. Jae-Jin always said that if you must fail, fail better than you did the first time. Shin didn't know if this counted as that.

Standing with a nod, she glanced at the man one more time before quietly stepping out. The metal hatch locked behind her with a click. She knew that the next time they crossed paths, if she had the pleasure, it would either be in the infirmary or the morgue. It was a shame. He'd been at least… sort of nice.

As she turned to exit the observation room she was met with the unsurprising sight of her mentor Jae-Jin. The older woman was regal even in dim lighting, her sharp features positively predatory above the white surgical gown, a crisp blue folder tucked beneath her arm.

She adjusted her tight black ponytail and gave Shin an irritating pat on the head. "Anything?"

Shin declined to answer. Jae-Jin laughed. "That's what you get for treating an interrogation like a shogi match. I don't know how many times I have to tell you: we value facts over motives in these rooms." She tapped her papers on Shin's shoulder twice. "Well, that's okay. I was looking forward to this one anyway."

Shin looked at the door with a frown on her face. She kind of liked that guy. "Are you sure this merits a grade three? What'd he do?"

Jae-Jin tsk'ed at her for not properly preparing for the job, then licked her finger and flipped open his file. "Looks like the interrogation is just protocol; they want to know if he had accomplices. Guilty of arson, apprehended outside a children's hospital a few kilometers from here. Seven kids dead, fourteen injured." She snapped the folder shut and grinned a pointy grin. "Love your job yet, kiddo?"

Shin looked up at the ceiling, willing any color to stay in her face.

Best job in the world.

Shin Otari's father had not been… thrilled with her prospective career path.

His arguments were limited, however, as it was he who'd carted her off to a private shinobi tutor at the earliest available time slot. It sounded fancy, but it wasn't. Private senseis in border settlements were fairly common - the equivalent of a long, C-class mission for a Konoha jounin, assuring the Leaf was raising adequately ranked ninja in all corners of Fire Country. The Otari's were far too poor to afford anything but charity for Shin's education, and that suited Shin just fine.

For as it turned out, Shin never wanted to be a shinobi. According to a collection of colorful diaries gathering dust beneath her bed, her childhood dreams consisted mostly of becoming a dog painter. It was unclear if this referred to painting pictures of dogs, or painting actual dogs, and young Shin had never felt inclined to elaborate. And if that proved too shaky a future, she'd become a baker. Clientele shouldn't be a problem - everybody had to eat, after all.

But soon into her life as a civilian, the worst occurred.

The Otari family was known in modest circles for their perpetually bad luck. Illness, accidents, and financial crisis after financial crisis hounded them at every turn. At age six Shin's mother suddenly succumbed to a rare bacterial disease found deep in the mountains of Iwagakure – a place she had never been. At the foot of her mother's deathbed, it was decided that the only future for Shin was to become capable enough to survive any insane thing fate threw at her. So the arrangements were made, and a jounin sensei was at their doorstep within the week. She was taken kindly from her childhood home, and received word of her mother's passing two days later.

Shin displayed few talents as a ninja trainee. She was unexceptional in taijutsu, low in chakra reserves and just curious enough to put her on the better end of book-smart. Her affinity for genjutsu developed at a perfectly ordinary age, and was capitalized on by her educators to make up for what she lacked elsewhere. She had a few friends in town, an accomplished notebook of doodles, and no passion for the field whatsoever. She passed her graduation test unnoticed, slipped into the genin ranks with admirable ease, and held no further ambitions to ascend as a Hidden Leaf shinobi.

That is, until she was scouted.

Jae-Jin made for a decent mentor, all things considered. She showed her the ropes where it was needed and took it upon herself to recruit Shin as the first ever intern for Konoha's Eastern Interrogation Outpost. She was a cruel woman with a penchant for violence and public humiliation - but her eccentricities did not make her impractical. After a swift and psychologically damaging initiation, Shin was quickly relayed to paperwork duty. Her other responsibilities included wandering the halls while people screamed, and completing menial tasks whenever a superior caught her on break. Most of those tasks involved cleaning up bloodstains. And vomit.

Yes, she often revisited the rather arbitrary moment she'd agreed to take this job. It was a favorite past time of hers, to imagine slapping that version of herself silly.

The observation assignments began about three weeks into Shin's internship. She'd been undergoing a standard period of isolation, and was naturally thrilled to ditch her dirty bunk in the storage closet and engage with actual human beings. Only they weren't really human beings. They were the antagonists of common society.

However, she wasn't sure she would have made much better company to anyone else. She'd certainly experienced some odd physical changes during her time there, though it hadn't been more than half a year. Her hair had been growing in a darker shade of brown every time she cared to check, and her widely-blown pupils always blinked owlishly back at her. She suspected it had something to do with the lighting around here. She'd also gained some weight since her physical training had been cut down, and began to notice little quirks previously smothered by puberty and physical duress. A dimple on her left cheek she'd never noticed before. A slight click in her elbow, a natural inclination to carry weight in her hips. It didn't bother her really – she'd never liked hand-to-hand combat anyway.

All in all, isolation was an evil she was willing to put up with. After all, no one left this place the same as they were when they came in. They saw blood and heard grown men cry and beg for death and at the end of the day they brushed their teeth and tucked into a peaceful, dreamless sleep. It was awful, sure - but somebody had to do it.

The story doesn't start there, however. The psychological torment which began her time at the outpost was certainly exciting, but preliminary to the day Shin's life really got interesting. It began below ground, in an interrogation room, on just another observation assignment.

A bleak, cold Tuesday morning. She hadn't even had her tea yet.

Shin awoke on the floor, chin submerged in an impressive puddle of drool. She'd fallen off her bed at some point during the night. A nightmare? No – now that she thought about it, she'd done this on purpose. But why? Had there been a bug on her pillow? In her sleep-deprived haze, perhaps Shin couldn't summon the motor capacity to kill it. But why hadn't she taken her blanket with her? Or just used the other cot?

Nevertheless, she was startled into consciousness to the sound of Jae-Jin pounding on the storage-closet door.

"Get your ass out of bed and report to room 708!"

"Wha-" she began, but her mentor's sleek heels were already clacking down the hallway. Jae-Jin never repeated herself.

Already mourning the comfort of her cozy T-shirt and 'Icha Icha This' sweat pants, Shin peeled herself off the ground with a groan. Her bones creaked loudly. The months without training weighed heavily in her soft muscles.

She didn't know where room 708 was. By the time she'd gotten dressed and tamed her hair, she could already feel the weight of impending doom dragging her feet as she trudged towards the questioning rooms. She couldn't be certain that's where Jae-Jin wanted her to go, but it's usually where she ended up these days anyway.

As she turned the corner, Shin was startled to a stop.

The hallway was packed. It was a strange sight in itself, a small crowd of interrogation staff hanging around an observation window. But of all things, they seemed excited. Shin's eyebrows raised of their own accord - seeing a group of anything besides paperwork around here was less likely than the Hokage taking up belly-dancing. She didn't even know this many people worked here.

The dialogue that followed occurred as such:

"Any ID's on them yet?"

"Has Konoha been contacted? They must have records-"

"Looks like it's just some B-ranks causing trouble."

"What did they do?"

"The big one hustled some money out of a poker game. The little one freaks me out though..."

"Missing nin in a town like this?"

"Everybody shut up. Has anyone seen the squirt?"

Shin raised her hand listlessly from behind a tall red-headed girl. "Here, senpai."

Jae-Jin's bony hand shot out from the ether and yanked Shin forcefully to the front, bringing her face-to-face with a one-way mirror into a large holding cell she hadn't seen before. Chakra-resistant locks lined the door on all sides. It was too dark to really make anything out, and her eyes still stung from the rude awakening. She desperately wanted some tea.

"We snatched them up this morning at a motel not far from here. Reports came in yesterday of two foreign shinobi acting shady. The recon team found them loaded with A-class weaponry. We think they have ulterior motives for being in town, especially this close to Konoha. Freaky part is they let us apprehend them without a fight. Are you listening?" she briefed in that clipped, to-the-point way of hers. Shin nodded blearily. "Good. This one says his name is Kaicho. We don't have any files on him yet, so you'll just have to improvise."

Shin nodded again and let the older woman push her toward the chakra-sealed door. It wasn't until her hand was on the doorknob that she finally registered what was happening.

"Wait, improvise what-"

"Good luck, Shin! See you in ten," The crowd offered her a simultaneous, dead-eyed thumbs-up as the door swung open.

She was promptly shoved across the threshold and abandoned with her life.

Shin blinked as a distinct flare of chakra buzzed through the locks, effectively sealing her inside. Did they seriously just strand her with a questionably ranked criminal who clearly outclassed half the people in the facility?

What dicks.

"Hey little one."

Shin turned slowly, only to lay eyes upon the single largest human she'd ever seen. Even in the dark his silhouette was striking. Unnatural, imposing, an impossible mass of sheer muscle. 'Shady' was the understatement of the century; one glance and it was clear this was a ninja of the 'pop your head off and use it as a baseball' variety. No other features were distinguishable in the crappy lighting, which was doubtlessly a result of how rarely this room was used. It wasn't often shinobi of this caliber were detained here – not since the Fourth Shinobi War at least. Any rogue nin above Genin level were sent to more capable facilities in the Hidden Leaf.

Shin sat down cautiously, holding her gaze where she thought the man's face should be. "My name is Shin. I'm here to… uh… just sit here, I guess." She could almost hear Jae-Jin's colorful threats on her life. "They tell me your name is Kaicho. If there's anything you'd like to tell me before the interrogators come in, now's the time to do it."

He leaned forward, the metal groaning under his arms. She resisted the urge to flinch backward in her seat. His size was truly ridiculous. "You mean you aren't my big-bad torturer? And here I was thinking that cute face was some kinda decoy. Catch me off guard, cut my tongue out, rip my fingernails off and all that."

"...Nope."

Jae-Jin always stressed that being a good interrogator necessitated finding your own style. Using your quirks to your advantage. Lying was never Shin's forte, so being straightforward could only help her in the end – or that was the idea, anyway. She was careful to stay distant, never say anything too personal, but she didn't have a strategy either. Her lack of initiative drove Jae-Jin up the wall. Shin tried, but she couldn't fake what wasn't there. Information just didn't hold the same appeal for her as it did for everyone else at the outpost.

She was no interrogator. She had no plan.

The silence grew as Kaicho cracked his neck and Shin leaned back in her chair. A frown pulled at her lips. This was usually how her assignments ended up. She went in, introduced herself, sat for nine minutes in silence (or less, depending on how uncooperative the other party became), then left with few more answers than she'd entered with. Besides maybe a few interesting new swear words. Sometimes she was tempted to just make conversation - ask who the newest celebrities were in the outside world, or what was going on in the fashion scene. Living in this place was like being in a bubble where time just… stopped.

She didn't really expect anything of consequence to come from this guy, especially if he was a higher level ninja than she was. Shin drummed her fingers on the table. If nothing else, there was always the good old ice-breaker.

"So…" She looked up at the man half-heartedly. A chakra waver flickered across his face. Was his hair a shade bluer a moment ago?

"…You're a bad guy, huh?"

He grinned, and the light gleamed off his pointed teeth.

"Sweetheart, you've got no idea."

A/N: I haven't written for an audience in a lot of years so any feedback is good feedback! Did you love it, hate it? Gimme them deets.