Cherryboy 18

Kakashi was little if not a patient man.

Able to sit still for hours on end as he stalked a target, able to wait for the perfect moment in which to strike. Able to put up with mountains of the bullshit life had put him through. This patience had been the backbone which had upheld him through good times and hard.

His patient nature was all that kept him from bounding up to shake his young crossdressing student.

“So, just to make sure that I’ve heard you clearly.” The bedridden Jonin quirked his masked brow, his single eye staring intently at the skirt wearing boy within whom laid the Nine-Tailed Fox. “You want to go and assassinate Gatou. By yourself.”

The boy looked a bit sheepish, but then stopped and nodded.

“Alone.”

He nodded again, still seeming unsure.

“Without any help or protection from the rest of us and my blessing?”

The boy paused for a moment, then once more nodded, more tight-lipped than Kakashi’d ever seen him before this trip.

“Technically I wouldn’t be strictly alone Sensei. And I don’t want to just sit still until you’re better either.” He spoke, his voice a bit small as he glanced over at his teammates momentarily. “My body can train, but... But I can do way more than just train while we wait. Besides...”

The boy looked over at his team mates, then at the bridge-builder whom he’d seduced just the night before, his face taking on a lightly coloured, sheepish cast as he almost uncharacteristically seemed embarrassed, then steeled himself back into his usual cheerful demeanor.

“Besides...” Naruto continued. “I’m good at this kind of thing. I’m great at henge, every one of my teachers had to admit it. I’m good at blending in where there’s a lot of people too. And I’m extra good at getting into people’s beds. I know what men like sensei.”

Kakashi wasn’t sure he wanted to acknowledge that particular tidbit at the end. It was something that he’d been warned about long before their first official meeting. The whore fox, some of the more mouthy, and stupid, people in the know would talk about him. The genin asset who was unusually easy to lose, and almost always found in some man’s bed. Those Anbu assigned to keep an eye on him had essentially just accepted that they wouldn’t be able cockblock the boy’s night time activities, his skill and creativity in hiding his presence with Henge having become something of a minor legend among the corps. The boy had a certain genius for it, and such rapid, seamless Henge transitions that it was always hard to pick him out against an active crowd unless a sensor type had been assigned to the task.

And keeping those on internal rotation was its own special problem most days.

Which ultimately meant that the boy found himself with free reign to ‘train’ himself in the arts of seduction.

Kakashi half expected that a few of those Anbu had simply been amused enough at the boy’s self-debasement, that they’d allowed the problematic behaviors to fester until he’d become actually proficient in hiding it.

“I’m well aware that you have the skills suited to this particular self-assignment.” Kakashi sighed from his sickbed, shoulders slackening as he turned his head away. “But that is not the real question.”

“What question?” The boy’s eyes crossed as he tried to figure out just what his sensei meant.

It would be Sasuke who whispered the answer. “If you find this man, can you bring yourself to kill him?”

“I…” Naruto started, then seemed almost to fold in on himself, eyes cast down to the floor. Sakura moved closer, placing her hand against his own.

“I don’t know if I can either.” She spoke softly, her voice almost a whisper. “Let’s just wait. Do this together once Kakashi feels better. You don’t have to dive in with the safety nets torn up like this.”

Naruto let his head roll back against his shoulders then released a heavy sigh. “I want to just make everything better, just wave my arms around and make a jutsu to make everything better and make people stop hurting each other when they could be making better use of their time. But I know that isn’t realistic. And I know that even if we wait for Kakashi to get better, one of us might still end up needing to land the killing blow.”

“Yeah.” Sakura smiled sadly, a sick cast overshadowing her lips. “But at least you wouldn’t have to do it alone.”

“And then I’d just feel guilty.” He pleaded, not knowing if it was for or against his own point. His eyes caught Sasuke’s, and held for a moment, before the dark haired boy nodded his own head in agreement. “What if I could end this with only one death? One death neatly delivered, to spare everyone the fight that might get any one of us killed, or force us all to kill.”

From one of the pleats of his dress he produced a Kunai, then spun it about his finger before casually slipping the sharp blade across his own palm.

“There’s a lot I don’t have to worry about.” He closed his eyes, fist folded about the cut palm, blood streaming hot. “But what I do worry about makes my guts bubble and shake, makes my breath quicker and my heart pound. I’m an army alone, all but one of me can always come back if we’re hurt or caught.”

Naruto’s bleeding fist opened, red painting the surface of seemingly untouched skin.

“If I can do this, I’ll get over it and no one else needs to risk getting hurt.” His eyes burned with a determination which Kakashi had long noticed underlaid the boy’s usual bubble-headed act.

Kakashi sighed internally, holding his hand in supplication. “Alright. But clones only. The real you stays back to train with everyone else. Scout, plan, and ask my advice if your clones get information to you. Only strike if you have a proper opportunity, and only at this Gatou. This is an exercise in stealth and infiltration, even if it’s just your clones, take no undue risks.”

“Yes sensei.” Was Naruto’s final reply.

The others simply looked on, worry in their eyes.


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It would take a few hours to get into optimal positions, creating clones with as much Chakra as he had to spare before moving on to another place to create more. Each of them would change appearance, grab clothing and concentrate on slinking into the populace as seamlessly as possible, a skill which Naruto had honed over years of doing just that in order to slip past his guardians and find his ‘dates’ in town.

Slower going here than in the familiar streets of Konoha, though much of the basics which had held true there held true here as well.

Before the end of the night, a small army of infiltrators had been created. Each of different faces, some carried as pieces of equipment to be laid aside and ‘lost’ by others. Some as smaller beasts common to the area, those were the harder forms to keep ironically. Sticking to a regime of stealth would likely only work for this night, while the enemy was hurt and occupied. The cloned multitude slipped in like a knife, staggering arrival and spreading their influence.

Eventually he decided to put a small number of much more obvious clones on watch, seeking out the Ninja enemy.

Afterall, it would be better to present them with a surveillance that they could root out, leading them to the false conclusion of just who was the real target. If nothing else, to force the enemy ninja into a defensive stance with a certain amount of harrying.

At least that was part of the plan as laid out by his bedridden Jonin.

There had been a certain insistence in going over every aspect of what could go wrong before letting him sneak out into the night and cover the distance he needed in order to complete his self-appointed task. According to Kakashi the best hope he had for staying undetected long enough to complete the mission was simply to act as if he were conforming to some of their expectations in a way that would bring them to tighten their personal defenses in expectation of the confrontation to come in the next few days.

Enough that Naruto might be able to aim at his true target while they kept vigilant.

In truth, Kakashi had told him, it was an iffy bet. Afterall Zabuza was no slouch in infiltration and assassination, having glanced the blonde youth’s ability even in the passing chaos of the battle may have been enough to tip him off as to potential moves you might make towards ending either his own life, or the life of the one to whom he was currently contracted. The fact however was that much like himself Zabuza was critically injured and likely bed stricken until the next few days were up.

This would likely be an operation where the twin chunin and that hunter nin who’d assisted in the powerful silent killer’s escape were the ones on guard. What would otherwise be effectively zero chance became greater thanks to Naruto’s numbers and insane chakra reserves, putting him on the offensive side. The twins were strong ambush hunters. Creatures who thrived on surprise and disorientation to take down their prey. But the Hunter was at best an unknown quality.

Naruto would find himself being forced to think harder about his assassination scheme as he allowed his clones to scout the area. He himself keeping to clever shapes and placement to get into position to learn more.

It only took half of the day for those clones who’d slipped in first to have managed to listen in on conversations involving the man named Gatou, it seemed that he had his own small contingent of lower skilled bodyguards, two sword specialists with limited chakra training and no ninja background.

A little more flirting in the night revealed where the man slept, and his main holdings where he usually worked during the day. As well as the process which he was currently going through to apparently hire lower class fighters as a group of mercenaries for his purposes.

A little more coaxing revealed where much of the powerful merchant mogul’s current liquid assets were also likely kept.

The particular clone who’d gotten that info had decided that its mark had earned an extra nice blowjob for that particular tidbit and nearly had burst itself from the extra effort of going all out.

In the mean while the three practiced, sometimes together, sometimes apart. Pushing themselves in preparation…

And so night began to stretch over the second day.

Time was running thin.

Naruto needed to strike… he needed a plan.