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Becoming Isekai Villains in Japan (Dual SI)

Hellkaiser_76514
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Synopsis
Long Ago In a distant land. A soul had found himself isekai'd into a new world as The Shogun of Sorrow already ruling Japan and enslaved it's citizens to mine it's resources. Until a foolish samurai warrior welding a magic sword had stepped forth to oppose him but before the final blow was struck. The soul had tore open a portal through time and flung himself into the future Only to find himself in a very different world than the one he left behind. [Let's fast forward a bit here to a 1000s of years later] Another soul had made their way into the body of Oroku Saki better known as The Shredder and with his ever loyal foot clan by his side What is a man to do with all the power of The Shredder? Deal with the Turtles who are just teenagers Bah! that be a waste of resources No he'd rather claim some woman here in Japan and get more power to further his goal of just gaining a harem of bottom heavy women (Mostly) Either Way, These 2 forces of Evil will shake this world's Japan to the core. XXX (AN: for those who didn't read the tags this is a self insert of myself and my friend from discord. Don't like self inserts then don't read)
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Chapter 1 - Avoiding Death

[Japan, 1725]

Aku was known all throughout Japan as a vile demon or evil Incarnate. He was the one who (presumably) killed the emperor's son when he first started his attack upon their land.

Of course as any army would do they tried everything they could to harm the demon.

They shot arrows at him. He simply absorbed them into his body and shot them out faster than any man hoped to draw.

They shot catapults at him. A minor annoyance.

Their best efforts simply weren't enough to even scratch Aku.

He enslaved every man, woman and child regardless of age and put them to work in mines in order to obtain the riches deep beneath the earth. He created minions to keep a watch on them cause of course they rebelled sometimes but eventually like a horse they broke and simply did what Aku asked in order to avoid more pain.

The one who was most abused was the emperor who was often the punching bag of Aku's vile demons. All the while Aku laughed at the emperor's pain and broadcasted it to all his slaves.

Currently he is in his castle waiting for his demise to come and scared from Him

You see folks you aren't dealing with the average Saiyan warrior anymore- oops wrong script.

This wasn't the original Aku who had first conquered Japan but instead it was a person who had watched all this happen before since in his world this was a fictional series known as Samurai Jack.

In which Aku (Aka the new soul) had flung the samurai into the future and thought he'd gotten rid of him in order for his future self to deal with... for about 10 seconds and he got killed with the help of his own time traveling daughter.

Now Aku was stressed out since he didn't know what to do, was he destined to die by the samurai's hands? was it a canon event that couldn't be stopped and dragged everyone down with him.

Ok maybe he wasn't a saint whether as Aku or his previous life but he wasn't a monster like the original Aku. He didn't know how to feel about the enslavement of children to work in his mines.

Of course he set the children and elderly free and had been taken care of by his demonic minions. Of course no one batted an eye at this.

He made the excuse of them being "Too young/old to work for the great Aku" or something like that.

He was scared beyond belief since he'd been trying to track Jack as soon as he found himself in this body and realized he wasn't dreaming.

Oh he found Jack.... and he was on his way here! 

His hope of approaching the Samurai in hopes of being spared from the blade and leave Japan in peace. He knew it wouldn't work Jack was like John wick and wouldn't want anything but his demise but delusional hope had won out against the facts for him.

What could he do?

"AKUUUUU!" The voice of his destroyer was here but he didn't want to come out of his hole. He would have to come to him all the way down where he was. 

Could you blame him? He was scared.

Wait a minute scared? being scared is the result of fear and fear is a result of the mind? Hurt the Samurai mentally.

Aku smirked a wicked smile 

He emerged from his endless chasm and towered over Jack but they both kept their composure.

"Who dares summons The Master of Masters, The Deliverer of Darkness, The Shogun of Sorrow!?"

Aku stared down his doom and didn't know what to do? Perhaps fire breath?

"I am the lost son of the land you have pillaged-" He was interrupted by a blast of fire erupting from Aku's mouth

The samurai dodged out of the way. Aku then tried used his laser vision to kill him but the Samurai used his sword to block the laser which his sword seemed to nullify.

Aku looked shocked then enraged as he thought of what to do next.

The samurai took a swipe at Aku at his lower body which left a scratch and it burned.

Being cut by the sword was painful and how he could describe it was a paper cut being cut more while lemon juice was being squeezed into said cut.

"Agggh" Aku screamed out as he transformed his arm into a spike to impale it but the samurai was able to Parry it and then cut off his hand.

"Aggghhh damn it that hurts!" Aku screamed out in pain again. He needed to break the samurai but how.

He duplicated a human sized version of himself all the way from the bottom of his feet? legs? his lower half and it started to climb up the chasm fast but made sure to do it quietly as well as to not let the samurai's keen sense expose himself.

As for the main body Aku, he let out a sonic screech towards the samurai knocking him back as he transformed into a ape-like creature to try to squish him. The samurai ever-persistent while even being knocked on the floor rolled away Aku's fists attempt to crush him.

"Foolish samurai you truly believe you can defeat me!" It was fun to yell as Aku and it helped him with the stress of this battle.

The samurai said nothing as he charged towards Aku and slashed him hurting him once more.

Aku enraged had transformed into an octopus and used it's many tentacles to try to restrain him but each tentacle was being cut off causing more pain to Aku. He needed the samurai distracted so he could do this!

He had transformed again this time turning into a eastern dragon.

"You cannot defeat me fool! Surrender and become my right hand and I promise to be a bit merciful with your people" Aku knew he would refuse but he needed him to start talking to be distracted.

"No never you vile demon! I am on the side of righteousness! and I will defeat you!" Aku let out a bellowing laugh and then stopped.

He looked at the samurai and wondered if he should show him the worst thing that Japan did at least in his opinion which was The Nanjing Massacre to try and crush his spirit. No that wouldn't do since it would probably bolden his desire to destroy Aku.

Aku put a wall of earth up beneath the samurai to launch the samurai up as his human sized clone now transformed into deer with sharp antlers to impale him.

The samurai was momentarily distorted as he was launched and saw that another Aku was about to impale him.

He slashed the Aku clone in twain killing that clone of him. What he didn't see was Aku's hand from below and up intending to capture him in his claws. Which Aku was able to do and firmly grasp him.

He started to squeeze but his fingers had been cut and the samurai was out and had started to run up his arm.

Aku roared in pained didn't notice the samurai running up his arm but luckily he noticed in time as Aku tried to use his laser vision to fry the samurai but it mostly missed due to the samurai's speed and his sword absorbing his laser.

That's when Aku decided to slam his entire arm next to a wall to squish the samurai but didn't work since he was already so close to him as the samurai jumped and slashed at Aku's eyes causing him even more pain.

"Ahhhhhh curse you samurai!" the samurai wasn't done as he tightened his grip on his sword as stabbed into Aku's chest and started to fall with his sword acting as a grapple as he slid down Aku's body.

Aku's body started to become undone a lot as he was being sliced and being absorbed by the sword 

The samurai had jumped off as Aku began to be absorbed by the sword.

The samurai had struck the sword down in order to release Aku upon the floor.

"Ughghhhh so much pain" 

Aku saw the samurai about to strike him down for good. Couple of ideas had gone through his head.

Send Jack to the future? Hard No he'll still comeback and kill him anyways 

Send him to the sun or the end of time? No that sounds way too easy and cliche, sue him he likes a challenge.

Wait a moment, the future that's it!

Not to be rude but he didn't care for this land since it didn't have what a guy from his century would want. He wanted his technology again since he's missed that and sure he had magic to create what he wished but he didn't time to use it since Jack was already at his doorstep.

Aku coughed in pain before he tore open a portal in time to the future and shapeshifted into a smaller form as he rushed into the portal to avoid the samurai's strike.

 The samurai was confused as he wasn't sure what Aku did but it seemed for now that Aku had retreated? All he knew is that Aku wasn't here but he wasn't dead by his blade. 

But Aku was gone for now, he didn't know whether or not he would come back but it would be best to inform his father about this defeat?

No he wouldn't call this a defeat until Aku was dead and he didn't care how long it took, he would find Aku and strike him down or if not him then he would train students in order to hunt him down and all his wicked kin.

But for now he would head back home and prepare for the return of Aku.