The main protagonists including Lady Tsunade, the Leaf Village, and the Naruto universe are property of Masashi Kishimoto everything else is fictional.

please enjoy the story.

Day 1: Predator Meets Prey

Naruto Uzumaki raced down the hall and swung open the door. Inside was Lady Tsunade at her desk with her arms crossed and she raised her left eyebrow. Also inside were Kakashi, Kiba, Neji, and Sakura.

"You're late Naruto. I sent a message to you about ten minutes ago telling you to be here early." Said Tsunade.

"Yeah sorry about that I got caught in doing some training that I forgot about the message about being here early." Replied Naruto smiling and letting out a bit of a chuckle.

"This isn't a laughing matter Naruto. This is a serious matter. We have a mission to get on that's extremely dangerous." said Kakashi in a grave voice looking at Naruto with a critical look on his face.

Naruto gulped and walked in and closed the door behind him and got in line with the rest of the group. Kakashi looked at Tsunade and nodded and Tsunade cleared her throat and spoke.

"Your mission today is to protect a very dangerous man who escaped from a prison faraway from here in another village. They're making him his own prison just for him because of how malicious he is. The man you will be protecting is none other than Heartless." Finished Tsunade.

Everyone except Kakashi and Naruto gasped. Kakashi just closed his eyes and let out a sigh while Naruto just looked at everyone with a puzzled look on his face. Finally Naruto raised his hand and Tsunade raised an eyebrow.

"Yes Naruto." Said Tsunade Calmly.

"Who's Heartless?" Asked Naruto. Everyone except Kakashi and Tsunade looked at Naruto with surprised looks on their faces.

"He's ten times worse than the Akatsuki or any other criminal in the world. He's a sociopath that looks pleasant and nice to talk to but is completely bad. He got the nickname Heartless because he removes the hearts of his victims." Replied Kiba in a disgusted voice.

"That's sick but how was he captured here? Did someone recognize his face and then arrest him?" Asked Naruto.

"Well Naruto as confused this may make you he actually turned himself in this morning at the gate. No one knows why he did it but the fact is that he's apprehended now and we need you all to escort him to the docks where a ship will take him to his new personal prison that's underwater." Replied Tsunade.

"Wow an underwater prison. I never would have thought someone could think of such a good idea for a sick freak such as him." Said Sakura in a fascinated voice.

"All small time villages that have been affected by him decided to work together and build one but the man escaped before they could move him but the point is that we have him now and need you all to move him but there are some rules we need to go over with this kind of prisoner." Said Tsunade.

"What are the rules?" Asked Neji in a cool voice.

"Rule 1: Never let him out of your sight. Rule 2: Don't speak to him. Now that's all that I have to say for rules otherwise good luck and be on guard because there may be bounty hunters on the look out for him trying to collect for some reward by another village that still thinks he's on the run. Dismissed." Finished Tsunade and one by one everyone walked out and exited Tsunade's office.

"I hope everything goes well for them because this scumbag is sure one weird little psychopath but if everything does go right then everyone can sleep well at night not having to think of that bastard is on the loose trying to get more killing in. Why he does is it I don't think anyone will ever figure that out but I'm sure that this will all be over." Said Tsunade taking a sip of tea and returned to some papers that needed to be looked at and signed.

The group walked down the street and towards the gate. Everyone saw a young looking man who looked to be in his twenties with a steel collar around his neck that had a chain attached to it and steel manacles around his wrists and ankles. He wore a black t-shirt and blue pants with no shocks or shoes. He had by the looks of it a brown backpack on his back. When the gang arrived they looked at his body better. He had a decent amount of meat on his body so he looked that he would way one hundred and twenty pounds and stand five eleven. He had a small nose and black facial hair that looked to have been just shaved. His black hair was short and had blue eyes. He smiled at the group.

"How do you do there? You must be my escorts. The name's Dashi Noki or as others would call me Heartless." Said the man.

Kakashi walked up to the two black ops that were keeping an eye on him and spoke to them.

"So he's been quietly waiting for us?" Asked Kakashi.

"A little too quiet. Why would Lady Tsunade ask a bunch of youngsters to take on such a dangerous mission? They do know how sick he is right?" Said one of the Black Ops.

"These kids have been through some very tough challenges. I'm sure that tsunade is making the right choice." Replied Kakashi.

"Well the big thing that you guys need to worry about is not only the prisoner or bounty hunters but also your sanity. This guy will try to get into your heads so be careful." Said the other Black Ops.

"Don't worry we can handle it from here." Replied Kakashi in a confident voice.

"Well still be careful." Said the first Black Ops and the two Black Ops disappeared in a puff of smoke.

"Well let's get going don't want to be late for the prison they have for me." Said Heartless in a happy voice and he turned around and Kiba grabbed the chain for the collar and the group headed off to the Heartless's prison that was many miles away from home.

The setup for watching Heartless is setup like this: Kiba behind Heartless holding the chain for the collar, Kakashi behind Kiba, Neji in front of Heartless, Naruto on the right side of Heartless and Sakura on the left side. The group walked through the forest no one said a word and there was complete silence until Heartless opened his mouth and spoke.

"So, you guys are ninja's that must be a cool profession but let me tell you my job is lot more harder because you can get in a whole bunch of trouble." Said Heartless out loud to his escorts letting out a laugh but no one responded Heartless turned and looked at Naruto and smilied.

"So you're Naruto Uzumaki a.k.a the number one knuckle head ninja or as I would call you a freak of nature." Said Heartless in a calm but crazed voice.

Naruto ignored his comment and the group continued walking but Heartless smiled at Naruto and kept up his talk about him.

"I heard you have the legendary demon fox in you. I'm surprised that they didn't lock you up for fear of it trying to possess you but then again I wouldn't have been able to meet such a fascinating creature of the world such as you. Still I wonder what it would be like to take a blade and slit you open and study you're personality from another medical perspective." Continued Heartless.

Still Naruto did nothing until Heartless said something to make him snap.

"Of course though you're pal Sasuke or as I'd call him a dirty traitor that deserves to be hanged just like me. I'd consider him to be up to my state since I've heard about the fact that he went over to the dark side. No offense Naruto if I found him I'd dissect him and take his brain and I'd give it to you so he'd always be with you. Just think about it part of the squad once again…Get it 'part of the squad'." Finished Heartless and he let out a malicious laugh that sent shivers down everyone's backs except Naruto's and Kakashi's.

Naruto grabbed Heartless by the neck and everyone stopped and looked at what was going on.

"Shut your mouth you sick little Freak." Said Naruto to Heartless.

Hatred for this guy in Naruto's system was at an all time high. Oh how bad Naruto wanted to beat him up but he felt a hand on his shoulder and heard a voice speak to him.

"Naruto let him go it's not worth it. He's just trying to get into your head and you've already just broken one of the rules that the hokage gave us. Let me be beside this monster while you get behind Kiba." Said Kakashi in a calm voice.

Heartless let out a low chuckle and smiled.

"Can you tell me Naruto how a man with half a brain is smarter than a man with a full one?" Asked Heartless.

"Whatever sick game you're playing I'm not going to bite so lay off." Said Naruto in an angry voice.

There was a crash of thunder and soon it began to rain. Naruto let go of Heartless and got behind Kiba while Kakashi looked up at the gray sky with the rain that was coming from it and looked at everyone.

"Let's take a break and setup for the night since this shower looks to be a while. No sense on getting sick for this mission since it is a vital one." Said Kakashi and the team members nodded and the group walked deeper into the forest and stopped at a good clearing and began to setup for camp for the night.

Each team member would take turns watching the sociopath.

The time was Midnight and it was Naruto's take since he was the last one to watch Heartless now who sleeped on the ground on his back. Naruto watched Heartless and Heartless opened his eyes and stretched and looked around and saw Naruto he smiled and spoke.

"Sorry for upsetting you Naruto my fullest apologize." Said Heartless with a smile on his face.

Naruto snorted and Heartless raised an eyebrow.

"What? You don't believe I'm sorry?" Asked Heartless.

Naruto just stared at him with hatred and disgust for who he was looking at.

Heartless smiled and let out a Chuckle.

"Come on my dear boy say something." Said Heartless.

"You are a sick and messed up person. You have no feelings for anyone but yourself. I'll be glad when they put you away for good." Said Naruto in a serious voice with a hint of anger mixed in it.

Heartless smiled for he noticed the hint of anger and decided to take advantage of it.

Naruto watched as Heartless crossed his legs and then did a full stretch forward and recoil and smiled.

"You know who my first victim was? It was my teacher. I liked him and all but it drove me insane that when I got in trouble as a kid he whipped me with a belt. Oh how I remember the pain from the whipping. I didn't like getting in trouble because to be honest others got me into it. I was the good boy but I hated him for punishing the wrong kid. So when I went to visit him as my first victim I decided to take a wooden stake and stab him when he wasn't looking. What a mess I made but for all the blood lost I guess it counts as the number of years I had to endure the memories of everything that happened to me. Then one by one I secretly killed the one's who got me in trouble. So many bodies so many different ways of killing an asshole." Replied Heartless chuckling at the end of his sentence.

"So then I'm right you are a person who has no feeling for others." Retorted Naruto in a voice of disgust.

"They started the war and that's how I lost feeling for others. Sometimes you have to lose feeling to gain something new and thrilling inside. Well I'm off back to bed so goodnight Naruto." Finished Heartless.

Heartless fell back down and closed his eyes while Naruto just stared at the monster in front of him.

"The man that existed inside him long ago is long gone a monster is all he is. He should have been killed instead of us transporting him to a prison he doesn't deserve. What the hell is wrong with this picture?" Said Naruto quietly to himself.

Naruto let out a groan now frustrated with what was going through his head. This man acting as if he's so cool and intelligent and that this was some sort of fun game. Naruto looked up at the dark sky and saw that the sun was beginning to rise.

"Hopefully we get rid of this guy so I can get back home to our village and forget I ever heard of this man. He deserves his just desserts. Well even though I really want to terminate this guy it's best to try and ignore his words. " Finished Naruto letting out a yawn and looked back at Heartless who laid on the ground smiling an odd smile on his face.

Morning was coming and the adventure of escorting this mad man would continue but what awaited them on the road ahead was soon to be discovered by our fellow team and the prisoner known as Heartless a killer of fifty people and the most wanted man in the lands.