AN: To avoid confusion, I want to be clear that the first sequence in this chapter takes place a few weeks after Naruto figured out what his novel was going to be about (At about the same time when the Akatsuki scene from the last chapter took place). This chapter jumps around a tad, but I think it's necessary to fit everything together in an understandable way.

Please leave reviews (even if they're negative) so I know what you guys like and don't like about the story so far. Thanks!

And the Winner is...

"Hey, Naruto! I'm going out to do some research, wanna come?"

Jiraiya heard a loud 'poof' and shortly after, Naruto walked into the room. He was nursing his cheek with an annoyed look on his face. "Why would I want to go out perving with you, Pervy Sage?" He asked harshly.

His mentor noticed what looked like a bruise forming on his right cheek. He frowned. "What happened to you?" He asked with slight confusion.

Naruto just grumbled angrily about a clone 'calling him ugly.' Then after a few punches were thrown it was every Naruto for themselves. "It really makes no sense!" His outburst was slightly amusing to the older man. "He looks exactly like me!"

Jiraiya let out a sigh. "As much as I'd like to talk with you about your issues, there are beautiful women out there that I need to stare at." He thought about what he just said for a moment. "That didn't sound right…"

"Sounds right to me, because that's all you do." Came the young voice of his apprentice.

"Nuh-uh." His master shot back with a child-like tone. "I take notes!"

Naruto had no response to that. All he could do was put his face in his hands and wonder what it would be like to be trained by Orochimaru instead. 'Maybe it wouldn't be so bad.' He mused.

"You know, kid." Began Jiraiya, causing the boy to remove himself from his disturbing thoughts and look up at him. "You're gonna have to throw in the towel soon on this little bet of ours." His words caused the blond's face to scrunch up in annoyance. "While I really do enjoy watching you lose, we do need to get started on your training pretty soon. It has been a few weeks already and I haven't seen you make any progress on your book, at all. Honestly, I'm a little disappointed."

Naruto opened his mouth to retort, but he was swiftly cut off by his mentor.

"I understand that you really want to go after your friend, but a deal is a deal. I'm still going to train you, of course. I'll just stick to the training regimen I initially had in mind, but Sasuke is now gonna be off limits. Understand?" His tone was firm, yet not overly harsh. He had to be careful with how he phrased things, his student had a tendency to let emotions dictate his actions and the things that he says.

Naruto waited a short moment to ensure that his teacher had said all that he needed to say. Much to the surprise of the white-haired jonin, the blond was very calm and collected. He almost seemed like a different person.

"There are a few things I want to ask." He stated simply, to which the older man nodded his agreeance. "First, what is the difference between your original training regimen, and the one we were going to do had I won the bet?" His tone remained even, again, surprising the more experienced ninja.

'Something doesn't feel right.' He thought to himself. He shook off that feeling and began to answer his student's question.

"This bet was a test of your mental fortitude. Had you gone out of your comfort zone and written a book, something you have absolutely no business doing with your writing skills, it would have proved to me that your mind could handle incredibly strenuous training." He began, still watching the boy's unchanging reaction to his words. Instead of pressing the blond about his unusual behavior, he continued. "Unfortunately, now I'm not sure if you can handle it. I don't want to give you something that you aren't ready to take on. Something like that can cause lasting damage to the psyche of someone as young as you." Jiraiya paused, believing he said something that could possibly irritate the blond. "And that's not to say our training won't be intense! Rest assured, it'll still be the most difficult thing you've ever done in your life! We're just gonna take precautions, is all. Okay?" He clarified.

Jiraiya knew that he had stacked the deck against his disciple. It almost didn't seem fair and he felt a tad guilty about. However, Naruto needed to prove just how determined he was. He couldn't risk permanently harming his godson like that. He shuddered to think what Kushina would do to him when they met in the afterlife.

Had Naruto and his clones not just read a dictionary over the past few weeks, Naruto would have only understood about half of what the toad sage had said to him. He nodded slowly, affirming that he understood what his master had said.

"There was another thing I wanted to ask you." He began, continuing on as if he didn't hear a word the Sannin said to him.

Jiraiya's eyes narrowed. Now he was positive something weird was going on. Normally, the Naruto he knew would have interrupted him at least three times during that speech he just gave. "Okay, what is it?" He asked suspiciously. He glanced behind himself, making sure there wasn't another frying-pan-wielding Naruto ready to smack him.

"How can you say I've run out of time? You still aren't done with the research you have to do for your book. You were supposed to be done with your peeping about a week ago, but you aren't."

Jiraiya blushed slightly, embarrassed that he was being called out for his hypocrisy. "Well, you see, I've finished the majority of it!" He began, trying not to let the opinion his student has of him furtherly worsen. "We'll start our training tomorrow, I'll just have to do some research intermittently."

Naruto huffed. To him, it just sounded like more training where Jiraiya shows him how to do something once and then leaves the blond to his own devices while he goes around town and pervs the day away. That was not something he wanted to go through again. Not with the Akatsuki threatening to make their move in just a short couple of years. "You can take your half-assed training, and intermittent perv sessions, and stick them up your ass!" He crossed his arms across his chest in a defiant manner. "I'll have you know that there's no need for you to worry about training me and doing your research at the same time."

The sage couldn't help but hear the pride that was welling up in the voice of his student. If he wasn't interested in what was going on before, he sure was now. "Oh, and why's that?" He asked with genuine intrigue.

Naruto opened his mouth to respond but was cut off by a knock at the door.

"That's odd." The older man said to himself. "Wonder who that is?" He opened the door and was met with a face he did not expect.

"What are you doing here?" He asked dumbly.

-One Week Earlier-

A handful of Naruto's scratched their heads in unison, their gazes resting on a rather large stack of papers. "Is that it?" One of them asked. "Are we done?" Another clone spoke with hope evident in his voice.

There was a short pause as the blonds looked to one another for confirmation.

"No!" One of the Naruto's broke the silence that had fallen over the group and shot up to his feet. "Have you read the ending? It blows!" He shouted. The angry Naruto grabbed the offending page from the stack and pointed a finger accusingly at the words written on it.

The original blond swiped the page away from his doppelganger, a sneer forming at his lips. "What do you mean? What's wrong with it?" He asked defensively.

"It's so unrealistic!" Another blurted out. The rest of the group grumbled their agreement, much to the displeasure of the real genin.

His eye twitched in annoyance. It would have been bad enough if someone else critiqued his work rudely, but he had to deal with five versions of himself telling him that his hard work sucked. "What's unrealistic about it?" He didn't know whether to be angry or hurt. After all, if his own clones thought this, did he in some way think it too? He glanced at his clones. 'I've noticed that some of my clones have thoughts that I don't normally have. But how is that possible? They're me?' His interest was piqued, but he would have to come back to that thought another time.

"The guy never gets the girl in the end in real life!" A third one blurted out, unaware of the real one's musings. "Don't you remember what we learned? It's so cliché!" The clone was referring to the books they had read that were so beneficial in developing the blonds writing abilities. The other Naruto's immediately nodded their head in unison at that statement.

Their minds drifted to Sakura, their pink-haired crush. They all hung their heads in dejection. Naruto definitely knew that heroic acts don't always get you the girl from experience.

"Yeah, you're right…" They all sighed loudly. "Guess we should come up with a new ending. Any ideas?" All of the energy that was once present in the group had been sucked dry. The blond did not like to think about his chances with his pink-haired friend. Actually, it would be more accurate to say his lack of chance with Sakura.

He got ripped out of his thoughts as one of his clones tapped him on the shoulder.

"What about this?" The clone asked. He handed the original a few sheets of paper. "I actually wrote this earlier while you were so focused on trying to complete your love story." He teased himself lightly. "Tell me what you think."

Naruto was unsure at first. This clone looked a lot like the one who said the plot should revolve around ramen. 'Wait, what the hell am I talking about? We're all identical.' He frowned at his own stupidity.

He began slowly reading over the several pages that were handed to him. The blond scanned every word thoroughly. His expectations were very high. After all, he technically wrote this material himself. As he continued to read the clones work, he recalled a segment from one of the books that he had read. 'While the ending does not mean everything to a story, a well-constructed ending is perhaps an author's most useful tool to convey the message he/she is trying to tell. In essence, it is the backbone of what the author is writing about.' The blond kept that in the back of his mind while he continued to read. What message did he want to convey? He was unsure.

Page by page, every word he read caused his excitement to increase. This was exactly what he was looking for! He was sure of it. "This is it." His voice was low almost a whisper. So low, in fact, that one of the clones asked him to repeat himself. He finished reading. "This is it!" He was much louder this time, words overflowing with enthusiasm. He looked at the clones with pride in his eyes. "I love me." There was a tear forming in one of his eyes.

The clone responsible for the work puffed his chest out and allowed himself a cocky grin.

"We did it, boys!" They all cheered loudly in victory. "While I would love to celebrate with all of you guys, I have some work to do before the old perv gets home."

The clones nodded back in understanding. "See ya later, chief." One of them said as they dispersed into clouds of smoke.

Without wasting any time, Naruto darted across the room to where Jiraiya's stuff was. Without regards for his master's privacy, he began swiftly rifling through the old man's personal belongings. "C'mon. Where is it?" He muttered to himself as he continued to look.

After looking through everything his master had left behind in the hotel, he still could not find what he was looking for. "All I need to know is the publisher's name and address." He continued to speak as if his clones were still there with him. "Pervy Sage has to have that information stashed somewhere."

What almost felt inevitable, his eyes slowly fell on the book that was resting on the table. The book that Jiraiya had left him had remained there for over a week, untouched. The mere sight of the book made the blond uncomfortable. He shuddered. 'Anything but that. It's gotta be somewhere else!' The attempted reassurance did little to dissuade the apprehension that was building up inside him.

After a few more minutes of fruitless searching, he resigned himself to defeat. The genin slowly reached for the horrifying piece of literature. He took a deep breath, preparing his innocent mind for whatever his eyes may read.

He flipped the book open and started scanning the first couple of pages. His face quickly turned a deep shade of red. He had accidentally read a part of the first chapter. 'Who the hell reads this stuff?' His mind shifted to his other teacher, Kakashi. The blond sighed audibly. He had two insanely powerful mentor's, yet both were interested in this kind of material. At that very moment, Naruto did not know if he was lucky or cursed.

"There it is!" After a moment more of searching, he finally found it. "Land of Fire Publishing Company." His finger traced along with the words as he read them off the page. "The address is here, too! This is great!"

Once he was done copying down all the information he needed, he put the book right where it belonged. In the garbage. Naruto chuckled to himself. "A trashy novel, indeed." If his clones had heard him say that he would have definitely lost cool points.

-Present Day-

Naruto, interest piqued by his master's reaction, glanced over to the doorway. Standing there was a man in some of the most unusual clothing that the blond had ever seen, and this was coming from a person whose attire consisted of mostly bright orange.

The man was dressed in a grayish, almost green uniform along with a hat consisting of the same bland color. He wore dark goggles and had a bag strapped to the side of his body. From what Naruto could see the satchel contained a few small packages but mostly held what he assumed were letters. 'That's the weirdest looking mailman I've ever seen.' He thought to himself.

"596-03, at your service!" The man said enthusiastically. Naruto glanced up at his hat. Those very numbers were stitched into red cloth right below its bill. "I have a package for one, Naruto Uzumaki." The mail carrier seemed completely oblivious to the white-haired man's utter confusion.

"Who's this guy?" Naruto asked suspiciously. The man spoke in an odd, almost robotic, way. Yet, at the same time, he was enthusiastic. This odd behavior perturbed the young child.

"This is 596-03, and he says he has a package for you?" Hoping his apprentice would have an answer that would alleviate his current state of confusion. Initially, he was uneasy opening the door fearing it would be Anbu Black Ops members recruiting him for an emergency mission. Now he was just out of the loop.

"596-03?" Naruto repeated, dumbly, as he took his mail from the strange man. "That's not a name. That's just a bunch of numbers."

"That's right." The number man confirmed. "I am a courier ninja. Each courier ninja is designated their own set of numbers as a sort of identification marker. It is an important way to organize our operations.

The genin continued to eye the man up and down. "So, what are you? Like a postman or something?"

"Not exactly. Normal postmen don't risk their lives on a daily basis." Despite how robotic the man's voice was, he sounded very proud when he spoke about his work.

"Oh… so you're like an amazing postman!"

Jiraiya sighed. Sometimes his student's denseness was unprecedented. "Just shut up and let the guy deliver the rest of his mail, Naruto." The Sannin thanked the man and closed the door as the courier ninja took off for his next assignment.

"So…" Jiraiya crept over Naruto's shoulder. "What'cha got there?" He couldn't quite understand why someone would send Naruto anything, and how that person would know that they would even be here.

Naruto allowed himself a small smile. He was so curious about the amazing postman, that it had not even occurred to him what his mail could even be. Once his intrigue had worn off, he began putting the pieces together. There was a very strong chance that the outcome of their bet was located in his hands at that very moment. This was about to get interesting.

"Nothing you would be interested in, Pervy Sage." The youth said vaguely. He shifted his shoulder, effectively blocking his teacher from seeing what was written on the package's exterior. The nosey sage was trying to spoil the surprise and his pupil was not having it.

In fact, just to get on Jiraiya's nerves his used his body to completely block the older man's view.

This only furthered Jiraiya's welling curiosity.

Naruto opened the large manila envelope and quickly read its contents. It was a letter addressed to him from Jiraiya's publishing company. His smirk grew large and larger as he continued reading.

"Naruto!" Came the frustrated shout of his nosey master. "Lemme see!" Jiraiya was practically bouncing up and down. How he hated being out of the loop! As a specialist in infiltration and spy tactics, his whole job was to be in the loop, being out of it was infuriating.

"Read it and weep, Pervy Sage." The blond said as he held out the letter for his teacher to take.

Jiraiya quickly snatched it and began to read. He immediately recognized the header that this letter came from. It was the publishing company that published his masterpiece 'Icha-Icha' series. The gears slowly began to turn in his head. This was not good.

"Y-You…" He finally sputtered out. He rubbed his eyes and continued reading hoping that it was just his sight playing tricks on him, but the words on the pages didn't change. He had lost the bet. Naruto, the kid that can barely write his own name, was now going to be a published author.

"I what, Pervy Sage?" There was an immense smile plastered on the boy's face. "What were you gonna say just now?" He asked cockily.

While it was certainly fun to rub his victory in the face of his sensei, Naruto felt something that he hasn't felt since he completed the Rasengan and won the necklace from Tsunade. The blond had put everything he had into proving the sage wrong. He felt as though all of his hard work paid off. But there was a different feeling. It wasn't just about winning, it was about creating something that he was proud of. Something completely his own. Mastering the Rasengan was great, yes, but he wasn't the one who invented the technique. He created Menma and his story, and it was good enough to get recognized by a major publisher. This was a crowning achievement in his life.

"…" Jiraiya felt as though something was caught in his throat. "You won…" He finally said as his head dropped in defeat. "I can't believe you actually did it!" He continued with his head still down. "All without me knowing!"

"Yeah, I'm awesome!" Naruto stuck a finger to his chest proudly as he spoke. "Oh, and I also used your name as a reference, so they would take me seriously." The blond grinned sheepishly. "But I'm still awesome!"

Jiraiya sighed. He really did not see this coming. It had taken him over a year to write a piece of literature that was good enough to get published, and yet his pupil had done it in a matter of weeks! It was inconceivable. 'I hate my publisher.' He thought to himself bitterly. Jiraiya was convinced that it was somehow their fault.

"I have to say, Naruto, you exceeded my expectations. I asked a lot of you, and you proved me wrong." While the sage was certainly bitter about losing to his student, he also felt a great amount of pride for the young blond. "I'm proud of you." He finished with a genuine smile.

Naruto blinked. The orphaned genin was definitely taken aback by those words. Growing up without parents, or really any parental role models always left him yearning for the acceptance of the adults around him. To Jiraiya, those words were a simple congratulatory statement, but to Naruto, they meant so much more. For an instant, he could almost feel what it was like to have a father. As inappropriate as his mentor was sometimes, Jiraiya was the closest thing the boy had to a father. And he wouldn't trade him for anyone else in the world. "T-Thanks…" Was all the boy could muster out.

Jiraiya scratched the back of his head and sighed. "Like I was bragging about before, a deal is a deal. Although, instead it's gonna be me on the losing end." He chuckled. "Since it's getting late, we won't start training today. Training will begin first thing in the morning. Make sure you're ready." Was all Jiraiya said as he walked towards the door.

"Wait a minute." The blond began. "You're not going to still go out and do research, are you?" He asked, an annoyed tone to his voice.

"No." The white-haired jonin answered simply. "I gave you my word. Had I won, I would have forced you to stop chasing after Sasuke. The least I can do is honor my part, as well. Don't worry, from now on training is going to be our one and only focus." The genin could tell that his words were sincere.

"Then where are you going?" He was confused. 99.9% of the time Jiraiya went out it was to conduct research. Did he even do anything else besides eat, sleep, and perv? The blond did not know the answer, but he would probably put his money on no.

"I have to write up the training regimen that we are going to use for you. I was so sure that I was going to win that I didn't actually write anything down." He grinned sheepishly. "Looks like I'm not gonna be able to get much sleep tonight."

"Couldn't you just write that here?" The boy asked.

"Trust me, you don't want me here to keep you up." There was a dangerous glint that appeared in the Sannin's eyes. "Also, I don't want you getting nosey and spoiling the surprises I come up with."

Naruto gulped audibly.

"You're going to need every second of sleep you can possibly get." Jiraiya may have been incredibly proud of what his student achieved, but he was still a competitive guy. He was upset that he lost. However, he thought it would be a good idea to take all of those negative emotions and throw them on top of his pupil. Naruto would certainly get what he wanted. The boy was about to get the most intense training of his life.

"W-Why are you looking at me like that?" A now pale-faced Naruto stuttered out as he backed away slightly.

All he got in response was a sadistic grin by his sensei. He didn't like that.

Without uttering another word Jiraiya left the hotel room, his once sadistic smile now just a menacing grin. 'This is gonna be fun.' He mused. 'Well, it'll be fun for me.' He let out a laugh that reverberated against the walls of the hotel floor.

Naruto, now by himself once again, had a lot of things he needed to process. Most importantly, he was finally going to get the training he deserved. As terrified as Jiraiya made him about the prospect of their upcoming training, he also felt excitement. As he proved when he won the bet between him and the sage, and even his bet with Tsunade, he always rises to challenges put in front of him. This would be no different.

Then there was Sasuke. Had he lost, he would have to give up his pursuit to save his best friend from the grasp of that snake Orochimaru. Naruto loved training and getting stronger, but Sasuke was perhaps his biggest motivator for winning the bet. The fact he would be able to keep the promise that he made to Sakura was incredibly relieving. 'I'll save you, Sasuke. Don't worry one bit!' He thought to himself passionately.

The blond glanced over at the clock. It read 6:00 PM. As if on cue his stomach growled. "Guess I should eat dinner and then get ready for bed." He said aloud to himself. Based on how his master was talking the blond figured he was gonna get woken up much earlier than the 9:00 AM time that Jiraiya usually made him get up at. And if the training was going to be as difficult as the Sannin eluded to, the extra sleep would serve the genin well.

Naruto opened the cabinets in the kitchen and frowned. There was no ramen. How could Jiraiya expect him to train all day tomorrow without his premium fuel for dinner? This was already going terribly! After ensuring that the cabinets were empty his attention turned to the fridge. Inside there was a bento box with a note on it. He tilted his head in curiosity as he picked it up and began to read.

'I know you're probably upset that you lost the bet.' The blond allowed himself a smirk and kept reading. 'But it's for the best, I promise. As you probably already know our training starts tomorrow and you need to eat something more nutritious than ramen if you want to get stronger. Believe it or not, I made this food for you myself. And no, it won't kill you. Enjoy. -Jiraiya'

His teacher had clearly made the note with the presumption that Naruto had lost the bet. 'I guess I was supposed to find this after he went out perving.' He mused. A thought occurred to him.

"When did he have time to make food? I haven't left the hotel room in days?" The confused blond looked inside the bento box and to his surprise, the food actually looked edible. Jiraiya didn't come off as someone who knew how to cook so Naruto was a bit apprehensive at first.

It appeared to be steak, peppers, and other vegetables that Naruto didn't recognize. That wasn't surprising considering his fear of the word 'nutritious'. That was all served over a healthily sized bed of rice. He sat down at the table, picked up the chopsticks and slowly brought a piece of steak to his mouth. He took a bite and was shocked at the flavor he was tasting. "This is actually really good." The blond muttered to himself. The meat was tender and spiced wonderfully with spices that the boy did not recognize. The assorted vegetables were soft, but not too soft, and complemented the texture and flavor of the meat perfectly. "No way in hell he cooked this himself." He said as he continued to scarf down the delicious food.

Tomorrow was going to be a long day. Hopefully, that food would help give him the strength he needed to survive it.

Naruto finished the food and slammed the box back onto the table, his eyes brimming with determination. "I'm ready!"

AN: After a lot of buildup we're finally going to get into Naruto's training. This training trip will go relatively in-depth and cover a significant amount of chapters.

Please leave a review with your thoughts and opinions about this (also tell me what you think of the story so far).

Thanks for reading!