Author's Note: Welcome to 'A Bet of a Lifetime', where a small event can, and will, drastically change the future.

To New Readers: Naruto's character will evolve over the course of the story (he'll start out just like canon Naruto, though). If you're looking for a fic where Naruto is exactly like he is in canon, then this might not be the story for you. He'll have some similarities to canon Naruto, but there will be key differences that become more apparent the more you read.

Leave your thoughts, question, concerns in the reviews below. PM me if you would rather not leave a review, all feedback is good feedback. I want this story to be as good as it possibly can be, and that can only be done with your help! Thanks and enjoy!

If you're new to the story, tell me what you think as you go! I would greatly appreciate it!


The Land of Fire had such wonderful weather. There were a handful of fluffy clouds scattered about in the blue sky. The soothing, warm light of the sun caressed the top of Naruto's head. The birds were chirping and, in that moment, he was able to understand Shikamaru's love for cloud watching. It was all perfectly to the blond Genin's liking… he just couldn't properly enjoy it. Why, you ask? Well, the answer was quite simple. It was due to a certain old pervert with long, white hair. Normally, the Sannin wasn't much of a problem,. but his incessant giggling was irritating. The high-pitched noises that erupted from the Sannin were unsettling, to say the least. How was it possible for a grown man to hit such a high note? The young teen did not know.

"Ugh!" The Uzumaki expressed his annoyance as he sat up into a cross-legged position. Being around Jiraiya was, well, not all that bad. Even when they didn't do anything, Naruto was still glad to be there. He couldn't explain it, it just made him happy to spend time with the perverted hermit. However... when the two of them embarked on their adventure, he was promised training that would prepare him to get Sasuke back, and defend himself from the Akatsuki. The Sage was supposed to be teaching him super cool techniques, not creeping on girls at a hot spring all day!

Jiraiya's ears twitched in annoyance at the boy's attempt to gain his attention. Not only was it loud, but it threw off his delicate concentration. It's not every day you get to witness beautiful women like this, and he was certainly not going to waste this opportunity. After all, his loyal fans would never forgive him for slacking off on the job!

"Would you quiet down a little, brat?" Jiraiya whispered harshly, glancing back at his blond pupil. "Or are you trying to get the two of us busted?"

Naruto's ears perked up at his master's choice of words. He frowned and his eyes narrowed dangerously. "Us? What do you mean us?" He whispered back just as harshly. As dumb as he was, even he knew it would be bad if they alerted the women located just below their high perch. If he had to guess they were only about 25 feet away from the women.

"You're here too, aren't you?!" Jiraiya shot back at his young student. "Now if you don't stay quiet, you won't just ruin my research session, but you may also get us caught! Do you want us to get chased off again?!" Hoping that the conversation was now over he turned back to his telescope to continue his 'research'.

Now, Naruto may not be the most intelligent Shinobi in The Land of Fire, but even he knew what the white-haired Sannin meant when he said research. I mean, Jiraiya has unabashedly referred to himself as a 'Super Pervert.' It didn't take someone from the Nara Clan to figure out what was really going on here.

The blond snorted derisively. "If we were caught, who do you think those women would want to beat up the most? The cute, innocent boy, or the old perv holding a telescope that dragged him here?" Unbeknownst to them, the longer the conversation wore on, the louder the two of them got. They were so caught up within their own little bubble that they didn't even notice the girls in the hot spring, as they around for the cause of the disturbance.

The sage opened his mouth to retort, but quickly closed it once he realized that his student was right. If those girls found them in this... problematic setting, he would assuredly get one-hundred percent of the beating. However, he was going to keep that little bit of information to himself. The brat didn't need to know just how right he was.

Finally thinking of a retort, a smug smirk graced the Sage's lips. "I believe after explaining my reasoning for being in this… compromising position, the ladies over there would jump at the chance to help me get my inspiration. After all, it's not everyday that you get to assist an artist in creating their masterpiece!" His face got red as drool began to drip from the corner of his mouth, as if a new idea for a scene suddenly popped into his head. Somehow, he believed his own grandiose delusions to be true.

These were the moments that truly dumbfounded Naruto. How could a Sannin, one of the revered and universally admired Legendary Three, act this way? A man whose immense power struck fear into the hearts of countless shinobi was nothing but a big, foolish pervert. 'And he's my master. I'm doomed, aren't I?' Naruto mentally sighed at the realization.

"Oh, please." Naruto scoffed at the Sage's pretentious boasts. "We both know that you're just a big pervert who uses research as an excuse to spy on pretty girls!" He shouted as he pointed a finger at his master. The boy's patience was wearing thin, it had been a week since they had left the Village. That week had gone by, and they still hadn't done any actual training.

'I left the village to get stronger to go after Sasuke, not to tag along and watch him perv around all day.' He thought to himself bitterly.

Jiraiya's smirk only continued to grow, Naruto was positive more boasts were on their way. "I'll have you know that without my constant inspiration I would never be able to continue my world famous 'Make Out' series!" He shouted back defensively. "Without my books, how would my loyal fans be able to live on?"

A giant tick mark appeared on Naruto's head. "Are you serious?" They were shouting now. "I bet a five-year-old would be able to write better books than you! At least their books would have an actual storyline!" Naruto smirked. Jiraiya didn't seem to notice what their loud volume was doing but he certainly did. Things were about to get very interesting.

He had no idea how right he was.

Now it was the usually composed Jiraiya's turn to get upset. "Well, I'm very sorry your tiny brain is incapable of understanding the complexities of my literary masterpieces!" The amount of pride radiating from his master made the blond question whether he should just go home and train by himself. He was starting to think the white-haired jonin was a lost cause. "A compelling tale of lust, passion, and love all wrapped up in one complete package!" Jiraiya continued his smirk ever so present on his face. "It's simply perfect."

Based on the look of his face, Naruto was no longer paying attention to his bombastic instructor. Jiraiya's passionate speech had been extremely loud, and he had suddenly become very cognizant of where the two of them were. If Naruto knew anything, it was that he needed to get out of there immediately! He peered over the shoulder of the older man, and his fears were unfortunately confirmed. What he saw caused his complexion to go white, and his eyes to light up in fear. A sputtered, unintelligible response came from his lips as he backed away slowly and turned to leave.

The sudden change in attitude and body language did not go unnoticed by Jiraiya. "Naruto, what's the matter? Are you okay" He asked with actual concern in his voice.

Naruto quickly shook his head in an attempt to alleviate the worry. "I-I'm fine, Pervy Sage." The nervous tone in his student's voice only furthered the older man's suspicion that something was not right.

"Are you su-"

"Yeah, I'm fine!" The Genin exclaimed before his mentor could finish his follow up question. "I'm not feeling too well, I'll see you back at the hotel!" With that, the blond sped off, leaving a Jiraiya confused behind in his wake.

He heard the urgency in his protégé's voice, but he was unaware of the reason behind it. At least, for now, he was unaware. "What was all of that about..?" he asked himself aloud.

"Ahem!" The voice was light and firm, but a seasoned shinobi could feel the bloodlust behind it.

Jiraiya turned around slowly, and what he saw before him made him visibly pale. A group of very angry, half-naked women stood over him, and a few of them cracked their knuckles violently with unnerving looks on their faces. At that moment, the Sannin remembered where he was and what he had been doing prior to his dispute with his student.

Suspiciously crouched just outside of the women's side of the hot spring with a telescope in his hand. The spot also had a perfect vantage point of where the girls had been relaxing, something that the girls were definitely aware of. Jiraiya gulped. 'Compromising position, indeed.' He thought to himself.

"N-Now listen L-Ladies… I know this looks bad but I can explain!" His last-ditch efforts to sputter out a response fell on deaf ears. Despite being in a similar situation more times than he could even count it was still just as terrifying as ever. These women were clearly kunoichi, he could feel the large amounts of chakra radiating off them.

And it was all directed at him. 'If it weren't for the bloodlust, this would be kinda hot.' Even in this precarious situation, he couldn't keep his mind out of the gutter. He closed his eyes and braced himself for the inevitable pain.

The screams of the Great Toad Sage echoed through the town. Naruto, who only about 100 feet away from the beatdown, chuckled softly to himself. It had felt like an eternity since he last allowed himself to laugh like that. And knowing that Jiraiya would be okay allowed him to not feel bad for finding humor in his Master's misfortune.

For a moment, the weight on the genin's shoulders felt manageable. He needed that. 'Thanks, Pervy Sage.' He thought to himself fondly as he slowly headed back to the hotel.


"I can't believe you got away!" Naruto ran a hand through his spiky hair and sighed softly. "I was kinda hoping they would get a few more shots in on you." The boy added with a sheepish grin. He loved teasing his sensei almost as much as he liked eating ramen. Almost.

Jiraiya rolled his eyes at the verbal jab by his protégé. "I'm so sorry to disappoint you." He spat sarcastically, nursing a rather large bump on the back of his head. He reflexively winced away from the pain as he rested a bag of ice on it. "Maybe next time I'll grope a couple of them then they'll really give me a beatdown." Despite that being a joke, the sage blushed slightly at the thought.

"I doubt it." The genin said dismissively. "You seem impervious to serious injury no matter how many times those women kicked the crap out of you." Did pervs have some sort of defensive jutsu that they keep amongst themselves for times of danger? Naruto would have to look into that.

"When you have been beaten by Tsunade herself, no other beating can even come close!" The blond was fascinated by how his master could feel pride in those words. "Tsunade is scarier than all of those women put together, and that's only when she runs out of sake!" Jiraiya inwardly cringed at the last time Tsunade ran out of sake when he was around.

Naruto remained silent as a thought came to him. Jiraiya's mentioning of the Fifth Hokage reminded Naruto of why he was even here with the white-haired sage in the first place. He frowned slightly. While it was always fun to laugh at Jiraiya when he gets caught by women, that's not why they left the village with the intent to be gone for over two years.

"Pervy Sage!" Naruto's obnoxious voice broke through the peaceful silence that Jiraiya was entranced in. Well, went his attempts to soothe his growing headache. "When are we finally going to start my training?"

It has already been a week since they left the village and the blond genin was starting to get restless. He needed to get stronger as fast as possible. So many people were counting on him, and he wasn't about to let them down.

Jiraiya quietly weighed his options. Ignore him for now, or make up some lie to trick the less intelligent blond.

"Pervy Sage!" Naruto's impatience didn't give the sage that opportunity.

Jiraiya clamped his hand over his ears in an attempt to drown out his obnoxious underling, but to no avail. 'Where's a mute button when you need one.' He thought in exasperation.

"Once I get enough material to complete a few more chapters, we will start your training! I Promise!" Was his plead. He thought for a moment, trying to calculate how much peeping that would take. "I'd say another week or two should be enough." The Sannin added, in hopes that that would be enough to calm down his student. He didn't think it would, but his optimistic mindset got the better of him.

Naruto groaned in annoyance. That was definitely not the answer he was hoping for.

"Come on, Pervy Sage. We both know that I can't afford to be wasting time like this!" His young mind wandered to his best friend, Sasuke. He ground his teeth together at the thought of him being with that snake Orochimaru. "I have promises to keep! I can't just wait around all day wasting time!"

Jiraiya gave the boy a questioning glance. "Oh? Just what exactly are you promising people?" He asked genuinely curious.

Naruto's eyes hardened. "I promised Sakura that I would bring back Sasuke. I have to get stronger so I can get him away from that creep Orochimaru!" The conviction in his voice spoke volumes about the boy's commitments he makes to his friends.

"Naruto." The wise jonin began. "You need to forget about Sasuke. You have more important things to worry about. The Akatsuki will be coming after you and I can't always be by your side to protect you." He knew his student wouldn't like the idea of forgetting about his friend but he needed to at least try.

"So, train me! If they are so strong then you need to make me stronger!" The blond purposely avoided any mention of Sasuke, much to the annoyance of his white-haired master.

'I will bring him back. No matter what.' The young genin thought defiantly.

Jiraiya sighed. He expected that he wouldn't be able to get through to the boy. He was the exact same way when he was younger. "Naruto, I understand that you're in a rush, but we've got plenty of time. Two years is more than enough time to make you into a great shinobi."

"But why can't we use all the time?" The boy asked hopefully. "You could just stop your research and help me get as stronger. It shouldn't be that hard to write a book, anyway."

Jiraiya went silent. Maybe Naruto had a point after all. With the threat of the Akatsuki looming over the shinobi world, wouldn't it make sense to train the boy as intensely as possible in the amount of time they have? 'Maybe I've been going about this all wrong.' He thought to himself.

The sage let out a sigh. 'The only problem is I need the money that this book will make to fund my spy network. If only I had a bit more time to finish it, then I could focus all of my time on making Naruto into a splendid shinobi.'

He tried to think of what to do as his mind finally finished processing the last thing his student had said. His mouth twisted into a tiny smirk. 'I only need a little more time, Naruto.' He thought to himself. He needed to play this perfectly. Naruto's natural competitive fire can help him buy a little extra time so he can finish his book.

"Not that hard to write a book?" The well-known author repeated condescendingly. "Oh, so you think that you can do a better job than me, brat?" He asked with the mischievous smirk still plastered across his face.

Naruto's eyes burned with a fire that Jiraiya loved to see. That competitive fury that drives the young boy to new heights. It's that same fire that appeared when Tsunade challenged Naruto to learn the Rasengan in under a week. And, of course, he prevailed. The blond didn't even hesitate with his answer.

"No…"

Jiraiya had to conceal a small frown that desperately wanted to show itself. He was shocked. 'Wha- '

"I know I can do a better job than you!" Naruto finished smugly, cutting off the sage's inward surprise.

Jiraiya allowed himself a small chuckle. 'That's more like it.' He thought fondly. Now it was time for his challenge. Something he knew Naruto would never be able to turn down. A challenge was just another opportunity to show everyone how great he was. 'However, this is something completely out of your comfort zone, kid.'

"Fine, then. How about we make a deal then, Naruto?" This was a completely different Jiraiya from the one Naruto was with earlier today. Gone was the goofy pervert getting caught and beaten up by women; this Jiraiya meant business.

"I'm listening." The genin began, slightly unnerved. He still wasn't totally used to serious mode Jiraiya. "What is it?"

"You said you wanted to train seriously, right?" He inwardly chuckled at his own phrasing. That would easily catch Naruto's attention.

Naruto's eyes sparkled at the thought of intense training. So much so that he had already forgotten that unnerved feeling serious Jiraiya gave him. "Of course! I need to get stronger as fast as possible so I can save everyone!"

"Okay…" The sage began slowly. Naruto leaned forward in anticipation as he awaited his master's words. "I promise to devote every second we have to train you as hard as possible if…"

"If…" The impatient blond repeated eagerly.

"If you write your own novel and are able to get it published through my publisher." The Sannin finished with a large smile.

Complete and total silence.

Just as Jiraiya was about to break the silence to ask if his student was okay, Naruto voiced his opinions on the sage's challenge.

"What?" The blond blurted out in shock. He had not expected this. "What do you mean? You can't be serious!" Now while Naruto isn't exactly known for his modesty, if his time in the academy taught him anything it's that he was lacking in pretty much anything that had to do with academics. Writing was certainly one of them.

"Oh, I'm very serious. Believe it." He said in a mocking tone. "Just a minute ago you said you'd be the superior writer between the two of us. Why don't you put your money where your mouth is, kid?"

Naruto huffed at Jiraiya's mocking of his catchphrase. It didn't sound nearly as cool when it came out of the old man's mouth. Naruto was just about to retort when Jiraiya cut him off.

"Oh, and before you hastily agree to all of this, there's something else you need to know." The Sannin continued as he ignored the dagger-like stare that he pupil was giving him.

"Hmm? What do you mean?" He asked in annoyance. There couldn't still be more to this challenge, could there? He was already asking the boy to do something he had never thought of doing. What else could there be?

"There is one more stipulation to this little bet of ours."

"Sti-pu-la-tion?" He sounded the word out slowly in confusion. His face scrunched up as he contemplated the meaning behind the very large word. "What's that mean?" He resigned.

Jiraiya let out an exasperated sigh. He pinched the bridge of his nose as he debated if he should buy the boy a dictionary. This kid has a long way to go before he can become a competent writer.

"Never mind, Naruto." He did his best to brush off his pupil's confusion so he could continue. "What I'm saying is, you know what you get if you win. What happens when you lose?" The smugness in the man's voice did not go unnoticed by the blond.

Naruto scoffed. The phrasing of his master's words irritated. He was always written off before he was even given a chance to show everyone what he was made of. He pushed down any apprehension he had going forward. He was going to do this.

"No matter what it is I won't back down!" He exclaimed with a reenergized fire in his eyes. "There are too many people counting on me to quit now!"

The boy's determination reminded the Sannin of himself when he was younger. 'I don't think I've been giving him enough credit.' He thought fondly to himself. 'Maybe he can handle more intense training than I had initially thought. After all, the kid's got guts.' Jiraiya admired the guts to never give up more than anything else.

Jiraiya stared off into space for what seemed like a few minutes and it was starting to weird the blond out. He reached up with his hand and waved it in front of his master's face. Still no response.

"Uh, Pervy Sage?" He asked with a bit of concern in his voice.

The sage blinked a couple of times and snapped out of his daze, only to realize Naruto had closed the already small distance between them and was standing on a chair so their faces were only inches apart. It was safe to say the boy was a little too close for comfort.

"You okay, Perv?"

Jiraiya's eye twitched slightly as he felt Naruto's breath slam against his face and into his nostrils. 'What a surprise smells like ramen.' He thought to himself, slightly disgusted.

Jiraiya took a few steps back to distance himself from his pupil's ramen breath and cleared his throat. "Sorry about that." He began. Naruto noticed that Jiraiya's face shifted back into what he called serious Jiraiya mode. Something told him that he wasn't going to like what the Sannin had to say next.

"I know how important your friends are to you, Naruto. However, if you lose this bet, as your master I forbid you from trying to go after Sasuke."

He was curious to see his student's reaction to this stipulation. Last time they had this conversation Naruto didn't listen to the wise hermit at all. He was dead set on bringing his friend back to the Leaf. Would he continue to ignore the words of his master or, with the circumstances now different, would he instead honor them? The sage did not know.

Meanwhile, Naruto's mind was racing. Had he heard wrong? How could he even ask him something like that? Sasuke was his best friend! He glanced up at the older man's face and the expression written across it told him that he had heard perfectly clear.

'W-What do I do?" He asked himself in desperation. 'If I want to get strong enough to save Sasuke… there's a chance I won't even be allowed to try and save him at all if I fail.'

Jiraiya felt slightly bad as he watched the inner turmoil his blond companion was going through. The truth was that no matter the outcome of this bet the sage has already committed to training Naruto as intensely as he could. He just figured the blond would give up in a few weeks and that would give Jiraiya enough time to finish his book. However, with this added wrinkle it may have just become a lot more complicated.

'Maybe this will be good for him. Show me how much you've grown, Naruto.' He truly did only want what was best for his godchild.

"T-This is probably the biggest decision of my life." The blond was finally able to find his words after a few moments of silence. Despite the almost impossible choice that Jiraiya has given him, he doesn't hold it against his master. After all, given the sage's own history with his former friend Orochimaru, there's probably no one else in the world that understands the Naruto better.

"So, what will it be, Naruto? Is it a deal?" He asked carefully. He awaited his answer with an outstretched fist.

Their eyes slowly met and Jiraiya's eyes widened slightly at what he saw. The piercing stare of Naruto made him feel as if he were swirling back in time. Those blue eyes gleaming with confidence and excitement made him remember his late student of many years ago, Minato. The prospect of a new challenge was too much for The Fourth Hokage to pass up, and it seems he passed that on to his only child.

The young blond has yet to even open his mouth but Jiraiya already knew what his answer was going to be. It was written across the boy's face.

"I'll do it!" Naruto yelled with all the enthusiasm he could muster. He reached out with his own hand and fist bumped Jiraiya's.

Jiraiya smiled and chuckled at his pupil's steely confidence. "Well, of course, you will, brat! It would be no fun if you quit before it even started!" Seems like Naruto's enthusiasm was contagious as Jiraiya felt himself get caught up in the moment.

"Just you wait. I will win no matter what!" The blond exclaimed as he watched his sensei

Jiraiya dug into one of his bags that were littered around the room. After a moment, he took out a stack of paper and a pen. He came back and handed them to his protégé. "If you're so confident, why don't you show me if you have what it takes to be a world-renowned author like me." He said with a cocky grin.

The boy swiftly took the materials and stuck his tongue out at the older man. "I'll show you!" He looked down at the blank paper. He blinked… and blinked some more. A sudden realization struck him.

He twitched a little as he started to get more and more anxious. Naruto did his best to hide it but his master could see the sudden change in the genin's demeanor. What could be getting him so worked up?

Despite all his boasting and unshakeable confidence, Naruto didn't have the slightest clue about what his story would be about. 'Me and my big mouth…'


AN: Welcome all new readers! This is a story that has been on my mind for nearly 7 years now. The first draft I had of this fanfic all those years ago was admittedly atrocious. But, and I'm being hopeful on this one, I believe that this first chapter is much better than anything I wrote before. Well, at least by my standards.

IMPORTANT: This is a fic that focuses heavily on the Time-Skip and the events that happen within it. It also covers Shippuden, but pacing starts off slow in the beginning. If that isn't your thing, I ask that you read up to (and including) Chapter 8. That's when things really begin to pick up.

I want to spend a good amount of time developing Naruto's character and his abilities. I've never been a fan of when stories don't show his development. So, what I'm trying to say is, if you dislike pacing on the slower side, be patient. It won't stay that way.