Konoha: Naruto's abnormal life choices

Two Weeks Later

Two weeks had passed since their last adventure, and Naruto Uzumaki was now traveling with Jiraiya to a small town in the northern region of the Land of Fire, bordering the Land of Fields.

This town wasn't particularly famous, but it had one notable feature—a street mentioned in the original texts known as Tansho Street. According to Jiraiya, anything and everything you could imagine could be found on that street.

The old man seemed unusually excited about the place, which naturally piqued Naruto's curiosity as well.

By the time they arrived, the sun was already setting. They followed Jiraiya into a brothel known as Piaoxiang Sakeya, located right on Tansho Street.

What they didn't realize was that two elegant figures had silently followed them, observing them from the shadows.

One of the women—on the right—had an especially striking figure. When she saw Jiraiya dragging Naruto into the brothel, her expression twisted with disdain.

"Still the same old pervert," she muttered under her breath.

"Tsunade-sama, isn't that a bit harsh?" said the woman next to her—Shizune—who was dressed in black and holding a small pig in her arms.

Tsunade scoffed. "Harsh? Please. Watch closely. We're going to slip him a little something later."

"Yes, ma'am," Shizune replied, reaching into her pocket and pulling out a small pouch of powdered sedative. With a nod, the two women followed them inside.

Inside the Brothel

Naruto was… underwhelmed.

As it turned out, the hostesses here didn't provide "special" services—they only served drinks and chatted. That was it.

Still, Jiraiya was having the time of his life. With a girl on each arm and a bottle of sake in his hand, he was practically drooling as they fed him sips of alcohol.

Pathetic.

Naruto clicked his tongue in irritation and focused on the snacks laid out on the table.

One of the hostesses, noticing how well-behaved Naruto was, leaned over with a smile. Her voice was teasing and playful. "Little brother, would you like your big sister to feed you too?"

Naruto glanced up at her. She was somewhat attractive, but in his mind, she couldn't hold a candle to women like Uzuki Yugao or Yuhi Kurenai.

Tch. Do you think just anyone is qualified to feed me?

"No thanks," he replied coolly.

Jiraiya burst out laughing. "Haha! What's the matter, Naruto? Feeling shy?"

Naruto raised an eyebrow.

Was this man really suggesting he was shy?

This brothel was tame. The women weren't exactly stunning, and the entertainment was limited to drinks and small talk. What was there to be nervous about?

Old virgins really were hopeless.

Naruto was about to explain what it truly meant to understand women when—

[Passive Selection Triggered!]

Jiraiya looks down on you. Despite being a virgin, he believes he's far more experienced and mocks you. How do you respond?

Option 1 – Flirtatious: Engage in a deep conversation about women with Jiraiya until he admits defeat.

 Reward: 84% control over the Nine-Tails.

Option 2 – Reckless: Drag Jiraiya and forcibly engage the two hostesses publicly.

 Reward: Rinnegan.

Option 3 – Shy and Reserved: Say nothing.

 Reward: 300,000 Ryo.

Option 4 – Morally Upright: Stand on the moral high ground, criticize Jiraiya's lewdness loudly, and assert your noble spirit.

 Reward: Devil's Contract ×1.

Naruto's expression froze.

Since when did they offer Nine-Tails control at this level?

Even the Rinnegan was on the table. Of course, that meant the second option was completely unrealistic—getting Jiraiya to go along with something like that was absurd. The man was over forty and still a virgin.

Still, why was Option 1—just a conversation—so highly rewarded?

Could I actually pull that off? he thought, weighing his choices. Option 1 was tempting, but so was Option 4 with the Devil's Contract. He needed both for his growth. But as always, high rewards came with high risk.

There's no such thing as a free lunch.

"Pfft! Look at you—can't even lift your head. So embarrassed you're frozen stiff, huh?" Jiraiya mocked, pinching the hostesses next to him.

He glanced at Naruto and thought to himself, This brat was talking big earlier, saying he wanted some 'Yomi Tohka'—but the moment we get in here, he freezes up. Typical kid.

Naruto slammed the table and stood up. "That's enough, Master Jiraiya!"

Jiraiya blinked in surprise, still wearing a smug grin. "What, that's it? I've barely started. Don't worry, I'll call two more girls for you. Hahaha!"

"Master Jiraiya, have you forgotten the three shinobi prohibitions?" Naruto asked sternly. "No alcohol, no luxury, no women. And yet you bring me here to corrupt me?"

With righteous fury, Naruto pointed his finger. "I won't give in to your temptation just because you're one of the Sannin!"

"…What?"

"You sicken me!" Naruto growled, his finger trembling.

Jiraiya's mind was racing. Wait, what? Didn't you beg me to bring you here? And now I'm the problem?

He quickly composed himself. No, this brat is just scared. He's trying to escape the situation.

Jiraiya grinned and warned him. "Watch your mouth, brat, or I'll call the girls over to strip you of your 'chicken' status tonight!"

He mocked Naruto like a high school bully.

Tap, tap, tap—

Suddenly, the click of high heels echoed across the room.

Jiraiya's grin disappeared in an instant. He let go of the women clinging to him and sat upright like a soldier.

Naruto turned around, confused.

Standing behind them was a stunning woman in a green cloak.

She had an oval-shaped, porcelain-white face, long blonde hair tied into twin ponytails, narrow amber eyes that curved upward, and lips painted peach-pink.

She radiated maturity and sensuality—far more than Kurenai-sensei ever had.

This… was Tsunade Senju.

Now Naruto understood why Option 1 came with such a high reward—because even if he could outwit Jiraiya, he could never survive a punch from Tsunade midway through.

"Tsunade-sama, weren't we going to handle this quietly?" Shizune whispered behind her.

Tsunade growled, "I can't take it anymore. That filthy old frog is bad enough on his own—but trying to corrupt a kid too? Unforgivable."

Her anger erupted in one swift motion.

BOOM—!

Jiraiya was launched out of the brothel like a ragdoll with an over-the-shoulder throw.

Naruto was emotionally damaged.

"A kid?" I'm clearly gifted, thank you very much.

[Ding! Congratulations—Option 1 Completed. Reward: Devil's Contract x1 issued successfully.]

At least the reward soothed his wounded pride.

Half an Hour Later – At a Nearby Izakaya

Jiraiya sat across from Naruto, his face swollen and bruised.

"You brat… You set me up!" he hissed. "It was your idea in the first place!"

"Tsunade-sama!" Naruto cut him off and quickly grabbed her arm. "You must understand! Along the journey, Master Jiraiya has been drinking, peeking in women's baths, doing all kinds of lewd things!"

Naruto rubbed his head against her shoulder like a pitiful child. "He tried to force me to become the second coming of the Perverted Sage!"

"You little punk! Say that again and I'll—!" Jiraiya's eyes turned red with fury.

He turned to Tsunade. "Come on, we've known each other for decades. You know me. You really think I'd corrupt a child?"

Tsunade hesitated. As annoying as he was, Jiraiya was usually decent...

But Naruto tugged at her sleeve, his big blue eyes brimming with fake tears.

Cute + Blond + Widowed older woman = Critical hit.

Tsunade cracked.

WHAM!

Her fist smashed down on Jiraiya's head again.

He went down like a tree.

"Is he going to die?" Shizune asked, worried.

"Nah. He's got a thick skull. He'll live."

Tsunade grabbed Naruto's hand and walked away with him, leaving Shizune behind.

Shizune glanced down at Jiraiya, then pulled the pouch of sedative powder from her sleeve. She tore it open and poured the entire thing into his mouth.

"That should help Master Jiraiya sleep well tonight."

But—

As soon as she left, Jiraiya's eyes fluttered open. He sat up slowly, rubbing his jaw.

"Heh… Still the same Tsunade."

A smile tugged at his lips.

Getting you angry and punched by you... that's the only time I get to touch you.

He yawned, then stood up and dusted himself off.

His eyes narrowed as he turned toward the window.

He was here.

Orochimaru had arrived.