I do not own Naruto

Warning: Lemon

A Mentor's Duty

Tsunade stayed silent as she contemplated her longtime friend's request. She'd been surprised when Jiraiya came into her office, just a few weeks after completing Naruto's training of three years. She'd expected him to stay away for months; to check on the spy network he'd neglected by training the blonde jinchūriki. Nevertheless, here he was, asking her for a shinobi with the Byakugan. That alone would be no problem; there were more than enough Hyugas in Konoha to send on a mission with her longtime friend. No, the person he wanted for the mission was the real obstacle. "Why the heiress?"

Jiraiya chuckled, it wasn't a question hard to answer. "I'm curious." Seeing Tsunade's questioning gaze, he continued, "Her improvement is impressive. If memory serves correctly, she was a failure in her father's eyes until recently. I think it's about time we test her abilities."

Was that it; simple curiosity? Tsunade's eyes glared at the Sannin in front of her. "You want me to send the heiress of our most powerful clan with you, just to feed some simple curiosity?" If she knew Jiraiya as well as she thought, then every mission with him would be dangerous.

"Now, now, it's not a dangerous mission," he assured. "I would scale it as a C-mission, maybe a low B-rank." Tsunade wasn't assured, which surprised him. "Come on, you trust me enough to take care of Naruto, but not enough to take a chūnin on a simple mission?"

He did have a point. He was strong enough to take on Akatsuki, surely he could protect Hinata. She sighed, closing her eyes. "Fine," she conceded. "But this mission better be as easy as you say."

"Sure, sure," Jiraiya promised, his hands waving her worry away.

Tsunade sighed. Why did she have a feeling she was going to regret this?

Hinata was surprised when she was summoned to the Hokage's office by some ANBU soldiers. Kiba and Shino had been with her as well; practicing on the training grounds of Team 8, but they hadn't been instructed to come along with her. It made her wary of the reasoning behind her summoning; why just her, and not the rest of the team?

She greeted the people she knew as she strolled through Konoha. There had been a time where she hated the many people that greeted her; knowing that they only did so because of her heritage, but she felt that she lived up to that reputation more and more with each passing day.

Upon catching the Hyuga from the corner of her eyes, Tsunade greeted her with a smile. Hinata was relieved; the situation of her summoning didn't seem to occur due to any dire news. "You called, Hokage-sama." Hinata admired Tsunade; her strength, calm demeanor, and leadership an inspiration to all kunoichi.

A nod was the only response she received. Confusion filled her mind as she was told of the reason behind her summon. "A mission with Jiraiya-sama?!" Why her? She wasn't anything special. Yes, she had improved, but nowhere near enough to keep up with a legendary shinobi like a Sannin. Her prepared objection was quickly muffled, Tsunade silencing her with a halting hand.

"Don't worry," the Hokage said, wanting to calm the Hyuga as soon as possible with a strong, confident voice. "It's going to be a simple mission. While you should perform every mission with caution, I can assure you that you are fully capable of handling this assignment."

Hinata was honored to hear of the faith Tsunade apparently had in her. She knuckled her fist; this was her chance to prove herself. Bringing her fist to her heart, she loosened the muscles in her throat before she enthusiastically shouted, "Y-yes Hokage-sama!"

Kami, Jiraiya-sama was fast! Hinata knew that the Sannin wasn't giving it his all for her sake, but even when he was holding back she could barely keep up with him as they jumped from tree to tree. The meeting between them had been brief. She had been given a quick summary of the mission before they set off. They'd been traveling for a few hours now, and it was getting harder to see the road up ahead.

"Shouldn't we set camp soon?" Hinata exhaled, noticing the sky getting grimmer. It was turning dark, and she'd rather not have to travel blind, unable to see a potential assailant coming from every angle before it would be too late.

The Sannin agreed, but he knew the area better than anyone. "There's an inn a few minutes further from here. We should be able to reach it before nightfall." And surely enough, after a few more minutes of traveling, Jiraiya and Hinata came by a small inn.

Hinata eyed the sign next to the inn curiously. "Starlight Inn," she read out loud, wondering why she'd never heard of it before. It seemed quite small, or perhaps that was merely due to the size of the home she was accustomed to. The inn had been built with nothing but wood, suggesting that it has been standing here for a long time.

"Come on, let's go in." Jiraiya's urged for her to get inside, which brought her out of her trance.

They were met by an old woman at the counter, who gave them a bright smile. "Welcome, welcome!" she greeted enthusiastically, bowing twice. The welcome they were receiving was a bit too much, and if Hinata had to guess, she would say that this was because this inn didn't get too many customers. "How many days will you be staying here?"

"Just tonight; busy day tomorrow" Jiraiya quickly responded. "How much for two rooms?" he asked, reaching into his pocket for the money he would need.

"Two?" The lady behind the counter was confused before she shook her head. "I'm sorry, we only have one room left. It's been quite busy today, so I'm afraid you'll have to share one room together."

"W-what?" Hinata asked while blushing fiercely, apparently turning back into her old, stuttering self when distressed. "T-together?" She and a man… sleeping in the same room? Sure, she'd been on missions with Shino and Kiba before, but Kurenai-sensei had always with them. This would be just her and Jiraiya-sama… Jiraiya, although respected and admired as a shinobi, was also notorious for being the writer of the book series called Icha Icha – a series known for its adulterous content.

Jiraiya chuckled. "What are you so scared of?" he asked, putting a hand on her shoulder, making her jump. "Don't worry, there are two beds in the room." She sighed in relief as he received the key for their room, until she heard him mutter one last word: "Probably."

To Hinata's joy, there were indeed two beds in their room. Both were quick to sit on their respective bed as they entered their room; Hinata falling down on her mattress immediately, while Jiraiya merely sat down. It had been a long day for both, and they could use some rest.

It didn't take long before both noticed how quiet it was. Jiraiya didn't care much, he was used to the silence; usually performing missions alone. Hinata, however, was used to be in lively rooms filled with eccentric teammates or ex-classmates and found the silence to be haunting. It wasn't that she had much to talk about with the Sannin, though.

Hinata tried to find a topic to talk about, finding the silence uncomfortable. She shifted uncomfortably on her bed before she found the obvious question. "S-so..." she said, breaking the stillness, "what was it like to train N-Naruto-kun?" While Hinata tried to hide her flushing face as she spoke the name of her crush, it didn't go unnoticed by the Sannin.

So, Naruto has a secret admirer. Quite a cute one at that. A devilish grin appeared on his face. Not bad, Naruto. Not bad. Naturally, if this girl hoped to be worthy of Naruto, she'd have to go through him first. Naruto was his pupil, it was his duty – as the boy's mentor and godfather – to make sure that that all women interested in the boy were approved by him first, or so he told himself.

"It was good. He told me all about his ideal woman during our trip." At this, Hinata sat straight. Naruto-kun's ideal woman… Could it be her lucky day? Could she be anything like her, was she close to Naruto-kun's ideal? All hope was crushed, though, by the Sannin's next utterance. "Yep, he told me all about how he wants them experienced."

At this, Hinata gasped, red filling her cheeks entirely. "Really?!" Was that really something Naruto-kun would think? That she wouldn't be experienced enough for him? "B-but… Sakura-san," she argued, reminding the older Shinobi of her crush's own infatuation with his teammate.

Jiraiya cussed; he'd forgotten about Sakura. That girl wasn't any more experienced than the Hyuga in front of him. Nevertheless, Jiraiya had an answer. "Well yeah, but that crush started before he went through puberty." At this he gave a howl of laughter. "That boy sure grew up the last three years."

"Oh…" Hinata was dejected. Had Naruto-kun really changed so much? "Did he say anything else?" This couldn't be all Naruto wanted in a woman, right? Naruto was kind and sweet, he didn't only care about a woman's experience when it came to… to… sex.

"Something else… uhm… let's see." He brought the thumb of his right hand to his chin, cocking an eyebrow and pretending to think. "Oh!" he blurted, snapping his fingers. "There was something else now that I think about it." Hinata gave a sigh of relief. She might not be experienced, but she was sure that she would meet the second requirement. Her body leaned in closer, ready to jump up in excitement if needed. "He likes his women curvy."

"C-curvy?!" Hinata didn't even notice when her arms crossed over her bountiful chest in defense, squelching her soft cushions. "Did… did Naruto-kun really say that?"

Jiraiya nodded. "Word for word. I know exactly what Naruto's requirements for curvy are too, sooo…" Hinata was surprised when Jiraiya jumped up, pointing his index fingers in her direction. "Show me what you got!"

"W-what?!" she howled. What was the Sannin talking about?

"You want to know whether you're good enough for Naruto, right?" Jiraiya asked, waiting for the Hyuga to answer, which she eventually did with a hesitant nod. "Then we'll have to see if you're curvy enough for him."

Was he serious? Did he want to see her… her breasts? It wasn't until this moment that she noticed that her hands were plastered on her chest, squeezing her soft bosom until it yielded to her touch, which didn't take much of an effort. She swallowed away a heavy knot in her throat, rather embarrassed by the weight and size of her bust. When she was still a student of the Academy, she'd started to notice that her breast were developing much earlier than those of the rest of her classmates, and she has forced herself to wear width, heavy clothing ever since. But… Naruto-kun likes them? Could it be that her heavy burden – and she meant that literally – was now her biggest opportunity to win Naruto's affection?

"Come on," Jiraiya urged, a bit more demanding than before, feeling her unexpected consideration to his request. "You don't have to be scared."

An answer to her greatest question: would Naruto-kun find her attractive? That one, single question that always hung over her head could finally be answered. All she had to do was let Jiraiya-sama see her breasts. She closed her eyes and reached a decision. "A-all right…" she spoke falteringly. I can't believe I'm doing this… Hinata thought with a blush.

Jiraiya grinned, curiosity filling him as Hinata's hand reached for the zipper of her baggy jacket, pulling it down and stretching the cloth over her shoulders to show her glorious globes hidden under a very revealing mesh shirt. His mouth turned agape; they were big, perhaps even bigger than Tsunade's had been at this girl's age. What the hell! Has she been hiding those gorgeous melons behind those layers of clothing all this time?! Those are double-Ds, and she isn't even out of her teens yet!

Jiraiya almost choked when the mesh shirt was taken care of as well, the shirt extending to be pulled over her soft mountains of flesh. Her tits wobbled into view when her shirt was thrown over her head, but the pert tips of her large breasts were quickly concealed behind her arms.

"Hmmm… This won't do." The blush increased on both their faces as he stepped closer, which made Hinata take a slight step backwards. "To see if you meet Naruto's expectation, I'll have to look a bit closer..." His hands came up to shove Hinata's arms out of the way so that he could tend to the tit unhindered. He was met by two supple mounds of flesh. Her nipples – a bright shade of pink that perfectly complimented her pale skin – had already tightened; courtesy of the room's low temperature. How would she react if he…

She moaned softly when his fingers brushed against her chest; a flicker of his index finger against the side of her breast before his palm cradled it. She did nothing bust gasp when her breast was caught in his hand. Sensing no resistance, he soon caressed her other tit as well. His fingers made the globes yield instantly, her muscle tissue apparently no match for the natural softness of her bosom. His palms traveled to the underside of her breasts before he brought them up, testing their weight.

The attention to her sensitive bosom struck a heat within her that flew through her veins, most prominently in her loins. Hinata knew what this feeling was; she'd felt it before. Normally, she would be quick to dip a finger down there, but in front of another person – a Sannin no less! – she tried to keep her cool while he pinched and coiled her pert nipples. Unfortunately, her cool façade was quickly subdued when Jiraiya took a nipple in between his lips to suckle.

Her hands set themselves on his muscular shoulders. She cringed, her sensitive nipple being fully engulfed in his mouth, suckling greedily. He tended to her tits thoroughly, alternating nipples hastily and randomly. "Ah… J-Jiraiya-sama!" She squeezed into his shoulders, her crotch beginning to overflow with stimulation.

Had Jiraiya's lips not been as busy, he would've surely smirked by now. Hook, line, and sinker! he thought, suckling, licking and groping like a madman. He pressed his weight on her, making them fall on Hinata's bed, but the Sannin never relented in his attention to her bosom. Hinata moaned and gasped, her heat only intensifying, Jiraiya's dual assault of his suckling lips and groping hands leaving her melting. One hand reluctantly left her breasts to tend to another area. She felt his warm fingers on her flesh as it traveled down her stomach.

She inhaled deeply, making her chest expand, when he wriggled his fingers through the opening of her pants, pressing his fingers against her damp panty. She mewled adorably to his fingers' taps to her panty-clad sex, which only made him want her more. Expecting Hinata to become startled from what he was about to do, he placed his left hand on her shoulder to hold her still before he pushed her panty aside. He explored her slick folds, easing them aside so that his middle finger could probe the entrance of her depths. Hinata almost jumped when he inserted his finger, her breasts jiggling from the subtle movement, but Jiraiya kept her still, wriggling his finger further in her narrow channel.

Despite her status as a virgin, he couldn't feel her hymen. Musing that she probably broke it during her missions or while training, Jiraiya attempted to loosen her some more; if he would attempt to sheathe his cock into her now, he would surely meet more resistance than she would be able to handle. Jiraiya moved away then, putting some space between the two before he buckled his knees. He set his hands upon her shapely legs while his eyes rose to watch the pink hue that began to color the Hyuga's white cheeks.

The kunai holster on her right leg was unstrapped before embarrassment filled Hinata as Jiraiya stripped down her pants, his face heated as he appreciated her curves and the spread of her hips. While she gave a mewl of uncertainty, Jiraiya felt that he could cum when he rolled down her white underwear. He pulled her knees apart, and she could almost faint from embarrassment when he leaned in close to her vagina, the feeling made all the more powerful when he combed his fingertips through the short hair crowning her mound.

His middle and index fingers spread the engorged petals of her sex. With perspiration starting to cover his head, he watched her pink lips separate and expose her insides. Jiraiya returned his digits to her moist hole. It was a tight fit, but it had room to stretch. When his fingers sunk into her, tight walls clung tightly around him. His digits curled inside of her, massaging the contracting walls of her hidden channel. When he rubbed at the top, she squealed and impulsively swayed her hips into his hand. He smirked, they always went wild once he found their G-spot. He pumped his fingers in and out of her virgin channel, only retracting to give her a rest from emitting all those moans and gasps. She blushed furiously when he took his soiled finger into his mouth to taste her. "Ah!" he voiced joyously, clearly satisfied with her taste. "I think you're ready."

Ready? Hinata wondered. Ready for what?

The Hyuga quickly got the hint but kept silent, mesmerized as Jiraiya undid himself of his clothes; footwear and waistband quickly discarded. Hinata watched wide-eyed as he dropped his pants, his rock-hard length protruding in its full glory. Her hands came up to cover her agape mouth as she eyed the length, amazed with its size. Even though Hinata's knowledge of the male anatomy was limited, she was pretty sure that this was a whole lot bigger and thicker than that of the average male.

Suddenly, Jiraiya grasped her hips and maneuvered her to the edge of the bed before her legs were thrown over his shoulders, one hand set on her waist while the other maneuvered his cock toward her slit. Doubts filled her as the phallus edged closer and closer. She wouldn't – couldn't! – accept to lose her virginity here in an old inn to a man she barely ever spoke to. Before she could voice her opinion, though, something echoed in her head. "Naruto told me all about how he wants them experienced." Jiraiya told her this at the start of their conversation. If she did this, she would be experienced. She would be worthy of Naruto-kun! I have to do this. So I can deserve Naruto-kun! Nevertheless, she was still doubtful on another subject.

"Will… will it fit?" she asked, still sizing up his erection, wondering how it could possibly fit in what she considered a small hole. She was silent, eyes twinkling while he aimed for her cleft, uncertainty replaced by anxiety. She observed silently as her virginity was taken away. Not by Naruto, as she'd always imagined and hoped, but by the blonde's mentor, all so she can become worthy of Naruto in the future. At Jiraiya's command, she spread her legs just a bit wider for easier penetration.

Jiraiya pushed eagerly on her engorged lips once he found his mark, but his length and girth made the intrusion a slow – and painful – process. She shuddered when she felt his large, bulbous head rubbing against her folds; fingers were one thing, but it was an entirely new experience having a cock knocking for entrance.

"Wait!" Her hands were put against the pervert's shoulder blades to insinuate halt. "P-please wait!" she breathed out. "It's too big!" Jiraiya had expected such a reaction, though. He pulled back a little, pushed further in, pulled back again, and then made the final thrust forward, making the Hyuga cry out as he hit her cervix painfully. She arched her back in pain, her heavy breasts heaving upwards. Nevertheless, despite the pain, she managed to accommodate all of him inside her, a feat that would earn her respect from even the most experienced of women.

Jiraiya threw his head back, hissing in pleasure. While it hadn't been that long since he'd last had the pleasure to bed a woman, he couldn't even remember the last time he'd been embedded this tightly. They stayed still for a few minutes, giving Hinata the time to adjust to the phallus that spread her so wide and reached so deep.

Not surprisingly, it was Jiraiya who broke the silence. "I'm going to move," he announced. He was rewarded with utters of protest, but he waved away her fear, saying, "Don't worry, I'll go slow." As promised, his pace was slow and gentle for Hinata to get used to and enjoy. His thrusts, however, no matter how tender, did nothing to hide the pliantness of her springy tits; wobbling with any sudden movement. The Hyuga moaned softly, while his prick had hurt for a while during the initial impaling, her pussy slowly accommodated to his cock. "Ah, Jiraiya-sama!"

Jiraiya cussed under his breath, sweating profusely from trying to keep a controlled pace while Hinata continued to flex around him and coat him with her juices. Her breasts flopped up and down with each of Jiraiya's thrusts until her hands unconsciously began to knead the supple skin before tweaking the pink peaks. She groped the left one first, molding the flesh in a practiced squeeze before pinching the tip in between her forefinger and thumb. She was not rough with them; she was firm, carefully massaging them with the right amount of strength to produce pleasure without the risk of pain.

To see this girl pleasure her breasts so alluringly… The sight of the mounds bouncing in time with his thrusts was hypnotic, but Jiraiya found the display of Hinata touching herself, moaning with desire, to be even more mouthwatering. He wanted nothing more than to straddle her and push his cock between those soft cushions until he was spraying them the boiling-hot load in his testicles. The thought didn't do much to control his restraint, and in the next instant, he began to pull out before starting a relentless series of brutal thrusts that had her writhing. In short time, however, she soon came to enjoy the feeling of his cock clashing against her cervix, sobbing in pleasure. To help Jiraiya reach deeper into her, Hinata wrapped her long, shapely legs around the Sannin's waist, beckoning his thrusts. "It's so good, Jiraiya-sama!" she gasped and moaned.

Hinata's head fell back, mouth wide and eyes unseeing. Her pussy gripped frantically at Jiraiya's plowing cock, slowing his pace insignificantly. He gyrated his pelvis against her, changed the timing of his movements, and included his hand to thumb her aching clit; Hinata moaned approvingly as he caressed the protruding nub. However, he soon took that hand from her pussy to support her left breast, holding it in place so that his mouth could slip around the taut nipple. When he began to suck on it, nipping and licking, Hinata cried out.

Hinata's toes curled when the feeling of release built in her abdomen. Her strained mouth opened every now and then, only uttering sounds of rapture. Jiraiya may have been a legendary shinobi, but even his stamina wasn't everlasting. He pried his mouth off of Hinata's mound to proclaim his upcoming release. "I'm cumming!" he announced, his violent thrusts reaching its peak.

Perhaps Hinata didn't care, perhaps she was too caught up in heat to think, or perhaps she just didn't know about the risks – whatever the cause, the Hyuga did nothing but sob loudly, unable to bear Jiraiya's assault any longer as the Sannin proclaimed his upcoming release.

Jiraiya got in a few more weaker thrusts before shuddering and pushing into Hinata until he couldn't go any further, releasing his load inside her. It rushed up his urethra and transferred into the Hyuga's waiting womb in thick, strong bursts. Hinata arched her back when the deep thrust pounded against her cervical wall. The final trigger to her orgasm, however, was the sensation of his warm goo spreading into her. "Ah! Jiraiya-sama!"

Jiraiya kept himself firmly inside until he was sure that not a single drop could be spilled. When he was certain that all was spent, he pushed himself up and carefully withdrew himself. Some of his seeds needed to be cleaned up when they were spilled as he unplugged, but that was a price he would be happy to pay.

There was that awkward moment of silence as they collected themselves, still winded and experiencing the aftershocks of their orgasms. Both got to their feet, Hinata's breasts bouncing as she rose. "Wow…" was all she could say. She'd heard that sex was supposed to be good, but this… this had really been something. Still, Hinata – despite having let Jiraiya touch her most private of areas – was suddenly very aware and embarrassed of the fact that she stood naked in front of him; breasts and vagina bare for all – or in this case, just Jiraiya – to see. She hastily reached for her panty, lifting it upon her shapely legs, the rest of her clothing quickly following.

As they both cleaned themselves up, Jiraiya mused that she still had much to learn. He'd refrained himself from going down on her, nor had he asked her to suckle his prick. Not to mention the things I can teach her to do with those tits of hers. Perhaps he could persuade her for another lesson. One thing was for sure, though: That Naruto is going to be one lucky guy.