Bet on the big ass - One-short

Tsunade knew she shouldn't have bet against this brat, but she was half drunk and he didn't seem like he was going to do that. Tsunade had no faith in his ability to think rationally and solve equations. “Pass the written part of the first Chuunin exam with a passing grade!” - she said, more to Shizune's delight. The student literally applauded her for her sensible and safe way of testing the rapidly progressing Naruto and saw fit to leave them alone.

Naruto brushed it off, folding his arms and pouting slightly. “Ero-Sennin taught me some of it,” he admitted, ”but it's so boring! He quit on the third day and said a real ninja lives by intuition and heart!”. He set the paper aside. “Why do I need this now?”

An irritated Tsunade, in her alcoholic state, quickly came up with a solution. She smirked and offered her own solution to the problem, “Then let's make a bet.”

Intrigued, Naruto turned around and let her place the bet. If he passed the test, she would belong to him for the night. A not-so-rare wager between them; Naruto often won, and it usually led to blowjobs, hand-fucking, or - which was preferable to him - tit-fucking. She had laid him once, but it had nothing to do with betting - she just wanted to fuck him in her chair. Normally, on such occasions, Naruto would take her place and want to wear the Hokage's hat. “She'll be mine someday anyway,” he'd always say, and she'd give up just before the meal began, enriched with cum.

This time, however, it was different. It was only because she was drunk that she foolishly agreed. How foolish it was to bet against Konoha's fast-rising star. He had passed, and she couldn't believe it. He hadn't just passed, he'd gotten seven points out of a possible twelve (a solid twelve).

“How?” she was stunned, eyes glued to the test while the blond-haired stout man rubbed his hands together happily.

“It's time for a bet, Obaa-chan,” he beeped.

And, keeping her word, Tsunade was forced to concede.

“On the table,” he conditioned, and she, more girlish than usual, worried that someone might come in. Naruto had already picked up the phone and put on his Hokage cap. “It's okay.” Normal for him, not for the esteemed Fifth Hokage, granddaughter of the First.

Nevertheless, she honored his wish. Why couldn't he prefer that she get under the table again and thrust her tits over his meat? She would have preferred that, being plastered with his copious seed - she knew how copious his loads could be - than this.

She was wearing nothing but tight spandex pants that ran down her thick thighs to just above her knees. Next, of course, were panties.

Naruto wondered if he could do without them, but... “Simpler,” he said aloud, revealing her to his gaze.

She was all taut; ass raised, shoulders tense, fists clenched under a flushed and grimacing face. “You're overconfident, brat,” she warned him, ducking under the weight of the bet. “I...I'm sure you cheated!”

Naruto looked out from behind her heart-shaped back, smirking and chuckling, and feeling pleased with himself. “Of course! That's the point of the test, isn't it? It wasn't Shizune-ni-san! She was with a pig!”

At that moment, a thought flashed through Tsunade's mind. Shizune had left early because Tonton had an upset stomach! Naruto had asked the clone to impersonate her during this visit and then go in search of the answers to the test! After memorizing the answers, the clone dispersed to pass on the knowledge to the original!

“Damn you!” - her curse ended on a high octave, her first reaction to the touch of his tongue. But the pussy, glistening, moist, appetizing and gorgeously shaved, was not his target tonight. His appetite had switched to something else, and he licked that hole up and down, side to side, and pressed hard with the tip of his tongue to test its strength. Of course, it wasn't easy to penetrate her. Although the title of “Legendary Sucker” had a perverse meaning, Tsunade maintained her regal posture as best she could. She sucked and fucked her way out of debt, but she had limits.

Naruto disregarded those boundaries and nuzzled her dimple with pleasure. Her mumbles and mingled curses flew carelessly from his thoughts. All he could imagine running his tongue over the dimple of her ass was the sounds they would both make when he fulfilled his bet.

The amount of saliva continued to increase and as he agonized trying to pierce her, saliva dripped down the folds of her sex organ. It tingled and tickled, but Tsunade couldn't unclench her fists and treat her swollen clit to affectionate touches. All she could do was grit her teeth and endure the oral massage of her nape.

In response to his tongue's attempts to penetrate her, she let out a guttural “Ahn!”. Her muscles reflexively closed around his tongue, but they couldn't expel it, and the tip floundered and fished out what it could before the contractions inevitably won out.

That was good enough for him, and he leaned back in his chair, wiping away the saliva that had accumulated on his chin. “We have to do this now, Baa-chan,” he announced, as if she had a say in his proceedings.

Not wanting to admit it, Tsunade pulsed. She had enjoyed his tongue despite her doubts, and now longed for the anticipation to end. She had sobered when she saw his score - she knew now that it was a farce - but now lust possessed her. She wanted him to aim for the tantalizing unfolding petals, but as the zipper lowered and the flesh peeked through the open fabric, the blunt head rested against her anus.

Should she have? Perhaps she would have preferred to be finger-fucked a little, to relax in preparation; she knew what he was packing.

“Just do it,” the Fifth Hokage said, and the genin obeyed.

He entered her firm hole with good force, slow and impatient, like when he fucked her mouth or tits, but with restraint. She struggled to straddle his head, opening only a little at a time, her supple body refusing the unnatural invasion. But still he pushed forward. His mouth opened with a sharp gasp, but Tsunade let out a long, deep moan as her ass began to stretch and encircle him. No, he wasn't small; even for an adult, he was gifted! Tsunade had once advised Sakura to be more flexible when she was told they had a date. “Just advice,” the mentor had said innocuously with a smile and a belly full of Uzumaki's semen.

Of course, that same semen would go into her gut as well, but in a different way. “Ah!” Naruto thrust the knife in a little too insistently, not satisfied with the slow progression, wanting to burrow into her unprepared bowels without delay. Tsunade grasped the edge of the desk, needing support as Naruto shifted her insides. “Ah!!!” He did it again! This time Tsunade's uncontrollable strength crushed the desk in her hands. “Not so fast, you fool!” - She snapped back.

“Sorry, sorry,” Naruto said hurriedly, his eyes unable to find anything of interest except his cock confidently entering the sheath of the bustiest and most beautiful woman in all of the Five Lands! Her pussy he treated with the same reverence, but this was something greater. The small opening where his tongue had barely squeezed through was now doubled, tripled, quadrupled, accommodating his large cock, hugging and massaging it as he carefully made his way to her rectum. When it was only two inches away, he pushed his luck and hips, and with one furious thrust, he entered her.

Tsunade was grateful for the pause when he entered her ass completely: it gave her a chance to regain her composure. She did breathing techniques and even tweaked her chakra a bit to reduce the pain. But she could feel him. He had stretched her slender tract, and now she held him like a glove, too small for his girth. When his cock twitched, she felt it, and when his cum oozed out of him, she felt it too.

If they kept this up, would he cum? She wouldn't doubt it, but Naruto didn't know how to sit still. And sure enough, he came out of her and back in again. He didn't waste any time, she hadn't expected him to. It had been proven that she could take him all the way, now she just needed a little more to satisfy him.

“That's great, Baa-chan,” the boy wheezed, pressing his hips against her ass. “Do you like it?”

Tsunade, who received an ass-fuck in return, could do nothing but let out deep moans and wheezes. But eventually she was able to say, “Just...keep...going...ugh!..keep going...brat!”.

And he obeyed again, pushing her bowels harder and harder until it was easier to make longer and faster thrusts. From below, her pussy continued to produce the arousal that was building up in his straining sac. It was extra pork in Ichiraku's miso ramen! Naruto allowed himself to moan in ecstasy. Tsunade sunk her teeth into his forearm to keep from screaming and spurring the exuberant young man on.

For several minutes, or maybe just one minute, Naruto pounded insistently against Tsunade's back, bouncing off her cheeks only to come back again moments later. The inner walls of her body clenched and tried to return to normal, but his cock returned with renewed force each time. Attentive to every change in her body, Tsunade could feel her intestines readjusting, accepting the persistent intruder.

It continued to leave a wet trail behind it - now enough to form a puddle into which it slid - but it was still unable to pour a more copious volume into her. “Hurry up,” she growled, still clutching at the splintered table, and her lower half shook. A bit of essence leaked out of her slit, powerful muscles contracting, craving attention.

“I will,” Naruto wheezed, continuing to thrust his cock into her. His cockiness was quickly fading into the anguished look of a helpless man. His grandmother urged him to hurry up, and he wondered what had taken him so long to resist, thrusting into her ass. His body twitched as he held her hips unreliably, losing Tsunade for a moment as she pitched backwards. But he quickly reclaimed her and regained his rhythm, pulling her to him again.

Genin fucked the Hokage's ass as he sat at her desk, among the forms that were so important to stability and relationships in Konoha. Tsunade's pussy could have drooled over a few of them by now, but she didn't care about anything but the cock filling her ass. Oh, men! The debt collectors who were so enticed by the thought of her ass were all left unsatisfied in their desire! Even Dan had expressed a desire for a taste that she hadn't fulfilled before his death. And here was this oft-repeated boy...! Tsunade's cries began to increase, escalating into a roar of orgasm! The table in her hands was cracking and breaking harder and harder, and the pressure she was putting on it like a dead weight was testing its strength! Those scrolls and forms that hadn't been shaken off the desk, along with Naruto's swinging pouch, poured water as her empty cunt unleashed; a juicy explosion that blinded her entire workplace with passion.

Naruto would have had to be dead not to release in time to her guts thrusting at him. “Ya! That's it, Granny, okay!” A heavy stream of white liquid cascaded down the tight space of Tsunade's colon; moist heat soaked the ajar opening, rising up inside and flowing back down, though his cock was too tightly clamped to let much leak out around it. Maybe when he pulled out, but he was still in agony! His hips bucked against hers, bouncing in time with his enthusiastic thrusts. She, too, went limp, recovering from her rectal orgasm. His moisture seeped out and settled gently inside her, and his shaft steadily deflated so she could relax. Involuntary intestinal spasms pressed against the rod that had expanded and filled the entire space. Losing stability, the cock plunged deeper and deeper into her until....

Plop!

Naruto gasped as he stared at the closing hole, though his semen was already flowing to the surface in a milky trickle from the folds of her heated labia, and the bulk of it remained deep inside his grandmother's hole until the anus slowly closed on its own. Having gained experience and unloaded his balls, Naruto leaned back in his chair and took a deep breath, glad he had accepted the bet. Stupid grandma, he thought. She's easy to fool when she's drunk.

Tsunade was less awake, flushed and contemplating the fact that she would have to expel the substance that was now choking in her intestines later. Damn boy, she thought. He hadn't been so smart when he was younger.

But there was little time to resent him, for in her absent-mindedness she didn't notice him sliding off the table and closer to her face until his soiled cock was rubbing against her ruddy lips. Tsunade's honey-brown eyes tensed as much as her frowning lips, warning him that he was getting too bold; he fended off her tenseness with his goofy but charming smile, persistently guiding his cock to her refusing mouth. But eventually his jaws parted and she let that filthy cock inside her. She was better at it, better at sucking it than letting the petulant brat shove himself up her ass. Clamping down on his slick balls, she thoroughly laved his cock in her mouth, saliva ebbing and flowing from her compressed lips until she decided enough was enough.

Saliva dangled from her mouth and joined the head of his cock. “This is the only time.” She turned her head sharply, trying to swipe away the lewd saliva, but to no avail. The woman's eyebrows furrowed in a frown. “Don't expect it to happen again,” she warned, her hand breaking the unyielding bond and shoving Naruto's cock away before he could convince her to start sucking him again.

Less than a month later.

“Wow, that's it, it feels like I'm getting deeper!”

“That's the way it is! Ah! Keep it up!” Tsunade's mouth was ajar, and short, gasping moans never stopped coming out of it. She caressed her pussy with her fingers, stroking it to compare it to the stranger sensation of Naruto's shaft resting against her ass again. Unlike her previous position during her first anal sex, she was now sitting on the chair, jutting her ass out so that Naruto could more comfortably penetrate her. He pulled off the woman's underclothes, leaving only the high-heeled shoes...at least on one foot as he pulled her shoes off her in a frenzy to lick the high soles and suck on her toes. He kept her legs raised and open, straddling her ankles so she could caress herself with both hands. Sitting this way, he could watch her huge sloping breasts as he exposed them through the robe. They rippled and pulsed each time he inserted his cock into her ass, squeezing the space in her cunt.

They had been doing this for a while now, ever since Tsunade lost a bet that Naruto could beg Anko for some liquor.

They'd been so lucky last time that they'd overdone it, focusing on pleasure over safety. As he shoved his cock into Tsunade's ass as deep as he could, making her cry out in pleasure as he entered her even deeper than before, the door opened and Shizune - the real Shizune - walked in nonchalantly. “Tsunade-sama, it's time...” The raised lunch tray fell from her bright mood; thankfully, her fingers remained firm enough to keep the handles steady, preventing a mess on top of the one she'd walked in.

Tsunade gasped as she looked past Naruto; Naruto glanced over his shoulder at the medical student who stood in a daze. “Shizune!” - shrieked the master.

Shizune, stunned by the surprise, didn't stutter as she uttered: “Aiii!!!!”. Instead, she tried to comprehend what was happening, but she couldn't. All she could get out was, “What... what... what's going on?”.

Tsunade couldn't think of what to answer, not right away, not now, with his cock throbbing and leaking into her rectum, lubricating her insides. But Naruto straightforwardly, with a wide grin, hummed and said: “She lost the bet.” Then he turned away to finish the job, fucking Fifth in the ass while her assistant witnessed.