Hinata couldn't believe what she had put on. In the mirror, she stared in shock at her body barely covered by jet black lingerie, the stockings, thong, and embroidered bra all matching. The black material stretched tightly over her pale skin, her long black hair complimenting the look. After her failure to act last time, she had hoped that buying erotic clothing would give her the confidence to approach her love, but it had only embarrassed her further.
"Today isn't my day still, N-Naruto, but I can feel it! Soon I will be able to approach you and win your affections!" she cried out.
"Just tell him already before I get to that stud first!" Hanabi giggled, causing Hinata to blush intensely.
Meanwhile, at the Hokage Mansion, Shizune had almost forgotten about the deal Tsunade made with Naruto three days prior: if his mission in the Village Hidden in the Sand was successful, he would get to have fun with the assistant. When the brat slammed the door open, Kakashi and Sakura in tow, she felt true despair.
"Mission complete," Kakashi reported, "The Kazekage was safe and successfully gave his speech, Suna sent their warm regards and wishes for continued cooperation between our villages."
"Wonderful!" Lady Tsunade responded, "This is why I sent my best team for such an important mission. Here are your rewards." She handed each a sum of gold.
"Oh, you're too kind sensei!" Sakura glowed. She then turned to Naruto excitedly, "Hey, do you wanna get some food and then hang out at my place to celebrate?"
Naruto, his libido fully restored after three days of abstinence, was very interested in spending time alone with Sakura, but more pressing matters prevented him from doing so.
"Sorry, Sakura, but I gotta talk privately with Granny, we have important business to attend to." he said seriously.
Huffing in disappointment, Sakura left, Kakashi departed soon after, and just Naruto, Lady Tsunade, and Shizune remained in the Hokage's Room.
Unable to ignore Naruto's lecherous eyes undressing her mentally, Shizune spoke up, "Lady Tsunade, I will not stand for this. I had no say in your rash decision to auction me off. Not to mention, I happen to be in my late twenties and Naruto is just a boy!"
Naruto guffawed, "I am no little kid, I'm a man! And I believe a deal was made, so you'll get to see my manhood firsthand soon…"
They began to bicker until Tsunade yelled, "Enough! Shizune, I apologize for putting you in this spot, but I must make good on my promise as Hokage. To avoid causing you further embarrassment… I'll take over myself."
Tsunade had to applaud herself for her genius. A few days ago, she overheard Ino gossip to some non-shinobi girls about Naruto's dick size. She wasn't a cougar by any means, but she had happened to notice something of a snake in the jinchuriki's trousers once or twice. And amidst all the paperwork and legislation, she couldn't help but feel unfulfilled sexually. If only she could ride a nice, long dick without the headache of a relationship, especially as Hokage.
Thus, her plan hatched. She had a feeling Naruto would whine for more than just money, but offering herself would be uncouth. Instead, she presented her innocent assistant Shizune. Now, she could selflessly save her from such a shameful act while enjoying the brat's horsecock without strings or attachments. Everything had gone to plan, no wonder she was one of the Legendary Sannin, she proudly thought.
"A-absolutely not!" Shizune declared, "I will not allow you to degrade yourself for this insolent young man in such a way." Steeling herself, she approached Naruto, ripping her top open to reveal two jiggling melons. Lady Tsunade clenched her fists, barely containing her fury. She was so close to relieving her tension only for this to happen.
"Wow. Thanks Shizune. Okay Naruto, go crazy with her." she muttered through gritted teeth, turning a blind eye as the blonde began motorboating Shizune's tits. The assistant felt great shame as she allowed the genin to rub his face against her bosom; well aware of the power imbalance and age difference between her and Naruto. However, her duty always came first, and this wasn't the first time she had covered for Tsunade's dealings.
Shizune thought back to that time in a gambling house where she had to dance seductively while several men leered at her after Tsunade went into debt. Or that other time a business deal with the Cloud Village was falling through until Shizune took it upon herself to give a full body massage to the Raikage. The mental image of his erect rod still sent shivers down her back. In the present, she merely sighed as Naruto began pulling her taut nipples; at least he was just a boy.
As if reading her mind, Naruto frowned, "I hope you're not underestimating me again. Let me show you my Hokage-level cock!" With that, he brought Shizune down onto her knees, and standing right behind her head, proudly unsheathed his length. Shizune trembled as she felt the warm, hefty weight of a man's penis press against her cheek and lay on her shoulder. Tsunade gasped in awe at the sight.
Shizune, regaining her voice after the sudden shock of a penis plopping on her bare shoulder, shakily admonished, "T-this is not the place for such acts. The poor Hokage should not have to witness this depravity." She began to try and stand up, but Tsunade interrupted.
"Wait! There is no need for you to go elsewhere, Naruto will receive his reward right here, where I can monitor to make sure he doesn't go too far with my precious assistant." she decided, eyes still transfixed on the blonde's hardening dick.
Damn, the old hag can't get enough of my cock, Naruto realized. I've gotta rile her up while I enjoy Shizune… Making sure the horny Hokage had a great view, Naruto pulled Shizune's robe completely off, getting in front of her. Shizune squeezed her eyes shut in preparation, but was taken aback as she felt a hot length nestle between her well-developed breasts. Naruto moaned out, using his hands to squeeze Shizune's rack together as he began thrusting between the mounds. The assistant had never given a boobjob before, unsure how to respond.
"My goodness Shizune, you're a grown woman, act like it!" Tsunade scolded, "Lubricate your breasts." Shizune was flummoxed, staring at her superior in confusion. Rolling her eyes, the Hokage walked up, taking a bottle of sake she had stored in her desk. To Shizune and Naruto's surprise, she poured the alcohol between the woman's tits, allowing Naruto's penis to smoothly pump up and down.
"Ma'am, I thought you got rid of all of your sake after last time!" Shizune murmured, but suddenly realized that she was kissing the young man's cockhead! The sake had made Shizune's boobjob intensely sexy, causing Naruto to fully harden. His full-length member began rubbing on the black-haired woman's lips at the apex of his pumps.
"Mmm, just like Sakura…" Naruto purred, enjoying how Shizune awkwardly moved her head, trying to avoid kissing his tip.
Tsunade, drinking from the opened sake bottle, raised her eyebrows, bitterly whispering "Just like Sakura, huh? Even my protege has had a taste…"
Naruto grabbed the back of Shizune's head, holding her in place as he dislodged his erection from her alluring boobs, and aiming at her pouty lips, "Open wide and take my meat lady!"
"Y-you can't force me to- I'm your elder you bra- mmph!" Shizune said as Naruto inserted himself into her open mouth. Filling the assistant's tight throat, Naruto pulled out allowing her to gasp for air, glaring daggers up at him.
"You show no respect… at least be gentler…" she choked out, but Naruto seemed intent to use her mouth without mercy. Shizune felt like she was about to cry; how had assisting her hero, Tsunade of the Legendary Sannin, the feared Hokage of the Leaf, turned into being the bitch of this hormonal teenager? Preparing her throat, she opened wide, until…
"I won't wait a second longer!" Tsunade drunkenly screamed, jumping over her desk. Pushing her dazed assistant to the side, she told her, "This is how you suck dick."
Naruto almost fainted as Tsunade then throated his entire length in one suck, her expert tongue slurping and squeezing his glands. She pulled back before gulping him up again, applying torsion, suction, and pressure to the cock. Shizune stared at her boss in admiration, not only was she taking this monster-penis for her sake, but she also was a master of the blowjob too! To be expected for a kunoichi of her caliber, Shizune nodded. A part of her was appalled at the behavior, considering Tsunade was almost fifty and Naruto was… not, but the sake she had ingested blowing Naruto dulled her rationality.
The only thing going through Tsunade's mind was cock. She sucked the soul out of the genin, pulling him closer as he weakly thrust into her willing mouth. Popping his dick out, she pulled Shizune closer.
"Now you pleasure his right side while I enjoy his left, make yourself useful!" Tsunade slurred before beginning to run her mouth up and down the left side of Naruto's straining dick. The slightly intoxicated Shizune brushed her shoulder-length hair back before nodding resolutely, kissing and licking up and down the length's right side.
Naruto could not believe his eyes. His previous sexual encounters had all been otherworldly in their own ways, but this was truly special. Two sexy and mature women were slobbering all over his dick at the same time! Putting one hand on Shizune's head and the other on Lady Tsunade's, he pushed their mouths against his penis harder, trembling from their hot licks.
His pushing caused the two women's lips to meet at the tip of the blonde's penis, making Shizune blush intensely. Quick kisses turned into long smooches. For several incredible moments, she made out with her boss, their tongues and lips wrapping around Naruto's bulging dickhead. Maybe this reward isn't so bad after all, Shizune thought, admiring Tsunade's horny expression as they shared the teen's cock.
Tsunade then poured sake over Naruto's penis once more, licking her lips before deep-throating him as Shizune watched intently. Kissing Tsunade had turned her on, and the blonde's cock looked more appetizing now. She realized she could still be helpful, bending lower to take the young man's balls in her mouth. Sloppy sucking sounds echoed around the Hokage's Office as Tsunade slurped Naruto's length while Shizune gulped his balls. Eyes blurring, Naruto wondered if he was about to die from a blowjob-induced heart attack.
He stared at the room's ceiling, waves of pleasure cascading outwards from his pelvis as he orgasmed abruptly. When he looked down, he realized that both of the bombshells servicing his dick had been painted by several loads of cum. Tsunade was hungrily licking the semen off of her face and boobs while Shizune was bashfully wiping it off with her hands, Naruto's wet cock dangling limply below him.
Shizune quickly departed, mumbling something about needing a long bath while Naruto sat on the Hokage chair, getting a feel for it. His pants were still off, penis seemingly flaccid once more. Tsunade, still pretty drunk, was warning him to keep their threesome a total secret.
"Yeah, yeah, I got it Granny." Naruto yawned, enjoying the chair's cushions as she yapped.
"Lady Tsunade, it's Kurenai, here for the mission briefing you spoke about earlier. I'm coming in!" a pleasant female voice called out from behind the door.
Kurenai, leader of Kiba, Shino, and Hinata's team, entered the Hokage's Office to see a cheerful Tsunade sitting somewhat oddly behind her desk.
"Of course, I almost forgot about our b-briefing." Tsunade responded in the most sober fashion she could muster. More importantly, she had to ensure that Kurenai didn't find out that she was sitting on Naruto's lap. Her Hokage cloak billowed out to prevent Naruto from being seen under and behind her. This had the added effect of removing the only layer of clothing between Naruto's rapidly growing penis and the older woman's wettening pussy. Tsunade leaned forward, feigning interest in Kurenai's small talk, as she felt the blonde brat gyrate his hips up, his cock trapped against her voluptuous ass.
Naruto, hidden under Lady Tsunade's clothing, could see her entire naked body as he took advantage of the situation. If every man in Konoha wanted a piece of Ino, every man in the Land of Fire desired the view he had at the moment. His hands eagarly snaked around the sexy Hokage's hips, pulling her up just enough to let his cock spring up, tip pressing on her cunt. He grabbed the sake bottle and poured the remaining contents on his tip as lube.
"Are you alright Hokage-sama?" Kurenai wondered, "You seem rather uncomfortable."
Tsunade, silently cursing the hung jinchuriki for his actions, realized she had no choice, "Oh, I'm just fine, now let's talk about this mission I am assigning you." she said, sitting back down, the fat cock sliding into her. For the next several minutes, Tsunade jerkily explained Kurenai's mission, stifling moans and gasps as Naruto slowly flexed his member, fully sheathed inside of her pussy. His hands roamed Tsunade's unblemished body; although she was almost 50, she maintained a permanent Transformation Technique to have the body of her 20s.
"Well… I think I understand now." Kurenai said with slight concern, "I'll leave you to your duties." With that, she exited the office, and Tsunade sat very still, not saying a word. Naruto prepared for the worst, grimacing as he felt Tsunade place her hands on his knees. He then lost his breath as the older woman began bouncing her fat ass on his dick.
"I'll punish you later-" she huffed, "Just let me take this cock right now, Naruto!" His luck continued to astound him, perhaps this is good karma for his shitty childhood, he thought. Naruto sat on the Hokage chair and relaxed as Lady Tsunade fucked herself on his dick like it was a dildo. Plap, plap, plap, her thighs and ass echoed as they collided with the jinchurki's lap. Although he thought he was spent, he felt another surge of semen building in his testicles; the view of Tsunade's jiggly, naked body grinding against his was like porn. All at once, Naruto and Tsunade came, his dick unloading inside the beautiful Hokage, both moaning gratefully.
Outside the office, Kurenai was touching herself as she listened, "When was the last time Asuma gave it to me like that?"
In her bath, Shizune was also touching herself, replaying the day's events in her head.