Where the Bad Guys Always Win

Tsunade the Whorekage

Tsunade bit her lip as she looked out the window on the Hidden Leaf Village. A group of rogue ninjas known as the Akatsuki were going around collecting Tailed Beasts, like the ones sealed inside Naruto Uzumaki. Luckily, he had just left with Tsunade's old comrade, Jiraiya, to begin a training journey, which should be enough to protect the kid from being kidnapped. Still, something told Tsunade that something bad was about to happen. Her aide, Shizune, tried to calm her, but it wasn't working.

Then, several explosions rocked the Hidden Leaf. Tsunade demanded to know what had happened when a Leaf Ninja ran in, saying that the Akatsuki had launched a surprise attack. Shocked, Tsunade gave orders for the Leaf's Ninja Corps to defend the Village, while she and Shizune ran to the roof. There, she looked up and saw a man floating there with orange hair and studs in his body, wearing a black cloak. He introduced himself as Pain, and demanded Naruto Uzumaki be handed over. Gritting her teeth, Tsunade got into a battle stance and refused the rogue ninja. The battle soon began.

Several hours later, the Hidden Leaf lay in complete ruin. Pain alone was several magnitudes more powerful than anything Tsunade had ever seen. Combined with the other Akatsuki members, and the Leaf Village didn't stand a chance. Most of the Leaf Ninja were slaughtered, any surviving citizens scattered to the winds. Tsunade herself laid on her back in a pile of rubble, her body heavily injured despite her medical ninjutsu, with Pain floating above her. With a simple wave of his hand, he sent a blast of chakra into Tsunade, causing her to slip into unconsciousness.

Groaning, Tsunade awoke to someone yelling into her ear, and fluttered her eyes open. She saw Shizune happy to see her alive. Next to her was Tsunade's new apprentice, Sakura Haruno. As Tsunade sat up, she also saw Sakura's peers Ino Yamanaka, Hinata Hyuga, and Tenten all kneeling next to her. Stranegly, they all had their arms behind their backs. That was when Tsunade tried to pull her arms ahead and found she couldn't! Looking behind her, Tsuande found her arms bound behind her backs with chains. Shizune tried to say something to Tsunade, but the busty Hokage channeled her chakra in order to break the chains, but was suddenly flooded with painful electricity and fell back to the ground. 

Then, Tsunade heard someone yelling at her to stay quiet. She turned her head to find that the Leaf women were all in a giant cage being led along by two men in black cloaks. Akatsuki! Shizune and Sakura explained the situation. Pain and the Akatsuki had destroyed the Leaf Village. Most of the Leaf Ninja were killed. Pain was annoyed that Naruto wasn't in the village, but one of the Akatsuki, Kakuzu, apparently had an idea in mind. He and his partner, Hidan, gathered up as many female surviving Leaf Ninja as they could and another Akatsuki member, Zetsu, applied a rare sealing jutsu that blocked the use of chakra. Luckily, it didn't dispel Tsunade's visual jutsu, so she still had her younger form. Looking out, Tsunade found that there were several cages and wagons trailing behind them, all filled with forlorn Leaf Ninja.

Eventually, they arrived at their destination, a small village in the outskirts of the countryside, and a place where the seedy underworld was out in the open. Kakuzu and Hidan stepped down and began a discussion with a few men near a large, extravagant building bathed in red lights. Both Tsunade and Shizune recognized it as a brothel. Sakura, Ino, Hinata, and Tenten all gasped when they heard, but then they were interrupted by Kakuzu and the brothel owner coming over, the latter of which sneered upon seeing Tsunade and Shizune. They had skipped out on a gambling debt they owed, and now it was time for payback.

All of the Leaf Ninja, including Tsunade, were forced out of the cages and lined up on the road. Hidan, after some complaining, went around and slashed all of the clothes off the girls, leaving them all naked. Many of the girls tried to keep a straight face, but many were already scared and crying. The brothel owner stepped up and leered at Tsunade, his lust clear in his eyes. He groped her breasts, marveling at how huge they were, before reaching down to finger her cunt. Tsunade growled at him, but as she was, unable to actually to anything to resist. The brothel owner laughed and agreed to terms with Kakuzu, handing over several large briefcases packed full of money. Making sure it was all legit, Kakuzu and Hidan bid farewell and were on their way. Leaving the Leaf women to their fate. 

Though Tsunade, Shizune, Sakura, Ino, and Tenten all had bark still, there wasn't much they could do bound as they were and with their chakra sealed. The owner's men came out and forced the girls to march inside the house. They began to be divided up and were shuffled into various rooms. Shizune, Sakura, Ino, Tenten, and Hinata were place into one room, while Tsunade herself was dragged off on her own by the brothel owner. She knew what would happen to them and ordered the vile man to let them go. He merely laughed and continued dragging the now-helpless woman.

They entered the owner's office, where he threw Tsunade down on the ground and threw off his clothes. Tsunade tried to fight back, but he easily pushed her legs aside and began to lick and suck on her giant boobs. The former Hokage groaned as her body was manhandled, and she cursed how sensitive her tits were. Almost immediately, she felt her pussy began to dampen. In between licks, the owner crowed about how he dreamed he would make Tsunade his whore, but he never thought he'd actually succeed. She wanted to give a smartass reply, but instead she squealed when he bit down on her nipple. Tsunade blushed in shame as heat began radiating through her body. 

After what seemed like hours, the owner stood up, his cock fully erect. Tsunade groaned as she expected him to fuck her wet pussy, but instead he sat down on her stomach, grinding the chain binding her arms into her back. He flopped his cock in between her massive boobs and squeezed them around his shaft, then began to pump back and forth. He groaned in pleasure as he always imagined what it felt like to tit fuck such giant balloons and sighed as it was just as he imagined. Tsunade gritted her teeth, unable to do anything to stop him abusing her body like this. Soon enough, he couldn't hold out any longer and exploded, sending many streams of cum on Tsunade's face. His scent swelled through her nose, which only made her hotter.

When he got up, Tsunade was hoping the man was spent, but she always did have terrible luck. The owner shifted back until he was between Tsunade's legs. He slapped them open, then caressed her thick thighs, delighting in how soft they were. Then he noticed her wet slit and mocked her for enjoying her enslavement. Tsunade started snapping back, but he slapped her cunt, causing her to groan. The helpless woman before him made him erect again, and soon he gripped her hips and plunged into her wet pussy.

Upon entering the owner gasped in pleasure as Tsunade's warm pussy wrapped around his cock. The woman herself groaned as she was fucked, hating that this was happening to her, but she couldn't deny her body's heat. She soon screamed as she came, causing the man to mock her again. She glared at him, but he smiled and grabbed her big tits to use as handles to fuck her deeper. She wriggled in his grip, but could not escape. Tsunade eventually felt his cock spasm and began to empty into her. As he pulled out, she was shocked to find that part of her missed not having the cock inside her. But her new owner wasn't done with her yet.

A few hours later, the brothel owner sat down on his office chair, relaxing. Before him, Tsunade, unbound, was on her knees sucking his cock. It looked like he had broken her, but Tsunade was simply biding her time. If she could get to the others, they could escape, find someone to undo the sealing jutsu, then go regroup with Naruto and Jiraiya. After swallowing another load, the former Hokage felt a hand grab her hair. The owner got up and dragged her out of the room. Tsunade had no choice but to crawl after him.

They eventually came across one of the rooms from earlier, and the owner opened it up, eager to show Tsunade what was inside. Her eyes widened in shock. Shizune, Hinata, Ino, Sakura, and Tenten were all fucking various men, with Hinata and Sakura fucking two men at the same time, while Ino took one in her cunt and one in her mouth. None of the girls were bound, nor were they resisting whatsoever. In fact, Tsunade's ears were filled with the loud moans of pleasure as the girls came again. Much to her surprise, Shizune was begging for her man to fuck her harder. The other girls soon followed suit. Any escape plan Tsunade had in her head dissolved as her owner's laughter echoed in her mind.

Three years later, a wooden stage was set up near the outer edge of town. There, the brothel owner was describing his latest merchandise for sale to a large crowd of unscrupulous bad men. On the stage were six former Leaf Ninja, all naked. Sakura, Ino, Tenten, and Hinata were chained to posts, forced to stand up and unable to cover themselves from the lustful onlookers. Shizune was next to Tenten on her knees, scared of what was to come. The girls were there to be sold as sex slaves to the most depraved corners of the countryside, and there was nothing they could do to stop it.

At the front of the stage was Tsunade herself. While the other girls were very animated in their objections, Tsunade merely knelt there with her legs spread and head down. They had spent the past few years being whores, making their owner lots of money. But he soon received a lot of new girls from other villages, so he needed to cycle out some stock. Much as he was lament to giving up Tsunade, he knew he would fetch quite the price, especially since he was known as one of the biggest sluts ever AND a former Hokage. Tsunade had made plenty of enemies who would delight in owning her.

But the former Hokage did nothing to protest her upcoming sale. Guilt overwhelmed her. If she had been a better person, she would have been able to prevent the Leaf Village from being destroyed and condemning the women of the village to sexual slavery. Shizune, Sakura, and the others didn't deserve to be sex objects for the rest of their lives, but because of Tsunade, that was the reality. So, as the various bids rained down, Tsunade braced herself for her future as a sex slave. 

Sakura was sold to a nasty-looking man who couldn't keep his hands off of her. Shizune was sold to another brothel owner who set up shop near the Hidden Rain Village. Tenten was sold to a group of lowlife bandits. Ino was sold to a disguised corrupt noble. Hinata was sold to a ninja from the Hidden Cloud. All that was left was Tsunade. Her buyer was a rogue ninja from the Hidden Leaf, who had been banished by the Fourth Hokage, and was quite eager to enact revenge against the Leaf Village's former princess.

Watching as her former friends and allies were sold off to a life of sexual servitude, Tsunade tried to hold  back tears. She didn't resist when the rogue ninja snapped a collar to her neck and roughly pulled her to follow him. As the crowd scattered, Tsunade whimpered as she saw the last of her home village taken away. She knew none of them would ever meet each other again.

Tsunade was always a magnet for misfortune.

But the former Hokage knew there was no coming back from this loss.