Naruto didn't become a Ninja, he became a Boss

Konohagakure, a pinnacle of the ninja villages since it was considered the strongest of all the villages. However, like every village it had a dark/shady/criminal side that many weren't aware of or at least wouldn't speak about in the open. Konoha possessed a Red Light District and it was the only place that was lawless in the entire village... or at least that was how it was till about two years ago. Two years ago, a young man began taking over the different areas whether it was the brothels, the love hotels, the casinos, the fighting rings, black markets, the **** auctions, whatever, he was taking it over piece by piece and no one could stop him. Those that tried were quickly dealt with, either killed, enslaved to him, or sold off to others for their amusement.

His take over was so complete, so absolute, that anyone outside of the RLD noticed and wanted to investigate only to find it was still lawless and criminal filled, they just now answered to one man and had to pay a tax on anything of value they brought in or took out. The women flaunted their bodies more and had no shame or fear of what they did, the thieves picked in broad daylight anyone that didn't live in the RLD, the casinos pilfered and gave money depending on the luck with those in debt having to work off their debt in various other institutions and methods.

Because of his control and the money he was bringing into the village, he was given a seat on the Civilian Council that the Third Hokage had created to help get the village back on its feet with reconstruction and regrowth after the Kyubi attack years ago. Many wanted to challenge him having a seat, but with his control essentially boosting the economic wealth of the village five fold, there was not much room to argue with the Hokage and Elders agreeing to his position.

His name you ask? Naruto, Naruto Uzumaki

As you can no doubt guess, Naruto wasn't liked by his fellow villagers and was slowly chased/pushed from the normal living area to the Red Light District (RLD). There they weren't hostile or cold towards him since they honestly didn't care. The RLD hadn't been touched during the Kyubi attack and people had frequented there more often to cope or forget their troubles and brought more money for them.

Naturally, Naruto adapted to his area and started learning the trades by getting a place to live in a hotel by being a worker/runner for the manager. As he grew, he began learning from some retired shinobi and kunoichi in different items, styles, and ways of combat, which then led him to being a guard, bouncer, and protector for different areas while already working as bartenders, servers, moving shipments, and more. He grew his skills more through learning pickpocketing, stealth, infiltration, climbing, eavesdropping, blending with crowds, and throwing weapons. This also helped him in climbing the ranks in local thieves dens and working the casinos.

However, when he reached 15 he began enjoying the physical pleasures of the businesses too by sleeping with different madams and hookers to learn the trade and skills to please a woman with his chief asset being stamina, though he wasn't lacking in the other departments either. Of course, this plus working the thieves dens and casinos also gave him an information ring as eavesdropping worked easily during following a target or listening to losers at the casino ranting after drinking their worries away or celebrating. Pillow talk also helped with gaining information because Naruto made sure all the women he slept with were satisfied and comfortable with talking to him as he listened intently and diligently. This not only got him more information, but also got him some points with the women earning him repeat customers and allies.

Once his skills were adequate enough, he went into business for himself and began assimilating different areas into his control. It wasn’t hard since he knew the inner workings of each area and the brothels gladly came under his employ both for protection and to get him in their beds again.

The mercenaries and thugs fell in line next due to Naruto having established himself as the best fighter in the district and no one wanted to cross him.

The casinos fell next since Naruto literally had the Devil’s luck when it came to gambling and he would wipe out the casino vaults and then buy out the places using the money he had just won.

The bars and taverns went next with Naruto placing some of the prostitutes as waitresses and barmaids. This drummed up business for both businesses as the girls would flirt and draw customers and the customers would try to show off and buy lots of drinks before then heading to a hotel. The bars also reduced their prices since that made people buy even more drinks and get drunk faster, which let them buy even more drinks or made them an easy mark to be pickpocketed.

Especially if the poor sucker had just lost big at the casino.

The casinos served more **** and had more scantily clad ladies both as dealers, waitresses, show girls, and more. Plus every one in four dealers were sharks to swipe money from all the big ticket people.

The hotels were renovated to make them less........ derelict in appearance and the smaller ones still had decent prices for the not so rich.

The different black market and smuggling areas were taken over and renovated to add more security and ensure double crossers were handled properly.

The fight clubs were cleaned up but there were still plenty of the more brutal fights and women were added to some fights, which were both brutal and had lingerie or bathing suits options too.

And of course, every installation and area had cameras, security, and watchers observing and ready to handle any problems or assholes that wanted trouble. The RLD was his and he was ensuring no one could touch it without him knowing they wanted to.

However, Naruto also needed to expand and control more to get more goods and currency flowing both to himself and the village. that wouldn’t be hard though, he could easily hire a Shinobi team to act as his escort as he found more places to add to his territory and maybe some women to add to his service and bed.

Currently we find the 19 year old Naruto relaxing on a couch in his private office in his biggest casino. However he wasn’t alone as currently riding his dick was a blond bombshell named Tsunade who had J cup tits, a plump ass, wide hips, and long legs. Tsunade wore only a collar around her neck with The Uzumaki spiral on it, black lace stockings, and black heels. One could also see her nipples were pierced with rings, her ass had a tattoo above it that read “Naruto’s Senju Slut”, a cord necklace with a green crystal was around her neck, and her left ring finger had a platinum band with an emerald on it.

Beside them, standing at attention, was a woman no older than 25 with black hair wearing a maid themed outfit. It was a black lace mesh leotard with white frills to cover her nipples and mini apron that only just barely covered pussy while her ass was completely exposed. She had black cuffs on her wrists with white frills, black lace stockings with white frills, black heels, a maid bonnet, and a black choker with the Uzumaki spiral on it and a tattoo on her ass saying "Uzumaki Property". This was Shizune, a slut turned maid for Naruto and one of his popular floor girls.

Tsunade and Shizune had been an acquisition that wasn't intended but Naruto made full and pleasurable use of.

Tsunade had been a big gambler and drinker with a legendary knack for losing at gambling and Naruto played the understanding and friendly card in that she could pay off the debt with favors, nothing sexual to start just heal a person here, teach some medical skills there, be a server at one of his casinos, be a dealer at one, access to some jutsu, information on the clans, and so on with Naruto paying her for her work while also taking a bit of debt off. It eventually led to Tsunade being a bit insulted thinking he didn't find her attractive, which is what Naruto wanted and made it easier for him to start getting physical items and pleasures. A kiss, a grope, a make out session, a photo session, her masturbating for him, a hand job, a blowjob, being his personal waitress while he was "attended" to, a titjob, an assjob, a mixture of items, and then finally fucking him and letting him take her anal cherry. By the point he got to that last item, Tsunade was pretty much a "yes girl" for him and was giving him anything and everything he could want including her, which was helped by him giving her necklace back when she had to sell it off for debt.

The fact that she could gamble, drink, and have fun without fear or worry was another bonus to her and the constant fucking and showering of things just turned her more and more into a **** for Naruto.

Knowing she wanted kids and stability in her life, Naruto proposed the agreement of marriage in that he'd love, cherish, fuck, and care for her while making sure she got pregnant by him as many times as she wanted, and in exchange her entire clan assets would belong to him giving him complete control of the Senju money, possessions, jutsu, property, everything and THAT would expand his influence within Konoha to great heights.

Naturally, in her lust and addiction fueled mind, Tsunade gladly agreed and as part of her vows for the ceremony swore that her body was Naruto's property and she was a breeding bitch cumdump whore for her beloved boss and couldn't wait to bear him an army of children while serving his dick.

Shizune had been an acquisition when she tried to free Tsunade, but she wasn't going to wager things so Naruto made her a deal: Survive a week as his personal maid, but she had to obey her orders, he wouldn't order Tsunade for that week, she couldn't deny or refuse anything, and she had to give her all in being his maid.

If she won, he'd free Tsunade from his service and never make her do anything again.

If he won, she'd stay as his maid and **** and be bred right alongside Tsunade.

Shizune had accepted and had served wearing that outfit.

Naruto didn't fuck or make her do anything sexual, the first few days at least, just groped her and made her cum or made her stand ready while he fucked his bitches and whores in the district, not counting Tsunade, and kept teasing and building her up.

Day three was blowjobs.

Day four was titjobs.

Day five, she caved and wanted to be fucked since Naruto forbid her from masturbating and was only allowed to cum from him.

Day six she was fully into sex and fucking while still clinging to saving Tsunade with Naruto being merciful and not cumming inside her.

Day seven she walked in on Tsunade rapidly bouncing on his dick and shouting his praises.

Shizune had been outraged at him breaking the deal, and jealous of Tsunade riding him, but Naruto pointed out that he agreed to never order Tsunade to fuck him, her doing it herself was fine.

Tsunade agreed, fully stating that she loved being Naruto's bitch and had no intention of leaving or stopping letting him use her pussy and ass. Shizune was free to leave if she wanted, but Tsunade was forever going to be Naruto's bitch and whore just before Naruto flooded her pussy with cum again..

Shizune, finding that she went through all of that and resisted as much as she could for nothing, crumpled down and began crying before Naruto walked up and stood before her.

He told her that she had a choice: She could leave and forget about all of this and try to live a life or... she could stay and be his personal slut, whore, and cumdump, but in doing so he wouldn't pull out before cumming anymore. She would get pregnant and serve him just as Tsunade did and she'd get all the love, attention, and pleasure that she could from him from now on.

No more traveling.

No more dodging mercenaries, debt collectors, or assholes.

No more having to handle a drunk Tsunade and never getting to settle down.

No more any of the negative things in her life.

Just serving Naruto, pleasure, and a family she could have for herself.

Naturally, Shizune took it and swore her life and devotion to Naruto while licking and sucking his dick before she offered her pussy to him and begged him to grace her with his seed.

The two never looked back.

Jiraiya had been peeved that his desired woman was gone, but Naruto was a good sport and let him have plenty of "material" for his books just so long as Naruto got a piece of the profit. Tsunade and Shizune didn't care about being recorded, watched, leered at, or desired, they only cared about serving Naruto, pleasure, and following his orders.

The porn and added profits from Jiraiya only increased Naruto's wealth earning him the nickname "Daimyo Kage of Vices" and he earned that title since Tsunade's decision helped improve him a lot along with Shizune. Both trained doctors, medics, assassins, apothecaries, and soldiers for Naruto using their skills.

It was good to be Naruto, but he wasn't satisfied with this. He wanted more, and he'd get it.