A buxom messenger with a surprise

Hinata went to greet this guest, byakugan active. A kunoichi in standard lewd uniform, headband on forehead, long orange hair, and tits rivaling her own stood behind the door. She was unarmed, but had a vibrating anal toy wriggling in her. Things looking safe, she opened the door.

"Hello, I'm Orihime. I was told a young man with spiky blonde hair was here. You, do you know a whore named Rukia?"

He kept his cool, staring at her tits all the while. "What if I did? What's it to you?"

"According to her, she had the contents of her ninja bag stolen after being used by you, and master put two and two together. After punishing Rukia for losing four collars, he ordered me to give you this letter of challenge."

She placed it over her pussy, getting the center of it wet.

"If you accept it, simply tear a hole in it with your cock and creampie me. Rukia will taste it later to confirm you're the one we're looking for."

Ino met a guy most likely the master in question, so she had an opinion on the matter, but what came out was:

"He was going to cum in me, but of course it's up to my master. Do you want fight after using this bimbo?"

"You know what? Yeah, I've been waiting for a good opportunity to kick ass. Ino, you can cum on your own."

As he pulled out, she actually did cum on her own. He had to check later if that was coincidence or not. For now, he let his lust overtake him further and plunged his cock through the paper and into her slutty pussy.

"Oh, you're definitely in the top five cocks I've had in the last twenty-four hours."

He tugged on her nipples as though milking them, then gave her spankings as he fucked her from behind.

"Yes, thank you for this treatment I deserve."

He was already on the edge from before, so he barely had time for a question before filling her insides.

"Sorry for the lack of warning."

"Why? Even if I wasn't experienced enough to tell when a man is about to cum, this result was the entire point of our sex. Besides that, cumdumps like me don't need that much consideration."

"Yeah, that's the thing. You talk about what you do or don't deserve a lot?"

"I suppose it's somewhat redundant, but orders are orders. Master likes us to revel in our submissiveness."

Naruto didn't press further into it, but instead followed her out. He got dressed and supplied, but the girls only brought their bags and their contents, walking around fully nude instead of mostly, not that they care at this point.

"What are the conditions of this duel anyway?"

"Standard really, except for our village's unique twist: ownership of a sex **** is transferred to the winner. You each pick which to gamble with so you can think about who on the way."

Naruto was concerned about the stakes, then interested in the idea of expanding his harem. As Ino expected, they arrived at the Kurosaki Clinic. They were greeted by Masaki, face covered in jizz, dripping onto her tits.

"Oh Ichigo, Orihime came back with a group of whores and their well hung master. Oh, did you perk up a bit down there when I complimented your cock? You into milfs? You have a mommy at home to service you?"

"Mom, that's enough for now. Go clean yourself up before you drool all over another cock."

"Of course dear, mommy hears and obeys."

Ichigo has Rukia on a leash and all fours, wearing a blindfold and vibrators in both lower holes. Orihime promptly feeds her the sperm she had stored in her.

"It's him alright. It's the kind of taste that lingered in my throat."

"So, you accept the duel because you're confident, or did you just want to fuck Orihime?"

"Maybe both. What kind of fight are you going to put up? Are you a ninja?"

"Hardly. Born into a clan of samurai. I'm quite the prodigy really."

"I have a good pedigree myself, not that stuff like that matters when it comes to kicking ass."

"Backyard. Two more whores are waiting. Bring your four whores and we'll be all set."

In the backyard, one woman had dark-skin, golden eyes, and purple hair. She also had a cat tail sticking out, clearly fake with the base up her ass. She presents Ichigo with his sword, a large one at that. Next to her, a girl with magenta eyes and hair, wearing a bunny ear hat. Both are red collared.

"Now that we're all here, it's time to pick our bargaining chip. Since you're new around here, I'll ask if you want us to pick our own or pick the one we want from the other. Oh, almost forgot. Rukia, make yourself presentable!"

She got up and removed her blindfold and front vibrator and she and Orihime got in line with the rest. Naruto has a discussion with his girls and hears about Ino's encounter, with explicit detail.