Chapter 9

Prison Video

Beta: Old man of the mountain/Darklord331

Naruto stared at Anko who was all smiles and Ibiki a scarred up Jounin who was all frowns.

'It is like they are polar opposites of one another.'

"So you understand what we are asking for correct?"

"Yeah you want me to break this new prisoner through sexual acts? Isn't this classified as rape though? Not gonna lie it kinda makes me feel off." Naruto frowned, "I might be a ninja that spotlights as a fuck machine but that doesn't mean I will force myself in that manner on a woman. I do have some principles."

Anko rolled her eyes while Ibiki nodded.

"We are not asking you to do that. In fact quite the opposite, we want you to arouse her to the point that she'll spill her guts just to get some relief."

"So, pent up frustration and then fucking? Why not use some sexually stimulating drugs on her?"

Ibiki frowned,

"Nothing of that nature is available to us and other nations find out we are doing this to our prisoners and the lord finds out, then it could be trouble for us. So the best option we have is you." He turned to Anko, "From what Anko tells me your chakra can actually stimulate someone's ability to really get turned on."

"I guess." Naruto shrugged his shoulders, "I think it is a byproduct of me being a tailed beast vessel."

"I see." He sighed, "Look go in there, ask her questions and if she is still her cheeful self then you are free to arouse her anyway you please."

"Okay by the way does the old man know I'm down here?"

"Yes, in fact he is the one that agreed to this method with Tsume vetting for it. Given you knocked up one of the most desired MILF's in the village and from the rumors are leading her around, it is no wonder you are assigned this job."

Naruto rolled his eyes, "Yeah, yeah I fucked a MILF, I'm not perfect though." Remembering the titfuck he got from Hitomi was enough to annoy him. "So what is her name?"

"Guren." Ibiki looked down on the file, "From what we gathered she is apparently a bloodline user, jewel release or something like that. Tayuya and Kin confirmed this info and stated she was one of Orochimaru's highest ranking subordinates. Meaning she might have some information that we are missing. Might even know where the traitor is hiding out most of the time."

Naruto shrugged, fair point.

"Also, the old man doesn't want people getting to her for her bloodline right?"

"Yes." Ibiki sighed, "Already threw four of our own people in jail because they wanted to, 'inspect the prisoner' or 'give a full body search' when they were not authorized to do so. Got a strange feeling a lot of them are paid to do this but some are just horny." He smiled, "But I don't have to worry with you, as your being paid for this."

"True." Naruto sighed and stretched, "Okay take me to the frigid bitch."

Anko laughed while the two lead him into the private chamber. There, he saw the room was spaced out quite a bit but the woman in question was chained to the wall. Chakra suppression seals on the entire room for her and only enough wiggle room for him to use his chakra whenever he wants.

"Okay wish me luck."

Naruto opened the door and saw the purple hair woman glaring at him. He sighed, he really had to take her in at this point. Because while not as busty or exotic as some of the other women he is fucking, which reminded him he needed to give Tenten some love soon, he saw she was fairly busty. She at least was a D-cup if not E-cup, a large ass for herself, and even with the baggy prison suit he could see she was fit.

"Hello there my name is Naruto Uzumaki."

"….."

"So as you can guess, they sent me in here to get info from you so I have a proposal. You tell me what we need to know immediately and then we can see about getting you out of here. Don't and well, I have to get creative and trust me it is going to be cruel if you are not ready for it."

"Fuck you Leaf scum, I heard all about you from Lord Orochimaru."

"Good then you should know that I do fuck on the regular. I do have an opening on Thursday if you want to afterwards."

She growled, "Go to hell just because you are a bit stronger than expected and defeated Gaara, that means nothing to me. You won't get shit from me like you did with Tayuya and Kin."

"Oh them? So you know they are working for Snake Studio."

"So what? Always knew those girls would whore out if that meant staying out of trouble in the long run."

"Hey I wouldn't judge, they are just working there no fucking whatsoever."

"Whatever, fuck off and leave me alone."

"So my way it is, kinda hoping for it honestly wanted to work some stuff out." Naruto quickly unsealed a scroll on the table and she paled when she saw some of the stuff assembled. One was a quite big dildo that seemed to have some kind of rough texture with bumps. Another item was a small set of clamps which looked as if they were meant for her nipples. She also saw some kind of other dildo but it had a flat bottom with some kind of button on it.

"Okay now so what should we do first?" Naruto snapped his fingers, "We'll need to get you out of the jumpsuit first."

Naruto walked over to her and she growled,

"Don't you fucking touch me!"

"Geez calm down," Naruto pulled out a kunai, "Otherwise this might be more painful for you."

He put the tip against the front of her jumpsuit and after slowly slidding the tip down he opened a hole through the front of her jumpsuit from the neckline to the crotch.

She jumped up and tried to wrap her legs around his head but Naruto saw this coming.

He quickly put his arms up stopping her from wrapping her legs around his head but kept himself close to her crotch. While he couldn't see it through the bottom of the jumpsuit as it was still hidden, he could see just the smallest signs of her crotch through the opening. Without warning he leaned forward and dug her tongue into the crotch of her jumpsuit forcing it into her pussy.

She squirmed and soon a blush emerged with a small moan.

Her legs started to quiver, allowing him a chance to get out of her leg grab while holding onto her thighs. He pushed her legs down and grabbed the bottom of her jumpsuit that was cut and quickly pulled it apart revealing her pussy. There, he grabbed one of her legs and pulled it out and then did the same with the other leg. This left her bare to the world with only the sleeves intact but the rest of the jumpsuit hanging behind her.

She had E-cup breasts for sure, they just hung out for all to see and were very slapable with her having decent size nipples. Her stomach was taut and she had a small patch of fuzz above her crotch. Her ass was the biggest thing outside her breasts and seemed very bouncy, Naruto believed at least, compared to some of the women in his life.

Even though she wasn't a MILF he could tell she was stacked and it was going to be fun breaking her.

"Now then," Naruto walked back over to the table leaving a slightly horny woman standing there. "Do you want to talk or do you want more?"

"F-fuck you."

"Sweetheart you going to be asking me to do that later but for now how about this?"

Naruto grabbed the clamps and walked over to her. He then aimed them at her nipples and snapped one onto her right tit.

She groaned at this sudden sensation and was shaking.

"Oh so your sensitive there?"

"Y-you wish."

Naruto smirked. He quickly snapped the second one onto her chest while having a small line that connected the two clamps together and tugged on them gently.

"You sure you're not sensitive there?"

"F-fuck yourself."

"Oh well," Naruto quickly pulled harder on the clamps making her shiver and bite the inside of her mouth. Not wanting to scream from the sudden pain she was in.

"Well that was a surprise. You sure you don't want to talk? I mean we can always do this," Naruto dropped the line of chain connecting the clamps, he then grabbed the clamps and roughly twisted them.

"FUCK!"

"Oh, I think we hit something." Naruto's smirk grew, "Well guess if you still won't talk then we can move onto the next toy."

Naruto walked over and looked at the vibrator and the dildo and measured up. He wasn't 100% sure which one would be better in this situation but he figured more stimulation was needed before he rough her up some more. So grabbing the vibrator he walked over to her, and waved it in front of her face.

"See this? Nice little toy someone showed me a while back. Don't use it myself don't like getting pegged to be honest. Don't like too many things going near my ass but hey I hear it is a fun time." He looked at the bottom, "Supposedly there is three settings to this thing; slow, medium, and fast. But I see that there is a fourth option on this one. Not sure what it means but I think that we should give it a try no?"

Naruto quickly put the vibrator into her quivering snatch, before flipping the device onto the highest setting but he was shocked.

Literally.

The battery was releasing a small shocking pulse through her pussy through the entire body.

Guren's eyes rolled into the back of her head and she moaned wildly. Feeling her entire body shaking and her mind falling apart due to the sudden sensation.

The woman's body was just shaking wildly and her face was red as an apple. But soon, her body started shaking more violently before she just fell into a relaxed state while moaning on.

But the woman herself was dripping down the vibrator onto the floor.

"Well it would seem that this is too much for you." Naruto walked up to her and frowned, grabbing her chin, he lifted her up. Eyes glossed over and her mind vacant.

"Come on Guren, surely this is enough? Just tell us what we want to know and I can promise you," He leaned in close, "I'll give you release you never imagined and who knows? You might find something new to worship."

"N-no." She was whimpering and moaning at the shocking sensation. "P-please make it stop. I can't betray them."

Naruto sighed.

"How he gained your loyalty is beyond me but I guess it doesn't matter the old man and the interrogators want to know. So I'm going to have to break you and get that information."

Walking over to the table he showed her the dildo which made her eyes widened.

"So I'm pretty sure you can guess where this is about to go?"

"W-wa-wa-wa-wait,"

"Oh, do you want to talk?"

Guren frowned and bit her lip.

"Hm, it would seem that is not the case."

Naruto went to Guren and started reaching behind her with the dildo rubbing against her ass cheeks.

"I wonder, how uncomfortable this is going to be for you?" Naruto shrugged, "Oh well not my business."

Before Guren could moan out for a stop, he quickly pushed the tip of the dildo inside of her ass and her mind just exploded.

She screamed at the pain of her ass suddenly expanding without any hesitation. She was dry docked and she didn't like it for one second.

Naruto raised an eyebrow,

"Not a fan?"

"Of course not it hurts!"

"Good." Naruto twisted the dildo making her scream more, "Now then, if you are in so much pain tell me on a scale one to ten how does this feel?" He then did a complete 360 of the dildo.

She screamed and her eyes watered.

"10! It's a 10! Fuck please stop!"

Naruto smiled,

"Then tell me what I want to know." Naruto then jolted her again with the vibrator and added another small twist from the dildo. "Come on, the sooner you tell me the sooner I can take this out and who knows maybe I can give you some sweet loving if you want it?"

"P-p-p-please, stop. I'm begging you."

Naruto sighed,

"Already said what you need to do."

"No I can't I-," she felt the dildo slowly turning and she paled. "Wait what about the other girls you could ask them what you want to know bother them not me! Tayuya was literally in his inner circle."

"Oh they already told us everything we wanted to know and are serving as workers in our studio. But you? Well, I'm not sure what is going to happen to you. Might just leave this vibrator inside of you and have this dildo on a method of causing it to rotate constantly."

Guren paled even more and she finally felt her mind cracking.

"Please, please take it out I'll tell you everything you want to know just please stop it!"

"Now that is what I want to hear but I don't want you going back on your word so tell me everything and THEN I'll take this little puppy out." He gave a slight twist.

"FINE!"

On the other side Anko couldn't help herself. She was hot and horny seeing Naruto do this to the poor bitch. She had no sympathy for her but honestly she was not sure she would last that long in those kinds of interrogations. He really picked out the best methods to win this bout.

However, she was too horny to care about making money or hearing the information that she turned to Yugao and had her strip out of her uniform. From there the two of them started doing the 69 and eating one another out. They had a strap on put to the side for when they get to that part of the event.

Ibiki was sent away awhile ago but he knew that he would get the confession and info later thanks to the video. Once they did that, they would remove it from the tape and then send it out for Snake Studios while he got a discount on it.

Hey, he was scary man not a gay man.

Back in the interrogation room, Naruto had just finished hearing everything Guren had to say while making sure to twist to remind her who was in charge.

"So that is everything?"

"Yes."

"Are you sure?" Naruto gave a gentle twist, "Because I would hate to have to leave you here with this deep in your ass twisting every five minutes."

Guren paled, "I swear that is the location of all his bases, all of his people, all of his spies, and everything he has been up to since I known him. Please, just please take it out of me!"

Naruto looked at her and shrugged,

"Okay." He removed the dildo from her ass and her legs quivered before going limp.

Naruto then removed the vibrator from her pussy and he smiled,

"So you been a good girl now what do you want?"

Guren was huffing, "Please just anything. Anything, I'll do anything if you just let me feel pleasure for five minutes!"

"Oh and if I wanted you to commute your sentence as one of my studio's actresses?"

"I'll spread my legs and do group fucking if that is what is required but please, just give a little love!"

Naruto sighed,

"Sadly, I can't do that."

"WHY!"

"Simply put you have to earn it and as punishment for your actions siding with Orochimaru there are some people that want to punish you too." Naruto walked over to the door and opened it.

He deadpanned.

"Really?"

Anko was prepping the strap-on while Yugao was playing with her pussy, making sure she was nice and wet.

"What? We are women we can get hot and horny from watching stuff like this."

Naruto sighed, "Didn't say you couldn't. But come on, really? You just had to start on something like this right as I'm finishing?"

Anko rubbed the back of her head,

"Well," Naruto pointed into the room, "Get in there she is ready for both of you. And please, try not to destroy her she is still a person after all."

Anko laughed, "Come on you know me!"

"I know that is why I'm saying it."

"Asshole!"

"Maybe yours later."

Anko huffed before securing her strap on and walking into the room with Yugao looking conflicted.

"Come on your in there too. You got to make sure she doesn't break the poor woman."

Yugao smiled, rushing into the room with Naruto sighing.

"They call me insatiable."

Naruto sat down and started watching the video, he took his cock out of his pants and started stroking himself.

In the room, Anko stood there with a smile on her face and her strap on pointing straight at Guren.

"Well now Ms. Cocky not so high and mighty are you?"

Guren paled,

"What are you-,"

"Well you see, I got all hot and bothered seeing how Naruto basically destroyed you without his dick. So the two of us got a bit hot and decided to help relieve the stress." Yugao walked over to the table and admired the dildo that was used and turned back to Guren. "So we decided that if you broke then we get to play with you." Anko walked over to her and grabbed her by the breast clamps and smiled, "Seeing as how you were pretty mouthy against me I want to hear the insults again. What was it you said to me? Oh right that I was a worthless whore that couldn't satisfy Orochimaru?"

"I-I-I'm sorry."

"Oh you are?" She smirked before adjusting herself to be right in front of Guren.

"Well apology accepted."

She quickly thrusted forward making Guren moan from the sudden penetration of the dildo.

"W-wai-,"

"Sorry, no can do." Anko pulled back and started slamming into Guren while grabbing a hold of her thighs. "You see I'm now going to punish you by plowing the fuck out of you and unlike most women this is something I'm an expert at. Trust me, breaking you is going to be a fucking blast."

Yugao looked on and sighed,

"Guess I'll take the back door." Yugao quickly summoned a strap and tied the dildo from before onto it. Then walked over to Guren's ass and quickly pushed her way past the cheeks.

Guren started screaming and begging for mercy but neither woman was listening. Just both gaining steady rhythm with one another making the dildos tear through the woman's ass and pussy.

Naruto on the other hand sighed, "Okay this is hot as fuck. Might have to watch Anko do more work down the line."

"Naruto!"

Turning his head he saw Tenten running to him.

"Hey did you use the new-," She stared down at his dick, "You did already?"

"Yep they worked perfectly."

"Good to know." Tenten walked over and saw that he was watching Anko and Yugao with Guren. "Sheesh remind me not to let Anko near my asshole."

"Oh come on you know you love her."

Tenten rolled her eyes,

"Sure but not enough for that. Amazing she is taking two of those strap ons both in her ass and pussy."

"Not really by choice."

"Well want help?" She pointed down at his dick.

"Sure if you don't mind."

Tenten smiled lustfully, "Never will I mind bouncing on this dick." Quickly discarding her top and bra, she took off her pants and panties before jumping onto his lap. "Oh I have missed this."

"I have missed this too." Naruto twisted her nipples making her moan. "Go ahead moan for me and take my seed. You know you want it."

Tenten smiled before she started increasing the pace and power of her bounce.

All the while Guren was having her mind melted by Anko and Yugao and all anyone could hear from this area was moaning and the clapping of asses.

Chapter End