Earning Some Pocket Money (Naruto)

Premise: Even with his healing factor, sometimes Naruto gets hurt enough that the old lady bans him from ninja duties for a while! The nerve! Though, in truth, he doesn’t mind too much. It lets him slip back into an old and very fun pass time of his that let him get the funds for quality ninja tools.

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Naruto leaned back on the corner of his street; his Sexy jutsu in place, the clothing he’d bought was all clean and did well to accentuate his very feminine form. His orange skirt barely hid his lower parts and it certainly let people get a nice look at his ass even without bending over. All the while his orange top was strained to keep his nice juicy breasts held up as the buttons strained heroically to keep him “modest.” Not only that but he’d gone the extra mile and with his extra money from missions, had gone out and bought himself something to “invest” in his off duty hobby. Now, he had some tall high heeled boots to go along with his orange and black striped stockings and arm length gloves. Then as a cherry on top, he also was wearing a leather collar with a D-ring dangling from it. He did have a chocker he could wear instead, but the clientele he’d managed to gather over the years were on the kinkier side so they’d appreciate this much more, especially after how long he’d been gone.

Not that he’d be opposed to offering himself to someone new. After all, a new person could be fun to enjoy for a bit. Just so long as they were okay with his package downstairs. Though maybe he could change that in the future. Sakura was learning under Tsunade to be a med nin, so maybe he could borrow one or two of her text books on female anatomy and give someone the full Naruko experience. But then, the Naruko experience was what he had right now anyways.

Maybe a new form would be good for that?

Of course, he wasn’t the only Naruko out on the streets, just across from him was a clone of his, plying the same trade, offering herself to a man passing by, pressing her breasts into him and having her voice go all low and sultry. Naruto watched the show, his cock hardening a bit as he knew the clone’s own was doing as well. Made small of course, after all, some of his clients loved the idea of him being small and pathetic down there and all sexy up top, except for one or two. Those ones wanted the whole thing, both his sexy and feminine body and his nice big hard cock to suck on as he dominated them, so he usually just had two sexy jutsu’s up, one for his lovely body, and the other for his-

Then Naruto heard a clacking sound as something small and metallic latched onto his collar, and he felt a pull from the side. He made surprised sound as he was pulled a bit before someone grabbed him and pulled him into a kiss. Naruto made a sound but quickly closed his eyes getting right into the kiss his hands moving to explore this person, and was surprised it was a woman, feeling her breasts pressing up against his before he grabbed onto one. His other hand going for their ass and found this woman had quite the tush. As he squeezed a bit the woman, no girl, squeaked a bit, and Naruto opened his eyes to see Hinata groping and touching him. The shy girl of all things! For a moment, Naruto decided to take charge, trying to push forward, to sweep her off her feet and maybe even touch her down there, but she resisted.

Instead of him taking charge, the heiress instead pulled the collar backwards, chocking Naruto lightly before smacking his leg and having one nearly fall out from under him as she instead went in for the deep kiss. She held him close as she deepened their kiss, her tongue surging forth into his mouth. It was like an electric current was running through Naruto and he knew his transformed dick was just barely poking out, poking the Hyuuga heiress in the leg as it slid between his leg and lightly pressed against his crotch. Naruto moaned a bit as he fell into his enjoyable routine. He hadn’t expected Hinata to be so dominant, but he’d experienced some pretty unexpected things when he did his little money making hobby.

Eventually though, of course one of his clones broke the moment as he heard her cheering.

“Heck yeah Hinata, show her who’s boss!” she said as Naruto felt Hinata giggle a bit before pulling back, bringing Naruto up by the collar as the two pulled away from each other’s kiss. Naruto gave the Naruko a look but the clone was entirely unrepentant, grinning from ear to ear before running off, doing a ninja jump to mock him as well. Since she was a clone, she didn’t need to listen to the old lady unlike him. No, he had to wait until his injuries “fully healed” before he could go back to doing ninja stuff, even though they had. Of course he could try to ignore her, but she always knew. But whatever, she was just fussing over him and he didn’t mind it that much. Naruto just shook his head before looking to Hinata. 

“My clone already told you the deal?” he asked to which Hinata nodded. Like usual she was all red, but this time Naruto was pretty sure it wasn’t from the usual fever that Hinata regularly had but rather this time from being all horny. After all, why else would she seek him out? Then again, why would she seek him out when she had a fever anyways? Ah well, she’s just like that sometimes he guessed.

“We’ll head back to a place I rented for the night, oh, and uh… I… I have something you need to wear,” Hinata said, her blush growing even redder than before as she reached into her hoodie and pulled a chastity cage.

“Nu-uh, I did that once before and the guy wouldn’t let me cum for a week, and then kept me locked up for a month after he changed the rules on me before he finally let me out after I made all my clones stop fucking him, and I started to refuse him as well,” Naruto said, crossing his arms, which incidentally pushed his breasts up. 

“Please? Father won’t let me be with someone like you unless you wear it, and he’ll know, it’ll just be for the night, and you can have the key,” Hinata said holding up two keys before holding one out for him to have.

Well in that case. Naruto took one of the keys before making a clone of himself, this one a non sexy clone, and passed the key to his other self. 

“Keep it safe, I don’t want a repeat of last time,”

“Okay boss, I know where to keep it,” the clone said before jumping off and rubbing in his face that the old lady had forbid him from doing ninja stuff. God damn clones. 

“You’re not keeping it on you?” Hinata asked, and for a moment Naruto expected her to object, but instead he saw a dangerous glint in her eyes and a slight upturning of her mouth.

Maybe her Father isn’t forcing her then, though it doesn’t matter now. If she wanted to have a kinky fun time with him, then whatever, so long as she wasn’t trying to turn him into her personal… well it wouldn’t be a cum dump since she doesn’t have a dick, so sex slave. 

“Nah, you’re a friend, so I’ll put my trust in you, Mistress,” he added the last part, and couldn’t help his ear to ear grin as Hinata’s face lit up like a tomato, but thankfully she didn’t pass out, instead breathing hard as she tried to calm down. Damn, she really isn’t doing well. Maybe they could arrange something to help her deal with lewdness. After all, it wouldn’t do for a ninja who specialised in seduction getting Hinata to pass out just like that in the middle of a fight. 

Eventually though, she finally seemed to calm down a bit, but her smile never lowered. It looked like this was the happiest time in her life as she looked at him. Though now she lifted up the hand with the collar, and tugged at it a bit while she turned around. 

“C-come on then, Narut- s-slave,” she said, her stutter adorable as Naruto had to fight to keep from giggling at her. 

God she is adorable!

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They arrived at the apartment that Hinata had apparently rented out with some of her allowance. 

Imagine having that kind of money, Naruto thought as he walked into the apartment following Hinata still by the collar. Hinata hadn’t really wanted to be seen so she’d swept Naruto up into a bridal style carry, and had carried them both off; Hinata hidden under a cloak looked like any other ninja enjoying their time with a whore after a mission. Which in truth, really was what Hinata was doing.

Still pulling Naruto along by the collar, Hinata drew her in and Naruto had to whistle as he looked the place. Despite it being a place being rented for a bit, the apartment was kind of swanky, especially compared to his. His own was just a simple one room thing while this place had more than just a single room and a bathroom. It had to have at least three or four rooms! 

“Nice place you got here, Mistress,” Naruto said, the last word rolling off his tongue in a sultry way as he walked up behind Hinata, sliding his arms around her, causing her to gasp a bit as his taller form enveloped her and pressed his breasts and jutsu’d micro dick into her. He didn’t fondle her, that might break whatever idea of dominance she might have had, but just embracing her, and making her horny? Totally on the table as her face grew redder and her breathing became heavier. So cute and adorable. 

As he hugged her however she pulled away from him, and tried to catch her breath, trembling a bit, her legs rubbing together before swallowing, then looking right at him.

“Go-go to the bedroom and wait for me there,” she said, a slight tremble in her stuttering voice, even so, Naruto bowed deeply to her. After all, she wanted the full master slave experience… probably, and she’d likely pay him handsomely for it, not that he really charged extra for that kind of stuff. 

“Yes Mistress, I’ll wait you there~,” he said in a sing song voice as he sauntered off, making sure to sway his hips like so many of his clients loved. 

Entering into the bedroom, Naruto sat on the bed, wondering what exactly Hinata had planned. She wanted him to wear a chastity cage for some reason, so they’d likely be playing with toys. She’d likely want him to eat her out as his cock strained against the cage or something like that. Though that would already kind of happen if he kept the sexy jutsu on his dick going as well. Micro dicks aren’t exactly useful for much after all. 

As he thought on their fun, he heard the door slide open. Naruto looked up, and smiled. Definitely having fun with toys then, as Hinata entered, not only had she stripped to just a set of sexy underwear that didn’t hide her private places at all. The underwear instead showed them off, her nipples poking out of holes in the bra, and the only thing hiding her modesty down below, was the thick dildo handing from straps on her waist.

So she’s one of those, fun! Picking his feet of the ground, Naruto lifted them up onto the bed and spread his ass, looking over the rise of his breasts at Hinata and made a desperate looking expression.

“Please Mistress, I’ve been so horny lately, I need your thick dick,” he said while adding a cute little pout at the end, laying it on a bit thick and being a little campy, not that Hinata seemed to mind. She almost seemed want to jump him right there, her hands twitching as they lifted up a bit before stopping herself, and bringing forth the cage, and what looked like a glass of ice cubes.

“Naruto, can, can you, undo the henge on your penis, please?” she asked, and with a thought, Naruto did so. His micro dick poofing away in a puff of smoke to reveal his hard cock standing tall and proud. Hinata’s blush grew worse and her breathing grew ragged from seeing it, the pampered girl likely not seeing too many dicks in her day, but now she could, and it was obviously overwhelming the girl as she reached down, and touched it. Naruto cringed a bit as her one hand was really cold from holding the glass of ice, and she quickly pulled that one away, but her other hand. Most clients didn’t want to touch him down there, except for a few. Though if they did, they usually would jerk him off with a finger or two, which did admittedly feel good when he applied his sexy jutsu on his dick, but actually touching the full thing felt far, far better. To show his appreciation, Naruto let out a small moan for Hinata’s sake, and her smile widened before her mouth opened a bit. For a moment, he thought that she was about to go down on him, and suck him off.

But she didn’t, restraining herself. Hinata pulled back before she reached down and brought up a cold looking ice cube from the cup bellow. The moment she touched his dick with the ice cube, Naruto couldn’t help but gasp as the cold block was slowly slid along his dick, the cube never left in any one place and just kept moving. Slowly Naruto could feel his dick shrinking, losing its girthiness and slowly shrunk down. Some might have been surprised at its shrinkage; some men definitely were, but not Hinata. Rather she just kept continuing, the ice keeping his dick down as Hinata grabbed the cage now that he was only about half chub, and started to assemble the cage. 

The thing was made of metal, and thankfully wasn’t cold due to sitting in Hinata’s hand for a bit. With both hands, Hinata assembled it rather quick as she pulled his dick and balls through the base ring of the cage before she slid on the solid cage itself. Then with a final click, it was done, and Naruto’s dick was locked away so he couldn’t get the heiress pregnant even if he wanted to now. He expected the girl to be overjoyed, but Hinata made an almost disappointed sound as she caressed his caged cock. Pushing himself up so that he could actually see his caged cock over his breasts, Naruto looked down at Hinata, her hand holding the cage while her other hand fondled his balls, providing a bit of delight but not much even as his dick started to press against the cage. 

Surprisingly, the cage fit really well. He barely had any room to expand, and what little he could wasn’t uncomfortable at all. Not like the last cage. The last cage from the one man was too large, and he could still get kind of hard in that one.

Looking at Hinata, she certainly looked disappointed, looking longingly at the caged meat in her hand. She looked up at him and smiled a bit before standing up to look down at him, seemingly ready now. Hinata’s hands shifted as she grabbed Naruto’s hips, and pressed the dildo against Naruto, and now it seems that they were about to begin their fun.

“Puh-please Mistress, I can’t take it any more, stick your big hard cock in me~!” Naruto said in an exaggerated, needy tone. His sexy forms voice adding just the right tone of need to sound like some depraved slut who couldn’t be without her “mistress’” cock filling them. It drove the men wild, and seemingly Hinata as well as her blush darkened, and her nose started to bleed a bit, but she wiped it away and held up her cock to his ass. 

The thing had already been lubed up before, but rather than attack him directly, Hinata pushed forth and slid the dildo past his dick while from the side, she grabbed a bottle from an end table, and poured some of the stuff onto her hand. It was without a doubt lube, especially judging by the hearts on the bottle and the smell coming from it. 

Leaning down, Naruto felt Hinata’s lubed hand and fingers start to press into his ass, sliding in without much trouble as she used her other hand to reach forward while her shorter body pressed against his, her hand pushed against Naruto’s far bigger breasts, gripping one of his tits, before she gently squeezed it. 

“Naruto, I’m going to-to fill you up. I’m-I’m going to fuck you with- with my big thick dick,” she said in an almost out of breath way, her tone almost sounding like she was living a dream.

“Please Mistress, please fuck this slut. Fill my ass until it can’t take anymore, fuck my bitch button and make me yours Mistress,” Naruto said, going along with the foreplay, pushing himself down closer to her with his hands as he pushed his head down, but failed to kiss her. Thought that didn’t seem to matter as her heart sped up all the same and her fingers pushed in harder and faster. Thankfully, despite his time away from this job, he still wasn’t as tight as he used to be when he first started this kind of stuff, and like riding a bike, his ass never truly forgot. She’d already gotten three fingers in now, finger fucking his asshole, the pads of her hands sliding up and down his prostate, knowing exactly where his p-spot was as she played with him. 

Holy fuck, she-she’s good! Naruto could help but think as Hinata kept pressing against his special spot as she made his legs writhe against her form while his dick twitched and pleasure bloomed in his ass spiralling up his spine and filling his head as the lust started to fill his head. The lust fogged his thoughts, and left the only clear thoughts left were ones regarding sexual delight, how to receive it, and how to give it. 

“Please Mistress, please fuck me,” Naruto pleaded, this time being genuine, as the teasing, the pleasure from his ass while great, was nothing compared to what it could be, and how it would feel as she slid her nice thick strap on into him. He wanted it, to feel her slide into him and fuck him deeply, to bring him pleasure while they touched each other, while he wrapped his legs around her and helped her fuck him, the cage rattling between them as they fucked. 

“Okay-okay Naruto, here, here I come!” Hinata said as she pulled back from him, her hand then leaving his ass before he felt her cock pressing against his ass. She didn’t wait long as she pushed in, the cock opening him up and spreading him out. Naruto moaned as she slid into him. While he’d done it in the past, his ass had still had some time to recover, and it was enough to change this size of cock from something he could take easily, to something magical. How it spread him felt amazing, his ass opening for her while blooms of pleasure shot through him, and that was before she even got to his-

“Gha~! Ah, oh~!” Naruto cried as he couldn’t help but close his eyes, and his legs coming together around Hinata. Her big thick cock that filled him so fully finally smashing against his prostate. Hinata’s cock was filling him up and pressing hard against his special spot, applying pressure which translated to pleasure in his mind as his cock bounced wildly, the lock on the cage clinking around while his ass clenched around Hinata’s strap on. His breathing grew ragged as she kept fucking him, sawing in and out, mauling his breasts, her face completely red with a blush as the blood continued to drip from her nose. Yet Hinata didn’t seem to care as there was a look of absolute joy on her face as she fucked him her moans mixing with his as he cried out while being fucked. his girlish Naruko voice reached up higher and higher as he cried out in ecstasy while Hinata hit him right where he loved it.

“Oh God mistress, thank you~!” he cried out as the pleasure continued to explode in him with every thrust, the vicious pounding making his legs go limp as Hinata pulled back from his breasts while his legs fell, and instead grabbed his legs. She grabbed Naruto by his knees and pushed them up, easily forcing them due to his sexy forms greater flexibility up by his head. 

“Naruto, Naruto, this is, this is the best day of my life!” Hinata cried out as she continued to fuck him, filling his hole as she kept increasing in speed, and he could even feel a bit of chakra being used as well, boosting the power of her body as her thrusts kept sliding into him deeper and deeper while she went faster and faster. It was like a constant barrage of pleasure that assaulted his ass, his own regeneration helping keep his ass tight and never let the force of her assault damage him, leaving only pleasure as Naruto started to feel that strange, almost-cumming sensation. The sensation right as he reached climax, and he cried out in elation as he felt his cock twitch, and yet the feeling never subsided, continuing on and on while his eyes rolled up and his mouth opened wide, his mind unable to process the pleasure as the sexual delight he felt increased four fold as it suddenly felt like his whole body was orgasming, and soon enough his vision went white as pleasure filled his mind and became his world. 

His mind was breaking, Hinata was mind breaking him, just like in that hentai he read~!

“Hinata! I’m breaking, you’re breaking my mind,” he screamed out as she kept pounding him and more and more, filling it with so much pleasure that he’d never be able to live without her strap on again. As she kept fucking him, Hinata grabbed hold of Naruto’s hands, taking both of them in her own hands, intertwining their fingers as she leaned down. Naruto couldn’t focus long enough to see her face, but the rapturous expression he saw for a moment was enough as she leaned down, continuing to thrust into him as she kissed him on the lips, her tongue sliding in as they battled while she continued to fuck him silly. Then she pulled away.

“Then break my beautiful Naruto, break for me and become my slave~” Hinata said to him before they kissed once more and Naruto closed his eyes, their fucking continuing on and on into the night, Hinata never stopping for a moment as she destroyed his mind with the most amount of pleasure he’d ever felt in his life. Were he a regular human, he’d have never survived, but his demonic regeneration saved him and allowed the pleasure to continue on well into the night until finally, with a final slam into him, Hinata collapsed onto Naruto. 

The two were breathing hard, hugging each other while a massive pool of cum filled the bed, soaking the sheets, and filling the room with its scent. Completely exhausted, it was all Naruto could do to try and pull himself and Hinata away from the completely soaked part of the bed before they fell asleep. Before they did though, Hinata spoke.

“D-did you like that, Naruto?” she asked, and Naruto couldn’t help but giggle a bit, the girlish voice of his sexy jutsu making it sound all light and airy.

“What do you think?” he asked before kissing her again, and pulling a moan from her. 

“I’m glad,” she said, before their eyelids drooped.

“Hey, did your Dad really want you to make your lovers wear chastity cages, or do you just like that?”

“Both.”

“Oh, okay,” and with that they fell into a peaceful rest.

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