Naruto the Prostitute

Naruto the Prostitute

Naruto Uzamaki was the main trouble causer in the Konoha high school, not that he picked fights or made fun of people. The way he caused trouble was by openly admitting he was a cross dressing, bisexual prostitute that would do anyone, in anyway and anywhere, as long as they had the cash. He flirted with the students and the teachers, he purposely failed assignments and tried to make up for them another way. He dressed in a girls uniform that was a size or two too small, the skirt just hiding his cock stuffed panties at times and the shirt showed off his stomach.
Although no one would admit it, Naruto actually looked pretty good in the uniform. He loved to stand out and he loved knowing peoples true sexualities, most of the girls were straight as a ruler, but none of the boys were. Some of the men were bi like him, but less obvious about it, and some were gay, some more obvious than others.
It was a sleazy school in a sleazy town with sleazy teachers and students, but neither student or teacher would admit they were sleazy, another thing they wouldn’t admit was how many times they’d actually fucked, or were fucked by, Naruto. The blond cross dresser was annoying and a total slut, but he kept the privacy of his clients so they’d come back for more, although in a town and school like this one it wasn’t very hard for news to spread fast. Everyone knew Naruto had been fucked, screwed and paid by everyone in the city at least once, most of his business came from the school, but no one talked about it.
Naruto’s appearance also caused a bit of trouble as well, his blond hair was shoulder length and smoothed down, his build was more of a woman’s than a mans and he wore a little bit of make up to help his facial features slightly, even some of the girls wanted tips from Naruto

“So where’s your essay Naruto?” Iruka asked, knowing what the answer would be before he even asked the question
“Sorry teach, I didn’t do it, I guess I’ll have to make up for it somehow” Naruto smirked, winking at Iruka, causing him to clear his throat and move onto the next desk
“that’s totally sick dude” Kiba whispered to Naruto, he tried to convince everyone he was straight, but he was bi “flirting with a teacher”
“nothing wrong with flirting with someone Kiba dear” Naruto chuckled at Kiba “Iruka’s private lessons can be very, long and rewarding”
“Please your making my stomach churn” Kiba leant back in his seat away from Naruto as Iruka said
“See me after school Naruto”
“Of course sensei, I’ve got to pass this somehow, right?” Naruto smiled seductively as the bell rang for the afternoon lunch break.
The students stood up and started filing to the door, Naruto blew a two finger kiss toward Iruka as he passed him, making the teacher blush slightly “Um… Naruto-kun… would… would you like… um” Hinata asked nervously as she walked by his side
“Sorry Hinata, but I got a few appointments for lunch,” Naruto smiled at Hinata, leaning in and whispering in her ear “But if you want to make an appointment, wait for me after school and I’ll see what I can arrange”
Hinata blushed furiously as he heard this “N… no, I wanted…. To um ask… if you wanted… to eat… um lunch together”
“Oh, well sorry, but I’m busy this lunch” Naruto smiled as he moved away, shouting over the crowd “But keep my offer in mind anyway, I had fun last time” he then ran to the boys toilets, his small skirt showing off his panties as he ran

Naruto walked into the toilets by himself, he hummed as he counted the stalls “Fourth stall down on the right” he thought to himself as he entered it, he left the door unlocked and sat down on the toilet, “Off with the panties, door unlocked and on with the show”
Naruto only had to wait a few minutes before he heard other boys entering the bathroom, he heard a few of them talking to each other and waited till one chose his stall, he smiled as he saw the door open and sure enough his first client showed up, Neji Hyuuga, self centred prick, extremely cute and gay. Neji closed the door as he moved close to Naruto, backing off slightly as he had more room, without saying anything his hands moved to his trousers
“Sorry cutie, but you now how this works by now, money up front” Naruto smiled, crossing his legs and leaning back. Neji stared at him and heaved an annoyed sigh, he reached into his back pocket and pulled out a hundred dollars worth of tens and handed them to Naruto.
Some people didn’t like Naruto’s prices but no one ever said he wasn’t worth every penny, for ten bucks he’d give you a hand job, or play with your pussy till you came if the client was a girl, for twenty five dollars he’d give you a blow job or a tongue fuck. For fifty bucks he’d give you two blow jobs, for a hundred he’d give you the full service, two blow jobs and fuck him in the ass or he’d fuck you. If you wanted to add anything to the game it would cost extra, toys, another person etc, the more kinky it got, the more it would cost.
Not everyone would have Naruto regularly but there were a few rich families in the school, the Hyuuga’s, the Uchiha’s. Most people needed a job to get the money, Neji was one of Naruto’s regular customers
“Now that’s out the way, let the fun begin” Naruto smiled as he put the money in his bag, he watched Neji open his trousers and pulled his already semi hard cock out of his underwear, Neji was a gifted person, he was smart, cute and had one of the biggest cocks between all the male students going to the school. When he was fully hard he must have been seven, seven and half inches big at least, needless to say Naruto enjoyed Neji’s business greatly.

Naruto took the cock head in his mouth and sucked on it hard, jerking Neji’s cock as he did so making him moan at the feeling. Naruto started to take as much of the cock as he could in his mouth as he felt it start to get harder, deep-throating it up to six inches once it was fully erect, making Neji moan louder and grab Naruto hair, feeling him lick up his shaft with is tongue and jerk what wasn’t in his mouth “I’m cumming” Neji moaned, trying to keep his voice down
“Hang on big boy” Naruto panted as he took the cock out of his mouth, he clamped his hand at the base of Neji’s cock tightly to stop him cumming, Naruto then stood up and turned round, bending over and directing Neji’s cock to his ass “How’s that feel?” Naruto moaned slightly as he pushed the tip of Neji’s cock into his ass, hearing the older boy moan louder as he let go of the cock, a second later feeling the hot cum shoot into his ass, making Naruto shudder at the sensation “That good?” Naruto chuckled as he sat down again, feeling the cum coating his ass cheeks and what little actually went in his ass
He felt Neji grab his hair again and push his cock in front of his face, Naruto opened his mouth happily directed the cock into his mouth, sucking and jerking Neji off at the same time, making him moan loudly as he felt the tongue dance around his cock. He felt Naruto continue to jerk him as he felt Naruto tongue lick up his dick, sucking on one of his ball as he squeezed his hand tighter, making Neji moan “I’m… cumming again”
Naruto smiled as he took the cock in he mouth and sucked as hard as he could, playing with Neji balls as he heard him moan and shoot his cum into Naruto mouth, who gulped it down as fast as he could

Neji leant against the side of the cubical as he panted hard, watching Naruto stand up and lift his skirt, pulling his ass cheeks apart and showing him his cum coated ass hole “What’s the matter big boy, you normally have more stamina than this” Naruto smiled as he watched Neji jerk his own cock a few times, making it semi hard again
“Just shut up” Neji positioned the head of his cock against Naruto’s hole and pushed in, both moaning at the feeling
“Ooh what ever you say, just don’t stop” Naruto purred as he felt more of Neji’s cock get stuffed into his ass, getting harder with each thrust, Neji wasn’t the biggest he’d ever taken, but it still felt good.
Naruto couldn’t help but moan as he felt Neji’s seven inch cock get pushed deep into him, he felt Neji grab his hips and start to thrust in him hard, making him moan even louder as he felt Neji’s cock slam deep into him, the cum from earlier making for a great lubricant
“You like this don’t you slut? Getting fucked in a toilet for money” Neji panted as he pounded into Naruto’s ass hearing the blond haired cross dresser moan
“Oh god you know it” Naruto could feel his erect cock slap against his stomach as Neji thrusted into him “pound my ass big boy”
“You love to feel people cum in your ass don’t you” Neji panted, feeling himself getting ready to cum again, feeling Naruto’s ass squeeze around his cock as he clenched
“Better believe it” Naruto panted, he wanted to touch himself but he knew he wouldn’t be able to keep balance with just one arm when getting fucked by Neji “Cum in my ass hard big boy”
“Fine you cross dressing slut, take my cum” Neji moaned as he felt himself shoot his load into Naruto ass, both of them moaning at the different feeling
Neji panted for a few seconds feeling his orgasm past, pulling out of Naruto and hearing him moan as the cock left him. Naruto turned around and sat down again, keeping his legs open and his skirt up to give Neji a good view of his hard cock and the cum leaving his ass “Same time tomorrow big boy?” Naruto asked
“No, the day after” Neji simply said, leaving the stall, letting the next boy enter

“Sorry I’m late Kakashi sensei, but I had to take care of some business” Naruto smiled as he stepped into the class room
“I’m sure you did” Kakashi said as he looked up from his dirty book, he was sure some of the things in there were inspired by Naruto “Don’t bother sitting down” he said as he say Naruto make a move for his desk. Everyone looked up from their work at those words
“Why Sensei, are you going to punish me for being late?” Naruto asked smiling, it wouldn’t be the first time he’d spanked him in front of the class, and probably wouldn’t be the last, out of all the teachers and staff out of the school, Kakashi was the only one to punish Naruto when class was actually in session
“Not today, I’m sending you to principal Tsunade” Kakashi looked up from his book to see Naruto role his eyes “but see me after school for disturbing my class”
“Yes sensei” Naruto sang as he left the classroom, closing the door behind him

“Hello Shizune, it the principle in?” Naruto asked, Shizune was Tsunade’s receptionist and girlfriend, a total lesbian, from what Naruto heard she hadn’t even been fucked by a vibrator or a strap on since she lost her cherry. Tsunade on the other hand was a very open, very mean bisexual
“Ah Naruto, is it the last day of the month already?” Shizune asked, looking up at Naruto. At the last day of the month, or closest they could get, Tsunade would call Naruto to her office after the afternoon lunch break to punish him for all the trouble he’s caused, not handing in reports, getting fucked on school property etc, Naruto didn’t mind, he enjoyed getting at least five hundred bucks from her
“That’s why I’m here” Naruto smiled, taking a seat next to Shizune’s desk
“I’ll see if she’s ready for you” Shizune stood up and knocked on the door, waiting a few seconds before entering and closing the door behind her
Naruto looked around the room idly for a few seconds before remembering something, he reached into his back and pulled out his panties, quickly pulling them on as he knew Tsunade liked seeing him in them, and she liked it even more when she pulled them off him
“Ok Naruto, Tsunade is ready for you” Shizune said as she entered the room again, sitting behind her desk as Naruto stood up
“Thanks, remind me why you haven’t asked for my services again?” Naruto asked, freezing at the door of Tsunade’s office
“I don’t do dicks, remember” Shizune blushed as she got back to her work, tensing up as she felt Naruto’s hands on her shoulders
“I do a good tongue fuck for twenty five bucks, ask around, I think you’ll be pleased with the results” Naruto smiled as he leant in on Shizune, he was going to kiss her cheek when he heard an angry shout from the other room
“Get in here you little pervert” Tsunade’s voice rang, Naruto sighed and moved away from Shizune, leaving her blushing and finding it hard to focus on her work
“Alright principle I’m here, you don’t have to burst a vein” Naruto sighed as he entered the office, closing the door behind him
“With all the reports I’ve got about you I do,” Tsunade pointed at a chair in front of her desk and Naruto sat down on it, crossing his legs as he did “not doing work, late for classes, flirting with teachers, getting paid to get fucked on school property. What do you have to say about this?” Tsunade picked up a small stack of papers and slammed them on the desk
“Well I didn’t hear any complaints at the time” Naruto shrugged “anyway, its not like I’m doing it every day”

“but you are,” Tsunade leant against her desk, she wore an expensive looking suit, dark blue jacket and trousers with black heels, but the problem some people had was that Tsunade didn’t wear a shirt under the jacket, and she didn’t always button it up fully so she showed of most of her ample cleavage. Tsunade was controlling, loud, scary at times and most definably a tease “How much did you get this lunch break?”
“only three hundred and forty five dollars, I don’t see the problem” Naruto shrugged again, every month Tsunade did this, she liked a bit of role playing, she liked dragging it out, she liked to build the anticipation on what everyone knew was going to happen
“Of course you wouldn’t know, to you there is no problem, but there is a problem for me” Tsunade walked around the desk and behind Naruto, it wouldn’t be long now “I can’t let this continue, but I don’t think there’s away for me to stop it either, even if I expel you you’ll just stand on street corners”
“So what you going to do?” Naruto asked, placing his bag on the floor, he felt Tsunade place her lands on his shoulders and whisper in his ear
“Punish you,” Naruto felt himself get push forwards, thrown over the desk, he made no effort to resist, it happened every month. First a spanking, then he would either tongue fuck her or she’d suck him, he would then fuck her in her cunt and ass then most likely Tsunade would fuck him in the ass, all depending on how much money she had.
Naruto felt Tsunade lift his dress up and stroke his ass cheeks with her hands through his panties “I’m going to spank you for everything on that list, by time I’m done you won’t be able to sick down for a week” Naruto watched as Tsunade lent over the desk, her breasts rubbing against his back, as she grabbed a wooden ruler “lets see, first thing on the list is, being late for class” she smacked the ruler on Naruto left cheek, making him gasp from the pain “Next is, being late for class again” she hit is right cheek this time, Naruto grunted as he bit his lower lip, his ass cheeks stinging already “improper uniform, work not complete, flirting with teachers” with every smack of the ruler Tsunade put more effort into the swing, Naruto crying out as the ruler struck both his cheeks “And these are for fucking on school property”
Tsunade grabbed Naruto panties and pulled them below his ass cheeks, smacking Naruto’s bare ass as quick and hard as she could, hearing the blond boy cry out in pain as the last swing hit “Now, will you do any of those things again?” Tsunade asked, panting as she put the ruler down, small sobs coming from Naruto as he answered
“N… no principle Tsunade”
Tsunade stood Naruto up and wiped the tears from his face, his ass cheeks red and feeling like the were on fire “Did that hurt?” she asked as she pulled Naruto against her chest
“Y… yes principle” Naruto sniffed, feeling Tsunade’s hand move down under his skirt, grabbing his hard cock and making him gasp at her touch
“But you enjoyed it didn’t you?” Tsunade smiled, jerking him off slightly, making him moan
“Y… yes… I did” Naruto moaned
“So did I, in fact I enjoyed it so much I couldn’t help but get turned on” she forced Naruto to lower on to his knees, she opened her trousers and pulled them down with her panties “So now I want to get tongue fucked by a cross dressing girly boy like yourself, understand?”
“Yes principle” Naruto blushed as Tsunade sat on her desk, Naruto place his mouth on her crotch and instantly went to work, his tongue playing with her clit and licking up and down her wet pussy lips, hearing Tsunade moan as he pushed his tongue into her, her hands grabbing fist full of hair, holding him in place as she felt the tongue move around in her
“Ooh, just like that, keep dong that” Tsunade moaned, she opened her jacket and started to play with her own breasts, flicking her nipples as she felt Naruto flick her clit with his tongue “Faster, harder you little slut”

Naruto couldn’t help himself and reach down, grabbing his own cock and quickly jerked off as he tasted her pussy juice “Hey, stop that you little freak” Tsunade shouted, Naruto looked up as Tsunade pushed him away, both of them only worked to half an orgasm “I don’t remember saying you could touch yourself”
“I… I’m sorry, you just tasted to good I couldn’t help myself” Naruto moved back onto his feet, his cock still hard as the small dress covered it
“Well if you need to cum that badly then why don’t you stick it here” Tsunade smiled as she separated her pussy lips with two finger, Naruto took a step forwards then stopped as Tsunade pressed her shoe into his chest “But first, get rid off the dress and panties”
Naruto nodded and pulled down his dress along with his panties, stepping out of them and closer to Tsunade, positioning himself at her wet cunt “No going easy slut” Tsunade purred as she wrapped her legs around Naruto’s back, forcing him to thrust in hard, both moaning as the dick pushed into Tsunade’s cunt. Without hesitation Naruto started to thrust in and out, quickly building a pace that they both enjoyed
“Oh Tsunade, you feel good” Naruto moaned, grabbing Tsunade’s breasts and licking one nipple
“So do you, now fuck harder” Tsunade moaned, grabbing Naruto’s ass and squeezing it, causing him to hiss into her ear as he felt a stinging pain shoot from his cheeks
“Easy, that hurts” Naruto picked his pace up and he bite one nipple gently
“Why, it makes you move even faster, and me even better” Tsunade chuckled, moaning as Naruto slammed into her
“God I’m going to cum” Naruto moaned, sucking on Tsunade’s tit
“than you’d better switch hole” Tsunade let Naruto go from her legs, she stood up and turned round, leaning against her desk as she felt Naruto grab her ass cheeks and position himself, pushing in slowly as he glided in “Ooh, now that feels good” Tsunade moaned as Naruto started to thrust into her ass “Hurry and cum in my ass”
“I’m trying” Naruto moaned, one hand moving down to Tsunade’s pussy and pushing two fingers in, making her arch her back and he pumped both fingers and cock into her
“That… that’s cheating… now… I’m going to… to cum” Tsunade moaned, feeling her orgasm building quicker with double penetration
“You know you love it” Naruto moaned as he could felt himself getting ready, pushing in faster into Tsunade
“Never… never said I didn’t” Tsunade moaned, she could feel her orgasm about to burst “I’m cumming” Tsunade moaned, hearing Naruto moan as well as he came in her ass, the hot feeling of cum filling her up

Naruto slid off Tsunade and into a chair, his cock going limp quickly as Tsunade continued to lay on her desk, her hand moving to her ass as she felt the cum leave her “Did I say you could cum in me?” she panted as she stood up, showing Naruto her cum stained fingers
“Never said… I couldn’t” Naruto panted
“Still, you shouldn’t have cum in my ass, now I’m going to have to repay the favour” Tsunade walked around her desk, opening the bottom draw and pulling out an eight inch long, two inch thick strap on dildo
“You can’t be serious” Naruto panted, seeing Tsunade slip on the dildo, reaching back to her ass and covering the fake cock with his own cum
“I’m dead serious, now you’d better get over here or I’m going to get an even bigger one and dry fuck you with it” Tsunade smiled as she watched Naruto pull himself onto his feet, walking up to her and bending over her desk “Now that’s a good slut”
Tsunade positioned the hard cock and pushed into Naruto, forcing half of the entire thing in one go, causing Naruto to scream/moan out loud as he felt his ass get violated, she pulled out a bit then pushed the last of the shaft into Naruto ass, causing him to shudder and moan as he felt all of it go into his ass “How’s that feel?” Tsunade asked as she grabbed Naruto’s ass cheeks squeezing them hard
“So full… so big” Naruto panted, moaning as he felt Tsunade start to pull out then start to pump into him, making him moan loud
“You’re being too noisy, I think we need something to keep your mouth busy” Tsunade smiled and shouted “Shizune, get your ass in here”

After a few seconds a nervous looking Shizune opened the door and entered the room “Y… yes Tsunade?” she asked, seeing Naruto laying on the desk and fucked up the ass by Tsunade
“This little slut is being too noisy, come over here and keep him quiet” Tsunade pulled almost all the way out of Naruto then forced the cock back into him, making him moan loudly and arch his back
“I… I don’t” Shizune couldn’t keep her eyes off of Naruto face, she new he was a boy but from this angle he looked like a slutty girl
“I want you to climb on my desk and get tongue fucked by Naruto, understand now?” Tsunade asked as she reached round Naruto’s waist and grabbed his hard cock, squeezing it tightly and making him moan even louder

Shizune bit her lower lip, not sure what to do for a few seconds before taking a step forwards. She moved in and climbed on the desk, pulling her skirt up to her waist and revealing she wasn’t wearing any panties, Tsunade never allowed her to wear any just in case she wanted a quick fuck at work.
She watched as Tsunade forced Naruto to straighten up, she then moved on to the desk more and lay on her back, covering her eyes from the embarrassing scene unfolding in front of her. Shizune gasped as she felt a tongue land on her pussy, licking it hard and fast making her moan as she felt her lips get parted “You like that don’t you?” Tsunade asked Shizune as she started to jerk Naruto off as she fucked his ass hard, hearing him moan into Shizune’s pussy “Tell me, what do you think off Naruto tongue? He’s had plenty off practise”
“It… it feels good” Shizune moaned, she could feel her pussy getting hot from the treatment from the cross dressers tongue, he knew the right spots to touch at the right times, when to move fast and light, when to be hard and slow, she couldn’t help but feel her orgasm coming quickly
“What about you Naruto, do you like how she tastes?” Tsunade chuckled as she jerked him off faster, feeling the cock twitch in her hand, hearing him moan into Shizune’s pussy loudly “I take it you like how she tastes then”
“Oh… god I’m Cumming” Shizune moaned feeling her orgasm hitting her quickly, feeling Naruto’s tongue push into her as far as it would go, making her moan loudly and cum in Naruto’s mouth as he clamped it around her dripping cunt
“I love to watch you cum” Tsunade chuckled, seeing Shizune shake as she came, a deep blush covering her face “But what about you? Ready to cum yet?” Tsunade moved the fake cock faster as well as her hand, hearing Naruto gasp suddenly and arch his back
“I’m… I’m about to…” Naruto moaned, feeling himself spray his cum into Tsunade’s hand and the cock get slammed into his ass one last time and stay there. He slumped onto the desk and panted hard as he felt Tsunade release her grip on his cock and chuckle
“Now that a good little slut” Tsunade chuckled as she grabbed a tissue from her desk and wiped Naruto’s cum off her hand, she detested the taste of a mans cum, first time she’d swallowed a mans cum she threw up less than ten minutes later.
She pulled out of Naruto and heard him moan as she left him, she watched as he stood up and Shizune moved off the desk, leaving the room with embarrassment, Naruto moved round the desk and sat down again. Tsunade pulled the plastic cock off and put it on her desk, she then reached into the lower draw again and pulled out a small bundle of cash “So how much this time?” she asked as she started to count off hundred dollar bills
“Lets call it… five hundred this time, I’ll give you the tongue fucking of Shizune for free” Naruto smiled cheekily, shifting around in his seat as his ass felt empty
“Alright Naruto” Tsunade sighed, that was five hundred she’d never place a bet with, she passed Naruto the money and watched as he put it in his bag “I don’t suppose you do a special offer for parties do you?”
“Why? Planning something special?” Naruto asked as he added the money he’d just been given to he rest
“Not personally, but I know a few people that might be interested in your services” Tsunade leaned back in her chair as Naruto stood up
“Well tell your ‘few people’ to set up an appointment, I’ve got a schedule to keep you know” Naruto putt his bag over his shoulder and left the room, seeing Shizune was missing from her desk as he passed it “Now lets see, do I have the teachers take me one at a time, or all at once in the teachers lounge?” she asked himself smiling

*

First part of my Naruto prostitute series, hope people liked the slutty Naruto cause I got a lot of chapter lined up, I feel obligated to tell you about the story that inspired my to write this, it was Devil with his Naruto punishment series in the AU section, check it out, I really like it