Pairing: Itachi x Naruto, Ino x Others, mentions of Itachi x Others
Warnings: Prostitution (consensual – and in Ino/Naruto's case, very willing), language, cross dressing, slight dub-con aspect (in the sense of prostitution/being made to please a client though this is only for the initial stage).
Written for the ItaNaru bingo - link on my profile.
Werewolf
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A raucous laughter hit Naruto's ears as he scrubbed the floor. A puff of smoke travelled over to him and he winced at the bitter taste of tobacco, turning to the laughing woman with a wrinkled nose.
"Do you have to smoke that when I'm trying to air the room out?" His words fell on deaf ears and Naruto sighed, rolling his sleeves up further and dipping his hard-bristle brush back into the soapy water at his side. There was still so much to do and he couldn't afford to spend time on civil conversation.
"I was just thinking of how much your mission partner has already brought in for us." The woman took another puff of her cigarette and sighed. "Are you sure she has to go back at the end of the contract?"
Naruto rolled his eyes and continued to scrub the floor. He longed to use kage bunshin, but that would give his identity away straight off the bat. He was supposed to be a general working boy at this entertainment house, not a shinobi on a mission.
"She is a kunoichi first and foremost," Naruto muttered, dipping the brush back in the water and working on the next section of floor. "I'm not going to comment on how much she's told me she's enjoying it, but in any mission, I know Ino would give her full."
The woman – the owner of the establishment – made a noise of agreement. While Ino was more than capable of using her clan skills to make a man believe they had got their money's worth, Ino had made it clear she preferred to do it the 'traditional' way. Which Naruto had been informed of with a devious smirk and a deadly wink.
He wondered if Sakura knew her best friend loved sex so much. Probably not, but he had no idea what the two women talked about on their own. Cocks could be high on the agenda and Naruto would never know.
"It was my understanding that she'd be using a clan technique to trick her patrons." The owner took another puff of her cigarette. "She gets the lowest paying customers and still pleases them better than some of our more established workers."
"Are you calling her a slut?" Naruto asked, narrowing his eyes and pausing in his cleaning. His hands were red and they welcomed the moment's rest.
"Not at all," the woman said, slamming her hand on her desk. "It's just a waste that I'll lose her without being able to train her as a full worker."
Naruto didn't say anything and returned to scrubbing the floor. While he didn't fully agree with the sex working industry, he knew that every woman in this particular house was here consensually and protected by the owner's hand. It was part of the reason Naruto was here, Ino as his mission partner. The owner was concerned about a particular group of men who visited the establishment on a regular basis and had hired two Konoha nin to help her protect her women.
"Still," Machiko said, standing up and stubbing her cigarette out. "If only we catered to women or homosexuals. I would have liked to see how you fared."
She left the room, laughing, and Naruto gritted his teeth. Ever since he'd arrived, Machiko had teased him endlessly. It was apparently her way of showing how much she liked someone, but it grated Naruto's nerves. He wasn't here as a whore and while sex was all well and good, Naruto had spent too much time in darker places with Jiraiya (genuinely for information – Jiraiya had sworn that he would never touch any of the women in those kinds of places) for him to be fully comfortable taking on a whore's responsibility.
Not that that would stop Machiko's teasing. If she had the clients for him, Naruto knew he'd be out there with Ino, working his charm and doing his job. He was lucky, in that respect, that he was only a cleaning boy, even if it did put him in line for Machiko's ribbing.
"Naruto!" a bubbly voice called out and Naruto turned, finally done with scrubbing the floor, to smile at Ino. She was still in her sleepwear, hair knotted and down and looked as though she had had a busy night.
"Want to accompany me into town? Machiko-san said that we have to entertain an important customer later and wants the town visits to be over and done with before lunch." Ino smiled, eyes wide and begging.
Fuck, there was no way Naruto could say no to that. Ino was a manipulative bitch when she wanted to be, that much was for sure. Naruto was just glad she seemed to be on his side most of the time.
"I'd go with the girls, but rules are rules and I'd need an escort anyway. I thought we could combine it with talk about our mission." Ino smiled wider and leant forward.
Naruto thought about it for a moment. While he did have a lot of jobs to do, if Machiko was to entertain an important client then everyone would be cleaning everything in fervour. It would be a good time to slink away and let his hands recover from the brutality of scrubbing every damned floor.
"Let me just change," Naruto said and he sprinted off, nodding to Ino's calls to meet at the worker's entrance of the pleasure house.
He changed quickly, throwing on a generic outfit of shirt and jeans. He only had to wear traditional attire when working (as did all staff), but when venturing out into town, everyone preferred to wear clothes that wouldn't mark them as belonging to a pleasure house. It was an unspoken rule that, admittedly, some broke.
Ino smiled at him as he joined her and they walked down the long path until they came to a low gate. It was unlocked and they slipped out, moving towards the nearby town centre, out of Machiko's district.
"We have to get back early. Machiko-san wants everything perfect for the clients." Ino flicked hair out of her eye line and patted her trouser pockets, checking that she had brought her wallet. "I think they're the main benefactor and I know for sure that without their contributions, Machiko-san wouldn't be able to protect the girls as she does now."
Naruto grunted in reply as they entered the main town. His stomach rumbled as the scent of cooking food hit him and he wondered if Ino would be willing to let him stop off for something to eat.
"I need to pick up a few personal things," Ino said suddenly, looking at Naruto with such a wolfish gleam that he took a step back. "One of the girls mentioned a technique that requires some equipment and I'm hoping to find it here. While I'm busy, you can shovel down some food or something."
Ino was a goddess, Naruto decided. Not only was she letting him off of seeing whatever sex toy she was about to inspect, he was also allowed to fill his stomach. Ino dug into her wallet and passed him some money, further cementing Naruto's adoration.
"You know, I'm not doing this without a reason," she said suddenly and Naruto raised an eyebrow, blood chilling. Had he unwittingly sold his soul and Ino was reminding him of the fact?
"As far as anyone back home knows, I'm a virgin who blushes at the prospect of sex. I've never seen a man's penis or another woman's vagina – family discounted – and I'd have no idea what to do in the bedroom." Ino narrowed her eyes and Naruto swallowed thickly, finally understanding that Ino's kindness was double edged with Ino's bribery.
"My father allowed me on this mission because I promised to use clan techniques and because you were going with me. He will never know that I like having no-strings-attached sex and will never know that I'm anything less than 'pure'." Ino smiled, looking at Naruto with a deadly gleam in her eyes.
Women were going to be the death of Naruto.
"I wouldn't have told anyone anyway," he muttered, clenching his fist around the money she'd given him. He should feel it was dirty – hush money – but the rumbling in his stomach was too persistent for him to be too bothered by what Ino was trying to achieve.
"Good," she said and patted his arm. "I'll meet you in a bit then."
She was gone a moment later and Naruto turned his attention to the smells of the town, tracking down a ramen stand with glee. He ordered enough for a small platoon and hunkered down at one of the tables to the back, planning to stay out of sight until he'd had his fill, just in case Ino changed her mind and dragged him off again. He hadn't had ramen in weeks now and was dying for a taste.
Naruto was four bowls in when he noticed the commotion outside. It wasn't a loud commotion, but hushed whispers were just as easy to hear when there was something going on. Naruto looked out of one of the shop windows, slurping noodles as he noted two cloaked figures moving through the town, drawing stares.
"Hey, old man," Naruto called, grabbing the attention of the shop owner. The man moved to join him with a smile, perhaps hoping Naruto would be ordering more. (Well, he would, but that wasn't what he was about to ask now).
"What's with all the fuss over those guys?" Naruto said and the old man raised an eyebrow.
"You don't know?" he asked, sounding a little taken aback. "They're the village's main patrons. We provide them with food and goods if they need them and they offer us a little protection. They're also the reason that Machiko's place has such a good reputation."
Naruto looked down at his ramen in thought. "Interesting," he muttered, looking out the window to try and spot the figures again. The town had returned to normal now and Naruto could see them in the distance. "So in return for food and things they need, you get their protection and influence?"
The old man nodded and Naruto thanked him, ordering another two bowls with a frown on his face. While benefactors for villages and towns weren't unheard of, they usually demanded taxes and outrageous terms. This group had to be immensely powerful and oddly generous and Naruto understood why Machiko would want everything to be perfect.
He paid for his ramen and left, looking around for Ino. He wanted to get back in good time for Machiko, now that he knew what those people did for the town. If everything had to be perfect, Naruto wouldn't be the one to screw things up for these people.
"I take if you know they're in town then," Ino said, surprising Naruto as she tapped him gently on the shoulder. There was a brown paper bag tucked under her arm and Naruto tried not to look at it too hard, afraid a dildo or something equally horrifying might pop out. Not that dildos scared Naruto, but the image of it being used in whatever game Ino was raring to try would push him over the edge of comfort.
Ino could be a sex fiend in private. Naruto had no wish to imagine her in any sort of light like that.
"Ready to head back then?" Ino said, starting to walk off. "Business will be raring tonight too. The top members of the organisation will be partaking in Machiko-san's patronage no doubt." Ino smiled softly as Naruto joined her.
"It really is a shame you have to miss out on all the excitement." She sighed and Naruto looked at her. "Machiko-san really is a kind woman. She protects her girls and would never force them. Yes, some may be there because they have no other choice, but Machiko-san cares for them all."
"I know that," Naruto said quietly. Machiko cared enough to hire them from Konoha at a hefty price. Naruto had seen Machiko cutting personal expenses back because of it and he knew that she was a good woman. Prostitution was never an ideal business for the women, but Machiko did her best and tried to keep her girls safe.
"I don't envy your job. We'll be entertaining clients and you'll still be scrubbing floors tonight." Ino smiled softly and shifted the paper bag to her other arm. "It's a shame your gender changing jutsu isn't undetectable."
Naruto laughed. "Ino, I don't know the first thing about having sex with girls, let alone having sex as a girl."
Ino looked at him curiously, wrinkles appearing on his brow.
"But you're a guy," she said, though it came out more as a question. "You know what guys like."
Shrugging, Naruto replied. "Still doesn't mean I'd know my way around a pair of tits and a cunt."
Ino's eyes narrowed and she looked away, amused. "I thought you would have a lot of experience, what with the time you spent in Jiraiya-sama's company and all."
Naruto scratched the back of his neck and gave a slightly nervous laugh. Jiraiya was a self-confessed super pervert so it was no surprise that people thought Naruto was of the same mould (especially considering the first technique he invented), but the truth couldn't be further from it.
"Well," he began, unsure how to proceed. "I was training in that time, you know."
The words sounded weak and unconvincing, probably because they weren't the complete truth. Naruto knew Ino could sense it and looked directly ahead, determined not to look in her eyes. If she gave him a look then he was screwed.
"I don't believe that you were solidly training for almost three years and didn't get a break. A man has needs and unless there was something dodgy going on, there was casual sex going on somewhere along the line." Ino ignored Naruto's wrinkled nose at the suggestion he and Jiraiya had been involved sexually and poked him in the side.
"Look, you know I'm not going to think any less of you for fucking whores. I'm a whore myself at the moment and enjoying it!" Ino laughed, rolling her eyes at Naruto. "I can't see why you'd hide it unless you didn't want anyone to know who you were having sex with, and even then-"
Ino cut herself off and Naruto closed his eyes tightly, ignoring the way she stopped dead in the middle of the path. She'd figured it out then.
"N-Naruto?" Ino stuttered out and Naruto opened his eyes, sighing. "But you… Sakura and… oh my god, Sasuke?"
Naruto stiffened and wheeled around, shaking his head.
"No. No. No!" he said, eyes wide. "Not 'oh my god Sasuke'. Just… no. Sasuke's my best friend."
Ino raised an eyebrow. "But Sakura?" she persisted and Naruto sighed.
"Well it's not exactly a secret," he said. "I don't care who knows, but I don't see why I should publicise any of my private life from the top of the Kage mountain."
"But you're Naruto," Ino muttered, picking up pace again. "You're too loud and stupid to have any secrets."
"Hey," Naruto said, mock-outraged. "I just don't see why anyone needs to know how much fun sucking cock can be."
The words were out before Naruto could take them back and he felt Ino's predatory grin before he saw it. He'd said the wrong thing to the wrong person and he was about to pay with his soul.
"We need to compare technique," Ino said, smile widening. "I have a few things that I can teach you – I bet you have some for me."
Naruto made an uneasy noise in the back of his throat. He really, really didn't want to talk about sex with Ino. He'd overheard her conversation with the other workers before and Ino was fond of overly-graphic descriptions. Things Naruto had never wanted to know were now stuck in his mind and he didn't need even more of that nightmare.
Fortunately, the gate to Machiko's was in sight and Naruto ran towards it, careful to stick to a normal pace, just in case someone was watching. They were still under cover and Naruto was just another civilian as far as outsiders were concerned.
Entering back into the large house, Naruto noted that everything was in a state of panic. Everyone was cleaning and Naruto changed quickly, grabbing a pan and brush to join in the frenzy before Ino tracked him down to talk sex or Machiko could accuse him of being lazy. There was work ready and Naruto was sent to join the group setting up the private rooms, abandoning the pan and brush for cloths and delicate flower vases.
"So they're coming here to renew the contract?" Naruto asked a little while later, looking to one of the women he was working alongside.
"Renew the contract and partake in pleasure," Reiko said with a grin. "They're a busy organisation so even though they pay us enough that they can drop by any time and request someone, we only get, on average, a member or two each month."
"Wow," Naruto said as he arranged another set of flowers. All of the finest rooms were being set up as these customers weren't any average set. They would get whatever they wanted. "They must be fucking loaded," he continued and the others in the room chuckled.
"One way of putting it," Katsumi said and Naruto nodded at him. "They're always nice though, regardless of who they actually are."
Ah. So they were a group of people who most would view as either unsavoury or dangerous. At least Naruto knew before he met them and could pretend that they were just normal people now.
The door to the room slid open and everyone turned to Machiko as she glanced around the room. Her eyes settled on Naruto and she called him out, leaving Naruto no choice but to put down the flowers and follow.
Machiko led them to her office and Naruto couldn't help the uneasy feeling in his stomach. Machiko seemed serious and her brow was wrinkled. When they entered her office, she dove for her cigarettes instantly, sitting down with shaky hands to light them up.
"Thank fuck," she muttered, letting out a huge puff of smoke. Naruto took the seat in front of her desk and waved the smoke away from his face, waiting to hear what had shaken Machiko up this much.
"Our clients are pretty much the top of anything you can think of," she began and Naruto nodded slowly. "We give them goods they need, they give us protection. I think they have that set up with a few villages, but I know that this is the only pleasure house they're… patrons of."
Machiko took another puff and sighed. "We give them whatever they want as long as it's safe. Any of the upper members can literally walk in here unannounced, order everyone to get down in an orgy and we'll happily do it."
In other words: that was how much money the group were pumping in and Machiko would never deny them anything, unless it endangered her girls.
"I didn't know they were coming today. Pein-sama apologised for the hurry of course, but it seems they've been highly strung lately… I don't know why, nor do I want to find out. We all know the Akatsuki isn't a group to open a flower shop."
Naruto flinched at the name and met Machiko's grave eyes.
"The group that protects this village is the Akatsuki?" he asked steadily, wondering if he should just leave now and be done with it. While the Akatsuki had been under the radar for months and hadn't been seen even attempting to catch any of the jinchūriki in over a year, Naruto didn't fancy his chances when he was so blatantly outmatched.
"As a worker, you have absolute protection," Machiko said. She lit another cigarette after dumping the first in an ashtray, pushing that to the side. "And I beg you to listen to what I have to say."
Machiko rubbed her temple with her free hand and it was the desperate look in her eyes that made Naruto stay. To protect this pleasure house was his mission and Naruto couldn't back away from that, even if smarter people perhaps would.
"One patron," Naruto filled in the gaps and knew she meant 'one of the Akatsuki members', "has a specific type when he comes here. Usually a blonde woman," Machiko said, voice quieter than usual.
"His usual entertainer is on leave and the others are all booked out." She smiled bitterly. "Pein-sama gave us very little warning so I'm inclined to say this visit was a snap decision and they all need a little down-time."
Naruto said nothing, unsure how exactly he could respond to that. He'd never paid attention to the sexual habits of close friends, let alone sometimes-enemies.
"What I mean to ask you is whether you'd entertain this client," Machiko said, getting it out there. Naruto eyes bulged and he was sure his jaw was hanging loose. "You'd only have to pleasure him orally… that's all he ever comes for."
Not even the inadvertent pun could shift Naruto's shocked face. While he had come to Machiko's prepared to 'please' however he could, actually being asked to give an Akatsuki member a blowjob was a little too much.
"I-" Naruto began, the words failing as Machiko looked at him.
"You'd be dressed as a woman and he wouldn't even touch you. He never does and the girls often complain when they come out." Machiko rubbed her eyes. "I would ask Ino, but she's enjoying this job too much. I don't know if she'd be able to keep her head."
And by that, Naruto knew Machiko meant Ino's inexperience would put her in a potentially precarious situation. Ino had gained good customer satisfaction, but that was with clients who valued her enjoyment too. Unlike her, Naruto wouldn't expect any personal gain if he took this appointment on.
Besides, Ino was recognisable. She was the heir of the Yamanaka clan and the Akatsuki would be able to spot her easily. Naruto, under make up and female clothes, would be much harder. And, though he didn't like to admit it because Ino was remarkably strong, Naruto was stronger. If something went wrong, he'd be able to take on whatever member of the Akatsuki it was long enough to escape from them.
"I wouldn't ask this of you unless I had to," Machiko said and Naruto looked at her sharply, noticing the waver in her voice. Her eyes were downcast and she looked as though she was about to cry.
"What would happen if I refuse?" Naruto said gently and Machiko nodded to herself, as if she had been prepared for this from the start.
"We'd have to politely decline our customer and offer him an alternate night. I doubt there would be any consequences from it," Machiko said, though her voice was stiff. There was always a potential for consequences and the worst would be that Machiko's house was shut down, the women here forced into less reputable areas and the whole village suffered because Naruto wouldn't take a cock in his mouth.
It wasn't as if the majority of the Akatsuki weren't an attractive bunch. Aside from a few, Naruto knew them all to be in prime condition and to be young. He'd never turned down a willing dick before (another fact that no one back home needed to know: Naruto loved cock) and there was more than his personal feelings to consider here.
"And what would happen if I accept?" he said and Machiko looked up at him, a glimmer of hope in her eye.
"We would prepare you, a few of the girls and I. We have an outfit that would fit as well as a wig. Your client would be waiting in one of the private rooms and it would be his until the morning." Machiko paused and Naruto asked the unspoken question.
"What happens if I'm discovered as a man?" His voice was calm and level, belying what he felt. Part of the thrill would be for this man to have no idea who he was, but it was dangerous too.
"If they attack you then you have my full support to protect yourself and fight back. I cannot predict what they will do, but if you need to get out, then get out." Machiko's voice was firm and Naruto nodded automatically, taking a deep breath.
"I'll do it," he said, the words rushing out his mouth, as if they might be held back should they be said slower. Machiko's eyes widened and she stood shakily, coming to Naruto's side of the table.
"This goes beyond what we asked Konoha for," she said, taking his hands.
"I have a history of missions not being what they always seem," Naruto retorted, thinking of a bridge in a faraway land. "I'm not going to change my mind."
Machiko grinned, grabbing a fresh cigarette and lighting it. She exhaled with a sigh, shaking her head in relief.
"You have no idea," she began, "no idea how much you are helping me. Helping all of us."
She held the cigarette between her teeth as she clapped her hands together and began walking off, looking over her shoulder so Naruto knew to follow. This was it, he thought, the moment when he threw away all inhibitions and dressed as a woman in a brothel.
He's been in worse situations, Naruto thought. He'd never had anything against cross-dressers and wasn't too bothered by the fact he'd most likely be put in a dress, accepting it like he would any mission.
Naruto also had a resolve of his own, a game if you will. Various partners had commented on his technique and Naruto wanted to make his 'client' experience the best oral sex he'd ever had at this house. A personal challenge Naruto would not be telling anyone about, but one that would help him get past the fact that it was an Akatsuki member he was going to suck off.
He took a deep breath as Machiko called upon a small army of women (which in reality was only two others) and entered the room he'd be getting ready in. A light dress hung on one wall and Naruto sat down, trying not to look at it just yet.
"Right, get the marks on his cheeks covered up and bring out the smallest pair of lashes. He's new to this so we'll try to be conservative," were the warning words Machiko gave before Naruto was pounced on.
Brushes and sponges covered his skin, smearing things in and covering blemishes. Glue was applied to his lids (he learnt that the hard way by rubbing his eye, getting glue all over and being prodded for his blunder) and lashes stuck on. His eyes felt heavy and his vision was framed by spider-leg-like creations, something that took a while for Naruto to get used to.
They finished quickly and handed Naruto a mirror. His eyes widened at the change; his jaw looked a little softer, eyes framed in dark powder and lashes looking oddly normal. The marks on his cheek were gone, covered expertly with make-up, and his skin had never looked so evenly coloured before.
The dress was a decent fit. It was high collared, perhaps a little old fashioned, but hid the fact that Naruto had no breasts at all. Machiko had considered letting Naruto wear a bra with false implants, but shaken off the idea, concerned that one would slip free if Naruto became careless.
"Now the wig," Machiko said, clicking her fingers as the girls began to pin it to Naruto's head. The hair felt heavy and Naruto winced as pins scraped his scalp and, not for the first time, he wished he could just use his orioke no jutsu.
After the final touch ups were made – just a hint of lip gloss, colourless so as not to mark when he got to work – Naruto was allowed to see his full self in a floor length mirror. He raised an eyebrow at the change – if he hadn't known it was himself staring back, he'd have been convinced that the reflection was a woman.
All in all, they had done a remarkable job, even without giving him breasts.
"Machiko-sama," a voice from outside of the room called. "Our patrons have finished their initial relaxation and have all bathed."
Machiko thanked the working boy outside and gestured for Naruto to follow her. He did as told, following Machiko down into a small room where a few other women stood, all dressed impeccably in various styles of clothing. All were made up to perfection though and Naruto knew these women were assigned to Akatsuki members, just as he was.
"You know the run down by now. These are our important patrons and they come here to relax. Whatever they want, you'll give it as long as it's in your parameters. Call if it's getting out of hand, get out of there if you need to. I want you girls safe." Machiko lit another cigarette and inhaled greedily.
"Do you know your rooms?" she asked and the women nodded, one stepping forward and smiling at Naruto kindly.
"He is in the magnolia room," the woman said and Machiko nodded.
"You are all dismissed," she said and the women all left, leaving Naruto alone with Machiko once more.
"Are you ready?" Machiko said, tapping her cigarette into a tin she kept in her pocket, closing the lid again when she was done and looking at Naruto. "You can still opt out."
It was too late, they both knew that, but Naruto appreciated the offer all the same. He'd be able to actually do something this way, help protect the pleasure house and relieve a hint of stress he'd built up over the past few weeks.
"I'm ready," Naruto said and Machiko nodded, leading him silently down the hall to one of the private wings of the house.
The magnolia room, it turned out, was a traditional-styled room. It was large and probably held a small table for refreshments as well as a futon. The walls were covered in flower printed cloths, the colours rich and yet not too hard on the eyes. It was a beautiful room and Machiko slid the door open, letting Naruto in and leaving him for the night.
Bowing his head, Naruto stepped into the room and the door slid shut behind him. The dress suddenly felt too short, though it came to rest just above his knees and was obscenely modest for what he was doing. He'd never been one to back down though and Naruto felt his confidence spark in him. He was going to do this and he was going to do it well.
"Machiko-san mentioned a new worker would be my companion," a deep, warm voice said and Naruto tried to control his reaction.
He should have known. He'd prepared for anyone to be his client, but apparently he'd forgotten all about Uchiha Itachi. Itachi – the one man many swooned over despite his crimes. Itachi – the one man Naruto would admit to swooning over (if you replaced swooning with a rather more fun activity). Itachi – the one Naruto had never considered would actually be the one he'd be giving head to.
There had to be a catch.
Oh. Right. Naruto remembered the dress, the wig and the makeup, and the fact that Itachi never reciprocated the attention. Maybe Naruto would have more in common with the dejected women who stumbled from his bed after all.
"Forgive my inexperience, Goshujin-sama," Naruto said respectfully, relying on the title all clients were given at the house. "It will not show," he continued lightly, head still bowed and voice a few pitches higher.
"I appreciate your effort," Itachi said and Naruto peered through a few strands of hair that had covered his face. Itachi was fully clothed, but he had moved to the futon now and was lying down, back pressed against the wall and hand resting on the top of his thigh.
Naruto moved forward, kicking the slippers he'd been wearing off as he stepped into the room fully. His mouth felt dry in anticipation, wanting to make Itachi squirm under his tongue. He'd fantasised about it before, never thought it could ever be possible, but now his fantasies were coming true.
He knelt before Itachi, careful to keep his eyes downcast and chest held back. It was probably the opposite of what Itachi was used to, but Naruto didn't want to be found out. This wasn't just about the whore house or saving Machiko's business anymore. Naruto wanted Itachi's cock, however creepy the scenario was (was it really though – Itachi was the one paying for sex after all…). He was going to get it and that was final.
Itachi's trousers were loose, thankfully, and Naruto slid them slowly over his hips, down until they pooled at Itachi's knees. Itachi made no move to kick them off and Naruto slid a hand over Itachi's thigh, pressing gently until he took the cloth and slid off of each leg, eyes tracking toned muscle and smooth skin. He kneaded the muscle slightly, fingertips tracing the inside of Itachi's thigh until he reached his goal.
Itachi wasn't hard yet and Naruto licked his lips, lowering his body until he was lying on his stomach. The dress tightened around his legs and he shuffled the fabric around his legs. It was soft on his skin and the silk underwear Machiko had forced him into rubbed against a waking erection. He twisted his hips a little as he cupped Itachi's balls, breathing heavily over the cock before him as his own began to swell.
He ran his hands over the length of Itachi's cock considering. It was thick, heavy in his hand, but not extraordinarily length. The tip poked out of his foreskin and Naruto curled his fingers as Itachi hardened fully, hiding a satisfied smile. Naruto risked a look up and flushed when he met Itachi's dark eyes, focusing instead on the light pearly bead leaking from Itachi's cock as he continued to move his hand.
Naruto licked his lips again, wetting his mouth, and was about to reach out with his tongue when a strong hand caught his, halting his movements. Naruto's heart shot out like a jackrabbit and he stared at the dark patch of curls before him, refusing to meet Itachi's eyes.
"Did I do something wrong, Goshujin-sama?" he asked quietly, trying to calm his breathing.
Seconds passed in silence and Naruto wondered if it was possible to die from a heart beating wildly. Then Itachi moved, despite his full on erection and the discomfort he must have been feeling, to collect his trousers.
"Goshujin-sama?" Naruto asked, a little desperately. What had he done wrong? How had he screwed everything up?
"Do not call me that," Itachi said, voice verging on disgust. "I thought I'd be okay to pretend, but when it comes down to it, I can't."
Naruto's eyes widened and he met Itachi's eyes. He was sitting on the ground now, looking up as Itachi paused in re-dressing. His cock was still out and Naruto swallowed thickly. How had he failed?
"I don't understand," he admitted, not bothering to disguise his voice. Let Itachi think he was upset, though that wasn't too far from the truth.
"This is a pleasure house that only employs women." Itachi sighed, one hand rubbing at his eyes as the other held his trousers up. "Knowing who you are, Naruto-kun, I cannot take advantage of you."
Naruto's eyes widened and his jaw slackened. Itachi knew who he was? Itachi knew who he was?
"H-how?" he stammered, wondering if the makeup had rubbed off or the dress had been too revealing after all.
"I was tasked to capture you, when that was our goal. I made it my life to recognise your chakra, no matter how concealed." Itachi sighed again and dropped his hand from his face, looking down at Naruto with a tender expression.
"Under different circumstances," he mumbled, running his hand over Naruto's cheek.
This was not what Naruto had expected when he'd agreed to what Machiko had asked of him. Never once had he considered he would be discovered and even then he'd never thought of what might happen after.
"What circumstances?" Naruto rushed out, wanting to follow Itachi's hand as he pulled his fingers away. His cock was straining against the knickers now and they were dampening, heated from Naruto's desire.
"You're working here," Itachi said, voice tight. "I can't-"
"I work here as a chore boy on a mission," Naruto said quickly, catching Itachi's hand. "Machiko was desperate tonight and I volunteered. This is the only night, the only time, and I want-"
Naruto broke off, swallowing as Itachi stared down at him. There was no hiding the lust in Itachi's gaze, but his self-control was admirable. If Naruto wanted him, he had to prove it was the right thing to do.
He set his hands on the waistband of Itachi's trousers again and Itachi's hand let him pull them down. Naruto supported thick thighs as Itachi stepped free of the legs, kissing Itachi's skin and making his way upwards once more.
"I've wanted you for a long time," Naruto said, voice low and husky. "I've fantasised about the things you could do to me," he continued and smirked at the jerk in Itachi's cock. He held it firmly with one hand, kissing the skin beside gently before moving to survey his prize fully.
"If it were you," Naruto said softly, licking his lips and looking upwards, "I'd let you do anything."
He wrapped his lips around the tip of Itachi's cock and licked the head gently. Itachi's hands twitched at Naruto's side and Naruto smiled, taking him in deeper. He shuffled forwards on his knees, ignoring the silk sliding over his cock and he dress catching around his arse. It felt good, to be before Itachi in such a wanton manner. This was how much he wanted Itachi, enough to keep on these clothes and bring him pleasure.
That and they felt good.
He sucked Itachi gently, drawing a moan from him. Naruto smirked, pulling back with a wet pop and carefully licking down to Itachi's balls, sucking them in his mouth one after the other. Itachi's hand moved to his head and the wig shifted uncomfortably, leading Naruto to ripping it off. The pins hurt, but Itachi's favourable moan as he moved back to the underside of his cock brought a thrill to Naruto that overrode the pain.
Slowly, Naruto moved his hips, pressing the heel of a palm to his cock. He wasn't too far off coming now, however short a time it had been. Every fantasy he'd dreamt of had come true in this night and he had somewhat of a right to come obscenely quickly.
Itachi's hips jerked and Naruto returned his attention to his task. He ran the flat of his tongue over the thick veins on the surface of Itachi's skin, moaning softly as Itachi jerked his hips. He closed his mouth around again, bobbin his head as a and cupped the base of Itachi's cock, moving in time with his mouth.
It was enough to send Itachi over the edge and Naruto stilled when he came, the groan that escaped Itachi's throat triggering his own orgasm. Itachi sank to the floor, Naruto still jerking him through his orgasm slowly, kissing him after he'd swallowed the come down, letting Itachi invade his mouth and taste himself. Naruto was pulled onto Itachi's lap and the dress moved upwards, come slipping out of the silk knickers and leaving a trail of evidence against Itachi's thigh.
Itachi moved his hand under Naruto's dress, but he shook his head, flushing lightly. The last time he'd come in his pants, he must have been in his early teens, yet here he was, dress hitched up to his thighs, come running down the inside of his thigh and the knickers completely ruined.
"Look at you," Itachi said, voice husky. His cock, while limp now, pressed against Naruto's side and Naruto moaned gently, trying to hide the state of his pants with his knee.
"It's embarrassing," he muttered, laughing as Itachi leant forward and kissed him. They were both filthy and Naruto could feel the come cooling already, shifting uncomfortably.
"How about," Itachi began, hands slipping the silk garment away from Naruto before he could protest. "How about I look after these for a while. I'll get them cleaned and you can find something a little more… comfortable to wear."
Itachi raised an eyebrow and Naruto knew he wasn't referring to Naruto's standard clothes. For that he was glad – this dress was too tight in the wrong places and Naruto was already brainstorming what he could do with a whole silk ensemble.
"Next time, I promise not to leave you so coherent when walking out that door." Itachi's smile said it all and Naruto grinned in return, the challenge fully accepted.
He left after shrugging on a spare robe, left in the room specifically for the workers. With a last, regretful look at Itachi (he couldn't stay for that would be out of habit and rouse suspicions), Naruto left and headed to the showers.
If he could just avoid Ino, his night would be perfect.
.
Notes:
There will be a sequel focused more on the cross dressing aspect here. I love the idea so I think it'll go ahead. The title largely comes from Fiona Apples Werewolf and, more significantly, Werewolf Heart by Dead Man's Bones. Not that they have much to do with the actual story, but I like them.
If anyone's disappointed that I didn't do a 'full' sex scene well… you don't need to have penetration to have lots of fun!
Thank you for reading and I appreciate comments of all kinds. Have a good week/weekend when it gets there!