This whole writing fanfiction is kinda new to me. I wrote an awful crack-filled Harry Potter fic once… back about 5 years ago and haven't done anything since. So it might be a bit rough for awhile, so if you see any mistakes… Review! Tell me what you think!

Summary: This story is bordering pretty close to AU. Instead of heading back to Konoha after a 2 ½ year long absence Naruto and Jiraiya are assigned a mission to infiltrate a host club. Naruto goes in as a beautiful (albeit a bit slow) hostess to seduce and destroy rich old men who are involved in funding the Sound. He's in for a shock when the clients turn out to be a bit different then he had initially imagined. The story will be eventual SasuNaru, but don't think it'll go the way of poor (emo-brat) Sasuke being tricked by a guilt-ridden Naru-chan into loving his female form. The story is mostly comedy based, and I've kinda cut out important events that would be happening in the universe at the moment. Gaara's kidnapping? Didn't happen. Sexy Sai coming in? Not yet, but I'm considering putting him into the story, if only because he's frickin awesome.

Disclaimer: Naruto was created by Masashi Kishimoto and not by me. But just you wait, in five years I'll come up with an idea that will make them go, "Naruto-who?" Yeah. That's right. kicked in the head

Chapter 1

"I thought issue #37 lacked the same sort of passion that made Icha Icha so great… Sensei, you know I of all people would never doubt your genius… But don't you think that Kaoru should've been topless in that last scene…?" The man had initially looked normal enough, or at least he came off that way when Naruto had first approached the Ramen stall. The owner greeted him with a friendly smile and efficient service. It was all going well until Jiraiya strolled up with his latest novel tucked under his arm. The owner noticed, and when Jiraiya introduced himself Naruto could almost see the stars of admiration coming from the eyes of the other closet pervert. It was like they were a secret club, of which his teacher was president. They could greet each other with nose-bleeds, rather then secret handshakes just to prove that they were members.

"HEY! I'm trying to eat my breakfast!" Naruto slammed down his unused chopsticks (he was just sucking in the noodles anyways) and glared at the man talking to the pervert-sannin. Jiraiya just turned and gave him a disapproving glare, his large upper lift curling upwards.

"Art is only ever distasteful to those who lack class. I'm so sorry sir, my student isn't like you… admiring the beauty and grace of a nubile young woman searching for love in a harsh world… " He shook his head and sighed, looking across the street. Naruto could tell by the light blush that he had probably spotted a nubile young woman himself. Youth being the understatement. It was so wrong that a old geezer like him was still trying to hit it with girls over thirty years younger then himself.

"Ah yes… About Kaoru… I didn't want to expose her quite so early… The tension adds fuel to the fire, eh?" Naruto rolled his eyes and finished his Ramen. The owner of the stall waved away his money.

"Anything for the student of the great author himself. I can't believe I met you in person!" He grinned happily and idly cleaned his counter. Naruto put his scarce savings back into his froggy purse. So what that he was fifteen and he still carried it around… He had also kept his precious seal cap until recently. It was so cute with its googly eyes! Tragically, it disappeared mysteriously one night… He suspected Jiraiya took it, if only because he always knew the man was jealous of its simplistic geniousiticness.

"I'm always honored to meet one of my fans and hear their suggestions. And have no worries for the future and Kaoru's virginity! My next issue will be the steamiest one ever! Secret preview right now…" His teacher leaned over the blue table and whispered something in the owners ears. By his reddening face Naruto could tell that whatever was being said definitely wasn't meant for the public.

"Oi! Pervert Hermit! I'm leaving! L-E-V-I-N-G! Now!" Naruto threw back the curtains of the Ramen stall and stormed into the busy street of Nara.

"Leving?"

"My student's kind of an idiot."


"What are we still doing here?" Naruto plopped down on his single cot with a huff. He placed his tan hands under his chin and pouted and glared at his teacher under his long blond bangs. Nara wasn't a bad city and the Thunder country wasn't bad in itself, but Naruto wanted to get back to training, and they had been here a week seemingly without any reason other then to rot in their hotel room.

"What do you mean? I took you out for Ramen and everything! Now you're complaining already… such a brat…" Jiraiya entered through the door of their cheap room, his white hair nearly touching the tip of the door frame. He passed a mirror and started to run his hands through his massive mane.

"Took me out for Ramen… Ha! That was on the way past the brothel! Stupid pervert. You just wanted to see the ladies in the window didn't you?"

"I was looking at the brothel, but not to see the lovely ladies. I was doing research. Now that you would actually comprehend something as useful as that."

"Research? Aren't you done you current book? Your excuses are almost as sucky as Kakashi-sensei's."

"No, it's research for our next mission. I got a message from Tsunade. There's been some suspicious activity there, meetings among… Sound nin's…" Jiraiya must have known what kind of effect those words would have on Naruto, but it couldn't be helped.

"So… were we sent in because… because… he'll be there?"

"Honestly, I don't know Naruto. But there is a reason we were requested… I not sure whether you're going to like it, but with you I guess one can never be sure." With this Jiraiya went into the closet and pulled out a long bag. It flopped loosely in his hands, but it was ambiguous enough that Naruto couldn't make it out.

"Eh? What's that? Where did you get that? Is it some kind of great and magical weapon you're going to give me? I swear it better be-" He stopped. He stared. The bag was open… and inside was…

A cute pink dress…

"AHHHHH!" Naruto screamed and pointed his finger violently at the thing sitting in the bag. "You have to be kidding!"

"Naruto there's no need to overreact like this! I know it may come as a shock to you…but-"

"YOU'RE A CROSS DRESSER!"

"-I'm sure the dress well fit you… Eh? What? I'm a cross dresser?" Jiraiya raised his eyebrow.

"… The dress will fit me…? EH! AHHHH!" Jiraiya ran over to Naruto and hit him over the head.

"Shut up!" Naruto just bit him in the hand and jumped off the bed.

"You can't make me become like you! I'm a BOY! Booooy! See no boobs!" He pulled up his black T-shirt to a blank faced Jiraiya. "You can put on your make-up… your high heels and stuff your bra yourself." He crossed his arms defiantly, and he could hear banging on the walls where their poor neighbors were trying to get them to quiet down.

"Damn brat. I don't cross dress… except that one time… That was one wild night… Hehe… Ahh… That woman had some weird feti… Er… That's beside the point. Don't you think you're over-exaggerating? We want you to use your Sexy no Jutsu to infiltrate a nearby club. It was you who created the infamous jutsu in the first place wasn't it? You willingly invented the great technique that single-handedly brought down the Third Hokage himself! I'm sure Tsunade thought long and hard about who was best for this mission. It's something only you can do!"

Only I can do... Hehe...

Jiraiya could almost see the sparse brain cells inside his students head turning…

It must be a super-important mission! A-class, just for me!

"Yosh! You mean like a super-exclusive deadly mission! Count me in! Wait… But Naru-chan would never wear pink like that. I want baby blue!"

Jiraiya was happy that Naruto accepted the mission so easily… It was good that he was starting to accept responsibility, even if he had to have his ego prodded to activate it. Sometimes he would admit that he really was a good student, always eager to…

Did he just refer to himself as Naru-chan?

"Uh… That's good Naruto. I was just wondering… Do you… happen to have any strange hobbies yourself? I mean, you did create a jutsu that turns you body fema-" Jiraiya just barely dodged the pillow thrown at him.

"Just tell me what my mission is!"

Four hours later found Naruto in Sexy no Jutsu form, wrapped in tight red satin with his blond curls falling down his back loosely. His blue eyes glowed in the mirror, and his lips pouted and posed as he modeled his body in different positions.

"Damn you are FINE."

Hands on hips. Hands in hair, twist the legs… Just like that.

"Super finnneeeeee."

"Are you done admiring yourself yet?" Naruto jumped as Jiraiya came up behind him and handed him his make-up bag. Jiraiya had gone to the store awhile ago, when he didn't come back right away Naruto started to suspect that he had lost the nerve to go to the cosmetics store without a female companion in sight.

"You should knock you know! Naru-chan deserves her privacy!" Naruto covered his rather ample chest and gave a coy pout to Jiraiya.

"Don't do that at me! And don't speak in third person to me like that. Normally it'd be cute… But it's you! Eh… It's stomach-turning to see such a beautiful woman… and know it's your brain behind those breast's. Anyway's, remember one thing. It's not Naru-chan, it's Kiku-chan. You grew up in a rural village outside of Nara. Majorly rural. Think a population that's the same number of your brain cells." Jiraiya was interrupted for a moment by Naruto growling at him while sloppily putting on his lipstick. "Your grandparents raised you in place of you parents and you are an only child. Make up a tragic story about your parents, get big eyed and tearful if need be. You moved to Nara for work and now you are the cute Kiku-chan, new host at the Kamikochi club."

The whole mission was based on the access to the club. Tsunade had heard of the club only through rumours, and as time went on she found trustworthy sources that could identify it as fact that high ranking Sound villagers and nin's often frequented the club. The nin's themselves were often not that important, or they would not be as foolish to continue a habit of visiting the same place multiple times. The people they were after were the rich lords who funded the Sound's ventures. If they could be identified and managed the Leaf could undermine much of the power that Orochimaru had gained.

Jiraiya could go inside with his long standing reputation and set up a mole, and while they had considered getting a proper kunoichi to complete the mission they couldn't manage to find a properly trained young woman willing to do the job. They would've used an older woman, but Kamikochi sold on the age of its hosts.

They would use Naruto, who was both used to seduction and who was used to his female form being objectified. That was where most kunoichi's would normally fail, as the attention from the older men could be damaging to their pride as strong independent women.

"Do you think I should make my boobs a little bigger? Kiku-chan wants to be a knockout." Jiraiya was fairly convinced that Naruto would have no trouble at all.


Naruto checked himself once more in a window just one more time. His hair was artfully placed in the regular pigtails, but two ribbons swirled around as ties that matched the red dress. His scars had been covered with make-up, but they remained faint, only creating the impression that his cheeks were a little fatter then they actually were. He had been a bit self-conscious about it before, but Jiraiya said it came across as looking cute, before looking faintly ill about saying anything at all.

When they had first met Naruto had initially gotten Jiraiya to train him using his Sexy no Jutsu, but it seemed as time went on the reality of the person behind the body being Naruto was enough to conflict even the super pervert Jiraiya. He knew many kind of woman he would never have a relationship with, but as long as they were sexy he would admire them. But Naruto's other form could have the face that launched a thousand ships and he still would only remember him making fart noises to make snot nosed little kids laugh.

"Yosh! Let's do it!" Naruto pumped his fist in the air Rock Lee style and began his somewhat tipsy venture across the street in his high heels. The Kamikochi itself included an extensive garden before the actual building, but the grounds were surrounded by a massive red wall and equipped with two burly guards at the gate door. They only stared out of the corner of their eyes as Jiraiya gave them a wave and pulled Naruto through.

Inside large willow trees bent over a wide stone pathway, all leading up to the elegant red Kamikochi with it's angled roof tiles shining under the midday sun. Small ponds and sections of flowers and rocks created a diverse garden that helped to calm Naruto down as he made his way down the path, occasionally grabbing onto Jiraiya if his heel found a certain crevice between the stones below.

"The owner knows nothing, I've only told her you're something of a simpleton, so that should cover most of your mistakes. But try to make a good impression at least, and watch the other girls working before you try any kinda… techniques you might think would work. You can't just take off your clothes and pose like you normally do (with those conveniently placed clouds) and hope they'll fall for your every whim."

"You did."

"Eh?"

"You totally fell for the Naru-chan attack! Back when I was twelve, I just did that and I totally owned you!" He grinned at his teacher and gave him a peace sign.

"Only for a moment."

"No. Total ownage. Hehe." They were in front of the steps now, and Naruto could feel the beginnings of butterflies in his stomach.

"Well, I be leaving you here. Machi-san should be waiting for you inside. You'll recognize her right away; she'll be the one with the enormous pipe and hair so big that it could support wildlife."

"Aren't you going in?"

"Er… no. I owe her a bit of money from our last meeting. She's pretty stingy about paying back your debts and all. Last time I was late she set her dog on me. Stupid tiny yippie thing. Kinda like you! You should get along! Good luck!" With this he slapped Naruto on the back and shoved him through the doors.

"Hey!" He shouted back but the doors swung closed behind him with a foreboding thump.

"Welcome…" A face of horrors loomed in the darkness… Lit up by the light of a pipe…

"AH!" He jumped back and slammed his body on the door behind him.

"The girls these days are sure jumpy… Geez, what's Jiraiya doing sending me idiot amateurs… Feh." The voice gained a proper face as Naruto finally made out the room to be the front coat area, lit up only by two simple candles, but decorated with richly designed carpets on the walls.

"Nashima Kiku, ne? Not bad looking. Your jumpiness could translate to liveliness. He did say you look a little dim…" The old woman, who could only be Machi-san walked right up to him. Naruto tried to resist the urge to climb right up with walls. 4 out of 5 instincts were shouting something between "EVIILLL!" and "This bra is going to give me a massive rash", which was somewhat irrelevant to the current line of thought.

Her face was a circle of wrinkles, out of which two tiny black eyes flashed out with an intensity that even his ex-teammate couldn't have matched. What was scarier was her massive head, covered in intricate tiers of hair that rose her almost past Naruto's height, which was no light feat considering she might've been under 4'0" normally. There were things attached to the thing… Sticks and baubles that swung around whenever she moved her head in any way. It was almost enough to distract him from her hand reaching out and poking his face with her crinkly demon hands.

"Eeehhhh, you'll have to do. I'm a girl short ever since that Naomi attacked poor little Kairi with a poker stick." A poker stick? What kind of girls were these hosts? Naruto scratched out any kind of idea he had to woo one of them out of his head. He had enough scary woman in his life, Sakura and Tsunade coming foremost to his mind (Machi-san was there now as well… She was so scary he wouldn't even try calling her Oba-san. Hell, he'd refer to her as Machi-chan if she insisted) and he certainly didn't need any more.

"Ah… ah… I'll give it my best! Haha, no problems here! I'll never touch a poker stick either! Haha… ha."

"… Farm girls. Come with me, I'll introduce you to the Kamikochi. And keep your mouth shut when I'm talking. I don't care for your questions yet, the only replies I want are 'Yes Machi-san', I won't take any back talking." With this she took out her long wooden pipe out of her tiny lips and blew out an enormous smoke ring that was a faintly blue in color. Naruto caught a glimpse of her yellowing teeth and tried not to grimace.

Following Machi-san into the hall allowed Naruto a full view of the main area of Kamikochi. His first impression consisted of circular tables with lush seating occupied by men in fine suits and hosts. Naruto himself had ended up wearing a sexy red number (he had originally wanted a cute fluffy blue dress, but the pervert-sennin had said no) but the women were clothed in all different styles. Jiraiya had explained that often Host Clubs offered different types, so all sorts of men would be satisfied. And it was true, there was a cool young woman in a dainty Kimono, a cute young girl in a flowing white dress and even a tall elegant young woman in a floor length evening gown. In all there was about seven hosts, but each was entertaining at least two men, all smiling graciously.

"I'll tell you something right now. This isn't a brothel, we're a Host Club. Allowing any hanky panky tells our customers that we are cheap. It's a warning, though Jiraiya told me your grandparents trained you well."

"Er… Yeah. I mean, yes Machi-san."

"Good girl. In fact Jiraiya went on to even say that on the farm you used to wear full body underwear just to protect your chastity. Yes, that's how I would raise my children…"

Full… Full body underwear? Naruto tried to squash the homicidal urge to chase down his teacher and strangle him with said un-existent underpants.

"…Yes Machi-san." He managed to choke out.

"This here is Iori-san, he's the bartender here, but if you have any problems with touchy-feely customers just shout for him." Machi-san gestured at the man behind the lavish bar beside them. He was tall and muscular, with shortly cropped hair and scars across his arms and face. He greeted them with a friendly and open grin to contradict his tough guy appearance.

"What a cute looking girl! Anything you need just tell me, I'll be there in a second."

"Yes Machi-san, I mean, pleased to meet you!" Naruto gave him a short bow, which he returned. With all this manners stuff that he had to do Naruto wondered if Tsunade had a double purpose to sending him here.

As he stood there thinking one of the hosts came up to Machi-san without him noticing. The girl was the one in the spectacular blue kimono, and up close she was one of the prettiest girls he had ever seen. But he didn't miss the cold calculating look she threw at him from under her dark thick eyelashes. She might have looked like a doll, but she was probably the crazy one with the poker stick whacking habits.

"What is it Naomi-chan?" Machi-san's voice was filled with more warmth then when she talked to Naruto, and her mouth almost looked like it was smiling. Did they both bond over their abilities to make one want to run fast in the other direction?

"Our regulars are here. Even Satoshi." No honorific. Were these the people he was looking for?

"Lead them to their regular table, and send your current guests over to Miho, she's good with large groups." Naruto followed Naomi with his eyes as she walked towards the doorway. One by one men began to walk in, until the group had to be eight strong. Two of the men's steps were entirely silent against the floor, and something told Naruto that not only were they his targets, but the two he had picked out were definitely shinobi.

The first he saw was plain faced enough, dressed in a simple business suit. It was only his posture that gave him away… The second was wearing a gray yukata, and had his faced turned away from Naruto. Instead he addressed Naomi in soft tones. She simpered at him, and all the hardness in her personality melted away to show a soft beautiful woman.

When he turned Naruto finally saw his face, and seeing the dark eyes, the dark long hair running down the sides of his cheekbones caused Naruto's breath to catch.

He almost looked like…

"Sasuke."