AN: I was in school daydreaming and this idea came up for no reason. It was a small spark that had to be protected until I got home to type it. I've written mostly angst and drama but hardly any comic relief so this whole story is a mixture of drama, romance, comedy, OC-ness, and lemons.

By the way I have limited knowledge of the law and what spies do (I watch too much Burn Notice) so if something seems wrong, sorry, and please do point it out so that I may correct it later. I have limited ideas on what they do or how they act so bare with me-it's just a fanfiction.

Full Summary: Uzumaki Naruto is your typical young adult male with high aspirations to reach the top ranks of the spy business. Of course no one said some cases would involve bizarre consequences like posing for a girl for the enemy. Meet Uchiha Sasuke, the wealthy son of a mobster who could care less if you lay in the street bleeding to death. When Naruto is picked to impersonate a woman to lure Uchiha Sasuke for evidence, everything seems on the brink of destruction. What happens when you are gradually falling for the enemy?

Warnings: Language, OC-ness, AU, Grammar mistakes, not beta-ed, some spelling errors, YAOI later, Lemons later, and some investigations that make no sense (probably)

Chapter 1:

Introduction of Two Worlds

Restless nights of remembering and wanting to forget were the primary causes of twenty year old Uzumaki Naruto's insomnia. This was closely related to his job in which reality crushed what he once thought was the world. Today was no different than any other workday. He stumbled out of his messy bed to collide against the cold wooden floor with a groan of pain. The alarm clock blared in his ears as he stretched an arm to shut it off. Finally succeeding to provide once again the peace of daybreak in his apartment, Naruto got on his feet to start a new day. He yawned and stretched still suffering from the aftermath of insufficient sleep. This was the start of his morning, a spy, who lived in the shadows.

Though his paycheck was generous to his previous childhood and adolescence income conditions, Naruto preferred to inhabit a small, but comfortable apartment facing the crystal lake of the city of Konoha. He walked, staggering, to his bathroom on bare feet. A white marble sink was on the right corner, the toilet next to it, a bathtub surrounded by empty ramen cups was took up most of the space on the left, and a medicine cabinet which had a mirror and storage to keep his toothpaste, and shaving materials made up his bathroom. There were no shower curtains for he lived by himself and his friends were mostly all male so there was nothing to actually hide.

Naruto flicked the light and squinted as he adjusted to the intruding bright lights. He used the facilities and washed his hands then took his toothbrush to cram toothpaste into his mouth leaving a burning sensation to take over as the bacterium in his mouth was being eliminated. He gargled and spitted in a continuous cycle until he felt his mouth relieved. The sleep was still clinging on to him so he splashed freezing water on his face. Grabbing a towel to dry his face, Naruto examined himself on the mirror. He was 20, a male, spiky matted hair betrayed combs by sticking out from all angles, cerulean bright eyes stared at the mirror, and three whiskers lines on each cheek combined to make up his attractive facial features.

Satisfied with taking care of hygiene first, Naruto walked back in his room to find his clothes wrinkled on a wooden seat. He sighed heavily, as he slipped into his work apparel which consisted of a suit and tie. Housework was no trade of his as he entered his kitchen that was shared with the living room; emptier ramen bowls were stacked upon another only to make amounting piles of mess. Naruto swore he saw a roach scuttle behind the protective shadows of a hole in his wall. Not that he cared to begin with because he wasn't intimidated by insects of any kind. He opened his half empty fridge which contained a few eggs, an opened carton of milk, leftovers, and an assortment of weird concoctions growing mold. He retrieved the milk carton taking a large gulp from it and grimacing at the expired milk that was now sour. "Damn it," he swore throwing it in the trash bin which was overflowing.

As tradition, Naruto reached for a cup of ramen from his orange cabinet and preparing it to perfection. Ramen was heaven on Earth. Nothing could substitute the texture and unique taste only ramen could cultivate. He inhaled the intoxicating fumes as he poured boiling water inside the instant noodles. Without fully waiting the allotted time of three minutes, Naruto muttered a quick Japanese appreciation for food (Itadakimasu) before attacking the food. Food became a problem for agents like him who were in a rush to actually eat or sleep for that matter. It was good to be home after the long strenuous hours of work but the solitary welcome of his apartment wasn't something he looked forward to.

Once he allowed his stomach a break from too much ramen, Naruto left the empty bowl on his table hardly taking a second glance. His living room was surrounded by glass windows that were shrouded by a flow of orange curtains to permit privacy for the blonde (he didn't need it though). His plasma television hung on the center where it was actually a piece of wall followed by pure glass that provided beautiful scenery at night. After becoming accustomed to his own every day environments, Naruto found hardly amusement in staring out now. Under his TV was a glass table top which held a few compartments filled with DVDs and video games. His consoles that were rarely touched unless he had a free weekend, rested on the floor to collect dust. A couch long enough for Naruto to sleep on whenever he couldn't stand the emptiness of his bed was full of garbage underneath the cushions.

Naruto glanced up at a digital clock on his wall to swear again. "I'm gonna be late again!" he exclaimed rushing into his room to get his own watch and his cell phone. Sure enough his pager rang causing him to jump in fright and clasp a hand over his thudding heart. 'Tsunade'. Crap he was really in big shit. He ran to his front entrance to quickly slip on his work shoes and grab a coat to protect him from the freezing temperatures. He grabbed his car keys from the table at the entrance that hardly offered the decorative intention Naruto hoped it had. He practically slid downstairs cursing in his mind that he was going to be chewed on at work.

And so was the life of Uzumaki Naruto, a promising young spy of Konoha…

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Daybreak was approaching gradually alerting the guests that their grand fest would soon be called to an end. It had been called to an end hours ago but many were reluctant to leave as they staggered from side to side while screaming nonsense. The wonders of holding unique and important parties were passing as many guests groaned from the aftereffects of alcohol, drugs, and sex. Car doors were slammed and breaks screeched under grey pavement. Uchiha Sasuke was in no mood to assure everyone that came was gone from the Uchiha premises. He groaned truly feeling a headache kick in. Another hangover to deal with, perfect. He sat up holding a hand to his head as if this were a remedy to his migraine. At least no whores were around to bother him.

Sasuke grumbled slumping back into the warm covers of his ridiculously large bed that could hold more than five people easily. The black satin covers were beckoning him to sleep more and ignore the duties in store for him today. But of course, his family had other plans for him. And to remind him of his tasks, there was a few knocks from the other end of his spacious room that soon grew loud enough for him to be unable to ignore. "Go away...!" He answered from under the covers.

"Sasuke-sama your father insists you dress and prepare for the plans of today," came a strict reply. Sasuke grinded his teeth muttering he was old enough to take control of his own life. Unfortunately coming from a wealthy mobster family came with limitations for creating a life separately. "You got ten minutes!" called the cool voice of a female. Sasuke knew when Karin meant his father wanted his presence, which meant he HAD to be there in less than ten minutes with no missing articles to send delays. Karin was his personal maid that seriously bugged him all the time with her eyes clearly drooling all over him. He got that a lot from the ladies.

Sasuke rubbed his face with one hand while leaving the comfort of his king sized bed. He had slept with his party clothes on taking no bother to change them. His room had a bathroom of its own. It was lavished with polished checkered floors of black and white with circular bathtub large enough to fit two people at ease. His bath tub was surrounded by different hair products and candles. The sink was attached to the wall and shaped like a bowl and as for his toilet. It was fancy enough to say no commoner would dare sit on it without glorifying the toilet. He closed the door behind him and locked it in case Karin "accidentally" came in.

He was in a terrible mood already. Sasuke slouched over the sink then a glance of himself in the mirror above his sink. His black raven hair parted with bangs at his sides and his hair was naturally sticking into angles resembling the behind of a duck. Though the description sounded unpleasant, he was truly very handsome. Sasuke possessed pale soft skin and toned muscles that added to his slim yet built figure. His coal onyx eyes sometimes appeared with a tint of crimson as to slap him across the face of the demon he was. Sasuke rubbed his temples before brushing his teeth, fixed his messy bed hair, added eye drops to his drooping eyes, applied cologne, and took the clothes from the ebony hamper. The clothes were also all black including the tie. Just the way he liked it: No scandalous colors.

He fixed his tie before examining his appearance in the mirror. So far so good or good enough to scrape by his father's expectations. Sasuke was twenty-one and second in line for the heir of the Uchiha clan. Yet his world was dominated and revolved around his father, Uchiha Fugaku who was the head of the Japanese mafia. Sometimes he wished run away far from the riches into a quiet desolate land where he could enjoy what he wanted: peace and pressure free. Sasuke though had long accepted his fate and was now battling his way to the top.

Sasuke came out of the bathroom and was greeted by sunlight. Great, the bitch undid the dark velvet blinds of his room to truly wake him up. Sasuke quickly exited out of his room hoping to avoid another encounter with Karin who he was planning to fire anyway. He passed corridors heavily decorated with precious paintings, family heirlooms, and pottery. All the floors were polished to a sandy marble stone. He took out his latest cell phone to see he had many missed calls (mostly from women) and some from his subordinates. He ignored them all by pressing the DELETE button on all of the selected.

Sasuke arrived at the grand entrance where the stairs separated into two magnificent arches and crimson carpet covered the stairs. Sure enough, Fugaku was at the bottom of the stairs holding his wife, Uchiha Mikoto in his arms. How his mother managed to stand his father for all these years and still appear young and beautiful was a mystery to the raven. "Sasuke we haven't got all day. Itachi was ready before any of us and I expect you to take your brother's footsteps too," Fugaku said rather brusquely earning a sharp gaze from his younger son. Mikoto smiled though to her son and spoke with her soothing calm voice that never rose more than necessary.

"Now, now, Fugaku-sama, Sasuke knows his responsibilities. He is still young and full of energy and we have time to waste," Mikoto came to the rescue. His mother always knew what to say and how to prevent a fight between father and son. She seemed fragile with her hair that was so dark sometimes in the sun it shined a deep blue, and the same coal eyes like Sasuke, her peach colored skin, and slender figure with the right curves. In truth, Mikoto was a strong woman who gave her eternal love for her husband and her two sons-Sasuke and Itachi. Fugaku merely pretended nothing had happened in the first place and dismissed the subject like that but Sasuke was upset.

Always comparing them two. Why can't you be like Itachi? Itachi has more sense for this type of skills. Try learning some tips from your brother or then I can't take pride announcing you are my second heir. Sasuke clenched his fists but released them when he saw the serenity in the smile of his mother. "Sasuke, honey," Mikoto began by motioning her son to come near her. Sasuke complied – he always did what his mother asked him to.

"Yes, mother?" Sasuke answered coming to a close range but saving distance from his father. Mikoto gave a melodic giggle.

"Your Father and I have been talking lately. We enjoy your parties immensely though we can see no improvement in finding a nice young lady to commit yourself to. Soon you need a wife to bare more children to carry out the Uchiha name and to fill the gaps of your life. I have suggested we introduce you to a few respectful young women," Mikoto said smiling again. Sasuke smirked, oh so that's how it was? His father was apparently using his dear mother to manipulate him into marrying. He was 21 not 30! Besides that, he hated women, they were untrustworthy beings.

"Mother that's very considerate of you but shouldn't Itachi-Nissan be the one marrying?" Sasuke asked kindly rejecting the offer. Of course, of course, Fugaku had to intervene.

"Itachi has no time for women at the moment but is helping this clan rise. You, on the other hand, can continue the family without interfering much into work affairs," Fugaku said. In other words, you're no good, Sasuke, you must provide the laborious tasks for the family. Sasuke shot a glare towards his father.

"Sasuke dear maybe you will like one of the ladies. Come, Mother has arranged all this just for you," Mikoto said using her trump card. Sasuke never refused his mother's wishes. After a few moments of hesitating and receiving expecting expressions from both parents Sasuke nodded.

"Alright though may I make it clear I will not choose a bride," Sasuke said. With that the family left the Uchiha estate to their summer villa near the ocean in Konoha.

It was lucky Naruto was alive and one piece when he arrived at the ANBU headquarters. He had sped through countless stop lights using his privileges as a secret agent as an advantage (which he wasn't supposed to). Naruto ran passing a few coworkers and rushing into the highly secured grey brick building. He impatiently waited as the security men checked his badge, and inspected his bag as well as clothes. Naruto ran at the speed of light almost bumping into a young woman then slamming a glass door open and alerting many curious eyes from work or computers. A man strolled next to him wrapping an arm around his shoulder in a friendly gesture. He had brown unkempt hair and red lines running below his eyes on both cheeks.

"Kiba not now," Naruto warned trying to avoid all time consuming obstacles. Inuzuka Kiba was his best friend who shared the same position in their department. They were partners in fact except at this moment Naruto had no time for Kiba.

Kiba groaned playfully. "Tsunade got your tail in a slum again? She's been calling ya for hours. How you come out alive out of this one, buddy, that's tough to answer," Kiba said energy radiating everywhere. Naruto was like Kiba, but when your boss is going to chew your ass for being late to work AGAIN then there was no room for cheerful spirits. Naruto's eyes widened grabbing Kiba by the collar.

"HOURS!? You guys said I had the night off! Argh, never mind you owe me lunch Kiba!" Naruto said attracting all eyes on him as he scrammed to meet Tsunade. Kiba shrugged helplessly in return as he watched his friend disappear behind another glass office where the curtains shuddered away social contact.

Naruto opened the door sighing heavily and then entering. "Uzumaki Naruto where in the world have you been for the past three hours?" A deadly calm voice said from the back of the dim room. Naruto, was a grown man mind you, but when hearing that sugar coated voice that secretly hid a tone of death then he was truly panicking.

"Hey sorry Gran for being late uh, again…" His voice faltered as he saw the older woman rising and demonstrating what cruel beauty really meant. She strode forward and waved a file in front of his face.

"I'm rather tired of hearing you apologize for your tardiness. Actually I've found the perfect punishment. You see this file is very important. This case is new and is something this academy has not trained you for," Tsunade warned an sly smile noticeable. Naruto shrunk back in fear. Oh the old hag certainly was planning his death.

"W-What kind of case is it? You know nothing is impossible for me Baa-chan," Naruto said regaining his composure and now gloating. Yes, he was one of the top spy agents in all of Konoha. But when Tsunade was ranting of his tardiness then this case probably consisted of long hours of painful torture seeing his boss was pissed at him.

"Glad you asked," Tsunade responded shoving the file in his arms. Naruto glimpsed at it briefly. There were multiple papers and pieces of newspaper clippings as well as a few photos. 'Gruesome murders' Read a headline making Naruto arch an eyebrow.

"Another murder case? Sheesh let does good-for-nothing detectives handle this," Naruto said dumping the file back on Tsunade's desk. His boss banged a fist on the table.

"Listen to me you ungrateful brat. Act like a civilized adult and not a delinquent teenager. Detectives have tried to handle this case but two of them were killed in the process. This has been handed out to us. And you're going to be on this case whether you like it or not!" Tsunade said jabbing a slender finger on his chest. Naruto gulped.

"Hey that hurts!" Naruto said rubbing his sore chest. "Ok fine but what the hell do I have to do? Do I have to jump from building to building?" Naruto asked a pout forming on his face admitting defeat. Tsunade's mouth itched into a mischievous smile.

"No nothing that strenuous. Actually I want you to hone your language and etiquette. Let's see you didn't take the rest of the information in that file into consideration I have to start from the beginning. Hey listen to me!" Tsunade said snapping Naruto from his daze.

"Ok , ok, calm down Baa-chan," Naruto said raising his arms in a peaceful gesture.

"I'm sure you remember the Uchiha clan. Well lately there have been strange murders and somehow they tie in closely to the clan. Of course we have no evidence they are deeply involved in this. Well a few years back the eldest heir to the clan was caught in some fishy business but no one found enough evidence to bring him to justice. We've had countless investigations and few pinpoint the Uchiha Corporation is conducting illegal laboratory experiments. You're job is to go undercover and dig up the truth. Plain and simple. We now the Uchihas are infamous mobsters who know how to play with us," Tsunade explained. Naruto nodded all of the sudden interested.

"So I have to play bodyguard or something like that?" Naruto asked familiar with pretending to be other people. Tsunade shook her head.

"Actually better. The youngest heir, Uchiha Sasuke, has been rumored to searching for a woman to take as his girlfriend. If a girlfriend or lover can be that close to clan itself then we can easily obtain information but sending in an actual woman is rather risky. You know? Pregnancy and such. So I want you to entice Uchiha Sasuke and dig these bastards six feet under," Tsunade said ending her explanation. Naruto blinked stupidly for a few second before laughing.

"Hahaha! Very funny Baa-chan. Seriously what's the mission? I got work to do right? Oh senile moments don't get better than this," Naruto said shaking from laughter. Tsunade gave him a serious expression. Naruto's eyes went wide. "Oooh hell no you can't fucking serious! There is no way in hell I'm going to pose as a woman! Ask Sakura-chan to take this mission! She is an elite agent more qualified than me in this area!" Naruto was rambling on and on. He was going haywire. There was no way he was going to get this case!

"Sakura is busy with another case. May I remind you this serves as perfect punishment for being late? I'll pay you overtime too. Kiba will be your noble distant relative and by that I mean bodyguard. Interrogations begin this evening so it's to the beauty salon for you brat. I've hired a few specialists for the job," Tsunade said waving away the reluctance that clung in the air.

"Come on don't be cruel Granny. What if that weirdo mafia guy hits on me? I'm not gay! I like women! What if he wants to rape me?! Hell no!" Naruto exclaimed throwing random accusations.

"Uzumaki Naruto! You will take on this case or I will fire you! Got it? Now please refrain from foul language. You are a noble wealthy young lady as of today. You will act accordingly to the situation presented once at the Uchiha takes you as a fiancé."

"I'll show you a lady. I hate this job," Naruto murmured under his breath. Today was not going to be a good day. Welcome to the nightmare world of an agent who has to cross-dress as a woman.

"Have fun at the salon. I'm paying so no need to worry. Kiba will escort you to the meeting scheduled with the Uchiha's. On the way he will give you the rest of the details."

"Ok hold up. If Kiba is in on this shit of a plan why isn't he the girl? What part of me resembles a woman? I'm going to kill that two faced bastard when I see him again!" Naruto growled already imagining how he could torture Kiba.

"He's being told of the case next door by Kakashi. Kiba has a more masculine built than you do. Now work your magic and solve this case," Tsunade said as she sat back down on her chair and threw the file at Naruto to catch. All the blond could do was complain how much he hated his boss (at the moment) and helplessly walk out of the office to have the whole department dead silent and staring.

The day couldn't get any worse. Oh it did…

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AN: Ok First chapter done! Please tell me what you think. Sorry for starting another story but my shoujo stories are on hiatus since I forgot what the plotlines for those were.