Author's note:

This is my first time attempting to write fanfiction for an established anime/manga. I've always put off doing it because I've never felt my writing was strong enough to work with characters that weren't my own. So, I implore you to please READ AND REVIEW!Let me know how I'm doing! If the story is received well enough I'll keep writing this kind of stuff...if not...well I guess there would be no point in my continuing ne? So hit that review button!

By the by: I don't own Naruto. I'm just playing with some of the characters for my own sick and twisted amusement.

Staring at the brass number on the worn wooden door before her the young Kunoichi, who had once fought against Akatsuki with merely an elderly woman by her side, felt her courage faltering. This was a foolish idea. Why had she come here in the first place? While staring at the aging wooden door Sakura began to recall the conversation she had with her friend Ino earlier that day.

The pair were guarded from the intense summer sun by the shade of an umbrella while they sat at a table of their favorite daytime cafe. The conversation had turned from chatter about the latest ninja armaments to Ino's newest boyfriend, or "boytoy", as Sakura liked to think of them. Her blonde friend was notorious for running through boys quicker than a shinobi ran through shruikens.

"Really Pig, can't you just find a nice onc and settle down?" Sakura remarked.

"And miss out on all the flavors there are to sample? I don't think so." Ino retorted. "Your problem is your annoying infatuation with love. You have to love a boy to kiss him, to date him, to have sex with him and that's why you're still a virgin. In the mean time, I'm out sowing my oats and enjoying my youth. We're young and we're Kunoichi. We need to enjoy what we have now; not sit around waiting for some romantic and whimsical relationship to fall into our laps. There is always a chance we won't come back from our next mission, so I believe in living with no regrets. If you died next week, are you telling me you wouldn't regret never experiencing sex?"

Sakura remained silent. Would she honestly regret being a virgin? Biting her lip, Sakura thought on the question carefully. While it was true she longed for a relationship with substance and feeling, honestly she knew the chances of this happening were very slim. As Ino had said, she was a Kunoichi. When she wasn't working at the hospital she was out on dangerous missions. The life expectancy of people in her profession was not high. Besides, when did she honestly have time to go out, meet a nice man, or go on dates and build the foundation of a relationship? She had none. Yet here she was, still holding out and going to sleep alone every night while longing for something that, realistically, she would never find.

Ino, Tenten, Temari and even Hinata had all confessed the joys of sex to the pink-haired ninja. Listening to the stories of their steamy encounters had always brought a warm flush to her skin and a tingling sensation between her legs. Her body craved the touch of another, yet the only hand her body knew was her own. How pathetic was she?

"Yes...I suppose I would regret it." Sakura softly conceded.

"Well then Forehead," Ino stood suddenly, slamming her hands down on the table, "we need to get you laid!"

Several people passing by on the sidewalk stopped to stare at the blonde's exclamation, much to Sakura's embarrassment.

"Pig!" Sakura hissed. "There is no need to make a scene. Sit back down!"

Ino ignored her. "We'll get you dressed up and take you down to a club, find you a looker and you'll be virginity free by midnight."

"Ino, I don't want to sleep with some random stranger."

"Oh?" the blonde ninja retook her seat.

"I don't want to just go out and have sex with the first good looking guy I see. A lot of people would consider that being a slut, you know." Sakura leveled a look at her friend to imply that is exactly what many people thought she was.

"Bah, I call it enjoying yourself." Ino drummed her fingers on the glass top of the table. "I suppose just pushing you off on some random guy might not be a good idea. We need to make sure whoever you sleep with first treats you well and does things right. How about a friend?"

"A...friend?" Sakura paused to think. "I...I don't know if I could sleep with any of them."

"How about Naruto?"

Sakura paled. "He's like a brother to me."

"Hmm...Neiji?"

"Tenten would kill me. They may not be official but she's made her claim on him well known."

"Chouji?"

Sakura wrinkled her nose. "I--- NO! He's...not my type." In truth Sakura couldn't get the image of Chouji eating during sex out of her mind. That was a truly disturbing image.

"What about Lee? He is the second green beast of Konoha and Guy certainly has some good moves."

"Ick! No! I could---wait," Sakura's eyes grew wide. "Ino...you..tell me you didn't!"

The blonde grinned. "It was some of the best sex I've ever had."

A wave of nausea over took Sakura. "I think I'm going to be sick."

Ino rolled her eyes. "It's true he's not much of a looker, but he more than makes up for it with that talented tongue of his."

Sakura was resisting the urge to stick her fingers in her ears and sing "la la la" until Ino was done talking. No matter how good the sex may have been, Sakura couldn't see anyway to justify sleeping with that eccentric man.

"And the only man to have a more notorious sexual reputation among the ladies is Kakashi." Ino stopped suddenly. Her face went blank as the idea struck her, and a large, mischievous grin bisected her face. "Eureka!"

The cherry blossom had a sinking suspious of where this was going.

"Kakashi would be the perfect choice for your first time."

"That's so inappropriate pig! He is my sensei." Sakura exclaimed.

"Was your sensei. You're jounin now, that puts you on equal footing with him. Plenty of jounin have slept with their old teachers and no one thinks twice about it."

Sakura found herself at a loss for words, Ino was right.

"Look, do you think he's handsome?"

"Well...judging by what's not covered by the mask...yes."

"And are you comfortable around him?" Ino queried.

"Of course." Since becoming Jounin, a deep friendship had bloomed between the former student and teacher. She often found herself chatting, even confiding, with him after work and the pair frequently sparred together on weekends.

"And do you trust him?" Ino continued.

"With my life Pig. What is your point?"

"My point is Forehead, Kakashi is the perfect candidate for this "mission". You have the basic foundations of a relationship with him already. Attraction, comfort, trust. It's all there. Meaning you can cling to your ridiculous standards and finally get some."

Sakura was blushing. "But...I...I don't think of him like that! I mean...the idea of dating him never once crossed my mind.."

Ino rolled her eyes. "We aren't talking about dating, we're talking about sex woman!"

Silence overcame the shinobi once more. The words of her promiscuous friend rang true. While she didn't think of Kakashi as a potential boyfriend she'd be lying if she denied having fantasied about him on more than one occasion. She had grown up with everyone her age and could only see them as brothers or boys. Kakashi she had always viewed as a man. A very experienced, talented man. It was quite a revelation to the young Kunoichi to realized that the thought of sex with her former sensei was not a revolting idea. Instead it intrigued and even aroused her.

"Besides," Ino drawed in a sing-song voice, "if you sleep with him you'll finally see what's under that mask of his."

That sealed the deal for the cherry blossom. With a clink of her glass against Ino's the pink-haired woman decided tonight she would truly start experiencing life.

So here she was, staring at the door of Kakashi's apartment yet all her resolve from this afternoon seemed to fail upon facing the reality of what she was about to do. If she left now without even knocking Ino would never let her live it down. Steeling her nerves Sakura clenched her jaw in a determined manner, raised her hand and gave a light, quick knock then waited three seconds before backing away to leave. There, she tried and he wasn't home! Ino couldn't give her shit about that.

However, before she could flee the door creaked open to reveal Kakashi looking at her with a raised brow. He was shirtless and wearing dark blue pajamas decorated with brown pawprints. His lean frame and toned abs caused Sakura to catch her breath and the kunoichi had to force her eyes to his face. His hair was sleep tousled and he wore a medical mask in place of the normal cloth one he favored. She was shocked to realize that he wore no hitai-ite, leaving his sharingan bare. The copy-nin's gaze was truly striking to behold when his scarred eye was uncovered. The tomoe in the crimson eye spun lazily as he continued to stare at her. It was almost hypnotic.

"I know I'm becoming forgetful in my old age, but I was almost certain I was safe to go to bed." Kakashi joked as he stroked his chin. "Did we plans today Sakura? At," He looked backed into his apartment, "ten in the evening?" He did not sound annoyed at her appearance on his door step, only curious. Sakura usually only came calling when he was late for a luncheon or spar.

"Yes. Well...no. Not exactly...not that you knew of. I mean..." She was blushing and stuttering as she tried to explain her presence to the half-naked man before her.

"Would you like to come in?" Further intrigued by her odd behavior, Kakashi stepped to the side to allow her entrance into his apartment.

Taking a deep breath, Sakura walked in and took a seat on his plush couch. Just down the hall she could make out his bedroom, the shruiken patterned comforter tossed haphazardly across the bed. Mr. Ukki sat large and leafy on the window sill. Silently she wondered what Kakashi had been feeding the plant to make it grow so large.

"To what do I owe the pleasure of this visit?" Sakura felt her back go straight at the sound of his voice. The copy-nin had that effect on everyone. Even when speaking softly his voice held the power of authority that made you snap to attention and stand just a little straighter.

"Well...you see..I came to ask a favor." She'd rehearsed this speech in her head a thousand times on the walk to his apartment.

"Hm?"

Looking up to meet his mismatched eyes with her own jade orbs her courage failed once more. Standing up suddenly the pink-haired medic made her way towards the door.

"Never mind...I'm...I'm sorry to wake you up. It was nothing. Really."

A hand on her wrist stopped her before she could flee. His hand was surprisingly soft for a battle hardened shinobi. The touch raised goosebumps along her skin. All afternoon Sakura had been thinking about what sex with Kakashi would be like and now, standing beside him, her body felt incredibly in-tuned to his. The sight of his bare chest had made her mouth go dry and awoken a heat in her stomach that was demanding attention. She'd seen his chest plenty of times before and never once had she reacted to it in such a way. Her hand trembled slightly in his.

"Sakura." His voice took on a more serious tone. "What's going on?"

The kunoichi silently berated herself. She was acting like a twelve year old girl again! Letting her anger at herself fuel her courage she spun around and placed her hands on Kakashi's shoulders then in one fluid motion kissed him roughly on his concealed lips. When he did not respond the young woman stopped. Kakashi was looking down at her, curiosity, confusion and a touch of sadness dancing in his eyes.

"Please tell me you haven't come to confess your love for me..." His tone was flat and held no hint of his usual playful teasing.

Blushing brightly Sakura shook her head. "N-no! It's...it's nothing like that!"

Taking her hands off his shoulders she looked down at the floor. Is that what he thought this was about? Is that how he thought of her? Some girl who continuously fell in love with those around her? Really, she only had herself to blame for that perception. Anger flaring to life once more, she glared up at her former sensei with determination in her eyes.

"I came here to ask you to take my virginity."

Kakashi's eyes grew wide. Whatever he had been expecting her to say, it had not been that.

"Why are you asking me this?"

"I need to stop existing and start actually living Kakashi. I am a shinobi and we rarely ever have the chance, or the time, to develop some fairy-tale relationship. So why not enjoy what you can get?" Sakura said.

"This sounds more like something your friend Ino would say Sakura." Kakashi observed.

Sighing, Sakura hung her head. "I had a talk with Ino earlier.."

"Ah...that explains it then." the white-hair shinobi crossed his arms. "Sex isn't a replacement for a relationship Sakura."

"I know that! I'm not looking to use it as a replacement for anything. I...I still want to have a relationship with someone. One day I'd like to get married, maybe have a child but I've finally realized the likely hood of such things happening are low. One day I may not come back from a mission and there are many things I have not experienced because I've been clinging to this dream. If I want to die with no regrets I need to stop crippling myself. I realized today that I don't have to have wait to have sex with someone I love. But I would like to experience sex with someone I trust." Sakura spoke, looking up at him with honest eyes.

Kakashi was taken aback. At first he had feared she'd fallen in love with him and had come seeking a relationship he could not give her. Then when she spoke of sex he had thought she had decided to use it as means to replace the companionship she so desperately sought. That was a road he did not want to see her travel down. It was a quick way to achieve satisfaction but the loneliness always returned after a fling was over. He'd been walking that road for years now. However her words revealed to him not a young girl looking for a means to quiet her loneliness but a woman who wished to live a life with no regrets. She had finally faced the cold reality of her profession and decided to live as best she could around it instead of depreciating herself by dreaming of a life she would never find. It spoke volumes of how much she had matured.

Silence stretched between the two as Kakashi considered her words.

"Have dinner with me tomorrow." It was a statement, not a question. While the copy-nin had heard the truth of words reflected in those jade eyes, he still could not think of her as a woman over the 12 year old genin he had trained long ago. Besides, taking in her emotional and mental state she was clearly not ready to do the deed tonight. Sakura had worked herself into a state of distress over simply asking this "favor" of him if he was going to do this he wanted her to be relaxed and ready.

Her eyes shun with confusion, he had not outright rejected her but...why did he want to take her to dinner? Worrying her bottom lip she questioned him softly. "...and...what about..?"

"Have dinner with me and we'll see what it leads too." Reaching out, Kakashi placed his hand on her check. "Trust me in this Sakura. Please?"

Nodding softly, the cherry blossom accepted his proposition. Leaning forward he placed a soft kiss on on her forehead with his covered lips.

"I'll come pick you up at Six. Now, off to bed with you."

Again Sakura nodded, she seemed to have lost her voice. Perhaps even her nerve but she couldn't deny that relief had flooded her system when he offered to take her to dinner tomorrow rather than ravish her senseless at that very moment. Heading out of his apartment the medic-nin managed a weak "see you then" then hurried left his building. Closing the door, Kakashi leaned against the cool wood and sighed. He didn't know what was worse, the fact that he was going to be seen out on the town with his former student on a "date" or the fact that he was seriously considering giving in to her "request". For now, he needed sleep and once morning came he'd figure out how to let her down without hurting her feelings. Why did he have a sinking feeling turning down her favor was going to be one of the hardest things he'd ever done in his entire life?

Second Author's Note:

Congratulations! You made it to bottom of the story. I sat on this story for about three months before finally gathering the courage to edit and post it. Originally it was going to be a one chapter deal but while I was editing the fic I decided to make this a multi-chapter adventure.

Unfortunately I feel as if I have hit every cliche there is for a Naruto fic of this nature. Unfortunately though, I don't feel brave enough to venture into something more..."original" at the moment so this is the best I can give you. Please, please hit the review button and let me know how I'm doing! All I ask is you not grade me on grammar, I actually learned very little of it through out my education. If I don't get reviews for this fic I am more than likely going to lose the motivation and courage to keep writing. So again, please review.

See you soon space cowboys(and girls!)