For those of you who have been with me, I'm going back through and trying to re-write the first 4 chapters so they're easier to read and less dumb. For you new peeps, please read the following.

Okay, so this is my first fanfiction. I have been with for 9 years now and I figured it was time for me to contribute back. That being said, some ground rules for my own sake and sanity. I accept criticism that is positively constructed and detailed. Please don't flame; it's rude and unnecessary. If you do not like what you read or see, you shouldn't be here and not everything you encounter is going to be pretty or pleasing. As a last note, I know that many people have different tastes about what they would like to see happen and with whom. Please feel free to express your ideas and I will take them into consideration. However, don't bash either. Characters are characters and I can't please everyone. I apologize for not being God (who doesn't please everyone anyway either).

So, the ground rules being established. I would like to introduce you to the plot idea and the overall structure. It's going to be a fic centered around Sakura and her interactions with the Akatsuki organization (also some slight KakaSaku too). There will be multiple, detailed pairings and this fic is rated M for future lemons, language, and some crude humor. Madara and Tobi are one-and-the-same, moreover, I need an antagonist and I pick him. I apologize again to anyone that loves Tobi and/or Madara. He is, unfortunately (or is fortunately?) my least favorite character and therefore, expendable as an ally.

What else do I have to say? Oh yes….beyond having X number of characters, I will also be tossing out one of my own creation. Her name is Kaylina and you will meet her shortly. I hope you like her (I certainly do and I pray she isn't a Mary-sue either).

Without anything else to say or establish, let us begin.

"Talking"

'Thinking'

'Inners' (Because everyone has one, no matter what they might say on the outside)

Walking from the hospital to the Hokage tower gave Sakura 5 minutes to think about why Tsunade had called her from the middle of her hospital shift (right in the middle of a trauma that Sakura had been patching up) and ordered her to come swiftly, silently, and not to worry about going back to work for the rest of the day. Usually when summons like this happened, Shishou would warn Sakura, that somewhere, shit had hit the proverbial fan and that she needed Sakura and Shizune, both as her right handed apprentices, to go and fix whatever, where-ever. Since Sakura was more than a little worn out from the hospital, she welcomed the idea of a mission away for a week or two and hoped fervently that it would be somewhere with a hot spring and massage available and a hot guy to flirt with.

'Ahhh yes, the male attention is great isn't it?'

'Shut it Inner, I don't want your perverted images in my head right now.'

'You enjoy them and you know it. Besides, without me, you wouldn't get any attention at all if I didn't pester you about it'

'True, but you could be less crude about it, ya know'

'And what? Leave the operations of trying to attain a date to you? Because you are so successful between work, training, learning, and missions to pay attention to the opposite sex? Don't make me laugh'

'Still…..they're disturbing.'

'They are not and it's what happens anyway, better not to be shy and unsure. If you can't be like that on missions, I wouldn't suggest it when you're trying to find a mate.'

'Kami, we sound like we're pursuing an experiment rather than other human beings.'

'As far as men are concerned, they are other than human so we might as well conduct it like an experiment'

'Hardy har har.'

Having reached the door to Tsunade's office, Sakura took a breath to gather herself and her scattered thoughts, before knocking. A sharp "Enter" was heard and Sakura pushed the heavy oak door open.

"Shishou."

"Sakura, glad you could come so quickly. I was worried when I was told you were in the middle of surgery. An embolism correct?"

"Yes, three actually. They were spread though out his body and I was working to decompress him while removing the embolisms as fast as I could so he wouldn't spend hours in the critical unit. Since you called me I turned the operation over to Kie with instructions to call me if things get out of hand. I doubt they will though. He's good at cardiovascular emergencies and he has a steady hand."

"That's good." Tsunade paused looking at her student. "I admire how I have trained you, ya know. You make me proud. I took a lost, confused girl and made her into a fierce kunochi."

Sakura blushed and stared at anything but her mentor's eyes. Tsunade wasn't known for complimenting people (more like turning them into pulp when they earned it) and to hear her say something of this caliber was more than Sakura was expecting. Of course she loved and respected the woman that had turned her into one of the best medics this side of the world, but she also looked to Tsunade as a mother figure as well. Therefore, Sakura craved her approval and worked hard to earn it.

"Thank you, Shishou."

"Hmmmm, well, moving on. There is something I would like to discuss with you Sakura and it's ranked S class."

Sakura's eyes harden and her expression became serious. S class wasn't funny business or something to take lightly and Sakura knew that if Tsunade had called her like this, then Sakura was going to be undertaking a difficult mission. One that Tsunade would only entrust to a few, very close personal friends.

"Alright, let's hear it."

"You know that the Akatsuki organization is a powerful and demented group that has every nation and hidden village on edge. On top of that, no body that I have heard about, talked to, or remotely know, has made a dent in their plans or their members. The ninja world is starving for information on these criminals." Tsunade paused, considering her next words.

"Beyond that, I'm having some difficult issues with the council about what we should be doing. I think another war is coming and I want to step up the rookie 9's training with intensity and diversity. I want weapons to defend this village that are just as deadly and effective as the Akatsuki themselves. On top of that, the council wants Naruto kept to the village for "safety" reasons, but I suspect Danzou is behind it. He understands that Naruto is firmly in my corner and will do everything to see Naruto an outcast once again. Therefore, the plan I'm about to propose should solve quite a bit of problems for me and the village and hopefully it will bear fruit." Tsunade's eyes had a faraway look in them smoldering with anger.

"What I propose, is that you and a partner defect from the village and earn your way into the Akatsuki organization. Right now, there are rumors from every slum and criminal gossip chain that the Akatsuki is seeking more recruits. I want you and another to be those recruits. Kami forbid that criminals that are more dangerous join their ranks without someone gleaning some kind of information about them and their inner workings. If you want to do this, I will give you some last minute training and Ibiki will help prepare you as well. I have no doubt of your skills and I think that you are a sufficient enough ninja to catch the Akatsuki's attention."

Tsunade paused to allow Sakura a chance to absorb this information. The pink-haired woman worked furiously in her mind to figure out how she felt. No matter what, she would do whatever to defend her village, her home, her friends, and her mentor. She also knew that Danzou couldn't care less who he used and how. The issue about Naruto was stunning and made Sakura mad. How can anyone be so blind when the rest of the ninja world was in awe of that man? How ridiculous. Besides that though, how would Sakura defecting help Tsunade step up rookie 9's training?

"How is my defection allowing you to step up rookie 9's training? Is Danzou also interfering with that?"

"Yeah, the council informed me today that they think rookie 9 should begin training younger recruits and taking on more missions to bring in more money. While I don't disagree with income, I find it hard to believe that the council cares about the next generation of ninja when they just blocked a proposal I had made to send the youngsters to Suna for some joint allied training sessions with Suna's up and coming ninjas. It smells something awful of Danzou's melding, the paranoid old fart. If you defect from Konoha, the outrage will allow me to press my idea for intense training of rookie 9 under the guise of keeping them from chasing after you and also to squelch anyone else's ideas of defecting. Not that anyone has any, but it's what I will use against the council. As far as Naruto goes, I will immediately send him with Jiraiya. Jiraiya has been informed about this mission and I have given him permission to explain it to Naruto after they leave."

"Who is to be my partner then?"

Tsunade smiled and her shoulders relaxed just a tad.

"Your partner is an old friend of mine who has helped me become the woman I am today. She and I go so far back, it's almost embarrassing. We both became medics together and developed some of the most impressive jutsus by working together. She is someone that I trust to watch over you and help you while you are competent enough to make her comfortable. You both are perfectly suited for each other and this mission. Her name is Kaylina."

Sakura turned around to find a woman leaning against the door to the office. She was shorter than Sakura's 5'4" height by 3 inches, but she was more built. She seemed to be around her mid-20's. Her long, sandy-blonde hair was up in a ponytail much like Sakura's lengthy pink hair and she wore all black. From her ninja pants, to the socks, to the ninja shoes, to the tank top that also had a mask covering her face except the eyes, everything was black. She had skin as pale as Sakura's own, but while her eyes were a shade of green; they were a bright, almost neon green. Sakura's eyes were the color of a leaf in the summer time and complimented her pink hair color. Much the same way, this woman's eyes and hair also matched. Sakura inwardly sighed as she noted that the woman's bust was bigger than her own B-32's. Not that Sakura was surprised as most women had a bigger bust than her, but she was once again reminded that she was the chairman of the itty-bitty-titty-committee and would be for the rest of her life (unless Tsunade sprung randomly for Sakura to have breast implants which Sakura had considered a few times when her boobs were made fun of .)

"I'm Kaylina. I've heard a lot about you from Tsunade and I'm pleased to finally meet you in person."

"Sakura, and I'm pleased to meet you as well."

"Tsunade tells me that she taught you her super strength and all of our medical knowledge."

"Yes, she did. I'm still learning though. It seems every time I turn around Shishou is kicking my ass in medical expertise over something. If I turn out half the woman she is, I'll count myself lucky."

Kaylina let out a laugh that sounded like tinkling chimes. Sakura realized that she liked Kaylina and wouldn't have a problem working with her. There was something about Kaylina that was relaxing and open. Like you could just sit down, pop a soda, and talk to her all night about whatever and she would enjoy the company and the talk too.

Kaylina looked at Sakura and grinned. Tsunade hadn't been lying when she described Sakura as a peaceful soul and beautiful on the inside and out. Kaylina felt a small regret at being shorter once again, but she reflected that she had never met anyone shorter than herself in all her 50+ years. At least she didn't look old and she had definitely liked Sakura off the bat. Knowing Tsunade, this kid would kick ass easily and Kaylina felt a small worry dissipate to the air.

"Well, now that you two have met. Let me further explain the details of this mission to both of you. Beyond integrating yourselves into the Akatsuki organization, you must win the individual member's affection and trust. What I ultimately want you to do, is to spread doubt about their goals and plant ideas of defection. I know it's a long shot, but I certainly don't want either of you trying to kill the members off since we have more than enough evidence of how well that idea works. By becoming close with these dangerous men, you will have a precious opportunity to obtain personal information about them. On top of that, figure out the ritual they use to extract the tailed demons and come up with an alternative that allows the host to survive. We can gain precious allies if we can save the people who are currently vessels. I don't want you girls to compromise yourselves for this mission, but I do want those men to be brought down. I leave how you go about accomplishing this factor up to you individually. This mission will be the longest either of you have ever undertaken and you have up to 5 years to see this through. If things even look close to falling apart, abandon the mission ASAP and return to Konoha. Your lives are more valuable to us here, when you're alive, then dead in a ditch somewhere else."

"So hearing all of this, do you Kaylina and you, Sakura, formally accept this mission? Are there any questions?"

Kaylina and Sakura stood side by side and each lost in her own thoughts. This could be as intense as ever and the chances of success weren't high. However, most S ranked missions never looked good, involved a great deal of personal risk with low stats on survival and both women knew in their hearts that if they could pull this off, the world would be a significant margin safer than before.

"Tsunade-sama, I accept this mission." Sakura stated simply with a hard look in her eye and her chin held high. On the inside, she was worried and slightly overwhelmed with the task she was undertaking, but if her mentor thought she could do it, than she could. Plain and simple.

"Old friend, you owe me a bottle of sake when I get back and some new pieces of the jewelry I love so much. Yeah, I'm in solid and will kick ass for you as always."

Tsunade beamed a smile at her friend and close-enough-daughter. A weight in her heart was lifted even if a different worry took its place for safety of the two before her. Tsunade reminded herself that she didn't have anyone else to trust with something like this and there weren't a lot of qualified candidates to boot.

"Glad to hear it. Go home for the night and rest. We have two weeks before I want you to set out. Also the next few days up to your departure will be filled with pure training. Don't bother going to work. Just report here tomorrow morning and Kakashi will explain and help you practice how you're actually going to defect from the village."

With that, Kaylina and Sakura bowed to their Hokage and exited the office. Tsunade sat back in her chair and thought about what was going to happen.

"So Sakura, you ready for the adventure of your life?" Kaylina asked.

"Yeah actually. I'm nervous and a little bit overwhelmed, but I think we can do this. We are going to have be extremely careful right before we meet the Akatsuki and right after we're accepted into the organization, I think. They're hardened, S-class criminals who scare just about everyone in this world witless. I can't imagine they trust easily and they will have their own personality quirks that we have to contend with as well…"

Sakura trailed off as she began to think about what she needed to do and how to go about doing it. Kaylina smiled softly and silently agreed with Sakura.

"First things first, kiddo, we have to gather all the information we know about the Akatsuki. If we're going to be willing recruits we have to act like it and showing up not knowing a damn thing isn't going to look very convincing….or we could flash them, I suppose….."

"Flash them?!" Sakura turned to Kaylina, gaping and slightly shocked to hear the woman cracking a joke about the mission. "You may have not noticed, but I'm not rockin' in the bust department. And I don't want to get raped my first day on the job either." She shot back.

"Good point, that would be awkward. On the brightside, I strongly suspect they are good looking men. That's an added bonus!" Kaylina chirped. She was silently pleased that Sakura was fast thinking on her feet and could banter. It would help to have someone around who could joke and tease just as easily as Kaylina herself could.

'Finally! Another woman who understands me! Stick with her hon, and we'll be laid in no time! After a year of deprivation, I'm ready for some hot action!'

'Good Lord Inner! This woman beside me maybe a virgin for all we know! And I don't need to be reminded of Tsai, thank you very much. I hope that bastard falls off a cliff.'

'You and me both sweetheart. On another note, I've been wondering something. Tsunade said that Kaylina and her go way back, but does Kaylina look 50+ to you?'

'Good point, she doesn't. Should I ask?'

'Might as well, you have to get to know her if you're going to be working with her for the next few years.'

'Kay.'

"Hey Kaylina? May I ask you a question? It's a personal question, I don't mean to be rude, you can totally refuse if you want!" Sakura squeaked at the end and waved her hands in a frantic, but placating gesture.

"Go head."

'This kid is adorable when she does that. She clearly doesn't want to offend me.'

'Ya think? The kid just learned that you and Tsu go way back. She most definitely has figured out that you could kick her ass royally if you're anything like Tsu.'

'Shut the fuck up inner and don't make me hurt you. I'm not going to scare the kid. I'm supposed to guide and watch out for her.'

'Yeah, because you're a stellar influence, tch…'

"How old are you? Tsunade said that you and her go way back, but you don't look a day over 25 if I'm any judge"

"You caught me. I'm actually 56, but I have a better handle on the same jutsu that Tsu uses to keep myself looking younger. We decided a long time ago we didn't want to feel our age, much less show it, and it confuses people to boot." Kaylina chuckled that tinklely laugh again.

"Ahhh that explains it."

"Yep. Say Sakura, how old are you?"

"I just turned 20."

"Oh really? So you can go to a bar right? Can I buy you a drink before this ridiculous mission starts?"

Sakura let out a laugh. Yeah, she would definitely enjoy working with Kaylina.

"Sure, there's a bar I know just down from my apartment that serves the best mixed drinks this side of Fire country."

"Let's go and we'll toast to the start of an adventure and a friendship."

"Sounds good!"

The next morning….

'OMG! WE ARE TOTALLY SCREWED!'

'Shut up inner, please! This headache is a killer, we are late for our meeting with Tsunade and I still feel slightly sick from last night! I should have known that Kaylina could put it away just like Shishou!'

'Well, I don't think Kaylina's doing any better than you cupcake. At least you didn't throw up like she did.'

'Hmmm, then again, I didn't take straight shots of everything the bar had to offer either!'

'Yeah, pretty impressive. Anyways, move it lead-butt or we're going to get pounded, headache or not!'

'I'm going! I'm going!'

Sakura burst from her front door and tore across the roof tops, knowing that being 30 minutes late was a good excuse for an ass kicking. Hopefully, Tsunade would remember that Sakura was very, very rarely late and could forgive her this once. Kaylina, on the other hand, hadn't bothered to budge from Sakura's couch yet…

'I hate you.'

'Good morning to you too sunshine! I'm so glad you're here to help make this headache worse! Remind me why I allow you to exist?'

'Because without me, you would be a dead woman who doesn't know when to quit while she's ahead of herself and not over indulge in things like drinking.'

'Ah, yes, the kill joy. Remind me how I have ever been able to have fun with you hanging around.'

'You have fun because I help you limit yourself and not burn out from over exposure to "fun". Now heal this damn headache, get your lazy ass up, and make sure Tsu doesn't beat the kid for your stupidity. Kami save that child from you and your bad influence.'

Kaylina groaned and rolled off the couch. She found that Sakura had already fled the premise and proceeded to follow. She might be one of Tsunade's oldest friends, but that didn't excuse being late or the sound ass kicking that might ensue.

"By the love of the first! Have you no respect for your betters! I told you yesterday to get into my office THIS MORNING so that we could get on with the plan! I don't recall anything about drinking to the wee hours of the morning, getting sick, being late, and encouraging that my apprentice do the same! You are 56 years of age, dammit! Act your age, not your height!"

Kaylina winced as every word beat on her poor head! Oh yeah, this is why she shouldn't have been out drinking or at least late to the office this morning. Tsunade and her temper would never change.

"I apologize Tsu. I figured Sakura and I could bond like woman over a couple glasses of wine. I guess we got carried away….."

Tsunade flopped back into her chair. "Yes, well, why don't you heal Sakura's symptoms and she'll heal yours? This way, you both get your first feel for each other and we can get on with the day's work." She huffed.

After Kaylina and Sakura relieved each other of their hangovers and various symptoms, Kakashi popped in to instruct them in their pseudo-defection. They would set fire to a number of important structures for a diversion, not that the fires would be serious, but enough to make ANBU jumpy and take action. They then would "threaten" the Hokage herself, steal some forbidden medical jutsu scrolls (which were completely fake) and then beat the hell out of Kakashi himself when he made an attempt to stop them.

Sakura blinked at that last part and looked up into his face.

"I don't want to beat you."

"You don't have a choice. I'm smart enough to figure out what's going on, part of ANBU, and I'll be posted on gate duty on the appointed day. If I just let you walk by, things look awkward for me and no one can guess the real idea behind this. You must truly appear to defect or the Akatsuki will know something is up."

"Kakashi…."

"Don't worry Sakura-chan, I promise I won't hit hard either."

"You are such a jerk."

Even though Sakura called him a jerk, she still smiled, knowing that it would be okay despite her reservations about whom she would be hitting. He smiled under his mask and continued with the explanations. They were to book it as fast as they possibly could to the border of Fire and then cross into Rain. Reports indicated that the Akatsuki were concentrated around that area so that would be the best place for Sakura and Kaylina to begin.

"And one more thing ladies. To add to this grand deception, you're going to have to cut across your headbands. Rest assured that you will receive new ones when you return, but this needs to be done before we even stage the fires."

Kaylina fingered her headband which was tied around her head, much like Sakura's was. This same headband had been with her since her days at the Academy. It had even deflected a kunai once. As scratched, dented, and chipped as it was, she was unhappy to fully disfigure something that represented the years of work and service she had given leaf.

Sakura was also thinking about her headband. She had kept Sasuke's band after he had left Konoha and she even had one from Naruto. To mar her own was something she hadn't thought about and it made her sad. This symbol represented her home and her allegiance.

After the meeting with Kakashi, Ibiki came next and began to instruct them in the arts of deception, concealment, psychological torture and survival, and manipulation. By the end of the two weeks, both Sakura and Kaylina retained the skills needed to help them work through the Akatsuki organization and implant seeds of doubt while keeping personal information to themselves. Tsunade and Kaylina helped Sakura perfect some complex healing jutsus and taught her how to store extra chakra behind a small mark of personal choosing anywhere on the body.

Sakura choose a small star to sit right below her breasts, just on the bottom lip of her sternum. Kaylina had hers on her hip while Tsunade retained the one on her forehead. On top of that training, Kakashi helped to create the special solvent that would burn like fire, but wouldn't spread rapidly or burn that hot. He also taught a variety of different elemental techniques to aid them, both in any scenario they might find themselves in and to appeal even more to the Akatsuki. Those two weeks were intense and exhausting, but also rewarding. Not only did Sakura feel more confident, but Tsunade felt less insecure about her friend's and apprentice's safety. Kaylina learned how capable Sakura really was and entrusted her safety to Sakura without reservation.

Soon the night for the staged defection came about. That night, Sakura and Kaylina sat in Sakura's living room, packing last minute scrolls with extra supplies, going over the plan for night for the umpteenth time, and trying to eat something before setting out. Sakura finished packing first and considered that she might have one too many kunai forcibly jammed into the bulging pack. She then shook her head and repeated the age old mantra, better to be prepared and safe, then caught unawares and sorry. Kaylina was thinking along the same lines as she too stuffed as much weaponry as possible on top of the tremendous supply of medical equipment. In truth, both women found comfort in these basic routines as the night weighed heavy on their hearts and minds.

"I hope Kakashi wears extra shin and arm guards. I'm upset at having to hurt him."

"Don't worry Sakura, he definitely can handle himself. Besides, I won't be hitting hard either. That man is too sexy to dent and I want to date him when we get back. Best not to leave the last impression of myself as having punched his lights out, ya know?"

Sakura cracked a smile and shook her head. After two weeks of training beside Kaylina, she had learned that the older woman's mind was often in the gutter and she flirted shamelessly with any male she found attractive.

"By the way, what is the deal between you two? I noticed that Kakashi seemed really over-protective of you and he made damn sure you knew every jutsu he could throw at us."

"Yeah…..he once told me that he regretted how much attention he had paid to training Naruto and Sasuke and leaving me to fend for myself. After Sasuke left and I had apprenticed to Tsunade, he started coming around more to "make it up" to me and I guess he just hasn't quit."

Sakura blushed slightly at the memory. Kakashi hadn't just wanted to make up for lost time; he had confessed to Sakura that he was somewhat attracted to her and would like to spend more time in her company. While not unused to the occasional confession of infatuation that came from being 20, beautiful (so she was told), talented, and a medical ninja; Sakura had been flabbergasted! Her mouth had dropped open and Kakashi had promptly told her that she resembled a fish when she did that and she had responded with a well laid punch to the gut that bent him over. Since then, they had hung out at her apartment and gotten along companionably.

Seeing the slight blush on Sakura's face, Kaylina understood instantly that there was a small potential seed of romance and wished it would bloom for Sakura. In the two weeks that Kaylina had been with Sakura, she had learned that Sakura had a temper to rival Tsunade's and that the she cared deeply for friends, family, and the village. Kaylina was also surprised to learn that Sakura was not, in fact, a virgin and had the standard 'he strung me along and dumped me' story that most women go through at some point. Kaylina had her own, but it was so far back she had forgotten the name of the poor bastard (which might have been for the better, since Kaylina was known for anger as well). Therefore, Sakura deserved better and a chance at romance even though it was a rare and special luxury for any shinobi.

Glancing at the clock (11:30 pm, fyi), Kaylina realized it was time to put their plan into action.

"Here we go kid. Remember to set fire to the wing of the hospital that has no patients and the corner of the local food mart. I'll be running around setting fire to electrical plant, the monument, and the Academy. We have to meet in front of the Hokage tower precisely at 12:00."

"I know. Did you remember to cut your headband?"

"I did, but I don't like it." A grimace of distaste flashed crossed Kaylina's face.

"Neither do I but it doesn't matter. 12:00 at the Hokage tower, 12:15 at the front gate, beat Kakashi within approximately 5 minutes and then we run like hell."

"Yep, yep. Let's move."

With that, the girls slung their packs across their backs, turned off the lights, locked the front door, and sprinted in opposite directions. Soon alarm bells could be heard urging anyone within earshot to help suppress fire and save property. Smoke was seen curling into the night sky and cries for water and sand stretched across the night. ANBU were scattered around attempting to track the arsonists.

Abruptly, the Hokage tower on the top floor burst apart as two figures dashed away. Tsunade stood there bellowing for the "traitors" to get back there and explain themselves and what the hell they thought they were doing! The dark streaks darted towards the gates were Kakashi engaged them both and was soundly whipped for his troubles. People stared in disbelief around them as the whole thing took less than an hour for utter chaos to follow. And the worst part was the whispered question, "Was that really Sakura who I saw?"

Alright! There is chapter one! Up and running! I hope you enjoyed and if you see something amiss, please inform me. I work to improve all the time, but outside opinions are the best way to see what's wrong.

I really don't have an update schedule down so I won't promise what I can't deliver. Besides that, I also don't know what the average length of the chapters will be.

I apologize if any part moved too fast or wasn't well explained, again, please let me know.

I ought to stop writing at this point because I'm sure I'm making stupid mistakes.

I will also try to incorporate more humor. I understand this wasn't very funny, but I figured I best be serious about the plot and the characters first, then lighten things up down the road.

Reviews are good things, so I have read, but don't really know since this is my first fanfiction. Let's give it a whirl, hmmmm? Maybe you'll like reviewing and I'll like reading the reviews – could be a beautiful relationship.