A/N: Hello, guys! It sure has been a while~ I've recently gotten back into the Naruto manga and it's just crazy. It seems that Orochimaru knew a lot more than he let on while Itachi had the foresight to plan everything.

This is going to be a revised version of Heartless (one of my previous works which I removed). It's going to be darker, grittier, and more mature. Consider the story AU, driven by the underlying idea: What if Itachi had been assigned as Orochimaru's partner in Akatsuki? What kind of ramifications would this have on the future events in the series? Bear in mind that Itachi is slightly older compared to canon.

Disclaimer: I do not own Naruto.

Prologue

The atmosphere in the room was tense, growing heavier with each passing second as the occupants were made to wait.

"Why are we even here?" Sasori threw out menacingly through Hiruko. Its iron tail sliced the air in agitation, speaking volumes of his repressed anger. "I hate waiting."

Leaning against the wall, arms loosely crossed, Kisame could not have been more in contrast to Sasori. "Beats me," he answered casually with a shrug, following the swish of sharpened iron with his beady eyes. "You know I work alone. If you don't know anything, considering you have a partner and are more in the loop, then I have less of a clue." He repeated the information he was given aloud. "All that I was told was to come here for a meeting. "

Usually a meeting consisted of more than two people. Sasori was less than impressed. "A meeting with two people, it seems."

"Make that three."

The occupants in the room turned their heads at the sound of that silky voice, eyeing the owner of it as they entered the room. Once again, they could not have been more different in how they reacted; Kisame looked with mild interest, ever the picture of a collected individual whereas Sasori, seething from waiting, willed Hiruko's iron tail to slice the air faster and sharper than before.

"Orochimaru," Sasori growled in lieu of a greeting, not bothering to wait for acknowledgement in return. "Where have you been?"

"Come to think of it, weren't you guys partnered for a long time?" Kisame shifted his gaze from one shinobi to another, confusion clouding his face. "I would have thought that you two would have arrived together."

"Orochimaru has a tendency to slither away from me."

"Sasori, dearest, you know I enjoy your company," Orochimaru drawled with a smile, crossing the threshold at his own leisurely pace, knowing full well that it would infuriate Sasori by making him wait. "But let's not make this anything other than what it is." His arm extended, hand reaching out to pet the head of Hiruko – only to quickly withdraw as its iron tail attempted dismemberment. "My, how feisty. Did my slithering away upset you so?"

Kisame chuckled at the violent interaction between the two partners. "Woah, settle down," were his jesting words with mirth, rather enjoying the display of violence. "Or maybe I should leave instead." He broke off from the wall, heading towards the exit. "You guys sound like you have some kinks to work out, huh?"

"Do not leave."

Out of nowhere, Pain's voice rang out sharply, drawing the attention of the three cloaked figures in the room. "The meeting is about to begin." How he managed to enter the room without being detected was beyond anyone, however they were not given time to ask for his voice echoed again, revealing the reason for their formal meeting. "A new member has arrived."

Everyone present swivelled their head to face the entrance, pairs of eyes scrutinising the person ascending the short flight of stairs. Sasori, controlling his puppet Hiruko from within, gave no indication he knew the person – much less particularly cared – while Kisame's frown showed his ignorance. Orochimaru, however, knew. There was no mistaking it, the identity of the young man taking his first steps into the black and crimson dawn.

Uchiha Itachi.

Itachi's gait was slow – calculatingly so, intended to convey the ease at which he approached Akatsuki and it worked; the room seemed to shrink around him, a feat considerable given the menacing auras of the S-rank missing-nins around him. He went a step further by unblinkingly staring at each Akatsuki member before narrowing on Orochimaru in recognition, seeing the criminal from the same village they had left behind.

"Uchiha Itachi, welcome to Akatsuki." Pain raised his hands as if to show welcome, though the gesture was anything but warm. It was Akatsuki, after all. "We have been waiting for you."

"Yes, and for far too long," Sasori cut in, not even caring anymore at this point in time, beginning to pace back and forth in restlessness.

Kisame grinned at Sasori, revealing a row of frighteningly sharp teeth. He then hefted Samehada onto his shoulder securely before stepping forward, widening his grin all the while in a predatory manner. "Itachi, is it? Well," he began, weighing his words as he was admittedly interested since he had been working alone up until now, "I guess you'll be my partner from here on out."

"No." Pain surprised everyone by turning to squarely face Orochimaru. "Itachi is going to be your new partner."

Hiruko twisted to regard Pain so fast and sudden that its tail scraped against the floor, leaving a huge tear in its destructive wake. If anything, the powerful display of Hiruko's tail added to what he said next, giving him a sinister edge. "New partner? Do I need to remind you of my existence?"

Orochimaru was just as surprised as Sasori, albeit he handled it with far more tact, playing the strange turn of events off in a coolly mocking fashion. "Sasori is right," he murmured, lip curling in amusement. "I am taken, so to speak."

"What happened to not making your partnership anymore than it is?" Kisame asked with a laugh, pointing Samehada at Orochimaru.

"What can I say, Kisame?" Orochimaru looked not at the sword, but at the owner of it, smiling darkly. "I like twisting the truth. It has that sort of malleable quality that I cannot help but make mine."

As the two men shared amusement on innuendo, Pain decided it was time to move onto business. "Stop getting sidetracked," he ordered, turning to face the man that better resembled a shark than human. "Kisame, you will work with Sasori from now on. This arrangement will do everyone some good with a change of partners. Some of the members have been getting restless. It will work."

"But why does it have to work?" came Sasori's demand rife with irritation.

Orochimaru echoed the sentiment when he stated, voice dripping with sarcasm, "I find myself thinking the very same question. Would you be so kind as to enlighten us?"

"You will all make it work." The edge to Pain's voice was unmistakable. They were asking questions, wanting answers they were not privy to. He made sure they were aware of that when he turned his back on them, stalking out of the room without so much as a second glance. "Dismissed."

Tobi's visible eye flickered to the door as the handle was turned, revealing Pain, who then came to stand by the rusty balustrade of the dilapidated building. Pain's ringed eyes drank in the sight of Amegakure from his position on the tallest remaining skyscraper.

"Sasori and Orochimaru have worked well together," Pain said at last, gripping the metal railing as he did so. "I don't understand why it was necessary to split them up."

"Is that what the three asked?"

"Yes. I, however, made it clear that it was not their business–"

"Good, because it's neither their business to know nor is it yours."

With that said, conveying his finality on the matter, Tobi disappeared into the metal rust that was Amegakure, making his way down the rickety walls. It was raining; the sky was crying. The fresh memory of Itachi crying as he carried out the Uchiha Clan Massacre for the supposed greater good flooded into the forefront of his mind.

Itachi had sought him out, apparently thinking he was Madara Uchiha, enlisting his help on the basis that it would be his revenge on the clan for abandoning him years ago. He had played along under the guise of Madara and briefly wondered if Itachi knew what had transpired – just who he was, in actuality.

Perhaps.

It did not matter, though – for now. There was plenty to do before the time came when the plans set in motion – both by his own hand and Itachi – would take fruition. That, and Itachi would have his hands full with Orochimaru – ironically hailing from the very village he had given everything to protect in secret. The Sannin represented everything Itachi was not due to his pacifistic nature. In a bleak world, that disposition was foolish.

Tobi knew Orochimaru would show Itachi just how foolish it was.