Challenge: Dark Orochimaru with Jiraiya.
"The preparations for the attack are completed. We are ready to move out at your command, Orochimaru-sama," and the dark spider child gave Orochimaru a deep bow, "Jiraiya-sama." The bow was repeated, though this one had the addition of a grin. Jiraiya grinned back. Kidoumaru was a good kid. A bit flaky at times, but his memory was flawless and his planning skills were unparalleled, which was why in Kimimaro's absence the minutiae of this mission had largely been left to him. At a dismissive gesture from Orochimaru, the young Sound shinobi turned and walked out of the room, presumably to join his cell unless something else went wrong. It probably wouldn't. Otogakure was a village composed of discarded children and missing-nin, but the kids tended to be loyal enough to border on fanatical and the missing-nin didn't like Konoha on principle. Even so, Orochimaru looked more grim than satisfied with the way things were going.
Jiraiya tapped his former teammate on the shoulder. "Something wrong, Orochimaru?"
The snake sannin's eyes flickered towards him. "Do you honestly believe you will be able to go through with this, Jiraiya? Konoha has no idea of your activities over the last ten years. According to their records, you're still a Leaf-nin, merely on a long-term sabbatical to pursue other activities. It would be far too easy for you to betray me at a critical point to join Konoha's forces, and they would accept you with open arms. If you are having second thoughts about this, I want to know now."
Jiraiya rolled his eyes. "I'm seriously getting sick of that question, Orochimaru." Even if it was one Orochimaru had to ask, it didn't mean there wasn't a point where Jiraiya just wanted to reach other and slug the dark-haired shinobi. "I've invested ten fucking years in half of these kids. You actually think I'd leave them to rot after spending so much time on them? Besides," and Jiraiya grinned with just a little too much teeth, making his expression sharp-edged in place of the usual cheeriness, "As long as you stick to the plan, I have nothing to object to, do I?"
From the way Orochimaru's eyes narrowed, Jiraiya's suspicions had been spot on. "The damage we could do to Konoha if you would just-"
Jiraiya's grin widened as his hands clenched. He didn't bother affecting a stern tone. If there was one thing he had learned from Orochimaru over the years, it was that one tended to take the imbalanced far more seriously than the stable. "Not a fucking chance. Konoha is a village with a disease, a sickness I've agreed to help you get purge. Wouldn't be very helpful to our childhood home if we got rid of the healthy parts along with the blight."
Orochimaru smirked and closed his eyes, so Jiraiya allowed himself to relax. His former teammate only broke eye contact when the argument was over, which meant that Jiraiya had won this particular bout. Good. It was too close to mission time for Orochimaru to bring it up again, and even if Orochimaru was the resident god to most of the brats, they respected Jiraiya enough that if the dark-haired sannin tried to push the issue during the attack, everything would go to shit, and Orochimaru wasn't stupid enough to jeopardize everything for minimal gain.
However, even if Orochimaru was willing to let the issue die, it didn't mean he wanted to change the topic. The snake was irritating like that. "So much anger in your voice after so long, Jiraiya. I would have thought that your temper would have cooled after twelve years."
Jiraiya didn't bother with an answer. He didn't even bother getting angry, just leaned back against the cool stone that made up the walls of Otogakure's inner sanctum and let out another sharp-edged grin. Orochimaru's baiting hadn't lessened over the years, just gotten more vicious as if to pick up the slack for Tsunade after their third's insults tapered off to nothing. Along with her sanity. Jiraiya knew Orochimaru well enough that the snake sannin's attempts to goad just came off as another way to alleviate the boredom, since no one else could summon up the courage to disagree with the almighty Orochimaru. "Shouldn't you be getting ready, Orochimaru? You heard Kidoumaru. Time to move your ass. Can't waste time thinking about old shit like that."
If Jiraiya knew Orochimaru better than anyone else alive, Orochimaru knew Jiraiya better than he knew himself, but the snake sannin didn't press the issue for once, just smirked and pushed himself to his feet before moving towards the door. He paused at the threshold. "Don't agonize over your nightmares too much tonight, Jiraiya, if you can possibly help it. Tomorrow your student will finally be avenged." The silent accusation went unspoken, but it still hung in the air. Tomorrow your student will finally be avenged… as he would have been twelve years ago, if you'd had the courage to go through with it.
Jiraiya didn't rise to the bait. "Sure. Just remember to wait on finishing off our dear old teacher until I get there, okay? Wouldn't want the Sandaime to go off to the happy killing grounds without knowing exactly who engineered his demise. It'd take all the fun out of it."
Orochimaru rolled his eyes. "Just be quick with the Kyuubi brat. I won't be able to stall Sarutobi-sensei forever."
Jiraiya grinned. "Of course. Even if it is the Nine Tails, in a human body, demons have human limitations. Easy as pie."
Orochimaru smiled back, though his non-threatening grin somehow managed to come off ten times as dangerous as Jiraiya at his most bloodthirsty. "I look forward to a souvenir." Then he was gone, leaving Jiraiya behind in the near darkness, remembering the demon who had murdered his sole remaining student, who had sucked the life out the Yondaime Hokage, leaving only a lifeless husk behind. Remembering his indecision twelve years ago to slit the throat of a baby as it slept in its crib, the soul of a demon sealed in its stomach. Knowing that his indecision had long been replaced by regret and bitterness. Twelve years ago, the demon should have died. Tomorrow, Jiraiya would finally complete his duty and kill Uzumaki Naruto, the vessel of a demon, murderer of one of the greatest shinobi the world had ever seen. Tomorrow, after he had corrected the mistakes of the past, Jiraiya could finally sleep.