Author's Note: Done on request from gsyh. Takes place after the end of "A Fox and a Shark Walk into a Bar," so minor spoilers for that story's ending.
By God the Akatsuki had comely women. This was the first thing Jiraiya noticed when he walked through the double-doors of the Akatsuki stronghold on his way to meet with the organization's commander. It wasn't an important meeting, really, seeing as Tsunade had hammered out all the important details with the older Uchiha months ago, but Jiraiya felt kind of bad for missing out on practically everything while he had been in the Grass Country working on the fourth book in the Come Come Paradise series, so after much prodding, his former teammate had finally relented and let him go to Kaizen to finish compromising with the Akatsuki on several details in their much revised treaty.
The mere presence of the woman who met him at the threshold to the Akatsuki's base almost made having to sit through negotiations bearable. A bit older than was usually Jiraiya's taste, but still immensely attractive even with the Akatsuki cloak thrown over her shoulders and the scratched Stone forehead protector wrapped around her left shoulder, with long flowing hair the color of cedar trees (would have looked better loose, but the braid was almost as good), shining green eyes, and best of all, didn't hit him when he suggested what they could do after he was finished meeting with the Akatsuki commander, but instead smiled pleasantly and said, "Ah, you must be Jiraiya. I've been told a lot about you." She then gave him the thorough examination he usually reserved for an especially tasty young thing and licked her lips. "The descriptions didn't do you justice."
Jiraiya was not used to being on the receiving end of that particular look, but damn… was it hot. "The information I was given seems to have been somewhat lacking as well." He shot the woman a lecherous grin. "If I'd known women such as you were members of the Akatsuki, I would have come over to… negotiate, a lot sooner."
The woman took a step closer to Jiraiya and ran a finger down the side of his cheek, but before Jiraiya could take proper advantage of their close proximity, she turned around and started walking away. For a few seconds, Jiraiya stood there, not exactly sure what had happened, but the woman soon turned back to him and said with a flirtatious wink, "Well, are you coming or not, sannin?"
Jiraiya grinned and started after her. They walked down the halls of the Akatsuki stronghold in silence, Jiraiya practically salivating in anticipation until he remembered the reason he'd come to begin with. "Hey, beautiful, I'm sorry, but I just remembered I'm supposed to meet with the Akatsuki commander in a few minutes (terrible timing, that), so if there is any way to postpone this until later I would be-"
"We're going to the main meeting-hall." The woman shot him a smirk over one shoulder. "That's where the negotiations are supposed to take place, are they not?"
"Uh…" Slightly thrown off by the fact that the woman hadn't been showing him the way to her bedroom, Jiraiya took several moments to respond. "Yes, I think so." A thought finally occurred to him. "Are you the commander's secretary or something, beautiful?"
"Why would you think that?"
The woman's flippant tone immediately informed Jiraiya that his first guess hadn't been the right one. "Well, you seem so knowledgeable about the goings-on here that I thought-"
She shot him another smirk over her shoulder. "I'm in a position to know things, handsome."
After several more minutes of walking down a series of halls that seemed pretty much indistinguishable from one another, the woman finally stopped in front of a particularly intimidating door gilded in metal and gave him one more smile before turning around and walking away. Jiraiya watched her go, the feeling of a lost opportunity making him feel sick to his stomach, but he steeled himself against the immense disappointment (hot, amiable and in his general age group? When the hell would he ever get that lucky again?) and pulled open the door, his eyes soon alighting on the sole occupant, a man with a face split in half by black and white and his body encased by a plant, of all things. For a moment, all Jiraiya could do was stare (he knew some of the Akatsuki were outright weird, but this just took the cake), but he soon shook himself free of his surprise and asked, "Are you the commander? I believe we have business together."
The man-plant turned to look at him, his golden eyes glowing eerily in the semi-darkness. When he finally spoke, his voice came as if two men were speaking in tandem. Very odd. "We are not the commander. We are simply here to act as advisor. The commander will be with us shortly after she retrieves some notes from Itachi's office."
Jiraiya's mouth dropped open. She? The Akatsuki commander was a woman? Why the hell did no one ever tell him important details like that?
He was still fuming when a small door to his right opened and the leader of the Akatsuki organization stepped through. She had long flowing hair the color of cedar trees, shining green eyes, a scratched Stone forehead protector wrapped around her left shoulder, and Jiraiya had been flirting with her for the past fifteen minutes and somehow had completely missed the ring on her right hand engraved with the character for nothingness. Her smile brightened as she caught sight of him. "Ah, Jiraiya! I see you met Zetsu. Don't worry about being outnumbered; he doesn't talk much."
She settled herself at the table situated in the middle of the room and gestured for him to take a seat. Jiraiya didn't move. "You- what- you're the Akatsuki commander?"
She tilted her head to the side and blinked at him in consideration, but her smile, if anything, gained a few more volts. "You're so cute! Not as cute as Orochi-kun, but you have your own points. I'm surprised you didn't find out who I was. I didn't try to hide it from you."
Somehow, only the second sentence managed to make it through to Jiraiya's brain, and instinctually he puffed up. "What do you mean I'm not as cute as Orochimaru? He's all snaky and creepy. I'm much better looking than he is."
The Akatsuki commander made a humming noise in her throat as Jiraiya ranted, nodding at the appropriate intervals, but after Jiraiya had run out of things to say, she steepled her fingers and gave him a slow grin. "Don't be offended, Jiraiya-kun. You are in many ways superior to your former teammate and Orochi-kun only edges you out because he comes with a bespectacled boy toy accessory, but actually, I think you might be more my type."
Jiraiya couldn't help but smirk in triumph over his small victory. "How so, beautiful?"
"You're straight, aren't you?"
Jiraiya went from smug to confused in three seconds flat. "What, you think I'm gay? I love women!"
"See, you're already more my type!" Somehow during Jiraiya's momentary befuddlement, the Akatsuki commander had made it to his side and had placed one hand on his shoulder. "We've never been properly introduced. I'm Hirayama Reiko, commander of the Akatsuki forces, but you can call me Reiko." She leaned in close enough that it would have set off an alarm in Jiraiya's head if she hadn't been so devastatingly attractive, and grinned at him conspiratorially. "You know, I find all these negotiations rather dry. How about I give you a tour of our base instead?"
Jiraiya, if he was being honest with himself, knew he hated politics with a passion, but he had promised Tsunade he'd be good… "Sounds better than this, but we should probably get some work done first…"
Hirayama Reiko sent him a pointed look. "The first stop on our tour is my bedroom."
Oh. Oh. "Well, that's different then." Jiraiya made an expansive gesture towards the nearest door. "Lead on."
Reiko's cheery smile returned. "Knew you would see it my way, Jiraiya-kun. You can give us exclusive trade rights to Konoha's northwestern route later, though if you sign this to hurry things along," she handed him a piece of paper and a pen, and Jiraiya scrawled his name next to the X without moving his gaze from the luminous green eyes staring so deeply into his own, "Thank you, Jiraiya-kun! Now, if you'll look to your left, you'll see where I usually sit and doodle penguins while my council is battling it out over expansion of the south barracks, and in front of you, you'll see the door to the corridor that leads to a bedroom styled in 18th century tapestries that I like to sleep in on Wednesdays…" as Reiko spoke, she gently guided the sannin towards the aforementioned door, dropping the paper containing Jiraiya's signature into Zetsu's waiting hands as she passed.
As the door closed quietly behind his commander and the toad sannin, Zetsu sighed and shook his head. Sometimes he couldn't believe the lengths Reiko went to in order to combine business and pleasure. In one fell swoop she had cut the negotiations short by at least a week and landed one of the few men in the world that actually stood a chance against her in fair combat, all in less than half an hour. No wonder she had ended up as leader instead of Itachi. Some genius just couldn't be taught.