Ficlet inspired by Senju Tsunade and the Shikabane-hime by Ashen Author. You can find it on page 17 of the Recursive Fiction Topic in the forum.
1. Orochimaru had first heard about Shikaku's daughter in passing - a comment from Inoichi on how Shikaku seemed even lazier than usual. He'd only paid attention to them because the frustration of his most recent failure had been such that he had wanted a diversion - any diversion. They'd talked about the baby Nara's diagnosis of chakra sensitivity and more intriguingly, the fact that she had survived the Kyuubi incident. She had been the only chakra sensitive child to manage that - he himself had lost twenty specimens - and he'd felt a vague stirring of curiosity. He hadn't acted on it in the end because he'd gone back to his labs from that meeting to discover a breakthrough with the Senju project and after his games with Danzo had taken all his attention.
2. The second time Orochimaru heard of Shikako she was again, nothing more than a footnote. Her name was mentioned only as the obligatory third team member of the genin team that would hold the Younger Uchiha and the Jinkurriki and in all there was only one sentence given. It stated that she would probably not prove to be a hindrance in the Younger Uchiha's growth until he could be successfully retrieved as she was by all accounts a 'serious kunoichi'. Orochimaru had snorted at that - Tsunade had been the same once - and wondered briefly if this Team 7 would suffer the same fate of all the others. There is barely any mention of the girl at all in the following reports.
3. The first time Orochimaru actually sees the girl in person, it's just outside the Forest of Death. He hadn't bothered infiltrating the first part of the exams, it would have been a waste of time, but this... Registration... is unavoidable. The hopefuls will be watched to closely going in and the the borders guarded. This is simplest and he can check on his dear former apprentice. He also takes the opportunity to note the feel of the Younger Uchiha's chakra and that of his teammates to be safe. The girl feels like gossamer shadows and damp earth - expected, as she is a Nara with an earth affinity - but there is something extra to her chakra that he can't quite categorise. It brings to mind vague, long forgotten curiosity. Still, he is here for a purpose. The girl is nothing compared to her teammates potential.
4. In the forest he is unsurprised to find the Uchiha's team together. Kakashi had by all accounts done an amazing job of reducing the Uchiha's potential as a flight risk. He is not surprised when the girl and the Uchiha manage to dodge his attack, though he hadn't expected it. He is mildly surprised that the girl can throw off the paralysing effect of his killing intent. It doesn't matter, she is nothing more than a particularly irritating fly and he swats her away absentmindedly. Then the Jinkurriki is there and he half ignores the girl again. Naras. Smart, intelligent but ultimately useless. She is within his notice only because her chakra never separates from his prey and using her questions to instruct the Uchiha is... Useful. But she interferes again, and now he is actually mildly annoyed. The Uchiha's choked cry of anguish as he takes his second teammate out is obvious to his ears and he absently makes notes of the boy's regard for her. Perhaps she is the one needed to awaken the boy's mangekyo sharingan? It is enough of a possibility that he doesn't kill her personally when he's finished with the Uchiha. She could be... useful. That doesn't mean he fails to mention her to his little puppets. They are so eager to impress after all.
5. It seems he was correct in his estimations. He had been mildly concerned at Kabuto's failure to locate them but his second had confirmed that his puppets were dead so the seal had presumably settled correctly. Of course, when Team 7 successfully makes it to the preliminaries and the girl once again shows that she is as smart as she is irritating. It is not difficult to sense the way her chakra unfurls inside her teammate, pushing up against his seal, again protecting her teammate. He takes the time to imagine someone of her intelligence and loyalty in his force as he toys with the Uchiha and feels mildly regretful he didn't make a move for her when she was younger. It is a fleeting emotion, easily suppressed by the amusement of once again succeeding in pulling the wool over his old sensei's nose.
6. Orochimaru is arrogant, prideful and dismissive of those he deems weaker - but he is not a fool and knows what his weaknesses are. The Invasion of Konoha should have done vastly more damage than it did. It had not, so his plans had failed and now, now he needed to know why. Ultimately, it was easy to conclude that there had been a leak of some sort. Less than a day after the preliminaries had finished, Kabuto was cornered by ANBU and forced to blow his cover to escape - apparently as a result of a number of different clans filing their suspicions. His own careful preparations had been limited by the resulting surge in security. Even Sensei had been better prepared than he had anticipated. Orochimaru narrowed his eyes in anger. If he ever found out who it was that had revealed his spy, he would take great pleasure in making them his next specimen.
7. The next month or so does not go as well as Orochimaru had hoped, but there had been progress. His arms were still damaged, but better than before, and Danzo had called on his skills. He had offered the location of his future host in payment. It had led to the chance to observe the most interesting confrontation. Not that his puppets knew he was watching, but he had enjoyed seeing how the boy was growing. The irritating girl was there, apparently well recovered from her run in with Itachi. His host definitely cared for her more than he would have preferred if his softly spoken query was any indication. In his distant hideout, Orochimaru narrowed his eyes. Those bonds would have to be weakened if he was to lure the boy away.
8. There had been no one who returned from the mission to retrieve the Uchiha, and only one live prisoner taken by Konoha. He wasn't concerned about Tayuya. If she returned to him, good, but if not there were others. Even if they were less skilled, they would have a purpose. It did mean that it took him time to find out what had happened. Time, during which he was forced to use his back up body. The girl hadn't played a major part in the so called 'Sasuke retrieval' mission, but it does not escape his notice that by all accounts she had latched onto her teammate and countered the Sound Four's manipulations. Sasuke had chosen to stay because of his ties to the village, to his team - to her. Perhaps his approach towards the young Uchiha was wrong...
9. Orochimaru rarely takes an interest in events beyond his own games, but the incident in Grass captures his attention. The rumours are disjointed, twisted by the budding civil war that has kept Grass so nicely distracted from his own activities... But they all agree that Nara Shikako had been under the Kantokusha Clan jutsu and had still been able to fight back and activate explosion tags. It shows a level of skill beyond what he had expected from the Kunoichi... It reminds him of all those moments he had been vaguely interested in the girl in earlier years. It reminds him of her intent to kill, her presence that had been coincidently on the outskirts of all of his greatest failures recently. Nara Shikako is interesting in her own right and if acquiring her will bring his desired host straight to him... Orochimaru smirks as he begins to plot.