Akane smirked at the boy when he finally noticed her presence, it took the kid long enough. When she joined him it seemed he was occupied with drawing out a little map, and the ronin was able to tell as much due to how... accurate it was. It was definitely strange, geography wasn't a common skill for a servant boy to pick up, normally one wouldn't need to know how to read a map much less draw one himself. Saku had a lot to hide, and Akane was starting to think that she wasn't dealing with a normal servant, well to be fair she started having these suppressions a little while ago.
Then it was his last question that really caught her attention, passing through a city gate unrecognized by guards. That was too way too specific to be a hypothetical question... "Well, to answer your first question, yeah we have to pass through Shinkawa if we want to continue heading north, not unless we want to use side roads, which I don't in case you're wondering." She explained, yet paused a moment to carefully look over the kid, but continued anyway. "As for your second... guess the best advice I can give is act like you belong there. Nothing causes a man to stand out more than looking like he's guilty, even if he necessarily isn't. Confidence but not bravado, there's a difference mind you, can get you pretty far."
Of course she wanted to ask why Saku wanted to pass through the gates without anyone noticing him, but Akane ended up dropping the matter for the moment. Hopefully she won't come to regret the decision for whatever reason.