In Turn 12, we saw that when Orange used the Geass Canceler, Shirley's neurons were rewired to how they were pre-geass, thus letting her be geassed again.
So no, that's not a mistake, and yes, if Lelouch and Orange worked together as a team like that, Lelouch could probably geass someone over and over and over again.
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So no, that's not a mistake, and yes, if Lelouch and Orange worked together as a team like that, Lelouch could probably geass someone over and over and over again.