Its connected to the Whore reputation! Just keep getting that higher and he'll find you more worthy. Fair warning, due to the WIP-ness of the mod, theres barely any content post-enslavement, and Issix is uhm. Kinda an asshole. I don't think his mood system is near complete :/
First off, if you didnt get it, its a map of the engineering block. Just walk around in the restricted section until you find a new button pop up. And wear the blindfold.