So "Secretary" just got updated, yay. Unfortunately this has introduced a bug or two into the situation, most notably you can no longer do VR hypnosis sessions with Dr. Trapper, when you try it you get the "you don't have an appointment today" scene and are sent on your way, accessing the "tasks" tab also gives an error. Not sure if this is a bug or not, but didn't notice it until after the update, if you unlock your chastity cage while at work then go to Mistress Antlers while unlocked, she locks you in a cage that can shock you, and your horny % becomes NAN, which locks you out of any horny based options while working, and forces you to choose the "sloppy" option for how to work.
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