When I was doing a thief run and had a cage, I did a non-combat pacify via a tuggy like any good christian would do and after I had "fucked them silly" I ended up losing my virginity to their backdoor despite the cage that I had no key for. Bug or just limited ending issues?

I'll take a look at it, been making sure new scenes are all chastity compliant while stamping out the last old scenes that aren't.