Going some pages back, I see I missed some discussion regarding femdom content (or the lack of it) in the game. It is kind of baffling that we have stuff like the cock stare skill (penis humiliation), pet cock skill (penis teasing), cock kick skill (CBT), amazon position from initiating vaginal sex, footjobs (where Karryn calls the nerd a degenerate), taunt (intimidation) and flaunt (seduction) but no unique femdom route for the corruption. I mean, you can turn Karryn into a sort of succubus, but half the time her dialogue won't fit the image of a dangerous succubus draining men. I would have been happy with just the game making a more immersive distinction between a maso Karryn and a succubi Karryn. I don't think this would conflict with the game's identity since, you know, it's already 'there' just not expanded upon in a satisfactory way.
If I were to have the fortune of making a Karryn's Prison clone, I would make two routes for the corruption: being violated and being desired. Being violated leads to a maso heroine, being desired leads to a succubi heroine. The end result is the "same" in a gameplay sense, winning through sex, but what options are available and how the heroine acts would be different. Perhaps a gameplay difference could be that for the maso heroine it's all about not passing out while being used until the enemies lose interest, while for the succubi heroine it's all about making the enemies pass out while using them. Right now in Karryn's Prison it's sort of an awkward mix of the two, gameplay and immersion included.
Yes, you can lose in the waitress job. As for that bug, I haven't experienced it, you should try one of the cheat mods and teleport yourself to an area like Karryn's Office. Should work.