Did you try Rachels punishments at the start of the game? I had no problem with the punishments, but fired up a more finished game (more quests done) and yep it no longer works. So one of the completed or in progress events breaks it. Maybe Rachels helping hand, or Aunt makes a mistake, not sure.ok looked at the walkthrough and many of those things just aren't happening at all. my level is all the way to game over, still no punishment things on the paddle. she's said she was going to punish me but nothing ever happens, regardless of her mood. when i get sent to susan she just makes me wait around for an hour, no femdom stuff at all... also chloe when her mood was 0 still did the bending over in the hot tub. for rachel, i did absolutely nothing she told me to do for several days, no spanking, no threats to kick me off the boat, just the you will be punished line but nothing ever happens. maybe i'll get it happening with the walkthrough cuz some things haven't been completed like the naughty doctor, just 1 star on it cuz i've only caught her 1 time. also have given rachel the sleeping pills but the first time, nothing about the clock at all, then somehow i did it again without linda's help and got the prompt about the clock, but she still woke up on time haha wtf?
For Susan and the waiting, that's tide to the punishments so makes sense there, that changes when you go for help not to get kicked off.
And for the sleeping pills, yeah doing it again without Linda also makes sense, it happens on the correct path. Maybe also happens on a first time fail.