Is there a walkthrough anywhere? I decided to try this and looked for a natural way for the character to change. The hints for Bailey say go to work while plugged and caged, so there's obviously something else that prompts you to wear those things.
Riley's hints say to keep going to social studies, so I did that for a bit and got to the point where she tells you to wear all-female clothes, then the next few times I went I just got a single line describing anal and a gif, then the part where Lexi leaves and Riley gives a bj, both gif and animated on the left.
Until I go to social studies again (says 23) and there's a line that says "You're wracked with guilt over what you did, and not sure what to tell Riley."
Something is definitely broken here since I never got any sort of choice or did anything, it went from going steady to this. I should mention that my "people" section is still blank at this point despite meeting many characters. I go to social studies again and apparently Riley is mad for some reason and won't dialogue. Next time, 25, my character is suddenly wearing a cage and Riley wants to talk about the other night, move forward. Tells me to put on my cage (which I never bought or found) and tells me to find what I'm missing.
Hopefully someone can tell me what I did wrong on this save, or didn't do. It's a shame because judging by the comments on this post this game has a lot of content. I might start a new save when the next version 1.10 comes out if someone can tell me a step-by-step guide for how to properly play through this game.