I totally understand where youre coming from with this. Ill look at making it like how breast enlargement was in the original game where the bigger your butt/breasts are the more work it takes to level them up to the next level.
No this is not a bug (although its not explained in the lore). Ive discussed adding a weekend in the other thread but this would be a very big undertaking and so im saving it for later down the line. Currently im just thinking of having it take you to the screen you usually see after school/the gym where you can choose between going to your dads or to the beach etc. But aside from this youll also be able to do tutoring on the weekends and im thinking about making another questline where youll get a job or something like that. Again this is all stuff thatll come much later in development though.
Ah yeah i think this is by design but if a lot of people have issues with it i can look at changing this. I think the idea is that your character is resisting their inner sissification and this leads to them being sexually unsatisfied until they start accepting it.
Ill look at this rn.
Its been a while since I played the original but I feel like that wasn't the same. I know you're just revitalizing the old game but if you're looking to improve on it then you could have the character have a thought on why he's still aroused. Maybe even make it more specific as he grows from straight to gay/sissy.