Just discovered this game and it's quite engrossing. So much so that I surrendered most of my evening to it. The women are superb, especially that mom. That being said, the storyline is problematic. Because your mom and sisters are so into you, it doesn't take much effort to seduce them. The fact that Bob was simply irked that his wife called out their son's name during sex and didn't press the issue bothered me. Given his wife's hot and cold moods, you would think Bob would have set up a camera to record his bedroom when he's not around. I feel it should have been Bob not Caroline who got a prostitute/call girl to occupy the MC to keep him away from the missus. I also take issue with the reason the MC needs therapy. As far as I can tell, he didn't make any threats or act out when Celia embarrassed him. Had he lashed out or acted predatory towards her, then I can see why he would need therapy. The fact that he's faced with expulsion if he skips therapy doesn't make any sense.
I'm not the happy with the school mechanic. Aside from certain story-driven events, there's no reason for the MC to attend school. He's not given homework or tests and he's always falling asleep during class. I would have made sleeping during class optional and added a 50% chance of the character getting caught during said act and getting detention. That way the MC would have to stay awake or risk losing time dedicated to other pursuits.