The most difficult thing is the transition between rejecting and slowly accepting that has to be kinda realistic 0.14b left with ms. Anna slowly opening up followed by Liza in the pool incident but the others not
Hmm, here's a shot in the dark
1- For Anna, we can see her rely on Bobby more like grocery shopping because she's nervous to go outside however, she could want to go out and explore outside like clubbing or going to the spa because she feels depressed to be locked up inside. Bobby could take advantage of her while she does that. Maybe trying to make outside even more scary like paying a homeless man trying to assault her and he could intervene as the hero or not and get more submission, like the workplace incident.
2- For Liza, She can be so blindly "in love" with her boyfriend that she goes back to set things right despite Bobby warning her being genuine. and it could be a trick of Liza as she can get drugged and taken advantage of by the boyfriend and his friend. However, Bobby can stop it by drugging her himself and having fun w/ her instead of letting her go. Intervening then you can bring her home and continue the party, or just take her home n sleep (cuddle w her), or let her get double oreo-ed.
3- Lucy, I think as a plot for her development Julia (the friend that raped Lucy) could be blackmailed by Bobby to do increasingly sexual acts in order for him to be willing in helping her fuck Lucy. He could record a video of it and hold it against her. Julia could try to steal it and can get fucked by Bobby as punishment.
Meanwhile, Lucy and Julia are going out to parties more, we can find out that Lucy does this because she's scared of failing her tests for school and we could have Bobby try to steal future tests, and we have the choice whether to keep it and let her pass or get a fake one and push her into failure. We can also continue the Study sessions as thanks to Bobby from Lucy, Bonny can get more sexual.
4- Jenny, We find out that our innocent little sister is actually a stripper and likes the thrill of it and gets money in the process but is unwilling to admit it because she finds Bobby to be a weird person to talk to about this stuff. We could have Bobby bring gifts in order to get closer to her and when that relationship is maxed out then Bobby could go to the Strip Clb w her of Blackmail her saying he'll tell ms. Anna unless she provides him with a reward.
Woah...Sorry had like 3 cups of coffee, I just really want this game y'know so that was a quick thing of where I think this could go...