Here's my save that should have you all set up so you don't need to grind too much. It starts where you get rejected by mom to sleep in her bed and then the memory of almost getting raped from work is triggered. Only two story lines to follow here are every day in Afternoon, visit Mom and make her dinner with wine and spend time with her. Sometimes choose not to spend time with her after making her dinner with wine. Then revisit her every night.
As for Lucy, visit her at Noon or Afternoon on some days and help her study, keeping a mix of trust and not overdoing the spankings.
She'll then ask for $300 for a dress and well, you'll see how the story line progresses. Just be sure to check the Pool and the Living Room every now and then to talk to her for getting your money back.
This save is for Taboo version and you can edit your console (Shift+O) and say money=700 every time you want to add more so you can keep making dinner's for the mom.