I've had a look. To progress in the story :
1) go talk to Linda
2) when spying on Rachel by the pool, stay until the end
3) when Rachel mentions checking Chloe's homework, go in the Interior at 13.00 and steal the homework, and stay to watch at 15.00
4) spank Chloe, raise her pain threshold by increasing the force of the blows. now she can take 15 medium and 5 light. she should be able with some training to take 20 hard ones
5) next time you have a study day (not chores), keep one hour of study and study at 18.00 on the Terrace with Em. it will unlock the BJ and lots of things will open from there
You're still in the early stages of the story, follow the hints of the events