For Sasha you need to win the wagon mini game
For Instructor, you need to take another route with her:
1. Don't go down on her
2. Force her to deep throat you
Yeah, that happens when you try to complete the mini game by replaying the old scenes from the journal. It won't work that way.
I dunno how one can get stuck there. I mean, if there was no bar, I'd get it.
But all you have to do is check what fills the bar, pick like four right answers and go hug her.