I don't think he's been experimenting with hookers. In Act 2 he mentions that Ms. Leadings hands were the first he'd ever felt. He's just a boy, after all. I think it is about him wishing he knew more about his mother, Ms. Terri (who happens to be a mystery since she hides everything from him). He regrets that he doesn't know much about her and I think Casey is singing in pain "Someday she'll be gone" because the boy will never ask his mother for the truth... and will never be able to find out once she dies.
The first song in Act 2 is about his mother being killed, by the way.
I don't think he's been experimenting with hookers. In Act 2 he mentions that Ms. Leadings hands were the first he'd ever felt. He's just a boy, after all. I think it is about him wishing he knew more about his mother, Ms. Terri (who happens to be a mystery since she hides everything from him). He regrets that he doesn't know much about her and I think Casey is singing in pain "Someday she'll be gone" because the boy will never ask his mother for the truth... and will never be able to find out once she dies.
The first song in Act 2 is about his mother being killed, by the way.