Naked Houseboy

Young man strapped for cash applies for position as naked houseboy.  CollarChris visited the basement a couple months ago in spite of his having no experience being spanked and having a very boring profile on Fetlife.  Nice smile and he seems to be open to learn.  Get him in lots of positions and redden up his butt some.  Says he's interested in returning.  Fast forward and he initiates a return visit.  But hard to find time.  He's so busy.  And he's short of money.  Maybe I could help him out.  Well,  think this boy needs to be whipped into shape.  Certainly the application  process should evaluate tolerance for spanking and paddling.  Got to get this boy in shape.  And not sure he's going to focus on the task at hand.  Think Bill's got a naked houseboy?