Humiliation Boutique - The next steps

I think with the next steps I'll do a mix of drawings followed by a "meeting" type drawing that sets up the next sets of themed drawings.  I'm not really sure though, but that's what I'm thinking right now.

In all honesty I would love to turn this into a comic sort of a thing but I'm just not good enough with backgrounds to do that yet.  I do have some characters in mind but I'm not all that confident that I can make them look similar in each drawing as well :P

I should add that I will probably be taking a small break from drawing on weeknights so I can catch back up on sleep.  Also, feedback/comments are always welcome.