On further consideration of who I might like to see, I'm thinking I might like to try some roleplay, maybe boss/employee (where the lady is the boss) or a job interview (where she's interviewing me).

Any recommendations?

Being in the wonderful world of web cam modeling has made me appreciate the art of role play so much more..
I love the teasing qualities of the naughtier things in life..

Sammie Jo would be fun for that routine.

Jaz has a couple of ladies I have seen over the years that can really do a show.  What I have done, is send her a couple of stories/hopes.  She would review and match up the right lady.  The best fantasy creators over the years have been Jordan or Angelica.  The scripted she took from my 'birthday surprise' went beyond any thing I could have written.          I would give her a call.  Not sure she would do for a first timer, but her girls can offer excellent time.

These can be really fun sessions.  Your 'stories' need to be simple enough that the lady can complete, clear enough so that your expectatons can be met, yet not excessively graphic to cross a line of decorum.  I am not sure the title is enough to let the lady know what you want.

Lets us all know the outcome.