brandon,
My first wax did not go back around the anus but I asked the waxer and she will do that next time. I believe it depends on the individual waxer and you should ask about it or request it before your appointment. As to going to someone you don't know for them to see "everything", I felt it was similar in mood to going for a pedicure or something. It was not erotic or embarrassing. I did offer to help move/hold things so she could focus on the wax and hair. The touch and feel is very clinical to me and not of a style that could cause any embarassing reactions if you know what I mean. Hearing other stories, I may have had less of a reaction than many customers though. My waxer started off the appointment by talking to me about any allergies, that kind of stuff which helped get the appointment off to an appropriate tone.