IF she is good with it and wants to I say put down a towl. Why would I want you any less just because you are having a few not so pleasant days.
Barefoot with painted toes................
I would view it as the ultimate orgasim. So Very hot...........................
Wife/Girlfriend: Yes and hope she would do the same for me.
Stranger: if it were a female and again hope she whould pleasure herself as well
Guy: probably not