Escorting Personal Talk

your plan of going for less "hollywood" escorts first to build up your experience is a good one - sounds like you chucked yourself right in the deep end for your first time
I recommend starting off with massages with a handjob at the end, just relax and enjoy yourself with a nice massage, then a hand shandy at the end (just look in your local paper for this, or look up naturist/erotic massage in your local area online)
this will help you relax in these situations, as you'll be naked with a lady etc's, as you build up your confidence to go back to the yank

one other thing, as callous as this sounds, you are paying the woman for a service, freaking out about whether or not she is going to enjoy herself or reject you isn't on the menu as she probably won't care either way - as long as you pay her