LOL~ My first was arranged by a young lady I met thru an add for "escorts". We met and she told me it would just be spending time with gentlemen, going out to dinner, dancing.... that sort of thing. I thought, well cool I can do that. I TOTALLY did not think about things being "intimate".
I was to meet him at a hotel for a dinner date. I arrived and soon learned that I was the dinner. Holy shit, I was sooooooo naive! He new it too as he came prepared with all the necessary items. Edit to Add: He WAS a complete gentleman so it turned out to be a very good experience.