I honestly don't remember what my first erotic massage was, but I remember two early ones, one of which was probably my first.
I think my first was with Jake Deckard at his place in Greenwich Village on a table. In my shyness I think I stripped down only to my boxers and he then "encouraged" me to get a little more informal. The massage was very, very good, as best I remember pretty much purely therapeutic, and the HE just standard, with MT of course, but I sure enjoyed it--that man just oozes masculinity.
The other was at my place, but the masseur brought a table. He was a natural bodybuilder with a fantastic, rock-hard build. The therapeutic part of the massage was a good as I've ever gotten from anyone, and after I flipped over and he finished the legit massage he oiled up his own front, climbed up on top of me, and we proceeded to have the hottest frottage session I can ever remember having. Like a lot of people, I get really, really sensitive after I cum. So we did the frottage with him on top of me, holding me tight. And, after I came, he kept moving on top of me, and there was nothing I could do since he was so strong and had me pinned to the table. I nearly passed out from the hyperstimulation. When he finally climbed off of me, I was simply unable to move for a while, during which he cleaned me up.