My most recent therapist has made me cum hands free twice (on separate occasions). He's not much to look at but he's a pretty decent masseur. The massages take place at a spa. He learned early on that I liked when he brushed his crotch against my hand. The first time I came he was slowly and rather lightly pressing his crotch to my hand and working way up my leg and I just let loose (I was still on my stomach, so it was a bit awkward to have to lay with my load on the sheet under me for a bit longer).
The second time I had flipped onto my back, was draped, and was again having my upper legs worked pretty hard when I just shot. He definitely knew this time as I couldn't control my movements and it was a huge load. He never missed a beat and just kept on with the massage.
The last time I saw him, I managed not to cum, but he was wearing looser pants and he very deliberately placed his bulge right into my upturned hand. I took that as an open invite to play with it, which I did somewhat gently. While I was doing this he was focusing on my ass and he ran his hand through my crack and against my hole several times. Other than that, he never really got hard and i didn't get to touch him again once I had flipped onto my back. It's a very peculiar experience each time, but I'm honestly quite pleased with it. I don't really want to get into anything more with him and it's just tantalizing enough for me to keep coming back.