I have a male therapist who massages me nude. I usually have a precum puddle and he grazes me and will do some pelvic floor massage, but he still has boundaries and will not stroke my cock. After one massage that I was particularly turned on by, I asked him if I could jerk off, and he said NO. So I went into the shower and shot in his sink because I was not going to be able to focus the rest of the day until I shot. In the bathroom drawers he has all kinds of anal toys and lube, but he has a “professional code” and won’t cross it, which I respect. He states that he will never remove his clothes and has a relationship, so there is a boundary there.
I once asked him about a prostate massage, as I read it can help to maintain a healthy prostate - and told him I had a prostate infection a couple of years prior. He told me he could do it. I came back for my prostate massage, and this guy was an absolute master of the prostate. He gave me a “tour” of my anatomy, which was very informative. I was rock hard and oozing precum. At the end I was dying to bust my nut and he said I could. I grabbed my cock and blew a gigantic load. A second time I asked for some prostate work, and after a while of edging and our time running out he did grab my cock to finish me off. It was hot as he was sitting with his legs out (clothed in sweatpants) and my naked legs were on top of his as he had his fingers up my ass and jerked me with the other hand.
Funny thing is next time I scheduled a “regular” massage and he gave me a great, yet clinical massage - me naked of course. I am not really attracted to this guy and I don’t get more than a slight semi when he grazes my balls. It’s almost like a tease, but after the “no” I got on a self jerk off And that I am mostly straight don’t really want to push him. A couple of times in his massages he will put me on my side in a complex position. My hand was cupping his dick which I could feel was slightly plumped - and was unusual for him. I did not squeeze it or take any forward action. He simply flipped me on my other side and continued as if all was normal. This has happened a few times, but I have never rubbed or squeezed his dick, and it has never progressed, but it does seem odd given these boundaries. Can’t really figure this guy out, but he gives great massages, and I like that things have stayed relatively clinical. I feel if he crossed the line it would ruin it for me and I would maybe not go back. But still having a hard time trying to figure out what the deal is here. Any thoughts?