The last time I went for a massage, was just looking to work out my tight back, my masseuse really went deep into my lower back and was just what I was looking for, then she went further south, massaged the glutes and then even deeper. She was very gentle around my starfish, and it felt really good. Was a bit apprehensive at first, but since she was fine with it, I just went with the flow.
Junior really responded well to this new service too.
She didn't penetrate me, but at that point I would have let her try.
Maybe next time.
I say, if it feels good, just do it.