My Mistress had me bent over the bed while she used a flogger on my bottom, a bit of stress relief for her. She likes to mix in some tease to keep me guessing, in between whipping she was caressing my cage and balls and then she started rubbing the skin between my balls and anus. I was really surprised how nice that felt. Later wondering why that felt so good I did a bit of reading and discovered that rubbing that area is one technique for prostate massage, the other technique being a more direct being a finger or toy in the anus. My research led to lots of contradictory views on if prostate massage is a health benefit and also if frequent ejaculation is associated with prostate health. Which leads me to a couple of questions - Do you practice prostate massage for health or for pleasure? Does prostate massage cause an orgasm, or is it possible to "milk" the prostate without an orgasm (more appropriate for being chaste)?
We do it for my GF's pleasure, though she would likely sarcastically tell you it was for my pleasure and health as well. lol She has said many times, however, that she doesn't care if I get any enjoyment from it - she does it purely to express her dominance over me. Fortunately for me, she usually does it long enough that I manage to cum from it, so it is enjoyable for me as well. Prostate orgasms are possible, yes. They are generated differently from "regular" orgasms, though. And yes, it is possible to "milk" a prostate without an orgasm. If someone sticks their finger up your back end and massages it with sufficient force, for example, it will cause you to emit some prostatic fluid, which is the "milk." If that occurs without the "waves" you'd feel with a prostate orgasm, then you've been milked without the O.
We don't. Neither of us are into butt stuff. There are no health needs for it, the body takes care of buildup.