My first experience with prostate massage was with a massage therapist. I was in my mid 20's and was just finishing up grad school. I had gone a few times to Asian massage parlors where they give you a massage, then a hand-job when you turn over. I saw an ad in the paper where those places usually advertise, but this was a Caucasian woman advertising, and I really wanted to try something different. I thought it would result in the same sort of hand-job, but I wan't sure. I had experimented a little with placing small items in my ass, but not much and without a lot of pleasure.
So I went for the massage at this woman's apartment and it was an older woman, in her late 40's and a little on the large side. She was wearing a dress that went all the way to her feet, not revealing anything. I was starting to think that this was just going to be a massage and nothing else, but I decided to stay. She told me to undress and get on the massage table and under the sheet on the table, and she left the room. She did a very nice massage on my back, legs, arms, etc, moving the sheet, but not exposing anything. Then, just as I was starting lose hope, she whispered in my ear, "Is it ok if I remove the sheet so I can massage your butt?" Of course I said "yes".
She massaged my ass and played a bit with my anus, just lightly pressing and rubbing. She rubbed my inner thighs softly and played with my testicles. I lifted up a bit and she reached under and touched my now very hard penis. The she asked my to turn over.
She started rubbing my nipples and rubbing my penis, then she asked if I had ever had my prostate massaged. I told her know and was only a little aware that it was something some find pleasurable, but, I was in the moment and letting her take control. She went down to the end of the table by my feet, grabbed hold of the sheet under me and in one pull pulled me toward the end of the table - strong woman. Then she had me spread my legs and put my feet flat on the table. She put a glove on her hand and lubed up my ass and her finger, then in she slid. I don't remember there being much resistance. It felt amazing! I was rock hard in a matter of moments. She played with my prostate and talked about what she was doing and she played with my cock until I couldn't take it anymore and exploded! She cleaned me up and massaged my face and arms and chest and then I got dressed and left. I finished school and moved away not long after. I will have to write, however, about a return visit a few years later. That involved not only a prostate massage but an enema as well!