My first experience with prostate massage was with a guy i had a crush on. He had me in a prone position and had reached under and edged my penis some to get me heated. He then started by inserting His finger and stroking my prostate. He continued to add fingers and at one point i panicked because i thought He was trying to get His hand inside of me (not sure i'd even heard of fisting at that point, i was still pretty naive), i literally turned my upper body in shock and challenged: "what are you doing?" He gently backed it down a notch and sort of dommed me into turning back prone. i may have panicked because i was close to having an orgasm? Looking back on the experience, the feeling was much like my first orgasm as a boy. i panicked then too, as a boy not realizing what was happening, i ran into the bathroom as i started to orgasm thinking i was going to pee in my bed. i had been a bed wetter till i was 13 and that had been a deep source of embarrassment and humiliation for me, i suspect the panic i felt with Him massaging my prostate may have evoked some deep seated emotions.
Even though i was naive, He was not. He knew exactly what He was doing and what His goal was. He read me and knew my panic meant i was close to having an orgasm, so He removed His fingers and slid His swollen cock inside me and continued to milk me with His cock. At that point a good sized wet spot of pre-cum had formed underneath me when i began to orgasm. It happened so suddenly, and i was momentarily shocked by what was happening and reached under trying to stop my penis, feeling i was about to wet His bed as i had a violent orgasm instead. i had a cacophony of feelings at that moment of fear, intense pleasure, embarrassment and adoration for this Guy who had just made me cum by fucking me. It was a first. Up to that point i didn't realize i could orgasm by being penetrated and properly fucked, so i was also in shock of sorts, apologizing for the mess i had made.
It's kind of strange that i was so ignorant of my prostate and what it could do. i had been putting things inside of me since i was 7 or 8 years old. i have always been anally oriented, i discovered my anus and rectum as a sex organ long before i discovered my penis, yet this Top totally opened me and touched a part of me i didn't realize was there. i suspect He's responsible for awakening a now long held desire that my anus, rectum and prostate would be the primary, if not sole, source of my orgasms.