I hadn't tried it up until a couple of years ago. I was a bit reluctant to try but this particular woman I went to (massage 'therapist' - offering FBSM massages) specialized in prostate massages.
She was very gentle, slow and explained everything before she did it. After a nice full body massage, she had me turn over, exposing my throbbing and bobbing hard-on
![Wink ;-)](./images/smilies/icon_e_wink.gif)
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She took her time, oiling me up (cock and balls) and then applying KY lube in my ass and her finger. She stroked my cock slowly as she gently pushed her finger in, very slowly, just a little at a time. She held it there for a bit until she felt me relax. Then she started the actual prostate massage. She pointed her finger up and started rolling the prostate around, with some flicks or plucking I guess. That's what it felt like. Very pleasurable sensations. Just having her finger wiggling in my ass was pleasurable alone, but working the prostate was intense.
After a bit, liquid just started oozing then flowing out of the tip of my cock, which she said was normal. I am not a pre-cummer (I wish I was) but it was exciting to see myself oozing like that.
At this point I was going insane with pleasure. I felt the impending orgasm, and I was bucking and thrusting my hips, but she told me to relax and remain still and she stopped. She left her finger in but no movement.
I settled down, relaxed then she continued stroking the prostate, but not touching my cock. Cum and/or pre-cum was coming out slow but steady.
I felt the orgasm rush fast approaching, and when I started to climax she grabbed my cock again and slowly stroked and fingered me until until I had "full release"
The actual orgasm was like none that I had ever had before. That point where you 'pop' that first squirt, then start pumping out surges of cum, well, for me, that 'pop' was more of a ramp up and the cum just started coming out, like a steady flow, but with small surges. She continued slowly stroking my cock and fingering. I was literally spent. She left her finger in and did small movements even after I went completely limp. There was huge puddle of a mess, lol, kind of embarrassing but exciting at the same time.
She has since moved on and I have yet to try and find another prostate massage girl. Wish my wife knew how. At the very least, be adventurous enough to put her finger in me while giving me a handjob.