Voting for my boyfriend, yes he has.

There have been a few times while rocking back and forth on my Rocks-Off Bad Boy, fully erect... pre-cum just flowing out like a river... I'd get that sensation that you get during the minute or two before you cum. That tingling that rings through your cock, except all down the perineum, the anus squeezing feeling the vibe like never before, and all the way up the toy to the prostate.
It felt so intense, and this lasted for about 4-5 minutes. I was in pure bliss!
But... I didn't cum. Granted, the second that I grabbed hold of my cock and gave it a tug or two, it exploded. But with the help of my hand :/

I honestly don't like that toy much, and want to get a better one. Looking in to Aneros and similar...
Maybe with a better toy, I'll get that extra little push and experience the legendary prostate orgasm.
If you've had one, feel free to message me telling me what toy(s) you achieved it with!

yes! words could not describe the feeling that overcame me, i just decided to try it one day and it happened, but im not complaining

I want to give this a try!

I have, it just varies person to person.

Yes, during anal sex. I think it depends on a lot of factors and is something that - for me - is difficult to replicate. But if a man is equipped just right (for me it has to do with the shape, not just the size/thickness/length) and has the right technique, it can happen if you just relax and let it happen. I think often times - especially during anal play - there is a tendency to grow tense and not relax, and this is prohibitive to achieving that prostate orgasm. But if you let your body take over and you've got a great partner, it feels really amazing when it happens. Unlike a "normal" orgasm, a prostate climax will build more slowly, and grow stronger as it is ongoing.

Unfortunately, no.

My girlfriend, who's genetically male, can't even orgasm from a prostate massage and she's been on hormones for a while, which we thought would make it easier for her. I guess not...

My husband has. It was kinda fun lol

Tried a fair number of times, but it never did anything for me. And, compared to just tugging for a few minutes, always just feels like a heavy time investment with extra clean up.

My boyfriend almost did once. He liked it a loooot.

Today close but no cigar, I keep getting a little pre-cum, I'll keep trying.

Anal is the best!

I have not tried prostate massage, and there is no such desire.