A comment from a Top:
hilaire;2347388 said:As a top I've managed to give three guys anal orgasms, the first guy I did it by accident, I wasn't even concentrating on him at the time ( I was young and a bit too horny to be giving ), so I was blown away when he started moaning and shaking and cumming without touching himself, he explained what I was doing afterwards so from then on it was all I wanted to do to him. We fooled around for a few months and he always came that way and it was madly intense.
So ever since then I've always been trying to get the guys I fuck to cum anally. Only one two other guys have, and one used to have totally wild orgasms. The trick I picked up was that as you first penetrate a guy do it slowly and concentrate on feeling for his prostate with your dick, if you don't find it at first try different angles and positions till you do, then when your sure you've found it go for it massaging it with your dick as you fuck him.
It depends on the guy I think, some guys prostates aren't as sensitive as others, and some guys find prostate massage of any kind uncomfortable. I think the bottom has to be already really intouch with their prostate and really sensitive to it being massaged, one of the guys I got to cum anally was big in to toys and fisting so I think he was extremely turned on by stuff in his arse.
It's also a chemistry thing, the bottom has to be really horny and the connection between you has to be there.