Not sure if you saw this post from earlier or not, but it kind of focuses on this very topic.
Regarding a prostate massage, I am no “old hand” at it, so I am going to ask my followers to chime in a bit. Ladies and Gents?
One thing I can say is this – if your guy is uncomfortable with ass play, mention it and see if he will do it on his own with an anal vibe. Once he actually experiences a prostate orgasm, I think he may be on board with things, in case he is not already.