Prostate Milking

Front view of prostate

Prostate milking is very different from anal orgasm, as I have discovered not long ago. 

First for the milking, I found its best done from both sides, your finger/fingers on his prostate, and your thumb on the outer side, on his perineum, you will feel when you are hitting the spot, from both sides produces a strong vocal indication. Usually I have 4 fingers in the inside and the thumb on the outside.  

Now, if I am only aiming at milking, (creating pre cum fluid) I am teasing, very gentle massage on the outer edges, very lightly in the middle always observing reaction.  If he is on the brink I'd stop and start again.   

Side view of prostate

If I am aiming at orgasm, then firm and purposeful massage, will tip him over the edge.  It is very similar to the g-spot massage, with the difference that we as women have this default condition not to cum and only something special sends us over the edge; men have default reaction of cumming unless instructed otherwise, or physically stopped.