No, I am NOT talking about time here. I am talking about “Prostate Milking.” I have recently done a little research into what the Internet presents as “normal” prostate milking. It's all wrong! Pay no attention to most of what you see, hear, or read about milking a prostate on the Internet.
Let's begin with what NOT to expect. Don't expect him to shoot gobs and gobs of semen like he does when he has a normal orgasm. If you see that happen, he HAS had a normal orgasm. He will not yell “woopie” or anything else. It just doesn't happen. In fact, he probably won't even get hard, though that is possible.
Here is what you should expect. When you are massaging his prostate correctly, you should see a few drops of semen, not a whole load by any means. By a few, I mean three to five drops is normal. If you keep massaging the prostate, he may continue to leak a few drops from time to time. The longer you do it, the more you will collect. Just don't expect a lot. Of course, there are always exceptions to this rule. You may get a larger amount, just don't expect it.
Secondly, he may do this whether his cock is hard or soft. It is usually soft when a doctor does it to obtain seminal fluid for testing. Don't believe me? Ask your doctor. I am she he/she will be happy to explain the process to you. How do you think I learned to do it?
Finally, yes, pegging, or anal penetration, may stimulate, or rub against, his prostate enough to cause his semen to leak out. It all depends on whether the prostate gets “massaged” or not suring the particular activity.
In any case, it is best if your guy is on his knees, so that the fluid can run in a downward direction. In other positions you may be successful and not even know it because so little fluid is produced that it may not reach the end of his penis. One or two strokes of his soft penis should be enough to coax any semen in his urethra out.
If you normally stroke your guy while massaging his prostate, chances are, you NOT milking him, but rather only jerking him off. You cannot expect get the same amount of fluid by milking his prostate as you get when he normally ejaculates. Keep that in mind.
Next time I will go into details about how to milk him properly.