I have written about this subject several times, but it has become clear to me that many of you, especially those of you who are new to it, are having difficulty with prostate milking. First of all, let's get one thing clear... There has been a great deal of discussion about the value and purpose of prostate milking. I have not been able to find one definitive study on the subject of prostate milking for health reasons. One camp says that if a guy is not allowed to ejaculate for an extended period he should have his prostate milked (for health reasons). On the other hand, I have found no proof that any damage is caused from prolonged abstinence. In other words, do it if you think you need to, don't if you don't want to. I know for a fact that many men (past and present) who practice abstinence with no side effects what so ever. So I don't feel it is a serious problem.
Having gotten that out of the way, let me talk about 'blue-balls' for a second. I'll bet you didn't know that blue-balls is actually a short term malady that effects men when they first start tease and denial. Yep. When you stimulate the male cock into arousal and don't allow it release, his semen will build up in his system as his body prepares itself over and over again for release that never comes (pun intended). But after a while, his body gets used to not being able to release all that excess semen and it quits making so much. It takes from one to two weeks for this to happen, but once it does, his blue-balls will go away.
So what can prostate milking do for you (or him)? Simply put, it can relieve his body of excess semen so that it will once again begin to think it needs to replenish the supply. In other words, he can get blue-balls again! Blue-balls are not as bad as people might like to think. They are an aching in the groin (and possibly the balls) that makes his balls more sensitive to the touch (or the punch, as might be the case).
So what does all this mean to you? Nothing really, but if you want to practice prostate milking for any number of reasons, including, but not limited to, humiliation, be my guest. The problem I most often hear from women who try is trouble getting anything out. First of all, don't stick your finger in as far as you can get it (unless you have pretty short fingers). When you can feel the sphincter tighten around your second knuckle, you are probably in far enough. It may take you many tries before you get the hang of it, and don't expect to get copious amounts of ejaculate every time, especially when you are just starting out. I read a Doctor's note about that once and in it he stated that five or six drops is about all you will get on someone who does not practice it often.
So, in conclusion, use lots of lubricant, wear protective gloves, and try it for at least 10 minutes as often as you can. Before long, you will become good at it. Once you have done it successfully, you will know what works best on your guy. So keep practicing even though you may not get results. The humiliation of having it done (successful or not) will be enough to keep your guy happy.