If you have been interested in prostate milking, but have not been able to achieve good, consistent results, I may have stumbled onto the answer. I recently became aware of a problem that is more common that I originally thought. It seems that many (me included) try too hard and reach too far when attempting to massage our partner's prostate. I did a little research and have come to the conclusion that this is an easy thing to do.
As you can see from the photos, you should only have to insert your finger up to the second knuckle. If you are pushing your finger all the way in, you may be reaching too far. You should also be aware that you may not get much semen when doing this. If you get a small amount, allow your partner a minute to rest before you continue your massage.
Never press too hard. A firm, but not hard, pressure is all you need to get the results you want. If your partner is complaining that it hurts when you massage his prostate, you are probably doing one or two things: 1) You are pressing too hard or, 2) you are pressing on his bladder. If you reach too far in, you may (if you are lucky) press his seminal vesicles. These can (if done just right) produce more seminal fluid than the prostate. However, it is much more difficult to reach these vesicles. If you only reach the tip of these vesicles, you will be pressing more on his bladder and this can cause a great deal more pain than you it should.
So, I don't recommend trying to massage the seminal vesicles. Once your partner becomes more used to having his prostate massaged, he will begin producing more fluid from the massage. Remember, you can do this several times until all the seminal fluid has been expelled. You will only get a total amount approximately equal to one full ejaculation. The reason for this is that only one ejaculation is normal for a six hour period. That is, it takes about six hours for him to replenish his supply of semen.
If you have ever made your partner ejaculate several times within a few hours, you should have noticed a decrease in the amount of fluid produced in each successive ejaculation. If you practice ruined orgasms, you will notice the same decrease in semen production with each successive attempt. So, don't expect to get a full ejaculation's worth at the first massage. You will need to do it three or four times to “empty the balls” so to speak.
If you use an 'Aneros' or similar device, you should use a rocking motion in order to get the proper contact with the gland. You may also opt for an “in and out” or side to side movement of the device. So long as it rubs against the prostate gland, it should work.
Again, be patient, don't press too hard, and don't reach too far, and you should be successful. If you have questions, don't be afraid to write me. I will be discrete, and I welcome your questions.