From a very long, detailed essay on male prostate milking:
When the tool is placed long enough inside him and is well lubricated. You will have to get a firm grip in the handle and push the inside end of the tool against his bladder. Then you slowly pull it 4 to 4* cm out of him. He can feel it as a pressure against his urine bladder. If you pull the tool too much out of him. It will slide over the bottom of the seminal vesicles with a small hump. If you can stop just before that happen and then keep the pressure on his bladder for a while. The trick is to move the contents of the seminal vesicles down against the valve in the bottom of the bladder and then extend the pressure a little so the valve has to open and let the content out. If this happens the milkman will suddenly fell the urge to empty his urethra . Therefore his muscles will tighten to try to do so. He will feel nothing else but this. No orgasm or excitement. Just the urge to empty his urethra and you pressing on his urine bladder. When he does so, some of the content of the seminal vesicles will spurt out into the urethra . You can feel this if you place your free hand in the area between his anus and his penis. Release the pressure and press the tool gently back in, to the top of his seminal vesicles. Do not touch his penis yet. Repeat this process 8 to 10 times or until you feel that you can’t get more out of it. If you want to help the semen out of him. You can do so by placing 3 fingers just below his anus and press along his urethra towards his penis. Some lubricant may be required.
Then you can try, to squeeze more out by massaging his prostate with the tool or your fingers. Anyway you can always secure that his Urethra is emptying by letting the tool slide from the top and along one side of his prostate to the bottom of his rectum. But this will produce some feelings similar to an orgasm and it will only produce a little more semen. When you decide that it is enough. Pull out the tool, and continue to massage the area between his legs. From his anus towards his penis, by pressing when you move forward and don’t when you move your hand back again. Do it 4 – 5 times and then when your hand is at the rod of his penis keep it there and keep up the pressure. Whit your other hand you take his penis between 2 fingers at the rod and squeeze them tight together while you pull out towards his penis head, to empty it. Do not do this more than one or two times. He could get some ideas, if you do it too much.
The more skilled you get and the more he is getting used to this treatment the better is the result. This was about emptying his seminal vesicles but what about his prostate? If you look carefully in the saucer you will see that the content is milky and thick. It doesn’t taste exactly like semen but pretty close to. This is, I think, because it is very difficult to milk out the content of the Ampulla or perhaps it has something to do with what happens during a normal sexual excitement, hormonal or other vice. I don’t know. But if the liquid is milky his prostate has emptied itself during the process, else it would be clear whit small lumps in it. What I know is, that it is possible to milk out about 90 % of the amount of semen from a normal masturbated orgasm. Without any amount of sexual excitement. That’s pretty good I think.
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Sperm Milking