At the end of this chapter (about male milking) I would like to share some individual experiences by practitioners on how a gland-milking can be performed. I found these accounts some years ago on the net. I wanted to have both sexes have their say, yet in the end I consider this distinction does not matter that much, at least when it comes to partnersex.
However, I did find the following how-to by someone called Jenny, thus assuming the author is an experienced lady, or, to be more precise, a dominatrix with a good deal of exercise in this discipline. I abridged slightly and made remarks to clarify flawed statements (in red and bracketed) considering commonly accepted facts. – So, ladies first then:
How to milk. Based on my experience.
Find the Spot
First you have to ensure that the Milkman is able to take two fingers up his anus, or at least a hard dildo with a diameter of 3.5 cm.
Next you must find out if you can reach the top of his bladder with your fingers. This is best done when he is lying on his back with his knees up aside his chest. You can slide your finger(s) up inside his rectum feeling the front of it. You better wear a thin rubber glove and use lots of lubricant.
You can feel his prostate as a round relatively hard ball in the size of a ping-pong ball. When you can feel the top of his prostate you will have to get at least 5 cm deeper inside him to feel the top of the seminal vesicles. It is not enough that you can feel his bladder with your fingertips, because you will have to make a pressure along and across both seminal vesicles at the same time. Some pressure on his stomach just below his ribs can force the bladder a bit down so it is easier to reach. If you can’t reach this, you will have to use some tool to milk him.
In the beginning I used the handle of a hairbrush covered with a rubber. It is 3 cm wide and 20 cm long with rounded edges. I made a mark on it, to show how long inside it needed to go. To set this mark you will have to rely on his cooperation, because he can feel it inside and can tell you when it no longer presses on his bladder, that is when you are past his seminal vesicles. Later on I started to use a hard dildo. It seems to be a better choice, because the end of it goes in between the two seminal vesicles and that way makes a pressure on both at the same time.
If he is not used to get anything up his rectum you will see some wage trace of blood on the tool when you pull it out. That is because so far inside the rectum the blood vessel are very close to the surface and the skin is very thin [although it is true that your rectal tissue is very delicate, traces of blood would be a serious matter hinting to an injury! Consider to consult a physician!].
One way to prevent too much friction to the rectum is to ad some heavy lubricant (heavy-duty Vaseline) into his rectum before entering the tool [using lube is mandatory! Not only to protect the rectal tissue, but to turn the whole milking procedure into a working practise if not a somewhat exciting experience for the milkee.]. That way the tool will catch up some of the lube when it passes through it, and it will decrease the friction against the inside of rectum. [I would not recommend Vaseline because it is much too tenacious, although it reacts with body-heat making it slightly more greasy.]
You will need something to catch up his semen too. I am using a small cup or saucer. I can then let the penis be untouched during the process and just let it drip out the semen. Much more degrading for him… To get an eye for the quantity of semen you can measure out about 5 ml of thick liquid into the saucer. Just to get a good idea of how it looks.
Position (if it is done by another person)
The best position will be with the Milkman lying on his stomach on a relatively hard surface. His lower abdomen and penis free of the surface and him resting on his spread knees with the saucer placed on something right under his penis.
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 4.5 cm out of him. 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 happens 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 feel 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. Release the pressure and push 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 onto his perineum 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 [it appears that Jenny is focussing on milking the seminal vesicles, yet we know that massaging the prostate does produce a fair volume of milk].
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 root of his penis keep it there and keep up the pressure. With your other hand you take his penis between 2 fingers at the root and squeeze them tight together while you pull down towards his penis head, to empty it. Do not do this more than once or twice, 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. [...] What I know is, that it is possible to milk out about 90 % of the amount of semen from the total of a regular masturbated ejaculation. Without any amount of sexual excitement. [A sub will certainly draw sexual excitement from the practise of milking, yet by the psychological aspects of it, despite the range of sensations within his reproductive system and anus.]
In the beginning and until his rectum got used to this treatment, not more than once every week. Especially not if you get traces of blood on your tool, during the first times. And that is almost unavoidable [it sure is I´d say! Pay close attention here, blood is the exception, not the rule!]. When he is more accustomed to it you can do it more often.
However I have never got any good results out of doing it more than 4 to 5 times a week. I think, that about 48 hours between every milking is a good choice, if he is not in some kind of chastity. If he is in a well working chastity device, one time each week will do the trick. If the purpose of this is to prevent him from having any orgasm, a chastity device is necessary. The milking can’t prevent this in itself. I have had orgasm with ejaculation after an effective milking. But it can reduce the urge for ejaculation and therefore reduces the pressure for having an orgasm.