When you are ready to start milking him, keep him in the cage for an extended period so that his seminal vesicles will be full and he will be desperate for release. Then tell him that today you want to try massaging his prostate. If he refuses, tell him he had better enjoy blue balls!
The best position for him will be on his knees, face down on the bed. This will give you easy access to his anus and a good view of his milk when it begins to flow.
The first thing to do is to relax his prostate gland so sperm can flow through. The easiest way is to insert two fingers into his anus and massage it with your fingertips. It's best to cut your nails short and use plenty of lube because the lining of the rectum is thin and easily damaged by sharp objects.
Of course you don't want anything in his rectum while you are trying to work in there so you should train him to empty his bowels first and clean his rectum with an enema before you start. If you have been training him well, he should accept this quite easily.
If he has not had anything inserted in his anus before, he will probably be very tight. Start with one finger and plenty of lube. There are two ring-like sphincter muscles to get past. Work slowly until you feel you are inside the second one. Now curl your finger gently downward towards his belly. There you should feel his prostate gland. It will be about the size of a walnut with a crease down the centre like a plumb. Work the tip of your finger around it to get an idea of its size and shape. The sensation for him will be quite surprising. An unfamiliar mix between the need to pee and the build up to an orgasm so be prepared for some unusual noises! By now his anus should have relaxed a little and you can work the second finger inside him.
Once you have both fingertips on his prostate, reach in as far as you can and squeeze gently downward then draw your fingers slowly outwards. Avoid the central crease because that is where the urethra passes through and you want to keep that open. Release the pressure and go back in again to repeat the stroke, changing position and pressure of your fingertips a little each time. After a few minutes, his prostate will begin to relax.
The prostate gland also controls erection of his penis so when it begins to relax, his erection will begin to shrink. That's a good thing because it means your massage is working and it will also get him used to the idea that his sperm can be extracted when he is not ready for sex.
You will also be putting pressure on the Cowpers gland so you should start to see some pre-cum fluid leaking from the tip of his penis. It should soon be followed by a thin milky fluid that is squeezed out of his prostate gland. It contains a little sperm, but there is much more stored in his seminal vesicles and now the way is open to empty them.
His seminal vesicles are too far inside to reach with your fingers so you will need to use a toy. A dildo or vibrator with a prominent tip and a stiff shaft is ideal. The stiff shaft is particularly important since you need to push it towards the front side of his rectum to squeeze his seminal vesicles and most silicone models are just too flexible to put pressure where it's needed. Some prostate massage toys will work, but they tend to be a little short. Something with 6 or 7 inches of insertable length is ideal.
Your fingers should have relaxed his anal muscles to ease the entry of the toy, but it will be a step up for him so use plenty more lube and go slowly. When you get the shaft fully inside him, start with the same motion as the prostate massage, squeezing forward towards his belly and drawing outwards. Work a little to one side and then the other on the next stroke. This will squeeze both of his seminal vesicles in turn.
After a few minutes, you should be rewarded with some thick creamy drops of sperm leaking from his penis. That might be all you get on the first try, but as your technique improves and he gets used to being miked, the drips will become dribbles and even the occasional spurt. If you want to measure your progress, you can put a small cup under him to measure his production!
When you have perfected the technique, you should be able to get somewhere between 4 and 8ml of sperm out of him depending on how long he has been in chastity. A week or two is usually the most productive. After that, his sperm will get thicker but not much more volume.
It takes quite a lot of practice to get the technique just right and empty him completely, but it's worth the effort. When he learns to accept having his sperm milked without getting an orgasm in return, he will become much less demanding in everything.
He will come to accept that milking is the way to relieve the pressure that builds up in his balls and he will begin to crave milking instead of orgasms. He will still be able to get erections so you can enjoy sex but it will be on your terms when you want it.
And there is something very satisfying about emptying a man of his most precious juice while he is in such a submissive position and completely unable to resist.
When you have mastered manual milking, you can go to the next level and get an e-stim machine to do it for you. That opens up another new world of possibilities and techniques. That's a whole other story!
