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1. He should empty his bowels and use a small enema to clean up before you start.
2. He should also COMPLETELY empty his bladder before you start because he will need to relax his prostate in a similar way to urination to allow his sperm to pass through.
3. Use a toy with a stiff shaft and a prominent knob. Most solid silicone ones are just too soft to put pressure where it is needed. It should have an insertable length of 6-7 inches. Most prostate massage toys are too short.
4. Tease him! Whatever gets him really hot is good. This will get his juices flowing and ensure a good supply is ready for milking. If he starts to leak pre-cum, he is ready!
5. Use plenty of lube and start slooooowly. Anal muscles take a while to relax, particularly for beginners.
6. Massage the area around his prostate first. It is just past the entrance to his anus on the front side of his body. It will be quite sensitive at first, particularly if he is very "full". It may feel a little like the need to pee at first, but if his bladder is already empty, it will quickly change to a sensation similar to orgasm build-up.
7. Work the prostate from the sides and back towards the center where the sperm tube passes through and collects the contents. The first few drips will probably be clear pre-cum followed by thin, milky prostate fluid.
8. When you start to see some thicker drips of real semen, it is time to go deeper and start massaging his seminal vesicles where most of his sperm is stored. They are further inside, beyond the prostate, but also towards the front of his body. Go as deep as you can and put firm pressure towards his belly then work the toy slowly back out while keeping the pressure on. He should relax in the same way as preparing to pee. This relaxes the prostate and allows the sperm to squeeze through. The sensation is amazing! You will both know when you have the technique just right by the big drops of thick semen that start to dribble from his cock
9. Try to avoid touching his cock while massaging his prostate. If he is erect, it means his prostate is tight and it will be very difficult to get any sperm out.
10. A cautionary note: This type of play should not be attempted if he has any known prostate health issues (prostatitis, inflamation, infection, cancer etc.) as massage could aggravate the situation. Any significant pain or blood should be a sign to stop.