The first thing you should know about prostate milking is that it’s very difficult to find their tiny little udders. OK, just kidding. In all seriousness, prostate milking is the act of massaging the prostate and causing ejaculation by manipulating the gland. Regularly massaging the prostate not only greatly increases the intensity of men’s orgasms, it can decrease the risk of prostate health issues, including cancer.
The prostate gland in men produces seminal fluid. It can be as small as a walnut in younger men and as big as a plum in older men. It surrounds the base of the urethra, kind of like a doughnut, and is located just below the bladder and above the rectum. A small lumpy portion of the prostate can be felt with a finger inserted 2-3 inches inside the rectal cavity. You can find it by feeling upward in the rectum towards the penis while the man is on his back. The prostate usually feels like a small lump with the texture of a kidney bean. It gets larger and more prominent with arousal and, with stimulation, may develop small ridges, like on the roof of your mouth. The fluid it produces is an alkaline seminal fluid that is used to counteract the acidic content of the vagina to help sperm live longer. It is believed that the biggest cancer-reducing benefit of prostate massage is from the oxygenation of the prostate. Oxygenation increases blood flow and causes the expulsion of viral, bacterial, and fungal buildups (potential carcinogens) inside the gland. With prostate massage, ejaculation can occur with or without erection. Either way, bam! Your pipes are clean.
So, how do you massage/milk a prostate safely? The man should lay on his back with a towel underneath him. First, inspect the rectum for obvious issues like anal tears or hemorrhoids. Make sure the area has been cleaned with soap and water. Put on a fresh latex/nitrile disposable glove and arouse the receiver by kissing, playing with his nipples, and massaging his entire body. Relaxation is not just key, it’s vital. Next, switch to a handjob or oral sex. Play around this way for 20 minutes minimum without allowing it to go too far. Once he is both aroused and relaxed, put silicone lube on his anus and all over one gloved finger. Some people prefer the middle and some the index finger; whatever feels better for you is fine. Remember to keep your finger well lubed, move slowly, and don’t pull out unless you need to. For the sake of comfort remember, wetter is better; you can’t use too much lube. (Get more tips on anal play in Anal Sex: After the Entrance.)
Slowly massage the outside of the anus with one finger and insert it slowly, pressing up toward his penis. Communicate with him about speed and depth. Pay lots of attention to detail and take direction carefully. This act can be difficult for many men, so go slow and steady. When your finger is half way in, stop. Don’t pull the finger out, but hold it still while stimulating the cock with your mouth or other hand. Keep arousing him and resume the rectal massage. Go in until you feel the bean-like prostate. Massage it slowly in a circular motion. Be very gentle. Keep stimulating his cock and switch back and forth - a little prostate massage, stop, play with his cock, stop, then back to the prostate, etc. When he is about to cum, keep steady pressure on the prostate but don’t move it around too much.
One thing to note is that the receiver’s penis will likely start to leak fluid soon after prostate stimulation begins. This fluid will be thinner and come in larger quantities than regular ejaculate. Use the fluid to give a slippery handjob or blowjob to finish him off while maintaining pressure on the prostate, giving him the best orgasm of his life. Studies show milking your prostate once a month will lead to a 30 percent lower chance of getting prostate cancer. Of course, you will also have amazing orgasms, increased happiness and better overall health.