Milking is also sometimes called a prostate massage. However, it's important to note that prostate milking refers specifically to internal massage of the area on the rectum's anterior wall. The more general term, prostate massage, can also refer to external massage of the perineum, which can indirectly put pressure on the prostate.
More About Milking
To milk your partner’s prostate, insert a finger or more inside the anus. Feel for the prostate, a raised area at least one inch inside the anus which is about the size of a large walnut. Massage it gently but firmly, starting slowly before increasing the intensity. Some people with penises also enjoy milking their own prostates during solo or couples' play. Commercial prostate massagers - including vibrators, dildos and anal plugs - are available. However, some people prefer to use one or two fingers to stimulate the prostate. This can work well, although in some instances a finger may be too short to reach the prostate gland.
The orgasm achieved through milking is commonly known as a prostate orgasm. This orgasm is said to be more intense and more pleasurable. There may be a sensation of the need to urinate before this orgasm, even with an empty bladder.
It can be difficult for cis-men in particular to accept something entering their anuses. Starting with a genital massage of the penis, testicles and perineum can help these men relax and make the process feel less clinical. Milking may also be incorporated with a hand job.