Prostate milking has a couple of different meanings, depending on who you ask. Some folks use the term interchangeably with a sexual prostate massage. Others use the term to refer to an ejaculatory orgasm that results from prostate massage (which can sometimes happen without touching his cock at all!).
For some people, prostate milking has the goal of stimulating the release of prostatic fluid, with or without erotic pleasure. Prostate massage wrings out the prostate like a little sponge and causes prostatic fluid to drain from the glands of the prostate into the urethra and out the tip of the cock, ranging from a few drops to an abundant flow. Some people suggest that draining the fluid from the prostate in this way may benefit prostate health by clearing blocked glands and stagnant fluid.
A lot of men who do prostate massage for sexual pleasure say that the fluid movement feels good, and those who eroticize fluids find it very sexy when they find themselves leaking fluid uncontrollably during high states of arousal. Also, it is common to say that prostate massage leads to a larger volume of semen when ejaculation happens, which corresponds with a more explosive feeling during ejaculation.
When the goal of a prostate massage is to drain out the prostatic fluid, the techniques are sometimes a bit different from other massage practices. Once the prostate is engorged with fluid (from arousal), try massaging from the side to the middle: left to middle and then right to middle. Repeat this stroke a little lower, until you’ve done side-to-center strokes over the whole gland. Finish with several downward strokes, from top to bottom. The idea is to massage the fluid into the urethra (which runs vertically through the gland) and then out of the penis.
Looking for more tips? Grab a copy of The Ultimate Guide to Prostate Pleasure for all the tools you need for prostate massage, milking, and all the other ways you can enjoy prostate fun!