Prostate milking is a highly pleasurable and intimate activity that you can share with your partner. Learning the basic techniques will allow you to confidently explore this new pleasure together.
Prostate milking is best done in the context of a full-body sensual massage. Share the kinds of touch you and your partner like best. Most men find that prostate milking feels best when highly aroused, so you can learn to incorporate it seamlessly into your lovemaking. While first learning this new intimate skill, however, it is best to devote most of your attention to using your hands to milking the penis, perineum and anus.
For comfort and quick hygiene, wear a nitrile or vinyl disposable glove on the hand(s) that will be touching the anus. Using a water-based lubricant, stimulate the outside of the anus, relaxing the sphincters and stimulating the highly concentrated nerve endings. Try circular strokes and smooth glides with one or two fingers. Experiment with speed- slower touch often feels more pleasurable!
Once the anal sphincters begin relaxing, use slow and subtle strokes to begin penetrating- never force your way in. The man receiving the prostate milking can focus on gently relaxing the pelvic muscles and breathing deeply. This relaxation is one of the most beneficial aspects of prostate milking.

After one or two fingers are gently inserted, locate the prostate by massaging towards the perineum (the part of the pelvic floor between the scrotum and anus). You will feel a walnut-shaped gland with a distinct texture. From this angle, you can feel the two sides of the prostate with a ridge down the center. This ridge is where the urethra is passing through the penis. Begin massaging by lightly sweeping from the far side of one lobe towards the center, then repeat on the other side. Alternate massaging each side from the outer edge towards the center, aware that you are manually expressing the fluid from the small ducts into the urethra. With your other hand, you can stimulate the perineum or penis.
Begin the milking with very light pressure, and communicate with your partner. If there is any tenderness or pain, reduce pressure or stop the milking. If the pressure you are using feels good, continue the milking. You can increase pressure gradually, always communicating with your partner about what feels most pleasurable.

Reading about a milking technique can only get you so far. You can learn prostate milking in the privacy of your own home with online flash videos. You and your partner can watch these videos together, learning new techniques while communicating about what looks exciting and also taking the time to explore any questions or concerns. Online video is an excellent resource, as you can come back to it over time to refine your skills and refresh your technique.