Many men enjoy including self prostate massage in their masturbation. By touching their own prostate, men can engage more of their sexual system, thereby enjoying more sexual sensation and improving health in the entire pelvis.
Self prostate stimulation can be achieved internally or externally, with or without toys. The most direct way of milking your own prostate is via anal penetration. If you are flexible and can reach, you should be able to feel your own prostate. Be sure to massage the anal sphincters first and only proceed to penetration when you are relaxed and aroused.
Many of the techniques we demonstrate in our Guide to Prostate Massage can be used for self prostate stimulation during masturbation. How you can touch yourself will depend greatly on your flexibility. Many men can reach their own prostate - some can't reach comfortably enough to enjoy this practice. If you can't reach comfortably, using a toy may help you enjoy self prostate massage.
Using a toy such as the Aneros will help you with internal prostate stimulation and may feel more comfortable than using your hand. Many men enjoy using the Aneros in the shower. Again, be sure to stimulate the external anal sphincters so you are relaxed and the toy penetrates easily. There never needs to be a moment of pain during anal stimulation.
External prostate massage can be done via the perineum. You need deep pressure to reach the prostate through the sling of muscles that comprise the pelvic floor. Push deeply along the perineum and see if you can feel sensation in and around your prostate. Do this while stroking your penis for maximum pleasure.
However you choose to do it, manually stimulating your prostate can be a pleasurable and healthy part of your masturbation.