What about the prostate?
A great deal of the pleasure you get from bottoming comes from the penis stimulating the prostate as it thrusts in and out of the rectum. You can get a “sneak preview” of what that will feel like by massaging your own prostate as you masturbate.
Step 1: Gently press your middle finger against your anus
Step 2: Inhale to a count of four and squeeze your sphincter shut.
Step 3: Exhale to a count of six and release the sphincter.
Step 4: Repeat until you draw in your entire finger.
Step 5: Gently probe the anal wall upwards towards your navel.
The prostate is located behind the anal wall in the direction of your belly button (two to four inches from the sphincter). Be careful! The prostate is very sensitive. Do not poke and prod. Caress and stroke. Press gently. Use feather-light touches. You’re looking for a walnut-sized fleshy ball hiding behind the anal wall. Finding it is a little like playing hide-and-seek, only you’re using your finger rather than your eyes. The prostate is behind the anal wall in the direction of your belly button (two to four inches from the sphincter). Be careful! The prostate is sensitive.
Step 6: Find and trace the contours of the prostate.
Once you locate it, trace your finger around the gland. Take a tour. Notice where it is. Make a mental note of how far in (and up) you had to go so that you can use this memory as a GPS for the next hide-and-seek adventure.
Step 7: Massage the prostate
You need to exert firm pressure without pushing too hard. Firm but comfortable is your goal. Start at the top of the prostate and slowly push down toward the center. Then go back up. Then start at the bottom and slowly push upwards toward the center.
Step 8: Massage the prostate while you masturbate.
You may or may not have had an erection while exploring the prostate. It’s now time to purposefully get one. Massage the prostate as you masturbate to climax. It is quite eye opening to feel your prostate enlarge as you’re about to orgasm and then feel the entire rectum—sphincters and all—rhythmically contracting as you ejaculate.
If you want to massage your prostate during masturbation but don’t want to go through the “hand yoga” contortions (let’s face it, you have to go through a bit of twisting and bending to reach the prostate with your hands) try using a commercial prostate massager like the Rude Boy.