On Skype, I’m sharing masturbation with my handsome friend who lives in another part of the world, when he grins sheepishly: “Do you mind if I insert my finger?” I tell him, “Of course not, please do!” So adding more lube, he carefully inserts his middle finger into his anus. I see on his face, the intensity of his bliss notch up even higher, as his knuckle stimulates his prostate while his other hand caresses his erection…
Eventually, screaming out and thrashing, this bate buddy shoots his load well over his head onto the wall behind him…
To add anal stimulation to your masturbation is not a requirement for superb masturbation practice. Still, if you haven’t really explored the options “Down Under” in this sense, it’s totally worth a try. Some fellows simply are not wired this way, it seems, but evidently most men can enjoy anal stimulation and prostate massage, either somewhat, or incredibly much.
In real life, entering the anus, with a finger or something a bit larger, to not only enjoy but love it, is not so quick and easy as it usually appears to be in gay porn.
The truth is, your body gets aroused front-to-back, so you really should not even attempt this until you’ve been stimulating your penis and other front parts of your body for at least a half hour or more. Take your time, start on the surface, and you will be rewarded as your body invites you inside.
First, however, there’s the matter of hygiene, aesthetics, and a touch of psychology. Since infancy, when you were potty trained, you’ve probably been conditioned to think of this part of your body as dirty and even forbidden. Well—surprise!—it can be incredibly pleasurable fro most men, and this has nothing necessarily to do with whether you identify yourself as straight, bisexual, gay, or anywhere along that famous spectrum.
Make sure to evacuate your bowels ahead of time, or be sure you have recently. Of course, shower well and clean between those buttocks with a mild soap (such as Ivory) or even soak in a hot tub of bubble bath.
Next, be sure, also, to trim your fingernails short, and carefully file them smooth.
Then, as you consider entry and the quest for the prostate, which can become a powerful pleasure partner with your penis for states of ecstasy you may never have imagined before, court your anus like a sweet new lover that you really, REALLY want to keep on good terms with. Use plenty of lube. Start with your fingertip circling, crossing, dabbing slightly in and out, but not forcing your way inside.
Pay full attention to how this feels; take your time, and the rewards can increase beyond your expectations.
You’ve actually got an external anal sphincter (that powerful ring of muscle that makes it pucker) under voluntary control, and just inside it an even stronger internal ring of muscle that will only relax easily when you really want to be penetrated.
Your body will tell you when it’s ready, so go on and explore with that middle finger!
(CONTINUED in Anal Stimulation Masturbation Techniques, Part 2!)