There are two aspects of this: 1) the ABCs of anal sex and 2) the experience of a prostatic orgasm.Tom Allen wrote: If you're interested in discussing more, I'm interested in hearing about it.
In regards to the former, it's definitely not easy for everyone. It certainly wasn't for me. Frankly, the sensations are very foreign and it lot of it comes down to letting your body learn that the sensations are just different, not necessarily bad. When learning, three things are paramount:
1) trust and relax
2) lots of lube
3) warmup time
Of the three, the first is the most important. Umpteen years ago, when, as a very uptight closeted fella, I was learning to do this with my partner, the thing that got me over the mental part was the use of aspercreme the first couple successful times. The benefits were probably wholly psychological in nature and I wouldn't necessarily recommend it to others. But the point is that fear and worry makes your muscles tense up and that's exactly what you DON'T want to happen. Straight guys might have some other psychological baggage to deal with in regards to penetration--but to be honest, pegging is, while not exactly a mainstream practice, certainly not so far out on the spectrum of kink in the minds of younger folks today. Sex is about making each other feel good and as far as I know there's no official rulebook that says that you can't bring sporting equipment along.
Once you learn to adapt to the sensation of penetration, a nice benefit you get to experience the sensations of all those sensitive nerves in your perineum, around your sphincter, and, I find, up the front wall of your rectum, leading up to your prostate.
In respect to the actual orgasm, it's hard to describe. It's definitely possible to come from prostate stimulation alone and not necessarily as pure a "milking" operation. When it's happened to me, it's usually been after at least 2 or so weeks of being locked up and as part of an extended play session--sometimes after my having sort of stewed in my juices all day. (Wicked, wicked tumblr.)
Every once in a while, you see men and women try to verbally describe their experiences of orgasm. One rough analogy is "men sneeze, women yawn," and certainly a lot of men have described their orgasms as feeling very focused on their cocks. Women, on the other hand, talk about things like waves of pleasure radiating out to their limbs from their centers. A prostatic orgasm is much more like the latter than the former.
When I experience it, it's usually through some gentle dildo play (Vixskin) and perineum massage (along with my getting to touch and kiss my partner). I just relax and enjoy the sensations coming from the stimulation, and, of course, I'm straining against my tube. If the angle, rhythm, and penetration is just right, then there's a slowly building crescendo leading up to that tight lower abdominal tightness of the prostate charging that I think most men are familiar with. But then the sensation changes as my pelvic floor muscles begin to move, my lower abdomen begins to pulse around the dildo, and the dildo presses in and milks the prostate. Due to being locked, the usual spurts through a fully erect cock aren't there, but the pulsations are still happening, even if the release is more of a gentle flowing sensation. And warmth is really suffusing my body and radiating to my limbs. Afterwards, I'm wracked with aftershocks as my body shudders and my limbs quiver, sometimes for several minutes. And I seem to recharge a bit faster from this sort of orgasm than from the standard sort.
It's by no means as easy to achieve orgasm via prostate stimulation as via direct stimulation of the penis--in fact, it's only happened to me when all the conditions were right. But what a thing.
