It's possible IF you can locate the prostate gland & stimulate it. Personally I've never had any success in managing this, either with fingers or with butt plugs / dildoes / vibrators, however, on several occasions when I have had anal sex & have had a genuine penis up there, that has usually found the spot & has resulted in far more powerful orgasms from direct stimulation than from secondary stimulation via the penis, be it from masturbation or penetration. Furthermore, whenever I am penetrated by another man I always lose my erection (curiously, only when by an actual penis - with artificial articles I maintain my erection), but it doesn't affect my having the orgasm, even when totally flaccid, yet when it is as a result of anal stimulation the orgasm is always without ejaculation (at least it is in my case - I can't answer for everyone).
I have had great success with dildos and real penis'. When alone and using dildos I can control how fast, deep and how big it is. I can move the way that makes me feel best and i can cum every time. Sometimes I like it slow and sometimes I just want to be fucked senseless. I tend to prefer the dildos on the bigger side and when I masturbate while using the dildo I can keep my erection and it is always an incredible experience. If I use a very large dildo it still feels great but it is harder to keep the erection. There have been several occasions where I have been entered anally and have not masturbated and have been semi-rigid but had a great orgasm with full release. The couple of times I've had a real penis in me I thought it wouldn't feel any different than what Ive known already, but surprisingly it did. Someone else had control (it also helped that he was 8 inches) and while my erection came and went and came back, the orgasms were just mind blowing. Cumming from anal is not only possible, but is my favorite way to cum.
