Last week I had my first anal orgasm! I have long ago given up trying to achieve an anal orgasm. I had long since given up on thinking this was possible for me. I had tried prostate massagers, vibrating prostate massagers, butt plugs, vibrating butt plugs, dildos, orgasm denial for a month, hypnosis, you name it.
What made it finally possible for me was some combination of not expecting an orgasm, a week of orgasm denial, and fucking my p-spot really hard with a Lovense Gravity portable fucking machine. It felt completely different than a normal orgasm, with mind blowing pleasure but from deep inside. It didn't leave me feeling averse to sex like a normal orgasm does, but there was some smaller reduction in horniness and no longer feeling so full and needy. It also didn't come shooting out, but dribbling out over ~10s.
Since having my first I have been able to have several more in the last week to better determine under what circumstances it happens (hard fucking the p-spot), how much denial I need for it to happen (1 day is enough), and the feelings associated with it.
Where I'd like to go from here is to stay in chastity without penis based release for maybe the rest of the year while focusing on this new source of pleasure. I'll see if my wife is up for that