I experienced an anal orgasm two times in my life, and I am 30 now (there’s still hope I’ll have more ?)
My first one was when I was still in the closet, and at the time I would mostly gain sexual satisfaction from solo play or cybersex at home. I usually just played with my extremely sensitive nipples and masturbated, but as one of my regular cyber sex partners once asked for a visual of me being penetrated, I quickly looked around my room and saw a can of body spray that had a blunt bottom edge, and I thought it suitable for that purpose. I was a bit concerned about the thickness of the container, since at the time I’d never had anything of such girth penetrate me anally. In any case by the time we got there we had lots of foreplay where he simulated nipple play and I simulated fellatio. We were both very verbal and pretty much uninhibited, but one thing I never did with him during foreplay – masturbate. I would usually get so excited that my natural lubricants would pour out of my penis. By the time he is close to ejaculating from masturbating all the time, I would usually just need a few strokes to match him and we would climax together. This time he wanted to “be inside me” so I scooped the juices that leaked from my penis onto my belly and applied some to my anus and the container of body spray. As I started working it into me, I instantly felt unusual sensations that hit the tips of my penis and nipples. My natural self usually gets somewhat womanly and slutty when having sex, but this time for whatever reason it felt like I was truly a woman and I had this urge to get out from the experience bred and pregnant. Anyways, it didn’t take long before my gentle attempts at penetrating my anus and the very idea of being penetrated with such a “thick” object sent me over the edge. It caught me off guard, and I didn’t mean to ejaculate, but it just happened. It was a usual way in which I ejaculated, except that my penis did twitch and contract and expand well before the orgasm itself as well as during. My second time happened 7 or 8 years later. I met and got married to a man with a huge 8″ penis. We eventually ended up divorcing and if there’s anything I’ll miss about him it’s actually the girth of his penis (and his hairy body ?) which, as it was proportionate to his length, could fill me just enough to touch my prostate. The length itself actually turned out to be quite uncomfortable. Anyways, I was able to get myself to experience those same sensations and orgasm while on top and facing him (unfortunately as a pathological control freak that he is, at all times he had to have the lead and he’d usually just penetrate me from the back, so my joy ride was sadly a one-time experience). Now I’m on the lookout for a disproportionate penis (i.e. not too long, but thick) attached to a mentally sane and stable man (which in reality takes precedence over anything else; otherwise I would have stayed with my ex husband) who won’t mind letting loose in the process of love-making and accepting my (actually very sensitive) effeminate bedtime side.