Yes I have it was amazing, like nothing else.
Dunno. Haven't had a cock in me yet, but I have ejaculated from prostate stimulation with toys up my ass. I have NOT had an orgasm from it, however, and those experiences are precisely how I learned the difference.
At least the handful of times I accomplished this, it was highly pleasurable to feel (and see!) cum shooting out of my cock, without a doubt. But I remained in the heightened state of pre-orgasm, and hadn't yet achieved that sense of completion and release that comes with even the smallest real orgasm.
Not saying it can't happen. It may be that guys with a lot more anal experience than me may have experienced a full orgasm from anal penetration. But I do have enough experience to know that orgasm and prostate milking are not necessarily the same thing.
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I also am having trouble achieving that ultimate anal orgasm. I have tried many different toys, but to no avail 
Quote by garterbelt
I have cum many times hands free when wife fucks me with her strapon. Feels amazing
Does your wife have a sister?
I have tried different size dildo's and even though some felt really really good, I did not achieve an orgasm. I have a prostate toy which, after a lot of practice, can give me a remarkable and longer orgasm. Several have been hands free. I havent tried pegging would welcome the opportunity or maybe one day the real thing.
I came every time my fwb put his stiff cock in my ass. I tried dildos and vibrators of various sizes and shapes. But, nothing could imitate the feeling of a live, throbbing cock moving in and out of my tight hole. He didn't have to touch my cock. I was hard almost from the instant he pushed against my sphincter and exploded within a couple minutes, usually before he did.
It’s hard to do yourself, it requires someone else’s fingers via prostate massage or being topped, and they have to know what they’re doing. That’s coming from someone who has done Tantric courses on this subject. I didn’t have one with those Aneros things or any other devices until I let someone try via fingers/prostate massage, and that’s when I started experiencing them. As a Top myself, I learned all the positions that hit the prostate and how to build that, and then push them towards it. Doesn’t always work but I’ve gotten some men close or they’ve had them while I’ve topped them.
I often cum hands free when being fucked from behind standing up. At that angle his cock hits my prostate and if he had girth and stamina I get the most amazing full body anal orgasms complete with ejaculation. Being caged also helps as then the (w)hole are becomes swollen and engorged with blood and so hyper sensitive.
Quote by Alfresco
I often cum hands free when being fucked from behind standing up. At that angle his cock hits my prostate and if he had girth and stamina I get the most amazing full body anal orgasms complete with ejaculation. Being caged also helps as then the (w)hole are becomes swollen and engorged with blood and so hyper sensitive.
It’s good to know what positions do it for you. When a bottom tells me, it helps, otherwise I’m searching for one, which is kind of hot too. As soon as I find it, that’s when it’s time to send them to heaven.
