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Anal orgasm

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I've been trying a lot lately to orgasm just by riding a dildo or by using a p spot vibrator but I just can't seem to get there. I know I'm getting close because I leak precum and that feeling of build up is there but I just can't reach the peak and I have to finish with the usual stroking of my cock. I've tried all sorts and sizes of dildos and still, though it's pleasurable, it isn't enough. Has anyone any suggestions as to what I can do to cum hands free so to speak???
I date a TS for 3 years. She enjoyed fucking me but I think if she had to choose one over the other forever she would rather bottom. But there was times I might not want to get fucked but she would not be denied. She loved shooting her load in my ass. Sometimes when fucking her she would be about to cum and stop one enough to turn me over and press her head in my ass just enough to watch her cum leak out of my ass. I always wanted it in my mouth.
I have cum many times hands free when wife fucks me with her strapon. Feels amazing

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.

I also am having trouble achieving that ultimate anal orgasm. I have tried many different toys, but to no avail sad

"Sometimes you have to believe in someone else's belief in you before the belief in yourself kicks in" ~Les Brown

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.