Yes,I have. My wife knew all about prostate play and orgasm when we met (her 1st husband was into it) and now I can do it using a dildo
I've tried several prostate vibrators and dildos, but they've never made me cum. I still play with them anyway. While I'll wear one of the prostate vibrators around the house until the battery dies, as SantaCruzRob observed, they're more fun with a friend; someone who can help me insert a dildo and hold it while I fuck it to the point of exhaustion. I might not cum, but it'll sure give me a dopamine buzz. If I jack off to orgasm while getting fucked, it's more intense, and I cum a lot more than otherwise.
I've never experienced a hands free orgasm with any of my toys. I have cum hands free while being fucked when it hurt just right.
Did it today out in the garage. It was already in dripping mode and I really started to work on the dildo and that was it. Hands free
I have orgasmed hands free only twice from fingering myself and it was intense bliss. I have tried dildos,thrusters, and vibrating prostate massagers but(t) can't hold them in the needed position long enough by myself.