Prostate Orgasm

Do you orgasm when you bottom cock hard or soft?
If it's a sizeable object (or cock), I stay soft-ish until just moments before and then it's rock-hard as I shoot. Unless I'm in a cage... I will cum thru the cage but I don't get hard whatsoever.
 
Amazing thread. Big time fantasy to have my wife help me cum like this. In the meantime, I have only been successful in making my cock drip while riding a dildo. I don’t think I’ve reached orgasm though.
 
Amazing thread. Big time fantasy to have my wife help me cum like this. In the meantime, I have only been successful in making my cock drip while riding a dildo. I don’t think I’ve reached orgasm though.
Believe me, you would know if you did!
 
My lady brought it up recently while in bed. She very much wants to pleasure me in ways since I do a variety of things to her. Any insight on helping her manually stimulating my prostrate is appreciated.
 
My lady brought it up recently while in bed. She very much wants to pleasure me in ways since I do a variety of things to her. Any insight on helping her manually stimulating my prostrate is appreciated.
Maybe get her to peg you.
 
My lady brought it up recently while in bed. She very much wants to pleasure me in ways since I do a variety of things to her. Any insight on helping her manually stimulating my prostrate is appreciated.
My wife gave me a really good prostate massage last weekend. We watched this video together.


More often than not, she pegs me and/or uses a massager on me. She hasn’t given me too many massages with her finger but this one was the best.

I don’t know why I never learned this before, but for me to have a milked prostate, I need to masturbate or be masturbated near the edge and then the finger, massager or whatever puts me over the edge. (I love humiliating orgasms).
 
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