Prostate massage?

I have a glass dildo that she uses on me when she milks my prostate. Still struggling to achieve a true hands free. The precum flows freely and we get to a point and then it just seems to stall. This said when she massages my cock at the same time I still have the most intense orgasm I have ever had and nearly pass out afterwards.

As another form of prostate play I love to put my Aneros Helix in about an hour before we play and then we have a normal play session with lots of oral, cowgirl etc. and definitely find that with the Helix in I am much much harder and cum a massive load.
I had an extensive session with the Evolved massager Monday but never got anything to really build. I did find a position the was more pleasurable than usual, but i had to switch to my pegging dildo just to get close. I felt it build and just perpetually felt like I was on the brink of imminent orgasm but couldn't tip past the point of no return.

By then I was already about 45 minutes into it. Close to 2 hours with prep, so i just ended up grabbing my limp cock and finishing off. Felt intense, but i had been hoping for the hands free to finally.. come.

It annoys me to no end that remain soft the entire time.

I might just bite the bullet and spend the money on the Vice 2, despite my dislike of the Helix Syn5.
 
I got a halfgasm the other day in the shower. I squatted down using just my fingers. I totally relaxed my ass so I actually touched my prostrate. Took about 10 minutes and just as I thought a full one was Cumming I kind of crapped in my hand. Not a lot but I'd never done that before. I kept going but the thought of shit on my hand ruined it. Sorry if TMI but I'm sure I'm not the first that has happened to.
 
I got a halfgasm the other day in the shower. I squatted down using just my fingers. I totally relaxed my ass so I actually touched my prostrate. Took about 10 minutes and just as I thought a full one was Cumming I kind of crapped in my hand. Not a lot but I'd never done that before. I kept going but the thought of shit on my hand ruined it. Sorry if TMI but I'm sure I'm not the first that has happened to.
Relatable.

I've had a couple of amazing build ups only to feel the pendulum swing the other way and realize that next contraction is not going to be the explosion I was chasing. Off putting and discouraging to say the least.
 
Relatable.

I've had a couple of amazing build ups only to feel the pendulum swing the other way and realize that next contraction is not going to be the explosion I was chasing. Off putting and discouraging to say the least.
I have exactly the same. I guess my question to myself is that when that contraction doesnt come whether I (or the wife) are being a bit impatient and need to just keep going.

Either way the final is mind blowing but I want the illusive hands free
 
I got a halfgasm the other day in the shower. I squatted down using just my fingers. I totally relaxed my ass so I actually touched my prostrate. Took about 10 minutes and just as I thought a full one was Cumming I kind of crapped in my hand. Not a lot but I'd never done that before. I kept going but the thought of shit on my hand ruined it. Sorry if TMI but I'm sure I'm not the first that has happened to.
First time I've heard of a halfgasm and I'd love to try.
 
I've dropped a bullet vibe into two (yes, two) condoms and put that up my ass. Can't say for sure it laid against my prostate, but it was in close enough proximity the sensation was pretty damn intense.

The doubled up condom was for extraction. One wouldn't be strong enough, but two, if you're careful and don't let them stretch too much, will do the trick, if you're relaxed enough.
 
I've dropped a bullet vibe into two (yes, two) condoms and put that up my ass. Can't say for sure it laid against my prostate, but it was in close enough proximity the sensation was pretty damn intense.

The doubled up condom was for extraction. One wouldn't be strong enough, but two, if you're careful and don't let them stretch too much, will do the trick, if you're relaxed enough.
šŸ¤£šŸ˜‚I thought you said actual 0.22 or 0.5 cal bullets at first!
 
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