Holy smokes. After being a follower of this thread for years, it finally happened. Here’s what I learned and my process:
Toys of Choice:
- njoy Purewand
- njoy Pure Plug (large and xl 2.0)
- Liberator Wedge
- Aneros Syn Trident
- Aneros Progasm Ice
- Lelo Hugo
Lifestyle Prep:
This was the biggest change to my success. I would have sessions using the Purewand, both Aneros and the Hugo, be relaxing and trying to make something happen out of it with no success. Then, after being fed up, I would take care of myself the normal way with whatever toy inserted and then head to bed. These orgasms would be great, as I would feel contractions while orgasming mashing against my prostate, but they would always end at ejaculation. So, I made the decision to stop trying for a prostate orgasm. This is where my success came from. I focused more on reporgramming. Reprogramming is a real thing. Instead of trying for a prostate orgasm, I switched over to using the Pureplugs and Aneros Prograsm around the house or while taking a shower just for the sensation. Once I was comfortable with them and I would feel good and relaxed, I would take them out and just get used to the feelingleft by the massaging of my prostate (and lack there of once removed). Rinse and repeat, no orgasms after those sessions, and honestly, it still brought pleasure once removed. The big learning that the Pureplugs and Progasm bring over most other smaller toys,is that they taught me to be able to relax my muscles as I had no fear that the toys would fall out and listen to the sensation of my prostate.
Prep right before:
I took a shower to start to relax myself and used the Aneros Progasm while I was in the shower to start to decompress and lube (plenty of it!) This part is all about getting into the mindset.
Actual Session: After the shower, I whipped out my handy dandy Purewand and as I was already prepped from the Progasm, went straight on with the larger end of the wand. I started face down (doggy style to insert) on the wedge, and then once inserted flipped over to my back with hips in the air due to the wedge. Purewand was curved up at this point in time. Since it had been so long for trying for an prostate orgasm, this time I focused on just pressure and listening to my body. I think a big peice that is missed when using a vibrating toy / trying for a prostate orgasm is that we are chase for the orgasm, rather than just listening to the body. Also, I forced all muscles to relax (especially the sphincter muscles ie think of trying to open up to the toy). Insertion depth for me on average through the session was about 3 inches. I used one hand to hold it there and to be honest, did not move it at all from that point, so long as I felt just a little bit of pressure on my prostate. From there, continue to relax your muscles. There were times in the session in which my muscles would semi voluntarily contract, and it was important for me to force myself relax that. Naturally, the njoy continued to slide into me until it was around 6" in. I slowly worked it out and then my arms started to shake and I had a massive convulsions and thought something wrong happened. I am going to use @Cumalot82 's saying of
This is pretty important to keep in mind as I was not ready for that. First prostate orgasm was a wasted one
I reset after this, again just focusing on the building pressure of the Purewand against my prostate and forcing myself to relax my sphincter muscles. As I feel the pressure staring to build, I continued to force myself to relax, which brought more uncontrolled contractions and allowed the orgasm to continue to build.
Mindset during the session:
My mindset honestly was just to relax. I wasn’t terribly turned on, my focus was just listen to my body and in a dream like state. I was focusing on what scenarios turned me on, did not have any visual stimulus, just my thoughts.
The sensation:
This is the wild bit. Take everything you know about a penis initiated orgasm and throw it out the window. This was a complete full body orgasm for me that honestly started in my fingers and then went throughout the body. My fingers tingled, then started to shake followed with my arms, legs and then full body shakes. After the second orgasm, I focused on relaxing and adding pressure during the orgasm to my prostate which allowed me to extend the orgasm out to about a minute and a half (it felt that way at least). Naturally I would mash the purewand against my prostate, so I would force myself to relax my muscles to keep going. The focus of this was for me to prolong the orgasm, and honestly I stopped the orgasm by removing the pressure, rather than the orgasm stopping itself. I stopped the orgasm by pushing njoy slightly deeper, so I ended up having some convulsions when I was taking the toy out at the end. The ending of it was wild too. Unlike with a penis initiated orgasm of which I immediately feel tired after it for a few minutes, this was the opposite. I was wide awake, alert and ready to hit the ground running (as well as you can with a Purewand still inserted). 
TLDR: Patience is everything, don’t rush it and don’t expect results immediately. Learn to relax both mentally and your muscles. Focus on the sensation of pressure on the prostate as it starts to build.
Shout out to @UKlovingcouple for all the tidbits!