How to level up from pleasure to orgasm?

I have been enjoying prostate play for about 10 years, and while I enjoy the feelings, I have never experienced an orgasm from only prostate stimulation.

Does frequency of practice play a part? Is there a position that works best? Am I doing something wrong? What is the secret to going from “this feels good” to cumming?

I have a Helix Syn and an nJoy pure wand.