After a handful of sessions with essentially the same results I decided to try something a bit different. Instead of lying on my side I decided to lay on my back for starters. Also, I tried out a more passive approach. After approximately 15 minutes into my session focusing on my breathing and relaxing I tried to create as small a contraction as I possibly could. Holding this contraction created some very interesting sensations, almost like a warm and tingly feeling. And suddenly I was completely aware of a whole new spectrum of sensations. Until now I was really only aware of sensations directly at my anus and the pressure on my perineum.
I could now feel the contours of the Aneros inside my rectum and the slightest pressure being exerted on my prostate. While maintaining the slightest contraction I began to notice some small involuntary contractions. I've made the mistake in the past to get too excited when this would happen, and try to force the next involuntary set to begin by increasing the intensity of my contractions. I decided to just focus on a very slight contraction. While doing this each set of involuntary contractions became increasingly intense along with more sensitivity of my prostate. After a while of climbing this hill the sensations became truly pleasurable. Every small movement of the Aneros was creating these amazing sensations from the inside. Warm, tingling, buzzing is the best way I could describe this.
These feeling persisted for another 20 minutes after the intensity of the sensations reached a plateau. And just like that my body was saying that it was enough for now.
Each session I have learned something new but this last one was the biggest step so far.