A brave new world

Here is where I record my journey with this strange and novel first time anal toy/device experience.

The first day was a Friday where I wouldn't have to get up early the next day. I took out the aneros helix trident hidden away, laid out the towel on the bed, and proceeded to lube myself up. I have fingered myself in the past, trying a prostate massage, but only one finger and I only felt pleasure from the prostate right before cumming, where it seemed to swell up and become much more sensitive. This time, I tried a finger as a warmup, then proceeded to try to relax and slowly push the device in. It took a minute or two and went pretty smoothly, not encountering as much resistance as I expected. When it was fully in, the thickness was not overwhelming but intense. I tried squeezing my anal muscles, but couldn't feel much. Later I tried masturbating normally with my dick, but the thickness in my anus was hugely distracting from my normal fantasizing. While eventually I did cum a lot, it wasn't anything special. Maybe my legs weren't relaxed, since I did some exercise a few hours before.

The next day I proceeded after a hot shower to get my muscles relaxed. The aneros was actually harder to put in this time, maybe because I didn't have enough lube or more likely was proceeding at the wrong angle. After more lube I got it in, slightly not as deep, and it felt more natural than yesterday. I tried squeezing my anal muscles, and I seemed to get a hint of pleasure from squeezing somewhere. However after 20 minutes or so, the feeling of needing to pee became overpowering and took away any subtle pleasure. I hypothesize I have to really concentrate on a horny, butt-focused fantasy to get pleasure.

Something unusual I've experienced during my fantasies (for years now) is that if I focus on very bottomish thoughts, like: thinking about my butt and thighs being squeezed, being fondled, being called a fucktoy, crossdressing and moaning like a cute bottom, etc. (fantasy rather than real life), I feel these weird sensations originating from my anal area - not pleasure, but a sort of adrenaline wave or sensitivity, somewhat like the wave of adrenaline when scared. If I continue to focus on these, I get teary-eyed, not sadness crying but somehow emotional. I cannot explain it and I've never heard of anyone else experiencing this, so I'm interested if anyone else has had something similar.

The only other time I've had what could be prostate pleasure was a bizarre circumstance many years ago when I sitting at a desk really needing to poop, and squeezing the pressure somehow felt good in my butt. I haven't experienced anything like that since.

The following week was my third time trying. I felt more comfortable with the massager inside me and less like the feeling of having something large spreading my butthole wide. I could perform kegels and definitely felt a pressure on my prostate, however there was no pleasure. The only time there is pleasure is in the inevitable period a second before cumming where any touch of my prostate is extremely pleasurable, however this only lasts one second and seems to be due to cumming rather than any pure prostate pleasure.

I'm interested in any of your thoughts and tips for continuing my journey. I'll try not to put any expectations or rush myself.