I purchased my first prostate massage toy, an Aneros Helix SYN, one and a half month ago and would like to share my personal journey with you. I haven't yet experienced an orgasm with it, but reading the Aneros wiki as well as personal experiences of other users helped me understanding my body better. Questions, comments and suggestions are welcome.
My pre-Aneros experience
One of my favorite things to do (if time permits) is watching porn without touching my penis. I like the warm, pulsating feeling, the feeling of my erect penis rubbing against the fabric of my underwear and I also enjoy the flow of pre-cum. I guess this started when I was a teenager and couldn't whip out my dick in front of the computer. I still do this sometimes until I got quite a bit of pre-cum in my pants. I have never experienced a hands-free orgasm in all these years. At some point I get so horny that I need to jerk off using my hands.
Sometime around 2008 I discovered a video of someone using an Aneros. Interest in Hand-free orgasms and prostate milking led me to exploring my own anal canal and prostate. I had (and have to this day) severe problems finding my prostate with my finger. I did manage to get a flow of pre-cum running, but I didn't find the whole experience very enjoyable. Although I didn't find a magical button that is giving me instant pleasure, I enjoyed getting to know my body a bit better.