My first experience was when I was 16, I found out about prostate stimulation from the movie "Road Trip." haha. Anyways, I locked myself in the bathroom and insered my gloved index finger into my ass. I lubricated it with Pond's cold cream. It was a very cold, stimulating feeling. You could call it love a first finger? I have never had any type of anal stimulation other than by myself, but I'd be very interested to hear at what age everyone else's first times occured and how it went!!