In my teens I had an encounter with a lady in her mid 60s - honestly sets my pulse racing to remember it even now... at 18 I had a fling with a 60yr+ colleague (despite numerous satisfying sexual encounters with girls my own age, I'd held back losing my actual virginity until it was going to be something worthwhile and memorable... this full bodied, mature woman couldn't believe it when I rubbed my cock against her wet cunt and told her I was a virgin, then eased my cock into her and told her I wasn't anymore).
I worked in a hotel for a while - loads of mature/older ladies on business trips or at functions would flirt a little, then be delighted to find I was more than receptive to them.
At 19 had a longer fling with the ...... of a guy I'd went to school with, and an encounter with one of my teachers from school... in my early 20's had a fling with the 50yr+ ...... of a guy I had been mates with lived down the road from back when I was 13, and another with a 60yr+ widowed colleague... in my mid 20's I had a brief fling with the 50yr + ...... of an ex-girlfriend... about 10 years ago I had a couple of encounters with ladies aged between 65 and 70 arising from a (very innocent and worthy) charity photography project. The sexiest thing I've ever heard is a woman look over shoulder at me and confess "I haven't had a man inside me for more than 25 years... I need to feel you cum in me!"