What are the biggest age gap you've ever had with a sexual partner? Both older and younger.
Obviously I don't want to hear about underage stuff. Keep that stuff to yourself.
Older was when I was 21 or 22 and I met a 40 something woman in a bar. I guess she was a cougar before the term was created. We both were drunk and flirty, and we ended up at some no-tell motel for the night.
Younger age gap was when I was 55 and she was 42. We had been platonic friends for years until one New Years Eve party she came to me and asked if our friendship could survive one night of love.