Threesome with a woman half my age and a woman twice my age.
It was always going to be a tough ask, with prossying starting at 18, I'd have to be 36 and the next one up would have to be 72. Try convincing an 18 year old to have a three-way with a woman 4 times her age, it ain't happening.
As I get older, the range of women half my age (or less) opens up but the older end dries right up, literally and figuratively.
Anyway, I HAVE shagged a woman twice my age, but that isn't a feat in your 20s, and shagging a woman half your age isn't a feat at 40+, just doing both at the same time seems a huge challenge.