I have played with my own ass while masturbating on occasion since my teenage years....

My first encounter with someone elses ass was my first wife's in a weird transitional period... I think I was 23 at the time...

I've played by myself with vibrators and butt plugs sometimes.... I had a girlfriend fuck my ass with a strap-on she wore a couple of times

With a kid in the house, it's been a while since I've been able to fuck my wife in the ass.... but thinking about it is great fodder for masturbation excitement... (I will sneak a finger or two into her ass while she sucks my cock or while I'm eating her pussy.... )

The truth is that if I go straight to the ass, I'll cum very quickly.... better to save anal for a 'second go' when circumstances allow.