I had my awakening in my 50s. Started buying cock rings and a few toys. I introduced them to my wife slowly. It wasn't until I was 56 or 57 I bought a prostate massager. It was great but as most of them are, they are meant to be used and not worn. I branched out and bought a couple small plugs. Then some larger ones, and eventually a rubber dildo with suction cup. I am working slowly to introduce them to my wife because I dont believe she knows my true love of anal. To conclude my favourite in my collection is a silicone cock and ball ring strap with a stainless steel butt plug I wear out constantly, to work or other events.
It’s feels really good at first, as it is really tight. But as you go it will loosen up and the sensation will get less. It is very erotic for sure.
I didn't even answer my own question. A wonderful woman( 20 yrs older) I met when I was a Bartender introduced me to anal pleasure. When she went from sucking my cock , she continued on to sucking my balls, then eating and fingering my asshole. There was no looking back. When I wanted to play with my wifes ass, she asked me how I would like something poking in my ass. She was surprised when I said YES! , then she proceeded to slide her hard white plastic vibrator up my ass. Many vibrators, buttplugs and dildos have happily visited since.