Anal Sex, Yes or No!

To have or not to have, that is the question.
I am 49 years old and my ass is a virgin, literally.
I have had tongue and a few fingers in it but no penis penetration.
I have attempted a few times and for as much as i have a pain/pleasure fetish I have a low tolerance for pain and those attempts were very painful or I'm just a pussy, lol. Either way I want to experience it at least once, so what should I do to prepare my mind/body for it. What are the pros/cons to it ** should I just stay anal sex free