I first experienced anal nearly 60 years ago - with my wife, and not long after we married. We both thoroughly enjoyed sex 2 or 3 times a week (it was, of course, much more than just sex for the sake of a fuck), and we both resented those days when a period intervened, so when I told her about the Italian girls who stayed virginal for marriage by taking it anally she was willing to try. After a good deal of trial and error and a lot of buggering about (sorry, couldn`t help that) we both got the hang of things, and whenever her period started the jar of lube appeared on the bedside cabinet, the lubing became more a foreplay than just a necessity, and bareback was the order of the day because she always wanted to feel me cum inside her and she always came herself. This continued until her periods stopped, but then, of course, no contraceptive protection was necessary, and she`d discovered the delights of riding me to several orgasms at a time.
After she died I tried anal a couple of times; the first time with a girl who advertised anal, and it was as about exciting as dipping my dick in a milk bottle. The second time the girl rode me, but apparently I thrust upwards a bit too hard and she leapt off my dick screaming - very nearly circumcising me in the process. I decided that I was never likely to find another anal partner like my late wife and haven`t tried since.