Back in my teens, when I first started having sex - that was the big attraction to anal - being able to fuck and cum inside my girlfriend (now wife) without a condom. I remember how intense and intimate those orgasms felt compared to sheathed variety. Fortunately we never experienced any adverse effects from it.
Anal intercourse ended for us when my wife developed a hemorrhoid during childbirth (30 fucking years ago) - she never got comfortable with the idea after that - until recently that is.
My wife stayed on birth control pills because going off of them caused her to have hormonal issues, so consequently, I never got a vasectomy. She finally quit taking them as she approached menopause and we went back to condoms. If I had known it was going to drag out this long I certainly would have gotten vasectomy - but we figured a year or so and it would be over. Plus we were only having intercourse about once a month due to her diminished libido. She really just didn't care for sex at all.
Fast forward to the present. My wife's libido is making a strong comeback and we are having intercourse a lot more - 4 or 5 times a week - with multiple rounds! But she still insists on condoms as things heat up. It's kind of funny actually - "I have to put on a condom because YOU are about to cum"? She has said that we will stop using condoms when she goes a full 12 months without a period. I had 6 months knocked out, then boom - another period - back to square one.
Back on topic - with her increased libido, she is also back to loving anal stimulation - but her asshole is incredibly tight. At first even a well lubed finger was a challenge. But as she is learning to relax and enjoy, we've moved up a bit and now a couple of fingers and smaller probes are possible. A couple of times she thought she was ready for my cock, but it just seems to be a bit larger than she can relax and accept. I'm confident we're getting close as we gradually work with slightly larger toys or an additional finger.
When we finally do get there - you can bet there won't be any condoms involved - as I can't wait to drop my seed deep in her ass!