Physically the first time was OK, but it got a lot better. Emotionally, the first time was beautiful. We had been talking about it and he had been training me for about a month. We had used lube and some toys (which I didn't like until after we got into anal sex, now I love them) and mostly his fingers.
It was slighly uncomfortable at first, but he went slowly, letting me guide him and telling me what I good girl I was and how good it felt. I felt so loved
the first time. (Well, I always do feel loved when we are having sex. But, this was so intimate and wonderful, it was different.) I did bleed a little afterward (weird, because I didn't even bleed the first time I had PIV sex.) but we didn't use enough lube and I have flare ups of....er..... hemorrhoids since our babies were born. Sorry. The next time there was no blood and no discomfort.
The next time was much better. It's so much better now, and we both enjoy it a lot. I was glad I didn't let my fear prevent it. He knew to go slowly and let me guide the action, though. That makes a difference.