I’ve only had anal with an ex many years back. It was toward the end of our relationship and it happened accidentally the first time when moving from missionary to doggy I accidentally put it in the wrong hole. We had both earlier had quite a bit to drink and so perhaps that helped cause my mistake. She didn’t want me to remove it and she orgasmed after a minute or so. The next time we are together (may have been our last time in bed together I think) I’m about to enter her vagina when she asks me to enter her ass instead. I was caught off guard by this as I hadn’t even really considered anal again. So I did what she asked and after a minute or two she orgasmed, and then she orgasmed again after another couple of minutes if my memory serves me correctly. She was quiet during the anal sex, like she always was during vaginal, but her orgasms from anal were different. During anal orgasms her entire body would lightly vibrate. During vaginal orgasms she would tell me she was coming and her face sort of freeze, that’s the only way I even knew. I don’t think she faked the vaginal orgasms because they were so rare anyway.
So she rarely orgasmed with me vaginally and here she was having orgasms left and right anally. Of course my insecurity reared it’s ugly head later on when I got to thinking about it. I had started becoming a bit more aware that thickness can matter to women (back then I mainly thought in length) and then I started thinking about what I had heard a few times, that women prefer smaller men for anal. At about 4 1/2” midshaft and 4 3/4” base I thought I might be on the small side and I started thinking she enjoyed anal because of that and I even started thinking she would have had more vaginal orgasms if I had been thicker.
I didn’t get shit on my dick either time.