Two of the girls I have dated let me take their anal virginity. One girl actually approached me about it, saying she’d been reading lots of stuff about it online and wanted to try it. The other girl took some convincing.
There are definite differences between girls who are prepared to have their assholes penetrated and girls who are not. Things went really smoothly with Girl #1. She had prepped like a pornstar and knew what to expect. She even got herself ready with an anal plug. It was awesome and we tried anal several more times during our relationship.
Girl #2 was a totally different story. She was uncomfortable, unprepared, and had an embarrassing flatulence incident. She complained so much that I was happy to never put my cock up her butt again.
Some girls are just naturally anal sex sluts, while others aren’t even close. At my age, I’m not likely to get to dip my dick into virgin pussy territory, but I can still be the one to delve into asses that no man has entered before. I’ll take it.