We are late 50s, married 35 yrs. We tried anal 3 times ever, didn't go well....all good.
We're late bloomers I guess, we got into mfm fun in out mid 50s. Many times with our one guy friend. Weird and very awkward first times, easier as we got more comfy with each other.
One night he was doing her from behind. He said they were going to try back door, I thought she won't. HE put lube on his dick, some on her butt hole, got lined up and started to slide in. It looked like her eyes were ready to pop out but she stayed with it. He went super slow and got it all the way in. She grunted like crazy. He took probably 8 or 9 full pumps really slow. He pulled out and she said WOW. Since then he's fucked her butt a few times. He's cum in her butt, there's been nights we've both fucked her butt. I've done anal with her quite a few times.
Our fun with him has really changed our thoughts about sex fun.