A boomer having her first anal at 50? I don’t think so. I’m Gen X and I’ve had lots of boomer females previously and all have tried anal at least once. Granted, anal wasn’t as such a focal point for boomers as it was for Gen Xers like me, my friends and classmates considered anal sex the ultimate goal. I’m thinking unless she lived a sheltered life and had boring husbands and boyfriends, she’s had anal before and simply lied about it to you.
My wife's first anal was in her 40's while married to her now Ex... but it wasn't with him. On vacation they met a couple and were drinking and chatting all innocent. He always goes to bed early and gets up early and went to bed while she stayed in the hotel lounge with the couple. Eventually they went back to the couples room and all got naked and played. He wanted her ass but she said no so his wife did and my future wife watched... right up until his wife passed out from the alcohol. He begged and finally my wife gave in... and had her first anal bent over a naked drunk wife. It was painful but she managed and before long she was slipping into bed next to her clueless husband with a sore ass full of another mans cum!