I was taught a valuable lesson in my early 20s by a woman about anal sex:

I wanted to fuck a very cute brunette woman in the butt that I knew and had dated a few times. She had the cutest round butt I had ever seen at the time, so one night I asked her and she said okay I could fuck her with lube back there. However, when I finished it would be my turn to be fucked by her and not to forget I have the same hole, and she had a cucumber 🥒. This caught me off guard but she was right, and the more I thought about it the hornier I got. So I agreed and she bent over the bed, I lubed up with KY jelly and gave her a slow butt fucking till I came and slowly pulled out of her. She went to the kitchen and came back with a fat cucumber and told me to bend over. She taught me a hard lesson.