Anal sex...way befor married....I tried with every girl I was naked with. Some...no way....Some ok let's try, it hurts so stop. Some were clearly into it. Others said...I've never done it befor but let's try, obviously they had done it before but didn't want to admit it, I'd slip right in and she was cool with it.
Married my wife, her 2nd marriage. We tried anal 4 times, never went well. All good.
About 4 years ago we got into mfm fun with a guy, it's become a pretty regular thing for us now. Long story but we just worked up to enjoying it with less guilt.
We'd done it with him about 10 times over more than a year, we were all comfy together. One night he was doing her from behind, he pulled out, reached for the lube. Was a normal thing. He put some on his dick then started to lube her butt hole, she said what are you doing? He said he was going to do her butt, she said no but didn't pull away. He got lined up and she just let it happen. I was thinking no way. He slid it in VERY SLOW. Looked like her eyes were ready to pop out. He got it all the way in, started SLOW full pumps, she grunted with each pump. He went for maybe 20 pumps then pulled out. Wife said WOW.
Next time we got together after we had each fucked her once, same deal, slid in SLOW, SLOW pumps, she seemed OK but was grunting with each pump. Maybe a minute or two and he cummed in her butt hole. He pulled out, she plopped onto her belly and said WOW.
Since then I've done her butt many times, he has too. I guess it has to be gentle.