I have had anal sex with four LTRs. The first was with my College girlfriend our freshman year, both virgins. That changed in short order. One night we were going at a doggy, and I started toying with her bum. It got to the point where I worked my thumb inside her ass. She really seemed to like that. Then she surprised the hell out of me when she said “put it in!“. With a lot of saliva and my wet c*ck,….. and a lot of patience, I Slowly worked my way Inside. Surprisingly, she loved it. She had a crazy orgasm with the help of her frantically rubbing her clit. That became a regular thing. Added benefit was no pregnancy risk (we had a couple scares with broken condoms) Our pattern became PIV sex with a condom until she came, then I would pull out, take off the condom, and move into her ass. it was so nice coming in her bare without worrying about her getting pregnant. With numbers 2&3, I think they just did it to please me. it did not happen often, before it stopped happening at all. With my current wife it took a little convincing….. her ex-husband did it once and was too rushed and rough. LSS I finally got her ass, on the condition that if I got hers, she got mine! SWEET! What really surprised me, what was the first time we did that she had a major anal only orgasm. WOW! of course turnabout is fair play, so she started pegging me. Loved it. we would have what we called AON…. anal only nights a few times a month. She would write AON on our calendar when I knew she was ready for it. Good kinky nights! I sure miss those days. It’s been years.