3 For Me.
My first high school bf wanted to try a few times. We were dumb and unprepared. I didn't hate it but i hindsight we could have done so much more to make it better. At 14 I wasn't the brightest.
Later in my 20's I really wanted to experiment more with sex in general but ESPECIALLY with anal. I was too shy to say it outright, and all the guys I dated seemed to be very good with vanilla boring sex. Eventually one night during round 2 I rubbed my partners dick against my pussy and back to my ass crack. Eventually i "accidentally" slipped him into the wrong hole...nothing special to report. The sex was never anything special and neither was that.
Many years later I met my husband. It was instant attraction (now I recognize that it was his very dominant energy I was picking up on) and he was not shy about telling me that he had anal sex. it wasn't a question of wether I was interested...it was what he did. I could either get on board or not...I guess you could day I got on board. It wasn't long before I was begging for anal...often 5, 6, 7 times a day. He would have to say no after a while bc he was chaffing.
After a decade together we still have a great sex life. So much so that there is discussion about playing with others. I REALLY want to try out a club, or a lifestyle friendly vacation, etc. and have the experience of taking 4-5 people up my ass in one night. Does anyone have any experience or advice?