Was 7 months ago. the age of consent where I was living at the time. I was having a fling with a much older man. The first experience was during foreplay he casually placed his hand back there between my vaginal and anal area and pulled it up between my cheeks and a finger grazed my bottom. I noticed it only because it was different. Days later, he did it again only this time it clearly wasn’t accidental. His hand paused and a finger massaged my bottom; I was already aroused but the feeling was like, hmm, okay that feels unexpectedly nice. Over the weeks, I began anticipating it and wanting it. His fingering became more focused and there were the beginnings of pleasant penetration. Then one afternoon, I think he was likely testing me, he ignored my bottom. We were in out usual configuration for intercourse to start and I interrupted him and placed his hand back there. Over the next few weeks he got some lube and got his finger fully inside me back there. The next big anal experience was being licked back there. That was a complete shock. The licking was quickly followed by him working his tongue inside me. I got to thinking about anal intercourse and we talked about it and he bought me some butt plugs and showed me how to use them. And finally full anal intercourse with a very different but very satisfying orgasm.