My first time was with one of the twin boys that lived behind my grandparent's house. I was all alone at my grandparent's house so he came over. One thing led to another and we were busy doing our usual play. We were playing with each other and sucking each other. He asked me if I had ever been fucked. I hadn't even thought about it and told him I don't know. It really didn't sound appealing to me at the time. He started sucking my dick and would get a finger wet and start rubbing it on my hole. It felt good and I let him continue. He kept getting more spit on his fingers and would rub it on my hole. He never put a finger inside my hole, but I was pretty naive and didn't know better. He turned me around and bent me over. Next thing I know, he tried to jab his dick into my hole with no lube. His dick wasn't very big, maybe 5" long and pretty skinny, but DAMN, that hurt like a mother fucker!!! I jumped forward to get away from him and told him that he wasn't going to try to fuck me again. I was in horrible pain and told him that he needed to leave. He got mad because he still hadn't gotten off, but I told him that wasn't going to happen.
I didn't try anal sex for MANY years after that. The next guy was my first boyfriend. He asked if I was a top or bottom, and I had to tell him the story about my first time. His dick was MUCH bigger than the guy from the first time and I wasn't sure if I really wanted to bottom. He told me he would take it slow. He worked my ass for a long time with lots of lube and spit. He started to push his dick in and it was pure heaven! I'm glad I tried it again, it was so worth it!