Anal sex is the best...
The first time a boyfriend asked me to try anal sex was in school. I was 19. And because I loved him — in the way you can only when love when everything is fantastical and a first — I agreed to try it. We dated for three years, and basically introduced each other to every type of sex there could be.
The first time we went for it, he started by going down on me. It was as good as it always was and right when I thought I couldn’t take it, we started having "normal" sex. It was slow and sensual and he made sure to focus on kissing my neck and ears, getting me more and more turned on. He then flipped me over and we had really hard doggy style for a while, and without lube or anything, he easily slipped inside my backend.
Like before, it was painful, but he told me to breathe as slowly eased all the way in. He then reached around and started to play with me with his fingers as he gradually moved faster. I got more comfortable as he went on, and almost forgot where he was. As I let go more.. It didn’t hurt as much. And without even thinking about it, I had one of those explosive orgasms that you feel all the way up to your face.
For the duration of our year-and-a-half relationship, we worked in anal sex at least once a week. We got into such a steamy rhythm that we eventually tried different anal sex positions — including missionary and spooning. It easily became one of my favorite ways to have sex, and though the clean-up was pretty messy every time, I loved how the orgasms varied and how much fun we had with it.
My biggest recommendation? Though my first anal sex experience was sans lube and it was fine, lube will be your best friend. And a nice, warm shower before you get it on.