Once we make it exclusive, I casually bring up the topic of things to try in bed, just like my previous ex-boyfriends had done. 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. As I let go more, the tension faded. Check out our video on sex positions for small penises:. I got more comfortable as he went on, and almost forgot where he was. The first time a boyfriend asked me to try anal sex was in high school. Though my first anal sex experience was sans lube and it was fine, lube will be your best friend.