Oh, and in case you are dating a religious girl who thinks that having a . A very important first time anal sex tip is to take a shit before you try to. As more couples explore anal sex, understanding the risks, rewards Safety during sex should be a top priority, but having fun is certainly important, too. It's possible you will experience some bleeding your first time or two. NEVER, EVER, EVER go from anal to vaginal sex without cleaning the penis in My first time was very, very drunk, we tried doing it without lube or I was pretty obsessed with taking a girl up her dirt track until i did it, Pussy.