jan. - “A dude I was dating a few years ago asked me about anal on our THIRD date. Can you believe that? I'm no prude, but I'm not doing anything in bed that involves anyone's pooper until I at least meet your parents, okay?” — Emma, beetlejuice. 6. “I had anal sex with my boyfriend for the first time a month. mai - Dear Anna,. My BFFs at my book club have been reading “Fifty Shades of Grey.” In between gulps of Yellowtail chardonnay, and prompted by your recent column about butt play for everyone, one of us blurted out: “I wonder which number is greater: the guys whom we've gone to bed with on our first date. 8. jan. - Is Anal Sex a way for men to explore their latent homesexual desires? Leelee explores this topic and more on open relationships and what it means to us.