Dear Mistress Maeve,
My boyfriend has never had, and swears he will never have, anal sex, so how in the world do I get him to do it with me? I've told him over and over how much I love it, but he's pretty vanilla when it comes to sex. I'm very open with him sexually and have told him how hot it gets me. What will help him take the plunge?
You say that you tell him over and over how much you love anal play, but have you given him the chance to tell you why he's reluctant? People have many misconceptions about anal pleasure — it's messy; only "sluts" like it; only men get off from anal penetration. In all this noise, the eroticism of anal sex gets lost. Your man could be buying into these misconceptions, so you need to get to the "bottom" of his objections.
Have a talk with him outside the bedroom, reiterating that you deeply desire to try anal with him, and tell him you want to discuss his hesitation further. Be sure to validate his feelings and be a good listener. He may have reservations that are easily remedied. For instance, he may worry anal sex is messy, and you can explain that condoms and baby wipes are an easy fix for any unforeseen mishaps. Or his issues with anal may be more deeply seated and demand more care and understanding. He could be worried that he'll hurt you, or reluctant because of his lack of anal experience. Whatever the case, give him a copy of Tristan Taormino's book The Ultimate Guide to Anal Sex for Women. You can get a version written for men, but it may ease his fears of penetrating you to read about anal pleasure from a woman's perspective.
If he decides to give anal a try, the responsibility will be on you to guide him through it. The formidable Susie Bright once said, "No lover is able to look into your eyes and figure out how you want to get fucked in the ass." She's right — he will be relying on you to play coach and cheerleader in your anal fantasy. If he still balks at your back door, it may be time to try another knocker…