Originally published February 1, 2007:
When I was a promiscuous young man (read: straight college boy), I had lots of casual sex. I particularly loved anal sex. And I very particularly loved rough, unlubricated anal sex with women who enjoyed same. I swore thatI would never be with a woman who didn't love anal.
But I am now dating a woman whom I love intensely and who is open to anal sex, but we just can't make it happen. Toys, fingering, eating ass, fucking—it all hurts her. She is a ballerina and, therefore, small with a tight frame. Is there a best plan of action here? She wants to do it, but obviously neither of us wants to see her hurt. Please help. This is important to me.
Boy Wants Anal Action
My response after the jump...
Toys, if they're too big and ineptly employed, can hurt. Fingers, with bony knuckles and sharp nails, can hurt. Fucking, which involves fucking, can hurt. But eating ass never hurt anyone. So unless you're wearing a diamond-encrusted grill or you studied eating ass under Jeffrey Dahmer, there are only three plausible explanations for this baffling assertion, listed here in ascending order of plausibility: 1. Your tongue is four feet long and it irritates her esophagus when you rim her. 2. She's got a very serious medical condition—chronic fissures? terminal hemorrhoids? suppurating gunshot wound?—that she hasn't told you about because she doesn't want or need your damn pity. 3. She doesn't like anal and never will, but she's telling you what you want to hear.
But let's take her at her word: She wants it. So what can you do to make it happen? First, forget those women you met at college who liked their anal rough and unlubricated. (Where the fuck did you go to college? The University of North Carolina at Bloody Stool?) Most people—sober people, male and female people—require tons of foreplay and gallons of lube before buttfucking. The foreplay can include rimming, fingers, vibrators, and the sensuous application of lube—lots of lube. Then, once everyone is nice and relaxed, you slowly penetrate your partner, giving his or her anal sphincter additional time to relax.
If you've been doing all this and it hasn't worked, well, then dating this dancer means going without anal.