Navy Blue Hanky
I want to speak up for a group of women who are invisible—those of us who prefer anal sex to other forms of lovemaking. I just like the way that it feels! The more regular type of intercourse is boring to me and does not give me a strong climax. And there is the side benefit of not needing to worry about birth control. But I am tired of the attitude I get from some of the men who are attracted to me until I ask for what I really want. One guy assumed that if I liked anal sex, I must want to be hurt. But I am no masochist! I know there is a myth that anal sex is incredibly painful, but I have never found it so, if my lover is even minimally aware of foreplay. As long as I am turned on and relaxed, there's no pain or even discomfort. Other potential partners have been turned off by the thought of anal sex or they resent “being told what to do.” Some don't want to use condoms, but I would expect that no matter what kind of sex we were having! Another asked if I wanted to be “treated like a boy,” whatever that means. More than once a man has commented that he is not gay. This really surprised me.
Is there any way I can tell before I get a man home how he will respond (or not) to my desire? Should I worry about cultivating more of an interest in vaginal intercourse?
Until everybody starts signaling their sexual interests with hankies in their back pockets, you won't be able to tell what a potential partner likes without talking to him. But there's no rule that says you have to wait until you take somebody home to have that conversation. Just say, “I like something a bit different. Do you have a sense of adventure?” Few men will be able to say “no” to that question. Then ask him if he has any experience with anal sex. That should avoid the “don't tell me what to do” button. (Although I'm not sure why you'd want guys who get threatened by this. Maybe it's better to just find out who they are as quickly as possible so you can move on to somebody else.)
I'm not sure where you are looking for sex. The Internet's primary saving grace is the ease with which you can talk to people about their likes and dislikes before meeting in person. Face-to-face social situations demand a lot more boldness. You have to get up the nerve to spell it out in person. This can be nerve-wracking, but I think it's much easier to deal with rejection when it isn't in your own bedroom.
I appreciate the way that your letter sums up all the negative stereotypes of anal sex. If you find a gem of a guy who may not have a lot of experience, but is open to trying anal sex, perhaps Tristan Taormino's book The Ultimate Guide to Anal Sex for Women, would be a good resource. I agree with you that the key to making anal sex pleasurable is to use effective foreplay, be gentle, and make sure everyone is turned-on and slippery. Let's not forget that vaginal sex can be pretty damned painful if you aren't relaxed and ready!
I'm glad to hear you are insisting on condoms. Birth control is not a concern with anal sex, but staying healthy is still important. Condoms are the only way to prevent transmission of many sexually-transmitted infections.
Should you cultivate an interest in vaginal sex? Only if you are curious about it or it starts to feel good. “Regular” intercourse might be a nice option once in a while. But if you try to do it just because it's expected of you, that might ruin the experience. Listen to your body. She knows what she wants.