Intro: Think Positive
First let's get one thing straight. Positive thinking is essential to achieving anything in life. You've got to go at this with the right attitude. So here are the top three things to keep in mind:
1. Anal Sex is Perfectly Natural
2. She's Gonna Love It
3. It Won't Hurt a Bit
Don't just learn this list. Make it your mantra, your religion. If you don't believe it, after all, how will she.
Step 1: Preparation and Study
Before you even think about broaching the subject with her, you've got to do your homework. A woman is much more likely to consent to anal sex with a man if she's convinced that he knows what he's doing. After all, would you want to offer up your delicate behind for some clumsy amateur to experiment with?
Read, Read, Read
Study up on anal sex. Read everything you can get your hands on. We recommend Tristan Taormino's modern classic The Ultimate Guide to Anal Sex for Women.
The bottom line is that you need to devour as much material as possible from as many viewpoints as possible, because she's going to have questions and concerns. You need to be able to answer all of them with confidence and precision. Even if you've never enjoyed anal sex before, you need to seem like you're an expert. The most important first step to creating that illusion is good old-fashioned book learning.
Don't look to commercial porn for pointers on anal sex; the way they cut the action, you'll never get a good sense of proper lube or the initial insertion. However, there are some instructional videos specially designed to teach you the ropes. Anal Sex for Women is available on video, as is Nina Hartley's Guide to Anal Sex.
Talk to Your Gay Friends
Forget about your straight friends; they're just going to lie to you about their anal sex experiences. Your gay friends, however, are likely to have a lot of good information on the subject. Quiz them on their experiences, their favorite techniques, and the most common gotchas. Ideally, try to talk to people who have been on both ends of the stick to get a complete perspective.
Based on your research, you should go shopping and get all of the paraphernalia you might possibly need. That's sure to include condoms and lube, and might also include things like latex gloves, enemas, baby wipes, dildos/butt plugs, etc. Buy plenty of it all and have it at the ready; you never know when you might get your chance.
Now that you've done preparation on your end, it's time to start getting her used to the idea.
Share your anal sex experiences, hints, and tips:
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