This series of articles describes a strategy to help your wife or girlfriend not only try anal sex, but learn to enjoy it. In the last article, Laying the Groundwork, we discussed helping your lover begin to recognize her ass as an erogenous zone. In this one, we will continue with that particular lesson, but we’ll also add a component of penetration.

To help illustrate our discussion, we’ve been following the fictional example of Roger and Alison, who have recently celebrated their five year wedding anniversary. Though happy enough, both have felt that their sex life has grown a little mundane. Roger’s plan to enliven it is to add anal sex to their repertoire.

Alison? Well, anal sex hadn’t sounded like a good idea at all to her, but lately, she’s been wondering if her initial reaction was the wrong one. A few weeks ago, Roger introduced a new wrinkle when he took her to bed. When he was giving her oral sex, he surprised her by putting his tongue there, up between her cheeks. And even though it makes her blush a little to admit it, it felt really good to her. So good, in fact, that she’s hoping he hasn’t forgotten about it. It’s been a few weeks and he hasn’t tried it again…

If you’re following the instructions I provided in the last article, you’ve waited for a least a few weeks since your first exploration of your wife/girlfriend’s ass. This allows her time, like Alison, to think about what happened, to remember how it felt, and to come to terms with the idea that she enjoyed it. It also gives her time to start to wonder if you’ll do it again…perhaps even to hope you’ll do it again.

And you will. When you’ve allowed enough time to pass, choose a night when your lover is in the right frame of mind. Move down between her legs and use your tongue to give her pleasure. When she is already excited, slide your tongue further south, up between her cheeks. If all has gone as expected, she will welcome the sensation. With any luck, she’s been hoping for it!

Your goal for tonight is to penetrate your wife’s ass. However, remember that you need to be satisfied with small steps and incremental progress. That means that you’re not going to jump all the way to anal sex this evening! Instead, you’re going to penetrate her with your finger, so that she can get used to having something inside her ass, and so that she can relax and enjoy herself while it is inside her.
One challenge that you’ll need to overcome is lubrication. As a general rule, you should always use some sort of lubrication whenever you insert something into your lover’s rear entry. However, because we want this to be somewhat of a surprise, and to have it seem to your lover that it just kind of “happens”, and because your finger is relatively small, I believe that breaking out some kind of lube and applying it is a mistake. Instead, I’d suggest that you use your wife’s natural lubrication to solve the problem.

If you’ve been using your tongue correctly, she’ll have plenty of lubrication available! Slide your index finger into her vagina to get it very moist and slippery. Then, move your tongue up to caress her clitoris and simultaneously ease your lubricated finger into her anus. Go slowly and gently, but be firm as well—you want to be sure it enters her. Stop when you’re inside to the second knuckle. Now, spend a nice long time simply giving her oral pleasure while you keep your finger inside her ass. There’s no need to thrust or move your finger around inside her—simply let it rest there, so that she can feel it, get used to it, and enjoy the sensation. Hopefully you can bring her to climax in this position.

When Roger’s tongue found Alison’s ass, she gasped and drew her legs up and back, giving him full and enthusiastic access. When Roger’s finger pressed up against her anus, she caught her breath, holding it as she felt him penetrate and slide up inside her. And when Roger spent the next fifteen minutes with his tongue between the lips of her vulva, she reached a shuddering orgasm twice, tossing her head and clutching the sheets as she came. Afterwards, Roger mounted her and took her, and she clutched him close, wrapping her legs around him as she felt him ejaculate.

By successfully following the steps in this article, you will have accomplished two things. First, you will have cemented the idea that her ass is an erogenous zone in your wife or girlfriend’s mind. And second, you will have let her experience penetration in a mild, non-threatening format, allowing her to relax and enjoy the sensation, and come to associate it with pleasure and excitement.

Now that you’ve reached this plateau, you should stop and consolidate your gains a little before trying to climb higher. Repeat the exercise you and your lover have just gone through several times over the coming weeks, whenever you and she feel like it. I’d counsel not doing it every time—anything can get old if it’s repeated too frequently. But making it a fairly regular occurrence is a good idea. Each time you penetrate your wife’s ass with your finger and she enjoys it, it further drives home the idea that it feels good to have something in her behind, and makes her wonder what it would be like to have something larger than your finger slip up and in. And eventually, she’ll be ready to try it

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