Alison’s hands are twisting knots into the sheets, and her breath is coming in gasps. Roger grasps her hips to hold them steady as his tongue flicks lightly between the lips of her vulva. Buried deep within her warm, dark asshole, the anal plug vibrates, sending pleasure rippling down her legs to her toes. “Should I ask her,” Roger wonders? “Will she say yes?”

If you recall, Roger and Alison are the fictional couple we’re using to illustrate how you can help your wife or girlfriend learn to enjoy anal sex. They have made substantial progress since they started on their journey—originally, Alison was not at all enthusiastic about trying anal sex. In fact, her attitude could have been summed up with one word: “No!” If you’re joining this discussion in the middle, you might want to go back to that inauspicious beginning and start reading there. That way you’ll understand all the intermediate steps that Roger and Alison have taken to reach this point, the point at which anal sex is finally going to become a reality for them. You’ll also have a complete picture on how you and your wife or girlfriend can reach that same point.

In the previous article in this series, we worked on helping your wife to overcome her fear of placing a relatively large object into a small hole, using an anal plug to do so. We also continued our ongoing focus on allowing her to perceive her ass as an erogenous zone, and come to associate having something inside it with sexual pleasure. You should have practiced this together several times by now, so that your wife or girlfriend is fully comfortable with it.
If you have done so, then you are ready to take the plunge together. This time, rather than the anal plug, you’re going to slide your penis deep into your wife/girlfriend’s rear entry, and if all goes well, both you and your wife will very much enjoy the experience!

One decision you’ll need to make is whether or not to use a condom. Obviously you won’t have to worry about pregnancy, but that’s not the only reason a condom is employed. The choice is, of course, yours, but I’d say that if you have concerns about transmission of any STDs, they should be magnified when considering anal sex. If you and your wife have a monogamous relationship, and you routinely don’t use a condom for traditional sex, then perhaps you might choose to forego protection. On the other hand, if you’re not necessarily so monogamous, or you have concerns about potential STDs, then you might choose to use it.

Pick a night when you are both “in the mood”. If you have a vibrator, it would be a good idea to place it somewhere close by to use. Spend plenty of time on foreplay to warm things up, then move on to using your tongue to add additional heat. Use your finger to apply a good amount of lubricant both inside and around the rim of your wife/girlfriend’s anus. When she is ready, go ahead and insert the anal plug. Give her oral sex with the plug in place until she’s highly excited. Then, pop the question.

I’d suggest saying something like, “Honey, I want you so badly right now. I want to try putting my (insert your favorite word for “penis” here) where this plug is.” From here, there are two paths the night can go down. The happier (and IMHO more likely) path is the one where your wife has, herself, been wondering about this very same thing, and agrees to try it. Let’s follow this path to its conclusion, and then come back and take a look at the second, less happy path.

On the happy path, your wife/girlfriend says “Okay,” or maybe “Okay, but go slow.” You should gently remove the plug, and if you’re going to use a condom, now’s the moment to put it on. Once the plug is out, keep the intensity high by going back down on her for few seconds. Then, it’s time to mount her. If you choose to mount her from the rear (either doggy-style or with her laying flat on her belly with her hips slightly raised) it will be easier to penetrate. However, there’s much to be said for mounting her missionary-style as well—it’s a closer experience for you as a couple, as you are face to face and can hold each other. If you decide to do the missionary thing, lift her legs up and back over her head, exposing her ass for your entry.

Though her anus should already be loosened by the plug and well-lubricated, it will nonetheless be more difficult to enter than her vagina. You’ll need to be good and erect to get into her easily, and it might help to add additional lubricant to the tip and sides of your penis if you’re having trouble. Once you’ve penetrated, slide in about half way, then wait to let her become accustomed to having you inside. After that you can go deeper, and then begin thrusting slowly.

She will be tight around you, and you may have difficulty lasting very long due to the tightness and the newness and excitement of the experience. Be gentle—it will be tight for her, too, and you definitely don’t want to make it painful! Go slow and easy, and do your best to give her pleasure as well. If you have a vibrator, this would be a good time to employ it—use it to stimulate her clitoris (another advantage about the missionary position is that it’s easier to do so).

Be sensitive to her experience—you can judge whether she’s enjoying it by her reactions. If she has liked the plug to this point, then the chances are almost 100% that she’ll enjoy having you inside her instead. If she’s feeling any discomfort, slow down and let her relax a little—hopefully it will pass and you’ll be able to continue. Last for as long as you can provided she’s enjoying herself. With any luck, she may beat you to orgasm!

When you are done, be sure to stay close and cuddle with your wife. She’s just done something very nice for you (and hopefully for herself as well!), and shared a new level of intimacy. Make sure she knows you appreciate it! As always, you want this experience to be positive for her, so that you can share it with her again.

If you followed this happy path all the way to its end, you’ve had a good first experience with anal sex together, and can now add it to your sexual repertoire for use in the future! I’d suggest allowing a couple days before staging a repeat performance to allow your wife’s rear to rest and recover a bit, but beyond that and some advice that it’s not good to go there every time (even anal sex can get monotonous eventually), you should have a green light to try again.

However, let’s now go back and take a look at the less happy path. This path begins where you ask your wife if you can try inserting your penis where the plug is, but this time, her answer is “I don’t want that,” or maybe, “I’m not ready”. Even though I believe it is less likely than a “yes” answer, I recommend that you set yourself to expect this response! That way you’ll be prepared if it happens, and will know exactly what you should do. And if you get surprised with a “yes” instead, then even better!

If your wife/girlfriend’s answer is similar to those listed in the last pargraph, here’s what you should NOT do:

  • get angry
  • yell or raise your voice
  • try to do it anyway!

Instead, be understanding and sympathetic. Your response should be something along the lines of, “Okay, but we should try it a different night. I think you might like it.” Then go on with your standard, familiar sex activities, again trying hard to provide maximum pleasure to your wife. By doing this, you’ll plant the seed of possibility in her mind and you’ll avoid putting pressure on her that might just nip that seed in the bud.

Do NOT bring the topic up with her, either directly or through innuendo, for at least a month! Allow the seed you planted time to grow. Have sex as usual, and feel free to use your tongue, finger and the Anal plug in her ass, so that it is further incorporated as an erogenous zone in her mind. After at least a month has passed, start this step over and when you get to the right spot, ask again. You may find that her answer has changed, and you can follow down the happy path this time around.

Let’s go back to Roger and see how he’s doing:

Roger lifted his head from between Alison’s legs. “Ali,” he said. “I want to try something. I want to put my cock in your ass instead of this butt plug”. He bent down and ran his tongue up and down through the moist slit between Alison’s legs again, then lifted his head once more. “Can we do that?”

Alison gasped out, “Oh God, yes!” She looked down at him, her face flushed with passion. “Do it! I want to feel you there!”

For a moment, Roger was flummoxed. He hadn’t expected such a strong answer from his normally demure wife. Quickly, though he seized his opportunity, and in just a moment, he felt the wonderful sensation of his wife’s tight, little asshole opening to swallow the head of his penis. A few seconds later he was fully immersed in her warm, velvet grasp, and she was gasping and clutching him close in the first of several orgasms.

If you’ve reached this point, you, like Roger, have now had successful and enjoyable anal sex with your wife or girlfriend, and are positioned to continue having it as desired in the future. Congratulations to both of you—you have a new source of sexual pleasure to enjoy!

For a woman’s perspective on anal sex, you can read Joy’s thoughts here.

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