Do you want to have anal sex with your wife or girlfriend, but are uncertain about her reaction? Many women are curious about anal sex, but are scared about comfort and safety issues. Some women who are unwilling to try anal sex with their current partner may have had a bad experience with an impatient or ignorant lover in the past. That's why I don't recommend asking a woman for anal sex without some careful preparation. Instead of asking her to try anal sex, it's better to make her want anal sex.
Anal sex can be very pleasurable for women because the rectum shares a wall with the vagina, and the sexual nerves are actually closer on that side, which makes the sensation unique, stronger and quite possibly orgasmic. My post Anal Sex from a Female Perspective describes what anal sex feels like for a woman. I am a firm believer that once a woman experiences the sensual pleasure that anal play can bring, she’ll allow you to explore the possibilities a little further, and, given sufficient time and patience, will eventually allow you to take it to the ultimate step of full anal penetration.
The key to the approach I recommend is to "train" her to associate anal sensations with sexual pleasure. The next time you’re going down on her (twice as many women orgasm from oral sex as from intercourse), move your hands around and cup her butt cheeks, squeeze and massage them, and then let your finger(s) wander into her crack a little bit. Get her to pull her legs back towards her head (so you can have better access to her vagina), and lightly bite/nibble around her butt in places you can reach, and run your tongue as close to her crack as you can comfortably (for you and her).
You must keep your eyes and ears open during this to gauge her response. If she moans a little louder, squirms a little bit more, or provides some other positive feedback, then go on to the next step. If she jerks away or gives you a negative reaction, don’t press the issue. Just try again the next time and hope for a more positive reaction.
If you’ve gotten your positive feedback, and are confident about proceeding, lube up a finger and slide it down into the crack of her butt and over her anus (this assumes she’s pulling her legs back for easy access). Don’t let it linger there. Just run it right over the anus slowly and see how she responds. Again, judge her reaction to decide whether or not you should proceed.
If you get another favorable reaction, try it again and this time, let your finger linger there, and perhaps perform some light massage on the anus, especially as you are performing cunnilingus on her. Her nerve endings will already be lit up down there, and everything in that area is interconnected anyway. As long as she doesn’t think you’re about to invade, you should get a noticeable increase in positive feedback.
Assuming you are successful, put a little lube on your finger and slowly, with circular motions, stroke the outside of her opening. Then gradually insert your finger inside the anus. Do not move it at first. Just allow her to enjoy the sensation of fullness in the anus.
Slowly insert the finger up to the end and make circular motions with the whole wrist, without moving the finger in and out. These motions will be felt in the vagina. While you're doing this, do something else, such kiss her breasts or stimulate her clitoris. Try to make her experience pleasurable. A woman who enjoys anal foreplay will eventually begin to give anal penetration some serious thought.
Getting her highly aroused goes a long way toward reducing inhibitions. If you take advantage of her uninhibited state, you can probably progress to the point where she’ll allow you to penetrate her anus with a finger, then two, and maybe even proceed to the point of using a small sex toy. The key here is to make sure that you don’t rush things. If you take your time, and let her get comfortable with the idea of anal play, you should eventually reach the point where she’ll seriously consider allowing you to try full anal penetration with your penis.
When she does, be sure to follow the 10 Steps to Great First-Time Anal Sex unless you want the first time to be the last time. A bad experience can turn her off to anal sex altogether - at least with you. On the other hand, anal sex can be one of the most erotic and satisfying sexual practices a woman can enjoy. It's a different, tighter sensation than vaginal sex, and, if the clitoris and/or vagina are stimulated while you're inside her, it can take her to another sexual realm.
My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.