The Ultimate Guide to Anal Sex for Women

Insertive Anal Penetration

As the insertive partner in anal sex, your job is to go slowly, be gentle, communicate, progress at a reasonable pace, and let your partner take control of the ship.

Review the basic preparations, especially the relaxation exercises. Start out with some fun, stress-free foreplay. Getting someone aroused in an overall way will make the transition to anal play easier and smoother. Kiss her on the favorite spot of hers. Stroke that place you know will drive him wild. When your partner is ready to progress to anal stimulation, make the transition slowly. Start out by massaging the buttocks and inner thighs. Work your way around the anal area with your fingers, your mouth, or a vibrator. The more you stimulate the entire area, the more the blood rushes there. You can combine anal stimulation with stimulation of the clitoris, vagina, or penis to get the entire genital region engorged and excited.

When your partner is ready for penetration, begin with one well-lubricated finger. Insert only the tip, up to the first knuckle, and stay there. Since the first instinct of the sphincter muscles will be to tighten, let the anus get used to having something inside it and let the sphincter muscles relax. A good way to further relax the receptive partner’s anus is to slowly and gently push up and down against the opening.

Often, the sphincter muscles of the anal canal will respond to penetration by contracting around the object, then releasing. Many sex educators call this motion “winking.” Never poke the anus; instead, stroke the opening with the pad of your finger. If you gently caress the anus, it will wink at you. The anus will open, and you can slowly slide a well-lubricated finger inside.[44]

There are so many nerve endings in the anal area that every sensation is magnified. Keep in mind that a light touch, a slim pinkie, and a slight wiggle all go a long way toward arousing your partner. The simplest caress can be extremely pleasurable. If she wants more, deeper, faster, or harder, she’ll tell you. In the beginning, it’s best to err on the side of caution and gentleness.

It’s important that you focus on your partner as you’re giving him or her anal pleasure. The receiver should feel comfortable to talk as much as he or she wants during the experience. Ask her how she feels; ask him what he wants. You should also listen to your partner’s body. Feel how the sphincter muscles contract around your finger and respond to your touch. Observe the level of tightness and openness of the anus in addition to the rest of the body’s response to anal stimulation. What verbal and nonverbal cues is she giving you? How is her breathing pattern? What kinds of sounds is she making? Tell your partner what you’re doing, especially each time you are about to move on to something new. Also tell her or him what you’re feeling, what’s turning you on; it will enhance the communication and pleasure between you. Ask her to tell you what she likes does she want more teasing? Some rimming? More pressure and fullness? Less in-and-out motion? Ask her.

The person receiving the anal pleasure should be the one in control. Encourage him or her to breathe deeply; stay where you are on the inhale and nudge farther in on the exhale. Or, instead of you guiding the insertion, the receptive partner can take you inside at her or his pace. As a receiver practices controlling the sphincter muscles, she or he can actually suck you inside.

Make sure your partner knows that if she wants you to stop, she need only say so and you will stop. Never coax or pressure a partner into having anal sex. If your partner isn’t interested in exploring anal sexuality or isn’t in the mood on a particular occasion, respect his or her wishes.

Anal sex can be very highly charged even for the most willing, aroused, or experienced receivers. Having your anus penetrated can be intense, emotional, even a little scary. Keep all these factors in mind, and remember that your partner has put a tremendous amount of trust in you. Respect that trust as well as your partner’s body. Realize that she or he may be feeling particularly vulnerable or maybe a little anxious.

Reassure your partner that she or he is in charge.

Receptive Anal Penetration

Relax, relax, relax. Take a deep breath. And another.

Relaxation is so important to having pleasurable anal sex; yet I think that with the hectic pace of our lives, it is one of the hardest states to achieve. Because the anus can be a place where we store much of our stress and tension, we need to give our bodies plenty of time to release that tension before venturing into anal pleasure. I find that doing about fifteen minutes of deep breathing helps my body to unwind, and the breathing actually gets me in touch with how my entire body is feeling. A warm bath, candles, and a sensuous massage are also great relaxers. We must also relax our minds, and some people like to meditate or even do some positive visualization to calm and prepare themselves for anal penetration. Ultimately, our bodies and minds are intrinsically linked, and relaxation is a reflexive process.

You need to figure out what your anal erotic desires are and take responsibility for communicating them to your partner.

Although it may seem paradoxical, you are the one in the driver’s seat. You set the pace and control the action. You need to be well aware of your body, and specifically of your anal sphincters, because you have the ability to relax them. Talk to your partner before, during, and after about what turns you on, the sensations you experience, what you’d like more of, and how everything feels.

The more information you can give your partner, the better equipped he or she will be to please you. As discussed in chapter 3, it is equally important that your share your fantasies and your fears about anal sex. The more in touch you are with your needs, your desires, and your own body, the better the experience will be for everyone.

Once you are relaxed and ready for penetration, put some lube in your anus and find a position that’s comfortable for you.

Some people like to be on their back with their legs in the air or on the insertive partner’s shoulders; this way, you can face each other, have easier verbal and nonverbal communication, and incorporate other stimulation with anal penetration. Some women like to sit on top of their partners (also facing each other) so they can control the pace and depth of penetration. Many people like to be on all fours, belly down with their butt in the air. This “doggie-style” position can allow better depth and requires the least bending of the rectum. Experiment with various positions until you find what’s most comfortable.

Because you are in control of the action, you must be prepared to tell your partner to slow down, change activities, or stop altogether. Listen to your body; if you feel any discomfort or pain, you absolutely need to stop. Don’t fool yourself that the pain will subside or pressure yourself to continue even when it no longer feels good. Anal sex does not have to be uncomfortable or painful at all.

For Both Partners

If your partner is interested in being penetrated with something bigger than a finger—several fingers, a butt plug, a vibrator, a dildo, or a penis—it’s a good idea to set some realistic goals. Set a series of goals that will give both of you room to relax, practice, and feel free from pressure to do too much at once. As penetration progresses, each time you either add a finger or increase the size of the toy, be sure to add more lube and let the anal canal and rectum get used to the new sensation. Just as you let your partner take the lead in the pace, let her or him take the lead in the depth of penetration. Let her ease her anus down onto your fingers or that favorite plug, taking as much as she wants at her pace. You should always begin small and work your way up to big, and remember that you don’t have to reach the ultimate goal in one single night.

Once you’ve worked your way up from fingers to toys or a penis, remember your anatomy lesson and those two curves you’re going to run into in the rectum. Each person’s rectum is unique, so don’t assume that a technique that worked on one person will make your current partner scream in ecstasy. Going slowly will help you navigate the curves of the rectum and begin to discover the individuality of your partner’s anal canal and rectum without causing discomfort. There will be plenty of time later for a hard-and-fast frenzy, if that’s what you both want. But, in general, you shouldn’t make any swift or jerky movements. Likewise, whenever you withdraw anything from the anus—if she asks you to stop, after she’s had an orgasm, or when you’re going to take a break—always pull out slowly. Even if your partner says “Get it out of me now!” don’t withdraw too quickly or you can hurt or tear the tender rectal tissue.

Positions for Anal Penetration

All the positions people employ for vaginal penetration can be used for anal penetration. Since everyone has individual needs, tastes, and desires, it is important to experiment with all kinds of positions to discover what works best for you and your partner.

Among hip, liberated women, the missionary position has gotten a bad rap in recent years because it works well for men but usually affords women no clitoral stimulation. There are plenty of ways to slightly amend this “traditional” position to make it work for you. This position finds the receptive partner on her or his back and the insertive partner on top. Because both partners face each other, it is easier to communicate, especially nonverbally, plus you can attend to other parts of your partner’s body suck on her nipples, kiss his neck, nibble her lips. Many people in the receptive position like missionary-style anal penetration because lying on their back either feels more comfortable or allows them a sense of surrendering to their partner.

The receptive partner may find that a pillow under her butt makes for easier penetration, and she can bend her knees or either bring her legs to her chest or rest them on her partner’s shoulders. Although the latter position may create a better angle for entry, it is one that even the most flexible among us often find hard to sustain. In this position, your partner usually cannot provide clitoral stimulation, but you can provide your own with your hand or a vibrator.

In the receptive-partner-on-top position, the receptive partner can control the angle and depth of penetration. Straddling the insertive partner, she or he can sit straight up, or lean forward or backward according to her or his own desires. Again, facing each other means you can talk and communicate as well as stroke, rub, pinch, and stimulate other parts of each other’s bodies; this position is also great for clitoral stimulation. Receptive partners can really take the lead in this position and be in charge of the depth of insertion, the amount of movement, and the rhythm of whatever is doing the penetrating—finger(s), butt plug, dildo, or penis.

Insertive partners who are inexperienced, nervous about how to penetrate their partners anally, or fearful of hurting their partners may find this position most relaxing because the receiver can do much of the decision making and work. The partners on the bottom often report liking this position best because they get a great view of their partner and can watch them as they receive pleasure.

The doggie-style position is probably the first one many of us think of when we think about anal sex. Doggie-style is also a popular image in porn magazines and videos. This position, with the receptive partner on her hands and knees and the insertive partner behind her, is best for deep penetration.

Because the rectum is in the most straight (not bent) position, the insertive partner can get good depth that is also comfortable to the receiver. If the receptive partner is a woman, this position also makes it easy to reach around and rub her clitoris.

Doing it doggie-style also means both partners can have lots of pelvic movement. The insertive partner can do a lot of deep, hard, or fast thrusting; the receptive partner can move back on or ride fingers, a dildo, or penis from this angle. Many people like to have their partner penetrate them from behind for a fast and frenzied kind of fuck. As when the receptive partner is on top, she can also be in control of the action if the insertive partner does less of the movement and lets the receiver come to her.

In a variation on this position, the receptive partner is on her stomach with her knees either bent or straight. Although this one may seem awkward on first try, it just takes a little practice. This, too, is a good position for medium or deep penetration because the rectum is in an optimum position for smooth entry (as long as you don’t forget that important curve!).

In the spooning position, both partners are on their sides either facing each other or facing the same direction. This position is comfortable, flexible, and easily maneuver-able, and it gives both partners good control over the angle and depth of penetration; it’s an ideal position for partners who are of very different heights or sizes. Some people find that lying side by side gives them greater access to their partner’s vagina, clitoris, penis, balls, and other parts of each other’s bodies for exploration and stimulation. You don’t get the depth of penetration this way that you get with other positions; however, spooning is good for a long, slow anal fucking session, where no one’s in a rush to get somewhere. But don’t get me wrong you can still have ecstatic orgasms this way.

I have gone over the major positions, but I have by no means covered all the possible ones. There are plenty more for you to explore. Some people like to reverse the receptive-partner-on-top position and face the same direction rather than each other. Couples who are similar in size may find they can have anal sex standing up or with one person bent over a bed or table.

Think of each new position as an opportunity to explore different depths, speeds, rhythms, and dynamics; there’s lots of erotic territory to find simply by changing your point of view.