The Ultimate Guide to Anal Sex for Women

6 • DOING IT FOR YOURSELF Masturbation and Anal Eroticism

The best introduction to anal eroticism starts with your own behind. In the 1970s, consciousness-raising groups spawned by the women’s movement encouraged women to explore their vaginas and do gynecological self-examination with a speculum to gain a better understanding of their bodies; the more knowledge women have about our own bodies, the more in touch we can be with our gynecological health as well as our sexual pleasure. But many of us are not familiar with how our own anuses look and feel; we are taught to think of them as private, dirty, and absolutely not a source of pleasure.

Unlike men, who only have to glance down to see one important source of their libido, women have to find a well-lit room, a comfortable position, and a mirror just to see our own vaginas and clitorises. The same is true for our anuses. Looking at your anus, touching it, stroking it, feeling how it responds to even the lightest touch can give you a world of information about anal eroticism. While you’re exploring your anal area, you will want to use the preparations outlined in chapter 2: Relax and be patient with yourself. Go slowly in the beginning and don’t try to do too much all at once. Make sure you have a big bottle of lubricant nearby in addition to latex gloves and anal toys, if you wish. Do what feels good, and stop if and when it stops feeling good. Also remember that anal stimulation may be something you want to reserve for your “sex for one” occasions, which is fine; there will be plenty of time to bring anal eroticism to sex with a partner if and when you’d like to do that.

In addition to being fun, exciting, and arousing, exploring anal eroticism during masturbation is also the best way to prepare for anal sex with a partner. If you want to have your anus penetrated by your partner, exploring it by yourself will help you figure out what you enjoy andwhat you don’t. Experiencing anal pleasure by yourself can also help to reassure you that it can be pleasurable with a partner; you’ll know what it feels like when it feels good. Your own exploration can also serve to get your anus used to stimulation and penetration. If the first finger that slips in your anus is your own, then someone else’s won’t seem so scary and may even feel better than you had imagined!

If you want to penetrate someone else’s anus, exploring your own anal area by yourself will give you insight into what’s going on down there, including the ins and outs of the anus, anal canal, and rectum: the sensitive tissue, the all-important curves of the rectum, and the various sensations of anal stimulation and penetration. Self-pleasuring your anus will give you a good sense of what your partner might feel as you give him or her pleasure. 1 believe the best way to become skilled at doing something to someone else is to practice it on yourself first.

Remember, because of the contractions the anal sphincters can make during arousal and climax, the anus can actually “suck” objects into it. There won’t be anyone else in the room to prevent a toy from going too far inside your rectum. It is crucial that anything you put in your anus besides your finger have a flared base.

When you’re ready to explore anal eroticism during masturbation, you might want to begin by taking a warm, leisurely bath or shower. The bath or shower will help you relax as well as give you an opportunity to get your anus nice and clean and ready for fun. Also make sure your hands are clean and your nails are trimmed neatly. Begin by masturbating as you usually do; start by doing what you know first, which for most of us will mean stimulating the vagina and clitoris. Bring out that favorite vibrator or dildo, turn on a hot porn video or a steamy movie—do whatever will get you aroused. Don’t jump right into exploring your anus; instead, simply masturbate and get your entire body aroused.

When you feel juiced up and ready to pay some attention to your anal area, you may want to use a mirror so you can see exactly what’s going on down there. Find a comfortable position. Lying on your back or sitting in a comfy chair or on the edge of the bed might be best at first so you can look in a mirror. If you’ve already practiced with a mirror or aren’t using the mirror, you can lie on your stomach, lie on your side, or stand up (perhaps in the shower); find a position that works for you, one that allows you to stimulate your clitoris and reach your anus.

Begin with some relaxation techniques like deep breathing or meditation; you may also want to do some Kegel exercises to get warmed up and get the blood flowing to your anus. Gently massage your buttocks, your inner thighs, and the area around your anus. Note how the opening responds to the massage around it. Put on a latex glove (if you want to) and pour some lubricant into your hand. Make sure your finger is good and slippery.

When you feel comfortable, gently touch your anus. Stroke it, rub it, let the lube glide over your skin. Just stimulating the opening can be extremely pleasurable because of all the nerve endings in the anal area. You may also want to use a vibrator to stimulate the outside of your anus; vibrations can both relax the area and get the blood pumping there. Spend time feeling your way around and exploring how your whole body responds to your anus being stroked, rubbed, played with, and teased. A good next step is to use your finger to press gently at the opening. Feel how your body responds to the pressure against your anal opening. Keep touching and pressing until you feel ready for more. You may want to continue to stimulate your clitoris to get further aroused; remember, masturbating gets the whole pelvic area stimulated and engorged.

Continue by adding more lube to your finger and inserting just the tip into your anus; stay there and let yourself get used to the feeling. Add some lubricant. Move your finger gently against the sides of the opening without going any farther inside. When you feel ready, venture a little farther. See how the sphincter muscles feel around your finger. You may want to continue to masturbate with your other hand or use a vibrator. Remember to be patient with yourself, go at your own pace, and listen to your body. If at any time you feel discomfort or pain, stop. There’s no rush. Keep nudging the finger inside until it’s as far as you want it to go.

Experiment with all the different sensations you can create with just one finger. You can try a slow probe, venturing inside inch by inch, experimenting with a variety of depths. Some people like a circular motion, creating circles just inside the anus with a finger and feeling the walls of the anus contracting around the finger. Other people enjoy the feeling of simply having something in their anus; see what it feels like to rub your clitoris while your finger stays still in your anus. You can also practice some in-and-out play, trying different speeds and rhythms as you slide your finger in and out of your anus. Savor each new movement and sensation.

As you get more experienced, you can repeat this exercise with more lube and more fingers. When you can comfortably fit about two fingers inside, you may want to graduate to a slim butt plug, dildo, or vibrator. Remember, plugs are good for that full feeling, dildos for in-and-out action, and vibrators for in-and-out and, of course, vibration. Because these toys are longer than your fingers, you can use them to probe more deeply into the rectum. Make sure to use plenty of lube and start out slowly. Pay attention to how the muscles contract around the toy; make sure to let your anus get used to the feeling each time you inch a little farther inside. You’ll notice a difference as your tool moves from the anal canal into the rectum. In the anus, you’ll experience more resistance and a tighter feeling. In the rectum, you will feel like there’s more room.

If you rush penetration, your anus is likely to get sore and you’ll have to stop all activities before you might want to. If you listen to your body and give your anus a chance to get fully aroused, it will open up and give you plenty of room for penetration by a slim dildo and, eventually, even bigger things.