The Anal Sex Position Guide (5 page)

One of the worst mistakes that people make when it comes to anal sex is that they rush the process. Remember, the ass is delicate and sensitive and needs to be handled gently. The slower you go in the beginning, the better it will be for everyone in the end. Progressing too quickly is a recipe for discomfort and pain, and a virtual guarantee that your partner will
not
want to go to the backdoor again. Be patient. Take a deep breath. Don’t let your enthusiasm overcome you! Take it very slowly, and check in with your partner along the way.

The objective is not to “stretch” the ass, but rather to learn to relax the sphincter muscles to make penetration comfortable and pleasurable. If your partner has never experienced anal penetration, then the first time you explore it, don’t expect you’re going to end up with your penis inside her. Set a much more realistic goal for that maiden voyage: try one finger in her ass, your tongue, hand, or a vibrator on her clitoris, and a rousing orgasm. Not only will this be fun, it will be a positive introduction to anal pleasure and a solid foundation to build on. You want her to have a series of pleasurable experiences—and you want her body to remember—so that each time you begin to stimulate the area, all her senses associate it with arousal, pleasure, and satisfaction.

Great anal sex is all about the warmup. You’ve got to take your time, relish each sensation, and tease her into a frenzy before serious anal penetration begins. Start with some external stimulation to get the ball rolling. Analingus (commonly called rimming) is a great way to begin the arousal process and get you both in the mood. Use your mouth and tongue to explore the folds of her puckered opening. Swipe your tongue around her anus or lick back and forth. Experiment using the wide flat part of your tongue, then try the pointy tip. If you feel comfortable, you can slip your tongue just barely inside her anus or move it in and out. While you do this, you can use your hands to play with her vulva and clitoris at the same time.

If you or your partner don’t enjoy analingus, you can use the pad of a well-lubed finger in a circular motion to massage the outer area of the anus. Or press a vibrator against the opening. Whatever you choose, the idea is to bring awareness to the area and begin to “wake up” the anal erogenous zone through gentle, focused touch.

When you slide your finger into someone’s ass, you can tell a lot about how they are feeling: our sensitive digits can assess how relaxed, nervous, or turned on someone is—and that’s valuable information when it comes to anal sex. Many people feel especially connected to their partners when they use fingers for penetration; there is nothing quite like the feeling of having a part of your body inside your partner’s body. Fingers can help warm up her butt for a toy or intercourse, or they can be the main event all by themselves. For all these reasons and more, fingers make great penetration tools.

If you are going to use your fingers for anal exploration, first make sure they are butt-friendly. Your nails should be clean, short, and well-filed; beware of sharp or rough edges because they can irritate the delicate tissue of the anal canal and rectum or even cause a scratch or small tear. If you’re unsure about how nice your manicure is, you can always wear a latex (or non-latex) glove. Gloves are not just safer-sex barriers; they work well for penetration because they transform your hand into a smooth, seamless tool. Gloves are ideal if you have long nails and don’t want to cut them just to have an anal adventure: Just put a small cotton ball in the tip of each finger of the glove to protect your nails and make sure the glove doesn’t tear. Always use plenty of lube with gloves.

To begin, lube your index finger and touch the pad of it to your partner’s anus. Wait for the opening to relax, then slip your finger inside just to the first knuckle and stay there. Let the ass get used to the feeling of your finger. Don’t make any sudden movements or try to go farther. When the sphincter muscles begin to relax around your finger, you can venture farther inside. Again, when you have your finger all the way inside, stay put. Check in with your partner. When you feel her ass continue to relax and she tells you she’s ready for more, begin experimenting with different sensations. Take some slow strokes where you move in and out of the anus. Try speeding up and see if there is a particular pace that she likes best. Experiment with long strokes, then short, quick ones. Twist your finger as it moves inside her. Aim it toward the front of her body and press down slightly for indirect G-spot stimulation.

When she’s ready for more, withdraw the index finger, take your middle finger and cross it on top or below it, then lube both fingers. Slide back inside gently and begin with some slow strokes. As you discover what kinds of stimulation she likes best, establish a rhythm with your fingers.

From there, let her set the pace as you work your way up to more fingers or a sex toy (see next chapter for more information on toys). You shouldn’t move on to the next step until everything feels great, and you should move on to intercourse only when she has taken the number of fingers or toy that is similar in size to your penis, or just shy of it. How long it takes to get used to this new sensation, to be comfortable with anal play, and to work up to a penis in her ass will totally depend on her. Don’t be so focused on how long it will take; just enjoy all the fun you’ll have getting there.

When you’re ready to penetrate her with your penis, make sure you use plenty of lube. Keep in mind that you’ll need a solid erection to make things go smoothly, so make sure your penis is good and stiff. If it’s not, it’s incredibly difficult to penetrate her ass because the sphincter muscles make the anus incredibly tight.

To get inside, you can proceed in a few different ways:

• Press the tip of your penis against the opening and stay there. Have her move back or down onto your penis so she controls the initial penetration.
  
• She can spread her butt cheeks to help give you a clearer view and an easier time.
  
• She can also reach around and guide your penis with her hand.
  
• Hold your penis with your hand and gently push against her anus. Do not put too much body weight behind you; this can cause you to go in too far too quickly.
  

Just as you did with your fingers, once the head of your penis has slipped past the sphincter muscles, stay still. If you need some thrusting in order to maintain your erection (which some men do), move slowly, gently, and don’t penetrate her fully. You need to give her body a chance to get used to the feeling of being penetrated by your penis. As you feel her ass relax around your penis, you can begin some slow thrusting. Take it easy at first: not too fast, not too deep. If she continues to feel tight or tense once you’re in, you may need to come back out and warm up some more with fingers or toys.

The initial penetration is usually the trickiest part. Once you’re past those tight sphincter muscles, as long as she is aroused, you’ll find the rectum has expanded to accommodate you. Some people like anal intercourse to be more sensual and intimate, with shallow thrusting accompanied by kissing and lots of eye contact; in the upcoming chapters, you’ll learn about positions that put a focus on these elements. You’ll also read about which positions work best for powerful thrusting or deep penetration, if you both like that. The ass can take a good hard pounding—if that’s what you both what—but only after proper warmup and plenty of lube.

While you are doing all this careful warmup, don’t forget what’s going on nearby; in other words, don’t neglect her vulva and especially her clitoris! The more aroused a woman is, the easier and better anal penetration will be, so don’t forget all the things you already know about the rest of her body as you explore anal eroticism. Suck on her nipples or gently take them between your fingers, kiss the back of her neck, lick her ears, and work all her other magical spots. The more fired up she is, the more open she will be—both physically and emotionally—to anal pleasure. Pay lots of attention to the rest of the area between her legs: Massage her inner and outer labia, slide a finger inside her vagina, stimulate her G-spot, rub her clitoris, and so on as you penetrate her. For some women, genital stimulation during anal penetration fuels their arousal, intensifies all the sensations, and makes their orgasms bigger and better. For others, clitoral stimulation is absolutely necessary in the process; without it, anal penetration doesn’t feel good at all, and an orgasm isn’t even possible. Make sure to ask your partner if she has a preference and what she likes.

And speaking of speaking, keep doing it! Make sure to check in with your partner about how everything feels and if she wants something different. Tune in to her body language and pay attention to how her body responds to certain things. Let her guide you as to the pace, the sensations, and what works best for her. If you can’t reach her clitoris to stimulate it, encourage her to touch herself or use a vibrator. Tell her how much fun you’re having and what you like about anal intercourse; just hearing this can be a real turn-on for her.

Relaxation is a key ingredient to satisfying anal penetration, but different people relax in different ways. Before sex, you may want to take a warm bath, ask your partner for a massage, light candles, or burn incense. If you are multiorgasmic, you may want to have an orgasm—by yourself or with your partner—before beginning anal exploration of any kind; for some women, this can really take the “edge” off and turn them on at the same time. Try some deep-breathing exercises where you take a deep breath through your mouth and let it out through your nose. Feel the breath move through your entire body as you do it. You and your partner can try to synchronize your breathing; this can help relax you both in addition to keeping you focused on and connected to each other. Ladies, remember to keep up the deep breathing as he penetrates you.