The Ultimate Guide to Anal Sex for Women (16 page)

Make sure your partner knows that if she wants you to stop, she need only say so and you will stop. Anal sex can be very highly charged even for the most willing, aroused, or experienced receivers. Having your ass 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 may be a little anxious. Reassure your partner that she or he is in charge.

 

DON’T GO FROM ASS TO PUSSY

It can’t be said too often: putting something in the ass and then transferring it directly to the vagina is a perfect route to a vaginal infection. Bacteria that lives naturally in the rectum (possibly along with some fecal matter)
will be transferred to the pussy, and since the pussy doesn’t naturally flush itself out, bacteria can set up shop, multiply, and live there until you treat it. Some women get yeast infections or urinary tract infections, others get bacterial infections like gardinerella.

Once anything—a finger, a toy, a penis—has been in the ass, it must be thoroughly washed or covered with a new condom or glove before it goes anywhere near the vagina. In addition, you should be aware that lube that goes into your ass and drips out of it can make its way to your pussy, which could also cause an infection. To prevent what I call “the drip-down effect,” have a box of baby wipes handy to make a clean swipe of the area (always swipe front to back).

 

GETTING STARTED

When you’re ready to introduce anal stimulation, start out by massaging the asscheeks and inner thighs. Work your way around the anal area with your fingers, your mouth, or a vibrator. Remember that 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.

In the beginning, I like to start penetration with fingers rather than small toys since fingers are sensitive and connected to our brains whereas toys aren’t. Putting your finger in someone’s ass can give you a good idea of how that ass feels and responds.

When your partner is ready, use one well-lubed finger. Instead of going straight inside, touch the pad of your finger to the opening; this trick usually relaxes the anus, allowing you to slip your finger in comfortably . Go up to the first knuckle and just stay there. Since the first instinct of the sphincter muscles will be to tighten, let the ass get used to having something inside it and let the sphincter muscles relax. A good way to further relax the receptive partner’s ass is to
slowly
and
gently
push up and down against the opening. Gently apply pressure downward toward the bottom of the anal opening; do the same thing upward, to the left, and to the right. I call this the North-South-East-West technique, and it’s a simple, gentle way to let the ass know you’re there. When your partner is ready for more, slip farther inside slowly and gently. Encourage him or her to breathe deeply; stay where you are on the inhale and nudge farther in on the exhale. Don’t go too far too fast.

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. The simplest caress can be extremely pleasurable. In the beginning, it’s best to err on the side of caution and gentleness. If your partner wants more, deeper, faster, or harder, he or she will tell you.

WORK YOUR WAY UP

Once you have one finger inside your partner’s ass comfortably, you can begin to experiment with different sensations. Stay still and stimulate his or her genitals, and see how the body responds. Move your finger in and out and explore different speeds. You can also try to make a twisting motion as you go in and out. Make sure that the receptive partner is the one in control of the action—and she should let you know if she wants more or less, slower or faster, deeper or not-so-deep. To get one finger in and bring your partner to orgasm is a good goal for an evening. I know it sounds like a small step, but the idea is to have a series of hot, pleasurable anal sessions to build on.

If you’re both feeling ambitious and want more, slowly slide your finger out and add more lube. To go from one finger to two, cross your index finger over your middle finger , make sure both are well-lubed, and touch the pads of the fingers to the opening just like you did with one finger. Slide both fingers inside slowly, be still, and let the ass adjust. 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 ass—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.

As you did with one finger, experiment with different sensations with two fingers. By now your partner should be pretty turned on, so angle your fingers toward the front of the body to hit the G-spot indirectly or the prostate directly. The G-spot and prostate like firm, deliberate stimulation. Use a “come here” motion (almost like a pulling motion) with your fingers to press on the sensitive spot. Because you’re putting pressure on the area around the urethra, your partner may feel the urge to pee during G-spot or prostate stimulation. When coupled with arousal, the pee feeling may be pleasurable for some, or annoying for others. Get feedback from your partner about how it feels. In your very first (or first few) anal play experiences, using two fingers is a good goal; two fingers plus other stimulation leading to a rockin’ orgasm also works. There will be plenty of time later on for more.

From two fingers, you can progress to three (depending on the size of your fingers) or a slim butt plug or dildo. Remember that you can put a butt plug in, then move on to another activity—vaginal penetration, cunnilingus, mutual masturbation—while the plug works its magic to relax and arouse the ass. When the plug comes out, the ass will be ready for something bigger or longer, or it may be spent. That depends on the ass.

I’ve outlined a slow, methodical process that may seem like it’s a lot of time and effort, which begs the question: Does the receiver always have to warm up for anal penetration? The answer is yes. No matter how experienced you are, you always must begin with fingers or small toys before moving on to a cock or dildo. However, the amount of time it takes your ass to open up and relax will gradually decrease the more you practice.

Afterward, have a little debriefing session to review how it went and get feedback you can use for next time. Remind each other about goals you set.
Did I go too fast, did I use enough lube? Was there enough in-and-out movement, or do you want more of just that pressure feeling? What did you like about my fingers versus the butt plug? Is there something I can do differently next time? Do you want more genital stimulation while I’m playing with your butt?
Compliments always feel good—criticism does not. Be generous when you communicate with your partner. If you want to tell her or him about something you didn’t like, why not start that conversation with something you did like? But make sure you do talk about what didn’t work as well as what did work. There are many elements you need to have a pleasurable, pain-free anal sex experience: lots of foreplay and warm-up, plenty of lubrication, and communication and trust between you and your partner. Communication at all phases of an anal sex experience will ultimately help both partners to articulate their needs, and, ideally, help everyone get what he or she wants out of anal sex.

When you’re ready to move on to a cock, a strap-on dildo, or a bigger toy, the same rules discussed in the previous section apply. In this section, all the tips and techniques can apply to penetration with a penis or a dildo, so when I use the word
cock
I mean any cock, whether rubber or flesh.

After your partner is warmed up and ready for your cock, your erection must be solid to make anal penetration work. While not a problem for cocks of the silicone variety, if you have a flesh cock, make sure it’s stiff. Sometimes, a man can have a semihard penis and manage to “stuff” it into a woman’s pussy, but that trick won’t work on her ass because the anus is such a tight opening. When you’re ready , lubricate your cock and relube her ass. Place your cock at her anal opening and hold it with your hand to help you guide it. Now, you have a few options:

Have her move her body toward your cock (forward or backward depending on your positions), while you guide it inside.

Rub your cock against her opening. This external stimulation should relax the anus. As the sphincter muscles contract, the opening appears to “wink” (open, then closed) at you. As it winks open, take the opportunity to slide in.

Press your cock against her opening and gently push against it (she may want to either relax or bear down in order to let you inside).

Penetrate her ass with your finger, withdraw it, and while her anus is open, gently insert your cock. When you first enter her, just put the head of your cock inside, stop, and stay where you are. Let her sphincter muscles and anus get used to the feeling. Keep your movements slow, gentle, and subtle at first. When she’s ready, you can venture farther inside. Sometimes, she will actually suck you inside—when we are aroused, our rectums start to contract and we can often pull a cock right in. If she doesn’t suck you in, slide into her very slowly or let her come back or down onto the cock so she can control the entry. Now you can start some slow thrusting. Remember when possible to angle toward the front of the body to aim for the G-spot or prostate. She should tell you if she wants you to go deeper or faster or both. Then, it’s simply a matter of exploring what feels good for both of you.

 

STRAP-ON SEX TIPS

Review the tips for selecting the right dildo harness in chapter 8, and make sure your harness fits snugly. As a woman doing the penetration, you should experiment with different positions (see pages 109-118 for a detailed discussion of positions). I know that the first few times I fucked someone in the ass with a strap-on, I had the person in traditional doggie-style position for several reasons. Doggie-style gives you a clear view of the butthole, so you can see exactly what you’re doing , and the position allows for a good angle of penetration toward the G-spot or prostate. It’s also an easy position in which to get your balance, establish a rhythm, and get some good thrusting going. So, you may want to start out that way, but you can also try any of the other positions in this chapter.

Learning how to skillfully wield a strap-on takes practice and patience. If you feel like the dildo is moving around too much or it doesn’t feel secure, then your harness isn’t tight enough and you should adjust it. In the beginning, you may want to guide the dildo with your hand, which will give you more control of exactly where it’s going. When your partner is ready for penetration, be gentle and go slowly. Press the tip of the
well-lubricated dildo against the opening, and have your partner come back on it. This may help him or her feel less vulnerable and more in control of the pace. Once you are inside, and the receiver is ready for some movement, begin slowly. You want to establish a thrusting motion with your hips, one that feels good to your partner and won’t tire you out too quickly.

As a woman, you can enjoy penetrating a man or another woman on many different levels. The trust and intimacy between you can feel especially heightened and very arousing. The naughty, taboo aspects of both anal sex and a woman with a dick can really get your motor going. The power she feels as the penetrating partner can also add to your fantasy and pleasure. Plus, strap-on anal sex has the potential to be physically stimulating for you. (Again, see discussion of strap-ons in chapter 8.)

A word to novices: like just about everything else, it takes practice. So, all you guys out there who are thrilled at the idea of a girl with a cock doing you: have some patience while she practices her technique, remember the first time you used that tool of yours, and give her a break while she figures hers out. And all you women fucking with dildos: make sure you talk to your partner, ask what she or he likes, and try different positions (like those discussed later in this chapter) to see what works best for both of you.