The Whole Lesbian Sex Book (32 page)

•
Relax!
Both the insertive and receptive partner need to be relaxed for successful anal penetration. Bathe together. Kiss and touch. Trade massages. Talk to each other. Share your anal sex fantasies. Feed your desire for anal play with each other.

I had the pleasure of introducing my girlfriend to her first anal experience. I tried to do it in the way that I would like to have had it done. I spooned her from the back, kissing her neck and rubbing whatever my hands could reach. After whispering in her ear what I was about to do to her, I began massaging her butt, working my way to her anus. I put plenty of lube on one finger of a gloved hand. I played with the outside for several minutes, all the while kissing her neck and talking to her. I asked her how it felt and whether I should continue. Finally, I inserted the tip of the finger. She was relaxed, not tense, no sharp intake of breath. I increased the penetration until I got about half of my finger in. We decided that that was enough. Since that time, almost two years ago, she has become more adventuresome, taking in whole fingers or a cute pink plug.

Illustration 12. Anal Finger-Fucking

Finger-Fucking

Your fingers are perfect tools for anal play—they’re communicative, sensitive, and agile. As with vaginal penetration, you can use your fingers as a prelude to penetration with a dildo or hand, or as the main event.

Begin with your partner lying on her belly, with her legs open and her hips propped up on a pillow, or on her back with legs spread and a pillow under her butt. Slip on a latex glove and put some lube on your finger. Spread your partner’s asscheeks. With the palm of your hand facing up, run your lubed finger over the opening. Caress the anus with the pad of your finger; don’t poke into the anus. Circle the opening slowly and then more quickly; and then run your finger across the opening. Watch her responses. Ask her what each stroke feels like. Build up a rhythm of touches and responses.

As the receptive partner, you are in charge. You can tell your partner exactly which touches you like and which you don’t. You can ask her to slow down, to touch you with more or less pressure, or to add more lube to her finger. You may feel shy talking about your butt while a finger is stroking you. Or you may find it difficult to put words to such subtle physical sensations. Here’s an opportunity to build up a vocabulary for anal sex. Soon you’ll be telling your partner exactly how to stimulate your butt!

The insertive partner can put that information to good use. When the receptive partner indicates that a particular stroke is unpleasant—not enough lube, too hard, too scratchy—the insertive partner can watch for corresponding physical responses. Can you notice tension in the opening of your partner’s anus? Has her anus closed? Are the muscles in her ass and thighs contracting? Do you notice a change in her breathing?

Similarly, when your partner is cooing with pleasure, notice how that translates into physical response. Can you notice her muscles relaxing? Has her anus opened? Is it contracting or pulsing with engorgement? Has the color of her anus deepened as blood fills the tissues? How’s her breathing? What sounds is she making? Can you bring her to moans by gently caressing the anal opening with the pad of your finger?

You can ask her to instruct you in exactly how to enter her. She may say, “Just the tip of your finger, please” or “Slide your finger in very slowly.”

Draw your fingertip along the crack of her ass until the pad of your finger lies across her anal opening. Slip the pad of your finger into her. Enter her until just the tip of your finger is inside. Stay still until she adjusts to the pressure and fullness. As her internal sphincter muscle relaxes, her anus will seem roomier. Wait for her to tell you to insert more of your finger or to move inside her. She may like a subtle pulsing or fluttering of your fingertip; or she may prefer a subtle in-and-out motion.

When she’s ready, push your finger in a little further—perhaps to the second knuckle. Again, stop and give her a chance to adjust to the sensations. Then push your finger all the way in. As necessary, pull your finger out and add more lube. Reenter slowly.

What if it hurts? If your partner feels pain,
stop.
Anal sex is not supposed to be painful. Pull out, lube up your finger, and start over. Caress the outside of the anus. Ask her to tell you when she’d like you to enter her again. Go slowly. But don’t fill her as deeply—stop before you reach the point at which she felt pain. At each step of the way, let the receptive partner take the lead. As with vaginal penetration, give her just a little less than she seems to want. Let her desire grow to engulf your finger.

Once your finger is inside, ask her what kind of movement she likes. Experiment. You can circle the walls of her anus or rectum, or you can press against the front wall of her anus, providing indirect stimulation of her vagina, clitoris, and G-spot. You can gently thrust in and out. Remember that as you add more fingers, more fullness, more pressure, or try new strokes, you may need more lube.

Anal finger-fucking is a slow build-up. She may want two or three fingers as her arousal increases. Or she may be satisfied with one. The first time you play anally, you may get no more than part of one finger inside her—that’s fine. The goal is quality, not quantity.

Some women reach orgasm easily with anal penetration. The mounting pleasure in those ultrasensitive nerve endings radiates into an intense orgasm. If you prefer indirect clitoral stimulation, you may enjoy two fingers pressing rhythmically against the front wall of the rectum. That may be enough stimulation for your clitoris and G-spot. Or, you may like direct clitoral stimulation from fingers, a tongue, or a vibrator. You may like to be filled both vaginally and anally. Once you’re fully aroused, you may like a hard thrusting motion—just remember to add plenty of lube.

Anal Fisting

Everything said about vaginal fisting applies tenfold to anal fisting, since the tissue of the rectum is less pliable and more easily torn than that of the vagina. Anal fisting requires patience, trust, and desire—and prodigious quantities of lube. Why would anyone want to put a whole hand into a partner’s rectum—or feel her own anus and rectum stretched to receive a partner’s hand? Like vaginal fisting, anal fisting is very intimate and intensely pleasurable.

Your anal fisting journey may begin one day when you feel sexually insatiable. Or, after a session of anal play, your partner may turn to you and say, “I felt so open, I swear I could’ve taken your whole hand.”

Isn’t anal fisting dangerous? Won’t fisting stretch you out? No, fisting will
strengthen
your sphincters, not harm them. As one fisting devotee put it, “Training a muscle to do new and sometimes extraordinary things generally doesn’t interfere with its function.”
⁴
Tales of fisting enthusiasts wearing diapers are pure urban myth.

Anal fisting is a great activity for women who enjoy a long, slow session of anal play. You can’t rush anal fisting. It also helps not to be goal oriented. Never force the body to accommodate more than feels pleasurable at the time. If you don’t get a whole fist inside on the first try, you may on the next. Even if you never take an entire hand, you can have a lot of fun in the process of trying!

As the receptive partner, you have to
want
your partner’s hand inside you for your anus and rectum to open enough to receive it. You have to trust your partner not to hurt you—to know what she’s doing—and to treat your openness and vulnerability with respect and caring.

Fisting her anally is a huge rush. I am filled with aggression, yet am tender in my attempts.

As the insertive partner, you have to slow your desire down to the pace of your partner’s responses. You have to want to feel your partner from the inside—badly enough to make an art of a practice few understand. You have to trust your partner to communicate at every step of the way.

As with all anal play, make sure your partner is aroused before you penetrate her. Begin with one or two fingers. Slowly increase the number of fingers until you have four fingers inserted up to the widest part of the hand. Add more lube frequently. As in vaginal fisting, when you meet resistance, pull back. Add lube. Resume, slowly. Your partner may like you to slide straight in or rotate your hand to twist your way in.

Illustration 13. Anal Fisting

When you’re inside, up to your wrist, be still until your partner adjusts to the intense sensations of fullness. She may want you to go no further, or she may ask for even deeper penetration. She may want you to gently rotate your hand, apply pressure on the front wall of the rectum, or thrust in and out—but by millimeters!

She may be too overwhelmed to even
think
of an orgasm—or she may feel an intense need to come and then have your hand out of her. You can stimulate her clitoris with your fingers, tongue, or a vibrator to bring her to orgasm.
Even if she demands that you remove your hand immediately, pull your hand gently and slowly out.

Fisting is an overwhelmingly intense and vulnerable activity. Make sure you take time to care for each other afterward.

Strap-On Dildos

There’s just something about being fucked in the ass with a dildo that really gets me hot. I like the way it make me feel vulnerable and open and used. Not politically correct lesbian stuff, I guess, but it’s one of the best ways to make me orgasm.

Having a big, tough dyke pound her enormous cock into your butt is a great fantasy—but in reality, you’d do best to start with fingers, working up to a small butt plug, then perhaps a slender dildo, to a wider plug, and finally a sizable dildo.

You might want to purchase a strap-on dildo just for anal play—not only is that hygienic (see “Anal Penetration—Safely,” below), but you may find that though you like a thick, hefty dildo for vaginal play, you may be more comfortable with a long, slender dildo for anal play.

Receptive partner on top is a good position for anal sex with a strap-on dildo. The receptive partner can control the depth and speed of the thrusts. Rear entry can work well, too, if the insertive partner remains still as the receptive partner pushes back onto the dildo. The receptive partner stays in control, because the insertive partner doesn’t have nerve endings in the tip of her dildo and the rectal tissue is easily torn. Remember that rectal tissue is much more delicate than vaginal tissue.

Tristan Taormino’s

“Beyond Our Bodies: Emotional and Psychological Aspects of Anal Eroticism”

Our emotional, psychological, and spiritual well-being plays a major role in our erotic experiences, and our experiences of anal sexuality are no exception.

People have a lot of fears and negative feelings about anal eroticism. Some of them stem from our society’s myths and taboos about anal sex. Myths about anal sex being unnatural, perverted, dirty, painful, and dangerous have become very real fears in people’s minds. It is important to realize that we are all made aware of the anal taboo and myths starting in childhood and therefore we are all affected in some way by them.

As the Receptive Partner, What Are Your Fears?

• My lover will think I’m weird for wanting it.

• I’ll get hemorrhoids.

• It will be messy, and my butt will smell bad.

• I’ll get constipated or have diarrhea.

• It will hurt; something will get ruptured.

• It won’t feel good—I won’t like it.

• I won’t be able to take her dildo.