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I like to have my lover on her back with a pillow under her butt, her knees bent and legs up in the air. l put one hand on each of her cheeks, and spread them apart. Then, I cover her hole with my tongue and lips, slipping the tip of my tongue just inside her ass.

Rimming can be incredibly pleasurable for everyone involved, including the person giving the pleasure. Nina Hartley demonstrates in her anal sex video:

Rimming is extremely, extremely pleasurable… It’s important to keep in mind that if you’re performing analingus, give your mouth a good time. Again, it’s never something that you’re just doing to the other person; it’s something you’re sharing with each other. As happy as my [ass] is, his mouth is equally as happy.[39]

HE IS CUTE LITTLE PUCKER-KISS OF AN ASSHOLE

He comes into view, looking for all the world like its there for your delectation. You extend your tongue and lick the sweet, tangy little entrance. He groans.

— LINDA JAIVIN[40]

Analingus and Safer Sex

If you plan to venture around and inside the anus, and you are nonmonogamous, you should definitely practice safer sex by always using a barrier for anal contact. Rimming without a latex barrier is considered a high-risk activity for the transmission of STDs and HIV.

If you are monogamous or fluid-bonded, you may still wish to use a barrier. Some women and their partners choose not to, but be aware of the risks you are taking if you make that choice. Remember, fecal matter in the rectum and anal canal may contain hepatitis A, amoeba, parasites, intestinal viruses—all of which can infect you or your partner and make you sick.

A barrier can be a dental dam (a square of latex usually available where sex toys are sold), plastic wrap (like Saran Wrap), an unlubricated condom cut lengthwise, or a latex glove cut into a usable shape. Dab some lube on the side that covers the anus. Some people like to cut up latex gloves for analingus and cunnilingus because you can use one of the glove’s fingers to stick your tongue in (see figure 8).

If you’re not using a barrier, rinse thoroughly with mouthwash after rimming before putting your mouth elsewhere (like on someone’s vagina or penis) to prevent the spread of bacteria.

8 • ANAL PENETRATION

Insertive Anal Penetration

A captain steering a ship through a turbulent ocean knows that it is the water that is in control; the captain’s job is tuning in and maneuvering through the tides and currents.[41]

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.

Go Slowly, Be Gentle

I like to give a long and titillating anal massage which builds up externally for a long time and then becomes penetrative with a finger and sometimes toys.

Where the other person just receives. I also like humping the butt (not penetrative), with the other person face down and me on top of them.

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.

HE CLAMPS UP TO PREVENT ME FROM RUBBING HERE, but aggression has risen in me and I press on, massaging a moistened finger at the entrance. Its slick there, and I can imagine the smell which excites me; I know that he’s concerned about the smell too—how I’ll find him—and this excites me. The thought pops into my mind that i fI had a dick, right now i fI had a dick, I would wear him out…”

— MAGENTA MICHAELS[42]

For me, it helps to relax my anus if I’m having clitoral stimulation… If it’s just my butt, it’s like a hot piece of intense sensation. If I put something on my clit like the vibrator, the whole area becomes like a giant clit… Every time you stroke your clit, [your ass] relaxes and opens up.[43]

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.

I love feeling the tightness of that hole around my fingers, the heat. I love the feeling that I always have to push my way in, like I’m discovering a new hole.

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.

Listen and Talk to Your Partner

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.

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1. Hartley, Guide to Anal Sex.

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Linda Jaivin, Eat Me (New York: Broadway Books/Bantam Doubleday Dell Publishing Group, 1997), 220.

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1. Herrman, Trust, 43.

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Magenta Michaels, “Taking Him on a Sunday Afternoon” in Herotica 2: A Collection of Women’s Erotic Fiction edited by Susie Bright and Joani Blank (San Francisco: Down There Press, 1991), 19.

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2. Hartley, Guide to Anal Sex.

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3. Sex educator Robert Morgan.