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Excerpted from:
The Ultimate Guide to Anal Sex for Men. This is the third in a series of excerpts from Cleis Press titles, appearing in our Be Our Guest column.
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The safest and most comfortable way to experiment with anal sex, at least initially, is in solitude. If you want to try anal with a partner, it just makes sense to experiment with your own body first. You can never fully appreciate how something feels to your partner if you lack direct experience. Learning to give yourself anal pleasure is the very best way to understand what it takes to give your partner the ecstasy he or she desires.
Relax
Lying in a comfortable position, take some slow, deep breaths. Breathing is a key to comfortable anal play, as it helps to relax the anus, and relaxation is one of the three essentials to anal erotic pleasure: relaxation, lubrication, and communication.
One excellent relaxation technique is to work your way up the body, alternately tensing and relaxing various body parts as you inhale and exhale: the toes, ankles, knees, tops of the thighs, pelvis, belly, chest, shoulders, elbows, wrists, fingers, neck, face, forehead. At the end of the sequence, tense all of the parts at once on the inhalation, hold for several seconds, and then collapse completely on the exhalation. You can repeat this part as many times as you wish. Later on, you can share this activity with a partner.
Exploration
Now find a comfortable position where you can stay for a while. With a hand mirror and some good light, position yourself so that you can see your anus in the mirror. How does it look? Does it look tense, relaxed, or somewhere in-between?
Gently massage the area around the anus -- the inner thighs, the butt, the top of the butt around the tailbone. Notice how your anus responds. Gradually work your way down to the anus and begin to touch it gently. Notice the sensations you feel in your anus and the rest of your body. Don't penetrate the anus, just stick to external touching for now. Stop when you've explored enough. You can repeat this exercise as many times as you like. You may want to combine touching with masturbation and see how that feels.
Exploring Penetration
It's a good idea to have a bowel movement and to wash the anus before penetrative play. In fact, taking a bath or shower beforehand is an excellent way to relax.
 You can use your bare fingers or slip on form-fitting gloves made of latex or nitrile for penetration play. (Vinyl gloves tend to be baggy and thus I don't recommend them for any kind of anal play.) It's a good idea to wash your hands with antibacterial soap or dishwashing liquid both before and after. Your nails should be trimmed and filed so that they're smooth and have no edges or rough spots. You'll also need some lubricant.
Get Greasy
I recommend that you use an oil-based lube if you're playing alone. However, oil-based lubes will destroy latex, which may not be an issue for you in your solo exploration. If your glove or condom starts losing its integrity, though, you'll know why. (In any case, don't use an oil-based lube with latex condoms or gloves when playing with a partner!)
Silicone lube is a good second choice, since it has a consistency similar to "pre-come" and stays moist for quite a while. However, don't use silicone lube with silicone toys, as it may ruin them -- the lube and the silicone toy aren't compatible.
You can also find thick, water-based lubes marketed especially for anal play. Water-based lubes tend to dry out and need refreshing with water. If you do choose water-based lube for your exploration, a small plant mister or similar water-filled spray bottle comes in handy for reviving lube.
Don't be afraid to get greasy! One of the wonders of this type of play is the sense of limitless abandon that one can achieve, which is its own form of ecstasy. It's much easier to attain this sense of freedom when you don't have to restrict your body movement because of logistical or aesthetic concerns like grease on the couch. Have enough towels on hand to avoid worrying about staining the sheets or furniture.
It All Starts with a Finger
Begin massaging your anus with a single lubricated finger. Experiment with different types of motion to see what feels good. Many people like to use a slow, circular motion; others prefer an up-and-down or a back-and-forth motion. You can also try rubbing first on one side of your anus and then the other, pulling outward with a stretching motion. You can use more than one finger at once if you wish. There's no correct way to do this, as long as it doesn't hurt. If something hurts, then stop doing it and rest. Then try doing something else. Just keep breathing deeply, and don't go any faster than is comfortable.
 When you feel comfortable, try slipping the tip of your lubricated finger into your anus using slow motions. Find the two sphincters and notice how elastic they are. If it feels good, you can try dipping the finger in further, adding a second finger, or spreading the sensation outward from your sphincters in different directions. It's all up to you.
Exploring with Toys
Jack Morin's "biofeedback" exercise is helpful when you're starting your exploration time. With this exercise, you simply slip your lubricated finger (or fingers) into your anal canal and describe the current tensed or relaxed state of your internal sphincter. Insert your finger so that you can feel the sphincter and say aloud, "tense, tense" or "relax, relax" as you feel the internal sphincter tensing or relaxing. Increase the number of fingers as you feel comfortable doing so, until you're ready to try inserting the toy. Again, deep, conscious breathing helps to develop body awareness and relaxation. You always want to insert on the exhalation.
Make sure that you use a toy designed for anal play, which will have a base at least an inch wider than the penetrating part. Don't insert the toy any more quickly, any further, or for any longer than is comfortable for you. If the toy you're using is too wide to accommodate initially, experiment with alternatives such as putting it in a little bit with an in-and-out motion, or switching to a smaller, narrower, or differently shaped toy. Don't push too hard on anything that's making you sore. Let the sphincters do the driving. When the mind and the body are aligned, the toy will be more likely to find its way in.
Masturbation
Did I mention that it's OK to masturbate in conjunction with all this activity? You probably figured that out, anyhow! Masturbation aside, the main purpose of the exploratory process is to focus on the anal region so that you become more comfortable with its look, its feel, and its sensations. Furthermore, since the outer sphincter of the anus tends to tighten in conjunction with any genital contractions, I recommend saving masturbation to orgasm until after you're comfortable with any touching or penetration, especially if you're inserting anything larger than your finger. If your anus gets too tight, you can stop masturbating for a while and go back to the breath work and gentle finger stimulation until it relaxes again. Don't restrict your masturbation to the genitals, either. Some people discover that stimulating other erogenous zones, such as their nipples, enhances their anal experiences. As always, it pays to keep an open, experimental mind.
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Copyright © 2002 by Bill Brent. Reprinted with permission of the publisher.
The Ultimate Guide to Anal Sex for Men by Bill Brent (Cleis Press, 2002, ISBN 1-57344-121-X)
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