by H.L. Shaw

I'm talking, of course, about anal sex.

Butt sex, sodomy, buggering, taking it up the poopshoot, going in the out door, poking out your brown eye, sitting on it, rag time blues, Greek sex, and even rimming, fingering, fisting and plugging. I want to be very clear.

But, by now, in 1999, it's almost a fad. It's time to get to know your anus, become connected to this powerful porthole in your body. You've heard about the nerve endings, yes? How they say there are thousands and thousands there, making that area extremely sensitive? I can vouch for it; anal sex has been some of the most moving sex I've had. Now, I'm not saying you should feel bad if this doesn't turn you on; everyone is different etc. etc. But, if the rest of you don't mind, I'd like to give you my own guide to exploring your butt.

First of all, you're gonna need lube. I recommend Liquid Silk's Maximus, though any thicker lube, such as ForPlay or Probe, will do. The thicker lube will stay put; the anal canal extends further than the area you'll be using, and a thin lube that works fine in your vagina will get pushed up inside, away from where you need it the most. If you're playing alone, it doesn't matter whether or not your lube is latex safe, but I say be prepared for that from the start, and make your investment in a water-based lube.

SOLO PLAY

Here's where I mention showers. If you're afraid of, well, shit, then be sensible and shower first. If you've recently bathed, there's nothing really that dirty about it. You'll get to know your body, and eventually can predict when will be a good time for anal play. And even if you do get it on your fingers, trust me, honey; you'll live.

Ok, ok, here's a hint: latex gloves. You can get them cheaply, in bulk, at your local drugstore, usually near the condoms and pregnancy tests. They're cheap, reasonably thin, and make clean-up a breeze. Pull them off over your fingers, and everything that was on your fingers is safely within the glove. And if you're alternating between anal and vaginal penetration, you can put several layers of gloves on, snapping them off before changing venues (so as not to give her the nastiest infection of her life).

Get yourself comfortable in the place you usually masturbate (if you don't masturbate and would like to know how, then send us mail and let us know - for now, this is an advanced course). In fact, start masturbating the way you usually go about it, let yourself become turned on and comfortable.

Start walking your fingers back there. Try lying on your side in a half fetal position, with your top arm falling behind you. Use that hand to explore your hips and buttocks. Start tracing the cleft between the cheeks, increasing pressure, lingering at your anus, whatever starts to feel good. Even if you're not wanting to penetrate yet, spread a little lube on your fingers and circle your hole with them. Vary the amount of pressure you use, breathe evenly and relax. Pay attention to how it's feeling, try new variations and find which is the most tingly and exciting.

As you circle, start to press in a little harder. Let the tip of your finger scoop between the ring of muscle, breathe into the sensation. Resist the natural reaction of clenching your cheeks at this initial entry; try to think of them as loose and open. It's very encouraging for your fingers if your body starts to press back, to open to their massage. As you get better at this, let your finger slide up inside. (You'll want to angle most penetrations away from the spine). Circle just inside the sphincter, feeling the walls of your anus and the unique texture there. Here's where you meet those thousands of nerve endings. Push in deeper, letting yourself rock back to meet the probing.

If you have a toy, now might be a good time to try it out. There are two standard small anal toys: plugs and probes. A probe is usually about 4-6 inches long, slender and tapered so it's narrower when you start. A plug has a large bump in the middle, with a narrow neck right before the flared base. This bump will (usually) hold the plug inside you without a harness. You'll want to cover it with a condom or, since most butt plugs and probes are small, a latex glove. This makes for easy clean up later, and gives your toys a longer life. Put some lube on the tip, and line it up with your anal opening. Move the tip in and out, circling like you did with your finger. Again, push back to meet it, open to the sensation.

If you get in all the way, pushing slowly and working your way back, you might want to leave it there for a bit. Relax your body and gently acknowledge the sensation of penetration. If it's feeling good, try clenching and releasing your sphincter around it. Pull "up" with that ring of muscle; open your butt to the plug and try to pull it further inside you. Rock back and forth; play with your clit or penis or whatever feels good. Keep rocking and/or pulsing and resume your other masturbation. Try rotating the plug around without withdrawing it. As you get more comfortable, you'll want to work the plug or probe in and out, circling on penetration to increase the amount of friction. Come, or not.

HOWDY, PARTNER

I'm not trying to scare you, I'm just being realistic.

(I do not mean to discriminate when I say "he". Many couples use a strap-on dildo to allow the *her* to penetrate. Unfortunately, at press time your author did not feel that she had the expertise to advise in this matter. Hopefully a future column on this subject will appear after the situation has been rectified).

For convenience in pronouns, I will use "he" to mean the penetrator and "you" to mean the penetratee.

Lie in the "spoon" position, in front with your ass pushed up against his groin. Relax, stroke and play with each other. Have him stroke your thighs, side and buttocks to relax you. He can also reach around and play with your breasts, tummy and groin, but you're going to have to rely on something other than your hands. Tilt your ass up, rotating it around until you feel his penis lying along the crack of your ass. Clench and release, catching him slightly as you do so. Respond to his caresses and wiggle your hips - let your excitement play off each other. He can push up slightly, rubbing his dick along the crease, teasing you in many places at once.

As your excitement grows, so will his erection (if it hasn't already). If you're not a fluid-bonded pair, here is where you might consider putting that condom on, even if you're not ready to be penetrated yet. Skin-on-skin contact puts both of you at risk for sexually transmitted diseases and possibly even pregnancy, so play it safe.

If you didn't already engage in finger-play before you spooned, you might have him scoot back and let his fingers walk around your hips and down the swell of your ass. If he's already been stroking your vulva, bend your top leg so your knee is in the air, leaving him room to walk his fingers further back. Reaching from behind is probably easier, though, so when his exploration gets a little more intense, lean forward, pulling that outer knee up beside you, giving him fuller access to your ass.

(Once a finger or a toy goes into your anal canal, however, make sure it doesn't go anywhere else. Going from the anus to the vagina without changing gloves or washing your hands will result in a nasty infection).

Let him play with you in the same way you play with yourself. Feedback is incredibly important; establishing communication is vital. Tell him when you want more, and exactly how you want it. You'll want to work up until he can get at least one finger up inside you easily. If you find yourself clenching up, have him stop immediately, but don't have him withdraw any more than is necessary. Having him hold perfectly still while you relax around him is a basic skill in beginning butt sex. Perfect it.

Hopefully your finger play has involved lube, but even so, you'll want to place a dollop of it on the tip of his erect penis, swirling it around and down to encourage it to spread evenly. Get back into your spoon position, again, lifting your outer leg and leaning forward to ease access. Place his penis at the opening to your anus. You should reach back and hold him in your hand. Twirl the tip of his penis around the opening, pushing in and scooping as you did when you first tried finger penetration. Push back a little, guiding him into your opening, but don't push too hard. If it starts to hurt, just pull forward a little and let yourself relax. Rub him around the outside where it feels good and isn't threatening. Breathe. Let him nibble on the back of your neck and shoulders, turning you on more. Then try again.

Keep in mind that YOU'RE IN CONTROL. You. The bottom. He should be paying close attention to your reactions to everything, but you've got to let him know that you're calling all the shots. Once you get practiced at this, he can do some pushing, but for right now, I want you to push back onto him, not the other way around. Ok?

Ease back onto him again, this time taking him in a little farther. Take your time, there is no rush and that anal tissue is delicate and needs time to adjust to this new penetration. There are two ways to get him all the way in. The first option is to push until it hurts, then stop and relax, without having him pull out This can be exciting as you'll feel fuller, and very vulnerable. Once he's all the way in, you can pulse your anal canal, pulling along his member, clenching at him and letting it release around him. I find that a "pulling" motion -as if you're sucking him in- can be very arousing and often leads to orgasm if coupled with digital manipulation of your clitoris.

Sometimes it works best if you push back until it hurts, pulling out a little to relax when it does. This sort of in-out slow motion will not only let you get used to his girth inside you, but may make actual intercourse easier later. The idea is to slowly push and pull, increasing the distance of each stroke until you're taking him all the way inside you each time. You're not building up speed yet, but duration of strokes. When you finally get him all the way inside, you're going to want to relax before you start taking full strokes again, even if the stroke that got him there involved almost his entire length. When he does pull out again, concentrate on the glorious feeling of withdrawal; when he's almost out, feel his member stroking between the skin of your cheeks. When you push back down on him, feel him move along the length of your anal canal. The tissue is very thin and sensitive; if you're relaxed you should feel shudders of excitement running up your spine from each stroke.

Go slow at first, but don't be afraid to increase speed and pressure slowly if it's feeling good. He should still be stroking you and arousing you in other ways as well. The intimacy of what you're doing can be very heady; if he's very concerned and tender it can be a very intense and bonding experience.

Don't expect orgasms the first time. I find that when I come from anal play the anal canal becomes too sensitive, effectively ending the anal sex. If he does come inside of you, notice the pulsing sensation of his spurts - you can feel it quite clearly and it can often trigger your own orgasm. (Encouraging him to come inside you can be a real turn-on). When you need him to exit, have him pull out slowly and steadily. Let him take care of clean up as you let your anus relax. Sometimes the feeling of emptiness is as exciting as being full up, and you can masturbate, or have him play with you, until you have another orgasm.

You'll probably feel as if you have to go to the bathroom afterwards. Go ahead, but don't strain too much, as it may be a, er, "phantom shit". You'll might seem a little loose immediately after, but don't worry, your muscles are already tightening back up.

Frequent anal sex will make each time easier, but don't overdo it at first. Build up to more frequent anal play, giving yourself time to recover between sessions. Before long, you too will become an anal aficionado.