by Robert W. Belsky

Some sexual fantasies are more difficult to initiate than others, and telling your lover that you're interested in entering their exit is one of the toughest. Anal sex is a difficult subject to discuss because many people consider it taboo, or dirty, or immoral, or painful, or they may be afraid to try it simply because the idea horrifies them.

But if you're comfortable with each other, and you're agreed that it's something you'd both like to try, and you're ready to experiment in a relaxed and open atmosphere, then anal sex can be a fantastic experience.

Right off, let's admit it -- the first time, the first few times you are penetrated anally, there will be pain. There are several things you can do to minimize this, but you should be aware at the onset that you're planning something for which your body isn't naturally designed.

Before you begin… Safety

You'll have to decide this for yourself. If you're in a long-standing, utterly monogamous relationship, you may feel perfectly safe entering your partner's rear end without using a condom. I would advise it anyway. Anal sex is one of the most common ways of transmitting the AIDS virus, and there are plenty of other diseases and infections that can pass back and forth through thin membranes that really weren't intended for this sort of friction. Wear a condom.

Cleanliness

Let's get this out of the way as well. This should be a no-brainer, but make sure everybody's parts are clean. It's not a bad idea to have a bowel movement an hour or so ahead of time, and be sure to bathe afterwards. If you're very nervous and you feel you won't be able to relax for fear of "accidents", you might consider giving yourself an enema beforehand. It's not absolutely necessary -- "accidents" are unlikely under normal circumstances and your lover should certainly understand anything that happens -- but if it helps your peace of mind than be all means, go to it.

Lubrication

At the top of the list for utterly necessary components is a good lubricant. The rectum doesn't generate the natural slipperiness that the vagina and mouth do, and every little bit helps.

Oil-based lubricants tend to work better than their water-base counterparts because the water-based lubricants can dry out in the middle of the act and cause pain from the friction. You don't want to have to keep stopping and starting. Vaseline is an old stand-by -- most people have Vaseline in the house -- because it will stay in place and will lubricate better than other, thinner lubricants. Coca butter works well also. Massage oils are next in line and at the bottom of the list is baby oil.

Communication

Most vital of all, and the ingredient that will make it all work. Is he moving too fast? Not fast enough? Maybe you need a minute to relax, or you've changed your mind, or you think a different position might work better, or you're really, really enjoying this. Let your lover know!

Positions

There are several positions that can make anal intercourse easier and less painful if you take the time.

The most basic position is for your partner to be on their back, legs spread and/or pulled up. Putting a pillow or two under their behind will help position them better for ease of access and for comfort.

Another position for your partner is to have them on their elbows and knees (doggie style). This position makes for easier access, but it also naturally encourages your partner to tighten up their stomach and groin muscles. You can get past this by placing some type of support under their chest or stomach, such as a pillow. Leaning forward onto a pillow is more comfortable and it causes your lover's legs to spread out and to the side, an easier angle for penetration.

You may also want to try having your partner on their side. The legs need to be a scissors position: the upper leg extended in front or drawn towards the chest and the other leg straight down. This is easier for both of you to maintain for a longer time and it may help remove some of the psychological edge if both of you are on the same level, pushing towards each other.

The person receiving can also choose to be on top, where they can have complete control over the proceedings.

Getting Started

Analingus

As with any type of sex, you'll need to work your way up to it. Start off with hugging, kissing, touching, licking and playing with each other's erogenous zones, everything you'd regularly do to excite each other. If you're the one providing the phallus, you're going to want your partner as excited as possible before you begin. I'd suggest oral sex. Get them good and panting and then, very naturally, work your way gradually down towards the anus.

Important note -- once any part of you (tongue, fingers, genitalia, toys whatever) has touched their anus, do not bring it back up to the vagina or clitoris as this may cause an infection later.

Spread your lover's ass-cheeks apart and see what you can think of to get them relaxed. You can give a gentle flicker around the center or gently push their tongue in. You can make your tongue as rigid as possible and work deeply inside. You can widen their tongue to apply pressure over the entire outside area. And be sure to make some time to firmly lick or suck on the perineum (the area between the anus and vagina). Very sensitive area, lots of nerve clusters.

No reason to let your hands stay idle. Stimulate her vagina or caress her clitoris or stroke his cock while you tongue away, and don't be surprised if things come to an explosive head faster than you expected.

You can try any or all these methods, but what you need to be aware of and pay close attention to is what your partner enjoys the most. As with any type of sex, you will get feedback, either from moaning, thrashing around or talking. Pay attention to it. If you do something that gets a powerful, positive response, do it again. And again.

Finger Stimulation

After your lover is used to your tongue, you may want to switch to your fingers. Make sure that before you start, your fingernails are trimmed and smooth.

This is the time to apply the Vaseline or other lubricants to the anus and your finger. You may also want to use a rubber or latex glove, the surgical type. Entirely up to you.

Remember, once you start penetrating the anus with your finger, do not use that finger near her genitalia to avoid infection.

Now that you are ready to start, gentle touch the anus, circling it with your finger before penetration. It is very important that you work your way up to it slowly, gently stroking the area right around the opening, gradually pushing gently at the center but not actually penetrating.

Your partner should be as relaxed as possible. Work your way in a millimeter at a time, letting your partner get used to your finger's presence.

Once you are inside, concentrate on stimulating the side nearest to her vagina. A pressing motion is very useful. Place another finger in her vagina and press along the same wall from both sides. The wall is thin enough that you will feel each finger from the other side, and so will she. If your lover is male, let your finger slide naturally along the inner curves until you feel a small bulgy bit. This is the prostate gland, and this is one of the most erotically charged parts of the human male anatomy. Again, don't be surprised if these sorts of maneuvers result in unexpected climaxes.

Using your finger helps stretch the sphincter to make it easier for the phallus to enter.

Anal Intercourse

Now that your partner is accustomed to all that attention back there (especially if they've ripped off a few orgasms along the way), it's time for the actual anal intercourse.

First thing you must do is to make sure that both the penis and the sphincter are very well lubricated. You cannot have too much lube here. The next thing you need to know is to take your time and don't rush it because this can cause a good deal of pain and make it a bad experience, and that'll make this the last you'll ever see your lover from this angle again. You want to make the experience as pleasurable as possible for both of you.

Remember to be very careful when you penetrate. Start off very slowly, just pushing slightly at the opening, not actually going in. Add the tiniest amount of pressure each time as you push, letting the sphincter muscle get used to your penis. Going slow also helps assure your partner that they're in control. You can also just lie there and allow your lover to push back, impaling themselves at their own speed. Don't be surprised if you lose it yourself at this point.

The key is to get through the initial penetration with the head of your phallus passing through the sphincter muscle. Once the head of the penis has passed, the sliding of the rest of the phallus should be comparatively painless. Once you're safely inside and things are going well, you may want to shift the angle slightly so that the head of the phallus is pressed harder against the inside where the passage is closest to the vagina or that prostate I mentioned. You will find that this will bring great pleasure to the both of you.

Once the both of you have had anal intercourse several times, you will find that it becomes easier because your lover is more relaxed, the trust is there, and the penetration is nearly painless. Talk about it, see what both of you thought, and talk about whether you'd ever want to do it again. You can choose to move on to different positions and new toys, you can make it your preferred sexual move, you can decide that once was enough for one lifetime, or you can save it as a loving act for a special occasion. And remember, turnabout is fair play.