A by Dr. Al Cooper and Dr. Coralie Scherer :

You are not alone in having mixed feelings at the thought of anal intercourse or as it is also known, anal penetration. It is not as frequently talked about as penile-vaginal intercourse nor as commonly practiced . As with any sexual practice, do not allow yourself to be pressured into any activity that does not feel OK.

You, as well as your partner, have the right to say no and either of you can change your minds in either direction at any time. That is what the phrase, “between consenting adults” is about. You are wise to gather as much good information as you can to help clarify your decision. Then you may decide to give it a try or to keep things as they are.

So here are some things that are good to know about anal intercourse. Is it safe? Well, certainly, there is reduced danger of becoming pregnant. However, one drop of seminal fluid or semen spilled too closely to the mouth of the vaginal opening can lead to impregnation. Keeping track of such secretions can be a chore when in the throes of passion. Make sure that such fastidiousness is not the last thing on your lover’s mind if you choose to experiment with any type of sex that might result in sperm being deposited in the general area of your vagina.

Also, while anal intercourse does not cause AIDS or other sexually transmitted diseases (STDs), it can lead to transmission of AIDS or other STDs when either partner is infected. This is because the rectum is not self-lubricating like the vagina or even the mouth. The delicate tissues there are easily irritated or damaged and can be an easy route into the body for infecting agents.

And of course, there is the matter of fecal matter. It is filled with bacteria that can cause very painful infections if transferred to the mouth, penis or vagina. It’s not a good idea to have anal intercourse followed by vaginal intercourse without carefully washing the penis and using a fresh condom. If not, unseen but highly infectious fecal matter might be introduced into the vagina, often leading to serious vaginal infections within a week or two.

Therefore, there are some very important things to do if anal intercourse is to be a safer and more pleasurable experience:

1. Use lots and lots of lubricant. This should be water-based (have no oils in it), especially when used in conjunction with condoms. Oil-based lubricants can weaken condoms and result in condom breakage during their use. More than one pregnancy or infection has been the result of this mistake.
2. Use condoms to reduce the possibility of transmitting STDs or transferring feces. Remove the condom and carefully wash the penis before engaging in any other activities.
3. Entry should be gentle and thrusting slower and shallower than in vaginal intercourse to prevent or reduce irritation or tearing of rectal tissues.
4. Experiment with angles of entry and positions to reduce discomfort and increase pleasure

There are some serious safety issues regarding anal sex that you need to be aware of at all times. First and foremost, whatever touches the anus shouldn’t be touching anything else. Never never never take the penis out of the anus and put it into the vagina. That can lead to serious infections and other complications. After any kind of anal play, you should immediately change condoms and wash the relevant body parts thoroughly.

Of course, STDs are also a major concern with anal sex. This isn’t just limited to AIDS; herpes, genital warts, syphilis, gonorrhea, etc. can all be transmitted through anal sex. You shouldn’t be having anal sex without a condom; it’s not worth the risk to either partner.

Tip #2: Lube, lube, lube

One of the most important thing to remember when thinking about anal sex is that, unlike the vagina, the anus isn’t self-lubricating: you gotta bring your own grease.  And, the more lube you use, the better. It will make the initial penetration much more easy and less painful for the woman and make the whole experience, for both of you, much more pleasant. The most common suggestion we get from our readers is to use LOTS of lube; we just can’t emphasize this point enough.

All kinds of lube are used for anal sex, from spit to Vaseline to high-tech silicone-based lubes. We’d strongly recommend spending a little money to get a high quality water-based lubricant; remember, an oil-based lubricant like Vaseline will degrade the latex in a condom, destroying its usefulness. We’d recommend products like AstroGlide or KY Jelly, available in any drug store. Note, though a condom may be “lubricated”, they typically don’t offer as much lube as we’d recommend for anal sex.

There are some specialty lubes designed for anal sex that include an anesthetic to numb the woman’s sensation and make anal sex less painful. We’d advise against these products. The simple fact is, pain is a way of your body telling you that something’s wrong. If you’re in pain during anal sex, you need to focus on solving the root problems, not anesthetizing yourself so it’s easier to endure.

Tip #3: Start Small

Simply put, a penis is an awful big to be the first thing you stick up someone’s butt . Better to start with something smaller and work your way up. Fingers are an excellent beginning point. Use one finger, then two, to initiate your partner into the mysteries of anal penetration. Try it while performing oral sex for an extra thrill. Be sure your fingernails are trimmed, not to forget the lube, and you might even want to wear latex gloves.

As your partner gets used to your fingers, you might graduate to a butt plug or a small dildo. Dildos are available in all shapes and sizes. Go shopping together to get one she thinks she can handle. Remember, though, don’t put the dildo into the vagina after putting it into the anus. The safest way is to put a condom on the dildo before using it, and to wash it thoroughly immediately after.

Tip #4: Turnabout is Fair Play

Whether you’re trying to convince someone to have anal sex or trying to figure out how to do it in a gentle, pain free manner, there’s no better preparation that exploring anal play with yourself.

A partner is much more likely to consent to anal sex if she’s seen that you’re open to being on the receiving end as well. Encourage her to use her fingers inside of you, or even purchase a butt plug or small dildo and let her use that. Once she’s seen you’re willing to do it, it’ll be hard for her to resist exploring it as well.

Of course, anal play on yourself is a great way to learn how anal sex feels and to learn how to make it more comfortable for your partner. You might also be surprised just how much you like it…

Tip #5: Clear the Way

Before having anal sex, the woman should have a good, complete bowel movement. If she doesn’t, the man may find himself encountering far more fecal matter than he might have liked (i.e. packing the fudge). Now, for some people doing this on-command might not be the easiest thing, and straining to defecate is not healthy. A high fiber diet may help things along and is good for your health in any case.

Of course, if you really want to clean things out in a hurry, you can purchase an enema from any drug store. There’s some controversy about this; some people feel having an enema first can actually increase the irritation during anal sex. If you’re going to go the enema route, we’d recommend doing it several hours before you plan to have anal sex, rather than right before the act.

Anal sex is usually safe, assuming you take some precautions. In fact, many people consider anal sex to be an exciting way to spice up a relationship — there are numerous nerve endings in that region that feel great when stimulated!

Before you get started, though, it is important to understand that the anus, unlike the vagina, has no natural lubrication. This puts you at a greater risk of tearing or pain. A lubricant is necessary for comfort, and I suggest using a condom as well. A condom will aid a feeling of smoothness and reduce the risk of an STD (for those who may not know their partner very well). Also, keep in mind that it is unsafe to follow anal sex with vaginal intercourse because of the risk of introducing bacteria. So make sure he gets a thorough cleaning before moving on!

As you’ve never indulged in anal sex, I recommend starting small in your initial exploration. Have him use his finger (but clip those fingernails!) before you actually engage in sex. Perhaps repeat this activity a few times, until you feel ready to graduate either to larger intimacy products or to your partner.

Also, remember that it is essential for you to be relaxed when experimenting with anal sex or your body will be more likely to respond negatively. Try sharing a hot bath or an erotic massage beforehand. Most important, listen to your body from the beginning and stop if there is any pain. If you do feel pain, practice patience and continue exploring later. If you are cautious and take your time, the experience you seek is likely to contain all the pleasure and excitement you anticipated!

Learn more in the Everyday Health Sexual Health Center.