Tip No1: Play Safe
There are some serious safety issues you should be aware of at all time regarding anal sex. First and foremost, whatever touches the anus shouldn't be touching anything else. Never-ever take the penis or sex toy out of the anus and put it into the vagina. This 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.

STDs are also a major concern with anal sex. This isn't just limited to AIDS, herpes, genital warts, syphilis, gonorrhea, etc. which can all be transmitted through anal sex. Safe sex should always be practiced when giving anal sex. It’s not worth the risk to you or your partner.

Tip No2: Lube, lube, lube
One of the most important things to remember when thinking about anal sex is, unlike the vagina, the anus isn't self-lubricating, so don’t forget your anal lube. The more lube you use, the better it is. This makes the initial penetration much easier and less painful and makes the whole experience, for you both much more enjoyable. The most common suggestion we hear is to use LOTS of lube and relax; this point just can't be emphasized enough.

All kinds of lube are used for anal sex, from Saliva to Vaseline to high-tech silicone-based lubes. We strongly recommend spending a little money to get a high quality water-based lubricant; if you use an Oil or Petroleum based lubricant like Vaseline it will degrade the latex in a condom, destroying its usefulness. We recommend products like Erozon Bodyglide or Wet, available online. Note, a condom may be "lubricated", they typically don't offer enough lube for anal sex.

There are some specialty lubes designed for anal sex that include an anesthetic to numb the sensation and make anal sex less painful. We 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 No3: Start Small
Simply put, a penis is a bit big to be the first thing you stick up someone's butt. It’s best to start with something smaller and increase in size gradually. Fingers are an excellent beginning point. Use one finger then two, to initiate your partner into the mysteries and enjoyment of anal penetration. Try it while performing oral sex for an extra thrill, but ensure your fingernails are trimmed, do not forget your lube, some people chose to wear latex or rubber gloves.

As your partner gets used to your fingers, you might graduate to a butt plug or a small dildo. Butt plugs and Dildos are available in all shapes and sizes. Have a look around together on our site to get one you both feel comfortable with. Remember, 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 No4: 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.

Your partner is much more likely to consent to anal sex if they have seen that you're open to being on the receiving end as well. Encourage them to use their fingers inside you, or even purchase a butt plug or small dildo and let them use that. 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 No5: Clear the Way
Before having anal sex, your partner should have a good, complete bowel movement. If they don't, you might find you meet far more fecal matter than you 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.

Tip No6: Relax
Chronic anal tension is a common cause of anal discomfort during sex. Hemorrhoids and constipation is usually a sign of this condition. Tension can be relieved by gently touching the anus and becoming more familiar with it. An ideal time to explore the anal opening is while taking a shower or bath. Deep breathing also affects the anal muscles. Tensing the anus and then letting go is another way of learning to relax it.
No physical injury from anal stimulation results if both partners refuse to tolerate pain, never use force and avoid the use of drugs.

And don't forget ENJOY!