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The most important pieces of advice anyone can give on anal sex are: lubricants, condoms. The most commonly available lubricant is KY-Jelly, available at most drug stores and discrete online sex shops. Do not use anything that is oil-based. Make sure the lubricant you buy is rated "condom compatible." Nothing else will do. Oil-based lubricants such as Vaseline or baby oil will destroy a condom long before you're done having sex. 

The rectum is home to lots of infectious bacteria so a condom should always be used. Initial penetration is always the most difficult part of anal sex the anus is a tight ring of flesh at the opening of the rectum designed to control the elimination of bodily waste. It is partially under voluntary control, and partially reflexive to stimulation. Your partner has to relax, and you have to go slow to coax it into opening enough to receive your penis. Start with a well-lubricated finger or a slim dildo. The dildo is more realistic, but your fingers can flex and feel what they're doing inside her ass. Slide one finger in slowly, letting her adjust to it. 

Take your finger all the way out, then push it back in again. Give her anus time to get used to this kind of activity. Then slide a second finger in. Consider how big your penis is and realize that two fingers is probably enough. For actual intercourse, picking a position can be important. Many women want to be on top, to regulate how fast penetration occurs. Other like to lie on their stomachs, or crouch doggy-style, or to be penetrated while lying on their sides. 

Choose what's best before you start. As always, control yourself. Take your time and use lots of lubricant. People who like anal sex say that "too much lube is almost enough." Listen to her if she tells you it starts to hurt, back off. Eventually, a time will come during your lovemaking where her anus will relax enough to allow the head of your cock to 'pop' into her. If she is completely relaxed, that pop should feel completely painless. Now just because you're inside her is no reason to start pounding away like mad. Let her body adjust. Take your time. Eventually you will both be ready for more. 

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