Dear Juicy Justine: Is there an easy way to have anal sex without a lot of pain and mess? Is there something I can do before during and after to help? We were using anal ease but it doesn't work as well anymore. Any advice?

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First, if it hurts you're not doing it right! Anal ease (and other numbing agents) are BAD! Pain is your body signaling you that something is wrong. If you can't feel the pain you will go beyond your body's physical limitations and can do some serious damage.

Get aroused first. Lots and lots of foreplay! Self-stimulate or use a vibrator on your clitoris during anal sex. It will take your mind off it and help you relax.

Work your way up to a penis/dildo by starting with smaller fingers and toys first. It will take time, patience and practice but it's totally worth it.

RELAX! If you think to much about it, you won't be able to enjoy it. Take a deep breath and just go slowly.

Doggie style is not a good position - it will go too deep too fast and hurt. Missionary with your legs up is a much better option because you have more control over the speed and depth of penetration and it's also more intimate, better for non-verbal communication, etc.

Communicate. Communicate. Communicate. Slower, Harder, Faster, Deeper, a little to the fucking right. Tell your partner what you want and need. Tell them if it feels amazing and tell them if it doesn't. Don't let your partner think they are doing an awesome job when it's not.

Lube, lube, lube, lube, lube and maybe you might want to add a little more lube. It will reduce the friction and feel better. Silicone lubricants stay slick longer but water-based works too. I recommend all-natural, organic and body safe lubricants that are paraben/glyercin/oil free.

Also, use condoms, even if you are in a monogamous/fluid bonded relationship. It will help with the mess and decrease the increased risk of STI/HIV transmission caused due to tiny micro tears. It will also make it a smoother entrance and feel better.

If fecal matter is a concern make sure you have a healthy bowel movement before hand. You can also insert a wet soapy finger to clean yourself out. If you want to use an enema you can but it's really not necessary.

If you've tried all these things and it still isn't working out maybe anal sex is not your thing but don't worry, there are lots of other fun things to try! See http://juicyjustine.com/sex-tips for ideas.