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Anal Sex! Eight Steps to Satisfaction

By: Jordan LaRousse

Tags: Anal Sex Ask Jordan Sex Advice Sex Toys

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Dear Jordan,

I'm single and enjoy dating. I've had a few relationships, and am getting a little bit serious with the guy I'm dating now. We haven't had the exclusive conversation yet, but have been together for about four months. He's talking about wanting to have anal sex. I'm not so sure, never having had it. Is there a good rule of thumb to follow as far as when I should do it, and what steps can I make to ensure that it's an ok experience?

--Booty curious

Dear B.C.,

First let me say that anal sex is extraordinarily pleasurable. The anus is an erogenous zone that is ignored by a number of couples because our society still considers it to be a taboo sex act. In the words of Cathy Winks and Anne Semans, authors of The Good Vibrations Guide to Sex "It's a pleasure to challenge our society's irrational anal taboo, to spread the word that anal play is safe and stimulating, and to celebrate the sheer entertainment value of the subject matter (p. 206)." If you are one of those curious anal sex virgins who hasn't broken the taboo in your own bedroom, then follow these simple steps to enjoyable anal sex:

YOU GOTTA WANT IT. Be sure you want to do this for yourself and not just for him (but do it for him too!). Do it for yourself because it feels so good and is so much fun. At the same time much pleasure can be derived by the knowledge that you're giving him something a little extra special in the bedroom. It is super exciting to let your man explore the road less traveled; and it's a titillating experience even if you're a seasoned anal sex queen. Anal sex is incredibly intimate and will add a whole new dynamic to your sex life.

LUBE lube lube lube. I would say it a thousand more times, but that would be tiresome. Unlike the vagina, the anus doesn't have any naturally slippery secretions to take the friction out of fucking. My personal favorite lube is Astroglide, I find it works well for both anal sex and toy play (and the exciting combination of both). This is a water based lube that can be used safely with condoms and is also safe for vaginal sex. However, anal sex can also be enjoyed using an oil based lube. Oil lubes usually stay slippery longer and don't get sticky, but I wouldn't recommend using oil based lubes vaginally as they can cause irritation. There are some lubricants made specifically for anal play, they have the added ingredient of benzocaine, a numbing agent to help prevent any pain - however if anal sex is played correctly there wont be pain regardless of the type of lube you use.

START CLEAN Before engaging in anal play, be sure to clear your bowels and scrub your bumhole sparkling clean (some people choose to use an enema wash before anal sex, this can be fun, it works, but it isn't necessary). A clean playground is more enjoyable for everyone. (Although honestly, even if a mess happens, it's not the end of the world, especially if you're playing with a partner who you trust. After all, sex is no fun unless it's DIRTY!)

STAY CLEAN Never ever let your man go from anus to vagina without washing off his penis or replacing the condom with a fresh one. Anal to vaginal contact is a sure fire way to contract bacterial infections including e-coli. EW! Anti-bacterial wipes by the bedside are an easy way to do a quick clean up when moving from anus to vagina. Or enjoy your anal play in the shower, and do a quick scrub with soap before moving back to the vagina. Moving from vagina to anus, however, has a green light, no washing necessary.

CONDOMS are particularly important when engaging in anal sex if you are with a partner whom you don't know to be STD free and/or monogamous with you. (This goes for you too B.C., since you and your man have only been a couple for four months and haven't declared monogamy.)

RELAX. If this is your very first time, take it extra slow. Make sure your partner enters you ever so carefully, inch by inch allowing your body time to relax and adjust to the new sensations. A glass of wine and a bubble bath before play will help you to relax, the lube will make things go more smoothly, and the addition of clitoral stimulation at the hands of yourself or your partner will make anal penetration an even more enjoyable experience. But please, if you experience PAIN don't continue, you must understand that the rectum is lined with very thin and sensitive tissue and if not respected as such it can tear. Some individuals are more prone to anal fissure than others, so play it safe and know your body! Anal sex, when done correctly, is never painful. Relaxing your sphincter is the key to enjoying anal penetration. Once you relax, and sexual excitement overpowers you there are no bounds!

POSITIONS. Anal sex can be enjoyed in practically any position that you can think of. Some favorites include doggy style with you on your hands and knees and he kneeling behind you, or with you bent over the edge of the bed with him standing behind you. Anal virgins may want to try it from on top for the first time, this allows you to control the speed and depth of penetration, and allows easy access to your clit. Also try it from on top but facing backwards. And of course anal sex can add an exciting twist to the missionary position!

TOYS! Oooh la la there are so many exciting anal toys out there, it makes exploring anal sex that much more alluring. The Good Vibrations Guide to Sex offers the following suggestions for selecting anal toys:

"Make sure any toy you insert anally is completely smooth and nonabrasive, has a flared base so that it won't slip out of reach into your rectum and (if longer than four inches) is flexible enough to align with the curves in your rectum (p. 202)

"You'll probably find it helpful to select a dildo that curves up from the base rather than one that is set perpendicular to the base as this will align more naturally with the curve of the rectum (p. 206)."

This leaves plenty of toy options, from anal beads, to butt plugs, to vibrators and dildos. Anal sex opens the doorway to double penetration games, light D/s play, and a whole new world of sensation during sex and masturbation.

ORGASMS. So can a woman really enjoy an anal sex orgasm? My answer is absofuckinlutely yes! Anal sex orgasms are among the most intense orgasms a woman can have (remember we are gifted creatures with the ability to experience orgasms from a number of erogenous zones including the clitoris, the vaginal walls, the g-spot, the anus and sometimes for a few lucky girls the nipples!). Although I can't find any study on the physiology behind the anal orgasm, I know from experience that they are very real.

Once you have your first anal sex orgasm, you will be addicted for life. Let your inner anal kinkster out to play!

More resources & Suggested Reading:
Ultimate Guide to Anal Sex
The Ultimate Guide to Anal Sex for Women

The Illustrated Book of Anal Sex
The Illustrated Book of Anal Sex

MasterClass: anal sex
MasterClass: Anal Sex

Good Vibrations
The Good Vibrations Guide to Sex


Originally published November 2005 - "Taboo!"

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