A Newbie's Guide to Anal Play

Contributed by Kelly Jones, Lavalife

Homophobes worry that anal sex will make them gay. Froufrou females assume it's just a painful form of male domination. Mysophobes believe that going in through the out door is messy.

Hypochondriacs are convinced their sphincters will get all loosey goosey for life. Wrong, wrong, wrong and wrong. If you ask a single person what they're looking for in a partner, chances are that somewhere on their wish list would be a mention of their performance in the sack.

Although technically illegal in some American states (mostly owing to archaic common law), anal sex, done right, is a completely healthy, pleasure-inducing form of sexual interaction. Despite its bad rap from Freud and later, the growth of HIV in the '80s and '90s, this now-hip hoopla is taking the world by storm. Heck, even one episode of Sex in the City focused on the chocolate starfish last year.

But before you cross what some consider to be The Last Sexual Frontier and let fanny frolicking intensify your orgasms, talk to your closest pals and learn more by picking up The Ultimate Guide to Anal Sex for Women and its companion book for Men both by Tristan Taormino, or Anal Pleasure and Health by Jack Morin, PhD. There's a lot to know about that sphincter of yours, and it would be a shame to exhaust your enthusiasm by starting things off on the wrong rump.

Shoot the Backside Breeze

Some mistakenly believe that all men want to try anal sex and all women deem it disgusting. Not so. If tush tickling is something you'd like to try, what harm is there in asking after your lover's curiosity? Though you could breach the subject by asking them to stick a digit in your derrière, there are more delicate ways of suggesting you'd like to experiment. Communicate your interest by gently touching their perineum (between the genitals and anus) during an intimate session or by guiding their hand to your perineum. Gauge their comfort and progress accordingly (see below). Make sure they know how to tell when you like it -- be it moaning or panting or lighting fireworks. Both parties must be comfortable expressing, "Stop, this doesn't feel right."

The Lube Tube

Unlike the vagina, the rectum doesn't produce its own lubrication, and its lining membrane can easily tear. In other words, use lube. Slather the finger, butt-toy or penile penetration from top to bottom to avoid discomfort. Some lubes are designed specifically for anal play, but whichever you choose, pick something long-lasting, non-sticky but thick, and safe for use with latex (read: no oil-based lubes, which can both disintegrate condoms and encourage infection).

Tush Toys

Consider playing with a butt bauble before something more organic. Anne Hooper, in her recent publication XXX Sex...Tonight!, writes of anal beads, vibrators, butt plugs and other sex toys. These come in a randy range of materials, shapes and sizes, and are known to give the user a more intense climax. Visit your local sex shop or surf on-line to compare sassy styles and butt-blissful brands. Always clean your toy carefully between uses, and never engage in vaginal intercourse immediately after anal penetration without washing first.

Analingus and Finger Foreplay

Also known as rimming, mouth-to-anus attention is a great way to stimulate and prepare the butt for penetration. And, like going down on a lover for fellatio or cunnilingus, analingus preferences vary from playmate to playmate. To determine what feels most titillating, try a combination of gentle tongue flicking, swirling around in circles, flat-out across from bottom to top, or pressing inward with a rigid tongue. Expand your licking to the perineum. Once the analee is ready to be probed deeper, SLOOOWLY press a finger tip on the anus, holding it there a few moments before proceeding just inside. Let them relax into this sensation of welcome intrusion. Retract the fingertip and reinsert, simulating rhythmic vaginal penetration, with increasing depth. Many find a combination of genital and anal play to be intensely arousing, so feel free to pay attention to their other bits and pieces simultaneously. If at any time pain results, stop and let the analee decide if they want to try another approach.

Pecker Penetrating Positions

Different lovers prefer certain anal sex positions, and dudes' and dudettes' druthers can depend not just on physical sensations but on emotional states as well. Almost all vaginal sex positions can -- in theory -- translate into anal sex poses, but it's unlikely all will feel first-rate. Experiment with doggie, on the side from behind, or with the woman lying on her back with her legs draped over her shoulders. While the woman-on-top arrangement gives pace and depth of penetration control to the straddler, engaged stomach muscles can make relaxing more difficult. And feeling relaxed is a requisite to rear-end romping. Use pillows to help maintain a position. Anal sex shouldn't hurt. If it does, try a different approach or top up the lube quotient.

Go Through the Motions

The basic motions of anal sex are similar to vaginal sex. Make sure to start slowly and smoothly, and play with different angles until you find one that feels just right. For many damsels, the most alluring angle is the one where the head of his trouser-snake hits the inner wall separating the anus from the vagina. For women pleasuring men with a finger or toy, the target to hit is the part of the anus closest to the prostate.

In Closing...

Anal sex need not be painful or messy or feel like your sexual orientation has somehow changed. Just like all things in life, slapdash situations can result in ouchie outcomes. Listen to your body, listen to your partner, and only move in motions that make you feel good. Embrace lube as your bestest friend, and try not to be goal-oriented: just enjoy the ride.