So you want to try anal sex.  You’ve heard about it, read about it, and maybe even had secret fantasies about it.  As an anal virgin you are curious, maybe a bit fearful, and wondering what it’s all about.  We are taught as children that the anus is a dirty, secret place and many of us carry those taboos with us into adulthood.  But, the anus is a very sensitive area, and, when given the proper attention, can bring one to a whole new level of ecstasy.  For men, the anus is the gateway to the prostate, a very sensitive area that many men may achieve orgasm from when stimulated.   Anal expert, Tristan Taormino notes that the “anus, anal canal, and rectum are wonderfully erogenous zones, rich in nerve endings and super-sensitive to stimulation and penetration. At the right angle, many women find that you can indirectly stimulate the G-spot through anal penetration.”  Many sex experts recommend that you arouse yourself in the regular ways, until you are good and hot before attempting anal play and to continue stimulation throughout.

The most important thing to consider with trying anal sex with a partner for the first time is that the person being penetrated is the one in charge.  Communication is essential with any type of sex play and even more so for anal play.  It is important to go slow, get fully aroused, use plenty of lubricant (and then some), and to listen to your partner’s needs and body language.  Because the anus has a very thin lining it is important to be careful not to tear it and to use condoms for safe sex purposes. Always stop if you experience pain or discomfort.

Solo Anal Play

The best way to try anal sex for the first time is through masturbation.  That way you are really in control and can decide how big, how far and how fast on your own.  Self exploration is important as it allows you to discover what feels best and how your body responds.  You also don’t have the pressure of performing or trying to satisfy your partner’s needs.

Warming Up: The Rosebud of Pleasure

Developed by massage therapist and sex educator Joseph Kramer, this is a good way to begin exploring anal pleasure.  First, begin with massaging your buttocks to get the blood flowing.  Try squeezing your cheeks with your fingers, raking your fingernails over your ass, and even slapping it.  Slowly begin to clench and unclench the asshole.  Next, lube your finger very well and rub the pad of you finger around the anal rim, exploring the sensitive rosebud.  Lube up the crack and slide your hand up and down.  Finally, when you feel ready, you can insert a finger inside the sphincter, gently stretching it and massage the silky skin inside.  It is also recommended to stimulate other areas of your body as you would naturally, to get yourself good and aroused.

Sex Toys for Anal Play

There are a large variety of sex toys available for anal play.  These include butt plugs, anal beads, anal vibrators, prostate stimulators, and anal dildos.  They all have different purposes and will give your body different types of pleasure.  Butt plugs have a narrow head and flared base.  They are generally used for anal training, starting from small and slim, to allow you to get used to having something in your anus.  These are inserted and then stay in place for as long as you want to keep them there.  Tantus makes a whole line of excellent butt plugs called Flirts in various sizes all made of medical grade silicone.  Anal vibrators and dildos are more for stroking penetration, similar to regular penile sex play with a partner.  They can often be used on a harness for lesbian penetrative sex and bend-over-boyfriends.  The Rude-Boy prostate stimulator is a great toy for men who want to try a bit of buzz, while the Vivid Red Hots Briana Vibe is a good choice for women.

Prostate stimulators like the Aneros are used to put pressure against the male prostate and are used in a rocking motion rather than in and out.  The male prostate is an area of immense pleasure and will often lead to intense orgasms when stimulated.  Anal beads, like the Bendybeads by Fun Factory, are one of the most non-threatening ways to begin anal adventures for anal virgins and can be used simultaneously with vaginal penetration or clitoral stimulation.  They are inserted one by one and then gently pulled out.

Any anal toy should have a wide base or a retrieval ring so the toy is easily removed.  When first exploring anal play it is important to start small and work your way up to larger sizes.  The most important “toy” for anal play is lubricant!  This cannot be stressed enough.  If you want to have a healthy, happy experience with anal play use lots of lube.  Good ones to try are Moist Anal Lube and Adam and Eve Anal Lube.

Anal Insertion

Like the vagina the anus can also receive enormous pleasure from the insertion of fingers or toys.  Start small, using a fingertip after you have stimulated the rosebud for a while, making sure to use lots of lubrication.  If your fingertip feels good you may want to insert the entire length of the finger, or even try two.  After a while, your anus will get more used to the feeling of fullness and you can try larger toys like slim butt plugs, anal beads, and anal dildos.

At first, anal play will feel strange and you will most likely want to push what is entering back out.  This is after all a natural reaction.  If you relax into it, however, anal insertion can be a wonderful experience that can intensify sexual play and orgasm.

Many people worry about mess during or after anal play.  Be sure to empty your bowels before anal play.  You can also choose to flush yourself out with an anal douche about an hour before play.  I found it much easier to enjoy anal play in the bath tub with toys designed for underwater fun.  It allows you to focus more on the pleasure and sensation, instead of worrying about messy accidents.  Also, a warm bath will help you relax, which is essential for anal play.

Anal Sex with Partners

Now that you’ve experienced a bit of solo play, it’s time to try out your new found passion with your partner.  Both men and women enjoy the experience of anal sex with a partner, no matter if you are GLBT or straight.  Most important is who is in control.  The partner being penetrated should always be in control of the pace and degree of penetration.  Anal sex is not supposed to hurt and if it does you are perhaps not ready or doing it wrong.  To avoid hurting your partner, make sure that you both communicate with each other.  “Mmmm, that feels good,” “More…”, “Back up a bit,” whatever works for you.  Express yourself.  Make sure you are ready for the experience and not being pressured into it just for your partner.  Try to relax, because a tight sphincter muscle can cause pain.  And use plenty of lube.  Oral anal play, called rimming, is a good way to arouse that area and make your partner relax for penetrative anal sex.  Learning the ins and outs of anal play will make you an expert.  For more expert information on anal play I recommend the DVD: Nina Hartley’s Advanced Guide to Anal Sex - For Men and Women; and the following books: The Ultimate Guide to Anal Sex for Men and The Ultimate Guide to Anal Sex for Women.

Bend Over Boyfriend

Some straight men have some misconceptions about anal sex (getting penetrated) that make them hesitant to try it out with their partner.  The prostrate is a very erogenous zone and the ultimate pleasure zone for men.  Anal sex will not make you gay.  That is a myth and many straight men enjoy anal play once they get over the social taboos.

Make sure your hands are clean or use gloves.  Also, trim your nails first as you don’t want to damage the delicate lining of the anus.  Next, you can saddle-up Cowgirl and move up to a dildo and a harness to give your guy the ride of his life!

Anal Do’s and Don’ts

Anal Do’s

•    Clean yourself and your toys.
•    Use a condom or latex gloves.
•    Trim nails of rough edges.
•    Relax, breath & take it slow.
•    Use lots of lube. I mean lots.
•    Stop if there is pain.
•    Only use toys with a flared base designed for anal play.

Anal Don’ts

•    Insert toys in the anus then the vagina as it may cause infection.
•    Insert sharp or foreign objects or anything too big.
•    Do it if you really don’t want it.
•    Hurry or force it.
•    Pressure your partner into it if they are not ready.

Domina Doll is a sex writer who writes articles and reviews for various magazines, zines and adult toy stores.  Visit her sexuality blog CherryBoxxx at http://cherryboxxx.wordpress.com/.

In my last post, I admitted that I kissed a girl… and I liked it. Well, the truth is, I’ve done much more than that with a woman…and her husband… and my husband, too.

Yet my husband and I eschew the title “swingers.” We don’t attend parties, answer ads on craigslist, or frequent dating sites to hook up with other swingers. On a lark, my husband once typed in an e-mail reply to a hot guy on Craig’s List for me, but by the time my face had blushed from bright pink to red to purple, he deleted it. I can’t imagine hooking up with a complete stranger.

In fact, our “swinging” lifestyle occurred by accident. Six friends, lots of alcohol, some yummy chocolate cordials whose filling tasted even better licked off the breasts of my best friend—and we all stopped short of having sex. Sadly, no sex occurred that night even amongst significant others and we have since dubbed the night, “The orgy where no one got laid.”

But it got four out of the six of us talking. And planning. And we have now strengthened our friendship in wonderful, beautiful, naughty ways.

Many swingers claim the worst thing a couple can do is have sex with friends. It’s like… well… having sex with a friend. It can get complicated. In his book My Boring-Ass Life, Kevin Smith shares this observation about threesomes: “Post-menage relationships are awfully difficult to maintain…. There’s this fall-out involved in crossing that line that makes for awkward conversations in the light of day, once everybody’s clothes are back on… that’s not unlike chatting up your ex, but even more delicate.”

He recommends sticking to threesomes (or foursomes) with total strangers or people you will never see again.

Maybe I’m just lucky, but for us, playing with another couple has turned into a beautiful expression of our friendship. Our friend once observed, “I like playing with you guys—there’s no drama.”

How do you keep a swinging relationship drama free—amongst friends or strangers?

No Drama

Set ground rules. Alcohol can be a great social lubricant (and, in moderation, can help prolong the night’s festivities.) Set ground rules before the first Mojito is mixed, and stick to them. Discuss what’s okay and what’s not. And remember—whatever you, as couples decide, can be okay or can be off-limits. There are no wrong choices.

Ground rules should include discussion of safe sex. Condoms should be mandatory, but if you have all been recently tested for the gamut of STDs and the women are on another form of birth control, you can discuss this, too. Partners in previously monogamous relationships may not be accustomed to condoms, so you’ll want to discuss preferences, hang-ups, and maybe even consider brands designed for greater sensitivity.

If you choose not to drink at all, that’s okay, too. Things may get started a bit more slowly, but everyone will have greater control. Some swingers ban alcohol entirely from their relationships.

If someone crosses the line, stop him or her firmly, but gently. Be understanding. During our first get-together, we decided we weren’t ready for penetration. When hubby got a bit too close, our darling friend simply smiled and said, “Now, now, none of that,” in a friendly, gentle tone. No one was made uncomfortable.

In the heat of the moment, passion can take over. A gentle warning should be all that’s needed. By all means, if the party doesn’t listen, you have a legitimate gripe and may want to put an end to the night and re-consider the entire relationship. Even then, the friendship might be saved with good communication, even though the swinging aspect may disappear.

Don’t compare yourself. I don’t know if guys do this, but it’s inevitable for a woman, faced with another naked woman, to compare—her boobs, her belly, her butt… anything below the neck is fair game. Feel comfortable complimenting your female counterpart, but don’t make yourself uncomfortable because she’s got 34Ds and you’re barely an A. All women are beautiful and one thing I can guarantee is that the men are not comparing.

A little jealousy is normal; enjoy it but don’t harp on it. Your partner may be admiring the physical attributes of your counterpart; this is normal. You may get a pang of jealousy, but this adrenaline rush is part of the thrill of swinging. Don’t let it consume you or ruin the night. Do some ogling of your own. Vive la difference in all body types!

Games can loosen you up. Simple dice or spin-the-wheel games, strip-anything (poker, darts, Wii…) or adult board games that get you talking about your turn-ons are a great way to start the night.

Getting Started

So, is swinging for you? Are you sexually open, not overly jealous or competitive, and looking for a creative way to spice up your love life? Sex with friends—or strangers– might be just the thing.

How do you broach the subject with your attractive neighbors or even lifelong best friends? That’s a tough one. Start with flirting and let it evolve organically.

In most foursomes, two parties are the “communicators.” This may be the men, the women, or a combination. They might be closer friends who share everything on a normal basis, or they could be the two parties who analyze every situation ad infinitum.

Let the natural communicators get the wheels turning and bring the conclusions back to their partners… if you’re close enough friends, and you’ve already been getting vibes about the possibility of a hook-up, no topic should be “too weird” to discuss.

One last point: for a great instructional erotic video on swinging and tips from a woman who knows far more than I do, check out Nina Hartley’s Guide to Swinging DVD.