Anal sex has come a long way, baby! Nearly 20 years ago, about 20 to 25% of women and men had engaged in anal sex. But in 2009, when ndiana University conducted the National Survey of Sexual Health and Behavior (NSSHB)--the most recent, up to date study of sexual behavior in America--they found that one of the most striking changes in American sexual behavior in nearly 20 years had to do with anal sex. As many as 40% to 45% of women and men in some age groups reported having engaged in it.
Anal play is more than just intercourse. It can involve fingering, licking, and toys. It's fantasy and role play. It's for men who are on the receiving end, it's (quite often) prostate stimulation. Let's start with the basics: anal fingering.
Anal fingering can be a comfortable and gentle place to begin exploring anal penetration. Unlike when using a sex toy, during finger-play the fingerer can feel for himself what is going on inside a partner's bum and get a sense of the interior landscape. Fingering is often used to warm up the butt for bigger things to come--sex toys or a penis--but it can be an enjoyable end point all on its own.
The anal tissues are delicate and can be torn easily, so make sure to trim and file your fingernails well before anal sex begins, thus eliminating any rough or sharp edges. If your nails are particularly long, pack them in cotton and wear a latex or non-latex glove. If you're fingering or being fingered by a non-monogamous partner, "no glove, no love" is a policy you might want to take literally.
What to Do:
Find a comfortable position in which the receiver can relax. A great deal of trust is involved when it comes to putting things in the butt, so many people like to start with the finger-ee on their back. In this position, partners can maintain eye contact and the person being fingered can see what is happening, including how many fingers are going in at once (that way, there's no surprises!) A pillow under the lower back is an easy way to prop up the behind without the receiver having to contort or balance on elbows.
There's not enough lube in the world to compensate for a lack of warm-up. So before anything is stuck anywhere, focus on the kinds of foreplay you typically enjoy together such as kissing, dirty talk, breast play or oral sex to get in the mood. Turn off the phone, dim the lights, play some relaxing music. And make sure to keep everything you'll need--gloves, lube etc.--bedside to avoid moment-killing fumbling. Lubrication is often the key between a good anal experience and the kind that turns people off of anal sex for life. Unlike the vagina, the anus doesn't lubricate on its own when aroused, so it's important to use a personal lubricant. Lubes are made from various ingredients and come in a multitude of consistencies.
When you're ready to try anal fingering, start by caressing the butt cheeks or teasing with kisses. With a well-lubed finger, circle the opening and "ring the doorbell"--tap the rosebud with the pad of a finger. This can be a good way to relax your partner's anus and gently open things up.
Ask your partner if it's okay to proceed. If given the green light, gently insert your index finger up to the first knuckle. Let your lover get used to the sensation and give the sphincter muscles a few seconds to relax; it might not be a bad time to check in again and make sure everyone is still having a good time. If and when your partner is ready for more, ease your finger further in; again, give your lover a chance to get used to the new sensation. If at any point your partner wants you to remove your finger, do so slowly and carefully.
If the two of you have decided to go in further, experiment to see what your partner likes. Explore the rectal walls with a gentle circular motion. Give a little wiggle. Try sliding your finger in and out, mix up the speeds and find out what pleases.
If you're the one getting fingered, don't be afraid to dictate the action. The first fingering is un-chartered territory for your partner and your feedback is all that he or she will have to go on. If something feels good, speak up! Everyone loves a compliment--especially a sex compliment. If you want something deeper or faster don't be afraid to ask. And definitely stop if something feels uncomfortable or painful.
Having mastered one finger, you might want to try two or more. One technique is to cross your gloved index and middle fingers into a mega-finger (make sure that mega finger is properly lubricated). Use the same methods as with one finger--go slow, and check in often with your partner. Again let the catcher be the one to call the pitches. (For the non-sports fans in the house: the person receiving the fingering gets to say what does or doesn't happen.)