Anal sex is considered taboo in many social circles. It's also a sexual practice that can provide tremendous sexual pleasure for the participants. The following information is a guide to anal sex for both men and women that should facilitate pleasure and intimacy between partners in a safe way.
To set the stage, I recommend starting with a healthy bowel movement at least two hours prior to trying anal sex. The rectum should actually be devoid of any poo poo. If that is done, you shouldn't have to worry about things getting too terribly messy. I suggest the use of an enema and you can get a premixed formula at the drug store for less than $2.00 or use the good old fashioned kind your grandmother used to give you from the red bag. After that, a shower to clean any trace poo poo away should set the stage. If you have any cuts, hemorrhoids, or anal tears, DO NOT, I repeat DO NOT attempt anal sex, not even with a condom.
The key to anal sex is start small and go slow. While I like small butt plugs and vibrators as an introduction, my preference is tongue. It's much softer and pliable and gives a lot more pleasure. It's also more intimate. Depending on the experience of the giving party, they may or may not be comfortable with "tossing the salad" or licking someone's ass so again it's a personal call. It's imperative to constantly ask for feedback and give encouragement for both parties. Sex is mostly mental so it's about getting the person relaxed and aroused. Tell him or her how sexy their asshole, how much it turns you on to know that they are giving it to you, sharing it with you, how much pleasure you want to give them, how good it tastes, etc. If it's a guy, jerking him off is essential while licking him, if it's a woman, have her use a vibrator on her clit because she'll know her body better than anyone and can create more arousal. Extreme sexual arousal is the key to great anal sex.
After sufficient licking, about 15 minutes or so, start with a finger. There are actually two actions that will help relax the muscles around the anus that will make anal sex less painful. "Squeezing" and "Pushing" should be used in tandem to help relax the muscles. Use a lot of lubricant. There's no such thing as too much. The recipient should push out, like they are trying to have a bowel movement. That allows for easier penetration. With the tip of your finger in, then tell them to squeeze, squeeze, squeeze, like they are trying to hold in an urgent movement, which causes the sphincter to get exhausted. After they've done that, go back to stimulating the pussy or dick and just leave the tip of your finger as still as possible. Once they have done that for a few while, tell them to push out again, which should allow your finger to go in without any real effort on your part. Once you are in a little deeper, let them get used to the feeling of your finger in there and then tell them to squeeze for dear life. Each time they squeeze, the anal ring will get weaker and weaker, making it looser. By this time, they should be loving every second of it so you should just keep on with the verbal encouragement. I find dirty talk increase stimulation so try your hand at some explicit language to heat things up.
