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.
A couple more rounds of squeezing and pushing and you should have one finger all the way in. Always follow each round of pushing and squeezing with being completely still. The receiver usually has no idea how much finger they have taken so once you are all the way in; just feel around and get comfortable with the way their ass feels. That's excellent to do so you can get an idea of the angle of their ass. Nothing's worse than someone trying to fuck someone in the ass and going in at the wrong angle. Men usually jump out of their skin when your rub their prostate, a little marble sized gland located at the base of the penis inside the anus. At that point, if you've done everything right, they should be begging you to finger fuck them harder. Again, don't be afraid of water-based lubricant, more is better. Silicone-based lubricant is also very good but I have concerns about what elements are introduced into the body.
Whatever lubricant you use, be sure to use it liberally.
After you've gotten up some serious finger fucking, inserting another finger should be a piece of cake. You might have to go a couple more rounds of squeezing and pushing but I'd let the recipient control it at that point so they can drive the ship for a while. It's been my experience that you can get a third finger in and the receiver has no clue how many fingers are in them. I would like to caution you to NOT engage in fisting activities, or insertion of the entire hand into the rectum, because I'm not comfortable with that sort of hazardous practice that could cause serious injury. There are many people that engage in the practice but it seems awfully extreme when there are so many other anal options.
Because I personally don't have a real dick, I have to use toys, so for me, I usually start with a battery operated vibrator first and move on to the dildo. Use the same techniques for the small vibrators. More lube, more pushing, more squeezing. It should go in very easily so the trick is to start out slow with the vibrations and increase the intensity. Position the recipient on their knees with their face down in order to facilitate the best penetration. The dildo/dick comes next and you should basically let the recipient control the pace. Do a lot of touching and stroking and caressing all over their body when you put the head to the asshole and continue to use your pushing and squeezing techniques until the head is in. Once the head is in, DON'T DO A THING until the recipient tells you it's okay to proceed. Here is where the pushing out really comes in handy because with the tiniest bit of pressure they can accommodate the entire thing.
After about four inches of the dick/dildo is in, you are going to hit a little kink in the colon that is like a little bend. For many, that is the spot where they experience the most pleasure. Once the head is past that point, you are on your way to becoming an anal expert. If you've done all that and continued to talk to the person the entire time, you should be ass fucking like a pro. Go slow, get lots of feedback, and enjoy. It's incredible pleasure for both the giver and the receiver.
AND ALWAYS, ALWAYS, ALWAYS USE A CONDOM!
The information provided is NOT from a medical professional and should be considered opinion.
Please consult a physician or licensed sex therapist for further information.
