If you haven't come from there, you may also want to visit the previous page "Anal Sex 101" and the next one on "Fisting" (both mentioned again at the end of this article).
For various reasons anal play or sex - yes, there is a difference - appeals to many people who are into the many forms of erotic power exchange. Although personal motivations may vary, the need for the sub to actively cooperate as well as the fact that many people have a mental barrier here are the most common factors for this subject's popularity. Anal play is certainly not without risks, so you should be very aware of what you are doing. When you understand and know how to minimize them, the risks are minimal.
The first thing to be aware of every time you enter into it is that anal contact is HIV-risk number 1. If you are playing with a partner you do not know, just met, or are having a one night stand with - and possibly most important - if you have a bisexual partner - take all precautions necessary. Maybe you have heard this before but the time required for HIV to be discovered varies from person to person and can be as long as seven years. In other words, having known each other for three months is no guarantee for protection...so protect yourself.
There are five different forms of anal play and the differences as well as the effects can to a large extent be compared to vaginal play:
finger- and/or fist play
Don't worry, we'll get to the differences. First. Let's try to clarify some other - more general - aspects.
Anal play is nothing to be ashamed of, although many, many people are. We started it in our earliest childhood. In fact it is generally acknowledged as the first sexually related exploration every baby does and even some fetuses do it prior to birth. Let's face it, the odor of plain shit - but called "musk" - is used in almost every perfume and even more so in male cosmetics because it is generally known as sexually appealing. For you animal lovers out there: the scent is derived from the musk plant, not the deer. Any biologist will explain that in all mammals, the genitals and the anus were deliberately placed close together, simply because the smell of the one points the way to the other. So, if you like it, or feel attracted to it, there is absolutely nothing wrong with it.
Plus, the anus is an erogenous zone by itself, whether you like it or not. Stimulating it will cause sexual arousal and feeling somebody "touching your vagina from the outside" (which is one of the effects) is an amazing sensation for a woman.
Kinsey - the sexologist best know for his extensive research of the sexual behavior of both men and women - said it as follows: "The contractions of the buttocks reflect, more than any one factor, the development of the tensions involved in erotic arousal." The buttock muscles are among the strongest in the human body and they come into play during almost any form of sexual intercourse and even masturbation - especially for women. Some women even masturbate just by contracting and relaxing muscles and these include the "back door". In the event you thought anal sexual attraction is just for a few, Kinsey - in his extensive research - found that fifty (!) percent of both men and women had had some experience with anal stimulation or anal intercourse. More recent research in the USA shows that some ten percent of the heterosexual couples regularly have anal intercourse.
The anal and vaginal region and the penis share the same nerve roots and this is the physiological explanation for the sexual attraction of the anus. And - coming back to erotic power exchange - anal play and intercourse to many has strong connotations with terms of dominance and submission.
Penis/anal penetration - For the man the main advantage of penetrating the anus with his penis is that the anus is not only very narrow, but also the circular muscle around it is much stronger. As a result he will feel much more sensation, compared to penetrating the relatively soft and receptive vagina. The vaginal contractions he feels only during the female orgasm is what he feels constantly while penetrating the anus. To the majority of those being analy penetrated the attraction is in two things: one being the "giving" of this to their partner and of course the stimulation itself.
Fingerplay and fisting - Stimulating the anus with fingers, although desirable all by itself, causes very relaxing feelings when done carefully, and is mainly foreplay to something else: either anal intercourse or anal fisting. If anal play is new to someone, they may have trouble relaxing the anal sphincter muscle. To break through this mostly mental block, they may require gentle massage and training to open up. (For information on fisting use the link provided later).
Toys - Toys are mainly used as devices to train the anus for further play. To avoid all sorts of unwanted mishaps, please only use specially designed toys (like butt plugs) for this purpose and not, for example, vibrators. Apart from this, vibrators and dildos are usually too stiff for the anus. Toys for anal play should be very flexible, made from latex or silicone (which is a different type of silicone than used for plastic breast surgery).
Rimming - Rimming is stimulating the anus with your tongue. The technique can be compared to oral stimulation of the vagina.
Enemas - An enema is technique where (usually) fluid is brought into the bowels to force them to expell their content. This may be used for various purposes - cleaning before fisting, as a punishment, humiliation, training and sexual arousal, all of course depending on your own preferences.
The use of latex gloves when using your hands is a must, to protect yourself, to protect your partners, their insides and for hygienic reasons. Never move your hands, fingers, penis or toys from the anus to the vagina without thoroughly washing them first!
Cover your penis and toys with condoms at all times, to protect yourself, your partners and your toys.
When penetrating a partner you do not know well, use a double or even a triple condom and do buy condoms designed for anal play (GaySafe for example).
Item number two in any form of anal play is lubricant. Lots of it. Don't be shy about using lubricant! Be as generous as you can and add repeatedly, especially during finger play and fisting. Always use water based lubricant only. Oil based lubricants, as well as butter (don't laugh, this is still frequently used) will ruin latex and render your protection useless.
Rimming without dental dams is outright unsafe unless you have been married or lived together for a long time and have had sex only with each other.
Before finger play or fisting - even when wearing gloves - file your nails to avoid damaging tissue. Run the pad of your thumb around each nail, if can feel your nails at all the odds are you'll cut your partner...or your glove. File them again.
Wash thoroughly before and after. Some people prefer the use of enemas before anal play to clean out the area. The best way to do this is the old-fashioned way. Use an enema bag and fill it with about a mug full of lukewarm water or milk, or buy a Fleets enema kit at the store (USA - brand names in Europe may vary). Never ever buy an enema kit from a sex boutique. No matter what they tell you - use the correct and safe equipment or none at all!
Additionally, the following things are best NOT done:
anal play during illness of any kind.
using objects or toys that were not specifically designed for anal use.
applying force of any kind (the anus will swallow your finger, even fist, or toys, all by itself).
Anal sex should be avoided if one has hemorrhoids, infections or small wounds around the anal area for various reasons. One is the HIV risk, another is that your movements around the area may spread bacteria from the inside to the outside and last but not least, it usually hurts too much.
Except for the HIV-risk, ejaculating inside is not a problem at all.
The intestines are anything but straight. The rectum (the part just before the anal opening) ends in a sharp, ninety degree upward curve. (For some of you this is why you cannot get all of your penis in). If you attempt to push past this turn, you will only cause tremendous pain, for both yourself and for your partner. When penetrating with your fingers or fist remember this turn is the second hurdle you have to take, which requires just as much attention, ease and patience as the anus itself. The upward turn has a second ring of muscle around it (which is what holds the feces inside) and this one needs to be relaxed as well.
Also, remember that whereas the vagina is literally a dead end, the intestines are not and this is the main reason to use only toys designed for this kind of play. They are designed in such a way that they cannot accidentally slip inside and disappear. Should this happen anyway, please do not hesitate to visit your doctor or the nearest emergency room. It may come out by itself, but there is no certainty here. Yes, if it happens it is embarrassing, but do remember that doctors and nurses have seen it all before and are only there to help you (which is what they will do) not to judge you.
The inside of the intestines has very delicate lining that is damaged easily, a good reason to wear gloves at all times. Fingernails can do a lot of damage but so can rough or unexpected movements.
Getting in takes time, especially the first times. Take all the time in the world. If you fail the first time, that is not a problem. In fact it is normal. Simply try again later or another time. Go slow and be careful. The anus, when massaged carefully, gently and long enough, will open up itself and is usually capable of doing very unexpected things.
The trick is to relax, so be sure to put your partner into a comfortable position. Do it step by step. Get one finger in first, then slowly and gently add the next one and maybe after a while another one. If you want to penetrate with your penis, now is the time to do so.
Getting out is done in the same careful way. Go slow, even if the anus tries to push you out.
There is a very good chance your partners will need to visit the bathroom immediately after a session. If they don't, ask them gently and even accompany or encourage them to do so. Even if they doesn't "have to," being open about it will at least take the tension away and help them relax.
Most people, especially when inexperienced in this area, will need lots and lots of support, love, care and tenderness, before, during and after a session. Remember that most people need to break through a huge mental barrier and that barrier will not be gone after the first time. It takes quite a while to get over the feeling of shame. Communication is paramount here.
Another very practical thing to remember - but it makes a great form of after care as well - is that anal play to many people will stimulate the digestive process. In other words, your partner may very well be hungry afterwards. Think ahead and make sure you have a bite to eat readily available (which is good advice after most scenes, as the stress and fatigue of a session will make you and your partners hungry). Sweets, i.e. sugar, will help regain some energy quickly and be sure to offer something to drink as well. Both the emotions and stress have a draining and dehydrating effect.
If you let your partners drink an isotonic drink first (like Gatorade) they will quickly regain their energy. This will also help prevent another thing. If you are planning to have an alcoholic drink later, remember that after a scene a body will absorb any liquid like a sponge and if it is has alcohol will get them very drunk. The isotonic drink will prevent this from happening.
For some additional related information your can see the previous anal sex page plus here's a page on fisting; you can also look for Jack Morin's book "Anal Pleasure and Health" (ISBN 0-940208-083, Down There Press, Burlingame, CA) which is a very good reference.