Why Anal Play?

The first time I ever told anyone I wanted to touch their anus they said "Ewwww, why would you want to do that?"

Why indeed?

The most basic answer is because it is enjoyable. This in itself is answer enough. However, many people find it useful to explore the issue on a deeper level.

Anal play feel very good on a simple physical level. The anus is extremely sensitive and therefore can be an excellent receptor to simple sensual pleasure. Many men enjoy having their prostate rubbed, and some women are capable of orgasm simply from anal penetration.

Many people see receiving anal sex as a submissive act. My answer to these people is if you enjoy it as a submissive act do so, but it doesn't have to be if you don't want it to be. Anal play is what you make of it.

Others see receiving anal play as an inherently female act. They seem to think that someone who allows something phallic into their body is acting as the female. I disagree with the simple minded approach, but personally enjoy roleplaying as a female during anal play. And yes, those are my panties
: )

Some see anal play as a "dirty" act. It doesn't have to be. After a good enema, anal sex can be as clean is vaginal sex. However, if you like the idea of touching and playing with shit, or enjoying a sexual act simply because it is dirty, go for it. (Make sure to think about safer sex, however.)

These ideas, concepts, prejudices, and emotions are all wrapped up with the idea of using the anus for sexual pleasure. This is all cultural baggage. I say, if these ideas get you off and help you enjoy yourself, more power to you. You are taking the negative cultural images and using them for your own pleasure, you wonderful pervert, you. : ) If one of these concepts stops you from enjoying anal play, I urge you think more about where your idea came from.

Anatomy

To understand what's going on down there you need to learn about anatomy.

Outer Sphincter:

This is the exterior ring of muscles in the sphincter. As you slide a finger into the anus, you can feel this muscle relax first.

Inner Sphincter:

The interior ring of muscles in the sphincter. The outer and inner sphincter make up the anus.

Rectum:

The rectum is where objects inserted into the anus go. It can be fairly large, volume wise.

Prostate:

Present only in men, the prostate can be rubbed by a finger inserted into the anus. It can feel very good. With the man on his back, insert your index finger most of the way with the palm side of your hand facing up. Make a "come here" motion and you will stimulate the prostate. It is analogous to the g-spot in women.

Pubo-Rectal Sling:

This is a "sling" of muscle that pulls the lower rectum towards the belly button. It helps control bowel movements. In order for a large object to be inserted into the rectum the pubo-rectal sling needs to relax for the rectum to straighten out.

Sigmoid Colon:

This is where the large intestine takes a big left turn. In general, you won't be inserting anything that far up.

Lubricant

Unlike the vagina, the anus and rectum does not produce lubricant. Therefore, to enjoy sensation there we need to add some. We don't need to add just a little, but lots. An icon of pornography, using vaginal lubrication to lube the anus just doesn't work. There's a saying which illustrates this:

Oil-based lubricants:

The rectum is self cleaning. Any liquid you put in is going to come back out eventually. Therefore, it is okay to use oil-based lubricants, assuming you aren't using a condom on whatever is being inserted. Mineral oil, commercial oil based sex lubricants and food oils are all fine. Crisco (regular flavor) is a long time favorite of the gay male community.
The problem with oil-based lubricants is that they dissolve latex.

Do not mix oil-based lubes and condoms.

I have heard reports that the latex in gloves is thick, and does not break down quickly enough to be a problem.

Water-based lubricants:

Water-based lubricants don't have this problem. They are also much easier to clean up. Many commercial water-based sex lubes are available. However, only the thick, goopy lubes should be used for anal play. "Runny" lubes such as thin Astroglide don't work well as they will not work their way into the rectum.

Personally speaking I prefer water-based to oil-based lubes. I find that oil-based lubes feel greasy and tacky. I find water-based lubes to feel wet and squishy. I like that. My personal favorite is ID. You can buy it in pump bottles.

Push the piston up all the way, put the nozzle of the lube container against it, and inject the lube, pushing the piston down. Now gently slide the injector into your warmed-up partner at a good angle. (More on this later.) Tell your partner when you are about to inject the lube, as it can feel rather good. : ) There is one drawback to inserting this much lube, your next bowel movement tends to start out similar to diarrhea.

     Make sure you add more lubricant as time goes on if you are playing for more than a few minutes. You can do this by simply pulling the inserted object most of the way out, adding more lube, and sliding back in. One last word about lubricants. You can buy lubricants with numbing agents, such as "Anal-Ease". Basically they contain novocaine or similar drugs to "alleviate painful anal sex." If it's painful, you are doing it wrong! These lubricants are dangerous! I hope someone sues the manufacturers of these products soon and get the damn things off the market. I feel they reinforce the concept that anal sex is something to be "endured" for the sake of one's partner. BULLSHIT.

Angle

The rectum is not a straight tube, at least when you start out. The pubo-rectal sling pulls the rectum into an "S" curve. If you don't insert an object, or your fingers, at the right angle, it won't feel good.

Aim for the Belly Button:

As you start to insert something past the anus, into the rectum, aim for the belly button. If you are inserting fingers, or something finger-length or shorter, you are all set. If you are inserting something longer, you will probably have to adjust your aim.

Stop and Pull Back:

After a few inches, your partner will tell you, if you have good communication, that it starts to hurt. You've hit the curve. Pull the object back just a smidge. Let your partner know that you aren't going to move, and DON'T move.

A fraction of an inch feels like a foot when it's YOUR ass.

Aim for the Head:

When your partner signals she/he is ready to go deeper, move your aim up towards the head, and slide back in slowly. As you relax more, the pubo-rectal sling elongates, lessening the curve and increasing the comfort. I highly recommend flexible dildos for anal play because of the curve of the rectum.

Eventually the rectum takes a left turn into the sigmoid colon, but you should not be going up that far unless you really know what you are doing.

Relaxation

This is both the most important and hardest part of anal play.

The tightness of the anus is a direct indicator of emotional tension. It's like a mood ring. You need to relax and have fun before your anus can relax and have fun.

Convincing the anus to relax takes time. I mean this in two ways. The simplest is time during a play session. This means start off with something small and work your way up when you are playing. The other is on a longer time scale. If the receiving partner has never had anything in her or his anus, don't try anal sex the first time. Work your way up to it over several sessions.

Short term:

Over the course of a play session, if things are going well, your anus will relax. You will be able to accept larger things into the anus. Your pubo-rectal sling will elongate and you will be less sensitive to the shape and angle of the inserted object. You will also be able to enjoy the sensation more. You need to take things slowly though. Start off with one finger and work your way up. Don't do something stupid like thinking you can just shove the large butt-plug in with a smile and a grunt. Take your time and enjoy yourself. It's not a race.

Long term:

As you do more anal play over time, you will be better at it. It's an athletic activity. Don't expect to be able to dunk like Michael Jordan the first time. If you are a beginner, only try one finger the first time. Maybe on the second or third time, try two fingers. On the fifth or sixth time, try a small dildo.

Physical Aspects:

You have to realize that the sphincter is not your average muscle. It's large, strong, but not normally under conscious control. As children, we take delight in defecation. But as we get older, we learn to disassociate with it. We don't even think about it. When you do anal play, you need to get re-acquainted with your anus. You will feel new sensations. When someone is new to anal play and you ask them if it feels good, they will have to think about it. We have to learn to communicate with the anus, and communication is a two-way street. Give it time and it will happen. Your muscles will remember what to do after a bit of training. Just give yourself time to learn.

Emotional Aspects:

Many people have fear and apprehension about their backsides. You don't trust what you can't see. Issues with cleanliness, comfort level with partner, fear of pain, fear of injury, and bad past experiences will all affect how well you can relax. These are all things you're going to need to talk to your partner about.

Cleanliness

Many people, including me, have cleanliness apprehensions about anal play. Usually, feces stay in the bowels, and only move into the lower rectum right before a bowel movement, so you are not going to encounter them very often. Simply go the bathroom beforehand, and there probably won't be a problem with this.

However, you will often encounter small amounts of feces, like tiny flakes of shit. Usually the lubricant will turn a pale brown. If this bothers you, you will probably want to have an enema beforehand.

The easiest way to give an enema is with the disposable enemas you can buy at any drug store. These cost less than one dollar, and are simple to use. Although they are not very big volume-wise, they do the trick. Make sure to get water or saline enemas, not oil or detergent ones.

As far as external cleanliness, it helps to have the hair around the anus trimmed back, for those of us with hairy rear-ends.

Another option is to do anal play in the shower. Any "uncleanliness" you encounter is simply washed away. You do have to use more lube though, assuming you are using a water-based lube. It too will get washed away.

Health Issues

It's very hard to enjoy your anus during sex when you are used to it being a source of pain in your normal everyday life. In general, if you are having anal health problems, I recommend you go very light with the anal play. However, completely foregoing anal play because of a health problem can make you feel so negative about that part of your body as to make your problem worse. You need to work with your anus.

Hemorrhoids:

Hemorrhoids are characterized by puffing or swelling of the tissue of the anus. It can be accompanied by a burning, itching, or painful sensation, especially during defecation. MANY people, especially as they get older, get mild hemorrhoids. Think of all those Preparation H commercials to think of how many people have them.

Anal Fissures:

Anal fissures are cracks in the skin of the anus, similar to paper cuts. These are usually radial. They can cause sharp pain during defecation, with a small bloody smear on the feces or toilet paper. They are often slow to heal. They can be caused by straining during bowel movements, and stretching the anus instead of letting it relax. They can also be caused by sharp fingernails.

Management & Healing:

In order to get better you're going to have to do two things. First, you should find yourself a good doctor, and second, you are going to have to change your diet and bathroom habits.
     When I was having problems and went to my general practitioner, he didn't even know what a butt plug was. I soon gave up on him. I suggest finding a gay doctor, regardless of your gender or orientation. I feel they tend to be much more open to the concept of using the anus for sexual pleasure. If your doctor is not doing what is needed to help you get better, find another one.
     A high fiber diet is essential to improving anal health. It bulks up the feces and helps trigger the natural elimination process, meaning you don't have to push very hard. Fruits and vegetables are a natural way to get fiber. However, Metamucil works wonders. The smooth texture orange flavored Metamucil mixed with a large amount of orange juice does not taste bad. Also, pay attention when you are going the bathroom. Sitting and straining is a major cause of anal problems.

The Myth of the Permanently Stretched Anus:

Here's the health problem than people fear the most from anal play:  loss of control of bathroom functions. It just doesn't work that way. It would take extreme force to tear the muscle. When you are accepting something into the anus, you are doing it by relaxing this ring of muscle. After you are done with anal play, it will resume its normal state - closed.
     There is anecdotal evidence that the use of a butt plug for long periods of time (many hours per day) can cause loss of anal muscle tone. This is often referred to as butt plug training. It would appear that an exceedingly high level of plug use can lead to dependence on a butt plug. While I'm not sure if this is true or not, I would suspect that interfering with the natural action of a muscle this much could cause problems.

Safety

STDs:

Studies have shown that unprotected anal intercourse is THE MOST EFFECTIVE method of transmitting HIV. One way of thinking about it is if you are going to have unprotected anal sex, consider that you might as well have a blood transfusion with the person.
     Besides the specter of HIV, there are less dangerous but avoidable ills such as herpes and hepatitis that can be transmitted to and from the anus. There are now hepatitis vaccines available. They are fairly inexpensive, and with some insurance companies, free. I suggest you discuss getting a series with your doctor.
     Another issue as well is the bowels' natural bacteria. Rimming (mouth to anus contact) can transfer enough bacteria to make you sick.

Latex:

The best way to prevent transmission of disease, after abstinence, is latex barriers. This means latex gloves, dental dams, and condoms. One nice thing about the BDSM scene is that latex is pretty much taken for granted. It really becomes second nature.
     Dental dams are much easier to get these days. They are also being made in forms designed for sex. Real dental dams are on the small side. I've tried the trick where you cut a condom up the middle to make a dam. I found that you don't get a wide enough piece. A better idea is to cut the fingers (NOT the thumb) off of a latex glove. Then you cut the latex up the pinkie side and you are left with a dental dam with a tongue protuberance where the thumb would normally go. You will probably want to wash the icky tasting powder off and to lube the latex on the anus side for more comfort and better sensation. Personally speaking, nothing gets near my anus without lube.
     You can get latex gloves at just about any drugstore. If they have a size gauge on the side of the box, use it to decide which size to get, or take one out of the box and try on for fit. This is one case where size really does make a difference : ) Gloves that are too big wrinkle and are hard to use; gloves that are too small are tight and don't allow you to move well. Whenever you use gloves for anal play, put a glove on each hand. This means if you want to switch hands halfway through, you don't have to try to put on a glove one-handed. I learned this trick from Mentor.
     Everyone knows you don't mix oil-based lubricants with condoms. However, there seems to be some evidence that latex gloves are thick enough to stand up to oil for the time of a play session. Unfortunately, Consumer Reports won't be doing scientific tests anytime soon. Some people will use two gloves on each hand. You can also purchase Nitrile gloves, which are special surgical gloves that hold up under oil-based lubricants.

Cross Contamination:

One thing to watch out for in female receptive anal sex is transference of bacteria from the anus to the vagina. This means nothing that has been in the anus should go into the vagina without changing latex or a thorough washing. Going from vagina to anus is fine.
     Women who use the same dildo in both their ass and vagina often use a condom on the dildo when using it in their ass.

Anal injuries:

People occasionally hurt themselves during anal play. They can either go too fast, or get a small cut because of a fingernail. The result is a small amount of blood, usually followed by sharp pain during defecation for the next several days. There will often be blood smeared on the toilet paper. If this doesn't go away in a week or so, see your doctor. Medically speaking, this is not usually a big deal. However, it is a clear sign you went too fast and really need to slow down next time. A distributed burning sensation is also a sign you went too fast or didn't use enough lube.
     If a large amount of blood shows up directly after anal play, and you think you may have perforated the rectum, go to the emergency room now. A perforated rectum can cause death in a few days. The only way this could happen is if you are using a sharp object or extreme force.

Toys

Butt plugs:

There are also many different butt-plugs out there. Most are made of a rubberish jelly substance. These are great except that they are often WAY too big for most people. Remember you mother saying "Your eyes are bigger than your stomach" when you ordered the 3 serving banana split all for yourself? Well, be careful that the same thing doesn't happen when you are buying adult toys.
     Most "smalls" are a good start for most people, not being much bigger than a wide finger. Most "mediums" are too big unless you are fairly experienced. Don't EVEN get me started on the "larges".

Inflatables:

Inflatable butt-plugs and dildos are also available. These can be nice as you can insert them, and then inflate them gently to stretch the sphincter. Just be careful about inflating them too much; the cover may separate from the base and produce a large farting sound : )

Dildos:

Just the thought of a strap-on dildo has made more than one submissive weak in their knees. Be careful though, successful use of a strap-on takes some patience. You need to experiment with positions in order to find the right angle.

Ripplely Things:

This is my absolute favorite toy. The ripples feel amazing going in and out, and you can take your time to work up to the larger bumps. This one is also very flexible, meaning you don't have to work as hard to find a comfortable angle.

Vibrating Eggs:

A vibrating egg is little egg shaped plastic container that holds a vibrator and is attached to a control unit by a wire. Because of the risk of the wire breaking off, always use the egg in a condom and pull the egg back out by the condom. Also be sure to pull it out gently and straight back, as not to cut into the sphincter.

Anal Beads:

Anal beads are round beads on a string which are inserted and then gently pulled out for pleasure. Be careful about anal beads. The plastic ones that have a weight inside are known to occasionally break, and the plastic mold lines have not been removed, leaving sharp edges. It appears that the brass, rubber-jelly, or solid plastic ones are a better choice. Always make sure the beads are smooth and cannot break. Just keep your eyes open.

Speculum:

A partner can inspect the inside of your anus with a speculum. A speculum is used by gynecologists to inspect the vagina. The two hinged pieces are shaped like two duck-bills and are inserted and then spread apart. Be sure you're familiar with how it works before using one. I would recommend the small clear plastic ones for most people. (You can also use an anal scope, a small cone of clear plastic, but these can be harder to find.) After an enema it's neat to see just how pink and clean the rectum is, and you can sometimes see where the rectum takes its left turn.

The Issue of Flanges:

Most people recommend only using dildos that have a flange for anal play. The fear is that you might suck the toy into your ass. The rectum is simply not capable of creating a suction. What can happen though is that the dildo is inserted past its widest point and the sphincter closes down and pushes the dildo in, or you simply can become too excited and push it in.
     In general, using toys with a flange is a good idea. This is especially true if you're playing by yourself. However, you can safely use toys without a flange if you and your partner are careful. If for any reason something does go into the rectum, don't panic. The rectum was made to push things out. Simply bear down gently as during a bowel movement, and it should come right out.

Cleaning:

First of all, you need to decide if the certain toy is going to be used by one person or more people. I strongly suggest having only one person use any given toy. If you play with multiple partners, either they can keep their toys with them, or you can write their name with permanent marker on their toys. If you have a toy you want to use on multiple partners, you should either always cover it with a condom, or it should be a toy that can be sterilized to a medical tolerance.
     If you choose not to use condoms to cover your toys, you should clean them after each use. Assuming it is a single person toy, you can clean it with soap and water. The important thing is to make sure it is dry. If an anal toy is left un-cleaned and wet, all kinds of nasty things can grow on it.

Anal Sadomasochism?

A large part of this guide deals with avoiding pain. But what happens when you want to give or receive anal pain? You should approach anal sadomasochism with trepidation. When you are flogging someone, you can visually see much of the damage you cause. You don't have this advantage with anal play. Therefore, you either have to rely on your experience or feedback from the submissive. Neither one of these are foolproof.

All players have limits. Intentional anal pain is one that you really need to discuss. If you are the top, you should make explicit whether you intend to inflict pain there. If you are the bottom, you should make explicit whether you will accept pain there.

Let's Play!

Now it's time to get down to business.

Pre-Play Set Up

The very first thing you need to do is to communicate with your partner. Anal play is not something you can just start doing without talking about it and hope it comes out well. You need to negotiate.
     If you are the inserter, find out about your partner's past experiences with anal play, the things that really turn them on about it, and things they're afraid of. Talk about things like fantasies.
     If you are the insertee, tell your partner what you want them to do to you. Tell them about any problems that you think will come up. Tell them if you want an enema first. Just talk.
     After negotiation, you need to find a place to play. Most people will play in a bed or a shower. You'll want a place where you are not going to be disturbed. You'll also want a bathroom nearby. Get all the things you're going to need together. This will include plenty of lubricant, latex, maybe some toys, towels, some good music, and an enema if you want one. Make sure to trim and file your fingernails beforehand. Sharp nails can cause small cuts.

Let's Go!

First of all get into a comfortable position. Personally I find it works best if the receiver is on their knees with their ass in the air. On your side, or on your back with a pillow beneath your butt also works. Either way, you'll probably want a towel beneath you, as all that lube can get messy.
     The insertor should put a glove on each hand. Squirt a bit of lube onto your finger. Use that finger to spread the lube around the surface of the receiver's anus. Don't go in yet. Just let the person get used to the feeling of having their anus touched. Add more lube.
     When the receiver says they are ready, slide the tip of one finger over the anus so the anus is underneath the middle knuckle. Now slide the tip of your finger back towards the anus, pushing in gently the whole time. When the tip of your finger is directly over the anus, you'll feel the tip pop in just a bit. Your finger is now through the outer sphincter. Underneath your finger, you'll feel the small ring of the inner sphincter. It can feel like you're pressing on the center of a small cheerio. Add more lube.
     Straighten out your finger and aim it towards the belly button. Push in with a gentle and steady pressure. Your finger is now inside the receiver. Check in with your partner and make sure everything is okay. You are now at a point that can be especially terrifying for someone who hasn't done anal play before. We normally associate the feeling of something in our rectum with going to the bathroom. The receiver will all of sudden feel like they have to go the bathroom and usually are afraid of going on their partner. This is a false sensation. In time it will go away. Gently pull your finger out. Add a lot more lube.
     Slowly slide back in at the same angle as before. You can now gently begin to finger fuck your partner. This should feel rather good. Make sure to keep talking. If you are the receiver, tell your partner how it feels. If you are the inserter, tell your partner how it feels to have a finger inside their ass. If you like to, talk dirty. Keep communicating.
     If one finger is feeling fine you may want to move onto two. Add more lube and keep going as long as it feels good. If you want to, move onto the other toys or a penis, but remember to add more lube and be careful of the insertion angle. Having an orgasm with something deep in your ass is a wonderful feeling.

Finishing Up:

When you're finished with anal play, the inserting partner should pull out slowly. After anal play, many people feel they need to use the bathroom and expel lubricant. They often will and this is normal.
     Afterwards, it is time to cuddle. Later on, make sure to talk about your experience.

Self Play:

I highly recommend exploring your own anus. Without any pressure to perform, or worrying about what someone else thinks, you can learn about how your anus feels. You can also see what your anus looks like. Get a mirror, and look. On your back with the mirror between your legs, you can watch as you insert an object. You can really see how the muscles move as you relax. Part of the problems with relating to your anus is that you can't see it.

Fisting:

I won't go into great depth with this subject, because, personally I have never done it. It can be done safely if done with patience, care and plenty of lubricant. Fisters overwhelmingly prefer Crisco. This is because Crisco's high viscosity helps it work its way in deep, and the lubricant holds up over the time of a long fisting session. If fisting is something you want to learn, I suggest you check out some of references below, or better yet, find someone who is experienced and apprentice to them.

References

Note from The BRC Editor:  Links from the titles of the books were added into Matchstick's info since I thought that might make for easier purchase of the books mentioned for those interested.

Much of what I learned came from Anal Pleasure & Health by Jack Morin, Ph.D. It is a GREAT book, and the authority on all things anal. It's also a great help to those whose anal health problems are interfering with their sex life.

There is also a fisting book out there, Trust: The Hand Book, which is all about anal fisting (insertion of the hand into the anus). I haven't read it myself, but I hear it is good, despite the author's slanted view of BDSMers.

Just recently a new book came out, The Ultimate Guide to Anal Sex for Women. I flipped through it, and it looks pretty good.

You can also find a lot of information on the Internet. Check out my links page to find some of the best.