Some notes:
This is a strictly physical how-to guide. Anal sex is obviously not for everyone but it is my belief that if done right it can be lots of fun with a partner or with a favorite sex toy.  It is my intent to provide a step by step how-to with common sense advice, as a result this will not be even remotely erotic.

Please read the Everything2 medical disclaimer before making any decisions based on this node.

Preparation:
There are a few things that you will need before attempting this for the first time:

  • lubricant: some women can just move some excess vaginal lubricant down to the anus and it will work fine. But this is not the case for all women. If you aren't particularly juicy , or you're a guy, go to your local sex toy shop and pick up some lubricant. I recommend Astroglide. It's the only brand I've ever used but it works wonders and I have friends who have experimented with other brands and prefer this one. Please follow the astroglide link for more details. Spit can get you started but it doesn't generally last long. K-y is probably the best known lube but it gets sticky too quickly.
  • a very caring partner, or a vibrator/dildo.

Getting there:
Ok, before you even get to the point of inserting anything sizeable into your anus I recommend moistening your middle finger and lightly running it over your anus while you are masturbating or being sexually stimulated in any other way. It is very important that you don't clench it up. If you do the more sensitive part will get sucked in and it won't feel terribly interesting. This stimulation alone can feel quite good but if it doesn't to you I don't think you're going to enjoy taking it any further. Take your time with the following steps. Some people may get all the way to full anal sex the first time while some may take many times to relax enough.

Everything from this point on is dependant on you being able to relax your anus. This can be difficult the first couple times as you're whole life you've been working on keeping that hole closed. It can also depend on you feeling emotionally relaxed enough to let yourself physically relax that much in the presence of another person. Deep breathing can be very helpful in relaxing the anus. Also, just getting used to being touched there can help you to relax. It should go without saying, that you should not do this if you have to poop , unless, of course, you or your partner are into excrement. Also remember that the anus is not a sanitary environment so nothing you insert should go anywhere near a vagina without being thoroughly cleaned first. It is also very important that your fingernails are short and don't have any sharp edges. This is also a very good rule when inserting them into a vagina as long or sharp nails can create micro-lesions on the vulnerable inside walls which can lead to infection. This is not something you want in either place. Like everything else in life, take a break if it hurts and stop if you see blood.

When you are ready relax your anus and slowly insert your finger; I don't recommend moving up to anything larger yet. Go slow and use a back and forth motion to get it in. A straight push may hurt depending on how much lubricant you have and how relaxed you are. Once it's in there you'll probably be a bit tight. Just leave it there without moving it until you fully relax. The sensation can feel similar to having to poop. In my experience this goes away after the first couple times or possibly after you get to the stage of actually having anal sex. Once you have relaxed enough try moving your finger in and out and wiggling it around inside. You will start to learn what does and does not feel good for you but this is only the tip of the iceberg.

If you press your fingertip into the side near the opening you should be able to feel the two sphincter muscles. They are about a quarter of an inch apart. The outside one is controlled by you. The inside one is controlled by the autonomic part of your nervous system and will react to fear and anxiety. So you really need to be comfortable with your partner and surroundings.

Moving your finger around in there may feel interesting but not be all that you hoped for. Don't worry, the sensations get more interesting when you finally move to something larger. Some people will find this to be more than enough fun and actually more pleasurable than actual anal intercourse. Be careful what you do with that finger when you're done.

When you finally move to something larger you will find that you only want to insert it so far. After that it will start poking into uncomfortable parts. Some angles may also be uncomfortable for you. Be sure to use plenty of lube. You will generally find that , like vaginal sex, you need to start off slowly. If you're moving up to a penis be sure that you have a caring and sensitive partner with you who will pay attention to your needs. Anal sex can be uncomfortable, or even painful, if done without paying attention to what the receiver needs.

"Diet contributes to the enjoyment of anal sex. Regular bowel movements are the major function of the anus and rectum. There must be sufficient fiber in a person's diet to make his or her feces soft, bulky and well formed. This allows a bowel movement to be produced without force or effort. Forced evacuations irritate anal tissues, causing discomfort and adding to muscular tensions. Fresh fruits, vegetables, whole grains or unprocessed bran are important sources of fiber. " -sexuality.org

Now, that you know the basic mechanics let's move on to how to make the experience as pleasurable as possible.

Satisfying the anus:

  • with vibrator/dildos
    • Be careful not to turn vibrators up too high. Otherwise, your anus can go a bit numb for a while afterwards. This is because the sphincter closes much more tightly around it than a vulva usually can and thus absorbs more vibration.
  • with a penis:
    • Beware of penises that are too large. Too large is uncomfortable. Penises that are too small can occasionally get pushed out when you clench too hard. You don't have this problem with a dildo because you can hold it in. The man penetrating you won't be expecting it and will usually get pushed out at least a little bit.
    • as long as you are lubricated you shouldn't notice a difference between a penis with or without a condom in terms of friction.
  • with either:
    • Most of the sensation for you and your partner comes from the sphincter muscles at the opening. In and out motion can be very stimulating here, the more the better. Like vaginal sex, really fast is a completely different sensation from really slow. Just be sure to not poke in to far or at the wrong angle. Like vaginal sex there really isn't that much to it. It's simple, and fun.
    • Doggie Style is not the only position you can do this in. Some people find lying on their backs with their butt and lower back propped up with pillows to be a great position for receiving. You can also do it while spooning, bent over a table, riding your lovers penis, or strap-on, or any other position that sounds interesting to you.
    • If the receiver here is a male don't forget to stimulate the prostate "which is just beyond the rectal wall, a few inches in, towards the front of the body - can be a source of pleasure when massaged by a finger, an object, or a penis. Also, the lower end of the penis, or "bulb," is near the anal opening opening. It is stimulated indirectly by most types of anal sex" -sexuality.org
    • after orgasm some people find it uncomfortable to keep anything inserted into them.

Satisfying the penis and man:

  • Clenching your anus can enhance the sensation for a man penetrating you
  • The greater their range of motion the more stimulating it is for them. So, the more deeply they can move in and out the better.
  • Men generally find anal sex to be very pleasurable because of how tight it can get, so don't forget to squeeze.
  • Some men also find it visually stimulating with a doggie style position because , unlike with vaginal sex, they can see everything that is going on.
  • Some men also find the taboo of not using a condom (which I don't recommend for many reasons) to be a turn on. There is of course the whole argument about it being more sensitive without one but I will leave that up to you.

Afterwards:

  • Obviously be sure to thoroughly clean off anything you've inserted before it touches anything. You may want to have a washcloth or saran wrap or paper towel nearby to set your dildos on without having to get up to wash stuff in the middle of everything.
  • If you want to go quickly from anal sex to vaginal sex just be sure to have condoms on your partner or dildo and change them between orifices.
  • When you're all done you may feel a warm, almost tingly, sensation for up to 30 minutes afterwards. Not everyone experiences this and it isn't a bad feeling at all. You may also feel like pooping. It seems that sometimes that much action seems to set things in motion and you end up going sooner than you would normally expect.

Common Questions:

Isn't it dirty? Not really so long as you have pooped recently and/or don't feel you'll have to go any time soon. But, remember that sooner or later you are bound to encounter a little piece of brown. Don't get freaked. It 's not going to hurt you and if the penis in question wore a condom it will have never actually come into contact. Your dildo/vibrator won't care in the least.

Will it hurt? Not if done correctly.

Can I come from anal sex alone? Yes, well, some of you will be able to but we're actually a minority. Most people will also need some genital stimulation to reach orgasm.

What about condoms? Use 'em. Just because there's almost no chance of getting pregnant this way doesn't mean you can't catch a disease this way. I hear tale that those little spermies can cross the wall adjoining the vagina and then make their way to awaiting eggs but this sounds highly suspicious to me.

Will I go to hell for this? Only if you die before you make it to confession.

Is this really illegal? In America almost every sex act that isn't heterosexual missionary position sex is illegal . I can't comment on other countries.

What about analingus/rimming? That's another node entirely. I'll link to it once I get it written.


I'd like to say thanks to all the men and women who helped by answering my questions. That means you too randir. ;) If you think I've left anything out please /msg me. Also I'd like to thank the creators of sexuality.org. I found a few things I'd left out there. And no, I didn't copy this from anywhere.

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