One of the most common questions couples have is about the various forms of anal sex (analingus, and actual anal penetration).

Anal activities make many people feel more than a little uncomfortable.

• In fact, there is a unique form of pleasure to be gotten from anal stimulation.
  • For men this is because of the prostate, which is an important sexual organ and can only be directly stimulated through anal contact.
  • For women it is because the rectum shares a wall with the vagina, and the sexual nerves are actually closer on that side, making the sensation different and sometimes actually stronger.
  • Anal sex is high on the list of sexual play for many people, and can be a fun change of pace for almost anyone who isn't bothered too much by the taboos against it.

Things To Consider

• Be Sensitive
• If you and your partner haven't already discussed it, it may be a difficult subject to bring up.
• There is a reasonable chance that they have already thought of it, and were afraid to bring it up themselves.
  • But there's also a chance the idea would horrify them.
• If your relationship doesn't already involve open, relaxed, and frank discussion about sex, you probably should work on that long before you worry about testing the waters on this subject.
• The anus really isn't meant to be entered, that's not to say it's bad.
  • Just keep this in mind...One should be very gentle when experimenting with these things.

Cleanliness

• This matters more to some people than others, but having bathed more recently than the last bowel movement is a good idea.
  • Oil-based lubricants are a great insulator for anal contact.
  • They tend to cover up any potential smell and transfer of fecal matter.
  • If you use Vaseline the odds are that a simple wiping off with a dry cloth will result in finger/penis/whatever seeming to be just about perfectly clean.
• Enemas may seem like overkill
  • This is worth considering in actual penis penetration; since one gets a lot deeper than even the most dilligent bathing process is going to be able to clean.
  • But it is still not a really common practice, even for actual penetration.

Lubrication

• With anal sex of any kind, lubrication is a definite must.
  • Oil-based lubricants tend to work better, because of the greater pressure/texture involved.
  • Drying out like water-based lubricants do is a more serious problem than with other kinds of sex.
  • Oil-based lubricants are a threat to a latex condom, which will be damaged by it.
  • Although not latex friendly - Vaseline followed by Cocoa Butter are the best lubricants for anal sex, because they will stay in place and lubricate much longer than thinner lubricants, and yet not provide their own resistence like thicker ones will.

Positions

• For most anal sex, there are a few positions which make it easier to access the butt.
• These generally apply to analingus, manual penetration, and actual anal sex.
  
  
• Position #1
  • Female partner lies on her back, legs spread and/or knees pulled up.
  • Put a pillow or two under their butt...this is a big help that's easily overlooked.
  • This can be the most awkward of the positions, but it can be the easiest for your lover.
• Position #2
  • Female partner to be on her elbows and knees, as for doggie style sex.
  • This is easier for access, but it also tends to require your lover to tighten their butt muscles a bit.
  • This may work better if your lover has some support under their chest/belly to lean on, so they can relax more, and possibly even so they can lean forward a little, extending their legs out and to the side behind them, which might put things at an easier angle for access.
• Position #3
  • Female partner lies on her side.
  • Their legs need to be in a scissors position, perhaps the upper one extended in front of them and the other straight "down" (as if they were standing), else the upper leg drawn up toward the chest or straight upward (bent, either way), and the lower leg in whatever position is comfortable.

Analingus

No matter what position you're using, your hands, or your partner's will probably be necessary to make access easier.

You have far more control and better contact if their butt-cheeks are spread away from their actual anus.

• Some prefer a light flicking, gently licking around the center, or gently pushing at it.
• Some prefer a deeper probing, with your tongue held rigid and pushed firmly inside.
• Another method is to widen your tongue to apply pressure over the entire outside area...this is often much more stimulating than you'd imagine.
• Another good idea is to try firmly licking, or even sucking on, the perineum (the area between the anus and genitals.
• The best method would be to combine all of these, and pay close attention to what your partner enjoys most.

As in all sex, pay attention to your partners signals so you can learn what they like (it is different from person to person, this may be the most important secret of sex.

If you're going to engage in this for a long time, especially if you won't be switching back and forth between analingus and fellatio/cunnilingus

You probably will want to provide some stimulation to their genitals, as analingus is a pretty mild form of contact that probably won't bring them to orgasm, or even keep them heavily stimulated, all by itself.

Hand-stimulation, is often a vital part of oral sex

• The range of things one can do with analingus is a bit more limited than with cunnilingus and fellatio.
• Many people won't really want to do a lot of probing with their fingers while licking.

Manual Penetration

Fingers unlike the tongue are rough.

This is true no matter how smooth your hands are.

Caring for them ahead of time with some hand-softening lotion and the careful removal of as much fingernail as comfortable is a good idea.

Fingernails are an important consideration. Even being well-smoothed may not be enough.

Rubber/latex gloves, especially the surgical kind, are definitely worth considering, especially if either of you are just starting to experiment with anal-finger stimulation.

The difference it makes is just astounding...discomfort which was actually assumed to be from other issues usually disappears completely.

Gently touching the anus is a good way to get started, once you're worked up to it.

• It can be exciting to just be touched there.

Next you might gently circle it with your finger.

• Even without penetrating, there is a difference in sensation between pushing right in the middle, and pushing/circling the area right around the center.

Actual penetration usually requires that you work your way up very gradually, gently stroking the region right around the opening, then pushing gently at the center but not actually penetrating.

Actual penetration may, be best accomplished by locating the exact opening

Don't assume you know where it is, sometimes even your partner can be mistaken if they're trying to guide you.

• Once you have found the opening try making a rhythmic pushing motion at it, very gently, and only penetrating perhaps a millimeter more each time, especially until you've gotten the rounded part of your finger well past their actual sphincter muscle.
• They should, as with penis penetration, make a point of relaxing as much as they can.
  • A good way to ensure relaxing enough to allow entrance is to make what feels like a slight pushing motion, as if having a bowel movement.
  • If they can comfortably isolate that relaxing motion from real pushing, they're almost sure to be able to relax enough for almost any kind of penetration.
  • It is stimulated by any attention to the region though; including the perineum is also very stimulating as well.
  • You can gently push/massage the perineum with your fingers, even if you're not penetrating his anus.
  • If you are penetrating him, once you're well inside, work your way gradually to the prostate.
  • Make this very gradual, as hitting suddenly can either be very uncomfortable, or cause him to suddenly have an orgasm, before you actually planned it.
  • Sudden, strong stimulation of the prostate can, in some people, cause spontaneous orgasm, but it may just be really uncomfortable.
  • Stimulating the prostate for a while, until orgasm, also causes both a much different feeling orgasm, and more "watery" ejaculate.
  • The prostate provides lubricant, whereas the testicles provide the actual sperm.
  • Performing fellatio when using your fingers to stimulate his prostate is a very good idea.
  • You simply allow a finger to, in the course of keeping it out of your way, stretch back past her anus, so that your pressing motions will happen to incidentally press lightly there, too.
  • You might even work your way up to allowing a pinky to press against the opening itself, and perhaps even work its way inside, a millimeter every dozen strokes or less.
  • When attempting to penetrate her anus you should have a different finger inside her vagina and make the main stimulation there, let the anal penetration take a good, long time to actually progress.
  • Make sure to provide lots of lubrication.
  • Once you're pretty well inside, concentrate (very gently) on stimulating the side nearest her vagina.
  • A pressing motion is very helpful.
  • In fact, you might not even do much sliding in and out, depending on how relaxed/excited she is, and how well lubricated you are.
  • You might take several sessions to get to the point of actually concentrating your effort on the anal part, keeping it a secondary form of stimulation at first.
  • That depends on how well she enjoys it and how much discomfort, if any she encounters.
    • Remember, gradual is safer, because you can always build up but if you go too far it may be hard to recapture the mood or continue the experiment.
  • Once/if she's really into it, one thing you can do is to press along the same wall from both sides -- both press toward the rectum from the vagina, and toward the vagina from the rectum.
    • The wall between them is thin enough that you will easily be able to feel each finger from the other one.
  • Do not swap fingers, the anus can carry common intestinal parasites that you'd never notice, but which might not have reached the vagina.
  • This allows your lover to get used to the feeling, and to relaxing their anus in the right way.
  • Even better is to work your way up to more than one finger.
    • Remember though, that fingers are a great deal rougher than a penis, so be careful.
    • A glove is very useful for manual anal penetration, and is almost a prerequisite when attempting multiple finger insertion.
  • When working up to actual penetration, use your hands to stimulate your partner.
  • Be very careful about penetration.
    • Done wrong, this can be extremely painful.
    • Done correctly, it's not painful at all, and can be very pleasurable.
  • Be careful about "hitting the hole".
    • This is far more difficult to target than a vagina.
    • This is also another reason to start out with finger penetration.
    • There tends to be a slight softness, in most people, above or below the anus that can fool you, no matter the amount of care, into pushing at slightly the wrong angle or spot, so that neither of you realize it's wrong (yes, that's right, this mistake can be made even from inside your partners body.
  • Also of importance is angle of penetration.
    • You need to figure this one out with a lot of care and observation.
    • Just remember that most angles are the wrong one, so you need to make an effort to make it better than random.
    • Prior experimentation with fingers would help with this problem before attempting penile penetration.
    • A fingertip already inside a relaxed lover can be the perfect guide, actually making insertion of the penis easier and less painful.
    • If the position allows, and you're both comfortable with the idea, you may also have your lover help guide you in they may not be able to tell, perfectly, either, but at least they will know what hurts and what doesn't.
    • You should still be using your own hand as well, so you can feel what they're doing and when to do what yourself.
  • When attempting penile penetration go very slow about a millimeter.
    • Go very slowly.
  • The best method is probably to make a slight pumping motion, starting out just pushing slightly at the opening, not actually penetrating at all, and simply adding the tiniest, bit of pressure each time.
  • It should take minutes to make any real progress.
  • A big factor is your partner.
  • The more they can relax the better.
  • This means both their mind, and their sphincter/anus.
  • No amount of lubricant is too much, either, if there is any concern about pain.
    • The big key in getting through this is the initial penetration of the bulge of the penis head getting past the actual anus sphinctor muscle.
    • Once this is past, sliding in if at the right angle should be nearly painless.
    • There are guys, though, whose penis is shaped in such a way that it still gets wider along the shaft, but the average penis, which is about the same width all the way along except the head/glans, the difficult part is past once the head is inside.
    • Make sure the shaft was also lubricated, by the way, in case a "snag" from a dry area might cause discomfort.
    • Once safely inside, and once you've found the right angle, and everything is going well basic sexual pumping works fine, here, but you may need to start out slower, though that's a good idea even with vaginal sex and gentler.
    • It may be a good idea to shift angle just slightly, so that the head of your penis is pressed more against the inside where the anus is closest to the vagina.
    • This will make things, perhaps in a subtle way but in a way that will accumulate in effect, more stimulating for your partner.
    • As for the man, this is about the tightest form of sex he is going to encounter, which many people find very stimulating.
    • Once you've done the full penetration thing a few times with your partner, and they are getting to the point where relaxation is easy, and pain is not really an issue you can consider trying more unusual positions and methods.

Men

The key to anal sex with a male is the prostate.

If your partner is lying on his back, his prostate is on the "up" side of his rectum, several inches inside.
Women

The best way to engage in manual anal penetration is to at the same time engage in cunnilingus, and add the finger as a part of your technique.

One great way to start stimulating her anus is to make incidental contact with it, while you're stimulating her vagina with your fingers.
Anal Sex

It is a very good idea to start out with fingers, even if your real goal is anal sex.
Once you've worked your way up to the penis part, don't forget the importance of taking your time.

You might even engage in vaginal sex first.

Stimulating your partner can be very important, especially to make the experience as pleasurable as possible for both parties.