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Previous - Anal Sex Preparation, Cleanliness and Lubrication
Stimulation of the ASS
No matter how naturally soft your hands are and how carefully you manicure your nails a finger and how gently you apply them they will be relatively rough when compared to the tongue or penis. You need to take extra care when using your fingers to stimulate the ass. Take it slowly and always consider the finger nails and their potential to rip the delicate wall of the anus inside. Done correctly and carefully the finger and be very effective in preparing and stimulating an ass so that you can penetrate with a cock later.
Sometimes a persons work might cause their hands and fingers to be less then perfect for such a task. Manual work may make hands rough with callus and insensitive. A solution then may be to use 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 (getting or giving). The difference it makes is just astounding...discomfort which was actually assumed to be from other issues (like being thought a matter of penetration itself, or nervous tightness) sometimes disappears completely.
Gently touching the anus is a good way to get started, once you're worked up to it. Because this area's not really messed with as much, it can be exciting to just be touched there. The next step might be gently circling it with your finger. Consider whether you're using lubrication and/or gloves as to how lightly you do this. 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 takes some time. It's generally important 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, especially if you're not using both gloves and lubricant (and even more especially if either of you is new at this) be best accomplished by locating the exact opening (DO NOT assume you know where it is, try to make a point of eyeballing it, sometimes even your lover can be mistaken if they're trying to guide you), and then 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 sphinctor muscle (the ring of muscle that squeezes to close their anus shut).
They should, as with penis penetration, make a point of relaxing as much as they can. Hopefully they did relieve themselves shortly before cleaning for this, so they should be able to relax a lot without fear of any accidents. In fact, a good way to ensure relaxing enough to allow entrance is to make what feels like a slight pushing motion, as if having a BM. Not a real pushing motion; much of the basic BM action is actually just a relaxing of the muscles in that area, and the internal intestinal pressure is what actually pushes the waste out. 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.
The best way to engage in anal finger-sex (well, I can't find an official name for it) is to be going down on her, and add the finger as a part of your techniques. First, be sure to follow the advice above, especially for penetration.
One great way to start stimulating her anus is to make incidental contact with it, while you're stimulating her vagina with your finger(s). 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 (be sure there's a lot of natural or artificial lubrication against the opening itself, and perhaps even work its way inside, a millimeter every dozen strokes or less.
Once everything's cleared for actual penetration, you work your way inside using exactly the same technique (assuming she or you are new to this)...have a different finger inside her vagina and make the main stimulation there, probably her g-spot, and let the anal penetration take a good, long time to actually progress. Lots of lubrication, and/or a latex surgical glove (surgical because this will interfere with sensation the least).
Once you're pretty well inside, concentrate (very gently) on stimulating the side nearest her vagina. A pressing motionis very helpful. In fact, you might not even do much sliding in and out, depending on how relaxed/excited (both at the same time, ideally) she is, and how well lubricated/gloved 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. But that depends on how well she enjoys it and how much discomfort, if any (some people are just "naturals", I guess) she encounters. Remember, gradual is safer, because you can always build up but if you go too far (this is true of any kind of sex) it may be hard to recapture the mood or continue the experiment.
Once/if she's really into it, one neat trick 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.
Make an effort to not swap fingers, though. The anus can, theoretically (I believe it's not common) carry common intestinal parasites that you'd never notice, but which might not have reached the vagina. We're not talking about any real major VD/STD or anything, but something her gynecologist might notice and complain about, anyway.
So assign one or two fingers to each opening, and keep them that way. In that case the "risk" is almost nil.
Next - Anal Sex Preperation, Cleanliness and Lubrication
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