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There are many people who have never heard of fisting, or have no idea what is really involved. There are two types of fisting, vaginal and anal, this article is focused on vaginal fisting. First off, I would like to bust the biggest myth about fisting. It is NOT true that your partner must be "well used", or "worn out" in order to insert your fist.
The human vagina is incredibly resilient, and muscle tone allows women to give birth, but also to tighten down enough to grasp a finger. A word of caution, the skin of the vaginal lips, as well as the interior skin is very sensitive, and prone to small tears, unless caution (and patience) is used, infection can occur with these tears. Things will go smoothly if both partners are patient, and some simple precautions are observed. First, it is important for the fister to thoroughly wash his or her hands. It is also helpful if the fistee is shaved, or at least trimmed of pubic hair. The fister must also make sure that the fingernails are trimmed, and have no ragged edges.
Another important factor is lubrication. I recommend a water soluble lubricant like KY jelly, or the generic equivalent. Astroglide may work for you, but for my taste it is not as kind to the skin while it is being stretched. How much lube do you use? Well, when you think you have enough, use more. I have at times, used half a tube. It can get messy, so use plenty of towels. Messy sex can be the best kind anyway, so use the lube liberally. The application of the lube can be integrated into the foreplay. I sometimes find that giving my girlfriend one or more orgasms before fisting really helps things along. Of course, before you can get your hand in there, you've got to get your fingers in there first. After the third finger, you begin to get to that "stretch zone".