Of course using your hands for their genitals will leave you short-handed for keeping their cheeks spread, so this is where recruiting them to do either the spreading or the stimulation is pretty useful.
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Anal sex can be a perfectly safe activity as long as you take the necessary precautions. You should remember that your anus and rectum do not have their own natural lubrication nor the kind of elasticity the mouth and vagina enjoy. That is why anal sex must be practiced with care.
The best positions for anal sex depend largely on what stage you and your partner are at in your experiences. Rear entry or the "doggie style" position is the one position most people associate with anal sex. However, rear entry allows a penis or anal toy to penetrate most deeply, and may not be the best choice for the beginner. A good starting position is the "spoons" position, with each partner laying on his or her side, one behind the other.
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With anal sex of any kind, lubrication is worth seriously considering. And oil-based lubricants tend to work better, because of the treater pressure/texture involved. Drying out like water-based lubricants do is a more serious problem than with other kinds of sex. Bear in mind, of course, that oil-based lubricants are a threat to a latex condom, which will be damaged by it.
Another good idea is to try firmly licking, or even sucking on, the perrenium (the area between the anus and genitals. On a guy this is especially useful, because it indirectly stimulates both their balls and prostate.
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