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Once a woman is accustomed to anal stimulation, and you are aware of when her anus is relaxed, and not tensed, you can start exploring anal penetration. The anus and rectum are very delicate so be sure to only insert smooth objects that do not have any sharp edges. Trim your fingernails. Wearing rubber or latex gloves will make your finger(s) easier to insert. Massage the anal ring and wait for it to relax and open up. Once it has, start pressing the tip of a single finger slightly into the anus. If you feel it tighten, stop, withdrawal your finger, and resume the anal massage for a couple of minutes. When her anus has relaxed again, slowly insert your fingertip again. Go slow and do not try to insert your entire finger in the beginning. In fact, only a small portion of your finger may enter before the anus tightens. If you go to fast, she may experience considerable discomfort, ruining the moment and possibly ending your exploration of anal sex. She can also learn to sense when her anus is tensed, and learn to relax it. Doing Kegel exercises while a partner's finger is inserted will help a woman learn how to do this. This will come in handy later when larger objects are inserted. In the beginning you just want to insert your finger without moving it around. You want to condition her to the feeling of something being in her anus. She will likely enjoy the feeling of something being in her anus when she experiences orgasm. Once she is comfortable with being dilated, slowly start to move your finger in and out, and around. Gently stretch her anus by pushing outward on her anal ring. Once a woman has learned to enjoy the insertion of a single finger, start inserting a second. Always go slow and be sure she remains relaxed. Once you are able to insert two fingers, you may want to acquire a couple "butt plugs" to help condition her to further dilation. Butt plugs are tapered dildos with a flared base. The taper allows you to slowly dilate the anus. The flared base prevents it from accidentally slipping all the way up into the rectum. You should never insert anything into the anus that does not have a flared base, as the rectum can draw objects in, and it can be difficult to get them out. Requiring an embarrassing trip to the doctor. Butt plugs come in many sizes, from the size of a slender finger, to the size of large fist. For the majority of people, a small and medium butt sized plug, 0.5 to 1.5 inches across, will do the job. For women who like the intense feeling of large objects being inserted, the sky is the limit. Silicone dildos are the best choice as they are smooth, flexible, and easy to clean. They are more expensive, but will serve you far better in the long run. It is also a good idea to put a condom on the butt plug, or dildo; it will make clean up easier, and protect non-silicone toys. To use a butt plug, massage and slowly dilate her anus with your finger(s) first. Once you are able to insert one or two fingers comfortably, place the small butt plug at her anal opening, then with a single finger, slowly press it in a little ways. Then allow her anus to push the butt plug back out. Then press it back in again. Using only a single finger to press in on the plug to help prevent you from using too much force. Very slowly repeat this process, inserting the butt plug a little further each time, if her anus permits it. Try to caress her clitoris while doing this. With patience the butt plug should slip all the way in and stay in place, due to its slender base. The smaller butt plugs may not stay in as well as larger ones, because their base is almost as big around as the largest part of the tapered section. Once the plug is in, leave it alone and make love to her. Perform cunnilingus and have vaginal intercourse if she so desires. More importantly, bring her to orgasm. Allow her to enjoy the feeling of something being in her anus during orgasm. After a couple sessions you can start to work the butt plug in and out, stimulating her anus. If she is comfortable with the butt plug being inserted, allow it to remain so for fifteen to twenty minutes to help condition her anus to dilation, after you are done making love. Many women may enjoy the feeling of the butt plug when it is inserted. It is okay to leave it in for longer periods of time if she is comfortable doing so. Once you are done, slowly slip the butt plug out, and wash and dry it in preparation for the next time. Once she learns to enjoy the small butt plug, switch over to the medium sized one; you may need to use the small one in preparation for the medium one during the same session. Go slow and have fun. Do not be goal orientated. In preparation for anal intercourse you will probably want to buy a dildo that is equal in size to your penis, if you are male; lesbians can choose any sized dildo for their harness. Using a dildo will provide you with more control over the amount of pressure applied to the anus during insertion, and greater control over your own movements. Get one with a flared base so it cannot slip all the way in. Again silicone dildos are more expensive but a better buy. Slowly stretch her anus with fingers and butt plugs first, then slowly and gently insert the dildo. At first, just let her get use to the dilation. It does not have a small base, so her anus will be fully dilated all the time. This may be very intense for her. Allow her time to adjust to the greater constant dilation. When she is relaxed, slowly move the dildo in and out. Go very slow at first. Allow her to guide your movements. As always, be sure to bring her to orgasm. By the time you consider anal intercourse, she should be so accustomed to anal penetration that she has no apprehensions at all. There should be no fear of hurting her. She needs to welcome the idea of your penis entering her anus. Prepare her anus with your fingers and butt plugs first. Go slow. Schedule an entire evening or day for this special occasion. During the insertion of your penis, she must be in control of how far your penis enters her, and the movements of your bodies. So she needs to be on top, or on her hands and knees. She needs to lower herself down onto or push herself back onto your penis. She must open and receptive to your penis, versus you pushing your penis in. Once the head of your penis is in, she should stop and relax for a couple minutes, to get use to the dilation; and feel your body heat. When she feels comfortable, she can take in the remainder of your penis, once again she needs to stop and relax. When she is comfortable, she can either remain still, or start moving slowly back and forth or up and down. Go slow, the sensations can be very intense. It helps if while doing all of this if one of you massages her clitoris and/or breasts. Bring her to orgasm prior to penetration to help her relax, and be more receptive. Once you are in, bring her to another orgasm.

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