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Think of a hotdog sliding in and out of a bun. Knowing this I always like to tease a bit and build up some anticipation before sliding in fully the first time. This usually involves rubbing your penis head on the inside and out of her pussy lips and rubbing the tip of your penis on her clitoris. I explain a technique called the CAT here that works great for giving her a clitoral orgasm during penetration. Watch him drilling wondrous 4: Right click on the link and "Save target as For example, one of my favorite moves is to give my woman five or so deep thrusts and then, on the sixth one, thrust deep and just leave my penis deep inside of her vagina for about a second or so, and if your woman is doing Kegel exercises, she can squeeze your penis with her vagina at the same time.
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After both partners have been warmed up, feel free to pick up the pace and vary often to keep her guessing; but always take care with the initial penetration. In looking how to penetrate a vagina, it is important to know the experience of your partner. Whether it is her own natural lubrication, or a product, you want to make sure there is a low amount of friction to make it comfortable for both you, and especially her. How experienced is she?
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