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Hold it against your anus while you keep masturbating. Do not take muscle relaxant drugs to help you loosen up. Otherwise, after the years you start getting way too loose. Pull on the sides of your asshole again. It's all done by gradually applying slow steady pressure and being very carefull not to try to progress too quickly. Anal Sex and Anal Play are a lot about noticing certain sensations and training your mind to feel pleasure from them. I thought that I was wierd because it hurt so much.
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That is one nasty piece of work! A Speculum up her Ass helps to get more Balloon in her fuck holes. She asked to be fisted, so I obliged!!!
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Always very sexy when you can see a sliver of areola when a woman is going low cut

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