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We recommend something like Wet Platinum Premium Silicone lubricant, which is available at where else? Crouch down and put your weight on one of your clenched fists. But for many people, the hesitance to engage in anal sense could potentially be wrapped up in any lingering issues of sexual identity. It's also very important to remember that he should only go in as deep as it still feels good. And it really helps if she pushes out against it. Kimmie KaBoom: I would experiment with positions.