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I thought it was super hot when his pussy cheeks were quivering and his hands shaking, looked like an anal orgasm to me. But how often do you think this sissyboi can take a fucking like this? One a month, once a week, once every night?
Let him squirm, let him whimper, let him cry, let him try to get off that cock, just don't let him get away because he asked for it when he got naked and exposed that ass and mouth for you to use. If you breed him deep he will be back for more of the same.