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Anonymous1: I'd go for Ben's ass first. I'd make him scream and squeal
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Anonymous2: I'd start in Gwen's pussy, with a condom mostly to numb myself to avoid shooting too soon until she came twice. I'd give Ben a reach-around while I plow his cousin. Then I'd pull Ben over and drive my cock into his ass hard and deep, pushing his shoulders down and stroking his little dick until he came hard. Finally, I'd rip off the condom, tossing it onto Ben's sweaty back, and shove my bare dick into Gwen's ass, press her into the bed, driving myself deep into her until I came hard, filling her up.