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I watched and listened as the guy reminded the girl to keep her legs parallel to the ground and I heard a loud gasp as she felt the rope press against...her pussy. She managed to keep reasonably quiet but her face told me that she’d had an orgasm as she came down. Also, her face was bright red when she was back on her feet in front of the guy and me.When she set off to go to the next obstacle I started climbing the ladder, I wanted to cum with that guy looking up at me, and I did, but this time I. Given how little pain there is (and there is pain), and looking back at him, I realize its just a finger, readying me for what Im about to endure. Maybe 30 seconds of having his finger in my ass, another tiny humiliation, before its removed. I feel a heat at my last technically virginal hole, as his cock rests against it. I try to brace myself, not knowing what Im going to feel. He starts pushing, slowly at first. I can feel the pressure build up, but its nearly a minute before it feels like my. More

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