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Unless he won. I wasn't sure what he meant by that, but he explained further. We went to the casino, if he came out ahead after three hours of playin..., then I would reward him with my anal cherry. I laughed, but agreed pretty certain he would fail. And he did. Until the last night.He actually won back everything he had lost up until that point and a lot more! I was nervous as he cashed in knowing what would happen when we got back to the room. What I didn't know was how amazing it was. I stroked it trying to figure out what to do with it. Finally I said, "Fuck it." I bent over, put my one hand on the toilet lid, hiked up my skirt, looked over my shoulder, grabbed an ass check, spread myself open and said, "Be gentle hun." He positioned himself behind me and with cock in hand he slipped the head of his cock between my pussy lips. I was so excited that I just knew that my pussy juice had probably drenched his cock as he opened me up. He slowly worked the head of his cock into. Trish bit her lip a little bit, I could tell she wasn’t enjoying it that much, well at all, but at least she was letting me enjoy it, and enjoy it I was. ‘Trish, tell me to fuck your arse, tell me to cum in your arse’ I whispered. Trish looked at me and smiled. Now that’s my kind of woman, I am buried in her arse, fucking her for the first time anal-style, she’s not really into it, but she wants to please me and return some pleasure I have brought to her all night. ‘Stewy you big stud, fuck my. “It will cause intense pain.”The boy on hearing this whimpered loudly and squirmed in his bonds, which only allowed him limited movement. The spectators leant forward, their eyes gleaming with the light of the braziers and watched Jeremy take hold of the end of the wire. Jeremy waited, smiling at the boy and drinking in his terror. It was in the boy’s eyes and expression, the way he shook and trembled, that they could all taste his terror.As Jeremy pulled on the wire, the boy flung his head.
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