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That night they made love again, and her hands repeatedly gripped and squeezed his bruised and sore rump flesh. Soon, the canings became as routine as the practice sessions. She beat him soundly every time, and he began to love and crave this new and bizarre form of attention. Being still young and naive, he didn’t see any drawbacks or dangers in his newly acquired masochism. Indeed, the thought that things could escalate or spiral out of control didn’t occur to him at all. After a particularly brutal 24-stroke caning one rainy Wednesday, he gasped when she produced a fiendish-looking purple strap-on cock. “No way!” he shouted. “Nonsense, Alan. You will learn to take it and thank me for it. This will become part of your training and practice regime. It punishes the inside of your bottom, just like the cane punishes the outside.” “This is too much, Madeleine!” “Nonsense, my boy! Surely you’ve had a penis up there?” “Certainly not! I’m straight. Can we change the subject please?” “No,. Her breasts were closest to the ground, and her back arched and stretched her shirt so tight that it was actually beginning to tear at the seams. Her breasts were hanging almost completely out, and her nipples clung to the very edge of the fabric, trying as hard as they could to stay covered. Her skirt had ridden up so that it was bunched around her waist, and she hoped that the bit that hung down was enough to shield her pussy from this wild man's watching eyes. It soon would not be. He transitioned from stroking himself to full-on masturbating, slowly pumping his member and cupping his balls. She knew she should be indignant, but her mind was dominated by thought of stroking his dick and cupping his balls. She wanted to suck on and lick the head cock and jack him off till he came. Suddenly, she felt something on her ass, moving against her skin all the way up to her neck. It felt hard like a penis, but it was too long and snaky. Then she felt it pull up sharply, and her skirt and.
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