As the bulbous head of his cock began pushing into her, she tried to relax her anus and allow him easy passage into her. However, he kept giving her a...short, hard thrust that she couldn’t prepare for and made her clench. She realized that this was a punishment and it was supposed to hurt, so she stopped trying to make it easier on herself. She gritted her teeth as the head made its way past her anal ring. Once it did though, he thrust himself in her all at once. The pain took the wind out of. But, just as I was getting that familiar feeling in my groin and thought I was about to cum, she stopped. She explained that prisoners are not allowed to cum, and any trustee who allows a prisoner to cum will immediately be placed in a pillory and lose his/her Trustee rights. She then gave me one last lick and turned and walked away, leaving me immensely frustrated. It would not be the last frustration of the evening. Watching her wiggle her naked ass as she walked made me want to cum even. More

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