Without further ado, the plug was inserted into my back passage, quite easily I thought, though I let out a gasp as my little bottom was again violated, and then rotated back and forth until my mistress was satisfied that it was a good fit. Taking a metal chain with clips at each end from the holdall, Miss Bolton attached a clamp to each of my nipples and then adjusted them somehow until she could see I was starting to wince from the pinching of my sensitive nubs.“Now we are going to stretch this little sissy cunt of yours until there is no doubt that you will be able to accept the headmaster’s cock in there” she said as, alarmingly, I suddenly felt the plug expanding in my rectum. Miss Bolton continued to pump the bulb until it felt like the inside of my botty hole was going to pop! By the time Miss Bolton was satisfied that I had been stretched sufficiently, the plug must have expanded to at least double its size as I was letting out little groans of both discomfort and pleasure as. She knew what was about to happen. She got nervous and Nick felt it, her asshole suddenly gripped his fingers tightly. "Shh... you'll take it, and like it" he said to her in a soothing voice. After a few thrusts of his fingers her felt her puckered hole relax and he took the opportunity to slide a third finger inside. Leah gasped lightly, trying to relax. Nick was playing rough, but not stupid enough to shove his nine and half-inch hard cock into her asshole without some work first. He didn't want to hurt her. Leah knew this and she relaxed herself even more, focusing on trying to relax her anal muscles. Nick felt it, and after 20 minutes of lubing, fingering, and stretching her asshole, he thought she might be ready to try to take some of his cock. Leah felt him push the head of his cock to her asshole and tried to stay calm. Nick pressed the head into her opening, slowly, letting the head push through. He felt a pop as he entered her rear. Leah felt it too. She moaned in pain, and.
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