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It felt huge, like her asshole had been stretched 10 centimeters wide. Her sphincter was gripping his dick tightly, but now the dick was inside the ring, stretching it out, not just pushing against it from outside. Christ, it was huge. Now baby, just relax he said. Easy for him to say, thought Caitlyn. At least he’s in now and he’ll come, she thought.But he wasn’t in. Only the tip was in. He put both hands on her hips and bent her over, fully 90 degrees. She was still teetering on the silver heels, holding onto the bookshelves. He didn’t care about her clit anymore even though she hadn’t come. He held her hips firmly and thrust against her. The rest of his penis started to follow the head, penetrating her anus. 1 cm, 2 cm, 3 cm. The pain was intense, it felt like he was splitting her bum open. 4 cm. Unnnngggghhhh. With every centimeter it went in, her ring was stretched wider and wider until the full thickness of the thing was inside her. 5 cm. She wanted to scream but she didn’t. I was seated at a table with 5 other people, two men and three women. All were nude. And all of the firm, trim body variety. I later learned that Melissa had deliberately placed me at a table of very attractive people as part of my conditioning. Everyone at the table welcomed me and we chatted. I found myself talking directly to their faces. That is, I was sent here because I had a habit of staring at women’s chests. Now that I was surrounded by naked breasts, with no constraints on looking, I felt it would be rude to stare at them. After the meal, we went back to the living quarters where there was a game room. Several of us played cards. The only concealment was when the women held their playing cards in front of their chests. It was normal to be naked. If someone had an itch, they scratched it. Wherever it was. After dinner, most people went to the camp’s bar. There was a small band playing. I didn’t know many people yet, so I hung back. But then Melissa appeared and.
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