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Slap. “Do you know why this is happening?” He asks her again. “Because,” she breathes out heavily, her body shaking from both pleasure and pain. Slap. “Because why?” He demands an answer out of her. “Because I embarrassed you tonight,” she cries out. Slap. “And what are you never going to do again?” He asks her. Slap “Embarrass you,” she is panting heavily. “I am never going to embarrass you again.” “Good,” he smiles at her and slaps her ass one final time. Slap. Brian rubs at her ass again, admiring his handy work. Her ass is beautiful and red and it is bound to have a slight bruise when she wakes up in the morning. She will think of him all day tomorrow, every time she sits down or moves just right. That alone feels like the perfect punishment to him. “Stand up,” he demands of her. Laurel works her way to her feet, though her legs have almost completely given up on her at this point. She knows that she is not going to be able to take much more, but she wants more. “Get on your. I informed him that I would go slow and that I knew his body well enough to know if the pain was too much and that he was too trust me. He murmured o.k., closed his eyes, and slumped against the table. After generously applying more lube, I moved in behind him to get ready. It was at that moment that I thought he might be right, that thing was huge. I gently squeezed and massaged his cheeks around the head of the dildo and slowly began pushing it into him. He was loosened enough from the previous dildo so that his ass accepted the new one, but I could see how much more it had to stretch and I could feel his apprehension under me. I went very slowly and it actually took several minutes for the head to pass his sphincter. He moaned loudly as it slowly began to enter him. I could tell he wasn't relaxing like he normally does but boy was this starting to look good. The site of that huge dildo slowly sliding into his ass got me going again. I held back though so as not to be to rough too.
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