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She screamed delightfully loud. Then louder when I broke through her cherry. After a while I got her pussy full to the limit. Tears streamed down her face, she was in pain, but she looked at me and said, "Fuck me!" Well of course I was, but it proved she was being brave and trying to endure. Eventually she did reach the point where some pleasure started to mix with the pain. Which meant it was time for the next step.When she felt the tentacle at her asshole her face changed to a look of shear panic. She shrieked with pain as I forced my way in and took her anal virginity. Very tight back there too. Took a long time to get all the way in. She was crying and moaning nonstop with her mouth hanging open, pain, pleasure, didn't matter anymore, so I was able to go straight in. That and the introduction of action on her clit caught her body off guard. She finally broke through the pain and came. After it was over and she was on the floor, tired, sore, and coated with my cum, I heard her. ” Elaine’s breath was becoming ragged, and her heart felt too big for her chest. Somehow she typed, “I’m looking forward to it.” She almost giggled at her audacity. Instead she shook her head. “So am I,” Gary typed back, with a grin. “I’ve almost finished describing the items in the list you had question marks over. I’ll send it back to you tomorrow. Let me know when you’ve finished it. Then we’ll talk about it, okay?” “Yes, Sir.” “Okay. Good.” He started typing again. “I’m just trying to think of anything I might have forgotten. Well, there is one thing. I want you to remain realistic. I’m not perfect. Don’t expect some perfect man or perfect gentleman or perfect lover. I make mistakes just like anyone else. I forget things and I can’t do everything on my own. I recognise my imperfections and I’m not averse to talking about them. I like to know when I screw up so I can do something about it.” “That’s a good trait, Sir.” “And I just thought of something else.” .
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