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I told her, “Just be patient on this. If I could dip my middle finger also inside your asshole, I’m pretty sure we can have anal sex.” She breat...ed heavy and whispered “Ok. Don’t tell me what you are doing. I’m really scared.” I then pressed her inner flesh down and slowly tried to dip my middle finger inside. I could initially penetrate but then, I also stretched her asshole from outside by pressing my thumb just over her asshole and dragged it up.I then managed to put my middle finger in in a. To keep you up to date on where we are in my timeline. When this story takes place im 17 and its summer. So its roughly a year after the last one. Mark and I had continued to have sex and explore although hadnt done anything new. I had approached him about anal sex but he told me he wasnt really into it and turned it down but at the time I didnt really mind, it was only something I thought about trying. So... on with the story.It was during school holidays and it was pretty warm, even without. More

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