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Wouldn’t anyone, if they were in my shoes?Still, I selected “no.” Whatever strange force—and yes, I already believed something supernatural was at play—had infected my camera and posed me a question with such an obvious answer had wasted its time. Sure, I wanted change. Wanted it more than anything. That’s why I was going to force it; tonight, by my own hand.Then, would you like to change the lives of those you hold dear?I hadn’t expected another message.The faces of the two women I lived with—my aunt and my younger sister—surfaced momentarily from the depths of my selfishness, but I closed my eyes to them.Aunt Riley was getting by just fine without my help, and Jessie—You’re running away from it.—was better off without a useless brother like me. I selected “no” again.There was no third prompt.Since I didn’t have anywhere in particular to go, I walked aimlessly around my small coastal Florida town of Navarre taking pictures of whatever happened to catch my attention. I’d like to say. I laid on the bed on my stomach and she helped me put a pillow under my hips. She started by inserting a cotton swab with Vaseline into me so I could get used to something going in. After 2-3 insertions of the cotton swab, she changed to a pencil wrapped in a condom. This did not bother me at all, actually it was pleasurable. Then she put on a disposable glove and slowly inserted her middle finger, the feeling of my asshole being penetrated like this was odd, but I was getting turned on. Slowly she moved her finger in and out, in and out. Many times she would rotate her finger around. I started breathing heavily and could feel myself getting very wet. She told me that she felt I was ready for something bigger, her 6 1/2 inch strap-on, I took a deep breath and told her to go ahead. She put some lube on the strap-on and around my asshole. She told me that when I feel her pushing in to push out and the head will go in smoother.I felt the head push against me and I pushed out and the head.
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