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She brought home a video showing two women experiencing anal sex. I was quite turned on. After a couple wine coolers I told her lets experiment. She led me to the bedroom, I undressed as she got everything needed to take my anal cherry.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. "See ya," she yelled as she slammed the door shut.Minutes later, she arrived at Ray's house, rang his doorbell, and stood shivering a bit on his front porch, as she waited for him to answer. She could hear Ray yell something that sounded like "coming," as she heard his footsteps approach the door. He came to the door looking a little scruffy, his face unshaven with a couple days of stubble, and wearing a pair of baggy shorts and a wife beater t-shirt, that actually showed off his muscular arms and shoulders. He was in decent shape for a sixty-something year old guy, Misty thought to herself as she looked him over. He was sexy, in a dirty kind of way.Ray smiled as he saw his favorite teen neighbor at the door, smiling at him, and shivering a bit in the cold."C'mon in, sweetheart," Ray said, motioning her inside. "It's nice to see you again. What'cha got there, for your friend Ray?" he said, looking at the plastic box of food, as he checked out her ass in the tight jeans she was.
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