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She wanted to be a cheerleader but she would never be one with her tiny tits, and dorky glasses. Following that she would leave to shower, the re-enter about 15 minutes later in her towel to change. I would masturbate every night as I watched her change. You see, I'm friends with her brother who's my age. He would tell me sometimes how his sister, Ann, was socially awkward. She had a few close friends but no boys were very interested in her. One day I couldn't stand watching anymore and I decided to pop Ann's cherry. I knew she didn't know me very well and wouldn't go for it. Especially since she probably just learned what sex was, and never even masturbated. So I devised a plan. I took a job her parents were offering to baby sit her and her little brother. One night they called me and told me they were going to a funeral out of town and needed me to sit over-night. They said Ann was to young the go and for the first night her little brother would be at an over-night birthday party.. “You were MASTURBATING!” she said enthusiastically. I was mortified. “Um, well, I...I...was just...” I stumbled. Chrissy lunged at me and grabbed the pillow away. “Don't stop!” she gushed. “I want to watch.” I was embarrassed and dumbfounded. However, I had just read a story of sucking and fucking. And, I was looking at photos of big tits and hairy pussies. Plus, there was a cute 18 year old girl in a tee shirt and short shorts standing in front of me; and she was not horrified as I expected; in fact, she was turned on. I slowly resumed stroking my dick. Chrissy was entranced. “It's so BIG.” she said. I am not porn star huge but I had jerked off with a few buddies over the years and none of them where any near as large as me. Anyway, I looked at the photos and continued jacking off. Chrissy grabbed one of the other magazines and quickly scanned the photos. “Are you going to ejaculate?” Chrissy asked. Girls. What is the point of masturbating other than to climax? I just laughed and.
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