1. My first time wit the old babysitter


    Date: 8/15/2015, Categories: True Story, Author: Kevin1997, Rating: 81.8, Source: sexstories.com

    This is a true story that happened during the summer between my 9th and 10th grade. Let me introduce myself. My name is Brian. I’m like 5 foot 7 inches tall and weigh around 120 pounds. I am told that I am good looking. We lived in a nice suburb near Chicago. I am an only child and both my parents worked. My Dad had just received a big promotion at work and we were about to move about 90 miles away to be closer to his job. They had already bought the new house but since all my friends were in my old neighborhood, they let me stay at the house until it sold. My only job was to make sure I cut the lawn and I cut the lawn for our elderly neighbor who was in the hospital. It sucked because it would take like 4 hours to cut both lawns and it was a hot summer. Being a typical teenager, I got up at the crack of Noon. It was about 95 degrees out with high humidity. Unfortunately, I had been procrastinating and I hadn’t mowed the lawn and people were coming to look at the house the next day. So the first thing I did was throw on gym shorts and a tee shirt and then turned the air conditioning on in the house. When I was about half-way done with our lawn, I decided to take a quick break and cool off a little in the house. I walk in the house and its like 90 degrees in the house. The air conditioning wasn’t working. Great. So I figure there was no use sitting in the hot house and went back outside to finish cutting the lawn. It was so hot and humid that my tee shirt was so soaked with ...
    sweat that I finally just took it off. I finished cutting our lawn and then I went next door to Mrs. Kendall’s house to cut her lawn. Just after I started cutting the lawn, I hear a woman calling my name. I turn off the mower and turn around and standing on the porch of Mrs. Kendall’s house is an older woman around 30 with a sexy tight two piece bikini. Her legs were long and tan and her breasts looked like they may burst out of the bikini top. Of course right away, a bulge starts to form in my shorts. Luckily I was holding my tee shirt in my hands and was able to hide my excitement. She asked me if I was Brian. I told her I was and asked how she knew that. She said don’t you remember me? I’m Cheryl. I still had a confused look on my face. She goes on to say that she is Mrs. Kendall’s daughter. She told me that when she was in high school, she used to baby sit me. That’s when I remembered her. But she was much more of a woman now. I hadn’t seen her in like years. I thought she had gotten married or something and moved to California. She then said to me, you look tired and worn out. Why don’t you come inside the house and I’ll give you some lemonade. I follow her into the house and I am immediately hit with a cold breeze – her air conditioning was working. And it was working real well since I noticed Cheryl’s nipple start to poke through her bikini top. She didn’t seem to mind that I was staring at them. She then motions for me to sit down at the table and she gives me a glass ...
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