My first job was doing pool maintenence in our neighborhood. Nearly every house had a pool and I would sweep and skim them of leaves and junk. I would ride my bike from house to house in just my swim trunks and sandals since I was always jumping in the water. One of my customers was a single divorced woman who was about 30. Her ex was a lawyer she caught cheating. I had never met her and had always dealt with the house keeper. But this Saturday morning I went around to side of her house like always and when I entered the gate this knockout blonde in a tiny yellow thong was sunbathing and drinking a pitcher of marguritas. She had on sunglasses and was on her belly on the pool chair with her almost bare tanned ass catching all the sun’s rays. Her top was also untied. None of my customers ever looked like this.
She looked up and said “you must be the pool boy.” She introduced herself as Kristy and I told her I was Andy. I was frozen looking at her then I noticed she was also looking at me. Now I wasn’t a bad looking guy at all, and all my swimming and pool cleaning had given me good muscles and a nice tan. Still, I was only about 5′ 4″ and weighed about 120, kind of small for 15, and never in my dreams did I think I would appeal to a woman like that. I went about my work and had to get in the water to sweep the deep end. Next thing I knew, Kristy had dove in and swam up next to me. I could tell she was a little buzzed and she stood up and put her arms around my waist. “How did I get so lucky having such a hot looking pool boy?” she asked. She was about the same height as me so I could look down and I could see her tits under her loose top. She knew what I was looking at so she asked “do you like them?” and I nodded yes. Next thing I knew she had removed the top and those huge bare breasts were right up against my chest. “Oh, your body’s so hard” she said as she grabbed me. She hadn’t seen anything hard yet! I realized this woman wanted me and I wasn’t going to pass up this opportunity. So I leaned forward and kissed her mouth and her tongue went straight to mine. As we frenched in the water, her hands went down under my shorts. She was panting and sand “Andy, I’m tired of fucking old guys. I want some young meat!” That was music to my ears. I thought the next question might end it though when she asked “are you a virgin?” She could see in my eyes that I was, and said, “good, I’m going to teach you right.” We got out of the pool and dried off and went into her living room. She had a lot of big throw pillows on the floor in front of the fireplace and a big soft white fur rug. First she removed her bottom thong then arranged the pillows and laid down. Her pussy was shaved and smooth and gleaming with wetness. I dropped my shorts and joined her naked on the floor. “Oh, I love your body!” she said and she kissed my chest and licked her way down to my dick. She took me in her mouth all the way and got me all wet but then stopped sucking and let go. “You need to have your first orgasm in my pussy” she said and she climbed on top of me. The pillows and rug where so soft against my head, back and ass and it was like I was on a cloud. Then she lowered her pussy onto my dick and the rest of the heavenly feeling followed. She was already flooded with cum and she screamed “oh god you feel good!” She was riding me up and down and I grabbed onto her huge breasts and couldn’t believe this was actually happening. My best friend had joked that this would probably happen sometime while I was cleaning pools but I never took him seriously. Boy, I couldn’t wait to call him that night! First though, I was getting ready to have the best cumming I ever had. My balls seemed to erupt as I shot my load into her. She smiled and said “cum, baby, cum!” When I was dry she leaned over and kissed me and said “you were great!”
We cuddled and fucked once more then I had to get back to work. She told me I was welcome any time, so we fucked a lot for the next few months. Then she sold the house and moved away, and unfortunately the new owners were nothing like her. Still, I loved my experience as a pool boy stud! (P.S. – later, she invited my best friend over and took his virginity too. We had some awesome 3 ways when we were both 15!)