Not all the way

When I was 15 I was just like every other horny teenager lusting after the girls. I would have fucked any girl really, didn't matter how old or who she was, I just wanted to have sex. Oh I did the normal teen boy shit, stole some playboy's and looked at any other porn I could get my hands on, but it wasn't the same. I needed to fuck a girl and it didn't matter how or who.

My grandma lived in a gated community in Florida, and every summer I would go stay with her for a month. They said it was because my grandma wanted to spend time with me, but I think it was so my parents could be alone. Honestly I think my parents were into swinging and I think this was their time to play, but i never could prove that.

Normally the stay with grandma was boring as hell. Not too many teenagers in a retirement community in Florida, so I spent most of my time watching TV or sometimes in the pool around 2pm. That was went most of the old people took a nap and the pool would be empty. I also went swimming around 9pm because no one was in the pool then either. Mostly because they were in bed by then.

I get up one night and decided to go swim. It was about 10:30pm or so. Grandma was asleep, like everyone else. I grab my towel and head down, slipping into the water quietly as I didn't want to disturb anyone. I had these rings that sat on the pool bottom, so I was diving down, getting them, and coming back up. At one point I surfaced to a middle aged woman standing there in a red one piece swimming suit. We both startled each other and made an "omg" sound.

She explained that she was there to clean the pool, so I politely got out. As she cleaned we chatted about the community. She asked if I was having fun, but I told her how it was boring with all the old people around. I told her that she was the first pretty woman I had seen in days, and she kind of giggled like a schoolgirl. I took her giggle as a sign and I figured I would keep flirting with her. I asked her why she wasn't wearing a bikini instead, and she said it was because she wasn't the woman she was in her teens. I told her that couldn't be true. Honestly she looked great with not one bit of fat and nice tits, she could have pulled off a bikini very easily.

I kept on the topic telling her she should show me what she had and let me be the judge, but she kept on saying no. Finally she said she was finished cleaning the pool, so I helped her carry the tools back to the pool house. We were putting the tools away when I asked again to show me her naked body. She spun around with this look like I thought she was going to smack me, but instead she told me if she did I couldn't tell anyone. I promised never to tell, and with that she slipped her swimsuit down off one shoulder and then the other. She paused for a second and said "I can't believe I'm doing this", then pulled her swimsuit down and dropped it to the floor stepping out of it. I could not believe she just took off her swimsuit. My dick got instantly hard as I stood in front of this naked woman. She had some stretch marks on her belly obviously from having kids, but not many, and other than that she was perfect. I moved closer to touch her but she stopped me saying that was all she would do. I commented on how beautiful she was and asked if she wanted to see me naked. She laughed and said sure. I quickly stripped my shorts off and stroked myself a couple times. I tried once again to move closer to her, but again she told me no. I started stroking myself again, this time a little fast. My intention was to jackoff in front of her, but I never have been one to get off easily. She just watched as I vigorously stroked myself for several minutes. Finally she asked if it would help for her to play with herself. I shook my head yes. She sat back on a lounge chair in the corner and spread her legs. Her pussy opened up and I remember thinking it was the beautiful thing I had ever seen. She started rubbing her clit, then licked her fingers. She rubbed herself against and then pushed 2 of her middle fingers into herself. She laid back and used her other hand to rub her breast. I mad the comment that I would eat her pussy if she wanted, but again she said no. I told her we didn't have to fuck, I could just eat her pussy, but she still said no. I continued jacking off as I watched her finger her own pussy and rub her own breast until finally I ejaculated all over myself. The cum was dripping off my dick when she stopped fingering herself and got up handing me a towel. We put our clothes back on and headed out of the pool house. She leaned in and gave me a kiss on the cheek saying "I hope you had fun". I shook my head yes and commented that it would have been better if we had sex. She responded with "I would have, had you been older". I walked her over to her truck where I asked if she would be back again. She told me they rotate to different areas and she wouldn't be back to that community until sometime next month. I never saw her again, but I can still she her on the lounge chair rubbing her beautiful pussy.

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