Straight Male / 28
I told this story to a good friend a couple of years ago, close to the time it took place. By the look on his face I decided to keep the story to myself in the future...that is, until I found this website.
By 22, I was already tall and looked older than that age so when I offered my brother help in his import food retail business, which interested me since working there might promise some paid travel, Danny took me on. A week after I began, Danny introduced me to one of his earliest customers, Penny, a woman in her 50's, thin as a rail and almost as tall as I am. She was the sort of woman who when walking by on the street, you take little or no notice.
She would come in every week or so and outside of a courtesy greeting there were no words passed between us. I certainly did not find her attractive. Also, I figured her to be Mom's age...or older.
About two months after I met her, she started to give me long looks and a quiet, Mona Lisa type smile, as if we shared a secret but this was all feelings I had. One day, she purchased enough goods to need help so I carried some of her foods and drove her home. I stood just inside her kitchen by the door as she put things away. Then, she said, "Just wait a minute" and ducked out of the room. In a few minutes she came back and said, "He's soundly asleep from two beers, let's be quick about it." I had no idea what the devil she was talking about but then she lifted her skirt up to her waistline and DUH! I got it. Surprisingly, my penis got hard and I unzipped my trousers, watching my handful of junk pop out. We moved close to each other, wordless as usual, and she closed her eyes. For some reason she seemed prettier and almost angelic with her eyes closed.
Without guidance or help, my cock slipped into her vagina easily. It was wet and warm. I easily entered her fully and my thrusts were long and slow. I was not terribly experienced but I was not a virgin. I had never felt anything like that. Her vagina slowly pulsated and vibrated, sometimes strongly so. Despite all, I found myself enjoying a fantastic fuck from this skinny, elderly lady. She would grab my hip and pull me deeply into herself, meeting my thrusts with equal vigor. In a few minutes she whispered, "I hope you're close because I'm about to come." That said, we had an unbearably passionate, simultaneous climax and I could feel my anus pulsating hard as I thoughtlessly shot strings into her. She whispered not to worry about coming into her.
For the next two years, Penny and I fucked standing in her kitchen almost weekly. The more we did it, the hotter it became until I found myself wanting to bite her neck and shoulder while engaging her. After a few months she handed me a condom and whispered, "Get into the back door." Quickly, the condom slipped on and I slid inside her rectum, almost seeing stars. The "back door" became a sporadic part of our kitchen door routine. Her climax was just a strong from anal sex.
Into our second year of standing trysts, while in the store she announced that her husband had been transferred so she had to leave town. I was crestfallen but she said she would call and perhaps we could arrange something once in a while. So far, it has not been more than phone sex but this old. skinny gal has pretty well ruined me for other women. We did it all without ever removing our clothes or sharing more than a few words. Yet, it was vividly memorable.
By 22, I was already tall and looked older than that age so when I offered my brother help in his import food retail business, which interested me since working there might promise some paid travel, Danny took me on. A week after I began, Danny introduced me to one of his earliest customers, Penny, a woman in her 50's, thin as a rail and almost as tall as I am. She was the sort of woman who when walking by on the street, you take little or no notice.
She would come in every week or so and outside of a courtesy greeting there were no words passed between us. I certainly did not find her attractive. Also, I figured her to be Mom's age...or older.
About two months after I met her, she started to give me long looks and a quiet, Mona Lisa type smile, as if we shared a secret but this was all feelings I had. One day, she purchased enough goods to need help so I carried some of her foods and drove her home. I stood just inside her kitchen by the door as she put things away. Then, she said, "Just wait a minute" and ducked out of the room. In a few minutes she came back and said, "He's soundly asleep from two beers, let's be quick about it." I had no idea what the devil she was talking about but then she lifted her skirt up to her waistline and DUH! I got it. Surprisingly, my penis got hard and I unzipped my trousers, watching my handful of junk pop out. We moved close to each other, wordless as usual, and she closed her eyes. For some reason she seemed prettier and almost angelic with her eyes closed.
Without guidance or help, my cock slipped into her vagina easily. It was wet and warm. I easily entered her fully and my thrusts were long and slow. I was not terribly experienced but I was not a virgin. I had never felt anything like that. Her vagina slowly pulsated and vibrated, sometimes strongly so. Despite all, I found myself enjoying a fantastic fuck from this skinny, elderly lady. She would grab my hip and pull me deeply into herself, meeting my thrusts with equal vigor. In a few minutes she whispered, "I hope you're close because I'm about to come." That said, we had an unbearably passionate, simultaneous climax and I could feel my anus pulsating hard as I thoughtlessly shot strings into her. She whispered not to worry about coming into her.
For the next two years, Penny and I fucked standing in her kitchen almost weekly. The more we did it, the hotter it became until I found myself wanting to bite her neck and shoulder while engaging her. After a few months she handed me a condom and whispered, "Get into the back door." Quickly, the condom slipped on and I slid inside her rectum, almost seeing stars. The "back door" became a sporadic part of our kitchen door routine. Her climax was just a strong from anal sex.
Into our second year of standing trysts, while in the store she announced that her husband had been transferred so she had to leave town. I was crestfallen but she said she would call and perhaps we could arrange something once in a while. So far, it has not been more than phone sex but this old. skinny gal has pretty well ruined me for other women. We did it all without ever removing our clothes or sharing more than a few words. Yet, it was vividly memorable.
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