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My Strangest Sexual Experience

Posted by: Age: 21+ Posted on: 3 comments
8 likes 6 views Category: Sex Stories General Tags: Older woman, younger boy, fucking,

My friend tricks a woman into taking my virginity.

When I was younger I was a real car nut. Still am, but no longer have the “hands on” involvement that I had in the past.

I used to hang out at a local speed shop. I even worked the counter on Saturdays when the place got busy even though I wasn’t paid. The shop also had a race car that was used to promote the business at local tracks and I drove the race car for the shop owner. Because of my close relationship with the owner, he would let me bring my own personal hot rod into the shop and work on it. The speed shop had a large work area in the back that held about eight cars in various stages of repair or modification.

Anyway, it was a Sunday and the shop wasn’t open but the owner had come in to set up a new machine in the machine shop area and I was in the back preparing to work on my own hot rod. The owner came back to the shop and he had a pretty good-looking older woman with him. Probably 30-35 years old. He introduced me to her and told her that I was an 17-year-old virgin and wanted to know if she could help me out.

I had no idea what was going on but decided to play along. He left and the woman put her arms around me and whispered in my ear that she would take care of me. We climbed into the back seat of one of the cars that was in the shop. My memory is that it was a large Cadillac or maybe a LaSalle, four-door sedan from the 1940’s.

We went about getting naked. During the whole time, I thought the owner was playing some kind of joke on me, and I expected him to show up with two or three of my friends who also hung around the shop. Everybody laughing and pointing at my total embarrassment.

But that didn’t happen. The woman proceeded to take my “viginity.” I wish I could remember the details to pass on to you readers but this was in 1956 and all I remember is that the two of us fucked. I think she might have made me wear a condom since this was way before the pill. After we finished and pulled our clothes back on, she gave me a kiss and went back to the front of the shop. I never saw her again.

I asked the shop owner who she was and he just said she was a friend who he thought I might have some fun with. I’ve always wondered if he ever told her the truth about me. I have also wondered if maybe she was a hooker he had hired.

Now here is the kicker to the story. She thought I was an 17-year old virgin but the truth is that in 1956 I was married with two kids and had fucked at least five or six different girls and women. Many, many times. I have always looked very young for my age and even today when a stranger guesses my age, they are usually at least 15 years off. So I could easily pass for 17 when this session took place.





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