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Lifes Strange Twists

Life can take strange twists and my story is about one of those. Over 40 years ago, while in high school, I dated a pretty blonde girl from a neighboring town. We dated for two years until we were both seniors. The word on Jill was that her parents were very strict and were not warm and friendly with the boys she brought home. Jill was supposed to be “cold” in a sense that she was hard to get to any “base” with.

Well that wasn’t true with me. I hit it off with her parents very well and we became involved somewhat sexually as well. In fact, Jill was sick one Sunday and her parents were going to be gone for the afternoon. They asked me to come up and sit with her while they were gone. Jill was in her robe when I arrived and her parents soon left. It was nearly an hour after her parents left that I realized that she really wasn’t that sick. She came back from using the restroom with her robe open and her beautiful body in full view.

What happened next you wouldn’t believe, coming from a guy telling this story. We certainly played around but I decided not to go all the way with her. Soon after we broke it off and the main reason was that I thought we were getting too serious. I know it’s hard to believe! ?

We each went our separate ways after high school. I went to a small private school in NW Iowa and played basketball and baseball. I completed my degree in the education field and taught and coached before becoming a principal and superintendent of schools. Jill went to a private school in north central Iowa and became a social worker.

Jill married a guy from her high school that went on to law school. Shortly after joining a law practice he began cheating on her and they ended the marriage after two short years. Jill moved from Iowa City to Sioux City and married again. This marriage produced two children but was not a bed of roses.

I married wonderful women that I met in college and we raised three kids. My wife was a cheerleader for the basketball team that I played for and that is how we met. We’ve now been married for 38 years and have five grandchildren.

Fast-forward the story about twenty years when I was an elementary principal. Jill and her husband moved to same town and enrolled her kids in my school. Her daughter had a severe hearing loss and I helped her obtain services. We talked many times but we were always professional. Jill became an officer in our school’s PTA so we saw each other a lot.

Jill and her husband moved to Missouri and I lost contact with her until she called me one day. She explained the services for hearing impaired weren’t very good and I helped her research additional help for her daughter. My suggestions worked out and she said she owed me a drink.

Jill sent me an email and said she would be back visiting her dad who was now in a nursing home and wanted to “pay up” the drink she owed me. I often went back to my hometown to hunt and fish with my brother and set up another trip. My wife didn’t accompany me and our oldest kids were in high school so it wasn’t unusual to have me head out for a day or two without the family.

It also wasn’t unusual for me to head out at night as quite a few of my high school friends and many that I played competitive softball with were still around the area. I went to meet Jill at the lounge connected to the motel where she was staying. We visited for nearly an hour before she asked me to have one more nightcap in her room.

Jill fixed me a drink and she had a glass of wine. We began talking of old times and the people we double-dated with. She gave me static about breaking it off and told me she was sad we didn’t hook up at a wedding we both attended when in college. She said, “I had plans for you and you went to play a softball game instead of going to the reception.” I responded, “You had plans for me?” She said, “I sure did.”

We continued this conversation for a while longer and I said I’d probably have to be heading home soon. Yes, I know it’s hard to believe that I’m such a dipstick! I stood up and Jill came over to where I was standing and our eyes met. We had the same thing in mind.

I put my arms around her and kissed her. She responded with a second passionate kiss and asked if I could stay just a while longer. Next, she unbuttoned her blouse and said, “I may not see you again and I’m not going to let you get away this time. We were both in our mid-40s and she still looked great. I helped her remove her bra and soon those 38D’s were in plain view.

We passionately kissed again and I sucked and nibbled on her tits. She moaned with pleasure and there was no turning back. Jill reached and unzipped my pants and soon had my shaft out. She licked, sucked, and teased me before taking the entire package in her mouth. Wow! She was very skilled!

She undid my pants and I let them fall to the floor. Within minutes we were both naked and I found myself using my oral skills. Jill thrust her pelvis into my face as I stimulated her clit and fingered her pussy. She begged me to complete the job and I guided my cock deep inside her. She squealed with pleasure and was soon having the first of several orgasms.

The night ended and I made a return trip the next night. We went the next decade meeting at least 3-4 times per year. Most were back in our home area but a couple of meetings were arranged in Kansas City and Minneapolis. Each time we met was more exciting and intense than the last. We screwed like there was no tomorrow.

The story actually ends there. Jill’s bad second marriage ended and she me a great guy that is taking good care of her. As I said in the beginning of the story my wife and I are in the 38th year of our marriage. While I carried on a decade long affair, I still love my wife and see no reason to believe we won’t spend the rest of our lives together. Jill was my first love and there has not been anyone else nor will there be again.

Life really does take strange twists. I’ve often wondered what would have happened if I would have skipped the softball game and went to the reception nearly 40 years ago. Would that evening just been a one might stand or would we have gotten back together?





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