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My Fling With an Older Woman

Years ago, I had a fling with a woman much older than myself. I met her while on summer vacation on the Vineyard. I was still trying to decide whether or not I wanted to go to college or just continue working. I was twenty-one and she was 45. She was there with her friends, trying to decide whether or not to return to her emotionally distant husband who made tons of money as a Wall Street stock broker, but worked all the time doing it. She didn’t set out to have an affair and neither did I, but as the saying goes, shit happens.

We met innocently enough at a mutual friend’s house for afternoon cocktails and conversation. We hit it off right away. She was one of those classically beautiful women who oozed sexuality out of every pore and made it to where guys didn’t care about her age. Almost immediately I knew that I wanted to have sex with her. I began to plot how I would convince her that a sexual relationship with me, no matter how brief, would be a wonderful thing.

Fantasy to Reality

In between my thoughts of sweaty sheets and erotic fantasies, I realized that she was a good listener. I told her about how my father was pressuring me to go to school, saying, “You’ve had three years to screw around. Now you need to get your ass in school so you can get an education and make some real money, son.” Trouble was, by my estimation, I was already making money. College really wasn’t my dream and I wasn’t sure if I wanted to live for my father’s dream for four years. My new lady friend seemed genuinely interested and understanding of my plight. In turn, she told me about her problems with her husband and her marriage. I could see that she enjoyed telling me things, probably because I was a stranger willing to sit and hear her side of things. She said that she really didn’t want to get a divorce after spending twenty years with this man. Admittedly, most of those years were happy, satisfied years. She felt that that was a lot of work to just throw away. The marriage had only been on the rocks the last couple of years. They had never had children, so that wasn’t a concern.

So here we were two lonely people. Without thinking too much about the consequences, I asked her to go to dinner with me. I didn’t think there would be any harm in asking and no one would think anything about it. She hesitated a moment and I could see all the conflicting emotions cross her face. Then, just when I thought she would say no, she nodded. We worked out the details and I left to shower and change clothes.

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The Age Difference Didn’t Matter

I will admit that I hurried through the shower. I was afraid that if I was late that she would decide not to go. But she was there when I knocked on the door of her cottage. We ate dinner and the wine and conversation flowed. The chemistry between us was great and I have yet, even years later, to find it again with another woman. There weren’t awkward silences. It was great. Afterwards, I suggested a walk on the beach. Again, she hesitated, but agreed. The night was perfect for walking on the beach. We continued to talk and laugh. Finally I walked her up to her door. As she opened her door, I said goodnight and was about to walk back to my car when she touched my sleeve. She asked me to come in for a night cap. I smiled and nodded and followed her inside.

Yes, we ended up in bed that night. But before that, we had a long talk about the age difference and how she didn’t go around seducing much younger men. She was very attracted to me and was very embarrassed by the strength of her attraction. I told her that I felt the same and didn’t know if I should just ignore my attraction or go with it. We went with it and that night was the beginning of a great relationship. Even though I wasn’t a virgin, she taught me how to really please a woman sexually and in many other ways. Our affair lasted the summer and was very intense. When it ended, I wasn’t sure if I could let go of her even though I always knew that our time wasn’t forever. But it did end and we both went back to our lives.

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