The Mis-Adventures of a Lesbian Online Dater pt. 5

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In a past post, I defined the term 'cougar'. At the time I was going through a fetish phase that was exclusive to older women. No, I wasn't looking for grandma, nor was I looking for someone my mothers contemporary. My cougar had to be late twenties to mid-thirties; coincidentally, I found her when I wasn't even looking...


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Jamaican Fruit Fly: Most of my online dating has come from wanting to fulfill some desire. In this case, I had wanted to find a woman slightly older than myself. I had some thought that she would be able to show me something that I couldn't experience with someone my own age. No fantasy ever plays out exactly how one might imagine, especially when you are your own worst enemy.

I found her through a Craig's List posting and she was easy to talk to. It turned out she had a daughter in the army, and was in a relationship with a man. Usually, I would turn my back on a situation such as this, but I was also involved, and I'd be willing to work with her. We exchanged photos and I was taken back by how beautiful she was. A few days after exchanging emails, we exchanged phone numbers and decided to meet at a bookstore. After work I headed straight to our meeting place and was pleased that she was there first. (Punctuality is always a turn on for me) Upon entering the bookstore, I found her walking between the aisles and she was just as beautiful as her photo. We talked and shamelessly flirted while looking at books and walking around the store. She walked me to my car and gave me a peck on the lips before we parted.

It was no time before I was trying to see her as much as possible. It's horrible how you can lose yourself in something that you know isn't good for you. As we got to know one another, it became harder for me to accept her relationship. My own relationship suffered, yet it made no difference because I only wanted to see her. During the few months we spent together, she always talked about returning to the Navy, and I did my best to shoot down the idea. We went on a few dates, but spent most of our time indoors. It wasn't a highly sexual relationship, but I enjoyed my time with her. She had a way of being so closed that made me want to break down her walls. In my opinion, she loved the man she was with, but at the time he wasn't providing her with something she desired. 


What I learned from Jamaican Fruit Fly,  was that I am not as closed off from my emotions as I think. I ended our relationship abruptly because I felt like I would never have her the way I wanted her. For some reason I lost sight of my original intentions, believing a woman that had all that she did would completely switch her life for me. Those things only happen in fairy tales, but I was lucky enough to realize my own stupidity before she had to tell me. Looking back at the short relationship now, there is so much I would have done differently, but then it may not have even happened...

Part 1, 2, 3, 4 of the Lesbian Online Dating Series


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