Here is a nice one from the history vaults. I was trying to ‘cultivate’, so to speak, this potential sugar baby. Mind you she wasn’t a tall blond bombshell with big boobs of the age of 20. She was tall enough, but she had dark brown curly hair, and she was almost 40 years old, and elementary school teacher with a Master’s degree in Education. Why did I like her? Because she had those all American looks. She liked hockey, classic rock and had met many guitar legends. You know, God, grandma and apple pie kind of girl. So I was attracted to her. She was very hesitant, she never done this before, she told me that in the past she only had massage arrangements. To me, that sounded totally, totally, ridiculous. Probably because I don’t really like massages. they are way to gentle for me and I end up not feeling much. Anyways, I had kept in contact with her, emailing and texting on and off for a year. Over Italian dinner one day she told me she was ready. I was sort of surprised as she seemed pretty straight laced, but I figured that she had a change of heart.
We made plans to meet a few days later, at her place. And then it happened. For full disclosure I asked her if she had any no no’s in bed. Why did I ask? Well, in the past I had been chastised for not communicating more about these things, by someone else. Who? By Lady Dracula’ in Houston, who even features in my book ‘Sugar Daddy Diary’.
So this time I wanted to be communicative so I asked in a very polite way. Now mind you, she was the type that gets overwhelmed easily. She has to deal with young kids, prepare each day’s lessons, and on top of that she was considering to get in-vitro fertilization as she wanted a child. I guess all that got to her and she texted to me a day later ‘Sorry Dave, but I need to step back from this. It will complicate my life’. Blast!! I tried telling her that I am low maintenance and that I am the last guy that will do anything to complicate peoples lives. After all, I see this type of dating lifestyle as a little vacation, of sorts. We both have our regular lives but whenever we meet we just leave it all behind and have a good time. Like a mini-vacation. What’s not to like? She wouldn’t have it. And all this time I invested…go figuh!
Like I say: You lose some you win some. Only in this case it sucked!!