Sugar Baby Weekly

Friday, September 15, 2006

Just Lunch

The Gentleman and I were off again.

For a while he'’d send me an instant message and I'd flirt back, but it got to be quite boring, especially when nothing was coming from our exchanges. There were no appointments made and I was consciously keeping the conversations to mundane topics. He was not going to get free wanking material from me.

Once or twice he brought up the subject of our relationship. Mostly I ignored him because we'’d discussed that topic ad nauseum and it was always the same: He thought I was great, we had a great time together, wouldn'’t it be great if we could be together? Let's not forget his (non-sexual) relationship with his longtime partner or that he didn't know me at all since I only revealed what I wanted him to know, or that I worked really fucking hard to make every visit unforgettable for him.

I didn'’t mind that--the work. All the preparation was like foreplay for me. I loved the planning, the gathering of props and the final, costumed performance. It really was like theater. The Gentleman always behaved predictably, making my choreography of our meetings smooth and seamless. I could manipulate conversations to topics I was interested in having, stretch out the cockteasing for as long as I wanted and when our time was getting short, bring him to orgasm in moments.

Come to think of it, maybe the meetings were too perfect. Could I have made myself seem any more perfect? Probably not. I was attentive to his desires, imaginative and a fascinating conversationalist who could make him cum with a few deft strokes of my tongue. Who wouldn'’t want to have more of that? I supposed I couldn't really fault The Gentleman for feeling conflicted about paying to play with a whore and being jealous at the thought of her fucking someone else, but that was the nature of our relationship. He knew it.

I made myself invisible in Instant Messenger, basically writing him off. I wished him well, but I knew I couldn'’t sustain that kind of tug and pull every time we spoke. If we had had a regular arrangement, the way it was meant to have been, and I could have counted on him to honor our appointments, I might have been able to stand his insecurities. As it was, seeing him maybe once every six weeks, I knew they would make me crazy and I would lash out at him sooner or later. I told The Gentleman goodbye, knowing I'’d be hearing from him again. As soon as I was unavailable he'’d start plotting to put money aside that his accountant/best friend wouldn'’t notice so he could see me again.

I decided I needed to move on and, comfortable in my ability to handle negotiations like this, answered an ad posted by The Benefactor.

Middle-aged, he fancied himself a "sugar-daddy type"” who wanted to help a girl out with her bills. Again, he wanted a regular meeting 2-3 times a month "“for mutual benefit."” He didn'’t want to be specific about money, and I was less interested in the per-meeting sum than the reliability of The Benefactor as a regular date. We met for lunch.

Just lunch.


  • At 2:24 PM, Anonymous Anonymous said…

    I am so glad to see a new post. The new guy has no idea what he is on for.

  • At 2:24 PM, Anonymous Anonymous said…

    in for.

  • At 9:47 PM, Anonymous Anonymous said…

    I've been in a sugar daddy relationship with a woman for almost 2 years. It has been fantastic though an emotional roller coaster at times probably for some of the reasons you mention. Our time together is almost perfect. She's attentive to my desires, willing to do almost anything, I get to act out many of my fantasies. As you said who wouldn't want more of that? We often do things outside of the bedroom such as hiking, sightseeing and have traveled extensively. This has blurred the sugar daddy - baby relationship line. If we were closer in age I would consider pursuing a normal relationship with this woman.

    Anyway, it is interesting to read about the "other side", from the sugar baby perspective and I wish you would blog more than you do.


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