2 Checks

First trip to Staten Island, on the ferry. Hey, I have only lived in New York City for nearly 30 years –> Check

Sex with a 55 year old woman, first in a long time –> Check

So what happened?  Nothing to do with sugar but noteworthy nevertheless.  We were at a friends dinner party the other day, and started talking about the stock markets, interesting trades, old stories, and the general lack of quality financial education that is concise and practical.  And we were all very concerned about that because we all have young children, so the sentiment was: Wow, they teach them math and history, but what about finance and investments.  No wonder when they all grow up and become adults, on the average, they have no idea how to manage their finances.  So I started talking with one of the ladies there that was divorced and concerned about her investments.  She then wanted me to meet on Saturday during the day and review her 401(k). She had taken a beating over the past month, being 100% invested in stocks.  You would think people would have already learned their lesson between the dot com bubble and the credit crunch but noooo.  So I took the trip on the ferry and went to a casual restaurant on Staten Island, an Italian family place for lunch.  Then we started going over her statements, positions, and discussed her viewpoints and risk tolerance etc etc. At that point she was looking into my eyes in what I thought was more than just pure financial interest.  We started talking about families, kids, how tough it is to raise them and teach to stay away from dirty old men, how to become more independent and self confident, and all that.

We ended up on her couch, she gave me a Guiness and by that time I was thinking it was all a ploy to get me in her house and take advantage of me.  Oh well. So we ended up having sex on a quiet Saturday afternoon, which is something I really like anyway.

Will I repeat?  I am not sure, she is quite older than me, and I haven’t been with an older woman in a very long time. I feel ambivalent about it.  I don’t want to just dump her as she is a very nice person. However, my preferred age group now is 27 to 33.  Another post will explain why.  So I have no idea what to do when/if she emails or calls. I may have to just let her know that what happened should not have happened, and hopefully nothing will ever get back to my friend at whose party we met. Sticky!!

This entry was posted in Dating, sex with older women, Sugar Daddy. Bookmark the permalink.

5 Responses to 2 Checks

  1. Linda says:

    I really like reading your stuff.. insight from a SD is always great! 😉 I’m new to the whole SD-SB scene..

  2. Jade says:

    You are playing with fire, arent you?

    I dont know why I have that impression that ultimatelly you would like to be caught.Or that you need a kind of a beginning but you just act at your instinctual level without naming things as you are very responsable and loving towards people around you.
    And of course i could be 100% wrong for which I appologise.

    By the way the lady knows the situation you are in and you know what you preffer. Instincts are the best adviser when indoubt

    If more people errr men would be like you this world would be more ellegant and more sophisticated.


  3. @Jade thanks for your kind words Re: elegant etc.
    Do I want to get caught? Well, I’d rather not. I do find close calls very adrenalizing, however.
    But the last thing I would ever want is to hurt family, just because I like adventures.
    Anyways, sounds like a topic of a very lengthy discussion over drinks…Did I mention that I tend to be flirty sometimes?

    @Linda: thanks and enjoy the reading. If nothing else, this lifestyle is a fun trip full of discoveries about human nature.

  4. Jade says:

    I can tell you are flirtatious and actually charming. Thats why the SBs call you after a long time.

    I was reffering to a more complex psychological thing but did not elaborate. Men love adrenaline but in the same time they call for attention doing what nature is calling for. Its similar to screaming children, excuse the comarisons, women do the same thing shopping and meeting other men. So we are equal, but for men its ingrained in their genetics to hunt. For women, power its an aquired taste and it comes or not, depending if they chose to dominate their genetics or not.

    And of course you know that already.

    So I really wish you as much adrenaline as possible in a safe way.

    I am passionate about human nature, to me its interresting to read what a man thinks about women, him being in an objective power situation without necessarily enforcing it(as the modern douches are doing-class levell, lack of it)

    Anyways, you dont need to publish my comment, unless you chose to. I responded for the sake of the conversation.

    May I ask a question? If you would have the possibility to chose what would you chose:sacrificing yourself forever to make y

  5. SGF says:

    Your blog is great I love it. Makes me sad though to see yet another man who prefers women that young. I am a very sexy 42 who looks and acts about 34. But I am over-the-hill for most men my age and even men much older than me. Feel like I have so much more to offer now than 10 years ago and look hotter than I did when a teenager. :(

Leave a Reply

Your email address will not be published. Required fields are marked *


You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>

This site uses Akismet to reduce spam. Learn how your comment data is processed.