Two men, lil ‘ol me….. and what the hell am I thinking?

Posted on Updated on

I had my second date with the pilot last Wednesday.  We shared a bottle of wine and talked over lunch, at a hotel restaurant.  We flirted throughout the entire lunch.  Small touches of the hand, legs touching, hand on the knee, etc…  I made sure to wear the shoes I bought with the money he gave me, on our first date.  I also wore a dress to show off my legs and the shoes.  He couldn’t stop touching my legs and saying how soft they were.  We went back to the room and had a little play time, before parting ways.

This past Friday, we met again.  Lunch with a skyline view.  A bottle of wine from his private wine locker and a few hours in a hotel suite.   As usual, our conversation was full of interesting things and flirtatious.  In addition to the hobbies that I know about, he told me about his love of Harley’s.  I was excited to hear this.  I LOVE riding.  He really does draw me in even more, each time I see him.  There is still the slight problem of he and my sugar buddy.  He is still seeing her as well.  She seems to be bothered by it more than I, however.  I am getting what I need from him and that is all that matters.  On top of his generosity, we have great conversation and a sensual connection.  It is hard to find that chemistry, so I will continue to see him and grow our connection.

In addition to The Pilot, I started to see a new man as well. I will call him SS. He claims that his friend set up his profile (without his knowledge), as an experiment.  The friend apparently said that I was the first and only woman that he felt was worth contacting, from the site.  So….he was intrigued and contacted me.  We e-mailed for about a week, before meeting for lunch last Saturday.  #1 He is YUMMY gorgeous! #2 He is a sugar daddy and didn’t even know it.  You see, he approached this meeting with a curiosity about the sugar world, thinking he knew nothing about it.  Come to find out, his last relationship lasted three years and he supported her throughout it’s entirety.  To the tune of roughly $2000 per month.

He text me about 10 minutes after leaving the restaurant and asked to see me again.  We had dinner the following evening, followed by drinks and some dancing at a club.  I ended up staying over at his house and slept with him.  The whole situation was not typical of how I like to approach and/or progress in a sugar relationship but, I don’t see him really in that way.  Not sure really how I view him, to be completely honest. We did end up meeting for drinks again a few days later.  He was at a seminar near my house and had a little time to kill in the afternoon.  Perhaps it is HIS mystery that intrigues ME, as opposed to how this normally works.  Although he has expressed his intrigue with how I look, talk, act, etc… I am not used to feeling off kilter in these situations.  He throws me off my game.  I don’t like that, because I like to have a handle on things and some control.  At the same time, I am even more attracted to him…because of this.  #FML  I don’t know how this will play out, but I think that SS is actual BOYFRIEND material.  Holy shit!  I cannot believe I said that.  Someone slap some sense into me…..


7 thoughts on “Two men, lil ‘ol me….. and what the hell am I thinking?

    loveyoursugar said:
    April 21, 2013 at 9:56 pm

    Missed reading your posts. Looks like you have a lot to work with. Have fun!

    simplysurrealblog said:
    April 21, 2013 at 8:08 pm

    Uh oh, danger zone to find this guy boyfriend material! Be weary, he may screw you over!

      sugardaddydiaries said:
      April 21, 2013 at 8:14 pm

      Oh no…I’m too smart for that :)

        simplysurrealblog said:
        April 21, 2013 at 8:15 pm

        Excellent! Us women cannot fall for traps!

        sugardaddydiaries said:
        April 21, 2013 at 8:17 pm

        Absolutely!! Men are a dime a dozen. I won’t waste my time on something that goes nowhere.

        simplysurrealblog said:
        April 21, 2013 at 8:22 pm


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s