Well, it was after the whole thing with Malone was over. It was also Sep / Oct 2008 with all this financial bullshit going on and I remember sitting on my living room floor watching the evening news and press releases etc, in a fetal position while hiding under my blanket. Bear in mind I was still in Houston so I had lost some of my old Wall Street contacts so I was just getting stock market news from stockbrokers and the regular news. Not good. Not only that, but even the commodity market I was involved in was not doing so hot either: hell in a basket. So I needed a diversion for a day and a strong drink. I think I put a variation of my famous ad back on and got a response from someone who let’s call ‘Gypsy’. Why that name? simply because she said she was of Spanish decent back in the 1800’s and part of her heritage was gypsy. She now was working in Houston and San Antonio for some military intelligence or police unit that sounded like NCIS. We decided to meet for a casual after work drink at my favorite English pub (the Black Labrador) but was held up in traffic that evening so I arrived 15 minutes late and by that time she was gone! I called her up and asked where she was and she sounded like she was giving up by saying ‘Oh it was never meant to be’. So I responded ‘Sure it was, you are not that far anyway why don’t you turn around and we can just sit and have a beer and relax’. And turn around she did and arrived at the appointmed place a bit later. She was dressed nicely but the first thing I noticed is that she looked old. She said she was 55! Still good looking though. This was not a sugar meeting, just to make it clear to everyone. It was just a regular date. Many women don’t like eating in front of a man they don’t know on a first date, I noticed. She was one of those, so we just started having those Lone Stars. After the 2nd one she asked me what I thought of her and I said she was attractive and a good conversationalist. She told me her line of work and she said she interrogates people for a living, which I found fascinating. If I ever get out of finance I want to do that, seriously! So what she did is that if someone from inside the military was suspected of some wrondoing from espionage to drug dealing to masturbating she would question them and pay special attention to things like body language. I asked her what she thought of me and my body language or facial expressions. She said ‘Can’t tell much. You are polite and soft spoken’. Fair enough. I told her that her face had a very warm expression on her like that of a mature woman’s. After all she WAS 55. And then she came back with the memorable line ‘What does this face say? Does it say ‘fuck me?’ Took me by surprise and I just responded with a smile ‘It might’. She apologized for being so upfront to which I told her she doesn’t need to apologize we are just two grown ups attracted to each other. And attracted we were…
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Welcome to Sugar Daddy Diary
Blogger, Author, and Sugar Daddy on the down low, David Montrose shares his tips and tricks on navigating the Sugar Daddy lifestyle.
He dated and had mutually beneficial arrangements with attractive women of all ages and walks of life: Attorneys, college students, single moms, air stewardesses, and aspiring models.He blogs and writes about his experiences and likes to share his stories of a 'mature and generous gentleman'. His book 'Sugar Daddy Diary' is available on Amazon and the Kindle
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