How I Was Able to Snag My Rich Older Man with a Simple Look

  By: - December 4, 2014 high_end_dating_novemer21_13

It was early spring, when the flowers of love should be blooming. My husband and I were packing to leave for the Kentucky Derby, an annual affair for the two of us. I turned to him and said, “I am an affair waiting to happen.” He never changed expressions, instead asking me if I had dry-cleaned his lucky jacket.

I had been married to the love of my life for twelve years. As far as others could see, we had a great life. We owned private, for-profit educational institutions. They afforded us a beautiful home, Mercedes and BMWs in the driveway, and yearly trips to the Kentucky Derby.

It wasn’t a bad life. However, all sexual activity between us ceased when I was diagnosed with cancer a few years earlier. I was no longer able to bear children at that point, making me very undesirable to the love of my life. I tried everything to renew my desirability to my husband, including breast augmentation, “Botox”—you name it, I did it. But nothing changed our dynamic; we were friends at best.

My husband was sharing in the responsibilities of raising my son from my previous marriage. However, he really wanted his own biological children. As a result of the cancer, that wasn’t in the cards and he was punishing me for it.

My son’s biological father had rescued me from my own family. My father had the ability to provide us with expensive things, including luxury cars, as he owned a very successful firm. When prosperity turned to despair as a result of an expected downturn in the market, I met my son’s father. Though he wasn’t a handsome or sophisticated man, he was my savior, taking me from an imminent, undesirable change in lifestyle.

Consequently, six weeks later I agreed to marry him. He rescued me, because he could afford me. He owned homes and small airplanes. Money was not an issue. I enjoyed that lifestyle for six years, until I allowed love to destroy it.

Unfortunately, I met and fell in love with a man that was far from rich, but who became my second husband anyway. I did it backwards; I married first for money, and the second time for love. I had even disappointed my mother.

Needless to say, I didn’t get much out of my first marriage in the way of money. I married my second husband in spite of his unemployed status. But we both worked hard, and eventually it paid off, becoming very lucrative as a result. However, my son was about to graduate high school, and I knew my husband would file for divorce upon that graduation. I was a very short time from losing the lifestyle I loved and had grown accustomed to.

How was I to face what was ahead of me? I laid awake at night, tormented, knowing that I couldn’t make the amount of money I needed to sustain my lifestyle. I couldn’t do it on my own. During those nights, I would dream of a man with a private jet rescuing me. Although I had married the love of my life, the situation transformed him into a selfish, cheating monster and me into a desperate, needy victim.

I would not give into poverty and become a pauper, while he drove his sports cars. I was a loyal wife for years before I decided I needed more. The stress of the situation had caused me to have quiet affairs with several men, including a world-class sports star and the owner of a very lucrative corporation rooted in the deep South, meeting all of them at blackjack tables. My second husband was a die-hard gambler, and in my efforts to make our marriage work, I even learned to play blackjack. However, these affairs didn’t go anywhere. They afforded me some nice gifts and good times, but they weren’t my future.

I knew the Derby was a target-rich environment for a woman seeking affluent men. I just didn’t know how well off they could be. The Kentucky Derby provides two days of racing. After the first day of racing, I met up with my best friend, who had agreed to meet me at the casino where we were staying. She was privy to all my secrets, and knew I was looking for my next “life,” so to speak. We had spent many evenings canvassing blackjack tables, searching for rich, exciting men who would feed our egos and allow us to hold court and perhaps rescue me.

The evening of the Oaks race was no different. We canvassed the casino, table-to-table until finally we were disappointedly only left with the desire to play blackjack. It seemed there were only local rednecks everywhere we looked. Until suddenly, I noticed an older man, not all that great looking, but well dressed, wearing a presidential “Rolex” on his left wrist. The blue sapphire-and-diamond ring could blind the average person. He wore a beaver Stetson hat and was staring intently, all while smiling at me as I sat cross-legged, swinging my leg invitingly. I sat with a half-ass smirk on my face, as if to say, “So you know you want some of this, don’t you?”

Truthfully, my first thought was he was some small Kentucky landowner who thought he was much more than I did. But I was just in enough of a mood to play along. I tossed across to my friend that he was watching me, half thinking she would confirm my assessment with one of her typical responses in the usual way she makes fun of men. Instead she surprised me with, “Don’t be foolish, he could be the one, follow me.” I stated the obvious: the table was full. However, before I knew it, I was following behind her and walking directly toward his table. And by the time we got there, in the very powerful, yet understated manner that only large amounts of money can buy, he had cleared the table for me.

As we approached, I caught his eye. He was better looking up close, but not someone I would glance at twice without the presidential Rolex, beaver Stetson, and cashmere jacket. And yet, I allowed myself to be reeled into the seat next to him. Since he had cleared the table, only the man in the Stetson, myself, my girlfriend, and his personal attorney were now playing blackjack at the “Kentucky landowners table.”

He very quickly told me that “I was hotter than donut grease.” I must say, I hadn’t heard this line before. But I found myself enjoying the attention I so desperately sought after at home. So, just who was this diamond-dripping, cocky cowboy that was making the scene all about me? I flirted with him, asked questions, and laughed my sexiest laugh, even when he wasn’t all that funny. Just who was he exactly? Was he worth my time? How much was he worth really? How much could he truly mean to me?

He was definitely into me. If he had enough zeroes on his financial statement, I might actually be able to get into him, Stetson hat and all. As the evening wore on, I continued to flirt, just in case he was worth it, as my friend did my research. I could hear the attorney telling her about the cowboy’s private jet, the race horses they were about to purchase, the miles of white fencing that surrounded the ranches he owned, the draft horses he loved, and much, much more. The people that were run off the table hung around to become spectators to the unimaginable amounts of money the cowboy was gambling. Just who was he, and how much was he really worth?

All I had was a first name, a very common first name at that. As I reached into my bag for more chips, the man in the Stetson handed me a few black chips. I tossed them back his way and informed him, “I have more money than God,” as it was too early to consider taking his money. However, if he proved to have deep pockets, this strategy would be beneficial.

He was taken back, but loved my spunk, I could tell. His personal power was intoxicating, and it was all focused on me. As the wee hours of the morning approached way too quickly, rest was on the agenda. It was time to make our exit. As I rose to leave, he handed me his business card, which I tucked safely into my bag. He half attempted to kiss me, but I pulled away, as my husband was somewhere in the casino.

We strutted off laughing, thinking those two were full of it. But I had enjoyed his attention and charm. And he seemed to really like me. And truthfully, I was a bit sad to see the evening close. But once out of his eyesight, we raced to my friend’s hotel room. We had his information. My friend immediately pulled out her laptop, and we began our research.

Upon her initial Google search, she excitedly said, “Look at these barns; his cows live better than I do!” The attorney was telling the truth. Not only did the man in the Stetson possess all of which my friend was told, but he was one of the richest privately held moneymen in the United States. He had a great financial statement, and he held many positions of status. Kentucky landowner? Heck no! How about one of the top-15 landowners in the country.

I grabbed his business card, as I dug in my bag for my cell phone. No answer, but the standard voicemail allowed me to leave a message. I left one of the sexiest call-me-back messages I could at that point. I later found out he and his attorney were lost on the way back to their hotel. But most importantly, he had my number. I would wait to see if he acted upon it. I wished I had flirted even more and done something to be sure he returned my call.

The following day, I was in the Millionaires Club at the Kentucky Derby, pacing, wondering and thinking about the man in the Stetson cowboy hat. I had never met a man of those financial means. Had I done enough for him to think of me today? Had I flirted enough? Had I made it enough about him? Or was I too cocky in thinking he was only a “Kentucky landowner” with not enough zeroes for me?

I was a nervous wreck. I kept looking at his business card, when suddenly my cell phone rang; it was the man in the Stetson hat. I couldn’t believe he actually called me! Me, the little girl from Kansas without an education…he was calling me! He was in the Owners Box and wanted to see me! I couldn’t believe it! My husband had secured our tickets from the Foxborough Casino, and they were coveted tickets. The Stetson man couldn’t get to my seats, but I could get to his! Talk about the luck of the draw!

I immediately agreed to see him. I was a nervous wreck. Last night’s drinking and staying up late, I felt, had taken a toll. I ran to the ladies’ room and fixed as much as I could. I had on a tight, pink-sequined top, black pants, pink heels, and a darling hat. I added light-pink lip gloss. It was as much as I could muster at this point.

I walked to the escalator, wondering what he and I would think of each other today. As I descended upon the escalator, I immediately spotted him; suddenly, he was the best-looking man I had ever laid eyes on. He was waiting for me, with another cashmere jacket, more diamonds, the Stetson hat, and a great smile. I knew what that smile could do for me.

We talked, we flirted, and he asked if he could see me again. Of course, I agreed. We briefly kissed a very sweet kiss. And he was off to his private jet for his trip home. I found out later his attorney was excited he had found a way to convince his cowboy boss/client to purchase thoroughbred race horses…thinking I was into race horses. The cowboy had agreed to venture into the racing business as a way to see me. You see, he was married. After our exchange, I slowly made my way back to my seat in the Millionaires Club, knowing my life was about to change forever! I just didn’t know how much.

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