"I do not appreciate being treated like a whore! I told you I didn't want any money from you and was pissed when I found this in my vest pocket. Please take this fifty-dollar bill and do something good with it or give it to charity. If we are going to have some sort of relationship, I don't want your money!" Miss Ruby was totally confused; every man she had been with had loved receiving money from her. She quietly took the money and slipped it into the pocket of her robe.
I was keeping her off guard in always being different from what she had been used to. I didn't appreciate her take-charge attitude when it came to me and certainly didn't like her making plans for me when I had other things planned. Another issue was my car. She had ordered someone to have a key made to make it more convenient to move my car from one place to the other when we rode together in her limousine. It unnerved her that I was not impressed by the limo, her driver or any of the trappings that made her life different from mine. Though I was only a tender nineteen year old, I had already formed personal habits, which were just the opposite of the many men she knew. That impressed her, even though she still wanted me to be impressed with what she had accomplished. Soon, I found out that the gig we had at the Iron Gate had been arranged by her and was a payoff for something the owner owed her. We had been there weeks before I met her and before discovering what influence she had in the local entertainment industry. She tossed around her power to award or punish as she saw fit and wanted to have a lot more influence on me than I allowed. Often, all she wanted was for us to talk. She was fascinated by my ideas and ideals; and at some point asked, "Would you help me change my life?"
I was constantly in somewhat of a state of shock in dealing with her. I knew she was older than I but her age was a town secret. Some weeks had passed with us having intermittent encounters and occasional sexual interludes, which always freaked me to the maximum. Here I was, a young man still feeling his way in life, with a very beautiful, yet barely educated woman, who had a huge legacy of success dealing with the gutter end of life. Which I abhorred.
I constantly wondered if seeing her at all was too large a contrast for what I wanted from life; but my ego always climbed in the equation, causing me to succumb to her desires. It was easy to see that I had become someone special to her, perhaps because she came to realize I would not be overwhelmed with her lifestyle nor in what I could "get" out of her. We walked a fine line to continue that relationship¾whatever it was called. One day I came home from Harris Teachers College knowing I had to grab a nap before going to work at midnight after getting homework done. Miss Ruby called, begging, pleading that I meet her as soon as possible. Since explaining my situation didn't move her, I finally agreed for us to meet. She gave me an unfamiliar address not too far from my home so I wasn't too concerned. I went and knocked on the door to find her in jeans and an oversized man's shirt. I had never seen her in other than her finery, and was pleased to see an ordinary woman who was still just as beautiful as ever.
Ruby hugged me vigorously, "This is our new place. A place where we can meet and not be around the crowd or the bodyguards and all those people you don't care for. I want you to help me invest money in places so you'll think better of me." While she still had an almost begging expression on her face, she seemed satisfied that she was doing what I would have her do.
I was still somewhat confused, "why me?'
She went through a long explanation about never having met someone who wasn't trying to get all they could from her and she knew months before that she wanted me in her life. I couldn't help but be impressed that she thought enough of me to buy a small house where we could spend time together alone, but it caused me additional concern, wondering how deeply I was getting with her.
She told me she knew I had to get back to get some sleep, but I could stay there if I wished. As she planted the key in my hand, she hugged and kissed me more like a close relative would than a lover. We continued our occasional interludes, but she grew more dependent on my advice and ideas to the point that on more than one occasion she handed me a bag of cash to help her count. Always those sessions led to a discussion about purchasing another apartment building or house that would produce additional income. I had saved what I considered good money from my earnings from entertaining but wanted to leave that life because it kept me in a quandary, not really wanting to be in that life.
So I became not only her lover but also a confidant she grew to depend on more and more. I learned she had arranged for another Madame to handle her girls and was no longer involved in the gambling trade in town. She began to see that she could take the money she earned from her lounges and taxicabs and invest it in other legal enterprises and make even more money. It thrilled her like a child who had been given a new toy and it kept me visiting her regularly. There came a time we were at our house discussing investment strategy when she fell apart. She simply blurted out that I needed to step up to the plate and be more of a man for her, so she could step out of the limelight and be a housewife.
At first I thought she had lost her mind but then recognized that she was a very lonely person needing someone to share with her. It was then I told her about my girlfriend whom I later married. I was surprised that she already knew about her. She made a few specific demands to me, while I told her in no uncertain terms I could not be who she wanted me to be for her. After my suggestion that she find someone more her age I soon discovered she took it the wrong way because she went into a rage about having a lovely body, firm good looking breasts, a tight perfect ass and legs of perfect proportions. There was no doubt she was right in her assessment, but I was speaking about a more mature man who could satisfy her needs. Her only reply was, "but I want you."
We fell into one of the deepest sexual forays we'd had up until that point. We never spoke of it again. It became known in the streets that I was helping her change her life. This caused many encounters with men of all ages making sleazy inquiries as to how good was she in bed? Was she an alcoholic? Did she give good head and was her entire body as perfect naked as it was in clothes? I was the envy of many of the men she did business with, but it really was not a satisfying ego trip.
It did allow me to be recognized just about any place I went and accepted as well. Miss Ruby did in fact have a real influence in my life. A year or so after she accepted I was seriously involved with someone else, she had purchased a number of four-family flats, duplexes and a few houses; and I became her bookkeeper and created form letters to send to tenants when needed.
I received my first draft notice in the spring of 1966 and was mentally preparing to go to war. She wanted me to meet her little girl down south who lived with her sister before I was to leave so we prepared for the event. After deciding that she wanted her daughter to come to St Louis, she became a nervous wreck and fell into a depressive state. My attempts at getting her to go visit and not have the child to come here fell on deaf ears. Not known to me, she was preparing to create a life in which to introduce her daughter and keep her away from the real life style she had lived. I found her looking at every sort of magazine available and cutting out articles from the newspapers to help give her ideas of what to do with the child when she arrived. I didn't feel good about the pretense, but she insisted. When her daughter arrived, a beautiful nine-year-old child, I accompanied her to the bus station to meet her. Miss Ruby did not look like herself in that she was dressed in a light colored sundress with sandals as shoes. She was obviously nervous and felt out of place with a child by her side. I took the lead and talked with the little girl as a friend of her mom's and the child suggested that her aunt had wanted her to visit the zoo. We went to eat and took her daughter to the little bungalow she called our house. A handful of friends showed up to greet the child but didn't stay long. The next morning we took a daylong trip to the zoo and her daughter had a blast. I had to work the next day so I didn't see her till late and found Miss Ruby in a frustrated state because of the child. I took her to my house to play with my little sister and when some neighbor kids showed up, she fell into a good playing groove. The next three or four days were similar with the child being happy to play with the other kids. After her daughter went back down south, Miss Ruby fell deeper into her now almost continuous depression. She hated hiding her real life from her child and felt so ashamed. Nothing I did or said helped her get out of the depression that gripped her. It became common when I went by the house for her to be in a drunken stupor; yet she always wanted to engage in sex. Unfortunately, I could not tolerate drunks and refused to accommodate her. On one of those occasions she threatened to get another man who would take care of her needs. When I simply said OK, she went into a rage. She started throwing things around the house and screaming that I couldn't let her do that. I kissed her and walked out leaving her in a sobbing heap.