This story is found on Literotica but I'd like to do a different ending!
I had just passed my 30th birthday and I was already wealthy beyond my wildest imaginings. I had always been a bookworm and intense student in my school years, a nerd if you will, and I was easily able to translate my single minded focus to excel and succeed in any challenge placed before me into an entry level job as a junior financial analyst at a major hedge fund. I have to admit of course that luck can often play a significant role in anyone's success, and that I began my career at the ground floor of a major stock market surge as it climbed out of its most recent severe recession. But I must also say that I have an innate talent and instinct to analyze often esoteric financial data to discover obscure corporate strengths and weaknesses and spot trends before they become obvious to all. So my recommendations, even from the very beginning, were very frequently ahead of a wave as the market crested upward. This did not go unnoticed, as my rapidly rising salary and progressively increasing bonuses clearly attested. I also rose to full and then senior analyst, and was a full fledged 'Master of the Universe' in very short order. Banking and betting on my own acumen as well, I invested heavily and often with my own funds, and as I approached my 30s my net worth easily measured in the tens of millions.
But I was growing increasingly tired of the 16 hour work days, which usually included even more time on the weekends. And although I was very good and successful at it all, I came to realize that I had no great love for it, or even doing it, and it was not how I wanted to spend the rest of my life. And I also knew that I now had more than enough money that if I just carefully managed my own portfolio I would never be required to ever work again. I could retire most comfortably and use whatever time I needed to seek some other life challenge in which to excel and conquer and fully ensnare my desire and devotion.
And so I did. At first I did nothing at all, allowing myself a well deserved rest. It wasn't very long however before I became bored, but instead of spurring me forward I became even more indolent. And without some immediate urgent task in front to engage me, as I had always made sure to be the case in the past, I came to understand what I always had refused to acknowledge. I was crushingly lonely.
I was an only child of a pair of professionals who divorced when I was only ten, who obviously cared and were more dedicated to their careers than to each other. Or to me. I spent most of growing up years in boarding schools and then college before embarking on my own career. I maintain a correct but not close relationship with both parents, and while they both profess happiness at my success, I suspect this is in large part because they no longer feel any financial obligation for me.
Given this upbringing I had never developed much in the way of social skills, nor ever had much of a social life. During my school years it wasn't that I was unpopular as much as that I was invisible, spending most of my time in books and studies, and later on totally enmeshed in my career work at the fund. In idle moments I did frequently think desirously of women, but I had never had a girlfriend or even ever been on a date. I always had the feeling that women all had some knowledge and understanding that I sorely lacked, which they would see, and which would never allow me to measure up.
But now I had money and plenty of it, which I thought might go a long way to leveling the field for me and at least get me to first base, if not hit a home run. So while I took this time to discover a new life challenge and path, I also decided to try to develop a social and personal life. To aid in that regard I moved out of the functional but drab apartment in which I had been 'living' and bought a swank three bedroom condo with spectacular harbor views on the lower west side. I also seriously upgraded my wardrobe, although I must admit that my fashion sense was very limited. Still, I was soon ready to plunge forward and make my too long delayed mark on the social scene.
Unfortunately, as I soon painfully learned, having the financial wherewithal does not automatically confer successful know how or ability in this realm. Despite numerous forays to different clubs and bars with their many opportunities to meet and interact with women who were seeking to connect there as well, I not only never could get to first base but consistently struck out time after time. I just didn't have any idea on how to approach any of them, either being totally tongue tied, or apparently saying wrong or stupid things. Whatever the reason the lack of interest in me proved universal, serving to daunt me even further. It wasn't long before I became so intimidated that I stopped trying.
Instead I retreated back to my condo, which had been meant to be a 'playboy's lair' but now was rather a 'loser's sanctuary'. I was clearly good at making money for people but apparently little else. And it appeared that this was all anyone would ever want or need of me. While I might desire more, I was coming to the dismaying conclusion that I really didn't have anything more to offer of myself. To anyone.
I began going out less and less often, even ordering in delivered take out for all of my meals. While never a 'neat freak' I had always been orderly in my daily activities and existence. But now, even with an overabundance of time on my hands, I had no energy or motivation to clean or tidy up after myself, as the rising accumulation of empty food containers, unwashed dishes, and general disarray in the apartment amply attested. It finally reached the point where even I realized that something had to be done, even as I had no inclination to do anything in this regard myself. So I went onto the web to search for domestic cleaning services and found there a local company called 'Maid to Order'. I called them and arranged for someone to come for three hours, three days a week.
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