Back in the mid 2000's, I had it all. I worked for a financial investment firm as an account manager. I was actually pretty good at my job and managed to slowly climb up the corporate ladder. I was confident, I was handsome and I was very, very sure of myself. I had a revolving door of sexual partners and considered myself to be quite the Adonis. I managed to establish myself in my career and was in no way shy of showing off the fruits of my labor. I drove around in a black Porsche 911 and I lived in a swanky high-rise apartment building. My home was the ultimate bachelor pad which boasted impressive jetliner panoramic views of the city below. I was proud of my achievements and would flaunt my success pretty much everywhere I went. To those looking in, I'm sure it seemed like I had it all figured out.
Sadly, when the global financial crisis shook our world, I, along with most of my fellow colleagues, found myself out of a job. For the first time since college, I was unemployed and it was utterly terrifying. Thankfully, I had a reserve so I didn't really have to alter my lifestyle all too much. Thinking back, I should've been more careful, but I always just assumed that things would eventually get better and I'd go back to my old life once more. I was wrong.
In time, my savings completely eroded and I found myself in dire straits. The first extravagance to go, was the Porsche. It was particularly difficult to part ways with my baby and I actually broke down and cried when she was gone. The odd thing was, I saw that car almost as an extension of my masculinity and now that it was gone, it drove home the fact that I was no longer the man I used to be. Shortly thereafter, I defaulted on my mortgage. Eventually, my home was repossessed and I found myself jobless, homeless and penniless.
With no other options, I moved back home. To my childhood home.
My parents still lived in the same middle class suburb and nothing had really changed since I moved out when I was 17 years old, they even kept my childhood bedroom as I left it. It was mortifyingly humiliating moving back home and I felt like the ultimate failure. I lost everything and now, I had very much reverted back into a teenager. I lost all zest for life and became a lay about. I spent days sleeping and spent nights playing video games. In other words I had given up.
Eventually, my father approached me with an ultimatum: get a job and pay rent, or move out.
Bear in mind my parents lived in the deep burbs and there were no roles available that were in line with my qualifications and experience. In other words, I had to look for something outside of my discipline. I had no idea where to start and I certainly didn't want to end up working in a department store or a fast food joint, I still had some pride. A small part of me still clung to the hope that one day, I'd reclaim my image and get everything back... after all, I was just going through a rough patch.
My mother happened to be close with our next door neighbor, Jane Kirkland, who just so happened to be an office manager at a medical distribution firm. I always had a thing for Jane. She seemed to be an independent career driven individual and always donned tight power suits. On some level, I was always rather intimidated by her, but also found her to be quite intoxicating. She was in her mid-fifties and was in tremendous shape, thanks to a strict exercise regimen. I'd often see her jogging around the neighborhood during early hours of the morning. She was tall, overwhelmingly so. She had long brown hair and piercing green eyes. In other words, she was an absolute goddess.
I recall coming home one fateful day, only to find my mother and Jane deep in conversation. They both glanced over at me as I froze like a deer in headlights. Yes, Jane still intimidated me. I'd known her since I was eight years old and despite now being well over thirty, I still felt like a small child in her presence. Of course, this was mostly due to the fact that I was still smitten, still holding on to a silly boyhood crush, puppy love. Somehow, she made me feel weak. Just with a simple grin, or her crystal stare, it was enough to make me shudder, it was enough to make me loose all my cool and I quickly turned into a stuttering blubbering moron.
"Timmy!" she called out to me. I hated being called Timmy. My name was Timothy and back in my old life, everyone referred to me as either Mr. Johnson or Sir. Now I was being called 'Timmy' like a little kid. I hadn't been called Timmy in well over twenty years. My cheeks burned red in embarrassment as a shiver went down my spine. I certainly didn't want her to see me as a kid. I was a grown ass man and I wanted nothing more than to impress her. I was a captain of industry and a juggernaut in my old world. I was a man. An impressive, powerful, masculine man. I wanted to show her this side of me. I wanted more than anything to show her that I was more man than she could ever possibly handle. Unfortunately, all that came out was, "Hi Miss Kirkland....." in almost a whimper.
My mother and Jane shared a knowing look followed by muffled giggles, "you're still such a sweet little boy," she said with a wide eyed grin.
"Your mother told me you're looking for work," she added, eyeing me up and down.
I swallowed the lump in the back of my throat. I couldn't speak. All I could do in that moment was nod. "Well, we actually have a position open if you're interested. You'll be working in the bullpen in quotes and tenders. How does that sound?" she asked.
Before I could respond, my mother chimed in, "that's right up his alley."
My fate was sealed. My mother made all the arrangements with very little input from me. Jane occasionally glanced over at me with a sympathetic, yet impish grin as they discussed what I needed to do for my interview with her. Essentially, the job was mine, but I still had to go through the process as part of a set of mandatory procedures. So, an interview was set for the following day. I was told to dress well and be prepared to go through a physical assessment. On her way out the door, Jane leaned into me and in almost a whisper said, "Don't bring your mommy. Put your big boy pants on and come alone, okay?" She shot me a condescending grin and practically waltzed out the door.
That evening, I rubbed myself raw with images in my mind of her panting, heaving underneath me, gasping for more, more, more. Yes, she was still part of my masturbatory fantasies and in these fantasies, I was a sex god. I was an impressive specimen of a man and she would fall to her knees in adoration, both overwhelmed and impressed by my masculinity and my prowess as a lover. In my mind, I was an alpha, a dominant confident male specimen with plenty of machismo to boost. In my mind, I left her heaving and satisfied, begging for more as she gazed over my impressive body with an approving, lustful gaze.
This was a silly fantasy, but one I'd had of her for years and years.
