The Path Not Taken: #MasturbationMonday

The blogging meme started by Kayla Lords might be dead, but that doesn’t mean I have suddenly run out of things to say on the topic, so I am just going to continue using the hashtag for my own purposes. In my last post in this series, I explored some of my earliest and most persistent fantasies, I recently noticed a fairly notable omission from that story so I decided I would rectify that situation here…

The backstory is long so bear with me. It was the summer of 2001, I was 21 years old and in the prime of my youthful exuberance. My life was in a state of eclectic chaos. Due to a history of school expulsions, I had just finished up a final semester of high-school. I landed a job at an early dot-com start-up, and had already been promoted from a warehouse grunt to a database administrator in a few short weeks. The problem was that I was not yet far enough removed from the street-life that had been so key to my survival in the hood. I was still running with my crew of thugs on the weekends, and trying to keep my dragon of a girlfriend under control, while still dealing with being on probation for some earlier conviction and out on bail while awaiting a trial on some fresh charges…

In the midst of all of this my girlfriend’s mother called me one evening, notable because this same woman was currently seeking a restraining order against me and very much hated me. My girlfriend had run-away from home(a common occurrence) and it was somehow all my fault…It was then when I realized that I had had been so busy with work that it had been several days since I had even spoken to my gf. I set to work on tracking her down. This was in the days before cell-phones were ubiquitous so this involved me having to hit the pavement. In a giant sprawling metropolis of 5 million people it wasn’t an easy undertaking…

To make a long-story short, I eventually found her at a youth shelter in an obviously sketchy neighborhood of downtown Toronto. I had used all of my powers of persuasion to convince her to leave the streets and go back to her mother’s house. I was waiting to meet her on a subway platform to take her home while she was checking out of the shelter and saying a few goodbyes when the subject of this story takes place…

I was sitting alone on a two-person bench, late at night, on the nearly deserted and somewhat dirty subway platform. A few minutes into my rather anxious wait I notice a person round the corner. I paid attention enough to note that it was a woman and not my girlfriend, and went back to my own worrying. From quite the distance I began to notice that this woman, whom appeared to be in her mid-40’s, was walking; well, stumbling; down the length of the platform towards me. She was white, heavy-set, not particularly attractive, and very drunk. I’ve seen these sorts of trashy bar-flies before in some of the least-fine pubs I have been in. With her unkept hair, worn stretch-pants, and sloppy demeanor it was not surprising that she’d seemingly struck-out at whatever seedy dive she’d wobbled out of…

As she approached closer I was greeted by a miasma of liquor,(whisky to be precise, perhaps bourbon). There were other benches spaced all along the route that she had just walked, but she continued to approach and wordlessly squeezed her oversized body into the seat beside me…

I’m sure most normal people would have been holding back a retch or two when confronted by this situation, but I’m actually the farthest thing from normal in my sexual appetites so of course I was trying to hold back a growing erection(Mature BBW’s are my kryptonite). Her fat rolls spilled over and under the flimsy armrest between us as her ample thighs pressed against mine. I sat there frozen for a while, not having any understanding of what was actually going on. She seemed to take encouragement from the fact that I didn’t immediately flee, but I was doing my best to pretend that nothing was out of the ordinary and this was just another case of having to be uncomfortably close to the dregs of society that happens so often in the core of a large city…

I could see that a train was approaching and was relieved that I would soon be free of this awkward situation. As the train came to a stop, I made no move to get up from the bench, to my dismay neither did she. So again I sat there for another ten minutes, pointedly avoiding looking at the woman whom was, with ever increasing boldness, rubbing up against me. The wait was made even more anxious by the fact that my girlfriend could have come around the corner at any moment and I didn’t even know how to explain the situation let alone want to have to try…

A second-train approached the platform and again I made no move to board. The woman this time did stand-up, only I hadn’t noticed that she had covertly grabbed a fistful of my shirt first, and was literally trying to drag me onto the train with her. I stared at her in shock and in my bewildered state I could only manage to shake my head ‘no’ as I yanked my shirt back out of her grasp. Looking directly at her face for the first and last time only to see it crushed by rejection and humiliation. It didn’t trigger any sadistic pleasure, only a terrible sympathy. I knew the fact was, that had I not been waiting for my girlfriend that I most certainly would have gone along with this women and had who-knows-what sort of crazy misadventure, but I didn’t and in the 25 minutes this happened we had not even spoken a single word between us…

But that’s really the point of this story. It was that almost-encounter that later served as the jumping-off point of years worth of dark, twisted, and disturbing fantasy for me to safely knock out some self-orgasms without the risk and danger of doing truly crazy things with total strangers. The path not taken became whatever adventure I could dream up, and in retrospect, I probably got way more enjoyment out of those fantasies than I ever would have from the memory if I had gone and just fucked some random trashy drunk cougar…

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