Introduction
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My sexual discovery began early in adulthood, like so many others. As a young man I spent most of my time outside of college either working or playing video games, both offline and online. As this was the earlier days of the modern internet, I also spent quite a bit of time downloading and watching porn of all sorts, exploring new kinks to see if they excited me. I remember spending quite a bit of time on various different sites looking at pictures, and what limited videos were available at the time, to find new and exciting visuals to get myself off. I also spent quite a bit of time in different chat rooms having cyber sex and role playing with what I told myself were women, though I'm sure many were catfishing.
To me, it didn't really matter as we were weaving our own erotic stories that helped me blow load after load, sometimes orgasming more than 10 times in a day. Like most young men I couldn't think of anything else most of the time, which led me down some paths that shaped many of my fantasies to this very day. In this series of stories I plan on telling some of my more adventurous exploits and possibly telling some entirely fictional stories that were woven during my cyber sex and role playing in those early chat rooms. All of these stories will be from after I turned 18 and take place mostly from the summer before starting college through my mid-twenties, though much of my experimentation started long before that. I am also a first time writer, so please bear with me as I get better with my writing. Constructive criticism is always welcome.
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I remember spending quite a few nights in my bedroom jerking off to all sorts of porn. I also remember spending quite a bit of time on an old website that was dedicated to playing truth or dare. The site was set up in a way where you could post truths or dares and other people could then post their response, including images proving you did the dare. I fantasized quite a bit about the different dares and reading about ones that people had completed. I especially liked the ones where people posted pictures as it gave me more visuals to jerk off to. There were some dares that stood out more than others though, some that I remember to this very day.
One that still stands in my memory, very vividly in fact, was one where you took an old pair of jeans and cut a slit on either side of the seam right in the crotch. Once the modifications were complete you then went to a public place like a store and "accidentally" dropped something so you had to bend over to pick it up. Of course part of the dare meant you had to bend at the waist and not the knees. The goal was to get your balls or pussy lips to expose on either side of the seam in your pants when you bent over. I read this dare thread multiple times a week and fantasized about doing it myself. Seeing pictures of people who had their friends in on the dare so you could see what others saw excited me to no end and even now, while writing this, I feel myself getting harder and more horny. So what was I to do after fantasizing about this for weeks but attempting this myself?
I dug through my old jeans to find a pair that were pretty worn out. I was working in fast food at the time so had plenty of jeans that had seen better days. I found a pair that was a bit tighter than the typical loose fitting baggy jeans of the time, and took to modifying them. I cut a couple slits about 2 inches long on either side of the seam and then tried them on. I never wore underwear so it felt pretty normal, other than the cool fresh air that could now reach my balls and dick. To be honest, just standing in my room wearing my modified jeans was getting me super worked up and I couldn't stand the massive hard on I had so I pulled up some porn and started rubbing my cock through my jeans. The slits had opened up a little more as my cock pressed on the jeans so I was able to pull my cock through the slits and finished jacking off before taking the jeans off. I was disappointed in myself for not going out right then, but unfortunately I had to get to work so I changed and went off to work with the thoughts racing in my mind of when and how I was going to expose myself in the local department store.
I spent the better part of the next few days at work and in class thinking about those jeans I had sitting in my closet. To be honest, part of me was so scared at the idea that I kept talking myself out of it at first. It didn't matter though as I kept playing out the adventure in my mind and couldn't stop thinking about it, jerking off to the thoughts. So much cum was shot thinking about doing this that I finally made up my mind and decided to head over to the store on my next day off.