All of the usual disclaimers apply. If it is illegal for you to view materials of this nature, please leave now. This story is a partial work of fiction. Although the events are accurate, the names of those involved have been changed.
As I've mentioned in the last three installments in the category, these stories represent instances where sex appeared to be a sure thing. Unfortunately, unforeseen circumstances prevented them from happening. These stories are dedicated to the vivid fantasies of what could have been.
I'd been in my apartment for nearly a year. I had grown rather comfortable with the many opportunities I'd had to mess around with other guys. At this particular point in time, I had been able to mess around with a number of the core dudes that hung around the place. Now, it seemed my next challenge was to seduce the "fringers" that previously seemed untouchable.
Shannon had been a semi-regular for several months. He was brought to our group by a number of mutual friends who also enjoyed coming around my apartment. Most of the guys that hung out at my place had above average looks. Shannon, on the other hand, was one of those guys that drew your eyes to him when he entered the room.
Shannon was about 5'8", probably 120 to 130 pounds, dark dark brown hair and had eyes that could cut right through you. I would have to say for the most part, Shannon was smooth all over. Perhaps with the exception of a small patch of hair under his arms and around his dick. He also appeared to be trying to grow a mustache, but was only able to yield a very space patch of tiny, thin black hairs on his upper lip.
There was just something sexual about him. He seemed to charm you without really trying. Shannon was known for his prowess with the ladies. He'd had a number of girlfriends during the time I knew him and in each case, had a number of first time conqests under his belt. One of the more attractive features about him was how sure he was. When recounting his past experiences there wasn't the slightest tone of embarrasment. He seemed very sure of himself. Aside from being drop-dead hot, his certainty was his next best attribute.
Although Shannon loved getting laid, his first love was the buzz. Shannon loved to get drunk and high. In fact, there weren't many things he wasn't willing to try. This would serve to be the one ray of hope that someday, he may approach messing around with guys as matter of fact as his drug use. This assumption really started showing signs of being accurate.
Out of the blue one night, Shannon knocked on my door. I was a little surprised to see him and even more surprised when I realized he was alone. In my mind, I felt as if this was going to be the night that I would work my magic again and finally bagged the untouchable Shannon.
I had already had a few beers by the time he'd arrived and as we talked that night, Shannon and I polished off the better part of a case of beer. As I said, I started working my magic. The beers we were drinking made me feel a little more confident than usual, so it didn't take me long to start in with seducing him.
Like many conversations of this nature, it started out pretty light. He seemed rather curious about what sex was like between two guys. I don't know if this was just genuine curiousity coming out, or if he was using the opportunity to actually have sex with me. In either case, I treated the conversation as a sales pitch to him. As the banter became more direct, I found it more difficult to speak about it. So, rather than spending the better part of the evening struggling through questions to him, I chose to write it down and pass the paper to him like kids in school.
I remember asking him in our letter, if he'd ever consider having sex with a guy. Rather than giving me a direct answer, he told me that it would depend on the situation. I then asked him if there were any of our mutual friends that he would be interested in messing about with. Again, a cryptic answer. These ambiguous answers just went on and on. At this point, I was getting pretty arroused.
At this point, he became a little frustrated with the passing of the pen and paper and asked me to just talk to him about it. I was pretty nervous at this point, so I indicated to him that it would be much easier for me to just write this stuff down.
As we became more involved in the questioning, the mood in the room transformed from a hypothetical scenario to one of actual planning. I still wasn't getting direct answers to his questions and I took this as him wanting me to make the move. I sat for a moment longer in an attempt to muster the courage to ask him to go into my bedroom with me and fool around. JJust as I was about to pop the question to him, there was a knock at my door. For a brief moment, I thought that if we remained quiet, maybe the person on the other side of the door would just go away. However, my stereo was on and the lights from my livingroom were certainly visible to my guest in the hallway.
I gestured to Shannon that this was only going to take a few seconds, then stood and answered the door. Much to my regret, the person that came to visit was one of my geeky friends from highschool. He invited himself in and for those first few moments, I gave him the eyes that said, "can't you see I'm fucking busy!!??" He appeared oblivious to his intrusion and plopped down on my couch. My mind was torn from my conversation with Shannon and thrust into a meaningless conversation with my new guest.
I kept suggesting that Shannon and I were in the middle of soemthing and tried politely to suggest to Matt that he needed to leave. During my attempt to brush off Matt, Shannon must have decided our time together was over and reached for his coat and announced he would see me later. Regrettably, I acknowledge his departure and watched as this great chance had just slipped through my fingers.
Once I was certain that Shannon had left my building, I jumped all over Matt for having ruined my chance with Shannon. He seemed shocked to learn this and I just shook my head in disbelief that anyone could possibly be that stupid. Once he figured out what I was talking about, he laughed at me for losing a lay. With that, I told him to get the fuck out and not come back. I was pissed!
Several years passed and I ran into Shannon at a favorite watering hole of mine. I was belly up to the bar with my brother on the right of me and Shannon to my left. Although we'd not spoken in nearly ten years, I reminded him of that fateful evening. I wasn't sure how he was going to react to the subject, but threw caution to the wind. I laughed when I told him that I was pissed that Matt stopped by because he and I were so close to having sex that night.
He tried to convince me that I was wrong and that he had never once entertained the idea of having sex with me. I laughed out loud at that. Why did he feel the need to convince me that he never considered it? I followed his attempts to prove he wasn't interested with the fact that if I had really wanted to have sex with him that night, it would have happened. From that point on in the conversation, I think we agreed to disagree. Besides, even if we had actually had sex that night, he'd probably still try to convince me that it never happened. In either case, deep down, he knows I'm right and he will always be left with the same "what if" as I do.