Please Note: This story is a work of fiction based upon actual events. Names have been changed and certain aspects have been embellished for artistic purpose and readability. Which parts are true is up to the reader to decide!
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I think that perhaps I had always been curious about other men, but it was not until my early 20s that nervousness and prudence gave way to curiosity and desire. Those early forays into gay sex are stories for another time, but for now I'd like to share with you a tale of surprise and happenstance that occurred after I had already indulged in curiosity once or twice.
First, a bit of background. As a young man of 19, I had finally grown out of teenage awkwardness, and through a lot of hard work, shed the excess pounds of an overweight childhood. Even though I was short in stature, I had learned to make use of what I had. After the weight loss, I had a nice frame. I had piercing gray eyes, and I had tamed a shock of formerly unmanageable wavy brown hair into a close-cropped cap that worked nicely with my strong Scandinavian chin and jawline. Girls were (finally!) noticing me and I was getting some much needed self esteem going. My only problem was that I was painfully shy and sometimes blissfully unaware that I was being flirted with.
It was around this time that I had started my first full time job. I had not yet decided on whether or not college was for me, so I took one of the local factory jobs that was abundant in my neck of the woods. Within the first week I had become fast friends with a girl my age named Jess. She was all of five feet tall and quite thin. No breasts to speak of, and a rather sharp nose on an otherwise pretty face. Of course I fell madly in love, but was unable to act on my feelings. As is often the case, she naturally already had a boyfriend. Although they did break up shortly thereafter, I was too afraid to make a move, but our friendship still continued and I was content. I even had started dating someone else, and lost my virginity to her, although the relationship itself didn't last long. After her, there were a few others as well.
Fast forward two years. Jess and I had both turned 21 recently and were out drinking, celebrating the fact that I had decided to finally go to college. Near the end of the evening, she asked if I knew of a guy Max at work. I thought I knew who he was, and replied that I did.
"He's older, right? Works in receiving?"
"Yeah, that's him. He's 29. Well, I wanted to tell you that him and I have gone out a few times."
By this point in our friendship, I knew that any romance between her and I wouldn't work out, so I didn't feel any jealousy or weirdness, and I said that was cool and asked how it was going.
"Well," she said. "OK I guess. To be honest, I don't think it's anything long term but..."
"But what?" I asked.
"Um, we fucked last night, and well, he's really, really big. Like long, I mean." She giggled nervously. "I'm sorry, I don't know why I'm telling you this, it's just I've never even seen one that big before. It's gotta be like 9 inches long!"
Jess and I had talked a lot about our sex lives over the years, so this was nothing shocking, but I still had no idea what to say. In fact, and maybe it was the booze talking, but I was actually mildly aroused. Eventually the moment passed and the conversation moved onto other things, but for the rest of the night, in the back of my mind, I couldn't shake the thought of what a penis that large would even look like. Of course I had seen big ones in porn, but when thinking in real world terms I couldn't even imagine what it would look like placed next to my own modest 6 inches. Later that night after returning home, I furiously stroked my rock hard cock while I imagined Max's long dick pumping in and out of Jess's slick pussy.
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College had come and gone. I was back in town, living with my folks temporarily while I looked for a job and my own place. As is often the case, my friendship with Jess had faded over the time I was away. While in college, as mentioned earlier, I had experimented with other guys a few times. Nothing hardcore, just some stroking and oral. Enough to know that even though I still liked and preferred women, I had a bit of a cock fetish and enjoyed getting my hands and mouth on one occasionally. I spent a good deal of time online in those days, as many of us did. In the mid-2000s, the chat rooms on Yahoo were at their peak and I would idle many hours away there when I had nothing better to do. Sometimes, when I was horny and in the mood for dick, I would go into the M4M rooms and chat or even cyber with someone, jerk off and call it a night. One afternoon, however...
The IM window popped up with a ding.
"Hey," said the messenger. "Those initials in your screen name, is that what state you're in?"
I replied that that was correct.
"Cool. I'm from there too. Whereabouts?"
I responded, and come to find out, we lived in the same town. Now, for some of you this may not seem like a big deal, but I'm from a quite small town, so here it was relatively surprising. We chatted for the next hour or two, in which I discovered that he was a straight guy who had heard that guys give better head. He said that he loved getting his dick sucked, but a lot of women either didn't like doing it or weren't very good. He was now engaged and while he was otherwise happy, his future wife was just not good at servicing him orally. He went on to say that he had made the same complaint to a friend of his, who told him how he had solved the problem. He told me how his friend Steve had told him that since his wife couldn't suck dick well, he had gone and found himself a guy to use as a regular cocksucker for those times when he just needed a good blowjob. The guy I was chatting to remarked how he had been thinking more and more about what his friend said and had decided he was ready to try it out for himself. He said that his main concern was that he was worried about diseases, as he certainly didn't want to bring anything home to his fiancΓ©e. As we talked, I told him a little about my experiences and I had had many of the same fears, including personal safety and discretion. I admitted that part of the attraction for me was the secrecy, that there was something hot about being a straight guy to the outside world, but liking cock behind closed doors. He considered that for a moment and said that he could see himself getting turned on by the fact that it was his straight cock that was turning an otherwise heterosexual dude into a bit of a bitch behind closed doors.
We talked for a bit more along those lines, until eventually there was a pause in the conversation. I assumed that he had either lost interest or got weirded out, and was about to log myself off when suddenly the IM dinged back to life.
"So, you want to do this?" He said.