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The Yuppie Sex Chronicles, Part 3

by J.R.W.


November 23, 1981

I suppose an explanation is in order. I haven’t written anything down for almost a year. From what I gather, I was completely infatuated with an intern named Raymond. Well, time really does fly when you’re having fun—or at least before it dissipates into total monotony. But enough with the apologies already! Here are the complete details.

The intern eventually changed into a part-time employee. As I said before, Raymond is slightly younger then me, an incredible departure from my usual choice of older sex partners. What can I say? The guy roped me in with his jet-black hair, green eyes, Catholic schoolboy demeanor, and well-proportioned body. At first it didn’t even matter that his skin was smooth and luminescent, that all of his hair glistened in wave after wave of curl, that his long torso remained tucked in youthful and muscular splendor. I had no trouble conversing with him on dates. We listened to the same kinds of music. We were familiar with the same types of films. I didn’t mind that Raymond and I were almost identical to each other, based on our similar ages and backgrounds. I liked how everything seemed like a new discovery to him, partly because he did just graduate from college (he was the quintessential sacrificial lamb that wolves are akin to).

Sex was awesome in the beginning. It was a treat lying on top of another smooth body, sliding my throbbing dick into a firm and hairless asshole. He was inexperienced all right, having been with only two men prior to me. I was so intrigued with his relative virginity that I allowed him to fuck me as well. His short dick was compensated by girth, and I would spread my cheeks to the fullest before sitting on it (even though I knew that my asshole would still be tight around his cock). I was the first guy that he ever penetrated, and I made it worthwhile by riding his dick to headboard heaven. It was so good that when he came, Raymond would still lie there (with his mouth wide open for two minutes straight) until the ripples in his hips subsided. Because of his youth and previous college stint as a gymnast, Raymond was incredibly flexible. We fucked in positions that I didn’t believe were possible. My favorite one was Raymond in a handstand, with his split legs in the air. I would come so much that the semen would spill down both his chest and back. Raymond was also a bit lighter than me in weight, enough for me to pick him up. I used to fuck him against the shower wall, pumping him so hard the tiles would shake.

I can’t tell you when things started changing for me. It couldn’t have been when his job status changed. I’ve had no real qualms about fucking new or former co-workers before. We still had some great conversations, and I felt very comfortable sharing my ideas and plans with Raymond. For a while there, I thought about introducing him to my parents, as the so-called “friend” of course. I remember watching him sleep one night, wondering why I felt so much emptiness for a guy that seemed almost perfect to me. When we would go out, though, I felt my eye wandering around. There was a need that Raymond could not fulfill in me, something that bordered around wanting absolute dominance. When we would fuck, I felt that he was not as grateful, like in the beginning. His inexperience and versatility, while having some positive benefits, did not have the stubbornness that I lusted after in my older sex partners. He was not set in his ways. There wasn’t a long-established top to conquer. Raymond’s body was way too tight for me after while. When I would slap his ass in the doggie-style position, nothing would jiggle—not even the sheer muscularity was disturbed. His ass was smooth without even the slightest down of hair (no wrinkles were there either). Monotony started setting in. I felt like I was fucking the lightweight instead of the heavyweight champion. I kept imagining my sweaty chest against a furry back, putting my hand underneath a rough and bristly chin as I place a wet tongue in a velvety ear. The fact that Raymond couldn’t even grow a mustache or beard made all my hopes crumble. I could no longer have a romantic relationship with Raymond anymore.

Raymond seemed to take it well, but I knew that he had developed some strong feelings for me. Before I broke it off with him, Raymond would cry out during sex how much he loved me, and it would always make me feel too guilty to finish performing. When we slept together for the last time (it was pity sex on my part), I wanted to be cold and distant but ended up being slow and gentle. When he came inside of me, Raymond’s eyes were shut tight, and he appeared in such a trancelike bliss that I thought he might never get off of me. After awhile, he kissed me on the forehead, and then withdrew his dick. I felt obliged to let him stay the entire night, but Raymond insisted on leaving. He left his spare key on the dresser, and said with feigned cheerfulness “I’ll see you around sometime.” I didn’t really know what to say, but a simple “yeah definitely.” When the door shut behind him, I felt that familiar emptiness again, and I wondered if I had made the right decision.

With the continual shifting at the office, I didn’t see Raymond for a while. It was not until two months after the breakup that I actually ran into him. We conversed naturally, and it seemed like there were no hard feelings between us. He still looked better than ever, and he had just started working for another sector of the corporation. Raymond was so ecstatic about it that he asked me if I wanted to have dinner with him. I had some apprehensions about the situation, but I figured it would be rude to turn down his offer. Besides, I had missed his companionship.

In the restaurant, we were having an enjoyable ex-lovers meal (at least in my eyes) when suddenly my nose began twitching. There was this incredible aroma invading my senses, a combination of cologne and sexual energy merged into one. I turned just as Raymond began talking about politics, when before my eyes were the most gorgeous man I had even seen standing by the bar. He was not as good-looking as Raymond, but he could have been a dead ringer had Raymond been twenty-six years older. This man was at least 6’ 4”, with the same dark features that attracted me to Raymond. His green eyes still glowed underneath thick arched eyebrows, locked in a sexy fierce look punctuated by the deep wrinkles in between. He had an olive complexion with a generous amount of wrinkles. The man had a thick mustache and an afternoon shadow on his square jaw that drove me insane. Even though his hair was thinning, you could still see traces of waviness accentuated by salt and pepper streaks. He looked like a former football player, with a monstrous upper torso that boasted a chest at least the span of a Cadillac hood. His abdomen had a little bit of gut sticking out, through the firm sides were still contoured by a fitted white sweater. His biceps popped out tremendously, arms stocky and hairy, the skin looking coarse yet fresh. The lower body was my absolute favorite. The legs looked thick and shapely—this was definitely a man that kept in great shape. He had slightly full hips, hugged generously by black slacks that enveloped my favorite part of any man: the waist.

By now, I had made an adequate survey of the man’s features, but I hadn’t looked at his ass yet. I turned back to an unsuspecting Raymond (who was wholly interested in his conversation topic), keeping the man in my peripheral vision. Raymond excused himself to use the restroom, and I now had the chance to look at the man again. He was leaning against the bar, and let me tell you, I almost came in my pants when I saw what stood before me. His ass looked like two luscious cantaloupes. It was not firm and young like Raymond’s. In fact, they jiggled in those black slacks. I wanted his ass, and I was ready to do just about anything for it. From what I gathered by the man’s conversation with the barkeeper, he seemed like a regular. When I looked at him again, I saw that he had already finished two shots of Jack Daniels. The barkeeper and he were laughing about this year’s sports statistics, when he looked at my direction midway. I think he felt my eyes devouring his amazing body. He looked at me, smiled, and winked. At that moment, I knew he was going to be mine.

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