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The Yuppie Sex Chronicles

by J. R. W.


September 30th, 1980 At two in the morning, I brought forty-seven year old Gary home after meeting him at a coffee shop. He possessed a strong broad chest from working construction, and years of weightlifting gave his appendages a stocky appearance. After removing all of our clothes, Gary reclined on my leather sofa. By his calm composure, I could tell that Gary was accustomed to being serviced, and he was waiting for me to make the first move. He had a sly grin under his red mustache, and his green eyes were as mysterious as those of a sheik. By his body language, I could tell that Gary was a top, and the fact that I'm a younger guy only confirms my assumption. Still, that did not matter to me because I was going to have him one way or another. I directed him to my bedroom, and he stretched himself out on his back. I encouraged him to lift up his legs so that I could bathe him with my tongue. His hairy torso folded over with muscle as his hips lifted from the bed. I dove into him, and he groaned with ecstasy. Ten minutes later, Gary had an enormous erection, and his entire body was growing increasingly hot. While oiling my finger with lubricant, I asked him if he ever had somebody insert a finger in his anus. He shook his head in disapproval, and claimed that he only liked to be rimmed. As he answered me in his Irish brogue, I swiftly inserted my long digit inside him. For a moment, Gary tightened up, and he started squirming uncomfortably. Before Gary could get up, I immediately started stroking his stiff penis, and he was overcome by my pacification. Eventually, I convinced him to allow me to insert another finger. Then, after going down on Gary for a while, I persuaded him to let me penetrate. It was an incredible feeling to slide inch by inch inside of him. His orifice secured a firm grip, and Gary's slippery rectum seemed to curve to the shape of my penis. Both of his legs were fanning in the air, and he had a look of sweet agony on his face. When I was going for the long stretch, Gary's crimson face grimaced as his own body simultaneously exploded with orgasm. October 1st, 1980 While grabbing a late dinner on Wall Street, I happened to run into an old buddy of mine. Trevor Hernandez was approximately twenty years older than I was, and he had worked for the same stock company at which I am employed. We had slept together only once before, and that experience was mind-blowing. After dinner, Trevor seemed genuine when he insisted that we have a platonic drink at his penthouse. Once we got through the front door, though, Trevor and I became consumed with fiery passion. As I tore Trevor's shirt and tie from his body, I noticed that he had grown a little soft around the midsection. I could still make out a six-pack, but a layer of fat surrounded it. This really turned me on because it gave Trevor a much more masculine look. Trevor had always looked so trim and boyish before, but now he appeared huskier. While we were French kissing, I unbuttoned Trevor's expensive slacks, and let them fall to his ankles. I dropped to my knees and pulled down Trevor's silk boxer shorts. I hungrily drank his member--like expensive Dom Perignon--until my nose was buried in his blond pubes. He bucked his hips, and rested his hands on my shoulders for balance. Trevor started breathing intensely, and he begged me to release him. He started trying to push my face from his groin, but all it did was make my open shirt brush against his ankles more vigorously. How could I possibly stop? The musky odor emanating from his pubic hair only made me suck harder. Succumbing to my friction, Trevor began screaming my name (in a Spanish accent) as he released his seed into my torrid mouth. The evening ended gloriously on Trevor's couch. Trevor's face was pressed against a sofa cushion, and his buttocks were held high in the air (pants still around the ankles). As I slid my hard penis into his pink, hairy anus, the scent of dry-cleaned clothes simmered off of his clammy brown flesh. October 5th, 1980 I balanced my weight on all fours while Derek Takamoto was thrusting into my backside. It had seemed like a tedious evening beforehand. I had circled the bathhouse three times by midnight, and there did not seem to be any good candidates. Then I came upon bookish Derek who was sitting with his legs crossed like a virgin. Derek looked to be a thin man in his late thirties-- with almost no body hair except for the sparse wilderness that decorated his lower abdomen. After befriending him, I found out that it was Derek's first visit to the bathhouse. In fact, Derek claimed that he had yet to sleep with a man, and the bathhouse seemed like the right place to go. So, I took it upon myself to be his patient teacher. After teaching him a few moves, I started questioning whether or not Derek was actually telling the truth. He took well to kissing, for his lips were wet and tender. Derek plucked my erogenous zones like a guitar player. I took his erect nipple in my mouth as he placed his hand between my buttocks. I bit down on Derek's earlobe, and his body convulsed electrically. I could not bear the heat any longer. Taking a tube of lubricant from a shelf under the bench, I told Derek to massage my anus with his finger. He did this eagerly, and I could see that Derek was enjoying the experience. I looked down between my knees to see that his penis waved frantically in the air. My excitement overtook me, and I started backing myself into Derek's crotch. At first, he did not know what I was doing. But, when he started feeling his penis being devoured by my aperture, Derek must have got the hint. He wrapped his arms around my waist, and thrust forward with a loud cry. Throughout our encounter, I continued pushing against his pubic region. After ejaculation, Derek's body seemed to be more accommodating and elastic. Standing in a bent position, Derek had to hold onto my lower legs just to keep himself from falling over. Beads of sweat journeyed down his spine as his entire body jerked with my long, deep thrusts. October 12th, 1980, 4 PM There have been no adventures since my steamy hour with Derek. Although, the intern Raymond might be giving me the lovesick eye. He looks to be in his mid-twenties like me, and there's never a day when I don't see him pass by my office. Sometimes Raymond delivers a message to me from the main boss, and we both blush like Catholic schoolboys. We've been doing this for the last six months. As a sit here writing this entry, I find myself hoping that Raymond will deliver some message to me, but he has passed by only once today. I want to just ask him out on a date, but I'm afraid that he might not be gay. My work shift is officially over, but I'm still waiting for him to come by. I know I would enjoy having sex with Raymond, but I'm questioning if that would be a good idea. Instead of sleeping with him on the first date, I want to know more about him. The thought scares me because I've never felt this way for anyone. I hope I'm not falling in love.

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1 Gay Erotic Stories from J. R. W.

The Yuppie Sex Chronicles

September 30th, 1980 At two in the morning, I brought forty-seven year old Gary home after meeting him at a coffee shop. He possessed a strong broad chest from working construction, and years of weightlifting gave his appendages a stocky appearance. After removing all of our clothes, Gary reclined on my leather sofa. By his calm composure, I could tell that Gary was accustomed to

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