The Long Con

Published on Jul 27, 2022

Gay

The Long Con - Part 1

Disclaimer: This story contains homosexual themes and explicit sexual acts between males. If you are offended by such topics or not of legal age to read such content, please stop reading now. This is a work of fiction and any resemblance to real people or events is completely coincidental.

Questions, comments, concerns, feel free to e-mail me at spfiction@graffiti.net

If you're on LiveJournal visit my "sicpuppyfiction" community and read some more of my work.

This is my first submission to Nifty. Enjoy!

- SP

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The Long Con

Part 1 by SP

From above deck Sean Holtz watched the coastline, back-lit by the setting sun. It was the last day of summer, a fitting day for celebration. Sean downed some of his rum and cola and the sickly sweet taste brought him right back to his childhood in Darlington. Here he was, a barber's son from Alabama, bobbing up and down on a motor yacht in Miami harbor, a few million richer than he had been that morning. The American-motherfuckin'-dream.

"Who wants margaritas?" Sean turned around and there was Rupert, coming from below deck with a pitcher in one hand and a cocktail glass in the other, both were filled to overflowing with neon-green liquid.

"No thanks," said Sean, distracted. Despite the indifferent welcome, Rupert saddled up next to him along the railing. Rupert was an inch or two shorter than

Sean, and was dressed like someone who might actually own a yacht, all pastel and preppy. In contrast, Sean was wearing a worn, red t-shirt from his high school football days and khaki cargo shorts.

Rupert gestured grandly with his hands full, "Where's Janey?"

"She's taking a shower, coloring her hair," answered Sean.

"Ah ha," said Rupert not unlike a detective would in an old murder mystery. He proceeded to take a swig out of the pitcher and toss the glass and its contents into the turquoise ocean. With a dramatic sigh he flashed Sean a demure smile.

Sean squinted as the sun was now bright in its position, but he refused to look away. This was as much out of appreciation for the spectacular sight was it was an attempt to ignore the theatrics of present company.

Sean and Janey had been working their way towards the east coast, pulling cons for three years before teaming up with Rupert. Originally, Rupert had been a mark in one of their schemes. Rumor pegged him as a young, rich heir with more libido than common sense. In reality, his inherited fortune had long been swindled away from him and Rupert, immediately wise to their scheme, had integrated himself into their Bonnie and Clyde act with great enthusiasm. He was a calculating, resourceful and, Sean suspected, a flaming homosexual.

"Enjoying the sunset, boys?" called Janey from below. Sean turned to see her, still rubbing a towel through her hair. She caught his eye and broke out into a grin. "Hey, baby!" she cried out playfully. Sean reached out pulled her towards him then buried his face in her hair. She smelled a little like chemicals from the hair dye.

"Cheers," Rupert held up the pitcher of alcoholic slush, "To us, to our unfortunate slob of a benefactor and to the unfortunate slobs to come."

Sean weakly raised his glass above his hip and mumbled something that might have been "Here."

Rupert turned to face Janey exclusively and gave a little bow. "And to our leading lady, who once again proves that her beauty is matched only by her ingenuity."

Janey was their come-on, their sweet, young bait conceived to make powerful men throw caution to the wind. More than just looks, she came with no background or subsequent baggage, nothing but an uncanny one-dimensional personality made up of the qualities each individual appreciated above all in a lover. Usually they targeted married men on the verge of a sizable fortune, or whose star was quickly descending into obscurity, blackmailing them less their exaggerated, scandalous affair taint their budding reputation or put a nail in its coffin.

"While we're toasting," Janey addressed the both of them, "let's not forget our upcoming, final performance in Miami starring my ingénue understudy." She waved a fake glass of spirits in the air and gave Sean a slow, lavish wink. Sean laughed. It sounded forced even to him.

This next con had been boiling on the back burner for the last year or so. They were almost too hot to be working in Miami anymore. A few of their previous marks had come forward and even if the general public wasn't wise to them, the social circles that mattered were tainted by rumors of their exploitation scandals. Rupert had been working, forging connections on west coast in anticipation that they'd pack up and move out that way – a process that was proving to be long and expensive. With this last con they'd broke even without liquidating their assets, something they were all unwilling to do less the transcontinental move fall through. One more con would put them over the top. If they wanted to stay in Miami and retire, they'd live comfortably, if they continued on the path to California they'd be able to fund that endeavor and maybe keep a few bills in their pockets.

So, they were going to pull one last scam. Their mark this time was one of the fresh-faced, new money variety. Lyle Park: Property mogul and real estate developer. He had been busy making a name for himself here in the southeast and had quickly gained favor with the "good ol' boys" of Miami. He was also, and Rupert swore this up and down, a homosexual who preferred his dalliances to be as discrete as possible.

Thus Sean's new role in their signature drama. He threw back the rest of his drink and savored the syrupy sweetness. He then returned to watching the sun's rays flirt with the peaks of the waves in the harbor.

*

Later that night, after an excessive celebratory party that had swept like a hurricane through South Beach, the three were lazing around the pent house of some high-rise hotel. Sean, easily the most intoxicated, rolled back and forth on the king size bed, knocking decorative pillows off the side in his wake.

Janey pinned him down between her pale, slender arms. Playful at first, she grew quiet and serious, staring down at Sean with an oddly intense gaze.

Sean threw his arm over his eyes to shield himself from Janey's glare as well as the overhead lights. "What?" he practically moaned.

"I'm gonna pluck your eyebrows," she said matter-of-factly. He tried to throw her off, but she kept her balance like an expert bull-rider. Janey giggled. "What guy would want to date someone with your spectacular lack of style? Come on, let me do some grooming!" Sean grabbed her wrists as she ran her hands down his sideburns.

Sean forced a laugh, "You are enjoying this too much, missy." She slid off him lithely. No sooner had the warmth of her body faded than Rupert plopped down on that side of the bed and threw his arm over Sean's horizontal form. Sean squirmed reflexively. "Hey, Rupert-" Sean twisted his head to look out the window at the cityscape.

Rupert grabbed Sean's chin and wrenched it upwards.

"Woah!" Sean yelped.

Rupert brought his face within a few centimeters of Sean, eventually bringing his forehead to rest on Sean's forehead. His breath smelled strongly of premium vodka. "Let's give us a kiss, lover boy. Show me what you got," Rupert moved to put his and Sean's lips together. Sean jerked his head to the side before Rupert could properly kiss him. Undeterred, Rupert used his tongue to trace Sean's jaw from the corner of his mouth to his ear.

"Rupert, Rupert, come on, man!" Sean pleaded as Rupert lapped back and forth along the bridge of his ear.

"Don't be such a pussy," Janey giggled girlishly, flipping her long hair over one shoulder. Her face then assumed a mock-serious look, "How are you going to go through with this if Rupert gets you all flustered. You don't know the first thing about guys."

Sean pushed himself into a sitting position, elbowing Rupert away. "I am a guy!" He motioned to Rupert who was propping himself up in bed and rolling his eyes, "If you think I appreciate that kind of nasty joshing, you're wrong. No guy would ever find that sexy."

Rupert and Sean exchanged looks of annoyance with each other.

Janey fidgeted in silence for a moment. "That's it, y'all need more booze." She made a move for the bar while saying this, a smile lighting up her face.

*

A few hours later and maybe twenty minutes of sleep, Sean crawled out of bed where Janey was curled up, crept past the couch where Rupert had passed out, and slid into the bathroom.

He closed the door behind him with a sigh. After turning on the lights he was temporarily blinded, not only because the light was glaringly bright but it was also reflecting off every gold plated surface in the room, of which there were many.

Still trying to be as quiet as possible he ran some cold water and washed his face in the sink with his hands. Finishing, he sized himself up in the gilded mirror above the sink. He had a ruddy complexion, all freckles if one looked close enough, and pin-straight brown hair that shone like bronze when the light hit it. These features might have seemed plain on someone who didn't have Sean's strong, angular face.

Right now, he looked a little beat; it was all in the eyes. Wasn't it always like this? Rupert and Janey would be laughing victoriously as if they were literally in the front seat of the getaway car, driving off into the sunset, their backseat piled high with sacks with dollar signs on them, bills fluttering off in their wake. Meanwhile, Sean waited like a man who has a date with the executioner, making hatches in the cell wall every day they went without being arrested.

He sat down on the edge of the tub and rubbed his still damp face in his hands.

"Can't sleep?"

Sean looked up with a start to see Rupert leaning against the door's frame. He tried to mask his alarm with agitation. "Shut up," he glowered, "Janey's asleep."

With a warm sigh, like a mother would use to comfort a child, Rupert crossed the small, gaudy room and put his hand on Sean's shoulder. "You shouldn't be nervous. You're nervous aren't you?" He sat himself next to Sean on the thin ledge of the fancy tub. "Janey and I would never let you go through with this if we didn't think it was going to be a wild success." Rupert rolled his eyes as he said this, meanwhile his hand was traveling in a slow circle between Sean's shoulder blades.

Sean shrugged Rupert off, not aggressively, but the action wasn't all that friendly either.

A look of indignation crossed Rupert's face. "See, Sean? Janey and I have been talking and we are concerned because you're so hesitant to open up to people. You come off cold without meaning to be. Janey always says you're a hard man to love and I like to think, for the sake of this next con, that you're going to put on a good show and be someone warmer. Though, sometimes I wonder if you even know how." Rupert brushed his dark hair behind his pale, delicate ear.

Sean flinched, not so much at Rupert's accusation but as a response to Janey calling him "a hard man to love." "Sorry," Sean responded without looking Rupert in the eye, "I'm a little more discriminate when it comes to who I fuck."

Rupert laughed and it was eerie sounding. He also laughed a little bit longer than was called for. Sean cautiously glanced out of the corner of his vision to watch this odd outburst of mirth.

With his face still contorted into a grin, Rupert leaned forward and put his hand back on Sean's shoulder. "Was that a thinly veiled insult or a blatant come on? No, I think you just challenged me," Rupert's voice grew gravelly and his grip on Sean's shoulder tightened.

"What?" Sean whispered, confused. Rupert responded by brushing the knuckles of his other hand lightly over Sean's pecs.

Sean jumped and had to steady himself. As his hand were clutching at the enamel, Rupert continued to feel him up undeterred. He slipped underneath Sean's tee shirt. Rupert pushed his hand up Sean's hard stomach, which nonetheless, was quivering with each breath like a feather caught in an updraft. Effectively pinned up against the wall, Rupert could lift his other hand from Sean's shoulder. It came to rest on Sean's leg. "Stop it, stop it," Sean pleaded under his breath as Rupert aggressively rubbed Sean's thigh with that other hand. He was pulling, tugging, massaging the skin there and moving upwards slowly, at a menacing pace. The hand on Sean's bare chest began to knead the sensitive spots perched there that Sean didn't even know he had.

Finally, by the time Rupert's industrious hands reached Sean's groin, the struggling man was already half-hard. Sean was pushing Rupert away with all his strength now, but the humors in his body were being diverted elsewhere and his strongest wasn't enough to keep Rupert at bay. "Rupert!" Sean cried out as his nimble attacker grabbed his fledgling erection through his khakis while Rupert's other hand busied itself pulling down the waist of Sean's shorts.

"Shh," Rupert whispered, bringing his lips right up to the crest of Sean's ear, "Janey's asleep, remember?" He continued to sliding Sean's pants down over his hips, while deftly steering his cock free of the restricting material. Sean refused to watch as Rupert stroked his stiff member through his navy boxers and bit down on his lower lip so not to cry out when Rupert tightened his grip, finger by finger.

He gave Sean's penis a long, thoughtful squeeze. "You know, Sean," Rupert purred, "They say men can't really tell if they're in love or not until they sleep with a person. I wish I had the time to train you properly; I'd turn you into an irresistible sex fiend, no problem." Rupert wet his lips, never taking his eyes off of his handiwork.

Sean was completely exposed now and, with the addition of complimentary moisturizer the hotel provided in an intricate plastic bottle, was very close to climax. Rupert's hand twisted the flesh beneath it on its way up Sean's slippery shaft. He ran his thumb along the edge of Sean's circumcised head, pushing on the skin there, mixing tiny droplets of precum with the vanilla-scented lotion.

Still twisting and tugging at the length of Sean's penis, Rupert snuck a hand down to lightly tap Sean's ballsac. "You going to come now?" Rupert asked, completely composed.

"Nn," was all Sean could vocalize, but in response he resumed trying to push Rupert off.

"Let me rephrase that: you're going to come now." Rupert slipped past Sean's balls and pushed up against the stretch of skin beyond that, applying steady pressure while pushing once down on Sean's erection then jerking it again for good measure.

Sean came with a pitiful sound as though someone had just branded him with a hot iron. Even his jizz seemed to burn his skin where it landed.

Already thrown off balance, Sean fell back into the waiting expanse of the tub. Rupert made no motion to help him. Sean's reflexes were fast enough so that his head only hit the wall behind the bathtub after rebounding off his arm.

Rupert stood as Sean scrambled to pull his pants back on without getting out of the bathtub. With a disinterested air, Rupert wiped his hands on a gold embroidered towel and checked himself in the mirror. "Good night," Rupert said to Sean as he paused in the doorway and smiled over his shoulder.

Covered but still breathing irregularly, Sean stared up at the plaster ceiling. He couldn't even think; the pounding in his ears was so loud. He sat there till his heart stopped battering around.

His first thought in the absolute silence: How the fuck was he going to do this?

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[sic] Puppy

spfiction@graffiti.net


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