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The Bet

Renders by Vuffer – Story by Daddyshere


The one secret you should know, before you delve into this story, is that our hero, Jake, has been around for several centuries! Yes, CENTURIES!


Betting has been a sport for Jake since the early 1700s when he first came to the Americas from England, although, before that, he’d been raised, as a child named Jacob, in Germany. His family heritage was Jewish. Named Yaakov, after his father and great grandfather; a name we now recognize as Jacob, he’d Anglicized his name from Jack to Jake, which he preferred among all the names he’d gone through over the many years that he’d enjoyed his sensuality and sexual playfulness. In Germany, he was often called Jakob, in France, Jacques, and in Italy, all the young men fell in love, much to their distress, with Giovanni!


The Friday evening, when Jake’s father was dying, he called his son in for a final blessing, a Sabat, and somehow, inexplicably, that blessing became more than anyone could have ever conceived.


He was 18 years old at that time, and as the years went on, his family and friends couldn’t help notice he’d never changed over the years. He was a beautiful and handsome young man, well endowed; full of energy and sensuality!


It soon became obvious that he’d have to constantly keep moving about while those around him kept aging as he continued to stay young. At first, he thought he’d been cursed instead of blessed, but he soon accepted his eternal role in life and grew to the challenge of not only maintaining his personality, but altering both his birth name as well as his surname.


He’d learned he had also had an amazing instinct for gambling and gathered a fortune over the centuries in a variety of gambling games and races; be they horses, dogs, boating, cars…no mater, he could instinctively figure out who would win. He kept his money in a Swiss bank account and through years of schooling and education he learned how to pretend he was his ‘father’s’ son year after year after year, ‘inheriting’ the family fortune.


No one questioned his financial withdrawals when he needed money and he always managed to keep one step ahead of the game!


And so, another game begins!


The twenty-first century had finally arrived and he’d now lived in America in a beautiful manse in upstate New York. It was remote and he could afford to keep it secured and private, so the locals really had no idea who actually lived there, except for the young, good looking, blond youth who could sometimes be seen driving in and out from the manse in his expensive, red sports car.


He had one person who lived with him in his home who was now his personal man and who had been, over 80 years ago, a hot, horny trick that he had bet into working for him as a handyman.


His name was Christoffer Hansen and was, at one time, a damned near doppelganger look-alike to Jake. He was young lad from Denmark whose surname Jake had eventually adopted as his own. As Christoffer grew older, he came to know Jake’s secret and was willing to hand over his identification in trade for a permanent position and the occasional pleasure of enjoying Jake’s body, now and then.


Unfortunately, now nearing 90 years old, Christoffer was getting much too old to keep up and knew he would not last much longer. Jake Hansen would have to find a replacement. Another bet was on the way!


It was way too easy for him to get other gay young men to serve him, with his looks, money and his impressively wide, 10” cock, therefore he most often hunted down straight guys; making financial bets that, in exchange for sex, they could never refuse.


A year ago, near Halloween, he went down to the city where he met two other young men at a local strip bar. Their names were Troy and Jeremy and they were wearing Batman and Robin costumes. He watched them as they were getting all roused up checking out the female strippers as they were sliding up and down their dance poles; showing off all they had to ‘bare’!


Watching the boys grope themselves into hard-ons, Jake knew this was a good time to get to them.


Jake was dressed like the leatherman from the “Village People”; most famous for singing “YMCA”. He’d slapped on a fake mustache along with his leather gear. He wormed his way through the crowd and began chatting with them and buying them loads of drinks; showing off his money. He finally talked them into going back with him upstate to his home and having a party there! Figuring this guy was a ‘flake’ and ready to hand out money every few minutes, the happily agreed to go.


It wasn’t long before he had them in his basement, getting them high on liquor and grass, when he decided to make a bet with them. “On the count of three, we strip out of our costumes and whichever of you two can get into my costume the fastest, wins one thousand dollars! The loser has to serve the winner and do whatever he tells him to do. I’ll just go along for the ride and do whatever the winner wants too.”


By now, Troy, who was Batman and Jeremy, his sidekick, Robin, were so stoned and having so much fun, they totally agreed, not even considering that either of them might be the loser!


The two boys could hardly stop laughing as Jake stripped down and out of his leathers, standing there in his full glory. His leathers lay on the sofa.


Getting serious now, Troy was out of his Batman costume and into Jake’s leathers before Jeremy could hardly get his Robin cape off.


“Hah! You lose!” Troy yelled out at Jeremy.


Jeremy was stone silent and staring at Jake’s humongous cock waving back and forth in front of him as he was still sitting on the floor, finally removing his second boot.


“Holy, shit! Is that for real?” Jeremy slurred through his quivering lips.


Troy then noticed it as well and stared wide eyed. But hell, he won, and relieved he said, “Hey! I don’t have to worry about that swinging monster. You do, Jerry!” and he laughed it up royally.


Troy, being the winner, immediately grabbed Jake and Jeremy with his leather gloves, pulling them up to the sofa in the basement and ordered Jake to sit with his hands behind his back while Jeremy was order tickle the shit out of the naked Jake.



Jake, although he wasn’t ticklish, went along, laughing like hell over the tortuous tickling when Troy suddenly ordered Jake to start sucking his cock!



That was only the beginning of the evening. By the time the night was over, Jake had gotten both boys to serve him and give him everything delight he wanted. They weren’t very good at sucking cock, but their asses were tight and very pleasurable to fuck!


The next morning, he’d taken the boys back to the city, each rewarded with a load of cash and an experience they would never forget. It didn’t dawn on either of them, until Jake had left, to think about where exactly he lived. They really didn’t pay attention to how they got there and back, so they were never able to get hold of him ever again.


But now, this was a new year and a more serious situation. He had to find another young man who could replace his man, Christoffer, when the old man could no longer work for him.


It was another trip to the city, but before he’d gotten nine or ten miles from his home, he spotted a very tall and tan young man hitchhiking in the opposite direction along the highway. It was an exceptionally warm fall day and the young hitchhiker was wearing only a tank top, shorts, sweat socks and sneakers. Jake had to check this guy out!


Finding the next exit off the highway, Jake circled around and went back hoping the guy didn’t catch a ride before he could get to him.


There he was, still standing with his thumb out and his package showing off very well in those tight shorts. He tapped his horn as he passed the boy by a few feet and pulled over, watching in his rear view mirror as the lad ran up to his car.


“Hi!” The young man said as he opened the door. “Thanks!” He got in the passenger seat and buckled up. The seatbelt, tightly hugging across his lap, only helped to emphasize the sensual bulge in this guy’s shorts.


The young man was long and lean with short, dark hair and deep, brown eyes and he wore a great smile that immediately drew Jake’s attention.


“I just saw a car go by the other way that looked just like yours,” said the young passenger.


“That was me,” Jake replied. “I couldn’t bear to see you stuck hiking on the highway like that. Where are you going?”


“How about to your place,” The young man asked.


“Wha…?” For the first time ever, Jake was stunned. “My place? You want to go to my place? Do you know me?”


“Nope, I don’t know you, but I’d sure like to get to know you! By the way, my name is Boy.”


So surprised at all of this, Jake was relieved he hadn’t started back on the highway yet as he probably would have been too shocked to drive and might have had an accident.


“Uh, hello, uh…Boy?”


“Yeah. My dad was a big Tarzan fan and insisted I was baptized with the name, Boy. My mom thought that was ridiculous, but she wasn’t about to refuse him. Disgusted with his aloofness and lack of sex in bed, she left him within a few years after I was born and that’s when I learned my dad had sexual interests other than women. He was bi, and so am I, but I still prefer guys and you’re a cutie!”


Jake smiled as he looked the young man in his eyes, then turned to the driver’s window to check oncoming traffic and pulled out onto the highway.


“You are something else!” Jake said as he continued to drive. “Do you always come on so strong?”


“Not always,” Boy replied. “But the second I opened your car door, I got a really good vibe from you and I knew, by the look in your eyes, you were as interested in me as I was in you.”


Jake laughed. “Okay, you got me. Sure, let’s go to my place.”


They drove a little further when Jake asked Boy, “Say, are you much of a gambler?”


Boy smiled, “What have you got in mind?”


Jake returned the smile. “We’ll talk about that when we get to my place.”


In about ten minutes or so, they were pulling into the driveway of his manse. Boy was in awe of the home. “Wow, you sure have a big house. You live here by yourself?”


“I have a few guards about the property and a butler who takes care of my needs. He’s been with me a long time and, uh, …he’s about to…umm…retire.”


His man, Christoffer, met them at the door and took Jake’s light jacket from him as Jake introduced his guest.


“Christoffer, this is Boy, and yes, that’s his real name. Boy, this is Christoffer, my personal man.”


“Hello, Christoffer! It’s a pleasure to meet you!”


“My pleasure, as well, said Christoffer. Shall I prepare something for you to eat, sir?” Christoffer asked Jake.


“Not now, I think I may already have something to eat!” Jake grinned and Boy blushed.


Jake led Boy into his huge, finished basement. “This is my playroom.”


“Nice!” Boy responded. “Dark, mysterious, yet warm; and that sofa looks pretty comfy.”


 So, about that gambling idea; think you’re up to making a bet?”


“Sure! I can’t think of anything I wouldn’t want to do with, or for you, so why not?”


“First, let’s strip down to our underwear,” Jake insisted.


Off went their shoes, socks and other articles of clothing. Jake stood next to Boy, admiring his smooth, tanned, muscular chest, stomach and abs. “Okay,” Jake continued, as he spread out his arms, we both come up with a torture and see who can hold out the furthest. Nothing bloody or deadly, just something that you know will drive one or the other of us crazy enough to say, ‘Give!’”



Boy couldn’t help but smile widely at Jake’s enthusiasm over this game he wanted to play and immediately thought exactly what he would do to make Jake give up first!


Before Jake could say anything further, Boy grabbed him from behind, wrapping his left arm over Jake’s shoulder and grabbing his throat with his hand. At the same time, he held his right hand over Jake’s nose and mouth, making it impossible for Jake to breathe!



“Okay, let’s see how long you can hold your breath before you pass out, and when you do, you can be sure that I’ll take full advantage of you!” He said, smiling all the while.


Jake was taken a bit by surprise, but he was not frightened at all. He’d dealt with this ordeal on several occasions over the centuries and although he pretended to struggle, he enjoyed being wrapped in Boy’s muscular arms and had no problem holding his breath.


Boy was certain Jake would give up soon, but was very surprised to see his new friend didn’t seem to be having a problem with his breath being held, already, over two minutes! He felt Jake’s ass bumping against his crotch as he struggled, exciting him and making it difficult to concentrate on holding him steady. Three minutes up and he finally let go of Jake and collapsed on the sofa, his crotch swollen with excitement.


“That’s it?” Jake asked. “I never said I give!”


“I know,” said Boy, “but you also didn’t seem to be having any problem with having your air blocked from your lungs, and I couldn’t take any more of your pounding that cute butt of yours against my dick!” He gestured at his bulging underwear.


“Ho! Ho! Well, then, I guess it’s my turn! Stand up, Boy, arms in back of your head and stay perfectly still,” Jake ordered. He then began to lightly stroke all and every possible ticklish spot on Boy’s body with his fingers.



“Oh, no! Nooooo!” Boy laughed and cried at the same time. Unlike Jake, Boy was enormously ticklish and this was indeed torture! He almost fell to the floor.


“No way! You have to stand here and take it!” Jake continued to tickle at Boy’s ribs and belly, occasionally tickling at his balls within his briefs. “Okay! Okay, I give! Stop! Stop! Please stop!”


Jake stopped and pushed him down on the sofa, collapsing on top of him. They were both laughing out loud when Jake suddenly took Boy’s face in his hands and kissed him full on the lips!


Boy immediately responded, opening his mouth and giving Jake his tongue as they continued making out. Even though Boy gave in, there were no winners and no losers in that bet as they shared each others body throughout the night, making fervent love!


I’m sure you, my reader, have figured out by now, that Boy wound up moving in with Jake, knowing his secret of eternal life and taking over Christoffer’s position as Jake’s personal man, as well as his lover. Christoffer lived a few more years in a private room of his own, with Jake and Boy taking care of him until he finally passed away.


It’s been about ten years now and Boy was aware that Jake would outlive him, but he was content to be with this most magnificent and extraordinary young man for as long as life would allow him.


As long as Boy was with him, Jake made a vow that the bet they made, the night that they met, would be his last bet until Boy was no longer with him.


The End



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