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The Highest Bidder


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Guest ericbb99
Posted

Jason had just turned 18 years old a few months ago. He'd always been a risk taker and loved to gamble on anything and everything. He was able to read people well, so he won more often than not. He'd been playing poker since he was a kid. And had taken plenty of money from his friends. He'd always wanted to play online poker, but he had to have a credit card. So the day he turned 18, he went and applied for one and got an account with some shady website.

Jason was a young white kid, kind of a twink, but he had nice abs and some muscles. He was just a thin guy--he always had been. He was good looking. He had curly blond hair, and was naturally hairless below the neck. He had blue eyes that were piercing. He was straight, though he hadn't had sex yet. He'd never had much luck with girls, but he definitely wasn't into guys.

It was summer break and Jason was free during the day and bored with nothing to do. He was wearing just his undies and no shirt. He sat down at his computer and logged in to play some poker. Unfortunately, they were playing with a high buy-in that day. $100 just to play. He usually played with lower stakes. But Jason wasn't worried. He knew what he was doing. He clicked OK and jumped into a game. He was dealt a shit hand, got rid of a card, and got another three. But by the end of the hand, he still had nothing. And he'd lost another $300 on top of his initial $100. But that's how poker worked. You were down one minute and up the next. He decided to keep playing. After all, he had to win back his money. It was just a credit card, after all. And he knew he didn't have the money to pay it off if he didn't win.

(to be continued)

Posted

Hopefully looking forward to the next chapter.   This really could go in a lot of hot directions.  No luck with girls absolutely not in the guys yeah right.  He’s going to have to pay off that debt somehow might as well with his ass.

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Guest ericbb99
Posted

Jason played another 10 rounds. He lost the second, won the third and fourth, but then lost games five through ten. He was $3k in the hole, which was his credit card limit. With his card declining, he was blocked from playing any more. Fuck. He felt his face get hot and his head go a little dizzy. How was he going to get the money back? His parents, who he still lived with, were going to murder him. They'd only let him get the credit card for emergencies, not to use. And it's not like they had money and could pay it off for him. They weren't rich. What was he going to do?

He laid down on his bed and started to breathe hard. He's never had a panic attack before, but maybe this is what it felt like. How had he been so stupid? He loved the risk, but he'd never really lost before.

He closed his eyes and started brainstorming. Then it clicked. He knew what to do. Jason jumped up to his computer and went to the "Contact Me" page on the site. He started an email to them:

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To whom it may concern:

This morning, my little brother got on my account and played a bunch of games. He didn't know what he was doing, and I had no idea he was on here. He racked up a big charge on my credit card, but it wasn't me. Please, I need you to refund the charge. It was fraudulent use! Thank you!

Jason

 

He laid down on his bed and waited. He pulled up some porn in the meantime. He loved porn where the girl was getting used really hard... choked and slapped around and all that. He'd never do that to a girl, but loved seeing the guys get so aggressive. He admired it in a weird way. It turned him on to see how masculine they were. He was jerking to some James Deen porn, when he heard his email ding:

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Sorry, we don't do refunds. Your account was two-step verified. You lost. That's how this game works. Don't play if you can't pay.

It was harsh and rude and very matter of fact. Whoever ran this website didn't care about him at all. His dick went soft as he typed out a reply. Jason decided his only chance was to come clean and beg for mercy:

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Hello,

Please. I'm literally begging you. I'm just an 18 year old kid with my first credit card. I live with my parents in Fort Lauderdale, and they'll kill me if they find out about this. I don't have the money to pay it off, and neither do they. I'm begging you. You can ban me from the site forever. Just please refund that money. I've learned my lesson. I swear!!! I shouldn't have done this!! I'm so sorry!! Please, I'm begging you!!!!!!

Jason

Suddenly he was hard again. Maybe from the begging. That was weird. Huh.

He started jerking off, but the ding came soon:

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Hmm... we normally don't refund for any reason. But you're in Ft. Lauderdale, huh? Me and the other guys who started this site are in Miami. Meet me at the Panther Coffee Shop in north Miami around 4pm, and we can talk about refunding the charge. I want to know that you are who you say you are, and that your story is true. And it's a public coffee shop, so you'll be safe. I know it's a little unorthodox, but if I'm going to give back $3k, the guys are going to want to know why. Let's talk. I'll see you at 4pm. I'll be in grey joggers and a white t-shirt. I've got tattoos down my arms. I'm early 30's and have short brown hair. Don't be late or you can kiss your refund goodbye.

Jason was rock hard and he had no idea why. He didn't like the idea of meeting someone from a seedy website, but the guy was right. It was a public place. He'd be safe. He decided to go, and he got dressed. About 3:15pm, he left the house and started on his way. His heart was racing the whole drive there.

(to be continued)

Guest ericbb99
Posted

As Jason got to the coffee shop, his heart was still racing. He got out of his old Jeep Wrangler and walked inside. He was wearing jeans and a t-shirt and flip flops. Nothing special. He just threw something on. He brushed his blond curls out of his eye as he walked through the door and looked for the guy. There he was, in the corner, kind of away from everyone. At least Jason wasn't going to feel embarrassed having to explain his situation with strangers in ear shot.

The man was well built and looked young for thirties. He had short brown hair with a tight fade on the sides. Jason was expecting someone a little bit more business like, since he ran a website and all, but Brent just looked like a normal Miami fuckboy. In tight trainer sweats, expensive shoes, and a designer t-shirt, he was nothing like what Jason expected. But it didn't matter. All that mattered was getting that refund.

Jason walked over to the man and said hello. He looked up, smiled, and introduced himself as Brent. Jason sat down. They sat there, awkwardly silent for a minute, and Brent said, "You are young. Can I see your ID? To make sure you are even old enough to be on the site?" Jason nodded and handed it to him. Brent smiled and said, "Good," and handed it back. "You just turned 18, huh? Tell me your story. What happened?" he asked. Jason told him what had happened. He didn't leave anything out. He told Brent that his parents were broke. He told him that he couldn't pay his credit card bill. And he begged and pleaded for Brent to refund the money. "I'll do anything," Jason kept pleading. And then he sat silently and waited as Brent rubbed the back of his head and thought for a minute.

"Ok, come with me," Brent said, and he got up and walked down a back hallway. Jason was stunned. Did Brent have the cash with him? Did he own the coffee shop--were they going back to his office or something? Or out the back door to his car maybe? But he didn't have a choice. He stood up and followed. Brent took a detour into the men's room, and Jason stopped to wait in the hallway. Brent held the door open for him, and looked at him expectantly. Jason said, "I'll wait here." Brent chuckled, realizing Jason didn't understand, and replied, "No, kid, you've gotta come in here with me. I'm not giving the money away." Jason didn't fully understand what Brent meant, but he stepped inside, and Brent locked the door behind them.

"Get on your knees," Brent said with a rough voice as he tugged at his growing bulge. Jason held up his hands and just said, "Oh." He stood there stunned for what felt like an eternity, and Brent pointed toward the floor and flashed him a little smile. "No, man, I'm not into that. Sorry," Jason said. But Brent just shook his head, "I knew you didn't really want it. You said you'd do anything. This is nothing. It's just a blowjob. Who even cares? It's not a big deal." Jason was still stunned. "It's cool," said Brent, "Just walk back out to your car and go home and figure out how to pay off your credit card on your own."

Jason thought for another minute silently. Brent could see the wheels turning, and his bulge grew even more. "On your knees," he repeated. And Jason dropped down on his 18-year-old knees to the dirty bathroom floor, his head hung low.

Brent pulled the trainers down and pulled out a huge dick. It was at least eight inches long and really thick, and it was uncut. His pubes were trimmed nicely and his balls were shaved. Jason took it in his mouth and it grew even more. He started to suck and Brent reached down to play with Jason's hair. Brent moaned. Jason sucked and sucked. He just wanted this to be over. It took about 10 minutes, and finally, he felt Brent start to buck into his throat a bit and picked up the pace. Brent was on his tip-toes with his eyes closed, and he was letting out little moans every once in a while. Then all of the sudden, with no warning at all, and with his dick most of the way down Jason's throat, Brent shot a massive load in the boy's mouth. He pulled his dick out, slapped Jason on the face, and said sternly, "Swallow. Don't be rude."

They put their clothes on and walked out of the bathroom, and then out of the coffee shop together. They stopped in the parking lot, and Jason timidly asked, "So, will the money be refunded to my card, or do you have cash or something?" Brent burst into laughter and doubled over. "Oh fuck," he squealed, "You think that blowjob was worth $3k? Fuck no, kid! That would have been $30 from any boy on the street, or I could have gotten it free from a dozen guys with just a text message. I just needed to see if you were game." He laughed some more as Jason looked at him shocked.

Brent was still chuckling as he handed Jason a piece of paper. Jason unfolded it and found an address. "Be there tomorrow by 5:30pm," Brent said. Then he added, "And you are a virgin, right? Just need to be sure." Jason was pissed and terrified, but he didn't have a choice. He nodded yes and started to walk back to his Jeep defeated. Then he paused and turned back, "Wait, isn't the Super Bowl tomorrow?" Jason asked. Brent smiled, "Yep," he said, "and we have a few friends coming to a Super Bowl party. They'll want to gamble, and they'll have real money with them. I know how much you like gambling, after all. You see, I can't give you a refund. Against the policy. Sorry, kid. But I can let you keep gambling to try to win back your money." He smirked again as he got in his BMW. As he pulled out of the parking lot, he stopped and looked at Jason, who was still standing there in disbelief. "You going to be there, kid?" he asked. Jason just nodded yes, and Brent nodded back to him and drove off. Jason was left feeling used and broken. But he didn't have a choice. He tucked the address into his pocket and got back in his Jeep to go home.

(to be continued)

Posted

Great story so far!   Has me wondering, does Jason just lose his cherry, does Brent become his pimp, is Jason sold into sexual slavery to a sadistic master.  Please keep writing

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