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The Highest Bidder


Guest ericbb99

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Guest ericbb99

As Jason pulled up to the house, he was trembling. It wasn't cold outside, but he was literally shivering. He sat in his Jeep and focused on his breathing to calm himself. Brent hadn't seemed like a bad person, after all. He just wasn't willing to break the rules--Jason knew the no refund rule when he signed up for the site. He just didn't think he'd lose. Anyway, he didn't have a choice now. He was weeks away from getting a credit card bill he couldn't pay. He needed Brent's money.

He'd worn trainers like Brent had on at the coffee shop, and he didn't wear any underwear. Now he was regretting it. He had a chub and he was worried it was obvious. He had on a simple t-shirt and sneakers. Nothing fancy. He figured since Brent was so casual last time, it would be ok.

Jason walked to the door and rang the bell. He was surprised how nice the place was. The website must make a lot of money. The house was huge. And right on the beach strip. It looked pretty new, and it was modern in design. Lots of glass. It must have cost at least a couple million.

Brent came to the door looking dapper--light brown oxfords, purple socks, light grey pants and a button down that gripped his abs perfectly. He took one look at Jason and laughed, "Really decided to class it up, huh boy?" Jason blushed and felt embarrassed, but Brent ushered him inside. "It doesn't matter," he said as soon as the door was shut, "you'll be naked anyway. Get your fucking clothes off."

They stood together for a minute in the foyer. Jason couldn't believe how rude Brent was. He ignored him. "What am I going to have to do tonight?" Jason asked timidly. Brent replied, "For a fucking start, get your fucking clothes off. And don't make me ask twice again." Brent scared him a little bit, and Jason hesitantly complied. He stripped by the front door and handed his trainers, t-shirt, shoes, and socks to Brent who was waiting for them. "Didn't even wear undies, huh slut?" Brent laughed again. Brent walked into the study, which was right by the entryway, and put Jason's clothes in a safe and locked it. "You can have those back when you're done tonight," he said matter of factly. Jason started to get even more nervous.

They walked together into the living room. Jason's boner had gone down now. He was too scared to be turned on, even though he was naked. The living room was massive, with high ceilings and a full wall of windows. Jason was worried about being seen by someone outside, but there wasn't much he could do about it. There was a bar and a massive TV--it had to be 80" or more. But there were no other guys there. Just the two of them. That made Jason feel a little bit better. Brent walked over to him and began to touch him. Jason shuddered. Brent felt Jason's abs, which were toned and sexy. He touched Jason's butt, and even worked his fingers to rubbing Jason's tight 18 year old hole a bit. Then he got on his knees and kissed Jason's legs. And then his nipples. Brent ran his fingers through Jason's hair, and Jason realized he was hard again.

Jason thought Brent was about to kiss him, but instead, he took the boy by the hand and lead him to a bathroom. He turned on the shower and said, "Get cleaned up. The other men will be here soon. Oh, and if you want to make that $3k tonight, you'll need to give up that tight virgin hole of yours. So use this hose and get it nice and clean inside."

Jason got in the shower and Brent left to go get a few things ready. He heard people coming in as he showered. Lots of people. He tried to calm his anxieties by turning his attention to the hose. He'd never cleaned his hole before, but he figured it out. The rush of warm water felt intense. And good. As he cleaned up, he couldn't help but think how tight his hole was. Thinking of getting fucked was scary. He tried to put his finger in his hole, but it hurt too much. He used some conditioner as lube and tried again, but it still hurt too much. Oh well. By that point, he was clean all over, inside and out. He stepped out of the shower, dried off with a towel, and used a drier for his hair. Then he nervously walked back into the living room with the towel on.

As he stepped into the room, the guys erupted in cheers. There were at least thirty men there, all in their 30's and 40's, and fairly attractive. Brent walked over to him and pulled the towel off angrily. The cheers got even louder. Then they went back to their conversations. Brent led him to the bar and told him he'd be bartending the first half of the night. "Get some drinks out there," he said sternly, "I'll give you $500 just for bartending. More if you do a good job and don't put up a fight when the guys want to touch."

Jason started walking around and asking what the guys wanted and bringing back beers and whiskeys. As he walked around the house, the men groped him, making rude comments about his body. "You got a sexy boy this time," one of them yelled to Brent. Another leaned into Jason's ear and whispered that Jason's ass was going to get used. But most of the guys just called him names like 'slut' and 'whore' as he walked past, slapping his ass or cupping his balls or pinching his nipples.

After a while, Brent quieted everyone down and welcomed them. Based on what Brent was saying, Jason guessed that this was an annual event, with more people invited every year. And he also guessed that there was always a boy in his role. Brent announced that the game was about to start and explained the betting. He told the guys what bets they could place, the odds, and how much they could wager. He explained that he'd be taking the bets and keeping track of the cash. And then the guys started calling out their wagers. Brent's mouth hit the ground. They were betting tens of thousands of dollars, each trying to outdo the guy before. They were seriously competitive.

When the game started the betting was closed, and Brent pulled Jason aside. "Go get on your knees in front of Danny and suck him off," he told the boy, pointing to a guy about 40 years old, fit, and tall. "He was the highest better," Brent explained, "It's one of our traditions. You'll learn the others soon enough." Jason shook his head no, but before he could get the words out, Brent added, "I'll give you another $200."

Jason walked over to Danny with his head hung low and looked at him. "Get on your knees. Stop blocking the game," Danny said abruptly, and Jason obliged. The guys ignored him as he took out Danny's cock and started to suck. They were focused on the game. Jason took his cock into his mouth. It tasted salty, and it was oozing precum. He sucked and sucked, and finally he heard a little moan, and Danny came in his mouth. Remembering, Brent's comment about swallowing last time, he swallowed it all down, zipped up Danny's pants, and walked back to the bar.

"Not bad," said Brent, as Danny gave him a thumbs up from across the room. "You've got $700 now. Only $2300 to go," he said sarcastically. And Jason hung his head in shame.

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Guest ericbb99
26 minutes ago, ericbb99 said:

Brent walked over to Danny with his head hung low and looked at him. "Get on your knees. Stop blocking the game," Danny said abruptly, and Brent obliged. 

Ha, meant Jason... woops. I wish the site let us edit things after they get posted.

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Guest ericbb99

The Super Bowl went on and on, and the guys got drunker and drunker. It was obvious that some of them were about to lose a ton of money and were drinking their blues away. Others were about to win big and wanted to celebrate. But everyone was drinking. Brent pulled Jason aside and explained the rest of the night: "When the game is over, I'm going to have to pay out a lot of money. I might make money tonight, and I might lose money tonight. Your job is to make sure I don't lose money. At the end of the night, I'm going to auction off your virginity. And one of these guys is going to get to use you. I'll keep 80% and you keep 20%. I figure your virginity will go for around 10 or 15k, so that will get you what you need to pay off your credit card. Deal?"

Jason nodded silently and went back to serving drinks. As the game neared its end, Brent brought him over to a table. He had Jason lay down on his back on the table, then Brent handcuffed Jason's arms to the legs of the table so they were spread wide, and he tied Jason's legs back over his head so his hole was out for everyone to see. When the game was over, there was a lot of cheering. And then Brent stood up and began the auction, "As you know, gents, our boy tonight is an 18 year old virgin. He says he's straight, but you all saw him suck a dick earlier, so that's bullshit. The winner gets to "deflower" him however he wants. Rough, gentle, anything is fair game. You can give him a great first time or tear his hole apart. I don't care. And the best part is he isn't on prep!" The men cheered. Jason didn't understand what that meant. Brent continued, "Take a few minutes to look him over. You can touch, but nothing goes in his hole yet. The bidding will start soon." And with that, the men circled up around him. They were groping him even more, and they were feeling his hole. "Fuck he's tight," on of them yelled for the room to hear. "I'm going to tear him apart," another guy growled. Jason was terrified. Brent just stood back and smiled.

(to be continued)

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Guest ericbb99

The bidding started at a thousand dollars and went up fast. $1500. $2k. All the way to $6k before it slowed a bit. Jason started to get nervous. Brent was going up by $250 and then $100. And then the bidding stalled at $7100. Brent didn't seem too surprised. "Sold!" he called out. The guys all cheered, and a few laughed. They patted someone on the back loudly and congratulated him. Jason couldn't see them as they were bidding, so he had no idea who had won. Jason whispered to Brent, "You said it would be more." Brent leaned over and whispered back, "These guys lost a lot of money tonight. More than they usually do at my Super Bowl Party. They just didn't have as much to spend on you, boy." Jason shook his head in disbelief, and the men started mingling around and getting more drinks. Some music came on and everyone started to have a good time. It seemed like the party would go on for a while.

Jason did the math in his head. $2120. How was he going to come up with another $880? This was supposed to get him the money he needed. But it hadn't. And Brent didn't seem to care.

For the most part, they ignored Jason, still tied to the table, nerves building. He had already been won. He was owned. They were no longer interested.

Then a man walked up to him. He was about 30 years old, tall with short hair. He had a punk vibe--a short beard, a septum piercing, a gauge in his ear, and tattoos. He was muscled and wore a tight shirt that showed he had nice abs. He was confident, cocky even. He rubbed Jason's chest, and pinched his nipple. "Guess we're going to have some fun tonight, boy," he said, "or, rather, I am." He chuckled. "I'm Ben," he said as he slipped his finger just inside Jason's mouth. Jason instinctively sucked it a little. Ben seemed to like that. He leaned over and sneered at Jason, "You drew the short straw, boy. Sorry. My cock is as big as a baseball bat, and I'm a bit of a sadist, so I want you to feel it. I can't wait to hear you scream, you worthless bitch."

He walked off for a bit, and Jason began to cry softly to himself. How had he gotten into this mess? What was he going to do?

Then Ben came back with the key to the handcuffs. He unlocked Jason, untied his legs, and led him to the couch. The other men started to quiet down to watch the spectacle. "Wait, can't we go to a bedroom?" Jason begged. But Ben just shook his head no as he pulled his shirt off. Jason noticed a really distinctive tattoo, really cool. It was a big scorpion. Its head started on Ben's chest and its body went down toward his crotch, where Jason could imagine the tail resided. Ben pulled his jeans down and kicked off his underwear, and sure enough, the tail pointed right to what had to be the biggest cock imaginable. Ben asked Jason, "You know what the scorpion is all about?" and Jason shook his head no. "Good," Ben said, "I'll tell you later." He stroked his cock a bit and it got even bigger. It was 10" at least, and bigger around than a soda can. It was veiny and uncut and massive. The other men grabbed Jason and held him down. They held his wrists so he couldn't get away and pulled his ankles back up by his head so his hole was exposed. They pinched his nipples, slapped him, called him names, and held him tightly in place. And then they all got quiet. Ben stepped up to Jason's hole, rubbed some spit on his giant cock, and lined it up. Jason could feel his head rub the spit around the outside of his hole. Ben paused to laugh for a minute. "I've never hurt a boy as bad as I'm about to hurt you, kid," he said with disdain in his voice. And then he began to push.

(to be continued)

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19 hours ago, ericbb99 said:

Ha, meant Jason... woops. I wish the site let us edit things after they get posted.

Fixed it for you. Just report a post that needs editing, and it will get taken care of. 

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