The Bet - Chapter 46 (Tuesday – week 7 Part 8 of 9)

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 8 of 9)

Chad surveyed the dinner, such as it was. Hamburgers… and chips. Not much. Why had they even wanted him to cook? But he had done the best he could. He had “snitched” a bit of one of the burgers to test it and surprisingly, the seasoning mix had done a fairly good job. They didn’t taste too bad at all. Too bad he wouldn’t be getting to eat any of it. Baby food was most likely his lot.
He glanced at the clock. It was already eight minutes past his deadline. He was a lot closer to leaking now, but it still hadn’t happened yet. He prayed it would soon because every minute meant that much more misery. He went into the living room where everyone was talking. The minute he entered he caught everyone’s attention. He curtseyed. “Dinner is ready.”
“About time!” Stacy complained as she hefted herself out of one side of the couch.
Chad stood back and watched as each of them found a place at the table.
“Get me a coke!” Jillian ordered.
Chad ran to the refrigerator. “Diet for me,” Stacy called next.
“Me too,” both Cassie and Sandy said at the same time.
Chad pulled the cans out of the refrigerator and set them all on the counter. One by one he opened each one and handed them out. Then he stood back again to see if anybody would want anything else. He watched as Jillian picked up one of the hamburgers and took a huge bite out of it. Then her face seemed to register shock… then rage.
“Shit!” she said angrily with her mouth still full. “What did you do to it?”
Chad stammered. “I just… added some seasoning to make them taste better.”
“They’re not supposed to taste better,” Jillian returned. “They’re supposed to taste the same!”
Chas saw Stacy take a tiny bite of hers. Her head cocked to one side as she tasted and chewed it. “Mmmm. I think it’s pretty good.”
Sandy and Cassie each took a small bite of theirs and both of them agreed with Stacy.
“Shit!” Jillian exclaimed as she grabbed a handful of chips.
Sandy glanced up at the clock. “You’re going to be in for it, I’m afraid,” she said to Chad. “You better start leaking soon.”
Chad curtseyed, and realized that nobody had said anything about him not curtseying a minute ago. He wasn’t going to bring up the point either. “I’m trying,” he said again. “I’m really trying!”
But it was Jillian, with her mouth full of hamburger who answered instead – without so much as glancing in his direction. “Try harder!”
Chad grabbed his latest bottle of water and started drinking again as the women sat and ate and talked.

“This is so good!” Mel exclaimed as she took another bite of the deliciously broiled fish in front of her. She didn’t often eat seafood and had never been to this restaurant, but this was where Ray had taken her and she had to admit, it was a great place.
“I can’t believe you’ve never been here,” Ray said as he took a bite of his own dish.
“I never had a reason, I guess,” Mel replied. “Actually, I never even thought of coming here. It certainly is a nice place though.” She looked around the room and was glad she had dressed up tonight. All the other women were very nicely dressed too, as were the men. The word “swanky” came to mind. She had a feeling that Ray was out to impress tonight. Well, she was certainly impressed so far. Not that it mattered. Ray himself looked awfully good in his nicely tailored suit. He was more than handsome, he almost bordered on… pretty. Pretty handsome? She almost laughed. The guy was a hunk!
She took another sip of her wine, and as she set her glass back down, a formally dressed waiter was suddenly at her side. “Can I pour you another glass madam?” he asked quietly. She nodded. This was so nice!
“So, did you wear that dress in court today?” Ray asked.
Mel’s eyes went wide. “This? In court? Actually, I didn’t have any cases in court today. But I’d never wear this there!”
“Why not? I’ll bet the judge would be easily swayed by someone looking like you.”
Mel laughed. Small talk. And it was so nice.

“I’m leaking!” Chad suddenly exclaimed.
All talk at the table ceased and all heads turned in his direction.
“It’s about time,” Sandy replied as she glanced at the clock. “Geez! You’re twenty minutes late!” She turned to the women at the table. “This is going to take a while,” she said.
Jillian never even raised an eyebrow. “You got anything better to do tonight?” she asked as she stuffed the rest of her hamburger into her mouth.
Chad didn’t know what to do. He was just standing there, leaking, while the women were all eating and talking as if they didn’t care in the least about him. But then, if they planned on punishing him, then he wasn’t the least bit anxious for them to pay that kind of attention to him. With nothing better to do, he just stood back out of the way and continued to drink more bottles as the women seemed to enjoy their dinner.
He saw both Sandy and Cassie push back their plates early. They had each not even touched their second hamburgers. It was a while before Stacy and Jillian finished their meal. Chad noted that even though Jillian had complained about the way he had made them, she had finished two full hamburgers.
“I think it’s time to play ‘Beat the Sissy!’” Jillian suddenly announced as she pushed her plate back.
Chad’s eyes went wide as he watched everyone getting up from the table. Beat the Sissy?
“Let’s go doll,” Stacy said as she headed for the living room. “I’ve been looking forward to this all day.”
Chad inwardly gulped as he nervously followed everyone into the living room. He noticed that Jillian went straight through into another room, the bedroom he was guessing.
“Well don’t just stand there. Get that dress off!” Stacy ordered.
Even more nervously, Chad began removing his dress. Mel usually beat his naked bottom. Were these women going to do the same?
Jillian came back a few minutes later, her arms loaded with things that immediately sent fear into Chad’s heart. He saw handcuffs, and chains, and what looked like leather cuffs all jumbled together. She dropped all of it on the old scarred coffee table. “How do we want to do this now?” she asked everyone.
“I want him across my lap!” Stacy exclaimed immediately.
But before they could go any further, Cassie thought of a point she figured she better raise. “Um… I think we need to keep in mind that Mel has been training him to be totally incontinent. Whatever we do, we better plan in case he pees all over the place.”
“Shit!” Jillian exclaimed. “Is he that far gone?”
“Trust me,” Cassie replied. “I’ve seen it with my own eyes.”
“Yuck!” Stacy exclaimed. “That’s going to ruin everything! It’s not as much fun if we can’t spank his bare bottom!”
“You could try protecting your lap with a couple of diapers,” Cassie suggested. “That should work, I would think.”
“You think?” Stacy asked hopefully.
Cassie nodded. “It should.”
But it was Jillian who was all action. “Get that diaper off sissy boy!” Then she turned to Stacy. “Your usual paddle?”
Stacy just smiled wickedly. “Yeah! That’s what I want.” She glanced at Chad who’s diaper was just hitting the floor, revealing the chastity device underneath. “Holy cow! Look at that!”
Jillian paused in mid-stride toward her bedroom and came back to see. She stared in amazement and moved in for a closer look. “I don’t believe it!” she said. “I never actually saw one of these before.” She reached out and grabbed his chastity device and gave it a bit of a tug. “It’s on pretty secure!” she said.
Stacy who had been prying herself off of the couch, finally arrived and leaned over for a closer look too. “Damn!” she said as she reached out to touch it. She too pulled on it a bit, causing Chad to lurch off balance for a moment. “He ain’t gonna get no fun with that thing!” she announced. She looked up straight into Chad’s eyes. “Are you?”
Chad just shook his head, totally embarrassed. “No,” he replied.
“Hey!” Jillian exclaimed. “He didn’t curtsey before he spoke!” She looked back toward Sandy, “So that means we can punish him for that too?”
Sandy smiled. “That and he also missed it twice earlier!”
Jillian’s eyes lit up. “I’m gonna enjoy this!” With that, she hurried off to the bedroom.
“So go get me some of your diapers to protect my dress,” Stacy ordered. “And hurry up!” Then she went back to settle herself on the couch again.
Chad didn’t exactly hurry to his diaper bag, in fact he tried to take his time about it. But the apartment wasn’t that big so getting a few diapers didn’t take very long. Reluctantly, he handed the diapers to Stacy who spread them out as much as possible to protect her clothes. By the time she was ready, Jillian was just coming out of the bedroom again. A muted smacking caught everyone’s attention as Jillian smacked the paddle in her hand against her other hand. Chad turned quickly at the sound, but Stacy was more than ready for him and grabbed his arm and pulled him off-balance, down onto her lap. Fortunately, with a cry of alarm, he landed pretty much right where she wanted him. With a loud smack, her bare hand hit his bare backside. “Ha!” she exclaimed. “Perfect!” She took the paddle that Jillian held out to her and held it up to show to Sandy and Cassie. The paddle had holes drilled through it at various places. “Now hold still Sissy!” she said. Crack!
Chad’s whole body jolted and he cried out in pain. He hadn’t expected it to hurt that much. How could he have ever considered this monster as “sweet?”
“Make sure you warm him up good for me,” Jillian said.
“Don’t worry,” Stacy replied, “I’ll have his sweet little ass a nice cherry red in no time.”
Cassie and Sandy looked at each other as Stacy began wailing away at Chad’s backside – and Chad began wailing in pain. They hadn’t expected for Stacy to take such a role tonight. Jillian was the one they really expected to punish Sissy. Not only that, but Jillian and Stacy were pretty much acting like Sandy and Cassie weren’t even there. After watching Stacy spanking Chad for a few moments, Cassie leaned over and whispered to Sandy, “I’m glad we’re not doing the spanking tonight. I think he’s had enough already.”
“And they’ve just started,” Sandy replied. “Jillian hasn’t had her turn yet.”
Cassie nodded. “We might have to step in if it gets too bad.”
This time, Sandy nodded. “Hey,” she called to Stacy. “He was only twenty minutes late. Don’t overdo it.”
Stacy just smiled back wickedly. “Don’t worry, I’m not hitting him all that hard.”
Chad had a different opinion about that. He couldn’t believe how much her paddle hurt! He kept writhing around on her lap as she hit him. A few times he tried putting his hands back over his backside to protect his aching flesh, but each time her paddle landed squarely on his hand, hurting him even more and forcing him to take his hand away again. He finally writhed himself into such a position that with another cry of alarm, he fell on the floor.
“Damn!” Stacy cried. “What did you do that for?”
“My turn!” Jillian declared. “And it looks like we’re going to have to make sure you won’t get away like that again!”
Before Chad could get up from the floor, he suddenly had Jillian sitting on his back, keeping him there. She grabbed his arms and pulled them back behind him. She only held them there for a moment before he felt something cold and hard begin fastened to one wrist. A second later, the handcuffs were on securely and his arms weren’t going anywhere.
Jillian got off of him and looked around. “Now, let’s see. Where shall we put him?” Her eyes finally landed on the coffee table and stayed there. “I think that will do,” she declared. With one swift push of her arms, all the bondage junk she had deposited there earlier went flying off onto the floor. She reached down and grabbed Sissy by his arms that were locked behind his back and helped haul him to his feet. She led him over to one end of the coffee table. “Lay down on it!” she ordered.
“Hey!” Stacy cried, catching everyone’s attention. She held up one of the diapers that had been protecting her lap. “He peed on it!” Everyone but Chad laughed a bit.
Jillian grabbed the wet diaper from Stacy’s hand and threw it down on one end of the coffee table. She pointed her finger at it for Chad’s benefit. “Down!” she ordered.
Chad thought about defying her, but with his hands cuffed behind his back he wouldn’t get very far. Slowly and carefully, he did his best to lay down on top of the coffee table so that the part of him the really needed the protection of the diaper was right on top of it.
Jillian went into action and quickly sorted through the junk on the floor. Leather cuffs were quickly attached to each of his ankles and the ankles were in turn chained to the legs of the coffee table, making sure that his rosy red backside would stay right where she wanted it. Then it was her turn with the paddle. Before she started, she leaned down close to Chad’s head. He voice was almost a whisper. “I understand that you have deadlines, and from what I’ve just seen, you have trouble meeting them. Well, I’m going to give you something to think about to help encourage you to try a lot harder.” She stood up and moved back behind him. Grabbing the handle of the paddle with both hands, she swung it as hard as she could, connecting it with his backside.
The sound of the smack was loud, but Chad barely heard it as his body was too preoccupied by the pain that had been induced. He cried out in alarm, but all he got for his effort was another smack on his other butt cheek. He writhed on the table, but with his hands cuffed behind his back and his legs straddling the table and chained to the table legs, there was no place he could go. Jillian repeated the blows again to each of his butt cheeks.
Sandy looked at Cassie once again. A spanking was one thing, but Jillian was swinging awfully hard. They didn’t want her to hurt Chad. But just then, they saw Jillian look up and wink. Sandy held off from saying anything and waited to see what would happen.
Jillian bent down to speak softly in Chad’s ear again. “That was just to let you know what I’m capable of and that I’m serious about this. Just so you’ll have something to think about for the future.”
Chad heard her, but his mind was mostly focused on the incredible pain from how hard she had hit him. “No more,” he blubbered. “Please, no more.”
“Oh, there’s going to be more. I’ve only just started. Like I said what I just gave you was just something to think about. What I’m capable of doing. Now I’m going to give you your real punishment. After this, maybe you’ll try harder to get your diapers leaking on time… not to mention learning to curtsey when you’re supposed to – sissy boy!”
She stood up again and moved back behind him.
“No…” Chad pleaded as he started crying before she had even hit him again.
She didn’t hold the paddle with both hands like before. And she didn’t even try to hit him with all her strength, but she didn’t go all that easy on him either. As fast as she could, she pounded away on every square inch of his backside, reddening it far more than the little warm-up that Stacy had done. Only when she was satisfied with the way that it looked did she finally stop. Sissy was crying and sobbing pitifully.
Jillian went back towards his head to speak with him. “Are you going to be a good sissy boy now?” she asked.
“Y…Yes!” Chad barely managed to get out as she sobbed.
“Are you going to try even harder to make your diapers leak on time?”
Again Chad barely managed to answer… “Yes.”
“Are you going to remember to curtsey when you’re supposed to?”
One last time, Chad blubbered out his barely understood, “Yes.”
Jillian looked up at Sandy and Cassie. “You know, I really think we should work on the way he speaks. I’m sure we can… improve it.” She suddenly had a very big, very wicked grin on her face.
After seeing the beating that she had just given Chad, Sandy was ready for anything that wouldn’t be so violent. She looked over at Cassie. “Sounds like a good idea to me. What do you think?”
Cassie was of the same mind as Sandy. “I think it’s a great idea.”
Sandy remembered something else though. “Maybe we should feed him his dinner first, if you don’t mind. I don’t want Mel to be mad at me for forgetting it.”
But Jillian was all smiles. “Sounds good to me. And I think there’s still a couple of hamburgers leftover from dinner.”
Now it was time for Sandy to smile. “Oh no! He doesn’t get that! He’s too much of a baby. I brought plenty of baby food for him. And tonight, I figured it would be more fun if we fed him.”
Jillian brightened even more. “We’re going to feed him?”
“Trust me,” Cassie replied, “it will be a lot less messy this way!”
Jillian and Stacy were suddenly all giggles. “Should we do it at the table?” Stacy asked.
Sandy looked around. “Actually, we can do it right here if you like. We just need to get him sitting up… And I think it would be a good idea to put another diaper on him and set him on his next time limit.”
“Oh yeah,” Jillian replied. “I almost forgot about that.”
While Cassie and Sandy went to get his diaper bag and their big bag of other things, Jillian began unfastening his legs from the coffee table. “Hey,” she called. “How about his hands? Should we leave them or do you need me to take the cuffs off.”
Sandy looked at Cassie, but Cassie was already answering. “Leave them!”
A few minutes later, Chad, his arms still handcuffed behind his back, and still trying to get his crying under control, laid painfully down on the floor to let Sandy put a fresh diaper on him. Sandy wanted to say something to him about the beating he had just gotten, but she didn’t want to upset either Jillian or Stacy, so she said nothing about it. “An hour and forty-five minutes,” she said as she finished and checked her watch. “I hope you make it this time. I ‘really’ do!”
When he was ready, Sandy had Chad straddle the coffee table again and sit on it, which was obviously very painful to him – which brought giggles from both Stacy and Jillian.
Cassie tied a big bib around his neck while Sandy started pulling jar after jar out of the plastic bag. Twelve jars in all. Every jar containing something different.
“Can we feed him too?” Stacy asked.
Sandy smiled. “Do you have four spoons? We can all feed him.”
Within minutes, they all had a spoon and each woman grabbed a jar of baby food. Sandy went first. “Open wide,” she said. Chad opened his mouth and let her spoon the mushy cereal into it.
“Me next!” Stacy called out. Chad hadn’t even finished swallowing before she was trying to shove the cereal into his mouth. But he opened up and took it.
Jillian was next. At least Chad had a chance to swallow before she stuck her spoon in his mouth.
Cassie was a bit more patient and Chad actually had tome to swallow and open his mouth again before she stuck her spoon inside.
But before Sandy could get a chance again Stacy was anxious to get her next spoonful of baby food into him and was pressing her spoon up against his closed lips while he was trying to swallow. Chad had no choice but to open his mouth that was again partially filled with food and let her stick it inside.
And then Jillian was back all too fast and Chad was forced to open his mouth yet again while it contained even more un-swallowed baby food. Which for some reason, both Stacy and Jillian found funny. Sandy and Cassie kind of chuckled too. Before Chad knew it, all four women were pressing the food at him faster than he could chew and swallow which caused more than a little to get all over his face and drip down onto his bib.
By the time they finally finished, Stacy and Jillian had each fed him four jars of baby food while Sandy and Cassie had only fed him two. Chad was just glad the onslaught was over. If he had know it would go like that then he would have gladly skipped dinner altogether.
As soon as the baby food was out of the way, Stacy and Jillian took turns holding one of his baby bottles to his mouth for him till he could finish it, which he made every effort to do as quickly as possible.
When he was finally finished, Sandy wiped off his mouth while Jillian finally removed the handcuffs. “Let’s get him dressed again,” Sandy told everyone. “Hey, want to see how he does ‘Mary Had A Little Lamb’? It’s a riot!”