The Bet - Chapter 29 (Saturday – week 4 Part 6 of 9)

The Bet
by Karen Singer

Chapter 29 (Saturday – week 4 Part 6 of 9)

Mel kept a close watch on him as she worked on various things around her apartment. She had filled every empty baby bottle she possibly could for him. She also checked his diaper every half hour or so. And he was indeed wetting himself. At the rate he seemed to be doing it, she was fairly sure that he wasn’t holding back at all – which was exactly what she wanted. She just had to keep him doing it.
But the clock was ticking down, and so far, no leaks at all. She saw Chad keep glancing worriedly at the clock too. Well, he’d probably better be. It was a good sign. At least he was trying.
“Three… Two… One! Are you leaking anywhere?”
Chad looked down at his diaper and glanced frantically around at each of the leg openings. But so far, not a sign of a leak… anywhere! He looked up at her with tears forming in his eyes. He had tried. He really had! He curtseyed and let out more baby nonsense.
Mel stifled her smile. He was learning. She felt his diaper – it was certainly well soaked. Enough that she was surprised that it hadn’t leaked. But rules were rules, and the point here was to keep him trying to make them leak. It was the best way she had been able to come up with to make sure that he wouldn’t hold back and to try to break the incredible control he had evidently built up.
“No leaks,” she said. The tone of her voice carefully calculated to show him how disappointed and displeased she was. In truth, she really thought he had done fairly well. She wasn’t really sure if two hours was a fair test for his diapers. The exercise had to be made difficult so as to keep him constantly trying. But by the looks of things, he had almost succeeded. But the real point here was that she had to keep him doing it… And, he needed plenty of incentive!
“It looks like you tried… and it looks like you almost made it.”
Chad looked up at her hopefully. Did that mean that she wouldn’t punish him? He had tried to make the diaper leak, he really had!
“But almost isn’t good enough!” Chad’s heart fell. “You obviously wasted too much time before you wet it the first time. So now we’re going to have to teach you to not waste that time again.” She paused for only a moment as she put a sterner look on her face. “Go get your diaper bag and meet me at your punishment spot!”
Chad nearly jumped to do her command before he remembered. He curtseyed quickly and let out more of his baby nonsense. He was relieved to see Mel smile at him as he quickly went in search of his pink diaper bag.
Mel grabbed her stick and set it close by where she could reach it easily as Chad hurried back with his diaper bag. Instead of having him lay down to change his diaper, she simply made him hold the hem of his nightie out of the way while she untapped it and pulled the overly soaked thing off of him. She noticed that his penis, trapped inside of the chastity device, was still very small. She was stuck once again by how odd it seemed to see a man’s penis that small. She didn’t think it was possible before. It certainly didn’t look like anything a woman would ever find useful. She briefly wondered how big it could grow. Certainly a lot bigger than it was now… but it looked so tiny. There was no way that it looked like it could grow anywhere close to being an interesting size. She quickly put her weird stupid thoughts aside. They were in the way right now. She grabbed her stick. “Bend over!” she ordered.
Chad was surprised. She hadn’t rediapered him. She was going to beat his bare bottom! Having no choice though, he dropped his curtsey, let out his baby noises, and bent over. As he grabbed the back of the chair, he was all too aware of his naked backside as he stuck it up for her to hit. How many times would she swat him? She had never said. He prayed that it wouldn’t be very many.
Mel smiled yet again as he raised his bottom up for her to hit. Despite the diaper covering it earlier, it looked a bit red. Well, it was about to get even redder! Whap! Her stick connected solidly right on target. She saw his whole body jerk as it landed. And when she pulled the stick away, the mark that it made was definitely red. She waited.
Chad stood up, turned and curtseyed to her, and let out a short bit of baby language as the first tears began forming in his eyes again. Then he bent over once again, grabbed the back of the chair, and raised his backside up for her to hit once again. Whap!
Ten strokes. Ten curtseys. Ten bits of baby nonsense mixed with crying sobs. And a whole lot more than ten tears streaming down his face. Chad hated being punished. He especially hated it because he had tried so hard. And he thought he had almost succeeded. Maybe Mel had been right. He had wasted too much time before he wet his diaper the first time. Next time, he vowed he would try harder. He didn’t want to get punished again. And it looked like next time was coming all too soon as once again Mel only grabbed one single diaper from his diaper bag.
“Hold your hem up,” Mel commanded as she grabbed the front of him. Chad would have curtseyed at her command, but the way she had just grabbed him, it just wasn’t possible. “Spread you legs a bit more,” she commanded as she held the diaper up against his backside.
Chad was very surprised as she brought it through his legs and taped it in place while he was still standing. And by the feel of things. She had done a darn good job of it. The diaper actually felt fairly tight… all over.
“Two hours!” she told him. “And this time I better see it leaking!”
As Chad dropped another curtsey along with some baby nonsense, his thoughts immediately turned back to forcing himself to pee. It looked like it was going to be a very long day.
Maybe it was the fact that he was trying so hard to pee… or maybe it was the position she had diapered him in… or maybe it was the clean, dry diapers themselves… or more possibly it was all the bottles he had already consumed… but most likely, it was just bad timing! Because before Mel had even gotten to her feet again, Chad felt the sudden pressure from the suppositories she put up inside of him earlier starting to go to work. He knew from experience that there would be no way to stop them. And Mel had just changed his diaper. He had to warn Mel about it! He had to find some way to tell her! He dropped a quick curtsey and launched a desperate string of baby talk at her.
Mel was shocked to see him suddenly going crazy. She could see that he desperately wanted to tell her something, but the baby language wasn’t exactly getting the point across. “What?” she asked, knowing that he couldn’t tell her anything. But as quickly as he had started going crazy, he stopped again. His eyes went wide, his breathing became quicker… and he grunted with effort. And Mel knew exactly what was happening – right there in front of her.
She couldn’t help it. She absolutely couldn’t help it for the life of her. Because as his face turned red in shame… and the mess was still sliding out of him… and a tear started forming in his eye… she laughed. He was obviously so ashamed of what he was doing in his diaper just then, that she laughed. And as he moved around a bit, trying to help the unstoppable mess distribute itself inside his diaper better, she laughed even harder. He looked so funny! He wasn’t sobbing, but there were tears streaming down his face. He looked so much like a child… a very young child, struggling to mess himself. And it seemed to go on and on, longer than she thought it would. His antics settled down to an occasional wiggling of his butt, which amused her all the more. Still laughing, she had to tell him. “You look so much like a baby!” And then she laughed again as his face turned even redder.
After a while, he just stood there with a very forlorn look on his face. She almost felt sorry for him… almost. “Are you finished?” she asked. He looked up and she could tell he was about to launch into some more nonsense, but she quickly stopped him with a raise of her hand. “Tell you what. Let’s just take you back to your place where you can get cleaned up better and then get dressed.
Chad gratefully followed her outside, dressed just as he was, back to his own apartment. Fortunately, she had a key and opened the door for him. The mess in his diaper felt weirder than usual since his diaper was still dry. That didn’t last long as his overly bloated system let out another bit of pee. Why did Mel insist on still using the darn suppositories on him? To humiliate him further? That thought registered as the most likely answer to him. And it made the most sense.
Mel let him clean himself up and jump in the shower while she pulled one of his maid’s dresses out of his closet for him to wear. He had messed himself right in front of her. And it looked to her like he couldn’t control it either. And… he had done it with no suppository in his system. She had faked putting one into him earlier, but the results were the same – and very encouraging.
When he got out of the shower, she again put a single diaper on him and warned him that he had only two hours to make it leak. Then she pointed to the clothes she had laid out for him and told him to get dressed. “And hurry up about it. We’ve got some shopping to do. And don’t think that just because we’re out somewhere that you can get away with not flooding that diaper, because I will be checking constantly to make sure you keep wetting, and I will punish you if you don’t flood it two hours from now. So get as many bottles as you need for while we’re out and put them into your bag to take with you.”
Chad was totally surprised. They were going shopping? And the worst part was, that even while they were out, he would be forced to keep trying to wet himself. He now saw the genius of Mel’s new game. No matter where they were, or what they were doing, he would still be forced to keep trying to pee. And nobody would know it! Nobody would know it that is… until he did actually start leaking. What then?
Chad quickly dropped a curtsey, more baby language, then hurried to find one of his girdles to put on. The moment Mel saw the girdle, she stopped him. “No girdle today. You can wear your bra and waist cincher, but no girdle. No pantyhose either. Nothing that will cover up your diaper… except your dress that is.” She giggled a bit to herself as Chad dropped another curtsey and mumbled something around the pacifier in his mouth.
As Mel watched him struggling to put his bra on, then trying to push the breast forms into it again, she said. “That reminds me, we’ve got to glue them on again later.” Chad half curtseyed and mumbled something as he kept struggling to get the breast form in place.
A little while later, completely dressed as her maid again, his makeup and hair fixed, a pair of strappy three inch heels on his feet that Mel had picked out, and worried about what would happen because he’d be out with only one diaper… and no girdle to cover it, Chad followed Mel out his bedroom as they headed for his front door. Before they could leave though, she made him pull his skirt up so she could check his diaper. She was pleased to see that he had already wet it. But her diaper check reminded him of something else… something important.
Mel was surprised to see him desperately trying to tell her something again. Yes, he had curtseyed before he started. No problem there, but she still couldn’t understand anything he was trying to say. She almost laughed at his plight. “Now what?” she asked, knowing that he had no way of letting her know what his problem really was. But instead of standing there and letting loose with more baby nonsense, he ran back to his bedroom and came out a moment later with a large plastic bag. He dropped a quick half-curtsey, mumbled some more nonsense, then opened the bag and dumped it out. All the wet bed sheets along with his wet onesie tumbled out. He knelt down next to them, picked up a bit of girly material and mumbled more baby sounds, hoping that Mel would understand.
“You wet them?” Mel asked. “You need to wash them? Is that what you’ve been trying to tell me?”
The relieved look on Chad’s face told Mel everything, even though he did stand and curtsey along with some happy mumbling.
“You can take care of it later after we get home.” She smiled at him. “Very good by the way. Not only did you find a way to tell me, but I’m also happy that you wet so much last night that you soaked everything. We must be doing something right.” Chad dropped another curtsey and mumbled something else as she turned happily to the door. She had been right in restricting him to baby talk all day. What he had wanted to tell her earlier could wait. Easily. As she held the door wide for him to go through with his purse and diaper bag now over his arms, she cautioned him once again. “Don’t forget, only baby talk today… even while we’re out. And I’ll be checking your diapers even in the store!”