The Bet - Chapter 43 (Saturday – week 6 Part 4 of 8)

The Bet
by Karen Singer

Chapter 43 (Saturday – week 6 Part 4 of 8)

While Chad was depositing half the diapers they had just bought in his own apartment, Mel filled her big pot with water again and put it back on the stove to make more tea. She was way behind with the little chore so she needed to catch up. She could have had Sissy do it for her, but she just figured that this was part of her responsibilities. Besides, he might not make it as strong as she wanted it to be. Not to mention that she didn’t mind making it at all. It kind of gave her something easy to do while she thought about other things.
She heard her door opening again and went out of the kitchen to see Sissy just setting his purse back down on the floor under the table by the door. He was still dressed in his pink sissy dress and he still had the new pacifier in his mouth. “Grab another bottle,” she told him, “your time is running out.”
His time was running out? He glanced at the clock, he still had almost half an hour. That wasn’t so bad at all. And he was still peeing very frequently. But he did grab himself another bottle, his eighth of the morning so far. It was way too many! Way, way too many!
“Clean up the kitchen from breakfast,” Mel ordered as he started drinking.
Chad set about the little chore, which really wasn’t much. The only odd thing about it was that she was working in the kitchen making more tea while he was working around her.
“Don’t forget to wipe off your highchair,” she told him. “You’re going to need it later at Sandy’s.”
Ugh! He was going to Sandy’s again? He didn’t want to even contemplate what Sandy would be having him do this week!
Once his chair was wiped clean, along with the rest of the kitchen and the few dishes that needed to be done, he wondered what he should do next. The laundry definitely needed tending to. He started for her laundry basket.
“Where are you going?” she asked as he was about to walk out of the kitchen.
“To get started on your laundry,” he replied.
“Curtsey when you say anything!” she ordered sternly. “Or would you rather get beat again?”
Chad was shocked. She seemed to be getting more serious about this! He curtseyed. “To do your laundry, Mistress,” he replied in his sissy voice.
“You can do it later,” she replied. “Go stand on your perch and finish your bottle. Stay there till you start leaking.” She glanced at the clock. “Time is running out!” she finished.
Chad looked up at the clock. She was right, time was running out! Fortunately, his diaper was seriously getting to the leaking point – or past it. Hating to do it, he carried his bottle to his corner and carefully climbed up onto his perch. Having to hold his bottle up so he could keep drinking from it made the whole ordeal even worse. With no way to see anything beyond the two walls coming together or the corner of the ceiling, he couldn’t see the clock to see how much longer he had – making his imperative to leak all that much more urgent.
As quickly as he could, he sucked on his bottle and finally drained it. Leak! Leak! Leak! But he didn’t feel anything yet. He had peed a few times while he was drinking, but for some reason, he didn’t feel anything running down his legs yet. With his bottle empty, he finally pulled the arm that was holding the baby bottle back down to his side and lowered his head which relieved his aching neck. That much felt much better. The only problem now was that his eyes were even closer to the two blank walls, cutting off even more what little vision he had. He closed his eyes and concentrated on trying desperately to pee.
Leak! Leak! Leak! Why wasn’t he leaking? His diaper was certainly wet enough! He knew that for a fact. Yet it was remaining horribly stubborn. He had already consumed eight baby bottles this morning, more than enough to drink. Why wasn’t it leaking? Leak! Leak! Leak! How much time had elapsed? How much time remained? He couldn’t tell. Was he over his time limit? It certainly felt like it. Was he going to get punished as soon as he got off of his perch? Leak! Leak! Leak!
Mel glanced at the clock. Time was running out for him. He only had five minutes left. “Are you leaking yet?” she called.
“No Mistress,” he replied, his voice filled with frustration.
“Better hurry!”
“I’m trying!”
Mel smiled. She knew that he had to be trying. Plus, she knew how much he had already drunk. But rules were rules. Four minutes left!
Leak! Leak! Leak! He tried desperately to pee, pushing hard on his bladder, trying to force any pee that might be in his body out. Leak! Leak! Leak! But no matter how hard he tried, nothing was coming out. Frustration built in him and he tried harder and harder, but still he felt nothing. Leak! Leak! Leak!
Mel watched the seconds ticking down on the clock. She watched as the minute hand reached the allotted time. He didn’t make it. She shook her head. She could just barely see the bottom of his diaper under his silly dress from where she stood in the kitchen. From what little of it she could see, it certainly looked wet enough. More than wet enough. But it wasn’t leaking yet. Too bad – for him.
Leak! Leak! Leak! Chad had no doubt now that time had run out. It felt like he had been up on his stupid perch for an hour now, even though he knew it was far less. But it had to be longer than his time limit. Why wasn’t he leaking? Leak! Leak! Leak! Still, he pushed hard to try to pee, over and over again, but still, he felt nothing.
Then, wonder of wonders, he was startled to feel a tiny bit of pee running down his leg. He was leaking! But he never felt himself peeing again. Not wanting to waste time to think about it, he called out. “I’m leaking!”
“About time!” Mel called back as she poured tea into another baby bottle. “Get down off of there.” She looked up at the clock. A full twenty minutes over. Not very good – unfortunately. “Get the floor ready,” she called as she pulled over another baby bottle to fill. She briefly looked up at him. “And take that dress off. I don’t want it to get messed up! You can put it back on afterwards.”
Chad wasn’t too happy to hear that last part. He’d just as soon take the dress off and leave it off – permanently. It took him a few minutes to spread enough diapers out on the floor to protect it adequately, then he took his dress off. His diaper sagged heavily and threatened to fall off of him. It was amazing that it took that long to make it leak. More pee had escaped out of it and a few tiny rivulets of it were running down both his legs, even though he still hadn’t felt himself peeing any more. Was he? He briefly wondered if he should remove his shoes too and was about to kneel down to do so when Mel walked out of the kitchen.
Mel went straight up the corner where she kept her yardstick and picked it up. She looked him over briefly. He looked totally ridiculous standing there in just his soggy diaper with the pink heels and the cute ankle socks.
“I was just about to take my shoes off,” Chad told her.
Mel quickly swung her yardstick and caught him on the side of his leg. “Didn’t I tell you to curtsey every time you say anything?”
Chad was still trying to recover from her suddenly blow. The spot where she had hit him stung. He quickly curtseyed. “Sorry Mistress. I was just about to remove my shoes.”
“Don’t bother,” she told him. “Just get that diaper off before it dissolves completely.
Chad pulled on one of the tapes that held his diaper closed. The plastic on the diaper seemed to stretch more than the tape was ripping off. The added pressure from his pulling sent a long stream of pee out of the diaper running down his opposite leg. The thing was really saturated. Why couldn’t it have leaked earlier? He got one tape unfastened and noticed that the whole thing felt like it just wanted to fall off of him. Instead of pulling another tape open, he carefully eased it down his legs all the way to the floor and then eased his heels out of it, trying not to get any on his socks – or anywhere else for that matter. He stood up again, glad to have the soaked thing off of him.
Mel stared at him for a moment. She had watched him removing the soggy diaper – totally amazed that the thing hadn’t leaked long before it did. She really hated punishing him when it was obviously so wet. But it hadn’t leaked so she had to punish him. The odd thing was though, that for once, she didn’t really seem to mind. It had been a while now since she had thoroughly spanked him. He probably needed it by now – just on general principal. Besides, he needed to pay more attention to little things like curtseying every time he opened his mouth. Maybe punishing him for this would make him pay more attention to little things like that.
She was about to tell him to get into place, when she noticed a tiny bit of pee dripping out of his chastity device. He didn’t seem to notice that it was happening. Was he peeing just then? She ignored it and pointed to the back of the chair. “Get ready. You were twenty minutes late. You’re going to get plenty of practice curtseying today!”
Twenty minutes! Chad wasn’t glad to hear that. But better twenty minutes than thirty… or forty. It was little consolation. Twenty swats. Twenty painful stinging swats. No, he wasn’t looking forward to it at all. And he had tried – he had really tried. Some diapers were just harder to make leak than others. Hating it, he leaned forward, bracing his hands against the chair in front of him. He took a deep breath to get ready, then stuck his rear end up higher as if inviting her to hit him – which he guessed he was. Swat! Ouch! Her first blow stung horribly. It was always a terrible shock to his system. He stood up and curtseyed. “Thank you Mistress.” Then he got back into position. Nineteen to go!
Mel swung her stick again, catching him perfectly on the meat of his backside. She wasn’t swinging as hard as she could, but it was still plenty hard enough. She could already see his skin turning a rosy pink where she had hit him. There was no anger in her at all today. Today, it was simply an exercise that had to be done. Yet, strangely, she was still enjoying it. She watched him curtsey to her again. So cute! Especially with those crazy pink heels and cute little socks on – and nothing else.
She didn’t really need a reason to punish him. The terms of the bet spelled that out implicitly. But it was a chore she didn’t usually relish. Yet it was another way of expressing her domination over him. Another way of showing him how much in control of him she was – whether he liked it or not. And in this case, she was fairly sure he didn’t like it – which pleased her all the more because she could still do it.
Two swats later, she noticed a tiny bit more pee dripping out of his chastity device again. Did he know it was happening? Or was he trying to ignore it like she wanted him to? It didn’t really matter, she was glad to see it. She didn’t want him controlling himself one little bit – ever! So seeing it was a good sign. She just couldn’t help wondering if he knew it was happening. Swat!
After eleven swats, Chad was starting to worry. If he didn’t manage to pee while she was hitting him, then he would get an additional five swats! He had to pee! He almost felt like he could, but no matter how hard he pushed, he couldn’t feel anything happening. Swat! He stood up again and curtseyed. “Thank you Mistress.”
Mel watched as he leaned over again, preparing himself for yet another blow. A tiny bit more pee dripped down onto the diaper below. She noticed that the spot below him was starting to grow wetter and wetter. Well, it should! Swat!
After fifteen swats, Chad’s backside was on fire! He wanted to rub it to ease the pain, but he dared not touch it. He was starting to cry openly. Tears were already leaking from his eyes. He was sorry that he hadn’t made his diaper leak. He really was. He had tried. He really had. But it just didn’t happen. And now he was starting to panic inside because he hadn’t yet peed while she was punishing him. He was trying! Just like he had tried to make his diaper leak earlier. He was pushing constantly – non-stop! Hard! But just like earlier, nothing was happening – no matter how hard he tried. If he didn’t pee soon then she would hit him more, and he had already had enough! Pee! Pee! Pee! Nothing! Nothing! Nothing! Swat! Curtsey. “Thank you Mistress.” Pee! Please!
Mel watched as the wet spot below where he leaned over grew a bit bigger. Still, only a tiny bit dripped out of his chastity device each time, but it was almost every time he leaned over like that. Did he know it? She was coming to the last few blows. She would find out soon enough. Swat!
Chad couldn’t help it. He was crying pitifully. His backside hurt horribly. Each time he tried to thank her, the words were almost unintelligible. He couldn’t help it. He was crying because she was punishing him. He was crying because he had failed to make his diaper leak on time. And just as much, he was crying because now he had failed to pee during his punishment. He had already finished eight baby bottles and it was still only mid-morning. How much did he need to drink? He had failed! Failed! Failed! And now she was punishing him for it. He felt miserable – in more ways than one. Swat! Number twenty! He stood up again and curtseyed. The movement made his backside hurt even more. “Thank you Mistress,” he managed to sort of blubber again. He had failed to pee – again. Knowing that he had no choice, he leaned back against the chair. Five more! Ouch!
Mel had counted twenty. He was crying like a baby – and rightly so. She actually loved seeing it. Had she miscounted? Or had he? Or was he waiting for more because he didn’t know he had been peeing through most of his punishment? The last seemed very unlikely. “How many is that, Sissy?”
Chad turned his head. “Twenty, Mistress.”
She quickly swung at his backside, harder than before. “Curtsey when you say anything!”
Chad stood up and curtseyed, now feeling self pity because he had forgotten to curtsey again. “That was twenty, Mistress… now twenty-one.”
“That last one didn’t count!” Mel replied. “That was for not curtseying when you should have.” She looked at him a moment, trying to figure out what was going through his mind. Was it possible he didn’t know he had peed? Such a little bit had dripped out almost continually through the whole punishment. Was it possible? “What happens now, Sissy.”
A huge sob escaped his lips before he could reply. He almost forgot to curtsey, but remembered just in time as he sobbed, “I tried, Mistress. I really did! I tried so hard to pee while you were hitting me but nothing came out! I really tried! I did!”
Was it possible? It certainly sounded like it. “So what should we do?” she asked.
Chad remembered to curtsey. The words were hard to say and his crying increased at having to say it. “Five more strokes.”
“So you think you need five more strokes?”
He didn’t think that at all, but he’d never get away with telling her that. He curtseyed. “Yes, Mistress.”
“Five more strokes for what?”
He curtseyed – what an annoying pain – “For not peeing during my punishment.”
She nodded. Unbelievable! She smiled wickedly at him. “Say please!” Then she watched in delight as he dipped another curtsey and asked her to please punish him for not peeing. Delightful! And the poor sap didn’t know that he had been peeing through almost the whole thing! Well, she wasn’t going to tell him. “Very well, Sissy. Back in position. Since you said please…” Swat!