The Bet - Chapter 45 (Monday – week 7 Part 6 of 7)

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 6 of 7)

Sandy felt like she was letting Mel down. Besides, she absolutely loved watching Sissy make such a fool of himself – especially as a baby – so she guessed she was disappointed for herself. But tomorrow night was out. She and Cassie had plans and there was no way she could watch Sissy for Mel. Unless… Unless… She and Cassie were just going to visit some friends for the evening. What if they agreed to let Sissy come too? Now that she thought of it, the more she liked the idea – really liked the idea!
She picked up her phone and called Cassie to see what she thought, then she called one of her friends to get her opinion. No problem! Finally, she dialed Mel’s number.
Mel was just driving home from work when her cell phone rang. With one hand, she quickly dug it out of her purse and answered it. “Hello?”
“Hi Mel, it’s Sandy.”
“Hey Sandy. What’s up?”
“Did you ever find someone to take care of Sissy tomorrow night?”
“No!” Mel answered, totally frustrated with the problem. “Got any ideas?”
“Maybe one… if you’ll agree to it.”
Agree to it? That sounded fairly ominous. Especially knowing Sandy. But she was desperate. “What did you have in mind?”
“Well, Cassie and I are just going to visit some friends tomorrow night and… well… I thought that maybe Sissy could come with us.”
Mel wasn’t too sure about the idea though. “Don’t you think your friends will object to someone like Sissy being there?”
“Oh no! They’re very… open minded. In fact, they’re both a bit… wild!”
Wild? That shook Mel a bit.
“But don’t worry,” Sandy continued, “I already checked with them and they said they didn’t mind at all.”
Mel was still trying to contemplate what wild meant. But desperate was desperate! “Um… I guess it’s okay, as long as they don’t mind. But Sandy, the real reason I need someone to watch Sissy is to make sure he keeps wetting as much as possible. You know, like with the time limits I put on him. Do you think they’ll mind that too?”
Sandy giggled. “No problem! I already told them about Sissy. In fact, they’re looking forward to seeing him. But don’t worry, just because they’re a bit kinky, they’re still good people.”
Kinky? “Um… I’m sure they are,” Mel replied. But she also realized that Sandy had already been through and checked with everyone. “Then I guess I don’t see any problem at all. Especially if you can make sure he keeps to his schedule. In fact, I appreciate it a lot!”
“Great Mel!” Sandy replied enthusiastically. “And I was thinking, maybe we could even offer to let Sissy cook us all dinner too?”
That part didn’t really bother Mel in the least. “That’s fine. He seems to like showing off his cooking talent.”
Sandy laughed. “It’ll be great! I can’t wait to show him off in that silly baby dress to everyone… Oh, hey! Gotta’ go! Talk to you later!”
Mel was suddenly left with an empty phone connection. Sandy wanted him dressed in his baby dress? What kind of evening did she have in mind? She now didn’t know if she was worried… or if she wanted to be there just to share in the fun!

Chad glanced at the clock. Mel was running late. But more importantly, he was worried about how much time he had till his diaper had to be leaking. He already knew that Mel would be home shortly. He also knew he was going to get a beating tonight for taking his thumb out of his mouth earlier with Robin. He didn’t want to make things any worse by not getting his diaper to leak when it was supposed to. So he was drinking furiously from his third baby bottle now since he had gotten home.
He heard the apartment door opening and he rushed out and saw Mel just coming in. He curtseyed. “Welcome home Mistress,” he said in his sissy voice.
Mel smiled at seeing him curtsey and hearing his silly sissy voice. The aroma of something good cooking in the kitchen filled the apartment too. “Thank you Sissy,” she replied as she set her things down on the little table by the door. When she turned back again, Chad was hurrying away back to the kitchen. She followed after him. “Something smells good,” she said as she watched him hurrying to the stove where he grabbed a large spoon to stir something in a pot.
“Thanks,” he replied as he set the spoon down again. “Dinner will be ready in just a moment.”
Mel shook her head. “I’ll be adding five more swats to your punishment tonight for not curtseying before speaking to me just then!”
Chad was shocked. He had been busy cooking! And she still expected him to curtsey every time he opened his mouth? Ugh! He curtseyed now. “Yes Mistress,” he replied sullenly.
Mel noticed that the table was very nicely set already. “I’ll be right back,” she said to him as she turned and headed toward her bathroom.
Chad dished out her meal. But it was only a meal for one. He hadn’t bothered to make any for himself since she had declared that he would be eating mostly baby food from now on. There was a whole cabinet full of it that he didn’t even want to look at. Mel came back as he was looking everything over one more time to make sure he hadn’t forgotten anything. This time he remembered to curtsey first. “It’s all ready Mistress,” he said as he stood back.
Mel smiled and sat down. Everything looked so nice. The food smelled so good. All that remained now was… “Sissy, back to your perch!”
He had been expecting it, but he still hated to hear her say it. He quickly grabbed himself one more desperate swig from his latest baby bottle, then headed sullenly back to his little corner where he climbed up onto his perch. His body was pressed up against both walls. The only thing he could see was the blurry vision of the two walls. He closed his eyes and tried to concentrate on staying as still as possible. Back in his little corner. Back up on his perch. Back to being out of sight and out of mind. Back to being – bored!
Mel ate leisurely as she watched him up on his perch in the corner. Dinner was excellent! He wondered what he would be cooking for Sandy and her friends tomorrow night. Whatever it was, she had no doubt that it would be something good. He didn’t know about that yet and she wondered if she should tell him or not. She decided to keep it from him for now. It wasn’t something he needed to be worrying about – yet. And knowing Sandy, maybe he should be worried! Sandy wanted to show him off in his baby dress? Her friends where wild? Kinky? She had a lot of mixed feelings about that. But mostly, she was jealous that she wasn’t going to be there herself.

Bored, bored, bored, bored, bored, bored, bored! Boring corner. Oh! I’m peeing! Excellent! Yes! Feels great! Is my diaper leaking? Leak! Leak! Leak! Please leak! Nothing… yet. Got to pee again! Got to start leaking! Need more to drink, but I can’t if I’m stuck here in this boring corner. How long have I been here now? How much longer? Isn’t she done with dinner yet? Ugh! I’m tired of this. My calves ache! My toes are all scrunched and hurt. I want to move them. I need to move them. But I can’t move them. There’s just no way. Stuck! Ugh! Want to move but I can’t. How much longer? Need to pee again! Come on! Pee, pee, pee!

Mel got up from the table and opened the cabinet that now held all his baby food. There was a lot to choose from. She started taking down jar after jar to see what it was. Gradually, she built a suitable dinner for him as she set the jars she wanted down on the counter. She grabbed a plastic child’s plate from another cabinet along with one of his rubber coated baby spoons. Then she opened jar after jar and dumped out the colorful mush onto the plate. When she was done, she was tempted to mix it all together into one big mushy pile, but she didn’t.
“Okay Sissy. Get yourself over here.”
Chad gratefully pulled himself off of his perch and stretched his legs and feet before trying to walk. He was just glad to finally be out of the corner again. He was especially glad to finally be off of his perch again. By the time he got to the kitchen, Mel was holding the tray to his highchair in her hands and was waiting for him to climb up onto it. He headed for the chair, but he saw a sudden look of anger in Mel’s eyes. He stopped and curtseyed to her again. He was relieved to see her smile. Only then did he climb up into his chair. She pushed the tray into place, locking him into the chair. Then she tied a bib around his neck. She delivered his dinner to him along with the tiny baby spoon. And finally, she put his latest baby bottle down on the tray for him to drink from. He grabbed the baby bottle first because he had to meet his leaking deadline.
Mel poured herself another cup of coffee and leaned back against the kitchen counter to watch him eating as she often did. “So it looks like you’re not going to get fired after all?” she asked.
Chad stopped eating momentarily and sighed with relief. “It looks like it anyway. Robin said she didn’t tell anyone.”
Mel smiled. “That’s good.”
“She was just so angry at me!” Chad said as he dipped his little spoon into some orange colored mush.
“What did you expect?”
Chad shrugged before stuffing the colorful food into his mouth. The action made him miss a bit and some of it spilled down onto his chin.
Mel chuckled. Actually, it was the first food he had spilled so far.
“I was hoping it would go a little better,” Chad finally said as he dipped his spoon back into his food again. He suddenly looked up at her. “And where did this sticking my thumb into my mouth thing come from?” he asked.
That was the part that had surprised Mel too. Surprised, and delighted her. But she wasn’t going to tell Sissy that. “I don’t know,” she replied. “I honestly don’t know.”
Chad went back to eating – and wondering what had gotten into Robin.
“Tomorrow night,” Mel said, surprised that it had come out of her mouth because she wasn’t planning on telling him about it yet. “I have a date.”
Chad was a bit surprised. “With Ray?” he asked.
Mel nodded. “Yes. With Ray.”
Chad felt disappointed and hurt. But he stopped himself from feeling any worse. Why shouldn’t she go out with a proper good looking guy? Why shouldn’t she have some fun with a real man? Who was he to say what she should and shouldn’t do? She was a good looking woman. She deserved to go out with a real man… not someone like him. Yeah, like she would ever go out with him… a sissy! Looking only down at the food on his plate he replied. “I hope you have a good time.”
Was that… disappointment she heard in his voice? Interesting. “I hope we will,” she replied. “And… I hope you have a good time too.”
Chad looked up quickly. “Me?”
Mel nodded. “You’ll be going with Sandy and Cassie to visit some friends of theirs. From what Sandy said, it sounds like she wants you to cook dinner for them.”
Chad’s surprise turned quickly toward being very interested. Cook them dinner? What should he make? It would have to be something that he knew was really good that would show off his cooking ability. A little problem quickly arose. “Will they be coming here?” he asked.
Mel shook her head. “No. Why would you ask?”
“Because I don’t know what kind of food they’ll have, or what spices they have, or what kind of pots and pans and other stuff they have available. Maybe I should go shopping before then and get everything I need. Then I can just take it all with me. Do you know how many will be there?”
Mel shook her head. “Don’t worry so much about it. I’ll check with Sandy tomorrow and let you know.”
As Chad finished the rest of his meal, he barely noticed anymore what he was eating. His mind was more focused instead on what he could make them for dinner. He wondered if Sandy’s friends were worried about eating only diet food.

While Chad was busy cleaning up the kitchen after dinner, Mel changed into a pair of shorts and a t-shirt. Then she put her ballet music on again and started making notes about what things she wanted to choreograph for Sissy’s ballet. It was slow going, but she was making progress. Her biggest problem was that he knew nothing at all about dancing, and he was absolutely not graceful in the least. But she supposed that none of that was the point. The point was to create something to show off what a sissy he really was… or so she thought. Since she was creating this thing, there was a certain amount of pride in showing off what she was capable of doing.
She glanced at the clock. The time for him to be leaking was quickly running out. “Sissy! Are you leaking yet?” she called from the living room.
Chad had heard the ballet music on her stereo and knew that he would be spending some time dancing again tonight. But that wasn’t her immediate question. “No, not yet.” he replied somewhat forlornly. He was close. He knew he had to be very close. But so far this diaper was proving to be stubborn.
“Did you curtsey before you answered me?” she called back.
Chad could have screamed! “No,” he replied once again with even more disappointment.
“How about then?” Mel asked.
Chad wanted to kill himself. This time he curtseyed, then replied. “No… but I just did then.”
“I’ll add ten swats to your punishment tonight. Better hurry up, your leaking deadline is getting awfully close!”
He knew it. He knew it all too well. There were still a few pots to finish cleaning, but he ignored them in favor of doing nothing but drinking from his latest baby bottle. Pee! Pee! Leak! Leak! It was impossible to try to pee any harder than he was already doing. It seemed like his whole life lately was dedicated to doing just that. With Mel around, it never let up! He briefly wondered about tomorrow night. Hopefully, he wouldn’t have to worry about it tomorrow night at all. That would be a blessing!
He suddenly felt himself peeing yet again. He spread his legs hoping it would help matters, but unfortunately he felt nothing leaking. He glanced at the clock – two minutes left. Pee! Pee! Leak! Leak! But he had just finished peeing. He finished his bottle and quickly grabbed a fresh one out of the refrigerator. He drank furiously from it – just as he had with his last bottle. And miraculously, he felt a tiny bit of pee coming out once again. Leak! Leak! But nothing. It had been too little. In frustration, he began pacing around the kitchen while he drank from his bottle. One minute left. But then he felt something a bit odd. Wetness? He really wasn’t sure. He felt down around the bottom of his diaper and right at the leg opening on one side it felt a bit – wet. Yes! “I’m leaking!” he called out victoriously.
Mel glanced at the clock and saw the second hand tick down to the final second. She smiled. “Did you curtsey?”
Chad really wanted to kill himself.

Chad leaned over and put his arms up against the back of the chair. His totally naked bottom already made an inviting target for the thick yardstick she was holding at the ready in her hands. But it wasn’t what she wanted. Not what he had to do. He had no idea how many times she was planning on hitting him. Fifteen for sure, plus… a bunch more probably. Hating having to do it, he purposely raised his naked backside up even higher, making it the perfect target for her cruel stick. The swish of the stick moving through the air was faster than usual. Smack! Ouch! She had really hit him hard! Wow! With is backside stinging horribly, he stood up and curtseyed. “Thank you Mistwess,” he said in his sissy voice. It was a horrible thing to keep thanking her like that for hitting him. But… what choice did he have? He leaned back over against the chair again and raised his backside up into the required position. Swish… Smack! Ouch!
“You know Sissy,” Mel said as she waited for him to stand up and curtsey again, “one way or another, we’re going to teach you to curtsey politely at the drop of a hat.” She waited while he went though his little ritual and started to get back into position. “One way or another…” Swish… Smack! “We’re going to get you so accustomed to curtseying that you’ll be doing it without thinking anymore.” Again she had to wait while he curtseyed and thanked her. “You’ll be doing it before you do anything!” Swish… Smack! “If I have to, I’ll have you curtsey to every door before you open it… every little thing before you even touch it!”
Chad tried his best to digest that as he once again stood and curtseyed to her. “Thank you, Mistwess,” he said in his sissy voice again. But the shake in his voice was almost as much from the things she was saying as much as the pain he was feeling. He was so preoccupied by worrying about the next upcoming blows from her stick, and with what she was saying, that he didn’t even notice when he started peeing again as he leaned forward to brace himself against the back of the chair.
Mel smiled as she saw the golden colored liquid squirting out from his chastity device. “Well at least that’s one less thing we’ll have to beat you for tonight,” she said just before she swung her stick again.
Chad wasn’t even sure what she was talking about, and he thought even less about it as the sharp stinging blow to his backside registered immediately with his brain, wiping out all other thoughts.
Fifteen strokes, fifteen curtseys. All for not curtseying before he spoke – and each time had been when she wasn’t even in the same room with him. He was just glad to get them over with. His backside was on fire!
“Okay, that was the easy part,” Mel said as he finished his last curtsey and thanked her.
Chad wondered what she meant by that. He certainly wouldn’t have called that easy!
“Now we have to punish you for not following Robin’s instructions.”
He knew it was coming, unfortunately, he just didn’t know what Mel planned on doing about it.
Mel pointed toward the back of the chair again, and regretfully, Chad got back into position.
“Since this is going to be a lot…”
A lot? Chad started to get alarmed.
“…then just stay there like that till I decide to take a break. Then you can curtsey and thank me.”
Till she takes a break? A break? How many times was she planning on hitting him? And he already hurt!
“You’re going to learn that when a woman tells you to do something – make that when anyone tells you to do something – especially a woman – then you had better do it – exactly like they tell you to! Ready?”
Ready? Of course he wasn’t ready! What was she planning? Before he could think any more about it, she swung her stick – hard again. And before he could even fully react, she was swinging again, and again, and again. Over and over again as fast as she could, she pounded away on his backside with her stick. And the pain from it grew, and grew, and grew!
Mel swung fast and hard, but she was carefully controlling herself. Yes, she wanted to hurt him, but not like she would if she had lost control. Over and over again she hit his bare bottom, making sure to cover every inch of it on both sides. Very quickly, it grew from a warm rosy red to a very deep dark red. Finally she paused. “You can thank me now.”
Chad had no idea how many time she had hit him, it had hurt so much that it seemed to go on forever. He had been crying a little and fighting the tears before she had started, now he was bawling full out. He stood painfully, turned to her and curtseyed. But the words that came out of his mouth around his sobbing weren’t completely recognizable. Fortunately, Mel didn’t seem to notice.
“That’s one,” Mel said and pointed towards the back of the chair again.
One? One? He couldn’t believe it. She wasn’t done with him? He looked at the back of the chair and hesitated. He didn’t think he had the courage to lean back against it again for more punishment. But his hesitation only cost him another stinging slap from her stick against his leg. Quickly, he found himself back in position again awaiting the next part of his beating. Once again, Mel flailed away at him unmercifully while he cried, and cried, and cried. Finally she stopped. He was still leaning against the back of the chair, but he couldn’t move.
“Are you going to do as you’re told from now on?” Mel asked.
Still leaning against the back of the chair, he nodded his head vigorously and tried to say, “Yes.” But the moment he did, she was back hitting him again. Five more quick swats of her stick.
“That was for not curtseying before you spoke again!”
Chad curtseyed again, but he didn’t even try to speak. He was crying too hard. Three minutes later, he was laying face down on the carpet on top of a fresh diaper while Mel was gently applying soothing lotion all over his dark red backside. The lotion felt frigid cold and stung as soon as it touched him, but it quickly warmed up. Even though she was only lightly touching him, her hand still felt all too painful as she rubbed the lotion all over his bare skin. He hurt so badly that he was glad when she finally finished and he could roll back over so she could finish diapering him again. And once again, he was working on another hour and forty-five minute time limit.

Chad stood in the middle of her living room, fully dressed once again. He had expected to be practicing ballet again tonight, but it seemed that Mel had other ideas. Ideas that he was not all that fond of. Mel had been working with him for the last fifteen minutes trying to craft just the right kind of apology for him to give to Robin tomorrow. It wasn’t that it was all that much or all that difficult. It was just that it was… embarrassing! But then, wasn’t any kind of apology embarrassing?
“I think that will work,” Mel declared from her seat in the living room. “Let me see it now one more time.”
Chad curtseyed to her immediately – he dared not even think about doing anything without curtseying first. Then he paused for a moment to get ready. He reached down and grabbed the hem of his skirt and dropped into as nice a curtsey as he could, spreading his skirt as wide as possible. He bowed his head momentarily, then rose again putting his feet together and clasping his hands contritely in front of him. “I’m sorry Robin,” he said in his sissy voice, “that I didn’t do exactly what you told me to do yesterday. I promise not to give you any more trouble and to do whatever you say from now on.” Then he dropped into an identical curtsey to the first one again and stood back up. He looked to Mel for her approval and curtseyed quickly to her once again as he did so.
Mel smiled. “Yes, I think that will work nicely. It’s not too extravagant and I think it sets just the right tone. Don’t you?”
Of course all Chad could do was to curtsey again and agree with her.
“Good, now do it again.”
Once again, Chad had to go through the little routine, followed by another practice run, followed by another one. Finally, Mel dismissed him to go finish another bottle while she went back to work on making notes for his ballet.
Chad hurried into the kitchen where his latest bottle was, and immediately put it to his mouth and started drinking. Her stupid little apology routine wasn’t very difficult, but it sure made him feel foolish as he did it. Of course, when he did it for Robin tomorrow – ‘if’ he did it for Robin tomorrow, then he wouldn’t be using his sissy voice. His girly voice wouldn’t be quite so humiliating.
He finished his bottle and was just opening the refrigerator to get another one when Mel called him back into the living room again – to practice the routine five more times.