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

The Bet
by Karen Singer

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

As Chad walked slowly up and down the rows of shoes, he didn’t really know what he was looking for, or if he really cared. He had plenty of shoes… but he liked shoes. Especially heels. Mel was looking at a pair of wild leopard print pumps and had told him to just go searching for whatever he liked. So… he was looking. The problem was, he liked everything he saw.
He came to the spot where a few weeks ago his diaper had leaked so badly that it had puddled on the floor. It made him think about his diaper now. It was certainly starting to feel awfully wet. But how long had it been now since Mel had put it on him? How long was left till it had to be leaking? He was fairly sure that he still had a little while to go, but he couldn’t have too much longer. But since he wasn’t wearing his watch today he had no way of knowing. In fact, the only jewelry he had on were the pink studs he had put in his ears earlier this morning.
He suddenly realized he was peeing again. Geez. There had been no warning again that he was going to do it. And again, he hadn’t realized it till it was already happening. He had to get with it! It would be no good at all if he didn’t even know when it was happening. He hadn’t even had anything to drink now in a while – not since they had left her apartment. Not knowing he was peeing wasn’t going to help him win this bet!
He realized too that his state of mind was such that it wouldn’t help him at all either. He was so upset over what Mel had done, that he barely cared – about anything. But how could he feel anything but depressed right now? All he could think about was Robin telling everybody else and what would happen on Monday. No matter what, it wouldn’t be good – that much he knew for a fact. Basically, the thought scared him… more than a little.
“Find anything?” Mel asked as she walked up.
Chad just shrugged again. “Not really,” he replied dully. He noticed that she was now holding a closed shoe box in her hands. Was she really going to wear those wild shoes? He didn’t think he had that much courage. What would they go with?
Mel was starting to get fed up with his depressed attitude. Yes, she knew he was depressed. Yes, she agreed that he probably should be depressed. And yes, she knew it was all her fault. But he needed to get with it a little more than he had been. She had been trying to be nice to him. He had shown a few signs of life, but they were very few. She was beginning to tire of his whole not caring attitude. “Can’t you even try to act a little better?” she asked, her voice containing more than a hint of the anger she was starting to feel. “Show some enthusiasm?”
Chad didn’t know what to say. He knew he wasn’t behaving… properly. But to tell the truth, he just didn’t feel like it. It was hard to feel enthusiastic about much when your whole life was in the process of being ruined. Not to mention that the very person who had caused the problem in the first place was the one who was asking the question – Mel. But what was he supposed to say to her? Finally he sighed. “I’m trying,” was all he was able to get out. And saying it in his sissy voice was somewhat difficult.
“Well try harder!” Mel replied. She tried to smile again as she looked down the rack of shoes. “Hey, now that pair would go great with your new dress!”
“But I’ve got shoes that will work,” Chad protested.
“So? I thought you liked new shoes.”
“I do but…” But the truth was, that he did like them. He shrugged again. “I guess I do like them,” he replied sheepishly.
Mel wasn’t sure if he was starting to come around or not. “So what do you think about those?” she asked as she pointed the pair out again.
The shoes were a pair of black patent sandals with a high, thin, elegant heel. The straps on top of the toes were decorated with black patent bows. Chad realized that they were really nice – and would go very well with not only his dress but the new clutch bag as well. “They would go well,” he agreed as he picked one up to look at it.
“Go find a salesman and get him to bring you some to try on.”
It was as if her words were there to make his decisions for him. Instead of answering, he simply turned and went in search of someone to help him.
Mel watched him turn and leave. His attitude was starting to get under her skin more and more. He was trying, but not hard enough. She had tried being nice to him, but maybe what he needed was some additional – prodding – of a different sort.
Chad found a saleswoman fairly easily – for once. He had dealt with this one in the past and he was sure she recognized him. She didn’t even bat an eye as she looked at the shoe he wanted and went in search of a box. She was back fairly quickly with it and just handed it to him. Chad carried the box back to Mel before trying them on. They fit perfectly. He was quick to notice though that the heel was about as high as on his pink patent heels, only styled to look a bit thinner. He took a few steps in them, then just nodded toward Mel. “They’re good,” he said with little enthusiasm.
“They look great!” Mel declared, watching him carefully. No facial reaction. It was time to get more forceful! “Show me your diaper!” she ordered quickly.
Chad was so startled by her sudden command that he couldn’t react right away. Her sudden command on top of his depression and non-caring attitude caused him to totally freeze up and just stare at her in surprise.
Mel saw the total shock on his face. It was the most emotion he had shown since they had left the house earlier. Finally, she was reaching him. She put a determined angry look on her face and repeated her command more forcefully. “Show me your diaper! Now!”
It still took Chad a moment to react. The angry look on Mel’s face seemed to be the final push he needed to force him into motion. Fear of reprisal if he didn’t react quickly seemed to reach his subconscious. Without giving any other thought to where they were or who might be around, he reached down and grabbed his skirt and quickly pulled it up as high as he could, showing off how soaking wet his diaper was.
“Aahh!”
The sudden shocked gasp from another woman customer turned Mel’s head. She hadn’t bothered to speak softly at all when she gave Chad his command. Now her loud voice had attracted the attention of several other customers who were quickly coming over to see what was going on. Oh well, it was too late now. Besides, she was more concerned with snapping Chad out of his fog and getting him back on the straight and narrow again. She took the time to notice that his diaper was getting awfully wet – but it wasn’t leaking yet.
Chad stood there with his skirt pulled up high. The sudden little scream from one of the other customers actually scared him a little – especially because it let him know that they were no longer alone. And Mel was now just making him stand there – fully on display! Talk about humiliating!
Mel noticed that nobody seemed to be complaining – yet. They were all probably too shocked. There were about four or five other people around – that she could see. Well, since nobody was voicing any arguments yet… “Sissy! Turn around slowly and show everybody how wet you are!”
Chad wanted to die! He couldn’t believe she would do such a thing! But she just had! Since everybody could already somewhat see him, there was no use trying to argue or not do it – as if he had a choice anyway. He slowly began turning around, feeling his face getting redder and redder the further he went. He couldn’t believe he was doing this. But then, hadn’t she made him do something similar in the grocery store once? By the time he was back to facing Mel again, he noticed there was a hint of tears in his eyes from the humiliation.
“Okay Sissy. You can drop your skirt now.”
Chad pulled his skirt back down, but pulling it down gave him nothing to hide behind anymore – as if it really mattered. Now there was nothing in the way of him seeing how many people were around. More than he wanted, that was for sure! He didn’t want to look at any of them so he stared at the floor.
“Your time is running out to get that thing leaking,” Mel told him, making no pretense to lower her voice. “You better get busy.”
Chad barely nodded as he continued to stare at the floor.
“Answer me properly!”
Chad was horrified again. Why had she suddenly gotten so angry? Hating doing it in front of the people, he dropped a curtsey and said in his sissy voice, “I’m still trying, Mistress.” He heard only a tiny chuckle from one or two. The rest of the people were still trying to figure out what was going on – not to mention trying to figure out what they should be thinking about it.
Mel knew it was time to get out of there, but he was finally starting to react more normally now. Maybe she should have been more forceful all along. Another little idea slipped into her brain. It was nasty, but… “Sissy! Since it took you so long to show me your diaper… and I had to tell you twice... take your skirt off!”
Chad looked up from the floor to stare at Mel in horror. Take his skirt off? Here? Now?
“You heard me. Take it off! Right now!” Seeing him hesitate, she added, “Get it off now or you’ll be even sorrier later!”
His face full of shock and shame, he couldn’t tear his eyes off of Mel as he slowly started removing his skirt, not just lifting it up to show everybody the diaper he was wearing under it, but removing it completely, putting his soaked diaper fully on display. The bright red top he was wearing only covered the very top of his diaper. Everybody could clearly see the entire thing now.
Mel reached out and took his skirt from him so he would have nothing to hide behind. As she did so, she noticed that it looked like he was no longer thinking about his problems from earlier. He now had other things to worry about instead. Good! She was making progress with him. “Now get those shoes off quickly and put your other ones back on. We need to get you home soon. You need another baby bottle to drink!”
Chad heard a few more sounds of astonishment from a few of the people still watching them. He sat down and did his best to change back to his old shoes quickly. He just wanted out of there! And then a miserable thought crept into his brain. The lousy suppository she had put up inside of him earlier hadn’t done anything yet, which meant that it was probably due to explode fairly soon. He was just glad it hadn’t already! He had even more of a reason to hurry now. Could he make it home before it did? He truly hoped so!
Chad had to carry his shoe box and his new clutch purse all the way back through the store to the checkout counters where the previous saleswoman had left their dresses for them. As they walked through what seemed like the entire store, he was very aware of his diaper being on display… it was really all he could think about! The things he held in his hands did nothing to cover or hide it. If he held them down in front of him, as he did most of the time, then the back was still on display – and he doubted that the shoe box really hid much anyway.
There were two checkout counters operating when they got there. Chad saw where their dresses were hung up and followed Mel, joining the short line there. He kept looking around as they waited, looking to see how many people were looking at him. Some! Most of whom kept staring at him totally shocked. In fact, it seemed like the only person who wasn’t staring at him was Mel, who was currently in front of him and was ignoring him.
Finally it was their turn to pay. Chad put his things on the counter along with the box that Mel had. Mel still had his skirt draped over her arm as she told the woman that the dresses hanging up were for them too.
The woman got the dresses and rang up the sale on them, then on the two boxes of shoes and Chad’s clutch purse. Then she noticed the skirt still draped over Mel’s arm. “How about that?” she asked.
“Oh, not this,” Mel told her. “This is hers,” she said, glancing back at Sissy. “She lost it a few minutes ago.”
The saleswoman glanced back at sissy and for the first time noticed what he was wearing under his red top. Partially hidden behind the counter, she hadn’t noticed before. Her mouth dropped open and her eyes went wide in surprise. She stared for a moment before trying to collect herself and finished ringing up the sale.
Mel paid for everything and grabbed the dresses to carry, leaving everything else for Chad. As Chad picked up the bag with the shoes and his purse, he was very much aware that everyone was still looking at him. Why couldn’t Mel have let him carry the dresses? Then he would at least have something to help hide his diaper… well, partially anyway. It was hard to cover it all the way around, but even partially would help in this case. He was so glad to get back into her car again and out of sight!
Chad got lucky – sort of. The suppository didn’t hit him till he had gotten out of her car back at the apartment project and he had started to climb the stairs. With one arm holding up all the new dresses and his other arm carrying the large bag full of the other things they had bought, he had one foot on one step and his other foot on the step above, when he suddenly felt his insides erupting. He couldn’t move. He didn’t dare move. His exposed diaper was soaked to the point where it was almost leaking, and now it was filling to overflowing from the back too. Yuck!
Mel had gone ahead of him up the stairs, leaving him to carry everything up for her. As she reached her door, she noticed that he had stopped on the stairs and wasn’t moving. She looked over the balcony and saw the expression on his face… and a tiny bit of movement in the back of his still diaper. She laughed as she walked closer to see him better as he continued to mess himself uncontrollably right there on the stairs in front of her.
Chad felt a tiny bit of a tickle suddenly creeping down one leg, then another one from his other leg. The added mess in his diaper had forced him to start leaking. By the time he was finished messing himself, he was seriously leaking! And all Mel did was to look down at him from up above and laugh! Once it was over – he hoped – he finally chanced moving again, but very slowly and carefully. He didn’t want any of the mess in his diaper to escape. Very gingerly he made his way up the stairs, all the way to the top where Mel waited for him.
Mel was still laughing a bit, but the moment he got close to her she noticed something awful – the smell! With nothing but the one diaper on, there was nothing to hide the smell at all. “Pew!” she said. “You stink!”
Chad said nothing. What was there to say? Slowly, he began heading toward her apartment.
Mel walked alongside him for a moment till they reached his apartment. “Wait a minute,” she said as she grabbed her keys. She unlocked his door. “Go get cleaned up here,” she said as she grabbed the dresses and other things from him. “Then come back to my place when you’re ready. Wear your uniform. And don’t forget to phone me as you’re putting your next diaper on!”
Chad was actually glad. The best way to get cleaned up now was in the shower. And a fresh diaper was sounding awfully good!

As soon as Chad had changed, Mel took him back to Sandy’s apartment where she had him get his highchair and diaper bag and carry them back to her apartment again. Then, all afternoon, she kept him as busy as possible with laundry and cleaning. She did her best to keep him extra busy, never letting him stop so he wouldn’t have a chance to think too much because she didn’t want him thinking about what she had done with Robin earlier.
Over an over again she ordered him to show her his diaper – not only because she wanted to drill it into him better, but it was another way to keep his mind occupied on other things. Sometimes he was quick enough, but more often he wasn’t. Since he really had no idea of how fast she wanted it done, she decided he needed a goal to strive for. She quickly decided on something that would be very difficult for him, but was also pretty much what she wanted all along. “Here’s how it’s going to work,” she told him. “From now on, when I tell you to show me your diaper, you’ve got exactly two seconds to get that skirt up high. Anything over two seconds is going to earn you an immediate punishment!” To emphasize her point, she grabbed her yardstick. “Show me your diaper!”
As quickly as he could, Chad grabbed his skirt and pulled it up.
“Not fast enough Sissy!” Mel came over and immediately slapped him on the leg with her stick. “I started counting as soon as I finished saying it, and I got to three before you got your skirt up. Next time, do better! Do you understand?”
“Yes Mistress,” Chad replied in his sissy voice. But suddenly Mel was back hitting him with her stick again!
“Curtsey when you say anything!” she ordered.
Fear was now the only thing that Chad was feeling. He curtseyed again as he repeated “Yes Mistress.” His eyes never once leaving the stick in her hand.
“That’s better,” Mel replied as she turned her back on him so he could get back to the laundry.
Chad grabbed his baby bottle and took another long drink – this time, more to calm his nerves than for the liquid it contained. She was getting really serious today! He was getting hit for almost no reason at all – frequently! The result was that he was constantly on edge, worrying about whatever she would demand next.
All afternoon and into the evening Mel kept her stick either nearby or actually in her hand, forcing him to start curtseying every time he opened his mouth. That part at least he seemed to pick up on quickly. And after a little while he was curtseying for no reason at all – which she loved! He had more difficulty though every time he had to raise his skirt to show his diaper. Two seconds wasn’t very much time, but she wanted him to get to where he wouldn’t be able to think about anything but doing it quickly – no matter what the situation. He was getting there, but the going was still slow. But since she wanted to make sure he had other things to occupy his mind than worrying about Robin, maybe that was a good thing.
One thing that he didn’t seem to have any more problem with today, was getting his diaper to leak on time. It was often very close, but she never had to punish him even once for it. Of course, she made sure he never stopped drinking his bottles either – which resulted in her realizing that she was going to have to make a lot more tea tomorrow. Well, that was no problem.
Later that evening, before she sent him home for the night. She removed his chastity device and cleaned it thoroughly. According to her schedule, she usually did that on Sunday night, but since they had dates for then she got it out of the way now. Then, before she pinned him into four huge cloth diapers for the night, she shoved another suppository up inside of him. She had faked it earlier and he had still messed himself uncontrollably later. The question that would be looming soon was… what would happen when she started leaving even more of them out. That situation was fast approaching.
With one more apology from her for what she had done with Robin earlier, she sent him home for the night. If he wanted to cry over it anymore, then he could do it there, before he fell asleep. Tomorrow would be another day. Another day when she would have to keep him busy again.
And tomorrow night… their date! She thought again about Ray and Derek. Both were unusually handsome. But there was something about Ray that turned her stomach a bit. She knew that it was just her reaction to what kind of man he really was. And then there was Derek. Sissy’s date – and friend. Seemingly the perfect man. Sissy didn’t want to be dating - or kissing – his friend. If he had to – which he really had no choice about – he’d rather be out with Ray for that. Ray wasn’t as close a friend to him like Derek was. Ray wouldn’t make him feel like he was violating their friendship. And her? She would rather be with Derek just because… well, just because he seemed so perfect.
They were both going with the wrong guy. The luck of the cards. Oh well. Darn!

Late that night… later than usual… Mel crept into his apartment like she always did. She peeked into his room. As usual, he was sound asleep. It was amazing how soundly the guy slept! Softly, she approached him and looked down on him. He was laying on his back this time. The pacifier in his mouth seemed so out of place somehow, yet she loved seeing it there. He always sucked on it now while he slept. She counted three empty baby bottles on the floor nearby. Just as there should be!
Quietly, she went out to his kitchen and left him his note for tomorrow. On a whim, she opened his refrigerator and grabbed one of the baby bottles full of her tea out of it. It was cool now, but not overly so. She went back to his bedroom. Did she dare try this? Why not?
She had to move the empty bottles out of her way so she could sit down on the floor next to him. Carefully, she reached over and pulled ever so slightly on his pacifier. It was firmly rooted in his mouth. She kept pulling till all of a sudden it popped out. He stirred unhappily and she saw his mouth moving to find it. His arm started moving now too to find the lost pacifier. Quickly she inserted the full baby bottle into his mouth and she actually felt him sucking the nipple in. His arm went back to where it was before and his face looked relaxed again. She almost giggled out loud. He was doing it again… drinking from a baby bottle while he was still asleep. Amazing!
He didn’t seem to drink as quickly in his sleep as he did when he was awake. She had to switch arms holding the bottle for him when she got tired. Last night, he had been laying on his side instead of his back so she could prop it up for him. But tonight was different. And tonight she was kind of getting a real kick out of doing this. She briefly wondered what he thought about it, but then she wasn’t sure he even realized what had happened last night. Would he realize it tomorrow morning when he saw the extra bottle?
When at last the bottle was empty, he still continued to suck on it, but she wasn’t the least surprised by that… the guy did suck on a pacifier all night. She held his pacifier ready in one hand while she pulled the bottle out of his mouth with the other. The moment the bottle was free, she inserted his pacifier again. He continued to sleep soundly. Whew!
She quietly got to her feet and left the empty bottle with the others. She checked to make sure the alarm on his clock was set for the time she wanted it to be and she also checked to make sure the volume control was turned all the way up.
She looked down on him one more time. She had done wrong today, very wrong. But that couldn’t be helped now. Somehow, she would have to fix things. She just didn’t know how yet. He looked so peaceful in his sleep. She envied him that. She didn’t sleep nearly as soundly every night as he did.
“Goodnight baby. Sleep tight.”