The Bet - Chapter 44 (Sunday – week 7 Part 5 of 9)

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 5 of 9)

Chad spent the afternoon thoroughly cleaning the apartment, doing laundry, and drinking more bottles than ever before. He was going crazy trying to get his diaper leaking faster. He had to! Mel had decided that she would only give him five swats from her stick for each minute over now, but if it looked like that wasn’t going to be enough, then she had no trouble raising it to ten.
While he was working, Mel was working too, but not on her computer. She had made tea yesterday, but he was going through the bottles so fast now that she had to make more to keep up. Not that she was that worried about the tea because he was also drinking a lot of water too.
As they both stayed busy, Mel kept her stick nearby – always. Whenever she thought he was least expecting it, she would order him to show his diaper, which always resulted in her giving him a quick stinging swat with her stick. And over and over again she pressed him to curtsey constantly. If he didn’t, then that brought another instant stinging swat.
Chad was getting more and more paranoid all afternoon. He kept a constant watch for Mel out of the corner of his eye. Just to avoid getting hit more, he started curtseying every time he saw her turn to him. She was already forcing him to curtsey every time he opened his mouth. And now he was doing it every time a conversation ended. It was very bothersome – to say the least.
He was fortunate to have his next diaper leaking on time. But he was only halfway through his next time limit when the stupid suppository, that he only thought Mel had put up inside of him, decided to go to work. Instead of changing him there, Mel sent him back to his own apartment to shower and make sure he was perfectly shaved all over before coming back again in a clean diaper. She wanted him freshly cleaned and shaved because the time to start getting ready for their date was getting closer.
When Chad came back, still in his maid’s uniform, he began worrying about what Mel intended as far as his diaper leaking later – during their date. Even if he got his current diaper leaking on time, which he was fairly sure he would, then what about the next one? By his estimation, the next one would have to be leaking sometime during the date. Surely she couldn’t expect him to have a leaky diaper then – could she? But then he remembered how obsessed she seemed to be about it lately – obsessed enough that he had been having trouble out in public on several occasions. And not always just a little trouble, at times it had been major trouble! So what was she expecting him to do tonight? He just couldn’t see himself having to change his diaper in front of Derek… or Ray either! If it came to that, he was sure he’d rather receive any punishment she might dish out, just so they wouldn’t know! If they didn’t know already. But that was another problem he had to worry about. Hopefully, Robin hadn’t told anyone yet. Hopefully.
So what did Mel expect for tonight? The thought bothered him so much that he finally approached her – and curtseyed as well as he was able to before he spoke. “Mistress…”
Mel looked up from her laptop. “Are you leaking?”
He curtseyed. “No, Mistress.”
“Show me your diaper!”
As fast as Chad could, he grabbed the skirt of his maid’s dress and pulled it up high. But by the time it was fully up, she was already coming out of her chair with her stick. He got a sharp slap on the side of his bare leg as punishment for being too slow before she sat down again.
“If you’re not leaking, then why are you bothering me?” she asked.
Chad pulled his dress down again and smoothed the skirt slightly before dropping yet another curtsey. “I… I was wondering about later,” he stammered.”
Mel was confused. “Later? We’re going out on a date later. What are you worried about?”
His curtsey was almost automatic. “My diaper leaking.”
“You’re worried you won’t make it?” Mel actually smiled. “Good! I’m glad you’re worried about it. Just make sure you get plenty to drink as often as you can tonight and… hopefully… you’ll be just fine. The restaurant really shouldn’t be much of a problem, but the movie theater… Maybe you should get an extra large drink before the movie starts.” She smiled broader. “In fact, I’m going to insist on it! Maybe Derek will even buy it for you!”
Chad actually shuddered at the thought. He almost spoke without curtseying again, but stopped himself long enough to complete the act just in time. “No, Mistress. That’s not what I meant. What happens when my diaper does leak?”
Mel’s face was still all smiles. “I’m so glad you’re actually planning on it. That makes me very happy! We’ll just have to wait and see what happens then… and deal with it… or not.”
Deal with it… or not? He couldn’t believe it. She was actually planning on him having a leaking diaper – during their date! He couldn’t! He just couldn’t! But… how was he going to prevent it? He was drinking so much already – and had been all day long. His system was so overloaded with fluids that even if he never drank another drop all night, he’d still probably be peeing constantly. And with the amount of time they were probably going to be gone, there was going to be no way to avoid it!” He actually shuddered at the thought as he dropped another curtsey and turned away from her in shock. He couldn’t believe it! He just couldn’t believe it! But what choice was he going to have? And then he realized that he had been set up. She had been pushing him extra hard all day, making him drink far more than ever. No matter what he did, there was no way he could avoid going out tonight and not having his diaper leak – probably over and over again. What were Derek and Ray going to think? What was he going to do? It was going to be… a disaster!
Mel continued to smile as she watched him walking away – obviously in shock. The funny thing was though, that he had asked the wrong question! She almost laughed. She was having so much fun today with him. Obviously, she was in a really wicked mood as far as Sissy was concerned. And she didn’t see any reason at all to stop.
An hour later, Chad looked up as he was folding laundry and saw Mel heading into her bedroom. What surprised him was that she closed the door behind her and he heard the faint sounds of her locking it too. He glanced at the clock and guessed that she was probably going in to get ready for tonight. Was he really going out on a date tonight? With Derek? As a girl? The thought still sent shudders down his spine. And what about his diaper leaking? He had purposely cut back on the amount he was drinking, but he was still peeing an awful lot and his diaper was getting awfully wet – already. Too soon in fact! He figured that it would be better if he was changed just before they left in order to put off leaking as long as possible. But if his diaper leaked too soon now, then what was going to happen?
He finished folding the clothes and looked around. He had a few things that he had just folded that needed to be put away in Mel’s room, but he couldn’t get there. The apartment was already spotless and even the kitchen was back in order again – the new order he had given it. So now what was he supposed to do? He was startled as Mel’s bedroom door suddenly opened and she walked out wearing only a full slip and headed toward the bathroom.
Mel paused on her way to the bathroom and saw Sissy just standing there near the laundry. But he wasn’t drinking anything and he didn’t appear to be working. “Show me your diaper!” she commanded quickly.
Chad raced to get his skirt up on time. But he knew before he started that he had failed. He especially knew it when he saw her hurrying to find her stick. A moment later, he was enduring not just one, but two hard stinging slaps from it. “What are you doing?” Mel asked. “I haven’t seen you drinking a bottle in a while now.”
Chad curtseyed. “I just finished folding the laundry,” he replied.
“And how about your bottle? You’re not leaking yet.”
Again he curtseyed. “I still have plenty of time,” he replied.
“I don’t care! Go get another bottle. What else are you doing?” she asked.
Chad curtseyed. “I just finished here,” he replied.
“Then get your bottle and get up on your perch and stay there till I’m ready for you. And your bottle better be long gone before then!” She glanced at the clock again. “We don’t’ have much time before we have to start getting you ready!” She saw him just stare at her for a moment. “Now go!” she commanded with a half-hearted swing of her stick that again caught him on the side of his leg. “And if you start leaking while you’re on that thing, just stay there and don’t bother me!”
Chad turned and started to hurry away, only to feel her stick hitting him one more time.
“You forgot to curtsey again before you left!” she yelled angrily.
Chad quickly dropped yet another curtsey, then hurried to the kitchen to get another bottle – of water this time. Mel was already in the bathroom by the time he emerged from the kitchen, bottle in hand. He was glad to see her gone! He reluctantly climbed up onto his perch and carefully brought the bottle up to his mouth. With his neck bent back and his body leaning into the corner, he started drinking again. Another bottle! How was he going to keep himself from leaking during the date? It was going to be impossible! He suddenly felt himself peeing again, but it had been such a short time since he had climbed up onto his perch that it held very little interest for him this time.
Having no other stimulation to occupy his mind, his thoughts naturally tuned toward the upcoming date. He was going as the girl this time. He was going out with Derek – his friend! At some point – possibly more than one time before they got back, his diaper was going to start leaking. And worst of all, before the date ended, he was supposed to kiss Derek goodnight – passionately! He couldn’t! He just couldn’t!

Mel left her dress and shoes off, but otherwise she was all ready. She walked out of her bedroom and straight over toward Sissy who was still in the corner on his perch. The empty bottle was still in his hand and down by his side where it belonged. She looked closely at the bottom of his diaper – it looked like it had just started leaking. Perfect!
Without saying a word to him, she left him and found her phone and punched in a number. “Hi Sandy? I just have to run and get him a few things from his apartment. If you want to come over in about fifteen minutes, we should be ready for you then… Great!”
Ignoring Chad completely, she threw a robe on over her slip, grabbed her keys out of her purse, and went out the door. The walk to his apartment was short and she was inside in only a minute. She went straight to his cardboard dresser where she got the few things she wanted. She was back home again a few minutes later. As far as she could see, he hadn’t moved. Actually, this time, she really didn’t care.
“Okay, Sissy. Let’s start getting you ready.”
Chad gratefully climbed off of his perch and stretched his ankles and legs for a moment. Then he went quickly into the kitchen to deposit his now empty baby bottle. He found Mel waiting for him in her bathroom – with another diaper for him. He wasn’t all that happy to see only one diaper in her hand again.
Mel had him remove his maid’s dress before she expertly removed his soggy diaper and did her best to clean him up. Then she added a layer of baby powder and smoothed it all over his front and backside. Then she finally pinned the fresh diaper in place. “An hour and forty-five minutes, Sissy,” she told him.
Chad still couldn’t believe it. What was he going to do? Especially since he realized he was peeing yet again. His dry diapers never stayed that way very long anymore! An hour and forty-five minutes! They would be in the middle of their date then. What would they be doing? Where would they be? He only hoped that they would be inside the movie theatre by then so that when it happened, nobody could see it in the dark. But what about after the movie – when his leaking would be much worse and that much more obvious? It was not a happy subject to dwell on.
“Sit on the toilet there,” Mel said as she pointed to it, “so I can do your hair.”
Chad was a bit surprised by that request, although it was only practical. It’s just that… he hadn’t done anything with a toilet – other than cleaning it – for a long time now. He put the lid down that Mel always kept up, and carefully lowered his already wet diapered bottom down on top of it.
Mel attacked his hair with her brush. It really wasn’t too bad at all, but she grabbed her curling iron and started reworking it anyway. Before she finished, she heard Sandy at the door. She left Sissy right where he was, holding the hot curling iron in place, and went to open the door. “Your timing is perfect,” she told Sandy as she let her inside.
Sandy came inside with a bag full of makeup. “Where is he?” she asked as she looked around.
“In the bathroom – sitting on the toilet.”
Sandy was startled. “He’s what?”
Mel laughed. “Don’t worry. He can’t do anything there. I’m just working on his hair.”
Sandy was a bit relieved. For a minute there she had thought that Mel might have let him out of his diapers! “So do you think he’ll need the smudge proof stuff this time?” she asked.
Mel considered that for a minute, then smiled. “No. In fact, I’d like him to be fussing with his makeup as much as possible tonight. So… lots of lipstick this time. And something that he can reapply often.”
Sandy giggled. “No problem!”
While Mel worked on his hair, Chad had to endure Sandy working on his face. Between the two of them, he didn’t know which way to move his head or where to look – or not look. He soon felt himself peeing yet again – which was really strange because for once he was sitting on the toilet while it happened. Unfortunately, he might as well have been sitting anywhere else, because with his diaper on, there was no place else for the pee to go. At the rate he was peeing now, how far into their date would he be before he started leaking?
Mel finished with his hair and sprayed it lightly with hairspray while Sandy stood back to check to see what still needed to be done. When Mel had finished, Sandy grabbed the lipstick one more time and put another coat on top of the two coats that were already there. She stood back again to eye him critically. Finally, she nodded. “There! I think that should do it!”
Mel was pleased. “Perfect!” she declared.
“Can I look?” Chad asked hesitantly from his seat on the toilet.
“Sure, have a look,” Mel replied.
Chad got up from where he was sitting and turned to look at his face in the mirror. He was actually a bit afraid to at first, but when he got there, he got a pleasant surprise, he looked… great! Well, fairly great anyway. As good a job as Sandy had done, when you looked close, there was no doubt at all that underneath it all he was still a guy. But still… he didn’t think he had ever looked this good before. Or… this sexy either. If you could call him that. Maybe it was just the makeup. With the bright red lipstick she had used, he thought he looked more like a girl heading out to a club somewhere than just to a movie.
Mel picked up the lipstick that Sandy had used on him a moment before. “Take a good look, because now you’ve got to keep it looking just like that, all night. I don’t want to see anything the least bit smudged or out of place – especially your lipstick. I want you checking it often, and refreshing it almost every time!”
Chad’s eyes went wide as he felt a tiny bit of stirring to his sexual excitement. He took the tube of lipstick that Mel was holding out for him. Fortunately, he didn’t have to use it yet.
“Are you ready to put his dress on him?” Sandy asked.
Mel stepped out of the bathroom to check the clock, then turned back again. “No, let’s wait a few minutes. There’s still almost half an hour till they’re supposed to get here.” She looked directly at Chad. “Plenty of time for you to have one more bottle!”
Chad nearly died. He was peeing so much now that he didn’t know what he was going to do during the date. He started out of the bathroom, but was stopped by Mel’s angry voice. “Sissy! You didn’t curtsey again!” She quickly looked around for her stick, but it was nowhere near. Instead, in the heat of the moment, she reached out to slap him, but stopped herself just in time. She didn’t want to mess up the makeup job that Sandy had so artfully done. “Remind me to punish you for it later! Now go get another bottle and get back up on your perch!” This time, Chad curtseyed before he hurried out – while Sandy giggled at him.
While Chad stood up on his perch in the corner, “reluctantly” drinking yet another bottle of water, Mel finally put her dress and shoes on to finish getting ready. Sandy appropriately ooed and ahd over it. But as soon as Mel was ready, she put her robe back on over her dress again to keep it clean. “Sissy…” she called. “Are you done with that bottle yet?”
“Almost, Mistress,” Chad called back from his corner.
“Well, we can’t wait any longer. You can finish it later. Get yourself over here right now.”
Chad gratefully pulled himself out of the corner and set his bottle down next to his perch. He hurried over to Mel and curtseyed. Mel pulled him into the bathroom again and had him lay down on the floor. While Chad was laying down, Mel got out three more disposable diapers and started preparing them while Sandy looked on. Chad was elated to see them. She wasn’t going to send him out in only one diaper after all! A few minutes later, Chad was once again happily well protected with three full layers of disposable diapers on him. Then Mel handed him one of the all-in-one girdles he wore to work every day, followed by a pair of pantyhose. A few minutes later, Chad was pulling his new blue dress on and fastening his new shoes on his feet.
Mel grabbed the perfume she had brought back from his apartment and sprayed a tiny dose on his neck and wrists. “There,” she teased, “Now Derek will find you irresistible!”
Sandy and Mel together loaded his new clutch purse for him with everything he should need, but instead of putting the tube of lipstick in it, she handed it to Sissy. “Your lips are all smeared from the bottle you just drank,” she told him. “Fix it!”
Chad curtseyed before he took the lipstick and hurried to the bathroom where he touched up his lips – which seemed to be already coated with more lipstick than he ever used.
Mel followed him back into the bathroom to watch. “Don’t forget,” she reminded him as he applied a fresh coat, “I want to see you checking your face and touching up your makeup all night!”
Chad half curtseyed again as he worked. “Yes, Mistress.”
Mel stared at his reflection in the mirror. “I guess tonight is going to be a bit different for you.”
Chad bent his knees a bit as he worked on his lips. “In what way?”
“Tonight… Tonight I want you to try to be as much of a woman as you can. Use your girly voice, don’t call me Mistress in front of your friends. Try to enjoy yourself. Forget you were ever a guy. You’re not anymore. Be the girl!”
Chad’s eyes went wide as he looked back at her in the mirror. He turned toward her and curtseyed. “I don’t know if I can,” he said nervously.
“Try,” Mel replied. She smiled at him. “You look very nice tonight.”
Chad curtseyed more nicely this time. “Thank you, Mistress.”
Mel smiled. “I really do love seeing you curtsy like that.” A sudden thought struck her. “In fact… I’ll bet Derek would like to see it too.”
Chad was horrified. Curtsey for Derek?
But Mel wasn’t done yet. “At least once tonight, I think you should curtsey nicely for Derek. And make sure I see you do it!”
The horror over that command was still registering when someone knocked on the door!
Mel smiled. “I’ll bet that’s the guys now!”