The Bet - Chapter 23 (Sunday – week 4 Part 2 of 3)

The Bet
by Karen Singer

Chapter 23 (Sunday – week 4 Part 2 of 3)

Chad glanced at the watch that he had struggled to fasten around his wrist. Damn, he didn’t have much time. And he still hadn’t been out for breakfast yet. Trying to get rid of his new breasts had taken way too much time. He finally decided to forget going out for breakfast, Mel would probably never know anyway.
He grabbed his grocery list that he had already put together and went over it as he drank his third bottle of the morning. He added yet a few more items that he remembered that Mel was running low on. When his bottle was finished, he put it, along with his other empty bottles from last night and this morning into a plastic bag to take with him to Mel’s apartment. He glanced at his watch again. It was almost time – close enough anyway.
With the bag of bottles in one hand, he slung his diaper bag over his shoulder, then slung his purse down into the crook of his arm. Fully loaded, he faced his front door and took another deep breath. It was time to go. Time to be her maid again. Time to face yet more humiliation. Why couldn’t he have just one day that was easy? He couldn’t remember a single day since the bet had started that had been easy for him. Not one! And now he was going out wearing a damn maid’s dress again. This would be his third day in a row without wearing pants. It still surprised him that he was actually doing it. With one more big breath for courage, he opened his door and went out.
He knocked on her door and took half a step back. As soon as the door opened he dropped a curtsey and said, “Good morning, Mistress.”
Mel smiled and let him in. “Good morning, Sissy,” she replied.
Chad dropped his diaper bag and purse on the floor next to the table near her door and handed her his bag of empty bottles. He saw her look into the bag and smile before she took put it in her kitchen for later.
“Do you have your shopping list?” she asked.
“Yes, Mistress,” he replied dropping yet another curtsey. “I’m afraid it’s a long one today. Some of the recipes I chose take a lot of ingredients.”
“That’s fine,” Mel replied only half caring as she quickly checked her hair and makeup in the mirror. She grabbed her purse to go out, then turned directly toward Sissy. She looked him over more carefully than she had before – and smiled. “You’re looking better and better,” she declared as she turned toward the door. “Time to go.”
Chad paused as he watched Mel opening the door and going out. He was dressed as a maid again and would once again be going out shopping as her maid. Would the humiliations never end? No, he knew the answer all to clearly to that question. With Mel, everything would be total humiliation. Taking a quick big breath for courage, he grabbed his purse and diaper bag and followed her down to her car.
The parking lot at the grocery store didn’t seem to be quite as crowded as it had been before, but that did nothing to ease his nervousness. He thought back to two weeks ago, the first time she had made him wear a skirt in public – she had actually called the police to get him out of the car. Now, he was not only wearing a dress, but a maid’s dress at that… and he was getting out of the car and following her inside like it was something he did everyday. Like there was nothing out of the ordinary about it at all. Mentally, he was screaming inside, but on the outside, he did his very best to look calm and confident – praying that people would see him as more of a woman than the sissy that was really inside the maid’s dress he was wearing.
As he pushed the cart around the store, Mel talked mostly about what foods she liked and also about what she liked about the dishes he had already prepared. He was grabbing item after item from the shelves and putting them into the cart while Mel put almost nothing in. Mostly, she grabbed a few snacks for herself but as far as Chad could tell, she wasn’t interested in shopping for anything else. Yet he needed so many things that their cart was filling up.

Mel felt good and relaxed as she walked with Sissy up and down the aisles of the store. It was good to be out with her maid. It made her feel good – important – powerful. She was making a man do her shopping for her, while dressed as her maid. The thrill she felt over it was electrifying. She let him do all the work, after all, he would be doing the cooking and he was the one who knew what would be needed. There were very few little things that she added to the grocery cart, mostly things that just kind of caught her fancy – that is till they got to the aisle where the baby food was. Then she stopped and looked at it all carefully.

Chad stopped and watched as Mel looked over all the baby food. His nervousness about that grew by leaps and bounds. He didn’t want her to buy any baby food, yet he now knew that she would – without a doubt. And he wasn’t the least bit surprised when she started to pick up jar after jar from the shelves and put them into the cart. She also picked up two more boxes of the baby cereal he hated to eat every morning. So much baby food in the cart. Way more than he wanted to see, yet the sight of it, knowing it was all for him, brought instant pain from his chastity device. Damn he needed some relief! It was all he could do to not show too many outward signs that he was in pain.
He watched in horror as she came across a display of baby bibs and started looking carefully though them. She pulled out a large plastic one and held it up, then with a smile, she turned and showed it to him before throwing it into the cart. Ugh! Another bib. At least this one just had pictures of farm animals on it and didn’t actually say sissy. He was so glad that Mel finally moved on.
The checkout line wasn’t bad at all, only one other person in front of them. Chad was all too aware though of the close scrutiny of all the people around him – especially while he was loading the groceries onto the conveyor belt – but there was nothing he could do about any of it. He was – in reality now – her damn maid. Her damn sissy maid. As he stood back and watched the purchases being rung up, that was the one thing that kept going through his mind. He actually was her sissy maid now. There was certainly no denying it. He was dressing the part and totally acting the part now. And he saw no way out – except eventually winning the bet. That thought reminded him of something – would Mel ask him if he needed to wet his diapers? He realized then that he had already been holding back without knowing he was. Total control. That was what was going to win the bet for him – especially since Mel knew nothing about that.
As she was about to pay for everything, Chad saw Mel turning toward him. He knew then that she was going to ask. “Do you need to wet yet?” Mel asked.
Chad desperately searched for an answer that wouldn’t get him in trouble. “No Mistress, I’m already wet,” he replied. It was a total lie. He was completely dry – for now. But Mel had no idea of the real truth. However, as he pushed the groceries out to the car, he allowed himself to thoroughly wet his diapers, reveling completely in how wonderful the sensation felt as he did it. Wet diapers were really so much better than dry ones! He should have wet them sooner – just so he could enjoy it more.

Once they were back at Mel’s apartment, Chad made trip after trip, carrying the groceries up to her apartment. The more he was out in public dressed as her maid, the more he felt like he actually was her maid. A point driven home again and again with each trip up and down the steps while wearing his maid’s dress.
He actually spent a quiet and fairly nice few hours with Mel after that. He put all the groceries up and made them each a salad for lunch – although he had to eat his with his fingers while sitting in his highchair. After which he lightly cleaned her entire apartment again – which didn’t need much cleaning and he washed what few clothes she had that were dirty. As he was doing that though, just as usual for that time of day, he once again felt the dire need to mess himself. Even though he hadn’t had any suppositories shoved up him that day, he knew that there was still enough of their chemical still in him to make it impossible to hold back so he didn’t even try. Besides what would have been the point?
But this time, he wasn’t wearing one of his girdles over top of everything and fairly soon the smell from what he had done was all too evident. He noticed it first, but there was nothing he could do about it. Mel noticed it though a few minutes later. “Sissy, it smells like you’ve got a very messy diaper!”
“Yes, Mistress,” he replied dropping a quick curtsey, then going right back to work on her laundry.
Mel got up from her seat to take a closer look. The closer she got to him though, the more she could smell him. She smiled at him as she approached, “And we didn’t even give you another suppository earlier.”
Chad stopped what he was doing. “Yeah,” he replied, “but there’s still so much of them up inside of me that it doesn’t matter. Until more of it get’s out of my system, I doubt I’ll be able to control it at all.”
Mel smiled again and lightly brushed his face. “Good baby. But then I’m sure a big sissy baby like you doesn’t really want to control it anyway.”
Chad didn’t really know how to answer that. As far as this bet went, yes he did want to control it, but otherwise…
“I’ll change you in a little while,” Mel said as she walked off again. Chad had to endure his wet messy diapers for another half-hour before Mel finally couldn’t stand the smell anymore and changed him. Then she handed him a can of air freshener and made him spray her whole apartment with it.
Chad did what he could around her apartment after that, including as much pre-preparation as he could for dinner. But eventually, he had nothing left that he could do. He approached Mel who had been sitting and reading a book. “Excuse me, Mistress,” he said dropping his usual curtsey.
She looked up, “Yes?”
“I’ve done about everything I can for now. Is there something you need me to do?”
“You’ve done everything?” she asked.
“Yes, Mistress,” he said as he dropped another curtsey without even thinking about it.
Mel smiled. She loved to see him curtsey that way to her. But he had nothing to do? That wasn’t really good, yet she suspected that just might be true. Her apartment wasn’t that big after all. “What time do you need to start dinner?”
“Probably about five,” he replied.
She nodded. “Ok, Sissy. Go stand in your corner then till I tell you to come out.”
Chad’s eyes went wide. In the corner! Why? He searched for any sign that she might not really mean it, but he quickly realized that she had really meant it. He sullenly walked over to his corner and spied the perch that was on the ground there. He turned back to her. “Do I have to…”
“Yes!” she said, already knowing what he was going to ask. “I want you standing on that thing whenever you’re in your corner – from now on!”
Dreading it even more, Chad climbed onto the darn perch. His feet were pushed close together and held at an awkward angle, as if he were wearing really high heels. He half fell into the corner with his arms dangling at his sides. He closed his eyes because there was nothing there to see. Stuck in his corner again! And once again standing on the damn bar. The stupid bar made it almost impossible to move his feet, denying him even that tiny bit of relief.
He stood there, and stood there. Boring! Boring! Boring! When he felt the need to pee, he held it for just a few minutes, but he was too bored. He let it out just for the pure joy of the sensation. Then he went back to standing there – totally bored!
He heard no sound from Mel at all and knew she was engrossed in her book. Why couldn’t he be allowed to read something instead of standing in the corner? But he wasn’t allowed to do anything except what he was doing – which was nothing! His feet ached horribly, more and more as he stood there. His legs ached more and more too. He suddenly wished he had his pacifier. He thought about putting his thumb into his mouth to suck on, but Mel wouldn’t allow him that much movement – besides, the damn long nails on his hands made sucking his thumb almost impossible anyway.
Why was she making him stand there so much? Just because there was no work to do? It was like putting him out of the way when he wasn’t needed – like a damn vacuum cleaner. Is that what she was doing? Putting him away like an appliance that she didn’t need just then. The more he thought about it, the more likely it sounded.
And then his bored mind realized something else – usually, children were made to stand in the corner for a reason – to teach them something. But he certainly wasn’t learning anything – except perhaps what a total sissy he really was. Standing in the corner like a complete child! Certainly not like the man he thought he was. He was a sissy baby, standing in the corner like a little child. Not a man at all. Not a man! A baby! A big sissy baby! He probably deserved to be treated this way. He was such a sissy. And then his chastity device started hurting him once again – damn! He probably deserved that too.

Mel looked up from her book occasionally to watch him. As far as she could tell, he hadn’t moved hardly at all since she had sent him to the corner. She wondered what he thought about as he stood there. He certainly couldn’t do anything else except to think. He had been there for a long time now – much longer than she had ever kept him there before. Yet the perch he was standing on seemed to be working perfectly. She hadn’t seen him move his feet even once – that she noticed. She really had been enjoying the book she was reading. She glanced at her clock. It still wasn’t five yet. She put her book down and went over to him. “Are you enjoying standing in your corner, Sissy?”
Chad was startled and a bit scared as he felt Mel approaching him. Would she release him? He could only hope. He was more surprised at her question. “No, Mistress. I don’t enjoy it at all.”
“Ummm. Too bad. I’ll bet you’re getting very used to it now though, aren’t you?”
Unfortunately, Chad knew the answer to that one. “Yes, Mistress.”
She laughed a bit. “Your perch is helping too. I haven’t seen you move your feet even once.”
His perch? Is that how she thought of the bar he had to stand on? He thought about her question. “I can’t move them,” he replied.
She giggled a bit once again. “Do you like how it keeps you standing there, as if you’re wearing very high heels?” she asked. “I already know you’d love for me to train you that way.”
He thought carefully for a moment before he answered. “My feet really hurt,” he finally replied.
“I’ll bet they do,” she said with yet another giggle. “Maybe I should have had you wear your highest heels today, so that when you finally get off of that thing, your feet will hardly know the difference. I’ll bet you would really like that.”
He thought briefly about what she had said, then shuddered. His feet really did ache horribly. Having to wear high heels after this would only keep them hurting. Yet at the same time, the thought did appeal to him – very much! “I’m not sure,” he finally admitted. “I think my feet hurt too much.”
“Maybe that’s just because you’re not used to it yet. Give it time, Sissy. Give it time.” She laughed again. “Ok, Sissy. You can leave your corner now. Go start dinner.”
Chad let out a huge sigh of relief and very carefully got off his perch and out of the corner. Even though he was wearing one inch heels, stretching his feet even that flat was difficult. His calf muscles ached horribly too. It took him a few moments of stretching before he felt confident enough to go into the kitchen to work.
“Get yourself another bottle while you’re fixing dinner,” Mel ordered. “You probably need it now.”
Chad thought about it and agreed. He really did need the drink!