The Bet - Chapter 15 (Saturday – week 2 Part 3)

The Bet
by Karen Singer

Chapter 15 (Saturday – week 2 Part 3)

Chad stood in front of his door and took a deep breath. He was ready to go, physically if not mentally. He was worried about what Mel might have in store for him today. Obviously she had something in mind because of the way she had worded her note to him last night.
After wearing only one diaper under his clothes all morning, he was surprised to discover that wearing two felt more normal. He certainly worried a lot less about leaking with the two diapers on. He had chosen a pair of heels that he hadn’t worn in a while. Most of his shoes had very high heels and these were actually the lesser of several evils. While the heel on them was about three inches high, they were actually fairly comfortable. And if Mel had him running around her apartment for a long time doing who knew what, then that comfort would be very welcome indeed.
With his pink diaper bag slung over his right shoulder, his purse hung on his left arm, his dress and apron neatly pressed and on a hanger also hung over his left arm, and his low heeled shoes in his right hand, he took one more deep breath to steady himself, and awkwardly opened his door and stepped out to go to Mel’s apartment.

Chad was two minutes late by her clock when she finally heard him knocking on her door. She opened it almost immediately and stood there waiting. She didn’t have to wait very long.
“Hello, Mistress,” Chad said as he tried to curtsey while his arms were so full.
She smiled and replied. “Hello, Sissy.” Then she stepped back and let him into her apartment. He walked in and she closed the door. He was standing there, waiting. She walked around him, looking at him. “Are you wearing two fresh diapers?” she asked.
Chad was surprised by her question. “Of course.”
“Where’s your pacifier?”
Chad grimaced. “I forgot it again.”
“I’ll punish you for that later!” She continued to look him over. “You still need a lot of work on your makeup,” she noted as she looked closely at his face. He said nothing, but just stood there as she continued to look at him. She noticed the gap between the bottom of his pants and the top of his shoes. She was glad to see it. It looked like he was wearing about three inch heels today. But then most of his heels were at least that high. His padded breasts didn’t stick out quite as far as she would like and they weren’t totally even in size, but they were close enough that she didn’t care. She looked at the things he was carrying, the dress and apron were on a hanger and looked well pressed, the shoes in his hand gleamed perfectly. “Go hang your dress in my bedroom and leave the shoes there too. Bring everything else out with you again.”
Chad still wasn’t quite sure what was going on. Why was she bothering to look him over so closely? But he did as he was told. He was glad to stop carrying them.
“You’re late!” she said as soon as he came back out again.
He was clearly surprised. “I am? I’m sorry Mistress. I didn’t know.”
“What does your watch say?” she asked with a hint of annoyance in her voice.
He looked at it. “It’s three minutes after now.”
She looked up at her clock. “My clock says five minutes after!”
Chad couldn’t believe that she would be so picky over two minutes. He searched for words to apologize but couldn’t find any. But she didn’t seem to be looking for an apology. Instead he watched as she went to her purse and pulled her cell phone out.
“I always keep my clocks set to the same time as my cell phone,” she said as she glanced from her phone to her clock. “They match. What time does your cell phone have?”
Chad had a feeling he was about to be in big trouble. He pulled his cell phone out of his purse and looked at it. There was no time available for him to read since the thing was broken. He held it up to show her. “It’s not showing a time anymore,” he replied. “I accidently dropped it this morning and broke it.”
“You what?” she said as she grabbed it from him. “How could you be so careless?” She opened the top, or tried to. The entire flip front came off in her hands. “You’re going to have to get another one first thing this afternoon. I can’t have you without one. I have to know I can reach you at anytime. You should have gotten a new one earlier on your own time!”
“I was too busy,” he replied.
“Doing what? The only thing I asked you to get was more diapers!”
Chad sighed. It wasn’t that easy today. I had to go to several stores to find enough. Then later I had to get an iron and ironing board and that took a long time too.
Mel grinned to herself as she turned her back to grab her purse. She could just imagine how it all went. “Good,” she replied, “you can tell me all about it while we’re driving.” Then she opened the door and held it wide for him to go through first.
Chad suddenly realized that he was going out shopping again. He only hoped that it would be to just buy him a new cell phone and that would be all. But he had a bad feeling that they would be making other stops too.
Mel drove them first to the store where Chad had gotten his cell phone before. As they were walking from the car to the store, Chad realized that he was not only scared again, but also getting that mental sexual arousal again. Earlier in the day when he had been shopping by himself, he had only felt nervous and scared over the way he was dressed in public. But now, with Mel, it was different. Yes he was scared – very! But with Mel along, there was also a feeling of sexual excitement about it too. He was thrilled to be feeling it. He was even more thrilled that his chastity device wasn’t giving him any problems at all. Scared and reveling in his excited glow, he held the door of the store open for Mel to enter ahead of him.
The store was packed with people. Way too many people. Not only for his comfort, but for anyone’s comfort. Chad had to take a number and wait his turn. While they waited, Mel left him walked around to look at the many displays of phones that were available. When she came back a little while later she said, “I want you to get a pink one!”
“Pink?” She had caught him off guard again. He had just gotten his current phone during the break up with his wife – make that ex-wife. He was planning on getting exactly what he already had. “Why? I was planning on getting the same thing I already had.”
Mel raised her eyebrow at him. “Are you questioning what I’m telling you to do?”
Chad backed off quickly. “No, Mistress.”
“Curtsey when you say that!”
Chad was horribly embarrassed, but he dropped a quick curtsey and said, “No, Mistress,” one more time. He suddenly noticed a lot more people staring even closer at him than they were before.
Mel felt the thrill of power over him. She too was aware of all the people staring, but she didn’t care. In fact, she loved it. “You’re a sissy!” she said in no uncertain terms and not lowering her voice at all. “Pink is a better color for a sissy. Don’t you think?”
Chad was burning with embarrassment now. “Yes, Mistress,” he replied as he dropped yet another curtsey. Somewhere in the crowd, someone laughed a bit. He felt so small. Mel in front of him looked so pleased. He also felt even more of a sexual thrill over it. Anymore, and he would be feeling the bite of his chastity device again. He was suddenly a lot more worried about that.
When they finally called his number, Mel told the salesman what phone she wanted Chad to buy. The entire exchange took a long time since he had to find the right phone then set it up. Chad was grateful that the salesman had to stare at his computer more than at him. But a little while later, Chad walked out with a pink cell phone in his purse, while most of the people in the store were still watching him all too closely. He just knew that there was a big hole in the ground somewhere around him that he could fall into and never be seen again.

He was hoping that they would go home after that, but Mel was heading in the opposite direction. She stopped instead at the same store where she had taken him before to buy the women’s pants. He felt the panic in him rising once again.
When they got inside, Mel started heading toward where they had gotten his slacks before, but her attention was caught by the bright jewelry counter near the front. She started looking over all the pretty things carefully while Chad stood back and watched her.
“May I help you?” the saleswoman asked Mel as she was looking at everything. Chad saw the saleswoman keeping a very careful eye on him, more so than on Mel.
“Oh… just looking today,” Mel replied without ever looking up from the display. But immediately something in the case caught her eye. “Oh, I really like that!” she said, pointing to something in the case.
The saleswoman was quick to pull out the tray of jewelry that Mel had been looking at so Mel could see it closer. From behind her, Chad could see that Mel was looking at some necklaces.
Mel picked one up in her fingers to look at it closer. Then she picked up another one and looked at that. Chad could see now that it was a simple gold heart shaped piece with a small light green stone offset in it. “I just love this one with the green stone,” Mel said as she pulled one of them away from the tray. She held it up to her neck and looked in the nearby mirror, admiring it.
“It looks lovely on you,” the saleswoman said. “And green is a good color for you.”
“Yes it is,” Mel replied without thinking. Then she turned and looked straight at the saleswoman. “But pink is a better color for him.”
Chad felt his face suddenly turn very red as the saleswoman stared even harder at him.
“I’ll take both of them,” Mel said with an almost evil look in her eye. “The green one for me and the pink one for Sissy.”
Chad wanted to look around for another hole to fall into as the saleswoman stared at him one more time, this time, she looked far more amused than before. As she pulled the two necklaces out and started to put them into boxes, Mel asked her. “You wouldn’t happen to have any rings that match the pink one do you?”
The saleswoman was surprised, but quickly answered. “Yes, we do. Right over here.” And when Mel told her that she wanted the ring for Sissy, she no longer looked surprised at all.
Chad was horrified to find himself trying to stick rings with bright pink stones onto the ring finger of his right hand. One, with an all too big stone almost fit, but fortunately not quite enough to go over his knuckle. He was really glad. But his glee didn’t last long because the saleswoman told them that the jeweler was in the store that day and she could see if he would resize it before they left. Mel jumped at the opportunity and Chad watched as the saleswoman carried the ring to the back of the store. Mel looked at him with that evil grin again. Chad just felt screwed.
While they waited, Mel continued to look at all the jewelry. But then something else caught her eye. “Sissy. Come here. Look at this.”
Chad dutifully went to see what she was looking at. Watches!
“I want you to buy this one,” she told him as she pointed to one of them. “That way we’ll both know that your watch works well too!”
Chad looked at the one she was pointing at. It was a mix of both gold and silver and appeared to have some tiny crystals around the tiny rectangular face and on the band. The watch looked more like a bracelet than a watch. “But I don’t need a new watch,” he complained.
“I don’t care,” Mel replied, leaving him no doubt about it.
But Chad still wasn’t happy. “But it doesn’t have the date or do anything else. It doesn’t even look like it lights up!”
“It’s a watch, not a Swiss army knife! And you’re getting it!”
Chad looked at the price. At least it wasn’t expensive. In his irritation he suddenly felt the urge to pee and caught himself starting to release it before he could hold back. Fortunately, only little had escaped.
The saleswoman finally returned with the ring. “He was able to make it a little bigger right away,” she said proudly as she displayed the ring. Chad held out his hand for her and she slipped the ring onto his finger and just over his knuckle. Chad actually felt both disappointed that the ring fit this time and another wave of sexual arousal because it did fit.
“Oh, it’s perfect,” Mel gushed as she grabbed his hand to look closer. “Here, let’s put the necklace on with it.” She grabbed the heart-shaped necklace with the pink stone and pulled it around his neck and fastened it behind him.
“Very pretty,” the saleswoman said as soon as she had done it.
Mel picked up the other necklace and fastened it around her own neck. “I just love them,” she said as she once again admired herself in the small mirror. Chad didn’t look at himself in the mirror, he was embarrassed enough. As Mel reached for her purse, she said, “I’ll pay for these things now, but he’ll be buying one of the watches you have over there too.” The saleswoman looked surprised again, but also very happy. Chad had no doubt that they were making her day with all the sales. As to his day? That was another question.
After he had paid for his new watch, and it was prominently decorating his wrist, Mel took his old watch and put it into his purse. “I’ll just hold this for you for a while,” she said as she did it. Chad had the sudden feeling that he might never see his old watch again. He already missed it. His new watch was not only way too feminine, but the dial was so small he could hardly read it!
As he had expected, Mel led him back to the same section where they had found the slacks for him last time. Unfortunately, the same woman who had helped them in the dressing room the last time was there and immediately recognized them. “Welcome back,” she said all too merrily as she approached. “Can I help you again?”
Mel seemed delighted to see her, even if Chad wasn’t. “He needs another pair of slacks,” Mel told her.
“Of course,” the woman replied. Then she looked him over carefully. “I see you’ve made a few changes,” she said. “I love his necklace.”
“We just bought that a few minutes ago up front,” Mel replied.
The woman smiled as she looked at Mel. Then she noticed Mel’s necklace. “And I love your necklace too,” she said. “And they almost match!” Mel seemed pleased at the compliment to her necklace. A sentiment that Chad didn’t feel at all. “So, another pair of pants?” she asked as she looked back at Chad.
“Yes, please. I think this time we need a pair that’s a bit longer to cover the heel a bit more.”
“Of course. That will be easier. Finding ones that were short enough last time was a problem.” That was news to Chad. “Do you want me to bring you some to the changing room again?” “That would be great,” Mel replied. “You were such a big help last time.” Chad wasn’t sure, but he got the impression that Mel and the saleswoman were exchanging some evil smiles together.
A few minutes later, Chad was standing in the dressing room with his shoes and pants off, waiting for someone to bring him something to try on. The curtain was abruptly pulled aside and both the saleswoman and Mel were there holding a few pairs of slacks. Chad realized that his diapers were all too visible under the pantyhose he was wearing. “Try these on first,” Mel said as she handed him a pair. Chad took them from her, but he wasn’t looking at her or the pants she held out. His eyes were watching the amused look on the saleswoman’s face as she stared at his diapers. He turned around with the pants in his hand and was glad to hear Mel sliding the curtain closed again.
He pulled the pants on. They fit fine in the waist, but the length was obviously too long. He walked out like that to show them. “Put your shoes on,” Mel said as soon as she saw him. We can’t tell if the length is right if you don’t.” Chad immediately went back in and slowly strapped his shoes on. He wasn’t exactly happy about it though. This time, the pants didn’t drag on the floor, but it was close.
Once again the saleswoman checked the fit. “The length is good, I think,” she said to Mel. She ran her hand over his diapered backside. “I just wish we didn’t have to keep them so loose fitting in front. I have a lot more styles I could bring you if they could be tighter in the hips.”
“I don’t want his diapers to be that obvious… yet,” Mel replied. Chad was suddenly very grateful. “Maybe later, but not yet.” That part, Chad wasn’t happy to hear.
Chad tried on three more pairs of slacks, each pair seemed to fit him just fine. But then Mel handed him a brightly colored skirt to try on. He looked at her with wide eyes. She just stared back at him for a moment then closed the curtain. That skirt was followed by more skirts and several dresses. Then he found himself trying on a variety of tops. He was getting really tired of trying on so many clothes. And all the while Mel and the saleswoman were talking about him and the clothes and touching him and pulling on the clothes to check the fit of everything. It was really getting tiresome!
When they were finally finished, Mel had selected only one pair of the slacks, but she had also selected two skirts and four of the tops. Chad wasn’t really happy about any of it, and by that time, he just wanted to get out of there. But as Mel started to drape the things she had chosen for him to buy over his arm to carry, he again felt the urge to pee. This time he caught himself first. But he was only able to hold it for a few seconds before the urge was too strong for him to hold anymore and he had to let it out. Unfortunately, that was the exact moment when Mel asked, all too loudly, in front of the saleswoman. “Do you need to pee yet?”
Chad could feel himself blushing under his makeup. “No Mistress, I just finished.”
“You just finished what?” Mel asked with a gleam in her eye.
“Chad tried to drop a small curtsey. “I just finished wetting my diapers, Mistress,” he said. The saleswoman went into a fit of laughter.
When they left the store, Chad was praying that they could go home now, but once again Mel was heading in the opposite direction. What now? Chad didn’t have to wait long to find out as Mel pulled into the parking lot in front of the book store. Books?
Once inside, Mel led them slowly toward the back of the store as she carefully checked the contents of each aisle. Chad was just glad that there weren’t many people in the store, and the ones he did see were more engrossed in looking at the books then in looking at him… most of them anyway.
“Here we are!” Mel finally exclaimed as she turned down one of the aisles. Chad followed her and was surprised when she stopped in front of the cookbook section. He realized he shouldn’t have been surprised at all. “I never expected you to be such a good cook,” Mel stated as she started browsing through the titles. “Too good in fact. If I keep eating like I want to with your cooking I’m going to be as big as a blimp in no time!”
Chad wasn’t sure if she was complimenting him or making a joke. “So I want to find you a book on low-calorie cooking.” That kind of made sense to him. He knew how he liked to prepare things for his own taste, but even his wife – make that ex-wife, had complained how fattening some of his creations could be. He just wasn’t all that interested in the diet meals himself. Mel pulled out a book and started browsing through it, then she turned toward him. “You’re the cook, maybe you should be looking too!”
Chad got the hint and started pulling down books. He wasn’t really a cook… well, maybe Mel saw him that way now, he just enjoyed dabbling a bit. Most of the books he glanced through looked good – at least the pictures did, but the more he read the recipes, the less interested he was. He set aside one or two to look through again. The more he looked, the more interested he found himself becoming. Diet cooking? Now that could be a real interesting challenge. The only problem was that all the things he liked the most weren’t exactly diet.
Between Mel and himself, they finally settled on one good sized cookbook which Mel was more than happy to pay for. As they walked out to the car, Mel told him, “I want you to pick out three or four meals in this book to prepare next week. Tomorrow when we go grocery shopping we’ll get everything you need. So make a list.
Grocery shopping? Chad had horrible flashbacks of his trip to the grocery store last week!
He was so grateful when Mel finally pointed the car for home again. On the way, she pulled into another fast-food restaurant and ordered them both dinner to take home with them. Chad was grateful. He was more than ready to get his all too humiliating image back behind closed doors again.