Holiday Jeers

Hi all!

First of all, thank you to everyone who requested to read my new Baby Bobby story and sent me their opinions. I value those and hope that they will help me to become a better writer.

Now!

Christmas is over and the New Year approaches. I hope everyone has been having a really great holiday season so far. Let me tell you a bit about how mine has gone up to this point.

We got together on Christmas Eve at the home of one of my step-sons. The entire family and all the kids were there for about an hour and a half. This year, for the first time, my wife and I had declared no gift giving to anyone except the kids (the young ones) and let me tell you, I was really happy about that. Yes, I do love to get gifts, but I was far happier this year (and actually more comfortable too) with not getting anything. I loved watching the kids opening their gifts while I wasn’t distracted with a bunch of stuff that I had to worry about. Plus, there isn’t anything they can give me that I really need. It went great! Everyone had a real good time for the short while we were all together.

Christmas day, my wife and I spent alone at home. We watched a bunch of TV and played some computer games together. Mostly it was a very relaxing day.

But on the day after Christmas, the sky fell down!

Remember that step-son whose house we were at on Christmas Eve? He went to work the day after Christmas. In the evening, as he was coming home, he phoned his wife and suggested that she and his daughter all meet out at a restaurant for dinner – which they did. After that, they went home where he laid down for a short while to take a much needed nap (he’s been working 12 hour shifts). When he got up a short while later, his wife threw him out of the house.

There was no warning, no hints… Nothing! As to a reason, she started making up ridiculous stuff that obviously wasn’t true, such as the fact that he doesn’t ever spend any time with her family. Her mother and father live less than a mile away and he and his wife’s father are very best friends and do everything together. He even helps pay his in-laws bills. As of yesterday, his wife still hadn’t given anyone an acceptable answer except that she’s not happy. Nobody knows what to make of it.

But in the mean time, everybody is shocked and mentally wiped out. He’s now living here with us and driving an extra forty-five minutes to get to work (about a two hour trip for him now).

And here’s an added kicker… His first wife left him the day after Christmas too. He’s a really good guy. He takes excellent care of his family and always has. He really doesn’t deserve this.

Whoever said that life is fair? We all know that it’s not. This is another prime example.

Well, sorry for ranting. I really do hope you all have a great – and safe – new year.

Karen

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.

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

The Bet
by Karen Singer

Chapter 15 (Saturday – week 2 Part 2)

When he pulled into the parking lot of the next store, he sat and thought for a minute. He didn’t need to carry his cell phone anymore, the darn thing was broken. But he still had to carry his wallet and his keys. He would also have to carry three more of the big bags of diapers. The first drug store hadn’t had any shopping carts. This one didn’t either – at least he didn’t remember seeing any from his previous visits. Carrying the three big bags of diapers at the same time was going to be difficult enough. He didn’t want to make matters worse by also carrying his wallet and keys separately. Bowing to the inevitable, he threw his wallet and keys back into his purse and picked it up as he left his car. Cursing all women for not having the sense to have decent pockets in all their clothes, he went into the store in search of more diapers.
He felt like such a fool carrying his purse around inside the store. He could only imagine what the other customers must all be thinking. He was wearing women’s slacks… but the top of them were covered by the long tails of his shirt which made him feel better. He was wearing women’s shoes… no buts there, nothing to make him feel more confident at all – except the fact that at least they weren’t high heels. His fingernails were an all too noticeably pink, which made him feel more self-conscious than ever. No, he didn’t want to think about what everybody else was thinking about him. None of it would be good. Even with the tails of his shirt covering the top of his slacks, everything about him still said “sissy.”
As quickly as he could, he found the adult diaper aisle and the diapers he needed. The store only had three bags left – was there a run on them or something? He put his purse over his arm and managed to precariously juggle all three huge packages of diapers in his arms. Why didn’t the store have shopping carts? He knew the answer… because people didn’t usually buy so many large packages in that store at the same time.
When he got to the checkout counter, he had to wait behind two other people. Something he wasn’t at all happy about. He prayed that the big bags would cover up and keep people from noticing his fingernails – and possibly his purse. But the longer he had to wait, the more he worried. What would people think about him buying three bags of diapers like he was, especially with his pink nails and carrying a purse?
And then he heard a slight snigger. He turned around slightly and saw a woman was now in line behind him. She had noticed something, but he wasn’t sure what. What he was sure about though, was that she was doing her best not to laugh at him. He wanted to say something that might explain it all, but there was no good explanation. His embarrassment and discomfort grew as he waited in a line that didn’t seem to be moving at all.
It took forever for the two customers ahead of him to pay for their things and leave. While he waited, he vowed that he would do everything he could to get out of there as fast as he could. As soon as his turn came, he set the three packages down on the counter and grabbed his purse. The woman behind him sniggered some more, he paused only slightly before he quickly dug out his wallet.
“Did you find everything you need?” the clerk asked him as he was pulling his wallet out. He looked up at her, she was smiling a little too broadly at him. He had no doubt that she was inwardly laughing at him.
“Yes, thank you,” he replied as he opened his wallet, willing her to hurry up. But she hadn’t even started to ring up his purchases yet.
“You know, we’re having a special today on everything in the store if you have a coupon. Fifteen percent off. Do you have a coupon?”
Chad was quickly convinced that the girl was trying to purposely slow things down so she could laugh at him longer. Gritting his teeth, he replied, “No, I don’t have a coupon.”
“I have some extra advertising papers here,” she said as she picked up a few newspapers from the counter, “would you like me to see if I can find one for you?”
Chad wanted to scream. “No thank you.”
Almost reluctantly, the girl began scanning his packages of diapers, one at a time. She hit a key on her register and told him the price. He handed her his credit card. She processed his card and handed it back to him while she waited for the receipt to print. She finally handed it to him along with a pen. As he was signing the receipt she said. “Pretty nails.” He said nothing because what he wanted to say would not have been very nice at all.
“Do you want bags for those?” the girl asked after she had gotten the receipt back.
Chad again gritted his teeth. “Yes please.” The bags would make carrying them much easier. Plus, it would help to hide what it was that he was buying. Again he had to wait while she first hunted around to find large bags, which she eventually found right where she had been standing to begin with. Then all too slowly, she put the packages of diapers into the bags.
“Have a nice day,” she said as she finally finished. Chad said nothing as he quickly grabbed the bags and left. He heard undisguised laughter behind him. Ugh!
If he hadn’t been absolutely sure that Mel would punish him badly if he didn’t iron his maid’s dress, he would have gone straight home and avoided any more embarrassment. But thinking about the ways she had punished him before, forced him onward. The closest store that he figured would have an iron and ironing board was Target, and he headed straight there. It was horribly crowded and he was very tempted to leave, but the morning was wearing on and he figured that on a Saturday, things would only get worse anywhere he went. Throwing caution to the wind, he grabbed his purse and headed inside, feeling more foolish than ever.
Target had lots of shopping carts and he immediately grabbed one. He put his purse in the child’s seat of the basket and pushed it out into the main part of the store. With his purse in the basket, he thought he’d feel a little better about it, but it almost felt like he was showing the darn thing off instead. He moved it down to the bottom of the cart so that it wouldn’t be so visible. Now all he had to worry about was his shoes and his all-too pink fingernails. He wrapped both his hands around the handle of his cart in such a way that would make his nails less visible – he hoped.
The store was packed with shoppers. Worse, he didn’t really know where to look for an iron in the store, so he was forced to walk up and down most of the aisles looking for them till he finally found them. He didn’t want to spend very long there, so he quickly picked one out. Then he looked further down the aisle for an ironing board to go with it. He grabbed one that came with a pad and threw it quickly into his cart on top of his purse.
He was half-way back to the checkout counters when he remembered that he needed shoe polish too. He quickly turned his cart toward the back of the store in search of the shoe department. He realized that he was having to traverse all too much of the store in search of a few simple items. Why couldn’t they have all been in the very front?
He easily found the shoes, but where was the polish? Not anywhere that he could see. But he figured that the store had to have some. There were people looking at shoes in every one of the shoe aisles so he had to leave his cart at the ends as he walked into each one to quickly search for the polish. He finally spotted a store worker stocking shelves in the very last aisle. He didn’t want to do it, but he decided to ask. “Excuse me,” he said to the woman.
“Yes?” she asked as she looked him in the face. He realized that she wasn’t looking anywhere else. Good!
“Do you have any shoe polish?” he asked.
“Sure,” she replied as she bent down to put the box she was holding on the floor. But then she noticed his shoes. She seemed to stare at them for a moment. Then as her gaze came up again, she stopped at his hands. Chad wanted to scream. “Very pretty,” she said as she kept looking at his nails. He wanted to hide them behind his back, but he forced himself to keep them at his sides.
“The shoe polish?” he asked again.
“Oh, it’s back this way. It’s kind of hard to find because it’s on the back wall.” He already knew it was hard to find. She led the way toward the back wall and pointed to it.
“Thank you,” he said politely, but with an ounce of irritation.
But she didn’t leave right away. “Oh, by the way,” she said, “there’s a sale on women’s dress shoes today.” She was staring at the shoes he was wearing.
Chad wanted to scream. He didn’t want to buy women’s shoes. All he wanted was some shoe polish. “No thank you,” he replied politely but with even more irritation.
“I just thought you’d like to know,” the woman said. And still she didn’t leave.
“Thank you,” Chad replied and quickly searched for what he needed. He picked up a can of black shoe polish and then as an afterthought, grabbed a shoe-shine kit that would have rags and brushes in it. The woman followed him back the way he had come, all the way to his cart.
“Anything else you need?” she asked as he put the items in his cart. Chad noticed she seemed to be looking all too closely at his pants.
“No thanks,” Chad replied. He quickly pushed his cart away from there. The woman was nice, but all too interested in him.
The checkout line was long and slow. Once again, he felt all too close to way too many people. There was no way to hide his hands which seemed to call most of the attention to him. The only good thing, he realized, was that Mel wasn’t there to humiliate him further by asking if he had wet his diapers yet. But that thought didn’t help a whole lot. Especially when he suddenly realized that he needed to pee really badly while he was standing there. At least this time, none escaped before he caught it. But once again, the urge to pee was building all too fast – and the line he was in was moving all too slowly. Realizing that he had no other choice, he allowed himself to wet his diapers while he was standing there. At least he was so used to doing that now that he could do it without anyone else realizing that he was doing it. He just hoped that his now thicker diapers wouldn’t show under his pants. Since he wasn’t wearing a girdle to hold it all in, that was a much bigger possibility.
When it was finally his turn at the checkout counter, he put everything but the ironing board on the conveyer belt. The girl ringing up the sale took care of those things first, then she grabbed a hand held scanner and came around to scan the ironing board. But she noticed his purse in the bottom of the basket under the board. She moved the board out of the way and started to grab his purse to look for a price.
“That’s mine,” he said quickly.
She looked up at him very surprised and quickly noticed his fingernails. She looked back down at the purse in his cart then back at him. “Sorry,” she said as she walked back around to the register. As he pulled his purse out of his cart, he heard a few chuckles from the people nearby. He hated his life once again. As he signed the credit card receipt, he felt all too exposed and humiliated by his pink nails and the purse slung over his arm. But what choice did he have?
He was glad he had no other stops to make as he drove straight home as quickly as he could. When he got home, he had to make all too many trips to carry everything from his car up to his apartment, all the while hoping that Cassie and Sandy wouldn’t come out to tease him. He was very glad when they didn’t.
As he closed his door after the last load, he dropped everything on the floor along with everything else he had just carried up, and looked at his watch. He was amazed to see that it was already lunch time. Where had the time gone? The trips to the store had taken him all morning! Worse, after looking at his watch, he realized that he was hungry again! He was frustrated. If he had known it was so late, he would have stopped on the way home earlier. Feeling like he had no other choice, he once again headed back down to his car.

Mel was bored. Her TV set was on, but she wasn’t really watching it. All she could think about was Chad. She had done nothing all morning because she could never decide what she wanted to do. What she really wanted was to have Chad under her thumb again so she could feel the power from it. That was all she could think about all morning. Chad, Chad, Chad! She knew it wasn’t right that she should feel that way, but she couldn’t help it. She glanced at her clock. Lunch time. The morning had dragged by and still too many hours till he would show up at her door.
She got up from her chair and put a diet TV dinner in the microwave for lunch. At least it gave her something to do.

As Chad walked back up the stairs with his lunch, he dwelled on his love for fast-food restaurants. He decided that the best thing about them was that he didn’t have to get out of the car and expose himself to anybody. Whoever was working the window and handed him his food could only see a little bit of him, and then he would be gone and he wouldn’t have to think about it again.
He sipped at his drink as he walked up the stairs. He suddenly felt the need to pee again and let it out before he remembered to stop himself. He mentally berated himself slightly when he realized it. He also worried that the single diaper he was wearing might leak now, but he was fairly sure it could hold it all with no problems. He’d change again as soon as he finished eating.
Once inside, he sat in the only chair he had and ate while he stared at the pile of things he had dropped on the floor earlier. He looked at the pile because he had nothing else to look at, not even an interesting picture on the wall to enjoy. It was so depressing. He decided that if he got the chance, he’d ask Mel if he could at least buy himself a picture for his walls. Anything was better than looking at nothing – or the only thing that was hanging from his walls – the contract for the bet.
Unfortunately, looking at the pile reminded him that he still had things to do before he went to see Mel later, and those things would probably take a little while to finish.

Mel glanced at her clock one more time. She had been reading a romance novel to help fill the time. But now it was nearly time for Chad to arrive. Close enough anyway. She put her book away and found herself staring at her door, waiting for him. How ridiculous. She really needed a life. She had friends, but she rarely ever called them, and as result, they rarely called her. She wasn’t dating now, and hadn’t since she ended her last engagement. She had no life right now, which was sad. She realized that Chad had suddenly replaced everything else in her life with this bet. And the funny thing was, it was thrilling her like nothing else had ever done. Why? She didn’t know. But she was smart enough to just accept it. Maybe when the bet was finished and she had won she would start dating again, but not right now. Right now she was more interested in Chad… and the power she could feel from controlling him… not to mention his tantalizing little tongue.
Now…. where was he?

The Bet - Chapter 15 (Saturday – week 2 Part 1)

The Bet
by Karen Singer

Chapter 15 (Saturday – week 2 Part 1)

In his dreams, he was awash inside of a desperate need. It seemed that everyone… make that everything, around him was in a constant state of orgasmic ecstasy… except him. He alone felt nothing. Numb! While all around him was in the deep throws of sensation, he desperately willed himself to feel something, anything. But no matter how hard he tried, all he felt was nothing.
A sudden sensation to the very part of him that was most numb suddenly came through to him and in his sleep he reveled in it. He realized he was peeing. The only feeling he was capable of feeling there now. He relished every bit of the feeling, concentrating on it more and more. As his peeing slowed down, the numbness began to return, till there was nothing again. The only thing he could feel anymore was gone again. He was angry that the feeling was gone. He wanted it back again, badly. It bothered him, more and more… till he awoke.
Sunlight streamed in past the shade drawn down on his window. His pink clock radio hadn’t gone off yet. He looked at the time – it was late. Surprisingly late. Mel usually told him what time to set it for at night, or she set it herself. Either way, his alarm wasn’t set. He quickly got up and waddled into the kitchen to see if she had left a note. She had.

Sissy,

You have most of the day to yourself today to do whatever you want – enjoy it. But while you’re off, make sure you buy at least five more packages of diapers.

I expect you here at three o’clock sharp!
Shave your legs
Two fresh diapers
Makeup
Girdle with padding
Pantyhose
The rest is up to you but don’t wear your low-heeled pumps.

For later -
Make sure your uniform and apron are clean and freshly pressed!
Make sure your low-heeled shoes are freshly shined!
Carry them with you when you come but don’t wear them.
I will be inspecting you later!

The rest of the day is yours to do with as you please.
Enjoy it and don’t call me!

Completely shocked, he continued to stare at the note without reading it. Most of the day off! It was so unexpected. Mel had never indicated anything like that. Other than the order by buy more diapers that he really needed, she hadn’t given him any instructions for anything till the time she had specified. Nothing at all. Not even a demand to drink another baby bottle. Thinking about the bottles, which had always been first on her list, he realized he was thirsty. Since he had nothing else in the house to drink, he went to his refrigerator and pulled one of the many bottles out and put it to his lips.
Sucking on it, he headed back towards his blow-up mattress to figure out what to do with his morning. His eyes fell on the maid’s dress that was still in the pile where he had dumped it when he came in last night. She had mentioned clean and pressed. The dress still had some faint creases from where it had been folded in the package. He didn’t even have an iron. As he sat down on his blow-up mattress with his bottle, he figured he could buy an iron. Heck, he probably needed one anyway. Buying an iron was something he would have had to do anyway since he had just moved in. Was there anything else he needed while he was at it? He decided to make a list.
He got up again and poked through some of the boxes that were stacked in his room till he found an old notebook to write on. He went out to the living room and pulled his pen out of his purse. Then he went back to his mattress again. Five bags of diapers. An iron. Then he realized that he’d probably have to get an ironing board to go with the iron, so he added that to the list. Mel had said he had to have his shoes freshly shined so he added shoe polish. But what else did he need? Nothing was coming to his mind right away so he nursed on his bottle while he tried to think of things.
He didn’t think that going to the store was going to take all that long so he also tried to figure out what else was he could do for the rest of the day? He had no ideas.

Mel rolled over in bed and stretched. It felt good to be lazy and sleep in for a change. The many orgasms she had enjoyed at Chad’s expense last night still left her feeling wonderful. The fact that her period was all but over wasn’t hurting either.
She thought about Chad and the note she had left him last night. She wouldn’t be seeing him today till much later. They had been stuck too closely together for a long time now. They both needed a little bit of space for a change. She thought again about what she had put into her note. Not much really. But hopefully, today Chad would start to realize that even in his freedom he was on a very short leash.
She needed some coffee. She got out of bed and headed towards her coffee maker, thinking about Chad in his maid’s uniform all the way.

Chad decided he was hungry and immediately thought about his favorite fast-food place. He had most of the day ahead of him, time to start making the most of it. He got up from his mattress and headed into the bathroom to clean up. He carefully removed his diapers and climbed into the shower to wash the mess off. He soaped himself up with the flowery scented soap that he had now and washed his hair with the equally fragrant shampoo. When he was done, he dried himself off, taking extra care around the chastity device that he couldn’t remove so as not to hurt himself by pulling on it too much.
He shaved with his pink razor using the moisturizer instead of shaving cream because it was all Mel allowed him to have. His legs! Mel had said he needed to shave them today! He had never done that before himself. He turned the shower back on and climbed back in, this time with his razor. He quickly discovered how difficult it was to shave his own legs. He bent over this way and that way, trying to reach different parts of his legs, sometimes feeling like he was going to drown from the constant shower water streaming over him. He put one leg up on the edge of the tub to reach places and then the other. It was difficult, not at all like trying to shave his face. And it took a whole lot longer.
When he finally finished, he got out of the shower again and re-dried himself off. Mel’s note had said that he could do whatever he wanted. As far as he could see, that included not wearing diapers, or anything else he didn’t want to wear. He didn’t have any underwear, but he could easily go without.
He left his bathroom and opened his bedroom closet. There was a very disappointing selection of clothing to choose from. The only male clothes in the closet that he could get to, were his shirts. No male pants or shoes or socks or underwear. Being able to wear what he wanted still didn’t leave him many options. Feeling a bit despondent over it and not having a whole lot of choice, he selected a shirt and a pair of women’s slacks. He put his shirt on and buttoned it up. It felt like total freedom. No girdle, not even a bra under it. Absolutely wonderful. He wasn’t as happy about pulling the women’s slacks on, especially with no underwear at all, but still, not wearing diapers felt like a tiny victory.
He stared down at the shoes. There was really no choice other than the low heeled pumps. All the others were high heels and today he was trying to be as male as he could, or at least less noticeably a sissy. The clothing choices available to him just weren’t helping.
As he was about to slip the shoes on, he suddenly felt the urge to pee and before he could react, he discovered that he was wetting himself. He ran back to the bathroom, still peeing all the way. It didn’t stop till he got to the middle of his bathroom floor. He stood still there, angry at himself for wetting like that. Why had he done it? Then another realization hit him. Why didn’t he stop it? That was totally stupid! He could have held it easily. Why didn’t he?
His slacks were soaked, as were his legs. He had to go back into the shower once again to rinse off. While he was in there, he realized that part of his problem was that Mel now had him so used to peeing constantly that he wasn’t holding back anymore. All his muscles were totally relaxed. He wasn’t even trying to control himself. He decided right then and there that he had to start controlling himself constantly now, no matter what Mel put him through.
He tried to tighten all those muscles, just to flex them. He hadn’t done it in a long time now… days probably! But he was having a problem doing it. It was like he couldn’t remember how to tighten them. There were muscles there, but his brain seemed to be looking in the wrong place to make them react. It actually took him a minute to figure out how to tighten his muscles again. He was only able to tighten them a little bit at first, but once he had done it a few times, it became almost normal again. The only problem now was that keeping them tight again didn’t feel normal, and it felt like it was difficult to do. It certainly wasn’t comfortable.
He couldn’t believe how affective all her baby bottles had become. Frighteningly affective! If he hadn’t caught himself now, he realized that she might just have won the bet, and all too quickly. But he was fighting back now, and he was more determined than ever. From his prior research, he knew that it took about three weeks for a person to really form new habits. But he was peeing unconsciously in his diapers now without ever giving it another thought, and it had only been two weeks. He found that thought, not only disconcerting, but strangely, arousing. Fortunately, his tiny little member made no effort to grow any bigger and he never felt any little pinpricks of pain from his chastity device.
When he got out of the shower again, he decided that it was easier to leave those muscles relaxed where they felt more comfortable and normal, and then he could always control himself only when the need arose. But because of that, he decided to err on the cautious side and wear just one diaper… just in case! As he pulled his second pair of women’s slacks on for the day, he was aware that even though he was wearing a diaper, the slacks felt more normal and comfortable because he had some kind of underwear on under them.
Just to be different, and to try to disguise the fact that his pants were women’s, he decided to try pulling his shirt out and leave it untucked. The tails of his button down shirt hung fairly low. It looked a bit sloppy, but overall, he was very pleased with the affect. Unfortunately, it was ruined a bit more as he finally slipped his low heeled pumps on. But what choice did he have? Other than high heels.
He headed for his door and picked up his purse. He was tempted to leave it behind, but he was only planning on going through the drive through, so nobody would actually see it. Hooking it over his arm, he walked happily out his door and down to his car.

Mel walked around her apartment wondering what to do with herself. Normally, before Chad, she would have spent several hours on either Saturday or Sunday, or both, doing laundry and cleaning her apartment. But she had Chad now to do that. It was wonderful, but now what was she supposed to do with her free time? She had some work that she had brought home with her that needed to be done, but she didn’t really feel like doing it just then. She could go shopping, but most of the stores probably wouldn’t be open for a little while yet.
She sat down in a chair in her living room and tried to figure out what she wanted to do. She had no idea. Her thoughts naturally turned to Chad. She wondered what he was doing.

Chad carried his fast-food breakfast up the steps along with his coffee, still in its cup. He let himself into his apartment and set it all down on the kitchen counter. He took a sip directly from the cup. No baby bottles! A distinct pleasure. He ate his sandwich greedily. With no suppositories in his system, he enjoyed it even more since there would be less of a chance of something else happening.
When he was done with his breakfast, he wandered around his apartment for a bit because he had nothing better to do. He wiped his kitchen counters down even though they really didn’t need it and he did the same with his bathroom. He would have cleaned his toilet but wrapped up in so many layers of Mel’s cling wrap, that was impossible. He only glanced at his toilet out of the corner of his eye. He always avoided looking at it because it made him feel funny. It was too much of a direct reminder of what he could no longer do.
Straightening up his apartment hadn’t taken very long so he went back to his living room and sat down in his one and only chair. He had no TV. He couldn’t do laundry because he didn’t have a washer or a dryer. He couldn’t get on the internet because he not only didn’t have an internet connection, but his wife – make that ex-wife, had gotten their laptop in the agreement. He briefly wondered if Mel might spring for a new laptop too when he finally won this bet.
The boredom finally got to him and he realized that he had been putting off leaving his apartment again. It was time to get the shopping over with. He got up and grabbed his purse again and stopped. Did he really need his purse? He only needed his keys and his wallet and his cell phone. But Mel had said that he always needed to carry his purse now. Just in case she might be looking out the window, he decided to carry the purse just to his car. Once he got to the stores, he could always just carry his wallet and keys in his hands.
He headed for his door and had to stop again as he felt the urge to pee come over him quickly. He was able to stop it, but not until some had already leaked out into his diaper. He was more glad than ever now that he had decided to wear the diaper. The thought that he had been able to control himself even somewhat, made him glad.
But he had another problem now, should he just pee into his diaper like he had been doing, or try to get undressed and pee into the tub instead. Unfortunately, the urge was quickly growing stronger… too strong. With a sigh of relief, he let it out into his diaper. Then, because he didn’t want to wear the wet diaper to go shopping, he went back to change it. The decision to change himself also gave him a reason to delay going out in public again. He was happy about that.
Once he was changed into a fresh diaper and fully dressed again, he had no further reason to put things off. He grabbed his heavy purse and went down to his car.
He stopped at a drug store first to get the five packages of diapers. He didn’t want to carry his purse inside so he just grabbed his keys, his wallet, and his cell phone. His hands were a bit full, but at least he wouldn’t be as noticeable or embarrassing. He got out of his car and headed into the store. As far as he knew, with his shirt untucked, the only thing really sissy that was visible about him was his shoes, oh, and his stupid electric pink fingernails. But hopefully, nobody would even notice.
There were a few customers in the store when he walked in, but it was early enough that there weren’t really very many. Something he was glad to see. He knew very well where the adult diaper aisle was and he headed straight for it. But when he got there, he discovered that they only had two bags of the diapers he needed. Nothing else in his size. Should he get the two bags or go somewhere else? He finally decided to get just the two bags.
With his keys and his wallet in his left hand and his cell phone in the other, he pulled out one package that was down on the bottom shelf. The large bag was awkward to carry with his hands full. He fumbled around with it till he got it stashed precariously under his left arm where he was carrying his keys and wallet. Then he tried to reach for the second bag. But the only hand he had to grab the bag with was only partially useful because he was still holding his cell phone. He finally nudged the bag out to where he could try to pick it up. It was a bit difficult to do, but he finally got it wedged between his body and his arm. He stood up and got halfway down the aisle, and the first bag slipped out from under his arm and fell to the floor. To pick it up, he transferred the bag in his right hand under his left arm where the fallen package had been. Then to make matters easier, he also carefully transferred his cell phone to his left hand too so that he would have all his fingers of his right hand available to help pick up and hold the second package. He found that it worked much better that way.
He was almost to the checkout counter though when he realized that he was having trouble holding onto his wallet, cell phone, and keys in one hand all at the same time. He didn’t have trouble long though, because his cell phone slipped out and fell to the hard tile floor. He stepped back to see where his phone had landed, and immediately saw that the cover had cracked at the hinge. He was so angry he wanted to kick the phone. But he controlled his anger as best he could. Feeling devastated by what he had just done, he dropped the two huge diaper bags on the counter and picked up his cell phone. He looked at it carefully. Broken! No doubt about it. He was going to have to get a new one.
He paid for the packages of diapers with his credit card so he wouldn’t have to deal with bills and change, and the clerk put each of the packages of diapers into a separate bag because the store didn’t have any bags big enough to hold more than one. Lugging the two big bags out to his car, he mentally cursed himself for dropping his phone, and for not carrying his purse which would have made it all easier, and finally for entering the bet in the first place. Unhappily, he drove out of the parking lot in search of another drug store that would carry the diapers he needed.

The Bet - Chapter 14 (Friday – week 2 Part 4)

The Bet
by Karen Singer

Chapter 14 (Friday – week 2 Part 4)

He could tell that Mel still wasn’t happy with him as they got back into the car again. He also figured that she’d take him out to dinner now and make him drink from his baby bottle in front of a lot of people again. He wasn’t looking forward to that at all. It was hugely embarrassing - one of the major things that made him want to crawl into a hole somewhere and stay there – forever. “Are we going to dinner now?” he asked, knowing that they probably were. “No,” Mel replied, “We have to go somewhere else first and I want to get there before the store closes.”
Chad didn’t know whether to be happy or scared. He was happy because he wouldn’t have to repeat the baby bottle thing in the restaurant, but he was scared of what Mel had in mind now. Her shopping trips could be miserable for him.
Mel drove quickly and determinedly towards the area where the store was supposed to be. As she got close, she started scanning the store fronts to try to spot it. There it was! She pulled into the parking lot of a row of stores. There were plenty of empty parking spaces right in front.
Chad looked up at the store in front of him as she pulled into the parking space. The brightly lit sign above the store said Uniforms. “Uh oh,” he thought to himself. He looked over at Mel, she was smiling wickedly at him as she pulled her keys out of the ignition.
“Leave your diaper bag, in the car again,” she said. “Now let’s go in and get you fitted.”
The saleswoman who greeted them as they walked through the door said a very nice hello to Mel, but she did a double take when she looked at Chad.
“Say hello,” Mel said quietly to Chad.
Chad dropped into a curtsey and said a simple, “Hello.”
The saleswoman looked like she was going to panic. She finally looked back at Mel. “May I help you?”
“Yes, I need a uniform for my maid here.”
The woman looked back at Chad again. Chad suddenly felt more embarrassed than ever.
“Okay…” the woman said, drawing the word out as she tried to compose herself. “What did you have in mind?” Then she quickly added. “We don’t carry any of that fancy French maid stuff. This is not a…” she was lost searching for the word.
“Don’t worry,” Mel reassured her. “I want something proper.”
The woman nodded, obviously reassured. “In that case, let me show you what we have.” She led the way to the back of the store where there was single rack in the wall with a lot of dresses hung on it. “We sell to a lot of caterers, and hotels, and any of these uniforms should work for most occasions.”
Mel started browsing through the uniforms. Chad saw mostly very plain looking dresses in a variety of colors. He saw Mel spending time considering a pink one, but then she moved on again. Finally, Mel reached the end of the dresses and started back through them again in reverse. She quickly pulled out one that was kind of a grayish black with white cuffs on the short sleeves and white lace all around the rounded neckline. Mel seemed to be really happy with it. “Oh, I like this one a lot,” she said as she held it up to inspect it closer. “Do you have one that he can try on?”
“Of course,” the woman replied. “What size does she… I mean he wear?”
Mel almost laughed. “I’m not sure. What do you suggest?”
Chad almost groaned. “He usually wore a size twelve and he knew that Mel knew that.”
The woman looked him over carefully, which Chad wasn’t too thrilled about. “I think we should try a ten, or perhaps a twelve.” She opened a closet in the wall and started sorting through a lot of dresses that were very closely packed together. She finally found what she wanted. “This dress isn’t exactly the same model, but we can use it to at least determine the right size.” She handed the dress to Chad who wasn’t really happy to take it. “There’s a dressing room right here,” the woman said, pointing to a door a few feet away.
Chad sighed and took the dress inside. He set his purse on the bench inside the room and began getting undressed. As he stepped into the larger of the plain looking dresses, he thought to himself. “Now I’m trying on maid’s dresses in a store. What will she have me doing next? And with that, he suddenly felt the little pinpricks irritating him again from his chastity device. He found the size label inside the dress – twelve. Good. At least she had handed him the right one first. He had to struggle to zip the dress up behind him, but it wasn’t too bad. But what was bad, was that trying the maid’s dress on was fueling his fantasies too much. And yet he could do nothing at all about it. It was so frustrating!
When he finally had the dress on right, he stepped out of the dressing room. He was glad that there were no other customer’s in the store just then.
“Oh, that’s very nice,” Mel said as soon as she saw him. But what was really interesting her, was that for the first time she was starting to really see her future vision for him. She walked over to him and started pulling on the dress in various places to see how it fit. “Is this the twelve?” she asked.
“Yeah,” Chad replied. “That’s what I usually wear.”
Mel’s angry look let Chad know quickly that he had messed up again. She continued to stare at him. He dropped a quick curtsey as he said again, “Yes, Mistress, it’s the twelve.” She seemed to be pleased again.
“I think I’d really like to see the other one.”
Chad was surprised, he always wore a twelve. But he took the other dress the saleswoman handed him and went back into the dressing room. He had to struggle a lot more to get it zipped up in back, but he finally got it. The whole dress fit him tighter. He could feel it pressing against his padded breasts. He could feel it hugging his entire body. He stepped out of the dressing room intent on letting Mel know that it was too small.
“Oh, that’s much better!” Mel said instantly. Chad was very surprised. Was she crazy?
“Yes,” the saleswoman agreed. This time she was the one who pulled on various parts of the dress to check the fit. “It fits almost perfectly.”
“Good!” Mel replied. “But do you have one in the style I want?”
The woman smiled and walked over to a drawer in the wall and pulled it out. The drawer was loaded with dresses folded and wrapped in plastic. “How many would you like?”
Chad realized that even Mel was surprised. “Just one for now. Then we’ll see about more later.”
The woman pulled out one of the packages and checked the label. She handed it to Mel. “Do you have any aprons to go with it too?”
“Of course,” the saleswoman replied. “We sell a lot of them. Do you want to pick one out while he changes back again?”
Mel just smiled and let her lead her away.
Chad headed back to the dressing room to change. As he pulled his own clothes back on again, he realized that the entire situation hadn’t been bad at all. A bit embarrassing for sure, but most of the things that Mel usually put him through were far worse. Before he left the shop, he had to curtsey and say thank you to the saleswoman one more time. Thankfully, there was no one else around.

As Mel drove along the busy street, she kept picturing Chad as he had looked in the maid’s dress. He hadn’t worn the one she had picked out, but it had been close enough – any maid’s dress would have been close enough. Now, as the busy Friday night traffic was all too thick, she suddenly couldn’t wait to see him in the dress she had just bought him – complete with the apron. But she had other places she needed to take him, other things she wanted him to buy. And they hadn’t even had dinner yet! But just seeing him in that dress… what it had done to her… was still doing to her. Cassie’s words were suddenly ringing very clearly in her ears. “If you’re not making a mess, you’re not having sex.” Right then, she wanted sex badly, very badly. All plans were off! She spotted a fast food restaurant right ahead of her and she turned in very quickly, almost too quickly.

Chad fully expected Mel to stop at another restaurant after buying the dress, but he was surprised when she pulled into a fast food restaurant and then went through the drive through, as if she couldn’t wait to get home again. He was more surprised to find out that that seemed to be exactly the case as he tried to carry his purse, his diaper bag, the bag with his new maid’s dress and apron, the bag containing their dinner, and the large size drink that she had ordered for him, up the stairs to her apartment – while she carried her purse and the other drink.
His hands were so full, that once he was in her apartment, he had to carefully juggle things to set everything down. Mel was at his side instantly with a pair of scissors. She grabbed the bag from the uniform store and pulled everything out of it. The item on top was a white apron, all folded and wrapped in heavy plastic like the dress. In moments she had cut the plastic from both the apron and the dress. She handed them to him. “Go to my bedroom and put this on.”
He took the dress and apron from her hands. Was it his imagination, or did she seem a bit flushed? Probably his imagination. He carried it into her bedroom and set the apron down on the bed. He spread the dress out open. It was a simple dress, but the white cuffs on the sleeves and the white lace around the collar made it seem much more interesting. For the first time he realized that the dress had two pockets in the front – not that they’d do him any good. He undressed, having to remove his shoes first because they were strapped onto his ankles.
He stepped into the dress and pulled it over his shoulders. As he did so, his chastity device once again began giving him little warning signs. He struggled to zip it up and then fasten the hook behind his neck. The dress felt tight against his body. He ran his hands down his body from just under his padded breasts to his thighs. The pinpricks of pain wanted to become much more, but he carefully controlled himself. He had to sit on the floor to buckle his shoes back on.
“What’s taking so long?” he heard Mel call from the living room.
“I’m almost ready!” he called back. He picked up the apron and shook it out. It was rounded on the bottom with a row of wide lace all along the edges too. He wrapped the wide straps around his waist and attempted to tie them in the back in a large bow. He was ready. He realized that he was about to show Mel her fantasy. He took a deep breath and walked out to the living room.
Mel was sitting on the sofa watching the door to her bedroom intently. There was food in the kitchen, but she wasn’t the least bit hungry, not for food anyway. Finally Chad walked out of the bedroom. He stood a few feet from the door and just stood there while they each stared at the other for a few moments. The excitement inside of Mel soared. She had done this! She had made him into her maid. He was standing there in front of her dressed as her maid because she had made him do it.
She got up from the sofa and walked around him. “The shoes are all wrong, but we can change that later,” she said. She stood back from him. “Thank me for your new dress, Sissy.”
Chad immediately dropped into a curtsey and said, “Thank you, Mistress.”
Mel had to press her thighs tighter together against the need that wanted to escape. “Sissy… you’re wearing a dress now. You can actually grab your skirt when you do that. I know we should have had you practicing that way before. I realize that now. But please try to remember to do it properly from now on.”
Chad had to fumble to grab the skirt of the dress as he dipped into another curtsey and said, “Yes, Mistress.”
Mel smiled at him. “It will get easier with practice. At least it better!” She turned her back on him and began sauntering merrily into the kitchen. “Sissy! I’ll have my dinner now!” She felt like a queen.
Chad immediately dropped another curtsey and said “Yes, Mistress.” Then he hurried ahead of her to the kitchen to get the burgers she had ordered out of the bag. He was about to set her burger in front of her, still in it’s wrapper, but luckily he stopped himself in time. He unwrapped it and set it out on a plate for her along with her fries. Her drink he poured into a much nicer glass than the one that it had come in. He set them all on the table in front of her and saw her smile.
“To your corner, Sissy.”
His heart dropped. He didn’t really want to go to the corner again while she ate, but he obediently went, slowly, and crammed himself in.
“Put your feet together!” her voice lashed from the kitchen. “Legs straight, not slouched!”
He quickly straightened himself up and tried to stay that way. He couldn’t see anything except the blank walls of the corner so he closed his eyes. He couldn’t hear anything either, she was being silent and was too far away. The seconds seemed to drag by. He had no idea how long he had already been standing there. How could it take her so long to eat just a burger? His feet were beginning to kill him in those shoes, the straps were digging in painfully. He moved one of his feet just a tiny bit to relieve the pain.
“Don’t move your feet!” her voice lashed out instantly.
Chad immediately brought his feet back to where they were. His whole body tense now in case she yelled again. But she didn’t, and he allowed the tension to drain away as the seconds ticked by slower than ever.
Mel had only been able to eat half her sandwich, she was too keyed up to eat anymore. She had him standing in the corner where she knew he didn’t want to be. He had moved slightly and after not moving for so long the tiny movement had been like a signal flare. She had put a stop to that quickly. And now she had him stuck there again. Glued to his corner like a child. Completely in her power.
She got up from the table and sat in one of the chairs in the living room where she could see him better. She suddenly wanted to see all of him better. “Turn around, Sissy,” she said. His whole body seemed to sigh with relief as he pulled himself out of the corner and faced him. “Back up into the corner and stay there,” she commanded. She could see the questioning look of surprise on his face, but he did as he was told. She made him stay there like that for a long time, just standing still in his corner.
Finally, she could take it no more. Her period be damned. It would probably be over with by tomorrow anyway. “If you’re not making a mess, you’re not having sex!” But he was in his maid’s dress and she didn’t want that to become a mess. “Sissy! Go take your dress off now. And hurry!”
Chad blinked in surprise. Now what? He tried to drop a quick curtsey where he was but he was too far into the corner and the walls got in the way. She hadn’t noticed anyway, she was fumbling around in her desk again. He headed for the bedroom.
“Sissy!” she called. He stopped and turned around. “Just wear your diapers and nothing else.”
“Yes, Mistress,” he replied with a better curtsey than last time, but she was back at her desk again.
By the time he came out again in just his diapers and plastic panties, Mel had completely covered half the sofa in towels. He was very surprised at that. She came up quickly behind him and grabbed his hands and tied them behind his back. He quickly became nervous. She positioned him in front of the couch and made him get down on his knees. But now Chad had a pretty good idea of what was going to come next. She tied his ankles together too, then left and came back with her scarf again. In moments, Chad was well blindfolded.
Mel walked around in front of Chad for a few moments, making sure he couldn’t see her. Then, tentatively, she began pulling her clothes off. The more clothes she removed, the faster off they came, till this time, she was completely naked in front of him. Knowing that he couldn’t see her. She sat on the couch in front of him, her desire growing fierce. “Ok, Sissy. Crawl forward.”
With great difficulty, Chad moved one knee forward. Mel felt her need rise a bit more. He swung his other knee forward, she started to breath in small gasps. He moved again, and she suddenly had clear visions of him in his maid’s dress. She wanted him to move faster now, but the wait was just as delicious. Another knee. He was turning his head now, trying to get a sense of where she was. “I’m right here, baby,” she said softly. He moved again in her direction. He was almost there. “Just a little more, baby.” Her voice helped to turn him in just the right direction. He moved one more time. She couldn’t wait anymore. She moved further onto the edge of the couch and grabbed his hair. Roughly she yanked him down into her waiting sex.
Chad let out a small scream of surprise as he suddenly felt her grab his head and yank him down. His face ended up right in her crotch. The force she had used hurt his nose a bit. He realized her crotch was very wet. The odor of her sex was almost overpowering. She was grinding herself against his face now. Wanting more. Tentatively, he reached out with his tongue and licked a tiny bit.
With the first touch of his head against her crotch, Mel almost came. It was wonderful. She needed more though, much more. And when she felt the almost tiny touch of his tongue licking her, she really did come… in one big gasping wave. But she had only just started. This was her dream. This was what she had always wanted. She was in full control. She didn’t have to worry about getting pregnant. She didn’t have to worry about anything. She had all the power. And he had nothing. He couldn’t get any kind of pleasure at all. She had fixed him so that he was totally denied. The power of what she had done drove her quickly to another orgasm. More, more, more!

Chad felt like his face was being abused badly as she thrashed around him. He could hardly breathe. She kept pulling him tighter and tighter into her, then she would back off slightly, only to do it all over again. And through it all, she was so wet! He was quickly becoming very tired. Not being able to breath wasn’t helping either. He tried to pull away, but her grip was too powerful, too fanatical. Helplessly tied as he was he had no leverage to fight against her. She was feeling orgasm after orgasm, and he wasn’t allowed to feel anything. She had locked him up. Completely. As great as his need was, he had no way to let it out. She was skyrocketing above him, using him to satisfy her utterly. And his need was locked away. The very thought of it refueled his wantings even more and he felt the pinpricks beginning again, but only for a moment. He was growing too tired. He tried to concentrate on his penis. Willing it to feel something in all this. He desperately wanted it to feel something. But locked up inside the device, he could feel nothing. Nothing at all. It was so frustrating. She orgasmed again. Wasn’t she done yet? It seemed not. But at least she was moving slower now, with less need.

Mel came down from another high, and slowly sanity began to creep its way back into her. Oh God it had been so good! She still rocked against him, feeling his wonderful face and tongue still stimulating her. Making her feel wonderful. She looked down. She could only see the hair on top of his head. He was still trying to lick her, but now that had become very weak. She pulled his head away from her, slightly, then all the way up. He was gasping for air, obviously very tired. She cared, but she didn’t care. It had been too good. His face was an absolute mess, not just wet with her sex, but red from her period too. The scarf around his eyes was probably ruined. She’d have to get another one.
She took a deep breath to calm herself, still holding onto his head with both hands. When she had calmed down enough, and she felt that he was stable enough and wouldn’t fall down, she got up and went to the bathroom. She wet a washcloth and brought it out to the living room and washed his face. She could tell he liked that, needed that. He looked better afterwards. She glanced at the couch. It was a good thing she had put down so many towels. They were a mess.
She grabbed Chad’s head softly in her hands. “Lay down Sissy.” And she helped him to lay on his side without hurting himself. “Stay there like that.” I’ll be back in a little while. She grabbed the towels from the couch and left him there. She went into the bathroom and peed, then she got into her shower and rinsed herself off thoroughly. She felt wonderful. Glowing.
She dressed quickly in jeans and a t-shirt and went out to him. He was sleeping, tied up where he was. He woke up as she started untying him. She took his blindfold off and helped him to his feet, then she led him into her bathroom where she removed his diapers. He wasn’t messy. He wasn’t even as wet as he usually was. She remembered that he hadn’t eaten or even had anything to drink all evening. His dinner was still on her kitchen counter.
She opened her cabinet and pulled out two of the super thick nighttime diapers and laid them under him. She spread the baby lotion over everything she could touch. She looked carefully at his penis, trapped inside of the device. So small, so denied. She had planned on taking the device off of him tonight to clean him thoroughly, but that was going to have to wait. She wasn’t up to it just then. She quickly shoved two more suppositories up inside of him and struggled to get the diaper pins through the extra thick diapers. Then she pulled his plastic panties up again. “Get dressed now,” she told him, “just wear what you wore to work earlier.” She left him and went back to her kitchen. Nothing had been cleaned up, she hadn’t given him time. She grabbed the large drink she had bought for him and found several empty baby bottles to pour it into.
Chad moved slowly as he dressed again. He was aching and sore all over, but fortunately, not too bad. The thick cloth diapers she had put on him felt strange, horribly bulky. He felt very tired just then. His stomach growled. She hadn’t even allowed him to eat. When he was dressed, he went out to find her.
“Where’s your dress?” she asked.
“I left it on the bed.”
“Get it. Bring it home with you.”
He turned around. Home? Already? He grabbed the maid’s dress and the apron that went with it and carried it back to her living room. She handed him a plastic bag with three baby bottles in it, filled with the drink she had bought for him. She also handed him his dinner that she had put back into the bag from the restaurant. “Go home now. I’ll leave a note for you later tonight like I usually do.”
Chad was bewildered. It almost felt like she was throwing him out. But she didn’t seem angry in any way. He grabbed the bags she handed him, grabbed his purse and diaper bag too. And with his apron and dress hung over his arm, he went back to his apartment. He switched on the light as he went in. The apartment seemed to echo its emptiness back at him. He set everything down in a pile on his floor, not even bothering to hang the dress up.
His stomach growled. He dug the food and the drinks out of the little pile he had created and carried them into the kitchen where he ate standing up at his counter. He didn’t know what to think. So he didn’t think. When he was finished, he got undressed down to just his diapers and plastic panties. Then, only because he thought he should, he put his baby doll nightie on. He laid down, and soon fell sound asleep. It had been a bit of a strange evening.
And in the middle of the night, the dreaded suppositories did their job on him.

The Bet - Chapter 14 (Friday – week 2 Part 3)

Reminder – My new Baby Bobby story is available for anyone who still wants it.


The Bet
by Karen Singer

Chapter 14 (Friday – week 2 Part 3)

“Giiirrrlfriend…” Robin turned her head towards her friends who were all waiting for her as soon as she entered the break-room. She quickly fixed herself a cup of coffee and carried it over to the table. There were no chairs available because there were already too many women sitting there waiting to talk with her. She set her cup on the table and looked for another chair to drag over. “We heard that you and Chad were arguing in the hall a little while ago…” the same woman asked.
Robin blushed. Sorry, I didn’t mean to be so loud. It’s just that he can be so….” She shook her head in frustration.
“I know what you mean,” another of the women replied as Robin finally spotted a chair and started to drag it over. Almost magically several of the women moved to make space for her because they were all so interested in whatever she could tell them.
And tell them she did… everything she could think of that she knew already. Which was a lot, but at the same time, almost nothing!
“Oh my!” one of the women said when she was done. “Wouldn’t it be fun if he did come down here to talk about makeup? Can you just see it?”
There was a lot of laughter from everyone. “Oh dear!” another woman said through her laughter. “I’m going to have that picture in my head all afternoon now. I’ll never get any work done.” There were more squeals of laughter.
But Robin’s laughter was suddenly more muted. Yeah, it was funny, but at the same time she felt for the guy, as frustrating and as contrary as he was. There was something major going on that she still didn’t know about. Yet.

Robin sat at her desk. The project she was working on was on her screen, but she wasn’t seeing it. Her mind was completely occupied by Chad. The guy wanted to discuss makeup… sort of. She understood his reluctance… sort of. After all, he had been wearing it to work all week! Could she use that in any way to learn more about what was going on? She just wasn’t sure. It seemed so unlikely. Little kids liked to play with makeup – well, girls anyway. She thought of him like a little kid playing with it. Playing at it and not really having any idea of what he was doing. She could play makeup with him, she guessed. But to be honest, she wasn’t too keen on the idea, especially in the break room where everyone could see them.
She looked at her purse with all her makeup in it, not really a lot, only what she needed, but it was probably enough, especially for him. He had a purse full of makeup too. At least, that’s what he had said. Now she wondered. If he did, what kind of makeup did he have? He didn’t even know if he had a mirror earlier.
Maybe that was a place to start though. Instead of really playing with the makeup, they could talk and compare. And in the process, maybe she’d be able to find out what was really going on.
It wasn’t much, but at least it was a plan.
She looked at her watch, it had been about an hour now since she had taken her last break. Now was as good a time as any.

Chad was working on his project when he heard Robin call his name behind him. He turned around and glanced at his watch. “Oh Robin, I’m sorry, I’ve been working on my project and I didn’t even start on the animations yet.”
Robin smiled at him. “That’s not why I’m here. Come on, it’s break time. Time for some coffee.”
Chad was surprised. He had almost forgotten. He was fairly sure he hadn’t actually promised he’d go down to the break room with her. “Uh… I’m not sure,” he replied, “I’m still working on this piece.”
“Oh come on Chad, get up out of that chair for a while and live a little. I’m going with you. It won’t hurt you to just get a cup of coffee. And while we’re there, if you still want to talk about makeup, then that’s fine. I don’t mind!”
But Chad still felt too uncomfortable about it. “Robin, I just can’t…”
“Oh come on!” she said. Then to help him along, she reached down and pulled out the drawer where she guessed that he had now stashed his purse. It was there. She grabbed it and handed it to him. “Here! Now come on!”
For the first time, Chad realized that she had her large tote bag with her too. Why was it that when a woman carried a purse you didn’t always notice? He seriously doubted it would be the same for him. “But…”
“Oh for heaven’s sake. Just stand up and walk with me.” It was like talking to a child. But finally he stood. Not wanting him to back down again, she linked her arm through his and walked him out into the hallway. She kept hold of him till they had gone well past the first turn.
If Chad thought he had been scared and embarrassed by the way he was dressed every time he walked down to the break room before, it was nothing compared to how he felt now, carrying his purse. But then he realized that at least this time he wasn’t wearing any makeup. That thought made him feel a bit better – very little, but a bit.
“So you’ve really got a bunch of makeup in there?” Robin asked as they walked.
“Yeah, all of it.”
“All? Then you can’t really have very much.”
“I think it’s a lot. Too much!”
“Chad, no woman ever thinks she has too much makeup.”
“I’m not a woman.”
“Then why are you doing this?”
Robin was hoping for a better answer, and she felt like she almost got one, but instead, he said. “It’s complicated.”
She sighed.

Neither Robin or Chad noticed the woman peeking around the corner of the hallway after they passed. She had sat at the break table earlier and laughed along with Robin over Chad. She followed them quietly. After they were inside, she stayed just where she couldn’t be seen and tried to peek around the doorway to watch them, hoping that neither of them would realize that she was there.

Robin went straight to the coffee pot and poured herself another cup. Chad waited behind her. When it was his turn, he took a cup, then had to figure out how to juggle his purse, the coffee cup, and the coffee pot all at the same time. Not for the first time did he wish for pockets again. He had to hang his purse on his left arm, and hold the cup in that same hand while he poured his coffee with the other hand. He was just glad he drank it black so he wouldn’t have to mess with the creamer or sugar too. He followed Robin to the back corner table where she had sat down. Her tote bag was on the floor. He set his purse down there too.
“Don’t put it down there,” she said, “I want to see what you’ve got.”
Chad hesitated, still not sure about the whole situation. He looked around, there was nobody there to see him. Throwing caution to the wind, he set his purse on the table and opened it.
Robin wanted to peer inside, but she controlled herself.
“You really want to see all this stuff?” he asked.
“Of course,” she replied.
Shaking his head and wondering why on earth he was really doing it, he began dragging all his makeup items out and setting them on the table.
Robin was a bit surprised to see quite so much. Picking up a powder compact, she opened it. “See, you do have a mirror,” she said, showing it to him.
“Not like yours.”
“Are you ready to carry something as big as this?” she asked, indicating her tote bag.
He almost laughed. “Not yet.”
“I’m surprised you bought so much since you’re just starting,” she said.
“Well, it wasn’t exactly my idea.”
“Your makeup lady?”
He nodded. “Yeah.”
“Does your makeup lady have a name? I mean, it might be easier than just calling her your makeup lady all the time.”
He was a bit reluctant to tell her, but finally he just said, “Mel.”
Robin smiled even though she literally had to drag every little bit out of him, but at least she had a name now. It was better than nothing.
“So what has Mel taught you?”
“Not much,” he admitted. “Really, she’s just concentrated on my eyes and then this morning she started with the foundation.”
“It was pretty bad this morning.”
“Yeah, I know. But it was the first time she’d really shown me anything about it.”
“What did she show you?”
Chad picked up one of the liquid foundation jars and started telling her about what Mel had him doing. Robin asked a few questions, and soon Chad found himself showing her other things. It wasn’t till his coffee was half gone that he realized he had been sitting there totally engaged in girl-talk with her. The very thought of what he had been doing quickly stimulated his overly repressed system, sending pinpricks of pain right where he didn’t want them. The pain reinforced his thoughts about talking about makeup like a girl, which quickly made the pain even worse. He winced against the pain, but it was too late, Robin had noticed.
“Is anything wrong?” she asked quickly.
“No!” Chad replied a bit too forcefully. But he couldn’t continue talking about makeup anymore. It was too painful. As quickly as he could, he started packing everything back into his purse again.
“What’s wrong?” she asked again.
“Nothing!” he replied. “Come on. I’ve got to get out of here.”
Robin had to hurry to catch up with him. She still didn’t know what had gone wrong. For once he was beginning to relax and open up to her, and then all of a sudden he had closed down… again! And the only thing she really had now was a name – Mel. Completely useless information!

The woman who had been watching them hurried back down the hallway before either of them could know that she had been watching them the whole time. She hadn’t been able to hear any of what they said, but she had seen most of it. He had really been there showing her his makeup. Amazing. A funny idea struck her. The more she thought about it, the more she wanted to do it. But it was Friday, her idea would have to wait till Monday.

Shortly before quitting time, Chad looked away from his computer. He really hadn’t been working all that much since he had taken the break with Robin. Had he really shown her all his makeup and been talking about it with her? He couldn’t believe it. But now his thoughts were more and more on Mel and what she might do to him for washing all his makeup off. Would it be better if he reapplied it before he went home? He decided, it was his only hope. Nobody was around. He pulled his purse back out of his desk drawer. Robin had shown him the tiny mirror in the compact. He found it and opened it. It was so small. He could hardly see any of his face at all. Carefully, he put some of the liquid foundation on his finger and began dabbing it in spots around his face. He began spreading it out, trying desperately to see it properly in the tiny mirror in his hand.
“You know, that works better if you use a brush.”
Chad turned in horror to see Robin standing at the entrance to his cubicle watching him.
“I don’t have a brush,” he admitted.
“Well, you can use your fingers like you’re doing, but if I were you, I’d get a brush. A good one.”
“Thanks,” he said as he went back to work. He was glad to realize that Robin had left him again. But she was back all too quickly.
“Here,” she said walking back into his cubicle and brandishing a small brush in her hand. “Let me help you.”
Chad was shocked and surprised, but before he could really protest, she had planted herself against his desk and was starting to run the soft brush over his face. Not knowing what else to do, he let her work on him. “There,” she finally said. Do you want me to add some powder or blush too?”
“No thanks,” he replied, wondering how the job she had done looked.
“You’re sure?”
“Yeah, thanks.” He grabbed his tiny mirror and tried to see what she had done.
Robin left again and came back a moment later with her larger mirror. “Here,” she said, “use this.”
He grabbed her mirror gratefully. Yeah, she had done an amazing job. He promised himself he would get some brushes to work with real quick.

“Are you going to do your eyes too?” she asked.
He was planning on it, but he wasn’t sure he wanted to do it with her watching. “I was thinking about it,” he finally said.
“Let me watch,” she said softly. “Maybe I can offer some advice.”
He looked at her for a moment then began sorting through the makeup in his purse.
She watched him doing his eye makeup, very, very slowly, but surely. Not really too bad at all. But then he had been wearing it all week now.
“You did very well,” she told him when he was finally all done. I’m sure that Mel would be proud.
He could only hope. Mel was his next big obstacle to face. His cell phone buzzed and he quickly pulled it out of the pocket of his purse. A text message from Mel. He read it quickly, then put it away again. He let out a big sigh. Her instructions were just what he had expected – go home and change his diapers, no pantyhose, and wear the open toed sandals, pad the cups of his girdle, and a big emphasis on not being late!
“Your makeup lady… Mel?” Robin asked.
He was shocked that she should ask. “Yeah,” he replied softly.

Mel hurried quickly up the steps towards Chad’s apartment, praying that he was ready. She was the one who was running behind and having to stop to pick him up took extra time. She fished the keys out of her purse while she was still going up the steps and had the door unlocked almost instantly. The first thing she saw when she opened the door was the surprised look on Chad’s face. “Are you ready?” she asked quickly without even closing the door.
Chad didn’t know if he should curtsey and greet her properly or answer her question first. He opted for the curtsey. “Hello, Mistress.”
She smiled broadly at him. “Hello, Sissy. Now are you ready?”
“Yes, Mistress,” he said being careful to remember to curtsey.
“Good! Come along, I’m running late.” But Chad’s curtseys had reminded her of something else that she had planned for the evening. “Damn,” she swore softly. She had to really hurry now. Chad was standing next to her, his purse in his hand, his pink diaper bag slung over his other shoulder. “Sissy, before we go, we need to practice something.”
Chad looked at her questioningly.
“Now show me how you’re going to say thank you to me all evening.”
Chad was suddenly shocked. All evening? Was she talking about doing this in public? Warily, he dropped another curtsey with his hands full and said, “Thank you, Mistress.”
“Good, and now show me how you say yes or no to me.”
He curtseyed again, saying “Yes, Mistress.”
“Good enough,” she said quickly as she headed out through the door. “Now come on, I don’t want to be late.” She closed and locked his apartment door behind them and hurried to catch up to him on the steps. As soon as she had pulled her car out of the parking space she said, “I expect to see you curtseying properly to me, all night… everywhere we go!”
Chad already had horrible visions of doing just that running through his head. His stupid chastity device was suddenly causing him pain again. But he obediently said, “Yes, Mistress.” He was going out in public again. He was wearing women’s heels, women’s pants, makeup on his face, the bra cups of his girdle each held a pair of pantyhose to pad them way out… and he was carrying a purse. He mentally screamed. And then he remembered again that they were heading straight to have their nails done! Aaaarrrrggghhh! It was becoming too much. The devilish little teeth of his chastity device felt like they were burning his skin. But fortunately, that’s all they did. He felt so stupid. He felt so embarrassed. He felt so incredibly excited! And at the same time, his need felt so denied.
It wasn’t till a few moments later when Mel made another comment. “You redid your makeup.”
Chad was suddenly very worried. “I’m sorry, I had to. I wore it all morning, but then after lunch…”
“What happened?” Mel asked.
“Well, Cassie…”
“I know very well what Cassie did. Did you cry?”
He was embarrassed to say it. “Yeah, a little. But it hurt!”
“So?”
“So, afterwards… I guess I rubbed my eyes, and I didn’t know it but it got all over my face.”
“You shouldn’t rub your eyes… wait a minute, you said you didn’t know it had gotten all over your face?”
“Yeah, Robin told me.”
“Robin?”
“She works with me.”
“Oh.” Mel digested that. One of his coworkers. “What did she say?”
“She made me wash it off.”
“She made you?”
“I tried to resist, but she threatened to drag me into the ladies room and do it herself if I didn’t.”
Mel almost laughed. She could just picture it. “So you decided to wash it off.”
“I’m sorry. But she wasn’t giving me much of a choice.”
“And then you decided to put the makeup back on again.” She turned her head towards him as she drove. “Good girl!”
Chad felt really good at her compliment. “Thank you, Mistress.”
Mel smiled broadly. “I noticed you did a really good job with the foundation this time.”
“Actually, that was Robin’s doing. She kind of helped me.”
Mel turned her head and looked quickly back at him. Suddenly she wasn’t so sure about things. She didn’t know why, but she suddenly didn’t like Robin. Not that Robin had done anything at all wrong. Was Robin pretty? Did Chad love her? Was she another reason that Chad was getting divorced? She knew she shouldn’t feel jealous, but she did. It was a woman thing she knew. She had unknowingly staked out her territory on Chad as part of this bet and she didn’t like any other women messing with her property. She brooded about that all the way to the nail salon.

“Hello, Sissy,” the little Asian woman who had done his nails last week said as he walked in.
“Hi,” he replied.
“Sissy!” Mel’s voice suddenly sounded like a gun being fired at his head.
He hated doing it, more than he realized he would, but he had no choice. “He dropped a quick curtsey and said, “Hello.”
The stare and look of astonishment on the nail technician’s face was almost priceless. It took her a moment to fully recover. “Ok, Sissy. Let’s get started.”
Mel smiled as she watched Chad walking away. His embarrassing evening was only just beginning. She was determined to make it even worse now after hearing about Robin.
“You cut you fingernails!” the little Asian woman complained after his toes were done and they had sat down to start on his hands. “And you did a bad job. You should have let me do it.” Chad said nothing as she tried to smooth the edges where he had left them a bit jagged. A little while later, Chad was looking at his almost electric pink fingernails. They didn’t look nearly as feminine as they had last week, not because of the color, but because they were so short. But he was very embarrassed by them never the less.
“Let me see,” Mel called again from the table where she was having her nails done.
As he had done last week, he walked over and held his hands out so she could see.
Mel gasped and pulled her hands away from the woman who had been working on them. “Sissy, you cut your nails!”
Chad knew she would be angry, but he was still glad he had done it. “I had to,” he explained, “they were getting in the way when I typed.”
Mel looked at him angrily in the face. “It won’t be happening again! Now thank the lady who worked on you properly, and make sure you leave her a good tip again.”
Chad figured he’d probably get punished a bit later for cutting his nails, but he still didn’t care. It was like a tiny way that he had found to deny her. He almost laughed to himself as he dropped another curtsey to the nail technician and said “Thank you for doing my nails.” He heard laughter from a few women who were sitting by the door waiting their turn. He didn’t care. After he had paid his bill and left her a tip, he sat in one of the few vacant chairs, proud of himself, not caring in the least about the other women watching him all too closely. The way things had been going lately, even minor victories seemed like major ones, and they needed to be savored.