The Bet - Chapter 36 (Saturday – week 5 Part 8 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 8 of 8)

After they got home again, Mel sent Chad back to his own apartment to change into his uniform. Chad spent the rest of the afternoon cleaning Mel’s apartment, doing laundry, and cooking dinner. Since there was a lot to do, Mel mostly left him alone… except for making sure he was drinking and wetting himself very frequently, and making him change his leaking diaper, and just calling him to her for no reason at all other than because she liked to see him curtsey to her – fun! While Chad was working, Mel had a hard time getting him in a ballet costume off of her mind. She was so tempted to give in and make him put on the parts that they already had, but she restrained herself. It would be much better once the whole thing was here.
As usual, Mel ate her dinner alone while he spent some “reflective time” on his perch in the corner. Then she allowed him to eat his own, now cold, dinner. But she insisted that he hold his spoon the way that Sandy had shown him earlier. “That’s how I want to see you eating from now on,” she told him as she stood back watching him make another mess of himself. There was just something about seeing him humiliate himself further and further that touched a tender part within her – and that tender part seemed to be awfully well connected to her sexual urges!
After dinner, and after he had finished cleaning up the kitchen, and while there was another load of clothes clogging up the dryer, she gave in to her earlier temptation – partially. She put her laptop away and sat in one of her chairs where she would be able to see him better. “Sissy!” she called. “Get in here!”
Chad came running from the bedroom where he had just finished making up her bed with fresh sheets. “Yes, Mistress?” he asked, as he dropped his usual curtsey.
Seeing him doing that, especially in his maid’s uniform, sent another huge thrill right through her. “I don’t suppose you ever took ballet lessons while you were growing up, did you?”
Chad was a bit surprised, and suddenly wary. “No, Mistress,” he replied a bit apprehensively.
Mel shook her head. “Of course not! Why is it that boys never learn anything good?”
Chad remained silent. He didn’t want to touch that question.
“Oh well, we’re just going to have to teach you then.”
Now Chad was getting more worried. Ballet? It didn’t sound good to him at all. Especially in light of the ballet costume she was getting for him – and her sudden desire to send him to work in it!
Mel got up from her chair and removed her shoes. She stood right next to him. “The first thing you’ve got to learn is the basic positions. It’s the first thing they teach every little girl. I’m not sure in how many ways you qualify as a little girl, but trust me, I’m sure you qualify!” She placed her feet, heels together, with her toes pointed as straight away from each other as possible. “This is first position.”
It looked awfully painful and silly to Chad who realized immediately that feet were never meant to go that way. He tried turning his toes out as far as possible. The task was made all that much more difficult because of the shoes on his feet, even though they were his lowest heels.
Mel laughed a bit. “This probably shouldn’t be done in heels… or shoes of any kind, but keep trying anyway. Can you turn your feet out even more? Ideally, the feet should be in a perfect straight line.”
Chad struggled to turn his feet out even further, but what she ideally wanted was clearly impossible. In fact, her own feet weren’t that much straighter than his!
“Good enough. Like I said that’s first position.”
Chad silently wondered what he was supposed to do with “first position.” How the heck could you dance if your feet were all twisted in ways they weren’t supposed to go?
But Mel was moving on. “Now, second position is kind of like that, only spread your feet a bit.” Mel moved her own feet to about a foot apart. Chad tried it but was instantly aware of how much more difficult the seemingly simple position was. He suddenly started to lose his balance and had to move his feet to a more normal position to keep from falling.
“That’s probably going to happen till you get used to it and get your balance. That’s why this is often practiced with a barre to hold onto.” Mel went back to her chair. “Now try it again. First position.” Chad did his best, but there was just no doubt that the position was awkward and uncomfortable. “Now second position.” Chad spread his feet, and almost lost his balance a bit, but he caught himself just in time. “Stand over there by the end of the couch and hold onto that,” Mel suggested. Chad moved back next to the couch and propped his hand on the back of it for support. He tried to go into first position and immediately found that something to hold on to was definitely an improvement.
Mel had him practice going back and forth between positions for a few minutes, then she got up to show him something else. “Now, between positions, put your foot out like this and point your toe. Then move to the next position.”
Chad tried it and found that so far, it was the easiest thing that he had done. But Mel wasn’t thrilled.
“Those shoes aren’t helping,” she proclaimed. “You’re supposed to be pointing your toe and arching your foot like this, but you can’t do that in shoes.” Mel was tempted again to tell him to take his shoes off, but she decided once again to let him leave them on – for now.
Even thought the positions seemed to be awkward and more than a bit stupid for dancing, he found that the added movement did ad a “flavor” of dancing to what he was doing. He even mentally hummed a little tune to himself as he did the steps over and over again.
“Not so fast!” Mel exclaimed. “Slow down! You look like you’re dancing a jig of some sort. This is ballet! It has to be graceful.”
Chad wanted to say something not exactly nice, but he held his silence. He guessed that perhaps she was right about it looking like a jig, but at least that seemed to be more fun than what she wanted.
Mel jumped up again and stood next to him. “In first position, try putting your arms like this.” She held her hands down just below her waist, her elbows bent outward. “Just do it with your one arm right now since you’re holding on with the other one.”
Chad tried it and immediately felt a bit foolish, if not more feminine.
“Relax your hand a bit,” Mel suggested. “Not so stiff.” Chad tried. “Better,” she proclaimed. “Now, for second position, hold your arm out to the side like this.” She brought her arm out. Chad duplicated the movement. “Your hand is too straight,” she complained. “Relax it more. In fact, relax your whole arm. This is not a martial arts contest!”
Chad wasn’t too sure about that but he did his best. Mel sat down again. “Practice!” she ordered from her seat, and Chad did just that. The added arm movements did add more of a dance flavor to it, and unfortunately, they also made him feel like he was moving more femininely. He had mixed feelings about that.
Mel sat back and watched him. Adding a suggesting comment once in a while, but mostly, she was just enjoying the show. He looked a bit odd doing it in his maid’s uniform, but that too added a certain flair of interest. “The Dancing Maid,” she mused. Or maybe, “Maid for Ballet.” She giggled at her own jokes. She immediately thought up another one, “Ballet Maid Easy!” She giggled some more.
But eventually, watching him started to arouse her sexually – especially when she again started picturing him in the entire ballet outfit she had just ordered. She couldn’t wait any longer. “Get that dress off!” she suddenly commanded as she jumped up out of her chair.
Chad didn’t know what was happening as Mel suddenly sounded angry. He removed his apron as fast as he could and was already removing the dress when she came back to the living room with a collection of ropes in her hand. Uh oh! He knew what was going to happen next – and he soon found out that he was right! Before he knew it, he was stripped down to just his single diaper, his waist cincher, and his bra with breast forms. He was down on his knees with his hands tied behind his back – tied to his bound ankles. Mel ran off and came back with towels that she spread out all over her sofa to protect it. Then she ran off again – and Chad knew why. She came back again just as fast as she had done everything else. She didn’t bother with doing or saying anything as she wrapped one of her scarves tightly around his head, blocking off all his vision. That was the part that Chad dreaded the most… no, he decided, not quite. It was what was coming next that would be the real hard part.
Knowing that he could no longer see her, Mel undressed completely. She sat right in front of him and grabbed his hair. She pulled him down onto her with a desperation she hadn’t felt in a while. As she hoped, his mouth landed right where she needed it to be. Ahhh! Almost unconsciously, she ripped the stupid pink bow out of his hair so she could hold onto him better.
Chad could hardly breathe as he felt her pulling him down into her. He realized that there was a desperation in her that seemed to be more than usual. Before he knew it, she was pulling on him even harder as he felt her legs on either side of his head coming up and gripping him too. He felt her explode, then come down again. He heard her gasping for breath. Finally, she relaxed her grip on his head enough that he could get some well needed gasps of air. He breathed in all that he could before she again pulled him closer.
Mel writhed in exquisite ecstasy. Now that her first orgasm had ended, she could almost relax and enjoy the second build up even more. Consequently, she allowed him, and herself, to go slower and easier. His tongue was as talented as ever. The control she exerted over him added just as much to her pleasure. But it had been the visions in her head of him dancing – especially when she imagined him as he would look in his ballet costume – that had finally pushed her into the frenzy she had been in. She couldn’t wait to see the real thing! And then her mind started to wander. What kind of ways could she devise to show him off? Her next orgasm came quickly as the ideas began flooding into her.
It wasn’t till she came down from her third orgasm that she finally eased up and pushed him away. Leaving him tied up and blindfolded, but laying on his side as she often did, she went in and grabbed a quick shower.
Chad had been thorough this the same way many times now. The waiting, bound and blindfolded, was a pain, but he knew she would be there eventually to release him. Time was the only thing that was hard to figure. How long had he been laying there? How long would it be till she came back to release him? He did his best to relax under the circumstances to help him endure his situation better.
Mel finally came back with her robe wrapped tightly around her. She gently untied the scarf around his head and waited a moment for him to blink a few times before she began removing the rest of his bonds. When he was free, she sent him into the bathroom to wash his face – understandably it was a mess! When he came out again, she sent him to her bedroom.
Chad knew what was coming next the moment she told him to lay on her bed. The damn breast forms! What he didn’t understand though, was why she insisted on tying him up while she glued the things on. He wasn’t going anywhere! But as usual, she soon had him totally naked except for his one diaper, spread eagled and unable to move. Before, when she glued the forms onto him, Sandy or Cassie had helped her. This time, she did it by herself. But the results were the same. Before long, the forms were strongly attached to his chest. Without the aid of the solvent, they weren’t coming off any time soon. He was well used to the weight of them now, so it only took him a moment to get used to them again.
He hadn’t leaked yet, and he still had a little while before he needed to be, but he suddenly felt her removing his diaper. She got a washcloth and wiped him clean. She spread many fresh cloth diapers underneath him – some of which were only there to protect the bed in case of “accidents.” Then, untying and retying the ropes, she had him roll over and pull his knees up under him. Chad hoped that she would use one of her toys on his backside. He couldn’t see what she was doing, but he could hear her moving things around in her end table drawer.
Mel looked through her choice of “weapons” to use on him. Her collection was certainly growing. Some of her available choices looked awfully interesting to her – personally. She spotted the double ended strap on. But she had just orgasmed multiple times – although a little more fun was certainly not out of the question. Cassie had said that she thought his sensitivity in that area was still increasing. She decided that it would be better if she chose a toy that would let her see better for herself. She selected the dildo that had the little rings that went all the way around it. She had used that one before on him and he seemed to enjoy it.
Chad was elated the moment he felt her spreading some lubricant on, and up him. He was even more elated the moment he felt her touching the tip of some kind of “toy” against his little opening. He relaxed, wanting it badly. He not only allowed her to push it in, slowly, but he also pushed back against her toy slowly. The feeling of the toy intruding into him, little by little sent waves of pleasure throughout his body. More! He wanted more! He needed more! Little by little, as Mel increased the pace, he not only went along with it, he eventually began setting it, which soon became more and more frantic. As his pleasure built, he pushed in and out harder and harder, faster and faster.
Mel found herself holding onto her the dildo for dear life. He was working it so hard! Obviously, Cassie was right! He was growing more sensitive to it. She watched as he frustration and sink tried harder and harder to achieve – something. And then, she heard him grunt in his head down toward the bed. He shook his head. Obviously, he wasn’t able to achieve any kind of fulfilling satisfaction this way. She didn’t really know if she felt that was good or bad. She slowly pulled the dildo back out of him. He didn’t move a muscle. She checked under him at his penis, completely encased in the hard plastic confines of the chastity device – just as tiny as ever. Amazing!
While he was still in the perfect position, she pulled out a jar of suppositories and pulled one out. “See what I’ve got for you,” she said as she held it where he could see it. Chad lifted his head enough to see the little pill, then put his head down and groaned again. Mel almost laughed. She knew he hated the things. But what he didn’t know was that he would be getting fewer and fewer of them as time went on. She had no trouble sticking it far up his backside after the reaming she had just given him. She untied him and rolled him over. Five minutes later, she had spread baby lotion all over him and he was once again heavily diapered for the night. She gave him his usual instructions to drink three more bottles before he went to bed and also reminded him that he should clean the holes for his pierced ears. Then she watched as he silently collected his things and waddled home.
But even as the door closed behind him, visions of him in a pink ballet costume – danced through her head.

The Bet - Chapter 36 (Saturday – week 5 Part 7 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 7 of 8)

The crowd of girls and women finally disbursed as he and Mel gathered up their things. Chad could feel where the pee had run straight down his legs a little – both of them. Yuck! It was an awful feeling. The minute they got out of the store where it was less likely that anyone would hear him, he said, “Mistress, my diaper is leaking.”
Mel looked at him. “Good! It’s about time!” She looked at her watch. “You’re a few minutes late!” she declared.
“But Mistress, I started leaking a while ago,” Chad countered.
“How long?” Mel asked.
“As soon as they pierced my first ear,” Chad admitted.
Mel only laughed as she led the way through the mall – in no great hurry. At one point she happened to glance back and noticed something amusing. “By the way,” she said, “did you know that the back of your skirt is wet? Probably from when you were still sitting on the stool when you wet yourself.”
Chad was shocked! “It is?” He quickly tried to feel the back of it, but he couldn’t tell much. In desperation, he grabbed his skirt and tried to pull it around where he could see.
“That’s not very lady-like!” Mel admonished. Chad immediately dropped his skirt. He would have to change it as soon as they got home, where he now hoped they were heading.
But Mel didn’t head toward the exit. Instead, she wandered, casually, into the food court. She was certainly moving much slower than Chad was happy about. He had no doubt that many people were noticing the wet spot on the back of his skirt.
Much to Chad’s horror, Mel led the way right into the ladies room. “In there?” Chad asked before going through the door.
“Unless you’d rather use the men’s room,” Mel replied.
Chad shook his head. The way he was dressed, it was possible that the men’s room could be a dangerous place for him. He followed her inside the ladies room with no further argument. Chad hadn’t been in a public bathroom much at all in quite a while. In fact, the only other time recently was with Robin at work – and that was the ladies room too. But here, this rest room contained quite a few women in it. Chad felt very embarrassed among them and very out of place. Mel walked all along the row of stalls, which all had their doors closed, down to the very end where there was a door open. “Perfect,” she said happily as she entered the only available stall. Chad was quick to notice that it was the stall for handicapped women. “If being male isn’t considered a handicap, then I don’t know what is,” Mel added as Chad entered behind her.
Mel closed the door and they both set down their collection of bags. The extra room in the stall was very much needed. Mel let Chad change his own diaper while she tried to stay back out of the way. In the busy rest room, Chad was mostly worried about all the noise changing the disposable diapers made. The tapes ripping open, and the noisy material seemed to make more noise than ever. He was sure that everybody on the other side of the door had to know exactly what he was doing.
As soon as he was done, Mel looked at her watch. “Two hours, Sissy.” Chad knew that perfectly well.
Before they could get out of the ladies room, Chad had to wait, just outside the stall so that Mel could use it for herself. He tried desperately to blend into the corner between the front of the stall and the wall, but he wasn’t having a lot of luck. The women all seemed to stare at him too much, making him more uncomfortable than ever. When Mel came out again, she walked up to the row of sinks and stared at her face in the mirror. She started to adjust her hair, then she turned to Sissy. “Aren’t you going to fix your makeup?”
Chad wasn’t the least bit happy with Mel’s “suggestion.” He looked in the mirror. But the first thing that caught his attention was not his makeup or his hair, it was the bright and colorful points of light now attached to his earlobes. His new earrings. Pierced earrings! He stared at them, not fully believing that they were real. He turned his head back and forth trying to see them better, but it was difficult. He touched each of them carefully – both were a bit sore. He could see them in the mirror. He could touch them. He knew they were real, yet he still couldn’t believe it. Had he really done it? It only took a moment of thought about all the girls in the store watching him as it was being done to answer that question for him. Yes, he had done it. And surprisingly, now that it was over with, he was happy about it.
“They look great,” Mel told him when she noticed what he was looking at. “Very pretty.”
Chad blushed a bit. “Thanks,” he replied. Then, because she had told him to fix his makeup, he dug through his purse and pulled out his lipstick. Just like many of the other women in the rest room, he refreshed his lipstick. He looked at his hair. Yes, the stupid pink bow was all too noticeable – he had forgotten about it… again. But his hair did look a bit better now that Cassie had trimmed it.
He glanced over at Mel to see if she was finished. “All done?” she asked. She had been standing there waiting for him, enjoying watching him looking at himself in the mirror – not very masculine in anything that he did.
Noticing several other women in the room staring at him, a few with amused looks on their faces, he replied. “Let’s get out of here!”
Mel led the way out of the rest room, and eventually back out to the car – although she spent almost as much time looking in store windows along the way as she did the first time through the mall. Chad was just glad to finally get out of there – pierced ears and all.

They were nearly back home when Mel suddenly cried out, “Oh gee! I forgot something!” Before Chad could ask what, Mel almost caused an accident as she quickly changed lanes and then pulled her car into a drug store parking lot.
Chad quickly realized that it was the same drug store he had avoided earlier that morning – and he was still glad that he had! “Why are you stopping here?” he asked.
“Because I need some things,” Mel replied, then added, “And so do you!”
“I do?”
“For your ears. You’ve got to clean those holes every day.”
“I do?”
Mel didn’t reply. She simply got out of the car. But she noticed that Chad wasn’t moving. “Aren’t you coming?”
“Can’t I stay here?”
“Of course not! Why would you want to? Besides, you’ve got more stuff to buy.”
Chad didn’t reply. He simply got out of the car and followed her into the store. He realized that he was being silly to worry. The two girls who usually gave him such a hard time every week wouldn’t be there now. In fact, it was really just an odd coincidence that he had met them at the store the last few weeks.
Inside, Chad quickly discovered what Mel had meant when she said that she needed some things as she headed straight for the period supply section and picked up several different boxes. Then she walked around the store till she found the astringent Chad would need for his ears along with some cotton swabs.
The store wasn’t crowded at all and as usual, there was only one cash register open. But Chad quickly realized that the woman there was the same one he usually dealt with every week – and unfortunately, the woman recognized him right away.
“We missed you this morning,” the woman exclaimed the moment Chad and Mel approached the register.
Mel had no idea what the woman was talking about, but one look at Chad’s face told her something had gone on that she didn’t know about. “You missed him?” she asked.
Chad opened his mouth to reply, but the woman was much faster. “Oh, he usually comes in every Saturday morning to buy a big supply of diapers. And we have a couple of girls that come in Saturday morning too. They usually spend some time… um… talking with him.” She looked at Chad. “They were soooo disappointed that you didn’t show up today.” She giggled. “I was too. And we waited a long time.”
“You didn’t come here?” Mel asked him.
“I went somewhere else,” Chad replied.
“Why? You’ve got friends here.”
Chad wouldn’t have called them “friends” by any stretch of the imagination. “I had to get some other things too. I thought a different store might be better.”
Mel turned to the cashier. “Do you ever see his two ‘friends’ at any other time?”
“Occasionally,” the woman replied.
“Well, if you see them, let them know that he’ll be here next Saturday. I’ll make sure of it!”
The woman giggled. “I’m sure they’ll be very happy to hear that!”

The Bet - Chapter 36 (Saturday – week 5 Part 6 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 6 of 8)

Mel’s next stop was a jewelry store. Chad first thought they were going to walk right past it, but suddenly Mel stopped and quickly headed straight for one of the display cabinets. Since the store didn’t seem to have too many walls on the outside, Chad carried his drink right up to the display case with her. “Gee that’s pretty,” Mel said, pointing to one of the rings in the case.
Chad looked at the ring. It had a rather large diamond in the middle of several smaller diamonds. He looked at all the rings in the case. They were all diamond rings. Wedding bands? Why would Mel be looking at wedding bands? Not knowing what else to say, he replied. “Yes. It is.”
But while Mel was busy perusing the rings in the case, Chad’s attention was caught by a slowly revolving display case on top of the main case. He walked over to it and looked inside. Earrings. Actually, very pretty earrings. He had always fantasized about getting his ears pierced and wearing such things. The thought that he could do it now made him stop and really consider it.
“What are you looking at?” Mel asked, noticing that his attention was solely on the case in front of him. She walked up next to him and looked. “Oooo. Pretty. Are you considering getting your ears pierced?”
Chad thought about it a moment more before he answered. The women at work kept telling him he needed to get them pierced. He had always fantasized about it. And now would be the perfect time – now, before he won the bet and his situation would change so that it would no longer seem… appropriate. But there was still just… something… holding him back. “I don’t know,” he admitted. “What do you think?”
Mel knew she could have easily told him to have his ears pierced and it would be a done deal. In fact, she had considered it in the past. But this one thing, she had always wanted to be his decision. Why, she didn’t know. “I think you’re the one who needs to decide.”
Chad wasn’t really glad to have the decision left all up to him. For everything else, when he had been told or forced to do something, there was always that little bit of an “excuse” that he could rely on. But this time, there would be no background excuse. She was leaving the decision all up to him.
Mel watched him. She could almost see the gears turning in his head as he thought about it. “What’s really stopping you?” she asked.
Her question seemed to change something in his head though. “I’ll do it!” he finally declared, taking the huge leap.
Mel silently wanted to applaud.
Chad looked around the jewelry store. “I don’t see a sign saying they do ear piercing here.”
Mel looked too. “I don’t either. But we can ask.” But just then something in the rotating case caught her attention. She looked closer, then quickly reached out to press the button to stop it from turning. She pointed at a pair of the earrings. “I like those! And they’d be perfect for you.”
Chad looked to see what she was pointing at. He should have known. Pink crystals – of some kind. They matched all his other jewelry. But he had to admit, they were kind of pretty. Could he see himself wearing them? He wasn’t really sure. “Um…” he stammered. “I really like them, but all the women at work have been on my case lately to start wearing other things besides the same stuff I always wear.”
That was news to Mel. “So why don’t you?”
“Because you told me I had to always wear what I’ve got now. Besides, what I’m wearing is all I’ve got.”
Mel realized that it was absolutely true. “Well, I think that you’ve grown beyond that point now,” Mel told him. “Why don’t we stop in one of the cheap costume jewelry stores and you can find yourself some new stuff. How does that sound?”
Chad considered it. “I guess it sounds fine,” he admitted. He took one last look at the pink earrings. “They are kind of pretty though.”
“So why don’t you get them?”
Chad considered it. “I wonder how much they are. I can’t see any prices on these.”
Mel smiled. “Every girl needs at least one good set of earrings.”
Since they had been standing there talking and looking at the jewelry so long, one of the saleswomen walked up to them. “May I help you?” But as soon as the words were out of her mouth, she stopped and stared at Sissy, obviously surprised to see a man dressed as a woman standing in front of her. Chad felt very self-conscious under her surprised gaze, but then, that was nothing new.
“How much are these?” Mel asked, pointing at the pink earrings.
The saleswoman recovered her senses and unlocked the case. She pulled the earrings out and opened the tiny box they were in and showed the price to Mel. Chad looked too. They were more expensive than he had thought, but really, not too bad. “I’ll take them,” he told the woman in his sissy voice. The saleswoman looked back up at Chad, further surprised, but she simply pulled the price tag off of the earrings and relocked the case they had been in. “Um…” Chad continued, “do you do ear piercing?”
The woman actually looked relieved when she replied that no, they didn’t. But there were many places in the mall that did.
“We’ll find someplace else,” Mel said. “You should have several pairs anyway.”
Chad paid for the earrings. And dumped the tiny bag he was given into one of his other bags. At least it wasn’t much to carry. As they were leaving the store, Chad had to ask, “Why were you looking at wedding rings?”
Mel just shrugged her shoulders. “I don’t know. I guess because every girl dreams of having one someday.” She looked at him slyly. “Don’t you?”
“Um… Not that kind,” he admitted. Mel just giggled.
Instead of moseying on in the direction they had been going, Mel led the way back toward a store they had bypassed earlier. Along the way, Chad finally finished his drink and was able to get rid of that big item from his hands. Now, he just needed to start leaking. But did he really want to leak while they were out shopping? No, he didn’t! But Mel didn’t seem interested in going home yet.
When they got to the store, Chad saw that it was packed with racks of inexpensive “girly” things. It was also packed with teenage girls. Mel didn’t hesitate one bit about going inside, but the moment Chad saw all the girls in there, he stopped where he was. Teenage girls and someone like him didn’t mix very well… he didn’t think so anyway.
Mel saw him hesitate. “What’s wrong?”
“Maybe we should find someplace else to look,” Chad suggested, never taking his eyes off of all the girls inside.
Mel looked around and guessed what was bothering him. “Nonsense! This is the perfect place,” she replied. But silently she was thinking that if any of the girls said anything to him, then all the better. He did like humiliation anyway.
Chad had little choice but to follow her inside. There was cheap jewelry, cheap scarves, cheap belts, hair decorations, and tons of sparkly “girly” things displayed on racks everywhere. Mel busied herself looking at several different racks of jewelry before she realized that Sissy was just following her and not looking himself. “What are you doing?” she asked. “You’re supposed to be here looking at things for you.”
Chad shrugged. “I don’t know what to look at.”
“Everything! Find things that you think you might like to wear! Find things that are fun!”
There was a nearby girlish giggle, but when Chad turned to look to see who had laughed, he couldn’t tell which girl had done it. He started looking at some long bulky necklaces on the rack next to where Mel was looking so he wouldn’t be too far from her. Most of the jewelry he was looking at seemed to be made of colorful wood, but he wasn’t really sure. He touched one that looked interesting, just to see what it was really made of.
“That will probably look real good on you,” a voice said from behind him. “Especially with that pretty bow in your hair. Chad turned around to see who had spoken just as the girl and her two friends broke out in peals of laughter. Chad’s face turned red, especially when one of them suddenly reached up and lightly flicked the bow that was clipped into his hair. The girls all laughed again as they moved on. Chad had again forgotten about the bow in his hair. Actually, he realized that he preferred it when he hadn’t remembered about it because now he was more self-conscious about the bow than ever.
“They’re right though,” Mel added from his other side. “I kind of like that one too. Good choice!” Chad hadn’t intended on buying it, but he realized that now he almost had to. He pulled the necklace down off of the rack.
“You should get several of those,” Mel added. “Then you can wear them together or separately.”
Together or separately? How was he supposed to know what to do with them? But as Mel suggested, he pulled two more of the long necklaces off of the rack and held them in his hand. They were all a little different, but in the same style. On the same rack, he found a large bracelet that kind of looked like it would go with the necklaces so he grabbed that too.
When he turned around to check where Mel was, Mel wasn’t there. He searched the store, but didn’t see her. Slightly panicked, he started toward the store’s entrance, but then he spotted her looking at things closer to the cash register. He walked up to her as if he wanted to see what she was looking at, but mostly, he wanted her protection because of all the younger girls around.
“Look at this,” Mel said as soon as she realized he was there. “They’ve got some nice starter earrings here. And, they do ear piercing!”
Chad looked around him. This looked like the last place on earth that he wanted to have it done. “I don’t think doing it here is a good idea,” he said.
Mel looked around too and again noticed all the girls in the store. “Nonsense! It will be memorable!” she replied.
Chad had no doubt of that.
Together they picked out three sets of starter earrings for Chad, then they finally found someone who was willing to help them – which turned out to be another teenage girl – who was more excited than Chad figured she should be to help them with Chad’s piercing.
Mel picked up on how excited the girl was over Chad immediately. The girl could barely control her giggling every time she looked at him. Mel recognized that maybe, if the situation presented itself, she could use the girl to help make this event even more memorable for Chad.
After they paid for everything, the girl brought out a simple wooden stool from behind the counter for Chad to sit on. “Which earrings did you want to use?” she asked.
The three sets of earrings they had picked out were lined up on the counter. Mel looked them over carefully. “I’m not sure,” she finally said. “I like them all.” She selected a pair, still in its box, and held it up to one of his ears. “What do you think?” she asked.
The girl looked. “I think they’re very pretty. They should do just fine.”
Mel selected another pair and held them up to Chad’s ear instead. “How about these?”
“They look good too,” the girl replied.
Mel quickly realized that they were drawing a small crowd. She handed the earrings she was holding to the salesgirl. “Hold these next to his other ear,” she instructed. The girl did as she requested. But instead of looking, Mel grabbed the first pair of earrings instead and held them up next to his ear on her side. Then she turned to some of the girls that were looking on. “What do you think? Which ones do you like better?” Mel was immediately rewarded with a noticeable increase of giggling from the girls who were looking on.
Chad felt so embarrassed the moment he sat down on the stool and noticed the attention he was attracting from the rest of the store’s customers. But the moment Mel asked for their opinion, his embarrassment went from bad to worse! Memorable? Yeah, this was certainly looking to be memorable! And he had no way to get away from it.
Mel heard differing opinions from the crowd of girls looking on. “Switch boxes,” she said to the salesgirl. Once the boxes were switched, Mel again asked for opinions, and once again she got the same mixed reply – amid much more giggling from the growing crowd of girls. Mel figured though that the consensus seemed to be that they liked the tiny pale blue earrings better.
“Wait!” she told everybody. “We have another pair to try too.” Mel put down the box she was holding – the blue ones that most of the crowd liked best, and picked up the third pair of earrings, the multi-colored ones. She held them up next to Chad’s ear while the salesgirl, who was now thoroughly enjoying the game, held the plain ones up to his other ear. Mel looked to the crowd, which seemed to be even bigger than it was a minute ago. “Which ones do you like best?” she asked again. This time, it was clearly the multi-colored ones.
“Okay,” Mel replied to them all. “So I take it, the plain ones are out!” There was a small chorus of “Yeahs” from the girls looking on. She handed the salesgirl the blue ones to hold up instead while she held the multi-colored ones. “Which ones?” she asked yet again to the crowd. As far as she could tell, every girl that had been in the store was now watching. Again there was some mixed opinion, but overall, Mel figured that the multi-colored ones were the crowd’s favorite. She handed the colored earrings to the salesgirl. “We’ll start him off with these,” she said.
The crowd, realizing what was about to happen didn’t disburse at all, as Mel figured they wouldn’t. She looked closely at Chad’s face. His eyes were very wide and he looked completely scared. Panicked, she realized. Perfect!
Chad didn’t know what to think. So many girls and women… mostly teenage girls, were looking right at him, watching closely at what was about to happen – to him! This was not what he had in mind when he agreed to have his ears pierced. The only thing missing here was the six-o’clock news! As the preparations got under way to pierce him, his panic didn’t abate at all, in fact, knowing that the deed was growing more and more imminent, his panic got worse with every little thing that they did.
And then the salesgirl put something hard around his earlobe. “You may feel a slight pinch,” she said, but that should be all.
A slight pinch? But before he could fully brace himself, he felt it… and at the same moment, he felt his bladder give way, flooding his already very wet diaper. He realized that he had been so preoccupied with what was happening to him, that he didn’t even realize he had to go. And as his bladder continued to empty itself out, the girl moved around toward his second ear.
He dared not move. Actually, he was too scared to even breathe! His bladder finally stopped emptying itself as she put the gun to his other earlobe. It took her a moment to get it lined up perfectly. And then came the “pinch” that she had warned him about. He almost didn’t remember it from the first ear. But he remembered it more this time. And as soon as the “pinch” ended, he felt the leaking from his diaper beginning. Ugh! Now what was he supposed to do? All these people – mostly girls – were watching him!
“There. All done,” the girl told him. Chad realized that he had been so preoccupied with his diaper beginning to leak that he hadn’t fully realized that he now had pierced ears. The girl was standing back a step, looking at him critically. “Perfect!” she declared as a few of the girls looking on began clapping.
Mel was all smiles. “They look wonderful,” she agreed. “Very pretty.” She turned to the crowd behind her. “Thank you for your help... All of you!” There were few in the crowd who outright laughed.
Very red-faced, Chad looked up at Mel. He desperately wanted to tell her about his diaper, but he couldn’t do that with everybody looking on. He decided he had to hope that nobody would notice.

The Bet - Chapter 36 (Saturday – week 5 Part 5 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 5 of 8)

Mel was ready and waiting for him when he knocked. She grabbed her purse, and his diaper bag and opened the door. She was immediately greeted by him with his usual curtsey. She smiled and simply pushed past him.
Chad was a bit nervous about going to the mall. The last time he was there was when she had dressed him up in one of his super sissy dresses and made him act like a super sissy inside. So embarrassing! Would anyone remember him from that? Quite possibly! Since he was still recognizable as a man wearing women’s clothes, he figured that it would be very easy for anyone to make the association. Not a good thing as far as he was concerned!
Mel parked the car. Chad hesitated a moment before getting out, as if he was trying to find the courage within himself to go into the mall again, but he delayed only for a moment. Then he followed Mel inside where she handed him his own diaper bag to carry so she wouldn’t have to lug it around.
Whenever he had been out with her before, dressed in his maid’s uniform, it was obvious to everyone that he was her servant. Now, strangely, she was walking beside him and chatting with him about things she saw in the display windows as if he was her best girlfriend. It seemed so strange. He often didn’t know how to properly reply to her comments but fortunately, she didn’t seem to mind the times when he said nothing.
She led him into many stores, always telling him to look to see if there was anything he wanted to buy for himself. But Chad wasn’t really interested in looking at anything for himself. He did get the “privilege” of holding her purse often while she tried on different outfits. Somehow, dressed as he was, holding her purse didn’t seem to matter much at all.
When they finally got to the department store where he had bought his makeup, Mel again teased him about asking for another makeup demonstration, but again Chad politely refused. He did have to ask for all the makeup items he needed in his stupid sissy voice though – since Mel was standing right next to him – which gave the makeup girl quite a shock at first, then sent her into fits of laughter. Embarrassing! But fortunately, Mel didn’t make him do anything else there to embarrass him further.
It wasn’t till they left the store and headed out into the mall area that Mel paused and stopped. There was a store stuck in the corner, just off of the entrance to the department store that had been there a very long time. But it was one of those stores that she had never bothered with before, so she barely ever noticed it. But now… now it sparked not only interest, but also, fantasies! Much to Chad’s horror, she headed straight for it.
The dancewear shop that they entered wasn’t huge, space wise, but the store was so packed with display racks that it was hard to move without constantly brushing against something. The moment they entered, Chad started to hang back neat the entrance. Horrible visions of her sending him to work in a pink ballet outfit were constantly running through his mind.
Mel walked right up to the woman behind the counter. “May I help you?” the woman asked politely.
Mel smiled. “I’d like an outfit for…” She looked around for Sissy, but he wasn’t there. She finally spotted him half hidden by one of the racks near the door. “Sissy! Get over here!”
Chad hated it, but he grudgingly moved toward the counter.
Mel returned her gaze back to the saleswoman. “I need it for… her!”
The woman looked Chad over carefully. Her surprise showed obviously in her eyes. “You’re serious?” she asked Mel.
“Of course,” Mel replied, slightly put off. Chad lowered his embarrassed gaze down to the floor, searching for that hole that never appeared to swallow him up.
The saleswoman finally shrugged and replied. “What exactly did you have in mind?”
Mel smiled again, wickedly, but she smiled. I think a pink leotard, white tights, a white tutu, and pink toe-shoes.
The woman looked at her for a moment to take it all in. “Okay, she finally said. “The tights are the easiest.” She moved out from behind the counter and went directly to a display rack against one of the walls. “How many pairs?” she asked.
“Just one, for now,” Mel replied.
The saleswoman looked at Chad once again to gauge his size, then selected a package of white tights in his size from the rack which she handed to Mel. “Now, as to the leotard…” She led the way to a rack of them in all different colors. “Let’s just get the style you’d like first. I’ve probably got the color in the back somewhere.”
Mel picked out a fairly simple leotard with a scooped neck and short sleeves. After glancing quickly at Sissy again, the saleswoman excused herself and went to the back room where she found one in pink and brought it out. “That’s the easy part,” she said to Mel as she handed the leotard over. “Now, what style tutu?”
“What’s available?” Mel asked. “I’d really like something that is wide, but not too long.”
“Classic or pancake style?” the woman asked.
Mel thought about that for a moment. “Probably pancake,” she replied. “Do you have any that I can see?”
Chad suddenly didn’t have a clue as to what they were talking about. The woman led them back up to the counter where she opened a book and started going through the pictures with Mel. Mel quickly pointed to one of the pictures. “That! That’s exactly what I’m looking for.”
The saleswoman smiled. “In white, I think you said?”
Mel nodded. “Definitely in white.”
The woman returned to the back room. She was gone a while, then she came back again. “I’m sorry,” she said as she returned. “But we’ve sold out of everything we had in that style. We should be getting some in next week or the week after if you’d like to check back then. Of course, we can always order you one if you like.”
Mel considered it, but decided to delay her decision. “How about the pink toe shoes?”
The saleswoman again looked at Sissy. “What size shoe do you take?”
“Ladies size nine,” Mel replied for him.
Chad winced. Size nine was fine, he could wear shoes in that size, but they were tight.
The woman went back to the back room again. When she returned, she was once again empty handed. “It seems were out of those too,” she apologized. “I’m afraid the dance schools all have their recitals this time of year and we’ve been selling out of some things as fast as we can get them in.”
“In that case, order a pair for me… the tutu too.”
Words that Chad very much didn’t want to hear. He could already see her dropping him off at work in the outfit and stranding him there. And curiously, for the first time in a while, he was aware of how sexually arousing the concept was… not that his main sexual member was even capable of reacting to it anymore.
“You’ll have to pay in advance, I’m afraid,” the woman said to Mel.
“No problem. That should be fine.” She turned to Sissy. “Get over here and pay for all this stuff. It’s all for you anyway.”
Chad was forced to pay for everything, but Mel gave the woman her own phone number and address so that she could pick the missing items up when they arrived.
Feeling slightly disappointed that she couldn’t get everything now, but still very happy and excited about what was soon in the future, Mel led the way back out of the store. Chad now had another bag to carry along with his bag full of makeup, his purse, and his diaper bag. Mel seemed happier than she had been all day.
Chad was more worried than ever! “Mistress,” he said in his best sissy voice. “I thought I’ve done everything you wanted. And now you’re still going to send me to work in the ballet outfit?”
Mel was amused. “I haven’t decided yet,” she told him. “Yes, you’ve done everything I’ve asked, but I can’t very well decide to send you like that in the future if we don’t have the outfit first.” She decided to let him stew on that thought for a bit. Besides, it was true!
But Chad’s fears were only partially allayed. No, she wasn’t planning on sending him to work that way… yet. But there was still the future to worry about.
A little while later, Chad checked his watch. His two hour time limit was quickly drawing nearer. He was very wet, but not yet wet enough for his diaper to be leaking any time soon. “Mistress,” he said in his sissy voice. “Maybe it would be a good idea if we went home soon. My two hour limit is almost up.”
“Are you leaking yet?” Mel asked, not even bothering to look away from the display window she was staring into.
“Not yet, Mistress. But something to drink would be a big help. I haven’t had anything in quite a while now.”
Mel realized that it was true. She wasn’t really helping matters by ignoring that fact. And keeping him wetting had to be her first priority. “Let’s stop and get a drink first,” she suggested.
Chad would have been a lot happier if they had just gone home first. A short while later, he was sipping on a very large soft drink while Mel continued shopping. Not being able to carry the drink into the stores, Chad was forced to stay out in the mall area while Mel went inside. During one of her trips into a store, he took the opportunity to sit on a bench and take the strain off of his tired and aching toes.
“Didn’t I see you here last week… doing some kind of dance and singing some crazy song?” a voice from nearby asked.
Chad, horrified, turned and saw an older man sitting on the next bench looking at him. He realized that the area he was sitting in was the same area he had “performed” in when Mel had brought him here in his super sissy dress.
But when Chad had turned to look at the man, the man definitely recognized him. “That was you!” the man added with a slight laugh. “You were wearing some crazy outfit too. I got a real kick out of it!”
“Uh… Thanks,” Chad answered, not knowing what else to say. “I’m glad you enjoyed it.”
“Most interesting thing I’ve seen here in ages!” the man replied. “Are you going to do it again?”
“I hope not!” Chad stated, fervently hoping that it would be true.
“Pity,” the man said. “I rather enjoyed it.”
Unfortunately, that was the point where Mel walked up. “Enjoyed what?” she asked.
“His little show last week,” the man replied.
“We’re glad you enjoyed it,” Mel said to him with a broad smile on her face. “We’re considering doing it again, only maybe something better next time.”
The man’s face showed his complete interest. “When?” he asked anxiously.
Mel shook her head. “I don’t know yet. “We haven’t decided.”
“Well, I’m here most days about this time,” the man replied. “Got nothing better to do, just getting out of the house for some exercise and people watching. I hope you do it while I’m here!”
Mel smiled at him. “We’ll try.”
Chad was beside himself. Do it again? Something better? Where was that tidal wave that was supposed to come through and wash everything away?

The Bet - Chapter 36 (Saturday – week 5 Part 4 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 4 of 8)

Once Mel had left, Chad was again strapped into the highchair with his right arm trapped under the tray while he attempted to eat his baby food lunch without spilling too much of it – a mostly impossible task! The sound of the door opening caught his attention while he was still trying to eat. Once again fear froze him in place. He was almost relieved when Cassie came in.
“Hi everyone,” she said fairly calmly, despite not being able to take her eyes off of Chad – and his mess.
“Hi Cassie,” Sandy replied.
But Cassie acted like she didn’t even hear her. She just stared at Sissy instead. “You’re looking rather colorful today,” she noted, referring to all the baby food that was spilled all over him.
Sandy laughed. “Simple little changes, and now he acts even more like a baby than ever!”
“I’ll say!” Cassie agreed as she watched Chad dropping more baby food from his spoon onto his already messy bib. She put her purse down on the counter. “Does Mel still want me to trim his hair again?”
“I guess so,” Sandy replied.
“Let me know when he’s done there and I’ll do him before you let him up.” She walked off toward their bedroom and out of sight.
Get his hair trimmed? That was news to Chad. He wasn’t sure how he actually felt about it either. As soon as Sandy had decided he had eaten enough, she took his plate and spoon away from him and again washed him thoroughly with her washcloth – including the also messy unfinished baby bottle that was still on the tray. Then she called Cassie. Chad, unable to leave the highchair and consequently having nowhere to go, just picked up his bottle and continued drinking – he did have another two hour deadline to meet!
Cassie came back a few minutes later – scissors, comb, and brush in hand. Chad put his baby bottle down as she ran the comb through his hair a few times. “I think we’re going to need to wet this before I can do anything else,” she declared. “You may as well keep drinking that thing while I’m working here,” she said to Chad. “You’re not going anywhere, and I’m not going to be doing anything that will get in your way.” Chad picked up his bottle again.
A few minutes later, Chad’s hair was soaking wet as Cassie combed and trimmed tiny bits off of his hair all over. He wondered how ridiculous he must look as he sat there with wet, must-up hair, sitting in a highchair, drinking from a baby bottle, while wearing only a diaper – that was now wet. He was glad he couldn’t see himself in a mirror just then, he had no doubt that he made an absolutely ridiculous picture of a baby.
As Cassie cut and combed, Sandy looked on closely and occasionally made some suggestions. But it wasn’t long before Cassie put her scissors down and picked up the blow dryer and curling iron. Chad’s bottle was long finished before she was. Sandy looked at him critically and smiled. “Looks great!” she exclaimed.
Cassie stepped back and looked at it too. “Yeah,” she agreed. “It’s only been a few weeks, but it’s starting to even out now as it grows in. Chad had no idea what his hair looked like. It mostly felt the same, but without a mirror he had no way of knowing anything.
“Wait a sec!” Sandy suddenly exclaimed. “It needs something…” She ran off towards her bedroom and came back a few minutes later. Chad saw a large pink bow in her hands. She clipped it to his head just off to one side and stood back again. “There! I love it!” she exclaimed happily. Cassie just smirked.
Sandy released Chad from the highchair and sent him into the living room where all the toys were. Since she had left him alone and didn’t follow him, Chad didn’t bother to “play” with any of the toys. Instead, he just laid down on the blanket and tried to rest. Curiously, he wished for his pacifier. He was very tempted to stick his thumb into his mouth, but resisted that impulse furiously.
“I don’t hear you talking to your toys!” Sandy’s voice called from the kitchen.
Chad groaned and sat up again. He picked up a plastic toy block and babbled at it. Then he switched it for another toy.
Sandy came in to see him a few minutes later. She had another baby bottle in her hands. “Since you’re on a time limit now to make your diaper leak, I brought you another bottle.”
Chad took the bottle gratefully, even though he could really have done without more to drink… but if he was going to meet Mel’s deadline, then he really had to keep drinking.
Sandy knelt down on the blanket with him and picked up a small doll that was there. “Here,” she said, “hold this.” Chad started to grab for the doll, but she immediately pulled it back away from him. “No, no! Put your bottle down first and use both hands. Babies need two hands to hold something this big.” Chad thought it was stupid, but he did as she wanted – he really didn’t have a whole lot of choice in the matter anyway. “Now,” Sandy continued as soon as he was holding the doll in both hands, “stick it into your mouth.”
Chad’s eyes bulged. Stick it into his mouth? She had to be kidding.
But Sandy quickly went on to explain. “Babies try to stick everything into their mouth to taste them or teethe on them. They often slobber all over most of their toys. So from now on, before you talk to any of your toys, I want you to stick it into your mouth first and make sure that part of it gets good and wet. Chew on some of them a bit if you have to. Since you have to keep drinking from your bottle today, then that should help.”
Chad couldn’t believe it. She really wanted him to do that? Obviously she did! As crazy as it sounded, she meant it. But then of course, Chad had seen babies doing exactly that many times. Now she was simply making him do it. Ugh! He took the doll he was holding and stuck part of the head into his mouth – yuck! It was dry and tasted awful. He had to chew on it for a moment before he thought it felt even a little bit wet. Then he gratefully removed it from his mouth again. He looked at it – yes, the head and part of the hair was just a little bit wet. He babbled at it for a moment, then put it aside and grabbed his bottle. He really needed to wash the taste out of his mouth.
“Now do that with all your toys,” Sandy told him.
Chad picked up the toy block he had been talking to earlier and stuck the corner of it into his mouth. He made sure that part of the block got good and wet before he pulled it back out and babbled some nonsense at it. Then he put it down again and grabbed for his bottle.
“That’s it! You’ve got it,” Sandy declared as she stood up again. “Now just keep doing that till Mel comes for you later.”
Till Mel came back for him? When was that supposed to be? And he had to keep doing it? He picked up another toy and stuck it into his mouth. Yuck!

Mel took the cover off of the huge pot on the stove, looked inside, stirred it with a spoon for a bit, then turned off the heat underneath. She picked up the heavy pot and with a great deal of effort, poured the tea that she had been making into a large pitcher. The pitcher made things much easier for her to pour the tea into the small opening at the top of his baby bottles.
She refilled the big pot with water and stuck it back on the burner again to start making more tea. Keeping him drinking it meant that she had to keep making it. She added half a dozen of her green tea bags to the pot and left it alone. It would be a while before it was done. In the meantime, she had a lot of empty baby bottles all lined upon her counter that needed filling. She picked up the now heavy pitcher and started filling the first bottle. So many baby bottles – for such a big baby. Yet she didn’t really mind making the tea for him like this. Something about doing it was kind of fun… and maybe relaxing. It took very little thought, yet it kept her busy. And… it was directly helpful to winning the bet between them.
When the pitcher was empty, she set it down and checked the pot on the stove, not ready yet, but getting there. She took the bottles she had filled and set them into her refrigerator to start cooling. By the time she was done today, a good bit of her refrigerator would be filled with the bottles – and Chad’s refrigerator too.

Chad noticed that he was peeing yet again. Since the bottles were a lot better in his mouth than the taste of the toys, he was drinking even more than usual. But the result was that he was also wetter than usual. He looked up at the fancy clock on the wall. He still had more than half an hour to go before he needed to be leaking. But just thinking about his diaper made him realize something else, the damn suppository was about to do its thing. He never even thought about stopping it or even trying to hold it back. As the mess quickly started sliding out of him, he simply got up from his sitting position into a crawling position to make the process easier – physically… emotionally, he still hated it. But as his backside finally finished emptying itself out, his front side resumed. He looked down under him and noticed that he was dripping onto the blanket under him. Uh oh! Trouble. He was sure that Sandy wasn’t going to be too pleased to see that! But what could he do about it? He let out a rather loud stream of baby babble, trying to get Sandy’s attention, where ever she was. But after almost a minute, he still got no attention from her. He figured that he had only one avenue left to quickly try to bring her attention to his problem. He did his very best to fake a baby crying.
“What is it Sugar?” Sandy asked as she came running out of the bedroom. Chad only looked down at the wet spot on the blanket below him. Sandy suddenly sniffed the air. “Oh! Pew! You stink!” Then she noticed the wet spot under him. “Oh darn!” she exclaimed. “Now I’ll have to wash the thing. You stay right there baby and I’ll call Mel.”
A few minutes later, Chad was crawling in his very messy and leaky diaper toward the door while Sandy fussed about how wet he had gotten the blanket. Serves her right, Chad mused to himself, happy that for once he had a way to make things unpleasant for her. Mel opened the door for him and he crawled outside, then stood up again. Finally! He immediately felt more pee running down his leg. Oh well, he was about to get changed anyway.
Mel opened his apartment door for him, but on the way through, he felt himself peeing yet again, which let loose even more pee running down his leg. He hurried into his bathroom and carefully ripped off his messy diaper as quickly as possible and jumped into his shower to get cleaned up. When he came out again, Mel was leaning against his bathroom door to watch him. He quickly dried himself, then grabbed only one diaper – knowing that it was what she wanted. He quickly taped it in place before he might have to pee yet again. Safe!
“Two hours, Sissy,” Mel declared with satisfaction. “Or less, if you can make it again.” Then she laughed as Chad’s face turned red.
“Hurry and find something to wear. I’d like to get to the mall before that diaper gets too wet.”
Chad curtseyed. “Yes, Mistress,” he replied as usual. “Is there anything specific you want me to wear?”
“Whatever you want,” Mel replied, knowing that the only clothes he had to wear were all women’s clothes. Then she looked at the bow in his hair and added with a small laugh, “Something pink might be appropriate.” She left him then to get ready herself.
Chad didn’t know why she had been laughing, but he found a pink skirt and a patterned top in his closet that he put on, over his bra with breast forms and waist cincher. Since he was wearing only the one diaper and was on another two hour time limit to make it leak, no girdle or pantyhose were allowed. It wasn’t until he looked in the mirror to start his makeup that he noticed the bow that was still in his hair. He had forgotten about it. He was about to pull it out, but decided to leave it. Mel had said that pink would be appropriate, probably because of the bow in his hair.
He stood back and looked at his hair more critically. It mostly looked the same as it had, only neater than it was before. But he could defiantly notice now where it was looking a bit longer at the sides and back then it had looked before Cassie trimmed it. He decided he liked it. Besides, since it was basically the same hairstyle, he knew how to take care of it. He quickly finished getting ready and headed out the door to Mel’s apartment.

The Bet - Chapter 36 (Saturday – week 5 Part 3 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 3 of 8)

It was still a few minutes before twelve when someone knocked on Chad’s door. Chad figured it would be Sandy, but he was a little surprised to see Mel there since he figured she would just use her own key and come in. He dropped his curtsey to her, “Hello, Mistress,” he said in his sissy voice.
“I know it’s not quite twelve yet,” Mel said, “but I just thought I’d come over to see if you were busy.”
Chas stood back out of the way to let her inside. “No,” he replied. “I was just giving my kitchen a quick cleaning. It was getting dusty.” As she walked in, Chad noticed the book she had in her hand – the child’s menu he had colored at the restaurant last night.
“Dusty? I guess you don’t really get to use it much.” She headed straight for his kitchen and laid the child’s menu out on his kitchen counter. Chad watched as she started going through the pictures. “I like this one… and this one the best,” she said as she placed one hand on one page to mark the place, and opened the book to the second picture. “Which one do you like?”
Actually Chad didn’t like any of them at all, especially since the ones that she had picked out were the ones that looked the most childishly colored. He had visions of having one of the pictures hung on his living room wall, right next to the one that was already there. How embarrassing… and what a terrible reminder of what he had been forced to do. He took the book from Mel, careful to hold the place of each picture, and turned back and forth between them a few times. The second one was a bit more mature looking, but not by much. “I like this one,” he said, indicating the second picture.
Mel smiled as she took the book back from him and opened it fully to that page. Chad wasn’t the least bit happy to watch as she carefully ripped the page out of the book. She handed the picture to Chad. “I think that Sandy would just love it if you gave that to her. And I want you to tell her that you colored it – just for her.”
Chad was shocked. “Give it to Sandy?”
“Unless you want to hang that one on your wall and give her the other one instead.”
Chad shook his head. “No, Mistress. I’ll give her this one.”
“Good! And don’t forget, tell her you did it just for her! Now let’s go see if we can find something a bit more childish for you to wear for her today. If you’re going to give her a childishly colored picture, then the least you can do is to dress a bit more appropriately.
Not happy about it in the least, Chad followed Mel back to his bedroom where she quickly picked out the onesie he had slept in last night. As he took his clothes off, Mel was careful to check the state of his diaper. “You’ve only got about half an hour to get that thing leaking,” she reminded him.
“I know,” he replied. “I think it’s getting close already. Can I just change it now instead?”
“No, not till it’s leaking. I don’t want you to stop trying.”
Chad wasn’t happy about it, but there was nothing he could do about it either. The sound of someone knocking on his door came before he even got the onesie on.
“That will be Sandy,” Mel said. “I’ll get the door, you get dressed.”
“Hi Sandy,” Mel said with a big smile the moment she opened the door.
“Hey Mel. Is he ready?”
“Almost,” Mel replied. “Come on in.” Mel led her back to Chad’s bedroom where he was just stepping into the onesie. She noticed how wet his diaper looked already. “I take it he hasn’t leaked yet?”
“Not yet,” Mel replied. She checked her watch. “But he still has another twenty-four minutes to go.”
“Then maybe we should just leave him in his diaper till then. That way we can see if he leaks. Besides, once he gets to my place, he won’t be able to tell us.”
“That’s true,” Mel replied with more than a hint of amusement. “Take it off again,” she told Chad. “You can start out in just your diaper.”
“For that matter, he can stay in just his diaper today” Sandy decided. “Maybe just a pacifier to complete his outfit and that’s all he should need.”
Mel smiled. “I like it!” She looked at Sissy. “Where’s your pacifier?”
“In the kitchen,” he replied, fully unhappy that the thing should even be mentioned.
“Then go get it. And hurry!”
Chad ran to the kitchen and came back a moment later with the pacifier in his mouth.
“Now that’s more like it!” Sandy declared. “Are you ready?” she asked him.
Chad just shrugged. “I guess so,” he said around the pacifier in his mouth. “What else is there?” He wasn’t taking any other clothes or anything else.
“How about his diaper bag?” Mel suggested.
“Yeah,” Sandy replied. “Good idea! I guess with him, it really is just like taking care of a real baby!”
“Oh wait!” Mel suddenly said. “We almost forgot something!” She looked right at Chad. “Isn’t there something special you have for Sandy?” she asked.
Chad blushed and Sandy looked a bit surprised. “I’ll be right back,” Chad said as he hurried out to his kitchen one more time to get the picture he had colored. As he carried it back to the bedroom, he saw Mel looking at him very intently. Her stare let him know that he had better do this right – the way she wanted him to do it. Sandy just looked quizzical since she was wondering what was going on. “Um…” he said as he stood in front of Sandy and held the picture out to her. “I colored this for you.”
“For me?” Sandy replied in a surprised voice as she took the picture from him. She looked at it and let out a small laugh. “You even color like a baby! Thank you, I know that Cassie will just love this too. We’ll find a good place to hang it in our apartment… maybe on the refrigerator. How will that be?”
Chad wasn’t happy about that at all. Why couldn’t she just take it and put it away somewhere – like maybe in the trash can. In her elaborately decorated apartment, it would stick out like a sore thumb – and everybody who went in would notice it. But he replied, “That would be great.”
“So are you ready now?” Sandy asked.
“Yes, Sandy,” he replied.
Sandy turned to Mel, “Are you coming with us now, since he only has a few minutes to start leaking?”
“I’ll be over in just a few minutes,” Mel replied. “I have something else I have to do first.”
Sandy stopped before she opened the door and turned to Sissy. “Remember the rules! No walking the minute you get to my apartment… and only baby talk!”
Chad dropped a quick curtsey. “I remember.” Ugh! Baby talk! What a pain!
Mel stayed back in his apartment as Sandy and Sissy left. She went straight to his refrigerator and checked it. As she suspected, he was just about out of bottles. Well, she would fix that problem soon enough. She went back to the child’s menu that he had colored and ripped out the other picture that she liked. She hung it right next to his other picture on the wall so he could “enjoy” them both.

“Climb up,” Sandy said as she took the tray off of his highchair. Chad crawled across her kitchen floor and climbed up into the chair. Sandy fastened the safety belt around him, being careful to pull it tight. She was about to put the tray back into place when she paused a moment in thought. “Put your right arm down in your lap.”
Chad was surprised by her request, but protesting or even questioning it would do no good. Besides, since he was limited to only baby-talk, he had no way to ask her why. As soon as his arm was down, she put the tray into place, locking his right arm under the tray where he couldn’t use it.
“That should work,” Sandy mused to herself.
Chad watched as she began dumping baby food, straight out of the jars onto the divided child’s dish that she had gotten for him – colorful baby food, that he had no idea what it was, even when he tasted it. She set the plate down in front of him, then set a small rubber coated baby spoon down next to the plate. “I want you to feed yourself this time,” she told him.
Chad awkwardly picked up the spoon with his left hand. He started to bring it toward the food, but she stopped him. “Not like that! Babies don’t hold anything like you’re holding that. Close your fist around it instead and grab it tightly.”
Hold it in his fist? Ugh! He managed to get the spoon into his hand the way she wanted it, which wasn’t all that easy since he only had the one hand to use. Then he shoveled some of the baby food onto the spoon. He wanted to change the position of the spoon in his hand to make it easier to bring it to his mouth, but with his fist wrapped tightly around it, he couldn’t do that. He had to awkwardly turn his entire arm out to get it around far enough that he could get the food into his mouth. Eating with just the tiny baby spoon had always been difficult, not to mention embarrassing. Doing it this way made the task twice as hard! He slowly reached out and grabbed another spoonful and managed to get it almost to his mouth before some of it dripped off of the spoon and onto his bib. It seemed that holding the tiny spoon the way he was, made it harder to keep it level. And the result was that more of the baby food dripped off. Just great!
“Perfect!” Sandy declared happily. “That’s the way you should be eating from now on.”
Not likely, Chad thought. But just then, someone knocked at the door. Chad quietly panicked inside while Sandy went to answer it. She came back a few moments later with Mel.
“Keep eating,” Sandy ordered as they got back to the kitchen.
Mel watched him eating awkwardly with the tiny baby spoon. “I must say, you found a way to make even his eating look more childish.”
“Babies don’t hold spoons the way we do,” Sandy explained. “And as far as I’m concerned, the more babyish he does everything, the better!”
Mel laughed. “I couldn’t agree more!”
Chad was about halfway through with the food. His face was a mess. His bib was a mess. And so was the tray in front of him because the food kept dropping off of the tiny spoon – not to mention that it was more difficult than ever to accurately hit his mouth the way he was holding the darn thing. He suddenly felt himself peeing again. Knowing that the time was running out for him to be leaking, he waited till he was done peeing, then he began trying to feel all around the leg openings of his diaper with the one hand that was under the tray. He couldn’t reach the diaper on his right leg very well, but he could feel around the opening of his left leg a bit. Nothing… Nothing… There! Was that a bit of a wet spot near the bottom? He felt it again. Yes, it did feel like it was starting to leak out. Since he had no other way to express himself, he let loose a tirade of baby talk. But Mel and Sandy were talking and mostly ignoring him. He tried again, harder. They both looked over at him.
“What’s the matter, baby?” Sandy asked. “You’re not finished with your dinner yet. Keep eating.”
But Chad had to let them know that he was leaking. He tried more baby talk instead.
“Was he asking for his bottle?” Mel asked. “You know, he does need to be leaking very soon. Maybe he needs a bit more to drink.”
Sandy got up quickly and got a bottle for him that was already filled with baby formula. But as she brought it over to him, Chad very emphatically let out more baby nonsense. Sandy set the bottle down on his tray and turned back toward Mel. “I don’t think that was it,” she said. “I think he’s trying to tell us something else.”
Mel came over to him and peered under the tray at his diaper. “Are you leaking?” she asked.
Chad let out a shorter and happier stream of baby nonsense to let her know that that was his problem.
“I guess that’s it,” Mel said to Sandy. “We can change him now and then I can get out of your hair for a while.”
“No problem,” Sandy replied as she took the bottle back off of the tray and also picked his food up too. “Wow, you’re really a mess, baby,” she declared as she looked at him. “Just like a real baby!” She grabbed a wet washcloth and spent several moments cleaning him up thoroughly before she removed the tray that was holding both him and his arm in the chair. She had to release the safety strap before he was able to climb down to crawl on the floor.
Mel led the way into the living room where Sandy had laid out a large blanket that was already covered with baby toys for him to play with later. She moved some of the toys out of the way. “Lay down here,” she told him and waited while he crawled over into position. Sandy brought the diaper bag over for her. With practiced efficiency, she quickly had his overly soaked diaper off of him and a new one shoved in place under him, ready to bring up between his legs. She reached back into the diaper bag and brought out the jar of suppositories. With a wicked smile on her face, she held the jar up where he could see it. “Your favorite part, I know!”
Chad rolled his eyes and turned his head away. The suppositories were his least favorite part. He hated the things – and especially what they did to him.
Mel reached into the jar and pulled out – nothing. “Lift your legs,” she ordered. Chad raised his legs up and she pushed them up even higher, totally exposing his bare backside. It took her only a moment to shove her finger way up inside of him – as if she were actually shoving one of the suppositories up there. He would never know the difference, and hopefully, the results would be exactly the same. She brought his legs back down and a minute later the fresh diaper was taped securely in place. She checked her watch. “Two hours, baby. Two hours.”
Since Chad had no way of responding in any recognizable way, he said nothing. He already knew the drill.

The Bet - Chapter 36 (Saturday – week 5 Part 2 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 2 of 8)

Chad stared at the shopping list he had made. He needed an awful lot of stuff. His makeup was running low, he needed shampoo and conditioner. He needed baby wipes and baby lotion. He needed pantyhose. And of course three more packages of diapers. It would take a long time to shop for all that stuff. Longer than he wanted to be out in public by himself, dressed as he was.
Today he was wearing pants again… but they were the tighter pants this time. With only one diaper on and knowing that he probably wouldn’t be wearing them for very long, they had seemed like his best option. It actually felt a bit strange wearing pants again, even with the high heels on his feet. He was also wearing his waist cincher to give himself a bit of a better figure. His shape wasn’t as good without the all-in-one girdle he usually wore too, but the waist cincher did help a lot. Naturally, he had added a bra and his breast forms too – at least they weren’t glued on to him today… yet. A simple casual top, his watch, ring, and necklace completed his outfit. Casual. Actually a lot more comfortable without the all-in-one girdle. It gave him a huge sense of freedom.
He checked his watch. Only a little over an hour to go before he would have to be at Mel’s apartment with a leaking diaper. His diaper was already getting very wet, but it still had a long way to go so he dared not hold back at all. Picking up his purse, he headed out the door and down to his car to start taking care of business.
His first stop of the morning was at the ATM machine to get a pile of cash to use during the week. The cash made life a lot easier, even though he no longer had the super long nails on his hands. As he punched the numbers into the machine with the tips of his nails, he was again struck by the strange purple color. Would he ever get used to them? They were kind of pretty though.
He needed diapers – three packages. But just thinking about shopping for them reminded him of the two girls who had been all too interested in him at his usual drug store for the last two weeks. Purposely, he avoided that store and went further down the road to the next one. The store was crowded as he went inside, but then he was a bit later getting there than he wanted to be this morning. He ignored all the other customers and went straight to the diaper aisle. He was glad to see that they were fully stocked this time. He pulled three big packages off the shelf, and holding two of them while trying to precariously balance the third, made his way to the checkout counter. He realized that the drug store probably also carried most of everything else on his list too, but he didn’t want to have to deal with buying all that along with the diapers. And just carrying it all would have been impossible anyway.
As he stood waiting in the short line, he saw some of the other customers glancing at him curiously. But at least none of them said anything or even looked overly long at him. He was glad. When it was his turn to pay, the saleswoman simply rang him up quickly, dumped all three bags of diapers into three different plastic bags, took his money, and gave him his change. Quick and simple. Just the way it was supposed to be. Things were definitely going better today – so far! He made a mental note to use this drug store all the time from now on.
He checked his watch again as he got back into the car – just over forty minutes to go. He was doing pretty good continuing to wet himself, but there were still no leaks. If he was going to make Mel’s deadline then he had to keep drinking – and he had to keep trying to wet. He drove further down the road to his favorite fast food restaurant and ordered a quick breakfast with a large cup of coffee through the drive-thru. He sat in his car the parking lot while he ate, then got back on the road again the minute he finished.
But where to go next? Time was running out before he had to be at Mel’s door with a leaky diaper. He could tell that his diaper was really wet, but he still hadn’t felt the telltale tickle of any leaks yet. He knew that someplace like Target or Wal-Mart would have everything else that he needed, but stopping at one of those stores would take too long. He turned back towards home instead to wait till after he could get changed before he continued his shopping. But halfway home, he noticed the drug store he had just stopped at a little while ago. The experience hadn’t been bad at all, and most of the things that he needed could be bought there. Trying to save a little time, he quickly pulled back into the store’s parking lot as he felt himself peeing yet again – but he still didn’t feel any leaks.
There were quite a few cars in the parking lot now, but he didn’t think it would be too crowded inside. He entered the store and grabbed a small handheld shopping basket from a stack near the door. At first glance, he was a bit worried about the number of people he saw inside, but he kept going anyway.
The makeup section was first – several long aisles of it. All of which had women looking closely at the various items – too many women for his comfort since he wasn’t all that sure about where to find what he was looking for anyway. He continued on to the next section instead and quickly found the shampoo, conditioner and other bath supplies that he needed. There were only two women in this section, but in the long aisle, that didn’t seem like too many at all. His basket started to fill up quickly, but as he turned from picking up one of the items, he noticed one of the women had been looking at him rather closely. Well, that was nothing new. At least she didn’t say anything. He glanced at his watch, time was running short. As he hurried to the checkout counter, he was pleased to feel himself peeing again – a lot – probably from the coffee he had just finished.
The store had two cash register lanes open now to handle all the customers, with a short line at each one. Chad chose the line that he hoped would get him out of there the quickest. He was aware, as usual, of all the stares from everyone around him, but fortunately, nobody said anything to him. But as he stood there waiting his turn, something suddenly felt odd… then grew more odd. The odd feeling was on his legs, just below his crotch, and it seemed to be expanding! He reached down casually and felt his pants just below his diaper. Wet! He was leaking, and the pants he had on were too tight to let any of it just drip down his leg. They were quickly becoming wetter and wetter as his diaper continued to leak!
He moved up in line, only one other person ahead of him now. He had a basket full of things to buy in his hand. He wanted to just drop the basket and run out, but he had come so far already. He heard someone grunt in surprise, then a moment later, someone giggled. He turned, two women were looking at him. Then someone else noticed him. That someone else grabbed her friend’s arm and pointed at him. Damn! Why didn’t he think about this when he got dressed this morning? His pants were too tight to let him get away with anything! Not only were the people noticing him because he was obviously a man dressed as a woman, but he was feeling extra embarrassed because he was now out with obviously wet pants, and the growing wet stains were letting everyone know that he had just wet himself! He was about to drop everything and just walk out, but just then, the person ahead of him finished and it was his turn to check out. He had come too far now to just leave.
As quickly as he could, he put everything up on the counter from his basket and waited while the cashier rang everything up. Fortunately, she couldn’t see his wet pants. But he had no doubt that everyone else in line was watching him. It took a few minutes to ring everything up, pay for it, receive his change, and wait till it all got bagged before he could finally leave. By then, there didn’t seem to be any use in hurrying too much. Everyone had already gotten an eyeful!
He didn’t dare to glance down at his pants to see how bad they were till he got out of the store and was standing next to his car. And what he saw was shocking. Just from what he could see, he had large wet splotches in several areas at the top of each leg, starting right at his crotch. Some of those wet splotches were starting to grow together. He couldn’t see behind him, but he could now feel how wet he was back there and it felt even worse than the front. He finally opened his car door and threw his bags across onto the passenger seat on top of the diaper bags. But as he started to get into the car, he stopped and noticed that there was a small wet area on the seat already. He had been leaking since before he went into the store and didn’t know it! No wonder some of the people in the store had been staring at him since he went in.
Not wanting to make his seat any wetter, he grabbed one of the large plastic bags that held his diapers and emptied the bag. He sat on the plastic all the way home. He left all his purchases on the seat of his car as he climbed the stairs up to Mel’s apartment and knocked on her door with just a few minutes left to spare. The door opened and he immediately dropped his usual curtsey and recited his sissy greeting.
Mel smiled. “You just made it!” But then she stopped and stared at his wet pants. “But by the looks of things, you could have been here earlier. Turn all the way around. Let me see how bad it is.” Still outside where everyone could see him, Chad slowly turned all the way around. “Why didn’t you come back sooner?” she asked.
“I was out shopping when it happened.”
“In the stores? With people around?”
“Yeah, the drug store.”
Mel smiled. “I hope you enjoyed yourself.”
That wasn’t exactly the way that Chad would have put it!
“Let’s go get you changed,” Mel said as she grabbed her keys from her purse and started toward his apartment. Chad followed behind, allowing Mel to unlock his apartment door for him since her key was already out.
“Did you get everything you need today?” Mel asked as he was removing his wet pants.
“Not yet,” he replied. “I still have to find some of the makeup I’m almost out of, and I need a few more pairs of pantyhose too.”
“Some of that makeup you’re only going to be able to get at the mall.”
He groaned audibly. “That’s the only place? Target or Wal-Mart won’t carry it?”
She shook her head. “Not that brand. You’ll have to go back to the makeup counter where you got it. Of course when you do, you can always ask for another demonstration again,” she teased.
Chad rolled his eyes as he pulled off his saturated diaper and let it drop to the floor. “No thanks. Not today,” he replied.
She smiled but said nothing as she waited for him to tape another fresh diaper in place. “Two hours, Sissy,” she said as she glanced at her watch.
Chad glanced at his own watch too. “Yes, Mistress,” he replied with a small sigh.
She paused before she left him. “Tell you what. I was thinking of going shopping today myself. I need a few things too. If you like, we can go to the mall together and you can get your makeup then.”
Chad thought about that for only a few seconds. It sounded like a better idea to him – despite what she might come up with along the way. Besides, if she was going shopping then he was probably going with her anyway. “Thanks,” he replied. “Maybe I’ll wait till then.”
Once Mel was gone, Chad went back to face his closet. Now what was he going to wear? Pants were obviously out! Since he wasn’t going shopping till later with Mel, he was tempted to stay in just his diaper till she came back at noon. And when Sandy arrived later, he had no doubt that she would have her own ideas on what she wanted him to wear today. But then he remembered that all the things he had bought earlier were still down in his car and they needed to be brought upstairs. He finally chose the most casual looking skirt and top that he could find and the low-heeled shoes that he wore with his uniform. He might as well be comfortable. Since he only had two more hours to go till he had to be leaking again, he pulled another baby bottle out of his refrigerator before going down to the car to get his purchases.

“I really appreciate this,” Sandy said as she opened the door to her apartment and she and Mel lugged the heavy highchair inside.
“No, it’s me who appreciates it,” Mel replied. “What do you have planned for him today?”
“I was thinking of a couple of things. But mostly, I’d like to start working on the way he does things… the way he moves. Babies don’t quite have the motor control we have, so they do things a bit differently. I’d like to try a few ideas on that line today.”
“Sounds interesting,” Mel replied. “Actually, that’s something I need to start working on with him too, although in a completely different way. He’s still got too many masculine mannerisms.”
Sandy giggled. “Well then, maybe between the two of us we can eliminate a few of them.” Mel giggled too.