The Bet - Chapter 39 (Tuesday – week 6 Part 2 of 8)

The Bet
by Karen Singer

Chapter 39 (Tuesday – week 6 Part 2 of 8)

Mel sat back in one of the chairs just outside of the room where she and one of her clients would be meeting with the judge. The meeting had been postponed for a short while till the judge would be ready. Her client had wandered off to use the rest room while he still had the chance. The opposing client and his lawyer were further down the hall talking. Mel had nothing better to do than to sit back for a while and wait.
But instead of concentrating on her client’s needs, her mind wandered instead to the upcoming poker game that night… and Chad. But this time she wasn’t really thinking about why she wanted him to go to the game, or why she should want to go either. She really had no idea as to the answers to those questions. So instead, she tried to concentrate on how she could make Chad’s evening more… memorable? Or exciting? Or fun? Or perhaps – just plain outrageous.
A few thoughts came to mind, but mostly she kept going back over the things he had told her in the restaurant last Friday – things he had been very worried about. As she went over each item from his list in her mind, she had to control herself to keep from laughing out loud as she pictured each thing that he had mentioned. They were all great ideas. But really, should she use them? They certainly were funny. And they would certainly be memorable – for everyone. And they would certainly be exciting. And they were without a doubt – outrageous!
She tried to imagine how he would look sitting at the poker table drinking from a baby bottle while everyone else was drinking from beer bottles. Now that really would be hysterical! She already had him using bottles in all the public restaurants. This wouldn’t be that much different.
And then there was his adorable little pink baby dress. Little was right! There was certainly no way he could hide his diapers with that on! And finally… the word would be out about him and he wouldn’t be trying to hide anymore!
And from there, he would no longer have any excuse at all for not using his sissy voice all the time – even at work. And she definitely planned to make him use it at the game later. Everyone was going to know! He would have no way of denying his sissy state at all. And presto! No more excuses from him – and consequently, no more trouble! Problem solved!
A clerk poked her head out the door and motioned that it was time for them to enter. She glanced up the hall to see her client just coming back – perfect timing. With a broad smile still on her face she went into the meeting. She already knew what the outcome would be. She had warned her client. She knew that the opposing lawyer knew what it would be too, yet both clients wanted to try to get more.
Both sides presented their arguments for getting everything… and then the bargaining began. It was a long and tedious dance, but for the client’s sake, necessary. Of course, the additional billing time she would charge wasn’t all that bad either. One item after another was put on the table, argued over, then removed. Over and over again she consulted quietly with her client, just as the opposing lawyer did, trying to get the client to accept the solution. Tempers flared between the clients and both lawyers had to calm them down. Near the end, they had agreed on most of it – an agreement built on compromise after compromise. But still the clients wouldn’t agree on the final outcome.
In the end, the judge finally stepped in and made one final decision and ordered both parties to just live with it – like it or not. Mel did her best to console her client, the opposing lawyer did the same. At one point she privately caught the eye of the opposing lawyer, it was obvious that they both agreed with the judge, but they were representing their clients so the meeting had to go as it did. Compromise after compromise. And in the end, the judge had decreed one more final compromise. But as happened so often in her profession, compromise was the name of the game.
She left the meeting feeling tired and wasted. Not at all ready to go back to her office and dig into more. She made a mental note to look for ways to charge her client a bit more for the extra effort.
She got back into her car and pulled her cell phone out of her purse. She punched in Andrea’s number and was rewarded to hear her assistant answer the phone promptly. “Hi Andrea, it’s me. Is there anything pressing going on there that I need to get back before lunch?”
“Nothing that I can see,” Andrea replied, already knowing exactly what was on Mel’s schedule.
“Good. I’m going to go shopping for a bit, then have lunch with Gloria. I’ll see you after that.”
“Good enough, Mel. I’ll hold the fort here.”
Mel chuckled. “Like always,” she replied before closing her phone. She started her car and headed out towards the mall and parked near one of the nicer major clothing outlets. Once inside, she wandered casually around the various sections of the store, looking at this and that. Finally, she stopped in one aisle and stared at the display for a moment. Perfect! It would be just what she needed – that is, if they had something else to go with it. That something else turned out to be fairly easy to find.

“Hey Sissy,” one of the women in the break room started, even before he had reached the table with his coffee, “did you ever work out that problem with your friend Mel that you were talking about yesterday?”
Chad was surprised that the woman would even remember. He was tempted to tell her that he wasn’t the one who had been discussing it, everyone else was – even though it was his problem and he had told them it wasn’t a problem. Women! “It really wasn’t a problem,” he repeated again.
“So what was it?” another woman asked as she too sat down.
“Nothing,” he replied with a small wave of his hand.
“Oh come on! It had to be something or we wouldn’t have been talking about it yesterday. What was it that you couldn’t do?”
Chad shook his head. “I’m not going to talk about it!” he repeated.
“Even though it’s not really a problem?” someone asked. She looked over at the woman next to her. “Sure sounds like a problem to me – he’s just being stubborn!”
“You got that right, girl!” her friend replied.
“Hey,” another woman called, “Are you still going out with Derek tonight?”
Chad was flabbergasted. “I’m not going out with Derek!” he replied testily. “Where’d you get that idea?”
“Well, excuse me,” the woman replied. “I thought someone said that you and he were going somewhere tonight.”
Chad shook his head. “No… well… It’s just a poker game – and we’re not going together! We’re just going to be there at the same time, that’s all.”
“Oh.” The woman said as if she really understood. “So are you two going to be getting together?”
Chad was more than shocked. “Get together? You mean Derek and I?”
“Well, yeah. You do hang with him don’t you? And you are going somewhere tonight – even if you’re not going together. I mean, you’re dressing like a woman, and he’s a man and… You know. Get the picture?”
Unfortunately, Chad totally got the picture. Women! Where did they come up with these things? “No! Derek and I are not – getting together – as you put it. We’re just friends. He’s been my friend for a long time. And that’s it!”
“I was just asking, that’s all,” the woman replied half heartedly.
Chad just couldn’t believe it. Women! Where did they come up with these things?

Chad rarely approached the door to the gym without feeling at least some measure of trepidation and today was no different. But as he opened the door this time, he couldn’t help but notice the overly excited look on the receptionist’s face as he walked in. He immediately began to worry, if only because she seemed to enjoy teasing him so much. He immediately became a lot less worried though as he saw Cassie standing nearby.
“Hi Sissy,” the receptionist said cheerily.
Chad wondered if her greeting sounded overly cheerful. He tried to ignore her since Cassie was right there. He dropped his required curtsey to Cassie and said hello to her in his sissy voice.
Cassie’s face immediately turned from pleasant to annoyed. “That wasn’t very nice!” she scolded. “You completely ignored Cindy’s very pleasant greeting. Now say hello to her before we go any further – and tell her you’re sorry while you’re at it!”
There was just no use trying to avoid it – he should have realized that from the start. He dropped another curtsey for the receptionist and said hello then apologized for ignoring her. He did it all in his sissy voice because he knew that if he didn’t she would only complain and he’d have to do it again.
“He really is so sweet,” Cindy said excitedly to Cassie.
Cassie just sighed. “Sometimes, Cindy. Sometimes.” She turned to Chad. “Let’s get you going.” This time, she let him lead the way towards the back. But before she turned the corner out of sight, she paused and looked back toward Cindy. She held up her hand with all five fingers extended. Cindy nodded, knowing exactly what Cassie was telling her – five minutes.
Back in the room, Chad got undressed while Cassie dug into his diaper bag. She pulled out one of his baby bottles, two fresh diapers, his jar of suppositories, some wipes and a plastic bag to put his used diapers into. She quickly slit the outer lining of one of the new diapers she pulled out so it could let the overflow pass into the other diaper that would be put over it. By that time, Chad was finally down to just his bra covering his glued on breast forms, his waist cincher, and the plastic panties covering his diapers. She waited till he laid down on the floor, then she handed him his baby bottle to start nursing on.
As soon as she saw him contentedly drinking from his bottle, she got to her feet instead of pulling down his plastic panties. She saw him look up questioningly. “Just keep drinking that thing,” she told him. “I’m not going anywhere.”
Chad went back to nursing happily on the bottle, but that didn’t last long as he realized that Cassie had just opened the door. He looked up and saw her moving back away from the door and just as quickly, someone else was coming in – the receptionist! Cindy! “Cassie, what are you doing?”
“Hush!” Cassie replied quickly as the door was closed again. “Mel left this totally up to me, and as far as I can see, you don’t really have any say in the matter.”
“But…”
“I said hush! Now go back to drinking your bottle.”
Cindy was trying, unsuccessfully, to stifle her laughter. He was laying there drinking a baby bottle – like a baby, with his diapers fully on display. Never mind the totally incongruous bra and waist cincher. They could easily be overlooked. “A bottle?” she exclaimed the moment she could get past her surprise. “He’s drinking from a baby bottle?”
“What did you expect?” Cassie asked as she again knelt down next to Chad to begin working on him. She noticed that Chad was still so shocked he hadn’t put the bottle back into his mouth. She reached up and guided it back towards his head. “You better keep drinking that or we’ll never get out of here,” she told him.
Chad barely realized that he was putting the bottle back into his mouth to begin drinking from it again. He just couldn’t believe it! Cindy! The receptionist! Here! Where he was getting changed! Why had Cassie agreed to this? It wasn’t right! His attention was suddenly torn partially from the fact that Cindy was watching as he felt Cassie pulling his plastic panties down his legs. And now Cindy was going to see him getting changed too! Was Cassie going to let her see everything? He was suddenly very worried about that!
Cassie pulled the plastic panties off of him, then reached up and grabbed one of the tapes holding his outer diaper closed. With more flair than usual, she pulled the tape up. The rest of the tapes on that diaper went exactly the same way.
Cindy actually held her breath as she watched Cassie pulling up the tapes from his diaper. She watched even more raptly as Cassie casually pulled the diaper back between his legs. And then she was hugely shocked to see a second diaper underneath! “Another one?” she asked.
“Sure! He can’t go all morning with just one diaper. I’m surprised he doesn’t start leaking before he gets here.” Cassie reached for one of the tapes, then stopped. “Why don’t you remove this one,” she said to Cindy with a wicked grin on her face.
Chad didn’t even think before he began complaining again. “But Cassie…”
“Hush!” Cassie ordered once again. “Which one of us is laying here drinking from a bottle like a baby? Which one of us is here to have their very wet diapers changed – like a baby? And which one of us is actually the real adult here? Do you think a baby should have any say in the matter?” Without waiting for an answer, she reached up and once again guided his bottle back to his mouth. Then she turned back to Cindy. “Okay, go ahead.”
Cindy was actually giggling – even more so after Cassie had finished telling him off. Excitedly, she reached out to grab one of the tapes, but she stopped her hand short. “Eww! He looks awfully wet! I’m not going to get any of that on my hand am I?”
Cassie just shrugged. “Probably not – but maybe. The tapes should be dry, well mostly dry. You probably should wash your hands after this anyway.”
Cindy plucked up her courage and grabbed one of the tapes. With a fairly hard tug, she ripped it open. She looked up at Cassie. “Not so bad.” One by one, she pulled the remaining tapes. “Now what?” she asked.
“Now you pull the front of his diaper down like I did the first one.
Chad, baby bottle in mouth, was doing his very best to lay still and ignore what they were doing down there – which was proving to be impossible. He still couldn’t believe that Cassie had allowed this girl to be back here with them – let alone help. But here she was!
Cindy reached out with two fingers and almost gingerly grabbed the very edge of the top of his diaper. Carefully and slowly she pulled it up and then down toward his legs. Then she dropped it with another huge shock. She stared and stared, but she couldn’t believe what she was seeing. “Is that… I mean, isn’t that a… God! And it’s got a lock on it too!”
Cassie just smiled. “That’s to keep him from playing with himself.”
“Does it work?”
“What do you think?”
Cindy was still too shocked to answer. Finally she asked, “Can I touch it?”
“Go ahead.”
Cindy reached out her finger carefully and just barely touched the plastic casing around his penis with the very tip of her fingernail. She quickly pulled it away again. Then, hesitantly, she reached out with the same fingernail and tapped on it a few times. “Huh!” she grunted.
As she was doing that, Cassie noticed something that Cindy wouldn’t have. His trapped penis inside the device was definitely a bit bigger than usual. Not a lot, but it was definitely bigger. She looked up toward Chad’s face. His eyes were open wide as if from fright, he appeared to be drinking from his bottle mindlessly but furiously, and… was that a look of pain registering on his face? She remembered the tiny teeth inside the device, designed to give him pain any time he got hard. Yes, he was probably in pain. How much, she didn’t know. She reached out and grabbed his chastity device with her fingers and shook it back and forth a bit. No further reaction from him. “Here,” she said to Cindy, “grab it like this and shake it a bit.”
“Uh… Are you sure?” Cindy asked tentatively.
“Yeah. Don’t worry, it’s not going to bite you!” Cassie didn’t add that if Chad got any harder, then the device would definitely be ‘biting’ him. She watched as Cindy lightly grabbed the device and moved it from side to side a little bit. “Harder!” she coaxed. “Pull on it if you want.”
Cindy wasn’t at all sure about what she was doing, but she grabbed the device more firmly and started moving it all around. Then she began pulling lightly on it as if she was going to pull it off of him. When the device refused to come off, she began pulling harder – and harder!
Cassie saw the pain registering in Chad’s face. He had stopped nursing on his bottle even though it was still in his mouth. Suddenly the pain must have increased because he gulped in a quick breath and his body seemed to jerk a bit. “That’s enough!” she said quickly to Cindy. She looked down at what Cindy was doing and just caught a glimpse of how hard she must have been pulling on his device.
Cindy shook her head. “I didn’t come off! I pulled pretty hard, but it really didn’t budge at all!”
“That’s the whole point,” Cassie replied. “What would be the use of locking it on him if he can get it off?”
Cindy said nothing. She just continued to stare at his chastity covered penis. She had seen very few naked men in her life and never once imagined anything like this.
“I think it’s time for you to get back out front now,” Cassie reminded her. “I’ve got to finish up with him.”
Cindy rose to her feet, still staring at his plastic enclosed penis. “Thanks Cassie. That was… incredible!”
“Did you have to do that?” Chad asked, as soon as Cindy was gone.
“Do what?” Cassie asked as she began wiping the front of him off.
“Let her in here.”
“I told you before, I don’t see where you have any say in the matter!” She paused before she asked. “Did she hurt you?”
“Yeah! When she pulled so hard on that thing it hurt a lot!”
“I think you were hurting a bit even before she started pulling.” When Chad made no reply, she leaned a bit closer to his head. “So it turns you on to have strangers see you like this?”
“It’s embarrassing!” Chad replied with a hint of anger.
Cassie just smiled. “Which means it turns you on.”
A moment later, she asked him to roll over so she could work on his backside. The minute she could see his backside though, she got quite a surprise. “Somebody’s been naughty!” she exclaimed. “That’s not diaper rash – for sure!” When Chad still remained silent, she reached out and touched the red area of his bottom – no real reaction. She grabbed a wipe and wiped him clean, noting as she did so that he defiantly registered pain from the cloth scrubbing his skin.
She poured a healthy amount of baby lotion into her hands and began rubbing it very cautiously onto his bottom. Chad jumped at the cold lotion touching him at first, but otherwise, he endured it fairly well. “Would you rather skip the other play?” she asked him.
That was usually the part of this that Chad liked the best. But somehow, he really wasn’t in the mood for it at all today – probably because of Cindy. “Can we skip it?” Chad asked.
“We can if you like,” Cassie replied and reached for the jar of suppositories. It was Tuesday, one of the new days he was supposed to actually get one. She saw Chad starting to roll back over. “Uh, uh!” she grunted, stopping him where he was. “We’ve got one other little matter to take care of first. Don’t forget these things,” she said as she held the jar up near his head. With more show than usual, she opened the jar and pulled one out, making sure that he knew she actually had one. She saw him look away, not wanting to see it at all – which was really just fine with her. Since she hadn’t played with his backside before hand, pushing the little thing up inside of him was a bit more difficult than usual, but really not all that hard. “There! All done,” she said, sounding very satisfied.
Chad rolled back over onto his back and picked up his baby bottle again to finish it. Would the humiliations ever stop? No, he was sure of that answer. They wouldn’t stop till he could win the bet. And if he didn’t win? He didn’t even want to think about that!