The Bet - Chapter 31 (Monday – week 5 Part 4 of 8)

The Bet
by Karen Singer

Chapter 31 (Monday – week 5 Part 4 of 8)

“Wow, that was something,” Cassie said as she closed the door behind them.
Chad just shrugged. He had been on such a high in front of all the customers, but now he was feeling awfully low. “I had to,” he replied. “I had no choice.”
“Yeah, I know,” Cassie agreed. In a way, she felt sorry for him, but there wasn’t much she could do about that – except perhaps to change his diaper for him now. Chad started to reach for the zipper in the back of his dress. “Don’t bother, Sweetie. Just hold your skirts up and I change you standing up.”
That surprised Chad. She didn’t ever do it that way. But why not? It was only the one diaper. He started grabbing his skirt and ruffles and pulling them up out of the way. There were so many ruffles though that Cassie had to help him. She kept pulling at them and stuffing them into his hands and under his arms until she finally had a clear view of his soggy diaper. From there, it only took her a minute to replace it with a fresh one. The new diaper actually felt good to Chad, despite how much he loved to always feel them wet.
A minute later, he and Cassie left the little office in the back together, this time Chad was carrying his pink diaper bag over his shoulder. Mel and Sandy were waiting nearby. “Pacifier!” Mel warned as soon as she saw him. Chad immediately grabbed it and stuck it back into his mouth. With Sandy taking one hand and Mel his other, they led him like a child back out to the car. He didn’t skip this time. He was done with that. He simply felt sorry for himself. Everybody had seen the proof of how much of a sissy baby he really was now. They had seen it! Everybody!
“Do you still need me?” Sandy asked Mel as Chad was trying to get his dress under control so he could buckle the seat belt in the car.
“No, I think I can handle it now.”
“Then, if you don’t mind, I’ll stay here. I can get a ride with someone later.”
“That’s fine. Thanks for your help,” Mel replied.
Sandy giggled. “Oh, I wouldn’t have missed that for the world!”
Mel closed the rear car door, leaving Chad buckled into the back seat of her car alone. She remained outside the car and pulled out her cell phone. She punched a few numbers. “Are you busy right now?” she asked in her most cheerful voice.
“Mel!” Gloria’s voice came over the line. “Not at the moment. My next client probably won’t show up for another half an hour. What’s up?”
“Just wanted to know if we could stop by for a minute?”
“Sure, I guess so… But Mel, I still haven’t changed my mind!”
“I know. I just want to show you something.”
Mel got back into her car and turned to face Chad. He was already sucking on his baby bottle again and seemed to be staring mindlessly out of the window, not paying attention to anything. Lost in his own little world. “Sissy!”
Chad’s head turned quickly toward her. Worry creased his brow. “Was I good enough, Mistress?” he asked hopefully.
Mel smiled. “Yes, you were very good.” Something in the back of Mel’s mind bothered her about that statement. She had originally wanted to punish him, and punish him good. But she wasn’t at all sure if he got the punishment, or even humiliation, that she thought he deserved. Yet he seemed very contrite and bothered right now. She put all thoughts of that out of her head for later. It was time to move on. She still needed him to be the super sissy again.
“So you’re not going to take me to work like this?”
She stared at him for a moment. “I am still considering it. Like it or not!”
“But you said…”
“I know! I know. And you were good in there. Very good in fact. So we’re going to make another stop instead. We’re going to go over and see Gloria for a few minutes. And Sissy, you’d better be awfully convincing to her again, or our next stop after that will be where you work!”
Chad said nothing. His eyes just sort of glazed over again as he put his baby bottle back into his mouth. At least Mel wasn’t taking him to work like this… yet. She was just continuing to hold the threat over his head.

The only other car in Gloria’s little parking lot when they arrived belonged to Gloria. Mel parked her car and turned around to Chad. “Don’t forget,” she said, the tone of her voice sounding more like a stern warning than anything else. “You’d better be convincing again. I want to see that same deliriously happy sissy you were at the gym.”
Chad removed the bottle from his mouth. He was about to ask why, but the quick no-nonsense look she gave him before he could open his mouth silenced any questions he might have had. “Yes, Mistress,” he answered in his stupid little sissy voice. He would have to do it all again. But at least this time there wouldn’t be lots of people around. In fact, hopefully, it would be just Gloria and nobody else. Taking a big breath for courage, he began digging through the mounds of ruffles to unbuckle his seatbelt.
The road Gloria’s small office was on was a busier one than the road the Gym was located on. Chad delayed getting out of the car as long as possible, but when Mel opened his car door for him, he knew he had no choice. Once again he was about to show the world what a total fool he was. He was still sitting in the car, but she was watching him, her look somehow disapproving. He grabbed his pacifier and stuck it back into his mouth. He could delay no longer.
In a mound of ruffles, he got out of the car. In the brighter sunlight, he felt like a big neon sign drawing everybody’s attention. Look at me! Look at me! How could they not look at him? How could they not see him? A car horn honked then another. He heard Mel’s car locking as she pressed the button on her remote. Trapped outside again! He glanced at all the traffic going by. He could see drivers turning their heads to stare at him. He wanted to get out of there… get away… before he caused an accident. “Mistress,” he started to say, worriedly.
But Mel already had everything planned. “Go on inside,” she told him. “I’ll be right behind you.”
Chad didn’t know if he was supposed to run or skip or what, so he started walking quickly for the door.
“Skip!” Mel’s voice lashed out behind him. “Like a happy little sissy!”
Chad began skipping to Gloria’s door. Fortunately it wasn’t very far. Another car horn honked at him. He opened the door. Mel would be right behind him. He had to be convincing! He did his best to smile again as he went inside.
Gloria was sitting at her desk in her private inner office. The door to her waiting room was opened wide so she could see if anybody came in. She was expecting Mel, but what she wasn’t expecting was to see a mound of pink and white ruffles forcing its way through her doorway… along with someone in the silliest sissy dress she could imagine. She watched in amazement as it got completely through her door. She tried to take the entire figure in, but it was impossible. She was speechless. And then the figure saw her and started skipping towards her inner office.
She didn’t know whether to be afraid or to laugh as the strange apparition approached. And then it stopped, right in front of her desk… and curtseyed – elaborately and strangely. She caught a glimpse of what looked like a diaper underneath the mounds of ruffles. She was finally able to bring her amazed stare up to look at the face clearly. Chad! She had sort of guessed the moment he had come in, but the shock of seeing the silly dress along with his childish behavior had kept her eyes locked on the rest of him and his antics. She was about to say hello to him, but he opened his mouth first.
“Hewwo, Gwowia,” Chad said in the silliest voice she had ever heard.
She had tried to control it, but this time the laughter burst out of her. When she could see straight again, she noticed a figure standing in the doorway behind him. Mel. But she couldn’t tear her eyes off of Chad long enough to even acknowledge her.
“Would you like to hear me sing ‘Mary Had a Little Lamb’? Chad asked in his silly childish voice.
Gloria would have said no, but he was suddenly off and singing it, right in front of her. She couldn’t help it. Despite trying desperately not to laugh, she just couldn’t help it. He was too much. Too funny! His silly pronunciation of the words had her in stitches by the time he was finished. Her stomach ached. His silly curtsey at the end barely even registered after the rest of it.
“Well? What do you think?” Mel asked from the doorway behind him.
“He’s too much,” Gloria replied, still trying to control her laughter. “When you said you wanted to show me something, I never expected… this!” She was wracked by another bout of laughter as the sight of him reminded her again of the silly nursery rhyme he had just finished. And the dumb guy was just standing there with the stupidest grin on his face behind that pacifier. Hysterical!
“Well?” Mel asked again.
“Well what?”
“What do you think about… you know… what I want?”
“No,” Gloria replied, still laughing a bit, but now more serious. “I’m not buying… this,” she said, waving her arm at Chad. “And I’m not changing my mind.”
Mel was a bit disappointed, but she had pretty much expected her reaction. Still, she had been hopeful… very hopeful. “How about lunch today?” she asked. “And that – I’m buying!”
Gloria rolled her eyes. “Okay, I’ll do lunch with you. But like I said, I’m not changing my mind! Now get out of here, both of you! Before my clients get here!”
Mel smiled. She still had lunch to convince Gloria, just as she had planned. And she had her arguments all lined up. “Come on, Sissy. Let’s get out of here.”
With one last curtsey, from Chad, Gloria watched as the two walked out of her office and out through the door. No, she wasn’t buying it one bit. She realized that Mel was probably pulling all the stops out here, trying to convince her to hypnotize him again and reset the suggestions to make him incontinent. On someone else, her ploy might have worked, but she recognized it for what it was. A desperate ploy. She was amazed that Chad even agreed to go along with it. And he certainly had been funny! But she still wasn’t going to do it. She still felt like what she had already done was wrong – totally wrong! She still felt guilty about it.
If only Mel would let her talk to him alone… hypnotize him alone. Then she could find out for sure – and maybe… maybe… she wouldn’t feel guilty anymore. Maybe.

Mel pulled out her cell phone while she was driving and dialed another number. “Is the coast clear?” she asked. “Good. See you in a few minutes.” She put her phone away again.
Chad heard her from the backseat. He could see that they weren’t heading for the building where he worked. He had been carefully watching for that. It was also clear that they weren’t heading home. And now it sounded like she still wasn’t done with him… still wasn’t done running him through her humiliation wringer… still wasn’t done trying to ruin his entire life. When this bet was over, he was going to have to move away from here for sure!
So where were they heading? He found out a few minutes later when Mel pulled into the parking lot of her own office. Whew! Chad breathed a sigh of relief. It looked like she was finally done destroying his life. At least for now. Of course he was still dressed in his sissy dress… and he did still have to worry about making his current diaper leak in a few hours… not to mention a host of other things he had to worry about. But he had been to her office many times now. He would be relatively safe there. Hopefully.
Chad started fighting past his ruffles to unbuckle his seatbelt while Mel was still pulling into her personal parking place. When she had stopped and turned her engine off, she turned around to him. “Okay, Sissy. You’ve been great so far, so don’t screw things up now. I’d still like to take you to work and show you off like that. And I still think it’s the right thing to do. But I won’t if you keep behaving like I want you too. At least I won’t do it for now anyway.
For now? Chad was momentarily afraid because it sounded like she still intended to do it. But at least it wouldn’t be right away if she did. Maybe he could find another way out before then.
“When you go in there,” Mel continued, “I think Andrea deserves to see your little show too. So just do it like you did for Gloria and I’ll be very happy. Got that?”
He’d have to do it yet again? This time for Andria? Why not? Besides, she had already seen him doing it at Mel’s apartment last night after dinner.
“Yes, Mistress,” he replied, really not caring anymore. “I’ll be glad to.”
When Chad got out of the car, he didn’t even wait for Mel. He skipped his way directly to Mel’s office door and went inside. He was amazed at how quickly the skipping got him out of the outside public exposure – fortunately.
Andrea looked up from her desk at the sound of the door opening. She was hoping it was Mel and Chad and not one of Mel’s clients. She had moved all of Mel’s early appointments to later in the day, but not the one coming up next. That one she had figured would be okay as it was. But still, the client would be due in soon, and if he got here before Mel and Chad did…
She was delighted to see the ridiculous pink and white ruffles of Sissy’s dress peeking through the door first, followed by Sissy himself. Pacifier in mouth, he came in and quickly stood right in front of her desk. She glanced back to the door, but still didn’t see Mel. Where was she? She watched delightedly as Sissy dropped his funny curtsey to her, and she had to giggle despite herself when she heard his silly sissy voice saying, “Hewwo, Andwea.”
“Hi Sissy,” she replied. “Did you have… an interesting morning?”
“Oh yes!” Chad replied as if he was very happy about what had gone on. “Would you like to hear me sing ‘Mary Had a Little Lamb?’”
Andrea sat back in her chair. Where was Mel? “Sure Sissy. Go ahead.” She had heard and seen it all last night, but it still brought a smile to her face to see him doing it right in front of her again. Her own private little show. Halfway through, Mel finally got through the door. Her arms were loaded with bags. She stood at the doorway watching.
Chad finished up and did his sissy curtsey again while Andrea clapped delightedly. “Wonderful, Sissy. Thank you. That was fun.”
Mel finally walked up. “He was even better earlier,” she told Andrea. “I’ll tell you about it later.”
“Speaking of later… You better get him out of here soon. Mr. Bieber is due in a little while. And if he’s early…”
“Yeah. You’re right. Come on, Sissy. Let’s get you situated in the spare office again.”
Chad was more than glad to follow her back to the richly appointed office where she usually had him go. Especially since he would be well hidden from any of her clients there.
“Get that dress off, Sissy,” Mel instructed as soon as they got into the office. “You’ll be spending most of the rest of the day right here. At least until I have time to take you out later. And don’t wrinkle that dress! Make sure it stays neat!”
Chad was instantly concerned because it sounded like she had more plans to take him out wearing the dress again later. He hoped not! But knowing Mel… He certainly wasn’t looking forward to it – whatever it was that she had planned.
Mel set her armload of bags down on the desk with an audible sigh of relief. She started hunting though them. From one of the bags, she pulled out another full baby bottle and set it on the desk. From another one, she pulled out the top to his baby-doll nightie. “Here,” she said as she set the nightie top on the desk. “Put this on after you get that dress off.”
Chad finally got the zipper down on his dress and let it fall off of his shoulders onto the floor. He picked it up and laid it over one of the beautiful leather chairs in the room where it would be out of the way. He felt strangely naked without it, standing there in just a single diaper and his shoes and socks. He felt better as soon as he had slipped the baby-doll nightie top on again. He was also happy to have his breast forms covered up, even though it was just himself and Mel in the room.
“Ugh!” Mel grunted as she finished looking into another of the bags she had set on the desk. “Must be in the other bag. Oh well.” She turned back toward him. “Just… stay here and try to stay out of trouble,” she told him. “I’ll bring you something to occupy yourself with later. In the meantime…” she glanced at her watch, “you’ve only got about an hour and a half to get that diaper leaking, so get busy. I’ll be back as soon as I get a chance.” She headed toward the door, then stopped and turned around again. She walked back to the desk and pointed to the phone there. “If you need anything, or if your diaper starts to leak, just push that first button to call Andrea. She’ll call me as soon as I’m free. Got it?”
Chad curtseyed. “Yes, Mistress,” he replied in his silly voice.
She smiled. She really did love seeing him do that! “Okay, I got to get to work. I’ll be back.”
Chad stared after her as she quickly left the room. With her gone, the room suddenly felt empty and quiet. After the morning he had just had, the quiet solitude felt very peaceful. He looked around the office. Now what was he supposed to do with himself? She had said she would bring him something later to keep busy with, but what? In the meantime, he had nothing to do at all. Spotting the baby bottle on the desk, he picked it up. He still had an hour and a half to go. Plenty of time. But in this game, wasting even a minute could have very painful consequences. He put the bottle to his lips and started drinking as he headed for the soft leather couch to lay down.

Mel glanced at her watch. She had been working hard since she got here. She briefly wondered how Chad was doing in the other office. She had meant to bring him some things to occupy himself with earlier, but she hadn’t found the time. She felt a tiny bit guilty about that, but then thinking about what it was that she had planned for him, she didn’t feel too guilty. But it was getting on toward lunchtime now. It was time to go meet Gloria. Still, she did have to check in on Chad.
She got up from her desk and went into the other office. Chad was laying on the couch drinking another baby bottle. He sat up straight as soon as she walked in. “Are you leaking yet?” she asked.
Chad glanced down at his diaper. “Not yet, Mistress,” he replied in his high-pitched sissy voice. The voice surprised Mel a bit, even though she had told him she didn’t want to hear anything else. She glanced at her watch. “You’ve still got a while to go. I’m going to lunch right now. I’ll get you your lunch later. Andrea will be here if you need anything.” She thought for a moment. “I expect to see you leaking by the time I get back!”
Chad watched her hurry out. It had been a particularly strange morning. First it had been overly nerve wracking when she had tried to take him to work to show off how much of a sissy he was, then to the gym and Gloria’s, and then finally back here. But since they got here, he had been nothing but bored. It had been relaxing – but boring! His only excitement had come when he wet himself each time. His diaper was getting fairly soaked, but it wasn’t quite ready to leak yet… he didn’t think anyway.
With nothing better to do, he laid back on the couch again with his latest baby bottle. He was startled a few minutes later when Mel burst back into the room. “Here!” she said rather breathlessly, “you can play with these till I get back.” She dropped a rather large plastic bag on the floor, then she hurried out again.
Curious, Chad got up and opened the bag. Baby toys! He recognized them. They were the ones that Sandy gave him every time she “babysat” him. Yuck! He dropped the bag back onto the floor without opening it. If that was what she had planned for him to occupy his time, then she shouldn’t have bothered! He laid back on the couch and put his bottle back to his lips.