The Bet - Chapter 47 (Wednesday – week 7 Part 5 of 8)

The Bet
by Karen Singer

Chapter 47 (Wednesday – week 7 Part 5 of 8)

Chad got out of his car with his pink diaper bag. He closed the car door and just stared at the gym door ahead. Yesterday Cassie hadn’t even been there when he got his diapers changed. The receptionist Cindy had done it all alone. And while she was doing it, she had played with him more than he was happy about. Was she going to change him again today? It seemed like Cassie was trying to take more and more of a back seat as far as that responsibility was concerned.
Knowing that he had to do it, he approached the door and went inside.
“Hi Sissy!” Cindy said brightly as he was coming in.
Chad looked around. He didn’t see Cassie today. He dropped his usual curtsey and said hello to her. Then he added, “Are you changing me today, or is Cassie around?”
Cindy’s face quickly lit up more than it already was. “Would you like me to?”
“Not if Cassie is available,” Chad replied.
Cindy pouted a bit. “What’s wrong? Didn’t I do a good enough job yesterday?”
“No, it was fine. It’s just that…”
“But if it was fine, why don’t you want me to do it again today?”
Chad shook his head. “It’s not that. It’s just that… I’d like Cassie to do it if she can.”
Cindy didn’t look all that happy, but she immediately came out from behind the long desk. “I’ll get her,” she replied sullenly.
Chad felt much happier about things. A few moments later, Cindy and Cassie came back together and Chad curtseyed and said hello to Cassie too.
“Let’s go Sissy,” Cassie said as she turned around to head back through the gym again.
Chad followed her back to the same room they always used and started getting undressed while Cassie began pulling things out of his diaper bag. “So how did Cindy do yesterday?” she asked.
Chad just shrugged. “Okay, I guess.”
“No problems?”
Chad shook his head. “Not really.” He paused for a moment before adding. “I didn’t really appreciate the way she played with me yesterday.”
Cassie stopped what she was doing and looked up at him seriously. “The way she played with you?”
Chad nodded. “I know she was just curious, which wasn’t so bad, but she didn’t have to bang on my chastity thing with the scissors!”
Cassie’s jaw dropped. “She did that?”
“Yeah,” he replied as he continued undressing again.
“Did she hurt you?”
“Not really. It’s just that… I didn’t appreciate it.”
“So does that mean that you don’t want me to play with you today… like I usually do?” she teased.
“No! Not at all!” Chad replied quickly. “In fact, I’m looking forward to it!”
Cassie just smiled. “I thought you might be. So what Cindy did wasn’t really so bad then.”
“I guess not,” Chad replied with a shake of his head.
While Chad laid back with his baby bottle in his mouth, Cassie undid his diapers. They seemed different today. “Hey,” she exclaimed. “You’re not nearly as wet as usual!”
Chad removed the bottle from his mouth so he could speak. “I had to change them at work this morning.”
Cassie was surprised. “You wet them that much? Were you leaking?”
“No, Robin…” But he didn’t quite know what to tell her.
“Robin? The same Robin that was there Saturday? What did she do?”
Chad realized that once again he had probably said too much. “She wanted to see my chastity device. So I had to…”
“And you let her?”
“I didn’t have much choice!”
“Why not?”
“She ordered me to show her. Mel has me kind of… following her orders the same as I do for Mel.”
Cassie was shocked. “And this is the same Robin who called everyone sick last Saturday?”
Chad nodded. “Yeah, it’s really weird. I never would have thought her the type.”
All Cassie could think of though, was Robin as she had been at their apartment last weekend. Robin had gone absolutely berserk over what they all were doing. And now Robin was dominating him too? “I never would have thought either,” Cassie finally replied.
She wiped off his front side, taking a moment to examine his chastity device closely for any signs of damage that Cindy might have done to it. Fortunately, everything looked just as it should. She had him raise his bottom up so she could swap the wet diapers under him for fresh ones. Then she had him roll over. “Goodness!” Cassie exclaimed as soon as she caught sight of how red and blistered his bottom was. “Is this still left over from last night?”
“Yes,” Chad replied. “It’s still really sore.”
“I can see why!” Very carefully she applied the baby lotion to his skin and started to gently spread it around. But because he was so sore back there, she didn’t massage it in like she would normally do.
Chad closed his eyes, hoping to feel the wonderful sensation of her messaging the lotion into his skin, but he wasn’t getting that at all today. Which he figured was probably just as well since he wasn’t sure he could stand her touching him any harder back there than she was.
“Do you want me to try to play with you again like I usually do?” Cassie asked. “Or are you too sore?”
But Chad really wanted it. Since he had managed to orgasm with Mel a few days ago, he couldn’t wait to try it again. “Yes, please,” he replied. A moment later, his body thrilled as he felt her fingers going in and out of him, lubricating his asshole in preparation for something… bigger.
Cassie dug into the desk drawer and pulled out her usual toy that she used on him. She put a little extra baby lotion on it to lube it up and then she stuck it up against his hole – and held it there. A moment later, he was trying to push back against it. She giggled to herself. He really wanted it! She only withheld it for a moment before she let him have it, a little at a time. But very soon Chad was pumping back and forth for all he was worth against as much of the thing as she dared let him have without losing her grip on it.
Every bit of Chad’s attention was focused on the delicious feelings of his backside. He wanted it, he needed it. But he also needed to orgasm again, and he tried harder and harder to get there. But he only got to a certain point, and nothing more happened. No matter how hard he pumped, no matter how hard he wanted it, an orgasm was simply beyond him. Had he really experienced it with Mel? He wondered for a moment. But he was sure that he had. So why couldn’t he orgasm now? Maybe it was too soon.
Frustrated and defeated, he slowed his motions and hung his head. He had tried. He had really tried. But once again, the impossible was just that… impossible!
“Wow,” Cassie remarked as he finally stopped and she could pull the toy out again. “You were really going at it there.”
Chad didn’t reply. What would be the point? As good as it had felt, it simply did nothing for him other than to further stoke his sexual need. But still, it had felt awfully good. He heard Cassie unscrewing the lid from the jar of suppositories. Ugh!
Cassie glanced at Chad’s head as she pretended to pull one of the little pills out of the jar. But he wasn’t even looking in her direction. She wondered why she was bothering to go to such lengths to disguise what she “wasn’t” doing. She pretended to stick the pill way up inside of him. There was no reaction from him at all as she did it. Not at all like when she stuck her other toy up inside of him. “Okay, roll over again. Let’s get you finished up.”

Mel returned to her desk, still thinking about her lunch with Gloria. She had really rubbed it in today about how great her date had been. Maybe too much? No, not really. Ray had been great. Totally! It was just that… everything had almost seemed so artificial with him.
But the one thing that was most on Mel’s mind was that Gloria had suggested that she give Ray her phone number. She knew that Gloria hadn’t been serious about it, but still. Why not? What did she really care if Ray went out with Gloria? As far as she could tell, Ray went out with every woman he came in contact with!
Figuring she was probably doing her friend a favor, she looked up Ray’s number and called him.
Ray’s phone rang and he answered it without looking at it. “Hi Ray,” Mel’s voice came though to him.
“Mel!” Ray replied as he stopped working and sat back in his chair with a pleased look on his face. “Did you enjoy yourself last night?”
“What do you think?” Mel asked sarcastically. “You know I did!”
Ray chuckled. He always knew how to treat them! “So when would you like to get together again?” he asked. Always best to get the dates scheduled as soon as possible!
“That’s just it,” Mel replied. “I have this special favor to ask of you.”
“A special favor? Anything! Do you have something special in mind you’d like to do together?”
“Um… Not off hand. This is something else.”
Mystified, Ray asked, “What?”
“Uh…” She hardly knew where to start with a request like this so she just barged in. “Let’s face it, I know you go out with a lot of women, and I don’t go out all that often, so while I really can’t wait to go out with you again… I was wondering if… you’d do a special favor for me and ask a friend of mine out sometime.”
That surprised Ray. A friend? His first thought was what was wrong with her friend? Then he had another thought. “This friend of yours wouldn’t be anyone like Sissy, would it?”
Mel almost laughed. “Oh, no! Not at all. In fact, she’s really rather pretty, and very intelligent too. It’s just that the hours she works doesn’t let her get out and meet anybody all that often.”
“Oh? What kind of job does she have?”
“She’s a therapist. She specializes in relaxation therapy.”
Ray had never heard of it, but it sounded plausible to him. Besides, he guessed he could always enjoy a nice “relaxing” date once in a while. “And you’re sure this isn’t someone like Sissy?” he asked.
“Absolute not! Listen Ray, Gloria is my best friend!”
Ray felt a little more relieved. “In that case, why not? You said her name is Gloria? What’s her number?”
Smiling, Mel told him the number she had memorized years ago. “You’ll like her, I’m sure of it,” Mel added. “Just don’t forget, I wouldn’t mind going out with you again sometime too. But please, call Gloria first, okay? Do me this favor?”
Since Mel still wanted to go out with him, he was feeling much better about this blind date kind of thing. Mel wouldn’t ruin her chances of going out with him again by making him mad if Gloria wasn’t at least decent. “You got it!” I’ll call her today,” he told her.
“Thanks Ray, I really appreciate it. And, I appreciate our evening last night too.”

Chad still had nothing to do. He wished Robin would assign him something – anything! But so far, she hadn’t even talked to him this afternoon. He thought back to his time with Cassie a little while ago. He was so glad that it had been just Cassie today. And he was glad that she had “played” with him again. He had really hoped to have another orgasm but it just hadn’t worked. It was almost like there was something missing. Some missing ingredient. He just didn’t have a clue what that might be.
Having nothing better to do, he typed in “fashion” in his search page – and a few minutes later wound up searching for shoes.

Robin poured over what needed to be done on their project. She knew that Chad in the next cubicle wasn’t doing anything at all. But she was going to be in charge of this one – no if’s ands or buts! Besides, there was no real reason why Tom couldn’t have assigned the whole thing just to her. He could have easily found some other busy work for Sissy to do. She knew that they were supposed to be splitting up the work, but, well, there was no way she was going to let Sissy do anything except the most menial boring parts of this project. Of which, she knew there would be plenty. But of course, since she had just barely started, she had nothing for him to do right now. Well, he was sitting doing nothing right now, and he could continue sitting and doing nothing for a while more. It wouldn’t hurt him in the least!
Two minutes later, she came across something, part of which she would have put off till later. But Sissy was there and he could take care of it for her right now. With a smile, she looked up toward the top of the wall between them and called, “Sissy! Get in here!”
Robin calling him totally surprised Chad. He got up and hurried around the wall to her desk. “You called?” he asked.
Robin turned around in her seat to talk to him. “I need you to…” But that’s as far as she got before an odd thought intruded in her head. Something that Mel had said in her email earlier. She stared at him. He was just standing there expectantly... waiting to hear what she had to say. But that odd thought… “Say,” she started again, “I hear from Mel that she’s trying to teach you to curtsey pretty much constantly.”
Chad felt his face blushing. “Sort of,” he admitted.
“Sort of? That’s not the impression I got.”
“It’s just… mostly… when she speaks to me and before I leave again.”
Robin nodded. It was more than that and she knew it! She was a bit perturbed that once again he was trying to get away with only telling half-truths… like a child! But she wasn’t going to push that issue right now. She did want to try one thing though. “Well then,” she replied, “I don’t see any reason why you can’t do the same for me. Whenever you come in here, I expect you to curtsey immediately. And you can curtsey again before you leave. Got that?”
Chad wasn’t exactly happy about it, but he curtseyed for her. “Yes,” he replied. “I’ve got it.”
“Good! Now look at this. I need you to go through all of these and…”
As Robin talked, Chad realized it was all boring busy work, but it was work that definitely needed doing and he had nothing better to do. But as he listened to her going through what she wanted, his mind was mostly occupied with the fact that she was now requiring him to curtsey every time he came into or left her cubicle. It was like she was trying to do everything that Mel made him do.
“Okay, got that?” Robin finally asked.
“Yeah, got it,” Chad replied. “I should have it for you in a little while.”
“See that you do,” Robin replied. “Now get on it!”
Chad started to turn away to go back to his own desk, but he stopped himself quickly and curtseyed to her before leaving.
Robin giggled a bit at his curtsey. Yes, there were definitely parts to this dominating business that were kind of fun! Now she just needed a way to deal with his other childish behaviors! Some of which definitely irked her!

Gloria was between clients and was using her time to get caught up on recording the notes on several of her last sessions. When her phone rang, she thought nothing of it. She even continued to type with one hand while she picked up her phone with the other. “Relaxation Therapy. Gloria speaking.”
“Gloria?” Ray replied. “This is Ray, Mel’s friend. She wanted me to call you.”
Gloria hit two wrong keys and stopped typing immediately. She couldn’t believe it! “Ray? The Ray Mel went out with last night?”
“That’s me,” Ray replied proudly.
“Wow! I can’t believe it. She really asked you to call me? I was only joking!”
“Well, the fact that I’m calling now should answer that. Mel said that you don’t get to go out very often. So I thought maybe we could fix that.”
Gloria was still a bit in shock. “Um… Yeah, sure! Definitely in fact!”
“Well, if you aren’t too busy, then how about later this week? Thursday or Friday maybe?”
Gloria’s mood suddenly fell. “Well, that’s just it. I can’t. I do a lot of my business at night, after hours, when my clients can get here.”
That was going to be a problem! But Mel had mentioned that her business got in the way. “There must be some time when you’re off,” Ray suggested.
“Only on the weekends. Saturday and Sunday are really the only evenings I have off… unless you want to get together for a little while during the week after nine thirty or ten.
But Ray had only needed to hear Saturday! “How about Saturday then?” he asked. “I could pick you up and I’m sure we can find something fun to do.”
Gloria didn’t even need to think about it. “Let’s call it a date!” Two minutes later, Gloria called Mel’s number and was very pleased when she answered. Instead of speaking, she sang! “I’ve got a date with a very handsome man!” Mel only laughed.