The Bet - Chapter 38 (Monday – week 6 Part 4 of 7)

The Bet
by Karen Singer

Chapter 38 (Monday – week 6 Part 4 of 7)

The receptionist at the gym spotted Chad’s car driving into the parking lot. She glanced around as he was getting out of the car with is big pink bag. There weren’t many people in the gym just then. For once things were fairly quiet. She wanted to tease him again when he came in… she really almost felt like it was her duty to do it. But she was at a small loss as to how. “Hiiiiiii… Sissy,” she said with a big smile on her face the moment he walked in.
Chad hated having to face her every time he came in, and lately, ever since his “performance” here last week, she had been so much worse! He was immediately wary when he noticed her forward attitude. “Hi,” he replied cautiously. “Is Cassie back yet?”
Clearly the receptionist was caught off guard by his question. “Back? From where? She didn’t go anywhere – that I know of.”
“Oh,” Chad replied. “She phoned me earlier to warn me that she might be late. So she’s here?”
“Of course!”
“Can you get her for me? Please?”
The receptionist might have been taken off guard by his question, but she recovered quickly. “You didn’t curtsey for me yet,” she noted.
Ugh! Chad would have asked if he had to, but he knew better. She could be so stubborn sometimes. He dropped a quick curtsey for her.
“And you didn’t say ‘Hello’ in your funny little voice.”
Double ugh! He curtseyed once again and said hello in his sissy voice for her. “Now will you please get her for me?”
She leaned over the counter and lowered her voice. “Are you here to get your diapers changed again?” She giggled the moment she finished her question.
“Yeah. As usual,” Chad admitted. He was worried about what else she might want to know. He clearly remembered her feeling him all over last week, trying to feel his diapers under his clothes.
“I suppose they’re all covered up so I can’t see them again.”
“Just like always,” Chad replied. Why couldn’t she just go get Cassie and leave it at that?
She pouted. “Oh pooh! It’s just no fun if I can’t see them.”
“I don’t know why you’d want to.”
“Because I do! I’m… interested!”
Chad didn’t think that was the real reason at all. “Will you please just get…”
But before he could finish his question, she was leaning forward again with a rather expectant smile on her face. “Can I watch today?”
Chad was dumbfounded. “Can you… No! Of course not!”
She had only just thought of the idea a moment before she asked the question. But now that she had asked it, she rather liked the idea. “I wonder what Cassie will say when I ask her?” She immediately hurried off with a slight giggle to find Cassie before he could say anything else.
Chad was stunned as he watched her back disappearing around the corner. He desperately hoped that Cassie would say no to her – rather frightening – request.
Cassie and the receptionist appeared at the same time. The receptionist hurried back to her place behind the counter, giggling and eyeing him all the way. Chad kept an eye on her as he dropped a curtsey for Cassie and told her hello.
“Let’s go, Sissy,” she said. “You know the way.”
Chad was relieved to see the receptionist staying where she was as he followed Cassie back through the gym to their usual office. As soon as the door was closed, he had to ask. “Did she…”
Cassie smiled broadly. “Yes she did! That is, if you’re wondering if she asked if she could watch.”
“And what did you say?”
“I said not today.”
Not today! But that didn’t rule out in the future. He started to get undressed.
“I also told her I would have to check with Mel first.”
The very mention of Mel made him stop what he was doing as he remembered the trouble he was in. When Cassie asked her, and he had no doubt at all that she would, would Mel say yes… just to punish him? It was entirely all too possible. Having something more to worry about, he resumed getting undressed.
A few minutes later, another baby bottle in his mouth, he felt Cassie unfastening his very soaked diapers.
“Wow! You’re even more soaked than usual today – if that’s possible!” Cassie exclaimed as she peeled the sodden diapers back.
Chad didn’t want to tell her that he had wet himself without knowing he was going to do it – more times than he was happy about that morning. He had only regained all his control a few hours ago, and even then, he had missed once or twice.
Cassie noted his still tiny penis trapped inside his chastity device. She grabbed the device and shook it back and forth a few times – no reaction. She didn’t bother spending any more time on it. She quickly wiped clean his front side before pulling his soaked diapers out from under him. Quickly, she slipped the two fresh diapers that she had prepared while he was undressing underneath him. “Roll over, Sissy. Let’s see your backside now.”
This was the part that Chad loved – usually… now. He set his baby bottle aside and rolled over, anxious for what he hoped she would do with him… to him.
Cassie quickly wiped off his backside. Then she liberally squirted some baby lotion into one hand and rubbed some onto her other hand. Then she placed her hands right down onto his backside. She saw his back arch a bit at the pleasurable feeling. She started rubbing her hands all around his backside, massaging the baby lotion into him. She watched as he laid his head down on his arms, lost in the pleasure. “I wonder what little Cindy would think if she saw me doing this to you?”
Chad came back to reality with a visible snap. “Cindy?”
“Our receptionist out front. She did ask to watch.”
“I’m so glad you said no. Thank you.”
Cassie giggled a bit as she continued to massage him. “I only said no for today. I don’t know what Mel will say when I ask her.”
Chad didn’t want to think about that, but the more he tried not to think about it, the more he couldn’t get it off his mind. What did interrupt his thoughts though was Cassie telling him to hike his knees up under him, making his backside a much better target for her attention.
While he was getting into position, she reached into her desk drawer and pulled out the toy she usually used on him. He got ready quickly. She squirted a bit more baby lotion onto her toy to get it ready. She didn’t put the toy against him right away. Instead, she pushed her finger up against his tiny asshole first. She felt him pushing back against her slightly, but not hard. She increased the pressure and saw an ever so slight shudder run along his body. She pushed a bit harder and her finger slipped inside.
She pushed her finger in slightly, then pulled it back slightly. In, then out. In, then out. Within moments, he was rocking back and forth to the rhythm she had set. She pulled her finger out and set the tip of her ribbed dildo up against him instead. She saw another slight shudder go through him. She pushed on it ever so slightly, then harder. But the moment it started to go in, he pushed back, harder than she expected. He wanted it that much! But she didn’t want him to have it all yet. She only let about half of it go in before she held it back. She pulled it out, then slowly inserted it again. Then she stopped keeping it in place for a few moments before she did it again. Each time she pushed it in, he pushed back, wanting it to go faster, harder. But by doing it the way that she was, she forced him to accept her pace, not the pace that he wanted. Eventually, she saw him stop trying to control it. Only then did she push it in and out of him more continuously.
After a while, he began trying to control it again – and she held the toy steady to let him. He began rocking back and forth, pulling it out of himself, then pushing it back in. Over and over again.
Cassie leaned over him and very quietly said, “I wonder how much little Cindy will enjoy seeing you do this?” She giggled as she saw his eyes suddenly open wide and look back slightly at her – while he kept rocking. In fact, his rocking suddenly got harder – much harder. Obviously the thought of someone else seeing what he was doing was affecting him.
Chad tried his best to get the relief he so desperately craved. He wished though that Cassie hadn’t mentioned letting the receptionist watch. The very thought of it scared him – and stimulated him too, although he didn’t know why. But as usual, no matter how hard he tried, he just couldn’t get there. He just couldn’t reach that place of ultimate pleasure and satisfaction that he so desperately craved. And then he suddenly felt something warm and wet splashing down his legs that were pulled up under him. He was peeing again – without knowing he was going to do it! He stopped his rocking quickly, pulling out as much as he was able as he tried to pull his now wet legs away from the dripping pee down on them. He tried to look down and under himself to see how bad it was.
Cassie saw him suddenly stop, which surprised her. But then she saw him just as quickly trying to look at something under him. She looked down and saw the pee still running out of him, straight down onto the fresh diapers she had just laid under him. Still holding the dildo where it was in him, she giggled as she watched till he was done. She leaned over him. “Are you going to do that for Cindy too?” His reaction was more like a physical jolt as he lifted his head to stare at her. But his quick motion also shoved the dildo further back into him again, which sent a new wave of pleasure into him. Once again he began fucking himself desperately on it.
Chad’s newfound desperation for pleasure didn’t last very long. Very shortly, he slowed, then stopped, dropping his head down to the floor to let Cassie know that he was finished. He didn’t even know why he bothered to try so hard. Getting what he wanted was impossible! He guessed he just liked it that much. He didn’t even bother to look back or move till he felt Cassie finishing putting the damn suppository up inside of him. Only then did he roll back over onto his back and grab his baby bottle again.
Cassie pulled the first of his two diapers up into place and taped it closed. She leaned closer to his head. “Wouldn’t it be fun to let Cindy do this for you next time?” she asked. She had to giggle again as she saw him shudder and his eyes open wide. He stayed just like that the entire time she pulled his second diaper into place and taped it firmly closed.

“What’s eating you?” Gloria asked as soon as she and Mel had both placed their orders for lunch.
“Ugh!” Mel grunted. “It’s just one of those days. You know?”
Gloria smiled. “That time again, huh?”
Mel nodded. “Plus, Sissy’s been giving me a bit of trouble today.”
“A bit of trouble? Like what?”
“Like not talking properly!” The moment she said it, Mel seemed to get more agitated. “He knows how I want him to behave! He knows how I want him to talk! But you should have heard how insolent he was when I called him at work this morning! Not only was everything all wrong, he outright refused to do it right! What’s gotten into him?” She leaned slightly closer. “It’s that Robin woman he works with! I’m sure of it! She’s probably filling his silly little head with all kinds of wrong ideas.”
Mel leaned back in her seat before continuing. “Well, I’m going to fix her. I’m going to fix it so that she’ll stay away from him – far away!”
Gloria had rarely seen Mel this worked up over something. And worse, she couldn’t be sure just how justified Mel might be in whatever she had planned. “Do I want to know what you’re planning to do?”
Mel smiled wickedly. “Probably… not!”
Gloria nodded. “I thought so.”
“You wouldn’t be willing to slip a few bits into your next session with him to make him mind me better, would you?”
Gloria shook her head. “I’m not even going to get into that!”

Chad stowed his purse in his drawer as he got back from lunch and sat down at his desk. He placed his cell phone on top of his desk. He didn’t want to have to dig it out so quickly again. Lunch had been great! Well, at least the part where he got to eat something. It was the first solid food he had eaten since Friday! Once again he had been through an entire weekend of eating just baby food… well, mostly baby food. The dinner he had cooked last night wasn’t really baby food, but Mel had reduced it to that just the same.
He heard Robin talking in the next cubicle over – probably on the phone. He figured it was safe enough. He clicked on the icon on his desktop to open up the spreadsheet he kept for tracking his progress on the bet.
He looked at the column next to today’s date. Twenty-five days to go. In some ways, an eternity. Yet in other ways, the time was definitely growing shorter. But the question was, could he still win? Could he still pull it off? He was fairly certain he could. After all, he knew his own body well and what it could do. He always regained everything very fast. The troubling thing though, was that after this past weekend, he had been having a lot of trouble regaining that control once again. Mel’s diaper games had definitely had an effect on him this time. But he was once again in control of himself – if you didn’t count what happened at the gym – and that was kind of understandable considering what Cassie was doing to him at the time.
He moved up to the row for last Friday. How long had he managed to hold back? He couldn’t quite remember for sure, but for some reason he thought that it might have been about eighteen and a half minutes. Or should he round it up to nineteen minutes? Either way, it was better than the eighteen minutes he had put down for the day before. Just as an attempt to be more correct, he filled in eighteen and a half minutes. Progress in the right direction! But what would he be filling in for today when he got to it. He had no illusions that he would make eighteen minutes again. He’d just have to hope for the best today and try as hard as he could.
He closed the spreadsheet once again, unwilling to look anymore at his reasons for winning the bet. Mel had left him with all too much to think about concerning that issue.