The Bet - Chapter 46 (Tuesday – week 7 Part 3 of 9)

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 3 of 9)

Gloria’s phone rang while she was waiting for her next patient. “Hello?”
“Hi Gloria,” Mel said cheerfully.
“Hey Mel. How is everything going? Lunch today?”
“Definitely!” Mel replied.
“Good, because I still want to hear all about your date!”
Mel laughed, “Somehow, I knew you would! See you later?”
“I’ll be there,” Gloria confirmed.

Mel hung up the phone with a smile. And that was when she noticed the email that had come in from Robin. She opened it and read it… and smiled. Amazing! But how to respond? An idea occurred to her, but… did she dare? She finally decided there was only one way to find out. She typed her reply: “Why don’t you meet me for lunch today so we can talk.” Then she gave Robin the restaurant, time, and where she and Gloria usually sat. If Robin actually showed up, she wasn’t too sure how Gloria would like it, but that was a small price to pay.

Robin read Mel’s reply. Lunch? She had to be kidding! Her reply was typed and sent very quickly. “No way!”
She glanced at the clock, then back at Sissy again. He had been doing his little apology continuously for about fifteen minutes now and she was sick of it – and him. “Sissy!” she turned toward him, stopping him in mid-curtsey. “Enough! Get out of my sight now before I find something else to make you sorry!” She watched as Chad hurried rather contritely toward his desk. The idiot! Mel wanted her to meet for lunch? Ridiculous!

Chad lugged his diaper bag toward the gym door. He was still a bit tired after all the exercise he had gotten that morning – curtseying so much. But today he was more interested than usual in having Cassie change his diapers – that is, if that receptionist Cindy wasn’t going to be in there with him again. She wasn’t yesterday, and by the way things had gone yesterday, he didn’t get the feeling she would be today. Maybe, never again! That would certainly be good.
He was mostly interested today because last night he had managed to orgasm from the anal play with Mel. And Cassie always played with him when it was just the two of them. Would he be able to orgasm today? He really hoped so. And now he couldn’t wait to find out.
Once again, he opened the door to see both Cassie and the receptionist Cindy already up front waiting for him. Yes! Yes! Yes!
Cassie turned toward Cindy the moment Chad walked through the door. “He’s all yours today. Just remember what I told you to make sure you do.”
Excitedly, Cindy replied, “Don’t worry. I will.”
Chad glanced back and forth between the two of them trying to figure out what was going on. He’s all yours? That didn’t sound good at all. He was especially worried when Cassie stayed at the front desk and it was Cindy who came out from behind it.
“Hi Sissy,” Cindy said with a mixture of excitement and taunting. Then she stood there and stared at him expectantly.
Chad again glanced back and forth between them. Then, again bowing to the inevitable, he dropped a curtsey and greeted first Cassie, then Cindy.
Cindy giggled. “You’re soooo sweet! Come along now, I’ll be taking care of you today.”
Wide eyed, all Chad could do was to stare at Cassie in horror as he followed Cindy back through the gym full of exercising women, some of whom said hello to him as he walked past. Still in shock, he followed her all the way back to the little room where Cassie changed him every day. Except this time it wasn’t Cassie!
Cindy appeared to be all business as she closed the blinds on the little window in the door and took his diaper bag from him. Chad just stood there and watched as she opened his bag and started pulling out the things she would need. “Aren’t you going to get undressed?” she asked. “I can’t change you with your clothes still on.” Almost in a fog, Chad started removing all his clothes. When he was down to just his two diapers and plastic panties, Cindy handed him his bottle and he laid down on the floor so she could change him.
As Chad drank his bottle, he noticed that Cindy seemed to be going out of her way to act like she knew what she was doing. In one way, she seemed to be all business as she pulled his plastic panties off of him and untapped his diapers, but the look on her face reminded him of a child playing a game – which, he supposed, was probably exactly what was going on.
Carefully, Cindy untapped each layer of diapers and pulled them back, being extra careful as she pulled away the last layer. Chad figured that Cassie must have told her that sometimes he started peeing at the least opportune moments. The memory of which embarrassed him – and excited him too. With the diapers out of the way, still acting business like, Cindy started wiping off his front side, being careful around his chastity device, as if it were some kind of physical injury to his body.
When she was done, she picked up the baby lotion – and stopped. With a broad grin on her face, she set the lotion down again and leaned over closer so she could inspect his device further. She reached out and grabbed the lock, wiggling it around a bit. “Does that hurt?” she asked.
Chad shook his head. “No,” he replied with the nipple to his bottle still between his teeth.
Cindy grew bolder. She reached out and grabbed the hard plastic of the device that encased his shriveled penis. She wiggled it back and forth a few times. “How about that?” she asked.
Chad didn’t know if she was serious or just playing. “No,” he said once again. He really wished she would just get on with it and finish diapering him.
Cindy wrapped her hand around the device as best she could and squeezed, but it was solid and she knew immediately that she wasn’t accomplishing anything. She tugged on it a bit, then leaned in close to try to see the teeth inside of it a bit better, then she tugged again, watching as the teeth seemed to bite into his delicate flesh. “How about that?” she asked.
“Yes!” Chad replied. “Please don’t pull any harder.”
Cindy’s only reply was to giggle. She pulled the device up a bit and grabbed his naked balls instead. She marveled at how strange they felt, like two little nuts inside of a soft leather bag. Maybe that’s why she had heard them referred to as “nuts” before. She squeezed a bit and watched his face. She saw his eyes go wide with concern. She squeezed harder and his eyes went wider. She squeezed a bit more…
“Please!” Chad cried in alarm. “That hurts!”
But as Cindy let go of him, her only reply was another little giggle. She went back to playing with his chastity device and flicked her finger against the hard plastic over top of where he penis was, as if she was trying to flick it against his bare penis instead. It made kind of a soft tinking sound as she did it. “Did that hurt?” she asked.
Chad just shook his head. What on earth was she doing?
Cindy flicked her finger again, but she didn’t have to ask to know that it didn’t hurt him at all.
She searched the top of the desk and found a pair of scissors and grabbed them. Chad grew concerned at the sight of something like that being brought so close to such a sensitive part of his body. But Cindy didn’t open the scissors. Grabbing them by the closed blades, she used them to tap on his plastic chastity instead. “How about that?” she asked. “Does it hurt when I do it with the scissors?”
Chad could certainly feel the added pressure as she tapped, but it wasn’t really hurting him. He shook his head without bothering to remove the bottle from his mouth.
Cindy tapped harder, the sound now making a much more distinct sound. She looked up at him. She could see the concern in his face, but she knew she wasn’t hurting him. Which was good! She didn’t want to hurt him. She just didn’t know a lot about men and getting the chance to play with this one – with his male parts all encased like they were, was just too much of a temptation. Besides, if she hurt him, then Cassie wouldn’t let her change him anymore. But for now, she could still play.
Since she wasn’t hurting him, she began teasing him by rhythmically tapping on it over and over again as if she were playing a song with the tapping. She didn’t tap really hard, but it was still hard enough for him to feel his device being driven down with each stroke, pulling on it at the base over and over again – and unfortunately causing the little teeth inside of it to dig in momentarily each time. The vibrations also stimulated him just a bit while at the same time, the tapping set his teeth on edge. With the extra stimulation, he could suddenly feel the teeth in his device irritating him more and more. “Stop!” he suddenly cried as he pushed her away with one hand.
Cindy looked surprised. “Was that hurting you?”
“Yes!” Chad complained angrily. It wasn’t really hurting – yet, but if she continued then he had no doubt that it would be.
Cindy was surprised and also a bit fearful. She hadn’t wanted to really hurt him, she was just… playing. She threw the scissors back onto the desk and picked up the bottle of lotion instead and began spreading that wherever she could. Chad was just grateful that she was finally getting on with it again. What the heck had she been doing anyway?
Cindy finished with his front side and ordered him to roll over. Chad put his bottle down and did as she said. He missed Cassie here. He had been really looking forward to Cassie playing with him again. He could feel Cindy wiping him off and then spreading the lotion all around, but it was absolutely nothing at all like the way Cassie did it.
Cindy finished with the lotion and wiped her hands off. Then she reached for the jar of suppositories. “According to Cassie,” she said as she opened the lid, “these are the most important thing we’re doing here.”
Chad disagreed completely.
She pulled one of them out of the jar and looked at it. “I just wish putting this thing into you wasn’t such a gross process!
“Don’t do it,” Chad suggested – ever so casually.
Cindy shook her head. “I have to. I promised Cassie.”
“But you don’t really have to. Cassie will never know – and I promise I won’t tell her!”
Cindy shook her head again. “Cassie said you would probably try to talk me out of it!” With that, she took the pill, placed it up against his tiny hole, and started pushing it in with her finger. Since she hadn’t lubed him in there the way Cassie did, not to mention she hadn’t stretched him out a bit first, the pill was hard to push in at first and Chad could easily feel the resistance. But her perseverance won out and it didn’t take long till he felt her entire finger invading him as far as it would go. Ugh! He hated those stupid pills! But as she got the pill all the way in, Chad felt something else too. He suddenly felt the urge to pee again. As he had tried to do all morning, he clamped down hard as soon as Cindy removed her finger and did his best to hold back against peeing. He couldn’t check his watch but that didn’t matter. What mattered was that he tried his best to hold it.
Cindy had him roll over again and she quickly swapped out his soaking wet diapers for fresh dry ones. She wasn’t as fast as Cassie was though and before she finished, Chad was really struggling to hold back. He didn’t want to embarrass himself any further by having an accident in front of Cindy, so he persevered and prayed she would get his diapers fastened up soon.
Cindy had no idea of the struggles Chad was going through, but she was all business again as she did her best to pull the first diaper up tight and tape it in place properly. But as she was pulling the second one up, she realized that the first diaper she had just taped in place looked a bit different – or was it just her imagination. She stared closer to see if she had made a mistake, and she noticed it changing some more. Surprised, she looked up at him. “You’re…”
“Yes!” Chad replied before she could get the word peeing out of her mouth. He was embarrassed that it had happened in front of her, but at least he had managed to hold on long enough for her to get the first diaper securely taped in place. A few seconds sooner and it would have been much more embarrassing!