The Bet - Chapter 41 (Thursday – week 6 Part 3 of 8)

The Bet
by Karen Singer

Chapter 41 (Thursday – week 6 Part 3 of 8)

The gym door loomed ahead of him. He stopped before he opened the door and just stared at it for a moment. Did he have the courage to face that darn receptionist again? But actually she was only a minor nuisance on the way to the only fun he was really allowed anymore – as long as Cassie was going to keep playing with his backside. And as long as the receptionist wasn’t going to be watching him, he was rather looking forward to that bit of stimulation today.
He looked through the glass door and could see her watching him… expectantly? Probably. Summoning up his courage, he opened the door and trudged inside. He knew better now than to try to get out of it. He dropped her his usual curtsey and said hello to her in his sissy voice. He was rewarded by hearing her giggle at him.
“Hi Sissy,” she said with a broad smile on her face. Then she leaned across the counter and got more serious. “Cassie says I have to ask your permission to go back and watch again today. So… can I? Can I… please?”
Chad was totally aghast. That was the last thing that he wanted. Before he could answer, Cassie walked up from the back.
“Have you asked him yet?” she asked Cindy.
“Just now,” Cindy replied.
Cassie looked to Chad. “So what is it? Yes or no?”
“Oh please…” Cindy begged again before Chad had the chance to vehemently refuse.
Chad shook his head. “I don’t think…”
“But I promise I won’t hurt you this time! I won’t even touch you… unless you want me to that is.” She giggled some more.
Chad shook his head again. “I don’t think it’s a good idea,” he finally got out – politely.
But Cindy wasn’t about to be put off that fast. “But it would be a good idea for me to be there!”
That surprised Chad. “Good idea? How could it possibly be good?”
“What if Cassie can’t be here? What if she’s too busy? What if she’s sick? You still need someone to take care of you. And I can do that!”
Chad was not just surprised, he was aghast! “But…”
“It’s really a good idea,” Cindy continued. “You’d have a backup in case Cindy can’t help you. And I’m more than willing.”
Chad had no doubt about that!
“She does have a point,” Cassie added. “What if I can’t be here? Maybe it ‘would’ be a good idea.” But then she thought of something else. “Are you really sure about this?” she asked Cindy. “Some of this is rather… unpleasant, not to mention down right disgusting! And you’re going to have to take care of all of it. Are you prepared for that?”
That stopped Cindy in her tracks. “You mean, he sometimes…”
Cassie nodded. “Not very often, but it has happened. And it’s a major mess.”
“But you said not very often, so hopefully I may never have to deal with it.”
“Yes, but there are other aspects that you may find just as unpleasant that you’ll have to deal with every time. Unusual aspects.”
The phrase “unusual aspects” registered on Cindy immediately and instantly got her curiosity up even higher. “Really? What?” she wanted to know.
Cassie shook her head. “Things I can’t discuss here.”
Chad was silently praying that Cindy would back off now. He didn’t want to imagine Cindy playing with his back end the way Cassie did. Well, he was curious about it, but he simply didn’t want Cindy there!
Cindy turned things over in her mind very briefly. But now there was another aspect to the silly sissy here that she wanted to know about, an unusual one. She was more interested now than ever. “I still want to. More than ever now!” she declared boldly.
“Okay Cindy. You’ve convinced me. You can watch again.” Cindy let out of squeal of delight. “Better go find someone to watch the desk while you’re back there.”
Chad could feel himself backed into a corner he didn’t want to be in. What had happened to needing his permission? “But I thought…” But that’s as far as he got. He looked at Cassie in horror.
Cassie just looked at him with a dominating smirk on her face. “And what say does a big sissy baby like you have in the matter?”
Chad said nothing, because he knew he really had no say in the matter at all. Meekly, he followed Cassie back toward the little office they used every day. Cindy arrived excitedly just before they closed the door. He didn’t really want her in there at all!
“Pull that shade down on the window,” Cassie told Cindy. She looked at Chad who wasn’t moving. “Aren’t you going to get undressed? Neither of us has all day.”
Chad had a feeling that this wasn’t going to go very well at all. Not happy about matters, he began unfastening his skirt. As he removed each item of clothing, he had to listen to Cindy’s excited surprise over every little item he was wearing. Why did she have to be there? Finally, he was down to just his waist cincher, diapers, and plastic panties. He laid down on the floor to get changed – in front of Cindy again.
Cassie usually prepared everything for Chad’s diaper change while he was undressing, but not today. Since Cindy was so fascinated with everything that Sissy was wearing, she put it off till she could get all of Cindy’s attention… or at least, more of it. Once Sissy was ready, she knelt down next to him and motioned for Cindy to do the same. She pulled the diaper bag next to her and opened it. “Everything you need is right in here,” she told Cindy. She reached into Sissy’s diaper bag and pulled out one of his baby bottles. Instead of handing it to Sissy, she handed it to Cindy instead. “Here, want to give this to him?”
Cindy took the bottle delightedly. “Here comes your bottle, baby,” she crooned teasingly as she brought the nipple to his lips. Chad let it slip into his mouth and began sucking on it as he brought his hands up to hold the bottle. But Cindy wasn’t letting go. Was she going to hold it for him the whole time?
“Let him hold it,” Cassie said as she sorted through the diaper bag.
Cindy reluctantly relinquished her hold on the bottle. Chad felt a tiny bit better about the matter.
Cassie stopped what she was doing and looked into the diaper bag, then up at Cindy. Then she suddenly passed the diaper bag over to her. “Here. You want to learn how to take care of him? Then you should do this.”
Cindy squealed again with excitement.
Chad took the bottle out of his mouth to protest, but one determined look from Cassie stopped him. He put the bottle back in his mouth and began drinking again. Oh great! Now the stupid receptionist was actually going to change him! Not good!
“You’re going to need two of those disposables,” Cassie told Cindy. “There’s a small pair of scissors in the bag, but I usually use the better ones on the desk there. You’re going to have to cut the lining of one of them.” She guided Cindy though her usual process of preparing the fresh diapers for Sissy.
All too soon, Chad felt Cindy pulling down his plastic panties… down his legs and off of his feet. Under Cassie’s guidance, she pulled open his soaked diapers. She didn’t do much else for a moment as she looked closely at his plastic enclosed penis.
“It’s so small,” Cindy remarked to Cassie. “Is it always like that?”
“It has been for a while now. But of course, as you can see, that thing won’t let it get much bigger.”
“But there is still some room in it.” Cindy noted.
Cassie smiled. “And that’s just the way it’s supposed to stay.”
But with Cindy now working on him, for some unknown reason, Chad was beginning to feel the faint bite of the teeth inside that chastity device – warning him, threatening him, reminding him of what might happen if he started to get the least bit hard again. But that was something totally out of Chad’s control. He did his very, very best to lay back and ignore what was happening to him below his waist.
Chad closed his eyes and felt someone wiping off his front side. He tried to convince himself that it was Cassie doing it, but that was difficult since Cassie was constantly telling Cindy how to do everything. And then the soaked diapers under him were removed and he set his bottom back down on two fresh dry ones.
“Okay Sissy. Roll over,” Cassie directed.
Chad set his baby bottle down and rolled over. Was Cassie going to have Cindy play with him… like she did? He worried about that the entire time she was wiping his backside clean. And then came the baby lotion being applied. Not massaged into him like Cassie did, just… applied. Wiped onto him. It was with relief that he next heard Cassie telling Cindy about the stupid suppositories and what she was going to have to do with them. He was glad to hear Cindy make an exclamation of how awful it sounded, but the stupid girl plucked up her courage and took the lousy jar anyway. A moment later, he could feel her cautiously trying to insert the miserable thing up into his rectum.
“How do I get it in?” Cindy started to say, then all of a sudden her finger and the pill went up inside of him. “Oh!” she exclaimed with surprise as she pulled her finger back out again, leaving the suppository just inside of him.
“You’re going to have to push it all the way in… up as far as you can reach.” Cassie told her.
“Do I have to?” Cindy asked as she held her finger up, thinking only how gross it was and wondering how long it would be till she could wash her hands.
“You’re the one who wanted to do this,” Cassie reminded her. “I told you that there were some unusual aspects to all of this.”
Instead of saying anything, Cindy put her finger back down on his little hole and pushed a bit, trying to get it inside. “I’m not hurting him doing this, am I?”
“No. In fact, he rather likes it!”
Very slowly and cautiously, Cindy stuck her finger all the way up into him as far as she could, pushing the little pill up further and further. Ewww! Then, very quickly, she pulled her finger back out again. Cassie handed her a wipe so she could wipe her hand off again. Cindy was surprised that her finger had come out of him… relatively… clean. She had expected it to be all brown and totally disgusting. But as she wiped her finger off along with the rest of her hand, she looked down at his backside and thought about what it was that the suppositories were supposed to do. “But with that thing up inside of him, won’t it make him…” She paused, trying to find a polite way to say it.
“Absolutely,” Cassie replied. “That’s the whole point.”
“And he gets one every day?” Cindy asked.
“Actually, he gets one now and one before he goes to bed every night too.”
Then Cindy wondered something else. “How long before they start working? I mean, will he, you know, before I get him diapered again?”
Cassie almost laughed. “No. But I’m not really sure how long before it goes to work.” She turned to Sissy. “How long before these things usually do their thing?”
Chad answered, but it was reluctantly. “It usually takes a couple of hours now. I suddenly find myself with… problems, by mid afternoon.”
“So who changes you then?” Cindy asked.
“Nobody, not till I can get home after work and take a shower.”
Cindy giggled. “So you’re stuck in messy diapers every day?”
“Unfortunately.”
Cindy giggled again. “Poor baby,” she said to him.
“Okay, Sissy. Time to roll back over again.”
Chad rolled back over and picked up his baby bottle again while Cassie directed Cindy in how to tape both diapers up. Then his plastic panties were pulled up onto him again.
“You’ll usually have to wait a few minutes till he finishes his bottle,” Cassie told Cindy. He has to finish it before he can get out of here.”
Cindy just laughed. “What a big baby!”

Mel checked her messages after lunch and found one from Cassie asking her to call. That was nothing new, Cassie called almost every day. Mel found that sometimes she enjoyed the break from thinking about her work cases. But she had a few minutes now so she tried to reach Cassie back again. She was rewarded to hear Cassie answer her phone. “Hi Cassie. What’s up?” Mel asked.
“Hey Mel. I just wanted to tell you about what happened today… before you could hear about it from anywhere, or anyone, else.”
Mel was immediately a bit anxious about what Cassie was going to say. It sounded like trouble! “Okay… What happened? What did he do now?”
“Him? Nothing. Me, on the other hand, well... Remember our little receptionist Cindy that I allowed to watch a bit before?”
“Yeah,” Mel returned cautiously.
“Well, I let her convince me to let her watch again. But she kind of suggested that it would be a good idea because if I’m not available for some reason, then she would be available to change him. You know?”
“Okay… I’m with you so far. So you let her watch again?”
“More than that, I let her actually do the work. I had her change him while I told her what to do.”
“I see…” Mel replied as she tried to think about the whole situation. “And what did Sissy seem to think of the idea. Did it seem to excite him?”
“Not exactly. And he wasn’t too pleased about it at all.”
“But he let her do it.”
“I didn’t exactly give him a choice in the matter.”
“Okay…” Mel replied as she digested that too.
“And how did she do?”
“Basically, she did just fine. I didn’t mention any of the ‘other’ stuff I usually do with him, but I did make her shove one of his suppositories up inside of him since it was his day to get one. I didn’t tell her though that he doesn’t get them every day anymore. I didn’t want to take the chance that she might tell him. So please don’t be mad at me. You said to use my own judgment on the matter.”
“Oh, I’m not mad at all,” Mel replied as she fully digested everything that Cassie had told her. “It sounds like it all went just fine, so I guess that now Sissy will have one more thing to worry about, or maybe look forward to, when he goes in there. You did say that she likes to tease him. Maybe it will prove to be… interesting for him in the future.”
“Maybe,” Cassie agreed. “And besides, like she pointed out, now there’s someone else here besides me who can take care of him… if necessary.