The Bet - Chapter 27 (Thursday – week 4 Part 3 of 6)

The Bet
by Karen Singer

Chapter 27 (Thursday – week 4 Part 3 of 6)

“So tell me, what’s so different about what you’re planning to do tonight that you couldn’t explain it over the phone?” Mel asked Gloria as soon as they had ordered their lunch.
Gloria smiled. “Well, I think I mentioned this before, but this week, along with reinforcing what we’ve already done, I think we’re going to let him talk to us, probably a lot. I’d like him to tell us, in his own words, how he thinks things are going.”
“Ok, that sounds like it should be a good idea.”
“Yeah, but I kind of wanted to warn you before we got into it, it’s probably going to seem a bit unnerving at first – because he’s going to seem like he’s completely awake and not in a trance at all.”
“But he still will be?”
“Yeah. That’s the idea.”
“How will you know in case he isn’t?”
Gloria shrugged. “It will be kind of hard to tell. You have to know what to look for. And even for me it won’t be easy.”
Mel thought about that for a moment. Can you have him keep his eyes closed the whole time? That might help… so at least I’ll know that he’s still under.”
Gloria smiled. “That’s a good idea. I can definitely do that. Now listen though. I need you to be especially quiet during this. I’m going to have a hard enough time keeping him under as far as I can get him. Any disturbance could wake him all too easily – and then he’ll realize what we’ve been doing to him all along. If he realizes it, well… I think he’ll probably be able to fight the conditioning fairly easily. That could make things a lot harder for you.”
Mel nodded. “Don’t worry. I’ll just sit and listen. Besides, I’ve been good so far, haven’t I?”
Gloria smiled and reached out her hand to touch Mel’s hand. “It’s been going better than I ever thought!”

“Hi Sissy,” the receptionist called out all too loudly for Chad’s comfort the minute he walked through the door to the gym.
Unfortunately, Chad’s discomfort over her greeting was compounded by two women he had never seen before standing in front of her counter. The receptionist was peering around them at him… which, of course, meant that the two women had turned around to look directly at him too. The surprise on their faces was very evident… as was the expectant look of the waiting receptionist as she continued to stare at him – waiting for his usual curtsey and return greeting. But he wasn’t about to give that to her this time. Not with those two women standing there. He just stopped where he was, well away from them and waited for the women to leave.
“He’s being stubborn today I guess,” she explained to the two women.
“Well, I didn’t believe it anyway,” one of them replied.
Chad’s face turned bright red as he realized that the receptionist must have been telling them about him.
“I don’t know,” the other woman replied as she again turned to look at Chad, “He’s certainly dressed completely like she said. Of course he’s not wearing a dress today, but still… I’ll bet he does!”
Chad was tempted to get out of there and skip the whole thing, but he really wanted his soggy diapers changed and this was his only chance. But these women had been discussing him! What was he supposed to do?
“Come on, Sissy,” the receptionist pleaded. “Won’t you please show us your pretty little curtsey?”
Chad was completely speechless. He couldn’t believe that the receptionist would ask such a thing from him. No, he could believe it! But what should he do? He didn’t really want to do it in front of these women. “Can’t you please just find Cassie for me?” he asked.
But the receptionist got stubborn. “No! Not till you show these nice ladies how pretty you can curtsey.”
Ugh! “Please just get Cassie.”
But the receptionist stubbornly shook her head and said, “No.”
The receptionist’s stubbornness only increased Chad stubbornness too. He wasn’t about to curtsey in front of the two strange women, no matter what. Their encounter quickly devolved into a staring match – with Chad staring at them and all the women staring at him. And this time, Chad won! The receptionist finally rolled her eyes. “Sorry,” she said to the two women. “It looks like he’s not going to be very cooperative today.”
“That’s ok,” the first woman said. “Men are always stubborn… no matter what they’re wearing,” she added with another cross glance at Chad.
Chad stood back and waited while the two women walked past him, both of them looking him over even more carefully as they went out the door. When they were gone, he turned back to the receptionist. She was again looking at him like she was waiting for something. He got frustrated. “Will you please just get Cassie now?”
She shook her head with disappointment. “Wow, you’re no fun at all today,” she grumbled as she left in search of Cassie. Chad only felt relief.
The receptionist was back a few minutes later with Cassie. Chad dropped his usual curtsey and greeted Cassie, but as he was doing it, he glanced at the receptionist with a rather “stick it up your ass” look. He saw her rolling her eyes as she walked behind the counter. Chad put her totally out of his mind as he followed Cassie to the back office again.
“She says you didn’t want to curtsey for some of our guests,” Cassie said as soon as she had closed the door behind them.
“No way! I don’t know them. They’re not Mel… or even you or Sandy!”
“Uh huh,” Cassie murmured as she watched him struggling to remove his clothes. Chad removed everything but his diapers and waist cincher, then he laid down on the floor and Cassie handed him his baby bottle to start working on. “It wouldn’t have killed you to be nice,” Cassie said as she started removing his diapers.
“It’s demeaning!” Chad replied through the nipple in his mouth.
Cassie looked up at him for a moment. He was laying in front of her so she could change his soaked diapers, he was drinking from the baby bottle stuck in his mouth, he face was covered with makeup, his nails were long and painted red, his hair was femininely arranged… and he was worried about something being demeaning? One thing was for sure, she’d never understand men! Once again she thanked her lucky stars to have Sandy in her life instead of some stupid man.
She poured a generous amount of baby lotion into her hands and went to work on his front side. As she worked, she kept staring at his penis locked up inside of the chastity device. The tiny little thing looked even smaller today than usual. She was surprised because she didn’t think they could get so small. She worked extra hard at trying to get a reaction from his plastic encased penis… but no matter what she did, or how she pulled on his chastity device, it was as if she wasn’t doing anything at all. She glanced up at his head. He was still sucking on his bottle. The look on his face suggested that he wasn’t even paying attention to what she was doing. Geez!
She cast one more glance down at the tiny nub that his penis was. It hadn’t grown a bit. “Roll over. This is becoming a waist of time.”
Chad put his bottle down and rolled onto his stomach, then pulled his legs up under him, exposing his backside high in the air for Cassie’s attentions. He was rather looking forward to this part again. The first part, where Cassie was working on his front side, had become nothing but uninteresting to him. He couldn’t get a reaction there and consequently didn’t pay all that much attention to it anymore. But his backside… He wondered yet again why he should find what she did to him there so thrilling.
“Your diaper rash looks a lot better today,” Cassie noted right away.
“It feels a lot better too,” Chad replied. Then he felt an electric shudder run through him for a moment as Cassie squirted some of the cold baby lotion right onto his backside. But the sensation of her hands running over him a moment later was pure heaven. He closed his eyes and relaxed into the sensations.
Cassie rubbed her hands all over his backside. She couldn’t see his face in the position he was in, but she could still tell how much he was enjoying it. She was a little disappointed that he hadn’t been nice enough to curtsey for the two customers earlier. She was tempted to just rediaper him and send him on his way, with no further fun that he now seemed to crave. And the more she thought about that, the more she liked the idea. But first… Why not tease him a bit?
She picked up the toy she usually stuck inside of him and place the tip against his backside, right up against his asshole. She placed it there ever so gently, not pushing at all… and she waited.
Chad felt whatever it was that she usually used on him being placed up against his asshole. The thrill was like lightning coursing though his body. He waited for her to push harder, but she was obviously teasing him because she wasn’t moving it at all. Please push… please… His silent pleas went unanswered though as she continued to keep it just as she had. He couldn’t take it anymore and he slowly pushed back against it, expecting it to slide right into him. But it didn’t. The more he pushed back, the more she pulled it back, keeping the pressure exactly the same. He started moving back and forth, pulling away, then thrusting back toward her toy again, trying to get it into him. But each time she kept it so that it only kept touching him and never anything more. His bucking became harder and harder, but it wasn’t getting him anywhere. His frustration grew till he finally stopped and slumped down as if he were exhausted. What kind of game was Cassie playing?
Cassie pulled her dildo away and set it down. “You weren’t nice to our other guests earlier, so I don’t see any reason why I should be that nice to you today,” she explained with more than and ounce of satisfaction in her voice. “But there is one thing I will stick up inside of you. For once I don’t mind shoving these suppositories up into you at all!” And with that, she shoved her finger up his asshole as far as she could. The fact that she was only pretending to stick anything up inside of him made no difference since it was Thursday and one of the days that Mel had told her to only pretend to do it. And since she was only pretending… “In fact,” she started, then she stuck her finger up inside of him again, “there’s a second one for you to enjoy today!” She felt a bit of satisfaction at her fake cruelty. He would never know that he had received nothing at all.
Chad was shocked… to the core. Not only was Cassie denying him the only pleasure he had been able to find lately, she had stuck not one, but two suppositories up inside of him. What kind of messy backside would that produce later? He wasn’t looking forward to finding out at all!
At Cassie’s prompting, he rolled over onto his back again and grabbed his bottle to finish while she diapered him again. He looked up at her as he finished his bottle. She was staring down at him while she worked, but she wasn’t saying anything at all. She did have a very self-satisfied look on her face though. In fact, she was smirking with vindication. All because he hadn’t curtseyed for those two strangers? The heck with it! Chad still felt justified and more glad than ever that he hadn’t done it. So there!
As he walked past the receptionist on his way out a few minutes later, he was tempted to stick his tongue out at her, but he held himself in check. A gesture like that would have been a little too childish. He had enough childish tendencies in his life to deal with already.

“Hi Mel. It’s Cassie.”
“Hi Cassie,” Mel replied into her phone. “How did it go today? Anything new?”
“Well, kinda’.”
“What happened?”
“I know I shouldn’t expect it, and I know I have no right to make him do something like that but…”
“Like what?”
“Well… you see, our receptionist said that she asked him to curtsey for two of our customers when he came in today, and he flat out refused. He wouldn’t even curtsey for her like he usually does.”
“He usually curtseys for your receptionist?”
“And me… well, I kind of got started making him do it at first, but now… well he just does it naturally.”
“Did he curtsey for you today?”
“Yeah, no problem.”
“But he wouldn’t do it for anyone else?”
“No. I know he probably doesn’t have to. But I was just wondering… seeing as how she did ask him nicely… or so she claims.”
“Hmmm,” Mel mused.
“I’m just not real clear on the lines of authority here I guess.”
“Don’t worry about it Cassie. Let me think about it a bit. I’m not real sure either.”
“Ok. Thanks Mel. No problem. Sorry to bother you with it.”
“Don’t be sorry. I’m glad you called. By the way, did you fake putting the suppository in him again?”
Cassie laughed. “Not just one, but two! I told him I was mad at him for his behavior earlier.”
Mel laughed a bit too. “Great Cassie. I have no doubt that two suppositories will really give him second thoughts all afternoon – even if they were fake!”
Mel hung up her phone. She had work to do, but her thoughts were completely focused on Sissy and his refusal to curtsey for Cassie’s customers. But should he have been required to? Or was what he did perfectly within his rights. On the other hand… he had no rights! None! Not as far as she was concerned. But should she do anything about it? That was the question that haunted her for the rest of the afternoon.