The Bet - Chapter 32 (Tuesday – week 5 Part 3 of 6)

The Bet
by Karen Singer

Chapter 32 (Tuesday – week 5 Part 3 of 6)

Mel sat at the table and watched as Gloria threaded her way through the restaurant toward their table. She put a big smile on her face as her friend finally sat down.
“Whew! I think the traffic gets worse every day!” Gloria exclaimed.
“I know what you mean,” Mel replied. She stared awkwardly at her friend, not knowing what to say. The silence between them mounted since neither one of them knew quite where to start. Fortunately, the waitress was there quickly to take their order.
When the waitress had left, Gloria was the first to break the silence. “You didn’t order much,” she noted.
Mel shrugged. “Sissy will be cooking for me tonight. It’s always diet recipes, but I’m still afraid to eat much anywhere else. His cooking is always sooo good!” she added quickly. That statement brought the subject of conversation close enough to some of the things she wanted to tell Gloria. She blushed ever so slightly as she continued, “It’s not just the baby thing you were talking about yesterday,” she began. “Yeah, I do like it and it does turn me on… but that’s really more his thing than mine.”
“His thing? So what’s your thing?”
The waitress was suddenly back, setting cups of coffee down in front of each of them. Mel picked her cup up and sipped at it, more to delay and collect her thoughts than from want of something to drink.
“My thing?” Mel finally said. Her face seemed to light up as she pictured him the way she loved him in her mind – in his maid’s uniform. “My thing… It’s… It’s like having the perfect personal servant. One who’s absolutely attentive to my every little need. And he cooks… like a dream! And he cleans the house… like a dream! And he’s so sensitive. I mean, he really listens to me – as if he’s really interested in what I have to say. Most of the guys I’ve ever gone out with, in fact none of them, have never been like that.”
Gloria was suddenly feeling more than a bit jealous. Her description was more like every woman’s dream… except for him being a total flake! She wanted to ask again if Mel loved him, but she didn’t bother. No matter what the situation really was, Mel would only deny it. “So he makes the perfect little maid?” she finally replied.
Mel only nodded as she took another sip from her coffee.
“I know you don’t want to hear this Mel,” Gloria continued softly, “but that still isn’t any reason for me to do what you want me to do with him. And like I said before, I’m not going to do it.” She was afraid that Mel might get angry again. Fortunately, she only saw Mel take a deep breath.
“I know,” Mel replied sadly. “But still, there’s got to be some way you can help me.”
Gloria shook her head. “None that I can see. Are you going to let me have him to myself for a little while so I can put my own demons to rest?”
That was the last thing the Mel wanted. There was too much of a chance that Gloria would undo everything else that she had already done to him. She shook her head. “No. Can’t do it.”
“I was afraid of that,” Gloria replied disappointedly.
Mel didn’t walk out, and neither did Gloria, but they both pointedly stayed well away from any conversation that had anything to do with Chad for the rest of their lunch.

Chad approached the door to the gym and paused. Yesterday he had made his debut here as a complete and total sissy – acting in ways that he never imagined he ever would… or could. So many people had watched him – closely. He felt embarrassed just thinking about it now. Could he make himself go in there again? Ever? With a mental sigh, he knew he had no choice. There was no way around it. With a courage that he didn’t really possess, he grabbed the door handle and opened it, and forced himself to go inside.
The beaming look of joy on the receptionist’s face was almost more than he could stand. “Sissy!” she exclaimed excitedly. She was looking at him, waiting. He knew he had no other option. He dropped a courtesy and said, “Hello, how are you?”
“Much better now that you’re here,” she replied. Her face darkened slightly. “That curtsey wasn’t nearly as much fun as the ones you were doing yesterday.”
What? The ones he did yesterday? He wasn’t about to do one of those again – if he could help it. “Um… I’m dressed a bit differently today,” he replied.
Her lips puckered a bit in frustration. “Yeah, I can see that.” Her face brightened again. “But can’t you do one for me anyway? Just so I can see it again?”
Ugh! Why? He didn’t really want to do it.
She saw him pausing and added, “Cassie says that you’re supposed to do anything I tell you to.”
Double ugh! And worse, he knew without a doubt that if he didn’t do what she wanted then word would get back to Mel, and that would mean trouble! Big trouble! He instantly did his best to curtsey flamboyantly for her, despite the dress he was wearing and the purse over one arm and the diaper bag over his other shoulder. It just wasn’t the same. But he was happy to see her smiling and giggling anyway. He was about to ask if she would go find Cassie now, but he didn’t get the chance.
She leaned over toward him, then cast a quick glance around to see if anyone else was near. Her voice came out as a giggling whisper. “Can I see your diapers again?” she asked. Chad couldn’t believe it. She had really asked to see his diapers. And worse, he knew he had no choice but to show them to her. Dropping his diaper bag and purse down on the floor next to him, he quickly looked around then lifted his skirt, just far enough so that she could see the bottom of his pantyhose covered girdle underneath.
“Oh pooh!” she exclaimed. They’re all covered up.
He nodded. “Sorry,” he replied as he dropped his skirt back down.
“Maybe some other time,” the receptionist replied with a sigh. “I’ll go get Cassie for you.”
Chad was grateful that she was leaving. He had a feeling that she might become a major pain from now on.
“Hi Sissy,” Cassie said as she and the receptionist walked up.
“Hi Cassie,” Chad replied, dropping a polite curtsey to her before he picked up his purse and diaper bag again.
Cassie looked at him funny. “She said that she’s disappointed that she can’t see your diapers today,” Cassie said, referring to the receptionist and trying to prolong the conversation a bit.
Chad shrugged. “I’m dressed for work today.”
Cassie nodded knowingly. “Did Mel tell you that you can talk like that?” she asked.
Chad was flabbergasted! She wanted him to use sissy talk? Here? Again? Now? Unfortunately she was glaring at him all too seriously. He dropped his bags on the floor again and dropped another curtsey. “Sowwy, Cassie,” he replied contritely in his high-pitched sissy voice. The receptionist giggled uncontrollably.
Cassie felt satisfied. She hated making him do it, but Mel had called her to specifically ask her to watch out for how he was speaking. And she knew that Mel would call her later and follow up. “Okay, Sissy. “Let’s go get your diapers changed.”
As Chad picked up his bags again, he wished that Cassie hadn’t said out loud what she was going to do. It used to be so much more private and easier when nobody else knew. The thought of no way to deny it, rang through is head once again. So many people had seen for themselves!
As he followed Cassie back through the room of exercising women, a few of them waved at him. “Hi, Sissy,” one of them called teasingly. Chad didn’t stop walking but he did smile shyly at her and waved a few of his fingers. He was ever so glad to get out of sight again in the back office – with the door closed behind him.
“They’re still talking about yesterday,” Cassie said as he started to get undressed. “Nice dress by the way.”
Chad momentarily stopped what he was doing. “Thanks,” he replied, referring to his dress. “I’ve had a few nice comments about it today already. What are they saying about yesterday?”
Cassie shrugged. “Let’s just say they’re still pretty excited about it. You’re all the buzz.”
Ugh! “I can believe it!” But what could he do about it? Nothing!
Getting out of his dress, pantyhose, and girdle, took a few minutes, but he finally was able to carefully peel off his plastic panties to expose his diapers and lay down on the floor in front of her. She handed him one of the baby bottles full of Mel’s green tea that she had pulled out of his diaper bag. He put it to his lips automatically and started sucking on it.
Cassie started peeling off his diapers. “Wow, you’re wetter than usual today,” she commented as she pulled the tapes open on the second one.
“Too much to drink,” Chad said before he went back to working on his bottle.
Cassie cleaned him up quickly, noticing as she did so that his penis inside of his chastity device was still as tiny as it was last week. And still no reaction to all her attention to that area as she was cleaning him. No sense in even trying anything else with it. “Okay, roll over,” she said. “Let’s get your backside now.”
This was the part that Chad really enjoyed and looked forward to – lately. He didn’t know why, but he just accepted now that he did. He rolled over onto his stomach so that Cassie could play with his backside again.
Cassie cleaned his bottom, then poured a generous amount of baby lotion into her hands. The moment she began messaging it into his backside, Chad let out a small moan of pleasure. “Scrunch up,” she told him. Chad pulled his knees up under him, raising his backside up into the air where she could get at it better. She reached into a nearby desk drawer and pulled out the toy that she kept there for him now. A moment later, that too was well lubed with the baby lotion.
She pressed her well lubed finger up against his tiny asshole and saw him almost start to push back against her finger, but he stopped, waiting for her. She pushed harder and her finger slipped inside. Just a little bit at first. She worked that much around a bit, knowing that he was enjoying the sensation, then she pushed her finger all the way in. He shuddered and buried his head under his arms.
She grabbed the ribbed dildo she used on him and, slipping her finger out of him, gently pushed the tip of it up against his hole. He arched his back and pulled his head up, waiting for it… wanting it. She didn’t disappoint him. Gently and slowly, she pushed it forward into him.
One by one, Chad felt the ribs of her toy slowly pushing into him. He no longer cared about why he loved it so much, maybe it was because Mel had rendered him incapable of any other form of sex. He only knew that he loved the sensation. He felt her pulling it back out, ever so slowly, then pushing it back in again. More! He wanted more! And he wanted the sensation to go on forever!
Ever so gradually, Cassie increased the speed of her thrusts, till he was pushing and pulling right along with her, eventually doing most of the work while she held the toy still. She saw him trying harder and harder to gain even more pleasure from it, but there was no additional pleasure to be had. She saw him finally realize that and slow down, finally stopping. She pulled the dildo out of him and watched as he seemed to deflate under her, his knees still pulled up to his chest underneath him.
With a soft moan of frustration, he rolled back over again and grabbed his bottle. His eyes were shut against the frustration as he put the thing to his mouth and started drinking again. If only he could get there! If only he could get the kind of relief from his ever aching sexual frustration that he so desperately needed. But the more he thought about what it was that he was trying to do, and how he was trying to get that relief, the more he realized just how impossible it probably was. So disappointing!
Cassie opened the jar of suppositories and pretended to pull one out. She realized she probable didn’t even need to bother pretending because his eyes were shut. He wasn’t watching anyway. She stuck her finger up inside of him as if pushing one of the little devils up there. His eyes popped open momentarily. They closed again as soon as she pulled back out of him. There was a slight look of annoyance on his face. She couldn’t blame him.
Chad worked on his bottle, his mind now moving away from unpleasant thoughts to more positive ones… like finally getting something solid to eat. A hamburger! A big, juicy hamburger! That’s what he wanted. With a ton of fries and a drink that wasn’t in a baby bottle. As he felt Cassie pulling the second diaper into place and taping it closed he was trying to decide – where was the best place to get the biggest, juiciest, best hamburger in the city?

Gloria walked around the little room where she worked with most of her customers one-on-one. Dust cloth in hand, she wiped down the furniture and decorations that made the room warm and inviting. Her next client was due in any minute now, but working with another client wasn’t the foremost thing on her mind. Mel was. Actually, Mel and Chad.
Mel was still going to be her friend, no matter what. She realized that now and she was relieved. But their relationship was still very strained – because of Chad. Mel was still pushing her to hypnotize him and reset the desires within him that would ensure her to win their bet. She, herself, also wanted to hypnotize him, but for a totally different reason – she was still worried about what she had already done to him. She had gone along with Mel’s games gladly… willingly… in the beginning. But after finding out how hard Chad was fighting against them, she knew how wrong she had been to do any of it.
They both wanted to hypnotize him again, only for different reasons. Her question now was, how could she possibly get Chad alone for a while – to work with him, to get answers out of him. Answers that she desperately wanted to know. Could she call him somehow? Ask him to come in for a special session? But she didn’t even have his phone number. He was Mel’s friend and he always came with her. Besides, doing something like that would be like sneaking around behind Mel’s back. And that wasn’t right – either.
So how was she going to get her answers if Mel wasn’t going to let him be alone with her? The outer door opening brought her back to where she needed to be. She walked out to warmly greet her next client.

“Thanks Cassie. I owe you one,” Mel said just before hanging up her phone. She sat back in her chair and stared at her office ceiling. Just as she suspected, Chad had not used his new sissy voice when he went to the gym. Actually, she never once doubted that he would use his regular voice. But that wasn’t the point. This was more like yet another way to deny him something male. In this case, the use of his male voice… actually the use of anything except his very sissy voice since he wasn’t allowed to pronounce certain letters when he spoke. The thought of her denying him yet something else masculine sent a small thrill through her. Very small, but it was still there.
Her mind flashed back to the strained lunch she had shared with Gloria. Gloria was still unwilling to help. It would be so easy for her to simply hypnotize him again and make him believe that he really did want to be incontinent. And he did want it! She knew that for a fact. She just didn’t really understand why he was fighting it, and her, so hard.
Speaking of which, she had put him through a lot for the last few days. She liked her idea of putting him in only one diaper all the time and then giving him only two hours to make it leak. And since she had checked him continually to make sure he was wetting all the time, there was no way he could hold back at all. But was it working? Was it helping? Was it having any affect at all on him? She had no way of knowing.
Once again she thought of Gloria. Gloria could find out for sure. Hypnotized, he would certainly tell the truth. If he were hypnotized, she could find out for sure if all her measures were having any affect on him. She could find out if her methods were removing any of his control at all. But Gloria… Ugh! How was she going to get her stubborn friend to help?
She forced her mind back to Chad and the fact that he did not use his sissy voice at the gym today. She had been totally right in her figuring that he would speak normally there… as well as everywhere else, she was sure. Maybe she couldn’t control him at work, but there were other things she could do to enforce… or force him… to speak the way she wanted him to at other times.
And the first thing to do was to add some punishment! She opened up her email program and began typing.