The Bet - Chapter 32 (Tuesday – week 5 Part 4of 6)

The Bet
by Karen Singer

Chapter 32 (Tuesday – week 5 Part 4of 6)

Chad knew he shouldn’t have had that extra large coke with his lunch. It was way too much. Especially after the baby bottle he had finished in Cassie’s little office. Now he was peeing like crazy every few minutes again, and holding back was harder than ever. But the burger and fries had been especially good. A meal to remember! Because of the tight waist cincher he was wearing, he hadn’t been able to even come close to finishing it. But that didn’t matter, his stomach was certainly full now, and he had really enjoyed it. Every solid bite!
The email notification flashed on the bottom of his screen and he clicked on it. He was a bit surprised to see the email was from Mel.

Sissy!

You didn’t speak in your new sissy voice at the gym today. And I’m very sure you’re probably not using it anywhere else. That’s two more demerits added to the one you already have today – thee total – so far! Be prepared for a very painful evening!

You are not to use anything but your new sissy voice. Anywhere! Anytime!


Chad closed the email before anyone could walk up behind him and see it. More punishment tonight. Oh great! Just what he needed! Or rather just what Mel thought he needed. Yeah right, like he was really going to go around talking like a stupid fool all the time. No chance!
Well, she had beaten him before, and she would probably do it again… in fact, she was going to do it again. He knew he’d cry a bit, probably a lot. Then he’d do his best to act as good as he could for her – while he was with her. But there was no way that he could talk like a sissy everywhere. She had to be crazy if she thought he actually would!
His eye caught sight of the icon on his desktop for the spreadsheet where he kept track of his bet progress. He opened it yet again. So far, he wasn’t making very good progress today. But things always got much better later in the afternoon. Hopefully, today would be no different.
He glanced down the list of reasons he had put on the sheet for winning the bet. Self-respect, friends, and a life were at the top. But he was a sissy. He couldn’t deny that now. Not at all. She had shown him that this weekend, over and over again. And then she had made him demonstrate it all too convincingly to other people – in public! Did he deserve any of the things on his list? After what he had done yesterday, did he deserve self-respect? He thought about that for a while and finally decided. Yes he did want it. He wanted all of it. But then, he also wanted his sissy life too. He was living the dream – and then some. He wanted it all. But all was just too much conflict. Too many things that didn’t fit together. Yet he did want to be able to hold his head up again and be proud of himself… for something. So he had to win this bet!
He glanced at the list again. A pool table, new TV, nice furniture. A place of his own that he could be proud of! A place that others would envy. That’s what he wanted. He thought again about having someone design such a place for him… but who? Sandy was still the only thought that came to mind.
Disappointed, he closed the spreadsheet again. He glanced at the flowers on his desk. Having them there made him feel a bit funny. Guys didn’t usually have flowers on their desks… and they didn’t usually have anyone send them flowers. But he had flowers. Mel had sent them to him last week. But then, he wasn’t a man anymore. He was nothing but a big sissy.
“Hey Chad. Ready?”
He glanced up to see Robin at the entrance to his cubicle. “Ready for what?”
“For break, dummy.”
“Oh.” He got up from his chair, took a moment to adjust his dress, and followed her out. He was halfway up the hallway before he even realized that he hadn’t given not going with her a second thought. Oh well. He would have only wound up going anyway.
The break room was getting crowded as they entered. He had to stand in a fairly long line behind Robin, waiting to get his coffee. Coffee that he knew he didn’t need, or even want to drink. It would be even more liquid in his system that he would have to get rid of. Maybe he could just pretend to sip on it and not really drink much.
He finally got to grab a cup and fill it. He turned away from the coffee to follow Robin. He looked up at where he was going, and locked eyes with Derek who had just joined the back of the line. He immediately felt his face flush. To get to the table all the women were sitting at, meant that he would have to walk uncomfortably close to his old friend… or else go completely around the room in the opposite direction. There was really no other choice.
He headed for the table, but he couldn’t tear his eyes off of Derek’s face. They got closer. Almost talking distance now. Closer still. He wanted to walk right past Derek, not say anything at all, but it was as if his body stopped of its own accord. Blushing, he looked down at the floor. “Hi,” he said simply.
“How are you… Sissy?” Derek replied,
Chad looked up again. It almost hurt to hear Derek refer to him with his new sissy name. “Okay,” he answered simply.
“You look nice today,” Derek continued.
Chad glanced down at his dress. “Thanks. I’ve been getting lots of compliments on this dress today.” Chad saw what looked like a slightly startled look on Derek’s face and he saw him glancing down and looking at his dress more carefully. Chad realized then that Derek probably hadn’t really noticed much about the dress at all. Like most guys, himself included, Derek had only really noticed the over impression.
“Yeah, nice,” Derek said about the dress.
There was an awkward pause between them. Chad finally held up his cup a bit. “Well, I gotta go,” he said as he glanced at the table full of women, all too many of which were watching him and Derek.
“Yeah, of course,” Derek replied. “See you around.”
“Yeah, see you around,” Chad replied and took a step away.
“Sissy…” Chad stopped and turned back to him.
“Um… Do you want to join us instead?”
Chad was shocked. He thought about it briefly and quickly rejected the idea. “No,” he replied. “Maybe some other time.”
“Some other time,” Derek repeated – almost sadly.
Chad walked away, straight to the table full of women and pulled up a chair to sit among them. He felt safer here with them now. More relaxed. It was like this was where he belonged.
“What did he want?” someone asked him, sounding fairly excited.
“He asked me if I wanted to sit with them,” Chad replied.
“So why didn’t you?” someone else asked. “He is your friend! Or at least he used to be!”
Chad shook his head. “I’m not… comfortable with doing that yet.”
“Well, Honey,” someone else spoke up. “You’re going to have to deal with it sooner or later. There’s women in this world, and there’s men. And we’ve all got to eventually deal with both flavors!”

Chad stopped at the light on his way home from work and shifted uncomfortably in his seat. His diapers were very wet and messy again. Way too wet. He hoped they hadn’t started leaking yet. Fortunately though, the mess didn’t seem to be as bad today. But then he hadn’t had much to eat for the last few days, at least not till his lunch today. He wasn’t looking forward to that mess when it finally came out of him.
As he waited for the light to change, his cell phone rang. He quickly fished it out of his purse before the light could change again. “Hello?”
“Sissy!” Mel’s angry voice said. “Why didn’t you answer with you’re sissy voice? “You know I don’t want you speaking any other way – ever!”
Chad was so surprised that he almost missed driving again as the car in front of him pulled way ahead. “But Mistress,” he replied, this time carefully using his new voice. “I didn’t know it was you.”
“It doesn’t matter!” Mel almost yelled back angrily. “Only sissy talk! All the time! That’s another demerit on top of the three you already have!”
Ugh! Another demerit. More beatings! There would be no arguing with her. He made a mental note to be more careful about checking to see who was calling before he answered his phone from now on. “Yes, Mistress,” he answered – regretfully.
“Go home,” she ordered. “Get cleaned up, and call me when you get out of the shower – before you put your diaper on! That’s if I’m not already there. I should be home fairly soon.”
“Yes, Mistress,” Chad replied yet again. The connection broke suddenly. He set his phone down inside his purse while he was still driving. It didn’t sound like tonight was going to be a fun night at all!

Mel felt fortunate to get out of the office as early as she did. She carried the box with the Aneros in it up to her apartment and stuck it away in one of her drawers. Then she went out again, directly over to Chad’s apartment. She opened the door and immediately heard the shower running. Good. She had gotten there before he could get dressed again. “Are you almost done in there yet, Sissy?” she called out as she entered his bathroom.
Chad was shocked to hear someone else in his apartment. Fortunately it was Mel, although he hadn’t heard her enter. “Just a sec!” he said as he quickly turned the water off. It felt good to be clean again, especially to have the mess in his diaper gone. The other part, the wetness, he didn’t really mind so much. In fact, he usually liked it. He stepped out of the shower to see Mel leaning up against the doorway of his bathroom. She was staring at him and smiling. The smile he took as a good sign. “Hello, Mistress,” he said, carefully using his sissy voice as he grabbed a towel and started drying himself off.
“Hi, Sissy,” Mel replied with a hint of amusement in her voice. She watched him as he dried himself off carefully. It didn’t take long since he had kept his head and hair dry. She noticed again that his hair needed a bit of a trim job and made another mental note to ask Cassie to touch it up for him.
His towel worked its way down his body, then carefully around his chastity device. She noticed how gingerly he seemed to dry himself off there – very carefully. Then he moved on. “Does that thing work anymore?” she asked, still staring at his chastity device.
He looked up puzzled. “What thing?”
She walked over to him and reached out, grabbing the device and tugging on it a bit. She saw no reaction from his trapped penis inside. “This thing,” she said.
“The chastity device? Yeah, it works, believe me!”
“No, I meant the tiny little thing inside there. Does it still work anymore?”
That surprised him. “I don’t know. I guess it does. But I haven’t given it much thought for a while now. But then I don’t try to get “bigger” anymore so it’s not too bad.”
Mel nodded and took a closer look, trying to see more of his penis inside. But she couldn’t see much. She let go of the device and backed off to the doorway again. Chad finished drying himself off. “One diaper again,” she said as he finished. Chad silently groaned. As soon as the diaper was in place, Mel glanced at her watch. “Two hours, Sissy. You know the drill. Wear your uniform tonight, you’re making dinner. And maybe this time I’ll even let you eat some of it. Maybe!” She turned then and left him, and went back to her own apartment.
Chad stood still for a moment and stared at the empty doorway where she had been standing. Another two hours. He was tired of this game! If it wasn’t for the fact that she kept checking his diapers all the time to make sure he kept wetting himself, he would try to hold back, at least a bit each time. But he never knew when she was going to check again. In fact, she might even expect to see him wet before he got to her apartment. Realizing that, he forced himself to relax all those muscles again, the way they had been for the last three days. It felt strange for a while as he began dressing himself, but all too quickly, it felt normal again.