The Bet - Chapter 40 (Wednesday – week 6 Part 5 of 6)

The Bet
by Karen Singer

Chapter 40 (Wednesday – week 6 Part 5 of 6)

“Break time Sissy,” Robin called cheerfully from the entrance to his cubicle.
Chad had been staring mindlessly at his computer screen. He was so tired that he wasn’t even pretending to work. “Do I have to?” he asked, and then immediately yawned.
“Female voice, Sissy! Or as Derek put it earlier, your ‘girly’ voice.” She giggled. “And yes, you have to.”
“I’d rather take a nap.”
Robin let out a frustrated grunt. “Don’t use your male voice! Now say it again!”
“I don’t want to!” Chad said stubbornly – in his male voice.
“You can be so damn pig-headed!” An idea hit her. “Should I call Mel and tell her you’re refusing to cooperate – or even try?”
Horror hit Chad once again. “No!” he said quickly, clearly frightened by the idea.
“Girly voice,” Robin taunted.
Chad was too tired to argue anymore. Had she been teasing about calling Mel? “You wouldn’t really call her, would you?” he asked – in his girly voice.
Robin smiled. “I might. I do have her phone number now.”
“You’re joking!”
“Wait a minute!” Robin ran back to her desk and grabbed her cell phone and brought it back to his cubicle. She quickly went to her phone list and recited Mel’s number that Derek had passed on to her. “That’s it, isn’t it?”
Ugh! Chad laid his head back down in his arms on his desk again. She had it. Mel had not only called her, but had actually given Robin her number. And knowing Robin, it wouldn’t be long till she knew all too much!
“Now come on, let’s go to break.”
Chad didn’t want to argue anymore. He was too tired and depressed. This was turning out to be another very bad day.
“And remember, only your girly voice,” Robin reminded him.
Ugh!
As they walked through the halls, Robin replayed a bit of what happened in his cubicle through her mind. Was it her imagination, or when she had threatened to call Mel on him, did he look scared. She knew he was tired, very tired, that could have had something to do with it. But really, she got the impression that there was more to it than that.
Chad looked around the break room for Derek, but he didn’t see him anywhere. He didn’t know whether he was glad or sorry about that. On the one hand, sitting with the women was going to be embarrassing for sure, but on the other hand, he was not comfortable about sitting with Derek too. Not to mention that all the women now seemed to think that he and Derek had a thing going between them – which was definitely not the case!
The table was fairly crowded when he and Robin sat down, and Chad was pleased that he was not the center of attention – yet. He sipped his coffee and half-listened to the inane conversation between the women. One of them was complaining about the outfits her daughter wanted to wear all the time.
“You should have seen it!” the woman continued. “She wanted to wear the most ridiculous looking outfit you could imagine. She looked worse than some of those girls you see in the rock videos on TV! Her skirt had a hole in it so you couldn’t miss seeing her panties right through it! And her top was cut so low that her boobs were practically flying out! And the heels she was wearing! Ugh! And you don’t even want to know about her makeup! I put a stop to that right away! No daughter of mine is going out with a boy dressed like that!”
One of the women laughed a bit. “It sounds a little like the kind of outfit that Sissy wore last night.” There was a bit of laugher from the women.
“Not quite like that,” the first woman replied. “But the general idea was certainly the same!”
“Sissy, is that what you were trying to do last night,” one of the women asked Chad, “look like one of those young girls in the rock videos?”
“It wasn’t really…” Chad started to say.
“Girly voice!” Robin quickly reminded him.
Chad gave her a rather exasperated look, then he repeated himself – in his girly voice. “It wasn’t really my idea,” he replied again. “It was something that Mel kind of came up with.” He knew he had to explain it better than that. “She seemed to think that it would be fun for me.”
“I’m betting it was!” another of the women replied.
“No doubt at all!” still another woman added.
“So what are you going to wear for your date? Cause what you wore last night was certainly… interesting! Do you think that Derek will be wanting you to wear something like that again?”
“That’s a dumb question!” another of the women said before Chad could even think of replying. “Derek is a man! All men like that kind of stuff!”
“All too true, Honey,” another woman agreed with a sigh. “All too true!”
Chad finally spoke up – carefully using his girly voice. “I haven’t even thought about what I’m going to wear yet. And I don’t think he really wants to see me in anything like that again.”
“You don’t think? Honey, he’s a man! All men have only one thing on their little minds all the time – sex! And an outfit like that will make sure that it stays on his mind. He may say he doesn’t like it, but trust me, he does! Hey, what the heck am I telling you for? You should know better than any of us!”
The noise around the table was a mixture of agreements and laughter. Chad actually felt embarrassed. “That’s not quite true! There’s more to it than that,” he started to say.
“Not much!” one of the women interrupted. There was a slight pause, at the table, then several of the women started laughing again.
Chad may have been tired, but he realized that any reply that he made would have been useless, so he sat there silently embarrassed. A few moments later, the conversation passed by him again and returned to the women talking about their kids. He hated these breaks. He hated this particular break even more when the stupid suppository that Cassie had shoved up inside of him decided to do its thing while he was still sitting at the break table. He squirmed in his seat as it happened, all the while trying to make it look like nothing at all was happening or even wrong. The only good thing about it was – if you could even call it that – was that lately, he had been eating so very little, that his messes were the same way – very little.

Mel glanced at the clock in her car as she drove home from work. It was later than usual, much later. It had been over an hour since Sissy had called to tell her ‘she’ was putting her single diaper on. Now, there was only about half an hour to go before ‘she’ would have to be leaking. Mel really hoped that Sissy would be good tonight, she really wasn’t in the mood to punish ‘her’ at all. But she would if she had to!
Dinner smelled good from the moment she walked through her door. Sissy immediately came running to greet her with his usual curtsey. So nice! She stared at him briefly, his maid’s dress looked perfect – as it should. “Are you leaking yet?” she asked, actually hoping that he would be.
“Not yet, Mistress,” he replied. “But I’ve still got some time.”
“I certainly hope for your sake that you make it every time tonight!” Mel replied. “I really don’t want to have to punish you again.”
Chad didn’t want that either. “I’m trying,” he replied.
Mel nodded, then quickly said, “Show me your diaper!”
Chad was caught off-guard by the sudden command and as fast as he grabbed his skirt to pull it all the way up, he knew it wasn’t fast enough.
“Just hold it there!” Mel ordered sternly as she went to her corner where she kept her yardstick. She came back with it and gave one smart stroke to the back of his legs. “Faster next time!” she ordered. Only then did she take the time to examine how wet his diaper was – definitely getting there – fortunately.
The table was all set and dinner was basically ready. It was only waiting for him to put it out on the plate for her. She sent Sissy to dish out her food while she went into the bedroom to change into something more comfortable.
Chad dished out her dinner and made sure that everything was perfect. Then he grabbed his latest baby bottle to keep drinking – he was determined to get his diaper leaking soon. But as he kept drinking, he became aware of how long Mel was taking. He had heard her going into the bathroom first and then into her bedroom to change, but it seemed to be taking her longer tonight than usual. He began to worry that all the food he had just put out might get cold.
Finally she came out and headed for the table. But just before she could sit down, he felt his diaper leaking. Involuntarily, he let out a small exclamation of surprise.
“What’s wrong?” Mel asked as she took her seat.
“I just started leaking,” Chad replied in his sissy voice.
“Good!” Mel said as she stuck her fork into the vegetables. Then she looked up at him. “I guess that means we have to change you right away, doesn’t it!”
“But your dinner… it’s already getting cold.”
Mel conceded that he did have a point. But there was a further point that had to be considered. “But, as of now, you’re already on another hour and forty-five minute deadline. So unless you want things to be even more difficult then I suggest you grab another diaper and put it on right away!”
Chad was more than a bit surprised, but he ran to grab another diaper. The clock was already ticking? Was she changing the game – again?
“Bring it back here where I can see you do it!” Mel called after him.
Chad came back to the kitchen with his fresh diaper. He pulled the skirt of his dress up high where it would be out of the way, then he removed his soggy, leaking diaper. He opened the new diaper and started to stick it between his legs when he noticed that he was peeing again. Not much, but there was definitely a small weak stream leaking out from his chastity device. Quickly, he pushed the diaper up where it could catch everything.
“Were you just peeing again?” Mel asked before she shoved more food into her mouth.
“Yes, Mistress. A little… I think.”
Mel said nothing. She just waited till he checked to make sure he was done, then she watched as he expertly diapered himself. She glanced at the clock. “An hour and forty minutes now,” was all she said… all she had to say.
Chad glanced at the clock too. This was getting harder and harder! He quickly grabbed his bottle and began drinking from it again. He really didn’t want to get punished tonight!
Mel watched him standing there with his bottle. The bottle appeared to be about three-quarters full – so it certainly couldn’t have been his first bottle since he had started preparing dinner. He needed to keep drinking, but she really preferred just then that he go to his corner. “Take that thing to your corner,” she ordered. “See if you can keep drinking it while you’re standing there.”
Chad wasn’t exactly happy about that order at all. It was bad enough having to drink from the bottle almost continuously. It was also bad enough to be stuck in his corner. But both? At the same time? Ugh! He carried his bottle to the corner and stepped up onto the perch. His body automatically leaned into the walls. He tried drinking from the bottle with it below his head, but he knew instantly that it wouldn’t work. The liquid had to be higher than his mouth. He had to fight a bit to get his arm up high enough to hold the bottle where it needed to be. It kept his head bent back so that instead of staring at the two blank walls, he was now staring at the corner of the ceiling – only a little bit better than staring at the blank corner walls all the time. The real problem now was his neck. He could already feel how tired the position was getting.
Mel watched him from her seat at the table. Why hadn’t she thought of this before? Obviously, he could make it work just fine. Feeling very satisfied with herself, she continued eating her meal… which tasted even better now than before.
Chad closed his eyes because he was going cross-eyed. With nothing really to look at, even in this position, he was spending more and more time staring at the bottle he was drinking from – which was difficult to see. He heard Mel getting up from the table… he even heard her coming over close to him. He was really expecting her to let him out of the corner, but she didn’t. She didn’t even say anything. So he was stuck standing there… stuck with nothing to do but drink his bottle. He opened his eyes and saw that he had finished about three quarters of it… the exact amount was hard to tell because of the angle and how close the thing was to his eyes. He closed his eyes again and heard Mel’s phone ringing.
Mel hurried to answer her phone, afraid that it might be some client problem that would call her out again. She checked the caller id, but didn’t recognize the number – not a good sign. “Hello?” she said into the phone.
“Mel? This is Ray – from the game last night…”
“Oh yes. How are you Ray?” In the back of her mind, she was almost hoping that he was calling to cancel the date they had set up for Sunday.
“I’m fine,” he replied. “I was just calling to see if you’re interested in having lunch tomorrow.”
“Lunch? I thought you had another date tomorrow.”
“I do, but that’s not till tomorrow night. Lunch is definitely doable though.”
Mel had a hard time believing it. Chad really hadn’t been kidding about this two-timing bozo! “Uh… I’m sorry,” she replied. “I’ve kind of got this standing lunch date that I try not to miss.”
“Not even for a chance for me to take you anywhere you like?”
Obviously, he wasn’t the type to give up. “I’m sorry,” she replied. “I have to be there – especially tomorrow.”
“Well, how about Friday then?”
“I’m afraid that Friday is out too. Let’s just wait till Sunday, and then we’ll see from there. Okay?”
“Fine by me,” Ray replied, although she was sure that he was defiantly feeling let down – good! “I just thought it might be a lot nicer to do it without anybody else.”
“I’m not quite ready for that yet,” Mel replied. “So is Sunday still on?”
“Oh yeah! I wouldn’t miss seeing Derek kissing Chad for anything!”
“You mean Sissy.”
“Chad… Sissy… whatever!”
Mel definitely didn’t care much for Ray, now more than ever. “We’ll see you Sunday then, Ray. And thanks for calling and asking me anyway. A girl can always use a boost like that to her ego.” She hung up. Why had she added the last part? It was dumb – especially since she really despised him more than ever now. Imagine, he had a date lined up for tomorrow night – and he still wanted to take her out to lunch! The two-timing moron! He was a hunk though. Pity.
Chad stood there finishing his bottle. It sounded like Ray had asked Mel out to lunch. He was kind of glad that she had refused, even though he really didn’t know why he should be glad. He just was. Now if she would just let him out of this stupid corner! He had a horrible cramp in his neck from the strain of the position he was in. He suddenly started sucking a little air with the contents of his bottle. A few seconds later, he pulled it out of his mouth and took a deep breath. Whew! Now, would Mel let him lower the bottle – and his head? He had to relieve the strain on his neck! He chanced it. Slowly, he brought his hand holding the bottle down, and even faster, he brought his head forward again. Much better!
Mel noticed the movement from Sissy in the corner. “Are you finished?” she asked.
“Yes, Mistress,” Sissy’s muffled reply came from the confines of the corner.
“Good, then get yourself out of there and into your highchair.”
As soon as Chad managed to extricate himself from the corner, he rubbed at his sore neck. That had been tiring! Still rubbing his neck, he carried his now empty bottle towards the kitchen – and his waiting highchair.
“Show me your diaper!” Mel suddenly demanded.
Chad was so surprised by the request that he dropped his bottle as he desperately grabbed for the hem of his skirt to lift it up high. Was he fast enough? Was she going to hit him again? He didn’t really like the look on Mel’s face, but at least she wasn’t running for her yardstick.
Mel had rather enjoyed his panic the moment she had given him the command – especially where he had dropped his bottle in the process. She just didn’t want him to see that she had enjoyed it. “That was close, Sissy! Very close! If you’re that slow next time, you’ll feel my stick again!” She examined his diaper. Yes, it looked like he had wet it while he was on his perch, probably more than once. But he had a long way to go with it – a very long way! “Okay, Sissy. Get into your chair.”