The Bet - Chapter 39 (Tuesday – week 6 Part 1 of 8)

The Bet
by Karen Singer

Chapter 39 (Tuesday – week 6 Part 1 of 8)

It was a familiar dream… or a similar one. He was off somewhere playing poker with his buddies and again he was dressed in his silly sissy baby outfit, complete with pacifier and baby bottle. He was playing cards while seated in his highchair at the same table with everybody else. He felt himself wetting… and the feeling disturbed him, made him sad. It made him sad enough that he started crying. And then Mel was there, talking softly and comfortingly, hugging him, calming him. She pulled his highchair away from the table and removed his tray. She unfastened the safety strap that held him in place. Then she picked him up out of the chair and carried him a short ways off. She handed him a fresh bottle to drink before she lovingly changed his diaper. He felt wonderful, loved, complete as she did it. It was the best feeling in the world.
And then his world suddenly turned upside down by the intense volume of his pink alarm clock playing rock music to wake him up. He was ripped out of his warm wonderful dream into the real world where the loud volume grated on his nerves, forcing him to roll off of his blowup mattress as quickly as possible and turn the darn thing off. Silence! Blessed silence! Except for the sound of his loud breathing as he tried to recover after being pulled out of his nice sound sleep so abruptly.
Ugh! It was morning… mostly. Another day. Another work day. Another day he would have to face horrible humiliation after horrible humiliation. Ugh!
He noticed the sting of his backside inside of his bloated and messy diapers. It hurt! Still! It felt kind of like the diaper rash he had endured a few weeks ago, only located solely on his bottom.
He waddled carefully and painfully out to the kitchen to see if she had left a note for him last night. She had said she would… and she did. He read it – same as usual. Nothing new. But he was still glad that she had left it. He pulled one baby bottle full of juice along with two more of her lousy green tea out of the refrigerator and carried them out to his lonely chair… his only chair. He started to sit down gingerly because of his stinging bottom, but stopped himself before he got very far. Maybe it would be better to not sit down today. His bottom already hurt, why make things worse by sitting on it? He set down two of the bottles on the chair and kept one of the bottles of tea to start with. He put it to his mouth and nursed on it, hardly thinking about what he was doing. But then drinking from a baby bottle now was mostly his normal way to drink anything. Drinking from anything else was becoming more and more of a rare opportunity.
As he drank, he wandered around the empty expanse of his living room. He actually found that he enjoyed moving around, if only because he wasn’t “locked” into staring at the embarrassing pictures on his wall – located directly in front of his only chair. Yes, this was much better than sitting in one place all the time. The only problem was, that his bottom still stung with every step that he took as his messy diaper rubbed against his raw bottom.

Mel was wide awake. She couldn’t sleep. And it was early! Okay, she didn’t feel all that great, but that was just her period. She was kind of used to that. The problem was that she couldn’t get her mind off of Chad this morning. Chad and her problem with keeping him from using his old male voice. Chad and her problem with making him incontinent so she could win the bet. Chad and her problem with why she wanted him to be at that stupid poker game tonight. Chad and her problem with… the beating she had given him last night… or rather the fact that she had lost control last night. That was the real problem. She had lost it. That was something that only happened rarely in her life. Why did it have to happen last night? Ugh!
Realizing that she wasn’t going to be able to go back to sleep, she rolled out of bed and put her robe on. A trip to the bathroom to pee and check her pad followed. She decided the pad could wait till she took her shower. It was only her second day after all.
The coffee pot was her next stop, and nothing else was going to interfere with that! She scooped out the coffee grounds, added the water to the pot and turned it on to brew. She remembered a few days ago when she had Chad come over early and he had fixed her coffee for her before she got up – again. Maybe she should have him stop in every morning before she got up. No, he was already getting up early enough… and he had more than enough to keep him busy in the morning. Maybe it was time to invest in another one of those pots that she could program to automatically come on before she got up. No, that wouldn’t work either. She couldn’t ever remember to set it up at night before she went to bed. Besides, in a few weeks she would have won the bet and Chad would be there all the time to fix her morning coffee – and everything else too. Yes, that was going to be soooo nice!
Once her coffee was made, she carried her cup back into her bedroom with her. She opened her closet to look through her clothes. The questions was, what was she going to wear to the poker game later. Something very casual for sure… yet sexy. That was a must. She really wished she wasn’t on her period. Sexy and period just didn’t go together very well.
She pawed through the clothes in the closet, moving hanger after hanger aside, until she came to one multi-hanger that held half a dozen of her skirts. She pawed through each one from the top down, not expecting anything to catch her eye. But one did, the very bottom skirt. She hadn’t worn it in about ten years. She didn’t even know why she still had it. It was too short… decadently short! The grey-black fabric was flecked throughout with shiny silver. It was stretchy and fitted. It was really… very sexy! And… it was perfect!

Cassie got to work early every morning because that was the only time that many of the gym’s members could take advantage of the programs and facilities. Very often, she was the first one there and opened the doors. But not this time. She found their receptionist, Cindy, already there, and oddly enough, waiting for her.
“Good morning, Cassie,” Cindy called brightly the moment Cassie got through the door.
“Morning, Cindy,” Cassie returned as she continued walking past the front counter.
“Uh… Cassie?”
Cassie turned to look back at Cindy. “Yes?”
“Did you happen to ask about… you know… I mean… um… if I can… you know… watch today?”
Cassie had completely forgotten about Cindy’s request yesterday to watch her changing Sissy’s diapers. She was tempted to just tell her no, that she couldn’t watch and not to ask again, but then she remembered Sissy’s reactions yesterday whenever she mentioned Cindy possibly watching. “Yes I did ask,” she replied. “And unfortunately, Mel left it all up to me. She didn’t say yes or no.”
“So?” Cindy asked hopefully.
Cassie shook her head. “I’m just not sure.”
“Please!” Cindy begged.
Cassie was getting a bit flustered by the request. She shook her head again. “You don’t know what we… I mean, there’s things we do there that…” She just didn’t know how to properly answer Cindy’s request. She wasn’t really sure she wanted Cindy to see everything that went on when she changed his diapers. Finally, she decided on an answer. “Tell you what. I’ll try to work something out, but don’t expect much. Okay?”
Cindy was totally elated though. “Yes, yes! Great! Oh, thank you!”
Cassie just nodded and walked toward the back. What was she going to do? She really should have just said no to her request. But…
Cindy’s face beamed brightly as she watched Cassie walking away. Now she couldn’t wait till lunchtime when Sissy would arrive!

The knock on Mel’s door was right on time – as it should be! Mel had just finished preparing his breakfast and had already dumped the baby cereal out into a pink plastic kiddies bowl for him. She wiped her hands on a dish towel and went out to open her door.
“Good morning, Mistress,” Chad greeted her with his usual curtsey.
Mel still thrilled every time she saw him do that one tiny little ritual. She really couldn’t get enough of it. “Good morning, Sissy,” she replied as she stood back and let him in. She waited till he had set his purse down under the table by the door. Then she looked him over carefully. “The blue earrings today, I see,” she commented.
“I hope they’re okay,” Chad replied. “I kind of wanted to try something different today.”
Mel smiled. They’re perfect! They go well with the blue in your skirt.”
“That’s what I was hoping.”
Mel smiled. “Into the kitchen,” she ordered. “I’ve got your breakfast all ready.”
Chad walked into the kitchen, but he paused before he sat down in his highchair. Sitting down was going to hurt and he knew it. He hadn’t sat down all morning since he got up just because of that. He turned around to put his back to the chair, and very slowly backed up to it. The highchair had been made from an old bar stool, so he had to literally climb up onto it. But once he had started, there was no way to stop or even try to sit down slowly. The process forced him to sit down hard on the seat and slide himself backwards all the way into it. The stinging pain registered immediately. He tried moving around to try to get it to hurt less, but all that did was to aggravate the problem further. He gave up and tried to sit as still as possible while Mel put the tray in place in front of him, locking him into the seat. No way out of the chair and off of his stinging bottom now!
Mel had watched him as he climbed up into the chair. Obviously his bottom still hurt. Once again she felt the guilt from what she had done to him last night. Why had she lost control? Okay, she had been very frustrated – with a lot of things… and okay, her period had started, but it had only just started yesterday. There was really no excuse! “It still hurts?” she asked, just for something to say.
“Yeah,” he replied in his sissy voice. “You could say that.”
She stopped as she was about to tie his bib around his neck and looked straight at him with a caring look on her face. “Did I say I was sorry?”
He nodded. “Yeah. I know.”
“Good!” She finished tying the bib in place and picked up the bowl of baby cereal she had prepared and set it down in front of him… along with a tiny baby spoon and a full baby bottle of juice. His usual breakfast. She refilled her coffee cup and leaned back against the counter to watch him making a silly mess of things.
Chad grabbed the tiny spoon in his left fist like he was supposed to and dipped it into the cereal. Very slowly and very carefully, he brought it to his mouth – which he opened as wide as he could while he leaned further toward the spoon so it wouldn’t have as far to travel. Success! He actually managed to get it all into his mouth without spilling any. And then he heard Mel chuckling.
“You look more like a toddler than ever!” she laughed outright. It was a moment before she could collect herself to say anything else. “Did you put plenty of baby lotion on your backside today?”
Chad nodded seriously. “A bunch. It still feels weird and wet back there.”
“It better feel wet – but not from the baby lotion!”
Chad only nodded as he dipped his spoon back into the cereal. “Don’t worry, it is. Several times over.” He sighed with a bit of frustration before he again attempted to get the cereal to his mouth without spilling any. This time, he heard Mel laughing before he got it to his mouth – which only caused him to spill it onto his bib – which only made her laugh harder. Ugh! But at least Mel seemed to be in a better mood today.

Chad looked at his desk chair the same way he had looked at the driver’s seat of his car… the same way he had looked at the highchair he had eaten his breakfast from… the same way he had looked at the one and only chair in his apartment after he got up this morning. That is to say, it didn’t exactly look inviting today. But he had endured worse and he knew he couldn’t exactly stand up all day. Gingerly, he sat down – and noticed Robin breezing by the entrance to his cubicle an instant before his bottom hit the seat. He paused just before it touched. “Hi Robin,” he called. Was that her gym bag that she was carrying?
“Hi Chad,” Robin returned, mostly from over the wall.
Chad sat his bottom all the way down into the chair. Yeouch! But the stinging soon turned to a numb discomfort that he was determined to ignore… hopefully.
As usual, Robin was back a moment later, her hands finally empty. “Let me see,” she said the moment she got in.
There was really no question as to what she was talking about, she wanted him to stand up so she could see his outfit properly.
“Uh… Do I have to today?” he asked.
“Sure. Why not?”
“Uh… Because I just sat down.”
Robin laughed. “You’re getting lazy in your old age!” She walked over and pulled playfully on his arm to get him to stand up – which he did, but slowly. At least standing up didn’t hurt as much as sitting down. “Hey! New earrings!” she exclaimed as he was still getting to his feet. “I like them. Where did you get them?”
“The same store I got the ones I wore yesterday.”
“I liked those too. How many pairs did you buy?”
“Three from that store and a nice pair of pink ones from a better jewelry store.”
“I’m surprised you didn’t get your ears pierced in the jewelry store instead. I would have felt safer about it.”
“I asked, but they didn’t do it there.”
“Oh.” She looked him over and smile. “You look pretty good again. That’s one of the necklaces you wore yesterday, isn’t it?”
Chad looked down and pulled the single wooden necklace out from his chest. “Yeah. Mel said that the necklaces could be worn separately or together, so today I wore just this one.”
She nodded. “Nice. So have you figured out what you’ll be wearing to the poker game tonight?” She smirked teasingly, “Derek will be there!”
Chad actually blushed. “Mel has that all figured out for me. She just hasn’t told me what it will be yet.” But in the back of his mind, all he could picture was the silly super short baby dress that she sometimes made him wear. “Hey, was that your gym bag I saw you with earlier?”
“Yeah. It’s Tuesday. I’ll be going right after work.”
Chad wasn’t really happy to hear that. He was still convinced that the only reason she had joined in the first place was to find out what he did at the gym, which he figured couldn’t really be very difficult to find out at all. He was only surprised that she didn’t know already – but he was still hoping to keep it that way! “Why bother?” he asked, still trying to dissuade her from going.
“Chad! We’ve been through this before. I need it! And besides, you know my husband won’t exactly be happy if I quit when I’ve just gotten started.”
Chad just nodded. “Yeah. Men!”
Robin nodded in agreement. “Men!”
It wasn’t till Robin had left his cubicle that Chad finally, gingerly, sat down again. Whew!