The Bet - Chapter 33 (Wednesday – week 5 Part 1 of 8)

A quick note – My wife left for a short trip to Louisiana in the middle of the night so I’m going to have a few days to play again. On the way home from work yesterday I made a quick stop and bought some pantyhose that I’ll be wearing to work today. After work I’m planning on stopping to buy diapers again (one of my passions) and then later tonight I’ll probably be shopping for a pair of heels to wear this weekend. I wonder what else I’ll think up to do.

So I’ll probably be blogging daily for the next few days.

Karen


The Bet
by Karen Singer

Chapter 33 (Wednesday – week 5 Part 1 of 8)

Her dreams were short and sweet, each one lasting only a few minutes. None of them seemingly related to each other. She dreamed of work, then nothing. She dreamed of love, then nothing. She dreamed of Sissy, then nothing. She dreamed of shopping, then nothing. She dreamed of the home she would someday have… with Sissy there to take care of it, then nothing. And again she dreamed of Sissy.
Each dream was different. None of them related. But as the night wore on, more and more of her dreams included Sissy… or Chad. Or Chad-Sissy.
Her dreams of Sissy gradually grew more disturbing as her conscious mind began injecting doubts and worries. Again and again she rolled over, throwing away the dream in favor of a new one. A better one. But the dreams kept coming. Some good, some not so good.
The dreams of Sissy and the worries and doubts began returning, again and again. Her troubled feelings mounting with each succeeding dream. Worry, worry, worry! Upon worry, worry, worry! Till at last she rolled over one more time and glanced at her clock.
With a groan, she forced her legs over the side of the bed and sat up. She brushed her long hair back off her face with both hands and pulled on it from the back for a moment, trying to clear her sleepy mind. With a sigh, she brought her hands back down to her lap and just sat. It was morning. Her alarm would be going off in a few minutes. She reached out and switched it off.
Her mind seemed still fogged with sleep as she made her way to the kitchen to start the coffee brewing. She stared still half asleep at the coffee maker for a few moments before she found the brain-power to fill it with grounds and turn it on. But as she stood there, watching the coffee brew, her mind slowly began to regain its function. The smell of the freshly brewed coffee began to wake her up, bring her back to life. Her thoughts turned finally to the day ahead… and then to Sissy.
Sissy! He would be up by now, probably long up! At least he better be up! She had set his alarm again last night while he was sleeping so he had no reason not to be up! She was always amazed at how soundly he slept every night. She wished she could do the same. She saw the coffee finish and she poured herself a cup. Mmmm! Wonderful. She carried it into her living room and curled up in her favorite chair. She had worked late last night on her laptop. Work got that way once in a while. It was just something she had accepted long before as part of the job.
While she had worked, she had made Sissy stand in his corner. The thought of it amused her. She had made him stand there, unmoving, for a very long time, and he had managed it just fine. It amazed her how much power over him she held now. Yes, he still rebelled – a bit – but overall, she was firmly in control. It still surprised her how much pleasure she received from having him so firmly in her grasp – and making him do the most outrageous things – and denying him the ability to be… a man!
And speaking of Sissy… She glanced at her clock. It wouldn’t be too long before he was due here again. She quickly finished the rest of her coffee and got up from her seat. It was time to throw some clothes on and make his breakfast. A baby-food breakfast! She giggled to herself at the thought.

Chad stared at his face in the bathroom mirror. His makeup job was… acceptable. He toyed with the idea of creating a different look for himself, something different. Women did it all the time. But he quickly discarded the idea. It had taken him forever to learn how to do just what he did now, not to mention that he didn’t have a clue as to how to do anything else with his makeup. And besides, his look was… acceptable.
His makeup was now done. He had already done his hair. He was already wearing his two diapers for the morning, along with plastic panties, a waist cincher, his overly tight and small all-in-one girdle, and his pantyhose. He hurried out to the kitchen where he grabbed his third and final baby bottle for the morning, this one, luckily, filled with apple juice. He started drinking it as he walked back toward his closet to decide what to wear.
He opened his closet door and glanced around. The only clothes in it were women’s clothes. Mel had long ago removed every masculine item he had in his apartment and put them… somewhere. His eyes quickly fell on the two new pairs of slacks that he owned. A hint of a smile crept onto his face. He hadn’t been able to wear slacks in… days! He grabbed a pair and pulled them off of the hanger. Now, what top to go with them? His eyes fell on a pink short-sleeved top that was fairly stretchy. It would fit a bit tight, but it was made to do that. And after wearing his colorful dress to work yesterday, the pink top actually seemed tame. He pulled it down too.
The pants fit tighter around his hips than the previous pairs that he had owned – much tighter. But he didn’t think they were too bad. Heck, the women in the break room had all said that he needed better fitting pants, and from everything he could see, these did fit a lot better. He stared at the front crotch. He couldn’t tell from looking at it that he was wearing diapers underneath it all, but… well… he wasn’t really sure, but he didn’t think it looked totally feminine either. Of course though, with two diapers and the chastity device crushed under his girdle, he supposed it couldn’t be perfect. He just hoped that his diapers wouldn’t become too visible later, when they were wetter, or worse.
He pulled the stretchy top on over his head and pulled it down over his fake breasts and pulled it into place. The bottom of it ended just over the top of his slacks. He looked at himself in the mirror. The first thing that he noticed was how well the pink color and v-neck of the top showed off the pink stone in the necklace he was wearing. He fingered the necklace for a moment and his eyes were drawn to the pink stone in his ring. Seeing them made him feel funny, both embarrassed and excited at the same time. He put his hand down and kept staring at his reflection. The tight top, over top of his waist cincher and girdle accentuated his “new” more feminine figure – quite a bit. That made him feel funny too, for the same reasons. He stared again at his necklace. There was a bit of a decoration on the top, right at the “V” that bunched up the material, adding visual interest to the top. The decoration did nothing to distract from his necklace though and seemed to accentuate his “boobs.” That made him feel funny too. Oh well. He had worn worse. Much worse. In fact, this was fairly tame. Comfortable too. Almost casual.

Feeling better, he slipped into a pair of three inch heels that were high enough to keep the bottoms of the pants from dragging on the ground. He checked his image one more time – acceptable – maybe even pretty good. Putting the baby bottle to his lips, he quickly finished off the last of it. He was ready. It was time to grab his purse and diaper bag and go. Mel would be waiting for him… Mel, and probably her idea of breakfast for him – baby food! Ugh!

Mel smiled as she heard the knock at her door. He quickly stirred the baby cereal in the pot one more time, then turned the stove off. It was ready. She hurried to open her front door. The wonderful sight of Sissy in a clingy pink top greeted her.
“Good morning, Mistress,” Chad said as he dipped a quick curtsey.
“Good morning, Sissy,” she replied as she stepped back out of the way to let him in.
He set his purse and diaper bag on the floor by her table and turned for her usual morning inspection. He handed her the bag of empty baby bottles which she didn’t even bother to check. Again. He wondered if he could get away with not drinking some of them, but decided he’d better not try it. Whenever she did open the bags, she would know for sure!
Mel looked him over carefully, very pleased with what she saw. She reached out and pulled on his necklace a bit. “That looks really nice with this top,” she remarked.
“I thought so too.”
She walked around him, studying his figure. “Those pants do fit better. A lot better.”
Chad was tempted to tell her that he was worried that they might show his diapers later, but he held his silence. Two minutes later, he was sitting in his highchair, bib tied around his neck, staring at the bowl of pasty colored baby cereal she had just put in front of him. Yummy – Not! He picked up the tiny rubber coated baby spoon she had set next to the bowl and began trying to shove it into his mouth. The stuff tasted awful, even though he was well used to it now. His problem was that it still kept falling off of the tiny spoon with every bite he tried to take. It took forever to eat it all.
Mel poured herself another cup of coffee and leaned back against the counter to watch him trying to eat. It never seemed to get old, watching him struggle like an infant. It seemed like the harder he tried, the more he failed. Sometimes she wanted to laugh out loud – occasionally, she did. Over and over again, she watched as he picked up his baby bottle between spoonfuls of cereal to wash it down. She had tasted the cereal many times herself while she cooked it. She didn’t think it tasted quite as bad as he claimed it was, but then she only took the tiniest of bites each time. Just enough to check the flavor. But then, it didn’t really have much flavor. None of the varieties she had did.
Denied masculinity. Denied the ability to be and adult… well, she was sort of working on that last part she supposed. But then there were so many ways and reasons she would never be able to take it all away from him. But still, the thought of it aroused her more than just a bit. Denying him everything he used to be, everything he probably ever thought he would be in the future. Remolding him into her own little plaything. Of course, all too many of those directions she was pushing him came from his own wantings, his own fantasies. Way too many. But still, she was surprised at how many of them she was really enjoying. And she knew without a doubt that the forced reality of the situation for him was far more horrible and embarrassing than his fantasies had ever led him to believe they would be. So she felt very satisfied in what she was doing to him. Very satisfied!

Just a typical morning. That’s what was mostly on Chad’s mind as he drove to work. He looked down and saw his pants covered legs. It had been a while since he had been able to wear slacks. They felt, and looked, strange to him now, yet he was oddly proud and relieved to be wearing them again.
Just another normal day… his “new” normal day. His life had been turned upside down and been twisted around in knots like he never knew existed since this bet had started. And “normal” lately didn’t seem to last very long. Just off the top of his head he realized that Mel had increased his nighttime bottles, his morning bottles, and he now only had two pairs of pants that he could wear. Only two days a week now that he could go without wearing skirts – to work anyway. Once he got home, the most likely scenario would be for Mel to have him change out of his pants into… something else.
Yet the day did feel normal to him. And for once, he was glad. In his new world, where things changed all too often, “normal” or “usual” were reasons to celebrate. A short while later, he was still feeling pretty good about things as he fired up his computer and stowed his purse in his desk drawer.