Tuesday, April 13, 2010

The Bet - Chapter 21 (Friday – week 3 Part 1 of 4)

The Bet
by Karen Singer

Chapter 21 (Friday – week 3 Part 1 of 4)

In her dreams, she reigned supreme! She gave the orders and everyone ran to follow them. People danced to her tune like puppets, doing absolutely anything she said – for her own amusement – like crowds of court jesters.
Those who tried to outwit her soon discovered that her mind was quicker and more devious than theirs, and one by one, they all fell to her superior abilities. Everyone admired her. Everyone praised her. Everyone wished they could be her. But there was no one like her anywhere. She was simply, the best! And it was so good to be the queen!
Her alarm clock broke her happy reveries, erasing them from her conscious mind, but not erasing the feelings of euphoria. It was another day, and an important day for her. Would Chad do as she hoped he would? Impatient and unable to stay in bed, she got up quickly and headed to her kitchen to make her coffee.

Loud music blared into the room from the small pink clock radio, blasting him awake. It took him a moment to collect his thoughts, then he quickly got out of bed to turn off the annoying music. Blessed silence soon filled the room.
Something was different, something small. Something about the light! He quickly glanced back at his clock radio. It was earlier than usual, by a full hour. Why? Why had Mel reset his alarm for so early? Did she make a mistake?
He headed out to the kitchen to see if she had left him a note. Hopefully she did and hopefully it would have some kind of explanation. As he walked, he took particular notice of how full his diapers were – not nearly as bad as they usually were. Yes, they were very wet and yes they were messy, but still, not nearly as bad as usual. But then Mel didn’t feed him nearly as many of her lousy bottles of tea last night. It was another minor victory – despite the fact that he realized that once again he had not woken up during the night at any time when he had to pee. Troubling!
As he entered his kitchen his heart soared. Yes, there was a note. His curling iron and brush that he had left in her bathroom last night were next to it. He read the note quickly – but remained puzzled. Not the slightest hint of why he was awake so much earlier than usual.

First bottle.
Get cleaned up and diapered.
Second Bottle
Do your makeup and get dressed.
Fix your hair properly
Third bottle

That was it! Nothing out of the ordinary except his hair. Ok, he figured that having to use the curling iron on it now was going to take a few minutes, but not all that long! Still puzzled, he grabbed his first bottle out of his refrigerator and headed to his solitary chair to sit and drink it. As he sat down he wondered once again, did Mel mess up? Another hour of sleep would have certainly been nice.
But a moment later, his problem of the day descended on him like a ton of bricks. “Shit!” he exclaimed as he bolted out of his chair and ran to his closet. He quickly opened the door and stared inside. His eyes swept everything desperately, but he didn’t spot anything that could relieve the awful feeling of panic that was now racing throughout his entire body. He didn’t see one pair of pants that he could get at. Not one! All his male pants were wrapped up in huge layers of cling wrap where he couldn’t even touch them. And all his female slacks were now in Mel’s laundry hamper. No pants! Of any kind! He was going to be stuck wearing a skirt to work today – or a dress – which amounted to the same thing!

Still feeling the complete awful panic throughout his system, he returned to the only chair he had and sat down. He put the baby bottle full of her tea mixture to his lips and began sucking on it. The liquid was cool and felt good inside his dry mouth. The feeling of sucking on the bottle was comforting, ever so slightly taking the horrible edge off of what he was going to have to face very shortly. No pants! Damn!

Mel dressed herself in comfortable jeans and a t-shirt. She put a pair of comfortable sneakers on her feet. If everything worked out like she hoped it would, these clothes were going to be necessary. She poured herself another cup of coffee and tried to imagine what Chad was doing next door.

Chad fussed very slowly with his hair. It wasn’t that he meant to do it so slowly. It was just that this was all new to him. Besides, having to hold bunch after bunch of his hair locked around the barrel of the curling iron till it was done took a lot of time. And as he worked on his hair, his mind continually returned to his clothes closet and what he had seen – or rather not seen. The tedious job of fixing his hair was beginning to get to him, yet he kept at it, carefully. Not so much because he wanted to fix it so femininely – he didn’t – not at all. But he did it because it was keeping him from facing his closet.
He finally put the curling iron down and unplugged it. Then he took his brush and lightly brushed his hair all over. Changing it, smoothing it. Making it go where it was supposed to, yet not where his heart wanted it to go. Making it finally look all too feminine. And bangs now – small though that they were, they were still there, all curled under in a row across the top of his forehead. Girly. That was the only way he could describe the final effect when he was finished – girly!
He felt himself suddenly peeing into his diapers and he closed his eyes to savor the feeling. So nice. Not only that, it was another small distraction from what he had to face next. But the peeing never lasted very long.
He glanced at his clock. Having to fix his hair had taken him almost a full half hour longer than usual. He was surprised it had taken that long, but then he wasn’t exactly hurrying.
Having no choice now, he faced his closet. He was already wearing his diapers – wonderfully wet, his girdle, and his pantyhose. He opened the closet and stared inside. Only skirts and dresses. But what was he going to wear? What would be the least noticeable? He pulled down a dress that he had owned for a long time now and was about to slip it on, then thought better of the idea. He threw it out of the way on the floor instead. He pulled out a skirt instead and slipped it on. It was fairly short and tight. Just the way he loved them. But was it too short and tight? He pulled it off again and threw that on the floor too before he selected another skirt instead, one that was slightly longer. But was it too long? How did he look in it? He didn’t have a big mirror to help him.
Over and over again, he pulled various items out of his closet. Some he tried on, some he just threw in the one big pile of clothes he seemed to be making. He finally glanced at his clock. Time was running out! He had to make a decision! He wanted to scream! What should he wear?
He finally grabbed a skirt and matching blouse outfit that Mel had selected for him last weekend. At least he knew they went together. The skirt wasn’t real short and was fairly full so it wouldn’t reveal his diapers underneath. It was the best thing he could finally think of. He slipped the skirt on and zipped it up at the side. He pulled the matching top down over his head. If only he had a mirror! Remembering the problem he had the last time he wore a blouse, he ran to his cardboard dresser and pulled out two pairs of pantyhose and used them to pad the cups of his girdle, instantly giving him the illusion of breasts. Why hadn’t he worn one of his male shirts? They were all still in there? His reason was simple, he knew that the blouse he had on went with the skirt. They were a set. Besides, since he was wearing a skirt, why bother with the male shirt?
He quickly put on all his jewelry, checked his makeup and hair in the bathroom mirror. And ran back to look at his clock. Shit! He was going to be a late! Where had the extra hour gone?

Mel paced around her living room in a fit. It was past time for him to be there. Where was he? Why was he late? Was he coming at all? Would he be wearing a skirt? Or would he totally chicken out and unwrap his male pants? She had pulled a pair of his female slacks out of her hamper and had them ready for him incase it looked like he couldn’t handle it. But hopefully, she wouldn’t need them. Where was he?
The knock finally came at her door and she ran to open it. He stood there looking more nervous than she had ever seen him before – except perhaps that Sunday when she had made him go to the grocery store in a skirt.
He dropped a quick curtsey to her. “Good morning, Mistress,” he mumbled through the pacifier that for once was already in his mouth.
“Good morning, Sissy,” she replied as if there was nothing out of the ordinary going on. She stepped back and let him inside and closed the door behind him. “You’re late!” she said sternly.
“I know,” he replied. “I’m sorry,” he said as he dropped a quick curtsey. “I had a lot of trouble figuring out what to wear today.”
She nodded, she had no doubt. It was part of the reason she had set his alarm clock to give him the extra hour. She took the bag full of empty bottles from him and checked it, perfect as usual. She started looking him over carefully. “Your hair came out really well today. I didn’t expect you to do such a good job for your first time.”
“Thank you, Mistress,” he said, dropping a quick curtsey.
“And your makeup looks good again too. You’re definitely getting better.” He said nothing to that at all, but she didn’t really need him to. She walked around him. “I like your choice of outfit for today. It looks like it will be perfect for your job.” She couldn’t help but notice the worried look on his face.
“I hope it looks ok on me. I don’t have a mirror that I can see myself with.”
She smiled at him. “It looks great on you. Go look for yourself.” She watched him turn quickly and head into her bedroom. She followed behind him and stopped in the doorway to watch him. He was turning back and forth, slowly, in front of her full length mirror.
Chad held his skirt out a bit trying to see down to his legs and the heels on his feet. It was a lot easier to see everything in the mirror. He stared at his reflection. He wasn’t really sure, did he look more like a woman now? He actually hoped so. It would make some things a lot easer. But others… not at all! The colorful pattern of the dress was strange to him. Did it make him stand out too much? He was suddenly very worried about that. He finally turned toward her. “You’re sure I look ok?”
She smiled at him. “You look very good,” she replied. Actually, he did – sort of. There was not doubt still that there was a man underneath the clothes, but at first glance now, she doubted that anyone could tell, at least not from a distance. “Come along now Sissy, it’s breakfast time and you’re already running late.”
Chad endured having to eat his breakfast in the highchair once again while Mel stood and watched him with a cup of coffee in her hands. He was trying to hurry through his breakfast, but the tiny baby spoon kept his eating pace to a crawl. For once though, he got through the cereal with only one baby bottle to wash it down.
As soon as Mel pulled the tray away from his chair and he stood up again, he felt himself peeing again. He stood still and enjoyed the sensation. It felt so good. But then it was time to go. Mel was already waiting for him by the door, holding his diaper bag and purse out for him. Every step he took toward her felt like he was walking toward his doom. When he had his purse over one arm and his diaper bag slung over his opposite shoulder, she opened the door for him. And he stood there. Hesitating. Reluctant to take that first step outside.
“Am I going to have to call the police again?” she asked teasingly.
He looked at her. He knew she was kidding. But her point was made. He forced his legs into motion and took a step, then another one. He was outside now. He turned in the direction of the stairs and took yet another step… and another...
“Have a nice day,” Mel called from behind him.
He turned to look at her, but he couldn’t put any kind of a mean expression on his face, he was still too preoccupied with having to go to work dressed as he was. He turned back to the direction he was heading and continued his journey toward the stairs, then down the stairs and to his car. He glanced up and saw Mel still watching him, still smiling. She waved. He opened his car and got in.
Mel watched him driving off. She felt both amused and elated. It was a major step! More so than he probably knew. But he was gone now and it was time for her to get busy. She quickly got her keys from her purse and went into his apartment. She would probably be spending a bit of time there today, more than she really had time for, but that couldn’t be helped. Some things had to be done right away.
As she walked into his bedroom, she was amused to see the huge pile of all his female clothes on the floor. He must have had a hard time deciding what to wear. She opened his closet and looked inside, with all his female clothes on the floor, and most of his male clothes wrapped tightly in her cling wrap, there was a lot of extra room. This was the second time that he hadn’t worn one of his male shirts. It was the cue she had been waiting for. She removed all of them from the closet and left just the hangers. She put them all into one big pile on his floor. Then she went back to his closet and wrestled his cling-wrapped pants out too. Then she pulled out the cling-wrapped box that held all his male shoes. She went back to the closet and searched for any other male items she could find. There were very few – two sports jackets and a few ties. They soon found their way into her pile on the floor.
She began searching the rest of his apartment once again, looking for more male items to add to her pile, not just clothes, but anything that she felt she didn’t want him to have anymore. There really wasn’t much. He really didn’t have anything. She looked carefully at the pile she had created. She would be back later for it. It was time now to get herself ready for work.

Chad sat in his car in the parking lot, watching as all the other employees walked into the building. He didn’t really want to get out of his car. Sudden movement just outside his car startled him. He was annoyed to see Robin walking up, waiting for him. Worse, she was waving at him through the closed window and looking fairly happy. “Hi Chad,” he heard her saying through his closed car windows.
He rolled his window down instead of opening his door.
“Hi Chad,” Robin repeated. Then she stopped and stared at him. “Chad, your hair looks great today. It’s all different! I love it!”
“Yeah, well…” was all he was able to get out, rather sullenly.
“Aren’t you coming to work today?” she asked. “Or are you planning to sit there all day?”
“I think I’d rather sit here,” he admitted.
“Just because.”
She shook her head. Then she stopped and stared at him a bit harder. “Chad, you’re wearing a blouse again today. Very pretty. Is that why you don’t want to get out?”
“Kind of.” He hit the button to roll up his window again. He didn’t want to talk to her and he was having trouble finding the courage to go into work while wearing a skirt.
Robin waited for him to open his car door, but he was just sitting there, staring straight ahead and trying to ignore her. She banged on his window. “Chad, open up!”
Chad turned to her. Why wouldn’t she just go away? He looked away from her again.
Robin banged on his window yet again and even tried opening his car door, but it was locked. “Chad! What’s wrong? Tell me. Come on, open up!” she yelled as she tried desperately once again to open his door.
“No!” he replied from inside his car.
In her frustration, she kicked his car door, harder than she meant to. “Oops!” She put her hand to her mouth in horror. Did she dent his car?
Chad heard her kick his door. The sound surprised him and galvanized him into action. Had she dented his car? He quickly opened his door and scrambled angrily out to see. As he slammed it shut again, instead of looking directly at his car door, he saw Robin staring at him. Shit! He finally looked at his car. There was a spot in the middle of the dirty side where she had kicked it, but it wasn’t dented or even damaged in any way – thankfully.
“Chad,” Robin said, still staring at him. “You’re wearing a skirt outfit.”
Shit! Like he had any choice in the matter! “Yeah,” he replied sullenly.
“Is that why you didn’t want to get out of your car?”
“What do you think?” he replied angrily.
“Well you’re the one who chose to wear it!” she returned, put off by his attitude.
“Shit!” he replied. “I wore this because…” But what could he really tell her? “It’s complicated!” he finally finished.
She actually swung her purse at him and hit him. “You idiot! Stop handing me that complicated crap!”
“Well, it is,” he replied more calmly.
“Yeah, sure. Now are you coming into work today, or not?”
He looked at her. She had already seen him now in what he had on. She had seen him in lots of different outfits now, just none with a skirt. Why should this be so much different? Because it was! With a sigh, he opened his car door and grabbed his purse. “Yeah,” he finally replied. “Let’s go.”
Robin fell in next to him as they walked toward the building. She was now a bit amused by him. “And you said yesterday that I’d probably never see you in a dress,” she teased.
He shook his head. “I hadn’t planned on wearing this. And it’s not a dress!”
“Close enough,” she replied. “Really the same thing.”
He didn’t answer. He knew she was right. He felt so weird walking into work wearing the skirt. He had worn skirts a lot recently, but now this time it just felt so different. He felt so much more exposed.
“You do look very nice, you know,” Robin stated as they walked.
What could he say? “Thanks.”
“And I’m glad you appear to have some breasts today too. Much better.”
Chad rolled his eyes and said nothing. Trust a woman to notice everything!
“And your legs aren’t half-bad at all!”


Rachel said...


wow - if all of this has happned by week 3 I dread to think what state poor Sissy will be in by the end of the second month!

Rachel Belle

davemcwish said...

Love your site Karen. I found your old site and was wondering if the What'll I wear program is still available ?

Karen Singer said...

As to my old "What'll I Wear" program - I have "something" in my files. It's an old zip file that I think I used to send out. I can send it to you if you like, but I don't know what version it is and I certainly can't guarantee that it will still work.


davemcwish said...

If you could, I like the idea of it.

Karen Singer said...

For my old What'll I Wear program - you'll have to email me for it at:

siskarensinger at yahoo dot com

Like I said, it's so old now that I can make no guarantees about it.