The Bet - Chapter 56 (Friday – week 8 Part 2 of 9)

The Bet

By Karen Singer

Chapter 56 (Friday – week 8 Part 2 of 9)

     Mel stirred the pot of baby cereal one more time before turning the heat off.  Now all she needed was him.  She poured it out into his childish bowl and found one of his tiny baby spoons.  She got a fresh bottle out of her refrigerator for him and set that next to everything else.  Now where was he?  Had she misjudged how long it would take him to get ready?  The knocking at her door actually brought a feeling of relief.  She hurried to answer it.

      “Good morning, Mistress,” Chad said in his stupid sissy voice along with his usual curtsey the minute she opened the door.

     He was really quite a sight standing there in nothing but one thin diaper and his bra.  His dark red purse and diaper bag looked more than a bit incongruous on his shoulders.  The plastic bag containing his empty bottles was in his hand.  “Good morning, Sissy,” she replied as she stood back so he could enter.  Like yesterday, there wasn’t anything for her to inspect about him.  So as soon as he had set his things down under her table by the door, she took the plastic bag from his hands and sent him into the kitchen to get up into his highchair.

     She had everything all laid out and ready for him so it took almost no time for her to stick the tray in place, tie his bib around his neck, and set his breakfast out for him.  One big baby stuck in his highchair eating baby food.  Perfect! 

     Chad carefully spooned tiny spoonful after tiny spoonful of the awful tasting baby cereal into his mouth.  At least he wasn’t spilling as much of it as he used to… but there was always some that never made it into his mouth. 

     As he ate, he watched as Mel again swapped out the empty bottles in his diaper bag for full ones, after which she was gone for a few minutes again.  He assumed she was adding more diapers to his bag.  After that, he watched as Mel refilled her coffee cup then leaned back against her counter to watch him. 

     Was she going to tell him what was going on today?  Yesterday she hadn’t.  But then when she did spring it on him yesterday, it had been a terrible shock.  He didn’t know what she had planned for him today, and that made him nervous… very nervous!  So in a way, he wasn’t looking forward to finding out.  But he still worried about it and wanted to know.  But like yesterday, she wasn’t talking.

       He had resigned himself to not knowing anything, when Mel finally opened her mouth.  Unfortunately, what she started talking about had nothing to do with what he was currently worried about.

      “Robin called me yesterday,” Mel told him, which instantly sent worry flags up Chad’s spine.  “She said she wants to be one of the judges for our bet.”

     That didn’t sound good to Chad at all.  “But how can she be fair?” he asked between tiny bites of his cereal.

      “She claims she’s going to be totally fair.  And, she’s somewhat insisting on begin a judge.”

      “And you’re going to let her?”  Chad was really worried.

      “As long as she claims to be fair,” Mel responded.  “And since that would leave us with an even number of judges, I finally convinced Gloria to be a judge too.”

      “Gloria?”  That surprised Chad somewhat.   

      “Yes.  But… Gloria is only doing it under her conditions.”  She saw the dubious look on Chad’s face before she continued.   “And… I agreed, I guess for both of us.  That is, unless you have some really big objections and then I’ll tell her no.”

      “What conditions?” Chad asked in his stupid voice.

      “The biggest thing, I guess, is that she’s not going to let us decide the outcome of this bet ourselves.  She’s insisting that all the judges will get together with us on Saturday to determine the winner.  Like it or not.  And the judges will decide the criteria for deciding, not us.”

     Chad thought about that for a moment.  He would have argued that they should be able to decide the thing among themselves, but he was the one who originally thought they might need judges to decide it fairly.  So he certainly couldn’t protest about that.  “Okay,” he finally replied.  “I guess it’s okay.”

     Mel nodded.  “I thought you’d approve.”

     So now was she going to tell him what was going on today?  But once again, she fell silent, and he went back to finishing his breakfast.  His nervousness increased with every tiny spoonful of the awful tasting mush.

     When he had finished, Mel wiped his hands and face with his bib and let him out of his chair.  “Okay Sissy.  Let’s go get you dressed.”

     This was the part that Chad worried about, but at least she had mentioned getting him dressed so she wouldn’t be sending him to work in just his diaper.  Silently, he grabbed his purse and now heavier diaper bag from under her table, while she just grabbed her keys.  Then he followed her back outside – still wearing only his diaper and bra – over to his apartment.  He was glad to get back inside with the door closed behind him.  It was awfully embarrassing being outside dressed as he was.  But now the question was – how embarrassed was he going to be when he left again – for work?

     Like yesterday, Mel took him into his bathroom where she did his makeup again.  And like yesterday, she seemed to go lighter with it than he usually did.  He didn’t get much of a chance to study his face because as soon as she finished, he had to follow her into his bedroom where she went straight to his closet. 

     Mel stared at all the clothes in his closet, but there were really only two outfits she was looking for.  She looked back at him briefly and smiled wickedly at him.  He looked very nervous.  She couldn’t blame him.  She looked back at his closet for a moment before suddenly springing on one outfit and removing it from the closet.  She held it up for him to see.  “Perfect!” she declared.  “I can’t imagine you wearing anything better than this.”

     Chad nearly died!  She was holding up his most babyish pink sissy dress… the one that left his diapers completely on display – all the time!  “No!” he groaned.  “Please Mistress, no!  Not that!  Anything but that!  Please!  Please Mistress, please!”

      “Oh come on,” Mel replied.  “You know you’ll love it!”

      “No Mistress.  Please!  Not that.  I can’t wear that!  Not to work!  I can’t!”

     Mel looked at him with a somewhat surprised look on her face.  “Gee!  I can’t imagine why you’re carrying on like that today.  Look what you wore to work yesterday.  This can’t be much worse than that!”

     Now it was Chad’s turn to look surprised.  “But Mistress…  It is!  It’s much worse.  I can’t hide my diapers at all in that!  Please Mistress.  Not for work!  Please!”

      “Holy cow you’re raising a fuss today!” she said, her voice sounding somewhat irritated.  “Okay, if you’re going to feel that strongly about it…”

      “I do!” Chad replied quickly.  “I do.  I can’t weary that dress to work!  Please!” he begged.

“Well then,” Mel replied as she held the pink dress in one hand and gazed back into his closet.  “I guess I could give you a choice.  You can either wear this,” she held up the pink dress again, “or…”  She reached into the closet and pulled out two hangers, “This!” she proclaimed as she held the garments up so he could see.”

     Chad stared in shock.  Of course!  He should have known!  He was relieved, but not by much.  In many ways, her second choice would be worse than the first, but not by much.  Reluctantly, his hand shaking a bit, he pointed at the second outfit – the bright miniscule skirt and itchy wool top of his sissy schoolgirl outfit. 

     Mel smiled.  “Somehow I thought you’d pick that one.”

     Chad was in no hurry to put the outfit on.  The sweater and knee socks were made of wool that was not only very warm, they itched something terrible!  As he was drawing the skirt up his legs, he realized something.  “Mistress,” he said.  “Are you going to add more diapers again?”  He wasn’t sure at all that he wanted to know the answer to that one because more diapers would mean that they would definitely show below the bottom of his skirt… but not adding more diapers would mean that he would be forced to make his diapers leak all day again.

      “No Sissy,” Mel replied.  “Robin has promised to make sure you leak like you’re supposed to all day.  So only one diaper I’m afraid.  Although I know how much you really like the diapers showing below your skirt.  You could always consider rolling the skirt at the waist a bit so your diaper does show.”

     Chad’s whole body shook for a moment at that one before he realized she was teasing… he hoped.  “No thank you Mistress,” he replied as he fastened the skirt in place.  But now came the miserable itchy sweater.  Why did she have to buy a wool one?  Did she have any idea how much the thing irritated his skin?  But then he remembered, she did know.  And that was the reason she had bought wool socks to go with the outfit.  Ugh!

     A few minutes later, Chad stared at his reflection in the mirror.  The bright green, red, and white plaid skirt – so short it was positively sinful!  But with only the one diaper under it, he couldn’t see anything below the bottom of the skirt – at least from his angle.  He pulled down on his skirt anyway in an attempt to tug the thing lower.  It didn’t move.  Above the skirt he was wearing his white angora wool sweater with the pink bow at the neckline.  He was already fighting to stop himself from trying to itch at his skin below it.  Below the sinful skirt were his red wool knee socks – itchy too.  And on his feet… saddle shoes.  The heart shaped necklace and dangly earrings that Mel had bought him to go with the outfit were his only jewelry today. 

     He stood there looking at himself as Mel fastened the white bow on top of his head.  Picture of a sissy!  Again!  At least this time he couldn’t actually see the diaper he was wearing under his skirt.  When he had worn the outfit all around the mall last weekend, Mel had stuck him in so many diapers that they could easily be seen below his skit.  He didn’t think anyone could see the one diaper he was wearing today, but he wasn’t all that sure about it.  How about from the back?

      “You took so long getting dressed,” Mel said to him, “that I hope too many people won’t be around to see you going into the building today.”

     Chad panicked again.  Yesterday she had gotten him up much earlier and had made sure he got to work before anyone could see what he was wearing – mostly anyway.  But today it was much later, and if he didn’t hurry, then he’d be arriving at prime time… when most of the people arrived.  He turned fast and ran out to the living room.

      “Get your pacifier!” Mel called behind him.  “And don’t forget your little sissy purse!”

     Chad grabbed his pacifier from the kitchen again and rushed to transfer his phone, keys, and a few things from his wallet back into the little purse again.  He looked up at Mel.  “Are you driving me to work today?” he asked since she had taken him yesterday.

      “No, I think you can get there by yourself today.”

     Chad opened his door to leave, but he turned back to Mel and quickly curtseyed.  “Bye, Mistress,” he said hurriedly through the pacifier in his mouth.

Mel giggled.  “Have fun Sissy.”

     Driving while wanting to itch so badly was nerve wracking.  In fact, just the itchy wool was nerve wracking without driving.  But he made it to work – early, but not very early.  He could see a few people pulling in and heading to the building from various parts of the parking lot.  But he knew that if he waited much longer, the amount of people would only grow – by a lot! 

     Hurrying as fast as he could, he opened his car door and got out.  He opened his rear door and grabbed his diaper bag.  Then, after closing the car doors, he ran for the building as fast as he could.  At least the saddle shoes were fairly good for running in.  The running also seemed salve some of the itchiness his body was enduring.  But at the same time, he realized that his running was also drawing all too much attention to him… from everybody that was around.  He couldn’t stop now though, it was too late.  Everybody coming in had already seen him.  He kept going, briefly wondering if they could see the diaper he was wearing under his skirt.  Hopefully, he was going too fast for them to tell what it was!

     He opened the doors and dashed inside.  More people in the hallways.  He slowed his pace down to a nervous walk since all those people were in front of him and most of them were going the same direction he was.  Well, most of them anyway.  There were two women talking and heading toward him in the distance.  Could he get to the corner and turn before they got there?  He walked faster, almost catching up to the man in front of him.  He got to the corner but the women were all too close… and the looks on their faces as they saw him told him way too much. 

      “Sissy…” he heard them calling as he turned the corner to head down the next hallway.  He purposely ignored them and kept going – still at his nervous pace.  A few turns and three people later, and he was finally at his desk.  Whew!  But he had been seen!  By more than one person.  And some of the people who had seen him were women that he knew!

     Now what was he going to do?

     As Robin got out of her car, her mind was totally occupied with wondering what Sissy was going to wear today.  But Mel had said yesterday that she was going to let him choose again, so she wasn’t expecting anything “interesting.”  Pity!  She had rather enjoyed yesterday.

     As she turned down one of the hallways, she ran into one of the women she met with every day in the break room.  “Robin!” the woman said as she hurried over.  “What’s with Sissy today?”

      “Sissy?”

      “Yeah, we were here a little early today to get some copy work done, and we ran into him as he was hurrying in.  The outfit he had on!”

      “Outfit?” Robin asked, not knowing what she was referring to.

      “And not only that…” she dropped her voice to a whisper.  “It looked like he had a pacifier in his mouth!”

     Robin’s eyes went wide.  “He did?”

      “Yes!  He did!”

     Robin wanted to laugh.  “I can’t wait to see what you’re talking about!” Robin replied.

      “Well, you better make sure he gets to break this morning, or I can guarantee that most of the company will be down there to see for themselves!  Me included!”

      “Um…  Okay.  I’ll do my best to get him there,” Robin replied.  What was Sissy wearing?  It sounded like Mel had put him in something else that was very interesting.  She was betting that it was one of his other pretty sissy dresses – especially since he had come in with the pacifier in his mouth.  She giggled at that thought as she headed for her desk. 

     She turned the last corner hoping to see him out in the hallway again, but he wasn’t there.  Was he hiding again?  If his outfit was anything like what he wore yesterday then she couldn’t blame him.  Halfway down the hallway, she saw his head poke out sideways again – and again she noticed the same white bow in his hair.  Yes!  Another little girl outfit.  But when he quickly stepped out into the center of the hallway and she could see his entire outfit, she was so stunned she stopped short once again just to look at him.  Unbelievable!  She was so stunned that it was a moment before she could continue walking.  She had expected a little girl outfit… but not… this!

      “Good morning Robin,” Chad said in his stupid sissy voice after curtseying and removing the pacifier from his mouth.  Then of course he had to replace the pacifier and curtsey again.

      “Good morning, Sissy,” Robin replied, although her entire attention was focused on what he was wearing.  Wow, that skirt was so short.  And was that top made of wool?  It certainly looked awfully heavy!  She had seen pictures of him in the outfit, of course.  They were among the ones that Mel had sent.  But seeing the outfit for real was totally different. 

     She set her bag down in the hallway and walked all the way around him.  His hands kept playing with the short hem of his skirt… no, he was trying to keep it tugged down.  On a whim, she picked up the back of his skirt a bit.  Yep, one very soaked diaper just barely covered by the skirt.  If he moved wrong the thing would show for sure!

      “Do you know,” she said as she got back toward his front side again, “that I just ran into one of the women we see in the break room every day?  She asked about your outfit, but of course, I had no idea what you would be wearing today.”  She giggled.  “She also mentioned that you had a pacifier in your mouth when she saw you.”

     Chad nearly died!  His pacifier!  In his rush to get to his desk, he had forgotten all about it!  How was he supposed to explain that?  For that matter, how was he supposed to explain anything?

      “Is that diaper leaking?” Robin finally asked.

     Blushing, Chad again curtseyed and removed his pacifier, “Yes, a little,” he admitted.  Pacifier, curtsey.

      “Good.  It’s always best to start the day with no problems.  Go change it,” she told him.

     No problems?  He had nothing but problems today.  Big problems!  But he curtseyed and hurried into his cubicle to change his soggy diaper.  He had forgotten about his stupid pacifier!  As if what he was wearing wasn’t bad enough!  He fought the urge to rub madly at his chest to relieve the constant itching from his sweater.  It wouldn’t do any good if he did!

     Robin watched as he simply pulled his tiny skirt all the way up.  He certainly didn’t have the problem he had yesterday where he had to deal with too many skirts.  His skirt today was the exact opposite of what he had to deal with yesterday – too little skirt.

     It only took him a few minutes to change.  When he was done, she looked at him for a moment.  Something seemed wrong.  Well, not wrong, just not what she thought she should be looking at.  “Take your pacifier out and suck your thumb instead,” she ordered.  She watched as he put the pacifier on his desk and stuck his thumb deep into his mouth.  “Much better!” she declared.  “Suck your thumb today, it goes better with your outfit.”

     With that, she walked out to finally go to her own cubicle and get ready for the day’s work.  The pacifier had been perfect with the babyish dress he was wearing yesterday.  But the outfit he had on now was… okay, she was guessing some kind of schoolgirl look, so it was still childish, but it was an older child.  And for some reason, she liked the thumb better with it than a pacifier.  She almost giggled at the thought that for him, his thumb in his mouth could be considered an accessory.