The Bet - Chapter 53 (Tuesday – Week 8 Part 1 of 10)

The Bet

By Karen Singer

Chapter 53 (Tuesday – Week 8 Part 1 of 10)

     Paper doll pieces littered the floor around him as he once again sat Indian-style like a child on the floor of Robin’s cubicle.  Paper doll pieces around him, but the doll in his hands was plastic – a real doll.  Under Robin’s watchful eyes, he removed the pretty pink patterned dress the doll was wearing.  He was surprised to see that underneath the dress the doll was wearing a diaper. 

      “She’s just like you,” Robin said in his dream.  “A little doll to dress up any way you want.  And she even wears and wets her diapers too – just like you.  And just like you, I think you should keep her wetting that diaper.”  With that, she handed him the doll’s tiny baby bottle.  “Stick that in the baby’s mouth now and feed her.”  He took the bottle and stuck it in the dolls mouth.  “Now here’s your bottle too,” his dream Robin said.  “You can’t stop wetting either.”

     Holding his own bottle to his mouth, he drank deeply while he fed the doll her bottle as well.  He felt himself wetting again, and at the same time, noticed that the diaper on his doll was getting wetter too.

      “You’re so much alike, you two,” Robin said.  “You’re both babies.  You’re both toys for others to play with and dress up any way we like.  And you both can’t help wetting yourselves.”  The dream Robin laughed.  “You both drink from a bottle at one end, and it comes out of both of you at the other end.  Silly sissy babies for everyone’s enjoyment.”

     It was as if her words were some kind of trigger, because all of a sudden all the women that usually sat at the break room table with them showed up at her cubicle.  All of them pointed and laughed at him and what he was doing.  All of them commented on the silly way he was dressed.  And all of them commented on how wet his diapers were – much wetter than his dolls.  And in his dream humiliation, he felt himself wetting even more at their words and laughter. 

     And then they started talking to him.  “So it’s true, you are a sissy,” one of them declared. 

      “We just knew it!” another one replied. 

      “It was obvious from your fingernails!” another one noted.

      “It was obvious from the start!” a third one added. 

     He wanted to tell them they were all wrong, but the problem was, they were all right.  He couldn’t deny it, he was a sissy.  A big sissy! 

     Their taunting became a sing-song chant.  “Sissy, sissy, sissy!  Sissy, sissy, sissy!”  The humiliating taunting went on and on, until strangely, it was accompanied by music… loud music.  Music that quickly drowned out not only the voices, but his entire delicious dream.  It was the alarm on his stupid pink clock radio.  And it was time to get up again.  Ugh!

     He rolled out of bed, knocking over a few empty baby bottles in the process and turned his alarm off.  It was another day.  He had to get ready for… another day filled with humiliation after humiliation.  And as much as he hated it, he also couldn’t deny that he loved every bit of it just as much.  As his dream had said…  “Sissy, sissy, sissy!” 

     He stumbled wide-leggedly out toward his kitchen where he expected to see a note from Mel.  It was there, right on his counter, right where he expected it to be.  Still rubbing the sleep from his eyes, he read what she had written. 

     Most of the note was the same old thing… the usual three baby bottles, so on and so forth.  She had also included a little reminder at the end of the note that he had to wear three diapers to work from now on instead of two.  The reminder wasn’t really necessary, but he supposed he appreciated it since she had taken the trouble to include it. 

     The part of her note that he didn’t really appreciate however, was her order that today he had to dress as sexy as possible.  “Wear your shortest skirt, your highest sexiest heels, and do your makeup as bold and sexy as possible.  Wear the garters and stockings today that you wore to the poker game.  And instead of your all-in-one girdle, wear the open bottom one instead.  Your choice of bra, but don’t forget your waist cincher.  If you like, you can borrow my skirt again that you wore to the poker game.  If I don’t like the skirt you choose, you’ll be wearing it anyway, so consider it.  Let me see what you can do!”

     Her order shocked him somewhat.  Dress as sexy as possible for work?  Wear his shortest skirt and highest heels?  And the garter belt and open bottom girdle?  Something about that smelled like a lot like trouble for him, especially if she didn’t like his choice of skirt and she made him wear her skirt instead.  That one had been a nightmare.  He distinctly remembered how he had to keep pulling it down to keep his diapers from showing.  And by the end of the night, they were showing below the skirt anyway.  Nightmare!  Yet the thought thrilled him too.  It was just hard to admit – consciously. 

     He grabbed his usual three bottles from the refrigerator and carried them out to his solitary chair facing his wall of shaming pictures.  He put the first bottle to his mouth, but his mind wasn’t on his bottle, nor was it on the pictures.  His mind was totally focused on her strange request.  Dress as sexy as possible?  How?

     Mel poured her first cup of coffee of the day, but the act was so automatic that she didn’t even think about it as she did it.  Her mind was instead on her problem from work.  How could she make sense out of the million pages of contract paperwork in so little time?  She took a few sips of her coffee and headed into her living room where she sat in one of her chairs to drink… and to think.  She had told Andrea she would see some of her regular clients today.  Maybe that’s what she needed to do.  Put this whole contract mess out of her head and get back to her usual business.  But the thought of “usual business” instantly brought thoughts of Sissy to her mind.  He was now her “usual business” too.  And he was also one that she’d much rather think about.

     She had told him in her note last night to dress as sexy as possible today. Well, she would see what he could do – but she didn’t have very high expectations.  It wasn’t something she had really had him do for himself before.  And that thought made her remember that she had to dig out and find that little black and silver skirt she had him wear to the poker game.  She seriously doubted that he would be wearing any skirt to work today except that little skirt.  And she also seriously doubted that the darn thing would be anything except a major nuisance to him – all day long!

     Chad stared at his reflection in the long mirror hung on his closet door.  Over top of his three diapers, plastic panties, and waist cincher, instead of his usual all-in-one girdle, he was wearing the very tight, very high wasted, open bottomed girdle he had worn to the poker game.  He was also wearing the same black lacy bra, garter belt, and smoky black stockings.  Fortunately, the only part of anything that showed was a little bit of the darker material at the tops of his stockings.  He turned his legs to look as carefully as he could to make sure the seams in the back were straight.  They looked perfect – or so he hoped.  

     He was wearing a somewhat conservative red top with white lace all along the v-cut neckline.  He was wearing this top because the low-plunging neckline on the first one he had chosen showed way too much of the fake breasts that were glued to his chest.  He had tried to put a little bit of makeup over the edge of the breasts where they met his real skin like Mel had done for the poker game, but he couldn’t get it right and it wound up looking worse.  So he had chosen this more conservative top instead.  He only hoped Mel would approve.

     Below his red top, he was wearing the shortest skirt he could find in his closet.  The skirt was supposed to look like blue denim, but the material was much softer.  It was also fairly full which was good because he would worry less when his diapers got bloated.  It was not one that he had bought with Mel, but rather one from before he had met her.  The problem with this skirt though, was that he had lost a lot of weight in the last two months and the thing didn’t really fit right anymore.  It kept slipping down from his waist to hang way too low on his hips.  If it wasn’t for all the diapers he was wearing that filled out his backside, the darn thing would probably slip off.  He didn’t think it looked all that bad though.  And it was somewhat short – especially when he took the time to pull it all the way up where it belonged.  It just wouldn’t stay there.  And fortunately, when it was pulled all the way up, it still hid most of the tops of his stockings and especially the big black bows attached to the garters hanging down from his garter belt.  And if… like at work… he didn’t bother to pull the skirt up when it slid down, then all the better because his stockings and garters would show a whole lot less!

     And of course, he couldn’t miss seeing the reflection of the shoes he was wearing.  His highest heels.  Not patent leather, but the black was almost as shiny.  They had a thin strap that wrapped all the way around each ankle.  And the heels - five inches long and tapered very thin.  They were just a little bit higher than the pink heels Mel often made him wear – and there was no way he was going to wear those pink heels to work!  The problem with these shoes though, was that they were not only a bit hard to walk in, they were very uncomfortable.  His toes already hurt.  He considered taking them off, but figured why not wear them.  He usually sat down most of the time anyway and he didn’t walk all that much during the day.  And if they hurt too much, he could always take them off for a while.

     Instead of the usual studs he wore in his ears, he had added the gold heart-shaped earrings and necklace Mel had bought him on Sunday.  He liked the way the earrings dangled down from his ears.  They were much better than the simple studs and much more exciting to wear.

     He stared at his overall outfit for a moment more.  It was the best he could do.  But would Mel think it was sexy enough?  He’d find out in just a few minutes because if he didn’t get going soon, he was going to be late. 

     Mel answered her door a few moments after he knocked.  She smiled broadly at his usual curtsey and greeting – she still loved seeing it.  “Good morning, Sissy,” she replied as she stood back to let him in.  Her eyes had started checking him out the moment she had opened the door.  As he put his things under her little table, she kept checking.  As he bent down, the back of his skirt revealed a bit of the black bows attached to the garter fasteners at the tops of his stockings.  But the back of his top rode up a little and she also noticed something odd about the way the waist of his skirt seemed to fit.  She said nothing though.

     Chad set his things on the floor, then stood up and handed her the bag containing all his empty baby bottles – noting that again she didn’t even look in the bag.  Instead, she seemed to be looking him over all too carefully.  We’ll, he had expected that today.  But would he pass?  He certainly hoped so.

     Mel started again from the top – of his head.  His hair was the same as always, although she did notice today how much longer it seemed to be getting lately.  Would it be long enough soon to do something else with?  But that was a question for after this bet was settled – after she won.  “I like your choice of jewelry,” she told him.  “We really need to get you some more earrings now that you can start wearing something other than studs in your ears.  Some really big hoops would have been perfect today.  If I had anything like that, I’d let you borrow them.”

     Chad wasn’t sure if he was glad or not that she didn’t own any large hoop earrings.  On the one hand, they would probably be too embarrassing to wear, but on the other hand, he would certainly love it.

      “You could have done a lot more with your makeup.  A lot!  I think it’s time to start teaching you to do it more dramatic so you don’t always look so… plain.”

     She stared at the red top he was wearing and particularly at the neckline where his breasts were.  She would have liked to see something much more low-cut, but she guessed that with his breast forms, anything much more “interesting” would be out of the question.  “You could have chosen a sexier top too,” she complained as her eyes scanned down to his skirt. 

     She stared at the denim skirt he was wearing.  Then she stepped back so she could see it better.  It wasn’t real denim of course, and it wasn’t a straight skirt.  In fact, it was rather full.  But it was somewhat short.  She remembered seeing the skirt in his closet, but she had never seen it on him before.  She supposed it was… acceptable.  Acceptable – except for one odd thing that she just now noticed.  She looked closer.  Yes, she was sure of it.  “Why is the hem of your skirt crooked?” she asked.  “It doesn’t look like that kind of skirt.”

      “Crooked?” Chad asked totally surprised as he quickly glanced down.  But he was guessing as to the reason for what she was seeing.  And as his body moved ever so slightly, he felt the waist of his skirt slip a little bit more.

     Mel quickly walked up to him and lifted his top up a bit.  She remembered that odd thing she had seen on the waist of his skirt a few moments earlier.  She looked closer now.  She pulled on the skirt, and it easily slid down his waist at least three more inches.  “You can’t wear that!  It doesn’t fit!”

     Chad remembered to curtsey before he answered.  “It’s the shortest skirt I had!”

      “Not if it slides that far down.  It will be just as long, or longer, than what you usually wear!  Take it off!  After breakfast I’ll get you another one.”

     Chad wasn’t at all happy about that, mostly because he already knew what skirt she would give him.

     Mel took a better look at his shoes as he was pulling the skirt off.  She had seen them in his closet as well, but like the skirt he was removing, she had never seen him wearing them.  Trust a sissy to buy the sexiest shoes possible.  The heels looked to be about as high as the pink patent leather shoes she liked to see him in.  Her first thought about them was how uncomfortable they looked to wear.  Her second thought was that she should have him wear them much more often. 

     A few minutes later, Chad – without his skirt – was sitting in his highchair with a bib tied around his neck eating rather bland baby cereal with a tiny rubber coated baby spoon.  Mel disappeared as soon as she had set his bottle on the tray for him.  She came back a few minutes later and he saw her throw the dreaded grey-black skirt on the table for him.  Only then did she go to the refrigerator where he saw her remove six fresh baby bottles to replace the ones in his diaper bag now.  Six bottles!  He fervently hoped that Robin wouldn’t make him drink so much today, but somehow he had a feeling that she would. 

     When he had finally finished his breakfast, he struggled to pull the shiny skirt up over his padded bottom.  Even after losing more weight, the skirt was still very tight.  Eventually, he got it all the way up – after which, he immediately pulled down the bottom to make sure it covered as much as possible – which was all too little.  There was no way though that it would even begin to hide the big bows over top of the clips that were attached to the tops of his stockings at the front and back.  They were going to be on display all day!  He worried a lot about that.  What would everyone think? 

      “Wait a minute,” Mel said as she was looking at how the skirt looked on him.  We need to fix something.  She bent down to his legs, and one by one, tightened each of his garter straps so that they pulled on his stockings much tighter.  “I think you’ve lost so much weight that the belt is sitting lower on your hips.  This should help.”

     Help?  But Chad immediately noticed how he could now feel the tug of each of the four garter straps against his stockings that much more.  He looked down.  Even after she had tightened them, he could still see an inch of garter between the bottom of his skirt and the big black bows attached to his stocking tops.  How was he going to get through the day like that?  It was going to be an absolute nightmare! 

     And then his brain turned to the one biggest thing he kept remembering from the last time he had worn this skirt – by the end of the poker game – no matter how he had tried to pull the skirt down, his diapers had shown down below it by.  He really prayed that wouldn’t happen again today.  He’d never be able to explain it!

     Mel looked him over carefully again.  She nearly laughed out loud at the display of garters and stocking tops.  That should give Robin something interesting to think about!  She forced herself to look past his garters to the rest of his outfit.  “Silver jewelry would go better with the silver flecks in that skirt,” she said to him, “but what you’re wearing will have to be good enough.”

     She kept staring at him.  “Wait right there!” she suddenly exclaimed before hurrying off to her bedroom.  She was back a few minutes later with a wide black patent leather belt that she fastened tightly around his waist over top of his red top.  Then she stood back to survey him again.  The belt made a big difference.  The big silver buckle didn’t go all that well with his other jewelry, but it did go better with his skirt and stockings.  It also emphasized the difference between his waist and his bust much more.  “We’ve got to get you more accessories,” she noted out loud.  “It’s the simple things like that belt that really make that outfit.  Okay, Sissy, you better get going.  You don’t want to be late.”

     Chad headed to the door where he picked his diaper bag and purse up from the floor, the minute he stood up again he realized that he needed to pull his skirt down – already.  Once again it looked like it was going to ride up all too easily.  He had to hang both bags over his shoulders before he could carefully bend down enough to try to grab the bottom of his skin tight skirt and pull it down – which proved to be a difficult exercise.  He congratulated himself for managing to do it without either the diaper bag or his purse falling off of his shoulders. 

     As he curtseyed and said goodbye to Mel, his thoughts were mainly on his skirt.  This was not going to be an easy day.  Two minutes later, things didn’t look like they were going to get any easier as the shoes on his feet made getting down the steps to his car a major pain – literally!