The Bet - Chapter 53 (Tuesday – Week 8 Part 2 of 10)

The Bet

By Karen Singer

Chapter 53 (Tuesday – Week 8 Part 2 of 10)

     Once he got to work, Chad carefully got out of his car, and pulled his skirt down.  Only then did he reached back into his car to grab his diaper bag and purse – after which, he was tempted to pull his skirt down again – but no amount of tugging was going to get it to cover up the black bows attached to his garter straps.  Ugh! 

     All too aware of what was showing, he braced himself and hurried toward the building.  He couldn’t wait to get to the safety of his cubicle.  He noticed a few people stopping to stare as he tried to hurry, but the super high thin heels he was wearing weren’t going to let him hurry all that fast.

      “Sissy?” he heard a woman somewhere behind him calling.  But he ignored her, acting like he never heard her.  He wasn’t about to stop to talk to anyone! 

     His toes were in agony by the time he reached the safety of his cubicle.  He was cursing his decision to go ahead and wear the stupid shoes!  But it was too late to do anything about it now.  Hopefully, he’d be able to take his shoes off in a little while.

     Ignoring his hurting toes, he quickly checked Robin’s cubicle and was glad to see that he had managed to get to work ahead of her.  She wanted him to be out in the hallway in front of her cubicle when she arrived every day to greet her.  For once, he was going to get it right!  Shifting from foot to foot to try to relieve his hurting feet, he waited for Robin to arrive.

     Robin didn’t exactly take her time getting from her car to the building, but she didn’t hurry either – just like she hadn’t hurried to get to work.  She didn’t hurry, mostly to give Sissy a chance to get there ahead of her.  Would he greet her the way she wanted him to – for once?  She would just have to wait and see.  With her usual armload of junk, she casually wandered through the hallways and finally turned down the last one.  And there he was – waiting right outside her cubicle like she wanted him to. 

     The moment she saw him though, she almost dropped her armload of stuff.  The closer she got, the more she stared at his strange outfit.  She couldn’t help it, she was simply shocked by what she saw him wearing.  His amazingly tight – amazingly short skirt absolutely couldn’t be ignored.  Nor could she ignore the dark stockings and very high heels he was wearing.  But the biggest thing that stood out were the crazy black bows attached to his garter straps – fully on display!  She wondered if Mel had anything to do with his outfit for the day – no she was sure that Mel had a lot to do with what he was wearing. 

     Chad curtseyed.  “Good morning, Robin.”  Then he curtseyed again, just like she wanted him to – to signify that he was done talking.

     Robin stopped in front of him and stared at him.  She wanted to say something about the fact that he had finally greeted her the she wanted, but those words were simply beyond her.  “Your outfit is… interesting,” she finally managed to say.  “Wait here.”  Almost in a daze, she walked off to her cubicle and unloaded her entire armload of things onto her desk.  Normally, she would have dug into her purse right away to find her mirror and check her face, but she didn’t even think about that, she went straight back to the hallway to look at Sissy instead.

     Chad was nervous about standing in the middle of the hallway dressed the way he was.  He only hoped that she wouldn’t make him stay there and practice curtseying again like she did all too often.

     Robin came back again and stood a short distance away from him – and stared.  No, it hadn’t been a mirage.  He really was dressed like that – for work!  While the top he was wearing wasn’t outlandish in any way – in fact, she rather like it – the wide black belt around his waist seemed to accentuate his figure that was becoming more and more feminine.  Unfortunately, while she had already lost a few pounds since starting at the gym, it also made her realize how much more weight she still had to lose.  Okay, she was a bit jealous!

     But her gaze was absolutely forced back to his legs again, and in particular to the big black bows that decorated where his stockings were attached to the garter straps.  She shook her head at it.  “Hold your arms out just a little and turn all the way around – slowly!  Let me see all of it.”  As his backside came into view, she was surprised to see identical bows on the straps attached to the back of his stockings as well.  His entire outfit was nothing less than… she didn’t know what… outlandish?  But that didn’t seem to begin to describe it.

      “How do you walk in those shoes?” she asked as she looked all the way down to his feet.

     Chad was careful to curtsey before answering.  “They hurt – a lot!”  He curtseyed again.

      “I believe it!  So did Mel dress you today or did you pick this out yourself?”

     Chad had to curtsey again.  “Most of it was Mel’s idea.”  Curtsey.

      “Most of it?  What wasn’t?”

      “Well, she told me to dress as sexy as possible and she also told me to wear the stockings and garter belt, but she let me pick out the rest.”

     He didn’t get the chance to curtsey again or even finish what he was saying before Robin asked, “And you picked that skirt and those shoes?”

     Chad curtseyed.  “I had picked out a different skirt, but she didn’t like it and made me wear this one instead.”  Curtsey.

      “Did the skirt you picked show as much as that skirt?”

     Curtsey.  “Not even close!”  Curtsey.

      “I didn’t think so.  And how about the shoes?  Did she tell you to wear them too?”

     Curtsey.  “No, unfortunately they were my idea.”  Curtsey.

     Robin shook her head again, then she smiled.  “I love it!  I really love it!  I can see right now that we’re going to have a very interesting day today.  Of that I have no doubt!”  She walked off again and went into her cubicle.  “Where’s your diaper bag?” she called without bothering to look back.

     Chad hurried into his own cubicle and grabbed his diaper bag.  A minute later, he deposited it on the corner of her desk – the only empty place big enough that he could find.  Robin opened the bag and glanced inside – six more bottles she noted.  “Do you have anything to work on?” she asked, remembering that yesterday he had been looking for something to do.

     Chad remembered to curtsey – he didn’t want to have to go back out to the hallway and practice again.  “Not really,” he replied.  “At least I don’t think so.  I haven’t even had time to boot up my computer yet.”  He curtseyed again.

     Robin smiled.  “See how nice it is when you curtsey like you’re supposed to?  Conversations are so much easier.”

     To Chad, that was a matter of debate.  Conversations were definitely much more difficult on his side.

      “Since you have nothing to do… work on this first.”  She reached into his bag and handed him a baby bottle.”

     Hating life, Chad disappointedly sank down to the floor and put the bottle to his mouth.  As he sat there though, he immediately realized that in getting down to the floor the way he did, his skirt had ridden up high enough to expose the bottom of his girdle. 

     Robin immediately noticed the patch of white below his skirt.  She also immediately realized what it was and that it was a different girdle than he usually wore.  “I can’t begin to tell you how glad I am to see you wearing a girdle.  It’s so nice to know that you’re suffering with them as much as I did.  Of course, I gave up on them a long time ago.”

     Chad tried to pull his skirt lower, but sitting the way he was didn’t let him move it a bit.  The bottom of his girdle would have to remain on display till he finished his bottle.  One thing that Robin had been right about, this was going to be an interesting day.  Too interesting!

     Robin didn’t even get her computer booted up before the phone on her desk rang.  “Hello?” she answered.

      “Robin!  What’s up with Sissy this morning?  I saw the way he was dressed when he came in.  I called to him, but he didn’t hear me.”

     Robin laughed.  She had no doubt that Sissy hadn’t wanted to hear her.  “Unbelievably, he really is dressed that way,” she replied. 

      “Why?”

      “I have no idea.”  Which was mostly a lie.

      “Well, please make sure he gets to break today.  Tie him up and drag him if you have to.”

      “Oh don’t worry, there’s no way I’m going to let him get out of not going this morning – even if I have to get everyone to help me drag him down there!”

     Mel sat wearily in her desk chair.  She had told Andrea to book a few clients today, but there were so many clients that were getting backed up that Andrea had taken advantage of the opportunity and over booked instead.  So now Mel was taking a break just to clear her head before going in to see the next client.  It was good to get back to her usual business though. Very good!

     Now that she had a minute to think of something other than her clients, she immediately thought about Sissy.  How was he making out today?  She tried to imagine what he must be going through, but she found the exercise simply impossible.  She really couldn’t imagine it.  She could only hope that Robin would fill her in later.  And speaking of Robin…  She opened her email program and typed a thank you note for all the pictures and videos Robin had sent yesterday.  With that done, she dragged herself out of her chair and headed off to meet with another client.

     Chad stared at his computer screen trying to figure out what he should do.  As soon as he had finished his bottle, Robin had sent him back to his desk with an order to find something to keep busy with or she would have him playing with the paper dolls on her floor for the rest of the day.  He didn’t want that at all.  So now he was staring at his computer screen wondering what to do.

     Well, first things first.  His feet were killing him!  He unfastened his shoes and slipped them off.  Ah!!!  So much better!  He stretched and bent his toes, feeling the relief of each little movement. 

     Feeling better, he decided to open his spreadsheet for tracking the bet.  He found today’s date and checked the columns next to it.  There were only ten days left.  It certainly didn’t sound like much, but at the same time it seemed like an eternity.  Especially since he hadn’t had a chance to hold back at all yet today – yesterday either for that matter… or Sunday… or Saturday.  He couldn’t even remember if he had tried at all on Friday.  Things weren’t looking good for him – of that he was sure.

     Was it possible that Mel could win this bet?  Everything he knew from his readings, and everything he knew about his own body told him she couldn’t win.  There was no way possible.  Yet in the meantime, his body was acting awfully incontinent.  Totally incontinent!  Could he get it all back in just two days?  Or at least enough control to show that he wasn’t completely incontinent?  He simply didn’t know.

     But those thoughts made him wonder, just how were they going to decide anyway who won this bet?  What if things got so close that they needed a better way to decide definitively exactly who had won?  He made a mental note to send an email to Mel just as soon as he closed the spreadsheet to ask her about it.  And since he didn’t have to curtsey or use his sissy voice in an email – it was really the easiest way to discuss it with Mel.

     He momentarily clicked in the column where he would have entered how long he had held back yesterday.  But he had nothing to put there – just like he hadn’t entered anything yesterday.  He hadn’t really been able to try to hold back at all.

     He quickly glanced over at all his reasons for winning the bet.  Were they still good reasons?  He thought so, but he wasn’t totally sure now. 

     Slightly frustrated, he closed the spreadsheet and opened up his email program instead.  Just how were he and Mel going to decide who won and who lost?