The Bet - Chapter 52 (Monday – week 8 part 3 of 8)

The Bet

by Karen Singer

Chapter 52 (Monday – week 8 part 3 of 8)

     Ray sat back in his chair and closed his eyes.  He had a date lined up for later tonight, but no date for tomorrow.  Once again his thoughts turned to the tiger… otherwise known as Gloria.  Damn, what an evening!  He had gone out with someone else on Sunday, but he didn’t think he had performed up to his usual standards!  He was sure he would have no trouble like that tonight.  But his real problem was that he couldn’t get that demented tiger out of his mind.  What a crazy woman!  Damn she had been good!

     But the fact remained, he still wanted a date for tomorrow night.  And first on his list was Mel – the rich woman!  The one that Gloria had claimed was… loooaded!  And better yet, Mel had already said she wanted to go out with him again.  Heck, she had practically pleaded with him!  Well, it would be another expensive evening, but if things went right, she would be a great one to eventually get engaged to.  Rich!  Rich!  Rich!

     With a bit of a chuckle, he dialed her number.  A moment later he said, “Hi Mel.  This is Ray…”

     Mel took the opportunity to sit down in her desk chair and relax.  She had been trying vainly to sort through the huge amount of material she had received that morning.  “Ray!  You couldn’t have called at a better time.  I need a break!”

      “How about a bigger break for lunch?”

     But big red flags suddenly went up in Mel’s mind.  As much as she really liked Ray and wanted to go out with him again, there was the new complication of Derek – which ordinarily wouldn’t have been a major problem, but since Derek now knew about Sissy, then she felt like she needed to stay close to Derek for a change.  The fact that she really liked Derek better may have influenced her decision too.  “Um… Ray… I think I better decline for now.  I have other things going on.”

      “Then how about a regular date.  I’m available tomorrow night and you did say you wanted to go out with me again.  I know I loved our last date a lot!”

     She had too.  But…  “No Ray.  Sorry.  Not tomorrow night.  I have too much on my mind right now.”

     Ray was disappointed, to say the least.  He tried to salvage what he could.  “Well, don’t forget about me.  I still want to see you again.”

      “Me too,” Mel replied.  “And thanks for asking, but not right now.”  She hung up.  She liked Ray – a lot!  But did she like Derek better?  They were both great.  And they were both… different!  But for the next few weeks, Sissy was one big complication that she had to get sorted out first.  And sorting out meant winning the bet!

     Ray hung up his phone disappointed.  She was busy!  But she was rich so he wasn’t about to simply give up on her.  No, he would try again tomorrow, and the day after, and the day after that.  Eventually, he’d go out with her again and take things from there.

     In the meantime, who could he call?  And still the only woman his mind wanted to conjure up was the wild woman – Gloria.  But she worked late during the week.  Darn it all!

     Chad had never felt more uncomfortable about things as he silently followed Robin back to their cubicles.  What were people going to think? 

     Before Chad could turn off to his own desk, without bothering to look at him, Robin said, “My place!” and she continued straight to her cubicle.  As soon as she got there, she turned on him.  “Skirt off!”

     Chad couldn’t believe it!  Things weren’t bad enough?

      “You want to make things worse?” Robin asked when he didn’t move immediately.

     Chad didn’t dare hesitate any longer.  He knew Robin wouldn’t hesitate to find some other way to make his life more miserable.  Quickly, he removed his skirt and handed it to her. 

     Robin threw his skirt on her desktop, then she opened his diaper bag again and handed him another bottle to drink.  “Get busy,” she told him. 

     Chad wanted to cry.  He had just finished a whole cup of coffee and now she wanted to make him drink this too?  He had yet to be able to start trying to control himself.  This bottle would be like pouring gasoline on a fire.  There would be no way!  Reluctantly, he put the bottle to his mouth and sank down to her office cubicle floor.

     Robin watched him put the bottle to his mouth.  The image of him putting it in his mouth and then sinking down to the floor seemed to burn itself into her mind.  She turned back toward her computer, but as she did so, she noticed the multi-colored bow again.  She picked it up and looked at it.  Did she dare put it in his hair now?  Now that everyone was starting to suspect there was more going on with him than they thought?  She held the bow out in her hand so that from her field of vision it kind of sat on top of his head, the long streamers hanging down covered his face.  But the recent image of him putting the baby bottle into his mouth came back to her – especially where his skirt was so obviously missing.  She mentally imposed the bow over where his skirt should have been and nearly laughed.  Now that would be funny!  She looked at the bow carefully.  It had the usual hair clip underneath.  But to do what she wanted she would have to find some other way to attach it.  She opened her desk drawer, but the closest thing to anything useful was her scotch tape, and she knew that wouldn’t be nearly strong enough to do the job.  But…

      “I’ll be right back,” she told him as she set the bow back on her desk and walked out.  The supply room for that part of the building was down several hallways, but not all that far.  She went inside and started poking around the shelves – and finally pounced on some wide clear packing tape.  Tape she knew was much sticker than the thin tape she had at her desk.  She was about to leave, but since she had come in there for tape, she remembered that she had been using more than her usual amount of her regular tape lately too.  She grabbed two more roles of that.  Her excitement growing, she headed back to her desk.

     Sissy was just where she had left him, his bottle only a little further along.  “Stand up,” she told him.  “You can drink that for a few minutes standing up.”

     As soon as he was standing, she grabbed the wide clear packing tape and pulled some out.  She fished her scissors out of her desk and cut it off.  She pulled that piece of tape through the wide clip of the bow.  Then she knelt down in front of him and pressed the bow onto the front of his pantyhose – right on top of where his silly chastity device would be under all his diapers.  She carefully pressed down on the tape to make sure it stuck.  Oddly, she noticed that his diapers felt thicker today.  She realized that they looked thicker too.  “How come your diapers feel so much thicker today?” she asked.

     Chad almost replied without curtseying, but he remembered just before he opened his mouth.  With Robin still on the floor in front of him, he dropped a little curtsey.  “Mel has me in three diapers now,” he replied.  Then he curtseyed again to signify that he was done speaking.

     Robin nearly laughed.  “They look awfully bulky.”

     Chad had to curtsey again.  “They are!  Of course it’s also because I’m so wet.”  Curtsey.

     Robin only chuckled as she pulled more of the packing tape out and cut it off.  She stuck piece after piece over that part of him to secure the bow to his front side as firmly as possible.  She realized she was probably ruining his pantyhose, but she didn’t care in the least.

     Finally she stood back and surveyed her handiwork.  Beautiful!  She laughed to herself as she pointed back down at the floor, telling him to sit down again till he finished his bottle. 

     Chad sank back down, totally aware of the big bow now stuck to his front side.  It certainly didn’t cover up the fact that he wasn’t wearing his skirt!  In fact, it drew attention to him down there.  He looked down for a moment as he paused in his drinking.  The streamers were hanging down and were draped on the floor.  He had a bad feeling about those streamers!  He tried to put the bow out of his mind as he went back to finishing his bottle.  How the heck was he supposed to try to hold back if they kept pushing bottles at him to drink?

     When he finished his bottle, Robin sent him back to his own desk to work again.  But as he moved, he felt the faint tickling of the streamers hanging down, tickling the front of his legs – almost down to his knees.  There was nobody around - but he still felt embarrassed by it!

     Mel tried to figure out what she needed to look at amid the impossible stack of paperwork, but it was so daunting a task that her mind was having trouble sticking to it.  With a small sigh of resignation, she gave up for a while and sat back at her desk.  Her mind turned to Sissy instead.  What was he doing now?  Or maybe she should be wondering what Robin had him doing?  She’d give anything to actually be there in person to see some of the things she made him do. 

     And speaking of things he was made to do…  She opened up an email to Robin and typed away for a while.  Then she added a few other items and clicked the send button.  With the email sent, she needed something else to think about.  Ray popped into her mind first.  But thinking about Ray immediately triggered thoughts about Derek.  Had Derek been so turned off by Sissy on Sunday that he wouldn’t call on her again?  She sincerely hoped not!  Besides, since Derek now knew all about Sissy, she needed to keep a close eye on that situation too.

     With a groan, she got up and went back to sorting through paperwork.  Ugh!

     Robin saw the email come in from Mel.  She opened it and noticed that there were a bunch of pictures attached, but not put in the body of the email.  She read what Mel had to say first.  It was quite a long email, and she was surprised that it was simply one she would have categorized as a “chatty” email.  The whole email was Mel passing along stories about what had happened with Sissy all weekend.  Much of it she found more interesting than she wanted to admit.  But the one big surprise that stood out was Derek!  That part had nearly dropped her through the floor! 

     When she was done reading, she opened up picture after picture to look at them.  The first pictures were of him at some club.  The club appeared to be very crowded with all women, but Mel had mentioned in her email that it was a lesbian bar.  Most of the pictures though were close ups of the way Sissy had been displayed all night long – on stage!  That would have been hard to believe if she didn’t have the proof right in front of her.  Pictures of him drinking his bottle.  Pictures of him sitting on the front of the stage being fed baby food by some strange woman.  And a picture of many women crowding all around him.  She couldn’t quite make out much in that picture other than that some of the women were looking intently at where his diaper would be and some of the others were holding his arms out to the side – to have a good look at his nails?  Maybe. 

     The last picture in the batch was of Sissy at the mall, in a very juvenile looking outfit.  She could actually see the bottom of his diapers sticking down below the ridiculously short skirt he was wearing.  She stared at the picture.  See, now if he came to work like that every day, then she’d have no problem always seeing him as a sissy instead of a normal person.  Or better yet, the ruffled dress that Mel had described, that she had taken him grocery shopping in.  Yes, now that would be really interesting!  That thought triggered something else that she had found out about last week – the trip he had taken to the gym.  She was sure she had heard about a different little girl dress there.  If only he could get away with wearing something like those outfits here at work!  But if he did, then it was all too likely someone would find out about what she was doing with him and she’d probably be fired for sure!  Wishful thinking, but fun.

     She clicked the button to type a reply to Mel’s email.  First she told Mel about where Sissy was currently wearing the bow.  She also told her what she planned on doing with it later.  Then she thanked Mel for what she had sent her.  Finally, she added a bit of her lamentation over the fact that it would be impossible to send Sissy to work in any of the outfits she had described, mostly because it would be all too possible for others to find out what she herself was doing with him. 

     With the email sent, she glanced quickly at the clock.  Lunchtime wasn’t far off.  Which meant…  “Sissy!  Get over here!”  She didn’t have to wait long for Sissy to arrive.  The bow attached to the front of his pantyhose absolutely begged her notice and attention.  She reached down and pulled on it lightly.  It still seemed to be stuck fairly well.  With a giggle, she pulled another bottle out of his diaper bag and handed it to him. 

     Chad was silently screaming as he sank back down to the floor with this latest bottle.  He was particularly agitated because he had yet to even notice he was peeing this morning before it was coming out!  And Robin was purposely making things worse!  He counted on these weekdays away from Mel’s time limits to regain and rebuild his control.  But with too much to drink… he didn’t know what he was going to do.

     Chad had to hurry to finish the bottle before lunchtime arrived.  When he did, Robin took it and stuck it back in his diaper bag while he stood up from the floor.  “I counted six bottles in your bag when you got here this morning,” Robin told him.  “After lunch, I expect to see six full bottles again.  And this time, don’t be late about it!”

     Chad well remembered the problem he had faced in the ladies room last Friday when he tried to refill the bottles.  He would have to come up with a better solution today.  “He curtseyed.  “Can I have my skirt now?”  And he curtseyed again.

     Robin handed him the skirt and watched as he started to reach to pull the bow off of his front side.  “Don’t touch that!” she ordered.  “Leave it right there!  Besides, I’m sure that Cassie will enjoy seeing it on you.”

     Leave it?  She was serious?  Unfortunately, he knew she was.  He pulled his skirt on and zipped it up.  He had chosen a somewhat full skirt this morning because of the extra diapers he was wearing, but he could still see a little bump from the bow underneath.  From his angle, he couldn’t tell if the ribbons hanging down showed below it or not.  But it was just something else he would have to worry about – not that he could do anything about it.  He curtseyed again, grabbed his diaper bag, and left for lunch.

     Robin giggled.  She could just see a tiny bit of the colorful ribbons peeking out below his skirt.  The bump in front was slightly noticeable too.  But the funniest thing she saw was as he was walking away.  His diapers had gotten so full that he was waddling very noticeably!  She was guessing that the extra diaper he was wearing was responsible for his more noticeable waddle.  The idiot!  Well, he deserved it!