The Bet - Chapter 52 (Monday – week 8 part 5 of 8)

The Bet

by Karen Singer

Chapter 52 (Monday – week 8 part 5 of 8)

     Chad peered intently at his computer screen as he worked.  As so often happened when he was concentrating on something, he lost total track of everything around him.  The only thing that existed for him was the task he was working on.  He typed a bit more, then he clicked the save button.  Then he started testing what he had created.  His spirit soared briefly as it worked – perfectly. 

     He went back to his list of things he had to do, and discovered that he had already accomplished everything.  He needed Robin to let him do more now.  But first, since everything seemed to be quiet…  He opened his spreadsheet for tracking the bet.  He found today’s date and noticed that there were only eleven days left before his testing would start.  Still eleven days, but today it didn’t sound like all that much.  He briefly wondered what he would do after he had won the bet.  How would he come to work?  Would everyone accept him again?  Not wanting to dwell on depressing matters, he put that out of his mind.  He looked at the column were he needed to fill in how long he had held back.  But last Friday things had been so weird that he couldn’t remember how long – or if he had ever managed to get a decent timing. 

     That thought led him to thinking about today.  When he filled out the sheet tomorrow, what would he put down under today’s column?  He had nothing to put there yet, nothing at all.  With a groan, he closed the spreadsheet again without making any entry for last Friday.  What would he put down tomorrow?

     It was only as he sat there brooding about it that he realized he was peeing again – he thought anyway.  The feeling was so slight that sometimes it was hard to tell.  He knew his diapers were certainly very wet and heavy.  And he didn’t recall noticing that he had been peeing all that often.  Of course the extra bottles Robin was making him drink weren’t helping any.

     He had to fight back… somehow.  Somehow he had to regain his muscle control, despite all the liquids being pumped into his system.  With a conscious effort, he tried to tighten all his sphincter muscles.  But nothing happened at first. He had to work to even find those muscles, as if his brain had forgotten how to contact them.  But eventually, he felt his muscles give a tiny squeeze.  He tried again.  Now that his body had found the muscles again, it was much easier this time and he was able to hold them tight for a few seconds. 

     He relaxed again before giving it one more go.  He counted to ten while he held them as tightly as he possibly could.  Then he let go.  Definitely better.  He had made ten seconds like that, could he make fifteen?  Allowing himself to rest for a few seconds more, he then tightened everything as hard as he could again and started counting the seconds.  But his body was already tired from his previous exercise so that by the time he reached ten seconds he was struggling.  He gave up at fourteen seconds.  Close, but not quite.  Next time he would manage it for sure.  He just needed a little more rest first.

     Feeling a bit better about things, he turned his mind back to the tasks he needed to be doing… and remembered he didn’t have any.  Did he dare ask Robin about it?  He would be off all next week, and he knew he had to make sure he got as much done as possible before then.  Chancing it, he got up from his seat.  He paused before leaving his cubicle to try tightening his muscles one more time.  Sixteen seconds!  Next time he would make twenty or more, he was sure of it!  Or maybe he was simply trying to tighten them too much?  Holding them that tight wasn’t exactly normal.  Next time, he decided he would go a little easier with it.

     He headed for Robin’s cubicle.

     Robin was hard at work when she was interrupted by the sound of his high heels entering behind her.  She turned around, annoyed at the distraction.  “What now?” she asked.

     Chad curtseyed.  “I finished everything you needed me to do.  I just wanted to check to see if you were ready for me to do anything else yet.”  He curtseyed again.

     Robin rolled her eyes.  He was finished already.  That was quick.  Sort of.  But she was stuck on figuring things out for her part still so she wasn’t ready to move on yet.  But since he was finished…  She glanced at the clock it was just over an hour since they got back from lunch and she had given him a bottle to drink.  “Grab another bottle since you’re done.  You can celebrate by sitting there and drinking it.”  With him taken care of for the time being, she turned and went back to her work.

     Mel ran her hand over the expensive pin-striped fabric of the suit she was wearing – or what would eventually be a suit.  There were a lot of custom alterations that had to be made first.  Both the skirt and the jacket were full of pins and chalk marks.  The material was certainly right, but she could only take it on faith that the finished suit would be what she needed.  But Lilly had never done her wrong yet… her or her mother.  Two suits.  One dark gray, the other dark blue.  Just what the job required.

      “That should be it, for now,” Lilly finally declared.  “They should be ready for a final fitting on Wednesday.”

     Mel nodded.  “Thanks Lilly.  Just let me know.”  She went back to the changing room and changed into the clothes she had arrived in.  As she was grabbing her purse to leave, her phone rang.  She had ignored it several times earlier, but this time she picked it up.  “Hello?”

      “Mel,” Derek’s voice replied.  “You’re a hard one to reach sometimes.”

     Mel sighed.  “That’s usually the case with my line of work.  How is your day going, because so far mine has been… lousy.”

      “Lousy?  Need to talk about it?”

      “I’m not sure,” she replied.  “It’s mostly just business stuff.”

      “Well, we can stop somewhere for a pizza later and you can tell me all about it if you like.”

     Mel figured that the good news was that Derek wasn’t totally put off by what was going on with Sissy… yet.  “Derek, you know I can’t do anything without Sissy for a while.  This bet is too close to being over with.”

      “You mean you won’t get away for even just a few hours?”

     Mel sighed.  “As much as I’d like to, right now I’ve got way too much work to do, and I’ve been pretty much trying to avoid it all afternoon.”

      “That bad, huh?”

      “You wouldn’t believe!”

      “Sure you don’t want to talk about it tonight?”

     Mel considered it again.  “No.  Not tonight.  But…  Just not tonight,” she repeated.  “It’s just something new that’s come up, that’s all.  Business, you know.  And somehow I’ve got to get a handle on it.”   

      “I understand,” Derek replied with a hint of disappointment in his voice.  “Maybe tomorrow?”

      “Yeah, maybe tomorrow.”  Mel replied.  Then she added, “Hopefully tomorrow!”  She did want to see him again – especially since he now knew about Sissy, and he wasn’t scared off! 

     As soon as she had hung up her phone and put it away, she sighed.  She couldn’t put it off any longer.  She had to get back to the office and dive in once again.  Somehow she had to make sense out of the mountains of paperwork attached to the merger agreement.

     Chad stood up, set the now empty baby bottle on Robin’s desk, and curtseyed.  The sound of him moving had caught her attention and she turned around to look.  “I’ve finished now,” he said.  “Is there something else I can help with on this project?”  He paused a moment to wait for a reply, but she didn’t move till he curtseyed again to signify that he was done talking. 

      “Not yet,” Robin replied, frustrated that her own work was currently going so slowly. But art work was often like that.  Sometimes the little details took a long time.  But since she knew he was so childish now and needed to be kept occupied…  She glanced at her clock, it was earlier than she wanted to do this, but…  “Get undressed again,” she told him.  “Down to just your diapers and plastic pants!”

     Chad wasn’t totally surprised, but he wasn’t happy about it either.  Carefully, he started to pull his pantyhose off.

      “Wait a minute!” Robin stopped him suddenly.  “Pull them back up again.”

     Chad had no problem doing that, he just didn’t know why.  He saw Robin fishing in her big bag for a moment, and then she pulled out her cell phone.  “Just stand right there!” she told him as she aimed the camera in the phone at him.  A moment later, he heard a clicking sound from her phone as she took the picture.

      “Okay, now you can get undressed.”

     Carefully, Chad removed his pantyhose with the bow still attached. 

      “Give me those,” Robin said before he could go any further.  She peeled the tape and the bow off of the pantyhose while he removed the rest of his clothes.  She was happy to note that the tape hadn’t damaged the thicker material at the panty portion of his hose at all.  Not that she was really worried about it. 

     Once Chad was down to just his diapers and plastic panties again, Robin was about to start dressing him again, but she realized that he was missing one very important ingredient.  “Where’s your pacifier?” she asked.

      “It’s…”  Chad stopped himself and curtseyed.  “It’s in my purse.”  He curtseyed again.

      “Well hurry up and get it!” she said.  “And I can see that we need to still work on you remembering to curtsey all the time!”

     Chad curtseyed and turned toward the entrance to her cubicle.  Since he was only wearing his diapers, he carefully looked up and down the hallway before rushing over to his own cubicle.  He fished his pacifier out of his purse and stuck it straight into his mouth before checking the hallway one more time and hurrying back.

     When he returned, Robin gave him the same Baby t-shirt she had given him last week to wear.  And like last week, she had to tie the bottom of it up in a knot so that his diapers would be exposed.  Then, once again, she tied the bib around his neck.  She still hated that it covered up the word “Baby” on the shirt, but there was little she could do about that.  She knew it was there.  But a moment later, she removed the bib again.  She pointed at the floor.  “Sit!” she commanded.  And as soon as he was down, she took several more pictures of him with her phone.  Pictures showing the t-shirt with the word “Baby” and the arrow pointing down toward his diapers.

     Then she tied the bib back around his neck – and took more pictures.  “You’re not drooling!” she told him. 

     Ugh!  Chad wasn’t happy at all that she wanted him to drool again – like an idiot.  But a minute later, his chin was damp with slobber as he sat on the floor and let her take picture after picture with her phone.

     Robin laughed a bit to herself as she took more pictures, including close-ups of the drool dripping down off his chin.  Since Mel had been so kind as to send her all the pictures earlier, she figured she would return the kindness with pictures of her own. Especially since Mel had said she wished she could see what she did with him.  But first, she had to take care of him.  She had to keep him occupied.  She reached into her desk drawer and pulled out the big envelope that held his paper dolls.  She pulled some of it out and gave it to him.  Just like a child, you had to keep them busy.  She snapped a few more pictures of him playing with the dolls on the floor.

     Her eyes noticed the big colorful bow she had just removed from the front of his pantyhose.  Picking it up, she placed it directly on top of his head.  Then she tried holding it to the side of his head instead, then at the back of his head.  She opened the clip and fastened it to his hair directly on top where it would be most prominent.  And of course, she took more pictures. 

     Finally, she downloaded all the pictures to her computer and started on the email for Mel.  She attached a lot of the pictures she had taken.  When the email was finally sent, she briefly checked on Sissy again, then turned and went back to work.  But as she was getting busy again, something inside of her felt very satisfied about what she had just done. 

The Bet - Chapter 52 (Monday – week 8 part 4 of 8)

The Bet

by Karen Singer

Chapter 52 (Monday – week 8 part 4 of 8)

     Cindy wasn’t totally happy.  Cassie had told her in no uncertain terms that she couldn’t change Sissy at all this week.  She had said that she might be able to do something with him later, just not this week.  She had asked why, but Cassie wouldn’t give her any kind of decent reason. 

     She noticed Sissy’s car pulling into the parking lot.  She saw him getting his diaper bag out and heading towards the door.  She saw him opening the door and come inside… and before she could say anything to him, she saw him curtsey to her.  She giggled despite herself as he did it.  But as he curtseyed… what were the odd bits of color below his skirt?  They certainly didn’t look like part of the skirt.  Noticing them completely disrupted her earlier train of thought.  She had to know what she had seen!  But before she could open her mouth to ask, she noticed something else – there was this odd little bulge under his skirt.  Not much, but enough that she could see it.  And it was right where a man’s…

     Chad had curtseyed immediately, not only because he knew he would have to, but he did it in hopes that maybe the receptionist would get Cassie quicker.  “Will you get Cassie for me please?” he asked.

     But Cindy barely heard him.  She was too intent on staring at the front of his skirt and trying to figure things out.  That odd little bulge… and yes, the odd bits of color!  “What’s showing under your skirt?” she asked.

     Chad glanced down at his skirt.  Damn!  She could see!  “Um…  It’s just…”

      “Let me see!” Cindy ordered before he could get any further. 

     Chad knew he would have no choice.  He slowly lifted his skirt, revealing the big bow with the streamers that Robin had taped onto him.  He held his skirt up for a moment as Cindy put her hand over her mouth and laughed.  She was still laughing when he lowered his skirt again and tried to tug it down further, which it wouldn’t do.  “Can you please get Cassie for me now?” he asked again.

     Still staring at him with her hand over her mouth, Cindy slowly moved from behind the counter to go look for Cassie.

     Chad counted himself as lucky because she hadn’t noticed his fingernails.  He also considered himself lucky when Cassie came up front and he only had to curtsey and greet her.  She didn’t ask to see the big bow.  But then, she was going to see it all in a few minutes anyway.  He followed her back through the gym of exercising women, back to the little room where she changed him every day. 

     Since Cassie didn’t ask about the bow when they got to the room, and because he knew she’d see it in a moment anyway… and just to get it over with, Chad got Cassie’s attention by saying, “Um…”  Cassie did turn from pulling things out of his diaper bag to look though.  Chad lifted his skirt and showed her the bow.

     Cassie smiled.  “How sweet!  And in just the right place too.  Robin?” she asked.

     Chad only nodded. 

      “It looks like you better be careful taking those pantyhose off then.  You wouldn’t want to mess it up.”

     Getting his pantyhose off wasn’t much of a problem.  But he was careful about doing anything that might make the bow come loose.  He could just see Robin trying to attach it some other way that might be worse!  A few minutes later, he was laying down drinking yet another baby bottle of Mel’s “wonderful” tea.

      “It looks like the three diapers are working much better for you,” Cassie noted as she peeled back the layers.”

      “Only because Robin won’t let me go very long without making me drink something too.” Chad replied as he took the nipple briefly out of his mouth.”

      “So she’s picking up now where Mel leaves off?”

      “Something like that,” Chad admitted.

     Cassie was tempted to say more – including about the bow that was attached to his pantyhose, but she was ready to move on with changing him.  “Okay, roll over,” she said instead.  She cleaned his backside, then applied some of the baby lotion and rubbed it in carefully all over.  Knowing what he really wanted from her though, she applied a bit more of the lotion in just the right spot, and inserted her finger up into him.  She was rewarded by his immediate reaction of pleasure.  She had always been fascinated by how he could derive such pleasure from being penetrated in his back end.  She was sure that the fact that any pleasure to his front side was denied him had a big role to play in it, but still, it never ceased to surprise her how he reacted to it.  She soon grabbed her ribbed toy and was holding on tightly as he pumped himself desperately against it.

     Every inch of Chad’s attention was on his backside and the feelings Cassie’s toy continually gave him.  But what he wanted was sexual release.  He had achieved it once, he thought, but that had only been with Mel and her strap-on.  Despite how often Cassie worked with him, he had yet to achieve that same orgasm here with her.  But he desperately tried to get there.  He tried as hard as he could.  But as usual, eventually the feelings did nothing more for him.  He couldn’t get there.  As much as he wanted it, the goal was impossible again.  Had it really happened that once?  He was starting to question it.

     Cassie removed her toy, and while he was still in the right position, she made a bit of a show of taking one of the suppositories out of the jar and pretending to put it up into him.  He still didn’t know!  She wasn’t sure if she should be amazed at that or not.  But right now, that was part of her job, to keep him from knowing it.

     A minute later, she was pulling the fresh diapers that she had laid out under him, up between his legs.  Diapers that were already a little bit wet since he had no control anymore when she was working with him.  As she taped the diapers in place, she had to wonder if he ever had dry diapers on anymore.

     Chad got dressed again.  He had to be extra careful to not tear the bow loose from his pantyhose as he pulled them up.  As soon as the hose were in place, he pressed down on all the tape again to make sure it was all stuck firmly.  He breathed a small sigh of relief as everything seemed to be secure.  He slipped his shoes on as he grabbed his skirt, but before he could get it all the way on, Cassie stopped him.

      “Wait a minute,” Cassie said.  “Give me that.”

     Chad didn’t know why, but he pulled his skirt back off again and handed it to her.  Cassie stood up and picked up his diaper bag and handed it to him.  But she kept his skirt.  “Okay, let’s go.”

     Chad was dumbfounded!  She expected him to…  But Cassie was already gone – with his skirt!  He had no choice but to follow her out through the gym full of exercising women.  He knew his face had to be very red before he got very far.  He never stopped walking, but many of the women stopped what they were doing to stare at him.  He heard more than a few chuckles, more than a few silly comments about his colorful bow.  By the time he got all the way through the long room, it was much quieter than when he started.  And there was Cassie, waiting for him with his skirt still in her hand.  But as soon as he got near her, she turned and kept going with it.  “Let’s go this way today,” she said without looking back.

     Since she had his skirt, Chad had no choice but to follow her.  She finally pushed open one of the doors off to the side of the gym and went through.  The door swung shut before Chad could get there.  He opened the door and stopped cold!  It was one of the rooms where they held some of their exercise classes – and class was currently in session!  And there was Cassie, his skirt still in her hands, up front talking with the instructor. 

     Even though Chad had stopped before actually entering the room, he had caught the attention of some of the women close to the door.  Their squeals of delighted laughter rang out and quickly built as more and more of the women saw him.  He was about to step back away from the door, but Cassie was motioning for him to come in. 

     Feeling so sheepish he couldn’t believe it, he slowly made his way toward the front of the room.  All eyes were on him.  When he got to the front, Cassie finally handed him his skirt back.  In front of all those women, he put it back on and zipped it up.  The oddness of what he had just done didn’t escape him – a man putting on a skirt in front of a bunch of women.

     Cassie bent down a little and pointed to the bottom of his skirt.  “See the ribbons underneath?” she said to the instructor. 

     The woman didn’t have to bend down.  “They just barely show,” she replied, “but I can see them.  Kind of like a little tease for what’s under there.”

     Cassie stared at Sissy for a moment more.  “See you tomorrow,” she said to him with a very amused smile on her face. 

     Chad immediately turned to go and started to hurry out.

      “Aren’t you forgetting something?” Cassie’s voice asked, stopping him in his tracks.

     Chad couldn’t think of anything.  He had his diaper bag, he had his purse… he finally had his skirt again.  He looked at her quizzically.

      “How do you say goodbye to all these nice ladies?” Cassie asked.

     Ugh!  Chad had to curtsey for them all, which raised more than a few chuckles.  He said a quick goodbye, then he hurried out of there at almost a run!  What had gotten into Cassie today?

      “So let me get this straight,” Gloria said as Mel sipped at her coffee.  “They asked you to work on this deal, but you don’t really know what you’re supposed to be doing?”

      “That’s pretty much it in a nutshell.” Mel replied.  “I asked, but all they said was that I needed to make sure the agreement was kosher and that I didn’t see any mistakes.”

      “Well, that sounds fairly clear to me.”

      “Yeah, but they’re all doing that.  Except that, from what little I’ve seen, they’ve all got it easier in that they’re each responsible for only a small part of it, just their area of concern.  As far as I can tell, I have to look through all of it.”

      “And you don’t think it’s fair?”

      “Not in the time I’ve got.”

      “Don’t worry honey, if I know you, you’ll do great.”

     Mel shook her head.  “I don’t know this time.  I mean, all those men…  And they were all major big time lawyers.  It was more than a bit intimidating just to be in the same room with them!”  She shook her head, then smiled and looked up at Gloria.  “You wouldn’t believe how pretty a man can look in an overly expensive, perfectly tailored suit!  I could have stared at some of them all day.”

      “Damn I should have gone to law school,” Gloria said.  “I get to see plenty of executive types, but when I see them, they’re all frazzled and neurotic!  Not exactly what you get.”

      “Hey, this is a first for me too,” Mel replied.

      “Yeah, but you said you knew a few of them from before.”

      “A few,” Mel admitted.  “But I didn’t know them well.”

      “So what are you going to do?”

     Mel sighed.  “Well…  For starters…  I don’t think I’m going back to my office after lunch.”

      “You can’t run away and you know it!”

      “I’m not running away.  I’m going shopping!  I’m not going to look that out of place again!  If they want to show off expensive clothes like that, then so can I!”

      “Go get em girl!  Now, let’s get back to this Derek thing.  What the heck happened?”

     Chad hurried from his car back to his office.  He was carrying his purse, his diaper bag, and a large bottle of water he had bought at a convenience store.  He had hurried as fast as he could through lunch so that hopefully, Robin wouldn’t be back yet.  He was also hoping he could get back to the safety of his desk before most other people got back too so there would be less chance of anyone noticing the odd bits of color below his skirt.  Before stopping at his desk, he checked Robin’s cubicle – empty.  Good! 

     He set everything down on his desk and pulled out all the empty baby bottles from his diaper bag and one by one, carefully filled them from the large bottle of water.  The big bottle was less than half full by the time he finished.  Did he really drink all that this morning?  Dumb question.  Sometimes he drank more than that – a lot more! 

     He was just finishing when Robin walked by.  “My place,” Robin said, barely pausing on her way to her desk.

     Chad hurried around to her cubicle, but when he got there he didn’t even get a chance to curtsey before she asked, “Where’s your bag?”

     Chad dropped a very quick small curtsey before going back for his diaper bag.  When he returned she took it from him and set it on her desk.  “Why is that skirt still on?” she asked.

     Chad suspected it was coming since she had left the bow on him earlier, so he wasn’t surprised.  He removed his skirt again and she took it from him.  She opened his diaper bag and checked all the bottles, then she pulled one out and handed it to him.  You may as well have another one now,” she said before turning away from him to go back to work. 

     Dejectedly, Chad sank down to the floor with another bottle.  How the heck was he supposed to hold back today?  Every time he turned around she was handing him another bottle to drink!

     Mel parked her car and stared up at the store in front of her.  She hadn’t been here in a long time.  The last time had been with… her mother.  She had often been here before that.  The store represented a world she had pretty much ignored for the last few years – the world of the wealthy.  It wasn’t that she disliked anyone she would meet.  On the contrary, some of them were incredibly nice.  But she had always felt determined to make her own way, to not be judged for what she did just because of her family’s money.  She was determined to succeed on her own merit and her own merit alone!

     But now her own merit had run crashing right back to the world she had started from.  Well, if she had reached that point, and she knew she hadn’t really, then she would have to be accepted by the people in that world.  And acceptance meant certain… compliances.

     She got out of her car and walked up to the door.  Her mind was filled with many images of her mother and her coming in here so many times in the past.  Now she felt alone and out of place.  Her mother wouldn’t be coming with her anymore.

     She didn’t get ten steps inside the door before she saw the look of surprise on the face of one of the older saleswomen that she remembered from so many trips in the past.

      “Melissa?  Is that you?”

      “Hi Lilly,” Mel replied, trying to sound casual.

      “Look at you!  You’re all grown up!  And you’re beautiful darling!”

     Mel smiled in spite of herself.  “Thanks Lilly.  You’re looking just as good as ever.”

      “Oh bull!  I’m getting old and you know it!  I was so sorry to hear about your mother and father.  So very sorry.  We all were.”

      “Thanks, Lilly.  I appreciate it.  I still miss them.”

      “I’m sure you do dear.  Now, what can this old bag of bones do for you today?  Oh!  You know what?  I have the most darling tea dress that would look absolutely divine on you!”

     Mel shook her head.  “Not this time.  I need something different today.”

      “Well, whatever it is, you know we’ve got it.”

      “That’s why I came here.  I’ve been… drafted to help with a deal that Feinbaum is brokering.  I need to fit in with all his suits.  Something that helps me look more… dominant… without the leather and whips and chains.  Although maybe that wouldn’t be a bad idea either.”

     Lilly laughed.  “With Feinbaum’s group, most of them would probably love it!  But I know exactly what you need.”  She was already turning as she added, “Right this way!”

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!

The Bet - Chapter 52 (Monday – week 8 part 2 of 8)

The Bet

by Karen Singer

Chapter 52 (Monday – week 8 part 2 of 8)

     The minute Mel walked through the door to her office, she was accosted by Andrea.  “Harry Feinbaum has called twice for you already.  He wants you to call him back immediately!”

     Mel stopped in shock.  “Harry Feinbaum?  Old Man Feinbaum?  Not Dick?”

     Andrea nodded.  “Harry!”

      “Damn!  As if my day hasn’t started off bad enough already.  Okay, thanks Andrea.  I’ll call him right away.”  As Mel trudged back to her office, her mind continually tried to figure out who in her client list would have attracted the attention of Harry Feinbaum!  She dumped her purse and laptop bag on her desk, looked up the number of what was arguably the biggest and most prestigious law firm in that part of the country, and dialed.  She spoke briefly to a receptionist before being put on hold till “Old Man” Feinbaum could come to the phone.  While she was waiting, she pulled her laptop out and turned it on. 

     She didn’t have to wait very long till Harry Feinbaum himself finally answered her call.  “Mel!  How have you been?”

      “Fine, Mr. Feinbaum.  How about yourself?”

      “Doing fine, Mel.  Just fine.”

      “And Dick… and his family?” she asked.

      “All fine too.  The kids are growing too fast though.  But it’s nice to have grandkids around once in a while.  How about you?  Any kids yet?”

      “No, Mr. Feinbaum.  I’m not married yet.”

      “Shame,” Harry replied.  “Family is important!  Any prospects though?”

     Mel really wished they could get past this friendly bit.  “Um…  Let’s just say I’m working on things.”

      “Well, good luck with it.  Like I said, family is important.  Your father knew that.  He was a good man, good lawyer too.  I miss him.”

      “So do I Mr. Feinbaum.  So do I.  Um… not to cut this short, but what can I do for you?”

      “Mel, are you familiar with Sunshine Corporation and Green Growers United?”

      “I’ve heard of them.  But I couldn’t tell you much about them.  I know they’re big though.”

      “Very big!” Harry replied.  “Sunshine is buying Green Growers.”

     She knew that mergers of this type were the main staple of what Feinbaum’s firm handled.  “So?  What does this have to do with me?  As far as I know, I don’t represent anyone that works for either group.”

     Harry was confused.  “Represent?”  But his confusion only lasted a moment.  “No Mel, you don’t understand.  We’re representing Green Growers in this.  We’re not interested in any individuals not on the boards of directors.”

      “So let me get this straight, you’re not pressing any kind of action against one of my clients?”

      “Action?  No, of course not!”

     Mel was relieved.  “Then what can I do for you?”

      “I’m looking for your help.”

      “My help?  With the merger?”

      “Exactly!  Our contract man quit very suddenly last night, leaving us in the lurch so to speak.  Your father always said you were great with contracts, and Dick threw your name out as a possible alternative.”

      “But Mr. Feinbaum, I’m sure your firm has any number of contract specialists right there that you can choose from.”

      “We do, but I’d like somebody fresh on this one.  Mel, I don’t have to tell you what the fees would be for something like this.  This merger is worth billions!”

     Billions!  But that was it in a nutshell.  That was the real reason he was calling in someone from the outside.  He needed a patsy… a fall guy... just in case something went wrong.  And if it did, her reputation as a lawyer would be pretty much ruined.  “And when is this thing supposed to take place?” Mel asked.

      “We’re to the point where we’re sure we can finalize it the beginning of next week.”

      “Next week!  And you’re calling me in now?  That’s ridiculous!”

      “Sorry, Mel.  Like I said, our guy quit quite suddenly last night.”

      “Ugh!” Mel grunted.  “There can’t be much left to do.”

      “Not a lot.  Just a few pesky little details.  Can you be in our offices by ten?”

      “Today?”

      “Of course.  You need to get up to speed fast.”

     That was an understatement.  “But I’ve got clients!”

      “I’m sure it wouldn’t be the first time you had to rearrange your schedule.”

     Ugh!  If it had been anyone else, she would have declined immediately.  But the first thing her daddy had taught her when she came to work here, was that you “never” say no to Old Man Feinbaum!  “Okay,” she replied reluctantly.  “I’ll be there.” 

     She hung up the phone.  Damn!  And next week she had cleared her schedule just so she could devote it all to Sissy and winning the bet!  A distraction like this was the last thing she needed!  And what a distraction it was.  Huge! 

     She picked up the phone again and punched Andrea’s number.  “Andrea, better clear the decks.  We got trouble in River City!”

     Chad had been working for almost an hour when he heard Robin calling him.  “Sissy.  Get over here.”

     Quickly, Chad got up and went over to her cubicle where he curtseyed.  “You called?”  He curtseyed again.

      “Of course I called!” Robin replied.  She looked at him.  Not wearing the skirt helped a lot.  He looked much more stupid without it.  She pulled one of the baby bottles out of his diaper bag and handed it to him.  Then she pointed at the floor.  “Drink!”  It was all she needed to say.  As he was getting down on the floor, her eyes happened to glance at the hair bow.  She was tempted to put it in his hair right then.  It would be something she could get away with.  But she decided against it… for now.

     Chad wasn’t happy about having to drink another bottle already.  And this was his fifth one of the morning – already.  He had so much liquid in his system still that he hadn’t even started to try to hold back.  And now Robin was making him drink another one?  Between her and Mel they were making things impossible for him!

     He suddenly realized that he had been peeing again.  He had almost missed it because he was too preoccupied with thinking about other things.  He knew he wasn’t always noticing any more when he did pee, especially when his diapers were already wet, which was ninety nine percent of the time.  Peeing automatically was becoming way too much of a habit!  He decided then and there that he would have to try to hold back more now, despite how much liquid was still in his system.  The only problem was, that he had just finished peeing, so he didn’t have any need to go again, and no need to hold back just yet.  He only hoped he would notice before the next time he had to pee.

     When he finished his bottle, Robin sent him straight back to work again – still without his skirt.

     Mel was lost… mentally.  She was sitting in the richly appointed meeting room at Feinbaum’s offices along with a large team of obviously powerful lawyers.  All men.  All wearing beautifully tailored expensive suits.  She felt like a fish out of water – totally!  She had a mountain of paperwork on the table in front of her.  Two bigger mountains on the floor behind her.  How was she supposed to get caught up before the beginning of next week?

     Harry Feinbaum was sitting in the chair at the head of the table, but it was his son Dick who seemed to be running the show.  “And that’s about it,” Dick Feinbaum finished up.  “Slatter said he’d have the updated agreement to us no later than Wednesday, so till then, you all know what you have to do.  Let’s get to it.”

     With that, the meeting ended and everyone got up.  The very handsome, and not to mention very married, Dick Feinbaum stayed behind and walked over to Mel.  “Glad to have you in on this,” he said as he shook Mel’s hand.  “You can imagine what a surprise it was when our guy suddenly quit last night.  No notice.  Not even any warning.”

      “I can imagine,” Mel replied.  “You can’t imagine how shocked I am to be here.”

     Dick smiled charmingly.  “If your half the lawyer your father claimed, then you’ll do fine,” he replied. 

      “So Richard Slatter is drafting the agreement?  And he’s on the other side?”

      “That’s the story.  You know him?”

      “A little.  Through my father.  The guy’s a legend.  I think he even wrote one of my law books when I was in school.”

     Dick nodded.  “That’s the guy.  At least you know what you’re up against.”

     Mel nodded.  “Yeah.  A legend!”

     Dick laughed.  “This is the big league now.”  He looked at the pile of work Mel had on the table.  “Can I get someone to help you with all that?”

     Mel looked at the mountains of paperwork on the table and also on the floor behind her.  “You better.  In fact, I hope I don’t have to rent a truck to get it all home!” 

      “Just wait right there and I’ll send one of our staff in to get it down to your car for you.”

      “I appreciate it,” Mel replied as she heard the faint sound of her phone buzzing in her purse.  Dick Feinbaum took off as she dug it out.  “Hello?”

      “Where have you been, girl?” Gloria’s voice asked lightheartedly. 

      “Ugh!  Busy!  I’ll tell you about it at lunch.”

      “Good!  Because I want to hear all about your date.”

      “And I want to hear all about yours too.  How did it go by the way?”

     Gloria paused before speaking.  Her voice wasn’t nearly as lighthearted.  “Let’s just say that I was a little too nervous, and he was a lot more handsome in person, so I drank way too much, and… well, since I knew I’d never see him again, I took way too much advantage of the situation.”

      “Huh?  What’s that supposed to mean?”

      “It means I made a total fool of myself and not only threw all caution to the wind, but I went more than a bit wild and tried to make up for all the sex I haven’t had in the last few years!  I was a total slut!”

     Mel was shocked.  “Okay…” she said cautiously.  “This I have to hear all about!”

      “Well, I’ll warn you, it’s going to be very ‘X’ rated!”

     Robin glanced at the clock on her computer.  Break time.  She got up, checked her face and hair, and grabbed Sissy’s skirt.  A moment later she was at his cubicle.  “Break time, Sissy.”

     Chad turned around in his chair just as Robin threw his skirt at him.  He was quick to get it on again and relieved the moment it was in place. 

      “Let’s go,” Robin said as she turned on her heel and led the way.  Quietly, Sissy followed behind her.  The moment they reached the next hallway, Robin paused a moment to let him catch up.  They walked sided by side, but silently, all the way to the break room.   

     Chad was more nervous than ever about being at break today, for several reasons.  Mainly, he was nervous because of his fingernails.  The other reason he was nervous was because of Derek.  Would Derek show up today?  Once they got to the break room, they joined the short line for coffee.  He knew Robin wasn’t going to let him go without any, so he grabbed a cup and filled it.  He held the cup so as to try to hide his sissy fingernails as much as possible.  Maybe nobody would notice.  There were doughnuts in a box beyond the coffee.  He ignored them as he waited for Robin to fill her cup.  He expected Robin to grab one of the doughnuts, but all she did was to look at them – a bit longingly.  Together they headed for the women’s table. 

     As the others arrived and sat down, Chad did his best to keep his hands low and in his lap so his fingernails wouldn’t be noticed.  Every time he lifted his cup to drink, he worried more about someone else seeing them.  Once or twice, he did see a woman staring at his hand as he held his cup to his lips.  Did they see what was on his nails?  Fortunately, they didn’t say anything.

     Robin sat back and relaxed a bit as she talked casually with a few of the women.  Out of the corner of her eye though, she noticed how Sissy was handling trying to hide his nails.  Well, unfortunately for him, that would never do!  She leaned over to whisper quietly to the woman next to her.  “Did you get a good look at Sissy’s nails today?”

     The woman immediately looked around Robin, trying to see better.  “I can’t see them.  They’re in his lap.”

      “Ask him to show you the design on them.” Robin whispered.

      “A design?” the woman replied with interest.  “I’ll bet it’s pretty!  He always has such beautiful nails.”

     It was all Robin could do to not break out laughing.  “Ask him,” she prompted.

     Since there were other conversations taking place around them, the woman leaned across Robin and asked softly.  “Sissy…  Let me see what’s on your nails.”

     Chad nearly had a fit!  His luck had run out and he knew it.  He looked at Robin to see if maybe she could help, but instead of help, she had a very pleased smirk on her face.  She had prompted this!  He just knew it!  Holding his cup in his right hand, he slowly and tremblingly extended his left hand towards the woman.  The woman’s sudden loud gasp of surprise stopped all conversation as everyone looked to see the woman staring at Sissy’s hand.  Quickly, Chad retracted his hand and hid it again.

      “Set your cup down,” Robin told him, “and show everyone what you did to your hands!”

     Chad nearly spilled what was left of his coffee as he set it down on the table.  Trembling more than ever with embarrassment, he held both hands out over the table so everyone could see.  The women practically climbed all over each other to get a good look.  The shocked exclamations and comments were only what he expected.

      “What on earth made you decide to do that to your hands?” One of the women asked.

     Chad looked up at her, totally embarrassed.  “It wasn’t really my idea.”

      “It wasn’t?”

     Chad shook his head.  “No, it was… kind of…”

      “A dare?” someone tried to finish for him.

     He was going to pounce on that one and go along with it, but he caught sight of Robin’s face first.  He shook his head.  “No.  More of a… suggestion.”

      “To do that?  My God!  It has to be awfully embarrassing!”

     Chad nodded.  “It is!”

      “So what made you do it?”

     Chad just shrugged.  “Trying new things I guess.”

     Robin knew that his answer wasn’t exactly the truth, but she liked him taking the responsibility instead of throwing it on someone else – in this case, Mel.

      “I think I’d remove it quick if it was me!” one of the women suggested.  “I mean, any other name would be fine.  A bit juvenile perhaps but still, Sissy isn’t the kind of name that would be best for… you.”

     Chad would like nothing better!  “I would, but… well… I kind of promised I’d leave it,” Chad replied.  It wasn’t quite the truth and he noticed an odd look from Robin after he said it.

      “Whatever for?” another woman asked, totally shocked.  “Do you know what it looks like?”

     Chad finally pulled his hands back and hid them in his lap again.  He nodded sheepishly.  “Yeah.”

      “Say it!” Robin commanded. 

     Chad just looked at her shocked.  Did she really want him to admit what he was?

      “Tell them what you think it looks like!” she said again.

     Unable to look any of them in the eye, he looked down into his lap and said, “It makes it look like I’m a sissy.”

      “Damn straight it does!” One of them exclaimed!

      “And you’re still not going to remove it?” another woman asked.

     Chad looked up briefly, then over at Robin, then back down into his lap while he tried to figure out how to answer that.  “Sometimes… people like me… have to put up with a lot.”

     This time Robin did burst out laughing, although everyone else looked shocked. 

      “I have no doubt about that!” someone replied for all of them.  “But this?”

     Chad just shrugged.  “It’s actually not much worse than some of the other things I’ve been through.”

     The woman shook her head.  “Well, you wanted this life, but if it was me, I’d still get rid of it.”

     Chad only nodded.

     Robin had no doubt though that now there were questions in every woman’s mind.  Questions over whether he was a sissy or not.  Questions that none of them probably had the courage to ask.  But they were questions that they would discuss privately with each other all over the company.