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!”