The Bet - Chapter 54 (Wednesday – week 8 Part 8 of 9)

The Bet

By Karen Singer

Chapter 54 (Wednesday – week 8 Part 8 of 9)

     Robin was slowly working through the changes she and Sissy had decided to try in their project.  For once, Sissy wasn’t sitting and playing like a child on her cubicle floor for the remainder of the afternoon.  She needed him working instead.  Especially since he would be gone all next week.  It bothered her a little that the situation meant she couldn’t change the way he was dressed today and see him acting like the child he really was, especially since he looked like such a normal woman again today, but there was work he had to get done and that had to come first.  The most she dared make him do right now was to bring him in every forty minutes or so to drink another baby bottle. 

     She laughed as she remembered the one he had finished right after lunch.  He had finished it and stood back up again.  Then he had curtseyed before he left – and had locked in his curtsey position for a few moments as all the blood suddenly drained from his face.  It had taken her a moment to realize that he had just messed his diapers again.  As far as she could tell, he messed them about the same time every afternoon.  Today might have been a little bit earlier though.  Of course, with all the extra liquids she was forcing into him today, that might be expected. 

     She thought about him sitting on the other side of the wall from her, trying to work with such a mess in his diapers.  But he did that every day… so it was nothing new to him.  Yuck!  The stupid sod deserved what he got, that was for sure.  How could she have ever seen him as anything but what he is – a childish sissy?  Well, she simply hadn’t known before.  In fact, before, she didn’t really know what a sissy was.  She guessed she knew now. 

     She was startled by the ringing of her phone.  Thoughts that something might have happened to her son momentarily hit her as she quickly dug it out of her bag.  “Hello?” she said quickly the moment she could answer it.

      “Hi Robin.  It’s Mel.  Do you have a minute to talk?”

     Relief that it wasn’t anything wrong with her baby washed over her so quickly that she didn’t even notice it.  “Sure,” she replied.  “What’s up?”

      “Well, you know there isn’t much time left in this bet between Sissy and myself,” Mel started, “and since you know what was in his email to me yesterday, you also know how concerned he is about how we’re going to decide this thing if it’s close.”

      “Yeah,” Robin replied.  “I remember.  So what did you decide?”

      “We’re looking for judges to decide for us – if it gets that close.”

      “And you want…  Wait a minute,” Robin said as she got out of her chair.  She walked out of her cubicle and headed down the hall – away from Sissy.  “Okay,” she finally said, “I wanted to get further away from him so that he won’t overhear any of this.”

      “You needn’t have bothered,” Mel replied.  “He knows I was going to ask.”

      “And he wanted me to be one of the judges?” Robin asked, not sure she could believe that.

      “Actually, I’m asking everyone who knows about the bet.  But the only ones we want to judge it will be the ones who are sure they can do it fairly.”

      “What do you mean by fairly?”

      “To judge it honestly… without regard for how they feel about either of us or who they would personally like to see win.”

      “And you’re asking me?”

      “If… you think you can do it fairly.”

     Robin had to think about that for a bit.  “I don’t know,” she finally said.  “I mean…  Let’s just leave it at I don’t know.  I’ll have to think about it and get back to you.  Okay?”

      “Yeah, that’s fine,” Mel replied.  “I need you to be sure... we both need you to be sure.”

      “Yeah, I get that,” Robin said.  But she was further away from Sissy now and alone where she was standing and looking out at the parking lot beyond a section of plate glass wall.  She didn’t feel ready yet to go back to her desk.  And… now that she was talking with Mel, one tiny little thing that had bothered her all day sprang to her mind.  “Mel,” she said quickly before the lawyer could hang up.  “Do you have a minute to talk?”

      “About Sissy?” Mel asked.

      “Of course!” Robin replied.

      “Sure,” Mel agreed.  Anything having to do with Sissy was a primary concern for her.

     But Robin wasn’t sure where to start.  “It’s just that…  You mentioned yesterday that you had some other outfits you had been thinking of putting him in.”

      “Yes…” Mel agreed cautiously.  “But we decided that there was no way we could do that with him at work.”

      “Yeah, I know.  And that’s still the problem.  But…  I guess, I was just curious about seeing some of his other outfits – especially the ones where he wouldn’t look like such a… I don’t know… a normal woman I guess!  I mean, that’s mostly the reason I make him wear my ‘Baby’ t-shirt and have him play on the floor like a child – so I don’t have to see him as a “normal” woman.  No… so I don’t have to see him as a normal person – which he’s not!  Not at all!”

      “I… think I understand,” Mel replied.  “If you don’t want him to look… normal… then I’m willing to send him to work dressed in something else… something you might find more interesting.  But the problem still remains, how could we make it work?  Would it matter if everyone there saw him that way?”

      “I guess that depends,” Robin replied.  “Mostly I guess it would depend on how it might affect me.  I don’t want to lose my job.  That’s why I try to keep what I do with him secret… mostly secret anyway.  Besides, I don’t want to cost him his job either.  I’d feel really bad about that.  So I guess, we’re stuck.”

      “Maybe, maybe not,” Mel replied.  “I’m not worried about him losing his job.  That’s not a problem.  But I certainly don’t want to cost you your job.”

      “No, I don’t want anything to cost me my job either – I need it!  But you’re not worried about Sissy’s job?  At all?  That’s rather cruel.”

     Mel smiled.  “Actually, early on in this bet I fixed things with Mr. Baxter, the owner of your company.  He’s taking a totally hands-off approach to what’s happening with Sissy.  So Sissy is safe as far as that goes… for now.”

     Robin was surprised by that.  “Does Sissy know that?”
      “No.  And he doesn’t need to know it.  I’d rather have him to continue to be nervous about his job there.  Although, to be honest, after I win, I have… other plans for him.”

      “Other plans?”

      “Personal plans,” Mel replied.

      “Oh.”  Robin wasn’t sure what personal plans Mel was talking about and obviously the lawyer wasn’t going to share.  “So what do we do about dressing him differently?” she finally asked.  “Is there anything you can do so he doesn’t look so normal when he comes to work… like he does today?”

     Mel sat back in her chair.  The contract was waiting.  So much work needed to be done with it.  But this conversation with Robin was a far more interesting discussion than what awaited on her desk.  “What problems do you see that we need to overcome?” Mel asked.  “How about him getting to work, for instance, when everybody arrives?”

      “Yeah, Robin admitted, that’s a problem.  Along with the break times too.  And lunch of course.  I guess it all depends on what he’s wearing.  But it will still be a problem.”

      “So we’re back to square one,” Mel replied.

      “Yeah,” Robin agreed.  “But...  What if…  I mean…  Maybe…”

     They wound up talking for so long that by the time Robin got back to her cubicle, Sissy was very late for his next bottle.  She made him drink two in a row on her floor.

     Chad was very aware that Robin hadn’t made him change his clothes that day.  She didn’t even make him play with the paper dolls on her cubicle floor.  The only thing she had done all day, if you didn’t count making him talk to Derek in the break room, was to force him to drink bottle after bottle.  Consequently, he was much wetter than usual.  The mess in his diapers wasn’t helping much either.  Despite his three layers of diapers, if it wasn’t for his plastic panties and the all-in-one girdle, he’d probably be leaking all over the place – if he wasn’t already.  

     The huge heavy bulk of his messy diapers was both aggravating… and sensual.  He loved it… he hated it.  And the wetter he got, the more he worried about it… and loved it, because it only intensified all those amazing humiliating feelings he seemed to crave so much.

      “Sissy…  Bottle time,” Robin’s voice came over the wall between them. 

     Chad got up and went around to her cubicle – with his thumb already in his mouth.  He curtseyed, but Robin just pointed at the diaper bag on her desk and turned back toward her work on the computer.  He reached into the bag and hunted around for a bottle that was still full, and didn’t find one.  Robin’s back was to him, but he dared not curtsey before he spoke.  “Robin,” he said after curtseying, “all the bottles are empty.”  Curtsey, thumb back in his mouth.

     Robin turned around and was glad to see him standing there with his thumb in his mouth.  “I know you have more drinks still at your desk.  Go fill one of the bottles and bring it back.”  She watched as he curtseyed and hurried out.  Then she turned back to her work – that had been delayed because of her lengthy conversation with Mel.

     Chad pried the lid off of what remained of his third large drink he had purchased with his lunch.  He looked inside the cup.  Most of the ice had melted now, which left all the remaining soda in the cup very watered down.  It also meant that there was more liquid in the cup than there had been before the ice melted.  He hoped Robin wouldn’t bother to check. 

     He carefully refilled his baby bottle from the cup and put the lid back on.  Should he put the remainder of the cup in the trash can?  But what if Robin made him drink yet another bottle before he left today – as he more than suspected she would?  His eyes glanced at the two large bottles of water on his desk from earlier in the week that were still partially full.  He had plenty of water, but for once he was enjoying something that tasted a bit better – even watered down. 

     He kept the cup and hurried back to Robin.  He saw her glance around as he stopped and curtseyed, but she didn’t look at him long.  He sank down to her cubicle floor with the bottle and put it to his lips.  As he hit the floor, he could feel how bloated his diapers were again.  It felt like he was sitting on a wet pillow – that squished a bit as he sat down or moved his legs in or out. 

     As he put the bottle to his lips to start drinking, he was aware though of something feeling a bit funny against his leg near the bottom of his plastic panties, but with everything he had on, he had no way to check to see what it was.  It simply felt… odd.  And he worried that he knew what that feeling was.

     By the time he finished his bottle, that strange feeling spot continued to feel odd… only worse now.  And curtseying and moving back to his own desk seemed to aggravate the strangeness even more.  Was he leaking?  He suspected it, although it was hard to tell because of everything he was wearing.  He sat down in his chair, aware again of the squishing feeling from his overly sodden and bloated diapers. 

     He worked, but as he worked, he was still aware of the strange feelings down there – that were now definitely spreading wider.  Ten minutes later, he was sure of it – he was leaking!  He was starting to feel a bit of wetness coming from the left leg on the underside of his girdle.  And that wetness seemed to be spreading – very slowly, but it was spreading.  But like everything else, it was something he couldn’t do anything about.  He did his best to ignore it and keep working.

     It was twenty minutes before quitting time when he heard Robin calling and telling him it was bottle time again.  He got up from his seat – a bit more gingerly than usual.  Before rushing to Robin’s cubicle, he felt the back of his skirt to see if it was wet.  His hand didn’t have to go very far to find the wet spot.  He glanced down at his chair and saw a dark stain on it as well.  Ugh!  Leaking for sure.  Now what was he going to do?  He stuck his thumb in his mouth and hurried around to Robin’s desk.

      “What took you so long?” Robin asked as he was still curtseying.  “I’m leaking,” Chad replied in his silly sissy voice before curtseying again and sticking his thumb back in his mouth.

      “You’re kidding?” Robin asked.  “Really?”  She let out a small giggle.

     Thumb out, curtsey.  “The back of my skirt is all wet.”  Curtsey, thumb.

      “Turn around, let me see.”  She waited as he turned.  “I can’t see anything,” she replied.  “But even if it is wet, the colors of that dress make it pretty much impossible to see.  You’re just going to have to endure it for a little while more.”

     Chad nodded, pulled his thumb out of his mouth, and curtseyed.  “Do I have to fill another bottle?” he asked.  Curtsey, thumb.

     Robin smiled.  “Of course,” she replied.  “Unless you’d rather fill two and drink both.  You can drink more if you like.”

     Thumb, curtsey.  “No thank you.”  Curtsey, thumb.  He grabbed an empty bottle and took it back to his desk and filled it.  Two minutes later, he was once again sitting soggily on Robin’s floor adding even more liquid to his overly hydrated system.  It was a very good thing he had worn the dress he had today, any other outfit would have shown his wet spot for sure!  But what would he wear tomorrow?  Since he had wet it, his current dress was out.  He’d just have to figure something else out for tomorrow that would be fairly safe.