The Bet - Chapter 59 (Monday – week 9 Part 2 of 5)

The Bet

By Karen Singer

Chapter 59 (Monday – week 9 Part 2 of 5)

     Robin’s arms were fully loaded as she struggled to open the door to the building.  Not only was she carrying her usual armload of junk, but she had something else with her as well that had refused to fit into the large bag she carried every day.  The long walk through the hallways was difficult as she struggled to carry not only her heavy bag, but also an armload of women’s magazines, and a large plastic container in her arms.  Turning down the final hallway was disappointing since she didn’t see Sissy waiting to greet her, but then he was going to be off all this week.  She wouldn’t see him until next week – at work anyway.  She’d also be seeing him on Saturday when she went to help judge his bet.  Passing his empty cubicle was disappointing too.  It made her feel that much more alone.  And she was alone down here, wasn’t she? 

     Finally dropping everything onto her desktop, she reached into her big bag and pulled out her mirror.  She checked her face and fussed with her hair a bit before putting the mirror away.  She then reached over and pressed the button to boot up her computer.  While that was in process, she pulled out a small piece of paper and a pen from her desk and wrote a short note.  By the time she finished, she was able to log onto her computer. 

     As the machine went through the rest of its loading and startup processes, she grabbed a bit of tape – the same tape she had used to bind Sissy with last week, and she taped the note to the top of the plastic container.  Ignoring everything else, she grabbed the container and headed out through the hallways again. 

     She’d had a lot of time to think about things this past weekend and had decided that this would be her best course of action – well, the start of her actions anyway.  She owed Derek now.  She owed him big.  Her scheming concerning Sissy had maligned Derek more than a bit.  It wasn’t a big thing… really.  But it wasn’t right either.  Besides, she didn’t need Derek to be angry with her for the next decade or so.  And she had promised to squelch all those rumors she had started about him.  And she would.  It just wasn’t going to be as quick or as easy as she had said it would be.  So what she was doing now was part of her plan to simply say… I’m sorry.

     She took the elevator up a level, then more hallways, all the way to his office where she expected to see him.  But he wasn’t there.  Just his empty desk.  It looked like he hadn’t been in at all yet.  Well, it was still early, but that was why she had attached the note.  She left the container prominently on his desk where he couldn’t miss it and headed back to her own desk… her lonely desk now.

     As she reached her own hallway, she was again struck by the loss of Sissy not being there.  He had been so much fun since his bet with Mel had started.  He was only going to be gone for a week, but already it seemed like an eternity. 

     The hallway was quiet.  Very quiet.  More than ever she was aware that not only was there nobody around, but nobody would be around – for the entire week!  She decided she would go to break early today… and probably stay later as well!

     Chad swung his legs back and forth and from side to side.  There wasn’t much else he could do while he was confined to his highchair.  He had long ago finished his baby cereal breakfast, and had also finished two of the three bottles she had given him – just because he had little else to do.  And now he was halfway through with bottle number three – of the breakfast bottles she had given him.  He had no doubt that he would be leaking well before his next deadline. 

     He was very pleased to see Mel come back from the bedroom.  She was dressed very nicely in a dark blue pinstripe suit.  She looked – amazingly professional!  And… somewhat more dominant than usual… he thought anyway.

      “All done?” she asked the obvious as she headed for his chair. 

      “Yeth Mithdweth,” he lisped in his stupid sissy voice.

     Mel removed his bib, then took his empty bowl and all the bottles off the tray.  She set the bowl in the sink and ran a little bit of water into it.  Then she returned to his chair and pulled the tray away that had locked him in place, releasing him from the seat.  She watched as he slid down off of what had once been a bar stool, but was now a very girly looking big baby’s highchair. 

      “Get your diaper bag Sissy, and bring it here,” she told him.  “We need to stock it up for the day.”  As Chad hurried off, she headed for the cabinet that held all his baby food.  Once Chad returned a few moments later, she pulled a number of jars of the baby food out of the cupboard and placed them into his diaper bag.  Then she went to the refrigerator and grabbed several more bottles.  She looked into the bag, then back at him.  She remembered that he was now actively trying to gain his reward time by leaking early.  “Grab another handful of your diapers,” she told him.  “At the rate I hope you’re going to be leaking today, you may need a few extras.”  While Chad hurried off to get more diapers out of her bathroom where she had some stored, she added his bib and one of his baby spoons to the bag.  Sissy returned a moment later and she stuffed the stack of extra diapers into his bag as well.  “Okay, grab your bags Sissy,” she told him, “and let’s go!”

     Chad picked up the now heavier diaper bag and slung it over his shoulder.  Then he followed Mel to the door where she had just gotten her purse along with her laptop case.  He stopped only long enough to grab his own purse before following her out the door.  Where were they going?  She was dressed for work so he figured he would be heading into the office with her.  But she surprised him by stopping at his apartment door and opening it for them both to enter.  He followed her inside where he set the diaper bag down along with his purse.

     Mel had headed straight for his bedroom so he went there as well.  She was just opening his closet door when he got there.  He watched as she looked around.  “Start getting undressed Sissy,” she ordered without turning around.  “I don’t want you wearing that maid’s dress today.”

     Chad started removing his apron first.  The dress followed shortly after as Mel was still pawing at the clothes in his closet.  He was now down to just his bra, waist cincher, his single diaper, and his shoes. 

     Mel looked back at him.  “Those shoes won’t work Sissy,” she told him.  “Take them off.”

     Chad slipped his shoes off… just as Mel started pulling something out of his closet.  And when he saw what it was, he died inside more than a bit. 

     Mel was smiling triumphantly as she held up the outfit she wanted him to wear.  “I think Andrea will just love seeing you in this today.” 

     Chad stared in horror as Mel walked toward him carrying his frilly pink and white little girl dress – the one with the ruffles that were nothing but an absolute horror… or heaven, depending on your point of view. 

     One silly pink little girl dress with a massive amount of frills – all with a mind of their own, one pair of very high pink heels, and one pink pacifier later, and he was finally ready to accompany Mel to work.  He couldn’t help but be aware of his silly sissy dress as it moved with every step that he took – heightening his already overly heightened sexual need.  Before grabbing his diaper bag again, Mel had him transfer a few things from his regular purse to the crazy little girl purse she required him to use with his silly outfits.  Then they were out the door again, only this time he was overly aware of what he was wearing… not to mention very embarrassed!

     There were a number of people down in the parking lot.  All of whom stared at him and several of them outright laughed, adding to his embarrassment… and excitement.  He was glad to finally get into Mel’s car where his dress was out of sight – mostly anyway.  And hopefully nobody would notice that he was sucking on a pacifier as they drove through the streets. 

     He was glad to see only one other car in Mel’s parking lot, Andrea’s he was sure.  Once Mel had parked, he quickly got out of the car and grabbed his diaper bag from the back seat.  Then he followed her toward the door – all too slowly.  He wanted to get out of sight, but he didn’t think Mel had ever “sauntered” so slowly in her life!  Finally she opened the door and went inside.  He pushed his way in after her… and received a rather excited little shriek from Andrea as he did.  By the time the door closed behind him, she was running at him all too excitedly.

      “He’s so pretty!” Andrea exclaimed as she hurried straight for Sissy.  She stopped in front of him and began pawing at his dress.  Touching this, pulling on that, examining it in minute detail.  “Oh Mel!” she exclaimed.  “I remember when this dress came in and you showed it to me!  But seeing it on him… it’s so much better than I imagined!”

      “I kind of thought you’d like it,” Mel replied with a satisfied smirk.

     Chad was just glad that he knew Andrea, but the way she was gushing over him was still all too unnerving. 

      “What’s he doing here?” Andrea asked Mel.

      “I need you to just keep an eye on him for me while I’m in the meeting.  I had nowhere else to take him.”

      “You couldn’t just leave him at home?”

     Mel shook her head.  “Not this close to the end of the bet.  And I need someone around with him all the time now.”

      “Me?  What do you want me to do?” Andrea asked as they all finally started moving away from the door toward her desk.

      “Nothing,” Mel replied, “except take note of the exact times he tells you he’s leaking.”

      “Times he’s leaking?”

      “He’ll tell you.  And the moment he starts leaking is the time I’m using now to start his next time period requirement.  I need you to be fairly exact about it, I’m afraid.”

      “Okay,” Andrea replied uncertainly.  “So you just need me to list some times?”

      “That’s it,” Mel agreed.  “And hopefully this meeting won’t last too long.”

      “What if it goes past lunch?”

      “It could,” Mel agreed.  “Just leave him here and take your usual lunch.  Then check with him to find out if he’s leaked at all when you get back.”  She looked sternly at Sissy.  “We’ll have to take it on faith if he leaks then.  But we should be able to tell how accurate he’s being by comparing it to the other times.”

      “Okay,” Andrea agreed.  “Is he supposed to be doing anything else while you’re gone?”

     Mel shook her head.  “Just trying to get his diaper leaking.  And that’s all.  Anything else is up to him.  I don’t care right now.  I have other big problems to worry about today.”

      “Yeah, like that merger!” Andrea agreed.

     Mel nodded.  “Thanks for holding down the fort,” she replied as she turned toward her office.  “Come along Sissy.  I have work to do.”  She led the way down the hallway and stopped in front of the office door where she had “kept” him before.  “Put your things in there,” she told him.  “And try not to bother me.  The office is supposed to be closed today so I don’t care what you do or where you go, just so long as you keep leaking on time and don’t make a nuisance of yourself.”

     Chad curtseyed.  “I’ll be fine,” he told her.  "So I just tell Andrea every time I start leaking today?”  Curtsey.

      “That’s it,” Mel replied.  “At least until I get back… which hopefully won’t take too long.  You never know with meetings like this though.”

     Chad nodded… and curtseyed.  “I’ll be fine,” he said again.  “And I do want to gain a little more reward time for this evening!”  Curtsey.

     Mel smiled.  “I was hoping you’d feel that way.  Sorry I have to be so busy, but that’s my job.”

     Curtsey.  “I understand.  Perfectly!”  Curtsey.

     Mel smiled and left him there.  She had to concentrate on the upcoming meeting now.  She didn’t have much to do, but she did need to get everything together and at least look through things one more time before she left.

     The break room was empty when Robin arrived.  She poured herself a cup of coffee, and even though it wasn’t on her diet, she helped herself to a doughnut as well. 
The doughnut would help her fill a few of the extra minutes before the others arrived.  She headed over to the women’s usual table and took a seat to wait.  It was almost five minutes before the others even started showing up.  Gradually, the table filled up and Robin was a lot less lonely as she chatted animatedly with the others. 

     As she talked, she did watch the time though – more than the others did.  She knew she had to straighten things out as far as Derek went, but she was having a hard time actually getting started doing it.  Besides, she didn’t want to ruin such delightful conversation with something like that.  But eventually she realized that if she didn’t do it soon then the others would be leaving and she would lose her opportunity.

     She finished what she was talking about with two of the other women and said, “Excuse me a minute.”  Then she stood up.  “Ladies…” she said to get everyone’s attention.  It was a moment before they all quieted down and looked at her.   This was the hard part now.

      “I have to straighten something out,” she told them.  “And I guess it’s kind of important.”  She could see she had everyone’s close attention now.  “It’s about Sissy… and Derek.”  She saw some of their eyes going wide, as if the women were hungry for more outrageous rumors to discuss.  “You know of course that, that kiss last week… was all a setup.  And that Derek doesn’t really like Sissy at all.  At least not like you think he does.  In fact, right now, I don’t think Derek likes Sissy at all.  And I can tell you for a fact that Sissy isn’t the least bit interested in Derek either.”

      “A setup you said?” one of them asked.

     Robin nodded.  “Yeah.  My doing actually.  I thought it would be funny.  And… it was!  At least to me.  I kind of… forced Sissy to do that.”

      “Forced?” someone asked.

     Robin nodded again.  “Yeah.  I kind of threatened Sissy to make him do it, but don’t ask what I had to threaten him with!”

      “Threaten him?” Someone else asked.

      “Yeah, believe it or not.  And I know it wasn’t nice of me, but...” she giggled a bit, “I just couldn’t help myself.  I’m afraid I was having a lot of fun at his expense.”

      “So what’s going on?” Someone asked.

     Robin shook her head.  “I’m afraid I can’t tell you that.  You’ll have to ask Sissy himself when he comes back next week.  I just wanted to straighten out the fact that Derek and Sissy are not really interested in each other.”

      “But they were friends,” someone threw in.

      “Yeah,” Robin replied.  “They were.  I’m not sure how good that friendship is anymore.  And I’m afraid I may have made things worse for them now.”

      “I never believed any of it in the first place,” someone stated.  “I mean, I’ve been out with Derek… several times.  He’s just not the type!”

      “I know what you mean,” someone else added.  “I had a hard time believing it too.”

      “So is Derek dating again?” another woman asked.

      “Oh yeah!” Robin answered, “just not Sissy!”

     There were a few chuckles.  “Hey!” someone threw in, it was fun to talk about anyway.  So what’s really up with him and the dresses and stuff?”

     But that was somewhere that Robin couldn’t go.  “What can I say?” she asked with a shrug.  “He likes it!”

      “So he is looking at getting a sex change?” one of them asked.

      “I doubt it.  But you never know what the future will bring.” 

     A few of them got up at that point because they had to leave and Robin sat back down.  The rumors about Derek would be killed – mostly.  But she had a feeling that more would be growing about Sissy.  And that part she didn’t mind one bit!