The Bet - Chapter 59 (Monday – week 9 Part 3 of 5)

The Bet

By Karen Singer

Chapter 59 (Monday – week 9 Part 3 of 5)

     The room was absolutely packed!  There were so many people that Mel had a hard time telling what was going on until the proceedings actually started.  Not only were all of the lawyers from Feinbaum’s team there, but so were the entire board of directors from Green Growers as well as a team of lawyers from Sunshine Corporation.  Mel took a seat along the wall next to a few of the other Feinbaum lawyers she recognized.  She was a minor player in all this and her attendance didn’t really mean anything. 

     Harry Feinbaum led the meeting from start to finish.  His son Dick was definitely taking a back seat this time.  Harry said a few opening remarks, then started quickly around the room introducing everyone.  He never used a single note about anyone, but he nodded and pointed to every member of the board of directors without hesitating.  Then he started introducing the lawyers that were present from Sunshine Corporation.  Mel saw Richard Slatter raise his hand as Feinbaum came to him.  Naturally, he had a seat at the main table along with Harry Feinbaum – and all the other major players.

     Harry then quickly went around and pointed out all the members of his team.  When he came to Mel, she partially raised her hand just like most of the others had done to acknowledge who she was. 

     Then Harry Feinbaum got down to business.  For something that was already a foregone conclusion, the meeting went into tremendous detail on many of the sub sections of the agreement.  Mel had a hard time trying to stay interested from her out of the way seat.  In fact, if she hadn’t been required to be there, she would have considered leaving.  Mostly, to her, it all eventually became boring.  And she was the one who liked contracts.  But somehow the time flew by, and before she knew it, they called a break for lunch. 

     Since going back to the office wasn’t really an option, she quickly called Andrea to make sure everything was okay.  Reassured on that front, she accompanied several of the Feinbaum lawyers to an upscale restaurant nearby. 

     It was nearly lunchtime when Derek finally got back to the office.  He had spent all morning out at the job site and he now had more problems to deal with than he thought he would have.  Unfortunately, some of those problems had to be run through Ray… pretty much immediately.  When he entered the building, he headed straight for Ray’s office.

     Ray had been having a lousy morning.  It was his own fault really, he had been kicking himself since yesterday when he had lost it at Mel’s apartment.  What an idiot he had been.  But he couldn’t help it, seeing Derek there yesterday had simply gotten to him.  Well, he knew he had blown it big time.  Mel was history to him.  But he still hated to see Derek winding up with the rich bitch instead. 

     So he wasn’t happy at all when Derek suddenly showed up in his office.

      “Hey!” Derek said as he walked in… as if nothing out of the ordinary had ever happened.

     Rey eyed him up at down as he approached.  Had he come to gloat?  He certainly hoped not.  “What?” Ray asked rather unpleasantly.

     Derek immediately caught the tone of Ray’s voice.  Warily, he said.  “We’ve got another problem out at the job site.”

      “What now?”

     Cautiously, Derek explained his problem.  He could see from the look on Ray’s face that Ray was in a bad mood.  His tone of voice so far had only confirmed that. 

     Derek wasn’t even finished when Ray suddenly said, “Fuck ‘em!”

     Derek did a double take as he heard the words come out of Ray’s mouth.  It wasn’t like Ray at all… ever!  “What’s eating you?” he asked, totally put off by Ray’s manner.

      “Fuck you too!” Ray said as he suddenly got up and walked out.

     Derek was left standing in astonishment as Ray walked past him and out the door.  Shaking his head in bewilderment, he went down to his own office before heading out to lunch. 

     When he got to his desk, he was very surprised to find a plastic container on top of it.  He quickly read the note attached to the top.

 

Derek,

As promised, I will kill all those rumors about you and Sissy – at least the ones that I am responsible for.  It may take a little while, but I can manage it. 

Please enjoy these as a little way of me saying I’m sorry.

Robin

     He pried the lid off of the container.  Chocolate chip cookies – homemade!  And they smelled heavenly.  One of them quickly disappeared into his mouth.  Really good!  Just the way he liked them!  He grabbed two more before putting the lid back on the container.  He could easily eat all of them instead of something a bit more decent for lunch!

     So Robin was going to hold up her end of the bargain – that he hadn’t really made.  Well, she had better squash all those lousy rumors – and fast!  Because he wasn’t going to put up with it much longer.  He had enough to worry about now with Ray behaving so oddly.  Ray had been in a bad mood a few minutes ago, the last thing he needed was more bad rumors circulating about him and Sissy!  Especially now that he had to worry about what he was going to do about Ray.  He wouldn’t be so worried about Ray except that he had to deal with him… and the job he was working on right now couldn’t proceed without Ray’s input!  So like it or not, this afternoon he would have to brace Ray again… and this time get a proper answer!

     He opened the cookie container again and extracted another handful of the sweet treats.  Then he left his desk and headed out for lunch.  A few beers wouldn’t hurt before he had to deal with Ray again. 

      “Sissy!” Andrea called.

     Chad was back in the same richly appointed office where he usually spent his time when he heard Andrea calling.  He put down the book he had pulled off of one of the shelves and hurried out to see what she wanted.  He would have considered not curtseying to her since Mel wasn’t around but… the sissy action kind of went well with the silly party dress he was wearing.  Curtsey.  “You called?” he asked before curtseying again. 

     Andrea giggled.  She simply couldn’t help it!  “Yes,” she replied.  “Mel just called.  She won’t be back till after lunch.  She said you had some food in your bag that you can eat and not to wait for her.”

     Chad curtseyed again.  “Okay,” he replied somewhat disappointed before curtseying a second time.

      “Why do you always do that?” Andrea asked.  “Why do you curtsey like that before and after you speak?”

     Chad shrugged… and curtseyed.  “Mel likes it… and Robin made me do it too.  I guess I just got used to it.”  He curtseyed again – as usual. 

     Andrea giggled… again.  She couldn’t help it.  In that dress, he simply looked absolutely darling!  Not to mention totally ridiculous… which she knew was the real point.  And all the silly curtseying seemed to go right along with the whole theme.  Especially when you threw in his ridiculous silly voice.  Totally ridiculous!  Totally fun!  With another little laugh she said, “I have go to lunch.  I’ll lock up the office here.  Will you be okay?”

     Curtsey.  “No problem.  I doubt I’ll be leaking for a while yet anyway.  I’ll be fine.”  Curtsey.

     Andrea nodded.  She knew he had been reading one of the old books that Mel’s father had kept on his bookshelf.  One of the expensive antiques.  He seemed to be handling it gently enough so she wasn’t all that worried about it.  And he had just reported that he had been leaking again not twenty minutes ago, so most likely she would be back in plenty of time to record the time when his current diaper started leaking.  She giggled again at that thought.  He was wearing a diaper under that ridiculous darling dress.  But that thought made her add one little piece of advice.  “Just be careful you don’t leak all over any of that furniture in there!”

     Curtsey.  “No problem.  I’m used to being careful now.  I won’t.”  Curtsey.

     She nodded.  “Okay.  Then I’m off.  I’ll see you later.”

     Chad watched as she went out the door and locked it before heading to her car.  He quickly retreated to the safety of the room where he had been staying out of sight – just in case anyone should walk up to the door and look in. 

     He had known that he would be eating the baby food for lunch that Mel had put in his diaper bag, he had just thought that he would have some company around when he did eat.  Now he was left all on his own.  Not a problem really, just… different.  With nothing holding him back, he opened his diaper bag and pulled out all the jars of baby food.  He examined each one.  A well balanced meal – if it had been regular adult food.  Rolling his eyes at his own fate, he pulled the baby spoon out of his diaper bag as well.  He totally ignored the bib that had been in there with it.  He sat on the leather couch and opened the first jar and started eating. 

     The meeting was only slightly late getting started again.  Mel had enjoyed her lunch with the other attorneys, but she was really wanting this whole affair to be over with.  Unfortunately, she had to wait as the proceedings moved as slow as ever.  She knew that there really wasn’t much more for them to cover though, and hopefully she would be out of there soon.  She couldn’t wait!

     Since he needed a few beers in his system before confronting Ray, Derek decided to have lunch at one of the bars near the office that he knew also served a decent sandwich.  He walked in… and immediately locked eyes with Ray who was sitting at the bar.

      “What do you want?” Ray demanded angrily.

     Turning a bit angry himself, Derek replied.  “Lunch!  And a drink!”

      “And you followed me here?”

      “You practically forced me to come here… for a drink… after the way you treated me up in your office.  Not to mention the damn ridiculous way you behaved yesterday!  What the fuck was that?”

     Ray stared angrily at Derek for a moment before backing down.  Much more contritely he said, “A mistake!”

      “A mistake?  I’ll say!  So I take it you were planning on having Mel all to yourself?”

     Ray turned away and stared down at the bar he was sitting at.  “Something like that.  At least… I wasn’t planning on seeing you there!”

     Derek said nothing to him for a moment.  Much less confrontationally he asked, “I seem to remember you were all hot yesterday over some money as well.  What was that all about?”

     Ray looked back up at him.  “I said it yesterday.  She’s rich!  Really rich!”

      “Oh come on!”

      “No.  Trust me!  She is!  I checked.”

     Derek stared at him for a moment again.  “Are you eating anything, or just drinking?”

     Ray merely gestured toward the drink in front of him.   

      “I thought so.  Why don’t you join me at one of the tables… and we’ll both have something to eat as well.  You look like you need some food more than that drink!”

     Ray looked from the drink on the bar to Derek and back to his drink again… and back to Derek.  Rolling his eyes, he grabbed the glass and stood up.  “Lead on.”

      “All opposed say Nay!”  The president of the Green Grower’s Corporation looked around the table at all the other board members.  As expected, there wasn’t a single voice of opposition.  “So be it!” he stated.  “The motion to approve the contract and finalize the merger tomorrow has carried.”  There was a lot of low level murmuring from all around the room.  It was a moment before it died down.

     Harry Feinbaum stood up and once again addressed everyone in the room.  Since the motion has now been approved, I think that ends the business for today.  We will meet again tomorrow morning in the ballroom of the Hilton Hotel to finalize the merger.  Thank you everyone.  I know how much work we’ve all put into it.”

     With that, there was a general sigh of relief as everyone realized the meeting was finally over.  Mel glanced at her watch.  Almost two in the afternoon.  Where had the day gone?  But at least she was finished now… until tomorrow morning anyway.  She stood up and spoke casually with several other attorneys as she slowly made her way out of the room… and eventually out of the building. 

     She stopped again on the steps out front to talk a moment longer with one of the other men she had known a long time ago when her father had been alive.  She finally said goodbye to him.  She was about to head for her car, when she caught sight of Richard Slatter staring at her from a few feet away.  There was something absolutely domineering about the man.  Maybe it was just his aura of confidence.  She was surprised when he started walking toward her. 

      “So you’re Mel,” Slatter said as he walked up.  “Daddy’s little girl.  I can see the resemblance to your father.”

     Mel blushed.  “I didn’t know you knew my father.”

      “Honey, I know everybody in this business!  Come to play with the grownups?” he asked smugly. 

     Mel was a bit caught off guard by that comment, not to mention shocked that he should speak to her that way. 

     Before she could make any kind of reply, he continued with a shake of his head.  “Obviously Feinbaum is doing charity cases again, because your father was a second-rate lawyer at best!  And you’ll never be half the lawyer he was!”  With another shake of his head, he turned and walked off.

     Mel was flabbergasted as she stared after him.  Second rate?  The nerve of the man!  She didn’t know if she was just angry… or simply insulted… even as the tears formed in her eyes.  The nerve of the man to call her father second rate!  Never mind her, the man had insulted her father!

     Hurt by his rude comments, she hurried for the sanctity of her car.  It was all she could do to try to hold back the tears as she drove recklessly for her own office.  She was amazed when she managed to reach it without an accident… or without the police stopping her.  She parked the car and hurried inside. 

      “How was the…” Andrea started to ask, but she got no further as Mel ran past her, all the way into her office where she slammed the door behind her.

     The commotion brought Sissy out of the other office.  He looked perplexed at Andrea further down the hall… who was looking just as perplexed back at him.

     Chad waited as Andrea came down the hallway to where he was.  “Was she crying?” he asked quietly.

      “I… think so,” she replied.

      “What happened?”

      “I haven’t a clue.”

      “I wonder if I should check on her,” Andrea said, more to herself than to him.

      “No,” Chad replied.  “Let me.”

      “Stealing himself for whatever he would have to face, he softly turned the handle on her doorknob and pushed it open. 

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!

The Bet - Chapter 59 (Monday – week 9 Part 1 of 5)

The Bet

By Karen Singer

Chapter 59 (Monday – week 9 Part 1 of 5)

     His sexual need was all he could think about.  Even in his dream he could feel the dildo sliding sensually in and out of his backside.  In and out.  In and out.  Delicious!  But he was still frustrated.  While the dream toy felt incredibly good, it didn’t give him the fulfillment he really needed.  He pulled the toy out and picked up another one – the one Cassie used on him.  In and out.  In and out.  It felt so different than the one from Mel that he had used just before.  But again, this toy wasn’t going to give him what he needed either. 

     His dream-self thought again about his regular male appendage.  But that was totally useless now.  Totally!  In his dream, he wasn’t even wearing the darn chastity device.  He could touch it if he wanted to… but he didn’t.  What would be the point?  It no longer functioned.  It no longer gave him the release he wanted. 

     He was a sissy, and as such, normal sex as a male was no good for him anymore.  He had been changed.  Cursed!  Reduced!  Because he was a sissy, he was no longer allowed to pleasure himself with his penis anymore… and as such, he never even thought about getting pleasure that way… not anymore.  Instead, his backside now yearned continuously for the stimulation he had come to realize would be his only means to fulfillment.  No sex as a male every again!  The only way he could receive pleasure was to be penetrated… not to penetrate.  More like a woman than a man.  But the truth was… it was not sex like a woman… it was sex for a sissy.

     Denied!  Cursed!  Reduced!  And the intense feelings and emotions about it drove him continuously in his dream in search of anything that would grant him the release he so desperately wanted.

     Music and talking found their way into his dream... disturbing it… disturbing him… irritating him… to the point where he had to wake up to acknowledge the commercial that was now playing from his pink clock radio.  He opened his eyes.  It was another day.  Another day that would be full of sissy humiliation.  But his brain also realized something else.  Today would be different.  Today was Monday and he wasn’t going to work today. 

     That thought quickly led him to wonder… and worry… about what Mel had planned for him today.  She had said last night before he left her apartment that he should get there a little early today.  Why?  What did she have planned?  He knew she didn’t go into her office as early as he usually went to work, so what was going on?  Only one way to find out – he would have to go over to her apartment and wait till she told him what was going on.  Which was exactly what he would have to do anyway.  There was no getting around it. 

     He rolled off of his blow-up mattress and onto his knees, knocking over one of the empty baby bottles near his bed.  He reached up and turned his radio off.  Even on his knees, his legs were splayed wide apart because of the heavy super thick bulk of all the diapers he was wearing.  He didn’t even have to think about it to know he was not only soaked, but messy as well.  Struggling to his feet, he felt the breast forms that were glued to his chest pull a little bit.  The bra he was wearing helped to support them and helped to keep them from pulling worse, but he could still feel them. 

     Wide leggedly, he waddled out to his kitchen.  He was again disappointed to not see a note on his counter from Mel.  Unfortunately, they were past that point now.  He went directly to his refrigerator and pulled out three of the baby bottles he had stocked in there yesterday.  He carried them as he always did out to his one and only chair that faced his wall of shaming pictures. 

     He rarely really noticed those pictures anymore, but today he looked at them more closely.  It was amazing how much they looked like a real child had done them… scribbled them.  Scribbling that didn’t even stay in the lines… colors that were all wrong.  Childish!  And yet it was he who had colored them that way – out in public – out in the restaurants! 

     His eyes glanced down the wall further and fell on the plans that Sandy had drawn up for his apartment if he lost.  Plans that would essentially turn his entire apartment into one big girly nursery.  As he looked at those plans, he again felt a twinge of sexual need stirring within him.  But as usual, he was forced to ignore that need.  There was nothing he would be capable of doing about it.  Part of him was horrified by what those plans would mean if they got carried out… but an equal part of him yearned for it just as much.  He was a sissy.  There was no denying it, or the sexual need the thought of such a life brought to him.

     That need did remind him though about the new reward system that Mel had instituted yesterday.  He had been allowed to play with one of Mel’s toys in his backside for a few minutes.  But he had been forced to do it to himself while she watched.  And most disappointingly, he had only been able to do it for a very few minutes.  He remembered vowing to try to do better today to leak before the hour and a half point whenever possible.  That would rack up more minutes for him to play.  And the best way he could do that?  He was already doing it – drinking from his bottle… bottles!  The more the better! 

     Maybe tonight he could actually play with himself long enough to succeed!  Long enough to achieve an orgasm!  He seriously doubted it, but it was a goal he couldn’t get out of his mind.

      “No!  No!  No!”  Mel screamed as she again shoved at Ray’s big body.  “Get out!”  He went… again, and again she worried that he would come back.  He had been doing that over and over.  She would throw him out, and he would come back again.  And it was all she could do to keep Ray and Derek from fighting with each other.

     Money, money, money!  That was all Ray wanted!  And she suspected that Derek was only interested in her money as well.  She had to protect it.  She had to keep both of them from finding out how rich she really was.  But she wanted them both.  Both of them!  Each of them were big strong handsome hulking men!  And as aggravating as each of them were, it felt so good to be out with them – either of them… or both of them as she really wanted.  But it seemed now that all they were interested in was her money.  Neither of them loved her for herself. 

      “Are you rich?” Derek asked in her dream.  “Get out!” she yelled at him too.  Then she ran for the safety of her bedroom.  Sissy was there with her.  She sat down on her bed and he was instantly by her side… holding her… comforting her.  He alone wasn’t interested in her money.  He alone didn’t make any demands of her.  He alone was the one she controlled – completely! 

     And even in her dream, she remembered that was part of her problem – her usual problem with men.  All men!  She liked being in control too much.  It was all she could do sometimes to play the little Miss Muffin submissive woman that they all seemed to expect from her.  But she was more than that.  Much more.  She was smart!  She was powerful!  Very powerful! She yearned to display that power… yet the only one she really controlled was Sissy.  At least he didn’t make any demands of her she didn’t like.  He wasn’t allowed! 

     In her dream, her bedroom door nearly exploded as Ray kicked it in.  He was back again!  “Are you rich?” he demanded. 

      “No!  No!  No!  Get out!” she yelled once again! 

     And then Derek was there.  “Are you rich?” he demanded as well.

      “Get out!” she yelled at him too.  But neither of them left.  They didn’t love her for herself, they only wanted her money!  “Get out!” she yelled again as she felt her dream tears falling.  “Get out!  Get out!  Get out!”  But each repetition of the words came with less and less intensity.  In her self-pity, she finally collapsed on the bed… and Sissy held her in his arms. 

      “It’s all right,” Sissy said to her over and over again as she cried.  “It’s all right.” 

     The annoying buzzing of her alarm clock forced its way into her dream, pulling her out of it.  It removed all memory of what she had been dreaming about, but not the emotions of the dream.  She opened her eyes only knowing that she had been upset and crying in her dream, nothing more.  She took a deep breath to try to calm herself.  It was just a dream.  Just a dream – whatever it was that she had been dreaming about. 

     She rolled over and realized that she smelled fresh coffee brewing.  Sissy!  Once again Sissy was out there as he should be… her morning coffee was ready and waiting!  Perfect!  Perfect!  Perfect!

     Chad was concentrating on how wet his diaper might be when he heard Mel calling from her bedroom.  His diaper certainly wasn’t wet enough to be leaking yet, but then he had only had it on for a little over an hour now.  Still plenty of time to go.  Her voice calling his name – his sissy name – galvanized him into action.  Forgetting about his wet diaper, he quickly poured her a fresh cup of coffee and hurried with it into her bedroom.  She was sitting up on her bed… smiling at him, he was happy to see.  He curtseyed, careful not to spill the coffee.  “Good morning, Mistress,” he said in his stupid, silly sissy voice.  Then he carefully curtseyed again.

      “Good morning Sissy,” Mel returned as she looked him over carefully.  As she hoped, he was attired perfectly in his maid’s uniform again.  She took the offered cup of coffee and sipped at it.  Mmm.  So good!  And she didn’t even have to get out of bed to brew it or pour it into the cup.  Sissy had done all that for her and brought it to her only moments after she had called his name.  Perfect!  Perfect!  Perfect!  “Thank you, Sissy,” she said with a bit of a smile.  “I’ll just have a couple of pieces of toast for breakfast this morning.  Oh, and put some strawberry jam on it as well.  And I’ll have it right here in bed.”

     Chad curtseyed and hurried out of the room.  An easy breakfast to prepare.  A moment later, he was loading bread into her toaster. 

     The coffee helped kick start Mel’s brain to thinking.  Thoughts of how nice it was to finally have Sissy there and doing what she wanted him to be doing were interrupted by thoughts of her day ahead – specifically, the meeting with Feinbaum’s group over the contract.  Even now, after having been through the contract so carefully, there was still something that bothered her about it.  And yet, she could find no fault at all with the thing.  The contract was a massive piece of legal art… constructed by one of the best in the business.  And today they would be meeting with Green Growers to recommend that they sign the thing and finalize it tomorrow.  Hopefully, she would merely be attending and wouldn’t have to even open her mouth there.  What would she say anyway?

     This contract had come along at the wrong time!  It was seriously distracting her from what she needed to be doing with Sissy.  She had mostly cleared her schedule for all this week just so she could work closely with Sissy and make sure she would win the bet, but there had simply been no getting around this deal.  You don’t say no to Old Man Feinbaum!

     So what was she going to do with Sissy today?  Her thoughts were interrupted by him coming back into the room bearing a tray with a plate and two pieces of toast covered in strawberry jam.  She let him place the tray on her lap, then she handed him her coffee cup to refill.  As he hurried off, she went back to her planning.  What to do with Sissy?  Obviously, the best thing she could do with him today would be to take him into work with her and leave him with Andrea till she could get out of that meeting.  Then she would be free for the rest of the day to do what she liked with him… or to him as the case might be.  She actually giggled a bit at the thought. 

     She was still giggling to herself as he came back in with the fresh cup of coffee.  “Have you leaked at all yet?” she asked him as he curtseyed and offered the cup to her. 

     Chad curtseyed again.  “Not yet,” he replied in his silly voice, “but I still have plenty of time.”  Curtsey.

      “How much time?”

     He looked at the clock beside her bed.  Curtsey.  “About twenty minutes yet.”  Curtsey.

      “So in five more minutes your chance of gaining some reward time will expire,” she stated.

     Curtsey.  “Yes, Mistress…  But I think I’m getting really close already!”  Curtsey.

     Mel was glad to hear that.  “How many bottles have you finished so far this morning?”

     Curtsey.  “I’m working on number six,” he replied.  Curtsey.

      “So I take it you’re trying hard to rack up some of that reward time.”

     Curtsey.  “Very hard!”  Curtsey.

     Mel was pleased.  Very pleased.  It was exactly what she had hoped for… exactly what she wanted to hear.  Hopefully, the little bit of reward he might gain every day would keep him trying harder and harder to continuously wet himself – and in the process, would keep robbing him of any ability he might still have to hold back and control himself.  Hopefully!

      “Very good, Sissy,” she replied.  “I’m glad to hear that.  And I hope you manage to gain a lot of reward time today.”  She switched subjects… somewhat.  “Have you eaten anything yet this morning?”

     Curtsey.  “No, Mistress.”  Curtsey.

      “Good!  You’re not supposed to!” she replied authoritatively.  “Now go start making your breakfast while I’m eating.  I’m sure you know by now what you’re allowed to have.  I’ll be in soon to set you up in your highchair with it.”  She watched as he curtseyed and hurried off.  Yes, despite having to still worry about taking care of him and making him incontinent, it was going to be so great when this bet was over with and he would be locked into her service.  Then, all she had to do would be to find a way to make it permanent.  Unfortunately, her thoughts were clouded with the one thing she didn’t want to think about concerning Sissy… the one thing she still hadn’t found an answer to yet – self-respect, friends, and a life!

     Chad had already finished heating his baby cereal and had poured it into one of his childish bowls by the time Mel came out of her bedroom – wearing nothing but her nightgown with a light robe over it.  She saw that he had his breakfast ready, but her first concern was his diaper.  “Are you leaking yet?” she asked, knowing that the deadline for any possible reward was only a little over a minute away. 

     Chad quickly took a moment to try to figure out if he might be leaking.  Then he curtseyed.  “I don’t think so,” he replied uncertainly.  “But I have to be very close.”  Then he curtseyed again.

      “Oh well,” Mel replied.  “Close doesn’t count.  Up in your highchair now.”

     Chad was disappointed, he had been really trying since he had gotten out of bed.  He wanted that reward time – and technically, he did still have a few minutes left.  Reluctantly, he headed for his highchair, but he stopped just as he turned around and started to climb up into it.  He looked up at Mel hopefully.  “It’s possible that I might be leaking now,” he told her without bothering to curtsey.  “Or if not… I could be very soon.  If I get up into the chair, I might not be able to tell.”

      “Lift your dress,” she told him.  “Let’s see.”

     Chad pulled his skirt up high and started feeling around the leg openings of his diaper while Mel looked on closely. 

      “I don’t see anything yet,” Mel said.  “But you do look awfully wet.”

      “I know I’m really close!” Chad insisted.

     Mel shook her head.  “Okay Sissy.  Grab your bottle.”  She glanced at the clock.  “You’ve got thirty seconds.  If you’re not leaking by then, then you’ll just have to start your breakfast and hope that you’re leaking before the next fifteen minutes gets through.  Otherwise I’m going to paddle you good!”

     As wet as his diaper was, Chad was sure he would be leaking before his second deadline.  What he wanted though was to be leaking in the next few seconds.  He attacked his bottle furiously, sucking as hard as he could on it while Mel watched.  Twenty seconds later, he felt himself peeing again.  As always, it was only a tiny bit, but it was more added to his diaper.  Still drinking from his bottle, he began feeling around the bottom of his diaper again.  Leak!  Leak!  Leak!

     He glanced at the clock.  Ten more seconds!  Please pee again!  Please leak!  The time was ticking down.  Leak!  Leak!  And he thought he felt something moist at the bottom of his diaper!  “I’m leaking!” he proclaimed quickly. 

     Mel glanced at the clock and saw it ticking down the final few seconds.  With somewhat of a smirk on her face, she said, “It’s so close I shouldn’t give you anything at all.  But you tried so hard, I’ll grant you a whole minute – this time.  Don’t expect me to be so lenient again!”

     Chad didn’t care.  He had done it.  He had gotten his diaper leaking ahead of time and now had one whole minute of reward time coming. 

      “By the way,” Mel said to him.  “You might want to get that diaper changed pretty fast.  I started your time running the minute you told me you were leaking.”

     Once Chad’s diaper was changed, Mel locked him into his highchair and left him not only with his usual breakfast and baby bottle, but she also set out two more bottles for him to drink.  “That’s just to give you something to work on while I’m getting dressed,” she told him.  Then she left him alone knowing he wasn’t going anywhere till she came back to release him. 

     Now, what was she going to wear for this meeting?  It was a foregone conclusion that she would be wearing one of the two new suits she had just bought.  But which one?  She considered that while she showered and did her hair.  She was still considering it as she did most of her makeup.  In the end, she wore the same blue suit she had worn to the last meeting.  Since the room had been full of men, she doubted that anyone there would really remember what she had worn anyway.