The Bet - Chapter 52 (Monday – week 8 part 1 of 8)

The Bet

by Karen Singer

Chapter 52 (Monday – week 8 part 1 of 8)

     Worry and confusion reigned supreme in her dreams.  Over and over again she labored hard to build herself a home, only to have either Derek or Ray come by and knock it down again, ruining everything she had worked so hard for.  But still she tried again and again to create what she so desperately wanted. 

     First she built a home for herself and Sissy, only to have Derek come by and angrily smash it all.  Then the next time it was Ray who ruined it.  After that, it was Derek again. 

     In her despair, she made a deal with Derek, she would build the home for herself and him – not with Sissy, not with Ray.  But once the house was finished, Ray showed up like an angry rampaging monster and totally destroyed everything.  All because she had built her home for herself and Derek and not for herself and him. 

     In her fear, she threw Derek out and made a different deal with Ray and built the home with him instead, but then Derek was back, angrier than ever and destroyed everything just as Ray had done.

     Finally, she tried making an alliance with both Derek and Ray together.  It was a very uneasy alliance, one that fed the hatred between them.  Derek and Ray fought constantly, always doing major damage to her house each time.  She lived in fear of both of them and it was all she could do to keep them from tearing each other apart. 

     And then Sissy showed up.  There was just something about him that she wanted to have close to her – something kinder, something calmer.  But Sissy’s presence enraged both Derek and Ray to the point where they both totally destroyed the entire house again.  Only then, did she realize that Sissy knew it would happen all along.  While he didn’t have the brute strength to destroy anything, he had been intelligent enough to make them do the dirty work for him. 

     And once the house was destroyed again, Sissy left her!  Coldly.  Without even looking back.  Because she knew she had deserved what she had gotten.

     She was filled with despair.  Each of them wanted her for themselves, yet she wanted all of them together.  And there was no way she could have more than one at the same time.  And in the end, she wound up with no one.  She was alone.  Alone enough that she wouldn’t even consider building the house for just herself. 

     It was in that feeling of total despair that she finally realized her alarm was buzzing.  The total despair ended as she opened her eyes to wakefulness, but bits of the feeling remained.  It took her a minute before she could bring herself to turn her alarm off.  Two more minutes before she could bring herself to sit up on the side of her bed.  She looked at her clock.  She had set it last night to give herself ten minutes more this morning so she could feed Sissy a larger breakfast, and already she had wasted more than half of it.  Feeling worse than ever, she forced herself to her feet and grabbed her robe.  It was more out of desperation than anything else that she made her way out to her coffee pot to get that started. 

     She couldn’t do anything till she got some coffee in her.  Not anything.  Just a sip of the coffee would do.  Soon now, Sissy would be there every morning with it already made, fresh and ready.  That first sip would be delivered to her instantly while she was still in bed.  Very soon now… very soon… very…  Of course, she did have to win the bet first.  The stupid bet!  Five minutes!  Five damn minutes still stood between her and what she wanted!  Five impossible minutes!  How the heck was she supposed to overcome that? 

     Ugh!  What a lousy way to wake up!

     One minute there was blissful silence, the next he was panicked out of his wits as the loud blaring music seemed like it would break the walls apart.  He moved as fast as his panicked body could move to roll off of his blow-up mattress and get to his knees where he could slap at the button to turn his pink alarm clock off.  Relief filled his body as the room was suddenly emptied of sound. 

     But the jarring music has done its job and jarred his brain into a working state.  The first thing he noticed was that he was dry.  Totally dry.  Not dry inside his diapers – not by any means, but dry on the outside.  Yesterday when he had gotten up, his bedding had been soaked.  Terribly soaked!  But today, everything was as dry as it should be.  That much was a relief! 

     However…  The horribly thick cloth diapers he was wearing were miserably bloated and heavy… and messy, just like they always were every morning.  He was still amazed that he could sleep through it all and never notice what was going on. 

     Next, his brain registered that his breast forms were once again glued on and were hanging from the bra he wore to help support them every night.  It had been pleasurable to not have them for the past two nights.  So as far as he could tell, things were once again back to normal.

     With a yawn, he started waddling his way out toward his kitchen to see if she had left him her usual note.  He was glad to see the note right where it should be.  He read it half-heartedly… most of it.  Most of it was the usual – three baby bottles before he got cleaned up… yata, yata, yata…  And then there was one last line added:  “From now on you will wear three diapers to work instead of two!” 

     Three!  He immediately began thinking about how much thicker three diapers were. Two were comfortable.  Perfect in fact.  He felt much more secure with two diapers than with one.  And two diapers didn’t add all that much more bulk around his backside.  But three!  Three would definitely make a difference.  Not only would they possibly show more, but just thinking about it, he could almost feel the bulk restricting his walking!  Three! 

     Mildly upset over the matter, he grabbed the three baby bottles out of his refrigerator and carried them to his one solitarily piece of real furniture – the chair stuck facing his wall of shaming pictures in his living room.

     It took time for Chad to sit and drink three baby bottles – two of which held Mel’s lousy green tea mixture and the third was filled with apple juice – a pleasant change.  It also took time for him to shave his face afterwards.  More time was needed for him to remove the thick and messy diapers he was wearing and to temporarily deal with them.  He dared not go more than a few seconds without some kind of protection anymore since there was way too much chance he would start peeing all over the place before he knew he was even doing it.  As fast as he could, he jumped into his shower, which also took time.  More so because he had to thoroughly clean his messy backend along with washing his hair and shaving all the stray hairs from his body. 

     The second he stepped out of his shower, he made a mad dash to get the first of his three diapers on.  He almost breathed a sigh of relief as soon as he simply held the first one in place so no harm could be done if he did start peeing.  The second and third diapers followed quickly, although each one seemed to take more and more time to get into place and to tape firmly so they wouldn’t come apart.  He immediately noticed the added bulk of the third diaper between his legs.  Not a major problem since he had dealt with it many times before, but still, it was something he was going to have to get used to more often now.  After basically, after spending all weekend in only one thin diaper, the three diapers now felt strange… but he was glad to have them.  At least he was no longer on any kind of time limit for them to be leaking.  Not until tonight at least.  And of course, as he was thinking about the added bulk between his legs, his body added yet more bulk as it let loose another bit of pee.  Well, dry diapers never stayed that way for long anymore.  He was lucky now if he could get them fastened before they got wet.

     He pulled on his plastic panties for extra protection, then he added his waist cincher and his all-in-one girdle over top of that.  Only then did he take the time to thoroughly deal with his messy diapers from last night.  And cloth diapers couldn’t be just thrown away like he usually was able to do.  Since Mel had rendered his toilet useless with her layers of plastic wrap, he had to rinse them in the tub to get most of the mess off of them before sticking them in a plastic bag to wash later – whenever Mel allowed him to take care of them. 

     His hair had to come next.  The blow dryer first, followed by the curling iron.  It took a lot of time to get it all just right.  And then more time was required to do his makeup properly. 

     Finally he was able to finish getting dressed.  He stared at the clothes in his closet – only women’s clothes.  All Mel had left him.  But what to wear?  He finally chose an outfit with a fairly full skirt so that he didn’t have to worry about the added bulk of his three diapers being too obvious.  Pantyhose, the skirt, and a colorful top all went over his all-in-one girdle.  His wooden necklace, and bracelet.  The blue studs in his ears.  The pink ring on his finger.  And his women’s watch on his other wrist. 

     A quick check in the mirror to make sure everything was as it should be.  Then he grabbed another empty plastic bag and put his three empty bottles from last night into it along with his three empty bottles from this morning.  He removed his wallet and keys from his new little girl sissy purse and stuffed them into his regular one.  He felt much more comfortable with that one as he hung it over his shoulder.  He grabbed his diaper bag… and headed out his door.  Off to Mel’s apartment first, then off to work – dressed as a woman!  His usual weekday routine. 

     He knocked on Mel’s door and waited till she opened it.  He curtseyed and said “Good morning Mistress,” in his silly lisping sissy voice.

      “Good morning Sissy,” Mel replied as she always did before she stepped back out of the way and let him enter.  She started looking him over immediately while he was still setting his purse and diaper bag on the floor under her little table by the door.  She looked him over more carefully when he stood up, waiting for her inspection.  “Are you wearing three diapers like you’re supposed to?” she asked him.

     He curtseyed.  “Yeth Mithdweth,” Chad’s sissy voice replied. 

      “Good!  Go get up in your highchair now.  I’ve made you a larger breakfast than usual since you haven’t been eating as much lately.”

     Chad hurried to his highchair.  More breakfast!  He wasn’t surprised, but he was still disappointed as soon as he realized that Mel had only made a larger batch of the same lousy tasting baby cereal she gave him every day.  Eggs and ham, or biscuits, or sausage, or… anything normal would have been really nice.  But still, he was hungry, so he supposed he should be grateful.  Two minutes later, he was locked into his highchair behind the large tray, his bib was tied in place, and he was spooning baby food into his mouth with a tiny baby spoon.  His fourth baby bottle of the morning was on his tray as well.  Four bottles before he went to work!  It was no wonder his diapers were so wet already. 

     While Sissy was busy eating, Mel pulled all the empty baby bottles out of his diaper bag.  She usually put three back in every morning.  Last Friday she had put in four.  But today, she put six in it.  She was hoping that the extra bottles would encourage Robin to make sure he kept drinking all day.  She made sure he had plenty of extra diapers and an extra pair of plastic panties.  Then on top of it all she added the t-shirt and bib Sissy had washed over the weekend.  Finally, she added the multi-colored bow she had bought at the mall yesterday.  His diaper bag was ready.  Now she just needed him to finish eating.

     Chad was running a bit late as he pulled into his parking space, but only by a few minutes.  Not enough to even worry about – except for Robin.  He was sure that the fault was in the fact that Mel had cooked him a double portion of the baby cereal that he had to manage to get down.  But Robin had demanded that he greet her every morning when she came in.  And if he was late, then there was more of a chance that she would already be there.  What then? 

     He grabbed not only his purse, but his diaper bag out of his car too before he hurried into the building.  Was Robin there already?  As he turned down the hallway where their cubicles were, he saw nothing to indicate either way if she was there or not.  Worry about Robin being mad at him for being late made him hurry straight past his own cubicle to check hers.  And there she was, her back to him as she reached for the button to boot up her computer.

     Robin turned around as she heard someone behind her.  Sissy!  “It’s about time you got here.”

     With his diaper bag and purse still slung over his shoulders, Chad curtseyed and said in his sissy voice, “Sorry, Robin.  Mel kept me a bit longer this morning.”

     But Robin only stared at him as if expecting something more. 

     Not knowing what else to do, Chad curtseyed again and said, “Good morning Robin.”

     But still Robin only stared at him… waiting.

     Chad was confused.  What did she want?  What was he supposed to do?  Anything?  Could he move now?  Could he go back to his desk?

      “Obviously you’re a slow learner,” Robin finally said.  “Are you done speaking to me?”

     Chad curtseyed before lisping his one word answer.  “Yes.”

     And again Robin only stared at him for a while as if waiting for something else.  Robin finally sighed.  “I expect you to curtsey whenever you’re finished speaking!” she finally told him.  “How else am I supposed to know when you’re done spouting nonsense out of your mouth?”

     Oh!  He had forgotten!  Mel didn’t require him to curtsey both before and after he said anything.  Doing it just before was bad enough!

     Robin stood up and grabbed his diaper bag from him and dropped it on top of her desk.  “Since you can’t seem to remember, back up into the hallway and start practicing.  You can say good morning to me… over and over again.”  Without another look at him, she opened his diaper bag.  But before she could really look in it, she realized that he hadn’t moved yet.  “What are you waiting for?” she asked, totally annoyed with him.  “Do you need something else to help you remember?”  Chad started to back out of her cubicle, but he didn’t get very far before she said, “Stop!” 

     He stopped, wondering what she wanted from him now.

      “Before you start practicing, take that skirt off.  Maybe running around without it for a while will help jog your memory and motivate you a bit better.”

     Take his skirt off?  She couldn’t be serious!  But the look on her waiting face told him she was very serious.

      “Do you need to remove anything else too to get you moving?” she asked since he hadn’t moved yet.

     Not wanting to make things any worse, Chad reluctantly removed his skirt.  Robin held out her hand and he gave it to her.

      “Now go out into the hallway there and practice curtseying before and after you say anything.  I’ll let you know when you can stop.”

     Without his skirt now, Chad carefully checked the hallway before he left the cover of Robin’s cubicle.  Nobody was in sight as usual.  Quickly, as if it would make his practicing get over with faster, he stepped out into the middle of the hallway and turned around to face her.  She didn’t seem to be paying the least bit of attention to him.  She was looking through his diaper bag instead.  He couldn’t believe how naked he felt without that skirt!  He pulled the strap of his purse that was still slung over his shoulder up more so it wouldn’t fall off.  He curtseyed.  “Good morning, Robin,” he said in his sissy voice.  Then he curtseyed again.  He realized he was peeing again, but he didn’t know if it was from fright, or humiliation, or because he simply still had way too much liquid in his system.  He paused only a moment before glancing up and down the hallway again and launching into the routine again.

     Robin purposely didn’t look at him.  It was bad enough that he had shown up to work today looking more “normal” than ever.  Or maybe it was more like a real woman than ever.  When he looked like that, it was hard to believe what a stupid sissy he really was.  It was the little things like his curtseying and his stupid sissy voice that helped to remind her of how she needed to deal with him.  She preferred the more visible reminders when she was able to dress him… differently.  More childishly.  Dress him more like the way he acted! 

     She pulled the hair bow out of his diaper bag and took a good look at it.  It was all different colored ribbons rounded over on top of each other, almost forming a complete ball on top.  Long streamers of the ribbons hung down from it at the back.  It was really very pretty.  Not something most women would wear, but it would be very pretty on a little girl.  The multi-color ribbons would probably go with almost anything too.  She set the bow aside and pulled out the bib and t-shirt she had sent home for him to wash.  They were both clean and neatly folded.  Good!  Those she set aside as well for later.  She also noted the extra number of baby bottles Mel had put in the bag today.  Well, that was no problem too.

     She really wanted to take his regular clothes off of him now, but it was too early in the day.  She was too afraid to do even that much yet.  She could hear his voice droning on in the background.  She glanced at him.  She had made him take his skirt off.  Did she have the courage to make him take everything else off this early too?  No.  Not yet.  But the skirt alone should be reminder enough for him.  If not… 

     She closed his diaper bag again.  “Okay Sissy.  Go get some work done.”

     Chad curtseyed one more time.  Could he get his skirt now?  Instead of going to his cubicle, he went back into hers. 

      “What?” Robin asked. 

     Chad curtseyed and pointed at his skirt.  “My skirt…”  Then he curtseyed again.

      “No!”  But when Chad had pointed to his skirt, Robin had noticed something else.  “Let me see your nails.”

     There was simply no way to get past the embarrassment of his fingernails.  Bashfully, he slowly stuck one of his hands out so she could see. 

     Robin read the word “SISSY” spelled out on his nails and almost cracked up laughing.  “And the other one?” she asked.  Slowly, Chad stuck his other hand out too.  “I love it!” Robin declared with obvious delight.  “Just the perfect thing for… you!”  With a laugh, she said, “Now get lost!”

     More nervous than ever, Chad went to his own cubicle and booted up his computer.  He prayed that nobody would stop by this morning.  How would he explain not having a skirt on?