The Bet - Chapter 57 (Saturday – week 8 Part 1 of 9)

The Bet

By Karen Singer

Chapter 57 (Saturday – week 8 Part 1 of 9)

     He whimpered.  And even in the real world, the sound escaped past the pacifier guarding his lips as his mind reacted to the events playing out in his dreams. 

     He whimpered, as once again he sat on Derek’s lap, fighting with him… struggling to get past Derek’s arms to wrap his own arms around Derek’s neck.  And once again the fatal kiss happened, just as it had happened before – just as it had happened numerous times already in his dreams.  His arms were locked behind Derek’s head and he forced his own head up toward Derek’s lips.  And their lips met once again in a long embrace.  He could feel the softness of Derek’s lips… just as much as he could feel the intense humiliation from having to do the act… just as much as he could feel the sexual stimulation that the situation was sending through him.  And yet, just as it had been in real life, the Derek in his dreams wasn’t happy about it in the least!  And in truth, neither was he!

     As soon as the kiss ended, he had to go and stand shamefacedly in front of all too many women where once again he tried vainly to explain why he had just kissed Derek… again.  Over and over, the women made him go back to Derek’s lap and kiss him.  He didn’t want to do it!  But because he was nothing but a big sissy, he had no choice since everyone was making him do it.  A sissy’s place is always to do whatever anyone tells him to do – especially women!  He was so ashamed!  And… he whimpered.

     The women taunted him.  They outright called him a sissy.  He was forced to curtsey over and over for them as he answered their inane questions.  They forced him to lift his skirts to show off his soaking wet diapers.  They made him suck his pacifier in front of them… or his thumb.  Then… they made him go back and kiss Derek again… and the dream once again repeated itself. 

     The background music caught his attention in the middle of one of his kisses, but the dream was too good to pay the music much attention.  He noticed the music more as he once again returned to curtsey in front of the women and show them his overly soaked diaper.  It wasn’t till one of the women in his dream asked him if he was leaking that he noticed the music more… music that something in his brain recognized as not belonging to his dream… yet it was something that he shouldn’t ignore. 

     With one last effort to hold onto the wonderful humiliating dream, his mind finally let it all evaporate into nothingness as the music came through much more clearly.  And then the music ended and he heard someone talking… a commercial to buy something.  Ugh!  But it was enough to make him open his eyes. 

     His first thought of the day was that this was a much better way to wake up every morning than with the obnoxiously loud rock music that Mel had set his alarm with every night.  His next thought was of what he had to do now that he was awake.  He rolled off his blow-up mattress, once again knocking over a few empty baby bottles in the process.  He didn’t bother to turn his alarm off, but he did check the time.  Not bad.  It was only five minutes after he had set his alarm to go off.  And he was up!

     His next thought was about Mel’s note that she left for him every day.  But she had said last night that there would be no more notes.  But did she leave one anyway?  Something in him really wanted her to have left a note.  He forced himself to get to his feet, despite the mass of very heavy and bulky diapers that he was wearing.  He rubbed at his chest where the breast forms were usually glued on, but they were gone today.  In a way, his body missed them.  But most of him was happy they were gone.  It felt strange to walk around without that weight bouncing around on his chest.  Yet… today, it was also a luxury.  He had no misconceptions about how long he would be going with the breast forms.  Mel always glued them back on the next day.  He had… a few hours now at best to enjoy being without them.

     He waddled very wide-leggedly out to his kitchen where his eyes went first to the spot on his counter where she always left her note.  Bare.  Empty.  Nothing.  No note.  He felt disappointed.  Continuing on, he went straight to his refrigerator where he grabbed three baby bottles of Mel’s lousy green tea from his dwindling supply.  He dropped his pacifier from his mouth on the counter top and carried the three bottles out toward his one and only piece of furniture… an old chair from his previous marriage set in front of his wall of shaming pictures. 

     He sat in the chair and put the first bottle to his lips.  As he started nursing, his eyes wandered over all the things on his wall.  The childishly colored pictures that he had done in the restaurants, the plan that Sandy had done for his apartment that would essentially turn the whole thing into one big nursery, and of course, his framed copy of the bet between himself and Mel.  The bet that would be over with very soon. 

     It was Saturday.  Next Saturday he would have to be judged to determine if he could indeed control his bladder like he claimed he could.  Next Saturday… the entire thing would be over with!  The end.  And whatever would come beyond the end was what scared him the most – no matter how the bet turned out.

     Next Friday, he would have all day to start regaining his control.  Could he do it?  Could he get it all back in just a few hours like he thought he could?  He certainly hoped so!  Otherwise he would lose and would wind up with an apartment that looked like a little girl’s nursery and would spend a year wearing diapers and a maid’s dress serving Mel’s every little need.  But… if he won, Mel would furnish his entire apartment for him according to Sandy’s “other” plan – a plan that included a pool table!  How cool would that be?

     And in between… he had what…  He had to count the days on his fingers to be sure.  Today which was Saturday, Sunday, Monday, Tuesday, Wednesday, Thursday…  That was six days. Six more days before next Friday.  Six more days of intense humiliation.  And he had no illusions that there would be any letup on that!  Six more days.  Not many, yet it still seemed all too far away.

     As he unconsciously nursed on his bottle, his eyes no longer saw the shaming things on the wall in front of him.  He was too preoccupied with wondering what would happen in the future… after the bet was over with.  Either he’d wind up as Mel’s servant and a year of more humiliation.  Or he’d wind up with a pool table and have to figure out how to rescue his life from all the humiliation that Mel had already put him through.

     And his big problem was, he honestly didn’t know which option scared him more – winning… or losing.

     She didn’t sleep as well as she hoped she would.  She kept waking up, over and over again, her eyes opening just a crack each time to check her clock… to see just what time it was.  Would he be there in the morning just as she hoped he would?  It was all her mind could think about.  So over and over again she woke up to see if it was time yet.  And over and over again she was disappointed as very little time had actually passed.

     Eventually, she did doze… and dream.  But it was a troubled dream.

     She was standing in the doorway of her new house, looking at the large dirty back of a truck pulled up to the door.  But where was Sissy?  He was supposed to be there to unload everything and put it all away!  Her furniture was all here… on the truck… but where was Sissy?  She ran back into the house, a house of nothing but bare empty rooms.  She glanced into room after room searching for him, but she saw no sign.  She stopped.  Sissy!” she yelled.  “Where are you?”  In her dream, the empty walls of her house echoed back her words, but that was all she heard. 

     She went back to the door – back to where the truck was.  Still no Sissy.  Nobody to move the things into her house and put them where they belonged.  But could he do that?  Furniture was heavy… and she had lots of it.  But Sissy wasn’t all that strong.  Probably not even as strong as she was.  Maybe that was why he was hiding. 

     Angry at him, she got up onto the back of the truck and struggled to open the door.  She was panting hard with the effort, but eventually, she forced the big door all the way up.  And inside, all jumbled together, were all the wonderful pieces of furniture from the house she had grown up in.  All her favorite pieces – of her mother’s furniture. 

      “Sissy!  Come help!” she yelled.  But once again he didn’t come.  Frustrated, she was forced to try to grab one of her chairs and move the darn thing by herself.  It was so heavy!  Not to mention big.  She managed to move it only a tiny bit before she gave up.  “Sissy!” she called again.  And as before, there was no response.  Where was he?

     She got down off the truck and went searching for him again.  All through the empty house she went.  Looking in every room.  Upstairs and down.  Nothing.  Nothing but empty rooms.  It was an empty house full of nothing… and no one.  Where was he?

     Totally frustrated with him, she started wandering back out toward the truck – the truck she had no idea how she would deal with now.  And half-way back, she realized why Sissy wasn’t there to help.  How could she have forgotten?  How could she have ever thought he was going to be there in the first place?  He wasn’t there… because he was never going to be there. 

     As despondency took hold on her emotions, she remembered what she had not wanted to remember… that she had lost the bet.  She had lost.  She hadn’t been able to make him incontinent… all because she hadn’t been able to figure out how to get past the three obstacles that stood in her way.  Sissy had regained all his control before the judging even started – because he had believed in the three things that now haunted her the most.

     Self-respect.  Friends.  And… a life!

     Chad checked his reflection in the mirror one more time.  He was as ready as he was going to get.  As far as he could tell, his maid’s uniform looked perfect!  Even the white apron on his uniform looked perfect – or so he thought.    He had ironed it as best he could last night.  His low-heeled shoes were freshly shined.  His hair was… well, decent he figured – for a guy dressing as a woman.  His makeup… okay, decent under the same circumstances.  Under his uniform he was wearing a bra with his false breasts just shoved into it to fill it out.  They would get glued back onto him later… sometime.  He was wearing his waist cincher to further reduce his waist that had been growing steadily smaller since this bet had started.  And the only other thing he was wearing was the single diaper that was already growing wetter, but it would take a lot more since he had put it on only half an hour ago.

     He was ready.  He looked… okay… for a guy who was dressing like a woman – or a maid as least.  And despite how much progress he had made in the last two months, there was still no doubt that underneath his dress, and underneath his makeup, and underneath his hairdo – he was still a guy in a dress! 

     He went to the door where he grabbed his diaper bag, his red purse, and his bag full of all the empty bottles he had finished last night and this morning.  Then taking a deep breath to brace himself for the upcoming day, he opened his door and went out. 

     He almost knocked on Mel’s door as he usually did, but that would have been disastrous this morning.  He was supposed to go in and get her coffee ready without waking her.  He fished his keys out of his purse and as quietly as he could, unlocked her door and went in. 

     Her apartment was mostly dark.  Only a little light filtered in from the windows and the doorway behind him.  Setting his diaper bag quietly on the floor under her little table, he went into the kitchen where he turned on the light.  Only then did he go back to close the apartment door – as quietly as possible. 

     He went back to the kitchen and started preparing her coffee.  Once the machine was set to work, he had time to further assess the situation.  The coffee was making, so what was he supposed to do now?  He certainly didn’t want to wake her.  But… was she awake? 

     He quietly headed for her bedroom, tiptoeing by the time he got halfway there.  But he was still worried about making too much noise so he removed his shoes.  In his bare feet, he cautiously approached her bedroom door.  It was closed – except for a small crack.  He pushed it open and chanced peeking in.  As far as he could see, which wasn’t much in the mostly dark room, she was still sleeping.  He pulled her door back to the position it had been before he had opened it further, and went back to the kitchen, picking up his shoes along the way.  She was sleeping… so what was he supposed to do now?

     He had already finished three baby bottles this morning and didn’t want to make matters worse by grabbing another one too soon.  Instead, he started opening cabinets, searching for something he had seen once or twice before.  There it was!  He pulled out a serving tray that she had stored down there.  If he was going to do this, he might as well do it right.  He pulled one of her cups that she liked out of another cabinet and set it on the tray.  What else?  He thought about a vase with flowers, but she didn’t have any flowers.  And just the cup by itself looked dumb on the tray.  He put the tray away for another time.  All he needed to do now was to fill her cup and bring it to her – when she woke up!  Whenever that would be. 

     So what was he supposed to do with himself now?  The coffee was almost ready.  He was ready.  But she wasn’t.  He thought about sitting down, but with his diaper getting wetter and wetter, what if he leaked.  That wouldn’t exactly be good for the furniture.  But what if…  He pulled the tray off of his highchair and climbed up into it, enjoying the luxury of just sitting down and taking the load off of his feet for a while.  Ten minutes later though, he gave into temptation and pulled yet another bottle out of her refrigerator and brought it back to his chair where he sat and drank it.  He did have a deadline to meet – if she was awake when it came.  He might as well sit and relax while he could.  His days were usually stressful enough.  Usually?  Always!

     So when was she going to wake up?

     Mel opened her eyes.  There was no alarm to wake her, yet something had pulled her from the tenuous sleep she had finally been enjoying.  The room was getting lighter so it was finally morning.  She glanced at her clock – yes, it was morning.  Not as late in the morning as she would have liked, but it was finally morning.  But what about Sissy… was he there yet?  It was then that her brain kicked in far enough to realize what her nose had already alerted her to while she was sleeping – the smell of coffee.  She smiled and rolled luxuriously around in her sheets.  Yes, he was here!  Yes, he had already made her morning coffee!  Yes!  Her dream was coming true!  She hoped anyway. 

     Should she call him now?  Or just enjoy the luxury of knowing he was there and would take care of her every need as she saw fit.  But he was learning to be a servant, and the main thing a servant needed to learn was to wait.  So with a smile on her face, she rolled over and tried to go back to sleep for a while.  It was early… and she had no reason to get up out of bed yet. 

     Happy in the knowledge that he was there, she once again dozed.

     Chad had a small problem.  He had now finished five bottles since he had gotten up this morning – and he was leaking already.  He had stopped trying to sit even in his highchair once his diaper started getting too wet for fear that his leaking diaper might put a wet spot on the back of his perfectly pressed dress.  But what was he supposed to do about his leaking diaper now?  Should he change himself?  Or would she finally wake up soon?  He had been waiting for her to get up for almost an hour now! 

     Changing his leaking diaper seemed like his best option, but what if she woke up and called him while he was in the middle of changing?  That would be an even bigger problem!  But if she slept much longer, then his diaper would not only be leaking, but there was a chance his uniform could get wet.  He finally decided he would have to change it and hope she didn’t call him while he was doing it. 

     As quietly as he could he got his diaper bag and carried it into the kitchen.  A moment later, the skirt to his dress was hiked up over his waist.  He grabbed a fresh diaper from his bag, and keeping it handy on the counter next to him, he opened one side of the tapes on his leaking diaper, letting it drop all the way to the floor.  He grabbed his new one quickly and started to pull it between his legs.  As he did, he felt his arm suddenly get wet.  He was peeing yet again without knowing it. He quickly finished pulling it into place and started fastening the tapes.  As far as he could tell, he was now peeing almost constantly.  Just a little tiny bit at a time, but it was so often now that it hardly ever stopped.