The Bet - Chapter 63 (Friday – week 9 Part 1 of 3)

The Bet

By Karen Singer

Chapter 63 (Friday – week 9 Part 1 of 3)

     Her dream was disturbing.  And the longer it went on, the more frustrated she seemed to get.  It was one dream, one subject, one event… but that one event managed to somehow play itself out over and over again – for various vague reasons.  The event of course, was Sissy’s testing. 

     In her dream she watched as Sissy quickly regained all his control – almost immediately.  She watched in despair as he stood over her… lorded over her… and preened and crowed about it like a proud rooster.  And she felt little and small and defeated at his feet. 

     Yet for some reason, she refused to accept that outcome, and somehow she managed to push everything back to the start again – back to the point before he still needed to try to regain his control.  And the dream played out differently.  This time she willed harder that she wanted to win, and for a while it seemed like she would.  But as before, once again he regained everything.  And he stood proud… and she felt defeated.

     Again she refused to accept it, and again the dream played out differently… and again he won.  And again… and again… and again. 

     She was becoming more and more despondent.  More and more frustrated.  More and more upset.  And then, on towards morning, somehow, she finally won.  And in her dream, she moved on to a new life, to a new house… only to find that Sissy wasn’t there with her.  He was gone again.  Gone because, despite the bet, she couldn’t hold him.  She had no way to hold him with her… because there were some things he still wouldn’t live without, no matter what. 

     So she got angry again… and the testing replayed itself… and as before, she lost.  And she lost… and she lost…

     His dream was chaotic, as if too many different things… too many different scenarios were all jumbled together at the same time.  He was home, in his apartment... his apartment that was decorated and stuffed with wonderful new things… and people.  But he knew that the one person who wasn’t there, was Mel.  She would never be there again.

     There were many people gathered around his new pool table, all having a great time.  His huge TV set was on and there was music blaring from his fantastic sound system.  So much great stuff now filled his living room… and everyone seemed to be enjoying themselves thoroughly.

     Someone approached him from the side.  “I’ll take one of those,” the man said. 

     Chad turned toward him and curtseyed before he held out the tray full of beer he had been carrying.  The man took one and deposited an empty bottle on the tray in its place.  “Thank you,” Chad replied in his sissy voice before curtseying for the man again. 

     He turned and walked toward the kitchen where he could deposit the empty beer bottle in the trash.  As he walked, he could feel the massive ruffles of his beautiful pink sissy dress caressing the tops of his legs.  Heavenly.  And humiliating. 

     So many people there, partying in his apartment, and he was once again reduced to nothing more than a total simpering sissy – right in front of all of them.  And he knew there was no way out for him.  He was stuck like that, and would be forever.  He was totally useless for anything except everyone else’s enjoyment. 

     And yet, he had won the bet.  Everything in the room seemed to confirm that very fact!  But still, he was once again demoted to being nothing more than a sissy – despite winning the bet.  The problem was, being a sissy was who he really was… and everyone knew it.  So that’s the way they always treated him.

     He carried his tray full of beer – beer that he didn’t like and never drank – out through the crowd of people again, his massive skirts brushing not only his legs, but they also brushed against so many other people in the crowded room – people who were all mostly ignoring him.  His journey through the room took him to his bedroom.  He entered to see who might be inside… who might want one of his beers. 

     Walking into his bedroom though was like walking into a different world.  Where his living room had been decorated with adult furniture and adult toys, his bedroom was instead decorated with baby girl furniture and baby girl toys.  It was a drastic contrast to the living room on the other side of the door.  It was a room for a sissy – a big sissy.  A room where any normal person would feel squeamish – and so did he.  But it was his room.  It was the only kind of furniture he deserved anymore – because he was nothing more than a big sissy. 

     And everything in the room confirmed what he already knew – that he had lost the bet. 

     He had come into the room to see if anyone there wanted one of his beers, but the only person in the room, was him.  As he looked around at his beautiful crib and his little play table and so many other things, he realized that nobody else would be in there… not even Mel.  But of course Mel wouldn’t be there.  She would never be there again.  Even though he has lost the bet.

     He went back out to the crowd of people on the other side of the door, the side where he had won the bet.  The side where he was still a sissy despite winning the bet.  Because no matter how things turned out, he would always be a sissy.  A sissy who deserved to be treated as nothing more than just what he was. 

     As he wandered with his tray of beer among the people, he was more aware than ever of the delicious swishing and caressing from his ridiculous but amazing ruffled underskirts.  If only everyone could feel what he was feeling right now!  He’d bet any of them would absolutely love to feel the wonderful caressing and teasing that his skirts were giving him just then.  So sensual.  So sexy.  And when coupled with the feelings from his super bulky and oh-so-wet diaper, it was almost more than he could bear.  All of it combined to make him feel so sexually alive.  To make him feel so much sexual need.  To make him feel… uh oh! 

     Even in his dream he knew better than to allow any of those feelings to affect his tiny little penis – always encased in its hard plastic shell where it belonged so it would be of no use to him at all.  He was a sissy, he wasn’t allowed the use of it.  He switched his thinking to imagine something long and sexy sliding in and out of his backside instead – much better!

     But even in his dream, he was aware that something felt different inside his diaper.  Something felt… odd.  Something felt… weird.  Something felt… wrong!  Even in his dream he realized that the massive bulk of his diapers – always pressing on him… were now also putting pressure on a little part of him that never felt that feeling before.  He was feeling things in a place where he wasn’t supposed to feel anything!  A place where it was dangerous to feel anything!  A place where such feelings could hurt!  Panicking a little, he was pulled out of his dream, and consequently out of sleep entirely.  His hand snaked down to press against the front of his bulky diapers… to press and to prod – uselessly against so many ultra-wet and bulky diapers.  And only then did he remember that he was no longer wearing the chastity device that had become almost a part of him for such a very long time.  He mentally breathed a sigh of relief because he wouldn’t have to worry about that kind of pain just then.  And a moment later, he revised his thinking – hopefully he wouldn’t ever have to worry about that kind of pain ever again. 

     He opened his eyes now to the light of day.  Full daylight – later than he usually woke up.  No alarm had pulled him out of slumber this time – there was no longer any need.  And the full realization fell on him in one huge swoop:  His period of servitude to Mel was over now.  A new period had just begun.  He now had today and tomorrow to prove what he had known from the very start – that you simply can’t make someone incontinent in only two months.  It can’t be done!  And now he would be the proof.  He now had two days to regain all his control and prove it – and consequently win the bet.

     The time had come.  Finally.

     But as he rolled off of his blow-up mattress onto his knees – not scattering any empty baby bottles as he usually did, a single odd thought came to his mind.  It was something remembered from last night.  Something she had said.  “Why can’t you just lose?”

     He struggled to his feet.  The massive bulk of his diapers keeping his legs spread wide apart.  His diapers were massive, and heavy, and wet, and yes, messy too – as always.  And he didn’t remember one time waking up in the middle of the night to wet… or to mess.  As usual.  That much of his control was going to take a bit longer to get back – or so he supposed.  But he wasn’t worried about that as far as winning the bet because he was more than sure he could regain all his daytime control very quickly.  And that would be all he needed to win. 

     Why can’t you just lose?

     Following a pattern that had been ingrained in him for two months now, he stumbled wide-leggedly out to the kitchen.  There was no note on the counter of course, but he did look for it.  He went straight to his refrigerator and pulled out three baby bottles… before he remembered that he didn’t need to drink them anymore.  He put them all back and closed his refrigerator again.  But as he turned away from it, he realized he was thirsty.  He was used to drinking three bottles first thing every morning!  He always did it!

     Turning back around – because he was thirsty, he opened the refrigerator again and pulled out one of the bottles – because he was thirsty.  There was no sense looking for a glass or anything else to use to drink from, he didn’t have any.  So he put the bottle to his mouth as he had done so often, and he drank – because he was thirsty.

     And following the same pattern he had always followed, he carried his one single bottle out to his one single solitary chair – that faced a wall full of shaming pictures.  He sat and put the bottle back to his mouth as he stared from picture to picture – to the bet contract – to the designs Sandy had done for his apartment – and back to the childishly colored pictures again.  And everything he looked at brought back a treasured memory. 

     His chance to live the dream was over now.  Once he regained all his control, all he would have left would be his memories.  Wonderful, amazing memories.  And he would very much miss all of it. 

     The dream was over.  Why can’t you just lose? 

     There was no smell of freshly brewed coffee to wake her.  No alarm, nothing to urge her out of her sleep… except time… and the need for coffee.  Even before she sat up in bed, she had the urge to call for Sissy to come and serve her.  But she remembered that he wouldn’t be there today.  Calling for him today would be useless.  And unless she won this bet, calling for him ever again would be useless.  And she already missed him.

     She forced herself out of bed and grabbed her robe as she headed out to her kitchen, or more precisely, out to her coffee maker.  She had to prepare the coffee herself, adding just the right amount of coffee grounds, filling the carafe with water, dumping it into the coffee maker, turning the damn thing on… and waiting… waiting… waiting!  It was so much better when Sissy had done it for her – even for such a short time as he had.

     The coffee finished making.  She filled her cup… and took a sip… and thought about Sissy – Chad!  Was he up yet?  Had he regained all his control yet?  Had he won already and she had lost?  She had no way of knowing any of it, and the wondering was already starting to eat at her. 

     Why can’t you just lose? 

     In a fit of frustration, she had yelled that at him just before he left last night.  It was what she wanted – naturally.  And she just knew that it was what he wanted too… he just didn’t know it.  Was she presumptuous to think that?  Not to her way of thinking.  Chad… Sissy… Chad might think otherwise though. 

     She carried her coffee out to the living room and sat in her usual chair with it.  Was it possible that he could win?  Was it possible that she could win?  When she looked at all the evidence she had so far – what little there really was, everything pointed to the fact that he was already totally and seemingly permanently incontinent.  At least it looked that way.  But looks could be deceiving.  And she knew that despite the evidence, he still seemed to be awfully confident that he could win this thing. 

     And if he won, then she would lose.  And she would lose not just the bet, but her dreams.  And… she would also lose… him.

     Why can’t you just lose?

     The massive bulk of his diapers were still in place as Chad shaved his face with his all too feminine pink razor and using women’s moisturizer instead of shaving cream.  It was amazing how good a shave he was capable of getting with it.  Better, he thought, than regular men’s shaving cream.  Maybe he’d continue to use it in the future.  Maybe. 

     With his face freshly shaved, he automatically grabbed a couple of disposable diapers to put on immediately after his shower.  And then he stopped himself.  Did he need them?  It was time now to start trying to regain his control – even though he hadn’t even started trying yet.  So did he need them?  But knowing that it would take a few hours at least to regain that control, he knew it would be safer to protect himself than be sorry.  The diapers could easily be pulled off as soon as he felt the need to go.  Besides, he hadn’t yet explored any of those boxes out there in the living room… the boxes that held all his old male clothes.  He still needed to find his old male underwear.  He’d look for it later – just as soon as he showered and got a couple of fresh diapers on to protect himself.  Then he could open all those boxes and enjoy exploring their contents.

     With that plan mapped out, he turned and entered the shower the same way he always did – not once looking in the direction of his toilet – still wrapped in layer after layer of plastic wrap so that he couldn’t get into it to use it.

     In the shower, he took the time to wash his whole body as well as his hair.  He shaved his leg… or rather he shaved his left leg.  He was just starting on his right leg when he realized that he didn’t need to do that anymore either.  But having just one shaved leg wasn’t very good – so he continued and shaved them both – before searching the rest of his body for any other stray hairs that needed to be attended to as well.

     Once his body was clean and dried, as fast as he could, he grabbed one of the diapers he had ready and got it on – before he leaked all over the place.  The diaper was fresh and dry, and was soon accompanied by a second diaper on top of it.  No use having to worry about changing too soon if by any chance he would have a little trouble with regaining his control – just as soon as he started trying.  Besides, the two diapers felt better than just one… more comfortable, sexier, and much more secure.

     He left the bathroom without once glancing at the toilet there that was still wrapped up in plastic.

     Why can’t you just lose?

     His thoughts turned back to Mel.  Was she up yet?  Was she dressed as well?  He was tempted to phone her… just to say hello, but he decided against that idea.  She was probably sleeping late today.  Probably very late!  They had been at it until midnight last night.  Yeah, he was sure she was enjoying a little much needed sleep.

     Wearing just his diapers, he went out to the living room and kicked one of the biggest boxes out into the middle of the floor where he could open it easier.  He pulled the tape off of it so he could open it. 

     Why can’t you just lose?

     Inside the box, he saw plastic!  He had to lug out the entire thing before he could see for sure that it was all his pants inside that plastic.  Obviously Mel hadn’t bothered to unwrap any of it before she shoved the whole thing into the box.  No problem, he would unwrap them just as soon as he got them into his closet. 

     Was she up yet?  What was she doing? 

     Why can’t you just lose?

     Mel wrapped her wet hair in a towel before stepping out of the shower and throwing her robe back around her.  Was he up yet?  He did like to sleep late.  And last night had been later than usual, so he was probably still sleeping.  She was tempted to call him, but there were too many reasons not to. 

     She stared at her closet for a few minutes before turning away and going to her dresser instead.  She pulled out a bra and panties and an old pair of shorts and a t-shirt – all of which got thrown on her bed before she got dressed. 

     Despite how casually she had dressed, there was no reason for her not to spend a little extra time on her hair – time she rarely bothered to spend.  With a tiny bit of makeup, the result was… pleasing. 

     Was he up yet?  Surely he had to be.  Had he regained all his control yet?  Stop it!  He’s probably still sound asleep!  And the more she thought about it, the more she wanted him to stay sound asleep.  The longer he slept, the less time he would have to regain all that control.

     Why can’t you just lose?

     He found his underwear – what little good it did him.  He left it in the box.  He didn’t have a drawer to put it in anyway.  He found his shirts, he even found his old wallet. Everything was opened and explored thoroughly – as if it was Christmas.  But it seemed like there were fewer boxes to open than he remembered having to lug up those stairs from her car yesterday.  All too soon, everything was found. 

     Was she up yet?  Surely she was.  What was she doing?  Should he bother to call her?  No, there was no reason.  She was probably glad to be rid of him for a while.  Glad for the little bit of solitude she could enjoy. 

     So now that he had found all his stuff, what should he do?  Get dressed he supposed.  He picked up the big package of wrapped up pants and carried them to his closet.  He struggled with the plastic wrap to rip it off so he could hang them all up – right next to his silly sissy dresses.  Men’s clothes in his closet again – yes!  And soon he would be wearing them!  He paid no attention at all to the yearning he felt to wear something feminine and pretty instead.  Today he could dress normally again.  Today he could dress like he should – like a man!

     Instead of hanging his shirts up, he just grabbed one.  He caught sight of his underwear in another box as he did it, but he knew he was going to leave the underwear alone.  He wasn’t ready for it yet.  He hadn’t started trying to regain his control yet. He did grab a pair of his old socks though.  Those he could definitely use right away. 

     Why can’t you just lose?

     He slipped the socks on out in the living room, his shirt as well.  The shirt seemed a lot bigger than he remembered.  Too big.  Of course, he was used to wearing everything now with those breast forms glued to his chest, so of course everything would seem to fit strangely, but for some reason, the shirt just seemed – to big.  He grabbed a different one instead, and that one seemed too big as well.  Had he lost that much weight?  Yeah, he knew he had. 

     Socks and a shirt… and diapers, he wandered back to his closet and selected a pair of pants.  He pulled them on – the first pair of pants, women’s or men’s, that he had worn in ages.  And as he pulled them into place – even over top of the two wet diapers he was wearing, he was surprised at how big they seemed – worse than his shirts.  The waist was particularly loose.  He tried another pair… then another.  All with the same results.  They were all too big.  He finally chose a pair of jeans and left them on, adding a belt that he tightened as far as possible to keep the pants from falling down.  The waist was bunched up horribly in several places.  They looked – ugly.  They felt just as bad.  He was tempted to grab a pair of women’s pants instead or maybe even a skirt, but today he could dress as a man again, and as a man, he could just tough it out.

     At least his old sneakers fit.  It just felt odd to wear them.  They were heavy and flat… and ugly.  Not that he consciously thought that.

     He surveyed himself in the full-length mirror hung on his closet door.  He looked… awful!  It was the best way he could describe it.  Not even counting his hair that he hadn’t bothered to do anything with, none of his clothes fit at all!  He looked – awful!  But today he was a man again.  And as a man, he would just have to make do.  He did make note that he needed to remove his earrings before he went out later.  The small sparkle from his earlobes was a bit out of place with the manly image he wanted to see.

     He briefly wondered what Mel was wearing.  Was she even dressed yet?  Or was she laying around her living room in just her robe?  She could look awfully sexy when she wanted to… or even when she didn’t want to for that matter.

     His stomach growled.  He was hungry.  No baby food breakfast for him today!  In fact, no baby food at all anymore – unless he wanted some.  His thoughts turned immediately toward going out to get some breakfast, but before he could go, he had to do something about his hair!  But what? 

     He grabbed his brush and brushed it this way and that.  But since Cassie had cut it so femininely, it was hard to make it look totally masculine.  He figured a haircut would be needed very soon.  Maybe he should ask Cassie to trim it before he went to the barber shop so it wouldn’t be quite so embarrassing for him.  But for today… and he guessed tomorrow as well, his hair probably had to stay the way it was.  And it would have to look awful – just like everything he was wearing.