The Bet - Chapter 64 (Saturday – week 9 Part 2 of 7)

The Bet

By Karen Singer

Chapter 64 (Saturday – week 9 Part 2 of 7)

     He rolled over on his blow-up mattress onto his stomach, his mind automatically preparing for the pressure he expected to feel from the glued-on breast forms.  But when that pressure didn’t happen, it was enough of a change to bring him totally out of his sleep – sleep that he had been gradually leaving for a while now anyway.  With a grunt of realization that the breast forms weren’t there anymore, he allowed himself to fully collapse the weight of his body onto the mattress.  It felt good, but at the same time, it felt strange. 

     He was awake enough now to start noticing his body more and take stock of everything.  His legs were forced wide apart by the bloated thickness of the three layers of diapers he had put on last night.  He couldn’t tell yet if they were as wet as they usually were every morning since he had drank hardly anything at all last night.  But they were definitely very wet… and definitely messy as well.  And once again he didn’t remember doing either after he fell asleep last night.

     He turned his head and the stupid pacifier in his mouth rubbed against his pillow.  It wasn’t usually a problem since he usually had to support his body more when the breast forms were there.  He remembered trying to go to sleep without the pacifier last night, but he had been having trouble sleeping and he got up to grab it, hoping it would help.  It must have. 

     But now he was awake again and his room was full of sunlight.  He didn’t know what time it was, and wasn’t even sure he cared.  Could he go back to sleep?  Why not?  He closed his eyes and snuggled into his pillow.  But sleep wouldn’t come… exactly.  His mind wasn’t exactly dreaming, and it wasn’t exactly awake either.  But instead it started thinking about deliciously erotic things that turned him on.  And he allowed himself to sink fully into those wonderful sexy images.  And inside his very bloated diaper, he felt his tiny underused penis start to grow.  The realization again brought that quick bit of panic over the pain his chastity device would cause him… but once again, he woke up just enough to remember that the device wasn’t there anymore, and he could dream these dreams to his heart’s content!  And… he did!  Purposely! 

     His mind dreamed about wearing diapers – like he was.  It dreamed about being controlled and forced to wear them – like he had been.  It dreamed about being forced to wear dresses and high heels and all sorts of feminine finery  - out in public – again, just as he had been only a few days before.  But this time it was different.  This time he could allow his body to respond fully.  This time there was no chastity device holding him back.  And this time, he was determined to ride the wave and enjoy it to its fullest!

     For the first time in a long while, his tiny little penis was no longer so tiny.  For the first time in a long while, it behaved normally – and it grew!  Normally!  And for the first time in a long while, he concentrated more on getting pleasure from it, than on getting that pleasure from the opposite side of his body – where he wasn’t supposed to “normally” get that pleasure. 

     The images of his fantasies played on, and he found himself trying to hump his blow-up mattress.  But getting the kind of stimulation he needed wasn’t happening.  His overly bloated and messy diapers were a bit too bloated.  They weren’t letting him get the right kind of pressure where he needed it the most.  Coming more and more awake, he put his hands down under him, right under where his penis was inside his mass of diapers.  As he humped and pressed his groin into the mattress, the fingers of both hands pressed up as hard as they could.  But that damn bulk of his diapers was still so much that he couldn’t feel it much more than before.  Frustrated, he pulled his hands back up and tried to figure out what he could do. 

     Getting to his knees, he grabbed his pillow and stuck that under him and he went back to work.  But just like with his fingers, the pillow did nothing for him at all… and his frustration grew.  So close!  And he was being foiled by the super bulk of his diapers!  Fully awake now, even though he didn’t really want to be, he knew that the only way he was going to get himself off, was to get his diapers off first! 

     He rolled off of his mattress and because of the bulky diapers forcing his legs so wide apart, he had to struggle to get to his feet.  He was tempted to take the diapers off right there in the middle of his bedroom, but fortunately he remembered that it was all too likely that he might wind up peeing on the floor.  Besides, his diapers were not only wet, they were messy too.  The bathroom would be the best place to go.  He headed there with his usual morning wide-legged walk. 

     In the bathroom, the first thing he noticed was his freshly cleaned, no longer wrapped in plastic, toilet – just waiting for him to use… still waiting for him to use… even once.  He hadn’t managed that little feat last night at all.  He purposely put that problem out of his mind.  He had more “interesting” issues to contend with first.

     He struggled with his plastic panties to pull then over his massive diapers and off his legs.  By the time he attacked the bulky diapers themselves, he was no longer feeling as desperate for release.  All the desire was certainly there, but the process of changing rooms and having to get everything off had interrupted the fantasies that had been playing out in his mind.  But still… he wasn’t going to let this opportunity go to waste!

     Just to be safe, before removing his messy diapers completely, he stepped into the tub.  It would be much safer there.  His diapers got carefully folded over and set out of the way in the very back of the tub.  He could forget about them for a little bit now.  His cock wasn’t so raging as it had been anymore, but he was confident that he could make it grow again.  But after being bound up in all those hot, bulky, smelly diapers, it was rather… disgusting to touch.  He turned the tub faucet water on and let it run for a minute to warm up, then he turned on the shower and quickly washed off that part of his body and his backside before turning the water off again.  Now he could get back down to it.  He was soaking wet, but it was from the shower and not anything bad. 

     But as he looked down to take matters in hand, he noticed that not only was he not hard anymore, the shower had taken care of that, but once again, he was peeing without knowing he was doing it.  Well, sort of peeing.  It was really just dripping out a little like he usually did now.  But it reminded him of his need now to regain all his control.  And the fact that he was quickly running out of time slammed home worse than ever! 

     For the first time in two months, he was no longer confident about winning the bet.  For the first time in two months, he was faced with the very real possibility that he really could lose the bet.  For the first time in two months, he was forced to seriously look at what might happen if he lost.  And that possibility was looking more and more likely with every passing minute!

     But as much as he needed to regain his control, this was still the first opportunity he had to orgasm normally – like a man!  Okay, he had to masturbate, but it was still like a man!  He grabbed himself the best way he knew how, and went to work.  He had to force all those wonderful fantasies back into his head.  But this time, with every fantasy that came to mind, the very real possibility that he could really be stuck that way for a very long time also hit him just as hard, or harder.  Despite the fact that it would usually add to his fantasies, this time it took much of the joy out of the process.  He had to work all the harder for his release because of it.  But there was no question about his perseverance.  This was the first opportunity he had in nearly two months, and he wasn’t going to waste it! 

     Fortunately, he hadn’t had a real orgasm in nearly two months, and in the end that helped him.  But the end result wasn’t anything fantastic.  Not by a long shot.  And when it was over, he wondered if maybe the wonderful orgasms he had experienced when Mel had reamed his ass might not have been better.  It was hard to tell though.  All that worry now definitely took the edge off of everything.  And now that he had finally had his “normal” release, something else was gone as well – his usual desire for all his sissy stuff. 

     She wouldn’t really force him to serve her for an entire year, would she?  But the more he thought about it, the more he remembered just how hard she had worked on him over the last two months – just how much effort and worry she had put into it… into him.  And he knew without a doubt, that Mel had every intention of forcing him to serve her for the full term.  And she was a lawyer, there was probably something in that notarized contract they had both signed that would carry at least a little legal weight. 

     So if he didn’t get his control back – very soon, then he had no doubt that he would be… screwed!  He smiled… no doubt – literally.

     He turned his shower on again, and this time gave his entire body a thorough scrubbing – but not bothering to shave his legs or anything else.  But he did notice that they didn’t’ really need it anyway since he had just done them yesterday.

     As he turned his shower off, he heard his phone ringing.  Who would be calling him now?  Mel of course.  But he was just coming out of the shower, and she would have to wait.  He wasn’t serving her anymore… unless he lost the bet later today.  But he still had no intention of losing.  In fact, he was more determined now to win than ever!

     Mel hung up her phone.  He hadn’t answered.  Was he still sleeping?  Or ignoring her?  Either way, she didn’t have any way of knowing what was going on with him.  No way of knowing if she was still winning or not.  And she was now guessing that she wasn’t.  She hated being ignored!  Why hadn’t he answered?

     Chad stared at the underwear in his hand.  His old male underwear – freshly washed – yesterday.  He was standing in the tub again because he was still dripping pee.  He had ran out as fast as he could and grabbed them, but instead of putting the underwear on right away, he had carried them quickly back to the tub again, all because he was still dripping pee.  Not a lot.  Not constantly anymore, but he still didn’t know when it was going to come out of him.  His hopes were that with the regular underwear instead of the diapers, he would be forced to be more careful… and consequently he would start to feel things normally again.  Besides, the underwear would let him know every time he wet himself.  All too often those diapers wicked things away before he even had a clue.  But now he was stuck with a decision.  Should he put them on and hope they worked… or should he go with a diaper instead for a little while more until he was more sure he could finally hold back? 

     His mind flashed back to last night.  He had tried.  He had tried hard all night!  But it wasn’t until later in the evening that he had made any progress at all.  It wasn’t until then that he had finally started feeling it again.  He had finally felt the need to pee, but not once had he been able to stop it.  And every time he felt it, he had started peeing almost immediately.  As usual, not a lot.  But even a little but was total failure.  But at least he had been feeling it again… and wasn’t just feeling it the first and most important step?  He had done that, and been proud of that fact when he had finally given up and diapered himself for bed.

     But now it seemed that in the cold light of day, everything that he had gained again last night was gone.  He wasn’t feeling it anymore.  And now he was trying to learn it all over again.  So… should he go with his old men’s underwear… or the diaper?  A little more pee dribbled out of him again.  Last night he had definitely made that progress while wearing a diaper.  With a bit of frustration, he tossed the underwear aside and grabbed a fresh diaper – but just one. 

     Feeling secure and safe, he climbed out of the tub and took care of his messy diaper from last night.  Then he shaved and brushed his hair.  But all the while, his mind was really doing nothing but concentrating on trying to determine if he was going to pee or not.  In the end, his hair wound up looking worse than it had yesterday.  Disgusted with that, as well as disgusted with the fact that he knew his diaper was a little bit wet again, he went out and got dressed – same too big pants as yesterday, different too big shirt.

     He wandered aimlessly around his apartment, much like he had done all last night, not looking at anything in particular, only concentrating on one thing – trying to feel if he had to pee or not.  And his stomach growled.  He realized he was famished.  He hadn’t eaten a single thing since lunch with Mel yesterday.  Mel!  She had called.  Should he call her back?  But he was hungry.  He needed to go get something to eat.  But he knew without a doubt that he would call her.  There was something about her… something he knew even though he did his best not to think about it.  He really cared for her. 

     He fished his phone out of his purse, and called her. 

     The minute Mel’s phone rang she answered it – rather desperately.  “Hello?”

      “Mel?  Did you call earlier?”

      “Chad!”  Relief swept through her.  “I’ve been so worried about you!”

     Of course she would be worried – worried about him winning the bet!  “I’m fine,” he replied. 

      “Why don’t you come over?” she suggested.

      “No, I’m hungry.  I’m going to grab something to eat.”

      “Why don’t you come here?  I’ll fix you something.  Or you can fix something yourself if you like.”

      “No, I think I’m just going to grab something quick and bring it back here.”

      “Well then at least let me come with you!”

     Chad thought about it for a minute.  “Sure, if you want.  But I want to go right now.  I haven’t eaten anything since lunch yesterday.”

      “Since lunch!  Chad!  Why not?  That’s stupid!”

      “So?  I didn’t feel like it!  But if you’re going with me, I’m leaving right now.”

      “I’m on my way!”

     Of course, he didn’t leave quite that fast.  He first had to get everything he needed back out of his purse again and transfer it all to his pants pockets.  But then he was ready.  He opened the door and walked out, just as Mel was coming out of her door as well.  He waited for her at the top of the stairs.

      “Good morning,” Mel said brightly, trying her best to put a smile on her face.  To her, he didn’t look very well.  And it wasn’t only his overly large clothes or his hair that looked… weird, it was a mess, even though she could tell he had brushed it – somewhat.  No, there was something about his face that didn’t look good.  He looked – worried.  But how much of that was from not eating since yesterday afternoon?  She followed him down the stairs, and followed him to his car this time.  She did her best to study him as he drove.  Yes, he definitely looked worried. 

     The trip to the fast food restaurant wasn’t far and Chad went straight to the drive-thru lane where he ordered the first breakfast the store had on their list.  He turned to Mel, “Are you getting anything?”

      “I’ll have the same,” she replied without thinking. 

     Chad passed the order through the system and drove around to the window.  Mel fished some money out of her purse.  “I’ve got this,” she said as she pulled her money out.  Chad took it without a reply. 

     Nothing was said between them until halfway through the drive home, and then Mel couldn’t wait any longer.  “Chad… I have to know how you’re doing!”

     Of course she would.  He was only surprised she had waited this long.  But how should he reply?  “I’m… working on it,” he finally told her.

      “Working on it?”

     He only glanced over at her without saying anything else.

     Mel wondered what “working on it” actually meant.  To her, it sounded like he had made some progress but perhaps wasn’t all the way there yet.  But it seemed that he wasn’t going to be very forthcoming with details.  “Why don’t you spend the morning at my place,” she suggested.

     He thought about it and shook his head.  “No.  I have to…”

      “Chad!  You don’t even have any furniture!”

      “I’ve got my chair if I need it.  It’s enough…” he turned his head toward her, “for now.”

     He could be so exasperating!  “Damn it!” she exclaimed.  “I want to spend the day with you!  Won’t you let me do that?  Please?”  She waited, but he made no reply.  “I’ll stay out of your way if you want.  I won’t even say anything if you want!  Please?  I want to be with you!”

     He looked back at her briefly before pulling into the apartment complex.  She really did seem… concerned.  And there was one other thing too, despite the battle they were currently locked into, he did care for her.  He really wanted to spend as much time as he could with her… even though she would most likely be totally out of his life very shortly.  He gave in.  “Sure,” he replied.

     Mel breathed a sigh of relief.  What was going on in that strange head of his?  But at least she could be with him… and watch him.  And… maybe she could figure out how he was doing.

     They carried everything straight up to her apartment and sat down at her table to eat.  Like yesterday, having him sitting across from her, so normally, while they ate, seemed almost surreal, but she didn’t say anything at all about that.  Instead she said, “The ladies will be here at one.”

     He nodded as he took a large bite of his breakfast sandwich.  “I know,” he said with his mouth full of food.

      “They suggested that we don’t have any lunch before that.”

     Still chewing, he replied, “I know.”

     She ate some of her own breakfast before saying, “I wonder what they’re planning?”

     He shook his head.  “I have no idea.”

      “Me either.  But it sounds… strange.”

     He thought about that.  “Yeah, it does,” he agreed.

     She leaned a bit toward him.  “Chad… please… how is it going?  Have you regained all your control yet?”

     He didn’t want to admit, especially not to her, how badly he was doing.  “I’m working on it,” he said again.

      “Damn it!  That’s not an answer!”

      “Yes it is!  I’m working on it!”

      “So you haven’t gained it all back yet?”

      “Not… all of it,” he finally admitted, thinking about the fact that he now pretty much knew every time he was going to pee, as well as the fact that he knew immediately after feeling it that he was already peeing.

     She wasn’t sure what that meant.  “What does that mean?”

      “It means… that some things have come back, but… but I’m working on it!”

     Mel felt totally frustrated.  And yet, he had told her some.  He had some of it back – which wasn’t good for her side at all.  But clearly he was very troubled about the part he didn’t have back yet – which sounded very hopeful for her.  So overall, she guessed that she was still winning.

     She ate some more of her breakfast even though she hardly tasted it.  “How about last night?” She asked.

      “Last night?”

      “Did you… did you wet yourself… you know… in bed… while you were sleeping?”

     He looked at her for a moment before sheepishly nodding.  “Yeah.  That part may take a while longer for me to control.”

     That had sounded promising to her too.  “And how about… um… the messing.  Did you mess your diaper last night… while you were sleeping as well?”

     Once again he paused before confirming it.  “Yeah, that too.  As usual, I slept through it.  But I still doubt it will take me long to get that control back too.”

     But we’re only concerned with today now.  That’s it.  Today is the day. This afternoon is when they’re all coming here to judge you.  After that, it’s all over and it won’t matter anymore.”

     “You don’t have to remind me, I know,” he replied rather sullenly.  “But what happens in the middle of the night isn’t everything!  The most important part is what those judges are going to see for themselves!  They’re only going to be interested in whatever happens right here in front of them!”

     She nodded, then pressed, “Yeah, you’re exactly right.  But I’m starting to get the feeling that it’s not going so well for you right now, am I right?”

     He stared rather angrily at her again for a moment before lowering his eyes.  “For now,” he replied.  He looked up defiantly again.  “But I’m still working on it!”

     Maybe it was the lawyer in her, but she pounced back.  “Yes, you’re working on it, but will you gain enough of it back before they get here?  Will it be enough?”  A broad smile cracked its way across her face.  “Because from what I’m picking up, it looks like you’ve already lost!”

      “Don’t rub it in!”

     She backed down a bit.  “I’m… not.  I mean, I won’t.”  Then she changed direction somewhat.  “Well, maybe a little,” she told him with a tiny bit of a chuckle.  “After all, I have put an awful lot of work into this.  I think I deserve at least a little bit of a victor’s chance to gloat.”

     He looked at her angrily for a few moments before his face changed and he actually chuckled a little as well.  “Yeah, I guess you do deserve that much.  And I guess… I deserve it too.”  His eyes suddenly shone bright with determination.  “And just think how that’s going to feel when I turn around and do it right back to you – when I win this thing!”

      “When you win?”  Suddenly she wasn’t as sure of this anymore as she was pretending to be.

     He nodded confidently.  “When I win!”

     There were broad smiles on each of their faces as she replied, “Then I guess we’ll soon see!”

     Despite the smile of certainty on his face, Chad didn’t feel confident at all that he was going to win.  Not… at… all!

     After breakfast, instead of sitting and talking, he did his best to be by himself… to concentrate and work.  And Mel did her best to leave him alone.  And all morning long, they both kept watching the clock. 

     But breakfast seemed to help Chad.  It was shortly after breakfast that he was able to hold back his pee for the first time.  Granted, it was only for two seconds before he felt it leaking past his muscle control, but they were two of the most important seconds in his life!  Now he just needed to feel the need to pee again so he could practice holding back even more.  But feeling the need to pee required that he have enough liquid in his system so he would have to go again soon.  He thought briefly about the baby bottles in her refrigerator.  He could grab one and carry it around with him like he usually… or like he used to do.  But after thinking about that, he opted for a cup of coffee instead.  The coffee did seem to help – that problem, but it did nothing for his ability to hold back.  That was going to take nothing but work and determination.  And the time was quickly running out!

     Mel watched him carefully.  Her laptop was in her lap, but she never bothered to even turn the thing on.  He paced here, he wandered there, mostly looking nowhere but at the floor.  No wonder he didn’t care that his apartment had no furniture, he never sat down.  And through it all, he carried that mug of coffee and sipped from it frequently.  She made another pot – twice while he did nothing but wander and stare at her floor. 

     Was he gaining anything back?  He had said that he had some… but some what?  What had that meant?  She saw him looking at the clock almost as many times as she did, but was he timing how long he was holding back?  She would have asked, but she felt fairly certain that he wouldn’t tell her.  And right now, he deserved the chance to do this – his way.  And still, she felt nothing but – hopeful… for herself.

     The clocked ticked its way around to twelve o’clock, and still he didn’t change his routine.  Not even the expression on his face seemed to change, except she could tell he was becoming more and more worried about the time.  Twelve-fifteen came and went, and still he wandered and sipped from his mug of coffee.  And still… she knew nothing more.  But in all that time, not once had she seen him even go into the bathroom.  And all that coffee he was drinking… how many diapers did he have on?