The Bet - Chapter 64 (Saturday – week 9 Part 5 of 7)

The Bet

By Karen Singer

Chapter 64 (Saturday – week 9 Part 5 of 7)

     Macy’s did have a nice selection of skirts.  In fact, they had a nice selection of all types of clothes… women’s clothes at least – or so Chad thought.  It was something he most likely wouldn’t have realized or even thought about two months ago.  Now, as strange as it seemed to him, he appreciated more the selection of clothes that was available to him.  He seriously doubted though that he would have felt as comfortable looking at the skirts if he wasn’t dressed as a woman – and if he wasn’t in the close company of so many “real” women.

     The one thing that did scare him while he was looking over their skirts, was that the nearest bathroom Sandy had told him about was a mile away.  He knew as soon as she told him that he would never make it there in time.  But that didn’t mean he wouldn’t try.

     As he looked over the selection of skirts, trying to find one that he thought would work well for the testing he was in the middle of – as well as go with the top he had on, he was suddenly struck by an idea.  If the bathrooms were so far away, and since he had no doubt that he would have to go… eventually, then why not head that direction now.  Maybe he could actually get there by the time he had to pee!  He stopped looking at the skirts and turned toward Sandy who was a short distance away looking at the clothes on another rack.  “Uh…. Where did you say those restrooms were… in the back of the store?”

      “My God,” Sandy exclaimed.  “Do you have to go already?  Okay…”
     Chad just shrugged. “I’ve had a lot to drink today,” he replied – as he was already heading quickly in that direction.  He was walking, but he was walking fast.  No telling when that suddenly little urge was going to hit him. 
      “I’ll go too,” Gloria said as she followed Sandy and Chad toward the back of the store.

     For a large store, it took a surprisingly short time to reach the public rest rooms there, and by the time Chad walked into the ladies room, along with Sandy and Gloria, he still didn’t have to pee.  But that didn’t necessarily mean he wouldn’t have to pee once he got to the toilets.  Not certain about it though, he went through the otherwise empty ladies room and entered one of the stalls.

      “We’re going to have to watch!” Sandy said quickly, so he wouldn’t shut the stall door.

     Chad still didn’t need to pee, but he didn’t really have that much of a problem with leaving the stall door open.  His bigger problem was that he still hadn’t felt the least little urge that he would have to do it yet.  He had figured that either the urge would hit him as he was walking toward the restroom, or that just walking into the bathroom itself would trigger it… or if not, then standing in front of the toilet would trigger it for sure.  But surprisingly, he felt nothing.  Nothing at all.  A tiny little thought that his body no longer associated bathrooms and toilets with peeing anymore flittered through his mind.  But thoughts like that didn’t help him any.

      “What are you waiting for?” Sandy asked.

     He had been standing in front of the thing, waiting to feel the urge, but nothing was happening.

      “Are you worried about if you should stand up or sit down?” Gloria asked.  “Because we don’t care.  Whatever suits you.”

     Chad hadn’t even thought about that.  Since he was male and his body was used to standing to do this, he pulled up his skirt, and pulled down the front of his panties, and grabbed himself – just like he used to do.  And he stood there… and stood there.

      “We’re waiting!” Sandy said impatiently.

      “Let me guess,” Gloria said.  “You didn’t really have to pee, did you?”

     Chad turned his head back towards them as he pulled his panties back up into place.  “I guess not,” he replied.

      “That’s not going to be allowed!” Gloria said with more than a hint of sternness in her voice.

     Chad pulled his skirt down again, and slowly backed out of the stall.  Well, he thought it had been a very good idea. 

     They got no more than a dozen steps back outside the rest room again when Chad did suddenly feel that nasty little need to pee.  Not saying anything, he quickly turned and ran straight back into the ladies room again and straight into the same stall.  He was fighting desperately to hold back as he pulled up his skirt.  He reached inside his panties and grabbed his penis in a crushing grip to prevent it from leaking before he wanted it to.  Only then did his other hand tug his panties down.  Aiming it as best he could, he released the pressure of his grip and the pee rushed out.  Not a lot, as usual now, but it was enough.  He just made it!  For the first time in two months, he peed into a toilet – like he used to – like any normal person.  As he did, he heard Gloria and Sandy rushing back in behind him.  And even though it was a little embarrassing for him to be watched by them, he felt proud of himself as well.  And as short as it had lasted, he knew that they were there in time to actually witness his success.

     Proudly, he finished up, pulled up his panties without bothering to wipe himself off, and pulled down his skirt.  He turned, still feeling proud.  But the looks on both Sandy’s and Gloria’s faces displayed anything but happy for him.  In fact, they both looked down-right perturbed! 

      “That was cheating!” Gloria told him.

      “But I made it!” Chad insisted.

      “I didn’t like the way it happened either!” Sandy said to Gloria. 

     Chad still felt proud of himself.  He had done it!  Boldly, he walked over to the row of sinks and washed his hands while both women looked on with disgruntled looks on their faces.  He didn’t care in the least.  When he was done, just as proudly, he said, “Let’s go back and tell the others.”  He led the way back out and all the way back to where he had been looking at skirts.

     What he didn’t see was Gloria and Sandy whispering back and forth as they followed some distance behind him.

      “What happened?” Robin asked as he returned.

     Still feeling proud, Chad looked over toward Mel who was desperately watching and obviously wanted to know the answer as well.  “That’s one for my side!” he declared happily.

     Mel was shocked… and suddenly scared.  He was getting it back – and it now seemed that he was getting it all back very fast.  It was time to start coming up with something to help her side.

     As Chad happily select two skirts – that he suddenly decided he really liked, Gloria went around to each of the judges and whispered something to all of them.  There were a number of raised eyebrows in the group. 

      “What is it?” Mel asked.

      “You don’t need to know,” Gloria told her.

      “We need to hurry up,” Andrea told everyone, it’s almost time for his second drink.

     Chad was allowed to pay for the two skirts he had found, but then the women all seemed to hurry him straight out into the mall again, without letting him take the time to change into one of his new skirts.  Cassie stopped in an out of the way place once they were clear of the store.  She set her backpack down and started digging through it.  “Since there’s no place close by to get you a drink, I brought a few cans of Coke with me instead.  She fished one out of the bag and handed it to him.  “Drink up,” she told him.

      “And don’t take too long with it,” Andrea added.

      “We need you to finish that thing as fast as you can.” Gloria remarked as well.

     Mel was delighted at the way they were forcing another drink into his system, but Chad wasn’t happy about it at all.  He would have taken much longer to drink it, except that the women all hounded him to keep drinking until the can was done.  He figured it was a good thing he was so used to drinking constantly and with the ladies encouragement, his drink was soon gone.

      “Now can I find someplace to change my skirt?” Chad asked.

      “Sure,” Andrea replied.  “Where did you want to go?”

     It was like a light bulb went off over Chad’s head.  “A bathroom somewhere?” he said hopefully.

      “Not a chance!” Sandy replied.  “At least, not for that purpose.”

      “Maybe we can find a changing room somewhere,” Andrea suggested.

      “I don’t see why he doesn’t just leave on the skirt he’s wearing now.  It’s not that wet in the back and he’s already worn it for quite a while now.”

      “If he wants to change, then that’s should be up to him,” Gloria suggested. “What do you want to do?” she asked Chad.

     But Chad was just standing there as if he hadn’t been paying any attention.  “Go somewhere to change,” he finally replied, totally disheartened.  “And I need another pair of panties.”  The darn urge had hit him so fast after that drink that he hadn’t had time to realize he had to go until it was already spurting out of him.

     Sandy giggled.  “That will be your fifth pair of panties,” she told him.

     Chad made no reply, but Mel gleefully remarked, “Another one for my side!”

     Chad’s only thought was – Damn!  And things had been looking so much better a short while ago!

     Chad got himself a fresh pair of panties, but he decided to leave on the skirt he was already wearing.  No use messing up a new one if he happened to leak all over it again.  Besides, the one he had on didn’t feel wet anymore and according to Gloria, it hadn’t really shown the wet spot much anyway. 

     Totally dispirited, he followed the group of women out of the bookstore where he had changed and out into the mall again.  But his thoughts remained on how poorly he was doing.  For two full months he had been convinced that he could get it all back almost immediately.  But that didn’t seem to be the case.  He would have never believed he would have the trouble he was having.  Part of the problem, he realized, was something he had noticed many times in the past few weeks – sometimes he could realize when he was peeing, and sometimes he never knew it.  And that’s kind of the way it was going today.  Sometimes, if he concentrated hard enough, he could figure out when he was going to have to pee, but other times, like what just happened, he didn’t have a clue!  It just happened.  And he had no idea what he could do about it.

     He realized that Robin was talking to him again, although he hadn’t been listening and didn’t have much of a clue what she had been saying.  He continued to ignore her while he sulked over his little problem.  Of course, what he was experiencing right now was exactly what he had often fantasized about, being totally incontinent.  Having someone strip all his adult control away from him and reduce him to the level of a helpless baby.  The thought stirred his under-utilized sexual needs once again – just as the fantasy had always stimulated him.  Maybe when this was all over – in just a little while – he would stop trying to control himself for a few weeks – just to see what it would really be like… just to enjoy it.  The idea sounded very tempting.  And he was sure that once he decided he’d had enough, he could always regain his control again within a day or two.  He no longer figured a few hours would be enough.  He now knew first hand that it wouldn’t be.

      “Chad!  Are you listening?” Robin asked. 

      “Huh?  Oh, sorry,” he replied. 

      “Where were you?” Robin asked.

      “Sorry,” Chad replied again.  “I’ve just been trying to concentrate on when I have to go.  I’m not doing very well though.”

      “Maybe you shouldn’t try so hard,” Robin suggested.

     Chad looked at her with a rather annoyed look on his face.  “It’s all the times I don’t try so hard that I mess up the worst!”

     Sandy giggled as she heard him say that.  She checked her list of bathrooms.  “The closet bathroom now is going to be in the back of the CD store across the way.  All the way to the back, then down a short hall and on your left.”

      “Thanks,” Chad replied, grateful for the information.  He was actually grateful for all bathroom location information that Sandy was quietly passing on to him.  He just didn’t usually say anything about it. 

     Gloria and Mel stopped to look at a dress in one of the display windows, which meant that naturally everyone had to crowd around and discuss it.  While Mel and Gloria discussed the merits of the dress, Robin and Andrea commented on the shoes the store had paired with it.  Sandy was more interested in the accessories.  Cassie and Chad were the only ones who said nothing at all about it. 

      “So get it!” Mel told Gloria.  “It’s gorgeous and you know you would look fabulous in it!”

      “Not today,” Gloria replied.

      “Oh come on…  Why not?”

      “Because today I’m here for a different reason.”

      “That doesn’t mean you can’t enjoy yourself.  And you know Ray would love it!”

     Gloria thought about it a moment more.  “Not… today.” She said. 

      “If it’s money you’re worried about, I’ll buy the thing for you!”

     Gloria looked at her.  “Don’t make it sound like you’re trying to bribe me.”

     Mel looked surprised.  “Me?  I wasn’t!”  The truth was, the idea had flittered across her mind.  But that wasn’t her main intent.  Gloria was simply her friend.”

     Gloria shook her head again.  “Not today.  Maybe some other time.”

     While the women were discussing the mannequin in the window, Chad was concentrating on whether he had to pee or not.  And he wasn’t totally sure, but he suddenly thought that he might have felt something… although it was so slight it almost wasn’t there.  Knowing how poorly he was doing, he turned in the direction of the CD store with the bathroom.  “Going!” he declared as he took off at a fast walk.

      “Here we go again!” Cassie said as she took off after him.

      “My turn,” Robin told the others and hurried off after Cassie.

     Chad was concentrating hard, but the fast walking he was doing seemed to be making his almost unnoticed need get worse.  Before he reached the store, his fast walk became even faster and more desperate.  By the time he got into the store itself, he was clamping down on those muscles for all he was worth.  A moment later, he broke out into almost a run.  He found the backroom hallway easy enough, and the single restroom off of it wasn’t hard to find either – and fortunately, it wasn’t occupied.  But he was now struggling more than ever as he opened the door and forced his way inside.  Even if Cassie and Robin hadn’t been running after him, he wouldn’t have bothered to lock the door – there wasn’t time.  He was desperate! 

     He pulled up his skirt and was grabbing for his panties – as his system no longer had the strength to hold it anymore.  Pee was gushing out through his panties by the time he was able to pull the front of them down far enough to grab his spurting member.  As he did so, the pee seemed to splash all over the place.  He finally pulled his penis out to aim it into the toilet, but what little was still coming out of him by then either hit the floor, or the wall, or the toilet seat.  A few drops only managed to drip into the toilet itself. 

     Totally disappointed and angry with himself, he was still startled when the door to the restroom crashed open and Cassie rushed in followed by Robin.  He was still standing there with his penis in his hand, the evidence of what happened was all around him.  He stood there and ignored them, only thinking about the futility of it all.  He had tried.  He had really tried.  He had tried so hard!  And yet, he hadn’t made it. 

      “Again?” Cassie asked.

     He made no reply. 

      “Eeww!  What a mess!” Robin noted as she looked around. 

     Chad looked back at her but didn’t reply to that either.  It was looking very much like his life was going to belong to Mel for the next year. 

     Cassie automatically handed him the box of wipes followed by another of the panties that Sandy had contributed – pink covered in white lace.  Chad was too dejected to appreciate them.  Robin only stood and watched, but Chad and Cassie both did what they could to wipe up his mess. 

      “That’s six,” Sandy counted when she saw Chad’s face as they all finally returned.

      “What happened?” Mel asked, although she could also see on his face the answer to that one. 

     But neither Robin nor Cassie spoke to her.  Instead they whispered what happened into the ear of each of the judges. 

     Mel wasn’t being allowed to hear but she had already guessed that he hadn’t made it.  “I guess that’s another one for my side,” she said to Chad.

     Chad merely turned away, totally disappointed with himself.  He couldn’t answer.

     Cassie knew she probably shouldn’t have told her, but she did anyway, even though she left out all the details.  “He almost made it,” she said to Mel.  “He was so close!  He almost made it.”

     Mel was left with mixed emotions.  He almost made it?  Which means that he didn’t make it, but at the same time… he was still getting it back – and despite a few setbacks, he was actually regaining his control… fast!  She checked her watch, there was still a little more than half an hour to go.  But for the frequency that Chad was used to peeing now, that could still be an awfully long time.  But could he get more of his control back in the next half hour?  She was fearful of exactly that!

     As they slowly walked the mall, Gloria was talking to her about possibly redecorating part of her office, but Mel was only half-listening.  She was more focused instead on worrying about Chad and the fact that he could still possibly win this thing.  She had to do something!  And she had to do it fast!  But what?

     As she listened to Gloria, now talking to Sandy about what she was considering doing with her office, Mel realized something else, as much as she was now afraid that she might lose, Chad was feeling the same thing – or probably worse!  She just needed to find the right lever to tip Chad away from winning.  But again, what could possibly do it?

     They came to the end of the mall where one of the big department stores was located.  She finally realized where she was.  She looked around… and she wasn’t at all surprised that she found what she was looking for.  Or rather, ‘who’ she was looking for – the elderly gentleman who she had always thought of as Sissy’s biggest fan.  The one who had claimed to Sissy that he was a sissy too.  Since she saw that he had noticed her as well, she figured it would only be polite to say hello to him.  The others were now gathered around a display of fine china near the entrance to the store.  “Excuse me,” she said softly to everyone as she extricated herself from the group. 

     She walked directly over to the bench where he was sitting… as usual. 

      “You have a lot of company today,” the man said to her. 

     Mel looked back briefly.  “Yeah.  It’s kind of… a special occasion.”

      “You’re celebrating?” he asked.  “Because, if you’ll pardon me, you don’t exactly look all that happy.  And I see your friend… Sissy, in the group too, and he looks less happy than you do.”

      “Yeah well, it’s not a party kind of thing.”

      “So what’s going on?”

     Mel shook her head.  “It’s a long story, and you’d never believe it.”

     The man brightened.  “But I like stories.  And you never know, I may get an idea from you for one of my books.”

     Mel remembered that the man was a writer who had said he wrote under the unlikely name of Karen Singer.  She shook her head again and let out a false laugh.  “I seriously doubt anyone would be interested in reading about this!”

      “You never know,” the man said.  “You never know.”

     Mel decided that there was really no point in talking to him any longer today.  She had done the polite thing and said hello to him since they were both there.  “Take care of yourself,” she said to him.  “Maybe we’ll see you again some time.”

      “I’m right here,” he replied.  “Almost every day.”

     Mel smiled and turned away.  It still didn’t seem likely that the man could be a sissy too.  At least, not like Chad was.

     As she returned to the group, she noticed that Chad was standing by himself, behind all the women.  She walked up next to him.  “Do you miss being here in your frilly pink dress?” she asked softly so the others wouldn’t hear her.

     Chad looked over at her with horror in his eyes.  “Not really,” he replied.

     Mel smiled mischievously at him.  “I’ll bet you do though.”  She could see that somewhere in the back of his mind, now that she had mentioned it, he was indeed remembering how he had felt during those little trips.  And she was sure that the memory had sparked something else within him as well.  “You know of course, if you win, you’ll never get to do that again.”  She left him then to think about it.  She was playing to his fantasies, one of the most powerful forces that drove him.  She would do whatever it took to win this bet!

     The group of women started to move on then and Chad followed with Robin at his side.  But his thoughts were now instead remembering the wonderful excitement of all the monstrous humiliation he had experienced every time Mel had dragged him through the mall – numerous times, whether he was wearing his pink sissy dress or not.  And he knew he would miss it – probably always.  But he also knew that he wasn’t going to throw this bet because of that!