Friday, September 30, 2011

The Bet - Chapter 42 (Friday – week 6 Part 8 of 8)

The Bet
by Karen Singer

Chapter 42 (Friday – week 6 Part 8 of 8)

Chad knew he was in trouble as they were driving home. It had been a very long time now since he had put his single diaper on and called Mel to tell her. But he wasn’t leaking yet. He was certainly very, very wet. That much was for sure. But he wasn’t leaking. Now, after dinner and the two large glasses of iced-tea, he was wetting fairly heavily again and often too, but he hadn’t started leaking yet. He was becoming more and more concerned about it – and even more concerned over his punishment for not leaking on time. And speaking of leaking… “Um… Mistress.”
“Um… Can I wash my sheets tonight… please?”
“Wash your sheets? Why can’t you do it tomorrow with the rest of your things?”
“Because I leaked all over them last night.”
“You leaked? And you were wearing how may diapers last night?”
“Four diapers and you still leaked?”
“I had way too much to drink!”
Mel just looked over at him wickedly as she drove. “Never!” She went back to concentrating on her driving, but a minute later added softly. “We’ll have to try that again – very soon!”
Mel finally pulled into her parking space and turned the engine off. She glanced at her watch. “Okay, Sissy. By my watch, you’ve only got thirty minutes left to get that diaper leaking!”
Chad was surprised. What had happened to an hour and forty five minutes? Not that he was about to complain. They had been gone for well over two hours now and he wasn’t looking forward to the beating he would have received. And as wet as he thought his diaper was, he was fairly sure he could make it leak in the next thirty minutes – hopefully. “Thank you, Mistress,” he replied gratefully as he got out of the car.
Mel had been very aware of the fact that she hadn’t given him enough to drink this time, but by not telling him, she was fairly sure that he hadn’t been holding back at any time. So hopefully, nothing lost there. Besides, she had other plans for him tonight that didn’t include punishing him.
Chad hurried up to his apartment where he quickly pulled the sheets from his blow-up mattress. He wondered briefly if Mel wanted him to wear his maid’s uniform again. But she hadn’t said anything about it so he left on the clothes he was already wearing as he carried the sheets over to her apartment. Before putting the sheets into the wash, he went to her refrigerator to grab himself another bottle – if he was going to make even this extended deadline, then he absolutely had to keep drinking! But when he opened her refrigerator, he was shocked to see that there were no bottles left. He knew her supply had been running low but he didn’t realize that she had none left at all. Even his own supply at home was nearly used up. Did he dare mention it since her lousy green tea tasted so… lousy? He grabbed one of the empty bottles from her cabinet that he had washed earlier in the week and filled it with water. The lack of taste was certainly an improvement over her green tea mixture. He drank continuously as he walked back to the washer to load his sheets into it.
While Sissy was busy getting something to drink and loading his sheets into the washer, Mel changed into a pair of shorts and an old t-shirt. Then she wandered out to her stereo system and began looking through her collection of classical ballet music. If she was going to have him perform a little ballet in public, then she needed to choreograph something for him, and for that she needed the right music. Ah! Swan Lake! One of her favorites. Perfect!
She turned to see what Sissy was doing. The washer was already running and he was just standing there next to it, drinking from his bottle. She glanced at the clock. Time was about to run out for him. “Sissy!” She waited till he turned toward her. “Show me your diaper!”
Her command was the last thing that Chad expected. As fast as he could, he grabbed the hem of his skirt and pulled it up as high as possible, totally exposing his soaked diaper underneath.
Mel shook her head as she headed for her yardstick in the corner. “Just stay like that,” she commanded. “It wasn’t fast enough again. One way or another, we’re going to get you conditioned so that doing it faster becomes like a reflex. You won’t have to stop to think about it anymore!”
Chad watched with growing trepidation as she grabbed her stick and approached. He had tried to pull his skirt up fast enough, but she had simply caught him off guard with the command. And now he was about to pay the price. He stood there as she walked around behind him and off to the side a bit. He squinched his face up preparing for the pain that he knew he was about to feel.
“You will…” Swish, smack!
Chad jumped as her stick stung the top of the back of his legs, just below his soaked diaper. Wow did that hurt!
“Do it…” Swish, smack!
Again the stinging pain erupted on the back of his legs. But this time, the moment the pain erupted again, his pee also erupted out from the other side.
“Faster!” Swish, smack!
Chad couldn’t believe how much her yardstick was hurting him. She was obviously swinging it extra hard.
“You will...” Mel repeated as she again swung her stick hard at his exposed skin on the back of his legs. “Do it…” And again she swung her stick hard. “Faster!” she finished with one final and extra hard swat. She backed off and could see how red the area was where she had hit him… after only six blows. “If you don’t learn soon, we’re going to have to come up with a more convincing way to teach you.” And then she noticed what Chad himself hadn’t been capable of feeling yet, the little thin line of wetness escaping out from his diaper and just starting to run down his leg. She glanced up at the clock. “Two minutes too late,” she told him.
Chad wondered what she was talking about. “Two minutes too late for what?” But instead of answering, Mel swung her stick again at the back of his legs. “You’re leaking,” she said right after she hit him. She swung one more time. “And it’s two minutes too late!”
With the stinging pain from her yardstick, Chad couldn’t even tell he was leaking. All he felt was pain.
“Now hurry up and get yourself another diaper. We have other things to do tonight.”
Chad ran for his diaper bag and pulled another diaper out of it. Only two swats for being late? Talk about lucky! He brought the fresh diaper back to Mel so she could change him.
“Do it yourself,” she told him. “And you better hurry up. Your hour and forty five minutes started five minutes ago!”
Five minutes ago! She was making it more difficult once again! As fast as he could, he removed his soaked and leaking diaper and put the fresh dry one on. It felt so totally different from the squishy heavy one he had just taken off. In some ways it was more comfortable. But in other ways it was a lot less interesting to wear! The problem now was that he had to make it interesting as fast as possible – too fast in fact. He grabbed the bottle of water he had been drinking and started working on it before he disposed of the used diaper he had just taken off.
Mel went back to her stereo and loaded the disk for Swan Lake. She found the track for the music she wanted and turned it on to listen for a minute. Beautiful, just beautiful! She looked to see what Sissy was doing. He was back to drinking furiously from his bottle again. She noticed that whatever he was drinking looked awfully clear. She didn’t really care, as long as he kept drinking. But now she wanted him to do other things besides just drinking. “Sissy, get over here. It’s ballet time again.”
Chad knew it was coming. He just hoped it would come later rather than sooner. He carried his bottle around to his usual place next to her sofa, grabbed the back of it with one hand to steady himself, and put his feet into the awkward first position.
Mel watched Sissy getting into place. Some things about what he did pleased her greatly, but something bothered her tonight. She was about to get much more serious with his ballet lessons, so… “Sissy, get undressed. Just leave your bra and diaper on. You won’t be able to dance properly with everything else.”
Chad got undressed - mostly, leaving just his one diaper and his bra with the falsies glued to his chest. He was mostly glad to be rid of the darn waist cincher he had to wear all the time. He felt much more comfortable without it. But once he got back into position at the end of her couch again, he discovered that for some reason, even just in front of Mel, he felt much more embarrassed about being exposed in only the one single diaper. How strange. He was also embarrassed to suddenly realize he was peeing again. Oh well, he guessed he better be. His deadline could come awfully fast and it was difficult to keep drinking while doing ballet.
Mel began trying to teach him what little she remembered from the tiny pieces of the ballet she had done in her childhood dance recitals – which didn’t amount to very much. But at least it was a starting point. Trying to remember exactly what she had done was difficult. Trying to teach it to Sissy was even more difficult since he didn’t have a clue about any of it. But her biggest problem turned out to be something else entirely. It was something that was really just a bit of a distraction at first, but it became more and more of a distraction as time went on. That was the sight of the single flimsy diaper he was wearing – that gradually grew wetter and wetter as she watched.
The wetter his diaper seemed to get, the more she noticed it and the more it made her keep looking at the clock to see how much time he still had till he was supposed to be leaking. It also kept reminding her that he needed to keep drinking more than he needed to be dancing, so she kept calling brief break periods so that he could drink from his bottle – or so he could go get another bottle. And when the washing machine kicked off and it was time to move his laundry into the dryer, that was another distraction.
Finally, with only fifteen minutes left for him to be leaking, she called a halt to the dance practice entirely. There were just too many distractions. Plus, she finally realized that the real reason she was so distracted was because she didn’t really know what she wanted the dance to look like yet. She didn’t have a full idea yet of what she wanted him to do. She needed more time to figure that out. For something as complex as what she had in mind, she needed to plan better. “Okay, Sissy, we’re finished here for tonight. Get your laundry out of the dryer… and finish that bottle! As soon as you’re done, meet me in the bedroom.”
Chad was glad to be finished. She had told him to do one thing, then she would change her mind and make him do it differently, over and over again. He was now more confused about ballet then when they had started – which really didn’t bother him at all.
He took care of his now clean and dry sheets and set about finishing his latest bottle of water. He was peeing automatically again – he had been since the restaurant, or earlier. It was hard to tell. And once again, he didn’t always notice when he started peeing. If he was busy concentrating on something else, then it was like his body was forgetting to tell him about the other. He wondered if there were times when he was peeing and he didn’t know about it at all. Possibly. But since he didn’t know about it, he couldn’t tell for sure.
When his bottle was finished, he went into Mel’s bedroom. As he suspected, her bed was prepared against any of his “accidents” and the ropes to bind him were already out and in place. Within minutes, he was firmly tied to her bed, which he thought was ridiculous because he had noticed the jar of glue remover already out on her nightstand. Obviously, she was planning on removing his glued-on breasts again – and he wasn’t about to fight her over that one little bit. He was actually looking forward to getting that weight and bothersome feature off of his chest for a while. Even if it was just for a while.
Just as she had done for the last few weeks, Mel slowly and carefully removed the breast forms from his chest. As each one was finally lifted off, he felt a huge sense of relief as the weight was finally gone. He noticed as she did it that she never once said a word to him. Through the entire process, Chad got the impression that her mind was elsewhere. She was there with him… but she wasn’t. Once the breast forms were removed, she unfastened his now very soggy diaper. That too felt strange as it was pulled away from his front side and she let it drop down between his legs.
Mel pulled his soaked diaper back, exposing his chastity device underneath. The diaper itself was so wet that she couldn’t believe it hadn’t started leaking yet. He was lucky tonight that she had too many other things on her mind and wasn’t overly interested in punishing him unless she saw that it was necessary. She carefully checked his tiny penis inside of the device. Just as tiny as ever. Perfect! Those teeth inside of the device really were affective!
She needed to wipe him off next. She turned away and grabbed a wipe out of the box she had on her nightstand. But when she turned back, she was surprised to see a small stream of pee rushing out from the end of his device. Fortunately, it was all rushing down onto the soaked diaper still underneath him. She looked up at his face. There was no hint there that he even realized what he was doing. But of course he realized it. He had to realize it. He probably just didn’t care! She suddenly saw him look a bit startled and he lifted his head, trying to see down toward the “business” end of things – which he really couldn’t see all that well. He briefly looked up into her eyes. Was she wrong, or did he seem to be a bit embarrassed. Well, she would have probably been embarrassed if she were him. She waited till he finished peeing again before she wiped off his front side.
She untied his legs next. Then she opened the jar of suppositories and pulled one out to have it ready. With his help, she lifted his legs way up into the air and up toward his head, totally exposing his backside. She pulled the soaked diaper out from under him and pulled four of his cloth diapers into place. Then she wiped his backside off carefully and before she set his legs back down again, shoved the suppository way up inside of him. Since he hadn’t gotten one last night or today at lunch, there was no way she would let him go without one now.
She let his legs back down and began the arduous chore of trying to pin so many super thick cloth diapers on him. It took her a long time to manage it and her fingers hurt before she was done, but she did finally manage it. Of course one of the reasons that it took longer than usual was because her mind was only partially on the task. A fresh pair of plastic panties soon followed to protect everything, and he was ready. She finally untied his hands and let him to his feet.
Chad gratefully stood up and breathed in deeply without the extra weight of the stupid breast forms. He noticed though that his chest felt strange now without them. As he moved, he also noticed how odd it felt for his arms to move in certain ways and not come in contact with them. Obviously, he had been wearing them for way too long now!
“Get your things together and go home now,” she told him, which was exactly what he expected her to say. “We have a busy day tomorrow,” she added – which wasn’t exactly what he expected to hear. He briefly considered asking her what was going on, but thought better of the idea. If he knew, then he might stay awake all night worrying about it.
He had trouble waddling around in the super thick diapers, as he gathered up his things. They were so thick and stiff that walking normally was completely out of the question. The awkward waddling he was forced to adopt wasn’t all that easy either. But once he had everything, he went back to her bedroom where he saw her still sitting on her bed, seemingly staring off into space. “Goodnight, Mistress,” he said as he tried to curtsey a bit with his arms full and the super thick diapers forcing his legs wide apart.
Mel snapped back to reality at his words. She smiled half heartedly. “Goodnight, Sissy. I’ll be in later to leave you a note as usual.” She watched as he attempted to curtsey again and failed miserably. She almost laughed at his attempt. Then she sat there and listened as he walked out and closed the door behind him.
She continued to sit on the bed as her mind tried to sort through too many different problems. Problems she wasn’t totally aware that she had – till now.
What was she going to do about teaching him a ballet that he could perform in public? She could of course easily drop the idea, but now that it had fully set in, she wasn’t about to even consider that course of action.
How was she going to completely overcome his ability to control himself? The only way she could clearly see right now was to keep doing just what she was doing. But was it enough? She worried about that constantly.
And then there was the biggest item on her mind. Her one piece of unfinished business for the day. Her business that had gotten ruined by odd events earlier. In a nutshell… What was she going to do about Robin?
She got up from her bed with all those things on her mind as she went into the kitchen to make herself a fresh pot of coffee. While the coffee was brewing, she got out her big pot and began making more tea for Sissy. She had let their supply run way too low. Making tea would be a good task for her to do while she considered things and tried to figure out her best course of action. Tomorrow would be a busy day. And tomorrow, she had to make some decisions – one way or another.
Her mind skipped back to Sissy, alone in his apartment. Was he still drinking his required three bottles before bed, or had he finished yet? Not that it mattered. She silently wished him a goodnight as she stirred the strong green tea mixture in her pot. “Good night, Sissy… Good night.”

Tuesday, September 27, 2011

The Bet - Chapter 42 (Friday – week 6 Part 7 of 8)

The Bet
by Karen Singer

Chapter 42 (Friday – week 6 Part 7 of 8)

Mel was silently fuming inside. This meeting wasn’t going at all like she had hoped it would. Nothing but problems, problems, problems! But her biggest problem was that it was hard to stay concentrated on the matters at hand when her mind was locked on her problems with Sissy. Robin was looking at wedding dresses? Who did that stupid tart think she was? She had hoped that this meeting would be over with long ago, instead it was dragging on and on and on!

Chad finally finished up the paper he was working on. It was stupid. Totally bogus. But he had finished it. He seriously doubted that Mel would accept the thing. But if she made him rewrite the darn paper then at least he would have the weekend to think up new material for it. Hopefully, better material than the dumb stuff he had included today. Glad to get the thing out of the way and off his desk, he hit the send button.
Now what was he going to do? He looked at the time. There was still over half an hour to go before he could go home and get changed. Robin was looking at wedding dresses for him. How dumb! He was tempted to go over to her desk to see what she thought would look good on him, but with the load in his diapers he decided to stay put right where he was. Wedding dresses? Why not? He typed the words into the search engine and happily started looking through the web pages that were found.

Mel finally “stole” a spare minute while Andrea was changing a few things in the paperwork before everything could get signed and finished. She hurried to her office where she picked up her phone. A quick glance at the clock showed her that it was time for him to be leaving work – already! She was running so late! And she had gotten nowhere with finding out what that stupid Robin woman had been talking about. She quickly dialed his number and listened impatiently as his phone rang.
Chad’s cell phone started ringing again as he was walking out to his car. It took him a moment to fish it out of his purse so he could talk. “Hello?” he said in his girly voice, knowing that the caller in all probability would be Mel.
“Sissy! Where have you been?”
“Um… I’m heading out to my car right now,” he replied.
“No, I mean earlier. I tried to reach you twice!”
“Oh, I had to go up to the HR office to pick up the paperwork approving my days off. I tried to return your calls. Andrea said she would tell you.”
Mel felt frustrated. She hadn’t had time to talk to Andrea about anything other than the client’s needs. “I haven’t had time,” she replied. She glanced at her clock. She had to get back. There was not enough time for details. “Call me after you get cleaned up and as soon as you put your one diaper on again. I’m running late tonight so you better be ready. We’ll talk later. Oh, and if you get the chance, drink another bottle before I get there. Just don’t be late!”
Chad suddenly found himself holding a disconnected phone. Don’t be late? He wasn’t late. And if he was supposed to wear only one diaper again, how was he supposed to make it leak if he had to be sitting in the nail salon for who knew how long? But then Mel didn’t always seem to care about details like that. Of course, that was probably why she wanted him to drink that one bottle before she got there. If he had time.

Mel partially ran a red light trying to hurry home. She glanced in her mirrors and all around hoping that no police had seen her. She was running late and stepped even harder on the gas pedal. She only hoped that Sissy was ready by now – he should be. He had called a little while ago and she had noted the time as he put on his single diaper. He had plenty of time to finish getting ready since then.
She had taken two minutes before she left the office to quickly read over the paper he had written and emailed. Most of it had been basically trash. But she had been caught off-guard by the final section of his paper. He “deserved” to be incontinent – because he was foolish enough to think he wanted it? Did that mean that he no longer wanted it? Did it mean that he was going to fight her even more now? She should never have assigned him that paper to write. She had originally thought that he might come up with reasons that would help to convince him to stop fighting it and just accept it. But instead just the opposite had happened. Now he had more reasons than ever to work against her! It was not a good situation!
Her tires squealed a bit as she turned into the apartment complex, warning her to slow down. Fortunately, she heeded the warning. She pulled into her parking space and automatically noted Chad’s old car where it should be. But was he ready? She turned the engine off and started to open her door when she saw him suddenly appear on the balcony above. Good! She restarted her car as he hurried down the steps toward her. Two minutes later, her tires squealed again as she turned out of the apartment complex back onto the road.
She wanted to ask him questions, too many questions. Too many questions about too many different things. But now was not the time. They were close to being late for their nail appointment and she didn’t want to be late. If they were late they would probably have to wait a long time before one of the techs got around to them. And she knew how crowded the place usually was. As it turned out though, they got there with plenty of time to spare.
“Now don’t forget,” she said before they got out of the car, “you curtsey to absolutely everybody! And no more ‘girly’ voice. I’m tired of hearing that. Sissy voice instead. Only your sissy voice!”
“Yes Mistwess,” Chad replied in his sissy voice. He had noticed from the moment he got into the car that Mel had seemed… distracted by something. He figured it had to be something at work. Probably the reason she was running later than usual.
There were several women seated in the waiting area as then entered the nail salon. As they walked in, Chad heard one of them say to a friend, “See, I told you he would be here again!” Chad purposely didn’t acknowledge that comment.
Unfortunately, Mel had heard it too and she stopped to say hello. “Oh, you’ve seen Sissy here before?”
The woman laughed. “Sissy? That figures. Yes, we loved how sweet he curtseyed last week.”
“Sissy!” Mel called, “It’s not polite to ignore these nice people. Say hello them.”
Chad hated having to do it, but there would be no help for it. He dropped a nice curtsey for them and said in his sissy voice. “Hewwo. It’s nice to see you again.” Both women burst out laughing as Chad felt his face turning red.
Out of the corner of her eye, Mel noticed both their nail techs waiting on them. “Okay Sissy, we don’t want to hold up the works here. You can talk to them later.”
Chad was glad to go before things could get any worse. And most likely, he wouldn’t have to see either of those women when he got finished. He had to properly greet his usual nail tech too before she led him back to the chair where she removed his shoes for him. One of the best things about sitting down to have his nails done was that he couldn’t curtsey to anyone while he was seated!
“So what color today?” his tech asked as she started to remove the polish from his toes.
Chad looked at his lavender fingernails. “I don’t know. Something pretty I guess.”
“All colors pretty,” the tech replied. “You want me to make suggestions again?”
“Mel suggested earlier that I look at something in a reddish pink today.”
“That leaves a lot of selection. We have lots like that.”
Between the two of them, they decided on one that was mostly a light red, but not quite in the pink line. Chad watched as she put it on his toes. He held up his long purple fingernails again to look at them while she did it. He didn’t know how it had happened, but the odd lavender color had grown on him. He stared at the length of his nails. Should he cut them? Maybe. He did think they made his fingers look more feminine the way they were. “Do you think you can shorten these just a little bit?” he asked. “I like them long, but maybe it’s time to take a bit off the length.”
“No problem,” the tech said. “We fix you up just the way you like.”
By the time Chad got his toenails done and the tech had fussed getting his fingernails perfect again – in the new color and shorter length, Mel had been finished for a while. He found her waiting anxiously in one of the chairs out front until he finished. She stood up at his approach and said, “Let me see.” Chad held out his newly formed nails, now in red. “Perfect!” Mel declared. “They’re lovely. And I like the shorter length. They’re still really long, but not overly so.”
“Thank you, Mistwess,” Chad replied.
“Curtsey when you say anything!” Mel replied sternly.
Ugh! Chad didn’t think he would have to. He especially hated having to curtsey in front of other people. But he did so and repeated his thanks – much to the amusement of the other customers. Then he had to pay his nail tech and curtsey his thanks to her once again. Finally, they could leave and get something to eat. Chad only hoped that she wouldn’t make him drink so much tonight as she had last night. He still felt sick every time he thought about it!

The restaurant was again the same one they had gone to for the last few weeks now. Chad didn’t know if that was a good thing or a bad thing. At least it wasn’t the same restaurant where they had eaten last night. That had been a major embarrassment when his diaper had fallen off as they were walking out. Once again, Mel made no mention of his baby bottle as they got out of the car… and he wasn’t about to bring it up either. He just hoped he wouldn’t have to guzzle so many drinks again like he did last night.
The waiting area was crowded again as they walked in. Sometimes it was, sometimes it wasn’t too bad. Tonight was bad. Chad remembered several weeks ago when it had been crowded like this too. Mel had made him curtsey over and over again with two little girls in the waiting area too. That had been embarrassing.
“You know what to do,” Mel said as she stood back out of the way. “And I’ll be watching.”
Unfortunately, Chad did know what he had to do. He had to wait in line behind several other people before he could put his name on the list. He recognized the hostess as the same one he had seen there before… and he could tell by her smile that she recognized him. He curtseyed and was about to ask her to put his name on the list, but she beat him to it.
“Sissy, party of two?” she asked.
Chad could only nod. She giggled as she wrote the name down. “I’ll call you,” she said with a big smile on her face. Unfortunately, Chad knew she would do exactly that. She would call his name over the loudspeaker system, even if he was standing right next to her. He curtseyed once again and said “Thank you.”
It was a fairly long wait since there were so many people there. When a seat along the wall came open, Mel moved into it and sat down. Sissy remained standing – where he felt all too visible. There wasn’t a single person in the waiting area that didn’t seem to look him over carefully. Many of them seemed to watch him the entire time they were waiting.
After a long while, the hostess disappeared for a few minutes. When she finally came back, she looked up at Sissy and smiled. Chad thought that she was finally going to call his name, but she didn’t. She just went back to looking at her list, and when another table opened up, she called another name instead. He heard Mel make an odd sound that he interpreted as frustration. Actually, she had been more tight-lipped tonight than usual. He figured she must have a lot on her mind so he didn’t bother to say anything to her at all.
The hostess disappeared again, then came back a moment later. But still their name didn’t get called. There were still quite a few people in the waiting area but as far as Chad could tell, everyone who had been there before them had already been seated now. Then he noticed the waitress who had served them for the last few weeks. The waitress walked up and pulled a menu out of the pile, then she picked up a child’s menu from another pile along with a box of crayons. Then she turned directly toward them. “Sissy?” she called loudly. Chad was glad it was finally their turn. He was only surprised that the waitress had called them and not the hostess. They followed her back to the same table they had sat at last week.
The waitress set Mel’s menu on one side of the table and the child’s menu along with the crayons on the other side. Chad felt strange as he watched her doing that, she hadn’t even asked, she had just done it. And without having to ask, Chad slid into the seat in front of the child’s menu. The waitress looked around at the table, then briefly at Chad, then finally at Mel. “No bottle tonight?” she asked, sounding somewhat disappointed. Chad could tell that even Mel was startled by the question.
“Not tonight,” she replied. “Instead, you can bring her two large glasses of iced-tea, both right away. And… I think I’ll have one myself.”
The waitress was clearly a bit surprised. “So that’s three large glasses of tea right away?”
“Yes please,” Mel replied.
The waitress just nodded and left. Chad felt nothing but relief. Two glasses of tea was definitely no problem.
The moment the waitress was gone, Mel leaned forward with a stern look on her face. “What the heck is going on at your company? Did you finally tell someone about our bet? Is it all finally out in the open now? And what’s up with this sex change thing? And most importantly, what the heck are you and Robin up to together? Why is she looking at wedding dresses? What’s she got in that crazy mixed up head of hers?”
Chad was totally taken aback by Mel’s sudden string of questions. “Uh… Robin?”
“Yes! What’s going on between you two?”
“Going on? Like what?”
But Mel wasn’t about to let him play so innocent. “Like why is she suddenly so understanding about everything that she’s now looking for a wedding dress?”
“Wedding dress?” Chad had to think for a moment before everything finally clicked. “Oh! She was looking for wedding dresses for me. She thought that…” He paused and shook his head. “It’s a long story.”
“A long story?” Was that blonde-headed tart planning on both of them wearing wedding dresses when they got married? “I want to hear all of it!”
Chad tried to figure out where he needed to start, which turned out to be fairly easy. “It all started at break this morning…”
Mel listened carefully to every word that Chad said as he explained how one of the women suddenly decided that he was dressing like he was so that he could ‘get together’ with Derek. She had no trouble believing it when all the other women picked up on it. She even had to admit that it sounded a lot more plausible than the real reason – their bet. “And what about this sex change business?” she asked.
Chad grunted. “I have Robin to thank for that one! She suddenly got it into her head that the reason I’m taking off at the end of the month is to get a sex change. I mean, how stupid!”
Stupid? Yes, that was how Mel saw Robin. She had plans for Robin, but things had gone so haywire today that she wasn’t sure she could make them happen as planned anymore. But there was one thing that Mel had to be sure about. “So Robin thought that you and Derek were going to get married?”
Chad shrugged. “I guess. Eventually anyway. And Robin even admitted later that she knew I wasn’t really getting a sex change this month.”
Something inside of Mel felt relief. She wasn’t planning on marrying him… that she knew of anyway. “But she still thought that you and Derek wanted to get married?”
“I guess. And that’s the strange thing. One of the women came back this afternoon and said that Derek had confirmed the whole thing. I can’t believe it! Why would he do such a thing? He’s even avoiding me right now just because of the kidding he’s getting about our date Sunday.”
Mel’s brain was turning. She knew for a fact that Derek hadn’t talked to Sissy. And she seriously doubted now that he had told anyone that he and Sissy wanted to get married someday. “Is it possible that someone else might have said it and not Derek?”
“Why? And why would the woman say that Derek had confirmed it if it wasn’t true? She seemed awfully excited about it when she told us.”
Mel had to admit that she didn’t know. “Is it possible she heard it from someone else?” It was all she could think of.
“I don’t know. I’m pretty sure she just said that Derek himself had confirmed it.”
Mel quickly saw the little flaw in that and pounced. “But that doesn’t mean that Derek himself talked to her. Isn’t it possible that someone else told her that Derek had confirmed it?”
Chad wasn’t so sure. “I guess it’s possible,” he admitted. “But she just seemed so sure of it.”
But Mel was past that point. She had no doubt now that Derek had nothing to do with it at all. “So who would do such a thing?” she asked. “Who would tell her that Derek had confirmed it?”
“I don’t know. There’s a lot of people in the company that are always teasing me – all the time. I think I’m their favorite sport.”
Mel was amused to hear that. She also had no doubt about it at all. “Okay, so let’s try to narrow it down a bit more. Who might want to tease not only you, but also Derek?”
“Derek?” Chad had to think about that one. “I don’t know. The only person that Derek really mentioned that was on his case over our date was Ray. But the woman said that Derek had confirmed it.”
More things suddenly clicked for Mel. “Ray? The Ray that was at the poker game? The same Ray who’s going to be my date Sunday night? That Ray?”
Chad nodded. “Yeah. So?”
“So that’s the same Ray that you told me cheats on his girlfriends while he’s engaged to marry them. The same Ray that obviously hits on every woman who crosses his path. The Ray who came across to me as a womanizing sleaze. The Ray that obviously can’t be trusted!”
“So you think that he… “ Chad had to think about it a bit. “I guess it’s possible.”
Mel shook her head. “I’d say more like very probable.”
“So what do we do about it?”
“Nothing! There’s nothing to do, and no reason to do anything.”
“Maybe it would be a good idea to cancel our date,” Chad suggested – hopefully.
“Not on your life!”
Chad wasn’t exactly happy to hear that. Especially since Mel seemed so adamant about it. That could only mean she had something awful planned for him.
Just then, the waitress came back with a tray full of large glasses of tea. She set them all out on the table, two in front of Chad and one for Mel. “Are you ready to order?” she asked. Chad realized that he hadn’t had time yet to look at the menu.
“The child’s steak for her and I’ll have the oriental chicken salad,” Mel replied for both of them.
The waitress soon left and Chad’s mouth was already watering. Steak! He was ready for a good meal.
“You haven’t touched your drink yet,” Mel said as she eyed the two large glasses in front of him. “Are you leaking yet?”
Chad hadn’t even been paying attention to whether he was wetting or not. But one thing he was certain of, he wasn’t leaking just then and wasn’t even close to it. And worse, he knew he had to be running out of time! He grabbed one of the large glasses of tea, with both hands like she had made him do last night, and started drinking.
“I read over that paper you wrote for me,” Mel said as he drank.
Uh oh! “I’ll do better next time,” he replied. “It was just hard to come up with things for something like that on such short notice.”
Mel mostly ignored what he had said though. “Tell me,” she said as she leaned forward toward him again, “what you said in the last part – the part about deserving to be incontinent just because you were dumb enough to think you wanted it – do you really feel that way?”
Chad had to stop and think about it for a moment. “I guess… Sort of.”
Mel just looked at him for a moment. “What made you put that in the paper? It was so different from everything else that you wrote.”
Chad just shrugged. “I don’t know… yeah, I do, but …”
“But what?”
“Well… It’s just that… Those stupid suppositories you make me get all the time. Not only is it every day, but it’s twice a day! And there’s no way to stop them. I have no choice but to mess myself whenever they decide to go to work. Right then and there, no if ands or buts! And I hate it. Yes I like wetting my diapers, I always have. But I hate messing in them and those stupid things don’t give me any choice!”
“So you messed yourself again this afternoon?”
Chad rolled his eyes. “I mess myself every afternoon. I can’t help it. Those stupid pills make sure I can’t help it!”
Mel was silently applauding. He had gone last night and again this afternoon without really getting one. He only thought he had gotten them. But obviously the results were still the same. “Too bad,” she replied with absolutely no sympathy at all. “You know the rules of the bet.”
“Yeah. I know,” Chad replied sullenly. “But can’t you just skip them once in a while?”
“No. I’m not going to skip any – ever! Obviously they’re working and that’s all I care about.”
Chad wasn’t the least bit happy to hear that. He had no answer so he just grabbed his drink again and emptied a few more inches from the glass.
“So you got your vacation time approved?” Mel asked as he drank.
“Yeah,” Chad replied as he took a breath and set his glass back down again. “And it came through awfully fast. It usually takes a day or two, but this time it went through in just a few hours.”
That didn’t really surprise Mel, given the rumors that had been floating around the company, not to mention the way Chad himself was dressing all the time now… not to mention the arrangement she herself had made with Mr. Baxter the owner of the company. “I’m trying to rearrange my schedule for that week too,” she told him.
That was news to Chad. Why would she do that? For that matter why had she asked him to take the days off? Were they going somewhere after all? “What’s going on that week?” he asked as he picked up his glass of tea again.
“You’ll find out when the time comes.”
That answer scared Chad more than a bit. What did she have planned? One thing he was certain of though, it couldn’t be good. Not by a long shot!
“You’re not coloring today,” Mel noted as he set his glass back down again. The nice waitress went through all that trouble to remember to give you the crayons but you haven’t even touched them yet.”
Feeling foolish, Chad dumped out the few crayons from the box and opened the same coloring book menu he had colored last week.
“See if you can make it look more… like a toddler would do,” she suggested.
Like a toddler? What was the sense? Chad picked up a crayon at random and started scribbling around on the page, not paying a whole lot of attention to staying in the lines or even what part of the page he was coloring. Like a toddler. “So how was your day?” Chad asked as he colored, trying to get the subject away from him for a change. He was hoping that if Mel talked about herself, then she wouldn’t find more humiliating little things for him to do. “You must have been into something difficult this afternoon since it made you run late.”
“Difficult? I guess you could call it that.” While Mel couldn’t really tell him about any of the details, she could tell him about general things and how a simple routine matter turned into something that became a major problem – when it should never have been a problem at all.
Chad listened, and colored, and drank his tea. All the while making little comments to show that he was interested and still listening. Before he knew it, the waitress was back with their dinners. The smell of the steak made his mouth water again. Once again, Mel took his plate from him, along with his knife and fork, and cut his dinner up into tiny pieces. Fearing she would keep cutting it like she did last night, he hurried to finish his first glass of tea. He was very grateful when she pushed his steak back over to him so he could finally eat – with only his spoon – held in his left fist – like a toddler.
Mel finally grabbed her own knife and fork and dug into her salad. So good. She continued to tell him little things about her day which was mostly uninteresting – other than the part since she had talked with Robin. She found it nice to be able to talk about her day with someone who seemed interested. But the one thing she didn’t talk about was the one thing that was now weighing heavily on her mind. How was she going to deal with the Robin woman now? She had been wrong in the conclusions she had drawn over the silly things that Robin had told her earlier. She knew that now. But Robin still had to be dealt with – and soon. But she had failed to set things up the way she needed to for Operation Robin. Could it all still work? Maybe. She’d have to think about it.

Friday, September 23, 2011

The Bet - Chapter 42 (Friday – week 6 Part 6 of 8)

The Bet
by Karen Singer

Chapter 42 (Friday – week 6 Part 6 of 8)

Chad would have skipped getting a cup of coffee, but he just wanted something to drink too badly. Besides, it might look odd if he suddenly didn’t take one like he usually did. But he was finally doing better at holding back now, so he allowed himself the small – luxury? He hated to think of it like that, as a luxury, because every bit of liquid he put into his system still had to come out the other end.
He was sitting at the table sipping at his coffee, listening with one ear as the women talked about problems with their kids, when another woman came hurrying into the room and right up to the table. “Girls, girls!” she called excitedly as she approached the table. “I just got the news!”
“What news?” several of them asked.
“Remember what we were discussing about Sissy and Derek earlier?” she asked as she looked straight at Sissy. “Well, it turns out that we were right! Derek admitted it to Ray just a little while ago and I heard it straight from him!”
The level of excitement at the table tripled at least. Chad just felt stunned and sick! “No! It’s not true!” he yelled. But nobody was listening to him. Every one of them totally ignored his pleas of denial.
“Sissy!” Robin yelled excitedly over the din of everybody else’s excitement. “You should have just told me! Derek confirmed it, so you can stop denying it now.” Then she thought of something else. “Girls! Girls!” she yelled excitedly to get everybody’s attention. “Sissy is taking some time off later this month. I’ll bet he’s going to get his sex change then!”
Chad was even more shocked. “I’m not getting a sex change!” he yelled over the incredible excitement all around him. But nobody was listening again. None of them would believe him. “I’m not getting a sex change!” he yelled once again in frustration. “And Derek and I aren’t getting together. There’s nothing between us!” But nobody would believe him. They were all too excited about everything.
“Sissy!” Robin yelled excitedly to him at one point. “We have to look at wedding dresses!”
Oh God!

“You’re sure you want to do this, Mel?” Sandy asked into her phone.
“Absolutely!” Mel replied.
“It just seems a bit… extreme to me.”
“It’s only about half what I’d really like to do to her!”
“It’s not her I’m worried about,” Sandy replied. “But, if you’re sure…” She giggled at the thought of it. “I’ll certainly do my part.”
“Great! Thanks Sandy. I appreciate it.”
“Dinner again this Sunday?” Sandy asked.
“Oh… No,” Mel replied. “Sorry, Sandy, not this week. We’ve got that date on Sunday instead. We’ll do it the next week for sure though.”
“No problem, Mel. Cassie and I have just been enjoying our little get-togethers, that’s all. Not to mention his cooking.”
“Yeah, I’ve rather enjoyed it a bunch too,” Mel admitted.
“Okay,” Sandy replied. “We’ll be ready.”
“Thanks Sandy.” Mel hung up her phone. Everything was now in the works for Operation Robin. As she had told Sandy, it was only about half what she’d really like to do to Robin. Of course she would also like to get a court order to keep her well away from Sissy – forever! But she knew that no judge would ever issue such a thing. So this was the next best thing… and also the more satisfying option.
It was now time for the next part of Operation Robin – the setup! She picked up her cell phone and found Robin’s phone number. She punched a few buttons and waited.

Robin was looking through web sites of wedding dresses when her cell phone rang. She just couldn’t believe that Sissy hadn’t told her the truth about him and Derek from the beginning. She would have totally understood. She didn’t know why even now he was denying it so vehemently. Not that it mattered. Wedding dresses were fun to dream about anyway – even if she was already married.
She finally picked up her phone and noticed that the call was from Mel. Wow, what timing! “Hello?” she said excitedly.
“Hi Robin? This is Mel.”
“Hi Mel. Oh! I’m so excited! Sissy should have just told me! I would have totally understood! I’m already looking at wedding dresses!”
Mel was suddenly confused. Told her what? Understood what? And she was looking at wedding dresses? Mel suddenly had even worse thoughts about her. “Um… Told you what?” she asked.
“About Sissy! And why he’s doing what he is of course.”
Mel was shocked. “He told you?”
“Well, no. In fact, he still keeps denying it. But we got confirmation from Derek himself!”
Derek? What the heck was the stupid tramp talking about? She just couldn’t believe that Sissy had told someone else all about the bet – and especially about his baby side! And now Robin was looking at wedding dresses? She didn’t know what to say! “Um…” But Robin was too excited to be held back.
“Mel, tell me, is it true? The real reason Sissy is taking a vacation later this month is to get his sex change?”
Once again, Mel was taken for a major loop. What the hell was going on there? All her plans were suddenly out the window. She couldn’t think properly. “Uh… Robin. Let me get back to you okay? I have to go now.”
“Please get back to me soon, Mel. I have sooo many questions!”
“Yeah, I’m sure you do. So do I.” Mel hung up her phone. Her head was spinning. According to that tramp Robin, Sissy had actually spilled the beans on everything – the bet, his diapers, everything. She was really surprised because he had so carefully protected that secret in the past. And now Derek had confirmed it? What had Chad told Derek? Was Derek the first person he confided in? And what the heck was that about him getting a sex change during their days off later in the month? That was definitely weird! And now that stupid blonde tramp was looking at wedding dresses? She was going to marry him? Not on her stupid pee-brained life! Sissy belonged to her… not to that stupid trollop!
Her next client was going to have to wait a few minutes. She had to get to the bottom of things – and fast!

Chad had actually been making progress on the paper Mel had assigned him to write when he heard Robin talking on the phone over the wall between them. His hearing particularly heard her say Mel, which grabbed his full attention. It had been a fairly quick conversation, but what he heard sounded like more of the gibberish all the women were bantering about the company now – unfortunately.
He was about to get up to go ask her about it when he noticed an email come in from his boss, Tom Robinson. He quickly opened the email and saw that the request he had submitted earlier to take off the end of them month had been approved. What surprised him was the fact that his request had been approved so fast – usually it took a few days. This one had gone through in just a few hours. At the end of the email, Tom mentioned that he should pick up his paperwork in the Human Resources office. With the speed that they had processed his request, Chad figured that picking up the approved paperwork sooner rather than later was probably a good idea – especially since Tom had gone to the trouble of mentioning it.
Talking to Robin was going to have to wait a few minutes. She wasn’t going anywhere anyway. He closed the email and hurried out to pick up the paperwork.

Robin was still looking at wedding dresses when she heard Sissy’s cell phone ringing on the other side of the wall between their cubicles. After the third ring, she wondered why he wasn’t picking it up. After the fourth ring she got up from her seat to see why he wasn’t answering it. She reached his cubicle on the fifth ring and was surprised to see that he wasn’t there. She saw his cell phone on the desk and went over to see if she could tell who was calling him, but the moment she got near his phone the caller gave up and the display on his phone went blank. Oh well. She’d just tell him about it when he got back.

Mel wanted to throw her cell phone across the room. Why wasn’t he answering? Was he too busy with Robin again? She’d strangle her if he was! Both of them! And now that the word was out, Robin was looking at wedding dresses? Why the hell didn’t he answer his phone? She needed answers! Who could she call? Ray’s name immediately came to mind, but something about that didn’t feel right. She wasn’t exactly up for Ray trying to talk her into going out with just him alone. Derek’s name was a fast second. She found his phone number and called.
Derek was driving through the city when his cell phone rang. He hated answering the phone while he was driving, but since it was usually the office calling about business, he had little choice. “Hello?” he said, wondering what kind of problem someone had called in with now.
“Derek? This is Mel.”
If traffic hadn’t been so light, Derek might have had an accident. Mel was the last person he expected to hear from. “Mel! I’m glad you called. It’s a little late for lunch, but if you’re interested in dinner…”
“No, Derek. That’s not what I’m calling about.” Mel sighed and forced herself to calm down and think logically, if not exactly straight. “Derek, what I’m calling for is… What the hell is going on at that company of yours?”
“Huh? What are you talking about?”
“I just talked with Robin and she told me some of the craziest things. What did Sissy tell you today?”
“Sissy? I haven’t talked to him.”
Derek shook his head and rolled his eyes. “Whatever! I still haven’t talked to ‘her’ since yesterday. Why?”
But Mel was now trying to make sense of things. “So you haven’t talked to Sissy at all? No emails? Nothing?”
Derek was confused. “Like I said, not since yesterday. Why? What’s going on? I’ve been out on a service call for the last hour or so.”
But Mel quickly realized that Derek was a dead end. He didn’t know anything – which meant that things were adding up even less. “Never mind,” Mel replied. “I need to find someone who actually knows.”
“About what?”
“That’s just it, I’m not sure myself.”
“Well, we could still discuss it over dinner.”
Some little piece in the back of Mel’s mind was tempted, but she couldn’t deal with that just then. Besides, she had other plans for later. “Sorry. I’ve got other things I have to do tonight. I’ll have to see you on Sunday. I’m looking forward to that.”
Sunday was the last thing Derek wanted to be reminded of. “Unfortunately, I’m not looking forward to it. Dating “Sissy” is not my idea of fun!”
Mel sighed. Actually, she still would rather be going with Derek than Ray, but… “I know Derek, but well… a bet is a bet. And I appreciate you doing it.”
“So go to dinner with me and prove it!”
Mel sighed. “Some other time Derek. Some other time.” She hung up the phone and immediately dialed Sissy again – and again got no answer. Where was he? Fretting about what was going on, she finally admitted temporary defeat and went out to meet with her next client. But she was determined to make the meeting as short as possible!

Chad hadn’t been to any of the offices upstairs in quite a while so he was more aware than ever of everybody noticing him as he walked past the various areas. More than once, one of the women he now knew from the break room waved to him or said hi to him as he walked past. New friends? He supposed. But it was hard to tell since they teased him so much. He really couldn’t blame them.
He turned into the Human Relations office and the secretary there looked up at him with a big smile. She picked up a paper off of her desk and held it out for him to take. “Good luck,” she wished him as he took it. Chad thought it was a very strange thing for her to say – till he realized that she thought he was taking this vacation to actually get a sex change. How stupid! “I’m not going anywhere!” he told her. “And I’m not getting a sex change!”
“Of course not,” she said as if she really didn’t believe him.
Knowing that it would be useless to argue further, he turned and headed back downstairs. He finally turned down the hallway where his own cubical was located. As he got closer, he could see Robin’s cubicle just past his. He was going to head straight there to ask about Mel’s phone call, but just before he reached his own cubicle, the stupid suppository that Cassie had stuck up inside of him at lunchtime decided to do its thing. It was a little bit later than usual, but not by much. Hating the experience, he stopped dead in his tracks as the little bomb did its work. Knowing it would be impossible, he didn’t even try to hold back on it, he just wanted the ordeal over with as soon as possible. But today, it seemed to drag out longer than usual. Was that because he had eaten more for breakfast and lunch? And worse, it almost felt like what came out of him was a little bit more solid than it had been in a long time now. But it was really hard to tell.
Troubled by it, he turned directly into his own cubicle instead of going on to Robin’s and he carefully sat down. As he did so, he noticed that when he sat, it felt different, a bit more squishy than usual. Ugh! For a few moments it was a bit more uncomfortable too. For as much as he loved wetting his diapers, he hated messing in them just as much if not more. But what chance did he have when Mel made sure he got one of those stupid suppositories shoved way up inside of him – twice a day, every single day! There was just no winning!
And then it hit him. The paper he was writing for Mel only contained two – tenuous – reasons and that was it. The real reason he “deserved” to be totally incontinent hadn’t even dawned on him till then. He again opened the paper he was working on and went to the very end where he started a new paragraph. “Anyone who is dumb enough to really want to be incontinent, deserves to be incontinent, just so they can be stuck with the total helplessness of the situation. No way out. No going back. Stuck with the mess. Stuck with the humiliation. Stuck with the discomfort. Stuck with everything that goes with it. They deserve to be incontinent just because they wanted to try it!”
In the next cubicle over, Robin thought she heard something in Chad’s cubicle. “Sissy, are you back?” she called over the wall.”
“I’m here,” Chad replied.
“Girly voice!” Robin yelled back.
Ugh! “I’m back!” he yelled again – in his girly voice. But he thought he heard something else from Robin’s cubicle and suddenly realized she was on her way over. Quickly he reached for his mouse to close the paper he was working on for Mel, but unfortunately he had been typing and the program asked him if he wanted to save his work before closing it. He clicked “yes.” Robin walked into his cubicle a moment before the paper actually closed.
“Hey, you finally found something to write about?” she asked cheerily.
“Uh… Sort of.”
“Can I see?”
“Um… No, it’s something private.”
“Are you sure?”
Gee she could be nosy! “Of course I’m sure.”
“But maybe it’s something I could help with?”
Chad briefly wondered if she and Cindy at the gym were related. “No, it’s nothing like that. It’s just something… personal.”
Robin finally gave up. “Okay. I just wanted to tell you that your phone rang a few times while you were gone. Where did you go anyway?”
More questions! “Up to HR to get the approval for my days off.”
“You mean for your sex change trip?”
“I’m not getting a sex change! Gee!”
Robin laughed. “I know. But it’s fun to think about you getting married. That’s what I’ve been doing all afternoon, looking at wedding dresses for you.”
Chad stared at her, not believing what he had just heard. “You’re kidding! Wedding dresses? I’m not marrying Derek! I’m not even doing this just because I want to ‘get together’ with him!”
But Robin picked up on the wrong words. “So you’re admitting finally that you do want to ‘get together’ with him.”
“No! I just said I’m not!”
“No, you said you’re not doing it ‘just because’ you want to get together with him. So you do want to and there’s just another reason too.”
Chad’s head was spinning. Where did she come up with these things? “No! It’s not that at all. Derek and I aren’t trying to get together at all! Period!”
“But you do want to.”
“No I don’t!”
Robin just smiled wickedly as she turned around. “I don’t believe you.”
Chad was left to stare at the empty entrance to his cubicle. Women! Where do they come up with these things? He picked up his cell phone to see who had called and saw that he had missed two calls from Mel. She probably wanted to remind him about their nail appointments later. No problem. He punched in her number and waited for an answer, but nobody picked up on the other end. He called her office phone, but unfortunately he only got as far as Andrea. Mel was busy with clients and it looked like she was going to be a while. But Andrea promised she would tell Mel that he called. Chad went back to finishing up the paper he was working on so he could get it sent.

Tuesday, September 20, 2011

The Bet - Chapter 42 (Friday – week 6 Part 5 of 8)

The Bet
by Karen Singer

Chapter 42 (Friday – week 6 Part 5 of 8)

Mel walked her client to the door and shook hands with him. Once he was gone, she turned back toward her office. The waiting room was empty except for Andrea who was typing something at her desk. She stopped in front of Andrea’s desk and waited till she had finished typing and could look up. “Okay, I give up. What’s so obvious? How can I keep Sissy from holding back at work?”
“You’re kidding, right?” Andrea asked. “You mean you really don’t know?”
“No! That’s why I’m asking.”
Andrea just shook her head. “Well, like I said, I’m sure there are things I don’t know about so you can’t do it.”
“Like what?”
“I don’t know! That’s the point.”
“Okay, well, there’s nothing I can think of. So what are you talking about?”
“I don’t believe you don’t see this already.”
“What is it?” Mel asked, her voice full of frustration.
“Well, you said that the only time he can work on holding back is when he’s at work, right?”
“Yeah. So?”
“So… Don’t send him.”
“Don’t send him to work. I mean, the guy’s probably got some vacation time, doesn’t he?”
Mel’s jaw dropped wide open as she stood there in shock. It was so obvious! Why hadn’t she seen it? “Thanks, Andrea! I owe you!” she said quickly before she hurried back to her office. Don’t send him to work! It was so obvious. This time, instead of emailing him, she picked up her cell phone instead.

“Break time Sissy,” Robin’s voice called from the entrance to his cubical. “Hey, what ‘cha looking at?” She walked in closer so she could see his computer screen. There were several pictures of models on it. “Hey, I’ve seen those. They’re beautiful, aren’t they? Have you seen the one in the teal print dress yet? It’s a couple of pages in.”
“Not yet,” Chad replied. “I haven’t gotten that far.”
“So go to the next page and see if it’s there. I want to show you the shoes she’s wearing.”
Chad started to click toward the next page in the website, but he was suddenly interrupted when his cell phone started ringing. He quickly picked it up and noticed that the call was from Mel. “Hello?” he said, carefully using his ‘girly’ voice.
“Sissy,” Mel’s voice replied. “What are you doing?”
“Um… Robin and I were just about to go to break.”
The stupid Robin woman again! Mel was so glad that she would be getting what was coming to her very, very soon. She could just picture the two of them walking hand in hand to break together. The very thought of it made her sick. “Sissy, I need to know if you have any vacation days available.”
Chad was a bit surprised by the question. “Vacation days? I guess so. I’m sure I have at least a week left.”
“Good! I want you to put in immediately to take off the entire last week of our bet together.”
“The whole last week?”
“You heard me. Now arrange it, or I’ll do it for you. Of course, you may not have a job left if I have to do it. Let me know as soon as you can get it arranged. Got it?”
“Yeah. The whole last week. I’ll let you know.”
“Good. How are you coming with the little paper I assigned you? I’m still waiting to read it.”
“I’m working on it,” Chad replied.
“Well get it done! No excuses!”
“I will.”
“Good. Don’t forget, nail salon tonight. Are you going to keep your current nail length or get them cut shorter?”
“I hadn’t thought about it,” Chad confessed.
“Well, if you do decide to get them cut, don’t get them too short.”
Chad was just surprised that the choice was going to be totally up to him. “Like I said, I hadn’t thought about it yet.” He glanced down at his long purple fingernails. Even in the lavender color, they looked so much more feminine with the longer nails. “I do kind of like the way they look when they’re this long.”
“Good,” Mel replied. “Oh, and you should consider a different color. Maybe something in the red to pink range. Maybe more towards the red end.”
Chad had to wonder why she was being so specific. What did she have planned for him now? “I’ll think about it,” he replied.
“Good. Let me know the minute you know about your vacation!”
“I will,” Chad replied. “I will.”
“What was that all about?” Robin asked.
“Mel wants me to take some vacation time from work.”
“When? The last week of the month?”
Chad did some mental calculating and realized that the last week of the month was also the last week of the bet. “Yeah,” he replied.
“So what’s going on? Where are you going?”
“I have no idea. She just wants me to take off.”
“So are you?”
Chad couldn’t tell her at all that he really had no choice in the matter. “Probably. I could use a few days off anyway.”
“Well, you just better not come back with a complete sex change without telling me first. I’ll kill you!”
Chad laughed. “No chance of that!” – he hoped. He had no idea why Mel really wanted him to take off or what she had planned for him. He wasn’t even sure he wanted to know. Knowing Mel, she might have the most outrageous plans for him. He just hoped it wasn’t really a trip anywhere. That would be most embarrassing!
“So are you going to cut your nails shorter?” Robin asked as they headed out into the hallway together.
“I hadn’t thought about it,” Chad replied as he again glanced quickly at his long lavender nails.
“I don’t know how you manage to do anything with them that long.”
Chad just shrugged. “You get used to it.” As they walked, he was a bit amazed. Wasn’t that the very thing he often wondered when he saw women with long nails? Now a woman was asking him!

Mel hung up her phone and stared at her back wall for a minute. It was so obvious! Why hadn’t she thought about it before? And now that she had ordered him to do it, she immediately felt better about things. With an entire week to work on him, she was sure she could win this bet! And speaking of taking off! She punched in Andrea’s number on her office phone.
“Yes?” Andrea’s voice came back.
“Andrea. Check my schedule for the last week of the month. Clear as much of it as possible. Everything if you can.”
“So you’re trying to take off too?”
“As much as possible.”
“Hang on a minute,” Andrea replied while she was still on the phone. She quickly glanced through Mel’s calendar. “I only see a couple of court appointments that will be almost impossible to get out of. But other than that, I can probably move things around so you have most of the time available.”
“Good. Do what you can Andrea. Thanks.”
Mel suddenly felt better than she had all day. Things would be even better now that she was going to take some time off too. Well, most of the time anyway. There were still a few pesky things she had to attend to at that time, but they were minor little things that couldn’t be helped. With that problem finally ironed out, she was able to turn her thoughts instead to much more happier things – like teaching Sissy ballet. She needed to come up with a routine for him now. Something he could perform in public. And she couldn’t wait!

Derek didn’t dare go down to the break room, even though he would have enjoyed a cup of coffee. Maybe he could just go out somewhere and get one, or maybe he could send one of his co-workers after a cup. But there was no way he was going anywhere near that break room while Chad… Sissy might be there!
Ray was on his way to confer with one of the other managers about the new government regulations on their industry when he had to pass by Derek’s office. He was a bit surprised to see Derek at his desk. The temptation to rub something in and get Derek’s goat a bit was just too much. He delayed his meeting for a moment and went in to see Derek instead. “You sly dog!” he announced as he entered Derek’s office.
“What?” Derek wasn’t at all happy to see Ray again, especially not with a grin that big on his face.
“You sly old dog!” Ray repeated excitedly once again.
“Now what?” Derek asked with more than a hint of annoyance in his voice. He just knew that Derek was up to something that he probably wouldn’t like.
“You should have told me!”
“Told you what?”
“You lost that bet on purpose!”
“I what? What are you talking about?”
“The bet. The poker bet. You lost it on purpose… you sly old dog you!”
“Ray, how could I lose that bet on purpose? Why would I ever want to do such a stupid thing? Especially with the consequences I’m facing now because I did lose!”
But Ray was still grinning from ear to ear. “I’m afraid the word is out now boy. You should have just told me. I would have understood perfectly.”
Derek was getting more and more frustrated with Ray, not to mention downright angry. “Told you what? What word is out?”
“Why, about you and Sissy of course. You should have told me.”
“Told you what?” Derek yelled back. “What about… me and… Sissy?” he spat the last word.
“Why, you and Sissy have this… ‘thing’ for each other. And he’s getting a sex change just so that you two can be together. You sly old dog you!”
Derek’s face was going purple. He was on the verge of exploding. “That’s not true and you know it! Stop this bullshit!”
“But I didn’t start it,” Ray replied happily. “It’s all over the company now.”
Ray was shocked. “All over…”
“You sly old dog you…” Ray said one last time as he walked out.
Derek was fuming. All over the company? Ray had to be kidding! It was the craziest thing he had ever heard. Common sense would show everybody that! He did his best to try to ignore what Ray had just said and chalk it up to more of Ray’s teasing.
Man did he ever need some coffee now. No, not coffee, a good beer instead! No, not beer, something much, much stronger!

The woman who Ray had originally gotten the rumor from was just getting up from her desk to go to the break room when Ray “just happened” to be walking by. He stopped just long enough to speak a few words with her about company business. But before he left, he added just a tiny bit more. “Oh, by the way!” he added. “Remember what you were asking me about earlier…. About Derek and Sissy?”
“Yeah?” the woman asked, suddenly very interested.
“Well, it looks like you were exactly right. Oh, he didn’t want to come out and just admit it, but I got enough out of Derek so that I know it for sure!”
“You’re kidding!” the woman replied, totally shocked and amazed. Now she couldn’t wait to get to the break room. Wait till the girls heard this!
The huge grin was back on Ray’s face as he watched her hurrying for the door.

Friday, September 16, 2011

The Bet - Chapter 42 (Friday – week 6 Part 4 of 8)

The Bet
by Karen Singer

Chapter 42 (Friday – week 6 Part 4 of 8)

Gloria took a sip of her iced tea and set her glass down. So far, the lunchtime conversation with Mel had been fairly nice – nothing at all about Chad or any of the usual things Mel had been consumed with for the last two months. But this time, Gloria herself was wondering about things. Things like… did Mel remember anything at all about last night during the time that she had been in a trance? Gloria was more than a bit worried about that, only because Mel was her friend and trusted her. But how could she bring it up without telling Mel what really happened? Her mind was so preoccupied with this question that she didn’t seem to realize for a while that Mel was talking more than usual, much more. And the things she was talking about were so disjointed that they almost made no sense. “Mel! Wait a minute!”
“You’re carrying on about nonsense.”
Mel slumped back in her seat. “Sorry,” she replied. “I’m just trying to keep things… light.”
Gloria was suddenly more worried than ever. Did she know she had been hypnotized? “I appreciate that you want to keep it light, but… jeez… you don’t have to work so hard at it. What’s bugging you so bad?”
As usual, Mel realized that her friend knew her all too well. “Sissy… and time!”
“I should have known.” Actually, Gloria was relieved. It meant that Mel still had no idea. Well, hopefully, she would never know.
“It’s just that, there’s so little time left in this bet, and I have way too far to go with him. You heard him last night, he still has so much darn control! I have to take it all away from him – in just three more weeks!”
“Sounds like a lot of time to me.”
“No it’s not! He should be totally there by now! He’s just… fighting me too hard!”
“And winning?”
“No! Never! At least… I hope not.”
“But he could win.”
“Not if I can help it!”
“Of course not.” Gloria was getting sick of Mel’s over obsession with Chad and their stupid bet. And Mel didn’t like to lose! “So what are you going to do about it?”
Mel shook her head. “I just don’t know. The problem is that he works on it constantly while he’s at work. I don’t let him work on it any other time.”
“So? You’ve still got three weeks.”
“Yeah, but… well, things may come up where I can’t control him as well.”
“Like what?”
“Ugh! Like this stupid date we’ve got this weekend. I wish I’d never done that!”
“Why? Just because of Chad?”
Mel just looked at her for a moment. “Partially.”
“So there’s more?”
Mel nodded her head a bit. “Kind of.”
“Okay out with it girl!”
“It’s just that… well… I think I’d rather be going with his date instead of the guy I’m stuck with.”
“Hey! I saw those pictures. The guys a hunk.”
“Yeah, but he’s a woman chasing, conniving, bastard who only wants to get it on with as many women as he can.”
“So? As far as I know, you’re not looking to get married anytime soon. Let him jump your bones and enjoy it.”
“Ugh! I’d rather it was Sissy’s date!”
“So you’ve got the hots for Sissy’s guy instead?”
“No! Not at… well, maybe. Just a little.”
“So let him jump your bones instead.”
Mel just rolled her eyes. “Not right now. Maybe when this bet is over with. But not right now.”
Gloria just shook her head. “Well, if you’re going to toss any of them away, send them in my direction. I’d give my right arm to go out with either of them.”

Chad stared at his blank computer screen, and stared, and stared. He still didn’t know what to write for Mel’s stupid paper. He had to write something though. He didn’t want to think about what kind of punishment she would dish out if he didn’t at least make a good effort. But there just wasn’t any good reasons he could put down. None!
Feeling defeated once again, he opened instead the spreadsheet where he kept his progress for the bet. Twenty-one days to go… still! Three weeks! Just one week less than a month! An eternity! He was more worried than ever about all the progress Mel had made in him. He had been having more and more trouble holding back every day. Every day he managed to hold back less and less. How could he hold out for another three weeks? It was way too much time. What was he going to do?
He moved to the space next to yesterday’s date and filled in the exact time he remembered – eight and a half minutes. Another minute lost over the day before. Another full minute! Mel was making more and more progress. Twenty-one days and yesterday he had only made eight and a half minutes. And so far, today was looking even worse. Twenty-one days. The way things were going, if he lost a full minute every day, then Mel could win this thing by next week! He had to find a way to fight back! But how?
He quickly glanced over at his column of reasons to win the bet. Respect, friends, and a life! The rest of it barely mattered right now. But even his three main reasons meant little to him today. All he knew was that he still wanted to win this thing, and so far, he was losing. Not wanting to think about it anymore, he closed the spreadsheet and went back to fretting about what to write in the paper Mel wanted.

Mel was looking at her calendar and her plan for Sissy. According to the schedule, this was one of the days when Sissy wouldn’t get one of the suppositories at lunchtime. He didn’t get one last night either. She briefly wondered if he would realize it, and more importantly, would he be able to control that part of him now? Her thoughts were interrupted by the ringing of her cell phone. “Hello?”
“Hey Mel. It’s Cassie.”
“Hi Cassie. What’s up?”
“Hey, I just wanted to tell you about Sissy today. You would have loved it.”
“What happened?”
“I got a chance to play with him again today like I usually do – when we’re alone.”
“But this time, just before I started using my little dildo on him, he claimed he had to pee. I had a bit more trouble getting the thing into him because his muscles were all tightened up to hold back, but eventually it went in and he got into it.”
“So what happened?”
“Oh Mel, you should have seen it,” Cassie laughed. “Every time I pushed the thing in, he squirted out a little pee from the other side. It was hilarious! And the poor guy didn’t even know he was doing it. By the time I finished, he thought he still had to pee, but when he went to let it out, almost nothing was left. I tell you, it was so funny!”
Mel chuckled a bit herself. “I can imagine,” she replied. “Say Cassie, did you put one of those suppositories inside of him today?”
“I thought he wasn’t supposed to get one today, so I just faked it.”
“Good. He’s not supposed to get one. I’m just wondering how they’re working, that’s all.”
“I guess you’ll have to ask him. I wouldn’t know.”
“Yeah. I guess I should ask. Say! While I’ve got you on the phone, I need your help with something I’m lining up for tomorrow. I’ll be talking to Sandy in a little while about it too.”
“Okay. What do you need?”
Mel smiled before she continued. Operation Robin was getting closer and closer!

Ray entered the little alcove where the copy machine was located and opened the publication of new industry regulations to the first page he wanted to copy. As he lined up the book properly on the copier he heard someone coming into the office behind him. Before he could hit the copy button, he heard a woman’s voice talking to the woman whose desk was close by.
“What do you think about Sissy and Derek?” the woman asked.
Ray stopped his hand from touching the copy button. The words Sissy and Derek completely caught his attention and he wasn’t about to do anything to prevent him from hearing what was being said.
“Oh God,” the woman at the desk replied. “I guess it makes more sense than anything else.”
“But he keeps claiming it’s not true!”
“Yeah, and they used to claim the earth was flat! I still think it makes the most sense.”
There was a slight pause before the other woman answered. “Yeah, I guess it does. Still… You’d think we would have caught wind of it before this.”
“I don’t know. You know how men can be. And something like that I guess I would want to keep a secret too.”
“Yeah, I suppose. Is this all the stuff for marketing?”
“That’s it. Thanks for picking it up this time.”
“No problem.”
Ray peeked his head out of the alcove and watched the woman walking away. What the heck were they talking about? Whatever it was, it sure sounded… interesting! He finally hit the button on the copier, then lined up five more pages and copied each of them.
On his way back to his office, he stopped at the woman’s desk. “Hey,” he said, “I couldn’t help overhearing you talking a minute ago. Something about Sissy and Derek? What’s going on?”
“Oh,” the woman said. “It’s nothing. Just something we were considering at break earlier this morning.”
“And what’s that?”
“Well, it’s probably not true anyway but… We got to wondering if maybe… since Sissy just got divorced and Derek is also divorced that… well… Maybe Sissy is getting a sex change so that he can be with Derek.”
Ray’s eyes went as wide as saucers.
“You have to admit,” the woman continued, “it kind of makes more sense than anything else. Sissy totally denies it of course, but then, I guess I would too if I were him.” She watched the startled look on Rays face for a moment before she asked. “You know Derek pretty well, what do you think?”
Ray was still groping with all the possibilities, but finally he replied, “I wouldn’t be the least bit surprised.”

Chad was grasping at straws. He had to write something, so he went for the thing that hurt the most – the truth. It might not exactly why he “deserved” to be incontinent, but it was the best he could come up with. And the painful truth was that he wanted to be incontinent just for the humiliation of it. Something inside of him seemed to know that fact so that’s what he put down. Now the trick was to fluff it out with enough trash to make it sound good. Having something he could finally start writing, he went to work.
A little while later, the humiliation factor led him to another thought. One that had been mentioned a few times when this bet first started. If he was incontinent and in diapers all the time, then he wouldn’t have to take bathroom breaks while he was performing his duties as a sissy “servant.”
Having two subjects to write about now made his task that much easier. He only hoped that Mel would buy it when he sent it to her. As he worked, he kept glancing more and more at the clock on his computer. Was it break time yet? The only reason he was wondering was because he was a bit thirsty. Since he purposely didn’t get anything to drink with his lunch, now he wanted something. Besides, Mel had him so used to drinking something almost constantly that now his body seemed to miss it. He was starting to do better at holding back though – finally! That much alone made being a little thirsty totally worth it.
As break time drew near, he closed the paper he was writing before Robin could get a chance to see it. He opened his web browser again and went back to looking at the fashion web sites. If only he looked like those models. Any of them!

Tuesday, September 13, 2011

The Bet - Chapter 42 (Friday – week 6 Part 3 of 8)

The Bet
by Karen Singer

Chapter 42 (Friday – week 6 Part 3 of 8)

Chad was becoming a bit concerned. He had only been able to try holding back a few times so far today. What concerned him the most, was that he just realized that he had peed again – without knowing he was going to do it. He was fairly sure that he hadn’t peed much at all this time, but still, he had almost totally missed it. And not for the first time today.
Too much to drink! He knew without a doubt that that was the problem. He had already had an extra cup of coffee that he didn’t usually get in the mornings – and that was on top of the unusual amount he had guzzled all last night. Way, way too much to drink. If he didn’t start cutting back on the amount he was drinking now, then Mel was going to win for sure! He promised himself that he wouldn’t drink anything at all when he ate lunch. That should help – he hoped – because right now, it almost seemed like Mel was winning this bet, and he couldn’t dare let that happen. He had to find a way to fight back harder. But how?
He stared reluctantly at the blank page on his computer screen. What was he supposed to write? Why did he “deserve” to be incontinent? He had to come up with something. He “wanted” to be incontinent – just for the humiliation of it. But that didn’t mean that he “deserved” to be incontinent. Besides, he “wanted” it – outside of the bet. For the bet, he didn’t want it. Or did he? Well, he did, he just couldn’t allow himself to be that way – yet.
Confused, he opened up his favorite web search program and typed in a query for reasons to be incontinent. He briefly searched through the pages it brought up – and found nothing – nothing that he could use to indicate why he “deserved” to be incontinent.
Frustrated, he closed the search program and stared at his screen again. He finally began typing, but it was only the title. He had written it just in the hopes that it might inspire him. But so far…
Still having no clue what to write, he again opened up his web browser and typed the word ‘fashion’ into the search program. Looking at what the fashion models were wearing was a lot more interesting than trying to write an impossible paper.

“No! I’m not going to do it!”
“Oh come on. Be a good sport,” Ray replied as he sat down on the edge of Derek’s desk.
“Being a good sport has nothing to do with it,” Derek replied as he looked up at Ray from his chair. “Especially in this case!”
“But it’s the proper thing to do.”
“Bullshit! And you know it!”
“Well I think you should,” Ray urged.
“Well I think I won’t! And that’s final. It’s bad enough I have to go out with him!”
“Ray smiled. “Don’t be a bad loser.”
“Well stop being such a gloating son-of-a-bitch winner! I’m not going to do it. So get that stupid thought out of your head!”
Ray got back to his feet. “Okay. Have it your way. I’ll pick you up on Sunday.”
As Ray headed back toward his own office, he mused, “Well, if Derek didn’t want to do it – willingly, then he’d just have to find a way to make it look like he did!” He smiled as several possibilities came to mind. Poor Derek. Riding his case and spreading gossip about him and Sissy was so much fun.

Chad pulled into the parking lot of the gym and parked his car, but he hesitated before getting out. If he didn’t need changing so badly he would have been tempted to skip coming here today. He wasn’t at all sure how Mel would feel about that, but somehow, he figured that she wouldn’t like it. Having little real choice, he got out of the car and grabbed his purse and diaper bag.
Cindy watched through the glass door as Chad walked across the parking lot toward the door. As a receptionist, she got to know more of the customers that came in than most of the other employees. But by far, the one that interested her the most was Sissy. According to Cassie, he secretly loved all the humiliation that got heaped on him. She couldn’t really understand why, but she had to admit, she enjoyed seeing the silly things he went through. And knowing that she too could tease him and humiliate him only added to her interest.
Her only problem was that Cassie had just told her she couldn’t “help” with him again today – not even watch. But Cassie had left her a possible opening.
“Not today,” Cassie had said. “Not unless he specifically asks you to.”
So now Cindy had just one thing on her mind, getting Sissy to ask her to “help” once again. “Hi Sissy,” she called brightly the moment he walked through the door.
Chad mentally groaned. Why did she have to be so cheerful? It had to be a very bad sign. What had she and Cassie cooked up to do to him today? Knowing that he wouldn’t get away with not greeting her properly, he dropped his usual curtsey and said hello.
Cindy giggled. There was just something about seeing him do that, that thrilled her all the way down her spine – right down to her toes. She leaned excitedly across the counter. “Can I change you again today?”
Chad was caught off guard by her question. She had asked that yesterday, and when he told her no, she had somehow turned things around so that the decision was taken away from him. “I don’t have any say in the matter,” he replied somewhat flatly.
“So that means I can be there?” she asked excitedly.
“Wait a minute! Is Cassie really giving me the choice this time?”
Cindy backed off, no longer so excited. “Maybe,” she replied noncommittally.
But Chad was grasping at his own straws. “If that’s the case, then defiantly – no!”
“But I did a good job yesterday,” she argued. “I didn’t even hurt you when I put that silly little pill up inside of you.”
Chad shook his head. “I’m sorry, but if I have any say at all in this matter, then I’d rather it be just Cassie. Will you find her for me please?”
But Cindy wasn’t about to give up yet. “Well then can I just come in and watch? Please?”
Chad shook his head again. “I’d rather you didn’t,” he replied politely but firmly.
“Oh pooh!” Cindy pouted. “I’ve been looking forward to it all day.”
Chad was suddenly wondering if he had just won this battle. Unfortunately, he couldn’t take anything for granted. “I’m sorry,” he replied. “But like I said, I’d rather it be just Cassie. I’m more comfortable with just her.”
“But if I’m there, then you’ll get more comfortable with me too!”
“I’d rather not!” Chad replied. “Now will you please find Cassie before I start leaking all over everything here?”
“Darn it!” she said as she sullenly left her post to go in search of Cassie.
Chad watched her leave, split between celebrating his victory over her and worrying about what Cassie might say when she came back. Fortunately, he didn’t have long to wait. He dropped another curtsey and another sissy hello as Cassie entered the gym foyer.
“Are you ready?” Cassie asked.
Chad noticed that she didn’t ask anything about Cindy. “Yes,” he replied as he shifted the weight of his diaper bag strung over his shoulder.
“Then let’s get busy.”
Surprised that there was no mention at all of Cindy, he followed Cassie back through the gym, noticing as he went that Cindy just went back to her post behind the front desk – rather sullenly, but she went back. But the question now was, would she stay there?
Back in the little office, Chad started to undress while Cassie laid his things out. By the time he was down to just his diapers, plastic panties and waist cincher, she had everything laid out and ready. She handed him his bottle as he laid down on the floor. As he put the bottle to his mouth and started drinking – and Cassie began removing his plastic panties to change him, he was struck by one thought – just like old times! This was the way it was supposed to be – private! Just Cassie and himself. Thankfully. And somewhere in the back of his mind he prayed it would stay like that, because it was always possible that Cindy could come in at any time.
Cassie unfastened his overly saturated diapers and pulled them down. “Somebody’s been wetting an awful lot this morning,” she declared as she did so. “I noticed that the inside of your plastic panties are a bit wet too. It’s a good thing you had them on.”
Chad didn’t doubt for a moment that he had leaked a bit this morning. It was only just a little while ago that he had begun getting back into the swing of things with really being able to hold back. Granted, he hadn’t been able to hold back very long… yet. But hopefully, that would change this afternoon. He had no intention of getting anything at all to drink with his lunch today. Hopefully, that should help a lot!
Cassie glanced at his tiny plastic encased organ as she wiped his front side and applied a bit of baby lotion to his skin. His trapped penis was just as tiny as it always was. She had to wonder if the thing ever grew anymore. But a quick glance at the wicked looking spikes just touching his skin on the inside of the device made her remember that he needed to stay as small as possible. It was the only thing that prevented those spikes from causing him major pain. She had seen him writhing on the floor more than once because of those spikes. She quickly slipped his soaked diapers out from under him and inserted two new ones in their place. “Okay,” she said. “Time to roll over.”
Chad set his bottle down and rolled over so she could do his backside. Would Cassie “play” with him today like she used to? He was really hoping she would. It seemed like so long ago since she had last done it, and he missed it – the only little bit of fun he seemed to get anymore. The feeling of her hands as she massaged the baby lotion into his backside was pure heaven. He shut his eyes and concentrated on it. And when he heard her telling him to “skooch his knees up,” the feeling of anticipation he felt in his stomach was almost painful. He couldn’t wait.
It had been so long now since he had been able to get any sexual relief at all. Never had he been allowed to orgasm since this whole bet started. He was kept painfully chaste with no chance of ever getting hard. And then stimulating thing after stimulating thing had been thrown at him – for so long now that his body seemed to react to the stimulation on the inside, but his under exercised organ no longer seemed to respond at all. And if by some chance it did, then he was very sorry for it almost immediately. So much so that he instantly wished he would never try to get hard again. But if feeling the excitement on the inside was all he had left, then it was far better than nothing, and now he couldn’t wait to feel Cassie’s usual toy that she used on him… at least he hoped she would use it on him.
The feeling of her finger starting to play with his asshole sent shudders of pleasure and anticipation all through him. He couldn’t wait to feel her pushing it in. But she was still holding back, teasing him, building his anticipation. He briefly wondered what Cassie did when she and Sandy were together. And for that matter, what did Sandy do to her? But those thoughts were instantly banished the moment her finger actually slipped inside of him. He held his breath for a moment as she pushed it in, then pulled it back out. In then out. Deeper, then shallower, then deeper still, then shallow. Over and over. He never knew how far in she was going to push it in.
And then her finger was gone completely and he heard her opening the desk drawer to get her toy. And that was the moment he realized that he had to pee again. He had to practice holding back! That was very important. He clamped down hard on his muscles, trying to do whatever he could to build up his strength there.
And then he felt Cassie’s hands again… and the tip of her toy playing with his anal hole. He felt her trying to push it in, pushing harder and harder. But with all his muscles locked the way they were, she couldn’t do it, she couldn’t push it inside of him! But he wanted it in! But he had to hold back!
“What’s wrong?” Cassie asked. “You don’t want it today?”
“Yes I do. Badly!” Chad replied.
“So what’s wrong?”
“I have to pee! Badly!” he replied.
“Oh.” Cassie wasn’t sure what to do. She pulled her dildo away. “We’ll just try another time,” she told him.
“No!” He wanted it too badly. He needed it too badly. The question was, could he possibly relax his anal muscles enough to let her get it inside of him – while at the same time manage to hold back from peeing? “Try it again,” he told her. “But go slowly.”
Cassie was a bit surprised, but she was willing. She put her toy back up against the little hole in his backside. “Ready?” she asked.
It was a moment before Chad felt he had enough control over things to nod that he was ready. Relaxing the muscles of his backside ever so slightly, he prayed that he would be able to hold off on peeing. He felt her pushing harder, then harder. He relaxed more and more. The rounded tip penetrated him further and further, but not fully. And then, almost suddenly, it went in, right past the first few ribs on her toy. He felt totally jubilant as he felt her slowly pushing it further and further up into him. And then she was pulling back on it again. And he was still holding back on his pee. Slowly in, then slowly out. Over and over, faster and faster, harder and harder. His attention now was completely on the wonderful feeling of her toy going in and out of his backside. He closed his eyes again in pure bliss!
Cassie watched him closely. Things were now almost back to normal again. He was slowly working himself into a little frenzy over the feelings he was experiencing. And then out of the corner of her eye, she noticed something odd. Then it happened again. She had to bend over to watch more closely to see if she was right. And she almost laughed. Every time she pushed in on her toy, he squirted a little bit of pee out of his chastity device. Almost like a little squirt gun. And it didn’t look like he even knew it! Over and over again, just a tiny bit each time. And it kept happening and happening. It was causing quite a little puddle on the diaper that was just below it. Fortunately, the diaper soaked everything up fairly quickly.
Chad was in heaven. But eventually, he reached the point where there was just no use continuing anymore. It was that total frustration point where he knew that the release he wanted so badly just couldn’t be obtained. Frustrated and disappointed, he stopped, but not before he pushed back and forth just a few more times for that last bit of enjoyment.
“All finished?” Cassie asked before she withdrew the toy.
Chad tried to look back at her, which was difficult, and nod. “Yeah,” he replied.
“How about peeing? Are you done with that too?”
Peeing? Had he leaked? He was still trying to hold back! He was still working hard at it! “What do you mean, am I done? Did I leak a little?”
“You’ve been peeing since we started!”
Chad was shocked. “I have?” He did his best to look down under him and saw how wet part of the diaper on the floor was. Ugh! He had leaked.
“Well, are you done yet?” Cassie asked again as she pulled the toy fully out of him.
“No, I’m still holding back.”
“Then why don’t you just let it go and finish what you started so we can get out of here.”
Still in the same position, Chad relaxed his muscles to let the rest of his pee out, but what came out amounted to only a little bit of a dribble before it finished. So frustrating! He had failed totally.
“Are you done now?” Cassie asked again.
“Yeah, I guess so,” Chad replied rather sullenly.
“Then roll back over so I can get you diapered up again.”
“Aren’t you going to replace the one I just wet all over?”
“Why? You wet them a lot more than that every time you come in. I’m sure you’re used to it. Besides, that’s the inner diaper that I went to all the trouble to cut slits in. I don’t want to do that again to another diaper.”
Reluctantly, Chad rolled over and set his backside down on the already wet diaper. He could feel the wet spot high up near the back of the diaper as he set his backside down on it. So much for starting the afternoon of in dry diapers. It was just a good thing he enjoyed them being wet!
Cassie grabbed the jar of suppositories and made a show out of opening it and pulling one out. She showed it to Sissy. “I know you just love these things, don’t you?” she teased.
Chad mentally groaned. “Just for once, can’t you please leave it out? Please?”
Cassie shook her head. “Sorry. These little beauties are one of the main reasons Mel wants me to change you every day. Lift your knees up for me.” Once Chad was in position, she pushed his legs up further, once again exposing his backside that she had just finished playing with a minute ago. Palming the suppository in her hand, she stuck only her finger way up inside of him. Once again, he would never know what he didn’t get… and hopefully, he would never see any difference.