The Bet - Chapter 48 (Thursday – week 7 Part 2 of 7)

The Bet
by Karen Singer

Chapter 48 (Thursday – week 7 Part 2 of 7)

Robin moved her mouse a little, then clicked it, trying to get some work done. But her heart wasn’t in it. As much as she tried to work, her brain was too preoccupied with feeling bad over what she had done with Sissy. Even this morning! It wasn’t right! It was all wrong! It was the very things she had been mad about in the first place. Mostly. But it had been like she couldn’t help it! Curtsey for her every morning to greet her? Ridiculous! And now she felt bad about demanding it. But should she go apologize to him? With as mad at him as she still felt, she just couldn’t do it.
So what should she do? With a frustrated sigh, she gave up all pretense of working. She wasn’t getting anything accomplished anyway. What was he doing over there on the other side of the wall? She knew he wasn’t working on their project. She wouldn’t let him! He was probably wasting his time searching the internet instead of doing something useful… like trying to learn something new to use here at work. Or at least stay up on the latest trends for their job. But somehow, she doubted that he was doing anything except goofing off – like a child!
So what was she going to do? She couldn’t think! Especially with him so close – right in the next cubicle. She needed to get away! Go somewhere else to think! Frustrated, she got up and headed out. She paused only slightly as she passed Sissy’s desk. Her quick glance showed her pictures on his screen, but she never paused long enough to really see what they were. But pictures weren’t work related, so just as she guessed, he was goofing off! Not that she really cared. Just as long as he didn’t touch their project without her say-so!
Not knowing where to go, she wandered the hallways as she tried to think. But no answers were coming to her. Eventually, she found herself in the break room, which was empty. She did notice that the coffee pot was filled and ready so she poured herself a cup and took it over to the women’s usual table. She sat and nursed her coffee for a long time while she pondered what to do.
If only she had someone she could talk to about it. Someone who could help without thinking she was crazy. She certainly couldn’t talk to Mel! Mel was the last person she’d want to talk to. But thinking about Mel reminded her of Mel’s friend Gloria. She had made more sense than anyone she had talked to in a while. She wouldn’t mind talking to Gloria – but it would have to be without Mel! And Gloria was Mel’s friend! So she was left with nobody to talk with at all.
She sat and nursed her coffee, no solution coming to her. But she didn’t leave. Eventually, she watched as a worker came in with two boxes of doughnuts and set them out. Then the worker checked the coffee to make sure there was enough. Then the worker left, and she was alone again. But only for a few minutes. Two men came in and headed for the coffee pot. They were the first ones to arrive for morning break. She got up and refilled her cup, grabbed a doughnut, and sat back down again. No answers. Nothing.

Chad glanced at his clock. It was break time, but where was Robin? He had thought he heard her leaving a while ago, but as far as he could tell, she never came back. He got up and went to her cubicle. She wasn’t there. Puzzled, he headed alone for the break room.
He was nearly in line to get coffee before he spotted her at their usual table. She already had her coffee. He wondered where she had been. He got his own coffee and one of the doughnuts and carried it over to the table. There was no seat open next to Robin so he took one a bit further away. All through break, he noticed that it looked like she wasn’t paying much attention to what was going on at the table – like she was thinking about something else. The few times anyone spoke to her, she gave mostly short answers that didn’t really say anything.
Robin was mostly annoyed anytime someone spoke to her, mostly because she hadn’t been paying attention so she had to try to remember what had been said. Fortunately, nobody really talked to her much. She was glad that for once Sissy wasn’t sitting next to her. He was her main problem. She just didn’t know what to do about him.
It wasn’t till break was nearly over that the idea hit her. It wouldn’t solve her problem at all, but maybe… maybe… she could at least get her own thoughts and fears figured out. Suddenly, everyone was getting up to go back to work. Good timing! She got up right along with them and headed back to her desk. She knew Sissy was following her, but fortunately, he wasn’t saying anything. She didn’t acknowledge his presence in any way, not even when she got back to her desk.
But working right now was not her first priority. She grabbed her phone and dialed Mel’s number… and started walking down the hall with it, away from Sissy. But she didn’t get through to Mel, she only got as far as Mel’s receptionist, Andrea.
“Mel just went in with a client,” Andrea said into the phone. She recognized Robin’s name as one that Mel wanted to be told about immediately if she called. But still… “Can this wait till she gets out or do you need me to get her now?”
Robin felt a bit of frustration. Mel was busy! It figured! But... “No, it can wait… a bit. But not too long I hope. Can you have her call me?”
“Absolutely! As soon as she finishes. Um… I estimate about half an hour. Will that be alright?”
“Sure,” Robin replied. “That’s fine. Thanks.” She hung up the phone and headed back to her desk. Half an hour. Not long, but still an eternity. She tried to fill the time by working, but she simply couldn’t concentrate on the job that needed to be done – which only added to her frustration. Ugh! She was falling further and further behind on the project!
She thought about Sissy, just on the other side of the wall, doing nothing! Nothing! And that fact irked her! And so did the sinking realization that she could put him to work, get him to help. Let him do what she wasn’t capable of doing today… just so the project could get back on track. Damn him! “Sissy!” she called over the wall. “Get in here!”
Chad nearly fell out of his chair at the unexpected summons. He quickly went around to her cubicle and curtseyed as he entered. “You wanted me?” he asked.
Robin actually winced at his curtsey. It wasn’t her! It wasn’t right! But she said nothing about that. “I need you to do some work for me,” she told him. She spent the next five minutes explaining what she wanted, then kicked him out again. And again she mentally winced as he curtseyed before leaving. She really needed to put a stop to that!
Chad was elated. She had found some work for him to do. Real work! Work where he would be making a definite contribution to the project. He wondered what had changed her mind… not that he was going to ask. As far as he was concerned, he was going to do everything possible to stay out of her way – completely! He quickly closed his internet browser and opened the project instead. Down to work!
Robin stared at the entrance to her cubicle where Sissy had disappeared from only moments ago. She felt guilty – for a number of reasons. She felt guilty for treating him badly. She felt guilty for not including him in the project so far, and now she felt guilty about making him work because she couldn’t. It wasn’t right. But she could do nothing about it. She glanced at her clock. Still fifteen minutes till Mel would call – probably. If Mel called.
Not wanting to sit at her desk again, especially now that she could hear the faint sounds of Sissy working on the other side of the wall, she grabbed her cell phone and began wandering the hallway’s again, but this time she didn’t go near the break room.

Mel walked her client to the door and shook hands with him. Then she turned and headed back toward her office.
“Robin called you,” Andrea told her as she passed her desk.
Mel was more than a bit surprised at that. “She did? What did she want?”
“She didn’t say other than she wanted to talk to you. I got the impression she wanted to talk sooner rather than later.”
Mel nodded. “Okay, thanks. I’ll call her right away.” She went back to her office and found Robin’s number and called.
Robin jumped when her phone suddenly rang. “Hello?” she said quickly.
“Robin?” Mel’s voice came through. “How are you? What can I do for you?”
Robin sighed before answering. Where should she start? “Um… I really hate to ask this,” she began.
“Anything,” Mel replied quickly. “And don’t be afraid to ask.”
“Well… You know your friend Gloria that I talked to at lunch the other day?”
“Yeah.”
“Well… Do you think you could call her and ask if I can meet her for lunch again?”
Mel was surprised by that. “Of course. In fact, you can join us anytime you want. We’d love to have you.” Actually, she wasn’t all that sure how Gloria would feel about it.
“Well… that’s just it. I mean… I don’t want to be rude or impolite, but… Um… I was really just hoping I could talk to her myself. You know?”
Mel did feel a bit put out… but under the circumstances… “Sure,” she replied as cheerily as she could. “I’ll call and ask her, then let you know. Okay?”
“Thanks Mel. I appreciate it. A lot!”
“Is everything going alright with Sissy? Is there anything you need me to do?”
“Oh no! Like I said, I really would just like to talk with your friend Gloria again. Please.”
Mel realized that Robin wasn’t going to tell her anything about what her problem was. “No problem. Like I said, I’ll let you know as soon as I talk to her.”
“Thanks again Mel,” Robin replied. She felt somewhat relieved, but only somewhat.

Mel hung up her phone. Robin wanted to talk to Gloria. Alone! She wasn’t sure how happy she was about that, but at least Robin hadn’t started yelling at her again. She picked up her phone and dialed Gloria’s number.
Gloria was just about to go into a session with one of her few morning clients when she heard her phone ringing. She quickly motioned to her client that she would be just a moment, then she answered the call.
“Hi Gloria,” Mel said. “I need you to do a favor for me.”
That didn’t exactly sound like the kind of thing that Gloria had on her list of things she most wanted to do. “What is it?” she asked. “I’ve got a client waiting.”
“Robin just called me. She wants to meet with you for lunch.”
Ugh! Just what she needed. “Do you mean just me, or both of us?”
“Just you.”
“I was afraid of that. You know I usually get a lot of money for things like this.”
“I know. But I figure that if she’s got a problem, then it’s my fault to begin with, so I’m responsible for it. So bill me for it. In fact bill me for both of your lunches too.”
“You know I was just kidding,” Gloria replied.
“But you also know me better than that. Bill me.”
Gloria shrugged. “Why not? Okay, tell her I’ll meet her outside our usual place.”
“Thanks Gloria. I appreciate it.”

Robin was still heading back to her desk when her phone rang again. That was quick! “Hello?”
“Hi Robin. I just talked to Gloria. She said she’ll meet you outside the restaurant where we had lunch the other day. Is that okay?”
“Wonderful!” Robin replied with relief. “And I’m so sorry about this. It’s just that… Well… Never mind. I just appreciate it.”
“No problem. Let me know if there’s anything else I can do for you.”
“I will. Thanks Mel.” Robin felt much more relieved as she returned to her desk. Gloria had made so much sense when she had talked with her. But the question now was, would Gloria be able to help her this time? She could only hope.

Mel stared at her phone for a few moments after she finished talking with Robin. She desperately wondered what Robin’s problem was… and she was sure there was some kind of problem because why else would she want to talk to Gloria?
But since she was fairly certain that Robin’s problem was related to Sissy, she was reminded of one other little technical thing she had to arrange for Sissy now. She picked up her phone again and called Cassie’s number. She listened to the phone ringing for a few moments and was about to give up when she heard Cassie breathlessly answer it. “Hi Cassie. It’s Mel.”
“Hey Mel. What’s happening?” Cassie asked.
“It’s time to make a little change again in Sissy’s suppository routine.”
“Okay, no problem. What do you need?”
“Don’t put any more up into him at lunch time from now on. I’ll continue to give them to him at night once in a while. But that’s being cut back too. I just need you to make sure he keeps thinking you’re giving them to him.”
“You think he’s ready for it yet?” Cassie asked.
“As far as I can tell he is. Besides, it doesn’t matter much. We’re running out of time and I have to stay on schedule.”
“Okay,” Cassie replied. “From what I’ve heard, he doesn’t have a clue anytime we do it or don’t do it.” Another little thought hit her. “Cindy isn’t going to like it though, because it means I can’t let her change him. I don’t want to take any chance that she might ‘spill the beans’ so to speak.”
“Well, it won’t be for too much longer anyway. Just the rest of this week and next week. After that, he’ll be with me all day.”
“Okay,” Cassie said. “No problem.”

Chad headed slowly toward the gym doors. Yesterday, Cassie had taken care of him. But the way things were going lately, he was betting that this time it would be Cindy, the receptionist, who would be doing it. When Cassie changed him, she played with his backside, giving him the most wonderful feelings in the world. Almost like regular sex. He just wasn’t able to orgasm from it with her… yet. He couldn’t wait to keep trying though. But today, if Cindy took care of him, then he had no idea what would happen – other than she would change his diaper. Oh yeah, and stick another stupid suppository up his butt. Ugh!
Bracing himself for Cindy, he opened the gym door and went inside. The first thing he noticed was that Cindy didn’t look as excited to see him as usual. Or maybe it was just his imagination. But that all changed when she leaned across the tall desk and smiled at him. Wickedly? He started bracing himself for the worst. But she was just staying right there, not moving, not saying anything. Waiting? Ugh! He curtseyed and said. “Hewwo, Cindy,” in his sissy voice – his old sissy voice. He was rewarded to see her smile broader and stand back up again.
“Hi Sissy,” she replied. But she didn’t say anything else or even offer to go find Cassie.
Chad saw her just standing there as if she was waiting for something again. “So are you going to be changing me again today?” he asked tentatively.
Cindy’s face brightened somewhat. “Would you like me to change you today?” she asked hopefully.
Chad wanted to be changed, he just would rather she didn’t do it. “I want to be changed,” he replied noncommittally.
Cindy leaned forward again and said a bit softer. “So then you want me to change you?” she asked hopefully.
Chad didn’t know why she wanted to drag this out. As far as he could see, the fact that she would be changing him instead of Cassie was probably a foregone conclusion. If she was going to do it, then he’d just as soon get it over with. “Yes,” he replied somewhat testily.
“Tell me again,” Cindy said with a bit of a giggle. “Tell me you want me to change you.”
Ugh! “I’d like you to change me,” Chad replied. Then, to end the pointless banter between them, he added the word, “Please!” Hoping it would get her moving.
Excitedly and almost defiantly, Cindy held her head high and said, “Then let’s go,” as she came out from behind the tall desk and led the way toward the back of the gym.
They met Cassie heading towards them about halfway through the big room. “There you are,” Cassie said. “I was beginning to think you were late today. Thanks Cindy. I’ll take him from here.”
“But he asked ‘me’ to change him today.” Cindy replied a bit defiantly.
“No!” Cassie replied sternly. “I told you earlier… No!”
“But!”
“No! And don’t ask again! Now get back up front where you belong!”
Defeated, Cindy headed back to her station at the front counter.
Chad was grateful, but he realized that he had obviously missed something. Maybe Cassie didn’t want Cindy changing him because of the way she had banged on his chastity device the last time with those scissors. Either way, he was glad that Cassie would be doing it!
“So, did you really want Cindy to change you instead today?” Cassie asked a few minutes later as she started pulling things out of his diaper bag.
“Heavens no!” Chad replied. “It’s just that she can be so…” he searched for the right word.
“Manipulative?” Cassie suggested.
“Yeah. Manipulative!”
“So you’d rather have me doing this than her?”
“I’d much rather you do it!” Chad replied with conviction.
Cassie reached into her desk drawer and pulled out the toy she used on his backside every day. “I wonder why?” she replied jokingly.
A short while later, she was holding firmly onto that toy as Chad pumped his back end against it furiously. Once again she was struck by how desperate he seemed to be. And once again, she noted how defeated he was when he gave up. But that didn’t seem to keep him from trying every day. She actually felt for him. She just wouldn’t let him know that. Just as she didn’t let him know that she was only faking putting the suppositories up inside of him – from now on.

The Bet - Chapter 48 (Thursday – week 7 Part 1 of 7)

The Bet
by Karen Singer

Chapter 48 (Thursday – week 7 Part 1 of 7)

The clock was well on its way towards morning when she dreamed her final dream of the night. She was on stage, in her beautiful pink ballet costume, dancing for a huge audience in a grand theatre. But it wasn’t her as she was now, it was her as she was in high-school – the last time she wore that ballet costume. She was thinner, lither… younger. Not that she noticed that in her dream.
The music started and she danced. Beautifully! Fantastically! And the audience was quickly on their feet in appreciation. But it was a short dance, only a small part of her program for the evening. The music ended and she finished with a pose that left her gesturing towards the opposite side of the stage, where Sissy was, also in his pink ballet costume.
The same music started again, but this time it was Sissy’s turn to dance… the same dance. The audience was shocked. He was doing very well! Not up to her ability of course, but far better than any other man could do. Far more graceful and… feminine! And when he finished his portion, the audience cheered… not just for him… but for her. Because this evening wasn’t about her dancing, it was about showing the world how she had taught him… a mere man… almost an animal… how she had taught him to dance so well.
Then it was her turn again. Another short piece of music, another dance… followed by Sissy repeating what she had just done. Back and forth they went, her demonstrating how she would do it, followed by him showing the world how well she had taught him. And the audience was amazed!
They continued back and forth like that, until midway in one of her dances, midway in one of her great leaps, her alarm clock buzzed.
Oh hell!
She reached over and turned the annoying thing off. It had been such a nice dream. Why did morning have to come now? She sat up on the side of her bed for a moment before getting to her feet. Grabbing her robe, she headed out to her kitchen, following her routine of habit that made her think of nothing but a fresh cup of coffee to help get her going. Coffee! It would taste so good!

He was partially awake by the time the miserable loud blaring rock music crashed out of his pink clock radio, but that didn’t make it any less shocking. One minute he had been laying in bed, enjoying the peaceful relaxation, and the next he was in a state of panic, scrambling as fast as he could to roll off of his blow-up mattress and turn off his alarm. Empty baby bottles were scattered everywhere in the process as he quickly rolled out of bed. Silence was returned to the room instantly with the click of a button, but after such loud noise, the sudden silence was a shocking silence.
Still on his knees, he took a moment to catch his breath and calm down after his panicked activity. A moment later, his brain began to wake enough to take in other sensations – sensations that really felt all too normal to him now. His diapers were heavily bloated – as usual. Messy too – as usual. His bra was holding up the heavy breast forms that were strongly glued to his chest – as usual. And his pacifier was again in his mouth – as usual. Overall… it was all just the usual. His normal morning wake-up situation. Normal for him… now.
He climbed awkwardly to his feet, struggling a bit against the bulk of his overly bloated diapers, and waddled his way out to his kitchen to see if she had left him a note during the night. He could no longer say that she always left him a note, but she usually did. He was glad to see that the note was there again today. The usual. And it felt… comforting. Most of the note could have been copied from many of the notes before it, except for one minor addition today. When he went to her apartment, Mel wanted him to have his pacifier in his mouth again. She sometimes asked for it, and she sometimes didn’t. So very often, he left it out. His life was so humiliating all the time, that any tiny little things he could do to make it less so were always welcome opportunities.
He grabbed three baby bottles out of his refrigerator and carried them out to his solitary chair. He sat slowly and gingerly, afraid that his raw backside might still be as bad as it was yesterday. But while he could feel it, it was much more tolerable today. No problem. He mostly closed his eyes as he sat drinking bottle after bottle, because there was nothing he wanted to see. Certainly not the childishly colored pictures Mel had made him do in the restaurants a while back… and also certainly not the framed contract of the bet between them. That he didn’t want to see at all! There was also the design that Sandy had done – the design for his nursery – if he lost this bet. But while just the thought of a nursery like that sent thrills through his under-exercised sexual needs, it was also something that he didn’t want to see – because he had to win this bet!
As he drank bottle after bottle, he noticed himself peeing a few times. No warning, no anything. If he had been busy with something else he might not have even noticed he was doing it. So interesting! It was amazing how interesting such a feeling could be… or maybe it was more like, it was amazing how interesting the lack of feeling could be. Later this morning, after his body had a chance to rid itself of all the liquid he was required to drink before he went to work, then he would start working on his ability to hold back again. But doing it now would be a useless exercise. Too much liquid pouring into his system too fast. It was better to get let it out of him as soon as possible. It was the only way he stood a chance.
With his bottles finally finished, he got up and headed to the bathroom where he would finally remove his bloated and messy diapers – and get ready for the day ahead. Things had been bad enough with just Mel dominating him. But now he had Robin at work to worry about too. He remembered spending hours yesterday sitting in the dark corner underneath her desk, with his thumb taped firmly in his mouth so he couldn’t remove it, unable to leave her corner. He prayed she wouldn’t do that to him again! Yet at the same time, the very same thought thrilled him. But then, what else would it do, he was a sissy.

Mel stirred the pot of baby food she was cooking for Sissy and turned the heat off. She poured the contents of the pot into a colorful child’s plastic bowl and set the pot back on the stove again. Now all she needed was Sissy. She glanced at the clock… and heard him knocking at her door at the same time. Right on time! A few seconds later, she opened her door for him.
“Good morning Mistress,” Chad tried to say around the pacifier in his mouth as he curtseyed for her. But what came out was mostly unintelligible. He realized as he said it though that talking with a pacifier in his mouth had one very good result, he didn’t have to worry about using his new and improved sissy voice, because talking with a lisp was pretty much out of the question!
“Good morning Sissy,” Mel replied as she stood back out of the way and let him enter. As she waited till he stowed his purse and diaper bag under her table by the door, she started looking him over. A simple skirt and blouse today. Not overly colorful, but he looked acceptable. She had already noticed the wooden necklace he was wearing earlier. She waited till he stood up straight again before she started looking him over more carefully. His hair was curled acceptably. His makeup was… acceptable. She noticed the pink studs in his ears today which seemed to go well enough with the red in the pattern of the blouse he was wearing. Overall, he looked… fine. Especially for a man dressing like a woman. For that, she was sure he was probably a bit better than fine. But was fine good enough? She decided she needed to start looking for ways to make him look even better. The more she made him look less like a man… the better! It would be like denying him yet more of his masculinity. “Okay Sissy, climb up into your highchair.”
Chad worked his way up onto his highchair and waited while Mel put the tray in place and tied a bib around his neck, just as she usually did. A minute later he was trying to spoon baby cereal into his mouth from a tiny rubber coated baby spoon held tightly in his left fist – just as usual. The routine was becoming so familiar now that it had become almost comfortable. Not that he’d ever let Mel know that. She would undoubtedly make things worse! Somehow.

Robin sat on her bed. She was all dressed and ready to leave for work, physically anyway. She stared at the large bag she carried every day. She had packed a few more items in it today than she usually did. She also usually carried a stack of magazines and other things in case she might want them during the day, but that stack was missing today. She was fairly certain she wouldn’t need them.
Her problem was… Sissy. And her. Last night it had all seemed so simple. So easy. But this morning, after a night to sleep on it, and after another night to think about what she had been contemplating doing with him, well… she was having second thoughts. Grave misgivings actually. What should she do?
It wasn’t right! Not by any measure she could think of. It wasn’t her! Not at all! She wasn’t that type! It was all wrong! And the things she had planned for him last night… They were wrong! Wrong! Wrong! Especially at work!
So why had she thought she could do it? And why was she still torn over whether she would actually do it or not? She just didn’t know.
With a sigh, she got up from the bed and grabbed her bag. One bag. No pile of other things. If she didn’t leave now then she would be late for work. She was probably cutting it awfully close as it was.
What should she do?

Chad booted up his computer and waited while it went through the many processes it had to run every morning. Robin wasn’t in yet. He had even gone to go to her cubicle to check. He glanced at his watch, if she didn’t get here soon then she was going to be late. Not that anybody would notice… or care. Of course, he would notice. But did he care? Yeah. Somewhat.
Like a breeze, he more heard the saw someone passing his cubicle. “Robin?” he called. He got up from his seat to go see.
Robin had just set her bag down on her desk when he showed up at her cubicle. She didn’t know if she was annoyed by that or not. She also wasn’t sure how she wanted to handle him today yet… in light of her thoughts earlier this morning.
“I was getting worried about you,” Chad said sincerely in his girly voice.
Robin shook her head. “Why? I’m not late!”
“Not really, but you’re never usually this late getting here.”
Something about that bothered her. Or maybe it was more that he, a sissy, should be concerned about her. She realized it was wrong for her to be bothered by it, but it still irked her. “Don’t worry about me,” she said more angrily than she meant to. Then she stopped and paused to think a moment. It was only because she felt a bit upset at him that she said it, even though part of her knew she shouldn’t. “Say… aren’t you supposed to be curtseying every time you see me? Not to mention… aren’t you supposed to be using your sissy voice around me too?” He was trying to get away with something again… like a child… again. And despite her earlier thoughts it still made her angry… a bit anyway.
Chad actually blushed as he curtseyed and said, “Sowwy Wobin,” in his sissy voice – his old sissy voice. There was no way he was going to use his new and improved sissy voice around her… if he could help it.
Robin watched his little curtsey and apology. It was so ridiculous. A man curtseying! But then Sissy himself was ridiculous – in so many ways. Yet she found she still liked seeing the silly little feminine action. An idea struck her, but then she thought again. It wasn’t right! None of this was right! So she couldn’t! She wouldn’t! But the idea wouldn’t go away. Once it was planted in her brain, it seemed like such a good thing to do. Despite her misgivings! So should she? But it was such a little thing. Nothing at all really. Not at all like the things she had planned last night for him. Finally, she gave into temptation. “You know,” she said, “I don’t see any reason why you can’t greet me real nicely like that every morning when I come in. You could even be standing out in the hallway next to my cubicle, waiting for me every day, just so you can curtsey for me and say hello to me every morning.” She still had her misgivings about it, but really, that wouldn’t be too bad, would it?
She had surprised him yet again. But really, her request was nothing much, just greet her politely every morning. It was only nice. But the problem with that was that she wanted him to do it out in the hallway where anyone else might see him. He thought of something else. “What happens if you get her before I do?”
“Just make sure you’re here ahead of me,” she replied as she reached over to turn on her computer. “Now get out of here and leave me alone. Please!” she added, because she really was having second thoughts now about the request she had just made of him. It wasn’t right! She needed to figure things out! And having him anywhere around wasn’t helping.
She sat in her chair and stared at her bag while her computer booted up. But she wasn’t seeing it. She was too torn over whether she should be dominating him or not. It wasn’t right! But if she didn’t… And this morning as soon as she saw him she had been all too quick to start giving orders again. Despite the fact that she knew it wasn’t right!
So what should she do? She was so torn over the problem. It wasn’t her! She was nice! She wasn’t mean! She wasn’t a bad person… not really. At least she hoped she wasn’t.
With her computer now ready, she opened her email program like she did every morning and was surprised to see an email from Mel – already. Curious, she opened it, even though she was now having serious doubts about everything she was doing.

Dear Robin,

Doing what you are doing with Sissy should always be on your own terms. I would expect nothing less. It still sounds to me like you are doing marvelously well and don’t really need much of my help. I did have one quick thing to mention, just in case you might be interested. Since you seem to like seeing him with his thumb in his mouth to help keep him quiet, in case you might need it, he should also have a pacifier in his purse too. Feel free to use that if you feel so inclined.

By the way, there is one other brand new development for him on my end. As of tonight, we’ve made a permanent change to his sissy voice. If you’re interested in hearing it, be on the watch for a lot of lisping and the use of other babyish words. Otherwise, it may sound much the same to you. But I definitely think the new things are an improvement.

As always, feel free to call or email me,
Mel

Robin couldn’t decide if she should care or not about the few things Mel had mentioned. She was more inclined right now to find a different way to deal with Sissy than to try dominating him like she thought she could. Something much… saner! But one thing did click in the back of her mind from Mel’s short email, what little she had heard out of Sissy’s mouth this morning hadn’t contained any lisping at all, so he was probably trying to hide something again… which still irked her even though she knew it shouldn’t.
Why should she care? She wasn’t that kind of person? It was all wrong! She was very tempted to march right over to his cubicle and apologize for the way she had behaved and to retract all her orders. But then what? She supposed she would just have to figure out how to work around him without getting angry. And probably without feeling totally repulsed by him too. And that wasn’t going to be easy. Not by a long shot.
Besides, she now had a different problem with him. Now that her eyes had been opened to what he really was, she was seeing different things about him that she had never bothered to notice before. Things that irked her terribly. He was so darn childish! In so many ways! And she couldn’t help it, because right now, it bothered her!
So… what the heck was she supposed to do?

Chad sat quietly at his desk, afraid to make the least little noise that might upset Robin. Once again he had nothing to do. Maybe he should start doing like Robin did and bring a bunch of magazines and stuff with him to look at. But he wasn’t really the magazine type. Besides, he could find everything he wanted on the internet.
He didn’t understand at all why Robin wouldn’t let him help with the project. It made no sense! But every time he had mentioned helping in the past, it only seemed to make her angry. So he said nothing and stayed as quiet as he could.
With nothing at all to do, he again opened up his internet browser. What should he search for? Today, he typed in the word ‘sissy.’

The Bet - Chapter 47 (Wednesday – week 7 Part 8 of 8)

The Bet
by Karen Singer

Chapter 47 (Wednesday – week 7 Part 8 of 8)

After Sandy left, Mel changed Sissy’s diaper, noting as she did it that his backside was still a bit bruised. As always, she put him on another hour and forty five minute time limit. But instead of letting him get dressed again, she left him wearing only his bra with his diaper and nothing else. “Okay, Sissy,” she said as soon as she had him ready, “ballet time again.”
Ballet time? Ugh! It had been a few nights now since he had had to practice ballet with her. While he loved seeing her do the dance movements, he wasn’t all that happy about doing them himself. But he supposed it beat standing on his perch in the corner. He went through the usual warm-up exercises with her, having to pause between each exercise while she made him “guzzle” some tea from his baby bottle. Then it was on to the next movement. But after the warm-up was over, she began teaching him exactly the routine she wanted. Chad was quick to realize that this time there was a big difference in the way she was going about it. This time she wasn’t continually trying different things to see how they looked. This time she seemed to know exactly what she wanted him to do from beginning to end.

Robin picked her crying son up from where he was screaming on the floor and held him and kissed him. He seemed to like getting into trouble and grabbing things he shouldn’t! She had only told him no! But he was getting tired now and the least little thing made him not just cry, but scream. Well, it would be his bedtime soon. She found his pacifier and stuck it in his mouth and cuddled him a bit more. It took a minute, but he finally stopped crying. She set him down on the floor where he immediately ran off as fast as his newly learned ability to run would let him – which seemed amazingly fast to Robin. Worried that he might try to find more trouble, she followed after him, but much more slowly. There was no keeping up with him! She had visions of him becoming a great track star when he grew up!
She got lucky. When she found him again, he was in the family room where her husband was watching TV. Her son had found his big toy truck to play with. She knew he wouldn’t play with it long before he moved on to something else – probably trouble – but the truck did seem to be his favorite toy – at the moment.
She sat down next to her husband and watched him playing. She loved him so much. He was so beautiful! So amazing! She felt so proud of him! But unfortunately, her thoughts were led to Sissy. The jerk! He acted like such a child! And so far, she found that dealing with him like a child made her feel the most satisfied as far as punishing him. Maybe as far as everything else went too. She simply didn’t dare not see him as a sissy anymore, because even now, after all these days, she still got angry. And she didn’t really like staying angry. She was still trying to make it up to her husband after the way she had behaved last weekend.
So she needed to keep reminding herself of what he was. What he really was! A sissy! It was just hard to do when she saw him every day because she had known him so long. She supposed that the old saying that old habits are hard to break was probably true. In this case anyway. So at least for now, she figured she needed all the visual reminders she could get. Anything that would let her constantly see him as a sissy – and nothing else.
But what did that mean? Images of him sitting on her floor sucking his thumb came to mind – along with an image of him in a dress, looking so much more like a woman than he used to be that it was almost frightening. But even though the fact that he was a man wearing a dress was supposed to mean that he was a sissy, so she figured, she didn’t really associate it that way. That woman image of him she still associated with an adult image. Maybe a different kind of adult, but still and adult. But that adult figure didn’t really help her as far as seeing him as a sissy. At least not the way he was dressed for work every day. It just didn’t help. So what could she do?
Her son was looking around now for something else to do. Even at one year old he seemed to be all boy. He liked playing with trucks and cars… and boy things. But Chad… or Sissy… was trying to be more… female. Or at least that’s how he saw his sissy side… and she supposed so did she.
Her son spotted her watching him and put a big smile on his face – she could see it even under his pacifier… and despite the drool and slobber that now ran down his chin almost to his neck. She held her arms out to him. “Come here,” she called. Laughing, her son got to his feet and ran, crashing into her leg where he held on and hugged her. She reached for one of her ever-present rags and removed the pacifier from his mouth and wiped his face clean again before putting the pacifier back in. “Is it bedtime yet?” she asked. But the only answer she received from him was to watch him take off straight for his father instead. It was his usual answer! No, he wasn’t ready for bedtime yet. But then, he was never ready for that!
Her thoughts turned back to Sissy. She wondered if he had a pacifier. Probably. That woman, Sandy, had been teaching him baby behavior? So she figured it would be very likely. Maybe a pacifier stuck in his mouth all day would help. An image of Sissy sucking a pacifier sprang to her mind… and seemed to overlay itself with an image of her son playing on the floor. There were differences. Huge differences. But… maybe some of those could be overcome.
Since she had a few minutes before she would put her son to bed, she went into her bedroom to search around.

Mel worked relentlessly with Sissy on his ballet, going over each of the mini-sections of the dance over and over again until she was satisfied with the way each one looked. She continuously had to stop to make him drink from his bottle, but drinking and making him keep wetting were her primary goal. Everything else she did was always secondary to that. It had to be!
She kept working with him until at one point during one of the easier movements, he seemed to pause as if he was confused. “What’s wrong?” she asked.
Instead of answering, Sissy looked down at his diaper and started feeling along the bottom of the leg band. “I think I’m leaking,” he replied in his new sissy voice.
Mel smiled as she glanced at the clock and noticed he still had a good ten minutes to go. “You’re getting better at this, Sissy,” she said.
Chad wasn’t sure if she was talking about getting his diaper to leak on time, or dancing.
“Maybe pretty soon we can see how well you can manage with an hour and a half.”
Ugh! Now he knew what she was referring to and he didn’t like that idea one bit!
Mel decided that they had done enough for one evening, although they didn’t really accomplish all that much towards his dance beyond the opening little bit she had planned.
But still, it was a good beginning. And the way she was working him, he was actually starting to look much better at what he was doing – in sections. Actually, much of what he was doing looked just plain silly, which was also something she was pleased with. “Okay Sissy,” she told him, “that’s enough of this for tonight. Go put something on my bed to protect it before we change that soaked diaper of yours.
Chad was glad they were done! He was starting to get really tired from all the exercise involved. And as much as Mel kept telling him that kids had no trouble doing all this over and over again, he wasn’t a kid! He was bigger, and the physical activity had taken its toll. He grabbed a stack of diapers that had been used before to protect either her bed or the floor and spread them out all over the top of her bed. Unfortunately, he knew the protection was absolutely necessary. When he was in this state, where he was on a constant time limit for leaking, he no longer had any control over where and when he was going to pee. It usually came as a complete surprise to… everyone.
As he was finishing laying out the diapers, Mel came in with a bunch of ropes in her hand and began fastening them to her bed frame. He wasn’t at all glad to see them, although he had to wonder why she would even bother. He wasn’t going to go anywhere, especially not when she was going to change his diaper for him.
As soon as Mel had her ropes ready, she had him climb up on her bed where she restrained him with his arms straight overhead and his legs spread-eagled. Then she pulled open the tapes holding his soaked diaper closed.
Chad expected her to just pull the wet diaper out from under him and stick a fresh one in its place, but he was surprised when she unlocked his chastity device instead. Now he knew why she had restrained him – to make sure he couldn’t touch himself down there while the device was off! Piece by piece he felt her removing it, till at last his penis was feeling the cool fresh air of the room. He was now so used to the heat inside the device and inability to feel anything down there that the sensation of the cool fresh air was almost a shock. Unfortunately, it was shock enough that five seconds after the air hit it, he started peeing again.
Mel had turned to the side to pick up all the pieces of his chastity device from the end table next to her bed so she didn’t see what was happening right away. It wasn’t till she turned back toward him with her hands full that she noticed what was happening. As fast as she could, she dropped the pieces on his stomach and pulled the wet diaper back up between his legs again. “I should know better by now!” she berated herself. “You can’t be left unprotected even for a second!” She smiled wickedly down at him as she picked up all the pieces to his device again before leaving to go clean them.
It was times like that, when someone caught him peeing uncontrollably, that Chad felt very humiliated… not to mention excited. Wasn’t that the feeling he had always dreamed of experiencing? He just wasn’t totally incontinent – yet. Not by a long shot. And with the short time-limit of this bet, he never would be. Too bad. But winning the bet was too important to him to even think about giving in.
Mel came back a few minutes later, most of the plastic pieces in her hands still dripping wet. She set them down on an out of the way part of the bed on top of one of the diapers protecting things. Then she took a good look at his tiny penis. Yes, it still appeared to be just as tiny as ever. Much more so than when they had first started this bet. She grabbed what little of it there was between two of her fingers and moved it around a bit to take a close look at it. As far as she could see, it looked just fine. No sign of any sores or irritation – other than the faint red marks from where the teeth from the device stayed in contact with his skin all the time.
She unfastened one of his legs and had him turn over so she could inspect his backside. As soon as he rolled over, she got a better view of the bruises still covering each of his rear cheeks. She could tell they had been heeling, but there were still places that were not only an angry red, but some spots were definitely still black and blue. And it looked like they might stay that way for a few days. She had no doubt at all that it still hurt him to sit down.
“Jillian did this to you?” Mel asked.
Chad was tempted to reply with “Yes Mistress,” in his sissy voice, but he opted to just say the word, “Yeah,” instead. The other way was much more humiliating and difficult because of all the S’s in it. Fortunately, Mel didn’t seem to notice.
“Maybe I need to have her give me some lessons in how to beat you properly!” Mel stated teasingly. It looks like she gives you a lot more to think about than I do. Obviously, I’m falling down on that job!”
Chad didn’t think so at all! But he said nothing for fear it would only lead to more trouble for him.
Mel carefully coated his bruised backside thoroughly with a cream to help heal it and to protect it from whatever else his diapers would press up against it. Then she pulled out her jar of suppositories and stuck one way up inside of him. He was getting less and less of them now, so every one she did give him seemed to be more important. Then she rolled him back over onto his back again where she heavily coated his penis with the same cream before putting his chastity device back on him and locking it shut.
From the position Chad was laying in, he couldn’t see what Mel was doing, but he could certainly feel it as she put each piece back into place. Each one feeling more and more familiar as the device was rebuilt. Till with one final click, the lock clicked home, securing everything and leaving him no way to touch or even feel that part of him. As used to it as he was, it was still very frustrating to him, not to mention that the sound of the lock still sent a momentarily twinge of panic through him. But all the manipulation Mel had just done with that part of him, and probably coupled with the shock of the lock clicking back into place again, suddenly made him pee all over again.
“Goodness!” Mel exclaimed as she quickly pulled the soaking wet diaper that was still under him back up over him again. This is becoming more and more difficult!” She looked up at his face. “Not that that’s a bad thing,” she teased. As soon as Mel was certain he was finished again, she pulled the wet diaper away and substituted a fresh dry one from a stack that she had already prepared.
Since it was still fairly early, Chad figured she would leave him in only one diaper again with another hour and forty-five minute time limit. But he was surprised when she started loading multiple diapers on him again – four of them! All followed by a pair of his plastic panties.
When she was done, she released him from the ropes. “That’s enough for tonight,” she told him. “I have other things to do tonight. Don’t forget to drink all your bottles before you go to bed.”
Chad got up from her bed and grabbed all his things, which fully loaded his arms. He tried to drop a curtsey for her, but with his arms so full, it was only an attempt. She didn’t seem to mind though. “Good night, Mistress,” he said in his new sissy voice, lisping the last part of the word mistress.”
“Good night, Sissy,” Mel replied, without bothering to get up from where she was sitting on the side of her bed.
She stayed there till after she heard the door closing. Then she headed back out to her kitchen where she started making a fresh batch of tea for him. While that was making, she again turned to her laptop to write to Robin. This time, she did have something to tell her. It wasn’t much, but it was something.

My Presidential Bid

I would like to formally announce that I will NOT be running for the office of President of the United States.

Although I am probably overly qualified for the position since I have never been elected to nor even run for any political office at all, the real reason I am not running is that I would make one, and only one, campaign promise – to piss people off! But unfortunately our world has somehow become so complex that people need more than that. They need details and promises that every politician is forced to make – and that they can’t in truth promise to keep. So in order for me to make and keep one promise, it would have to be that I would promise to piss people off. And I am sure that I could accomplish that with very little difficulty!

For instance, take the country’s economic situation. While congress is looking left and right for places to throw money – where it will do very little good in the long run, I would invest most of it in only one place – and surprisingly that would not be my pocket. What I would do is something so ludicrous that nobody in their right mind would consider doing it. And if that wouldn’t piss people off, then I don’t know what will.

First of all, I would put the money into oil. Don’t forget, it was the price of oil that precipitated this depression – and every other depression I can remember in my long lifetime. All regular gasoline sold at the pump would be priced at $2.50 per gallon. Not $2.50 and 9/10ths, but $2.50! And that price would include all federal, state, and local taxes – period! Diesel fuel for trucks would cost $2.75 – even though I understand that it’s cheaper to make.

Then the price of the fuel would be stabilized by law to remain at that exact rate for the next ten years. After that, it could only be raised by a very small amount and only by an act of congress.

So how is this supposed to help the economy? If you’re thinking of the savings to your wallet every time you pump gas you’re looking in the wrong place. Yes, you will realize savings – which will help a lot, but that’s not the bigger picture here.

With the price of fuel stabilized and relatively cheap, don’t you think that businesses would be very interested in moving back from overseas to build their plants somewhere where they can count on the price of energy to be stable? And don’t forget, the price of oil will also affect the price of electricity. Yes, the price of labor may be higher here than in other countries, but that would be more than offset by the stable cost of the power to run their business and the cost of fuel to ship their goods.

More businesses moving in, will mean more jobs for everyone – which will mean an improvement in the economy. It’s that simple.

Okay, that’s part one. Now for part two – and this will really piss people off! I would pass a law that in the next five years would require all brand new passenger vehicles sold in this country, including pickup trucks, to be required to run off of either electricity alone, or be hybrids that run off of both gas and electricity. This would help offset what congress would be losing by investing in oil and stabilizing the price. It would also drastically lower this countries dependence on oil.

Of course, I would also propose increased benefits and incentives for companies that produce alternative forms of electricity production. That would be a key part of the whole scheme too.

Then I would simply sit back and wait a few years and do very little else and let the economy take care of the economy. And of course, that would piss people off too.

So you see, since the only thing I can promise is to make everybody mad, I feel it’s better that I don’t run for office. Sorry, but that’s my final decision.

And I didn’t even start to explain how I would fix healthcare!

The Bet - Chapter 47 (Wednesday – week 7 Part 7 of 8)

The Bet
by Karen Singer

Chapter 47 (Wednesday – week 7 Part 7 of 8)

It was over an hour later before Mel had a chance to read Robin’s email. She read it through twice – carefully. Then she sat back to consider what she had just read. Basically, Robin was working with Sissy now on her own terms, but she would still appreciate any help that Mel could give her. On her own terms? Actually, Mel had expected nothing less. She chuckled a bit over Chad’s time-out predicament. Again, she wished she could be there to see it. It was getting late in the day now. She would send Robin a more detailed reply tonight or tomorrow – as soon as she figured out what she wanted to say. It still sounded to her like Robin was doing well enough on her own!
Her thoughts turned to Sissy and tonight. She had things she had to do with him tonight. Things that had been put on hold way too long. She smiled at that thought.

Robin turned off her computer and pushed her chair back. She glanced under her desk at Sissy, then she slipped her shoes back on again. He had only tried to move a few times in all the while she had made him stay under there, but it only took a little warning from her each time to make him be still again and settle down. Actually, she was impressed. She could never manage to stay in one place as long as he had. And an uncomfortable place at that! But then, she would never be stupid enough to put herself into that kind of position in the first place. The idiot!
She pulled her purse out of her desk drawer and checked her hair and makeup. She picked up the arm load of things she had carried in with her today but had never even looked at. “Good night Sissy,” she called just before she turned and walked out. “Don’t forget to turn off your computer.”
But as she left, the foremost thing on her mind was how she was going to manage to deal with him tomorrow. She couldn’t keep him under her desk all day again – not unless he really deserved it. So how did she want to deal with him? That thought plagued her all the way home.

Chad carefully eased his head backward from under her desk and fell flat on the floor. He breathed heavily for a moment at the relief it brought to his neck and back. His thumb was still taped to his mouth so it was more difficult for him to wiggle himself far enough out that he could stretch his legs again. Moving them was almost painful – but wonderful just the same. He rolled over and worked his way to his feet. First things first, he had to get rid of the tape securing his thumb in his mouth. He opened up Robin’s desk drawer and found a pair of scissors. One careful clip later, he felt a wave of relief as he was finally able to pull his thumb back out of his mouth. He pulled the tape from around his neck and wrist and threw it in the trash. As he walked back to his own cubicle, he stretched his jaw in relief and worked the kinks out of his thumb.
Somehow, he had managed to make Robin mad today. He promised himself that he would be more careful tomorrow! The only good thing about the situation he had been in, was that it was the perfect opportunity for him to work on his ability to hold back. Unfortunately, it had been too dark under there for him to see his watch so he had no idea at all how long he had managed. As he moved around now, he once again felt the urge building in him to pee. This time he had no trouble checking the time.

Mel opened her apartment door to the smell of dinner cooking, and it really did smell good! She saw him hurry out of the kitchen wearing his maid’s dress and drop his little curtsey for her. As soon as their greetings were over, he hurried back again. That was fine. He was cooking dinner for her and she wanted it to be just as good as it smelled.
She wandered into the kitchen after him. She watched as he stirred one of the pots on the stove one more time, then he turned the burner off and picked up the pot to carry it to the sink. “How long till dinner?” she asked.
“About ten minutes,” Chad replied as he held the pot over the stove, preparing to pour the excess water out of it.
“Put the pot down!” Mel ordered sternly as she hurried out to find her stick.
Chad quickly realized that he hadn’t curtseyed before speaking again, but he was clearly busy with something else! He was aghast that she would punish him that! But having no choice, he quickly returned the pot to the stove and nervously waited till Mel returned – which wasn’t long.
Mel swung her stick at his hip, knowing that she wouldn’t be hurting him at all – especially with a diaper on under his dress, but she also knew that it would get her point across. “When are you going to learn?” she asked as she swung her stick one more time.
Chad was very tempted to argue about it, but he knew it was useless. He curtseyed. “I’m sorry, Mistress,” he said in his sissy voice. “I’ll try to do better.”
“You’d better!” Mel replied as she turned to put her stick away. She was smiling to herself though as she walked away. Sometimes just picking on him could be fun! She headed over to her desk and pulled her laptop computer out. She needed to write Robin an email, she just didn’t know what she was going to say yet. She still had no idea what she was going to write by the time Sissy called her in for dinner.
As usual, everything was perfect and tasted fantastic. She banished Sissy to his perch in the corner again and said nothing at all as she watched him take a baby bottle with him this time. She watched as he climbed up onto his perch and precariously raised his bottle up so he could drink from it. He head looked to be at an uncomfortable angle. But that wasn’t her problem. At least he was still trying to keep wetting!
As she watched him, she wondered if it was more uncomfortable standing on the corner where he was or more uncomfortable under Robin’s desk. She was betting that standing on the perch was much worse for him… but Robin was certainly doing well! So what was she going to say to Robin?
She wasn’t quite done with her meal yet when she heard her phone ringing. Hating the bother, she got up and answered it. “Hello?”
“Hi Mel,” Sandy’s voice came back. “Have you heard it yet?”
Mel was confused. “Heard what?”
“His new voice!”
Now Mel was really confused. “What new voice?”
Sandy realized that Sissy hadn’t told Mel anything about what they had done last night. “His new sissy voice. We worked on it a bit last night.”
“You did?” Mel asked, totally surprised.
“Well, maybe we worked on it more than a bit, but I should have figured he wouldn’t tell you. Sorry.”
“So what did you come up with?”
Sandy paused. “Maybe I better tell you in person. Are you doing anything now?”
“No. I’m just finishing my dinner.”
“Then I’ll be there in a few minutes. Okay?”
“Great! I’ll be expecting you.” She hung up her phone. Sissy was finished with his bottle and his arm was back down at his side again. He hadn’t told her everything about last night… but then she knew that she had also made some assumptions. Evidently wrong assumptions!
She went back to the table and took another forkful of food without sitting down. So good! But with Sandy coming right over, she was finished now. She did grab her wine from the table though. “Sissy! Get in here and get up into your highchair!”
Chad carefully extricated himself from the corner. He had heard her on the phone but he didn’t know who she had talked to. Possibly business? Not that it mattered. He got up into his highchair and waited while Mel put a bib around his neck and put the tray back in place, locking him into the chair. He hadn’t picked out his own baby food meal this time because she hadn’t mentioned that he had to. But he watched as she went to the cabinet and started pulling out jar after jar. The knock at the door startled him and the usual fear ran through him.
“Don’t worry, it’s just Sandy,” Mel said as she went out to answer it.
Chad was relieved… somewhat. A minute later, he saw the two women come into the kitchen together.
“Oh hey,” Sandy said brightly. “It’s his dinnertime!” She turned toward Mel. “Can I feed him?”
“Be my guest!” Mel replied as she leaned back against one of the counters out of Sandy’s way. But she turned quickly towards Sissy. “And I don’t want to hear about it from you!” She saw Chad’s eyes go wide with surprise… or possibly fright, and he heard Sandy giggle.
As Sandy dumped jar after jar of baby food out onto his plastic dish, she started explaining. “Well, I guess I should tell you first about the beating he got last night for not leaking on time.” She looked briefly up at Mel. “Cassie told me that he was still red and sore when she changed him this afternoon.”
Mel looked over at Sissy sitting in his highchair. “That bad, huh?” She looked back to Sandy, “He told me about that this morning when he had trouble sitting in his highchair. He said they had some kind of paddle with holes in it and a whip.”
Sandy nodded as she put the last jar of baby food down and picked up his plate along with the tiny baby spoon she would use to fee him. “Yeah, they did. Actually, they have a bunch of stuff like that since they’re really into it… and last night, Jillian really seemed to be into it when she punished him for not leaking.”
Mel just shook her head. She felt for Sissy but… “But deadlines are deadlines. And in this case, he’s not allowed to miss one, no matter what the reason.”
Sandy nodded as she shoved the first spoonful of colored mush into Sissy’s mouth. “Yeah, and I did promise you last night that I would make sure that he either kept to his deadline, or we would punish him.”
“So he got punished.”
She nodded. “Royally!”
“Good!” Mel looked straight at Sissy. “Maybe it will help give him more incentive for the future! So what were you trying to tell me about a new voice?”
Sandy giggled as she continued feeding him. “Jillian didn’t think we had done enough with his sissy voice. Not by a long shot! So… she kind of made some suggestions and we tried them out. Actually, we were at it for most of the time we were there.”
“So what changes did you make?”
Sandy looked back and forth between Sissy and Mel for a moment. “Maybe it would be better for you to hear it. I don’t think I can really explain it all.” She looked at Sissy. “What’s my name?”
Chad was very embarrassed. He didn’t want to do this! But with Sandy and Mel right there, what choice did he have? In his sissy voice – his new sissy voice – he said Sandy. But what actually came out of his mouth was more like “Thanthy.”
Mel looked startled as Sandy looked around. She grabbed his baby bottle. “And what’s this?” she asked him.
Again, Chad felt very foolish. “Ba-ba.”
Mel just grinned as she watch Sandy handing him the bottle so he could take a drink. “I’m not sure I’m going to be able to understand him though.”
“I don’t know,” Sandy replied. “I think that once you got used to it, you’d have no problem at all. We managed last night pretty well.”
Mel shook her head. “I think I’ll have to hear more after you finished feeding him.”
As soon as his dinner was over, Mel and Sandy went into the living room where they sat on the couch together. Sissy had to come in and curtsey for them both as he stood in front of them. He wasn’t happy at all about trying to speak the way they had made him speak last night.
“Okay,” Sandy said. “I want you to tell us all about what happened last night.”
Last night? Ugh! And all in his ‘new’ sissy voice? He figured out where to start, then curtseyed before opening his mouth. He first explained how he went there to cook dinner for them last night. At first, Mel couldn’t tell much of a difference, other than the way he said anything with an ‘s’ in it – that kind of threw her a bit. But gradually, the more he talked… or tired to… the more subtle differences she found. He actually sounded more childish! Or maybe it was more like a much younger child than ever before. And at times, she almost laughed at the way he said things.
Finally, Mel got the whole story about exactly what happened all last night out of him, with Sandy occasionally adding to what he had said. And in the end, Mel could only laugh at the way he sounded when he spoke. “Okay,” she said as he finished. “I’m convinced! I love it!” She looked straight at Sissy. “This is how I want you talking all the time now… all the time! Everywhere!”
Chad only gulped. Wasn’t what he was already doing bad enough?
“Go clean up the kitchen now, Sissy,” Mel ordered. “Leave us alone for a while. And get yourself another bottle. Your deadline is almost here!”
Chad dropped a quick curtsey and hurried away. He was glad to get away from them. He didn’t like using the new… and improved… sissy voice at all! He quickly grabbed a bottle and started drinking as he tried to assess just how wet his diaper was. Very wet! Soaked! Fortunately. But time was still running out. Leak! Leak!
“It sounds like you had a lot of fun last night,” Mel said to Sandy.
“We did… kind of,” Sandy replied. “But to tell the truth, both Cassie and I were more worried about how badly Jillian was punishing him to really enjoy it all that much. We were both close to putting a stop to it several times. And the fact that he’s still so sore today… maybe we should have.”
“Don’t worry about it,” Mel replied. “I saw him having trouble sitting down this morning, but he didn’t seem to be hurting when he sat in his highchair a little while ago, so I think he’s probably okay.”
“Good!” Sandy replied. “Because I was a bit worried about it.” She paused for a second before continuing. “You know, I really do love his baby side. Completely! Well, let’s face it, I get off on it! Okay?”
Mel only chuckled. “I know.”
“Well, it’s just that… I really like it, but… I don’t think anyone else gets the same kick out of it that I do! I mean, you really like him better as your maid. And Cassie… well, I’m not really sure what Cassie thinks. Sometimes I know she feels sorry for him, but other times… well, I’m just not sure.”
“I think we all get a kick out of his baby behavior,” Mel replied.
“Yeah, I know. But not the way I do. I mean, I really do get off on it!”
“So? What’s wrong with that?”
“Nothing, I guess. It’s just that… I’d really like to figure out something I can do with him sometime to really show that side of him off. Something… that’s not really just inside of our apartment. You know what I mean?”
Mel nodded. “Something out in public.”
“Yeah. I guess.”
“So what did you have in mind?”
“That’s just it. I have no idea. No idea at all!”
Mel shook her head. “I don’t really know either, but if you think of anything, please let me know! I wouldn’t mind seeing it myself!”
“I’m leaking!” Sissy’s excited voice interrupted them from the kitchen.
Mel glanced up at the clock. He had made it, but only by one minute! “Did you curtsy?” she called back.
Chad’s reply was much less excited. “No.”

My Baby Bobby Story

For anyone interested, I finally posted my Baby Bobby story that I wrote several years ago to the Fictionmania website. It came out yesterday (Friday).

The Bet - Chapter 47 (Wednesday – week 7 Part 6 of 8)

The Bet
by Karen Singer

Chapter 47 (Wednesday – week 7 Part 6 of 8)

Chad worked through the stuff that Robin had assigned him. But he quickly realized that the job that he thought should take about an hour, was now easily finished in half that time. Oh well, maybe now that Robin could see how quickly and diligently he gotten this done she’d give him something else to do. Quickly, he saved his work and went to see her.
“Wobbin,” he said in his sissy voice to catch her attention. He saw her turn in her chair and he quickly curtseyed to her. “I finished.”
“Already?”
“It wasn’t as much as I thought it would be,” Chad explained. “Do you have anything else for me to do yet?”
“Not yet Sissy. Go back to your desk and leave me be for a while so I can work.”
“But I can help!” Chad protested.
“I don’t want your help!” Robin replied.
“But…”
“No buts! Now go!” Geez! It was like talking to a child! Again!
Reluctantly, Chad went back to his desk where he had nothing to do. He glanced at the clock. At least break time was coming up soon.
Robin worked for a little while more, then glanced at her clock. Break time… almost. Close enough for her anyway. She was ready for a break before she tackled anything else. She got up from her seat and walked over to Chad’s cubicle. She could see that since he had nothing else to do, he was just browsing the internet… it looked like he was looking at shoes – women’s shoes, naturally. “Break time Sissy,” she called.
Chad turned around quickly and smiled. He was ready for a break. Actually, he was ready to do something useful! He closed his internet browser and got up from his chair and started to walk out, but he didn’t get very far since Robin was still blocking the entrance. He looked at her quizzically. She looked like she was in deep thought over something. “What?” he asked.
“I’m trying to remember exactly what I told you about curtseying,” she said.
“You told me to curtsey every time I came into your cubicle and when I left it.”
Robin nodded. “That’s what I thought. I can see now that I made a mistake. Since I seem to need you to do everything possible to keep reminding me that you’re nothing but a sissy, I’m afraid you’re going to have to curtsey every time you see me – anywhere! And of course every time you leave me too.
Remind her that he was a sissy? Wasn’t the dress he was wearing enough? Wasn’t the sissy voice he was using around her enough either? But since he was a sissy and he really had no choice, he dropped her a curtsey.
Robin smiled. “I’m starting to see why Mel likes that so much.” She turned and started down the hallway. “Come along Sissy.”
Chad had to hurry to catch up to her. “How’s the project coming?” Chad asked as soon as he caught up with her. “Have you made any decisions yet?”
Robin briefly glanced at him as she walked. “I’ve decided that you ask too many questions!” Robin replied a bit testily.
“I’m only trying to help,” Chad replied.
“Well I don’t need your help!”
“But I’ve got nothing to do!”
Robin glanced briefly at him as they walked. “In other words, you’re bored.”
“Yeah,” Chad replied sullenly. “Something like that.”
Robin didn’t bother answering right away. He was just like a child. Why hadn’t she seen it before? Now he needed something to keep him occupied all the time? “Well,” she finally answered, “we’ll just have to find some way to keep you occupied later.”

They were early enough that they were among the first to reach the break room. They didn’t even have to stand in line to get their coffee so they were the first to sit down at the women’s table. None of the other women had even come in yet.
“Why won’t you let me help?” Chad asked as they sipped their coffee.
Robin wanted to scream. He was like a child constantly asking for something that you had already said no to. “Because I don’t want you to!”
“But we’ve worked together on projects before. Very successfully!”
Robin just looked at him. “That was… before! Before I knew what you were.”
It was a moment before Chad could reply. “What difference does that really make? I still have the same job. I’m still good at what I do.”
Robin’s answer was spoken almost angrily. “Because I can’t deal with you anymore like you used to be! Or at least like I thought you used to be. Every time I try to think of you now as anything but a sissy, it just makes me mad and upset all over again. Very upset! So the only way I can relate to you anymore is if I think of you as nothing but a sissy. Unfortunately, I still have to keep reminding myself of that! That you’re a sissy. You’re not a man. You’re not a woman. And you’re not even a man who’s trying to be a woman. You’re something else – a sissy! And from what I’ve learned, you need to be treated like a sissy. Heck, you even want to be treated that way. So for my own sanity, like it or not, that’s how it’s going to be!” Her voice softened, but only a little. “Like it or not.”
They were spared from further conversation by two other women arriving at the table.
Chad sat and brooded over Robin’s words as the conversation swirled around him. His biggest problem was that he understood how she felt. Completely. There was just nothing he could do about it. He was a sissy and that wasn’t about to change. Even if it could change, she would still probably never see him as anything else. Another thought occurred to him. What would happen between them after he won the bet… when he no longer had to dress like a woman when he came to work? How would she see him then?

After break, Chad walked silently next to Robin as they headed back to their desks. As he reached his cubicle he asked her one more time. “Are you sure there’s nothing I can do to help?”
Suddenly perturbed by his constant asking, Robin turned on him. “What do I have to do to get you to stop nagging me like a child? You’re just like a child in so many ways! I can’t believe I never saw it before. You try to hide things! It’s always half truths! You get bored easily! And it’s always nag, nag, nag! Just like a child! Do I have to treat you like one?” She stared at him for a moment, watching the surprise on his face as she contemplated her own words. “I guess I do.”
She stared at him for another moment before her next course of action sprang into her mind. “Since you like acting like a child, and I guess I’m stuck treating you like one, then we’ll deal with things one at a time. Since you can’t seem to stop nagging me, then we’ll have to deal with that the same way we did on Monday when you wouldn’t shut up and leave me alone. So you can stick your thumb back in your mouth again right now! That should keep you quiet!”
But Chad didn’t move since he was still shocked by Robin’s latest tirade and hadn’t had time to fully process what she wanted yet.
Robin saw him just standing there in shock and not moving. “Well?” she said. “What are you waiting for? Stick that thumb in your mouth and suck on it. Now!” She watched as Chad finally raised his thumb up to his mouth. She shook her head. “Just like a child. You’ve got to yell at them for everything. Over and over again! I said suck on it! Don’t let me see those lips not touching it – ever! Or so help me I’ll… I’ll glue that thing to your mouth!”
Wide-eyed, Chad sucked his thumb harder so she could see that he was doing it. The way she was speaking to him, she was actually frightening him.
Robin nodded her head. “Finally!” she muttered to herself. “Now I guess we have to deal with your other problems or I’m not going to get any peace this afternoon.”
Unfortunately, that was the exact point where Chad not only felt himself peeing uncontrollably again, that was also the point where the dumb suppository that he only thought Cassie had stuck up inside of him decided to go to work. Between being off-balance because of Robin’s attitude, and peeing uncontrollably because he was so distracted that he forgot to hold back, and now suddenly uncontrollably filling the back of his diaper too, his eyes got even wider as his whole face suddenly screwed itself up in distress. He moaned uncontrollably around the thumb in his mouth as his knees buckled under the sudden uncomfortable stress as his diapers continued to fill.
Robin was shocked as she watched him suddenly turn white, then seemingly go into mild contortions. “What’s wrong?” she asked quickly.
There were a few tears in the corners of Chad’s eyes now. He knew he wasn’t supposed to take his thumb out of his mouth so he left it there while he tried to talk around it, but the mumbled sounds that came out made no sense at all.
“Take that thumb out when you’re talking to me!” Robin ordered. “Now what’s wrong?”
Chad still wasn’t done filling his diaper as he was forced to answer. “I… I’m…” But how could he say it? He didn’t want to. Very embarrassed, instead of speaking, he put his thumb back in his mouth again and pointed at his backside instead.
Robin stared. Something about his bottom? What? And then it dawned on her. Incredulously she asked, “You mean… you’re… pooping in your diapers – right now?”
Chad could only stare embarrassedly down at the floor and nod his head a little. He felt like such a fool.
Robin shook her head. “God! I don’t believe it!”
Chad briefly removed the thumb from his mouth again. “I can’t help it!” he complained. “Cassie puts a suppository up inside of me every day at lunch, and then Mel does it again every night before I go to bed. She’s making sure that I can’t have any control over it!”
Robin stared at him, finding what he had just said hard to believe. “Every day?” she asked.
Chad stared back at the floor and nodded. “Yeah,” he replied. “Every single day! I hate it!”
“I wonder why!” Robin replied. “I guess we now know what you’re doing at the gym every day then. Is Cassie changing your morning diaper?”
Again, Chad only nodded.
“Well, that figures. So go deal with it then. Change yourself or whatever you usually do.”
Chad shook his head. “I can’t do anything. I have to stay this way till I get home from work.”
“You’re kidding?”
Chad sadly shook his head. “No.”
Once again Robin just shook her head in disbelief. Then the words just seemed to pop out of her mouth before she had fully comprehended the thought. “Serves you right! Idiot!”
Chad made no reply. What could he say? He just stood there staring at the floor with his thumb in his mouth.
“So you have to sit in it all afternoon?”
Chad’s nod was his only replay as he realized that what was happening down in his diapers was finally finished… he hoped. That alone was a relief. But now he had to deal with the mess like he did every day.
“So now what do I do with you?” Robin asked aloud, the shock of what had just happened had taken most of the anger out of her. Did she still need to do anything with him? He was bored, she remembered. And it was because of that that he had kept nagging at her. So she needed to do something! But she didn’t have anything for him to do. Besides, she was determined that he was going to keep that thumb firmly in his mouth for the rest of the afternoon. He behaved like a child! Images of something she had seen when picking her son up from day care flashed across her mind. “When the older kids at my son’s day care misbehave, they stick them in time-out for a while. Since my son is only one, I haven’t had to try that yet. He wouldn’t understand it very well yet. But you…” She stared at him for a moment again. Time-out? It would serve him right! But how could she do it? She suddenly grabbed his arm. “Come along, were going to my desk where I can keep an eye on you.”
Chad allowed himself to be dragged into her cubicle. Time-out? What was she going to make him do? Visions of himself standing on his perch in Mel’s corner flashed into his mind, but that couldn’t happen here.
Robin looked around her cubicle. When the kids at her son’s day care were put in time-out, they were made him sit on the floor facing the corner. But in her cubicle, she had no usable corners. Everything was taken up by her desk space. The only real corner in the room was… Perfect! She quickly pulled her chair away from her desk and moved it out of the way. She pointed at the floor where her chair had been. “Sit!” she commanded.
With his thumb still stuck in his mouth, Chad gingerly knelt down on the floor facing her. He could feel the mess in his diapers squishing into his bottom a bit more as it moved around.
“I said sit!” Robin commanded. “Indian style, with your legs crossed. And face the corner!”
Even more gingerly, Chad turned to face the corner under her desk and worked his bottom all the way down to the floor. The mess in his diapers along with the hard floor stung his still sore backside, but the mess was a problem he was long used to now so it didn’t bother him much. But since he was now sitting in front of her desk, he couldn’t figure out where she was going to work? His desk? That didn’t make sense.
Robin watched him sitting there for a minute, sucking on his thumb like she wanted him to. A thought occurred to her. She couldn’t trust him to not take his thumb out of his mouth when she wasn’t watching. She needed a way to make sure it stayed there. She looked around her cubicle and finally opened her desk drawer – and spotted… her roll of scotch tape! She grabbed it and bent over him and started wrapping it around the wrist of his hand that was up against his mouth. Then she started wrapping it all the way around the back of his neck and wrist, over and over again, pulling his thumb tighter and tighter up against his mouth. Finally she cut the tape and threw it back into her desk drawer. “There!” she said with an air of satisfaction, “that should keep it where it belongs.”
Chad’s thumb was pressed so tightly into his mouth that it felt like his thumb was completely filling the inside. And his teeth were digging into the skin below his thumb and hurting him. It was very uncomfortable.
“Now get yourself into that corner!” Robin ordered. “All the way in!”
Chad stared at the corner in front of him – under her desk! In there? It was dark under there. And his head wouldn’t fit! He tried to turn his head to look up at Robin to see if she was serious, but the stupid tape wrapped around his neck made that difficult. He suddenly felt her hand on his back, pushing him slightly. So she was serious! Reluctantly, he did his best to inch his way forward toward the corner, having to bend his head to the side a little to get it to fit under her desk. The constant sliding on the floor only made the mess in his diapers feel stranger. The skirt of his zebra print dress was gradually hiking up further and further too, fully exposing his girdle underneath.
“Keep going,” Robin told him. “I want to see both your knees touching the corner.”
Ugh! Chad kept going, still feeling her hand on his back as he inched along. The position he was in not only made moving very difficult, but it was horribly uncomfortable. His left knee finally made contact with the wall and he stopped.
Robin saw him stop and peered closely at him. It was a bit hard to see since there wasn’t as much light under her desk. She could see that his left knee was up against the wall, but his other one… “Both legs touching!” she ordered. Then she waited till he adjusted himself to her satisfaction. If he wasn’t all the way under the desk like that then he would be in the way while she tried to work. “Good!” she finally declared. “I think that should work just fine as a time-out corner for you. Now you just stay there like that for the rest of the day and contemplate how childish you are!” She stood up again and grabbed her chair and wheeled it back into place where she sat down in it. She moved herself into position to where she could work. He wasn’t in the way at all! She moved her legs out till they came into contact with his back. As long as she didn’t stretch her legs out much then she’d hardly know he was there. Perfect!
It was now almost totally dark under Robin’s desk since she was blocking most of the available light. He had felt her feet hitting his back briefly, then they had moved away. He moved his head from the side to straight forward but bent down a bit as the top of his head was against the desk top above him. He was stuck in a corner… again! Only this time he was sitting down instead of standing on his perch. But since his thumb was pulled into his mouth so hard and his neck was bent down at an uncomfortable angle, he couldn’t decide which corner was worse, this one, or Mel’s. And she wanted him to stay here for the rest of the afternoon? Ugh!
Robin pulled up their project to finally get back to work on it, but as much as she tried, she couldn’t concentrate on it at all. Her mind was filled instead with thoughts about what she had just done with Sissy… and what she had said to him earlier! Everything she had said back in the break room had been absolutely true. Every time she thought about Chad… the old Chad that she knew, doing the stupid perverted things that he was doing… well… it made her mad. Not just mad, but horribly angry. The idiot! The stupid, perverted, idiot! And now that stupid perverted idiot was sitting right underneath her desk, not a foot away from her feet, staring at a dark blank corner while he sucked his thumb. The stupid idiotic pervert! He deserved just what she was making him do!
A sissy? Yeah, he was certainly that! Even though she had only just come to realize what the term sissy meant. It still fit him perfectly. Well, he wanted it? Now he had it! As long as she continued to see him as only a sissy, then she seemed to have no problem being mean to him... or ordering him around… or just… she didn’t know what. Perhaps just dominating him. And as long as she only saw him as a sissy, then that was the way she would treat him. The only way. She had to. It was like payback for lying to her all these years. If only she had known!
So she would continue to deal with him. But she would only deal with him on her terms, and her terms only. Not Mel’s terms. And certainly not his terms. Her terms! It couldn’t be any other way, because every time she thought of him in any other way, she got angry all over again. So the trick, she supposed, was going to make sure that she only saw him as a sissy… a stupid childish sissy… and nothing else… ever! And she had a feeling that that wasn’t going to be all that easy to do here at work, because if anyone else ever found out what she was doing… well, she didn’t exactly want to get fired!
Her thoughts turned to Mel. She had asked for Mel’s help earlier. But Mel had been too busy to give her much of an answer. In light of how she felt now, maybe that was a good thing. Still, Mel had helped. Her idea to make him curtsey for her had been a really good one. So was her idea yesterday to make him use only his sissy voice around her. Both of those had been perfect to help her see him as nothing but a sissy. So she guessed she would consider any other advice Mel could throw her way. To that end, she guessed she owed Mel… something… even if it was just some consideration. She opened her email program and typed a rather long email to Mel telling her exactly what she was thinking – as well as exactly what she had done with Sissy.
When her email had been sent, she still didn’t feel like working. She moved her chair back to glance under her desk. He was still right where he was supposed to be, but then, he couldn’t go anywhere else. She slipped her shoes off of her feet and rolled her chair forward again. Then she walked her feet up his back and slipped each one over his shoulders to use him as a foot rest. She leaned back in her chair to relax. Finally, he was doing something useful!