The Bet - Chapter 25 (Tuesday – week 4 Part 4 of 6)

The Bet
by Karen Singer

Chapter 25 (Tuesday – week 4 Part 4 of 6)

Chad eased himself into his seat at work a bit slower than usual again so as not to irritate his rash any further. The single question on his mind though, was Robin... and getting her to tell him the best way to cure his diaper rash… without letting her know that he was wearing diapers. Mission impossible! He couldn’t think of any way to do it at all.
Dejected, he turned to his computer. Work would take his mind off of his raw backside, but he didn’t have anything to work on. He checked his email again – still no word from the client. Now what?
“Hi Chad,” Robin called as she walked past, returning from lunch.
He swung his chair around to say hi, but she was already gone to her own desk so he didn’t bother answering. But he still wondered how he could talk to her about the diaper rash. Robin was back a minute later though. “No word yet?” she asked.
He shook his head, disappointed. “No. I just checked.” Could he just blurt out the question… without her knowing why?
“So what are you gonna’ do this afternoon?”
“I don’t know.” Did he dare ask her? “Maybe I’ll take a nap. I could use one. I was up really early this morning.”
“How come?”
How could he answer without giving anything away? “The darn phone rang.”
“Don’t you just hate that?”
“I did today.” The diaper rash! Ask her about the diaper rash!
“So what are you really going to do?”
“I don’t know. How about you?” Come on Chad, don’t chicken out… it hurts!
“I don’t know either,” she sighed as she started to walk off.
“Hey Robin,” he called, stopping her before she got totally away.
“Yeah?” she asked.
But the words stuck completely in his throat. He couldn’t bring himself to ask something that he knew she would jump all over and pry things out of him that he didn’t want her to know. “Nothing,” he finally replied.
“Are you sure?”
He almost gave in, but finally, he shook his head. “No. Forget it.”
“I’ll be right here if you need me,” she said. And she was gone.
He had chickened out. And it was probably a good thing.

“Hi Mel,” Sandy’s voice came over Mel’s phone.
“Hi Sandy.”
“Are we still on for tonight?”
“Still on, Sandy.”
“Great! I know this won’t probably be much fun for him yet, but I’ve got to start somewhere.”
“Fun for him, or you?” Mel asked humorously.
Sandy giggled.
“Hey Sandy.”
“Yeah Mel?”
“Do you know anything about curing diaper rash?”
“Why, does he have it?”
“Evidently.”
“Well, there’s some good creams out now. Of course one of the best ways… on a baby anyway… is to keep them totally naked for a while. Let it dry out. I think sunshine on it is supposed to help too.”
Mel giggled. “I don’t think I’ll be sending him outside into the sun totally naked… at least I don’t think I will be.”
Sandy giggled too. “But really Mel. From what I remember with my brothers, let them go naked for a while, and a really good cream. Just be prepared for little accidents if you’ve got them naked… for a real baby, anyway.”
“What do you mean? He is a real baby!”
Sandy giggled. “And by the time I get finished with him, he’s going to be even more of one.”

Chad opened up his spreadsheet one more time. He looked at his reasons for winning the bet – especially his three main reasons. Self-respect, friends, and a life. Good reasons. Very good reasons. Why had he even thought about throwing the bet earlier and losing? Was he really that stupid? He thought about the bet as a whole and where it had brought him already. Obviously, he was that stupid.
At the bottom of the column of reasons to win, he added the word ‘relief.’ Another, very good, reason to win! And another thing he wanted very badly. He closed the spreadsheet once again as he felt the urge to pee come over him. He glanced at the clock on his computer screen and started timing himself.

Sandy backed her car out of the parking space in front of the grocery store, put the car into drive, and pulled away. She glanced at the bag on the seat next to her. She had bought more baby food to feed to Sissy tonight. Mel had said she could grab all she wanted from her place, but tonight was her turn with Sissy. Cassie got him every day at lunch and Mel… well, Mel had him all the time. Sandy was just thrilled that Mel was now going to allow her some “special” time with him every week.
Cassie and Mel were more thrilled and interested in the cross-dressing side of him, but Sandy found herself far more interested in his baby desires. That was the part that she found the funniest… and quite surprisingly, made her moist in places that only Cassie could really take care of.
She had no doubt that tonight would probably be tedious… for both of them. But there was no getting around it. She had this idea, and she wanted to try it. Mel had agreed to let her. She might have to even punish him a bit. No, make that she would probably have to punish him a bit. There would be no getting around it if he was going to learn.
With those thoughts in mind, she drove directly home. She’d have to pick up the highchair and a few other items from Mel later when she collected Sissy. She couldn’t wait!

“Hey Chad,” Robin called, coming into his cubicle.
“Yeah?”
“I’m going for more coffee. Want to come?”
Chad shook his head. “No thanks. There’s probably going to be more of your girlfriends down there… even now. I don’t need that.”
“Oh come on! Don’t be so stubborn. Did it hurt you at all to talk with Donna earlier?”
Donna? Was that her name? “No,” he admitted. “But…”
“Then get off your backside and come with me. You’re gonna’ get stuck to that chair if you don’t move once in a while.”
Chad shook his head. “No…”
But Robin had had enough. She grabbed his arm and pulled. “Come on! Get out of here. It’s just a cup of coffee!”
Chad reluctantly allowed himself to be pulled out of his chair and he reluctantly followed Robin out into the hallway. He didn’t really want another cup of coffee in his system. He was trying very hard to hold everything in… and so far, he was succeeding. Since he had wet himself the last time after lunch, he was currently in the process of timing himself yet again. And he was already up to eighteen minutes… although he wasn’t sure how much longer he was going to last.
When they got to the break room, Chad noticed a few guys talking together at one of the tables in the corner. He saw them glance quickly up as he and Robin walked in, then they looked away again… as if they didn’t know he was dressed any differently than he should be. Was it possible they didn’t realize he wasn’t a woman? He glanced at the men again, they still weren’t paying any attention to him.
“No donuts this time,” Robin complained as she poured herself a cup of coffee.
“I don’t need anymore donuts,” Chad replied.
“That’s right, whatever diet you’re on probably doesn’t include them… as if any diet I know of would! Unfortunately.”
Chad chuckled as he poured his own coffee. He really wanted to head back to his desk where he would be out of sight, but Robin was already sitting at one of the tables. He sat with her, cautiously, choosing a chair where his back would be to the table where the men were sitting. He sat down slowly and carefully again. The chair under him was hard plastic and even through all the padding on his backside, it hurt him more than the padded chair at his desk. He winced as he sat.
“You ok?” Robin asked, noticing his tortured look.
“Oh, yeah. It’s nothing.”
“Like the nothing you were going to ask me about earlier?”
“Just… nothing,” Chad replied. He took a sip of his coffee, and suddenly he couldn’t hold his pee back any longer. He let it out while he glanced at his watch. Twenty six minutes this time. Getting better!
“I can’t believe we still haven’t got the go-ahead on this project,” Robin said.
“Me either,” Chad replied. For the next few minutes, the two of them sat and talked about work and what they might be doing next. It was a very pleasant conversation for both of them… especially for Chad since nobody came in or made fun of him.
Sudden movement quickly caught Chad’s attention as the men in the room stopped to refill their coffee cups. Chad was instantly concerned. None of the men in the company even came near him any more. He didn’t know these men by the coffee pot, but that didn’t matter. He wasn’t really in the mood for any humiliation just then… as if he ever was.
The man at the coffee pot finished filling his cup, then turned around and smiled at Chad and Robin. “Uh oh!” Chad thought. “Here it comes.”
The second man finished filling his cup and turned around too. Both men smiled charmingly at Robin and Chad, then carried their cups out of the room.
Robin giggled and nudged Chad playfully. “He was eyeing you girlfriend.”
Chad was a bit confused by their behavior and wasn’t completely sure. In fact, it was entirely possible that they had been eyeing him. We’re the men blind? Or was it possible that he looked so much like a woman now that he had fooled them?
“They were pretty good looking too,” Robin added. “Which one did you like?”
Chad looked at her like she was crazy. “Neither of them. I was scared shitless!”
Robin giggled. “See, you don’t even have to be afraid of the men anymore… let alone the women.”
Chad knew better though. The men would have nothing to do with him at all… and as for the women, they could be the cruelest of all. He gulped the rest of his coffee down in one big gulp. “Come on, let’s get out of here,” he said as he stood up.
Robin was still giggling as they walked out. “How does it feel to know you’re making the men hot?” she teased as they entered the long hallway.
Ugh! “Don’t make me laugh,” he replied, seriously.
But Robin burst out laughing as they walked… which was just as well, because that was the exact point where Chad felt the suppository that Cassie had put up inside of him going to work. Yuck! And there was no stopping it… not that he even tried. By the time they got back to his desk, he was more worried than ever about his diaper rash getting worse – and he had no way to change himself. It was going to be a very long afternoon for sure!

The Bet - Chapter 25 (Tuesday – week 4 Part 3 of 6)

The Bet
by Karen Singer

Chapter 25 (Tuesday – week 4 Part 3 of 6)

It was still fairly early when Mel picked up her phone and called Cassie. “Hey Cassie,” she said as soon as Cassie had answered.
“Hi Mel. What’s happening? Still on for tonight?”
“Definitely!” Mel replied.
“Great! I know Sandy will be happy. She’s been working really hard for this.”
“I know. She told me.”
Cassie giggled. “Yeah, I know. So what’s up?”
“Cassie, I need you to make a tiny change in what you’re doing with Chad at lunchtime.”
“Sure, what?”
“Well, on Tuesday’s and Thursdays don’t put any suppositories up inside of him… but I need you to pretend you’re doing it so he doesn’t realize you’re not putting them in him.”
“Huh? Just pretend to do it?”
“Right!”
“Well, if you’re sure…”
“Yeah, please. But don’t forget. Keep putting them into him all the other days.”
“Ok,” Cassie agreed. “That should be no problem.”
“Thanks, Cassie. I owe you.”
Cassie giggled. Yeah, you do. See you tonight.”
“Yeah, Cassie. See you tonight.”
Mel hung up her phone. The next phase of her plan for Chad was now in effect! She opened her laptop and started working again, but her mind was still more on Chad and whether or not she really had the reason she thought she did last night to punish him. And because her mind was more focused on Chad, she was getting further and further behind on her work in the office.
Her work was further interrupted close to noon when her phone rang again.
“Hey girlfriend,” Gloria’s voice said over the phone.
“Hi Gloria,” Mel replied happily. It was good to hear a friendly voice once in a while.
“Lunch today?” Gloria asked.
“Ummm… Can’t today,” Mel replied regretfully. “Too much to do.”
“Ok, sorry girl. Maybe another time.”
“Yeah, definitely,” Mel replied. She was about to hang up when she found herself quickly saying, “Hey Gloria!”
“Yeah?”
“Hey, listen. Do you have a minute to talk?”
“Yeah, sure. What’s up?”
Where should she start? “It’s about Chad. I went at him again last night, punishing him a bit… Oh, and hey, you know he actually started crying! Like a baby! Completely!”
“He did? So it’s working then? The suggestions are working?”
“Yeah. They seem to be working great. Although I did notice he’s not quite completely incontinent yet. But he didn’t have a whole lot of control and wound up peeing on my carpet a little bit.”
“Hey Mel. That kind of brings up something I wanted to talk to you about. The next time you come in, I think I want to try something different with him, ok?”
“Like what?”
“Well, I kind of want to see what’s working and what isn’t. That way we can make changes to whatever isn’t really working, now rather than later.”
“Sounds great to me,” Mel replied. “You know I’d like as much info as we can get too.”
“That’s kind of what I thought. So I’ll work on what I want to do with him for Thursday night then.”
“Sounds great, Gloria.”
“So listen, Mel, what were you punishing him for this time?”
“Ugh! That’s my problem. I don’t really know if I should have, or shouldn’t have.”
“So maybe we should have lunch together after all?”
Mel thought about it. “Maybe I can juggle a few things around. Make it a quick lunch anyway.”
“Great Mel. See you in a few?”
“See you in a few.”

Chad had done next to nothing all morning… except to wet his diapers four more times and try to time himself – fourteen minutes so far. The two cups of coffee he had drank with Robin didn’t help things any. He was wetter than usual as he tried not to waddle too much out to his car. The worst part of it was though, that the extra wetting seemed to be irritating his diaper rash even more. He was very disappointed that all the baby lotion he had put on it earlier wasn’t helping much… if at all. As he climbed gingerly into his car, he made it a point to ask Cassie to put extra lotion on him when she changed him today.
He pulled into the parking lot at the gym and grabbed his purse and diaper bag. He glanced around as he got out of the car, at least Robin wasn’t there today, she had made arrangements to go to lunch with the woman they had talked with earlier in the break room – whatever her name was.
He walked through the door to the gym. The receptionist, as usual, was smiling broadly at him. “Hello, Sissy,” she said with more zeal than he was really happy about. Then she stood there smiling at him… waiting.
There was no getting around it gracefully and he knew it. He dropped a quick curtsey to her and said, “Hi.” She seemed satisfied though because she immediately giggled and went in search of Cassie.
Chad had to repeat his curtsey-greeting once again for Cassie as soon as she got up front, then he followed her back to their usual back office. “How are you today, Sissy?” Cassie asked as he started to get undressed.
Chad stopped removing his pants for just a moment. “Hurting a bit,” he finally replied.
“Hurting? What’s wrong?” she asked with some concern.
Chad looked a bit embarrassed. In fact he sounded embarrassed as he quietly answered. “I seem to be coming down with a case of diaper rash… and it’s getting worse.”
“Diaper rash!” Cassie repeated a lot louder than Chad was happy about. “Oh you poor thing. Let me see.”
Chad continued to get fully undressed down to his diapers and plastic panties. Then Cassie handed him one of the baby bottles out of his diaper bag to start drinking while she undressed him the rest of the way. As soon as she had untaped his diapers, she pulled both legs up toward his stomach. “Leg’s up. Let’s see how bad it is.” Chad dutifully attempted to keep his legs pulled up, but Cassie helped him hold them up and out of the way. “Hmmm. Yep, it’s all red. You’ve got a nice little rash started there.”
“I put a lot of baby lotion on it this morning, but it doesn’t seem to be helping.”
“You may have to get something special for it later. All I can do for it is to put more of your baby lotion on it again, but if that’s not helping yet, then I think you need to get something better.”
“Isn’t there anything you can do for it?” Chad asked hopefully.
She shook her head as she let his legs drop. “Nope. Besides, I’m certainly no expert on the subject. I’ve never had a baby… or even been married for that matter. Not that I’m probably ever going to either. Don’t you have any friends somewhere who’ve had kids? You should ask one of them. I’m sure anyone who’s had kids can tell you how to cure this.”
As Cassie began pulling the fresh diapers under him, Chad thought about who he knew that had kids. Unfortunately, the only one who immediately came to mind was Robin – his one and only friend. But Robin didn’t know about his diapers – and he meant to keep it that way. As Cassie began massaging the baby lotion into the front part of him, he sucked on his bottle, deeply in thought. How could he get Robin to tell him how to cure diaper rash without telling her that he wore diapers? And did he dare?
Cassie shook her head. “This is starting to be a waste of time. You don’t even know I’m playing with you here. Talk about no reaction. Ok, turn over.”
“But I hurt!”
“Tough! Turn over!”
Chad wasn’t at all happy about that, but he put his bottle down and assumed the position for her to work on his backside… the only part of him that seemed to feel anything remotely like sexual pleasure anymore.
Even though Cassie’s hands were coated liberally with baby lotion, the moment they touched his diaper rash, he hissed in pain and tried to move away. “Darn,” she said, “you’ve got it bad, don’t you. “It hurts a lot?”
“What do you think?” he returned angrily. “Yes, it hurts a lot! And I think it’s been getting worse all day!”
“Well, you’ll just have to suck it up, because I’ve still got to get the lotion all over you. Besides, you wouldn’t want to go without any, would you?”
“No,” Chad replied flatly.
As gingerly as she could, Cassie finished coating his backside with the baby lotion. She didn’t massage it in as she usually did because she didn’t want to cause him anymore pain than she had to.
But she wasn’t quite done with him after that. “I brought a present for you today,” she said with a little chuckle. Chad didn’t answer, but he did try to roll onto his back again as if he thought she was done with him. “Uh, Uh!” she said as she stopped him from rolling over. “You stay just like that!”
Chad wasn’t sure what she was talking about. A present? And she didn’t want him to roll back over? From his present position he couldn’t see anything.
The shock was instantaneous and electric. Cassie couldn’t help but giggle as she watched his whole body react the moment she placed the tip of her dildo, right up against his tiny asshole with more pressure than usual. She only kept it there for a brief moment before she applied even more pressure and began pressing it in.
It took Chad a moment to realize what was happening before he could relax his muscles enough to start to accept the toy she was using on him. He certainly hadn’t been expecting it. But once he fully realized what it was and what she was doing, he relaxed more and tried to “get into it.” He still didn’t know why, and it still really bothered him, but he loved it and he wanted more, more, more!
Unfortunately, very shortly into the experience, while her toy was buried deep inside of him, he realized that he suddenly had to pee. Yes, he wanted to feel the pleasure of peeing while the thing was in him! But no, he didn’t want to be peeing all over everything again… and worse, with her toy reaming him out but good, he knew for sure that he couldn’t hold back for long. “Cassie!” he called out with a bit of distress, “I have to pee!”
“So go ahead,” Cassie replied. “I already put fresh diapers directly under you.”
Chad wanted to argue against wetting the fresh diapers before they were put on him, but there wasn’t time. As Cassie pulled the dildo out, then pushed it in once again, he couldn’t hold back any longer. The pee came gushing out of him, into the short space available inside of his chastity device, and continued gushing straight out of the device to fall directly into the diapers below.
He heard Cassie giggling as he did it. Laughing at him! Damn! And worse, he knew he deserved to be laughed at. Damn! And worse still… because she was pumping the dildo in and out of him, and because he was peeing during it, and because she was laughing at him, and because he felt humiliated by it all… it completely fueled his sexual need to an unbearable degree. Damn he needed some relief. But there was no relief in sight. Nowhere! He wanted to pound his fists on the floor from the frustration of it all. But it would help nothing. He was trapped into Mel’s chastity hell! And so far, there was no way out! Thirty eight more days? It was way too much!
Getting relief! The only solution he could see for the near, and distant future, was to win the bet! As Cassie finally slowed down, his mind was locked firmly on his reasons for winning the bet. Forget all the reasons for losing that he had been thinking about all morning… he now had another reason for winning the bet – relief!
He finally felt Cassie pulling the dildo completely out of him. As much as he had loved the feeling, he gasped in relief. “Hold still another minute,” she said. Chad heard her fussing with something, then he felt her finger pushing into his hole once again as far as she could reach it. The damn suppository. He hated the damn things… and especially what they did to him.
Chad rolled back over and grabbed his baby bottle and began drinking it without hardly thinking about what he was doing, he was that used to it now. He felt Cassie pulling the diapers under him up and over him, which surprised him a bit. “I just wet those,” he complained.
Cassie shook her head. “They feel hardly wet at all. Not enough to worry about as far as I can see.”
Surprised, and disappointed, Chad stuck his bottle back into his mouth and sucked on it. Diaper rash or not, he was already starting the afternoon with wet diapers!

“Your jealous!” Gloria declared.
Mel rolled her eyes, then looked down at the table. “Totally,” she admitted. “But geez, shouldn’t I be?”
Gloria shrugged, “It’s only natural.”
“So what should I do about it? He’s got to work with her… every day!”
“Have you met her? Talked with her?”
Mel shook her head. “Not yet.”
“So why don’t you?”
Mel thought about it, then shook her head again. “Not yet. I’m just not ready for that yet. I mean, it’s probably perfectly innocent. They’re just working together.”
“But you don’t know that for sure.”
Mel shook her head and sighed. “No, I don’t know that for sure.” Just then, Mel’s cell phone rang. “Oh hell, probably more problems,” she said as she fished it out of her bag. But she smiled a bit when she saw the call was from Cassie. “Hi Cassie. How’d it go?”
“Hey Mel. It went fine today. I faked putting the little pill in him and I know he couldn’t tell I wasn’t doing it.”
“Great Cassie. I appreciate it. Now remember, none on Tuesdays or Thursdays, but do it every other day.”
“Got it Mel… Hey Mel. You know his rash is really hurting him. I think you’re going to need something more than the baby lotion he’s using to try to clear it up.”
“Rash? What rash?”
“The diaper rash all over his backside. You don’t know about it?”
“No, not at all. He didn’t tell me.”
“Well, I’m surprised because it looked like it was getting pretty bad.”
Mel paused to think. “Ok, Cassie. Thanks for telling me. See you tonight.”
“Great Mel. See you then.”
Mel hung up her phone. “He’s got diaper rash.”
Gloria stared at her in surprise, then giggled. “Well, you did want to make him more babyish. What could be more babyish than that?”

The Bet - Chapter 25 (Tuesday – week 4 Part 2 of 6)

The Bet
by Karen Singer

Chapter 25 (Tuesday – week 4 Part 2 of 6)

Mel watched the clock. It was just about time. His knock came at her door a minute early. She opened it and smiled.
“Good morning, Mistress,” he said with his usual curtsy.
“Good morning, Sissy,” she said as usual, stepping back to let him inside. She noticed immediately that he had decided on wearing slacks once again. Not a problem. But one day this week she knew that he would be forced to wear a skirt to work again. Probably Friday. She had a feeling he would try to put it off as long as possible.
She took his bag of empty bottles from him, but she didn’t bother to look at them – there was really no need. They were always perfect. She stared at him carefully, looking him over critically. His shape was really much better today. She remembered putting the instruction in his note for him to wear the waist cincher and there was no doubt that he had it on. She smiled – yes, he was really looking good now. She noticed that he was wearing high heels once again instead of the low heeled shoes he usually wore, but his slacks didn’t seem as short as they should have. She was puzzled. “I don’t remember those slacks being that long,” she stated.
He seemed to sigh with frustration before he replied. “They’re not. It’s because of the girdle and the waist cincher. The pants ride down too far on my hips now.” He grabbed the waistband of his pants and pulled them up, then released them to show her his problem. The pants fell right back down where they were before. They obviously wouldn’t stay up as high as he wanted them to. “I have to wear the heels or the pants drag too much on the ground. They don’t fit right with the waist cincher.”
She nodded as she suppressed a small giggle. The waist cincher was giving him a much more feminine shaped waist. But she was glad he had found a way to deal with the problem of his pants. “They look good with those shoes though,” she finally replied, letting him know that she approved of his solution.
Chad stood there for a moment, then he finally asked. “Mistress, what should I do when I have to wear the longer slacks though? I don’t have any heels that would be high enough.”
Mel shrugged. “Don’t wear them.”
“But I need them. I only have four pairs of pants.”
Mel smiled. “You’ll just have to wear something else.” She turned and walked off toward her kitchen with a devilish smile on her face. “Come along now, Sissy. I’ve got your breakfast ready.” As she led him into the kitchen though, her mind was concentrating on only one thing. If Chad couldn’t wear the new, longer length slacks, then he was now going to have to wear skirts to work more than once a week. She giggled slightly again as she wondered when the next day would be. Thursday? Probably.
Chad’s mind was on the same thing as he followed her into the kitchen. It would mean yet another day in skirts – at work! Damn! It wasn’t something he was looking forward to – at all! As he climbed up into the highchair, he asked. “Is there any chance I can buy some more slacks that fit better?”
Mel paused before she put the tray into place. “Maybe, Sissy. I’ll have to think about it.”
Chad never looked forward to her baby food breakfasts, but he had no choice in the matter. In just a few minutes, he had a bib around his neck and was shoveling baby cereal into his mouth… as much as he was able to get into his mouth without it dripping off of the tiny baby spoon he was using. Maybe he should try to put less on the spoon so it wouldn’t drip so much. Of course, then it would take him all that much longer to eat… not to mention that more of the foul cereal would wind up in his stomach. That was the only good thing about trying to eat with the tiny spoon - much of the cereal wound up on his bib or the chair and he didn’t have to eat it.
Mel sipped at her coffee as she watched him struggling to eat his breakfast. Yes, he was a real joy to watch. It certainly brightened her morning every day. But that reminded her, he was going to probably have an interesting evening later, something he didn’t know about yet. Which reminded her of something else… What was he going to be doing with the rest of his day today – while he was at work? Thoughts of him spending yet more time with his friend Robin filled her head. “Are you going to be working today, or reading magazines again?”
He shook his head. “I don’t know. It depends on how soon the client lets us know what he wants.”
Mel wasn’t exactly happy about that, but what could she do about it? “How long does that usually take?”
“Usually a few days at most. But this time we’re hoping to know right away. We really did some super work for them. I can’t see where they wouldn’t like anything we’ve got.”
Mel knew there was no help for it and it was silly, but she couldn’t help it. She was jealous of Robin and the time she spent with him. But he worked with Robin… it was part of his job. Was there any way she could limit the time he was spending with her at work? It was something she’d have to think about.

Chad shifted uncomfortably in his seat as he drove to work. He had wet himself a few minutes ago and now the wetness had worked its way toward the bottom of his diapers a bit… and for some reason, it was irritating his backside. He hadn’t expected that. He did coat his backside liberally this morning with the baby lotion, but it seemed that it wasn’t working very well yet. He had only wet his diapers once so far today. He was now a bit concerned over wetting them even more.
He pulled into a parking space and got out, forcing himself to ignore the urge to rub his padded and irritated backside as he walked into the building. He turned his computer on and sat down, a bit more carefully than usual. Not too bad, just a bit itchy on his bottom. As he checked his emails, the irritation faded to a more tolerable level that he hardly noticed.
“Hi Chad,” Robin called as she walked past his cubicle.
Chad looked up from his monitor but Robin had already passed. “Hi Robin,” he returned over the cubicle wall.
Two minutes later, Robin was at the entrance to his cubicle again. “Any word yet on the project?”
Chad turned his chair around to face her. “Not yet. I just checked the email. Although it is a bit early yet.”
“Yeah, I was just hoping. That’s all. So what are we supposed to do again today?”
He shrugged. “No clue! I’m not sure I want to read anymore magazines again though.”
Robin nodded. “Ok. Let me know if you do though. I’ll see if I can round up some more.”
Chad watched as Robin left and went back to her own cubicle. He turned around and opened up the spreadsheet he kept for the bet. Next to the date for yesterday, he entered twenty five minutes. He stared at the number. Geez! He was going backwards. But really, yesterday had been a bit tough in a few ways. He supposed that he probably could have tried harder while Robin had been sitting with him yesterday afternoon. Why hadn’t he? He vowed that today he would do better… well, he’d do better this afternoon anyway. He always had way too many bottles of Mel’s tea in his system in the mornings to control himself much.
He stared at the number of days still left. Thirty eight. He shook his head. A very, very long time still. Thirty eight more days of total… complete… humiliation. He hated it. But then he had to admit to himself that he loved it too. He was living his fantasies… and then some. It was the “and then some” part though that was bothering him the most. Who would have ever thought that he would be dressing completely as a female… all the time – even to work! Damn! And wow did he need some relief!
He glanced at the last part of his spreadsheet. Self-respect, friends, and a life! Worthy goals – and his main reasons for winning. He had none of those things now. Not at all! Yet he was living his deepest fantasies… and then some.
It would be so easy to make it look like Mel had really made him incontinent, so she could win and he could continue living the dream. Of course, he knew he’d have to fake it. There was no way she could really do it to him. Although he had to admit, there had been a few times already when it had seemed like she had already done it. Troubling times… yet also thrilling.
One thing he had learned in all this though, was how much he really did love wetting his diapers. And it was really so much easier than having to go find a toilet to use somewhere. Much easier, not to mention how really good it felt every time he wet himself. He was surprised at how good it always felt – every time! He never would have imagined it before.
Live the dream… With nothing better to do, he allowed his mind to drift into the fantasy of being totally incontinent, completely unable to control himself in any way… sucking on pacifiers, drinking from baby bottles… and not to mention wearing high heels and skirts. Totally conflicting fantasies – yet they were his fantasies… and he was living it all right then – in reality!
What would happen if he really did go along with Mel’s program? Maybe even tried a little extra harder to achieve his goals? Would it really happen? Could he really do it? He imagined it again, the total humiliation as he wet himself uncontrollably… And as he imagined himself wetting himself in his dream, he also began wetting himself in real life. And he loved doing it. And his need for sexual release went up several more notches.
But he was quickly reminded that he had no way to get any relief at all, and the frustration sunk heavily into him once again. He sighed with frustration as reality crept completely over him and he realized what he could and couldn’t have. It would never work anyway. He knew himself too well. Mel couldn’t actually make him incontinent, no matter how much he tried to go along with it.
And then there was the rest of it too – self respect, friends, and a life. Were they really worth it? Deep down, he knew that they were. But remnants of his dream still crept around the edges of his mind. Were his reasons for winning really that important? Really?
Frustrated, he closed the spreadsheet. Now what was he supposed to do with himself?
He sat back in his chair and stared at the walls of his cubicle. It was a bit like standing in Mel’s corner… or was it his corner? Either way, it was boring. Although standing in her corner hadn’t been quite as bad last night since he had been thinking about something interesting. And that turned his mind back once again to his new favorite subject. Just what would he do if he could get hard again? He knew it would feel great. He knew he wanted it. He just didn’t know exactly what he would do. And why, why, why did he keep thinking about something going in and out of his backside now instead of what it would feel like to stimulate his cock instead. It made no sense. Yet for some reason, it was easier to imagine the feelings from his backend than from his front! Why? Probably because of the damn chastity device and because he needed relief too much. Damn!
“Hey Chad.”
Chad nearly fell out of his chair as Robin’s voice startled him so much. He came to reality and saw her standing in his cubicle. “Yeah?”
“I’m going down to get some coffee. Want to come? There shouldn’t be anyone down there for you to worry about right now.”
Chad considered her offer. It would be nice. He wasn’t sure he needed any more to drink again this morning, but getting away from his cubicle for a few minutes would be a welcome change, especially since they didn’t have anything to do anyway. He nodded his head and smiled. “Sounds good,” he finally replied as he pried himself out of his chair. Getting up changed the pressure on his backside once again and he felt the tingling from his diaper rash. Once again he had to force himself to not rub it.
As he walked with Robin toward the break room, he felt the need to pee come over him yet again. He quickly checked his watch so he could time himself… not that he thought he would be holding it very long since it was still morning.
As they entered the break room, he was a bit annoyed to see another woman there making a fresh pot of coffee in one of the coffee pots. He also wasn’t happy to see her looking him over all too carefully and smiling, almost wickedly, at him. He tried to ignore her as he picked up a full pot of coffee and poured himself some.
“Hey, look! Doughnuts!” Robin exclaimed as she headed further down the counter toward several large, flat boxes.
Chad had been so intent on looking at the other woman that he hadn’t noticed the doughnuts. He was a bit hungry… baby cereal didn’t exactly fill him up much every morning. He carried his coffee over to the donuts and selected one – sugar-coated and filled with raspberry filling… yum! He stood back, waiting for Robin to finish pouring herself her coffee before walking back to their desks with it all. But as soon as Robin poured her coffee, she headed to one of the tables instead. “You’re not going back?” he asked.
“Why? It’s a lot easier to eat these here. Besides, what have we got to do back there anyway?”
Chad shrugged his shoulders and joined her at the table. It was good to get away from his desk for a while. And at least there was just the one other woman still there… hopefully, she’d leave soon. He carefully took a bite of the doughnut, enjoying the fresh taste of the raspberry filling as it filled his mouth.
“Hi Robin. Hi Sissy.”
Chad looked up in horror as the woman sat down with them. She had called him Sissy! And he didn’t even know her name.
“Hey girl,” Robin replied, obviously the two women knew each other well.
“It’s about time you got away from that desk and got out to see the world,” the woman said directly to Chad.
Chad was stunned and totally at a loss as to what to say. “Uh… I guess so,” he finally replied.
“By the way, you’re looking good there, Sissy. Real good. Better than last week. Did you lose some weight? To me, you look thinner.”
“You know,” Robin added. I was wondering the same thing. You are looking a lot thinner. In fact you look like you’ve lost a lot of weight recently. What kind of diet are you on?”
Chad wasn’t really sure what to say. His apparent weight loss wasn’t really from any kind of diet, it was mostly from the waist cincher and the girdle. Of course, he had been eating a lot of baby food lately… far more than he was happy about. He supposed that might have added to the affect. “Uh… he finally blurted out. I’ve been eating a lot less… and a lot more of the basics too.” How much more basic can you get than baby food?
“We’ll sister,” the woman replied, “whatever it is, it’s workin’ for you. It’s working, girl!”
“Uh, thanks,” Chad replied. Being referred to as ‘girl’ was both exciting and humiliating at the same time. He quickly shoved a lot more of his doughnut in his mouth. Not only would finishing it give him an excuse to leave, but it’s hard to answer questions with your mouth full.
“So how’s the baby,” the woman asked Robin?
Chad was grateful that the conversation finally moved away from him. Robin could talk all day about her son… which was just fine with him. He took the opportunity to finish his doughnut and coffee while Robin and the woman talked. Since he wasn’t the center of the conversation, he enjoyed it a lot more. Why couldn’t the women always leave him alone? Why did they have to make such a big deal about the way he was dressed all the time? Was it that exciting that they always had to talk about it? He rolled his eyes at his own thought. Yeah, in their shoes, he’d probably be just as excited and curious… what was he talking about? He was in their shoes – in a way. Wasn’t he wearing high heels on his feet too?”

The Bet - Chapter 25 (Tuesday – week 4 Part 1 of 6)

The Bet
by Karen Singer

Chapter 25 (Tuesday – week 4 Part 1 of 6)

Her dreams were not peaceful. It’s hard to dream peacefully when you’re worried that you may have done something you shouldn’t have. But did she?
In some dreams her life was ripped, mercilessly apart, by unknown forces – she was condemned and punished, again and again, for deeds she shouldn’t have done. Yet in other dreams, she was proven justified in the end and felt exalted. Dreams of vindication, that were followed by dreams of doubt once again. Over and over again, in her dreams, she was fighting in a court of law over the actions of her life – constantly being judged by unknown judges and juries that always seemed against her.
And in the background of every dream, Sissy stood silently – always unspeaking, always unmoving. He was the only one, never trying to condemn her. Over and over again she tried to tell him she was sorry, yet he never showed any reaction to her words and feelings. He was just there. Like a statue.
She tossed and turned all night long, till she could take it no more. She woke up and sat up in bed, tossing her hair and running her hands through it again and again as the dreams faded gradually, leaving her to finally wonder what it was that she had been dreaming about. She sat there staring at nothing for a long time, her mind not yet ready to deal with anything at all. Finally, her brain began to gain some semblance of thinking. Her eyes focused somewhat. Her room was mostly dark, lit only by the faint glow from her clock radio and the tiny bit of light seeping in through her curtains from the parking lot outside. She groaned, it was early… way too early.
Unwilling to even try to go back to sleep, she pulled her legs out from under the covers and sat on the edge of her bed. She turned off her alarm so it wouldn’t go off later, and got to her feet. She slipped into her robe as she walked toward her kitchen.
Her kitchen was a mess… her fault she knew. She hated that. Why didn’t she have Sissy clean it up before she sent him home last night? Because she felt guilty for punishing him… that’s why! She didn’t want to have to face him for one moment more than she had to. Had she been right in punishing him? Or had she been wrong?
Damn it! She had the right to do it whenever she wanted to! There was no doubt about it. It was spelled out in writing and hanging on his living room wall as part of their contract! She was thoroughly justified! So why did she feel that it was so wrong? Damn it! It wasn’t wrong! She had the right! But did she have the valid reason she had thought she had?
Angrily, she picked up a pan off of the stove and stuck it into the sink. She turned the water on to start it soaking, then stopped. This was his job, not hers! She should let him deal with this mess. Could she wake him up now to get started on it? She could phone him and wake him up, as early as it still was, to come over and clean up her apartment… completely! Yes! A great idea!
But instead, she put some coffee into her coffee maker, filled it with water, and turned it on. She watched it dripping into the pot, slower than she’d like it to. She needed some coffee. While it was dripping, she suddenly moved off and found her purse in the living room. She pulled her cell phone out and stared at it. Should she really call him? At this hour? She had the right. But should she? It really wasn’t a very nice thing to do… But damn it, she was his mistress. She could make him do anything she wanted him to do. Hadn’t she proved that with him over and over again? She was his mistress… totally. She had the right!
Throwing all concerns aside, she quickly punched his number.

Chad also tossed and turned in his sleep… as much as all the stuff he was wearing would let him. Yet he didn’t sleep comfortably… or as comfortably as he possibly could have given his circumstances. Not only did the breast forms bother him, but so did his chastity device and his super long fingernails, and his now super-thick, wet and messy diapers. And worse, there also seemed to be a lot of irritation across his entire backside where she had punished him – and then not put any baby lotion on him afterwards.
An odd, insistent buzzing brought him out of his sleep. It took him a moment to figure out what it was… his cell phone! Who would be calling him at this hour? It wasn’t even light yet! But the buzzing of his phone wouldn’t stop and he felt compelled to get up and answer it immediately.
As he got to his feet, he was made immediately aware of just how thick and wet his diapers were… more than usual he thought. But he didn’t have time to dwell on that, his phone was still buzzing. He waddled, very wide-legged, as fast as he could to his living room and followed the sound to his purse. He fumbled to dig the phone out with his super long nails and quickly glanced to see who it was… Mel. What did she want at this hour?
“Yes Mistress,” he said, mumbling breathlessly into his phone around the pacifier that he forgot was still in his mouth. His brain still wasn’t awake enough to comprehend much yet.
“Get over here right now!” Mel ordered.
He was a bit shocked. It was so early. Was she still mad about something? He couldn’t tell. “I’ll change as fast as I can,” he replied through his pacifier, “then I’ll be right there.”
“Don’t change! Just walk out your door and over here now!”
She did seem angry still. “Yes, Mistress,” he said with a mental sigh. He closed his phone and dropped it back into his purse. He stood still, just staring at his purse for a moment while he collected his thoughts. Go now? Damn. He wasn’t even awake yet. He grabbed his purse and opened his front door, praying that nobody would be outside at that hour to see him. As he waddled toward her apartment, he became more and more aware of the irritation on his backside. Damn. After the beating she had given him last night, he figured he was developing a diaper rash on top of it. And it didn’t feel like it was going to be fun!
He knocked softly on her door because of the early hour and stood back half a step. Mel opened it a minute later with a cup of coffee in her hand. “Good morning, Mistress,” he greeted her as he usually did. But this time, Mel didn’t return the greeting, she just stood back and waved him in as she took a sip of her coffee. He entered and set his purse down in his usual spot next to the table by her door. He turned to ask what she wanted him so early for, but she was walking away.
“Clean up the kitchen,” she said as she walked off, completely indifferent to anything else as she headed to her bedroom.
Chad stood where he was, staring after her for a few moments before he moved. Clean the kitchen. He couldn’t believe it! No, he could believe it. Shaking his head, he waddled awkwardly into her kitchen and stared around. It was still a mess from his cooking last night… a meal she had been less than happy with.
The light on her coffee maker caught his attention. She wasn’t around just now. A cup of coffee would be really good just then to help wake him up. He was very tempted to pour himself some, but he didn’t. If she came in while he was drinking it… from a cup… he knew he’d be in trouble for sure. He went to her refrigerator and pulled out one of his baby bottles instead and exchanged it in his mouth for his pacifier. It wasn’t coffee, but the cold liquid felt good going down his throat. With his bottle in one hand, he picked up a pot with his other hand and carried it to the sink to start cleaning up.

Mel stepped out of her shower and dried herself off. She felt a lot better. She quickly threw on some panties and a bra, followed by some jeans and a t-shirt. Then she picked up her empty coffee cup from the bathroom counter and wandered back out to the kitchen to check on Sissy.
She poured herself another cup of coffee before she sat down, noticing as she did so that the kitchen looked much better now. The dishes were all done, and he was just starting to wipe all the counters down. He was almost finished… already.
She watched him as he worked. The diapers inside his onesie were so huge that they wagged widely back and forth as he scrubbed the counters. She wanted to laugh. How did he walk in those things? Not her problem though. In fact, she was delighted to watch him in them. “You’re almost done already,” she finally said.
Chad turned and curtseyed to her. “Yes, Mistress. It wasn’t that much.”
Wasn’t much? It sure had seemed like a lot to her. At least a lot more than she wanted to deal with… which was why she wanted Sissy in the first place. Such a joy! “I noticed your diapers are… incredibly thick again this morning.”
“Yes, Mistress,” he replied once again. “They’re like this every morning,” he said with a small sigh. “Although I do think they may be a bit worse today than usual.”
She smiled although she really wanted to laugh instead. “I think it’s hilarious watching you try to work when they’re that bloated. Maybe I should keep you like that more often… a lot more.”
Chad said nothing in reply. But his face turned a bit red as he looked sheepishly down at the floor. But before he could look up again, he felt some very slight stings from the teeth inside of his chastity device beginning to make their presence known.
“Ok, Sissy. Go make my bed, then you can go home and get cleaned up.”
Chad waddled as fast as he could into her bedroom to make up her bed. Mel followed him and watched him with a huge smile on her face the whole time. He looked so humorous waddling around in his baby onesie with his breast forms jiggling around on top and his super bloated diapers stretching the seat of his onesie on the bottom, causing him to walk with nothing but a very wide-legged waddle.
When he finished, he dropped an awkward curtsey. “Will there be anything else before I get ready for work?” he asked.
Mel glanced at her clock. Things were running a bit late now. “No Sissy. I’ll see you back here in a little while. You’d better hurry now.”
Chad attempted to run toward his purse by the door, but all his thick diapers would allow him to do was a faster version of the waddling he had been doing. Since he had gotten up, he had wet himself two more times while he was cleaning her apartment and now his diapers were even thicker than before. He was more than ready to go home and get into the shower, especially since the itching on his backside seemed to be getting worse from all the moving around he had been doing. Dropping one more quick curtsey toward his mistress as he paused briefly by her door, he hurried out to get changed.
His alarm clock was blaring loud rock music throughout his apartment when he got home. He chided himself for not turning it off before he left… but really, Mel had just called so early that he didn’t think of it. Plus, he didn’t know he would be gone so long. He just hoped the neighbors wouldn’t complain.
He went to his kitchen to check for her note and found it as usual on his counter. It was very much like always, but this time it held one item that he wasn’t too happy about. Mel had left strict instructions that he was to wear one of his waist cinchers under his girdle to work. Oh joy! As he stepped into his shower, his mind clearly remembered how tight and uncomfortable his new girdle had been all day yesterday. Now he was supposed to wear the waist cincher – and the girdle? Ugh! He wasn’t looking forward to it at all.
A while later, his hair and makeup were done. He was dressed in two diapers with plastic panties, one of his new waist cinchers, and his girdle was strenuously pulled up over everything he was wearing and stretched tightly over his breast forms and shoulders. He grabbed a pair of pantyhose and found himself struggling more than usual to get them on. Way more than usual! Between his super-long fingernails and now the waist cincher under his girdle, the job was nearly impossible. He was so tempted to leave the damn pantyhose off, but he kept at it because it was another layer of protection to keep anyone from smelling his diapers. He struggled to bend far enough to get them onto his feet, but then grabbing and pulling them – without ruining them due to his long nails presented another challenge. The waist cincher plus the girdle made it hard to breathe and he had to stop twice just to catch his breath. But finally he got them pulled into place. Next time, he decided, he would chance not having the extra protection against the smell. Struggling to get them on wasn’t worth it… as long as Mel didn’t mind.
As he walked toward his closet to select his clothes for the day, he felt the added pressure against his backside from the pantyhose he had just put on. Between the girdle pressing on his diapers and now the tight pantyhose too, the raw area seemed to be even more sensitive. He wanted to scratch it but he didn’t dare. He tried to rub it a bit, but through the thick diapers and everything else, the rubbing did no good at all. He only hoped that all the baby lotion he had spread over the area would help… but so far, it wasn’t doing anything. As he opened his closet door, he wondered how long it usually took to clear up a diaper rash.
He stared for a few moments at the clothes in his closet… only female clothes now. The thought sent a minor wave of sexual thrill throughout his body… he was trapped now into only having women’s clothes to wear – once a major fantasy for him. But the reality was mostly fear and humiliation.
He quickly selected a pair of slacks and a blouse he had worn before and put them on. Just as it had been yesterday, his slacks rode down a lot further on his hips because of his new tighter girdle. But this time, because of the waist cincher, the problem was even greater. He had to select a pair of shoes with even higher heels to compensate for how much lower his slacks were. What would he do when he had to wear the one pair of longer length slacks he had? He didn’t have any heels that would be high enough. It was a problem he’d have to take to Mel for sure.
He added what little jewelry he had and stared at his reflection in his bathroom mirror. Robin had suggested that he get his ears pierced and start wearing earrings. Should he? Could he? It was another fantasy that sent minor waves of sexual thrill through him. He decided he better watch himself, he didn’t want any pain from his chastity device to make his day any worse.
He finally stood in front of his full length mirror and looked at himself fully. He immediately noticed his smaller, more constricted stomach. Did the waist cincher really make that much of a difference? Obviously it did. Did he look even more like a woman? Maybe. Only maybe.
He sat and drank yet another baby bottle of Mel’s foul tea. He was becoming very used to the drink now – so used to it that he hardly noticed the taste anymore. As he sat drinking his bottle, staring at his blank wall, his mind began wandering once again to his penis trapped inside of the chastity device… trapped inside of his diapers… trapped under the girdle and the pantyhose. Trapped where he couldn’t ever get hard or even have a prayer of touching it. What would he do if he could finally get hard? As he sucked on his bottle, he closed his eyes and dreamed about it.
In his imagination, he was touching it… pulling it… massaging it – and it felt wonderful. In his imagination, he could see it growing hard and powerful in his hands. It would feel so good. He tried to remember what it felt like to put his raging cock into his wife – make that ex-wife – when they had sex. He knew it had felt wonderful, but for some reason he couldn’t quite remember exactly how it had felt. He opened his eyes once again, still concentrating on his trapped cock. He wanted to feel something there again. He could almost imagine feeling something. He could definitely feel all the sexual desires he had raging through him – but all those feelings seemed to reside, spread out through his entire body now, no longer centered solely in his cock. In fact, his cock was probably the one place that felt those desires the least now, almost numb. He had no doubt that the reason for that was the chastity device… the damn chastity device… the damn device that prevented him from feeling anything at all. Oh how he wished he could remove it. And oh how he wished he could get some relief!

The Bet - Chapter 24 (Monday – week 4 Part 5 of 5)

The Bet
by Karen Singer

Chapter 24 (Monday – week 4 Part 5 of 5)

Chad was taken completely by surprised. Had he said something wrong? If so, he didn’t know what. He found himself being roughly dragged by the arm into the living room. Why was Mel suddenly so angry? What had he done wrong? He felt her roughly pulling at his apron strings to untie them, then she quickly unzipped his maid’s dress. He stepped out of it as he let it fall to the floor. Faster than she had ever done it before, she stripped him completely, till he was standing in front of her in nothing but the breast forms that were thoroughly stuck to his chest – with no way to remove them, and his chastity device that was locked onto his penis – with no way for him to remove it either. He was totally in shock.
He was further surprised when she roughly dragged him around behind one of her living room chairs and shoved him so that he was bent over the thing. “What’s wrong?” he finally asked as she bent him over it.
“Shut up!” she commanded in a voice that left him no doubt that she was upset about something. Fear suddenly began to creep into him… especially when she quickly tied some rope to one wrist and fastened it tightly to the chair leg in front. The other wrist was soon just as securely fastened to the other leg. Bent over the back of the chair as he was, he couldn’t straighten up at all. But Mel wasn’t satisfied yet. She spread his legs further and tied his ankles to the legs behind the chair. He wasn’t going anywhere, that was for sure. His fear quickly grew stronger… and she still hadn’t told him what he had done wrong.
She left him for a few moments, then he heard her come back again. “Damn you!” she yelled. But before he could react to what she had said, he felt the burning pain from her yardstick as she brought it swiftly down on his completely exposed backside.
“Ouch!” he cried out with pain and surprise. But before he could ask again what was wrong, he felt the burning sting from her yardstick again… and again… and again!
“Damn you!” she yelled once again as she again brought down her yardstick with all the force she could muster. His entire backside was already a bright rosy red color. “You belong to me! Not to anyone else… me!” Again she swung her yardstick as hard as she could… and again… and again! “I’m your mistress! Nobody else! You should be focusing ALL your attention on me!” Again she brought down her yardstick three more times. “Damn you! I’m the only thing that should matter in your life. Not anybody or anything else!” Again she hit him as hard as she could, over and over again.
Chad was in pain and shock. What had he done? He still didn’t understand. Not one bit. The only thing he clearly understood was the beating she was giving him… and the fact that she was very angry. But exactly what had he done wrong? And underneath, because she was angry with him, he felt really bad about it. He had somehow disappointed her greatly… even though he didn’t really know why. Something about her being his mistress? And not focusing all his attention on her? He thought he was! So she was punishing him – and because she was angry at him, deep down, he felt really bad.
Early on, he felt the first few blubberings of grief escape his lips. Those few faint cries quickly grew more intense till he was weeping openly. He couldn’t help it. Not only was he in pain from her spanking him, but he inwardly felt so bad because she was somehow so disappointed with him. But what had he done? And he cried because he didn’t know the answer to that question either. He would do anything for her if only she would be happy with him once again.
Mel’s sudden anger had run its course and she finally stopped hitting him. Fortunately, her anger had been fairly brief. She knew she probably shouldn’t have punished him like this, but damn it, all she could see was him paying attention to everybody else more than he paid to her! It wasn’t right! Besides, the contract for the bet gave her the right to punish him whenever she wanted to… for no reason at all. That was one of her rights. He… he had no rights as far as the bet was concerned. None at all! She was thoroughly justified in what she had just done.
She put her hand over his backside. It was bright red and warm and bruised. She had hit him as hard as she could with her yardstick. She knew she should be feeling more remorse for him just then than she did, but damn it! She was still a bit angry at him. Besides, he probably needed this reminder of just who was the boss here! Certainly not him!
And what did he feel about it? For the first time since she started, she took a big enough breath to pay attention to his reaction… and she was amazed to hear him crying into the back of the chair. He was crying? Actually crying?
She threw her yardstick down on the floor pulled his head up a bit so she could see him. There were big tears rolling out of his eyes and he was blubbering like a little baby… make that a big baby. She stared in disbelief. He was actually crying… for real! Finally! She didn’t know if it was all from Gloria’s hypnotic suggestions or the severe beating she had just given him… or more likely from both. But none of that mattered. For the first time he was actually showing the remorse she wanted him to feel when she punished him. And she felt elated inside. Not because he was finally crying… but because finally, she had been the one to see him doing something new… making another breakthrough. Not some other woman. She, his mistress, the one who was supposed to see these little steps of progress, had finally been the one to see it.
“I don’t understand!” Chad blubbered through his tears. “Why?”
“Shut up!” she commanded with more anger than she really felt. She heard his crying intensifying once again as she released his face to bury itself once again in the chair back. He didn’t understand? He didn’t realize he was paying more attention to those other women than to her? Typical of a man! Typical! And stupid!
“Ok, maybe she wasn’t being fair. Maybe it was all just nothing… and a lot of coincidence. But damn it, it had still made her angry. She listened to him crying – still, and her heart melted a bit. “I’ll be right back,” she said with a bit more kindness.
Chad felt so bad. He still had no idea what he had done wrong. And it didn’t really sound like she was going to tell him. Why? And it felt so bad to cry like this. He hadn’t done that since he was a child. But it just felt so bad and he couldn’t help it. He pulled at the ropes holding his arms stretch tightly over the chair. They wouldn’t budge. He pulled again. Still no relief. He sobbed in frustration once again.
He heard Mel come back. He heard her doing something behind him. Then, suddenly, he felt a warm washcloth cleaning his backside for him. He would rather it had been cold, but he was grateful for what she was doing… except that her attention was hurting his bruised skin. He felt her running the cloth as far under him as she could, trying to clean around his chastity device too. Then she was done and the cool air washing over his damp skin felt wonderful. He finally stopped crying completely.
Unfortunately, between the warm wet washcloth and now the cool air running over him, he suddenly had to pee, really badly. But he didn’t really want to pee all over her floor or the back of her chair. He clamped down tightly to hold it back. “Mistress,” he cried.
“Hush!” she commanded as she began untying his legs.
He was startled. But he had to warn her that he needed to pee… or she might be punishing him a lot worse. “Please…” he started to say.
“I said hush!” she commanded once again as she started working on his other leg.
Chad was in shock. He had to pee so badly that he didn’t think he could hold it very long at all. And Mel wasn’t letting him even warn her! What was he going to do? She was taking an awful long time getting the rope off of his second ankle. He continued to try as hard as he could to hold back. Mel finally went around to the front of the chair to start releasing his wrists, but not fast enough for his need. In his fear of wetting all over her floor and furniture, he was pulling back on the ropes too hard, making them harder to untie than they should have been.
Finally, she got the last of the ropes off of him and he stood up quickly. As he did, he felt a few drops of pee that had leaked out, running down his leg. But standing up and changing position only seemed to make his need to pee worse. “Mistress,” he began once again as he tried to grab his penis with his hands to stop the flow. But the hard plastic encasing him didn’t allow him any contact with that part of his body at all. His hands couldn’t squeeze his penis closed at all and yet more of his pee escaped.
Mel was about to yell at him to be quiet once again when she saw him grabbing himself. She instantly realized his problem, especially when she saw a bit of pee squirting out of the chastity device to land on the floor. “I laid out a diaper on the floor for you. Lay down on it,” she commanded quickly.
Chad finally noticed the diaper she had put down and as fast as he could, laid down on it and brought it up between his legs and held it there. With a small grunt of relief, he let himself pee into the diaper – thoroughly. He sighed. He knew he had wet her floor a bit, but fortunately, the vast bulk of it was going into the diaper she had put out. He had just barely made it.
Mel watched him fascinated. He obviously still had some control, but also just as obviously, not very much. She was kind of glad that he had managed to not pee all over her chair, but at the same time, she was disappointed too. If he were truly incontinent then he would not have been able to help himself. Obviously, he still had a ways to go… but just as obviously she was making pretty good progress. In the future, she’d have to be a bit more careful about that if she punished him again… or rather, when she punished him again – because she had no doubt that eventually she would do just that. “Stay there,” she commanded as she walked off to get another fresh diaper for him.
Chad still wanted to know why she had punished him, and severely at that. His backside felt like it was on fire as he laid on it. Not comfortable at all. In fact, very painful. He really wanted to rub it… but not with a wet diaper. For once, he was looking forward to being dry for a while. Hopefully, she would put some baby lotion on it and that would make it feel better. He hoped anyway.
Mel finally came back with a fresh diaper and put it under him. “Mistress…”
“I don’t want to talk about it!”
He was startled once again. He wanted to ask her why not… along with a host of other questions. But she didn’t seem to want to talk. Did she think that her reasons should be obvious to him? Because they certainly weren’t!
He was rather disappointed when she shoved two suppositories up inside of him and then began pinning him into the thick layers of his night diapers – without putting any baby lotion on him at all. None in fact. Was she being purposely cruel? Or had she just forgotten? He couldn’t be sure either way. But what could he do about it? She wasn’t letting him answer any questions at all.
A few minutes later, dressed in just his super thick diapers and plastic panties, she led him out her door to his own apartment. He had never even started to clean the dishes from dinner. Her kitchen was still a mess. She also hadn’t asked him to clean up where he had peed on her floor a bit. That surprised him too. And now she was obviously getting rid of him for the night. What had he done wrong? But she still wouldn’t talk about it.
She led him into his bedroom and put one of his onesies on him for the night over everything else he was wearing. The falsies stuck to his chest inside of it now made it look even stranger on him than it ever had before. She almost laughed… but she wasn’t really in the mood. She made him lay down on his blow up mattress, putting him to bed much earlier than usual while she went into his kitchen and pulled four baby bottles of her tea mixture out of his refrigerator.
Chad was surprised to see her bringing four bottles instead of the usual two or three. “Four?” he asked tentatively.
“You’ve got plenty of time,” she replied.
Chad wasn’t sure, but he thought there was still a hint of anger in her voice. He put one of the bottles to his lips and began sucking on it as he laid his head back against his pillow.
Mel walked back to the entrance to his bedroom and turned off the light. The room was instantly plunged into odd shadows as the light from outside cast a strange glow across everything. She looked back at him and paused. Should she have punished him? Did she really have a valid reason? Deep inside, she knew she didn’t. Yet she had thought so at the time and she had done it. Why? Why should it matter so much to her?
She watched him suckling on his bottle, watching her watching him. Almost as an afterthought she walked back to him and knelt down next to him. She kissed him lightly on the forehead. “Goodnight baby. Sleep well.”

Catching Up

Hi All,

It’s been a while since I’ve posted anything other than the story. I’m afraid I don’t have much to talk about here either.

First off, another huge thank you to all who have posted comments. You don’t know how much I appreciate them.

Next. I’m probably going to miss the next usual posting of the story on Friday due to a little vacation I’m taking with the family. Don’t panic, I’ll be back – I hope.

A short while back, one reader suggested that I post the parts of the story more often. I wanted to particularly address this. Yes, I’d really like to do that. I know this story must be really frustrating to follow since I don’t put up much of it each week. But…

I went through kind of a writing slump not long ago – and it lasted almost two months. I didn’t write hardly a word. Not only that, I was kind of depressed about other things too. I really wanted to write… but I just couldn’t seem to do it. The result? You are all now a lot closer to were I am in writing the story than I’m comfortable with. Yes, I am writing again – fortunately. And I have regained a tiny bit of the ground in front of you back again, but not much yet. In fact, since the slump, I’ve only completed one chapter that I had started before it, one more complete chapter, and I’m now halfway through the next chapter. But I’ve done all that in less than three weeks, so I’m fully back into it again.

If I ever finish this story, (in about a thousand years I think) then I’ll start posting faster – maybe.

On a very sad note – to me. I have gone ahead and gotten rid of all my “fetish stuff” I had hidden in the attic. I’m very, very sad to say that. I hate it. But my life has changed now. I can see that I’ll probably never be left alone again… at least not for a very long time. My step son has moved into the house with us permanently, and more often than not, at least one of his two daughters are always here. Not only that, but we desperately need to do some repairs to the house – right around the area where I had every thing hid. Not a good thing!

I’m still recovering from my heart attack too. It’s going to be a longer road than I ever thought. I fee pains and aches all the time that have me worried that I might be having another one. It’s very frustrating! I’m trying so hard to regain strength and get back to “normal” again. But it’s just not happening. A good friend of this blog suggested that I need to get used to a “new normal” instead. I can see more and more where he’s probably very right. I just have to figure out what that “new normal” is. I want so much to be like I used to be. I just don’t know how to get there. Getting older probably isn’t helping matters much either… I celebrated yet another birthday last month.

So a huge thank you to all who are reading and enjoying this blog and story. You’re all the reason I keep going.

Smile today!
Karen

The Bet - Chapter 24 (Monday – week 4 Part 4 of 5)

The Bet
by Karen Singer

Chapter 24 (Monday – week 4 Part 4 of 5)

Mel pulled into her parking space with only one thing on her mind – Chad. What was she going to do with him? Was she really going to punish him? Did he deserve to be punished? Not that it really mattered. According to the rules of the bet, she could punish him whenever she felt like it for no reason at all. But would that be a good thing? She trudged up the stairs and opened her door. The first thing she saw was Sissy coming quickly out of the kitchen in his maid’s uniform, large wooden spoon in hand. He dropped a quick curtsey and greeted her formally with a big smile on his face. Her entire mood brightened. Oh she loved this! Knowing that he was quickly becoming her greatest fantasy… and that he was doing so well really made her feel good. Punish him? Maybe not. She saw him motioning with the big spoon toward the kitchen. “Go!” she commanded. “Take care of it.” She smiled. Life was good!
The air in her apartment was filled with a rather pungent but interesting aroma as she put her things down on the table by the door. She wrinkled her nose a bit at the smell and wandered into the kitchen. “What’s cooking?” she asked.
Chad was just taking a tiny taste from the contents of one of the pans on the stove as she asked her question. The mixture was a bit stronger than he anticipated it would be. Not bad at all, just spicy. And it was hot! Way too hot! He opened his mouth and waved his hand to cool his tongue as tears formed in his eyes. Instead of answering her, he pointed at the cookbook on the counter.
Mel glanced down to look at the picture of the dish in the book. It certainly looked good. Colorful too. She glanced back up at Chad. He had reached into the refrigerator and grabbed a baby bottle full of tea and was drinking it quickly. He finally took the bottle out of his mouth with a huge sigh of relief. “Too hot,” he gasped.
She giggled. “How soon till it’s ready?” she asked.
“Just a few minutes. It’s taking a bit longer than I anticipated.”
“No problem.” She replied as she walked out on him. Having someone there every night to fix her meals and take care of her home was so nice. So wonderful. So great! Sissy might be a total flake, but he was just what she needed. Perfect! And the power that she felt from what she was forcing him to do was almost mind-blowing! Punish him? Why? It would only ruin her evening.
Chad dished the meal he had just prepared out onto two plates, his plate he stuck straight into the refrigerator as usual. Between how hot the food had been and his now burned tongue, he was actually glad to cool off his food for once. He put Mel’s dish, still steaming, on the table for her. He poured her a cold diet drink to go with it. Since he had needed a drink from his bottle to cool his mouth, then he had no doubt that she might need a cold drink too. He walked to the entrance to the living room. “Dinner is ready, Mistress,” he proclaimed.
Mel sauntered into the kitchen with a smile. “Please be careful,” Chad cautioned, “it’s still a bit hot.”
“Thank you, Sissy,” she said as she sat down. The food in front of her did look colorful. It smelled a bit stronger than she was used to, but not too bad. It looked like Sissy had been right about how hot it still was, she could see the steam still rising from it. She looked up at him and just stared.
Chad saw her staring at him and sighed. He knew what she wanted. He turned and wandered directly to his corner where he placed his feet over the bar and stood crammed into the two walls once again. Ugh! Just once he’d like to get away from this corner! Just once!
He couldn’t hear anything. Of course Mel was eating and wasn’t saying anything to hear. He couldn’t see anything either, except the two blank walls right in front of his eyes. He had to close his eyes to keep from going cross-eyed. He wasn’t supposed to move, so the only touching sensation he could feel was the two walls around him… and the growing ache in his legs and feet from having to stand on the miserable bar. He could still smell the dinner he had prepared. His stomach growled a bit. He realized he was hungry. He played for a moment with his slightly burned tongue. It felt a bit numb at the tip. He should have been more careful when he tasted the food. Bored, bored, bored! Stuck in his corner with no stimulation. Again! Ugh!
With nothing else to think about, his mind turned back to the topic that had occupied him happily for a while early in the morning. What would he do if he could finally get hard? A very interesting question. The problem was, he still had no real answers. No ideas at all. Oh he wanted relief for sure! But he wasn’t really sure he wanted to blow the experience too fast. He was to the point now where just getting hard would be an experience to savor. He supposed he would play with himself some, enjoying the pleasures… then he would stop and let things calm down again so as not to go too far. He figured he’d do something like that over and over again. It was a very wonderful thought. Very wonderful! In his imagination, he could almost feel it! Yeah, so nice!
But oddly, within his imaginary feelings, he suddenly found another part of his anatomy feeling some stimulation too – his backside. He found that very strange as his imagination went astray while he stood in his corner… His imagination was feeling stimulation from both his cock and his anus at the same time. Why? It troubled him a bit, yet it was only a dream – a pleasant dream, but a dream none the less. In the end, he was just thankful that even the imaginary stimulation and pleasure wasn’t making him get hard at all. He didn’t want to feel any pain from the teeth in his chastity device.
“Sissy! Get over here!”
Chad was startled by Mel’s voice. Quickly he climbed off of the bar he was standing on and allowed his dreaming to fade. But what an interesting dream it had been. He’d have to try dreaming about it again the next time he was stuck there. “Yes, Mistress?” he asked as he hurried toward the kitchen.
Mel was just getting up from the table. “Dinner was ok,” she said, “but not as good as the other things you’ve made so far. Cross this dish off your list.”
“Sorry, Mistress,” he apologized. “I didn’t have any way of knowing.”
“I know. Just don’t make it again. I know we can’t expect everything to be good. Get your dinner out now.”
Chad hurried to the refrigerator, very glad that for once he was going to get to taste something he had prepared – even if it wasn’t as good as some of the other dishes. He was also glad that Mel had been very understanding that he didn’t know how the recipe would taste. He saw Mel taking the tray off of his highchair as he pulled his dinner out. “Put it on the counter,” Mel instructed as she waited for him with the tray still in her hands. He did as he was told, then climbed up into the chair and held his arms out of the way as Mel put the tray back into place, trapping him in the chair. At least she didn’t bother with the seatbelt again. Of course there wasn’t much sense in the seatbelt anyway.
The fact that dinner hadn’t been as good as she had hoped had spoiled Mel’s mood a bit, but really, she did understand. Everything he was cooking was something out of a book and was new – to both of them. Even still, it was a bit of a disappointment after the other things he had made so far. She grabbed a bib out of her drawer and fastened it around his neck, then she placed his dinner on the tray in front of him. Having nothing but his fingers to eat with, he began picking up bits of the food and putting them into his mouth.
Mel pulled out another one of the chairs at her table to sit and watch him eat. She giggled just a bit. The food was covered with sauce and was a bit messy, and since he had to eat it with just his fingers, his face and hands were quickly becoming a mess… just like a baby. God, she loved making him behave so ridiculously! She couldn’t help it, it was just plain fun! “So how was your day today?” she finally asked.
Chad was a bit surprised at the question as he tried to shove a long thin piece of vegetable into his mouth. The vegetables were covered in a sauce, most of which wound up on his face. He had to stop to consider her question. “Strange,” he finally answered.
That surprised her a bit. “Why?”
Chad shook his head as he selected yet another long piece of vegetable. “Well, we got our project to the point where we sent it for the client’s approval, then we both discovered that we had nothing else to work on.”
“You and…”
“Robin, of course.”
The damn Robin woman again. Mel was suddenly sorry she had asked about his day. She knew it wasn’t right, but she still felt very annoyed every time he mentioned her. She bit back her irritation and asked, “So what did you do with your free time?”
He shrugged. “You wouldn’t believe it. We sat and read women’s magazines together for most of the day.”
Mel blinked, then stared. She wanted to laugh, but the fact that he had been doing it with Robin sent more irritation though her. “You read women’s magazines together?”
“Mm hmmm,” he replied as he chewed on a messy piece of meat.
“I didn’t know you liked to read women’s magazines… although since you’re a sissy, I’m not a bit surprised. Do you do that often?”
He shook his head as he picked up another piece of messy meat. “First time. I’ve never really bought any before.”
“But you bought some today?”
“No, these were some that someone had stuck on my desk for me last week. Then this afternoon Robin bought some more.”
Robin again! And what else was he doing with her? Her irritation had gown just a bit once again. She carefully tried to control her temper. “And did you enjoy reading the magazines?”
He shoved yet another piece of meat into his mouth as he considered the question. “It was ok, I guess. To be honest, I didn’t really understand most of it that well. I mean, I want to, but I just don’t have much experience with makeup and clothes and stuff. It was nice to have Robin there to answer a few questions. And at least she didn’t make me feel like I was doing anything wrong.”
Mel took in his answer. Fully. Especially the part about Robin. And the more she thought about it, the less she liked it. It sounded like he was far too comfortable with his friend Robin. And worse, Robin was getting to do things with him that she herself couldn’t do. She was missing out on too many things that she’d like to be seeing first hand with Sissy. First there had been Cassie, watching him lose control of himself right in front of her. Then Cassie had learned about his growing fascination with his back end. Then Sandy had done something with him in that regard that must have been fairly intense when she had babysat with him. And now Robin was continuing to make further inroads and was getting closer and closer to him. It wasn’t fair! He belonged to her… not any of the others. His mind and focus should be only on her and nobody else. She was his Mistress, not Robin! In her mind, she could just see him, dressed as he had been that morning, locked in the arms of a beautiful younger woman.
Her anger suddenly flared and she got quickly up from the table. She found her small collection of ropes and threw them all down onto her coffee table, then she went back into the kitchen. He still hadn’t finished his dinner yet, but she didn’t care. She quickly removed the plate from in front of him and put it onto the counter. His face and hands were such a mess that she didn’t want to touch him yet, so she grabbed a wash cloth and roughly wiped him clean. Then she removed the tray that had locked him in and pulled him into the living room.