The Bet - Chapter 46 (Tuesday – week 7 Part 2 of 9)

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 2 of 9)

Robin stared at her computer screen, but her mind was more on the apology that Chad had just given her and on the email that Mel had sent. So that was Mel’s idea of a proper apology? Well, she guessed it was a lot better than some. Not that she really cared. Should she answer the crazy woman like she wanted and tell her that she had received Sissy’s apology? Against her better judgment, she opened the email and hit the return button and typed: “Yes, he apologized.” Then she sent the email. Hopefully, she could put both her and Sissy out of her mind for a while.

Mel saw Robin’s email as soon as she got to work. She was glad that Sissy had actually apologized, but Robin certainly wasn’t very forthcoming with the details. She closed the email and opened up the one from Sissy. From what she read in Chad’s email, it sounded like Robin was still pretty angry – which made sense when compared with the email she had just gotten from Robin. So… now it was time to check on a few things. She opened Robin’s email again and typed a short reply.

Robin still had one or two little things left to do on her list from Tom Robinson, but it really amounted to nothing much. She could do it all in less than an hour, if she wanted to. But she was distracted from finishing any of it by another email from Mel. As much as she didn’t want to open it, because she really didn’t care what the woman wanted, she also couldn’t not open it.

Dear Robin,

I’m very glad he apologized, but I’m worried that he didn’t do it exactly the way that I wanted him to. Before his apology and also after it, he was supposed to give you a very nice curtsey, pulling his skirt as wide as possible in the process. I made sure he was wearing a very full skirt today so that his curtsey could be at its “sissy best.” Please let me know if he did this.

As always, feel free to call or email me,

Mel

Sissy best? That concept floored her. Yes, she knew the guy was a sissy, but it’s just that the label had never struck her that much. In the past, before she knew better, she had thought of him more as one of those cross-dresser types. In fact, since he had been dressing totally as a woman for so long now, she had started to believe that eventually he would be getting a sex change – no matter how much he denied it. But a sissy? That label brought to mind a whole new level of concepts – and the realization that she knew less about someone who was a sissy than she did about someone who was a cross-dresser – which wasn’t very much. But… was “sissy” an accurate label for Sissy?
Not knowing, and also not sure she wanted to know, she went back and reread the details of Mel’s little email. He was supposed to curtsey before and after – well, that much he had done. And the more she thought about the fact that he had curtseyed, the more she liked the term sissy for him. A woman apologizing to another woman wouldn’t curtsey in the process. In fact, there were very few reasons why a woman now-days would curtsey at all. She herself had rarely done it in her entire life! She barely knew how! So now the term sissy was starting to take on a whole new meaning for her.
And he was supposed to pull his skirt as wide as possible? Well, that much he certainly hadn’t done! She had been surprised that he had curtseyed in the first place. Although when he had done it, she had pretty much dismissed it, waiting to hear what he had to say instead.
So, bottom line, he had apologized, but not the way he was supposed to. She wondered what else he might have left out. Not that it mattered. She always believed that an apology should come from the heart for it to mean anything. So obviously, this was contrived and as an apology it didn’t amount to a hill of beans! Not that she really cared all that much. She was still pretty much angry and disgusted with the jerk and she still wasn’t all that sure how, or if, she should talk to him again. The idiot!
After quickly reading Mel’s email one last time, she was reminded of her problem with him yesterday where he hadn’t done as he was told. Okay, she was overly upset and sensitive yesterday, she guessed she still was somewhat. But at least she wasn’t as bad today – she thought. But still, the point was that obviously, when left on his own, he couldn’t be trusted to follow through with what he was supposed to do! Just like a child! But then he wanted to be a child – well, he wanted to be a baby. But that was still a child! Was he now acting more and more like one? She shook her head in disgust and typed a short reply to Mel. “He curtseyed, but not at all like that. What else was he supposed to do – or say?”

It was a while before Mel had time to check her email again. She wasn’t sure if she was surprised or not that Chad hadn’t apologized like she wanted him to. In fact, she had mostly expected that he wouldn’t. But the part that she was really interested in was that Robin had replied again – and asked for details! That alone meant a lot!
But how should she proceed? For once, she didn’t want to frighten Robin off, so she knew she still had to be careful. Very cautiously, she typed her reply to Robin. Again, it was short and simple, only telling her the text of what he was supposed to say. But just before she sent it, as an afterthought, she added one extra little tidbit.

It was almost break-time when Robin got the reply from Mel. Again, she was tempted to not open it, but like before, she was too curious as to what was in the email.

Dear Robin,

Thank you so much for replying to me. Here’s what was supposed to happen:

He was supposed to give you a very nice curtsey, pulling his skirt as wide as possible while bowing his head in respect to you. Then he was supposed to stand up straight with his feet together and his hands clasped nicely in front as he said: I’m sorry Robin that I didn’t do exactly what you told me to do yesterday. I promise not to give you any more trouble and to do whatever you say from now on. Then he was supposed to repeat the same curtsey he had given you at the start.

I was hoping that this simple but sincere little routine would be acceptable to you and would also get the point across to him that he needs to follow your direction just as if it were me.

Oh, one other thing. Did you know that his “girly voice” is not the way that I want him to talk? Even this apology was supposed to be given in his “sissy voice.”

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

Robin must have read the email at least three times. Nothing that Sissy had done was like Mel had wanted it to be. For someone who was supposed to be his… mistress – what a laugh – obviously Mel wasn’t all that good at controlling him. She knew without a doubt that she shouldn’t really care, but it still irked her that Sissy was supposed to give a “better” apology to her than he did – even if it was contrived by someone else. But what should she do about it? In fact why should she do anything about it? There was no way she was going to get drawn into that crazy woman’s games! Still, it irked her. And what the heck did she mean by his “sissy voice?”
She glanced at the clock. Break time. With a bit of a huff, she closed the email and left her cubicle. She stopped at the entrance to Chad’s cubicle. “Sissy, it’s break time!”
Chad looked up in surprise. Was she speaking to him again? He quickly got up from his seat and followed her out into the hallway. “Robin,” he started to say, but he got no further than that as she quickly turned on him and forcibly backed him up against the wall.
“What do I have to do,” she said forcibly, “make you go to break with your thumb in your mouth too? What’s it going to take for you to understand that I don’t want to talk to you yet?”
Chad was too shocked to do more than stare at her wide-eyed. One thing he had learned about her in the last two days was that she seemed to get awfully physical when she was really angry. Silently, he followed along behind her to the break room.
The act of walking seemed to stimulate Robin’s thoughts – which immediately returned to Sissy and Mel’s email. Why should she care? She didn’t! She absolutely didn’t. But she couldn’t stop brooding about it. Sissy should have given her a better apology than he did. He was supposed to… and… she deserved something better! And what the heck was his “sissy voice?”
In the break room, she headed straight for the coffee pot and poured herself a cup, never glancing once back in Sissy’s direction. She just knew he was there – like an extra arm or leg. She had already spotted the nearly empty box of doughnuts and grabbed the very last one. With a mocking look straight at him, she took a bite and acted like it was the best doughnut she had ever tasted – even though she hardly tasted it at all. Then she walked away toward the women’s table as if she were ignoring him completely.
Chad wasn’t all that worried about not getting a doughnut, he was more worried about Robin and what she might do. He finished pouring his coffee and carried it over to the women’s table where he found a chair nearby and sat down extra slowly so as not to irritate his backside any more than it already was. He decided to try to stay as quiet and as out of the conversation as possible today, just to be safe. But then, that was always what he wanted, the other women just never seemed to let him.
Robin noticed how slowly Sissy sat down. She wondered if Mel had beat him last night. But after watching him sit, she was betting that Mel had. Well, he deserved it! But obviously the lesson hadn’t stuck properly. Just like a child! The idiot!
She watched him as one of the women teasingly asked him about when he was going to see Derek again and again Chad tried to explain that he and Derek weren’t “dating.” As funny and interesting as that used to be for her – last week, now she knew that something much different was probably behind it all. She didn’t know exactly what, but those questions couldn’t be asked here.
As the other women laughed and talked, she sat silently, thinking, brooding.
“Robin,” one of the women broke her concentration. “You’re being awfully quiet today. Are you feeling alright?”
Robin shrugged. It’s just that… she looked straight at Chad… “the… baby… has been driving me crazy lately.”
Chad instantly understood which baby she was talking about. Not her own.
“Oh,” the woman said in reply. “Well, he’s what? One now? Once they reach that age where they can start moving around faster, they just seem to get into the darndest things!”
“Don’t they!” Robin replied, glaring at Sissy once again. She was saved from any further answer as the talk around the table instantly turned toward the ones with young kids. She had a baby of her own, a one-year-old who had just recently learned to walk and was now getting into all kinds of mischief. Was she now going to be saddled with another baby a – how old was Chad anyway? Not that it mattered. He wanted to be a baby and the more she thought about it, the more she realized he was acting like one! The jerk! He couldn’t even apologize properly!
The women started getting up from the table to head back to their desks and Robin did the same. So did Sissy. Amid a fairly large group of women, they both headed back out into the hallway. A few minutes later, Chad was trying to follow behind her as quietly and as unobtrusively as possible again. Robin knew he was still following her, she just chose to ignore him – for now. They turned down the last hallway where their cubicles were located. Robin walked right past his cubicle, heading for her own. But she stopped at the entrance and turned around. He had just turned into his own cubicle. “What the hell is wrong with you?” she asked.
Chad was taken aback again. What had he done wrong now? He knew he hadn’t uttered a word. In fact, he had hardly made any sound at all.
“I got an email from your… mistress,” she spat the word again... “a little while ago. And that silly little apology you gave me earlier wasn’t even close to what you were supposed to do!”
Chad saw her suddenly heading for him again and he backed away from her, straight into his chair where he winced a bit at the pain still in his backside as he fell into it.
Robin noticed the look on his face as he sat down. “What’s wrong? Did your… mistress… beat you last night?” When she got no answer, she yelled, “Tell me!”
Chad nodded, as the fear started to grow in him.
“I didn’t say nod your head. I said tell me! Did she beat you?”
“Y… Yes,” Chad stammered.
Robin nodded. “Good! I hope she beats you every night – because I can’t think of anyone who deserves a beating more than you!
“I still can’t get over that you’re doing such a stupid thing! It’s… insane! And worse… you want to be a baby too? I just don’t get it!” she said with a shake of her head. “Why would anyone… It’s stupid, stupid, stupid!”
She paused for a second. “You want to be a baby? Well, from what I see lately you’re behaving more and more like one every day! Take that stupid excuse for an apology you gave me earlier. What is it? You’re not ‘man’ enough to do it properly? Well, we know that already! You’re not even enough of an adult to take the responsibility of doing what you’re told! Like a little baby, you tried to get away with something and thought I wouldn’t know about it! Well I do know about it! I know exactly what kind of apology you were supposed to give me, right down to what you were supposed to say to me!”
She stared at him sitting fearfully in his chair for a moment. “Get up!” she ordered as she turned around and started out. “Let’s try it again!” She didn’t know if she was angry or what, but she went straight back to her cubicle.
Chad was in a state of shock. She knew what was supposed to be in the apology? Obviously she had heard from Mel again. Still feeling a bit fearful, he got out of his chair and headed back to her cubicle.
Robin was opening up her email program when she heard him enter her cubicle again. She turned on him quickly. “Did I say you can come in here? Back up! Back out into the hallway again!” She watched till he was back to the middle of the hallway before turning her back on him. She opened up Mel’s email and read it through thoroughly, paying strict attention to the words that Chad was supposed to say. Then she turned around to face him again. He was still in the middle of the hallway. Good! “Okay, I’m waiting,” she said. “Now let me see how you were supposed to apologize.”
Chad stood there for a second. He didn’t know why he felt a bit afraid, but he did. He inwardly gulped, then looked up and down the hallway to make sure nobody else was around that would see him.
“I’m waiting!” Robin said impatiently.
Chad again started with a small curtsey toward her.
“Stop right there!” Robin yelled angrily. “That’s not what your friend said you were supposed to do!” She turned quickly in her chair and read out loud from Mel’s email so that he could hear. “He was supposed to give you a very nice curtsey, pulling his skirt as wide as possible while bowing his head in respect to you. Then he was supposed to stand up straight with his feet together and his hands clasped nicely in front.” She turned back to him again. “Was that little… thing… you just did anything at all like what you were supposed to do?”
The fear inside of Chad grew a bit more. “N… No,” he replied.
“See! Once again you’re acting like a child and trying to get away with something! Geez! Now let’s see it properly!”
Once again Chad looked up and down the hallway to make sure nobody was watching.
This time he curtseyed exactly the way Mel wanted him to, pulling his skirt wide, bowing his head, and standing back up with his feet together and his hands clasped nicely in front of him. Then he launched into his little apology speech – in his girly voice. When he was done, he repeated his curtsy routine once again.
Robin stared at him for a moment, then grunted and shook her head. The term sissy was starting to grow on her. The idiot! She shook her head. “Come here!” Chad started moving toward her cubicle but she stopped him just before he could enter it. “Now tell me,” she said a bit more calmly, “what the heck is your ‘sissy voice’?”
Chad’s eyes went wide. Mel had told her about that too? He looked down at the floor bashfully. “Um… She makes me talk that way because it makes me sound more childish and like a…” his voice dropped to almost a whisper, “sissy.”
Robin just stared at him. More childish? Like a sissy? Well that figured. “What way? Explain.”
Chad was getting more and more uncomfortable talking about it. “Um… Well basically, I replace all the ‘R’ and ‘L’ sounds with ‘W’. He looked up at her finally. “So Robin comes out as ‘Wobin’ and hello sounds like ‘hewwo’.”
Robin nodded. “I see.” Even though she wasn’t entirely sure. “According to your mistress friend Mel, you were supposed to give me that apology in your sissy voice too. Weren’t you?”
Chad nodded bashfully. “Yes.”
“Then why didn’t you?”
He shrugged. “It’s embarrassing,” he finally admitted.
“And curtseying like a… I don’t know what, and everything else you do isn’t?”
He nodded. “Yes it is. Very!”
“So what’s the difference between this and everything else? What makes talking like an idiot any more embarrassing than… whatever?”
But Chad didn’t really have an answer so he just shrugged his shoulders indicating he didn’t know. He felt like a child being yelled at by a grownup.
Robin rolled her eyes and shook her head. “Now… Do you think you can go back there and this time, finally do it properly?”
Instead of answering, Chad just nervously nodded his head. Then he started moving back out to the middle of the hallway again.
Robin shook her head. “Geez,” she muttered. “Just like a child.” Then a little louder she said so he could hear, “You want to be a baby again? At the rate your going, you’re going to get there really soon! I can’t believe how childish you behave. Why didn’t I ever notice it before?”
Chad made no reply. He just backed up to where he had apologized from before. Twice! He glanced even more nervously up and down the hallway. Out in the open like this, doing it over and over again, was starting to tempt fate a bit more than he would like. Once again he dropped her the rather lavish curtsey and once again he launched into his little apology speech – this time in his sissy voice, and once again he finished with the same curtsey again. When he was finished, he just stood there in the hallway, staring at her, unsure about what he should do.
Robin had taken the whole performance in. Somehow, changing the voice the little bit that he had gave the whole thing a different meaning. Somehow, it made the whole thing seem more childish. Somehow, it made her think again about the term sissy – which was really starting to make more and more sense to her. She saw Chad suddenly start walking back towards her again. “Stay there!” she ordered, and watched as he backed up again to stand right where he had been.
Now what? Now what was she supposed to do with him? Send him back to his desk? Try to put him out of sight, out of mind? Somehow, that all seemed… just wrong! He had made her so angry – first when she found out about his stupid bet and his… inclinations, and secondly by not at least apologizing correctly to her. He had tried to shrug her off as not deserving of a decent apology. Well… She could deal with that!
“Do it again!” she ordered.
Chad was shocked. “Again? But I did it perfectly. I promise!”
“I didn’t say you didn’t. Now do it again!”
Chad briefly closed his eyes in frustration, then once again launched into his little routine.
Robin watched him carefully one more time. When he had finished again, she said. “Again!”
Chad was dumbfounded. She really wanted him to do it again? Why? But before he could begin again he heard her say, “And again… And again… And again… And again. Just keep doing it over and over again till I tell you to stop!”
Keep doing it? “But what if somebody sees me?” he asked nervously.
“I don’t care! You’re the one who didn’t do it right in the first place! You’re the one who likes being embarrassed. I hope someone else does see you! Now do it again!”
Horrified, Chad again launched into his little routine, but halfway through it, he saw Robin turn away from him and open up one of the programs on her computer like she was ignoring him. When he finished, he stood there and waited.
“Keep going,” Robin ordered with her back still to him. “Just keep doing it – over and over and over again.”
“How many times?” Chad asked, still not believing what she wanted.
Robin turned briefly back to him. “Only a child would ask a question like that. I said, just keep doing it. There are no set number of times. You’ll do it till I get sick of hearing you!” Then she turned away again.
What could Chad do? He went into the formal curtsey again and kept going.
Robin tried to work a bit on the things she had to finish, but something was nagging at her brain – besides the sound of Chad droning on in the background behind her. Giving in, she opened up the email from Mel and typed. “The apology he gave originally wasn’t even close to what it was supposed to be. I’ve corrected the situation and he is practicing it over and over again now. Do you always have this much trouble with him?”

The Bet - Chapter 46 (Tuesday – week 7 Part 1 of 9)

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 1 of 9)

It was the most peaceful sleep she had had in a while. But that doesn’t mean her dreams were without conflict – which doesn’t mean that her dreams were without pleasure too. For in her dreams, she was in bed, making love to… Ray – at first. Because in the middle of her dream, where things were just starting to get hot and passionate between them, Derek showed up and ruined it all. But this time it was an angry Derek. Angry enough to grab Ray and pull him right off of her. She was frightened by Derek’s rage, but the fright didn’t last.
Ray and Derek argued – over her! As she laid back in her bed, watching the two hunks, she felt nothing but thrilled as they continued to argue about which one of them was going to make love to her. She wanted Ray to win because he was there first. She had already started with him. But… but there was just something special about Derek too. She really kind of liked him better for some reason. So, she was torn.
The argument turned from a very heated discussion into a fist fight! In her dream, she sat up on the bed to watch and cheer for… both of them. She felt so honored that each of them would want her so badly. So special! But then someone else climbed up onto the bed with her, someone she hadn’t expected. Sissy was suddenly at her side, holding her, kissing her, caressing her in the most intimate ways. And his touch felt so good, so arousing, so sensual.
She laid back on the bed and let Sissy make love to her while she kept watch on the two hunks fighting over her in the distance. How perfect could anything get?
But one of the two big men noticed what Sissy was doing and their fight stopped. Together they rushed at her… and Sissy. In their rage, they both tore Sissy from her grasp and threw him angrily away from her. Together they kicked and beat him horribly, chasing him further and further away from her, until finally, Sissy had no choice but to run away as fast as he could – never to be seen again.
She felt heartbroken. Victorious, the two big men returned to her bed together, and together they caressed her and made sweet love to her, but it was a bittersweet love. Despite them, her heart ached horribly for Sissy, and despite the two hunks lavishing their attentions on her, she yearned for him.
The alarm on her clock buzzed and she awoke. She felt like she had gained something – but in the process had lost something bigger. She just didn’t know what that something was. She reached over and turned off the alarm as she sat up on the side of the bed. Her need for coffee was so ingrained in her that she didn’t even think about it. She grabbed her robe as she got to her feet and slipped it on as she headed out toward her kitchen.
As she watched the freshly brewing coffee dripping into the pot, her mind remembered that she had a date tonight – with Ray. She was looking forward to that. She was really hoping that it would be fun… and hopefully, would lead to – something else! But later tonight was still a long way off and other things soon made their way into her consciousness. Things like – Sissy. He had been so great last night – again! Really, the little sissy had the most wonderful touch. And his tongue! She remembered that he was supposed to be going out with Sandy and Cassie later tonight to visit their friends. She had a feeling that that was going to be an interesting trip.
Her coffee finished brewing and she reached for the cabinet to get a cup, but she had to stop and correct herself as to which cabinet to open. She hated change, especially when it involved anything that she had to do before she had her coffee! A minute later, her coffee poured, she took a sip and carried it into her living room where she sat in her chair.
Thinking about Sissy, soon led her to think about Robin. Yesterday had been strange. Not at all what she had expected. And Robin had actually ordered Sissy to suck his thumb! At work? Amazing! Did that mean… she almost didn’t dare to think the thought… did that mean that Robin might become someone who she could count on to help with Sissy while he was at work? It seemed too remote a possibility to really give credit to. But… was it possible?

One minute he was sound asleep, the next, loud blaring rock music poured out of his pink clock radio, jarring him from a sound slumber into instant confused wakefulness. And he had been sleeping so good! As soon as he could collect his wits enough, he rolled over onto the floor from his blow-up mattress, scattering a few empty baby bottles in the process, and got to his knees, where he immediately reached over and turned the overly obnoxious music off. What a way to wake up every day! Ugh! But he had to admit, it certainly worked!
He took a deep breath and took stock of himself. His diapers were overly bloated as usual – messy too. His backside itched terribly because of the beating he had gotten last night. He hoped it wouldn’t turn into diaper rash. He had put a bra on before going to bed last night to help support his glued-on breast forms. They still hung heavily from his chest. Of course, his penis was locked away inside of a chastity device and had been for a long time now. It had become mostly… useless. And last night… last night she had taken him in the rear… and he had orgasmed that way. Unbelievably!
He climbed awkwardly to his feet, hampered by the thick diapers he was wearing. He resisted the urge to scratch a bit at his irritated backside as he stumbled awkwardly out toward the kitchen where she usually left him his note. Once again, the note was there, but it might as well have been the same one she left every day now. Except… this one had one extra line added. “Wear something with a full skirt today!” What did that mean? Why? Wearing a skirt was a given now – he had no other clothes anymore except women’s clothes. And the way things had worked out, dresses and skirts worked the best for him – they helped hide the bulk of his diapers. Not to mention that she had restricted the number and style of women’s pants that he could own anyway.
Having no clue why she should specify a full skirt, he gathered his three required baby bottles from his refrigerator and carried them out to his only chair. Gingerly, he sat down and put the first one to his mouth as his eyes wandered over the childishly colored pictures she had made him create in the restaurants. But he had seen those pictures enough now that he barely noticed them anymore. Why a full skirt? And… which one should he wear?

Mel stirred his baby cereal in the pot on her stove. She glanced at the clock. – it was almost time for him to be here. The knock on her door was actually two minutes early. She turned the stove off and went out to open it.
“Good mowning Mistwess,” Chad said in his sissy voice as he curtseyed for her.
“Good morning Sissy,” Mel replied as she stood back out of the way to let him inside. She waited till he deposited his diaper bag and purse under the table she kept by the door. Then she looked him over. His hair was styled – good enough. His makeup looked – acceptable. She noticed that he was wearing the pink ear studs again today along with the rest of his pink jewelry. She could tell from his shape that he was wearing the required two diapers, waist cincher, and all-in-one girdle under his clothes. His reddish brown blouse was frilled along the entire neckline and went well with the colorful pattern on his skirt. And on his feet he was wearing a pair of brown ankle strap heels. Overall, he looked… not too bad – for a guy wearing women’s clothes.
She reached out and pulled his skirt to the side, seeing how wide it would go. Very good.
“This is the fullest skirt I had,” Chad said in his sissy voice as she pulled it to the side. But the moment he opened his mouth to say it, she got mad and rushed off. Chad knew he had messed up before the words were completely out of his mouth. All he could do was to curtsey as she rushed back toward him, her thick yardstick in her hands. “I’m sorry Mistress,” he said in his sissy voice. “I forgot.” There was nothing he could do but to stand there and accept the blows from her stick as she hit him on different parts of his body.
“When are you going to learn to curtsey every time you open your mouth?” she said angrily as she hit him. Chad made no reply.
“One way or another, you’re going to learn!” she said as she offhandedly hit him two more times. “Now get in there and get up in your highchair!”
A few minutes later, Chad was trying to shovel horrible tasting baby cereal into his mouth, using a tiny baby spoon held in his left fist, while he was sitting in his highchair wearing a bib.
Mel poured herself another cup of coffee and leaned back against the counter to watch him like she usually did. “I’m glad things went better with Robin yesterday than you thought they would,” she said.
Chad looked up from his breakfast. “I’m not sure it was good at all! She was so angry – even when she left yesterday.”
“I would say that ‘not getting fired’ is something good.”
Chad nodded. “Yeah! That part is a big relief!” He dug another spoonful of the mush out of his bowl.
“I want you to keep telling me about every little thing she says and does with you today. Like yesterday, if anything happens, I can’t help you if I don’t know what’s going on.”
Chad shrugged, which caused him to spill a bit of the baby cereal already on his spoon. “That should be no problem… unless she makes me keep my thumb in my mouth all day again. It’s really hard to type like that! And I still don’t know why she did it!”
Mel wasn’t exactly sure either. “Just make sure you keep doing whatever she says! And don’t forget to apologize to her as soon as she gets there!”
Chad said nothing as he shoved a bit more of the lousy tasting cereal into his mouth. The apology she had made him practice over and over again last night. He still wasn’t sure he would really go through with it – at least not quite like Mel wanted him to.
As soon as he had finished his breakfast, Mel released him from his chair, but she didn’t let him go to work yet. “Let me see your apology for Robin again,” she ordered.
Chad inwardly groaned. He dropped a small quick curtsey to Mel first – just in case. Then he launched into his little “routine” for Robin. He grabbed his skirt with both hands and dropped into as nice a curtsey as he could…
“No! Spread that skirt as wide as it will possibly go. I want it flared as much as possible! That’s why I asked you to wear it in the first place! Now do it again!”
Chad grunted, then dropped yet another little curtsey for Mel – just in case, then he tried it again. He grabbed his skirt and dropped into his curtsey again – this time pulling wide with both arms as far as the skirt would let them go.
“Better!” Mel commented. “Much better!”
Chad bowed his head momentarily, then he rose up again and brought his feet right together next to each other and clasped his hands in front of him. Then he launched into his little speech. In his sissy voice he said, “I’m sorry Robin that I didn’t do exactly what you told me to do yesterday. I promise not to give you any more trouble and to do whatever you say from now on.” Once again, he dropped into another curtsey, spreading his skirt as wide as possible and bowing his head, before he got back to his feet again and put his hands together in front of him. He turned to Mel and curtseyed. “Was that good enough?” he asked.
“Do it again,” was Mel’s only comment. She made him go through it four more times, just to make sure he had it down perfectly. “Now don’t forget. You do it exactly like that. And this time, use your sissy voice too. No sense practicing it this way and then messing up by doing it differently. Got that?”
Chad curtseyed. “Yes Mistress.” What else could he say?
A few minutes later, Mel watched him driving off toward work. She went back into her house and turned on her laptop. As soon as it was ready, she opened up her email program and began working on an email for Robin. “Okay,” she said out loud to the empty room. “Now we’ll see what we’ll see! Let the games begin!” And with that, she made a little flourish with her hand, and hit the send button.

Robin parked her car, gathered up a load of different things into her arms that she “might” want during the day, and headed in toward the building. She didn’t see Chad’s car yet, but that didn’t mean that he wasn’t here already. Her problem this morning was that she still wasn’t sure what to do about him – or how she should go about even talking to him. She wasn’t even sure she really wanted to talk to him yet… if ever. So she wasn’t really looking forward to seeing him again.
She had made the stupid jerk spend several hours yesterday afternoon sitting with his thumb in his mouth. And the idiot had actually done it! Well, he had deserved it! He wanted to be a baby? Served him right! She had been in no mood to be played with yesterday. She still wasn’t, but she was at least thinking a bit clearer today. It still galled her what a stupid pervert the guy had turned out to be – and she never had a clue! Imagine, wanting to be somebody’s… slave! The idiot! And he wanted to be a baby too? The two just didn’t jive in her mind. Not that anything about him did anymore.
As she approached his cubicle, she slowed her steps a bit. With a rather angry look on her face she looked into his cubicle as she walked past – and breathed a sigh of relief. The jerk wasn’t in yet! Maybe he’d stay out the rest of the day… wishful thinking.
She dropped her load of things onto her desk. Rummaged through her bag till she found her mirror and checked her face and hair. Stowed her bag into her desk drawer, and turned on her computer. Just a normal day, she tried to tell herself. But she knew better.
It took a few minutes for her computer to fully boot up. When it did, she opened up her email program that she kept open all the time. She was surprised to see an email from Mel – already! What did the crazy woman want now? Did she dare open it? But opening it was a foregone conclusion.

Dear Robin

I’m just checking to make sure that Sissy really did apologize to you “properly” as soon as he arrived today.

Please let me know as soon as he does – or doesn’t!

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

Apologize? Robin remembered from a previous email yesterday that she should expect a “proper” apology from him. Whatever “proper” meant. But so far, the jerk hadn’t showed up yet. Fortunately! She closed the email and opened up the internet to check the weather.

Chad knew he was running a few minutes behind, so he was fairly sure that Robin would be in already. He didn’t see her as he approached his cubicle, but that didn’t mean anything since her cubicle was beyond his. Treading lightly, he entered his cubicle. He wasn’t even aware of it, but he was trying to make as little noise as possible so as not to anger Robin, or even alert her that he was here. He stowed his purse in his desk drawer and closed it quietly. Then he sat down gently, as much from trying to be quiet as in difference to his still stinging backside. He started logged into his computer and was alarmed at how noisy the keys on his keyboard seemed to make.
“Sissy!” Robin’s voice called angrily over the wall between them. “I hear you in there! Are you supposed to apologize to me?”
Well, he knew he couldn’t avoid Robin forever. “I’m just booting up my computer,” he called back, looking for an excuse to delay things.
“According to your… mistress,” she spat, “you’re supposed to apologize – first thing! So by my book, that means first – before you do anything else!”
Chad gulped. She still sounded awfully angry. Would she make him sit here all day with his thumb in his mouth again? He hoped not. Instead of answering, he hurried out to see her.
Robin didn’t even know why she cared so much. Well, the jerk probably should apologize to her – for a multitude of things! Not that she was really in any mood to accept an apology from him. Still… She saw him coming around the corner and starting to enter her cubicle. “Stop right there!” she ordered quickly. “I don’t want you that close to me. Back up!”
Chad was surprised. Back up? But he backed away from her till he was just out of her cubicle.
“Further!” Robin ordered. “Like… the middle of the hallway, at least.”
Chad looked around, fortunately, he didn’t see anybody coming. He backed up further.
“Now. I guess I’m supposed to listen to some kind of stupid apology from you? So let’s have it so I can stop looking at you. Not that I’m probably going to believe anything that comes out of your mouth,” she muttered.
Chad was a little taken aback by her attitude, but he was supposed to apologize, so he figured he better apologize. He just didn’t see himself doing it quite the way that Mel wanted him to. Once again, he looked up and down the hall to see if anyone was coming – fortunately not. He wasn’t about to give her the full version, but he did drop a quick little curtsey for her as a start. “I’m sorry Robin,” he said in his girly voice, “for taking my thumb out of my mouth yesterday after you told me to keep it there.” Should he add any more? It was already more than he wanted to say, but he figured he better add one more little thing that was – sort of – what Mel wanted. “I promise I’ll try to do better and listen to what you want from now on.” Then, since he had no better way to show that he was finished, he dropped another quick little curtsey. He watched her just staring at him. Was it enough? Could he go back to his desk now?
“Huh!” Robin grunted as she shook her head. “Listen to what I want? I don’t want to see you! Get out of here!” She purposely turned her back to him, hoping he would get the point.
Chad was just glad it was over and hurried back to his desk. As soon as he was done logging into his computer, he decided he had better tell Mel about Robin’s reaction.

The Bet - Chapter 45 (Monday – week 7 Part 7 of 7)

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 7 of 7)

Instead of having him practice his ballet, Mel had him keep busy with cleaning the apartment instead. But every few minutes she called him back to practice his little apology for Robin again. She enjoyed watching him, she just wished she could be there to see it in person.
But finally, watching him curtsey for her over and over again had enough of an effect on her. She got up from her seat in the living room. “Strip down to your diaper and nothing else!” she ordered as she headed for her bedroom. Chad did just that, but not before curtseying one more time, even though she was walking away from him. It was better to be safe than sorry!
It took him only a few minutes to get himself down to just his diaper. Removing his bra left his glued on breast forms hanging from his chest with no support. They felt all too awkward and heavy that way as they pulled against the skin of his chest. Removing his waist cincher though was perhaps his biggest relief. The darn thing was all too tight and confining. He had a vague idea of what would be happening next, but knowing Mel, he dared not make too many assumptions.
She was gone a while, but eventually, she called him into her bedroom. When he got there, she was holding one of her scarves in her hand. Out of the corner of his eye, he noticed some ropes attached to her bed, but they were mostly pushed out of the way. The minute she approached him with the scarf, his assumptions became confirmed. He curtseyed to her – just because he dared not do it.
“I’m going to put this on you again,” she said, “and I’m not going to tie you up… yet.”
That surprised Chad a bit. He had already seen the ropes attached to her bed. But then she did say… “yet.”
“But so help me. If you even do anything to take this off – or if it somehow even falls off, then I’ll make sure you’ll regret it for a very, very long time!”
The way she had said it left him in no doubt, and his thoughts instantly went back to the beating she had given him earlier. His backside still burned terribly. He curtseyed. “Yes Mistress.” What else was he going to say? That he was going to do everything he could to get a look at her gorgeous naked body? He knew better! It wasn’t going to happen! Never once in their relationship had he been allowed to see her naked. He had only been allowed to touch her. But just touching her was reward in itself. She felt so… beautiful! A moment later his sight was totally cut off as Mel tied the scarf tightly around his head – then she pulled on it again, making sure it was extra tight and secure.
Finally feeling satisfied that he couldn’t see her, Mel began undressing. She still didn’t understand her strange aversion to him seeing her naked, but after all this time, it was just something that she accepted. She climbed up on the bed. “Make love to me,” she told him. It was Sissy standing there wearing nothing but a diaper, his breast forms hanging oddly from his chest – but it was Ray she was trying to picture in her mind. Ray, who had driven her wild in the movie last night. Ray, who she would be going out with tomorrow night. Sissy would be nothing more than a warm up before Ray. Something to take some of the edge off of her… anticipation.
Chad groped his way toward the bed, then up onto it. He felt for her body and his hand connected with her naked breast. Surprised, he kept it there as he brought his body over to lay close to her. The skin on her breast felt so soft, so smooth. He moved his hand over it, lightly flicking the nipple with the tip of his finger. He allowed his hand to roam further, feeling more of her. She felt… wonderful! Unable to help himself, he got to his knees next to her so he could feel her whole body with both hands. He allowed his hands to roam in opposite directions, sliding ever so tenderly over her ever so smooth skin. He heard her moan and felt her writhe slightly. The feeling of her was exquisite! And he was only using his hands! Having his sight blocked off allowed him to truly feel how wonderful she felt. It allowed him to concentrate harder on the things that were really important. He allowed both hands to probe, and squeeze, and caress, drawing as much pleasure from it as she did. The only thing was, that sexually, he was completely denied any reaction. All he received sexually was frustration. But he was so very glad that she was enjoying the full benefit of his touch.
Mel writhed and whimpered softly as his magic hands worked their way over her entire body. There was just something so sensual about his touch. Several times his one hand found her ever moistening sex and lingered there for a moment, but it was only a moment, leaving her hungry for more. The fingers of one hand seemed to grab her breast a bit firmer just before she realized he was lowering his head toward it. She was struck but the odd sensation of his breast forms, both of them, rubbing firmly against her other breast, stimulating it. But that was only a side sensation. She was more interested in watching as the hand on her other breast guided his mouth directly to her nipple. He sucked on it for a moment, like a baby? Then his mouth pulled away slightly and she felt his tongue flicking lightly over the tip of it. Her breathing quickened – especially when his other hand found her dripping sex again – and stayed there. She arched her back as his fingers began probing deeper – deeper but still lightly. As if teasing her. Making her want more… more… more! Moments later, she was rocked by her first orgasm. Exquisite!
Chad let her come down slowly from her orgasm. But before he could do anything else, he felt her hands grabbing his hair, pushing his head down between her legs. He resisted, but only to the point where he could move his body, climbing over her carefully to position himself better. But her hands never quit their grip in his hair, and as he dove down with his tongue into her, he felt her pulling his head harder and harder into her. He couldn’t see them, but he felt her legs writhing over his body on both sides, one of them moving up and down his back. Her second orgasm came fast and much stronger than the first.
Mel’s blurred vision stared at the ceiling, but she had no interest in seeing anything. All she was interested in was how good Chad’s talented tongue felt as it still worked away at her. She felt momentarily spent after her orgasm, but that didn’t matter. All that mattered was how delicious Sissy felt as he continued to stimulate her so wonderfully. He was going slower now and she let up a bit on her grip. She hadn’t realized she was pulling on his head so hard. She allowed herself t take a deep breath and close her eyes, the better to enjoy everything she was feeling. Heaven! And slowly, ever so slowly now, she felt her next orgasm building again. The only thoughts capable of getting through to her now were the feelings that she felt throughout her entire body.
Chad kept at her till eventually she had one more orgasm. He had gone slower that time, much slower. As she came down again, he was aware of her breathing slowing down, her legs on each side of him calming, her entire body seeming to relax. He felt her pulling on his hair again, but it was in a different direction, pulling him away from her. He pulled his head away, and climbed off of her, once again laying next to her. He put his arm over her and held her as she continued to relax more and more. Such a pleasure. He couldn’t help but wonder though at what it was that she felt. Women were capable of having orgasm after orgasm, while he was capable of… nothing. But that didn’t mean that he didn’t enjoy making her feel good. Worshiping her body by just touching her. He felt… honored that he was capable of giving her the pleasure that he could. He might not be any good in the ways that most men were, but at least he could do this much for her.
He felt her moving, rolling over on top of him. The weight on his breast forms was crushing, but he didn’t care. He felt her head come down next to his and he felt her lightly kiss his neck over and over again. If he had been any kind of a man, he knew that his useless penis would have responded quickly. But… he wasn’t that kind of a man. Not anymore. Not since she had locked away all of his main source of pleasure.
He felt her moving off of him again to his other side, kneeling next to him, just as he had been kneeling next to her a little while ago. Something tugged lightly at one of the breast forms glued to his chest, and he realized she was rubbing her hand lightly over it, just as he had done for her.
“Do you feel that?” she whispered. “Does that feel as good for you as it does for me?”
How could he tell her that all he really felt was the light pulling and pushing as the breast form tried to move under her hand. But he said nothing at all. He felt her hair tickling his chest, and realized she was kissing what would have been his breasts if he were a real woman. It was an odd sensation, totally useless in its intent, yet oddly stimulating never the less.
He felt her pull her head away from him again. “Scootch over a bit, this way,” she said as she moved back, and finally off of the bed. She pulled on his arm till he was laying on the very edge of the bed. “Stay there. I’ll be right back… And don’t fall off!”
He heard her leave. She was gone a short while. Then he heard her back again and doing… something. Something that involved the bed. He could feel her on the other side of it, doing… something. Then she was back again, right at his side. He felt her grab his arm with one hand while her other hand touched his body.
“Roll over to the other side now,” she instructed as she pushed lightly to guide him.
Chad rolled over onto his stomach and started moving his body sideways toward the other side of the bed. He quickly discovered that what he had felt her doing was protecting her bed. His hands encountered multiple thicknesses of diapers under his entire body.
“Okay,” she said as he reached the spot she wanted him to be in. He stopped and started to roll over onto his back again. “No,” she told him. “Stay face down.” But the position wasn’t quite what she wanted. “Up on your hands and knees,” she ordered.
Chad did as instructed, but now he was getting confused. On his hands and knees? He felt her hand on his back again as she told him to move forward a bit toward the head of the bed. He crawled forward slightly, then more, till she told him to stop. A moment later, she was pulling open his soaking wet diaper and removing it. The air felt cool and odd as it caressed the parts of him that were forever packaged inside of the warm diapers. A moment later he realized he was involuntarily peeing as the cool air stimulated him. He heard Mel laughing as she stood by and watched. As used to it as he already was, he felt embarrassed by his lack of control.
He felt her moving up towards his head more, and a second later he felt her tying the rope to his wrist on that side. She moved back and fastened his ankle next. Then she moved around to the other side of the bed and bound that side of him. He had to wonder why. He certainly wasn’t planning on going anywhere. And bound like he was he could still stretch out and lay down easily. But… it was her game.
He could hear her moving around near him, but he couldn’t tell what she was doing. Not till he felt the cold shock of her hands full of lotion suddenly rubbing all over his still hurting backside. But this time the hurt died quickly and was replaced by more and more pleasure, especially as she purposely moved closer and closer to his waiting back hole.
Mel let her finger slip slightly inside of him, and saw the immediate reaction as his whole body stiffened. He loved this. Well, tonight she wasn’t going to disappoint him. She played with him there for a minute, moving her finger in and out of him – as much to spread the lubricant as for his enjoyment. Then she pulled her hand away again.
On her nightstand, she had already selected one of the colorful dildos to use on him. The one with all the swirled ridges along its length. She picked it up and placed it against his asshole. His sudden intake of breath was obvious. So was the stiffening in his entire body again. She held the toy there for a moment, but she couldn’t keep it there long as he started pushing back toward it, wanting it, almost more like needing it. She let him have it, but only a little at a time. But the further it went into him, the harder it was to grip the toy, especially since the swirled ridges on it were acting like screw threads and the whole thing kept trying to turn around in her hand. She held on tighter though and he soon loosened up so that it wasn’t as much of a problem.
It seemed like no time till he was pushing and pulling like crazy against the toy in her hand. He seemed… desperate in some way. And she supposed she understood that – seeing as how she had completely denied him any chance of an orgasm. She was simply amazed at how desperate he seemed to be, pumping himself, screwing himself, fucking himself against the toy in her hand. But before long, she saw him shake his head again and he slowed down further and further. With the toy still buried half in his backside, he finally moved his hands forward and slumped down on his elbows in defeat.
She was disappointed that he didn’t try longer. But she understood that. Maybe… maybe he would enjoy a different toy? She opened her drawer and began sorting through all the different options available to her. Colorful options and… oh… Her eyes fell on the strap-on dildo she bought to use on him… but had wound up strapping to him and using it on herself instead. The thing had a small side that was supposed to stimulate her too. Would it work? Only one way to find out.
She pulled it out of the drawer, found the smaller end and fastened it to the back of the device. Then she set about fastening it to her. It was an odd process and it felt odd around her hips. It especially felt odd from the part that was buried inside of her. But now that it was there, she was starting to get sexually stimulated again. The odd fake penis stuck out in front of her strangely. As she moved around, it accidentally bumped against the side of the bed, stimulating the inside extension in the process. She found that very interesting!
He was still slumped down on his elbows. She didn’t want that now. “Get up again,” she ordered and waited till he had once again gotten to his hands and knees. But she didn’t want him to slump down again. She found two more lengths of rope, but before she used it, she grabbed one of his wrists and pulled it out to the side, pulling it against the rope holding it to the headboard, until she could place his hand on top of the phallic piece sticking crudely out from her groin. “Feel that?” she said. “That’s for you!” She wanted him to know what was about to be done to him. She wanted him to know that he was about to get screwed – like a woman!
She grabbed the rope then and tied his wrists to his knees on both sides. Now he couldn’t move his hands or his legs forward or back. He would be stuck in the position he was in. Perfect. Just the way she wanted him.
She climbed back up on the bed behind him, but the fake penis sticking out from her was harder to deal with than she thought. She had to maneuver around just to get it close to his asshole and she kept bumping and scraping it against him in the process. How did men manage to do anything with these things? And then it was even harder to get it exactly right and control how she wanted to push it into him. She had to use her hands to guide it into place and hold onto it. Then she pushed lightly with her hips till it finally slipped partially inside of him. Only then did she release her hands and grab the sides of his body instead. She could feel the pressure from the little piece inside of herself, but concentrating on it as well as what she was trying to do to him was difficult. Slowly and carefully, she pushed the fake penis attached to her inside of him.
Chad was a bit scared. Yes, he loved having her play with his asshole. Yes, he loved all her toys. But this… this seemed different. And once the damn thing was inside of him, it felt bigger, fatter than any of her other toys. He felt her pushing it slowly into him, further and further, more and more. He was just glad he was already so loosened up from her previous toy. And then he felt her pulling away again, pulling away with her body. And the toy that was in him was obviously moving with her body. It was such a strange sensation. Several more times he felt her pushing slowly into him all the way, then pulling back again, almost all the way but never quite removing the crazy thing.
Mel thought she had the hang of it now. It wasn’t really so hard at all – once she had gotten it into him. And yes, she did feel something from the little piece inside of her – and it really felt pretty good. Certainly not like anything real, but it was… interesting. Somewhat stimulating too. As she moved slowly back and forth, she could see him relaxing more and more, getting into it more and more. She leaned over him now, the new position made it harder to pump against him, but she kept going anyway as best she could. She reached under his chest and began fondling one of his breast forms. “Do you like this?” she asked. “Can you feel me playing with your tits the way that you play with mine?” She almost giggled. She was fairly sure he couldn’t feel much from his fake breasts at all – but you never know. “Does this make you feel more like a woman now? A real woman?”
Something about her words hit a nerve inside of Chad. He shuddered involuntarily at the thought and clamped down a bit harder on the phallic device inside of him as he began trying to actively pump back and forth against her – increasing the pace a bit.
Mel noticed his reaction, especially when he began speeding things up. She figured she must have said something that interested him. She almost giggled. She had wanted to imagine it was Ray making love to her earlier, but once he had started, she could only think of Sissy instead. So maybe… She leaned close to his head again and whispered. “Can you imagine that I’m Derek, and this is what Derek would be doing to you?”
Derek? Derek making love to him – like he was a real woman? Derek fucking him – like a real woman? But the feeling of the fake penis being pumped in and out of him made that scenario all too real and easy to imagine. He involuntarily felt his body tighten as that thought increased his sexual energy.
Mel noticed the change once again – and continued. “Can you remember Derek holding your hand in the movie? Dancing with you in the restaurant? Did you feel like a real girl then?”
Her words were having a profound effect on him, and he couldn’t help it. As much as he didn’t want to respond to them, he just couldn’t help himself.
“How did it feel to have Derek hold you in his strong arms as you were dancing? How did it feel when he hugged you so tightly when he said goodnight?”
Chad had no control of it anymore. He was pumping harder and harder, trying to feel more and more from the fake cock inside of him. He was being held and taken from behind by a living human body, and her words were sending images and feelings to his brain that he didn’t want to deal with in normal life. He was getting lost in her words and ideas and in all the many sensations. And it was building bigger and bigger, taking him further and further. Leading him towards…
“How did it feel when he pressed his lips up against yours and kissed you like he did?”
He could once again feel Derek’s soft lips pressing against his own, kissing him passionately. Derek’s strong arms were around him holding him tightly. He could again taste the thick lipstick on his own lips. He was helpless in Derek’s arms. Soft lips kissing his own. A man’s lips kissing his lips – like a woman…”
The strong almost cramping feeling may have begun at the base of his spine, but it quickly spread up and down throughout his entire body, from his toes to his fingertips. Even though Mel was still pumping in and out of him, he couldn’t move as all his muscles locked up tightly – then they suddenly started shaking – all of them! It felt like his whole body was straining in every direction at once. And the yell that finally escaped his throat was strained and high-pitched – and seemed to go on, and on, and on.
Mel was frightened at first, but soon her fright became amazement as she realized he was actually orgasming. She did her best to lean over and see just how bad his chastity device must be hurting him, but from everything she could tell, his trapped penis inside was just as tiny as ever – but there was liquid pouring out continuously from the device – and she could tell it wasn’t pee! Incredible! Incredible! Incredible! In many ways, she had just made him cum – as if he were a woman! A female! It was like stripping yet another layer of masculinity away from him. And as his own shaking started to come to an end, the added realization of what she had just done to him sent her over the edge one more time herself, except that this time, she was the one buried inside of him. She had no option but to pump harder in and out of him as she rode her own orgasm to its conclusion – which only caused him to keep pumping desperately in response.
It was a few moments before either of them could slow down – let alone settle down. It was an experience that Mel figured she’d never forget. She still didn’t believe it had just happened. Breathlessly, she slowly and carefully pulled her attached phallus out of him. She had taken him like a man – and he had responded like a woman!
Chad didn’t know what to think. He had finally had an orgasm… he thought. Although in truth he had never really felt anything like it – ever! Was it possible? He hadn’t thought so before, but now… Images of Derek kissing his lips again still swirled though his mind. He couldn’t stop them. He wasn’t even sure he wanted them to stop. Mel climbing off the bed distracted him enough to finally erase them from his mind – mostly.
Mel got down off the bed. She would have untied him, but she wanted to remove the crazy strap on device first and put something on to cover herself. As she was just starting to unbuckle the device, she heard a faint splashing sound. She looked over at him and saw a strong stream of pee rushing out of him again, splashing straight down onto the diapers protecting the bed below him. It puddled there a bit before starting to sink into the absorbent material. She smiled at the sight of it. In so many ways, it was hard to believe that he still had any control. Twice tonight she had seen signs that made her feel like she was winning this bet, but she knew better than to trust everything she saw. How long had he managed to hold back at work today? She had no way of knowing.
Chad felt so embarrassed as he realized he was peeing uncontrollably again. Actually, after what he had just experienced, peeing had been the furthest thing from his mind. Had he actually orgasmed? He was pretty sure. Yet the way it had happened – while feeling really great, had also been very embarrassing. What had happened to him? No, what was happening to him? Because the changes still seemed to be happening. But there was one other thought that seemed to lock onto his mind that he couldn’t shake – what he had once thought of as impossible, had just happened. It was possible! He had thought he could never orgasm that way, but he just had! But as his peeing came to an end, that thought led to one other thought – a very troubling thought. If the impossible was now possible, how about with their bet? He had thought before that Mel making him totally incontinent in only two months was completely impossible. But now? He still believed it couldn’t happen. Not at all. But… but now there was a tiny seed of doubt.
With her robe fastened tightly around her, Mel removed the ropes that held him in place. Then, while he was still on his hands and knees, she removed the scarf she had used as a blindfold on him. For no other reason than to be nice, she pulled away the wet diapers that were under him. “Roll over on your back,” she told him. “Let’s get you diapered again before you pee all over everything.”
Chad rolled gratefully to onto his back. He felt a mixture of pleasure, fatigue, and embarrassment. A moment later he felt a wave of frustration as Mel took out a jar of suppositories and shook it in front of him. “We can’t forget these,” she teased. She opened the jar and pulled one out. Chad turned his head away in disgust the moment he saw the capsule shaped pill. What Chad didn’t see though was Mel letting the suppository slip back into the jar as she put the lid back on. “Okay, raise up,” she ordered. Chad pulled his legs up high, exposing his bottom for her again. Mel stuck her finger way up inside of him – as if she were really sticking the pill up there. Once again, Chad never knew. But this was the second time today that his suppository had been faked. Her plan called for him to gradually get less and less as time went on now. But her big question was, would it make a difference? She could only pray that it wouldn’t. Just as she didn’t really know what kind of control he had over his peeing, there was no real way she could tell what would happen once she stopped the suppositories completely. And there wasn’t a lot of time left in this bet!
A short while later, clad in only the over-stuffed padding of four disposable diapers. Chad curtseyed one last time for her and gathered his things and took them home. Once again, Mel stared at the back of her closed apartment door after he left. Time was running out. Things always seemed to come down to time – precious time. Would she make it? Would she really do the things she bet him she could do? It had been a crazy bet from the start. A really stupid bet. She blamed it on too much beer that day. But the truth was, there was something else. Something else inside of her that must have realized she wanted to do this… maybe, needed to do this. But still, would she make it? She had to. She just had to! She couldn’t dare lose him. She didn’t want to contemplate what it would be like without him.

“Goodnight Sissy,” she whispered again. “Goodnight.”

The Bet - Chapter 45 (Monday – week 7 Part 6 of 7)

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 6 of 7)

Sandy felt like she was letting Mel down. Besides, she absolutely loved watching Sissy make such a fool of himself – especially as a baby – so she guessed she was disappointed for herself. But tomorrow night was out. She and Cassie had plans and there was no way she could watch Sissy for Mel. Unless… Unless… She and Cassie were just going to visit some friends for the evening. What if they agreed to let Sissy come too? Now that she thought of it, the more she liked the idea – really liked the idea!
She picked up her phone and called Cassie to see what she thought, then she called one of her friends to get her opinion. No problem! Finally, she dialed Mel’s number.
Mel was just driving home from work when her cell phone rang. With one hand, she quickly dug it out of her purse and answered it. “Hello?”
“Hi Mel, it’s Sandy.”
“Hey Sandy. What’s up?”
“Did you ever find someone to take care of Sissy tomorrow night?”
“No!” Mel answered, totally frustrated with the problem. “Got any ideas?”
“Maybe one… if you’ll agree to it.”
Agree to it? That sounded fairly ominous. Especially knowing Sandy. But she was desperate. “What did you have in mind?”
“Well, Cassie and I are just going to visit some friends tomorrow night and… well… I thought that maybe Sissy could come with us.”
Mel wasn’t too sure about the idea though. “Don’t you think your friends will object to someone like Sissy being there?”
“Oh no! They’re very… open minded. In fact, they’re both a bit… wild!”
Wild? That shook Mel a bit.
“But don’t worry,” Sandy continued, “I already checked with them and they said they didn’t mind at all.”
Mel was still trying to contemplate what wild meant. But desperate was desperate! “Um… I guess it’s okay, as long as they don’t mind. But Sandy, the real reason I need someone to watch Sissy is to make sure he keeps wetting as much as possible. You know, like with the time limits I put on him. Do you think they’ll mind that too?”
Sandy giggled. “No problem! I already told them about Sissy. In fact, they’re looking forward to seeing him. But don’t worry, just because they’re a bit kinky, they’re still good people.”
Kinky? “Um… I’m sure they are,” Mel replied. But she also realized that Sandy had already been through and checked with everyone. “Then I guess I don’t see any problem at all. Especially if you can make sure he keeps to his schedule. In fact, I appreciate it a lot!”
“Great Mel!” Sandy replied enthusiastically. “And I was thinking, maybe we could even offer to let Sissy cook us all dinner too?”
That part didn’t really bother Mel in the least. “That’s fine. He seems to like showing off his cooking talent.”
Sandy laughed. “It’ll be great! I can’t wait to show him off in that silly baby dress to everyone… Oh, hey! Gotta’ go! Talk to you later!”
Mel was suddenly left with an empty phone connection. Sandy wanted him dressed in his baby dress? What kind of evening did she have in mind? She now didn’t know if she was worried… or if she wanted to be there just to share in the fun!

Chad glanced at the clock. Mel was running late. But more importantly, he was worried about how much time he had till his diaper had to be leaking. He already knew that Mel would be home shortly. He also knew he was going to get a beating tonight for taking his thumb out of his mouth earlier with Robin. He didn’t want to make things any worse by not getting his diaper to leak when it was supposed to. So he was drinking furiously from his third baby bottle now since he had gotten home.
He heard the apartment door opening and he rushed out and saw Mel just coming in. He curtseyed. “Welcome home Mistress,” he said in his sissy voice.
Mel smiled at seeing him curtsey and hearing his silly sissy voice. The aroma of something good cooking in the kitchen filled the apartment too. “Thank you Sissy,” she replied as she set her things down on the little table by the door. When she turned back again, Chad was hurrying away back to the kitchen. She followed after him. “Something smells good,” she said as she watched him hurrying to the stove where he grabbed a large spoon to stir something in a pot.
“Thanks,” he replied as he set the spoon down again. “Dinner will be ready in just a moment.”
Mel shook her head. “I’ll be adding five more swats to your punishment tonight for not curtseying before speaking to me just then!”
Chad was shocked. He had been busy cooking! And she still expected him to curtsey every time he opened his mouth? Ugh! He curtseyed now. “Yes Mistress,” he replied sullenly.
Mel noticed that the table was very nicely set already. “I’ll be right back,” she said to him as she turned and headed toward her bathroom.
Chad dished out her meal. But it was only a meal for one. He hadn’t bothered to make any for himself since she had declared that he would be eating mostly baby food from now on. There was a whole cabinet full of it that he didn’t even want to look at. Mel came back as he was looking everything over one more time to make sure he hadn’t forgotten anything. This time he remembered to curtsey first. “It’s all ready Mistress,” he said as he stood back.
Mel smiled and sat down. Everything looked so nice. The food smelled so good. All that remained now was… “Sissy, back to your perch!”
He had been expecting it, but he still hated to hear her say it. He quickly grabbed himself one more desperate swig from his latest baby bottle, then headed sullenly back to his little corner where he climbed up onto his perch. His body was pressed up against both walls. The only thing he could see was the blurry vision of the two walls. He closed his eyes and tried to concentrate on staying as still as possible. Back in his little corner. Back up on his perch. Back to being out of sight and out of mind. Back to being – bored!
Mel ate leisurely as she watched him up on his perch in the corner. Dinner was excellent! He wondered what he would be cooking for Sandy and her friends tomorrow night. Whatever it was, she had no doubt that it would be something good. He didn’t know about that yet and she wondered if she should tell him or not. She decided to keep it from him for now. It wasn’t something he needed to be worrying about – yet. And knowing Sandy, maybe he should be worried! Sandy wanted to show him off in his baby dress? Her friends where wild? Kinky? She had a lot of mixed feelings about that. But mostly, she was jealous that she wasn’t going to be there herself.

Bored, bored, bored, bored, bored, bored, bored! Boring corner. Oh! I’m peeing! Excellent! Yes! Feels great! Is my diaper leaking? Leak! Leak! Leak! Please leak! Nothing… yet. Got to pee again! Got to start leaking! Need more to drink, but I can’t if I’m stuck here in this boring corner. How long have I been here now? How much longer? Isn’t she done with dinner yet? Ugh! I’m tired of this. My calves ache! My toes are all scrunched and hurt. I want to move them. I need to move them. But I can’t move them. There’s just no way. Stuck! Ugh! Want to move but I can’t. How much longer? Need to pee again! Come on! Pee, pee, pee!

Mel got up from the table and opened the cabinet that now held all his baby food. There was a lot to choose from. She started taking down jar after jar to see what it was. Gradually, she built a suitable dinner for him as she set the jars she wanted down on the counter. She grabbed a plastic child’s plate from another cabinet along with one of his rubber coated baby spoons. Then she opened jar after jar and dumped out the colorful mush onto the plate. When she was done, she was tempted to mix it all together into one big mushy pile, but she didn’t.
“Okay Sissy. Get yourself over here.”
Chad gratefully pulled himself off of his perch and stretched his legs and feet before trying to walk. He was just glad to finally be out of the corner again. He was especially glad to finally be off of his perch again. By the time he got to the kitchen, Mel was holding the tray to his highchair in her hands and was waiting for him to climb up onto it. He headed for the chair, but he saw a sudden look of anger in Mel’s eyes. He stopped and curtseyed to her again. He was relieved to see her smile. Only then did he climb up into his chair. She pushed the tray into place, locking him into the chair. Then she tied a bib around his neck. She delivered his dinner to him along with the tiny baby spoon. And finally, she put his latest baby bottle down on the tray for him to drink from. He grabbed the baby bottle first because he had to meet his leaking deadline.
Mel poured herself another cup of coffee and leaned back against the kitchen counter to watch him eating as she often did. “So it looks like you’re not going to get fired after all?” she asked.
Chad stopped eating momentarily and sighed with relief. “It looks like it anyway. Robin said she didn’t tell anyone.”
Mel smiled. “That’s good.”
“She was just so angry at me!” Chad said as he dipped his little spoon into some orange colored mush.
“What did you expect?”
Chad shrugged before stuffing the colorful food into his mouth. The action made him miss a bit and some of it spilled down onto his chin.
Mel chuckled. Actually, it was the first food he had spilled so far.
“I was hoping it would go a little better,” Chad finally said as he dipped his spoon back into his food again. He suddenly looked up at her. “And where did this sticking my thumb into my mouth thing come from?” he asked.
That was the part that had surprised Mel too. Surprised, and delighted her. But she wasn’t going to tell Sissy that. “I don’t know,” she replied. “I honestly don’t know.”
Chad went back to eating – and wondering what had gotten into Robin.
“Tomorrow night,” Mel said, surprised that it had come out of her mouth because she wasn’t planning on telling him about it yet. “I have a date.”
Chad was a bit surprised. “With Ray?” he asked.
Mel nodded. “Yes. With Ray.”
Chad felt disappointed and hurt. But he stopped himself from feeling any worse. Why shouldn’t she go out with a proper good looking guy? Why shouldn’t she have some fun with a real man? Who was he to say what she should and shouldn’t do? She was a good looking woman. She deserved to go out with a real man… not someone like him. Yeah, like she would ever go out with him… a sissy! Looking only down at the food on his plate he replied. “I hope you have a good time.”
Was that… disappointment she heard in his voice? Interesting. “I hope we will,” she replied. “And… I hope you have a good time too.”
Chad looked up quickly. “Me?”
Mel nodded. “You’ll be going with Sandy and Cassie to visit some friends of theirs. From what Sandy said, it sounds like she wants you to cook dinner for them.”
Chad’s surprise turned quickly toward being very interested. Cook them dinner? What should he make? It would have to be something that he knew was really good that would show off his cooking ability. A little problem quickly arose. “Will they be coming here?” he asked.
Mel shook her head. “No. Why would you ask?”
“Because I don’t know what kind of food they’ll have, or what spices they have, or what kind of pots and pans and other stuff they have available. Maybe I should go shopping before then and get everything I need. Then I can just take it all with me. Do you know how many will be there?”
Mel shook her head. “Don’t worry so much about it. I’ll check with Sandy tomorrow and let you know.”
As Chad finished the rest of his meal, he barely noticed anymore what he was eating. His mind was more focused instead on what he could make them for dinner. He wondered if Sandy’s friends were worried about eating only diet food.

While Chad was busy cleaning up the kitchen after dinner, Mel changed into a pair of shorts and a t-shirt. Then she put her ballet music on again and started making notes about what things she wanted to choreograph for Sissy’s ballet. It was slow going, but she was making progress. Her biggest problem was that he knew nothing at all about dancing, and he was absolutely not graceful in the least. But she supposed that none of that was the point. The point was to create something to show off what a sissy he really was… or so she thought. Since she was creating this thing, there was a certain amount of pride in showing off what she was capable of doing.
She glanced at the clock. The time for him to be leaking was quickly running out. “Sissy! Are you leaking yet?” she called from the living room.
Chad had heard the ballet music on her stereo and knew that he would be spending some time dancing again tonight. But that wasn’t her immediate question. “No, not yet.” he replied somewhat forlornly. He was close. He knew he had to be very close. But so far this diaper was proving to be stubborn.
“Did you curtsey before you answered me?” she called back.
Chad could have screamed! “No,” he replied once again with even more disappointment.
“How about then?” Mel asked.
Chad wanted to kill himself. This time he curtseyed, then replied. “No… but I just did then.”
“I’ll add ten swats to your punishment tonight. Better hurry up, your leaking deadline is getting awfully close!”
He knew it. He knew it all too well. There were still a few pots to finish cleaning, but he ignored them in favor of doing nothing but drinking from his latest baby bottle. Pee! Pee! Leak! Leak! It was impossible to try to pee any harder than he was already doing. It seemed like his whole life lately was dedicated to doing just that. With Mel around, it never let up! He briefly wondered about tomorrow night. Hopefully, he wouldn’t have to worry about it tomorrow night at all. That would be a blessing!
He suddenly felt himself peeing yet again. He spread his legs hoping it would help matters, but unfortunately he felt nothing leaking. He glanced at the clock – two minutes left. Pee! Pee! Leak! Leak! But he had just finished peeing. He finished his bottle and quickly grabbed a fresh one out of the refrigerator. He drank furiously from it – just as he had with his last bottle. And miraculously, he felt a tiny bit of pee coming out once again. Leak! Leak! But nothing. It had been too little. In frustration, he began pacing around the kitchen while he drank from his bottle. One minute left. But then he felt something a bit odd. Wetness? He really wasn’t sure. He felt down around the bottom of his diaper and right at the leg opening on one side it felt a bit – wet. Yes! “I’m leaking!” he called out victoriously.
Mel glanced at the clock and saw the second hand tick down to the final second. She smiled. “Did you curtsey?”
Chad really wanted to kill himself.

Chad leaned over and put his arms up against the back of the chair. His totally naked bottom already made an inviting target for the thick yardstick she was holding at the ready in her hands. But it wasn’t what she wanted. Not what he had to do. He had no idea how many times she was planning on hitting him. Fifteen for sure, plus… a bunch more probably. Hating having to do it, he purposely raised his naked backside up even higher, making it the perfect target for her cruel stick. The swish of the stick moving through the air was faster than usual. Smack! Ouch! She had really hit him hard! Wow! With is backside stinging horribly, he stood up and curtseyed. “Thank you Mistwess,” he said in his sissy voice. It was a horrible thing to keep thanking her like that for hitting him. But… what choice did he have? He leaned back over against the chair again and raised his backside up into the required position. Swish… Smack! Ouch!
“You know Sissy,” Mel said as she waited for him to stand up and curtsey again, “one way or another, we’re going to teach you to curtsey politely at the drop of a hat.” She waited while he went though his little ritual and started to get back into position. “One way or another…” Swish… Smack! “We’re going to get you so accustomed to curtseying that you’ll be doing it without thinking anymore.” Again she had to wait while he curtseyed and thanked her. “You’ll be doing it before you do anything!” Swish… Smack! “If I have to, I’ll have you curtsey to every door before you open it… every little thing before you even touch it!”
Chad tried his best to digest that as he once again stood and curtseyed to her. “Thank you, Mistwess,” he said in his sissy voice again. But the shake in his voice was almost as much from the things she was saying as much as the pain he was feeling. He was so preoccupied by worrying about the next upcoming blows from her stick, and with what she was saying, that he didn’t even notice when he started peeing again as he leaned forward to brace himself against the back of the chair.
Mel smiled as she saw the golden colored liquid squirting out from his chastity device. “Well at least that’s one less thing we’ll have to beat you for tonight,” she said just before she swung her stick again.
Chad wasn’t even sure what she was talking about, and he thought even less about it as the sharp stinging blow to his backside registered immediately with his brain, wiping out all other thoughts.
Fifteen strokes, fifteen curtseys. All for not curtseying before he spoke – and each time had been when she wasn’t even in the same room with him. He was just glad to get them over with. His backside was on fire!
“Okay, that was the easy part,” Mel said as he finished his last curtsey and thanked her.
Chad wondered what she meant by that. He certainly wouldn’t have called that easy!
“Now we have to punish you for not following Robin’s instructions.”
He knew it was coming, unfortunately, he just didn’t know what Mel planned on doing about it.
Mel pointed toward the back of the chair again, and regretfully, Chad got back into position.
“Since this is going to be a lot…”
A lot? Chad started to get alarmed.
“…then just stay there like that till I decide to take a break. Then you can curtsey and thank me.”
Till she takes a break? A break? How many times was she planning on hitting him? And he already hurt!
“You’re going to learn that when a woman tells you to do something – make that when anyone tells you to do something – especially a woman – then you had better do it – exactly like they tell you to! Ready?”
Ready? Of course he wasn’t ready! What was she planning? Before he could think any more about it, she swung her stick – hard again. And before he could even fully react, she was swinging again, and again, and again. Over and over again as fast as she could, she pounded away on his backside with her stick. And the pain from it grew, and grew, and grew!
Mel swung fast and hard, but she was carefully controlling herself. Yes, she wanted to hurt him, but not like she would if she had lost control. Over and over again she hit his bare bottom, making sure to cover every inch of it on both sides. Very quickly, it grew from a warm rosy red to a very deep dark red. Finally she paused. “You can thank me now.”
Chad had no idea how many time she had hit him, it had hurt so much that it seemed to go on forever. He had been crying a little and fighting the tears before she had started, now he was bawling full out. He stood painfully, turned to her and curtseyed. But the words that came out of his mouth around his sobbing weren’t completely recognizable. Fortunately, Mel didn’t seem to notice.
“That’s one,” Mel said and pointed towards the back of the chair again.
One? One? He couldn’t believe it. She wasn’t done with him? He looked at the back of the chair and hesitated. He didn’t think he had the courage to lean back against it again for more punishment. But his hesitation only cost him another stinging slap from her stick against his leg. Quickly, he found himself back in position again awaiting the next part of his beating. Once again, Mel flailed away at him unmercifully while he cried, and cried, and cried. Finally she stopped. He was still leaning against the back of the chair, but he couldn’t move.
“Are you going to do as you’re told from now on?” Mel asked.
Still leaning against the back of the chair, he nodded his head vigorously and tried to say, “Yes.” But the moment he did, she was back hitting him again. Five more quick swats of her stick.
“That was for not curtseying before you spoke again!”
Chad curtseyed again, but he didn’t even try to speak. He was crying too hard. Three minutes later, he was laying face down on the carpet on top of a fresh diaper while Mel was gently applying soothing lotion all over his dark red backside. The lotion felt frigid cold and stung as soon as it touched him, but it quickly warmed up. Even though she was only lightly touching him, her hand still felt all too painful as she rubbed the lotion all over his bare skin. He hurt so badly that he was glad when she finally finished and he could roll back over so she could finish diapering him again. And once again, he was working on another hour and forty-five minute time limit.

Chad stood in the middle of her living room, fully dressed once again. He had expected to be practicing ballet again tonight, but it seemed that Mel had other ideas. Ideas that he was not all that fond of. Mel had been working with him for the last fifteen minutes trying to craft just the right kind of apology for him to give to Robin tomorrow. It wasn’t that it was all that much or all that difficult. It was just that it was… embarrassing! But then, wasn’t any kind of apology embarrassing?
“I think that will work,” Mel declared from her seat in the living room. “Let me see it now one more time.”
Chad curtseyed to her immediately – he dared not even think about doing anything without curtseying first. Then he paused for a moment to get ready. He reached down and grabbed the hem of his skirt and dropped into as nice a curtsey as he could, spreading his skirt as wide as possible. He bowed his head momentarily, then rose again putting his feet together and clasping his hands contritely in front of him. “I’m sorry Robin,” he said in his sissy voice, “that I didn’t do exactly what you told me to do yesterday. I promise not to give you any more trouble and to do whatever you say from now on.” Then he dropped into an identical curtsey to the first one again and stood back up. He looked to Mel for her approval and curtseyed quickly to her once again as he did so.
Mel smiled. “Yes, I think that will work nicely. It’s not too extravagant and I think it sets just the right tone. Don’t you?”
Of course all Chad could do was to curtsey again and agree with her.
“Good, now do it again.”
Once again, Chad had to go through the little routine, followed by another practice run, followed by another one. Finally, Mel dismissed him to go finish another bottle while she went back to work on making notes for his ballet.
Chad hurried into the kitchen where his latest bottle was, and immediately put it to his mouth and started drinking. Her stupid little apology routine wasn’t very difficult, but it sure made him feel foolish as he did it. Of course, when he did it for Robin tomorrow – ‘if’ he did it for Robin tomorrow, then he wouldn’t be using his sissy voice. His girly voice wouldn’t be quite so humiliating.
He finished his bottle and was just opening the refrigerator to get another one when Mel called him back into the living room again – to practice the routine five more times.

The Bet - Chapter 45 (Monday – week 7 Part 5 of 7)

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 5 of 7)

Mel was actually at her desk when she saw Chad’s email come through. She read it with great interest – twice. Finally! Things were happening there. And best of all, it was sounding like Robin may not have told anyone yet – not where she worked anyway, which was all she cared about.
She started to write back to Chad, but before she could get started, she was reminded of the odd thought she had that popped into her brain earlier in the day. Was it possible? Would it be possible? There was only one way to find out! Instead of writing what she had planned on writing to Chad, she sent him a reminder to continue to do whatever Robin wanted. Then she asked him to send him Robin’s email address. Two minutes later, she had it. Very carefully, she crafted an email to Robin.

Robin couldn’t believe it when her email notification popped up and showed that she had an email from Mel. What did that crazy woman want now? She opened it and read it.

Dear Robin,

Did you know that Sissy is under orders to do whatever you tell him to? And if he doesn’t do exactly what you say, then I want to know about it!

Call or email me if you want.

Mel

Robin read her note with disbelief. The woman was crazy! She wasn’t about to get drawn into their weird little games! She closed the email faster than she had opened it. But she couldn’t go back to work. Instead, she brooded about what a jerk Chad was. And over and over again, just as she had seen it in her mind all weekend long, she kept picturing him in that highchair, covered in baby food, acting like an infant! The stupid perverted idiot!

Chad stared at his computer monitor – without seeing it. He was more concerned over whether Robin intended on telling anyone about… him… or not. Did he, or didn’t he have to worry about being fired?
Finally, he couldn’t take it anymore. Despite Robin telling him she didn’t want him to talk to her, and despite Mel telling him again to do whatever Robin wanted, he got up from his seat to see her. He had to know! He stopped at the entrance to her cubicle. She was just sitting there with her head in her hands. “Robin,” he said quietly.
Robin turned angrily at the sound of his voice. What did she have to do to get the point across? She didn’t want to talk to him!
“You didn’t tell anyone?” he asked.
She was out of her chair before she even knew it. “Didn’t I tell you not to talk to me? What do I have to do to get you to understand that? I don’t want to hear your stupid voice anymore!” She paused, but only for a moment. “And just for your information, no, I didn’t tell anyone. Nobody at all! Your crazy friend Mel said that it was your biggest secret. The one thing you didn’t want anyone to know about! So why the hell did she tell me? You can think what you want about me, but some people are more trustworthy than others. No! I didn’t tell anyone about you and your… perverted interests! Not yet anyway. Now get the hell out of here!”
She actually shoved him again as she said it. Chad backed off quickly and hurried back to his own cubicle. Well, he had to know. And best of all, it sounded like she wasn’t going to divulge his secret – not yet at least. He actually breathed a small sigh of relief.
Robin again stared angrily at her computer screen, but like before, all she saw was the image of Chad in that silly highchair acting like a stupid baby! The idiot! And he wanted to know if she had told anyone his secret? His deepest, darkest, most perverted secret? What did he think she was? The idiot! The stupid, perverted idiot!
And then his… mistress… what a laugh!... had the gall to send her a note telling her that he has to do whatever she tells him to do? He can’t even keep quiet after she told him – repeatedly – not to talk to her! It was like talking to a three-year-old – you had to tell them things and tell them, over and over again. No, not quite like talking to a three-year-old. A three-year-old had more sense!
He wanted to act like a baby? He had to do whatever she told him to? Well… she knew how babies acted, she had one of her own! And if he was so insecure about everything, then she knew just how to deal with that!
Determinedly, she got out of her seat and marched straight back to his cubicle. “You like acting like a baby?” she announced more than asked.
Chad turned around, totally surprised to see her again so soon.
“Then stick your thumb in your mouth! And suck on it!” she ordered. “That’s what insecure little babies do, they suck their thumb!”
Chad was totally shocked. So much so, that all he could do was to stare at her in disbelief.
Seeing that he wasn’t moving, Robin added. “Your… mistress!” she spat the word, “tells me that you have to do anything I tell you to! So stick your thumb in your mouth and suck on it!”
Still not believing it, Chad slowly raised his left thumb and stuck it in his mouth. Mel had told her he had to do whatever she asked? Was it possible? Well, Mel had asked for Robin’s email address. He just hadn’t expected anything like this.
“I said suck on it!” Robin yelled angrily when she saw that his thumb was only resting in his mouth. She saw him start sucking. “Harder!” she ordered. “I want to see your cheeks going in and out!” A moment later, she felt better about things. It was as if she had physically hit him to vent her rage. “Now keep it there,” she added. “Maybe that will make sure I don’t hear another sound out of you for the rest of the day!” With that, she turned and walked off!
Chad stared at the empty entrance to his cubicle. She had ordered him to suck his thumb! He still couldn’t believe it. Where had that come from? He was so shocked, that he sat there like that for several minutes before he slowly turned around again and took his thumb back out of his mouth. He couldn’t believe it! As per Mel’s orders, he opened his email program again and started to write about what had happened.

Feeling a bit more satisfied, Robin had almost worked up the nerve to do something other than brood, when she heard the faint sounds of him typing in the next cubicle. And it bothered her! How could he type like that if he had his thumb in his mouth? He couldn’t!
In a flash she was out of her seat again and back at his cubicle. He was typing – with both hands! “Damn it!” she yelled. “It is just like talking to a child. You have to keep after them and after them! Didn’t I tell you to keep your thumb in your mouth? What do I have to do, stand you in the corner too?”
Wide eyed, Chad stuck his thumb back into his mouth again and sucked on it hard like she wanted him to. Robin watched him for a few moments, feeling satisfied once again. But then she thought of something else. “Wait a minute! You’re right handed. Put your right thumb in your mouth instead!” She watched as a disbelieving Chad slowly switched hands – and started sucking just as hard on his right thumb now. “Better!” she declared with more satisfaction.
But Chad had a problem now. How was he supposed to type? How was he supposed to work? He pointed toward his keyboard and his monitor, hoping she would understand his question.
Robin smiled. Her voice sounded almost kind. “How are you going to work?” Her voice changed to angry command again. “You still have another hand. Use it!” She turned and started to stomp away again, but she paused and turned back to him. “I’ll be back to check on you. Obviously you can’t be trusted to follow simple directions – just like a child!” She left him then, and returned to her seat, where she reopened the email from Mel and typed a very short reply - He doesn’t follow orders very well, does he!

Chad hunted and pecked with his left hand at his keyboard. Using the mouse was even more awkward. He had to reach across his body to use it, and then the buttons on it were in the wrong place for his left hand. He was careful though to keep his right thumb in his mouth. He didn’t suck on it as hard as Robin wanted him to, but he doubted she would see that as long as his back was to her. Very slowly he continued his email to Mel.

It was a little while before Mel got back to her desk and found both emails waiting for her. She wasn’t sure which one to open first. She opted for the one from Robin because it had come in first. What she read surprised her greatly. He didn’t follow orders? Had she told him to do something? She was about to reply, but she decided to read the one from Chad first – and she was glad she did. When she was done, she sat back in her seat to think about things.
Robin had actually ordered him to suck his thumb? She couldn’t believe it. Did that mean… No, it was too much to hope for. But still, it might be possible. She opened up Robin’s email again and hit the Reply button. She had to be very careful about this. The wrong move or the wrong word could spoil everything. Best to keep it short and simple again.
She wrote – Expect a “proper” apology from Sissy tomorrow. As always, feel free to call or email me.
Then she sent another email to Chad!

Chad had to reach awkwardly across with his left hand to open the email from Mel when it came in. What really surprised him about it was that Robin had obviously emailed Mel first – and told her that he hadn’t exactly followed her orders. The rest of it was only what he expected – be prepared to be punished severely for it. Ugh!
“Turn around!”
The command came so suddenly and unexpectedly that Chad had no time to prepare for it. He quickly turned around in his seat and saw Robin standing at the entrance to his cubicle. Fortunately, his thumb was still in his mouth. He started sucking furiously on it, making sure his cheeks were moving in and out as he did so – just the way she wanted them to.
Robin saw him still sucking his thumb – hard again. Although she doubted he had done much more than keep it in his mouth while she wasn’t there. She walked over and looked at the email message still up on his screen. It was from Mel. She read it. “It sounds like you’re going to get… what? A beating tonight? I hope so! I can’t think of anyone who deserves a beating more than a stupid pervert like you!” She headed back out of his cubicle again, but stopped at the entrance. “I’ll be checking, so keep that damn thumb right where it is – and suck on it so I don’t have to hear your whining voice about anything!”
She walked off leaving him alone again and went back to her own desk. She couldn’t believe it! The jerk! He was actually still sitting there sucking his thumb – like she had told him to. Well, he better be! She wasn’t in any mood to be nice today at all! And there was a certain feeling of… satisfaction… in ordering him about – and actually seeing him do it! As long as she kept watch on him, she guessed. Ha! Just like a child indeed! She wondered how much trouble Mel had with him. And… she wondered why she should even think such a thought.

It wasn’t that Chad minded sucking his thumb so much, it was just that having to keep it in his mouth all the time made doing anything very difficult. He tried to get some work done – not that there was all that much he had to worry about – at least not today. But actually getting anything accomplished was very difficult. He hoped nobody came down to his cubicle to see him today – like Tom Robinson, his boss! That would be embarrassing!
It was kind of strange, sitting there, sucking his thumb, while at the same time trying to notice every time he had to pee and try to hold back as much as possible. It was like two distinctly opposite things going on at the same time. And when the miserable suppository that Cassie had stuck up inside of him at lunchtime decided to do its thing, all he could do was to stand up to make the process go easier and faster – and suck his thumb all the harder while it happened. Ugh! At least Robin didn’t come back while it was going on. What would he have said? Oh yeah, nothing. She didn’t want to hear anything out of him today at all.
But shortly after he had “managed” to sit back down again, Robin did come back. “Turn around!” she ordered from the entrance to his cubicle.
Chad hadn’t heard her coming again, but his back was still to her. He started sucking hard on his thumb again as he turned his chair around, wondering what she would want now. But all she did was to look at him, nod her head, and leave again. He couldn’t believe it, she had been there for no other reason than to check on him. As he turned back around to face his computer, he knew that until she told him otherwise, his thumb was going to have to remain stuck in his mouth – or until he went home.
Twice more Robin made an appearance at his cubicle, for no other reason than to make sure his thumb was still in his mouth. The first time, she merely nodded her head and left again, the second time she shook her head and muttered. “Just like dealing with a child!” And again she was gone.
As the time got closer and closer to the time to go home, Chad began to wonder what he was supposed to do when work ended. Did Robin expect him to walk out with everyone else while he was still sucking his thumb? She had a big surprise coming if she did – because he wasn’t about to go that far!
As the work day drew to a close, Chad got up from his seat with his thumb still in his mouth and got his purse out, ready to go. He watched the clock as it ticked away the final few minutes. With less than a minute left to go, Robin was back one more time. She stopped at the entrance to his cubicle, her things were already in her arms. “Stay there with your thumb just like that till I’m gone! That way I don’t have to worry anymore about seeing you without it in your mouth!” And then she left. Chad sat back down again as if stunned. What a day! What a weird day!