The Bet - Chapter 31 (Monday – week 5 Part 2 of 8)

The Bet
by Karen Singer

Chapter 31 (Monday – week 5 Part 2 of 8)

Chad stood outside her door and paused for a moment. He wasn’t exactly happy about standing there dressed the way that he was, but the thought of what she planned to do to him today was turning his stomach and making him ill. She couldn’t do that to him… she just couldn’t! He’d never get over it. He’d have to quit his job – if they didn’t fire him – and move away to someplace else. That is, if he ever did manage to win this bet – which he was still fairly confident that he could.
Of course, doing things like peeing on the floor this morning wasn’t exactly helping him win. That had been stupid! Why hadn’t he realized he needed to go and just held it? But then she had been forcing him to pee so much for the last few days that he hadn’t even thought about holding back. That wasn’t helping his side at all. He couldn’t wait till tomorrow when he could go back to work again and get away from Mel’s all too difficult and humiliating demands… that is… if he still had a job to go back to tomorrow… or if he dared go back.
A loud piercing whistle from the parking lot behind him brought him out of his mental struggles. He quickly glanced back to see two guys down below staring at him. More ashamed of how he looked than ever, he quickly reached out and knocked on Mel’s door.
The door was opened a moment later. “It’s about time,” Mel declared, still dressed in just her robe.
He curtseyed as elaborately as he could. “Good mowning, Mistwess,” he said in his all too sickening sissy voice around the pacifier in his mouth. The whistle came from behind and below him again. He did his best to ignore it, but Mel stepped past him with a broad smile on her face.
She waved to the men below. “I’d let you play with them, Sissy,” she said, “but we’ve got too much to do this morning.”
Chad was glad. Especially since he had already stepped inside her apartment. He wasn’t about to step back out again if he could possibly help it!
Mel came back inside. “Up in your highchair, Sissy. Breakfast time.”
Yuck! The thought of another breakfast of baby cereal started turning his stomach more than it already was. Why couldn’t she let him eat something else for a change? Some nice bacon and eggs sounded a lot better to him than more baby cereal. Or maybe perhaps an omelet – loaded with plenty of good stuff of course. Now that would be a proper breakfast! But the sight of the pot on her stove quickly dashed any hopes of anything better from his mind.
Sulking, he climbed up into his highchair and sat numbly still while she fastened a bib around his neck and slid the tray into place. A minute later, she placed a large bowl of the tasteless mush in front of him along with two baby bottles. How could he eat it? All he could think about was having to act like a total fool in front of everybody he knew. Everybody was going to laugh at him… everybody! They would all see just how much of a total sissy he really was. What could he do? How could he stop it? “Mistress?” he called desperately in his sissy voice before she could get out of the room.
“Yes, Sissy?”
“Please don’t do this to me,” he begged. “Please don’t take me to work and show me off to everybody I know.”
Mel smiled to herself. He was starting to panic. Not a lot yet, but a little bit. It was a good sign. Just what she wanted. “Sorry, Sissy. Like I told you earlier. It’s for your own good. Better get used to the idea.” With that, she quickly left him before he could ask anything else. Yes, so far things were going perfectly!
Chad sat and stared at the baby cereal in the bowl in front of him. But he didn’t feel at all like eating it. Visions of himself wearing that silly sissy dress she had found him, being pulled all around in front of everybody he knew, and singing for them in his stupid little sissy voice still filled his head. He felt nothing but sorry for himself.
“Sissy?” Mel’s voice called from her bedroom. “You better be eating all your cereal and make sure you drink all your bottles. Cause if you don’t, then I just might send you to work tomorrow wearing one of your other little sissy dresses too. Now wouldn’t everybody you know love to see that?”
Chad shuddered at the thought of it. Not that he’d really have to worry about it much. After today, he seriously doubted he would still have a job tomorrow. But then, it was hard to believe he still had a job now with the way he had been dressing for work lately. Very hard to believe! So maybe they wouldn’t fire him… not right away anyway. With that little bit of hope, he picked up his bottle to wet his mouth before daring the huge amount of baby cereal glop in front of him.

Chad was still forcing himself to eat the last of the baby cereal when a knock came at the door. Panicked, he wanted to hide somewhere, but he was pretty much trapped in the highchair where he sat. He heard Mel going to answer the door. He heard her talking to someone, then the door closing. A moment later, Sandy walked into the kitchen. She had a small plastic bag in her hand. “Hi kiddo,” she said as she spotted Chad in his highchair.
“Hewwo, Sandy,” Chad replied, none to cheerfully.
“Aww. The baby doesn’t sound too happy today.”
“Why should I?” Chad sulked.
“Because today should be fun! You’re going to get to show off your pretty sissy dress to so many people…”
“Ugh! Don’t remind me!”
“Aw. What’s the matter? Is the little baby going to cry?”
“I might,” Chad returned, still unable to come to grips with what was going to happen. “And I’d have good reason too!”
Sandy giggled. “Well, if you do, don’t worry about your makeup.” She held up the bag she had brought in. “I got you a bunch of waterproof stuff so we don’t have to worry about that little problem today at all.” She giggled again as she set the bag back down.
“Sandy!” Mel’s voice called from her bedroom. “Check to see if he’s wet yet.”
“Okay!” Sandy yelled back.
She reached under the highchair tray and grabbed the front of Chad’s diaper. With his hands trapped above the tray, there was little Chad could do to stop her. It seemed like her hand was staying there a lot longer than it should. He suddenly felt her groping around his chastity device through his diaper. With a mischievous grin, she finally pulled her hand away. “He’s wet, but not very,” Sandy yelled to Mel back in her bedroom.”
“Sissy,” Mel yelled back, “better get busy! Don’t make me beat you in front of your coworkers!”
Chad instantly felt even more uncomfortable than he already was as he imagined her spanking his bare bottom with her stick in front of everybody he knew. He quickly picked up the almost empty baby bottle on his tray and began finishing it.
“Just like a baby,” Sandy giggled.

“There, all done,” Sandy declared as she pulled her hand away from Chad’s face.
Chad, still trapped in his highchair, pursed his lips then stretched them. The sealer she had just smeared over top of the lip color felt weird… tasted weird too. Chad wasn’t really sure he liked it.
“How’s he coming?” Mel asked as she finally came out all dressed for work. Chad thought she looked particularly nice today in the skirted business suit she had selected.
“I just finished his makeup,” Sandy replied.
Mel studied Chad’s face critically, then smiled. “Love it!” she declared.
Chad had no idea what he looked like today. It was impossible to tell since he had no mirror to look in. And to be honest, he wasn’t sure he really wanted to know. Besides, nothing good could possibly come from what Mel had planned for today, so maybe it was better that he didn’t know.
“How much time do we have before we have to leave?” Sandy asked.
Mel checked her watch. “A while yet. But we’ve still got to get his dress on him and then I want to make him practice everything again.”
Ugh! More practicing? Chad clearly remembered walking around and around Mel’s living room yesterday, curtseying and talking in his silly new voice to her floor lamp. He wasn’t looking forward to doing that again!
Mel finally removed the tray that was locking him into the chair and let him get down. Before she led him back to her bedroom, she pulled another baby bottle out of her refrigerator and handed it to him. “Don’t disappoint me,” she warned.
Chad curtseyed, “No, Mistwess,” he replied. He kept the bottle in his mouth and drank from it continuously until he was forced to remove it while Mel pulled his dress over his head. Once again, the all too sensual ruffles swirled around his legs. Exciting him… making him feel strangely sexual. Yet he still felt nothing in the very area that he should have been feeling things, his forever trapped penis. The pacifier on the pink ribbon was still attached to the dress. Mel grabbed it and stuck it into Chad’s mouth before she fastened the large white ribbon back into his hair. She walked around him, surveying him critically. “Perfect!” she declared. Her eyes locked onto his and seemed to bore into him. “I’m more than sure all your little friends at work will just love seeing you today.”
Chad shuddered and realized he was wetting his diaper a bit again. “Mistwess, pwease!” he begged pitifully.
“Don’t even bother!” Mel replied quickly. “You’re going, and that’s that!”
The feelings of dread and despair in his stomach doubled.

Around and around. Curtsey elaborately to the lamp, making sure his diaper can be seen every time he did it. Talk in the stupid sissy voice. Try to act happy and excited. But acting happy and excited were pretty much out of the question today. How do you act happy when all you want to do is cry? Show them his diapers like a little baby. Answer their inane questions without any ‘l’s or ‘r’s in his words… and always use the stupid high-pitched voice. Over and over again. Around and around. Very quickly, the boring routine brought back all the silly little habits he had picked up by doing it a million times the day before. He barely thought about any of it after a little while as he just let habit take over.
“Okay, Sissy,” Mel declared. “Now skip around and sing ‘Mary Had a Little Lamb.’”
Chad took another swig from the baby bottle in his hand, then began skipping around her living room. A moment later, the childish song and voice were coming out of his mouth. At least he could bypass the lamp and ignore that every time around. It didn’t take long before the constant skipping and singing got very tiring. Visibly so.
“That’s enough, Sissy,” Mel declared. “We don’t want to wear you out too soon. Go stand in your corner now for a few minutes till it’s time to go.”
From one rotten thing to another. Chad headed to his corner, climbed up on the bar of his perch, and squeezed his whole body deep into the corner. The ruffles on his skirt tickled his legs even as he tried to stand still. He wasn’t thrilled about standing in the corner like that, but at least he wasn’t walking out the door… yet.
Mel busied herself in the kitchen, grabbing lots of jars of baby food and baby bottles from her refrigerator and stuffing them all into several plastic bags. One of his bibs and tiny baby spoons were put into one of the bags too. She checked his diaper bag and made sure he had plenty of everything they would need. At her request, Sandy had gone home to collect a few things for today too. She set everything she had collected by her door to carry out to her car.
Sandy finally came back carrying a large bag of things too. Together, they both carried everything down to Mel’s car and put it all into the trunk. That was it. They were ready. Now all they needed was Sissy.

Chad heard them both leaving – leaving him alone in her apartment. Stuck in the corner as he was, he couldn’t see anything or really tell what was going on. He didn’t really care. He’d rather they left him there all day than what they had planned for him. How could he get out of it? Of all the horrible things Mel had made him do since this bet started, this was by far the worst!
The apartment was quiet while they were gone. He found the lack of commotion around him peaceful, like the quiet before a storm. He concentrated on it, enjoying it while he could, because he knew that all too soon things were going to get worse. Much worse!
He heard their voices even before the door opened. They were back. He had no doubt that his simple quiet reverie was about to end. His panic erupted once again.
“Okay, Sissy. Get off of that thing,” Mel told him the moment she got through her door. “It’s time. Let me look you over one more time.”
Chad carefully climbed down off his perch, holding onto the wall for support. When he was sure of his balance, he carefully let go. His eyes never looked up from the floor though. All he could think about was what they were about to make him do. Life as he had known it was over, and in his fear, tears started running down from his eyes.
“Let me look at you,” Mel said as she walked over to him.
Chad’s eyes were still locked onto a spot on the floor in front of him.
“Look up so I can see you,” Mel commanded.
Very slowly, Chad raised his head to look at her. As he did so, the sobs he was trying to hold back broke forth. In his little girl style dress with all the ruffles tickling the tops of his thighs, crying his heart out, he felt like the biggest sissy ever. And there was nothing he could do about it. And then, to make matters worse, he suddenly felt himself peeing heavily into his diaper. He felt so small and stupid. A total baby.
“I told you the waterproof makeup would be a good idea,” Sandy said.
“Yes, you were certainly right about that,” Mel agreed. “That’s enough, Sissy! This is going to happen whether you like it or not. So stop that crying.”
But Chad couldn’t stop. He was going crazy with fear. “Please, Mistress, please,” he pleaded, careful to speak in his new sissy voice so as not to upset her. “Please don’t make me do this. I’ll do anything for you. I promise. Anything!”
He seemed so distraught that Mel’s heart almost broke. But she had been expecting exactly this and more, so she was well prepared for it.
“No, Sissy. I told you before, this is for your own good. Now stop that crying right now!”
Chad didn’t stop crying. Nor did he understand. “How?” he asked. “How could this possibly be good for me?”
They were getting closer to the heart of the matter now. “How?” she repeated. “Sissy, I told you that this was going to be a new life for you. A drastically different one. And until you accept that fully, your old life is only going to be holding you back. You won’t be able to fully enjoy or even embrace all your new sissy feelings until you fully accept what you are. And by showing everybody you know the real you… the true you… they’ll no longer expect the old you anymore. They’ll accept the new you instead… and you can move on and truly become the sissy you’ve always dreamed of being.”
Chad wasn’t at all sure about her logic. And he also was fairly sure he didn’t want to be the kind of sissy she had in mind.
While Chad was trying desperately to digest what she had just said, Mel’s eyes noticed her yardstick leaning up against the corner. She walked over and picked it up. Holding it tightly in her hand, she brought it back to where she had been talking with Sissy. “Better not forget this thing,” she mused. “We just might need it!”
Chad’s eyes never left the stick Mel was playing with in her hands. Was she threatening him with it already? He wasn’t really sure, but he had the distinct feeling that she might be. She wasn’t going to let him out of this no matter what. It was cruel! She was cruel! For his own good? He doubted that seriously. But she evidently thought so.
She was leaving him no way out, no way around it. Taking a breath to steady himself, he looked down at the floor again, trying to find the courage for what he had to do. Finally, he grabbed the skirts of his sissy dress, and never taking his eyes off of the floor, he dropped a curtsey and said, “Yes, Mistress.”
Mel smiled inwardly, trying not to let it show. What she had told him had been carefully crafted… artfully conceived as a way of convincing him to behave without letting him on to her real motive. Yet the odd thing was, that despite the fabrication she had just laid out for him, the reasoning had the ring of truth about it. Something she would have to carefully consider for later.
Sandy looked on wide-eyed through the whole exchange. She had listened to it all without saying a word or interrupting. She couldn’t believe it! She would have caved instantly under his pitiful pleas for mercy. She didn’t know how Mel could possibly be so unwavering about this. Something else though had caught her attention while Mel was explaining things to him. What exactly had she meant about him showing everybody he knew? The only person he knew at the gym was Cassie… and maybe the receptionist. Maybe she had heard it wrong or Mel hadn’t really meant it the way she thought it sounded. She’d just have to wait and see.
“Okay, Sissy,” Mel said. “It’s time. Down in the car. Time to embrace your true sissy self.”
Chad shook himself a bit. It was time. He didn’t want this – but it was time. No way out. He did his best to put a smile on his face, although the effort was minimal at best. He curtseyed again. “Yes, Mistress.” He headed for the door.
He stopped halfway there, a look of new worry creasing his face. He almost forgot to curtsey. “Mistress,” he said. “I haven’t had anything to drink in a while now. Should I get a bottle for the car?” He didn’t really want it, but if Mel was still going to make him show everyone he knew what a total sissy he was, then no doubt she’d also punish him severely if his diaper didn’t leak in time.
Mel was very pleased. “Of course, Sissy. Good thinking. Because I’ll have no problem paddling your naked backside in front of everybody while we’re out if you don’t make it.” She slapped the yardstick against her other hand to emphasize her point.
Chad saw how serious she seemed to be. Not bothering to curtsey like he should, he ran to the kitchen and pulled another baby bottle out of the refrigerator.

The Bet - Chapter 31 (Monday – week 5 Part 1 of 8)

The Bet
by Karen Singer

Chapter 31 (Monday – week 5 Part 1 of 8)

Like a child’s taunting singsong voice, the words kept echoing deep within his mind. “Sissy, sissy sissy. Sissy, sissy sissy.” Over and over again. He tried to deny it, tried to hide from it, but the outlandish dress he was wearing was not only proof, the dress itself almost seemed to shout the accusations. “Sissy, sissy, sissy.”
Like a puppet on a string, he was forced to skip and dance like a little child, lifting his skirts with glee, despite the horror he really felt. There was no way out. No way to fight back. No matter how hard he tried not to do it, his body kept singing and skipping. “Sissy, sissy, sissy.”
In his dreams, he finally realized that there was no place he could hide from it. Nothing he could do to stop it. Every time he ripped off one bizarre dress, another completely outlandish outfit took its place. No matter what he did, the bizarre clothing seemed to follow him, engulf him, till he no longer even tried to get away. “Sissy, sissy, sissy.”
It was hopeless. The clothing was soft and frilly. Sensual. Teasing him in ways he loved the most. Tickling him till he finally was forced to give in. Touch it. Embrace it. Love it. “Sissy, sissy, sissy.”
He was worn out, broken down. He could no longer fight it. He was forced by something very deep inside of himself to admit the truth. He loved it… he loved it all! He was a sissy! There was absolutely no way around it, he was what he was. A sissy! “Sissy, sissy, sissy.”
Like the petals of a flower just beginning to open, the feelings inside of him started to change and grow. Very slowly at first, then they began rushing faster and faster. Joy! It filled every part of his body, every part of his soul… till now he wanted to skip and laugh and sing. “Sissy, sissy, sissy.”
He was a sissy! That was what he was! He could enjoy the pretty dresses, and shoes, and clothes. He could enjoy the warm wet diapers. He could enjoy his bottles and pacifiers. He could enjoy all the wonderful sensations that it all brought to him without any reservations or guilt. He was a sissy! “Sissy, sissy, si…”
The indignant loud music suddenly began blaring from his pink clock radio. Shattering his dreams. Shattering his euphoria. Shattering he sleep. Erasing from his mind everything he had been feeling. Instilling instead, a sense of shock at being pulled so blatantly out of a much nicer place. Confused, he rolled off of his blow-up mattress, scattering empty baby bottles across the floor. He got to his knees and wanted to take stock of everything, but the darn loud music wouldn’t let him. He reached out and slapped at the clock radio, fumbling with the controls till the music finally ceased. Blessed silence once again filled the room. He breathed in deeply in relief.
Finally, he could allow himself to feel his own body again. His diapers were the first to grab his attention – heavy and wet, ugh – messy too. From his knees they felt bulkier than ever before… if that was possible. But then Mel had been putting four diapers on him for the last few nights instead of his usual three, so he supposed that bulkier was entirely possible. The breast forms glued to his chest also felt heavy, and bulky, and a nuisance. They stuck out way too inconveniently underneath his babydoll nightie top.
He struggled to his feet and quickly became more aware than ever of the weight and bulk of his diapers. Wow they were thick! The pressure between his legs was uncomfortable… and sensual. As he tried to waddle slowly toward his bedroom door, the super-bulky feeling turned him on slightly. Yet despite the pleasure he felt, it didn’t do anything at all for his completely limp penis trapped inside of his diapers… and trapped inside of his chastity device. He could no longer even feel his penis. In fact, he really hadn’t felt much from it for a few days now. But as long as those cruel teeth were still inside of the device, it was just as well. Those darn teeth could hurt!
He was halfway through his living room, on his way to see if Mel had left him another note when he remembered the very last thing she had said to him last night. His knees almost buckled, his progress almost stopped. A sick feeling of dread sank deep into his stomach. Nooooo! She was planning on dressing him up in his most outrageous sissy dress and take him into work to show him off to everybody there! Even Robin! Everybody! They were all going to see exactly what he was… not just a guy who was now wearing dresses to work like a woman… they were going to see him for exactly what he was – a diaper wearing, total sissy flake! Nooooo!
His progress toward his kitchen stopped completely. He was suddenly afraid to see her note. Afraid of what new demands she might have for him to make his worst nightmare come true. He couldn’t let her do it! He couldn’t! He would have to find some way to stop her. He would do anything! Plead, beg, anything!
He continued on to his kitchen, because in order to come up with an idea to stop her, he first had to know what she wanted of him. The note was there, where it always was.

Sissy,

First bottle – before you do anything else. And finish it – before you do anything else!
Get your shower and get cleaned up. Make sure you shave clean – all over!
Call me as soon as you get finished – before you put any diapers on!
If you can do this right today, I “might” give you two and a half hours to make your diapers leak instead of only two hours – if you can do it right!
And remember – Sissy Talk!

Sissy Talk! His stomach turned squeamish at the thought of it. Visions of skipping around Mel’s livingroom last night acting like a total fool filled his mind. Had he really done that? He didn’t want to answer his own question. His thoughts turned instead to something else – two and a half hours! Now that would be great. Just that extra half an hour would take so much pressure off of him. He was sure he could make all his diapers leek inside of that time limit… if he didn’t allow himself to slack off. Damn! That meant that the bottom line was that she was still going to be keeping the pressure on him. Maybe it was just because he was thinking about it, or maybe it was because it was just time, but he suddenly realized he was peeing again. The brief sensation felt all too wonderful inside of his super bloated diapers. Nice!
As he opened his refrigerator and pulled one of the freshly stocked bottles out of it, he thought again about what she had planned for him today. Again his stomach wrenched at the very thought of it. He didn’t bother to wonder if she would really do it. He knew she would!
He sat on his overly bulky diapers, in the only chair that he owned. He pulled his pacifier out of his mouth and stuck the bottle in place instead. As he started drinking the cool green tea from the bottle, his mind began running countless scenarios of Mel parading him around the company where he worked. The cool liquid from the bottle did nothing to calm the burning fear from what was running through his head.
Damn! How was he going to get her to not do it?

Mel took another sip from her coffee and glanced again at her cell phone. How long did it take him to drink one little bottle then get cleaned up? If he didn’t call soon, she was going to go over there with her stick and give it to him good! She had big plans for him today. Major plans. And some of them were things that had to be done at a certain time. She couldn’t afford to let him be late!
The sudden buzzing of her phone startled her. She grabbed it quickly. “Hello?”
“Hewwo, Mistwess,” Chad’s high-pitched sissy voice came over the line.
Mel felt a mixture of humor and relief at hearing his voice. “Are you naked?” she asked.
“Yes, Mistwess,” he answered.
“Good, I’ll be right there!” Mel hung up her phone and grabbed her keys. She was out her door quickly. She knocked softly on his door. It was opened immediately. He was hiding his naked body behind the door as he opened it. She was tempted to stand there and demand that he curtsey for her before she entered, but with him naked like that, she thought better of the idea and went inside… then she stood still, glaring at him.
Chad almost wilted under her gaze. He felt unusually uncomfortable standing in front of her naked. And now she was obviously waiting for him to curtsey to her again. There was never any question of resisting. “Hewwo, Mistwess,” he said in his new sissy voice as he dropped a quick curtsey for her.
His actions sent a wave of pleasure through her. She just loved seeing him do that! And now with his new sissy voice it was twice as good. “Hello, Sissy,” she finally replied. She looked him over briefly as he stood in front of her – naked, except for his chastity device and the breast forms that were glued to his chest. About as naked as he was ever capable of getting anymore. His hair was still wet and a mess from where he had just washed it, but otherwise, he looked clean… and clean shaven. Speaking of which… “Let’s go to your bathroom, Sissy. I need to check to make sure you didn’t miss anything today.”
Chad would have curtseyed to her again as he had been taught, but she was already walking off. He followed quickly behind her.
As Mel walked into the bathroom, she was pleased to see that he already had one diaper laid out to put on. Good, it would waste less time. “Okay, Sissy. Let me see you.” Mel had him turn slowly around while she inspected him critically all over. She stopped him at one point and grabbed his razor from the counter. Then she ran it lightly over his back where he couldn’t reach properly. Overall though, he had done a very good job of keeping himself well shaved. She was pleased.
When she got back to his front side, she couldn’t help but stare for a few moments at his penis trapped inside of his little device. It was so tiny. But then that was as big as it ever seemed to be anymore. It was hard to believe that that little thing might be capable of getting so much bigger. Was it still capable? An interesting question, but she wasn’t going to waste the time right now to find out.
“Okay, Sissy. Good job. You can…” All thoughts of finishing what she was saying died when she noticed a stream of pee running out of his chastity device to fall on the floor. And strangely, it was a moment before Chad even realized he was doing it.
“Oh shit!” he cursed as he realized what was happening. He quickly glanced around for a way to stop it or for something to catch it all. His eyes fell on the diaper he had laid out. He grabbed it quickly.
“Just let it go, Sissy,” Mel commanded before Chad could catch anything with the fresh diaper. “It’s too late now anyway.”
Chad stood before her looking very uncomfortable and embarrassed as the pee continued to flow out of him, down and out of his chastity device, and splashed in an ever-growing puddle on the floor. Mel backed up a few steps to avoid being splashed, but Chad had no such luxury. “Sorry, Mistress,” he mumbled awkwardly, not even bothering to use his new sissy voice.
“That’s okay, Sissy. In fact, I’m rather pleased. So pleased in fact, that I may find a way to reward you later… maybe.”
Chad looked up hopefully. There was excitement in his eyes. “Please don’t show me off around where I work today, Mistress. Please!”
Mel shook her head. “Sorry, Sissy. I’m not that pleased. Besides, this will be for your own good! Now clean that up and do your hair. No makeup, one diaper, the cute little shoes and socks you wore home last night, and your baby-doll top. Nothing else… oh, except your jewelry. Make sure you’ve got plenty of extra diapers in your diaper bag before you come over to my place. I’ll see you there.”
“Yes, Mistress,” Chad replied reluctantly, again not using his new sissy voice. He was clearly upset that Mel still intended to show him off to all his friends at work.
“You’ve got two and a half hours to get that diaper leaking today.” Chad was at least glad to hear that part. “Oh, and Sissy… The next time I hear you not using your new sissy voice, and the next time you don’t curtsey when you should… I promise, I’ll make things twice as bad for you when we get there as I intend to!”
Chad’s mouth fell open wide as she turned on her heel and left him. The very thought of prancing around and singing and talking like a total idiot in front of all his friends sent waves of dread running through his stomach. There’s no way she would actually do that to him, would she? No way!
Damn! He knew she would! Without a doubt!

Mel hummed softly to herself as she stirred the baby oatmeal she was preparing on her stove. She couldn’t get the sight of him peeing on his bathroom floor this morning out of her head. She was convinced that he didn’t even know he was going to do it because it had obviously been such a surprise to him. And then when he realized it was happening, he reached for something to soak it up instead of trying to stop it with his body’s muscles. Why didn’t he just stop it? But then that was the kind of behavior from him she absolutely wanted to see because it meant that he really was losing control. And him losing control also meant him losing the bet… and of course she would win!
She had been so worried because he had claimed under hypnosis at Gloria’s that he could hold back for so long. But maybe he couldn’t! Had he really lost more than he had claimed, or was his lack of control this morning really just some fluke happening? She had been purposely riding him extra hard for the last few days. Could that have had something to do with it? Unfortunately, the last scenario was more than likely. But if it was, then at least her plan was working… somewhat.
Bottom line - she just didn’t know where he really stood. And consequently she couldn’t trust him. She really needed Gloria’s help. Gloria could get information out of him without him knowing about it. And information was power. Of course, more importantly, Gloria and her ability to hypnotize him could insure that she would win this bet easily! Unfortunately, Gloria was being a bit stubborn about helping lately. But that was just something she would have to straighten out, and quickly. Hopefully today.
She turned the heat off and moved the pot away from the burner. It was ready. Now where was he?

Quick Reminder

Just a quick reminder, especially for those who have joined this story late. I have all of the chapters published so far available in a single text document (Chapters 1 - 30). Just email me at siskarensinger at yahoo dot you-know-where and I’ll send it by return email.

Also, I still have my Baby Bobby story available too. Just let me know what you want.

Stay happy everyone,
Karen

The Bet - Chapter 30 (Sunday – week 5 Part 7 of 7)

The Bet
by Karen Singer

Chapter 30 (Sunday – week 5 Part 7 of 7)

Dress number 2 was the blue outfit. A pale blue and white little girl style party dress with lots of stiff netting under the skirt. The outfit even had a pair of blue shoes to match along with its own pair of lacy anklet socks.
Chad quickly got his pink heels and socks off of his feet, then he went to work struggling with the buttons at the back of the dress he was currently wearing. It took a few minutes, but he finally got them open far enough to pull the dress off. He was grateful he no longer had the super long fingernails on his hands. The job would have been completely impossible. He dressed as fast as he could in the next outfit, being careful to again transfer his pacifier and ribbon to the new dress first. He checked his image in the mirror, and ran out of Mel’s bedroom before she could start wondering what was taking him so long.
Chad’s running caught the attention of all the women. As he came into view, Andrea let out a rather loud gasp of laughter. “Oh! I just love it she exclaimed as he ran up to the spot next to his perch.
Chad stood there, not quite knowing what to do next. He glanced at Mel. There was a look on her face like she wanted him to do something, but she didn’t want to tell him what. Hoping he was getting it right, he dropped another curtsey for everyone. Mel looked a bit more pleased.
“I like that outfit much better than the first one,” Cassie exclaimed. “Especially for tomorrow.”
Tomorrow? Chad had to wonder what she was referring to.
“Yeah, I really can’t decide between this one and the next one,” Mel replied.
Chad wondered again what they had planned for tomorrow. Mel had never really told him.
“I think he needs more work on his curtsey in this dress though,” Sandy noted. “All that netting underneath hides his diaper when he does it. Especially after we worked so hard on it this afternoon.”
“That’s a good point,” Mel agreed. “Curtsy for us, Sissy.” Chad again curtseyed like he had been told. “Yeah, you’re right. I couldn’t see his diaper at all.”
“Grab more of your petticoats when you do it,” Cassie suggested. “Lift them up out of the way.”
Chad looked to Mel for confirmation, then slowly, he curtseyed again, this time trying hard to grab as much of the stiff netting under his skirt as possible. It was very difficult to do and it took rather a long time.
“That’s a bit better,” Sandy noted as soon as he was done, but it looks like it was a bit difficult for him.”
“Try it again,” Mel ordered. Again Chad went through it, trying to do it faster this time. But he was only marginally successful.
“Hmmm. More practice?” Cassie suggested.
“Maybe,” Mel replied. But she really wasn’t sure. “On your perch,” Mel ordered.
Before Chad got back onto his perch, he quickly grabbed his baby bottle and took another hit from it. Mel had told him earlier to do it whenever he possibly could so he took advantage of the slight opportunity. Then he climbed back onto the bar. The shoes he was wearing were little girl shoes, not made for the position that he was forced to stand in, but the tiny thin heels on the shoes still grabbed over the top of the bar, locking his feet into position so he couldn’t move them.
Cassie got up from the table and walked over to him. “This is one of my favorite outfits for him,” she said. “I think it makes him look like a little Dresden doll. He just needs to be positioned a bit better.” With that, she grabbed his right arm and had him put his elbow up against his waist, then she extended the rest of that arm out to the side and up at a slight angle. His wrist she bent down. “Other arm now,” she said to him.
Chad copied with his other arm the limp wristed position Cassie had careful arranged with is first arm. He remembered doing this last week and the position still made him feel like a super sissy. But then, wasn’t he?
Andrea was laughing again as Cassie returned to the table. “He looks so funny!”
Mel pushed her chair back from the table. “Okay, Sissy. Get off that bar now and stand next to it, just like that.”
Chad extracted himself from the bar and did as he was told, finally rearranging his arms and wrists exactly like Cassie had wanted.
“Now curtsey for us again and go right back to that position again.”
Ugh! Curtsey again. How many times had he already done it today? But he knew very well that the evening wasn’t over with yet and he still had many more to go. He quickly bent down and tried again to grab as much of the netting under his skirt as he could, then he launched into the rest of his curtsey. He finally returned to the same limp-wristed position he had started in. Sandy was giggling, but he saw Mel smiling almost triumphantly.
Mel looked over at Cassie and Sandy. “I like it. And I think he’s almost got it. But I think with the petticoats like this he needs to pull them up higher when he does it so we can see more of his diaper. I like it when there’s no question that he’s wearing one under his dress.”
“Try it,” Sandy agreed.
“Got that, Sissy?” This time pull your skirts up even higher. Now do it again.”
Once again Chad went through the almost grueling curtsey routine, this time trying desperately to pull his skirts and all the netting underneath up even higher.
“Higher!” Mel ordered while he was still bent down.
Chad immediately stretched his arms as high and as wide as he could.
“That’s it!” Mel exclaimed excitedly. Chad allowed himself to come back up again and resume his limp-wristed position. “That’s exactly what we want to see from now on!” Mel declared. “If you’re going to do it, then you should do it right! And for you, right means showing off your diapers underneath!” All the women broke out into peals of laughter.
“Okay, Sissy. Next outfit.”

If Chad had a personal favorite… or rather hated dress… then it was certainly the next one. Like the blue dress he was taking off, the next dress was also very much a little girl party dress. But this one was mostly white with pink trim. What set this dress apart from the blue one however, was the huge amount of very soft ruffles under the skirt that fluffed it out enormously. And it wasn’t just that there were a lot of ruffles, it was that that unlike the stiff netting of the blue dress, these were very soft and almost sensual against his legs. There was no getting away from them constantly caressing his bare thighs with each little movement. It was very unnerving in a way.
Mel had paired the dress up with yet another pair of frilly ankle socks, and this time his new black patent mary janes. When he was completely dressed, he looked at himself in the mirror again. The whole thing absolutely screamed little girl, little girl, little girl! Or maybe it screamed sissy girl instead. He wasn’t really sure. Probably more like sissy girl because no normal little girl would wear such a thing. With his pacifier back in his mouth again, he hurried back to the ladies.
While Chad was in the bedroom changing, the women had left the table and had settled with their glasses of wine in the living room chairs. Chad was surprised to see them there. He quickly changed the direction he was heading and found a spot where they could all see him in the living room instead. When he there, he did his best to try to curtsey like they now wanted him to and then finally ended up in Cassie’s limp-wristed position. Several of the women were giggling at him again. Mel looked very pleased.
“That’s the first dress you got, isn’t it?” Andrea asked as she got up to inspect him more closely. “I think I like this one the best.”
“It’s probably my favorite too,” Mel agreed.
“I like the blue one,” Cassie said.
“I like the other one, the more babyish one,” Sandy added.
“Yeah, but I think for tomorrow, it needs to be either the blue one or this one.”
What was happening tomorrow? Chad still had no idea.
“Curtsey again for us,” Sandy ordered. Chad again went into his elaborate curtsey. The super massive ruffles making the task even more difficult in this dress. He did his best though to hold as much of it up high and wide as he could though. Again he heard giggling from the women.
“I think the pink is a bit more of a sissy color, isn’t it?” Andrea noted.
“You’re probably right. Pink is a much more suitable color for him. So this dress will be the one. Now we just have to get him to act more like a sissy. Just curtseying isn’t going to be enough.”
“It’s not?” Andrea asked. “Not quite understanding.”
“No, I think there needs to be more.”
“Like what?” Cassie asked.
“I don’t know,” Mel replied. “Any ideas.”
Sandy giggled. “He looks like such a little girl in that outfit. Why not have him act more like one.”
“How?”
“Do you know any nursery rhymes?” Sandy asked Chad.
Chad was taken completely off guard by the question. Nursery rhymes? He really didn’t know. He curtseyed again, then said, “I don’t know.”
“Oh come on! You must know some!” Cassie complained. “Think!”
But Chad wasn’t really sure.
“How about Mary Had a Little Lamb. Can you do that one?” Andrea suggested.
“Good one!” Sandy replied appreciatively.
Chad thought about it. “I guess so,” he replied.
“You didn’t curtsey again before you said that!” Mel lashed out quickly.
Chad grunted his frustration, then curtseyed again then repeated, “I guess I know it.”
Mel nodded as if satisfied. “Say it for us.”
Oh brother. And he knew she wanted him to do it in his new sissy language. He had to think about it for a bit before he started. And the more he thought about it, the more he realized how funny it was going to sound. He almost started saying the rhyme out loud, when he remembered the rule. He curtseyed once again. Then he began. “Mawy had a wittle wamb.” There was a lot of giggling from the women. “It’s fweece was white as snow.” All the way through the piece the women giggled more and more. Chad felt so small. He was very glad when it was all over.
The women were all laughing hysterically. “Do it again,” Cassie asked through her laughter.
Chad looked at Mel who was also laughing. She merely nodded and waved her hand. Once again he curtseyed and went though the childish nursery rhyme, his voice making it sound even more childish.
“He should do that tomorrow!” Sandy declared when he was finished.
“Mel nodded. “Definitely!”
“Practice it again,” Cassie said, still laughing.
“Wait a minute,” Sandy interrupted. “Have him skip around the room while he does it!”
The women all laughed harder. Skip? They couldn’t be serious!
But Mel was agreeing. “Do it!” she managed to get out despite her own uncontrolled laughter.
Chad couldn’t believe it. Now he had to skip around the room too? When would it ever end? He took a deep breath to steady himself, curtseyed for the women, then started skipping. A few steps later he started to say the rhyme. Damn he felt like a fool!
“Sing it!” one of the women called out.
Chad turned his head to see who had said it, but they were all laughing even harder. He started singing it instead as he skipped. He finally finished the rhyme and skipped back to his starting point where he stopped. Finally.
“Don’t stop now,” Mel said. “We’re all having too good a time. Besides, you need the practice!”
They wanted him to keep doing it?” Damn! Chad again curtseyed for them then began skipping and singing. Over and over, around and around. Singing the nursery rhyme with the distorted words was getting easier and easier – fortunately. And just as fortunately, the laughing from the women was finally getting less and less. But they weren’t letting him stop yet, so he had to keep skipping and singing.
And then without warning, he suddenly felt a ticklish something running down his leg. His diaper was leaking! He stopped with a rather horrified expression on his face. He tried to curtsey as fast as he could and knew he wasn’t getting it right, but he had to tell Mel. “I’m leaking!” he finally was able to say to her as he held out his leg to show the pee running down it.
Andrea laughed the loudest, although Cassie and Sandy weren’t far behind. Mel however looked excited and happy. “Excellent, Sissy. And you’ve still got plenty of time to go.” Chad just stood there while the three women tried to calm themselves after laughing for so long. “Go take that dress off now, Sissy. I’ll be in to change you in a minute.”
Chad took off for her bedroom. He was glad it was all over… he hoped. The three women were all still out there.
Chad took off his dress, then he had to wait for Mel for a few minutes before she came in to change him. When she was done with is diaper, she put his baby-doll nightie top back on him again, but left the black mary jane shoes on him. “Two hours,” she reminded him before she sent him back out, this time directly to the kitchen to start cleaning up.
While Chad worked in the kitchen, he could hear the women talking and laughing in the living room together, but he couldn’t really hear anything they were saying. They did seem rather excited about something though. What worried him the most was tomorrow. They had referred to it several times, but he had no idea what they had planned. He did have a strong suspicion though that it was going to involve him… and that he wasn’t going to like it very much!
“Sissy, come say goodbye to everyone.” Mel finally called.
Chad was more than glad to see them all leaving. He had long ago had enough! He had to curtsey for each of them again and wish each of them a goodnight. Every one of them did take the time to tell him how good dinner was, which made him feel really good… and proud.
The door finally closed behind their guests and Chad looked over at Mel. “You did very well tonight. Very well! No go finish up in the kitchen.”
Chad wanted to take the time to ask about tomorrow, but Mel was already heading to her bedroom. He headed for the kitchen instead. When he was done, Mel had him load up a plastic bag full of the baby bottles she had sealed with her tape and take them to his own refrigerator in his apartment. When all the bottles were loaded into the refrigerator, she surprised him by changing his diaper again. She stuck another suppository up inside of him, and this time put four diapers and his plastic panties on him so he would be diapered for the night. The four diapers felt incredibly thick after wearing only the one for so long.
Mel went back to his refrigerator and brought him three more baby bottles to drink for the night. Then she laid him down on his blow-up mattress. Chad set his pacifier on the floor where he could reach it easily and grabbed the first bottle. He put it to his lips and took a sip. But it was only a small sip before he removed it again. There was a question he desperately wanted to know the answer to. So he just had to ask. “Mistress, what’s happening tomorrow? You and the others kept referring to it all day, but I still don’t know what’s going on.”
Mel smiled. He couldn’t have timed his question better if she had told him to ask it. She stood up and backed up to his bedroom door. She turned out his light. She could see him still watching her, his baby bottle held waiting in both his hands. “Tomorrow,” she replied... “Tomorrow, I’m going to dress you up in your most sissy baby dress… Then I’m going to drive you to work and personally show you off to everybody there that I can find… Including your little friend, Robin!”
She turned quickly and left then. But as she opened his apartment door to leave she could hear his wail of despair. “Noooooo!” She smiled all the way back to her own apartment. The hook had been set!

The Bet - Chapter 30 (Sunday – week 5 Part 6 of 7)

The Bet
by Karen Singer

Chapter 30 (Sunday – week 5 Part 6 of 7)

The doorbell rang. “Sissy,” Mel called from her bedroom. “Don’t forget, I’ll be listening.”
Ugh! Chad felt silly. Not just for the way that Mel wanted him to behave tonight, but also for the way he was dressed. At least his diaper was fairly fresh, Mel had changed it less than half and hour ago. He had managed to make the last one leak again, something he was fairly proud of. But now he was working on yet another two hour deadline. His biggest problem though, was the way he was dressed. Mel had fussed extra long with both his hair and makeup. His hair was basically the same – if you didn’t count the big white bow she had fastened on top. He tried hard not to think about that. His makeup was a bit different too, brighter, bolder, and certainly more colorful. There was no way to miss his bright red lips.
He was wearing his bra and waist cincher – naturally. No girdle or pantyhose – nothing that would make it difficult for Mel to see how wet his diaper was. Of course, seeing his diaper would be no problem – for anybody, since he was only wearing the top to his baby-doll nightie. The only other thing he had on was the darn pink patent high heel shoes she had bought him yesterday… oh yeah, and his pacifier that was now attached to a long pink ribbon that was pinned with a fancy pink bow to his baby-doll top. It was a strange outfit, but he knew all too well that it was also only temporary.
He opened the door, Mel’s secretary, Andrea, was there holding a bottle of wine. Just as Mel had made him practice over and over again, he removed the pacifier from his mouth and dropped his elaborate sissy curtsey to her. “Hewwo, Andwea,” he said in his best sissy voice. He knew that Mel would be listening for sure. She had made him practice this greeting over and over again till she was happy with it.
Andrea was so startled she almost dropped the bottle in her hands. “Hello, Sissy,” she replied, still trying to take in the way Chad was dressed, let alone his voice and his curtsey. “May I come in?” she asked.
“Of couwse,” Chad replied, curtseying yet again, then standing out of the way. He didn’t turn to look, but he could just feel Mel watching him. Over and over again she had made her rules very clear for tonight. He had to always use his new sissy voice – always! He had to curtsey every time he said anything – always! He had to keep his pacifier in his mouth all the time, unless he was talking or drinking from his bottle – even if it meant taking it in and out constantly. And above all, she wanted him to do his best to try to show everybody just how much he loved being a sissy. Okay, he did love it. And deep down, everything he was doing thrilled him to the core. But still, he felt silly.
“Hi Andrea,” Mel’s voice called as she walked out of her bedroom. She was dressed semi-casually, but Chad thought she looked extra good tonight.
“Hi Mel. I brought a little bottle of wine, just in case you might need it.”
“Thanks, Andrea. Wine is always appreciated.”
“What’s with the way you’ve got him talking? I nearly jumped out of my skin.”
Mel laughed. “Don’t you just love it? That’s his new sissy talk we’re working on.”
“I wasn’t aware that he needed anything else to let people know what he is.”
Mel laughed. “True! Let’s just say that I’m trying to make sure there’s no question about it.”
“I don’t think you’ll have any trouble.”
Mel looked over at Chad. “Sissy, aren’t you supposed to be busy in the kitchen? And there’s something wrong with your mouth!”
Chad quickly grabbed his pacifier and stuck it back in place again. Then he headed back to the kitchen to finish preparing dinner. There wasn’t really much more to do. Everything was mostly ready.
A few minutes later, another knock came at the door. “Sissy!” Mel called from the living room where she was talking with Andrea.
Chad ran out from the kitchen, spat the pacifier from his mouth, curtseyed, said “Yes, Mistwess.” Then he hurried toward the door as fast as his very high heels would let him go. He opened the door again. Sandy and Cassie were there. Both of them seemed to be dressed nicer than usual too. Big sissy curtsey. “Hewwo Cassie.” Another big sissy curtsey. “Hewwo Sandy.”
“Well, hewwo to you too,” Sandy replied teasingly. “Don’t you look just… adorable! Love your bow. You should consider wearing one more often.”
Chad blushed as he stood back out of the way for the women to enter. As they walked past him, he reached down and grabbed his pacifier and put it back into his mouth before Mel could yell at him about it again. Then he hurried back to the kitchen. Everyone was here. It was time to serve dinner.
He had already set the table, so it was just a matter of dishing everything out. As he raced around the kitchen, he occasionally grabbed his latest baby bottle, this time filled with apple juice, and took a quick drag on it before sticking his pacifier back in his mouth. He looked over the table carefully. The food was finally dished out but as per Mel’s orders, the wine was not yet poured. Otherwise, everything looked perfect. Taking a deep breath, he headed into the living room where the women were talking. He pulled his pacifier out of his mouth and let it dangle from the ribbon it was attached to. “Excuse me, Mistwess,” he said as he curtseyed. “Dinnew is weady.” Then immediately, he grabbed his pacifier and put it back into his mouth again.
“Thank you, Sissy,” Mel replied.
“Wonderful!” Andrea exclaimed. “It smells so good, I can’t wait.”
“It’s always good!” Cassie replied as they all got up from their seats.
Chad hurried back into the kitchen ahead of the women. He grabbed the bottle of wine that he had already opened and approached Mel first. “Would you wike some wine, Mistwess?” he asked.
“Yes, please,” Mel replied and watched as Chad poured her drink. She watched him carefully as he asked the same question and poured drinks for each of the women. She was pleased. He was behaving perfectly. Exactly what she wanted. And when it came to cooking and serving dinner, he really was very good. She wondered briefly where he had learned to serve like he did.
As the women all began eating, Mel looked around the table, checking everything and everyone. It looked like nobody was going to need anything for a few minutes. Sissy could be spared. She looked towards him, he was standing attentively out of the way, watching them. “Okay, Sissy. Time to change.” She watched him as he curtseyed to her and said his little sissy reply. Then he hurried off.
“Change?” Andrea asked.
“You said you wanted to see him in some of those outfits I got him,” Mel replied.
Andrea smiled. “I can’t wait!”
Mel’s bedroom seemed to be filled with ruffles and sissy things. Earlier, Mel had carefully laid out three different outfits for him to wear tonight. Looking them all over, he couldn’t decide which one was the worst… or the best – depending on how he looked at it. But there was no time now for musing about such things. If he didn’t hurry, then Mel had promised a severe beating… and Chad was trying extra hard to not let that happen!
He hurried over to the first outfit. Unbelievably, it was the most babyish looking of all the outfits – not that the others were really very far off. The very short pink check pattern of the dress over top of the built in white blouse just seemed to look very juvenile.
He set about taking his shoes off, then his baby-doll top. First he struggled with the frilly new ankle socks she had made him buy yesterday. Lots of pretty lace around the ankles to go with the pink checks in the dress. Then he buckled the same pink high heels back onto his feet again. To him, the shoes seemed very out of place with the nature of the dress. But that hadn’t been his decision. Mel had decided. Each of the other dresses had their own shoes to go with it and Mel had decided on these for this dress.
Before he pulled the dress on, he carefully transferred the long pink ribbon attached to his pacifier to the new dress, then he slipped it on. Buttoning it up in the back was extremely difficult, but through sheer perseverance, he finally managed it. But by the time he did, he was beginning to worry about how much time it had taken. He quickly checked his image in Mel’s full-length mirror. He popped his pacifier back into his mouth and hurried out to the women.
All eyes turned to him as he returned and curtseyed yet again for them all. “I’m sowwy I took so long,” he apologized. “Does anybody need anything?”
“Oh my!” Andrea exclaimed. “That dress is just too much! And I love the way the bow in his hair matches the little white bows on the front.”
“Wait till you see some of the other dresses,” Cassie replied. “I think they’re even better.”
“I like this one,” Sandy said. “I think it’s the most babyish of them all.”
“You would like this one!” Cassie laughed.
“Okay, Sissy,” Mel commanded. “Go get your perch and set it where we can see you.”
“Yes, Mistwess,” Chad replied with another curtsey. Then he hurried off.
“His perch?” Andrea asked.
“Oh yeah!” Sandy replied. “Wait till you see it.”
Chad came back a moment later with his heavy wooden perch. He set it carefully in place on the floor, then he climbed onto it.
Andrea watched the whole thing raptly. After he was standing on the bar. He just seemed to stand there and do nothing. “I guess I can see why you call it a perch, but what purpose does it have?” she asked.
Mel smiled. “It keeps him in place. He seems to fidget a lot, especially with his feet. Once he’s standing on that thing then he’s not going anywhere and his feet are kept nice and still. No fidgeting!”
Andrea set her fork down and removed the napkin from her lap. She just had to get a closer look. She got up from the table and walked over to Chad, looking him over carefully. She reached out and felt the material of his dress. It was nice and soft. The dress was so short though that she could see the bottom of his diaper underneath, even standing this close. She walked around behind him and took a closer look at the “perch” he was standing on. It appeared to be a simple wooden bar held up between two supports, mounted on a triangular shaped piece of wood. She looked closer. As high as the heels were on his feet, they still weren’t touching the bottom of the platform in the back. All his weight had to be resting on the bar! In that position, she could see why moving his feet would be difficult. “Isn’t that rather uncomfortable?” she asked.
“A bit,” Mel agreed. “But that’s not our problem.”
Andrea perfectly understood as she returned to her seat. The discomfort and pain, if there was any, would be all Sissy’s to deal with.
“Sissy,” Mel’s voice rang out. “Show us your diaper!”
Chad momentarily panicked. But he had already been through this a hundred times today. He quickly bent down to grab the hem of his skirt, but the dress he was wearing was much shorter than the skirt he had practiced in earlier… and he missed. By a lot. He heard giggling from the women as he corrected himself and finally found it, so much higher than he was used to. He quickly pulled the front of his dress up as high as he could and held it there. He could no longer see the women through the material in front of his face, but he could hear their laughter.
“Oh my,” Andrea said, “his diaper looks awfully wet!”
“It better look that way,” Mel replied. She glanced at the clock. He still had quite a while to go before he had to be leaking again. It looked like he was once again going to be successful. She was pleased. “Okay, Sissy. Lower your dress again and refresh our wine.”
Chad dropped his skirt and tried to curtsey on the bar he was standing on, but with his feet locked in place he nearly fell as he tried to do it properly. He finally settled for dipping both knees as he held his skirt out wide. He carefully got off of the bar. At least he had only been on it for a few minutes. The heels he was wearing weren’t really much different than the height of the bar, so for once he didn’t need to flex his ankles after getting off of the thing. He hurried to grab the wine and he carefully refilled everyone’s glass. When he finished, he quickly took another long swig from his baby bottle before getting back onto his perch again.
He had just barely gotten settled on the bar though, when Mel decided it was time for dress number 2. Why couldn’t she have sent him to change before he got back on the bar? Still, he was grateful that he didn’t have to be on that thing any longer than he did!

The Bet - Chapter 30 (Sunday – week 5 Part 5 of 7)

The Bet
by Karen Singer

Chapter 30 (Sunday – week 5 Part 5 of 7)

Chad watched Sandy looking through his closet. His head was still spinning from walking around Mel’s living room for so long. He felt dull from all the countless times he had curtseyed and spoke his little greetings in his stupid high-pitched voice. At least that part was starting to get easier. He wasn’t particularly happy about Mel wanting him to use that voice, but at least she wasn’t making him speak in only baby language again.
Sandy pulled a wide multi-colored skirt off of one of the hangers. She turned around and threw it at him. “Here, put this on. That should be perfect.”
Chad turned the colorful skirt around and around and finally decided that the zipper was supposed to go in the back. He pulled it on and zipped it up easily. When he let go of it though, it settled a bit lower around his hips than he thought it should. But the skirt was fairly short so that when he looked down, he could still see his knees.
“Hmmm,” Sandy mused as she watched. “Looks like we need to fix that. It’s a bit big in the waist on you. Do you have any safety pins?”
Chad shook his head. “No, none.”
Sandy turned back toward his closet. “We’ll see if Mel has any when we go back. I’ll bet she does.” A moment later, she pulled out a simple top to go with the skirt. She threw it to Chad and watched as he put it on. She would have much rather seen him dressed like a baby again, but at least his stupid bra and waist cincher were covered now. And the skirt she chose was very full so it should be good for his curtseying practice.
Now, there was just one other thing she wanted to change. If he couldn’t be dressed as a baby, then she might as well see him struggling in some high heels! “Take those shoes off, Sissy. They’ve got to go too.”
She turned around again and started searching through his shoes. He certainly had a lot of heels for a guy. Most of them were fairly high ones too. She selected a pair of the highest ones she could find that strapped onto his foot and handed them to him. As he buckled them on, she was amused to notice that it looked like he had already had a lot of practice putting them on.
When he stood back up again she looked him over. “Good enough, Sissy. Better then you were at least. Maybe later we can do something else with your hair and makeup.”
Chad actually felt a lot better now that he was dressed. Or maybe it was the heels on his feet. Either way, he felt better, almost refreshed. He smiled to himself a bit as he followed Sandy back to Mel’s apartment.
“We’re back!” Sandy declared loudly as they walked into Mel’s apartment. “Just like you wanted, I chose something simple and easy. And see, that didn’t take any time at all.”
Mel looked Chad over as Sandy sat back down again. Yeah, he did look better. She noticed the heels he was now wearing. Not exactly practical for what he would be doing all afternoon, but that wasn’t her problem.
“His skirt’s a bit loose in the waist,” Sandy added. “Do you have any safety pins we can use on it?”
“I’m sure I’ve got a few,” Mel replied as she got up and headed for her bedroom. She came back a few minutes later with a large pin in her hand. “Come here, Sissy. Let me fix your skirt for you.”
Chad walked over to her, but all she did was to stare down at him, waiting. Letting out a big sigh, he curtseyed. “Yes, Mistress.”
“Turn around, Sissy,” she ordered. He turned his back to her. She pulled the skirt up where it belonged and pinned it tightly in the back. When she removed her hand, it stayed up where it belonged. Chad had been happier when it was loose, it was too tight now. She turned him around to face her again. “I’m waiting, Sissy!”
Ugh! “Thank you, Mistress,” he said in his sissy voice as he dropped another curtsey. One thing he noticed right away, he had been happier curtseying in his other shoes.
“I’d call that a half-hearted curtsey at best!” Sandy declared.
Chad wished with all his might that Sandy would just stay out of things!
“It wasn’t really very good,” Cassie agreed.
Sandy got up from her chair and headed for him. “May I?” she asked Mel.
Mel smiled. “Be my guest.”
“You’re not doing it very pretty,” Sandy told Chad. “Now grab the sides of your skirt as far down as you can easily reach.
With everybody watching him so closely, Chad grabbed his skirt and waited for what was to come next.
“Okay, now curtsey and hold it.”
Chad put his foot back and dropped into a curtsey.
“Spread you skirt out further.”
Chad pulled his arms open wider.
“Wider!” Sandy commanded.
Chad stretched his arms even wider.
“No, that’s not quite right,” Sandy said, half to herself, not at all happy with what she saw.
“Try having him hold his skirt up higher,” Cassie chimed in from her seat across the room.
Sandy was a bit surprised by her suggestion. “Higher? That’s not right.”
“Just try it,” Cassie replied.
“You heard her, hold it up higher.” Chad raised his arms. Sandy looked at it, but it just looked all wrong and kind of silly. “Is that what you wanted?” she asked Cassie.
Cassie was giggling in her seat. “It’s not exactly what I had in mind but close. I like it even better though because now I can see his diapers underneath.”
Suddenly Mel started giggling too. “Okay, Sissy. Curtsey again and hold your skirt as high and as wide as you can.
Chad was mentally screaming. What was wrong with the way he had always done it? It got the point across… whatever point curtseying was supposed to relay. He did as he was told though, dropping and holding his curtsey with his skirt held high and wide.
Cassie was giggling again. “Oh, that full skirt makes that look so much better. I just love it when his diaper shows underneath. He looks like such a… a… sissy when he does it like that. Although it’s not very lady-like at all!”
Mel was all smiles. That was exactly what she wanted. “Back to your practice, Sissy. And now we want to see perfect curtseys from you from now on.”
Chad wasn’t sure what to think. Curtsey like they wanted him to? Like a sissy? Okay, so maybe he was a sissy, but still! He started to turn around to begin walking around the room again, but Mel quickly reached out and grabbed him. “Are you looking to get punished?” she asked.
Damn! He had forgotten again! This was getting too complicated! He curtseyed again, as best he could, to Mel and said his “Yes, Mistress,” in his little sissy voice. Then he turned around and began walking again. Only half his thoughts though were on curtseying, the other half were on how his very high heels felt on his feet. He loved wearing heels. It was part of the fun of dressing up for him. But he could tell right away that if she kept him walking around and around again, then his heels were going to get very tiring, very fast. And the curtseying certainly wasn’t as easy in them either.
He stopped in front of the lamp again, dropped his curtsey – being very careful to spread his skirt as high and wide as they wanted, and said his little sissy greeting. Then he paused like he was supposed to.
“Smile,” when you do that!” Cassie commanded from her chair. “You look like you’re mad at the world!”
Ugh! Why couldn’t she just leave him alone? He dropped his second curtsey – trying hard to put a smile on his face despite the fact that he didn’t feel much like smiling at all, and again thanked the lampshade. Stupid! Totally stupid!
“You need to smile more!” Sandy said as he walked around the room. “Your attitude is all wrong. Act… happy!”
Happy? The next time, he addressed the lampshade, Chad did his best to put a happy smile on his face.”
“Happier!” Mel ordered. “You could sound a bit more enthusiastic too.”
Enthusiastic? Happier? They had to be kidding! They weren’t the ones who were forced to do this stuff! He didn’t ever remember ever seeing a real woman do anything like what they had him doing! Let them try this for an hour or so!
Round and round he went, each time trying to do exactly what the women wanted him to. Until finally, he was going round and they weren’t making any suggestions to him at all. Whew! This was hard!
Mel left the room and came back with a baby bottle in her hands. “You need to keep drinking,” she told him before he had even gotten to where he could curtsey for her.
He stopped, curtseyed, took the bottle, and said “Thank you, Mistress,” as he curtseyed yet again. Then he took off again around the room.
Mel was pleased. He was getting there, but there was still a long way to go. She walked over to Cassie and Sandy and whispered to both of them.
Chad put the baby bottle to his lips as he walked around the room. He was more than ready for a drink. All this walking and curtseying stuff had him tired and thirsty… not to mention having to use the sissy high-pitched voice all the time. He took a few swallows of the tea and felt the cool liquid running down his throat. Relief!
But suddenly, Sandy was standing directly in his way. What was he supposed to do? He stopped, confused. Hoping he was getting it right, he curtseyed and said, “Yes, Sandy,” in his silly sissy voice.
Sandy giggled. “I like your skirt, Sissy.”
She liked his skirt? She stopped him for that? He curtseyed again, “Thank you, Sandy.”
“Very good, Sissy. You can go now.”
He hesitated, then dropped another curtsey and thanked her yet again. She moved out of the way and he continued his walk. Geez! What was that all about? But suddenly Cassie was blocking his way now. What was going on? He stopped in front of her and curtseyed for her too.
“How are you today, Sissy?” she asked.
How was he? Stupid question! “Fine, Thank you,” he answered as he dropped yet another curtsey.
“You can go now.”
He curtseyed again, thanked her and continued his trek. He got to the lamp and once again did it for the lampshade. Then he was off on another round, sucking his bottle now for comfort. But suddenly Mel was in his way. He stopped, feeling more panicked because it was Mel. He curtseyed and said, “Yes, Mistress,” in his best sissy voice.
“Show me your diaper.”
His diaper? Now? He hadn’t hardly thought about it for a while now because he had been so busy with walking and curtseying. He realized though that his diaper was fairly wet. He reached down and pulled up his skirt a bit, exposing the bottom of his diaper.
Mel reached out and felt the front of it, although she could see perfectly well how wet it was. “Very good sissy. But time is still wasting. Better keep wetting it.”
Chad dropped another curtsey and was about to continue walking when Sandy yelled, “Wait!” Everyone looked to her. “Tell him to show you his diaper again.”
Chad fervently wished that Sandy had stayed home today. She could be such a pain!
Mel looked at Sandy quizzically, but she repeated her command to Chad. “Show me your diaper.”
Chad again pulled his skirt up exactly the way he had done it a moment before.
“He doesn’t do that very well at all for a baby!” Sandy declared.
“He doesn’t?” Mel asked.
“No. Babies and little girls don’t have any shame about showing off whatever is under their skirts. None at all. They hold them up as high as they can, quickly and proudly. They like doing it so much sometimes that you can’t get them to stop.”
“That’s true,” Mel mused. “And no matter how he’s dressed, he is still somewhat of a baby. Besides, if it’s for a diaper check, then he’s definitely doing it as a baby!” She turned to face directly at Chad, who was mentally gulping. “You heard her, from now on whenever someone tells you to show them your diapers, you lift your skirt as high as you can. And you do it quickly and gladly! Got that?”
Oh brother! Chad couldn’t believe it. It was so stupid! But he curtseyed like he was supposed to and squeaked out in his sissy voice, “Yes, Mistress.”
“Good! Now show me your diaper.”
Chad hesitated only a moment, knowing that if he didn’t do it right, they would keep after him until they were satisfied. He quickly pulled his skirt up in the front as high as he could and tried to act like he was proudly showing off his wet diaper underneath. He felt like such a fool doing it that way, not to mention like such a baby too.
“Very good,” Mel said. “You can go now.”
Around and around. Curtsey and talk. Around and around again. Over and over, one of the three women would stop him and ask him dumb questions or make some dumb remark, only to get him to curtsey to them. Occasionally one of them would ask to see his diaper. He was tired of doing it long before he had even started. He kept drinking from his almost empty baby bottle more out of habit now than anything else.
And then Cassie stopped him. Curtsey. “Yes, Cassie?”
“Show me your diaper.”
As he had done many times already, he enthusiastically pulled the front of his skirt way up and held it there. But Cassie face suddenly turned from bored to confused. “Hey Mel,” she called. “It looks like his diaper is getting awfully wet around the edges. You might want to consider changing it soon.”
“Let me see,” Mel said as she headed over to look. Chad just stood there with his skirt held high. He hadn’t felt anything running down his legs yet so he didn’t think he was leaking.
Mel looked at his diaper carefully. “Yeah, the outside of it is getting all wet around his leg openings. Why didn’t you tell me it was leaking, Sissy?”
Chad was surprised. “I didn’t know,” he replied in his silly sissy voice. “I never felt it running down my leg.”
Mel nodded as she glanced at the clock. “You’ve managed to make it leak almost twenty minutes early. Good job, Sissy. I’m proud of you.”
Chad felt very elated at her words. It was a strange thing to feel good about, but he was more than ready to take whatever he could get. He had made his diaper leak early… without much effort at all. He had been so busy that he hadn’t been thinking about it much. And now Mel felt proud of him!
“Aw, is the widdle baby aww wet?” Sandy teased as if she were talking to a real baby. “Does she need Auntie Sandy to put a fwesh didee on her?”
Cassie giggled. “Sandy stop! You sound more like a baby than he does.”
Mel laughed too. “Yeah, she does.” Then she stopped short and stared at Sandy. “That’s not right!”
“It’s not?” Sandy asked, wondering what Mel was thinking.
“No it’s not,” Cassie agreed, sounding more serious.
“It’s not at all right that you should sound more like a baby than him! Sandy, can you teach him to talk like that?” Mel asked.
Sandy was surprised. “I don’t know. It’s just something that I’ve always done with babies.”
The more Mel thought about the idea, the more she liked it. “Can you figure it out? I really want him to learn it.”
“Sandy looked really uncertain. “I don’t know what I do. I just do it.”
“Tell you what, see if you can figure something out while I change him. Okay?”
Sandy shrugged. “Sure, I guess.”
Chad wasn’t liking anything that he heard. Not at all! What they were considering would make him sound like even more of a stupid fool than he already did. And the idea scared him a bit.
“Come along, Sissy,” Mel said as she headed for his diaper bag. “Let’s get you changed.”
A few minutes later, Chad was in a fresh dry diaper with yet another two hour time limit to make it leak. Mel allowed him to get a fresh bottle to hold and drink while he was doing whatever else they came up with.
“I’ve been trying to figure out what I do,” Sandy said as soon as Chad was ready. “And I think I’ve figured out a few things we can try, but really, there are no rules to this stuff.” She looked at Chad. “God I wish you were dressed like a baby. It would make this so much easier.”
“I want him to talk like this all the time,” Mel said, “not just when he’s dressed like a baby. In fact, when he’s dressed like a baby, I’ll probably have him use the other baby talk that you’ve already taught him.”
“Oh!” Sandy exclaimed. “That’s an interesting idea. So this is going to be his… grown up language then? God, he’s going to sound like such a…” she tried vainly to search for the right word.
“A sissy?” Mel prompted.
“Yeah, that’s for sure!”
Chad was growing even more nervous. Talk like that all the time? Fat chance! But what other option did he have?
“Okay, Sissy,” Sandy said. “Let’s try to figure this thing out. The first thing we’ve got to do is to replace everything that has an ‘r’ sound with the letter ‘w’ instead. Try it.”
Chad didn’t know what to say. “And say what?” he asked.
“I don’t know. Think of words with the letter ‘r’ in them.”
Chad searched his brain. R? The word rabbit came to mind. “Rabbit?” he asked. Then he tried the new way. “Wabbit?”
“Yeah, that’s it,” Sandy said. “Perfect.”
“Wabbit!” It reminded Chad of Elmer Fudd. “I hunting wabbits,” he said, trying to sound humorous. “I’m going to get that wascally wabbit!”
“That’s it,” Sandy said excitedly while Mel and Cassie both laughed. “Just do that! It’s perfect!”
Chad shrugged. So they wanted him to talk like a high-pitched Elmer Fudd. Talk about dumb! It wouldn’t be the easiest thing in the world, but he could think of far worse.
“Okay, Sissy,” Mel said, “back to your practicing. And add this to your requirements for your sissy talk.”
Back to his practicing? She wanted him to start walking around and curtseying again? He wanted to scream! With a big sigh, he started walking around the room once again. He got to the lamp, stopped and curtseyed. “Hello, Mis…” he paused. The word had an ‘r’ in it. “Mistwess.” He said to the lampshade.
“Very good,” Mel said from across the room where they were all watching him.
“No it’s not!” Cassie interrupted. “I didn’t like the way he said the word ‘hello.’ I think that should be the same as with the ‘r’ sounds so that instead of ‘hello’ it should be more like ‘hewwo.’” She looked at Sandy and Mel both for approval.
“Definitely!” Sandy replied, looking to Mel for confirmation. “Good one, Cassie. Try it again Sissy.”
Oh brother! Now it was ‘l’ sounds too? This was going to be more difficult! He looked back at the lampshade, curtseyed again and said, “Hewwo, Mistwess.” He looked back at the women for approval.
“Yes,” Cassie declared.
“Good,” Mel agreed.
Chad just rolled his eyes, looked back at the lampshade, curtseyed again, and said, “Thank you, Mistwess.” As he stood back up, he was grateful that ‘thank you’ didn’t have any ‘r’ or ‘l’ sounds in it!
The women kept him practicing for a little while more, often stopping him to ask him different questions, forcing him to try to learn to use his new speaking requirements. He eventually got better, but it was obviously difficult for him.
Finally Mel looked at the clock and called a halt to it all. “I’m sorry, ladies, but Sissy has work to do now… that is if you ever want to eat tonight. So I need to get her busy in the kitchen.”
Chad was ever so grateful that it was all finished. He was tired of walking around the room in circles and talking stupid. He thought he sounded like a moron! And the heels on his feet weren’t helping matters either. Finally, he could relax and just make dinner – do something he actually enjoyed for a change!
“Sissy, don’t forget, you’ve only got about half an hour for that diaper!”
Damn! Didn’t it ever end? “Yes, Mistress,” he replied.
“Do it right!” Mel yelled quickly.
Did she mean for him to keep talking silly? Not to mention curtseying? He dropped another curtsey, being careful to spread his skirt like he did before… knowing that it probably showed his diaper underneath, and said, “Yes, Mistwess.” Damn! This wasn’t easy!
“Remember, Sissy, you never speak with curtseying… anytime! And I never want to hear anything except your new sissy voice. And that means either baby talk like Sandy taught you, or your new sissy talk. Never anything else! Period!
Chad wanted to cry. Did she really mean always? That would be almost impossible. “Yes, Mistwess,” he said rather forlornly as he dropped yet another curtsey.