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.