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?