The Bet - Chapter 37 (Sunday – week 6 Part 1 of 7)

The Bet
by Karen Singer

Chapter 37 (Sunday – week 6 Part 1 of 7)

In his dreams he was wearing his silly baby dress, sucking on his pacifier, and holding a baby bottle in one hand as he went into someone’s house. His friends were all there – his male friends. They had all come to play poker. There was a highchair at the poker table. He skipped from the door to the highchair and climbed up into it as all his friends laughed at him. Someone put the tray in place for him. “Fankyou, he said in his silly sissy voice. For some reason, he was saying the letters “th” as an “f.”
The cards were dealt and he played his from the tray on his highchair – although he didn’t really play since he wasn’t allowed to hold the cards in his hand. All his cards were arranged face-up on the tray in front of him where everyone could see them. Instead of playing, he sat and drank his bottle as someone else leaned over and looked at his cards, then played for him.
Eventually, someone requested to see him dance since he wasn’t really playing cards. His tray was removed and he jumped down. He pulled his baby dress off and amazingly, underneath he was dressed in a pink ballet costume. For some reason, it seemed like the pink leotard encasing his body was baggy and wrinkled, looking way too big for him.
With a silly little tutu surrounding his hips, he danced the same steps he practiced over and over again in Mel’s living room. Awkward steps, silly steps, with his feet turned outward. Between the steps, he jumped and leaped – terribly. Yet the men playing cards didn’t seem to mind, they only laughed at him harder. He danced all around the table, round and round while they played. He only stopped occasionally to drink from his bottle.
As he was drinking, he suddenly felt himself peeing a huge amount. His diaper started leaking through the tights and leotard he was wearing. His knees pressed together as he looked up in alarm. And then Mel was there. She took him by the hand and laid him down on the floor. She handed him yet another bottle to drink while she changed him… lovingly. He sucked away happily, knowing that he was loved and cared for.
And when Mel was done, she picked him up and held him to her as if he was a small child. One hand that held him reached down toward his diaper covered bottom and pressed through the diaper against his anal opening. Such a sexual thrill. Over and over again she pressed and released. His legs wrapped around her as the sexual tension within him grew. The feel of her body against his only added to his pleasure and heightened his sexual state.
Pain! Pain in an area where he didn’t want pain suddenly crept into his dream, yet he didn’t want to let the dream go. Over and over again, the dream Mel pressed against his backside. She felt so wonderful against his body. But the more his dream sexual excitement grew, the more the odd pain against his cock kept growing, intruding… ruining everything. It hurt! Too much!
He crawled his way out of sleep with the realization that his cock had been trying to get hard again inside of the chastity device. The miserable little teeth inside the device were hurting him horribly. He pressed his hands against the overly bloated front of his diapers, but his hands could have no affect – the chastity device was a world unto itself, especially underneath the incredible bulk that surrounded it.
Frustrated and hurting, he rolled off of his blow-up mattress and onto the floor, scattering empty baby bottles in the process. He climbed to his feet and glanced at the clock. The sunlight creeping past his window shades was a bit dim yet. His clock told him it was early, yet he knew he couldn’t go back to sleep. Not with the lousy pain still in his groin. Hurting and unable to do anything about it, he waddled out toward his living room and the kitchen beyond, hoping that doing something else would alleviate the sexual thrill that was still infecting his untouchable penis. It worked, but all too slowly.
He found her note, as usual, on the counter along with his cookbook.


Sissy,

Three more bottles this morning.

It’s grocery shopping day. Find something new again from the book to fix tonight. Cassie and Sandy will probably be joining us as usual.

Call me the moment you finish showering again so I can be there when you put your diaper on!


That was it – a very short note with nothing new at all… all the better. He went to the refrigerator and opened it. As he had discovered last night, it was once again fully stocked with a huge number of baby bottles. Most of them filled with her lousy tea. He grabbed three and carried them out to the living room, plopping the pacifier from his mouth down on the kitchen counter as he walked past.
He sat in his only chair – his only piece of real furniture. As he sat, he immediately noticed the added picture on the wall in front of him – a second picture that he had colored childishly in a restaurant. He had “presented” yet another one to Sandy yesterday. Having to stare at the pictures and knowing that it was he who had colored them so childishly, made him feel all the more childish inside, and silly, and small, and ridiculous. Staring at the pictures while drinking his bottle only made the situation that much worse. And doing all that while wearing overly wet and messy diapers compounded the situation yet again. Total humiliation! And the pain from his hated chastity device suddenly returned. Ugh! Why all of a sudden was it back? He hadn’t felt anything down there in a long time now! And the feeling was so irritating that he wished he’d never have to feel it again.
But one irritation seemed to lead to another. Before long, he became aware of an odd, almost numb feeling coming from his earlobes. His new earrings! He reached up and touched one while he drank. Instead of finding just the soft flesh of his earlobe, he felt instead the hard small earring that was stuck through it. He lightly pricked his finger on the pin in the back. He remembered all too well going to bed last night and being bothered by those sharp little points. Sleeping comfortably was becoming more and more of a problem.
He was supposed to have removed the earrings and cleaned the holes before he went to bed last night. Mel had even told him to do it. But he hadn’t bothered. He supposed he had just felt a bit too depressed once he finally got home last night. Mel had used him hard once again, and then she had played with her toy up inside of him for a while. Yet while he felt a tremendous amount of pleasure from her toy, he wasn’t able to achieve any level of fulfillment from it – as usual. Maybe that was why his chastity device was giving him so much trouble today – it was punishing him for feeling pleasure in a place where he shouldn’t!
Two bottles later, the pain in his groin was still there, but it was much less – or maybe it was just some left over irritation. Under all the diapers and totally incased inside the chastity device, it was hard to tell exactly what was going on down there. Either way, the pain was still a nuisance. He decided to grab his shower and get cleaned up before he drank the third bottle – hoping that a break from wallowing in his own humiliation would make the irritating pain go away again – permanently!
He glanced at his clock, it was still fairly early. He would have to phone Mel as soon as he got out of the shower. But was it too early? Would Mel even be up yet? But he needed to get his mind on other things for a while. He needed to do something to take his mind off of the chastity device – and the trouble it was causing him! Having nothing else to do, he headed for the shower to start getting cleaned up.
In his bathroom, he stared into the mirror. The twin points of color attached to his ears winked back at him. He reached up and carefully fumbled with the clip on the back of the earring to remove it. Fortunately, it wasn’t too difficult to figure out. Then, grabbing the front of the earring, he slowly began pulling it out. While he couldn’t feel much, he could feel it a little. An almost squeamish feeling wound its way up through his system as he removed it. Fortunately, it didn’t last too long. He breathed a sigh of relief as he set the earring down on his counter and rubbed his earlobe. Not too bad at all.
The second earring came off faster. He cleaned both his earlobes and the earrings as Mel had told him he should. Then he had to put the earrings back in again. Finding the holes proved to be fairly difficult and took some time. The thought that what he was doing was something that most women did all their lives didn’t escape him. Eventually, the hole was found and eventually, he managed to get the back clasp on it again. Whew! One down. While the second earring had come out faster, it certainly didn’t go back in any faster, but eventually that one too was back in place.
He looked at his image… and smiled. Yes, he did like them! And they too added to his feeling of femininity. And for the first time all morning, he realized that his chastity device wasn’t bothering him. Now if it would just continue to stay unnoticed! If not, then he might just have to clean his earlobes again!

Mel hadn’t been fully awake when her cell phone startled her away from the dream she was having. She mentally cursed at the irritation of having to wake up to answer the stupid phone! Whoever it was, had better have a good reason for calling so early! “Hello!”
“Good Mowning, Mistwess,” Chad replied in his sissy voice. “I just got out of the showa.”
Damn! It was Sissy! “Why are you calling me so early?”
“Your note said…”
“I know what my noted said!” she replied angrily. “Okay. I’ll be there in a minute.” She shut off her phone and stared at the wall for a moment. This morning wasn’t starting off real well… and her period wasn’t due to start till tomorrow! Still irritated, she pulled her robe on, grabbed her keys, and went out her door.
Chad had just finished drying himself off and was about to pull one of his disposable diapers into place when he heard Mel enter his apartment. He waited, holding the diaper around him in case he suddenly lost control, until she finally appeared in his bathroom doorway. She looked like she had just gotten out of bed… or maybe like she should still be in bed! “Hello, Mistress,” he said once again. She said nothing at all to him, the irritated look on her face didn’t change at all. He finished taping the diaper in place. “Two hours?” he asked, knowing that would be the drill.
She nodded. “Two hours. What are you doing up so early?”
“I couldn’t sleep,” he replied.
She grunted. “Remind me to wear you out more before I send you home for the night!” She turned to leave, then turned back again. “Uniform again! When you’re ready, come to my place and start cleaning… or whatever you need to do. Make coffee! I’m going back to bed so don’t wake me!” She turned and left. Chad just stared after her. Maybe he shouldn’t have woken her up so early.

The aroma of fresh coffee reached Mel’s nose as she laid in bed trying to hold onto sleep. But she had been awake once already and coming awake for the second time that morning happened all too easily. She breathed in and smelled the coffee again. Mmmm. This was a much better way to wake up in the mornings – coffee already made! She pulled herself out of bed and had her robe fastened around herself before she realized that she should have stayed in bed and had Sissy bring it to her. Oh well, next time she would remember it. She headed out to the kitchen, following the brewed aroma of the drink she seemed to crave.
“Good morning, Mistress,” Sissy said with a curtsey as soon as he spotted her. He was at the sink washing the few dishes she had used the night before. Even though she thrilled to see him curtsey to her, she ignored him and went straight for her coffee pot. A minute later, she was closing her eyes as she enjoyed the first sip. “Mmmm.” This was how it was supposed to be, her coffee already fixed for her in the mornings and waiting on her. She couldn’t wait to win the bet, then she would have him fix her coffee every morning – and probably bring it to her in bed! Soon! Very soon! But first, there was the little matter of winning the bet to get out of the way.
She leaned back against the counter and stared at his back while he toiled over the sink. Hunched over like he was, he looked more feminine than ever. And the uniform… it just seemed to thrill her in so many pleasant ways. Her maid. Her very own maid. And… something much more. But trying to define what that “something much more” really amount to was beyond her capabilities just then. Not that she was really concerned about it.
She watched as he finished with the dishes and dried his hands with a dish towel – and then seemed to stare at his lavender painted fingernails for a moment as if he was admiring them. Perhaps he was. The simple gesture seemed so totally feminine, not masculine at all. Which reminded her, she still had to address some of his other masculine habits! Eventually, anyway.
Chad put the dishtowel down and turned around toward Mel. “Would you like me to make you something for breakfast?” he asked.
Mel smiled. So nice! “Maybe just some toast. Have you eaten?”
“Not yet,” Chad replied.
“Then make your own breakfast too while you’re making mine. The baby cereal is in the cabinet.”
Ugh! Baby cereal. Now she was not only making him eat it, but she was making him make it for himself too! “Yes, Mistress,” he replied with a disappointed curtsey. Baby cereal again! Yuck!
Mel’s cup of coffee was halfway done by the time her toast popped up. She hadn’t moved from her spot leaning up against the counter where she was watching him stir the pot of baby cereal. Chad grabbed her toast and put it directly onto a plate. “Do you want me to butter it for you?” he asked.
She thought a brief moment. It would be nice, but… “No, I’ll take care of it myself. Just leave it there on the counter and get back to your breakfast.” As Chad turned the burner off under his cereal, she opened the refrigerator and chose one of her jams to spread on the bread. As she was fixing her single slice of toast, she watched him pour his cereal into a child’s plastic bowl and carry it over to set on the table next to his highchair. She warmed up her coffee by pouring more into the cup as she watched him pulling the tray off. She picked up her slice of toast and leaned back against the counter again as she watched him looking around, trying to figure out how he was going to work everything. She almost giggled. “Let me help you.”
Chad climbed up into the highchair, and she put the tray in place for him, essentially locking him into the chair. She picked up one of his bibs that she kept close by and tied it around his neck. As messy as he was when he ate the cereal, he really needed it. She picked up his bowl and put it on the tray for him. But there was still something missing… no, two things. “No spoon?” she asked. “Or would you prefer to eat it with your fingers?”
Chad looked around the tray for his usual baby spoon and realized he had forgotten it. “I forgot the spoon, Mistress. Please may I have one?”
So polite! She loved it. Instead of answering, she grabbed one of his spoons and stuck it down on his tray for him. “Don’t forget, you use that thing now like Sandy showed you.”
Chad felt instantly frustrated. “But Mistress, it’s hard. And I keep dropping more of the food.”
“It’s easy enough for babies. So it should be easy enough for you,” Mel replied with a bit of a wicked grin. She picked up the other missing item and also set it in front of him – his latest baby bottle that he had yet to finish.
Chad grabbed the spoon in his left fist and dug it into the mushy cereal. He got it mostly to his mouth before half of it fell off and landed on his tray. Even at the best of times he dripped a good bit of the cereal onto the tray, or his bib… or his face. But now, he had a feeling that he wasn’t going to get a whole lot of the cereal actually into his mouth this morning. It was humiliating enough having to eat the unrecognizable taste of the bland baby cereal every morning. It was worse that he usually dripped much of it off of his spoon and made a mess like a baby. It was even more humiliating to have someone watching him do it all the time. And now, having to hold the spoon like an infant and try to get everything to his mouth made the whole exercise that much worse – and humiliating. Yet a part of him was more thrilled than ever by that very fact!
“Any trouble with your earrings?” Mel asked.
He shook his head. “None. It’s a bit difficult trying to get them back into the holes after I cleaned them.”
“You’ll get used to it,” Mel replied with a small smile.