The Bet - Chapter 15 (Saturday – week 2 Part 4)

A huge thank you to everyone for all your well-wishes for me. I’m doing a bit better and am now “occasionally” getting allowed near the computer. Basically, I’m doing a lot better than I know I have any right to be doing, but I have a very, very long way to go. I hurt… and I’m still more than a bit scared. More some other time.


The Bet
by Karen Singer

Chapter 15 (Saturday – week 2 Part 4)

As soon as they were back inside Mel’s apartment, she sent him to her room to change into his maid’s dress. “When you come out, I expect you to be ready for my inspection!” she told him.
Chad went into her bedroom and changed into his dress and low-heeled shoes. After wearing the higher heels for so long the low-heeled ones felt like heaven. He tied the apron around his waist and smoothed the front of it. He didn’t know what else he could do since he had no idea what Mel might be looking for when she inspected him. He went back out to her living room to find her. She was in the kitchen, pouring the last of the drink she had just bought him into another baby bottle. She glanced up. “Just stand there in the middle of the living room till I’m finished.”
Chad waited the few moments it took her to finish what she was doing. Then she took a moment to wash and dry her hands before she came out to see him. “Are you ready for your inspection?” she asked.
Chad immediately curtseyed and said “Yes, Mistress.” Although he was really wondering what kind of new game she was playing now.
“Stand up straight… straighter. Head up. Look straight ahead!”
What did she think this was, the army? Chad did as he was told.
“Put your feet together. Keep your hands at your side. Now stay that way.”
As Mel walked around him, she could literally feel the juices flowing in her all too moist sex. She couldn’t believe how much she was enjoying this. As she looked him over closely, it was getting to her more and more. He really looked pretty good. There were a lot of areas though that needed improvement, but they were areas that were going to take time. His dress and apron were beautifully pressed. His shoes gleamed. His makeup… that was bad, real bad. And his hair… She loved the way his new necklace fell just short of the neckline of his dress. Perfect! His new watch was an improvement too. He was slowly looking more and more feminine, and that was what she loved. It was a HE that was looking that way… because she was making him do it. That was power!
She reached out and fussed with his apron bow behind his back, making it more even and puffing the bow up more. Then she stood in front of him with a very critical look on her face. “Your makeup is horrible! You need a lot more work young lady!”
Chad’s arousal suddenly soared the moment she called him ‘young lady.’ Had she slipped up? Either way, he was a thrilling moment.
“Now go fix my dinner… and I expect my fries to be hot this time!”
Chad immediately headed to the kitchen. Yes, the lower heeled shoes really felt good to him. So much more comfortable! His dress was really comfortable too. He could do without the white apron, but that was really no problem. He pulled her sandwich and fries out of the bag and noticed that his food wasn’t in the bag anymore. He realized she had probably put them into the refrigerator already. He quickly checked. Yep! There they were. Getting cold already. He went back to fixing her dinner, not only reheating her fries, but also the burger too.
All too soon, he found himself standing in the corner again while she ate. It was really becoming quite a pain. The corner was boring, boring, boring! And she didn’t even allow him to move. He finally noticed the slight urge to pee and he concentrated on it. It was at least something to think about, and besides, peeing felt good. Really good! The feeling built quickly and soon he found himself trying to hold it back. He mentally counted seconds to himself as he held it. He only got to twenty before the pressure became too intense and he started wiggling a bit to try to hold back longer.
“Stop fidgeting!” Mel’s voice cut through the room. He stood still and allowed himself to wet his diapers. Less than thirty seconds. Pitiful! He couldn’t believe how much control he had already lost in this bet. If he hadn’t realized that he was no longer holding back at all this morning, then Mel might really have won the bet – easily. Three weeks. That was the first milestone from his research. It took three weeks to form a habit. But after only two, he no longer ever thought about using a toilet anymore. He automatically went in his diapers without thinking. She had somehow shaved an entire week off of that part. But fortunately, he had realized what was happening before it was too late. And he was fighting back now. His legs were beginning to cramp a bit and he shifted his weight and raised one foot barely off the floor. “Keep your feet down! Stand still!”
It seemed like an eternity before Mel finally allowed him to leave his corner. She made him clean up the table and counters before she allowed him to sit on the floor and eat his dinner, along with three baby bottles of coke. He wasn’t really fond of cold hamburgers, and even less fond of cold French-fries, but there wasn’t much he could do about it. He was hungry.

As soon as he was done eating, Mel set him to cleaning her entire apartment again, even though it needed very little cleaning. She watched him closely from one of her chairs the entire time, all the while basking in the glow of her sexual arousal. She couldn’t wait to have him between her legs again. And today her period was officially over. She hadn’t even spotted all afternoon. But there was plenty of time for that later. She wanted to feel the power building slowly all evening first.
Somebody knocked loudly on her door. The sudden interruption made Mel want to scream. She glanced at Sissy. He was looking at her, obviously scared. She wasn’t going to let him run away though. “You’re the maid. Go answer it!”
Chad couldn’t believe it. She wanted him to answer her door dressed like this? But he realized she was completely serious. Hesitantly, he went to the door and took a big breath before opening it to steady his nerves. Then he pulled the door open wide.
“Hi!” Cassie said excitedly as soon as he had gotten the door half open.
“Aaaah! You’re a maid today!” Sandy squealed from right next to her. “I love it! Let me see you!”
Chad quickly turned back toward Mel. She was now walking toward them. “Don’t just leave them standing there, Sissy. Let them in. And don’t forget to greet them properly!”
Chad stood back and held the door open for them. “Hello, Cassie,” he said dropping quick curtsey as the first girl walked past. “Hello, Sandy,” he repeated as Sandy walked past.
“Oh, he’s adorable.” Cassie said, not taking her eyes off of him.
“He’s getting there,” Mel replied proudly.
“He still needs a lot of work with his makeup I see,” Sandy noticed. Mel sighed. “That’s been a major problem so far. He’s just not good at it. But really, I guess it hasn’t been all that long and I’ve only been pushing a little bit at a time, so I guess the fault is partially mine.”
“Don’t say that!” Cassie replied. “It’s never your fault, girl!”
“You want me to work with him a bit on it?” Sandy asked. “I used to do it in a department store for a while before I graduated.”
Mel looked surprised. “You did? I mean, did you do makeovers and stuff, or just sell the makeup.”
Cassie laughed. “Oh she does it all! Where do you think we met?”
Mel seemed confused. “But you don’t ever wear much makeup.”
“Oh, but she can be a real looker when she wants!” Sandy replied. “Trust me!”
Mel didn’t think she wanted to pursue that any further. “Do you really think you can help him though?”
Sandy looked at Sissy’s face critically. “I know I can!”
“Have you ever done a guy before?” Mel asked next.
Sandy laughed. “Not yet, but hopefully soon!” The three women laughed.
“You call that a guy?” Cassie asked. And they all laughed again while Chad felt his face turn red again.
The three women went into the living room to sit down, talking and laughing as they walked, leaving Chad standing alone. Mel turned back to him before she sat down. “Why aren’t you cleaning?” Chad instantly got back to doing what he was doing before he had been interrupted.
He couldn’t hear much of what they were talking about since they were all ignoring him and he was mostly in other parts of Mel’s apartment. But it didn’t seem like very long at all before Mel yelled to him, “Sissy, our company is leaving. Please get the door and say goodbye.” Chad hurried from the bathroom to the living room where all three women were standing by the door waiting for him. He dropped a quick curtsey and said goodbye to both Sandy and Cassie. Then he opened the door for them. “Oooo!” Sandy said as she walked out, “I can’t wait till tomorrow!”
When they had gone, Chad closed the door again and turned toward Mel. “Tomorrow?”
“Yes, Sissy. Sandy is taking you shopping for more makeup before we go grocery shopping. Isn’t that wonderful?”
Chad wasn’t sure at all about that. “Yes, Mistress,” he replied half-heartedly as he dropped yet another curtsey.
“Oh, and I’ve invited them both to dinner tomorrow night. So whatever you decide you’re going to be cooking, make sure that you get plenty for all three of us.”
Dinner – for all of them? He supposed he could do that with no problems. As he curtseyed yet again to say “Yes, Mistress.” He realized that he was actually looking forward to cooking for all of them. Mel seemed to think he was a really good cook. Maybe he could impress all of them. He just needed time to study that new cook book for a while. He went back to cleaning Mel’s already spotless bathroom.
Mel went back to watching Chad. When she could, she sat in her living room and watched. When he wasn’t where she could see him, she went to stand in whatever doorway of the room he was in. She realized she was being silly, but she didn’t care. She couldn’t help it. She was enjoying the sight of her maid too much. The way he looked and moved in that dress was doing something to her. In fact, it was doing a lot of things to her. Wonderful things to her.
Eventually, she couldn’t stand it anymore. As soon as he had finished cleaning her bedroom again, she stopped him. “Ok, Sissy. That’s enough for tonight. I want you undressed down to your diapers and plastic panties right now.”
Chad was grateful to stop cleaning. She had been following him around since Cassie and Sandy had left like a puppy dog. Unfortunately, he had been all too aware of her scrutiny and had put a lot of extra effort into his cleaning because of it. What he worried about now though, was whatever she wanted from him next? He had one major guess.
After he had hung his dress back up again and was wearing just his diapers and plastic panties, he went back out into the living room. His suspicion was instantly confirmed by the towels covering her sofa and the piece of rope on the coffee table that had already been moved. Mel was waiting for him, holding another scarf in her hands. “Must you,” he asked as she tied the scarf tightly around his head, blocking all his vision.
“Hush!” was her only sharp command.
He felt her roughly grab his wrists and tie them behind him. Then she pushed down on his shoulder till he was kneeling again and tied his wrists loosely to his ankles. After that, he could only hear her moving around in front of him for a long time.