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!