The Bet - Chapter 30 (Sunday – week 5 Part 6 of 7)

The Bet
by Karen Singer

Chapter 30 (Sunday – week 5 Part 6 of 7)

The doorbell rang. “Sissy,” Mel called from her bedroom. “Don’t forget, I’ll be listening.”
Ugh! Chad felt silly. Not just for the way that Mel wanted him to behave tonight, but also for the way he was dressed. At least his diaper was fairly fresh, Mel had changed it less than half and hour ago. He had managed to make the last one leak again, something he was fairly proud of. But now he was working on yet another two hour deadline. His biggest problem though, was the way he was dressed. Mel had fussed extra long with both his hair and makeup. His hair was basically the same – if you didn’t count the big white bow she had fastened on top. He tried hard not to think about that. His makeup was a bit different too, brighter, bolder, and certainly more colorful. There was no way to miss his bright red lips.
He was wearing his bra and waist cincher – naturally. No girdle or pantyhose – nothing that would make it difficult for Mel to see how wet his diaper was. Of course, seeing his diaper would be no problem – for anybody, since he was only wearing the top to his baby-doll nightie. The only other thing he had on was the darn pink patent high heel shoes she had bought him yesterday… oh yeah, and his pacifier that was now attached to a long pink ribbon that was pinned with a fancy pink bow to his baby-doll top. It was a strange outfit, but he knew all too well that it was also only temporary.
He opened the door, Mel’s secretary, Andrea, was there holding a bottle of wine. Just as Mel had made him practice over and over again, he removed the pacifier from his mouth and dropped his elaborate sissy curtsey to her. “Hewwo, Andwea,” he said in his best sissy voice. He knew that Mel would be listening for sure. She had made him practice this greeting over and over again till she was happy with it.
Andrea was so startled she almost dropped the bottle in her hands. “Hello, Sissy,” she replied, still trying to take in the way Chad was dressed, let alone his voice and his curtsey. “May I come in?” she asked.
“Of couwse,” Chad replied, curtseying yet again, then standing out of the way. He didn’t turn to look, but he could just feel Mel watching him. Over and over again she had made her rules very clear for tonight. He had to always use his new sissy voice – always! He had to curtsey every time he said anything – always! He had to keep his pacifier in his mouth all the time, unless he was talking or drinking from his bottle – even if it meant taking it in and out constantly. And above all, she wanted him to do his best to try to show everybody just how much he loved being a sissy. Okay, he did love it. And deep down, everything he was doing thrilled him to the core. But still, he felt silly.
“Hi Andrea,” Mel’s voice called as she walked out of her bedroom. She was dressed semi-casually, but Chad thought she looked extra good tonight.
“Hi Mel. I brought a little bottle of wine, just in case you might need it.”
“Thanks, Andrea. Wine is always appreciated.”
“What’s with the way you’ve got him talking? I nearly jumped out of my skin.”
Mel laughed. “Don’t you just love it? That’s his new sissy talk we’re working on.”
“I wasn’t aware that he needed anything else to let people know what he is.”
Mel laughed. “True! Let’s just say that I’m trying to make sure there’s no question about it.”
“I don’t think you’ll have any trouble.”
Mel looked over at Chad. “Sissy, aren’t you supposed to be busy in the kitchen? And there’s something wrong with your mouth!”
Chad quickly grabbed his pacifier and stuck it back in place again. Then he headed back to the kitchen to finish preparing dinner. There wasn’t really much more to do. Everything was mostly ready.
A few minutes later, another knock came at the door. “Sissy!” Mel called from the living room where she was talking with Andrea.
Chad ran out from the kitchen, spat the pacifier from his mouth, curtseyed, said “Yes, Mistwess.” Then he hurried toward the door as fast as his very high heels would let him go. He opened the door again. Sandy and Cassie were there. Both of them seemed to be dressed nicer than usual too. Big sissy curtsey. “Hewwo Cassie.” Another big sissy curtsey. “Hewwo Sandy.”
“Well, hewwo to you too,” Sandy replied teasingly. “Don’t you look just… adorable! Love your bow. You should consider wearing one more often.”
Chad blushed as he stood back out of the way for the women to enter. As they walked past him, he reached down and grabbed his pacifier and put it back into his mouth before Mel could yell at him about it again. Then he hurried back to the kitchen. Everyone was here. It was time to serve dinner.
He had already set the table, so it was just a matter of dishing everything out. As he raced around the kitchen, he occasionally grabbed his latest baby bottle, this time filled with apple juice, and took a quick drag on it before sticking his pacifier back in his mouth. He looked over the table carefully. The food was finally dished out but as per Mel’s orders, the wine was not yet poured. Otherwise, everything looked perfect. Taking a deep breath, he headed into the living room where the women were talking. He pulled his pacifier out of his mouth and let it dangle from the ribbon it was attached to. “Excuse me, Mistwess,” he said as he curtseyed. “Dinnew is weady.” Then immediately, he grabbed his pacifier and put it back into his mouth again.
“Thank you, Sissy,” Mel replied.
“Wonderful!” Andrea exclaimed. “It smells so good, I can’t wait.”
“It’s always good!” Cassie replied as they all got up from their seats.
Chad hurried back into the kitchen ahead of the women. He grabbed the bottle of wine that he had already opened and approached Mel first. “Would you wike some wine, Mistwess?” he asked.
“Yes, please,” Mel replied and watched as Chad poured her drink. She watched him carefully as he asked the same question and poured drinks for each of the women. She was pleased. He was behaving perfectly. Exactly what she wanted. And when it came to cooking and serving dinner, he really was very good. She wondered briefly where he had learned to serve like he did.
As the women all began eating, Mel looked around the table, checking everything and everyone. It looked like nobody was going to need anything for a few minutes. Sissy could be spared. She looked towards him, he was standing attentively out of the way, watching them. “Okay, Sissy. Time to change.” She watched him as he curtseyed to her and said his little sissy reply. Then he hurried off.
“Change?” Andrea asked.
“You said you wanted to see him in some of those outfits I got him,” Mel replied.
Andrea smiled. “I can’t wait!”
Mel’s bedroom seemed to be filled with ruffles and sissy things. Earlier, Mel had carefully laid out three different outfits for him to wear tonight. Looking them all over, he couldn’t decide which one was the worst… or the best – depending on how he looked at it. But there was no time now for musing about such things. If he didn’t hurry, then Mel had promised a severe beating… and Chad was trying extra hard to not let that happen!
He hurried over to the first outfit. Unbelievably, it was the most babyish looking of all the outfits – not that the others were really very far off. The very short pink check pattern of the dress over top of the built in white blouse just seemed to look very juvenile.
He set about taking his shoes off, then his baby-doll top. First he struggled with the frilly new ankle socks she had made him buy yesterday. Lots of pretty lace around the ankles to go with the pink checks in the dress. Then he buckled the same pink high heels back onto his feet again. To him, the shoes seemed very out of place with the nature of the dress. But that hadn’t been his decision. Mel had decided. Each of the other dresses had their own shoes to go with it and Mel had decided on these for this dress.
Before he pulled the dress on, he carefully transferred the long pink ribbon attached to his pacifier to the new dress, then he slipped it on. Buttoning it up in the back was extremely difficult, but through sheer perseverance, he finally managed it. But by the time he did, he was beginning to worry about how much time it had taken. He quickly checked his image in Mel’s full-length mirror. He popped his pacifier back into his mouth and hurried out to the women.
All eyes turned to him as he returned and curtseyed yet again for them all. “I’m sowwy I took so long,” he apologized. “Does anybody need anything?”
“Oh my!” Andrea exclaimed. “That dress is just too much! And I love the way the bow in his hair matches the little white bows on the front.”
“Wait till you see some of the other dresses,” Cassie replied. “I think they’re even better.”
“I like this one,” Sandy said. “I think it’s the most babyish of them all.”
“You would like this one!” Cassie laughed.
“Okay, Sissy,” Mel commanded. “Go get your perch and set it where we can see you.”
“Yes, Mistwess,” Chad replied with another curtsey. Then he hurried off.
“His perch?” Andrea asked.
“Oh yeah!” Sandy replied. “Wait till you see it.”
Chad came back a moment later with his heavy wooden perch. He set it carefully in place on the floor, then he climbed onto it.
Andrea watched the whole thing raptly. After he was standing on the bar. He just seemed to stand there and do nothing. “I guess I can see why you call it a perch, but what purpose does it have?” she asked.
Mel smiled. “It keeps him in place. He seems to fidget a lot, especially with his feet. Once he’s standing on that thing then he’s not going anywhere and his feet are kept nice and still. No fidgeting!”
Andrea set her fork down and removed the napkin from her lap. She just had to get a closer look. She got up from the table and walked over to Chad, looking him over carefully. She reached out and felt the material of his dress. It was nice and soft. The dress was so short though that she could see the bottom of his diaper underneath, even standing this close. She walked around behind him and took a closer look at the “perch” he was standing on. It appeared to be a simple wooden bar held up between two supports, mounted on a triangular shaped piece of wood. She looked closer. As high as the heels were on his feet, they still weren’t touching the bottom of the platform in the back. All his weight had to be resting on the bar! In that position, she could see why moving his feet would be difficult. “Isn’t that rather uncomfortable?” she asked.
“A bit,” Mel agreed. “But that’s not our problem.”
Andrea perfectly understood as she returned to her seat. The discomfort and pain, if there was any, would be all Sissy’s to deal with.
“Sissy,” Mel’s voice rang out. “Show us your diaper!”
Chad momentarily panicked. But he had already been through this a hundred times today. He quickly bent down to grab the hem of his skirt, but the dress he was wearing was much shorter than the skirt he had practiced in earlier… and he missed. By a lot. He heard giggling from the women as he corrected himself and finally found it, so much higher than he was used to. He quickly pulled the front of his dress up as high as he could and held it there. He could no longer see the women through the material in front of his face, but he could hear their laughter.
“Oh my,” Andrea said, “his diaper looks awfully wet!”
“It better look that way,” Mel replied. She glanced at the clock. He still had quite a while to go before he had to be leaking again. It looked like he was once again going to be successful. She was pleased. “Okay, Sissy. Lower your dress again and refresh our wine.”
Chad dropped his skirt and tried to curtsey on the bar he was standing on, but with his feet locked in place he nearly fell as he tried to do it properly. He finally settled for dipping both knees as he held his skirt out wide. He carefully got off of the bar. At least he had only been on it for a few minutes. The heels he was wearing weren’t really much different than the height of the bar, so for once he didn’t need to flex his ankles after getting off of the thing. He hurried to grab the wine and he carefully refilled everyone’s glass. When he finished, he quickly took another long swig from his baby bottle before getting back onto his perch again.
He had just barely gotten settled on the bar though, when Mel decided it was time for dress number 2. Why couldn’t she have sent him to change before he got back on the bar? Still, he was grateful that he didn’t have to be on that thing any longer than he did!