The Bet - Chapter 21 (Friday – week 3 Part 2 of 4)

The Bet
by Karen Singer

Chapter 21 (Friday – week 3 Part 2 of 4)

Mel tried hard to work with her clients, and mostly she did very well, but her mind was really on Chad. How was he doing today? What was he experiencing? What was going through his mind? Did he really like it – deep down underneath? She was betting that some part of him was. It was his fantasies after all.
Late in the morning, she went out to Andrea’s desk. “I’m going to be a little later than usual after lunch today,” she told her. “I’ve got a few things to do. But I’ll be back in plenty of time for my next appointment.”
“No problem,” Andrea replied as she looked carefully at Mel’s schedule for the day.
The door suddenly opened and they both watched as a delivery man came in with a fairly good sized box. Mel signed for it and they both watched till the delivery man left. There were no clients in the office. Mel picked the box up and started for her office, but she stopped and turned toward Andrea. “Want to see?”
“You don’t have to ask twice,” Andrea replied as she quickly got up from her desk.
Mel had no idea what was in the box, but she was betting it was another of the outfits she had ordered for Chad. She set it on her desk and attacked it with her scissors to open it. No mounds of ruffles escaped out of the box this time. Instead, she saw pale blue and white material wrapped up inside of plastic. She also saw a pair of socks, also wrapped in plastic, on top of everything. She pulled the socks out. They were fancy anklets trimmed with lots of pale blue lace. She giggled a bit and handed them to Andrea. Then she pulled out the main package. She was sure it was another dress, it was just wrapped up for shipping. But there was still another smaller box left in the main big box. She pulled out the smaller box and opened it. Inside was a pair of pale blue mary-jane shoes with tiny colorful flowers decorating the top. She couldn’t help but let out a giggle as she held them up for Andrea to see.
“How darling!” Andrea exclaimed as she started giggling too.
Mel handed the shoes to her while she attacked the plastic packaging around the dress. Finally she got it free and held it up. Free of the packaging, the skirt flared way out, supported underneath by a wealth of netting. While the dress didn’t have quite as many ruffles as the one that had arrived yesterday, it still had more than its fair share. The pale blue dress was heavily accented in white at the collar, the waist, the edges of the puffed sleeves and various places around the skirt. Without a doubt, it looked like a very sissyish little girl’s party dress.
“Oh, I love it!” Andrea screamed as she broke into complete laughter. I only wish I could see him in these things some time.
Mel was laughing too. “I’ll have to see what I can do about that sometime.”
“Promise?” Andrea asked, half kidding.
“Promise!” Mel replied, also kidding.

Robin stopped by Chad’s desk on her way to break. “Hi Chad,” she said as she walked into his cubicle. Chad turned around in his seat, but he didn’t say anything. At least he didn’t look as upset as he had been earlier. “I just wanted to see how you’re doing now, that’s all.” She was glad to see him actually smile – sheepishly, but still, he smiled.
“Better, I guess,” he replied. “Sorry I was so… off… earlier. It’s just that I was so worried about the way I’m dressed.”
“Why?” she asked. “You look great. Better than usual if you really want to know.”
“I do?”
“Sure.”
He shook his head. “I don’t know why.”
“What do you mean?”
“Well, it’s just difficult… all this.”
“Look, Chad. Stand up so I can see you better.”
Chad hesitated for a moment, but what could it hurt to stand up? So he did as she asked.
Robin surveyed him carefully. “Yeah, you really do look a lot better. Especially with your hair fixed that way. In fact, I’ll bet there are times when nobody would even know you’re not a woman.”
“I don’t think I look that good,” he replied quickly.
“No. Well, not really. But I’m serious, at first glance, I don’t think anyone would know.”
He sat down again. Her assurance was comforting. “Thanks… I guess,” he added.
She smiled. “Want to go to break with me… seeing as how you’re completely dressed like the rest of us now?”
He looked up at her horrified. “No way! No thanks!”
She laughed. “Suit yourself,” she replied as she walked out.
Chad watched her go, then eventually turned back to his computer. But his project was no longer on his mind. He closed it and noticed the little icon he had put on his desktop for keeping track of the bet. He double-clicked on it and suddenly felt himself peeing as the spreadsheet opened. Peeing felt so good. So wonderfully good. He stared at the spreadsheet, only half seeing it. He was supposed to be keeping track of how long he could hold back. He had just peed without realizing he was going to do it. He hadn’t held back at all. Like he was truly incontinent. And he was loving every second of wetting himself.
Even though he was staring at the spreadsheet, he still wasn’t really seeing it. What he was seeing instead was what the spreadsheet represented – winning the bet. But did he really want to win the bet? He had just wet himself without knowing he was going to do it. He had completely forgotten to hold back. In fact, he realized that he hadn’t been holding back at all this morning, and he really didn’t want to. He thought again about his struggles to hold everything in yesterday, timing himself so carefully – for what? This felt normal, holding back didn’t – and it was difficult and somewhat painful. This was his dream – wetting himself with no control. Why did he really want to hold back at all? Why did he really want to win this bet?
The spreadsheet told him there were still forty-two days left. Was it worth all the trouble he had been going through to try to remain on track and win? He put down thirty eight minutes in the column next to the forty-two, his best time yesterday. It certainly didn’t seem like a very good number – not that he really cared today. Wetting himself with no control really did feel great. So why should he bother trying to win? It made no sense at all.
He closed the spreadsheet and glanced back out to the hallway. Nobody was there. No one had seen the spreadsheet. That was good. Not even Robin. Robin – his only friend. She was down with her other friends right now – probably laughing at him. But he had no other friends. Not anymore. Only her. And he figured that she was only his friend now because she had to work with him. And it felt bad. He felt ashamed at himself once again for what he was doing through this bet. He had lost the self-respect he used to have because of the things that Mel demanded that he do. Not only did nobody want to talk to him, but he was too ashamed of himself to talk to anyone else. Was this the fate he really wanted?
He quickly opened up his spreadsheet once again and started a new column. For the header he put “Reasons to Win The Bet!” The first item he listed was “self-respect.” Under that he added “friends.” And under that he wrote, “get a life,” because somehow, when this was all over with, he would get his life back again. He thought about those first three things on his list over and over again – self-respect, friends, get a life. He didn’t just want those things, he needed them. Finally, he started listing other things too, a pool table, a new computer, a washer and dryer, and lots of expensive furniture.
He finally closed the spreadsheet feeling once again in charge. Yeah, he loved wetting himself with no control, and maybe one day he’d do it again. But next time, he wouldn’t lose everything important in the process. Now he couldn’t wait to feel the tiny urge to pee again so he could start timing himself to see how long he could hold back!

Robin laughed along with all her friends. They all had been plying her with questions about Chad and the fact that he was wearing a skirt to work today.
“Oh God, I wish I had seen him this morning,” one of her friends lamented.
“Me too,” another one added.
“Well, I did see him,” still another one said. “And I’ve got to say, while I was surprised, I really thought he looked pretty good – from a distance mind you.”
Robin laughed again. “Yeah, he really doesn’t look all that bad – especially from a distance.”
“I just wish I had seen him,” one of the women repeated.
“Hey!” yet another one exclaimed. “I’ve got an idea!”

It was almost lunchtime by the time that Chad suddenly realized he had to pee. He had almost missed the faint signs. He quickly glanced at his watch to note the time, but a moment later, he felt himself peeing. He tried to hold back, but somehow, he couldn’t remember how. His brain was having trouble remembering where the connection was to those muscles again. He remembered having that same problem a few weeks ago when he had peed on the floor of his bathroom. He stood up and tried to figure out what was wrong. He didn’t really have any problem with it yesterday, it was just today. Ok, he was really enjoying wetting himself and that was great, but why couldn’t he remember how to contract those muscles? Did the fact that he had to wear a skirt to work today have any affect on him? He had overly worried about it all night. Could that have had anything to do with his problem? It didn’t seem likely, but he had no other explanation. He tried hard to figure out how to work those muscles, but he couldn’t seem to find them – still. Why not?
“Hi Chad,” Robin said as she walked past his cubicle on the way to lunch. “Going to the gym again?”
“Yeah,” he replied, still mystified by why he couldn’t find some of his muscles.
“Ok,” she replied. “Don’t forget to get me some brochures and prices.”
“Sure thing,” he replied as he pulled his purse out of his desk drawer, then turned his project off on his computer. As he walked through the hallways, he was still preoccupied with trying to figure out how to tighten his muscles. It was like they didn’t exist! It wasn’t till he was walking out the door that he noticed how many people were staring at him. Shit! He should have delayed a bit like he usually did till most of the people were gone. He hurried across the parking lot as fast as the heels on his feet would let him go – still trying to figure out how to tighten his muscles as he hurried.

Robin watched Chad carefully from her car as she waited for him. He was earlier than usual today. It was a good thing she had gotten a head start on him. She watched him pull out of his parking space, then she followed him. She knew exactly where he was going, so she allowed a few cars to get in-between. But it wasn’t very far to the gym. She saw Chad getting out of his car and reaching for his pink bag as she pulled into the parking lot.
Chad’s head was buried in his car as he reached for his bag so he didn’t see Robin till he was halfway to the door. He stopped, terrified that she was there. “What are you doing here?” he asked.
“I decided that it’s not right for you to get the information for me. I can get my questions answered much better if I do this myself.”
Her explanation sounded all too logical to him, but he still wasn’t exactly happy. “But I’ll be glad to get it all for you,” he argued.
“Why?” she replied. “I’m already here.” She linked her arm through his and practically dragged him toward the door.
He went with her, but not willingly. “Why this gym?” he asked.
“Oh Chad, what a question. It’s supposed to be a very good place and it’s right near work.”
He wasn’t really buying it though. “You just want to see who I’m meeting!”
She laughed a bit. “Well, that would be a bonus, I admit. But, I mean look at me! Since I had the baby I haven’t lost any weight at all.”
Chad wasn’t too sure about the last part. Robin had never seemed all that worried about her weight even before she had her baby. He was more certain that she just wanted to see who he was meeting. He stopped walking as they approached the door. Did he really want to do this? No, he didn’t. Things were embarrassing enough! “I can’t!” he replied as he turned around towards his car.
But Robin wasn’t about to let him get away that easily. He had been infuriatingly stubborn about things for the last few weeks. She was here now – with him and she wanted some answers. Even a few answers would help. She grabbed his arm before he could take another step. “Oh no you’re not! Don’t be silly. Now come on in with me while I see just how expensive this place is.
Chad was reluctant, but he let himself be dragged through the door that she opened for him.
“Sissy!” the receptionist squealed as she caught sight of him. “That’s a very pretty dress.”
“Sissy?” Robin asked in mock surprise as she turned her head towards him. She already knew about the name, but now she wanted him to tell her.
Chad looked at her and his mouth gaped open, but what could he say? How was he going to explain it? He turned his head back to the receptionist, she was just staring at him with an amused look on her face. He decided to ignore Robin. “Would you please find Cassie for me?”
The receptionist just folded her arms and stood there as if she was waiting for something. He realized that she wanted him to curtsey for her again, but there was no way he would ever do that with Robin there. “Please just get Cassie,” he repeated.
The receptionist didn’t look all that pleased. “I’ll be back to help you in a minute,” she said to Robin, then she left.
“Sissy?” Robin asked again.
He turned away from her, not wanting to say or admit anything.
But Robin stayed right behind him. “She called you Sissy. She didn’t say it as if she was calling you a sissy – which obviously you are. She said it like a name!” But he still wouldn’t face her. She saw him turn towards the door, as if he was going to run. She moved to stand between him and the door, blocking it, and also confronting his face.
“It’s complicated, damn it!” he exclaimed angrily.
“Why? What’s so damn complicated? Tell me!”
He turned away from her again. “No!”
He could be so infuriatingly stubborn. She was going to press him harder, but the receptionist was returning with another woman.
“Hi Sissy,” Cassie said as she got to the front. Her gaze though was on Robin. “Who’s your friend?”
Chad didn’t really want to introduce them. He didn’t want Robin there at all. But what was he going to do? Rather sullenly, he said, “Cassie, this is Robin. Robin, this is Cassie, one of the trainers here.”
“Glad to meet you Cassie,” Robin replied. “Are you any good at helping someone get rid of the extra pounds from having a baby?”
Cassie was clearly startled by Robin’s question. For a moment she had thought that maybe this Robin woman had come in for a different reason, seeing that she knew Sissy. She smiled broadly at Robin. “It’s one of my specialties. When did you have your baby?”
“Ten months ago. But I just never did anything to really get back into shape… not that I was in all that great shape to begin with – as you can probably see.”
Cassie smiled again. “Oh, you’re not bad at all.” She dropped her voice to almost a whisper. “You should see some of the women that come in here.”
Robin laughed along with Cassie, “Yeah, I can imagine. So what would you recommend?”
“Why don’t you let me give you the tour?”
Robin’s eyes opened wide with surprise. “That would be great!”
Chad suddenly found himself alone with the receptionist as he watched Robin following Cassie back through the gym. Maybe Robin really did want to join. But then again, maybe not! And now she knew that everyone here was calling him Sissy – his new name. Self-respect, friends, and a life!
“Your friend seems very nice,” the receptionist commented.
He shrugged. But the receptionist was right. “Yeah, she is,” he replied.
“I like what you’ve done with your hair today. It really looks very nice.”
Ugh! Small talk. Feminine small talk. “Thanks,” he replied. Why were Cassie and Robin taking so long? What could they be talking about? Not him, he hoped.
“Did you fix your hair yourself?” the receptionist asked.
He was forced to turn his attention back to her more fully. “Yeah,” he admitted. “It wasn’t all that easy.”
“Why not get it permmed then, like I do? Then it’s easy to take care of.”
Permmed? No, not if he could help it. “I don’t think I want to go that far with it,” he replied.
He finally spotted Cassie and Robin coming back together. They were talking animatedly together. He just hoped they weren’t talking about him.
“Thanks, Cassie,” Robin said as they got back to the front. “You’ve given me a lot to think about now. I’ll call you later.” She then turned her attention back towards Chad. Smiling, she said, “See you later – Sissy.” And she walked out the door.
Chad watched after her, totally aghast. He turned back to Cassie. “What did you tell her?”
Cassie was surprised. “Tell her? I told her all about the gym and what we can do for her here. She’s really interested and it would do her a lot of good.”
Chad still had a feeling that the two women had talked about more than just the gym. This time, he led the way to the back room himself.
Cassie watched him as he undressed. He didn’t seem all that happy. She was guessing the cause of his problem was the woman she had just met. She dug his bottle and the baby lotion out of his diaper bag and waited till he laid down on the floor, ready for her to begin. “You don’t seem very happy today,” she noted as she handed him his bottle.
“I’m not.”
“Because of your friend, Robin?”
He nodded instead of answering with the nipple in his mouth. Sucking on the nipple felt good, almost comforting.
Cassie removed his diapers and placed a fresh one under him. Then she squirted a large amount of baby lotion into her hands. “Ready?” she asked. Her only answer was him rolling his eyes. As usual, she began rubbing the baby lotion into him. She played with his chastity device just a bit to try to get a reaction out of him, but just like the past few days, she got nothing.
Chad felt her rubbing her magic hands over him. She really did have a wonderful touch. He wasn’t all that happy about when she started rocking his chastity device back and forth though, but fortunately, he never even started to get hard from it. But the moment her hands left his device, another sensation hit him, and unfortunately, it hit him quick.
“Oh no!” he shouted as he dropped the bottle in his hands and moved both of his hands to his groin. The feeling of having to pee came all too quickly and he still hadn’t been able to find those muscles to stop it. Before he knew it, it was all rushing out of him. He grabbed the chastity device and squeezed it hard to stop the peeing, but that did nothing at all. He rolled onto his side and got to his feet, still fighting to stop the peeing, but it was still coming out of him, and worse it was going everywhere because he wasn’t standing still.
“Stand still!” Cassie ordered as she quickly held a diaper over the chastity device.
Chad was breathing hard now, totally panicked once again while Cassie continued to hold the diaper to catch what little might still be coming out of him. He felt so frustrated. “Damn!” he cursed softly. He glanced around the small office. He had made a mess. Damn! “Sorry,” he exclaimed. “I couldn’t stop it.” Damn!
Cassie was somewhat annoyed since some of his pee had wound up on her, but mostly, she was surprised and fascinated. The guy really was losing control – totally! “It’s ok, baby,” she said as she cautiously removed the diaper to see if he had finished yet. He had. She looked around the room and grabbed another fresh diaper to wipe the mess up with. Fortunately, it all came up easily. Fortunately too, the cleaning lady washed all the floors in the gym every night. “See, no problem,” she finally said as she noticed that Chad was still on his feet and looking somewhat horrified. She supposed that she would look horrified too. “Come on, baby. Lay back down again and let’s just finish. Ok?”
Chad reluctantly laid back down again for her. He picked up his baby bottle and began sucking on it again. Why couldn’t he remember how to tighten those muscles? Did he have some kind of major accident that injured him in some way that he couldn’t remember? It made no sense.
Cassie didn’t play with his tiny asshole. Instead, she just put fresh baby lotion all over him and inserted another suppository. Then she diapered him. Through it all, he just drank his bottle and stared at the ceiling like he was very distracted. “Ok, all done,” she said, indicating that he could get dressed now. But it took him a moment to come back to reality. “Are you ok?” she asked.
“I don’t know,” he admitted. “I’m not having the best of days today.”
“Again?” she asked, referring to yesterday.
“Again,” he admitted.