The Bet - Chapter 20 (Thursday – week 3 Part 2 of 5)

The Bet
by Karen Singer

Chapter 20 (Thursday – week 3 Part 2 of 5)

Mel handled several clients in her office, then had a mercifully short meeting with a judge before getting back to her office again – well before lunchtime. When she got there, Andrea pointed to a large brown box on the floor next to her desk. “That just came in for you a few minutes ago.”
Mel looked at the box as she dropped some paperwork on Andrea’s desk. “What is it?” she asked.
“I don’t know. It’s just got your name on it.”
Mel looked at the box quizzically. She didn’t recognize the name of the company that had sent it. She picked it up, it wasn’t all that heavy. She gave Andrea a wondering look and carried it back to her office. She set it on her desk and started attacking the box with scissors to open it. She finally pulled the lid of the box open and stared in disbelief as volumes of tightly packed white ruffles tired to escape out of the top of the box. She couldn’t help it, she laughed out loud!
Obviously, it was one of the things she had ordered over the internet with Cassie and Sandy last weekend. No wonder she didn’t recognize the company. She pulled at the ruffles to take everything out of the box. There were so many ruffles covering everything that it was hard to see what it was – let alone find the top. She held it at arms length – the only way she could even have a chance to see it clearly. Oh God! She couldn’t wait to see how it would look on Chad!
There was a small knock on her door, Andrea’s knock. “Come in,” she called as she turned around to face the door.
Her door opened and Andrea started to come in. “Hey Mel, these papers…” But Andrea couldn’t say anything else as Mel proudly held the garment up so Andrea could see it. Andrea’s eyes were as wide as saucers and kept going back and forth from Mel’s face to the huge mass of ruffles. “Obviously, that’s for…”
“Yeah,” Mel replied trying to stifle her laughing again. “And I can’t wait to see him in it!” Mel couldn’t contain her laughter any longer and let it out fully. As did Andrea – to the point where they were both going to have to fix their makeup.

Robin stopped at Chad’s cubicle on her way past. “Hey Chad,” I’m going to break. Do you want to come?”
Chad turned around in his chair and shook his head. “No thanks. I don’t think so.”
Robin shrugged. It was the reply she had expected, but she wanted to try anyway. “Suit yourself,” she replied and continued past.
Chad turned back to his computer and stared at the project on his screen. After a few moments, when he was sure that Robin wouldn’t be back anytime too soon, he minimized his work and opened up his spreadsheet for the bet. The count was down to forty-three days now. An eternity. But at least the number went down every day. He looked at the column where he was keeping track of how long he was able to hold back. Yesterday he had put down thirty minutes. His problem though, was that he didn’t really know how long he had held it yesterday. He hadn’t bothered to keep track at any time. Thirty minutes had been a conservative estimate though. So today he put down thirty-five. Feeling like he was still well on his way to ensuring that he couldn’t lose, he closed the spreadsheet.
But when he opened his work project again, he just stared at the screen. He was wetting himself in his sleep now. That wasn’t good – as far as the bet went. It wasn’t really all that bad either. The bet stated that he had to be completely incontinent, and he was fairly sure that just wetting himself at night wouldn’t let him lose – especially since he now had complete and perfect control during the day. Still, it was troubling… while at the same time, he found it fascinating and all too stimulating.
He was wetting himself in his sleep now just like a baby – with no control at all. Mel had actually caused him to do that. She had really done it! But that alone wouldn’t win the bet for her. It was a good thing that he was keeping track of everything else now or things would really get out of hand… and he could lose all too easily. It was hard to believe, but he supposed it could still happen. Forty-three days! Way too many. He would have to be very careful.
He felt the need to pee hitting yet again. He had only drank five bottles of Mel’s tea since he got up. The darn stuff kept him peeing constantly, which didn’t help matters. He had just realized that he had to pee. This time he glanced at his watch and took note of the time. It was time to find out for sure how long he could hold it. Twenty minutes later, he couldn’t stand the pressure anymore and had to let it out. He checked his watch. Not good! But then all those bottles of tea had to go somewhere. There was still probably too much of it in his system. He’d keep checking himself carefully all day. He knew he could do a lot better than that!

It was almost lunchtime. Robin already had her bag out on top of her desk and was ready to go. Chad was going to that gym every day. She knew he was meeting with one of the trainers for a little while, but that was all she knew. Even the receptionist didn’t know what they were doing. How could she find out more? Would he tell her if she asked? It was a thought that hadn’t occurred to her before. Her face drooped a bit. He was all too closed-mouthed about everything odd in his life lately – which seemed to be his entire life. Still, what could it hurt to ask?
She got up and walked around to his cubicle, he was just closing his project. “Hey Chad, want to go to lunch?”
“No thanks,” he replied.
“Still the same date again?” she asked. He nodded – sheepishly she thought. “Look, Chad… I saw you going to the gym down the road yesterday. Is that where you’re going again?”
Chad was suddenly horrified. “You saw me there?”
Robin was surprised. “Well, yeah. I mean, I had to drive right by it when I went to lunch!” There was no way she would admit to anything else.
It made sense to Chad. Someone was bound to notice him eventually. But that didn’t mean he had to tell her anything. Not really. “Yeah, I’m going there again.”
“But that’s a women’s gym. Isn’t it?”
“Yeah. So?”
“So what are you doing there?”
“Meeting someone. Ok?” he replied with a bit too much anger. She was prying too much again!
As she suspected, he wasn’t going to tell her. She just shrugged her shoulders. “Ok, I was just asking, that’s all. See you later.”
Chad watched her walk off. He had been spotted now going into the gym. At least Robin didn’t know what he was really doing in there. He wondered if Cassie could meet him somewhere else instead – like maybe his apartment. For that matter, maybe Mel would let him change his own damn diapers at lunchtime!

Robin watched as Chad pulled out of the parking lot and headed towards the gym. She purposely turned the other way. She knew where some of her friends were having lunch and it was about time she started joining them again. But halfway there, she had an idea about Chad and the gym. Unfortunately, it was way too late to try it today. But tomorrow… And wait till she told her friends!

“Hi Sissy!” the receptionist called out as he walked in.
“Hi,” he replied simply. The receptionist looked at him with a mock pouting expression. He sighed and dropped a quick curtsey and said, “How are you today?”
The receptionist immediately smiled brightly. “Much better now.” She giggled as she went off in search of Cassie.
It was little things like that, Chad realized, that were making his life all that much more complicated. “Hi Sissy,” Cassie’s voice called out as she got to the front.
He dropped yet another curtsey as he greeted her, then followed her to the office in the back. As soon as the door was closed behind them, he said, “One of my coworkers has spotted me coming in here.”
“So?” Cassie asked.
“So what am I supposed to tell her?”
“I don’t know,” Cassie replied. “That’s up to you.”
“Is there anyway we can meet somewhere else to do this?” Chad asked.
Cassie shook her head. “Sorry. We’re lucky to have what little time we do. This is one of the busiest times of the day for me.”
Chad was disappointed, but he understood. At least he had asked. He started getting undressed while Cassie dug into his diaper bag and pulled out one of the baby bottles. The sight of it made him feel the need to pee again. He quickly checked his watch so he could start timing himself again.
A few minutes later, he was laying on his back, sucking on his bottle, and concentrating on Cassie’s hands as they worked the baby lotion all over as much of the front of his groin as the chastity device he was wearing would allow. It really was a wonderful feeling. The tea he was drinking was increasing his need to pee, but laying on his back seemed to help take some of the pressure away. If he wasn’t trying to hold back so much, he would have wet himself before she removed his already soaked diapers, but he was trying harder today so he hadn’t. The good news today though was that while Cassie’s hands felt great, he wasn’t having to try all that hard to stay soft so the chastity device wouldn’t hurt him. Maybe it was his growing need to pee that was helping.
Cassie pulled her hands away and smiled. “You’re doing real well again.”
He pulled the baby bottle away from his lips slightly. “Thanks. I think it’s getting easier.”
She patted his hip. “Roll over and I’ll play with the other side again just a bit. Ok?”
He knew she really wasn’t giving him any choice. And as much as he hated what she was about to do, he also knew that he really wanted it too. So many changes in his life. Where would it all end? He rolled over and pulled his legs up under him with his head lowered toward the floor – making his backside an all too easy target. But that was just what he wanted… now.
Cassie began again by massaging him with the baby lotion, relaxing him, and he loved it. It was really sensual. As fantastic as Mel’s touch had been last night, Cassie was really much better. But then he felt her beginning to play around his asshole again and he waited breathless for her to really move her attention to it. Finally, her finger was there, pushing, then harder. He felt her finger go in. Why did he love it so much? He just did! He was suddenly moving in and out while she was doing the same with her finger. Fantastic!
But the need to pee in him was still building – invading his reverie all too much. He tried desperately to push the invading discomfort away, but it was getting more and more difficult, especially since he had just finished more than half of the baby bottle of tea already. The position his body was in now wasn’t helping either as it put all too much pressure on his insides.
And then it happened – all too quickly, certainly faster than he could stop it. Cassie pushed harder than she had ever pushed her finger before, trying to arouse him more. But it was more pressure than his bladder could stand. “Aaiiieee!” he exclaimed quickly as he suddenly felt a bit of pee escaping from him. “Stop!”
Cassie quickly pulled her hand away. “What wrong?” she asked, concerned that she had somehow hurt him.
Chad was rolling over and reaching under him, trying to grab his penis to squeeze it to stop himself from peeing, but the darn chastity device completely foiled that idea. The pee was still coming out of him and he couldn’t stop it.
Cassie finally saw what was happening and burst out laughing as she quickly grabbed one of the diapers she had handy to catch the remaining pee that was still coming out.
“Shit! I’m sorry,” he said as she held the diaper over his chastity device for him, feeling it getting wetter and wetter.
“That’s ok, baby,” she replied, still highly amused. “I guess we should have expected little accidents like that to happen.
He said nothing, but just rolled completely onto his back and stuck his bottle back into his mouth as soon as she had wiped up his messy puddle. He wasn’t really having a good day so far with holding back. But it was all different circumstances that were really giving him the problems. His troubling thoughts were momentarily interrupted by the feeling of Cassie’s fingers shoving another suppository up inside of him again. And that was another problem, he realized. How do you fight the damn suppositories?

Mel was getting ready to leave for lunch when her cell phone rang. “Hi Mel,” Cassie’s voice came over the phone.
“Hi Cassie,” Mel replied. “How did everything go today?”
Cassie started laughing a bit. “Oh Mel, you should have seen it. I was playing with his backside again, you know, trying to get a reaction from him, when all of a sudden he started peeing all over the floor!”
Mel burst out laughing. “He did?”
“Really!”
“Oh Cassie, that’s good news. I wish I had been there.” Mel was really elated. It was the first real sign that she was actually winning the bet. “Hey Cassie, if you think that was funny, wait till you see what I got in the mail for him.”
“Did some of those outfits you ordered finally come in?”
“Yeah, one of them anyway.”
“Oh, I can’t wait to see it!”
“How about tonight?”
“Like I said, I can’t wait.”
Mel remembered something then. “It’s going to have to be a bit later though, we have an appointment to go to first.”
“That’s fine, Mel. Whenever. Just let me know.”
“Great Cassie. Oh, and when you come over, do you think you can teach him how to fix his hair properly? I’ll get him a curling iron before we go home tonight.”
“Sure thing, Mel. I’d love to.”
“Great! See you later.”