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

The Bet
by Karen Singer

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

It was late in the afternoon when Robin stopped by Chad’s desk to talk again. “Hey Chad,” she said as she walked into his cubicle. “How much does that gym cost where you go?”
“I don’t know,” he replied. “I’m just meeting someone there.”
“Oh, well I though you might know since you’re there so often.”
“No. I have no idea, but I can probably get you some brochures or something if they have any.”
“Yeah, that would be great. Thanks,” she replied as she leaned back against his desk, obviously not ready to leave.
He turned all the way around in his chair and leaned back a bit. He had been working hard all day, and with taking no breaks, he was ready to clear his mind. “How’s your baby doing?” he asked, knowing that small talk was probably on her mind.
She smiled. “Well, at least I haven’t had a call from his daycare – yet.” She looked down at his legs and the shoes he was wearing. “How are you making out in those shoes today?”
He glanced down and raised one of his legs slightly and rotated his foot. “My feet are aching. I wish I had picked a pair of shoes that didn’t buckle so I could slip them off easier.”
Robin chuckled a bit. “Now you know what we girls have to put up with all the time for you guys!”
He looked up and smiled. He almost laughed a bit himself. But his feet really were hurting. It would feel so good if, just once, he could flex them a bit in the other direction and curl his toes. “At least I get to sit down all day,” he replied. “Otherwise, I think I’d really be in some pain.” This time, they both laughed together.
“So Chad,” Robin said as soon as her laugher had died down somewhat. “When are we finally going to get to see you in a dress?”
“Never, I hope!” he replied good-naturedly.
“Oh come on,” she replied. “I’ll bet you’d look soooo good!” she said teasingly.
He shook his head and actually laughed a bit. “Not if I can help it!”
“Want to get some coffee?” she finally asked.
Chad shook his head. “Not today. I don’t really want anything at all today.”
“Really? Not at all?”
He shook his head again. “Not today,” he replied confidently.
She shrugged. “Ok, I’m just going to grab one last quick cup for myself. See you later.”
Chad watched her walk out. Coffee wouldn’t be bad, but he was finally doing a lot better on holding back from peeing. All of Mel’s too many baby bottles of tea had finally worked their way out of his system and the one bottle he had from lunch seemed to be out of the way now too. The last time he had to pee, he had timed himself at almost forty minutes. That was really doing well and he was proud of himself over it. He was going to win this bet. There was no doubt at all!
He squirmed just a bit against the messy load in his diapers from where the suppository that Cassie had stuck up inside of him had done its job. At least it wasn’t as bad as it sometimes was. But the question was, what could he do about it? Even though he wasn’t getting as many suppositories every day as he had last week, he was still getting several every day. And there was just no fighting them!

As per Mel’s text message, Chad drove straight to her office after work. He was looking forward to their relaxation therapy session later – the one and only real bright spot in his life. As he walked into her building, Andrea looked up and put a big smile on her face. “Hi,” she exclaimed. “Wow, you’re looking better and better. You know that?”
Chad was a bit taken aback. “I am?”
“Yeah, really.”
“Uh, thanks, I guess.”
Andrea laughed a bit. “Come on, I’ll take you back.”
Once again, Chad followed her back to the same unused but beautifully appointed office. Mel came in a few minutes later with a big smile on her face. “Hi Sissy,” she said as she walked in.
Chad got up from the leather couch he was sitting on and dropped a quick curtsey. “Hi Mistress,” he replied.
Mel started digging through his diaper bag and pulled out the one still full bottle. She handed it to him. “Drink this and I’ll be back later to change you.”
Chad wasn’t at all happy to have to drink the bottle, but he had been expecting it. His record at holding back for the day was still less than forty minutes. He took the bottle and put it to his lips as Mel walked out again. He sat back down on the comfortable couch. The minute he started drinking, the urge to pee hit him again. He checked the tiny dial on his watch to note the time.
By the time that Mel came back, he had long finished his bottle and was now walking around the room, trying to keep from peeing. His need was so great that he couldn’t sit still on the couch any longer. His discomfort was further emphasized by the mess still inside his diapers from the suppository earlier.
“Ok, Sissy, let’s get you changed,” Mel said as soon as she came in. As she began pulling diapers out of his diaper bag for him, he began getting undressed, then he stopped. He had to pee real bad and didn’t want to do it too soon in the fresh diapers. He let it out while he just stood still. The feeling was pure heaven and he closed his eyes. It felt so good that he decided that when this bet was over, he was still probably going to stay in his diapers. Maybe forever. But before he could seriously consider that, he had to win this bet!
“What are you doing?” Mel asked, seeing him standing there with his eyes closed and a big smile on his face.
He quickly opened his eyes in surprise. He hadn’t meant to be so obvious about it. “Sorry, Mistress,” he replied. “I was peeing.”
Mel smiled broadly. “By the look on your face, it must have felt pretty good.”
He nodded quickly as he once again began undressing. “Yes, Mistress, real good!”
As soon as he was down to just his diapers and was laying on the floor for Mel to change him, she asked, “So you really do like wetting yourself?”
“Yeah,” he admitted. “More than I ever thought. It’s funny,” he mused, “it seems like with each day that goes by, I like it more and more. Really strange.”
Mel said nothing as she listened to him. She recognized Gloria’s hypnotic suggestions taking stronger and stronger root in him, even if he didn’t - which she hoped he had no idea of at all!
“Maybe it’s because I haven’t been able to have any kind of sex,” he continued as she finished wiping his messy bottom.
“What do you mean?”
“I don’t know. It’s almost like it’s the closest thing to a physical sexual feeling that I can have – with this damn contraption on me.”
She chuckled a bit. “How about the anal play you seem to be getting so fond of lately?”
He shook his head and she could see the confusion on his face. “I just don’t know about that. It’s really strange. I don’t know what to make of it.”
“Why not?” she asked as she pulled the first diaper into place and taped it closed.
“I don’t know. I guess it’s just too new. And it’s troubling.”
“Why?” she asked as she started on his second diaper.
“It just is. It’s not right.” He paused as she was finishing up. Then asked, “What do you think about it?”
She looked at him and smiled. “I think you should get dressed and then let’s go get a nice dinner together. We can talk about it more then.”

Once again, Mel drove them to the same restaurant they had been to every week before their therapy session. Chad hated going in there because she always made him drink from one of his baby bottles in front of everybody while they ate. He always heard way too many embarrassing comments from the surrounding people and he wasn’t looking forward to doing it again.
After they were seated, the waitress came by and set some menus on the table for them and asked what they wanted to drink.
“Would you like some coffee?” Mel asked him.
“Yeah, that would be good for a change,” he replied. He just wished he wouldn’t have to drink it out of the baby bottle. But at least one cup of coffee would be less to drink than a large coke that would fill his bottle two or three times.
“So, tell me about your day,” Mel asked while they waited.
Chad rolled his eyes a bit, but it was mostly light conversation and fairly comfortable. And Mel seemed to be interested in listening to him – which was really nice.
When the waitress brought their coffee a few minutes later, Mel ordered a large steak dinner for him and a salad plate for herself. Chad didn’t touch his coffee since he knew she would pour it into one of the baby bottles. But she just took a sip from her own coffee instead and asked, “So your boss likes how your project is going so far? Does he ever come down and make any suggestions in person?”
Chad shook his head – why wasn’t she pulling out a baby bottle? “No, he never comes down at all. It’s more like he’s purposely ignoring us down there. We hardly ever see him.” Still no move to get a bottle. He took a chance and picked up the cup and drank from it. Good coffee. Real good. Especially without the bottle. But would she realize that he wasn’t drinking from it now?
As he talked about his day, Mel felt the old bits of annoyance every time he mentioned Robin, but she had braced herself for it. Did he realize that she was purposely letting him drink from the cup instead of the bottle this time? She was betting on it. But tonight she just needed to talk comfortable with him for a bit, and losing the bottle would be a big help. It was helping already. The more he talked, the more relaxed about it he seemed to be getting. And she herself seemed to be relaxing and enjoying what was starting to become a really nice conversation about more than just his work.
By the time their dinner came, Mel found herself telling him about her horrible date with Detective Grey. She hadn’t planned on telling him, but she even admitted to trying to sleep with him and then throwing him out. They both laughed over it.
As they shared a final cup of coffee after dinner, she realized that it was one of the nicest dinners she had enjoyed in a long time. She had enjoyed talking with him. He wasn’t one of those guys that was interested in only himself. He was intelligent, funny, and seemed to be interested in what she had to say. A far cry from Detective Grey. Why, oh why did he have to be a flake? She glanced at her watch and gave a short exclamation. “Oh God! We’re going to be late!”