The Bet - Chapter 26 (Wednesday – week 4 Part 3 of 6)

The Bet
by Karen Singer

Chapter 26 (Wednesday – week 4 Part 3 of 6)

Mel closed the cover of the folder she had been working in and set it aside on her desk. She picked up the next folder to work on and paused. She was working hard. Was Chad? What was he doing today? He had said that he still didn’t have the go-ahead to get back to his project. Was he and the Robin woman spending all their time together again? The thought of it disturbed her. To take her mind off of it, she opened the folder in front of her and plunged back into her own work.
But it didn’t last. All she could see in her mind was Sissy and Robin talking together. Sissy, sitting and staring into the eyes of the beautiful, young Robin woman. She couldn’t stand it! She closed the folder in front of her again and stared at, hardly seeing it. How could she keep him from spending all his time with Robin while he was at work? The problem was that he was supposed to be working with Robin. But they weren’t working. Not just then anyway.
Maybe that was the solution. She couldn’t do anything about giving Robin any work that would keep her away from Sissy, but maybe she could give Sissy some work that would keep him away from Robin! But what?

The hallways were crowded as Chad and Robin walked back to their desks from the break room. Chad still did his best to not look at any of the men, he was too embarrassed about himself for that. He was embarrassed about being seen by the women too, but somehow they didn’t seem so bad to him just then.
As he sat down in his chair again, he noticed that the irritation from his diaper rash didn’t feel quite as bad as it did earlier. Was it finally clearing up? He could only hope.
He glanced at his computer and noticed an email had come in. He opened it. “Oh Roooobiiiin,” he called over the cubicle wall. “Check your email!”
A minute later, he heard Robin’s voice exclaim over top of the wall, “Finally!”
Chad walked around to her cubicle where she was just reading the email. “It took them long enough,” he declared as he walked in.
But Robin was intent on reading the details of the email and didn’t answer right away. “Did you read all of this though?”
“Not yet,” he answered.
“They not only liked what we did, but now they’re asking for a lot more… a lot!”
“Ok,” Chad replied as he leaned over her shoulder to read her screen. “I guess we’re suddenly busy again.”
“I would say so,” Robin replied.

Mel paused while typing the email message and glanced at her watch, it was lunchtime… a little past actually. Darn! Chad wouldn’t even be at his desk now. But that really wasn’t a problem. He’d get his instructions as soon as he got back. She finished typing her email to him and hit the send button. There! That should do it!
With a smile, she closed her computer and got up from her desk, wondering if Andrea would like to go to lunch with her for a change.

Chad pulled into the parking lot at the gym feeling happier than he had all day. He wasn’t happy because of what he was wearing. He was happy because he was definitely sure his diaper rash wasn’t as bad now. It was still there, just not so bad. Even all the wetting he had done that morning hadn’t made things worse. Now if he could just convince Cassie to not give him one of those suppositories…
He walked through the door into the gym and was immediately greeted by the receptionist who called out, “Hello Sissy,” all too loudly – and with a far bigger grin on her face than he was happy about. He immediately dropped a quick curtsey and said “Hi.” Then he waited till she found Cassie for him. He again repeated his curtsey and greeting for Cassie, then followed her back to their usual private office.
“How’s your rash today?” she asked, as he began undressing and she was closing the blinds.
“I think it’s starting to get better now,” he replied.
“Well, that’s good,” she said. “It looked pretty bad yesterday.
Chad waited till he had struggled to get his pantyhose off, then his girdle before he asked. “Look, is there any way we can please skip the suppository today? The rash is getting better, but the mess from the suppository will only make it worse again.”
She looked at him and smiled. He had the distinct impression that she just might go along with him for once. “Nope! Sorry. Mel’s instructions.” His hopes were dashed once again!
Cassie spent very little time working on the front of him – there just didn’t seem to be any point in it anymore. Since the chastity device prevented her from touching his penis directly, he wasn’t going to get any kind of a reaction as she worked on him there. He got very little of his bottle finished by the time she had him roll over onto his back and pull his knees up under him – exposing himself shamefully for her attentions. Attentions that he was now rather looking forward to – as long as she didn’t mess with his diaper rash too much.
As she carefully spread the ointment sensually over his red and blistered bottom, her hands still felt wonderful. Yes, the diaper rash was definitely better today – since he was getting that much pleasure from her rubbing her hands over it.
Even still, she didn’t spend long on it before he again felt the cold, hard tip of her toy playing with his asshole once again. He braced himself for it, and felt her pushing it into him, slowly… ever so slowly today. She was teasing him with it. He wanted to push himself forcefully onto it… impale himself fully. But this time, he restrained himself. He didn’t push back at all. He simply waited and let her push it slowly into him, then pull it back again, then push it a bit further… teasing him with it. She was doing all the work today, not him. He closed his eyes and gave himself to the sensations he was feeling. Why did he have to love this so much? It wasn’t right! It was wrong! Wrong! Wrong! He mentally sighed. It did no good to berate himself. He loved it, and that was all there was to it. He just did.
But as Cassie played with him, the stimulating feelings grew inside of him. They finally reached a point where he could no longer be just the passenger. He had to have more! He finally pushed back, then pulled away, then pushed again… faster and faster… harder and harder… searching, desperately trying to find enough feeling and sensation to get over the hump – the hump that would grant him sexual release. But it just wasn’t to be. No matter how hard he fucked himself against her toy, he just couldn’t get there. He finally stopped, totally frustrated.
He felt her pulling the toy out of him, then inserting her finger in him once again, pushing the suppository way up inside of him as far as her finger would go. He prayed that for once it wouldn’t do anything so his rash could continue to get better. But he knew all too well what would probably happen. As she pulled her finger out again, he opened his eyes. In his present position, he could just barely see his chastity device. His penis inside of it was no bigger than it ever was anymore. Not one bit bigger. Since Mel had put the new teeth into the device, his penis stayed smaller and more insignificant than ever – always. It had to, or the pain would be awful.
As he rolled over so Cassie could continue diapering him again, he tried to remember the last time he had felt any pain from those teeth – last night when Mel had dressed him in that ridiculous baby dress. The pain had been horrendous. He had no choice but to try to ignore his feelings of sexual stimulation so he could always remain small. Not just small, but tiny. And now, because he couldn’t ever get hard, and because he was loving the sensations from his asshole so much, he was starting to associate that area of his body with pleasure instead of his penis. It was like another small blow against him to realize that his penis was now becoming totally useless to him for anything except to pee out of. No pleasure from it at all. No reaction from it could be allowed at all… no matter what stimulation they threw at him. More and more of his pleasure was coming from his asshole instead. Mel was slowly stripping yet another male trait away from him. And once again, the very thought of it thrilled him sexually inside… there was just no reaction from the very place where there should have been one… his penis.
He picked his baby bottle back up again and sucked on it while Cassie finished with him. He barely registered what she was doing, his thoughts instead were locked on his more than ever useless appendage. Less of a male. More and more… less of a male. Mel seemed to be slowly winning the battle, at least in some areas. But how about the one big area that the bet was centered around – total incontinence? The thought of it made him realize that he had to pee again. He held it – purposely. Even though most of him wanted to just give in completely… she had stripped everything else away from him anyway, why not just give up? Part of him wanted to. But another part of him made him still hold on. That part was still fighting back.
He was slow to finish his bottle, lost in his thoughts, laying there on the floor in only his diaper. Self-respect, friends, and a life… not to mention relief… if he could still get any. He remembered how he had been last night, sitting in Sandy’s living room, crying and sucking his thumb. He had lost so much. He had no choice but to fight back! He sucked harder on his bottle to finish it faster so he could get out of there now. Cassie was sitting there staring at him, waiting on him. He finally began dressing again while he continued to finish his bottle. He had to fight back! Self-respect, friends, and a life!

Chad sat in his seat again, gingerly, but easier than he had before, since his diaper rash had improved a bit. Robin wasn’t back yet so he opened up the spreadsheet that he used to track his progress for the bet. Next to yesterday’s date, he filled in twenty-six minutes. Only one minute longer than he had managed the day before. It was progress, but certainly not much. He promised himself he would try a lot harder today. He checked the number of days still to go – thirty seven. Still more than a month. An eternity in some ways. Yet it gave him more time to build up his strength holding back. The only thing that really worried him was all the progress that Mel had made against him already in other areas. Surprising progress. Would he be able to keep his control – the control that would let him win the bet? He knew himself well. His body always regained everything quickly. But would he be able to make it? As far as the bet went, he was sure he could do it. His bigger question now was the other areas, especially his more and more useless penis when it came to sex. Would he ever get full use of it back too? That was a more troubling question.
He noticed an email waiting for him so he opened it. He was surprised to see that it was from Mel. What did she want now?

Sissy,

Since you seem to have so much free time on your hands, I want you to put it to good use. You said you’re having trouble deciding on outfits to wear. I want you to write me a fifteen hundred word paper – all about fashion and mixing clothes for different occasions. I expect you to email it to me before you leave work this afternoon. You can research everything on the internet. Do it, and don’t disappoint me!

Chad couldn’t believe it – a fifteen hundred word paper? Something like that would probably take him all afternoon, and then some. He reread the email again, then went back to the first sentence. He realized that Mel thought the approval for his project hadn’t come through yet. With a smile he opened a return message to Mel and explained that he and Robin now had the approval on their project and he was going to be too busy to do the paper for her. He happily pushed the button to send the message back to Mel. Then he put her whole paper out of his mind. One less thing to worry about!
Half an hour later, he was busy working on part of the project, when he saw another email come in. He paused in his work to open it and was not surprised to see that it was from Mel. He was surprised however at the contents.

Sissy,

I don’t care if you think you’re busy. I gave you an assignment and you better carry it out – no matter what! If not, then your diaper rash will be giving you far greater torments – for a very long time!

Chad stared at the email, totally aghast. Far greater torments? He had no doubt that she’d whip him severely for not doing her assignment. He closed the email and deleted it. A fifteen hundred word paper. And he had no choice. He would have to do it… probably before he did anything else for his job… or more likely, he’d have to do it while he was doing his job – both things at the same time. He only hoped that Robin wouldn’t notice what he would be doing.
He held up his hands and stared at the long claws that were his fingernails. He was going to have to type an awful lot with those claws? It would take forever! His nails gave him even more reason to hate doing Mel’s “assignment.” With a dejected sigh, he opened up his web browser to start doing research.
Only a few minutes later, his afternoon suppositories kicked in. As usual, he didn’t bother to fight against the inevitable. What would be the use? He’d only be making himself more miserable. As the mess gradually slid out of him and around his diaper covered backside, his primary thoughts were not so much the paper he was writing for Mel, or even the work he was supposed to be doing for his job, he was mostly thinking about his diaper rash and how much worse it was about to get.