The Bet - Chapter 49 (Friday – week 7 part 3 of 6)

The Bet
by Karen Singer

Chapter 49 (Friday – week 7 part 3 of 6)

Chad was getting more and more interested in what he was working on in the project. When Robin had first denied him anything to do with it, he had nearly gone crazy from having nothing to do. But now that she wanted him to work on it again, it was like a special privilege. Tasks that he normally wouldn’t think of as interesting were now not only interesting, but rewarding.
About an hour after he got down to work, he started working on holding back too. Even though the bottle he had just finished made the task that much more difficult. As usual in the mornings, he wasn’t able to hold back hardly at all. But that would improve as the day went on.
“Break time, Sissy,” Robin’s voice called from the entrance to his cubicle.
Chad was a bit surprised. He hadn’t even been watching the time. He got up quickly though to follow her, but once again she was still standing at the entrance to his cubicle and wasn’t moving.
“What are you forgetting?” Robin asked with more than a hint of steel in her voice.
Chad hated this. It was so difficult to have to curtsey even in situations where it clearly wasn’t called for. But he dropped her a curtsey anyway.
“And what else?” Robin asked.
Now Chad was confused, he didn’t have a clue what she was talking about.
“Your thumb!” Robin ordered.
Chad stuck his thumb into his mouth and was surprised to see her turn to start walking down the hallway. Did she really expect him to go to the break room with it in his mouth? He couldn’t! He just couldn’t! Panicking a bit, he followed her down the hall.
“You can take that thing out of your mouth as soon as we turn the corner,” Robin said without bothering to look at him. “Unless you’re more comfortable keeping it there – which I wouldn’t doubt for a minute.”
Chad’s thumb was out of his mouth before he even started turning the corner!
After the bottle Robin had made him drink, Chad decided to not get any coffee at all. As Robin entered the short line to get hers, he stood off to the side to wait for her.
“What are you doing?” Robin asked.
“I don’t want any today,” Chad explained.
“Yes you do!” Robin ordered. Then she stood back a step and motioned him to get in line in front of her. Coffee was the last thing that Chad figured he needed today. When his turn at the coffee urn came, he only half filled his cup. But when he started to move on, Robin stopped him. “That’s not very much,” she noted.
Chad just shrugged. “It’s all I need.”
“No it’s not. Fill it! Completely!”
Chad wasn’t happy about it, but he finished filling his cup. Then he moved down the line and grabbed a doughnut. But as soon as he turned around, Robin was there and she took the doughnut right out of his hand. “Coffee you need… doughnuts you don’t!” She took a bite right in front of him before turning to lead the way to the women’s table. “And make sure you finish all that coffee or you’ll be getting another cup before we leave!”
Chad sipped at his coffee as he sat and listened to the women talking. He was no longer the usual center of attention. More often than not now, he was ignored. Once in a while, someone would ask him things, but instead of being teased about everything, their comments and questions were more down to earth. Usually.
He took his last sip of his coffee as everyone was getting to their feet to leave. Before he took two steps, he felt Robin grabbing his hand that was still holding his now empty cup. She peered in it. “Good,” was the only thing she said. Chad tossed the empty cup in the trash on the way out the door.
As soon as they were alone and had turned the last corner back to their desks, Robin said one word only. “Thumb!” Chad once again stuck his thumb back in his mouth. He expected to get back to work right away, but Robin made him follow her to her cubicle instead. She pointed at the floor again and said, “Sit!” As he was sitting, Robin again opened up his diaper bag and pulled out another bottle. She handed it to him. “Just stand up quietly again when you’re done,” she told him. Then she ignored him again and went back to work.
Chad was horrified by the amount of liquids she was making him drink. Did she have any idea how much Mel made him consume before he came to work? He had already had three bottles before breakfast and another one with his breakfast. Now this was the second one of the morning since he had gotten to work! And that wasn’t even counting the full cup of coffee he had just finished a few minutes ago. He’d be peeing like crazy till after lunch sometime! And he could already tell that his diapers were wetter than they usually were – already.
Robin only checked on him once while he was sitting on her cubicle floor with his bottle. The idiot! He deserved this! He wanted to be incontinent? Then she had no problem with Mel’s little request. And seeing him with the bottle in his mouth only further strengthened her resolve. Not to mention that it again helped her to see him as nothing but a sissy instead of… a real person.
She turned around when she heard him getting to his feet. She took the bottle from him. “Now get some work done!” she ordered.
This time, Chad didn’t think twice about curtseying before he left. Between the coffee he had just finished and now anther bottle of Mel’s lousy tea, he could feel himself peeing yet again with very little warning. It was really coming out of him before he had a chance to start holding back. Robin had no idea how difficult she was making things!
It was half an hour before lunch when Robin called him back to her cubicle again – and handed him yet another bottle to drink. He wondered what Cassie was going to give him when he got to the gym later. But he had no choice right now but to finish his third bottle since he had gotten to work. When he finished it, he stood up again and put his thumb in his mouth while he waited for Robin to turn around.
Robin heard him get to his feet, but she let him stand there for a minute while she finished what she was doing. Only then did she turn back to him. She was pleased to see him sucking his thumb. She was also surprised to feel a slight tingle of excitement in places that her husband usually stimulated instead. The idiot! Sucking his thumb like… an idiot! She got up and grabbed the now empty bottle from him and put it back into his diaper bag. Then she picked up the bag and handed it to him. “Make sure all those bottles are filled again when you get back from lunch,” she told him. “Now get out of here and I’ll see you later.”
Chad was horrified. She was actually going to make him keep drinking them this afternoon too? It would be way too much liquid! How was he going to work on holding back? He curtseyed and backed his way out of her cubicle before going back to his desk. This afternoon too? It was way too much to drink!

Chad got out of his car at the gym parking lot and did his best to feel the back of his skirt without being too obvious about what he was doing. He had been peeing so much that he was very worried about his diapers leaking. He didn’t feel any wet spots, but that didn’t mean that there weren’t any. He didn’t have a clue what he would do if his skirt was wet anyway. He grabbed his diaper bag and headed into the gym, wondering who was going to change him today.
“Good morning, Sissy,” Cindy said with a big smile on her face as he was still walking through the door.
Chad was tempted to simply say hello without curtseying, but he doubted it would do him any good. So he curtseyed as he returned her greeting. “Are you changing me today?” he asked.
Cindy’s face went into a big pout. “No. Cassie say’s I can’t today.”
Chad was elated to hear it. “Can you please get Cassie for me then?”
Cindy was looking for something else to say to him… or mostly for a way to tease him, but nothing was coming to mind. So she simply told him to wait while she headed off to find Cassie.
A few minutes later, Chad was again following Cassie back through the room full of exercising women, some of whom said hi to him along the way. Chad figured it was the easiest he had gotten past the receptionist in a long time!
Cassie grabbed his diaper bag and started going through it while he was getting undressed. She pulled out a baby bottle and was surprised to see that it was empty. She pulled out another one… empty too! Finally she grabbed one that was still full and breathed a brief sigh of relief. Then she noticed a fourth bottle in the bag. When she checked it, it was also empty. “Didn’t you take the bottles out from yesterday?” she asked.
“Robin’s been making me drink them all morning,” Sissy replied. “I’m sorry there aren’t any full ones left. It wasn’t my fault.” Cassie just held up the fourth and still full bottle instead of answering. Chad was surprised to see it. Mel had put a fourth bottle in there? He should have checked earlier. He finally realized that Robin was now acting under Mel’s orders to feed him the bottles. How dense could he be? He should have realized it earlier!
A few minutes later, he was lying on his back with the bottle in his mouth while Cassie started pulling his plastic panties down. “Goodness!” Cassie exclaimed. “There’s pee puddled inside of these things! If it wasn’t for your plastic panties you’d be a real mess!” Very carefully, she peeled them off of him. “God, you’re so soaked!”
Having to be more careful than ever, she pulled his sodden diapers apart. But the moment the cool air hit his chastity device, Chad realized he was going to pee again. He also knew he wouldn’t be able to hold it back for more than a second or two. With no time to warn Cassie, he quickly reached down to try to grab his diaper.
Cassie saw him hurrying to grab the diaper again and guessed what was about to happen. She too grabbed for the diaper she had just peeled back, but as fast as she was, she had no trouble seeing the pee starting to erupt out of the end of his chastity device. Fortunately, the diaper was already high enough to catch everything that came out. After a few moments, she carefully pulled it back again. He had finished, but now she noticed the pee that had just come out of him was puddle in the diaper. The drenched thing couldn’t hold any more. She quickly grabbed the two fresh diapers she had already prepared for him and slipped them in place under him instead. Now at least if he peed again, the diapers would hold it.
She quickly wiped off his front side, then ordered him to turn over. She was glad to see that the bruises on his backside had diminished greatly since yesterday. She had worried about that because she felt partially responsible for them. She cleaned him up, then grabbed the bottle of baby lotion.
Chad felt her spreading the lotion all over his backside again – and today she was rubbing it in again! His bruises hurt a little, but it was so slight now that it barely bothered him at all. The feeling of Cassie’s hands far outweighed any discomfort from the bruises.
“Are you going to scrunch your knees up for me again?” Cassie asked.
Chad didn’t even hesitate. He pulled his knees up under him, raising his backside up high for her to play with. And very shortly, he was holding his breath as her wonderful hands started to play with his tiny asshole. It felt so incredibly good! It felt even better when she stuck the tip of her toy against it a few minutes later. And a few minutes after that, he wasn’t thinking about how good it felt, he was too preoccupied with trying to pump himself back and forth against the thing… trying desperately to reach the orgasm he wanted so badly. It was possible! It had to be possible!
Cassie was holding onto her dildo once again for dear life as he worked himself so strenuously against it. He seemed so desperate. She couldn’t help but feel for the poor guy. Out of the corner of her eye, she noticed him peeing again, but fortunately the diaper was under him and was catching everything. She had the impression that he was so worked up over what was going on in his backside, that he didn’t even know he was peeing. And before long, as usual, she saw him giving up. Again, she felt a bit sorry for him. He tried so hard, but in the end he always got nowhere.
She removed the dildo and while his backend was still up in the air, grabbed his jar of suppositories. But he wasn’t even turning around to look. She opened the lid – and screwed it right back in place again without pulling anything out. Then she stuck her finger way up inside of him again as if she really was inserting one of them. He didn’t know. It was obvious that he didn’t know. And hopefully, he never would.

Mel got back from lunch at her usual time. As she walked through the door, Andrea was already back from lunch.
“I need just a few more minutes to finish another contract,” Andrea told her. “Do you want the rest of the stack to sign now, or when I finish?”
Mel barely paused as she walked past. “When you’re done will be good enough.” She wasn’t that anxious to start reading through them anyway. She kept going all the way back to her office. With a few minutes to spare, she decided to review her plans for Sissy. Cassie wasn’t giving him any more of the suppositories in the afternoon. She hadn’t given him any at all yesterday either. So again, he would have missed the last three. She actually wasn’t too concerned over that issue because so far, all signs were good there.
She hadn’t heard back from Robin yet today about her request to have him drink more during the day. That part she was worried about. She really didn’t know what she was going to do about his holding back. Five minutes! It was impossible!
Her thoughts were interrupted by the ringing of her telephone. “Hello?”
Hi Mel, it’s Cassie.
“Hi Cassie? What’s happening. Did everything go okay today?”
“Oh yeah, sure. I just wanted to let you know about how wet he was when I changed him today. When I pulled his plastic pants down, there was a lot of pee that had puddled inside of them. It was hard to keep it from leaking all over the place. I’m amazed it didn’t leak out to his other clothes.
“That much? Wow! I wonder why it’s so much more today.”
He said that Robin had him drinking bottles all morning. It’s a good thing you put four of them in his bag this morning because three of them were empty.
Mel was definitely surprised. “They were?”
“Absolutely. And Mel, the poor guy has almost no control left. He could barely hold it long enough for the two seconds it took to pull the diapers back up when he suddenly had to pee again.”
“That’s great, Cassie! That’s just what I want to hear.”
“Well, I just thought you might want to know about how wet he was. Really, if Robin is going to keep him drinking that much, then he may need another change – before he comes here at lunchtime.”
“Okay, Cassie. I’ll have to think about that. Thanks for letting me know.”
“Anytime, Mel.”
Mel hung up her phone. It sounded like Robin had come through after all! She didn’t know what she was going to do about how wet he was getting before lunch though, but that was something she could worry about later. Instead, she turned to happier thoughts – like his planned public ballet performance – if she could get it set up! Andrea’s knock on her door interrupted her thoughts. “Come on in.”
Andrea came in with her inevitable stack of papers. “Okay, here’s the latest. And I finished all the changes to the last one you laid on my desk too.”
“Great,” Mel replied. “That was fast work!”
Andrea smiled. “We aim to please!” she replied as she turned to leave. She was almost out the door when Mel stopped her.
“Andrea… You got a second?”
Andrea turned. “Of course!” She went back to Mel’s desk. She was a bit surprised when Mel pointed to one of the chairs across from her desk and asked her to sit.
“What are you doing this weekend?” Mel asked.
“Well, you invited me for dinner Sunday night. Is that still on?”
Mel nodded. “Definitely! But are you doing anything else?”
“Not really. Nothing special anyway.”
Mel thought hard about what she was about to ask. It was a big favor but… “I’m trying to plan something special for Sissy. Would you be interested in checking something out for me, and maybe making an arrangement of two if you can? I need to stick close to him at all times now and I don’t want to take the chance of him finding out what I’m planning.”
“Um… I guess so,” Andrea replied. “What did you have in mind?”
Mel spent the next few minutes explaining what she needed.
Andrea was more than a bit shocked. “You have ‘got’ to be kidding!” When the expression on Mel’s face didn’t change she added. “Really?”
Mel nodded. “Really!”
“Oh my God!”