The Bet - Chapter 33 (Wednesday – week 5 Part 8 of 8)

The Bet
by Karen Singer

Chapter 33 (Wednesday – week 5 Part 8 of 8)

Chad glanced at the clock as he finished cleaning up the kitchen. He still had a little over half and hour left for his diaper to start leaking. He was fairly sure he would be early again since he was wetting now every few minutes. What he found so interesting was that more and more often, he would simply start wetting before he knew he was going to. Not always, but sometimes. It was such an interesting feeling.
He glanced around the kitchen. Everything was clean and shining, just the way it should be. Mel was again in her living room chair, working on her laptop. He didn’t know how she could stand to work such hours. It never seemed to stop for her.
Not wanting to be told to stand in his corner again, he decided he had better find something else to keep busy with. He went directly to her clothes hamper and started pulling out her laundry. A few minutes later, he was watching as the washer began its job. He glanced back at Mel. As far as he could tell, she had never once even looked up to see what he was doing. The look on her face seemed to be only deep concentration.
With nothing left to do till the washer was done, he grabbed a dust cloth and started wandering around her apartment, making sure everything was in its place and dusted. As he was working on the table by her door, he suddenly realized he was going to pee again. It was only a second or two before his pee started coming out, and all too quickly the pleasant sensation ended. As he moved away from the table, toward the living room, he felt it. That tiny little tickle running down his leg. “Mistress. I’m leaking!”
Mel looked up from her work. She had a slight headache from the tension of what she was doing, but she was almost done for the night. Just a few more minutes and she could put it all away till tomorrow. She glanced over at the clock. He had made it again with time to spare. “You’re getting better at this,” she declared. “Maybe we should be giving you less time from now on.”
Chad was horrified. “Oh no, Mistress. Please don’t do that! I’m trying so hard, I really am!”
“And you’re succeeding very, very well.” She looked at him for a moment. “Okay, we won’t change your time… for now!” She looked back down at her work for a moment. She really needed to finish it. “Okay, Sissy. I need to finish this. I’ll be with you in a few minutes.” She paused, thinking again. “In the meantime, get everything ready for your punishment. And make sure you spread some protection on the floor in case you pee again!”
Punishment! Chad’s heart fell. He had made it, but this punishment was for the demerit he had gotten earlier in the day for not using his sissy voice on the phone. How could he talk that way when he was at work? He couldn’t! It wasn’t fair! He grabbed a stack of disposable diapers and carried them over to her usual punishment spot. He spread a few of the diapers out on the floor, covering as much as he thought might be necessary. He glanced at her yardstick leaning up against the corner. He didn’t dare touch it, even though he really wanted to throw it away somewhere… somewhere where she could never find it or use it again.
Mel was still working, so he waited… and waited. More pee ran down his leg. He was worried about it running down onto her floor so he stood on top of the diapers he had just spread out. And he continued to wait, silently.
With a huge sigh, Mel finally finished. She stared at her laptop for a few seconds more, then turned it off and closed the cover. She took a deep breath to bring herself back to life. It was time to get away from work for a while. Time to do something else. And Sissy was waiting. She didn’t really enjoy punishing him, but she was ready to do anything other than work, and punishing him was physical activity, and she felt the need to do something physical just then.
He was waiting patiently, standing on some spread-out diapers. When she saw how much pee had run down his leg, she was glad that he had done it. The skirt to his maid’s dress was still pulled high up around his torso, completely exposing his overly sodden diaper. Two seconds later, she removed that diaper and he was naked from the waist down… except for his shoes and chastity device. She looked at his penis inside that device. Tiny again. Totally! Just what she wanted to see.
She walked over to the corner and picked up her yardstick and swished it through the air a few times. She saw the look of fear in his face. Good! She got into her usual position and waited till he bent over with his arms on the back of the chair in front of him. His legs were slightly spread, but he had put enough diapers under him that he was still standing on them. It reminded her of something. She swung the yardstick through the air at his backside – hard!
The sudden blow to his bottom sent a shock wave throughout Chad. No matter how much he expected it, or tried to prepare himself for it, her stick always came as a surprise, and it always hurt… a lot! He stood up and curtseyed. “Thank you, Mistwess,” he said in his best sissy voice. Then he got back into position.
“You know, Sissy,” Mel said before she brought her stick back down again. “Since you’ve gone to all the trouble to protect the floor so nicely, I think we’re going to make a new rule.” She brought her stick down on him again.
Chad barely had time to register her statement about a new rule when the blow came, emphasizing the point. Pain! What new rule? What could she possibly want now? He stood up, curtseyed again and thanked her. Then bent back over again.
“From now on, Sissy,” she said, “every time you get punished, I expect to see you peeing on the floor.” Swish… Whap!
Again, Chad barely had time to register what she said before the stinging pain hit him. He was fighting back the tears and was mostly succeeding – mostly. Now she expected him to pee every time she punished him? That was crazy! Again he curtseyed and thanked her and got himself back into position.
Mel continued speaking. “In fact, Sissy. If I don’t see you peeing during your punishment, then I’m going to add another five swats. Every time!” Swish – Whap!
Ouch! Another five swats? His heart fell a bit more. How could she? But unfortunately, he wasn’t in charge, he wasn’t in charge of anything. All he could do about it was to stand back up, curtsey, and thank her one more time before getting back into position for another blow.
Ten swats. Ten very hard, very stinging swats. Ten curtseys. Ten times thanking her for punishing him. But no pee had come out of him during his punishment. So it continued. He wasn’t able to pee again till after the thirteenth blow. He jubilantly told her the moment he felt it starting, as he was bent over, waiting for blow number fourteen. Mel was happy and praised him. He started to get up, but she made him stay right where he was, bent over as if waiting. The peeing didn’t last very long and when it was over, he tried to stand up again, but she made him get right back into position. There were still two more swats to go. Chad was heartbroken to discover that no matter what, he would still receive the full extra five swats. He was already crying somewhat, but now he openly cried much harder.
When they were done, Mel rediapered him in one of the wet diapers he had been standing on. Her diaper job felt rushed and not as secure as she usually did it, but he said nothing. Maybe the diaper would leek faster this way.
“Clean this up and check the laundry,” she told him. “Let me know when you get the clothes into the dryer.”
Chad tearfully bent down to start picking up the diapers he had been standing on while Mel headed into her bedroom. He carefully folded them and put them away. He heard the washer finishing and moved the clothes into the dryer. She was still in her bedroom. It was time to let her know that he was done.
He walked to her bedroom doorway and poked his head inside. He saw her reading something. Her bed covers were pulled back and he saw the ropes out once again. Uh oh! “Mistress,” he said hesitantly. “The clothes are in the dryer now.”
She looked up. “Good. Go get those diapers you were standing on earlier so we can cover the bed with them.”
Chad took one more look at the ropes on her bed and went back to get the diapers. He brought them back to her and helped her spread them out over her bed. She made him get a few more to make sure everything was doubly protected. Then she asked him to take his dress off. After that, she removed the diaper he was wearing.
As soon as he was as naked as he was capable of getting, she had him climb up onto the bed, kneeling on it, on all fours. She tied the ropes to his wrists first, then to his ankles. It didn’t feel as secure as she usually did it, but he knew he wasn’t going anywhere.
She was doing something behind him. Far enough away that when he turned his head, he couldn’t see what it was. A moment later, she was liberally spreading lubricant on, and in, his tiny asshole. His spirits soared. This was what he wanted! She was going to use one of her toys on him again. He mentally prepared himself for the pleasure. He could almost feel the toy going in and out of him already.
He felt her approaching behind him again. He was ready. Something hard touched his asshole and a wave of pleasant anticipation ran through him. That something was pushing against him now, trying to invade his insides, and he wanted it there! He opened himself up to it and felt it going in. But it felt different, like nothing he had ever felt before. And even though it was still going into him, all of a sudden it felt like whatever part of it was at the opening, was much smaller, almost tiny.
And then he felt her manipulating the device inside of him. Yes, it felt good, but nothing like when it was being pushed and pulled in and out. What was she doing?
Very quickly, he felt the sensation, like he was about to pee, but a little bit different. And suddenly, he felt it coming out of him. His cum was almost pouring out of him. Lots of it! She was milking him again. And whatever she was using on him wasn’t nearly as much fun as what he hoped she would use.
Mel watched, fascinated, as his sperm leaked out through his chastity device. She kept manipulating the oddly shaped Aneros device inside of him and the sperm kept coming. More than she would imagine. Finally, it slowed down and stopped. She carefully pulled the device out of him again. “Well, that went well,” she declared.
Chad said nothing. He felt totally defeated. He was still horny as hell and he knew he would remain that way. But wasn’t that his usual situation? So nothing had really changed… except for the fact that he might be a little more comfortable now since she had milked the sperm our of him. For a while anyway, but only a little while. It was as if she had just removed any chance he might have had for an orgasm, even though he knew that the ability was beyond him. He suddenly felt the need to pee again and let it loose right there on her bed without caring one bit. The bed was well protected anyway.
Mel smiled as she saw him peeing. He seemed to be a bit upset, even though she couldn’t see his face all that well. She didn’t really care. From everything she had read, what she had just done was supposed to be healthy for him. Who would have ever thought? She untied his wrists and ankles, then removed the sodden diaper that had caught most of what had come out of him. She replaced it with another one. “Roll over now, Sissy. It’s time to work on your other side.”
His other side? Work on it? Chad wondered what she was talking about as he rolled over and laid down on his back. Was she going to remove the chastity device, now that she had thoroughly milked him?
Once again, Chad found his hands and ankles bound to the bed, only this time much tighter. He was actually glad when she unlocked his device and began removing it. The moment she pulled the main casing off of him, he felt the cool air on his cock. It felt strange. The touch of her hands as she removed the rest of the device felt strange too. And very nice. Mel left him for a while, and as he expected, came back with a warm wet washcloth that she used to clean him up with. The washcloth felt even better than the slight touch of her hands had earlier.
After cleaning him, Mel looked closer at his cock. There were some hairs starting to grow that needed shaving. She would get them in a few minutes. She could definitely see some light red marks from where the teeth of the device constantly touched him, but other than that, she could detect no other problems. She grabbed his tiny cock with her in her fingers and pulled it up, inspecting it underneath. The thing stretched a bit, but it didn’t’ seem to be growing at all – in the way that she knew it was capable of. As far as she could see, his cock looked perfectly fine. It was just tiny. Very tiny. And so far, her slight manipulations hadn’t made it grow one bit. “I’ll be right back,” she said as she headed off to find her razor.
Once again, Chad enjoyed her wet washcloth going over him. He enjoyed her shaving him there too, but only because the little manipulations of her hands felt very good. They were tiny and brief manipulations, but they still felt nice. They were the only sensations that part of his body had been allowed to feel in such a long time now. He was a bit surprised that he wasn’t responding sexually to her touch there, even though he wanted to. But then, after being milked like she had just done, he wasn’t sure if he would be able to. Actually, he realized that she was being careful to not really grab him or try to stimulate him too much at all – which was so disappointing.
All too soon she was done. He really enjoyed feeling her spreading some kind of cream all over him down there, but again, her attentions didn’t last long at all. And then he felt her fitting the device back onto him again. The feeling of utter disappointment felt like a lead weight in his stomach. Piece by piece he felt the device going back on.
Mel looked at the large teeth that had been in the device, then back at his cock. The teeth hadn’t hurt him at all, but there were some small red marks from them. She decided to change them out for the medium sized teeth instead. As she fitted them into the device, she wondered if he would start to get any bigger now. Only time would tell.
With a feeling of dread, Chad felt his cock once again being enclosed as the device was slipped over him. The feeling and sound of the tiny lock sent an awful feeling through him too. And then he felt her untying his ankles. He waited for her to release his hands as well, but she didn’t. Instead, he realized she was just getting ready to diaper him again.
Mel took one last look at his penis inside the device. It was still just as small as ever, but would it be that small the next time she saw it? She reached for the jar on her nightstand that held the suppositories and pretended to pull one out. She knew he was watching her. She clearly saw the look of displeasure as she pretended to put it up inside of him. He had no idea that she had put nothing but her finger up inside of him at all.
She diapered him then, heavily, in four disposable diapers that would last him the rest of the night. Finally, she released his hands. “Put your dress back on,” she told him. “Then clean my bed up and make it. And when you’re done, see to the laundry.” She walked away from him then. There was nothing more that she needed to say. She was the lady of the manor and he was only her maid. It felt so good!