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

The Bet
by Karen Singer

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

Mel watched him, totally delighted with what she was seeing. Obviously, he was having a lot of trouble with such a simple task. And just as obviously, he was quickly learning how difficult the simplest tasks could become with heels on. Ok, so it wasn’t really a fair test, but the whole purpose was for her amusement anyway – and she did find it amusing – very!
It took a long time for him to just finish vacuuming her bedroom, and by the time he was done, she couldn’t stand it anymore. Before he could drag the machine out of her room, she herself reached down and turned the thing off. Then, grabbing him by the wrist of one of his high-heeled covered hands, she dragged him out into the living room and stood him in front of her sofa. She quickly went to her desk drawer where she dragged out the ropes she used to tie him with.
Chad was a bit shocked to see her dragging the ropes out again, although he knew he shouldn’t be that surprised. What he didn’t expect was for her to tie his shoe-covered hands behind his back before she even undressed him. But she seemed to suddenly be in a huge hurry. And when she pushed him down to his knees, still completely dressed, he was more surprised than ever. Very quickly, she had him spread his knees for balance, then she tied his ankles together. But she still wasn’t finished. She tied one more rope to his bound wrists and then wrapped the other end of the rope to his bound ankles. Pulling tightly, she pulled his body backwards, bending him back toward his bound ankles. His arms were stretched back torturously, keeping him very off balance. He was still on his knees, but staying upright wasn’t as easy. If his knees hadn’t been spread, he would have fallen over for sure.
Mel suddenly left him there and he had a few moments to reflect on his position, which was uncomfortable to say the least. She was back a few moments later though and his sight was quickly taken away as she tied one of her scarves tightly around his head. He knew what was about to happen, but he was a bit apprehensive about it. There was an urgency in Mel that he didn’t see very often. He was suddenly a bit afraid of the task he was about to have to perform.
Mel glanced down at her captive sissy maid. She had tied him tighter than usual, and doing so had gotten her juices really flowing. She felt more excited tonight than ever before! Seeing him in his maids dress tonight, all trussed up and helpless seemed to make things that much more exciting for her. He was her fantasy – her perfect maid! Even though that fantasy had seemed to change a bit over the past month. It was now a better fantasy than ever! And it was also now a reality!
She hated taking the time to run to the bathroom to get some towels to protect her sofa, but she knew better than to do this without them. As quickly as she could, she spread them out. Finally, she was ready.
She looked down at him. He was bent backwards, trying to take the strain off of his arms – it wasn’t working. She reached down and caressed his face lovingly. “You know what comes next?” she asked in a rather soft, sultry voice.
Chad gulped apprehensively. But he did know. He was about to have his face shoved roughly into her wet and waiting sex. “Yes, Mistress,” he answered.
She chuckled lightly. Checking once again to make sure he couldn’t see her, she took off her blouse and draped it playfully over his bound arms. She lightly rubbed her bare stomach over his face… ever so lightly. She removed her bra and draped that over his bound arms too. Then she grabbed his face in her hands and rubbed the smooth, soft skin of her breasts back and forth against his face. Over and over again. Exciting her. Teasing him with the feel of them.
She kicked her shoes off quickly and slid out of her slacks. As she tossed them aside, she noticed how obviously wet her panties were. It was a good thing that he was blindfolded and couldn’t see them. She grabbed his face again and spread her legs to either side of him, pulling his face into her wet, panty-covered crotch. She ground that crotch into his face for a few moments before releasing him and moving away. She was so worked up tonight. She didn’t know why and didn’t really care.
She quickly pulled her panties off, almost tearing them in the process and sat down in front of him on the towels that were protecting her couch. She grabbed his head roughly and pulled him toward her, rocking him on his knees, pulling him from leaning backwards to falling forward – directly into her wet and waiting sex. She felt the panic in his body as she pulled him forward and vaguely saw his raised feet off the ground, but in truth, she didn’t care about his discomfort. This time… this moment… was about her and her needs. Not his. She was his mistress and he knew it. Her needs were raging!

Chad fought the position he was in, but there was nothing he could do about it. Tied as he was, there was no escaping the gravity that pulled his face into her waiting crotch. And what a wet, messy crotch it was. Being unable to move his head and body anywhere else, he soon found himself fighting for air as she forced him to grind his face against her sex. She was using him hard already. He tried to do what he could with his tongue, but she was too demanding of him, pulling him too hard, too fast for him to do anything but let her have her way with him.
He felt her orgasm, then as soon as it was done she was pulling at him harder still, wanting more than she had before! She was all need and nothing else. Again he felt her orgasm, and again she began grinding against his battered face like never before. It wasn’t till after her third bout of ecstasy that she finally slowed down, almost seeming to luxuriate in the sensual pleasures of his face against her love spot. Chad took the few seconds of her slowed pace to try to catch his breath and also to wrinkle his nose to relieve the feelings of total abuse that had been wrought against it. What had gotten into her tonight? She had never been like this before?
Since her pace had finally slowed, and he could now breath again… and since she still didn’t seem to want to stop, he tried once again to reach out with his tongue into her very soaked sexual organ. He felt her shudder clear through to his own toes.

Mel breathed in deeply. Her eyes were closed – they had been for quite a while now. She concentrated on the feelings now coming from his talented little tongue. Marvelous! Marvelous! Marvelous! This was life. This was living. This was really what it was all about! All the rest of life was simply waiting, marking time, for this!
Now that she felt more satisfied, the feelings were building slower than they had before. They were more subtle, and as such, more interesting. She could relish in just feeling, and concentrating on, and appreciating – each and every variation of each and every sensation. Glorious… glorious!
It was slower and not as earthshaking, but still her next orgasm was one to appreciate and savor for as long as she could maintain it. Then, on the way down, her body was forced to catch its breath. Yet she didn’t let up on the sissy in her lap. She kept him there, forcing him to give her pleasure… pleasure beyond pleasure.
She felt his tongue slowing, tiring, yet she had no sympathy for him. Her final orgasm came much like the first… building ever so gradually, then staying at the peak for a very long time, then finally diminishing all too quickly. Only when she realized that she was finally done, did she open her eyes and push him backwards… back so that he was leaning backwards once again.
She stared at him. He looked awful… about as bad as she felt good. She felt so satisfied. Yet part of that satisfaction came from the knowledge that he couldn’t get any satisfaction at all. That was a huge part of the allure for her – knowing that she was denying him the very male birthright that he probably valued the most. Yet as she stared at him, there were other emotions in her gaze. Emotions she wasn’t ready yet to recognize… other than perhaps – fondness.
She got up and leaned down next to his side, putting her hands on him. “Here,” she said, “let me help you lay down.” Tenderly, she laid him on his side. She leaned down and kissed his sex soaked head. “I’ll be back in a bit,” she whispered. She stood up and headed to her bathroom for a much needed shower.
Chad laid on his side, blindfolded and tied uncomfortably, still dressed in his maid’s dress, his hands still encased in the high-heeled shoes she had taped onto him, his entire head soaked with the essence of her sex. He could hardly move. He was just glad it was all over. Now if she would just release him soon he’d be a lot happier. He took the time to try to relax as much as he could, but the way she had him tied was putting too much strain on his arms and shoulders.
She had been a terror tonight. Beyond anything she had ever shown before. Yet the fact that he had been able to please her that much, pleased him. He felt good about it, as if he had managed to accomplish something extra good. So why couldn’t she be kind enough to untie him now? Damn! At least she could remove the blindfold so he could see again!
Mel dried herself off after her shower and belted her robe tightly around her. She had left him out there, all tied up, for quite a while now. But she had no intention of letting him loose just yet. A few more minutes wouldn’t hurt him. She wandered back out to her living room and checked on him. As she expected, he hadn’t moved an inch. She saw him move his head a bit at her approach. She ignored him.
She walked around picking up her clothes and the towels that had been protecting her furniture, then she took them all into the bathroom to throw them into the hamper. From there, she went into her bedroom to prepare for what she needed to do next.
Chad mentally screamed when he heard her walking off. Why wasn’t she untying him? His arms and shoulder ached – damn it! But he remained silent as he laid messy and exhausted on her living room carpet. It was a little while later when he finally felt her coming back… actually he never heard her coming, he just suddenly realized she was next to him. She didn’t say a word as she began untying him. The ache in his arms and shoulders was suddenly much worse the moment the rope binding his arms back to his ankles was released. He wished he could stretch and rub them, but that much was still impossible. He felt her releasing his ankles, more new freedom. He waited for her to untie his wrists… but she didn’t.
“Stand up,” she prompted softly as she pulled up gently on his arm.
With her help, he worked his way to his feet and he let her lead him wherever she wanted him to go – into her bedroom he supposed. Finally, he felt her working on the ropes that bound his wrists together… and finally he felt the freedom that his arms craved. He moved them around a bit, trying to get the circulation going again and relieve the awful aching that had built up in his shoulders. He tried to rub them, but the shoes that were still taped to his hands felt strange and hard against his skin. He accidently poked himself with one of the heels as he attempted it. He didn’t dare try that again.
He waited for her to remove his blindfold… or even the shoes taped onto his hands, but instead he felt her loosening the apron tied around his waist that was part of his maid’s uniform. A minute later, she was unzipping his dress and pulling it off of his shoulders, guiding it down his arms and over the shoes on his hands. He stepped out of it as he felt it pooling on the floor past his legs.
She removed the shoes from his feet. His pantyhose and girdle came next. What a relief it was when they were off. Then she attacked his waist cincher… the relief was twice as great. He tried to rub his stomach for a moment, but again, the shoes on his hands felt too strange. Finally, she removed the plastic panties that added the extra protection he needed against his diapers leaking. She had stripped him of almost everything, except the blindfold and the shoes still taped to his hands… and of course his diapers.
She led him gently over to the bed and helped him climb up. A moment later, he felt her removing his sodden diapers, the cool air felt strange and oddly erotic against his bare skin there as soon as they were gone. The wet washcloth she used to wipe him up with felt wonderful too. Very wonderful!
“Roll over, Sweetie,” she said softly as she pushed gently against his side. He rolled over onto his stomach. She wiped his backside more thoroughly with her washcloth. “Your diaper rash is looking better,” she noted. She placed her hand under his stomach. “Hands and knees now, Baby.”
Chad pulled his knees up under him, but when he tried to brace himself on his hands, he found it next to impossible because of the heels still attached to them. No matter how he placed them, he just couldn’t find a suitable position to fully take his weight and brace himself for what he knew was coming. He heard Mel chuckling softly at his predicament. He finally wound up dropping down onto his elbows with his shoe covered hands out of the way. The position left his backside all too exposed up in the air, but he figured that was what she really wanted anyway.
“Here it comes, Baby,” he heard her say. He suddenly felt the hard cold point of her toy up against his asshole. He felt her pushing on it. “Open up, Baby. Let it in.”
And he did. He relaxed and opened up, because he wanted to let it in. He wanted to feel all the delicious sensations that it brought him. The only wonderful sensations he could feel anymore. The sensations that were now the closest thing to sex that he was capable of feeling.
But once she had worked it in and out a few times, loosening him up, getting him used to it, getting him to the point where he was wanting more and more from it, she began working her toy differently than before… almost more purposefully. Over and over again, despite how he wanted her to push it, she was angling it down, pressing with it against the same area over and over again. Within moments, he felt himself suddenly needing to release some fluid… but not quite like peeing. And there was no stopping it. “Good baby,” she crooned as soon as he felt the fluid leaking out of him – more and more with each stroke that she made with her toy. She was milking him again. Purposefully. And there was nothing he could do to stop it.
When she saw no more of his milky seamen dripping out of him, she pulled her dildo completely out of him, granting him no real pleasure at all. “Well, that job went easier than I thought it would,” she exclaimed.
He just sighed and buried his head in his arms.
A thick coat of diaper rash cream, one suppository, three layers of diapers, and plastic panties, and he was done. Finally, she removed his blindfold and washed his face with her washcloth. He felt better… much better. Now if she would just remove the shoes that were taped to his hands… But instead, she went out to the living room and brought back his highest pair of heels. She herself strapped them onto his feet for him. “Ok, Baby. Let’s go back to your place and have a look at your wardrobe.”
That fast, she had changed the mood… not to mention the subject.

Chad felt incredibly stupid, even in his own apartment, walking around with the stupid heels taped to his hands. They made his hands useless… well, next to useless anyway. There wasn’t much he could really do with them like they were. Fortunately, Mel was handling most of what needed to be done… if it involved hands anyway.
Now she was in his closet, pulling out blouse after blouse and holding them up against one of his skirts that she held in her other hand. “See, these all go together perfectly,” she explained. Actually, Chad was only partially understanding everything she said. But he acted like he was understanding it all anyway. At least when she was done with each skirt, she placed it back in the closet right next to a couple of blouses that she thought would go best with it. As far as Chad could tell, once again it looked like everything went well with everything else, and it was just a case of what your personal style was. Basically though, he was just glad to have some outfits sorted out for him.
As she was finishing with the last skirt, he remembered another question he had for her. “Mistress,” he started tentatively, “would it be ok if I didn’t wear pantyhose? With the waist cincher, they’re almost impossible to get on. How do you manage it?”
Mel laughed. “I’ve never worn a waist cincher!” she replied. Then she got a more angry look on her face. “Are you saying that I’m fat?”
Chad was aghast. “No! Not at all! Of course you’re not fat! I just wondered, that’s all. I thought you might have worn one before.”
Mel looked a little less angry, but only a little. “If you don’t want to wear them to work, that’s your decision. But whenever you’re in uniform pantyhose, or some kind of hose, are required! Got it?”
“Yes, Mistress,” he said dropping a quick curtsey.
“If it thrills you enough, as I suppose it probably does, you can get yourself some stockings and a garter belt to hold them.”
Chad was surprised at her suggestion. It did have a certain allure. “Thank you, Mistress.”
“And you better not be telling me that I’m fat!” she exclaimed once again as she closed his closet door.
Chad knew he was on thin ice. He hadn’t said she was fat… not at all! One thing that anybody could easily tell, Mel was not fat! She was… perfect!
Mel grabbed his baby-doll nighty and pulled it over his head. “Ok, Sissy. To bed with you. I’ll get your bottles for you.”
Chad couldn’t believe it. She wasn’t going to remove the shoes that were taped to his hands – let alone the shoes strapped to his feet. He held them out. “Mistress, are you going to remove them?”
She smiled. “No. They amuse me. Leave them.”
“How about my other shoes,” he asked, indicating the heels on his feet.
“They amuse me too,” she replied with a wicked smile.
With a big sigh of frustration, Chad made his way to his blowup mattress and laid down while Mel went out to the kitchen to get his nightly bottles. The shoes covering his hands made it impossible to pull the covers over himself properly. When she came back, she set both bottles along with his pacifier down on the floor next to him and pulled the covers up for him. “What am I supposed to do in the morning?” he asked as he held up his shoe covered hands again.
She chuckled lightly once again and her wicked smile returned. “We’ll just have to see, won’t we!” Then she held out one of the bottles for him to take.
Chad had a lot of trouble holding the bottles with the shoes on his hands. But once squeezed in place between them, he was able to lay there and drink it easily. Mel watched him to make sure he could manage well enough, then she walked over to his bedroom door and turned out the light at the switch. “Good night, Baby. Sleep tight.” And with another wicked smile, she was gone.
Chad laid there in the darkening room, wondering what he was going to do in the morning. He couldn’t manage anything with his hands handicapped the way they were. He couldn’t even phone her to ask for her help.
The heels still on his feet began to ache. He wanted desperately to remove them so he could flex his feet. But that was impossible because of the heels strapped to his hands. Impossible! Impossible! Impossible! His whole situation was impossible! His whole life was impossible! And that’s what he mostly thought about while he drank his entire first bottle, and his entire second bottle. He desperately wanted the pacifier she had placed on the floor next to him but he couldn’t pick it up to put it in his mouth. Feeling very frustrated, he finally fell asleep.

Late, late that night, Mel snuck quietly into his room as she did every night. He was such a sound sleeper that it would take a lot to wake him. She quickly set the alarm on his pink clock radio so he would wake up when he needed to. She knelt down next to him with the scissors she had brought and cut the tape that bound the shoes onto his hands. She slipped the shoes off as gently as she could so as not to wake him. He stirred, but didn’t fully come awake. Good. She saw him moving his lips and tongue a bit restlessly. She took a chance and picked up his pacifier from the floor that he obviously hadn’t been able to pick up earlier. She touched it to his lips and watched as he instantly took it in and began sucking on it. His restlessness suddenly ceased and he fell back into a deeper sleep. She leaned over and kissed his forehead with the barest graze of a kiss. “Sleep well, my baby,” she whispered ever so softly. “Sleep well.”