The Bet - Chapter 41 (Thursday – week 6 Part 8 of 8)

The Bet
by Karen Singer

Chapter 41 (Thursday – week 6 Part 8 of 8)

On the drive home in the car, Mel’s thoughts continuously worked themselves around Chad and the little time remaining in the bet. Realizing that she was going nowhere with her thoughts and having no further answers as to what else she could do to bring on his total incontinence, she forced herself to turn to other things. Business first! First thing, as soon as they got home, she needed to get another baby bottle into him. He hadn’t had anything to drink since they left the restaurant. She needed to keep him wetting! That much had to be done above everything else!
Next, she allowed herself to be reminded of what she had in the trunk of the car for him… which led to other more pleasant – and stimulating – thoughts. Without realizing it, her foot stepped harder on the accelerator. She couldn’t wait to get home!
But now she faced a small dilemma. She didn’t want him to see the tutu she had gotten him till he was fully dressed in the rest of his ballet costume. How was she going to manage that? Well, one way or another, she’d think of something. Her tires actually squealed a bit as she turned off the road into the apartment project. Realizing she was going way too fast, she forced herself to slow down… but not by much. She wanted to get home! She pulled into her parking space faster than she had probably ever done it before. “Okay, Sissy. Upstairs, and be quick about it!”
Chad didn’t know what her hurry was, he only knew that he was glad they had managed to get home safely. He breathed a small sigh of relief as he opened the car door and quickly got out. He was actually glad to get out of the car – despite the fact that his wet diapers were again fully on display. Being humiliated was one thing, but being killed in an auto accident was another! With his purse over one arm, he opened the back door and grabbed his diaper bag and his wet skirt. Then he hurried up to her apartment. So what was her big rush? He had been feeling nice and mellow after the relaxation session. Obviously, Mel didn’t get as much out of it as he did!
Mel hurried straight to her refrigerator and pulled another bottle out for him. She noticed as she did so that the number of bottles was starting to get awfully low again. She had to do something about that fairly soon too. It was another thing to worry about. She suddenly felt even more pressed for time from yet another direction.
Sissy had just set his things down under the little table by the door and was examining his wet skirt. “Here,” she said as she handed him the bottle. “Start drinking!”
More to drink was the last thing that Chad wanted. He still felt uncomfortably bloated from all the tea at dinner. And this bottle held tea too! Ugh! But he put the bottle to his mouth and… pretended… to drink, which seemed to appease Mel.
Mel grabbed the skirt out of his hands and threw it at the washing machine. “You can worry about that thing later,” she said. “I have other things I want you to do now. And keep drinking!” she added.
Chad didn’t know what had gotten into her. But this time he actually did take a small swig from the tea in the bottle.
She pushed him into the bedroom. “Start getting undressed!”
By her urgency, Chad wondered if she was about to tie him up for sex again. It had been a while now, and no doubt she was ready. And by her rush, probably overly ready. He started bracing himself for it as he began removing his blouse.
Mel watched him undressing and glanced at his diaper – which looked absolutely soaked – and she had put two diapers on him. Darn! The last thing she wanted right now was to have his new ballet outfit stained by his pee. As he started removing his shoes, she ran to the bathroom where she kept several stacks of diapers for him and grabbed one.
Before Chad had a chance to removed anything else, he found himself on the floor being quickly changed again. Being changed was nice, but unfortunately it was into only one diaper again – which meant that she still wasn’t finished with her games for the night. No wonder she had handed him the bottle to drink so soon. And if he had to be leaking again, then like it or not, he had better keep drinking.
As soon as Mel had him rediapered and in a fresh pair of plastic panties, she stood him up again to look him over. He still had on his bra over his breast forms and his waist cincher. She decided that for now he could just leave it all. She opened one of her dresser drawers and pulled out the white tights to his ballet costume. “Here,” she said. “Put these on.”
Chad was a little surprised, he expected her to be putting ropes on him, not the white tights. But the white tights were the ones that went to the ballet outfit she had bought him. He suddenly had the suspicion that she would have him dancing again very shortly. He worked the tights over his feet, up his legs, and over his diaper padded bottom. She immediately handed him the pink leotard that she had bought to go with the tights. The leotard was tight and a little hard to get into, especially since his diaper clad bottom didn’t allow the thing to go fully up into his crotch. But eventually, it did fit – well enough anyway.
Just the sight of him in the leotard and tights was enough to excite Mel. The odd bulge around his diaper only seemed to add to her thrill. “Get drinking again,” she ordered just before she hurried out of the room.
Reluctantly, Chad picked up the baby bottle and put it to his lips before he followed her out to her living room. As he expected, she was at her stereo system, hunting for the music she wanted. Within moments the now familiar strains of her favorite ballet music were pouring out of the speakers.
“Dance for me, Sissy,” she ordered.
With baby bottle in hand, Chad began trying to dance to the music. Mel watched him for a few moments, then she rushed out of the room saying she’d be right back. Chad kept dancing. She was gone far longer than he expected she would be, but when she came back, she was barefoot and wearing a pair of short shorts and a tee-shirt. But what surprised Chad even more, was that she immediately began dancing along with him. Something about her movements made him stop and stare – totally dumbfounded.
“What’s wrong?” she asked as she stopped dancing.
Chad shook his head. “You’re… beautiful! I mean, you’re so good! Great even!”
Mel blushed a bit. “Not really. But I took ballet for a long time when I was young.” She twirled gracefully on one foot with her arms over her head.
Chad was mesmerized. She was so graceful! Who would have ever thought?
“Now come and dance with me.”
Chad tried to dance, to follow what she was doing, but it was impossible. He was more interested in just watching her. He could never hope to come close to the fluid feminine grace of her movements.
Mel suddenly stopped. “Wait, wait!” she called as she ran for the stereo system to turn it off. “We need to practice the positions first!” She grabbed the baby bottle out of Chad’s hand and threw it onto the couch out of the way. “Carpet is not the best thing for dancing, but it’s all we have.” She pointed at the end of the couch were she usually had him practice the ballet positions. Once he was in place, she stood right in front of him. “First position!” she ordered as she herself immediately went into the odd stance.
Chad was holding onto the couch with one hand and didn’t really know what to do with his other arm, but her arms were gracefully curved downward. He tried his best to copy it with his free arm as he put his feet back to back in the awkward position. It was the first time he had done it without heels on. The feeling was totally different. One by one, she led him through all the positions he had learned so far. Then, she started doing them all over again, this time bending her knees down and moving her arms gracefully, then back up again, over and over. Chad was almost as mesmerized watching her do these exercises as he had been watching her dance. And her arms… Where he didn’t know what to do with his arms, hers just seemed to naturally flow into the most beautiful positions. While he did his best to copy her, he knew that next to her, he had to look like a total jerk! Obviously!
“Move away from that couch now,” she ordered. “You’re going to have to learn to keep your balance without holding onto anything.”
Again she took him through everything he had learned so far, but this time with nothing to hold onto. Chad actually thought he did fairly well… as far as not falling over. Maybe all the time he spent in high heels helped. But now she was making things even more difficult by requiring him to move his arms the way she did… gracefully – yeah right – and bending his knees down and then rising back up again. Everything was like its own separate little dance as he followed her directions and tried to copy what she did. And she was incredibly good at it!
Mel had actually been enjoying herself, but she suddenly stopped. While the sight of him in just the pink leotard and white tights brought back so many memories of her own girlhood, she had more to his costume out in the car that she desperately wanted to see on him. But even as she paused, she realized one other thing. All the dancing wasn’t getting any more liquid into his system. And she absolutely had to keep him drinking. Time was running out! “Grab your baby bottle and start drinking again,” she ordered.
Chad caught the urgency in her voice. What was her big rush? First she drove home like a crazy woman, and now she was hurrying things along again? Why did she even bother with the relaxation therapy if she was going to be like this afterwards? But he grabbed his bottle again and put it to his lips again, this time actually drinking it.
“Keep drinking, and keep practicing!” she ordered. “Switch hands on the bottle once in a while so you learn to do things with the other arm.” She looked at him with frustration. She wanted him to dance… yet she wanted him to keep drinking too! And it really wasn’t a very good arrangement. Growling slightly at the irritation, she ran to her purse and grabbed her car keys. “I’ll be right back,” she said. “I expect to see you practicing when I get back… and I expect to see that bottle nearly finished!”
Before Chad could fully understand her instructions, she was gone! Where? Why? And did he really have to keep at it if she wasn’t there? Okay, if she expected the bottle to be finished then he had to keep working on it. But as to the dancing, why bother? But what if she came back right away? She did say she’d be right back. Frustrated with the whole situation, he went back to first position and started dipping down then up again with his right arm curved up over his head – and his left arm curved to hold the baby bottle in his mouth.
Mel grabbed the bulky tutu and the box with the toe shoes out of her trunk and closed it again. As fast as she had run down the stairs, she was almost as fast going back up again – despite the items she was now cradling against her chest. Rushing back into her apartment, she was just in time to see him dipping down with one arm over his head and the other one holding the bottle in his mouth. Another small wave of pleasure ran through her body. She saw him turn quickly to look towards her. Well, the darn tutu was so big it was hard to hide anyway. Besides, she wasn’t going to wait another minute to start dressing him further.
“Okay, Sissy,” she said as she closed the door behind her and hurried towards him, “let’s finish getting you dressed.”
Chad saw the bulky white thing in her hand as well as the pink box. He quickly realized that the other things she had ordered for him had arrived. Oh goody! And yet he felt the first little signs of sexual arousal enter him once again… it had been soooo long!
Mel threw the tutu, still in its plastic wrapper, onto the couch. She opened the box and pulled out the pink toe-shoes. “Here,” she said as she held them out to him. “Put these on.”
Chad grabbed the pink slippers and held them up. They certainly didn’t weigh very much. They looked very soft too. He set his bottle down and sat on the floor to put them on. He pulled one of them onto his right foot. It was a bit tighter than he expected and his toes were pushed firmly up against the soft padding of the toe area. He didn’t know what to do with the long pink ribbons, so he ignored them for now and slipped the other one onto his other foot. But then of course, he had to figure out how to tie the ribbons. He started wrapping them around his leg, but Mel quickly stopped him.
“Not like that,” she said. “Here, let me do that for you. You just drink that bottle – and hurry up with it.” She grabbed just one of the ribbons from one shoe and wrapped it up and around his ankle twice, then she grabbed the other ribbon and did the same from the opposite direction, then she tied them off on the inside of his ankle and tucked the remaining ribbon under the knot. “There, that’s how you do it,” she said as she finished and grabbed one of the ribbons from his other foot. Very shortly, that one was tied firmly too.
Chad had watched her closely, knowing that even now that he had seen it, it would take some practice. He stood up again. The ballet shoes felt strange on his feet – and soft – very soft. The only problem was that she had purposely gotten them half a size too small so his toes felt very crowded against the padded tip of the shoes. And then he saw her grab the huge white plastic wrapped mass on the couch – the tutu. The moment she got the plastic off of it and he saw all the white net material bunched up all the way around, he felt his under-exercised sexual need lurch hard. Oh wow! He purposely checked to see if he felt anything from his miserable chastity device. No pain – yet. Good!
Mel set the crazy white tutu down on the floor and spread out the middle so he could step into it. One pink slipper covered foot, then the other. She instantly began pulling it up his legs, up over his diaper padded bottom. She held it in place just above his diaper – not quite down to his hips were it was supposed to go, but his diaper kind of made it necessary to fasten it a bit higher. Pulling it tight, she began fastening it up.
The higher the crazy skirt went up his legs, the more Chad felt that sexual urge that was running through him. That urge rose even more as he felt her fastening it, pulling it tighter and tighter. It didn’t weigh much, but he could certainly feel it attached to him. And then she finished fastening it and she stepped away. He continued to stare down at the front of the weird garment surrounding him. He moved his hips a little. Yes, he could definitely tell that the thing was there, but he couldn’t feel it moving at all – probably because it didn’t. He realized that his problem now was that he couldn’t see his feet! How was he supposed to learn ballet if he couldn’t see his feet? The full realization of what he was now wearing hit him. He was wearing a damn tutu! A stupid, silly, sissy tutu! For the first time, he felt a bit of irritation coming from his chastity device. Ugh! Feeling somewhat embarrassed, he turned around and faced her.
Mel stepped back further so she could see him better. She clasped her hands together as her eyes lit up with delight. The tutu was much higher on his hips than it really should have been, and now, standing back from him a bit, she could easily make out the odd bulges of his diaper below it. The only thing… the only thing… Perhaps a pretty tiara would help. Yes! She defiantly wanted a tiara for him. She made a mental note to get him one as soon as possible. Something sparkly! Without realizing it, her breathing began to quicken.
“Okay, Sissy, let’s try it again.” She quickly took her place in front of him and together she led him through the exercises again. But now, with the tutu on, he wasn’t doing as well. She saw him keep trying to look down at his feet – which obviously he couldn’t see anymore. “Don’t look down! Keep your head up high! Graceful…” But he was anything but graceful. Yet, she was absolutely loving every minute of it.
During one movement, she noticed the baby bottle he had put down again. Oh darn! She had to keep him drinking! But she was enjoying watching him dancing – he looked so absurd! “Keep your head up!” she told him once again – for the fourth time – at least. She watched as he pulled his head back up to look directly at her again instead of trying vainly to look down at his feet. An idea hit her. She stopped what she was doing. “Grab your bottle again,” she ordered, “and keep drinking! You can’t drink from that thing if you’re looking down. Maybe it will help you to keep your head up!”
Keep drinking? While trying to dance? And he couldn’t even see his own feet? She had to be kidding! But he once again grabbed his baby bottle and put it to his lips as he got back into position in front of her. Keep drinking? While dancing? It was absurd!
Mel smiled. At least his head was up now. And if he had to keep drinking from that thing then he wouldn’t be able to even try to look down at his feet. She wanted his head up – where it belonged. “Now… once again.” She started in on the exercises once again, moving gracefully where he was anything but. Even a little girl had more feminine mannerisms in her movements than he had! But still, wasn’t that also kind of the point? Sissy was in reality a he… not a she. And she was making him do something totally outrageous again. Not to mention that all this might even help remove some of his nasty male movement mannerisms.
She went back to the stereo and turned it on again. Then she continued with him again… dancing with him… watching him… taking in every little nuance of him and what he was doing. She was doing it again. She was taking away just a tiny bit more of what little masculinity he had. Making him do something totally feminine. Making him move more and more gracefully… more and more femininely. And hopefully, some of this training might stick as far as his everyday movements were concerned.
Chad didn’t quite know what to do. In order to keep drinking, he had to keep his head tilted back – further and further as the darn bottle emptied. And he had to try to dance too? It wasn’t working! And yet she didn’t seem to be complaining at all – fortunately – because he really didn’t know what else he could do other than to try like he was. Having to keep drinking from the bottle and keep his head back was so difficult that it made him lose all of the sexual arousal from his situation that he had felt earlier. He was forced to focus entirely on trying to do the dance steps correctly – while still drinking. Difficult didn’t even begin to describe it!
For some unknown reason, Mel was surprised when after a few minutes he actually started to look a little better – despite having to keep the silly bottle in his mouth. But just looking at him now was starting to make her wet and tingly in some very special places. His entire outfit was so much like one she had worn in several dance recitals when she was little. It brought back so many memories. Okay, so the tutu was a bit bigger – a lot bigger really. And of course the outline of his diaper underneath the tutu looked strange too – but somehow it only added to her excitement since she knew what it represented. And okay, so he himself wasn’t exactly a little girl, but… but wasn’t that kind of part of the whole point here? So many memories of herself as a child, and now he going through some of the same things – him… a man… sort of.
Her tingling suddenly became something she couldn’t ignore. She stopped dancing and ran for her drawer where she kept the ropes to bind him. She ran back to him and noticed that his bottle was almost done. She wanted him to finish it. “Keep drinking,” she ordered as she pushed down on his shoulders, guiding him to his knees in front of the couch.
She started with his ankles, binding them tightly together. But he still wasn’t quite done with his damn bottle! She ran to her room and grabbed one of her scarves. Moments later, she was tying it tightly around his head, shutting of his eyesight – completely. As she tied it, she heard the rattle of the bottle sucking air. Finally! She took the bottle from him and threw it to the far side of the couch. She grabbed his wrists and pulled them back behind him, binding them together, and finally, bending him backwards a bit to bind him wrists to his ankles. His usual position – and her favorite.
The couch had to be prepared! Quickly she ran and grabbed towels and some of his disposable diapers. Since she still wasn’t finished with her period she spread out the diapers over the area where things were most likely to get messy.
He was ready. The couch was ready. She couldn’t take her eyes off him as she pulled her tee-shirt over her head. Just the sight of him in that pink and white ballet outfit… and now with the pink slippers and that big white tutu! She stopped right there. Was she really going to do this? Make him service her orally before her period had even finished? “If you’re not making a mess, then you’re not having sex!” That phrase ran straight through her mind. She pulled her shorts off and kicked them far out of the way.
But she was on her period! It would be messy! And then it dawned on her. His ballet outfit – it might get stained! No! Should she stop? She only considered that option for a second – absolutely not! She grabbed one of the towels from the sofa that would probably do nothing and pulled it around his neck, tying it behind him. Then she ran to the bathroom where she did her best to clean herself up before things went any further.
When she emerged from the bathroom, she was totally naked and much cleaner in that most important spot… although she had no intention of staying clean for very long. Taking her position right in front of him, she grabbed his head and pulled him toward her – rocking him over on his knees so that his feet came up into the air and his mouth landed exactly where she wanted it. At the first contact from his face she nearly screamed with delight. She wasn’t nearly as silent a moment later as she felt the first little flick from his talented tongue touch the very place she wanted to feel it. Yes! Yes! Yes! Yes! Yes!
Chad had done this so many times now that he was becoming used to the uncomfortable position. Obviously Mel was used to it too since she kept doing this to him… not to mention that just as obviously she was getting a lot of pleasure out of it. And what did he get? Pain, discomfort, frustration, difficult breathing, and very little else! But… at the same time, he took a lot of pleasure in knowing that he was giving her so much satisfaction and pleasure. That alone made him feel good. So he kept at it, believing in the back of his mind that he was truly good at it and that hopefully, she appreciated that fact. His belief was further emphasized by the immense orgasm he realized she was having just then. He couldn’t even remember his own last orgasm – big or little. How long had it been now?
His tongue – his wonderful tongue! And all the little other feelings that went along with it! Mel was in heaven! She opened her eyes and stared down his pink covered back and saw the ridiculous white tutu skirt sticking straight up in the air… and the sight of it brought on another orgasm. So delicious! So wonderful! It felt so good! And just knowing that she had molded him into this silly mockery of human life brought additional pleasure on top of the fabulous pleasure that he was bringing her just then.
Orgasm after orgasm. Some taking much longer than others. She didn’t know how long she had been there and didn’t care. Finally, she realized that he had slowed down a while back and wasn’t getting any more spirited in his task. Growing tired herself, she pulled him away from her. He was an absolute mess. His face was not only wet and slick from her female juices, it was covered with red from her period fluids too. She grabbed one of the diapers she had been sitting on and used it to wipe his face somewhat. The rest could wait till later. She eased him down then to lay on the floor till she could finish getting cleaned up – and she really needed cleaning up now. She glanced at the clock as she headed to the bathroom and paused for a moment. She had been at it for almost an hour! Wow! Where had the time gone? No wonder she felt so good! But a much needed shower was next on her agenda. He could wait and relax for a while where he was… he certainly wasn’t going anywhere. She was tempted for a moment to stick another baby bottle in his mouth, but opted to head straight into the shower instead.
Chad was very grateful that his latest ordeal was over with. He had no idea how long he had been at it, but it seemed like an eternity. Now, he was exhausted. He wanted to move very badly, to stretch his limbs, but tied up like he was, that was impossible. He could feel the silly tutu he was wearing tickling his legs and arms as he laid there. It felt weird to him. So stiff.
He hoped that she wouldn’t be too long in coming back. Of course, just lying there and getting a chance to rest was nice for a change. He needed it now. If it wasn’t for being bound up like he was, he would almost wish to stay right there. Hopefully, she would let him go home soon so he could go to bed. It had been another long day… another long and very difficult day!
Mel tied her robe tightly around her as she finally walked out of the bathroom. She had been so smelly that she had to take a good shower. Now she felt… wonderful! So good! She never expected anything in life could make her feel like this… and her darn period wasn’t even over with yet! Maybe all she really needed was a dose of Sissy every day. That was a very pleasant thought. Soon! Very soon!
She stopped to look down at him for a moment. He was still tied just as she had left him. Well, he should be! She united the towel she had put around his neck to protect his ballet outfit and used it to wipe his face clean. Then she removed his blindfold. The ropes binding his wrists and ankles came next. She sat back on the floor and watched him painfully stretch his arms and hands and legs, rubbing thoroughly the places where the ropes had been. “Have you recovered enough yet?” she asked.
Chad closed his eyes, being able to move again was so good! He took a deep breath before answering in his sissy voice. “I think so.”
She didn’t move though, she just sat there on the floor and looked at him, while he looked back at her. So many emotions ran through her as she looked at him. Probably from seeing him in the pink and white ballet costume. So many memories of her own childhood. And yet, what she was feeling just then was mostly gratitude. Gratitude for the way he made her feel – frequently. “Tell you what, Sissy. Just lay there and I’ll get your things.”
She got to her feet and went in search of all his diaper supplies. She came back to him a few minutes later, her hands full of everything she needed. She unfastened the silly tutu from around his waist, and pulled it off of him. As she did so, she noticed the wet patch all around his crotch on the leotard and tights both. Darn! He had leaked all over it – terribly. She should have double diapered him! But the outfit should be washable so hopefully, no real problem. She moved down to his feet and untied his ballet slippers and slipped them off of him.
She let him get out of the rest of it himself. The minute she caught sight of his diaper she saw how absolutely soaked it was. No wonder he was leaking. She figured that he had to be peeing almost the entire time to get it that wet. But, that was exactly what she wanted… wasn’t it?
She pulled open the tapes on his soaked diaper and wiped him clean. Then she opened the jar of suppositories where he could see her doing it. As usual, he turned his head away at the sight of them. She only pretended to pull one out of the jar… just as she pretended to put it up inside of him, raising his legs high in the air to expose his backside in the process. Unfortunately, the act of pushing it up inside of him seemed to cause him to start peeing again – something she didn’t notice till she brought his legs back down again. She nearly burst out laughing at the sight of it, even though she had to clean him up all over again – a lot more of him.
She quickly slit one of his disposable diapers and got that taped firmly on him before he could pee again. Only then did she go back and prepare the other diapers for him. A few minutes later, he was ready – four disposable diapers and a pair of his plastic panties. “Get your things and go home now, Sissy,” she said. “Don’t forget, three more bottles tonight before you go to bed. And don’t forget to clean your earrings too!”
Chad nodded wearily. “Yes, Mistress,” he replied, but it was a moment before he found the strength to move.
She watched him closely as he struggled with himself before getting to his feet. She was so tempted to reach out and clasp his head in her hands and just give him a big kiss, but she resisted sternly. Finally, he was able to get up. She continued to just sit there. She was enjoying just watching him.
Chad finally struggled to his feet. The four diapers were monstrously bulky – especially after wearing only one thin one. He was glad it was over for the day… mostly. He still had to drink three more bottles before he could go to sleep. Ugh! He hadn’t stopped peeing since the restaurant! He was doing it so much now that he hardly noticed it anymore! Wasn’t enough – enough? He gathered up his things and said good night. Then he turned and left.
She was still sitting on the floor right where she had diapered him. She watched him leaving. Watched him walk out the door and close it behind him. “Good night, Sissy,” she said quietly. “Good night.”