The Bet - Chapter 39 (Tuesday – week 6 Part 5 of 8)

The Bet
by Karen Singer

Chapter 39 (Tuesday – week 6 Part 5 of 8)

Mel smiled as she watched him stare at his baby dress before finally walking out. Actually, she knew exactly what she was going to wear, and she knew exactly what he was going to be wearing – probably. And she knew that he wasn’t going to like it… or maybe he really would. It was a little hard to tell.
She went back to her closet and began making more preparations.
It didn’t take Chad long at all to clean up the kitchen. Just a few minutes really. It also didn’t take him long to finish his latest baby bottle. When he was finished, he went to find Mel. He found her redoing her makeup. She hadn’t changed out of her work clothes yet so he didn’t know which outfit she planned to wear. The fancy one with the skirt was really out of place – yet a part of him wanted to see her in it very badly. “I’m finished,” he announced quietly as she put down her mascara.
“Are you leaking yet?” she asked without turning around.
“Not yet,” he replied. “But I still have some time.”
“Not much,” she replied. “Besides, we’ve still got to get you ready.”
“I’m… working on it,” he replied. Although how he could try any harder or do anything more to leak sooner was beyond him.
“Good,” Mel said. “If you’re finished, then go stand in the corner. Take another baby bottle with you if you think you have to, but just leave me alone while I’m getting dressed.
Chad curtseyed, “Yes, Mistress.” Ugh! The corner! Again! But hopefully, it wouldn’t be for long. He was tempted to grab another baby bottle, but he had just finished two of them really quickly. Besides, since she was just getting dressed, he probably wouldn’t be in his corner too long. He ignored grabbing another bottle and just climbed up onto his perch. He leaned into the wall where he could see nothing, where he wasn’t allowed to move even a muscle, where he felt totally… ignored. Ugh! And all he thought about while he was there, was how could he possibly get out of this tonight? He couldn’t wear that dress, or even act like such a sissy baby in front of his friends – especially since they were all his male friends! He couldn’t! He just couldn’t!
He suddenly felt himself peeing yet again, and wonder of wonders, he felt his diaper leaking. “I’m leaking,” he yelled from his corner.
Mel didn’t hurry, but she did poke her head out of her bedroom to look at him. “Good! Just stay there and keep leaking till I’m ready for you.”
A moment later, Chad heard her closing her bedroom door. He was leaking – which was good, but he was still stuck in his corner. Would she even know if he moved at all? He had heard her door closing. But what if she had closed it just to fool him. What if she was still there watching him. With a quiet sigh, he resigned himself to standing still like he was supposed to. But at least he was leaking already!
Mel had moved his baby dress aside and was laying flat out on the bed. She pulled and grunted a bit, and pulled some more, trying to get the button on her jeans fastened. Why did this damn poker game have to happen in the middle of her period when she was so bloated? It wasn’t fair! Every damn man in the world should be subjected to eternal periods over and over again. Maybe then they’d be a little more considerate! The button finally slipped into place and she dropped her arms for a moment to rest her hands before she tried to pull the zipper up. Fortunately, the zipper wasn’t all that difficult.
She got up off of the bed. The jeans were form fitting and a bit stretchy, but today, they could have been a bit more stretchy. Still, she was determined to wear them. They did look sexy on her – she thought. She added a colorful top that stretched tightly over her breasts, exposing them just a bit and showing them off nicely. Some nice earrings, a necklace, a tennis bracelet, and a couple of rings for her fingers. She slipped a pair of heels onto her feet. Her heels weren’t nearly as high as Sissy’s were, but she considered them to be plenty sexy enough. Height wasn’t everything! She checked her image in the mirror, turning left and right so she could see as much as possible. It would have to be good enough.
Now it was time for Sissy! She made a few last preparations, laying all his clothes back out on the bed again. Finally, she opened her bedroom door and went back into the living room. He was still in the corner – still up on his perch. “Okay, Sissy,” she said, “Get out of there. We need to punish you quickly tonight so we can get you ready to go. So hurry up and get the floor prepared.”
Chad pulled himself gratefully out of his corner. Punished? Ugh! Why couldn’t she just forget it for once? He noticed that she had gone with the jeans outfit and was actually glad to see it – even though the other one would have been a lot more interesting. But as he spread the protective diapers out on the floor, all he could still think about was having to wear his silly baby dress in front of all the guys. He just couldn’t!
Mel got her yardstick and was in position with it before Chad had even finished. “That’s good enough,” she said. “Now get that dress off, and hurry!”
Chad got undressed as quickly as possible. In moments he was down to just his leaking diaper, bra and waist cincher. He saw Mel looking at him, waiting. He quickly began unfastening his diaper, which practically fell off of him since it was so wet. He got into position and leaned up against the chair. Her first blow came sooner than he expected… but then, she was in a hurry tonight. He stood up quickly and curtseyed… and realized he was peeing again. He rolled his eyes as he thanked her – trying to ignore the pee that was flowing out of his chastity device.
“That’s why we protect the floor,” Mel said as she readied her stick once again. He was still peeing as she brought it down hard on his backside again. She waited as he went through his little part of the ritual. “We’re going to be out with some of your friends tonight,” she said as she waited for him to get back into place. “And like it or not, I’m going to require you to use your sissy voice – even around them!” Swat! “So don’t even think about not being able to use it, because I’ll paddle your little bottom right in front of them every time you don’t!” She had to wait again while he curtseyed and thanked her.
“In fact,” she continued, “since it’s probably going to be very obvious that you’re under my thumb – to put it nicely – you’re not going to have any way of denying your sissy status!” Swat! “So think about that! You’re going to use your sissy voice all night – like it or not!”
Her words were all Chad could think about as the punishment continued – in fact he hardly realized that her stick was barely hurting him. He had more than enough worries with everything else that was about to happen – enough worries that nearly had him in tears. He couldn’t! He just couldn’t!
His punishment done, Mel had him lay down right where he was while she got his diapering supplies. When she came back, she was startled to see him suddenly start peeing yet again – he looked surprised too – he had just finished a few minutes ago! She knelt down next to him while she waited for the last of it to leak past his chastity device. He looked very embarrassed about it. “I’m glad to see that happening,” she said.
“I can’t help it!” he replied, sounding very frustrated.
“Like I said, I’m glad to see it.” She cleaned him up thoroughly, which took a few extra moments since she had to wipe down his legs too. “Would you like another suppository up inside you?” she asked in a teasing voice. She didn’t really plan on doing it, she just wanted to tease him with it.
Chad looked up at her horrified. “No thank you!”
“But the results will go so well with your baby outfit,” she countered.
He shook his head again. “Please, Mistress… no.”
Mel just smiled and pulled out some fresh diapers for him.
Chad was very surprised when he realized that she was putting three disposable diapers on him instead of just the one. Did that mean that he wouldn’t have to worry about leaking tonight? He was afraid to ask. He was even more surprised when she began pulling some plastic panties up his legs. Hooray! Even if he leaked, the plastic panties would keep everything dry and keep everyone from knowing he was wet! And three diapers would practically last him all night long – even without the plastic panties! “Thank you, Mistress,” he said as she pulled the plastic panties all the way up into place.
Mel just smiled. “Get into the bedroom now. Let’s get you dressed.”
Chad got up off the floor and followed her into the bedroom. The first thing that he noticed when he got there was that not only was his sissy baby dress laid out on the bed, but she had left her other outfit out on the bed too – the skirt outfit that she had decided not to wear. In a way, he was still a bit disappointed. She would have looked good in it for sure!
Mel let him stare at the clothes on the bed for a moment. “I’m giving you your choice,” she said. “The baby dress, or the skirt outfit. Personally, I’d rather see you go in the baby dress, but at the same time, I’d hate to see the other outfit go to waste. Which one do you want to wear?”
For Chad it was no contest. He just couldn’t believe that she was offering him this way out! “The skirt for sure… Mistress.”
She smiled. She had been very sure all along that he would choose that skirt – right from the moment she had found it in her closet this morning. She just wasn’t sure how happy he was going to be with everything else she had bought for him to go with it. “Okay,” she said, trying to sound a little disappointed. “If that’s what you’d rather wear, then we’ll go with it.”
“Please,” Chad pleaded. “I’d much rather wear the skirt!”
Mel turned away – just so he wouldn’t see the smirk that she knew she couldn’t hide. “Okay then,” she said as she headed over to her dresser. “If you’re going to wear that outfit, then you’re going to need some other things to go with it.”
With it? What was she talking about? Chad was suddenly very worried once again.
Mel pulled a bra out of her drawer and handed it to him. He held it up to look at it. There really wasn’t much to it. The whole thing seemed to be made up of fancy black lace, and the cups seemed to be only about half there, which would leave the top of his glued on breasts almost completely exposed. He looked up at her questioningly.
“If you wear that top, you don’t want too much of your bra showing. The bra you’ve got on now will be way too visible.
Chad unfastened his bra and pulled it off, leaving his glued on breasts to hang heavily from his chest. He started to try to put the new bra on, and found that as he expected, the cups really didn’t cover very much at all. In the end, Mel helped him to keep things moving along a little better – and to make sure it was adjusted to exactly the way she wanted it, which was to ensure that his breasts would show very prominently.
Once his bra was in place, she returned to her dresser drawer once again and pulled something else out. She turned around with it. “This has to be next,” she said as she held out the garment.
Chad took it from her, fairly surprised. It was another girdle. But unlike all his other girdles that were all-in-one girdles, this one had no built in bra and an open bottom. It did have a very high waist though.
“With that skirt, you’ll need something to hold your diapers in better so they don’t show as much,” Mel explained. It was at that point that Chad realized that everything she had bought had to be pre-planned. She had never really intended on him wearing the sissy baby dress at all. He actually felt grateful as he struggled to pull the tight girdle up where it belonged. It was tight – easily as tight as his newest all-in-one girdles had been when they were new. And with the waist cincher under it, his stomach felt even more compressed than ever. He took a moment to look at his figure in the mirror. Did he look more womanly now? He really didn’t get the chance to notice because all he could stare at was the very bottom of the girdle where his plastic panties were poking out just below the edge of the girdle. Well, at least he’d have the skirt to cover everything up.
Mel went back to her drawer once again and pulled more black lace out of it. It took Chad a moment to realize what it was. This time it wasn’t a bra, this time it was a garter belt. From what he could tell, it was a very close match to the bra he was wearing. It had two long garters hanging down in the front and two long garters hanging down in the back.
Mel helped him fasten it on before she again went back to her dresser drawer. Chad immediately began to worry about what else she might have in there. What she brought out next didn’t surprise him, at first. She handed him a pair of smoky black stockings. The moment he touched them he realized that they didn’t feel at all like the pantyhose he wore to work every day – not at all. As he drew them – easily – up his legs, he was surprised by how soft and sensual they felt. He was also surprised to see the long black seam running up the back! It wasn’t till he was fumbling with the garter belt clips that he realized that each of the garters had a fairly large black bow covering each of the clips that attached to the stockings. As soon as he had both stockings on and fastened, he walked around a few steps, trying to get used to the feel of the garters constantly pulling at his stockings – so strange and… sensual!
She had him put his pink patent mary-jane high heeled shoes on next. He again took a few steps around to get used to everything. She kept him dressed just like that while she went to work on his makeup. Chad was surprised by the amount of makeup she seemed to be using on him. She seemed to be breaking every makeup rule that both she and Sandy had taught him. He counted four coats of mascara alone. And the amount of eye-liner and eye-shadow she had used seemed like an awful lot. His eyelids felt stiff by the time she was satisfied. The lipstick she pulled out seemed to be much redder than any he had worn before. Two heavy coats of it, followed by two coats of a glossy sealer. He had been wearing lipstick every day for the last few weeks now, but his lips had never felt that strange.
Finally, she looked at him carefully and pronounced him almost done. We just need to change one last thing,” she said as she reached for his ears. Chad was surprised to feel her removing his earrings. He was more surprised when she opened a little dish that had been on the counter next to her and discovered it held a pair of earrings soaking in a pool of astringent. She reached in and pulled one out. It was a long collection of silver disks. “These are mine – so don’t lose them,” she said as she let the excess liquid drip off. “I know you really shouldn’t be wearing anything like this yet, but since it’s just for tonight, I think you’ll be alright. Besides, you really need something like this to go with the rest of your outfit. Those little ones just don’t look right.”
Look right? Chad was suddenly more concerned than ever with how he looked – especially since he wasn’t anywhere near where he could see himself in a mirror. He let her hook the earring through his ear. He immediately noticed the weight of it. As he turned his head slightly, he was very aware of the tinkling sound the disks made as they moved against each other. It startled him enough that he involuntarily moved more – which made them sound even louder. Oh great! How was he supposed to ignore that all night! A moment later, the sound was invading both his ears. He found both the weight and sound of his new earrings not only distracting, but actually sensual too. He reached up and touched each of them, feeling the little disks in his fingers… feeling the pull on his earlobes as he held them. So different… so strange… so… feminine?
“Get your skirt on now,” Mel told him as she stood up and began putting her makeup away.
Moving to get to the skirt brought a whole new cacophony of sound and feeling from his earrings as they moved and clanged and brushed against his neck. Even more distracting – and odd – and sensual – and exciting! He picked up the skirt and examined it. There was no zipper, no fastening mechanism of any kind. He realized that the whole thing was stretchy so he stepped into it and began pulling it up into place. It was very tapered so that the waist was extremely tiny. Once he got it up to the bottom of his diaper covered rear end, he pulled… and struggled… and pulled. He had to work the thing carefully and with a great deal of difficult just to get it over his diaper padded bottom. Once it was in place, he realized just how short it was. It didn’t even come close to covering his garters where they met his stockings. He glanced questioningly at Mel.
“It’s the style,” she told him with a slight giggle. “All the young girls dress like that now.” Chad had his distinct doubts about that. He had never seen any girls with stockings and garters visible below their skirts – hookers maybe, but not any young girls.
The pink top was next. The whole thing felt tight and kingly as he tried to pull it into place over his glued on breasts. Once it was in place, just as he had figured earlier, it exposed all too much of his breasts. He also discovered that the lacy black bra straps weren’t covered at all by the wide neckline. And was it his imagination, or did his breasts seem to stick out more. Of course, the bra probably had a lot to do with that too. The top just made it look more noticeable. “Um… I’m not sure about this outfit,” he said.
Mel only smiled. “The baby dress is still there. I’d really rather see you wear that instead, but the choice is yours.”
There really wasn’t any choice, not as far as he was concerned.
Mel grabbed her makeup once again, only this time she began putting it on his chest – all around the seam where his breasts met his skin. “We want it to look more natural,” she explained. Chad wasn’t sure if he wanted it to look natural or not… not it that outfit.
Once she was done, Mel added a long dangly silver necklace that matched the earrings he was wearing. He found it surprisingly heavy and he could feel it even more than the new wooden ones that he had worn recently. She fastened a silver bracelet around his right wrist that surprisingly went with both the earrings and necklace. Then as one final matching element, she produced a silver belt made up of similar, but very large silver disks, she wrapped it around his now further compressed waist and buckled it. The belt wasn’t tight in the least and settled into place just below where she had fastened it.
Mel finally stepped back to examine him critically. “Magnificent!” she declared happily. Only then did she allow Chad to look at himself in the mirror again.
Chad was afraid to approach the mirror – afraid of what he might see. And the minute he looked, he realized that he had good reason to be afraid. From the pink patent high heels that stood out all too prominently against the black seamed stockings… to the stockings themselves fastened to the black lacy garters – well below the hem of his super short skirt… to the super short skirt itself – so klingy and shiny… to the tight pink top that exposed his now more prominent glued-on breasts… to the fairly heavy and garish makeup that had totally transformed his face… to the silver ornamentation that now accented his entire body… he looked at his entire image, and the first word that came to mind was tarty! Totally tarty. The second thought that came to mind was… “I look like a whore!” he complained.
“The baby dress is still there,” she teased. “Waiting for you.”
Chad got the point. It was either this, or the baby dress – still no contest.