The Bet - Chapter 36 (Saturday – week 5 Part 5 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 5 of 8)

Mel was ready and waiting for him when he knocked. She grabbed her purse, and his diaper bag and opened the door. She was immediately greeted by him with his usual curtsey. She smiled and simply pushed past him.
Chad was a bit nervous about going to the mall. The last time he was there was when she had dressed him up in one of his super sissy dresses and made him act like a super sissy inside. So embarrassing! Would anyone remember him from that? Quite possibly! Since he was still recognizable as a man wearing women’s clothes, he figured that it would be very easy for anyone to make the association. Not a good thing as far as he was concerned!
Mel parked the car. Chad hesitated a moment before getting out, as if he was trying to find the courage within himself to go into the mall again, but he delayed only for a moment. Then he followed Mel inside where she handed him his own diaper bag to carry so she wouldn’t have to lug it around.
Whenever he had been out with her before, dressed in his maid’s uniform, it was obvious to everyone that he was her servant. Now, strangely, she was walking beside him and chatting with him about things she saw in the display windows as if he was her best girlfriend. It seemed so strange. He often didn’t know how to properly reply to her comments but fortunately, she didn’t seem to mind the times when he said nothing.
She led him into many stores, always telling him to look to see if there was anything he wanted to buy for himself. But Chad wasn’t really interested in looking at anything for himself. He did get the “privilege” of holding her purse often while she tried on different outfits. Somehow, dressed as he was, holding her purse didn’t seem to matter much at all.
When they finally got to the department store where he had bought his makeup, Mel again teased him about asking for another makeup demonstration, but again Chad politely refused. He did have to ask for all the makeup items he needed in his stupid sissy voice though – since Mel was standing right next to him – which gave the makeup girl quite a shock at first, then sent her into fits of laughter. Embarrassing! But fortunately, Mel didn’t make him do anything else there to embarrass him further.
It wasn’t till they left the store and headed out into the mall area that Mel paused and stopped. There was a store stuck in the corner, just off of the entrance to the department store that had been there a very long time. But it was one of those stores that she had never bothered with before, so she barely ever noticed it. But now… now it sparked not only interest, but also, fantasies! Much to Chad’s horror, she headed straight for it.
The dancewear shop that they entered wasn’t huge, space wise, but the store was so packed with display racks that it was hard to move without constantly brushing against something. The moment they entered, Chad started to hang back neat the entrance. Horrible visions of her sending him to work in a pink ballet outfit were constantly running through his mind.
Mel walked right up to the woman behind the counter. “May I help you?” the woman asked politely.
Mel smiled. “I’d like an outfit for…” She looked around for Sissy, but he wasn’t there. She finally spotted him half hidden by one of the racks near the door. “Sissy! Get over here!”
Chad hated it, but he grudgingly moved toward the counter.
Mel returned her gaze back to the saleswoman. “I need it for… her!”
The woman looked Chad over carefully. Her surprise showed obviously in her eyes. “You’re serious?” she asked Mel.
“Of course,” Mel replied, slightly put off. Chad lowered his embarrassed gaze down to the floor, searching for that hole that never appeared to swallow him up.
The saleswoman finally shrugged and replied. “What exactly did you have in mind?”
Mel smiled again, wickedly, but she smiled. I think a pink leotard, white tights, a white tutu, and pink toe-shoes.
The woman looked at her for a moment to take it all in. “Okay, she finally said. “The tights are the easiest.” She moved out from behind the counter and went directly to a display rack against one of the walls. “How many pairs?” she asked.
“Just one, for now,” Mel replied.
The saleswoman looked at Chad once again to gauge his size, then selected a package of white tights in his size from the rack which she handed to Mel. “Now, as to the leotard…” She led the way to a rack of them in all different colors. “Let’s just get the style you’d like first. I’ve probably got the color in the back somewhere.”
Mel picked out a fairly simple leotard with a scooped neck and short sleeves. After glancing quickly at Sissy again, the saleswoman excused herself and went to the back room where she found one in pink and brought it out. “That’s the easy part,” she said to Mel as she handed the leotard over. “Now, what style tutu?”
“What’s available?” Mel asked. “I’d really like something that is wide, but not too long.”
“Classic or pancake style?” the woman asked.
Mel thought about that for a moment. “Probably pancake,” she replied. “Do you have any that I can see?”
Chad suddenly didn’t have a clue as to what they were talking about. The woman led them back up to the counter where she opened a book and started going through the pictures with Mel. Mel quickly pointed to one of the pictures. “That! That’s exactly what I’m looking for.”
The saleswoman smiled. “In white, I think you said?”
Mel nodded. “Definitely in white.”
The woman returned to the back room. She was gone a while, then she came back again. “I’m sorry,” she said as she returned. “But we’ve sold out of everything we had in that style. We should be getting some in next week or the week after if you’d like to check back then. Of course, we can always order you one if you like.”
Mel considered it, but decided to delay her decision. “How about the pink toe shoes?”
The saleswoman again looked at Sissy. “What size shoe do you take?”
“Ladies size nine,” Mel replied for him.
Chad winced. Size nine was fine, he could wear shoes in that size, but they were tight.
The woman went back to the back room again. When she returned, she was once again empty handed. “It seems were out of those too,” she apologized. “I’m afraid the dance schools all have their recitals this time of year and we’ve been selling out of some things as fast as we can get them in.”
“In that case, order a pair for me… the tutu too.”
Words that Chad very much didn’t want to hear. He could already see her dropping him off at work in the outfit and stranding him there. And curiously, for the first time in a while, he was aware of how sexually arousing the concept was… not that his main sexual member was even capable of reacting to it anymore.
“You’ll have to pay in advance, I’m afraid,” the woman said to Mel.
“No problem. That should be fine.” She turned to Sissy. “Get over here and pay for all this stuff. It’s all for you anyway.”
Chad was forced to pay for everything, but Mel gave the woman her own phone number and address so that she could pick the missing items up when they arrived.
Feeling slightly disappointed that she couldn’t get everything now, but still very happy and excited about what was soon in the future, Mel led the way back out of the store. Chad now had another bag to carry along with his bag full of makeup, his purse, and his diaper bag. Mel seemed happier than she had been all day.
Chad was more worried than ever! “Mistress,” he said in his best sissy voice. “I thought I’ve done everything you wanted. And now you’re still going to send me to work in the ballet outfit?”
Mel was amused. “I haven’t decided yet,” she told him. “Yes, you’ve done everything I’ve asked, but I can’t very well decide to send you like that in the future if we don’t have the outfit first.” She decided to let him stew on that thought for a bit. Besides, it was true!
But Chad’s fears were only partially allayed. No, she wasn’t planning on sending him to work that way… yet. But there was still the future to worry about.
A little while later, Chad checked his watch. His two hour time limit was quickly drawing nearer. He was very wet, but not yet wet enough for his diaper to be leaking any time soon. “Mistress,” he said in his sissy voice. “Maybe it would be a good idea if we went home soon. My two hour limit is almost up.”
“Are you leaking yet?” Mel asked, not even bothering to look away from the display window she was staring into.
“Not yet, Mistress. But something to drink would be a big help. I haven’t had anything in quite a while now.”
Mel realized that it was true. She wasn’t really helping matters by ignoring that fact. And keeping him wetting had to be her first priority. “Let’s stop and get a drink first,” she suggested.
Chad would have been a lot happier if they had just gone home first. A short while later, he was sipping on a very large soft drink while Mel continued shopping. Not being able to carry the drink into the stores, Chad was forced to stay out in the mall area while Mel went inside. During one of her trips into a store, he took the opportunity to sit on a bench and take the strain off of his tired and aching toes.
“Didn’t I see you here last week… doing some kind of dance and singing some crazy song?” a voice from nearby asked.
Chad, horrified, turned and saw an older man sitting on the next bench looking at him. He realized that the area he was sitting in was the same area he had “performed” in when Mel had brought him here in his super sissy dress.
But when Chad had turned to look at the man, the man definitely recognized him. “That was you!” the man added with a slight laugh. “You were wearing some crazy outfit too. I got a real kick out of it!”
“Uh… Thanks,” Chad answered, not knowing what else to say. “I’m glad you enjoyed it.”
“Most interesting thing I’ve seen here in ages!” the man replied. “Are you going to do it again?”
“I hope not!” Chad stated, fervently hoping that it would be true.
“Pity,” the man said. “I rather enjoyed it.”
Unfortunately, that was the point where Mel walked up. “Enjoyed what?” she asked.
“His little show last week,” the man replied.
“We’re glad you enjoyed it,” Mel said to him with a broad smile on her face. “We’re considering doing it again, only maybe something better next time.”
The man’s face showed his complete interest. “When?” he asked anxiously.
Mel shook her head. “I don’t know yet. “We haven’t decided.”
“Well, I’m here most days about this time,” the man replied. “Got nothing better to do, just getting out of the house for some exercise and people watching. I hope you do it while I’m here!”
Mel smiled at him. “We’ll try.”
Chad was beside himself. Do it again? Something better? Where was that tidal wave that was supposed to come through and wash everything away?

The Bet - Chapter 36 (Saturday – week 5 Part 4 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 4 of 8)

Once Mel had left, Chad was again strapped into the highchair with his right arm trapped under the tray while he attempted to eat his baby food lunch without spilling too much of it – a mostly impossible task! The sound of the door opening caught his attention while he was still trying to eat. Once again fear froze him in place. He was almost relieved when Cassie came in.
“Hi everyone,” she said fairly calmly, despite not being able to take her eyes off of Chad – and his mess.
“Hi Cassie,” Sandy replied.
But Cassie acted like she didn’t even hear her. She just stared at Sissy instead. “You’re looking rather colorful today,” she noted, referring to all the baby food that was spilled all over him.
Sandy laughed. “Simple little changes, and now he acts even more like a baby than ever!”
“I’ll say!” Cassie agreed as she watched Chad dropping more baby food from his spoon onto his already messy bib. She put her purse down on the counter. “Does Mel still want me to trim his hair again?”
“I guess so,” Sandy replied.
“Let me know when he’s done there and I’ll do him before you let him up.” She walked off toward their bedroom and out of sight.
Get his hair trimmed? That was news to Chad. He wasn’t sure how he actually felt about it either. As soon as Sandy had decided he had eaten enough, she took his plate and spoon away from him and again washed him thoroughly with her washcloth – including the also messy unfinished baby bottle that was still on the tray. Then she called Cassie. Chad, unable to leave the highchair and consequently having nowhere to go, just picked up his bottle and continued drinking – he did have another two hour deadline to meet!
Cassie came back a few minutes later – scissors, comb, and brush in hand. Chad put his baby bottle down as she ran the comb through his hair a few times. “I think we’re going to need to wet this before I can do anything else,” she declared. “You may as well keep drinking that thing while I’m working here,” she said to Chad. “You’re not going anywhere, and I’m not going to be doing anything that will get in your way.” Chad picked up his bottle again.
A few minutes later, Chad’s hair was soaking wet as Cassie combed and trimmed tiny bits off of his hair all over. He wondered how ridiculous he must look as he sat there with wet, must-up hair, sitting in a highchair, drinking from a baby bottle, while wearing only a diaper – that was now wet. He was glad he couldn’t see himself in a mirror just then, he had no doubt that he made an absolutely ridiculous picture of a baby.
As Cassie cut and combed, Sandy looked on closely and occasionally made some suggestions. But it wasn’t long before Cassie put her scissors down and picked up the blow dryer and curling iron. Chad’s bottle was long finished before she was. Sandy looked at him critically and smiled. “Looks great!” she exclaimed.
Cassie stepped back and looked at it too. “Yeah,” she agreed. “It’s only been a few weeks, but it’s starting to even out now as it grows in. Chad had no idea what his hair looked like. It mostly felt the same, but without a mirror he had no way of knowing anything.
“Wait a sec!” Sandy suddenly exclaimed. “It needs something…” She ran off towards her bedroom and came back a few minutes later. Chad saw a large pink bow in her hands. She clipped it to his head just off to one side and stood back again. “There! I love it!” she exclaimed happily. Cassie just smirked.
Sandy released Chad from the highchair and sent him into the living room where all the toys were. Since she had left him alone and didn’t follow him, Chad didn’t bother to “play” with any of the toys. Instead, he just laid down on the blanket and tried to rest. Curiously, he wished for his pacifier. He was very tempted to stick his thumb into his mouth, but resisted that impulse furiously.
“I don’t hear you talking to your toys!” Sandy’s voice called from the kitchen.
Chad groaned and sat up again. He picked up a plastic toy block and babbled at it. Then he switched it for another toy.
Sandy came in to see him a few minutes later. She had another baby bottle in her hands. “Since you’re on a time limit now to make your diaper leak, I brought you another bottle.”
Chad took the bottle gratefully, even though he could really have done without more to drink… but if he was going to meet Mel’s deadline, then he really had to keep drinking.
Sandy knelt down on the blanket with him and picked up a small doll that was there. “Here,” she said, “hold this.” Chad started to grab for the doll, but she immediately pulled it back away from him. “No, no! Put your bottle down first and use both hands. Babies need two hands to hold something this big.” Chad thought it was stupid, but he did as she wanted – he really didn’t have a whole lot of choice in the matter anyway. “Now,” Sandy continued as soon as he was holding the doll in both hands, “stick it into your mouth.”
Chad’s eyes bulged. Stick it into his mouth? She had to be kidding.
But Sandy quickly went on to explain. “Babies try to stick everything into their mouth to taste them or teethe on them. They often slobber all over most of their toys. So from now on, before you talk to any of your toys, I want you to stick it into your mouth first and make sure that part of it gets good and wet. Chew on some of them a bit if you have to. Since you have to keep drinking from your bottle today, then that should help.”
Chad couldn’t believe it. She really wanted him to do that? Obviously she did! As crazy as it sounded, she meant it. But then of course, Chad had seen babies doing exactly that many times. Now she was simply making him do it. Ugh! He took the doll he was holding and stuck part of the head into his mouth – yuck! It was dry and tasted awful. He had to chew on it for a moment before he thought it felt even a little bit wet. Then he gratefully removed it from his mouth again. He looked at it – yes, the head and part of the hair was just a little bit wet. He babbled at it for a moment, then put it aside and grabbed his bottle. He really needed to wash the taste out of his mouth.
“Now do that with all your toys,” Sandy told him.
Chad picked up the toy block he had been talking to earlier and stuck the corner of it into his mouth. He made sure that part of the block got good and wet before he pulled it back out and babbled some nonsense at it. Then he put it down again and grabbed for his bottle.
“That’s it! You’ve got it,” Sandy declared as she stood up again. “Now just keep doing that till Mel comes for you later.”
Till Mel came back for him? When was that supposed to be? And he had to keep doing it? He picked up another toy and stuck it into his mouth. Yuck!

Mel took the cover off of the huge pot on the stove, looked inside, stirred it with a spoon for a bit, then turned off the heat underneath. She picked up the heavy pot and with a great deal of effort, poured the tea that she had been making into a large pitcher. The pitcher made things much easier for her to pour the tea into the small opening at the top of his baby bottles.
She refilled the big pot with water and stuck it back on the burner again to start making more tea. Keeping him drinking it meant that she had to keep making it. She added half a dozen of her green tea bags to the pot and left it alone. It would be a while before it was done. In the meantime, she had a lot of empty baby bottles all lined upon her counter that needed filling. She picked up the now heavy pitcher and started filling the first bottle. So many baby bottles – for such a big baby. Yet she didn’t really mind making the tea for him like this. Something about doing it was kind of fun… and maybe relaxing. It took very little thought, yet it kept her busy. And… it was directly helpful to winning the bet between them.
When the pitcher was empty, she set it down and checked the pot on the stove, not ready yet, but getting there. She took the bottles she had filled and set them into her refrigerator to start cooling. By the time she was done today, a good bit of her refrigerator would be filled with the bottles – and Chad’s refrigerator too.

Chad noticed that he was peeing yet again. Since the bottles were a lot better in his mouth than the taste of the toys, he was drinking even more than usual. But the result was that he was also wetter than usual. He looked up at the fancy clock on the wall. He still had more than half an hour to go before he needed to be leaking. But just thinking about his diaper made him realize something else, the damn suppository was about to do its thing. He never even thought about stopping it or even trying to hold it back. As the mess quickly started sliding out of him, he simply got up from his sitting position into a crawling position to make the process easier – physically… emotionally, he still hated it. But as his backside finally finished emptying itself out, his front side resumed. He looked down under him and noticed that he was dripping onto the blanket under him. Uh oh! Trouble. He was sure that Sandy wasn’t going to be too pleased to see that! But what could he do about it? He let out a rather loud stream of baby babble, trying to get Sandy’s attention, where ever she was. But after almost a minute, he still got no attention from her. He figured that he had only one avenue left to quickly try to bring her attention to his problem. He did his very best to fake a baby crying.
“What is it Sugar?” Sandy asked as she came running out of the bedroom. Chad only looked down at the wet spot on the blanket below him. Sandy suddenly sniffed the air. “Oh! Pew! You stink!” Then she noticed the wet spot under him. “Oh darn!” she exclaimed. “Now I’ll have to wash the thing. You stay right there baby and I’ll call Mel.”
A few minutes later, Chad was crawling in his very messy and leaky diaper toward the door while Sandy fussed about how wet he had gotten the blanket. Serves her right, Chad mused to himself, happy that for once he had a way to make things unpleasant for her. Mel opened the door for him and he crawled outside, then stood up again. Finally! He immediately felt more pee running down his leg. Oh well, he was about to get changed anyway.
Mel opened his apartment door for him, but on the way through, he felt himself peeing yet again, which let loose even more pee running down his leg. He hurried into his bathroom and carefully ripped off his messy diaper as quickly as possible and jumped into his shower to get cleaned up. When he came out again, Mel was leaning against his bathroom door to watch him. He quickly dried himself, then grabbed only one diaper – knowing that it was what she wanted. He quickly taped it in place before he might have to pee yet again. Safe!
“Two hours, Sissy,” Mel declared with satisfaction. “Or less, if you can make it again.” Then she laughed as Chad’s face turned red.
“Hurry and find something to wear. I’d like to get to the mall before that diaper gets too wet.”
Chad curtseyed. “Yes, Mistress,” he replied as usual. “Is there anything specific you want me to wear?”
“Whatever you want,” Mel replied, knowing that the only clothes he had to wear were all women’s clothes. Then she looked at the bow in his hair and added with a small laugh, “Something pink might be appropriate.” She left him then to get ready herself.
Chad didn’t know why she had been laughing, but he found a pink skirt and a patterned top in his closet that he put on, over his bra with breast forms and waist cincher. Since he was wearing only the one diaper and was on another two hour time limit to make it leak, no girdle or pantyhose were allowed. It wasn’t until he looked in the mirror to start his makeup that he noticed the bow that was still in his hair. He had forgotten about it. He was about to pull it out, but decided to leave it. Mel had said that pink would be appropriate, probably because of the bow in his hair.
He stood back and looked at his hair more critically. It mostly looked the same as it had, only neater than it was before. But he could defiantly notice now where it was looking a bit longer at the sides and back then it had looked before Cassie trimmed it. He decided he liked it. Besides, since it was basically the same hairstyle, he knew how to take care of it. He quickly finished getting ready and headed out the door to Mel’s apartment.

The Bet - Chapter 36 (Saturday – week 5 Part 3 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 3 of 8)

It was still a few minutes before twelve when someone knocked on Chad’s door. Chad figured it would be Sandy, but he was a little surprised to see Mel there since he figured she would just use her own key and come in. He dropped his curtsey to her, “Hello, Mistress,” he said in his sissy voice.
“I know it’s not quite twelve yet,” Mel said, “but I just thought I’d come over to see if you were busy.”
Chas stood back out of the way to let her inside. “No,” he replied. “I was just giving my kitchen a quick cleaning. It was getting dusty.” As she walked in, Chad noticed the book she had in her hand – the child’s menu he had colored at the restaurant last night.
“Dusty? I guess you don’t really get to use it much.” She headed straight for his kitchen and laid the child’s menu out on his kitchen counter. Chad watched as she started going through the pictures. “I like this one… and this one the best,” she said as she placed one hand on one page to mark the place, and opened the book to the second picture. “Which one do you like?”
Actually Chad didn’t like any of them at all, especially since the ones that she had picked out were the ones that looked the most childishly colored. He had visions of having one of the pictures hung on his living room wall, right next to the one that was already there. How embarrassing… and what a terrible reminder of what he had been forced to do. He took the book from Mel, careful to hold the place of each picture, and turned back and forth between them a few times. The second one was a bit more mature looking, but not by much. “I like this one,” he said, indicating the second picture.
Mel smiled as she took the book back from him and opened it fully to that page. Chad wasn’t the least bit happy to watch as she carefully ripped the page out of the book. She handed the picture to Chad. “I think that Sandy would just love it if you gave that to her. And I want you to tell her that you colored it – just for her.”
Chad was shocked. “Give it to Sandy?”
“Unless you want to hang that one on your wall and give her the other one instead.”
Chad shook his head. “No, Mistress. I’ll give her this one.”
“Good! And don’t forget, tell her you did it just for her! Now let’s go see if we can find something a bit more childish for you to wear for her today. If you’re going to give her a childishly colored picture, then the least you can do is to dress a bit more appropriately.
Not happy about it in the least, Chad followed Mel back to his bedroom where she quickly picked out the onesie he had slept in last night. As he took his clothes off, Mel was careful to check the state of his diaper. “You’ve only got about half an hour to get that thing leaking,” she reminded him.
“I know,” he replied. “I think it’s getting close already. Can I just change it now instead?”
“No, not till it’s leaking. I don’t want you to stop trying.”
Chad wasn’t happy about it, but there was nothing he could do about it either. The sound of someone knocking on his door came before he even got the onesie on.
“That will be Sandy,” Mel said. “I’ll get the door, you get dressed.”
“Hi Sandy,” Mel said with a big smile the moment she opened the door.
“Hey Mel. Is he ready?”
“Almost,” Mel replied. “Come on in.” Mel led her back to Chad’s bedroom where he was just stepping into the onesie. She noticed how wet his diaper looked already. “I take it he hasn’t leaked yet?”
“Not yet,” Mel replied. She checked her watch. “But he still has another twenty-four minutes to go.”
“Then maybe we should just leave him in his diaper till then. That way we can see if he leaks. Besides, once he gets to my place, he won’t be able to tell us.”
“That’s true,” Mel replied with more than a hint of amusement. “Take it off again,” she told Chad. “You can start out in just your diaper.”
“For that matter, he can stay in just his diaper today” Sandy decided. “Maybe just a pacifier to complete his outfit and that’s all he should need.”
Mel smiled. “I like it!” She looked at Sissy. “Where’s your pacifier?”
“In the kitchen,” he replied, fully unhappy that the thing should even be mentioned.
“Then go get it. And hurry!”
Chad ran to the kitchen and came back a moment later with the pacifier in his mouth.
“Now that’s more like it!” Sandy declared. “Are you ready?” she asked him.
Chad just shrugged. “I guess so,” he said around the pacifier in his mouth. “What else is there?” He wasn’t taking any other clothes or anything else.
“How about his diaper bag?” Mel suggested.
“Yeah,” Sandy replied. “Good idea! I guess with him, it really is just like taking care of a real baby!”
“Oh wait!” Mel suddenly said. “We almost forgot something!” She looked right at Chad. “Isn’t there something special you have for Sandy?” she asked.
Chad blushed and Sandy looked a bit surprised. “I’ll be right back,” Chad said as he hurried out to his kitchen one more time to get the picture he had colored. As he carried it back to the bedroom, he saw Mel looking at him very intently. Her stare let him know that he had better do this right – the way she wanted him to do it. Sandy just looked quizzical since she was wondering what was going on. “Um…” he said as he stood in front of Sandy and held the picture out to her. “I colored this for you.”
“For me?” Sandy replied in a surprised voice as she took the picture from him. She looked at it and let out a small laugh. “You even color like a baby! Thank you, I know that Cassie will just love this too. We’ll find a good place to hang it in our apartment… maybe on the refrigerator. How will that be?”
Chad wasn’t happy about that at all. Why couldn’t she just take it and put it away somewhere – like maybe in the trash can. In her elaborately decorated apartment, it would stick out like a sore thumb – and everybody who went in would notice it. But he replied, “That would be great.”
“So are you ready now?” Sandy asked.
“Yes, Sandy,” he replied.
Sandy turned to Mel, “Are you coming with us now, since he only has a few minutes to start leaking?”
“I’ll be over in just a few minutes,” Mel replied. “I have something else I have to do first.”
Sandy stopped before she opened the door and turned to Sissy. “Remember the rules! No walking the minute you get to my apartment… and only baby talk!”
Chad dropped a quick curtsey. “I remember.” Ugh! Baby talk! What a pain!
Mel stayed back in his apartment as Sandy and Sissy left. She went straight to his refrigerator and checked it. As she suspected, he was just about out of bottles. Well, she would fix that problem soon enough. She went back to the child’s menu that he had colored and ripped out the other picture that she liked. She hung it right next to his other picture on the wall so he could “enjoy” them both.

“Climb up,” Sandy said as she took the tray off of his highchair. Chad crawled across her kitchen floor and climbed up into the chair. Sandy fastened the safety belt around him, being careful to pull it tight. She was about to put the tray back into place when she paused a moment in thought. “Put your right arm down in your lap.”
Chad was surprised by her request, but protesting or even questioning it would do no good. Besides, since he was limited to only baby-talk, he had no way to ask her why. As soon as his arm was down, she put the tray into place, locking his right arm under the tray where he couldn’t use it.
“That should work,” Sandy mused to herself.
Chad watched as she began dumping baby food, straight out of the jars onto the divided child’s dish that she had gotten for him – colorful baby food, that he had no idea what it was, even when he tasted it. She set the plate down in front of him, then set a small rubber coated baby spoon down next to the plate. “I want you to feed yourself this time,” she told him.
Chad awkwardly picked up the spoon with his left hand. He started to bring it toward the food, but she stopped him. “Not like that! Babies don’t hold anything like you’re holding that. Close your fist around it instead and grab it tightly.”
Hold it in his fist? Ugh! He managed to get the spoon into his hand the way she wanted it, which wasn’t all that easy since he only had the one hand to use. Then he shoveled some of the baby food onto the spoon. He wanted to change the position of the spoon in his hand to make it easier to bring it to his mouth, but with his fist wrapped tightly around it, he couldn’t do that. He had to awkwardly turn his entire arm out to get it around far enough that he could get the food into his mouth. Eating with just the tiny baby spoon had always been difficult, not to mention embarrassing. Doing it this way made the task twice as hard! He slowly reached out and grabbed another spoonful and managed to get it almost to his mouth before some of it dripped off of the spoon and onto his bib. It seemed that holding the tiny spoon the way he was, made it harder to keep it level. And the result was that more of the baby food dripped off. Just great!
“Perfect!” Sandy declared happily. “That’s the way you should be eating from now on.”
Not likely, Chad thought. But just then, someone knocked at the door. Chad quietly panicked inside while Sandy went to answer it. She came back a few moments later with Mel.
“Keep eating,” Sandy ordered as they got back to the kitchen.
Mel watched him eating awkwardly with the tiny baby spoon. “I must say, you found a way to make even his eating look more childish.”
“Babies don’t hold spoons the way we do,” Sandy explained. “And as far as I’m concerned, the more babyish he does everything, the better!”
Mel laughed. “I couldn’t agree more!”
Chad was about halfway through with the food. His face was a mess. His bib was a mess. And so was the tray in front of him because the food kept dropping off of the tiny spoon – not to mention that it was more difficult than ever to accurately hit his mouth the way he was holding the darn thing. He suddenly felt himself peeing again. Knowing that the time was running out for him to be leaking, he waited till he was done peeing, then he began trying to feel all around the leg openings of his diaper with the one hand that was under the tray. He couldn’t reach the diaper on his right leg very well, but he could feel around the opening of his left leg a bit. Nothing… Nothing… There! Was that a bit of a wet spot near the bottom? He felt it again. Yes, it did feel like it was starting to leak out. Since he had no other way to express himself, he let loose a tirade of baby talk. But Mel and Sandy were talking and mostly ignoring him. He tried again, harder. They both looked over at him.
“What’s the matter, baby?” Sandy asked. “You’re not finished with your dinner yet. Keep eating.”
But Chad had to let them know that he was leaking. He tried more baby talk instead.
“Was he asking for his bottle?” Mel asked. “You know, he does need to be leaking very soon. Maybe he needs a bit more to drink.”
Sandy got up quickly and got a bottle for him that was already filled with baby formula. But as she brought it over to him, Chad very emphatically let out more baby nonsense. Sandy set the bottle down on his tray and turned back toward Mel. “I don’t think that was it,” she said. “I think he’s trying to tell us something else.”
Mel came over to him and peered under the tray at his diaper. “Are you leaking?” she asked.
Chad let out a shorter and happier stream of baby nonsense to let her know that that was his problem.
“I guess that’s it,” Mel said to Sandy. “We can change him now and then I can get out of your hair for a while.”
“No problem,” Sandy replied as she took the bottle back off of the tray and also picked his food up too. “Wow, you’re really a mess, baby,” she declared as she looked at him. “Just like a real baby!” She grabbed a wet washcloth and spent several moments cleaning him up thoroughly before she removed the tray that was holding both him and his arm in the chair. She had to release the safety strap before he was able to climb down to crawl on the floor.
Mel led the way into the living room where Sandy had laid out a large blanket that was already covered with baby toys for him to play with later. She moved some of the toys out of the way. “Lay down here,” she told him and waited while he crawled over into position. Sandy brought the diaper bag over for her. With practiced efficiency, she quickly had his overly soaked diaper off of him and a new one shoved in place under him, ready to bring up between his legs. She reached back into the diaper bag and brought out the jar of suppositories. With a wicked smile on her face, she held the jar up where he could see it. “Your favorite part, I know!”
Chad rolled his eyes and turned his head away. The suppositories were his least favorite part. He hated the things – and especially what they did to him.
Mel reached into the jar and pulled out – nothing. “Lift your legs,” she ordered. Chad raised his legs up and she pushed them up even higher, totally exposing his bare backside. It took her only a moment to shove her finger way up inside of him – as if she were actually shoving one of the suppositories up there. He would never know the difference, and hopefully, the results would be exactly the same. She brought his legs back down and a minute later the fresh diaper was taped securely in place. She checked her watch. “Two hours, baby. Two hours.”
Since Chad had no way of responding in any recognizable way, he said nothing. He already knew the drill.

The Bet - Chapter 36 (Saturday – week 5 Part 2 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 2 of 8)

Chad stared at the shopping list he had made. He needed an awful lot of stuff. His makeup was running low, he needed shampoo and conditioner. He needed baby wipes and baby lotion. He needed pantyhose. And of course three more packages of diapers. It would take a long time to shop for all that stuff. Longer than he wanted to be out in public by himself, dressed as he was.
Today he was wearing pants again… but they were the tighter pants this time. With only one diaper on and knowing that he probably wouldn’t be wearing them for very long, they had seemed like his best option. It actually felt a bit strange wearing pants again, even with the high heels on his feet. He was also wearing his waist cincher to give himself a bit of a better figure. His shape wasn’t as good without the all-in-one girdle he usually wore too, but the waist cincher did help a lot. Naturally, he had added a bra and his breast forms too – at least they weren’t glued on to him today… yet. A simple casual top, his watch, ring, and necklace completed his outfit. Casual. Actually a lot more comfortable without the all-in-one girdle. It gave him a huge sense of freedom.
He checked his watch. Only a little over an hour to go before he would have to be at Mel’s apartment with a leaking diaper. His diaper was already getting very wet, but it still had a long way to go so he dared not hold back at all. Picking up his purse, he headed out the door and down to his car to start taking care of business.
His first stop of the morning was at the ATM machine to get a pile of cash to use during the week. The cash made life a lot easier, even though he no longer had the super long nails on his hands. As he punched the numbers into the machine with the tips of his nails, he was again struck by the strange purple color. Would he ever get used to them? They were kind of pretty though.
He needed diapers – three packages. But just thinking about shopping for them reminded him of the two girls who had been all too interested in him at his usual drug store for the last two weeks. Purposely, he avoided that store and went further down the road to the next one. The store was crowded as he went inside, but then he was a bit later getting there than he wanted to be this morning. He ignored all the other customers and went straight to the diaper aisle. He was glad to see that they were fully stocked this time. He pulled three big packages off the shelf, and holding two of them while trying to precariously balance the third, made his way to the checkout counter. He realized that the drug store probably also carried most of everything else on his list too, but he didn’t want to have to deal with buying all that along with the diapers. And just carrying it all would have been impossible anyway.
As he stood waiting in the short line, he saw some of the other customers glancing at him curiously. But at least none of them said anything or even looked overly long at him. He was glad. When it was his turn to pay, the saleswoman simply rang him up quickly, dumped all three bags of diapers into three different plastic bags, took his money, and gave him his change. Quick and simple. Just the way it was supposed to be. Things were definitely going better today – so far! He made a mental note to use this drug store all the time from now on.
He checked his watch again as he got back into the car – just over forty minutes to go. He was doing pretty good continuing to wet himself, but there were still no leaks. If he was going to make Mel’s deadline then he had to keep drinking – and he had to keep trying to wet. He drove further down the road to his favorite fast food restaurant and ordered a quick breakfast with a large cup of coffee through the drive-thru. He sat in his car the parking lot while he ate, then got back on the road again the minute he finished.
But where to go next? Time was running out before he had to be at Mel’s door with a leaky diaper. He could tell that his diaper was really wet, but he still hadn’t felt the telltale tickle of any leaks yet. He knew that someplace like Target or Wal-Mart would have everything else that he needed, but stopping at one of those stores would take too long. He turned back towards home instead to wait till after he could get changed before he continued his shopping. But halfway home, he noticed the drug store he had just stopped at a little while ago. The experience hadn’t been bad at all, and most of the things that he needed could be bought there. Trying to save a little time, he quickly pulled back into the store’s parking lot as he felt himself peeing yet again – but he still didn’t feel any leaks.
There were quite a few cars in the parking lot now, but he didn’t think it would be too crowded inside. He entered the store and grabbed a small handheld shopping basket from a stack near the door. At first glance, he was a bit worried about the number of people he saw inside, but he kept going anyway.
The makeup section was first – several long aisles of it. All of which had women looking closely at the various items – too many women for his comfort since he wasn’t all that sure about where to find what he was looking for anyway. He continued on to the next section instead and quickly found the shampoo, conditioner and other bath supplies that he needed. There were only two women in this section, but in the long aisle, that didn’t seem like too many at all. His basket started to fill up quickly, but as he turned from picking up one of the items, he noticed one of the women had been looking at him rather closely. Well, that was nothing new. At least she didn’t say anything. He glanced at his watch, time was running short. As he hurried to the checkout counter, he was pleased to feel himself peeing again – a lot – probably from the coffee he had just finished.
The store had two cash register lanes open now to handle all the customers, with a short line at each one. Chad chose the line that he hoped would get him out of there the quickest. He was aware, as usual, of all the stares from everyone around him, but fortunately, nobody said anything to him. But as he stood there waiting his turn, something suddenly felt odd… then grew more odd. The odd feeling was on his legs, just below his crotch, and it seemed to be expanding! He reached down casually and felt his pants just below his diaper. Wet! He was leaking, and the pants he had on were too tight to let any of it just drip down his leg. They were quickly becoming wetter and wetter as his diaper continued to leak!
He moved up in line, only one other person ahead of him now. He had a basket full of things to buy in his hand. He wanted to just drop the basket and run out, but he had come so far already. He heard someone grunt in surprise, then a moment later, someone giggled. He turned, two women were looking at him. Then someone else noticed him. That someone else grabbed her friend’s arm and pointed at him. Damn! Why didn’t he think about this when he got dressed this morning? His pants were too tight to let him get away with anything! Not only were the people noticing him because he was obviously a man dressed as a woman, but he was feeling extra embarrassed because he was now out with obviously wet pants, and the growing wet stains were letting everyone know that he had just wet himself! He was about to drop everything and just walk out, but just then, the person ahead of him finished and it was his turn to check out. He had come too far now to just leave.
As quickly as he could, he put everything up on the counter from his basket and waited while the cashier rang everything up. Fortunately, she couldn’t see his wet pants. But he had no doubt that everyone else in line was watching him. It took a few minutes to ring everything up, pay for it, receive his change, and wait till it all got bagged before he could finally leave. By then, there didn’t seem to be any use in hurrying too much. Everyone had already gotten an eyeful!
He didn’t dare to glance down at his pants to see how bad they were till he got out of the store and was standing next to his car. And what he saw was shocking. Just from what he could see, he had large wet splotches in several areas at the top of each leg, starting right at his crotch. Some of those wet splotches were starting to grow together. He couldn’t see behind him, but he could now feel how wet he was back there and it felt even worse than the front. He finally opened his car door and threw his bags across onto the passenger seat on top of the diaper bags. But as he started to get into the car, he stopped and noticed that there was a small wet area on the seat already. He had been leaking since before he went into the store and didn’t know it! No wonder some of the people in the store had been staring at him since he went in.
Not wanting to make his seat any wetter, he grabbed one of the large plastic bags that held his diapers and emptied the bag. He sat on the plastic all the way home. He left all his purchases on the seat of his car as he climbed the stairs up to Mel’s apartment and knocked on her door with just a few minutes left to spare. The door opened and he immediately dropped his usual curtsey and recited his sissy greeting.
Mel smiled. “You just made it!” But then she stopped and stared at his wet pants. “But by the looks of things, you could have been here earlier. Turn all the way around. Let me see how bad it is.” Still outside where everyone could see him, Chad slowly turned all the way around. “Why didn’t you come back sooner?” she asked.
“I was out shopping when it happened.”
“In the stores? With people around?”
“Yeah, the drug store.”
Mel smiled. “I hope you enjoyed yourself.”
That wasn’t exactly the way that Chad would have put it!
“Let’s go get you changed,” Mel said as she grabbed her keys from her purse and started toward his apartment. Chad followed behind, allowing Mel to unlock his apartment door for him since her key was already out.
“Did you get everything you need today?” Mel asked as he was removing his wet pants.
“Not yet,” he replied. “I still have to find some of the makeup I’m almost out of, and I need a few more pairs of pantyhose too.”
“Some of that makeup you’re only going to be able to get at the mall.”
He groaned audibly. “That’s the only place? Target or Wal-Mart won’t carry it?”
She shook her head. “Not that brand. You’ll have to go back to the makeup counter where you got it. Of course when you do, you can always ask for another demonstration again,” she teased.
Chad rolled his eyes as he pulled off his saturated diaper and let it drop to the floor. “No thanks. Not today,” he replied.
She smiled but said nothing as she waited for him to tape another fresh diaper in place. “Two hours, Sissy,” she said as she glanced at her watch.
Chad glanced at his own watch too. “Yes, Mistress,” he replied with a small sigh.
She paused before she left him. “Tell you what. I was thinking of going shopping today myself. I need a few things too. If you like, we can go to the mall together and you can get your makeup then.”
Chad thought about that for only a few seconds. It sounded like a better idea to him – despite what she might come up with along the way. Besides, if she was going shopping then he was probably going with her anyway. “Thanks,” he replied. “Maybe I’ll wait till then.”
Once Mel was gone, Chad went back to face his closet. Now what was he going to wear? Pants were obviously out! Since he wasn’t going shopping till later with Mel, he was tempted to stay in just his diaper till she came back at noon. And when Sandy arrived later, he had no doubt that she would have her own ideas on what she wanted him to wear today. But then he remembered that all the things he had bought earlier were still down in his car and they needed to be brought upstairs. He finally chose the most casual looking skirt and top that he could find and the low-heeled shoes that he wore with his uniform. He might as well be comfortable. Since he only had two more hours to go till he had to be leaking again, he pulled another baby bottle out of his refrigerator before going down to the car to get his purchases.

“I really appreciate this,” Sandy said as she opened the door to her apartment and she and Mel lugged the heavy highchair inside.
“No, it’s me who appreciates it,” Mel replied. “What do you have planned for him today?”
“I was thinking of a couple of things. But mostly, I’d like to start working on the way he does things… the way he moves. Babies don’t quite have the motor control we have, so they do things a bit differently. I’d like to try a few ideas on that line today.”
“Sounds interesting,” Mel replied. “Actually, that’s something I need to start working on with him too, although in a completely different way. He’s still got too many masculine mannerisms.”
Sandy giggled. “Well then, maybe between the two of us we can eliminate a few of them.” Mel giggled too.

The Bet - Chapter 36 (Saturday – week 5 Part 1 of 8)

The Bet
by Karen Singer

Chapter 36 (Saturday – week 5 Part 1 of 8)

In her dreams, she was holding a tiny infant… so sweet. The precious baby felt soft and warm in her arms. And in her dreams, Sissy was standing there right by her side – supportive, attentive, waiting to hand her bottles or wipes, or whatever she needed for the baby.
But then, as so often happens in many dreams, the oddly unusual thing occurred. The face of the baby in her arms became Sissy’s face. Confused, she looked back at Sissy standing beside her, he looked exactly the same. Yet the baby in her arms was now him too! She felt startled by it, bothered. The baby in her arms was just an infant… a precious infant – and the Sissy at her side was her servant. Two Sissys! Yet in her odd dream she was sure that somehow they were the same person – one being.
Over and over she tried to think of ways to prove to herself that she was wrong, that they were different people, totally separate. They acted completely different and separately, showing no connection to each other at all. Yet something still convinced her that they were one and the same. She frantically ordered the Sissy that was her servant to run all over the place, bringing her things, taking care of things, handling things. And while he did that, the baby in her arms behaved completely as nothing more than – a baby. Yet the baby in her arms still had his face!
Over and over she tried to figure out how they could be the same being, while at the same time trying over and over to prove that they were totally separate. Her frustration over the problem grew and grew. It disturbed her more and more. The Sissy that was her servant… and the baby that had Sissy’s face. How could it be? Yet she knew that somehow it had happened. They were one and the same! She just couldn’t prove it and couldn’t understand it.
In her dream, her anger grew with her inability to reconcile the two. Finally, she began yelling at Sissy the servant. The moment she did, Sissy the baby began crying uncontrollably, as if yelling at one affected the other. But it wasn’t proof! Wasn’t it normal for a baby to cry when people were yelling around it?
She tried to console the baby in her arms, but the baby refused to stop crying. Her dream changed into being one long nightmare of doing nothing but searching for a way to stop the baby from crying. Becoming more and more frantic, she tried everything to calm the squalling infant. Bottles didn’t help, changing it didn’t help, holding it didn’t help. Nothing worked. The baby’s desperate screaming cries were getting to her more and more. She had to calm the baby! She had to find a way to make it stop crying!
With a sudden gasp of breath, she finally woke from her nightmare. As soon as she realized that she had been dreaming and was now awake, most of the dream wiped itself from her memory, leaving only vague upsetting feelings. What had she been dreaming about that was so disturbing? Why did she feel so irritated? As she searched her mind, she remembered that her period would be starting in a few days. Was that what it was all about? But it shouldn’t be affecting her too much yet! But her period was coming soon – ugh!
Wanting to get moving to shake her irritated mood, she quickly got up out of bed. Coffee! She had to have coffee! Coffee would help!

Chad labored to roll over on his tiny blow-up mattress and found that the job was easier today than it usually was. The breast forms were gone! Still half-asleep, he allowed his hand to rub his chest through the onesie he was wearing where the breast form had been. Pure bliss!
As he laid there slowly waking up, he realized he was once again sucking on his pacifier – as usual. But he certainly didn’t mind – anymore. The thing brought a certain amount of comfort to his stressful life. He thought again about how Mel had seemed to forget about making him use the thing during the day lately. He hoped things remained like that. It would be one less major humiliation in his already overly humiliating life!
He concentrated on his diapers. Hugely bloated and messy again. As usual. He was struck by how normal they felt that way now – who would have ever thought!
He finally realized then that his alarm hadn’t gone off… no loud music to wake him up! Oh yeah, it was Saturday. No work… at least not his regular job. There was no telling what Mel would make him do today!
Reminded of Mel and her never ending requirements, he rolled off of his mattress onto the floor, scattering empty baby bottles as he went – they were the required bottles he had drank last night before going to sleep. He struggled to his feet, letting his body get used to the weight and bulk of his super heavy diapers. He waddled his way out of his room towards the kitchen where he knew that a note from her awaited him… at least there usually was a note.
As usual, the note was right on his counter where it always was every morning. He reached out to pull it closer so he could read it easier, but he paused in the process as he noticed his purple fingernails… lavender. The odd color looked strange and all too noticeable, yet he felt oddly stimulated by it. Trying to put his purple nails out of his mind, he pulled the note toward him.


Sissy,

Today is Saturday. As usual, you have the morning off to take care of whatever personal business you need to. But today there has to be something different! I need you to call me this morning the minute you get out of the shower – before you put your diaper on. Take your cell phone into the bathroom with you so you can be drying off while I’m coming over. When I get there, I’ll also be expecting to see three more empty bottles that I want you to drink this morning. So drink up before you clean up!

Make sure you buy plenty of diapers today – at least three packages again. Make sure you have plenty of makeup and whatever else you may need for the week too. This is your chance to take care of those things.

At twelve o’clock, I’ll be at your apartment. Then afterwards, you can expect Sandy to come calling on you again. Yes, more baby lessons. I can’t wait to see what she teaches you today.

Enjoy your morning. I’m waiting for your call!


Chad grunted aloud as he finished the note, then read it a second time. He had no doubt that Mel wanted to see him putting on only one diaper again so she could time him. But if he had the morning off, then how was she going to do that? And as to the rest of it? Last weeks baby lesson had led to him having to use nothing but his stupid sissy speech all the time. He seriously hoped that this week wouldn’t lead to anything nearly as humiliating.
He waddled over to his refrigerator and pulled out three baby bottles. Setting his pacifier on the kitchen counter as he walked past, he carried all the bottles out to the living room and his single solitary chair. He sat down in his super thick, messy diaper and put the first baby bottle to his mouth. His eyes once again focused on the childish drawing he had colored at the restaurant a few nights ago. At least Mel hadn’t added another one from last night to his wall. But it was hard for him not to look at the picture since it was taped right at eye level directly in front of him.
Closing his eyes to it, he concentrated on nursing on his bottle instead – and just relaxing.

Mel had just poured her third cup of coffee for the morning when her phone rang. At least she was finally feeling a bit better now. She quickly answered her phone, expecting it to be Sissy. “Hello?”
“Hewwo, Mistwess,” Sissy said in his sissy voice. “I just got out of the showa.” Since he had to speak in only a high-pitched voice and wasn’t allowed to use the letters “L” or “R” in anything he said, he sounded mostly childish.
“Have you put your diaper on yet?” Mel asked.
“No, Mistwess. I’m stiw, wet.”
“Good! Dry yourself off and I’ll be right there.” She hung up her phone and grabbed her keys. A minute later, she was letting herself into his apartment. She went straight to his bathroom. He was there, still drying himself off. “Good morning, Sissy.”
Chad did a partial little curtsey. “Good morning, Mistress,” he replied in his sissy voice.
She stood in the doorway and watched him finish drying. His body was shaved smooth – good. His chastity device was still in place – as she expected. His hair was soaking wet – well that was to be expected. He would use the blow dryer and curling iron on it after she left.
As soon as Chad finished drying, he asked. “One diaper again?”
Mel nodded. “Yes! You got it!”
Chad mentally groaned but didn’t show any other outward signs that he was displeased – it wouldn’t do any good anyway. He put the single diaper on himself while standing up – taping it firmly into place.
“Good,” Mel said from the bathroom doorway. She checked her watch. “Two hours, Sissy. Remember that.”
“But Mistress, if I have the morning off to get the shopping done that I need to, how will you know if I’m leaking?”
Mel smiled. “I expect you to be knocking on my door with a leaking diaper before your two hours are up! If you’re out somewhere, plan on getting back to me before that two hours. Then you can go out again if you need to.”
Chad wasn’t the least bit happy to hear that. She was stripping away any chance he might have today of ever trying to hold back – even for a little while. But what could he do about it? Nothing! “Yes, Mistress,” he replied.
With a broad smile, Mel turned around and left him there. At work he could try to hold back, try to regain more and more control, but on the weekends she was in control – all the time. And if she was going to win this bet, then he couldn’t be allowed to exercise any control at all!

The Usual

Just a reminder. For those of you who are trying to catch up on the story from the beginning, or for those who are simply interested, I have the published chapters so far, chapters 1 through 35, available in a single text file.

I’ll be glad to send it out to anyone who’s interested. Just email me at siskarensinger at yahoo dot you-know-where and I’ll be glad to send it as an attachment in a return email.

Or, if you just want to contact me with questions or comments, that will be fine too.

Stay happy everyone!
Karen

The Bet - Chapter 35 (Friday – week 5 Part 8 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 8 of 8)

While Chad was picking up the diapers he had spread all over the floor, Mel wandered into the kitchen and picked up the child’s menu that she had made him color in at the restaurant. As she turned the pages, looking at the pictures, she was pleased with how juvenile looking they were. But she wasn’t surprised. As they had talked in the restaurant, she had watched him growing ever more cross-eyed as he tried to peer past the bottle he was holding up and drinking from – while he colored in the book. Trying to do such a thing would have made her dizzy for sure. But then, she would never put herself in a position to do anything even remotely like that. She made a mental note of a few of the pictures that she thought Sandy might get a kick out of.
As she stared at the pictures, her mind wandered back to their earlier dinner conversation. She still had no idea what she wanted to do with him at the poker game, but he had given her lots of interesting things to think about. And the more she thought about some of them, the more sexually stimulated she seemed to become. Imagine, making him behave like a total ass in front of all his friends – his male friends!
But the truth of it was, that she really had no intention of making him behave like that – yet. She didn’t think it was right to disgrace an obviously cherished event with things that didn’t belong there… Although the more she thought about it, the more interesting some of the ideas became. In her mind’s eye, she could just see him skipping into the room full of men, wearing that silly babyish outfit, his diapers showing obviously underneath. Maybe she’d add a baby bonnet to his head to complete the picture. His pacifier would be another good thing too – he could suck on it in front of them all evening… And speaking of sucking on something…
She closed the book and hurried out into the living room. He had already put the excess diapers away – no matter. While he was sorting through the laundry, she hurried into her bathroom and started pulling out towels. Moving faster and faster, she carried them back out into her living room and began spreading them all over her couch, layering them to protect the chair as much as possible.
She moved on to her desk drawer where she pulled out a jumble of ropes. Quickly selecting one, she carried it over to where he was bent over the laundry basket. He started to stand and turn around at her approach, but she stayed behind him and pushed him back down again. Grabbing his elbows from behind, she pulled them behind his back, pulling hard to bring them as close together as possible. She quickly wrapped her piece of rope around them, binding his elbows behind him. She grabbed the rope and pulled him to his feet, then kept pulling, forcing him to walk backwards as she dragged him toward her couch. She put him into position facing the couch, then forced him to his knees. She grabbed more rope. His wrists were soon bound tightly together, then his ankles. Another rope soon ran from his wrists down to his ankles, pulled tight so that his arms, even bound at the elbows, were stretched as far out as they would go. Feeling satisfied with her work so far, she hurried straight into her bedroom.
Chad had been very startled when she had suddenly come up behind him. Then even more so when she had roughly grabbed his elbows and pulled them back. She hadn’t bound his elbows like that behind him before and it hurt from the beginning – it still hurt now. The rest was more familiar. As he knelt before her couch, towels spread all over it, he knew exactly what to expect. Two minutes later, he heard her come back again, and faster than he expected, his sight was taken away as she tightly tied her scarf around his head.
Mel was breathing heavier now as she looked at him. He was ready. The couch was ready. All that remained was for her to remove her clothes. She still didn’t know why she didn’t want him to see her naked, but with the scarf covering his eyes, that wasn’t really a factor.
She walked around and stood in front of him, the crotch of her shorts pressed lightly up against his nose. She hooked her thumbs inside of the waistband of her shorts and wiggled her hips against his face, tantalizing him. Then very slowly, she kept wiggling back and forth as she lowered her shorts all the way to the floor. As she bent down, she allowed her body to rub against his face, till now his face was between her breasts underneath her shirt. She wiggled them back and forth against him before she stood up again.
She leaned into him again, letting her panties rub against his face. Letting him smell the scent of her sex barely masked underneath. Standing there like that, she pulled her top off, the motion causing her panties to rub against him once more. She stopped there like that and looked down at him, her pink pastel panties shoved into his face. She was getting so hot!
And then she felt it. Something unexpected. And her entire body shuddered. He had tried to stick his tongue into her, through her panties. She couldn’t have moved if she tried, hoping that he might do it again. And then he did! A moan escaped her lips as she reached down with both hands and locked them into his hair. Again his tongue reached out, harder than before… longer than before, she felt his head tilting as he licked the front of her with his tongue. Her back arched. She would have cried out loudly if her breathing hadn’t been completely locked up. By the time he tilted his head down again, she was panting hard. She reached back and removed her bra, freeing her breasts so they too could receive some attention.
She stooped straight down, rubbing her smooth breasts across his damp face – wet from the dampness that had come through from her soaked panties. With her hands still locked in his hair, she rubbed her breasts back and forth… round and round, all over his face – her nipples growing bigger and bigger as she did it. So good! But she needed more!
She stood up again, her panties once again pressed against his face. She felt his tongue reach out again even as she put her thumbs into the waistband of her panties to begin pulling them down. She had to pause till he withdrew his tongue again. Then just as she had done with her shorts, she rubbed her crotch against his face as she slowly lowered her panties. Down… down… till his face now touch nothing but her wet, naked sex. She rubbed it into him for a moment, then resumed her motion to bring her panties down to the floor, once again pressing her breasts against his face.
Slowly, she stood back up, never once letting her body leave his face, till her aching sex was once again poised right where she needed it to be. She ground it into him, spreading the wetness all over. Finally ending up again right where she wanted to press against him the most. She paused again, and once more she felt his tongue reaching out, only now there were no panties in the way. Now it could enter her further.
Again and again she thrilled as he licked at her, driving his tongue into her as far as it could go. But she knew it could go further… she needed it to go further. Still holding tightly to his hair, she quickly moved backwards, sitting down on the couch, dragging him down so that his feet, tied to his hands behind him, were lifted off of the ground and his weight rested on his face – mashed perfectly into her crotch.
She pulled tighter on his hair, pulling him harder into her waiting sex, and was rewarded to feel his tongue once again reaching out, this time seeming to probe her everywhere it could reach. Spot after wonder spot inside of her was touched by his tongue, the very movement of it driving her wild. And then it finally found the sweetest spot of all and lingered against it, flicked against it, licked against it… over and over again… driving her up, higher and higher, wilder and wilder, till at last… “Yeeeesss!” she screamed in ecstasy.
She felt his probing tongue slow as she finally came down from her high. Slower and slower, till she felt it withdraw completely. She wanted more though. She was nowhere near being finished. But before she could urge him to do it again, she felt his tongue reaching out once again, this time almost tentatively. Teasing her. Sending her in an altogether different direction. No longer thinking, she abandoned herself to his talented tongue, riding him once again to yet another wonderful high.
This time, when she came down, she felt his tongue withdraw once again. She realized he was breathing hard, almost gasping for breath. She took pity on him and pulled his face away from her crotch so he could breathe better. His face was a total mess, but she didn’t care. But the act of pulling him away and looking at him, seemed to ruin the magic. She no longer felt the desperate need she had felt earlier. Her hands still locked in his hair, she tilted him back till his feet returned to the floor. Then she slid down from the couch right in front of him. She pulled his messy face into her neck and hugged him, pulling his body as closely into hers as she could. She held him like that till they both calmed down. Then, slowly, she released her grip on him and leaned back. He was a mess! An absolute mess! And it had been wonderful – yet again!
As messy as his face was, she leaned in close and lightly kissed the bare patch of skin on his forehead just above the blindfold. She knew the moment she had done it that she shouldn’t have, but it was too late now. She moved around to his side, and gently pulled on him, helping him to lay down where he could be more comfortable. As soon as she felt satisfied with his position, she stood up and left him, going straight to her bathroom… and into her shower.
Chad laid in darkness, unable to see because of the scarf tied around his head… unable to move because of the ropes tied to his arms and legs. His arms ached terribly because of the way she had bound his elbows. But there was nothing he could do about it… unfortunately. The moment he heard her shower running he almost died, because it meant that she wouldn’t be coming back to release him anytime soon.
He waited, and waited – impatiently, yet unable to move in any way. He remembered that he was supposed to be making his diaper leak – again. Yet she had prevented him from drinking enough to keep working on it. Would she take pity on him and not punish him for failing? Somehow, he doubted it. She would be as ruthless as ever. Yet… he had felt the faint touch of her kiss on his forehead. It would be a moment he would always remember because it had surprised him so much. But was it worth her beating him again because he failed to make his diaper leak? He wasn’t so sure.
Mel wrapped her robe tightly around her naked body, tying it tightly to make sure it couldn’t slip open. Barefooted, she walked back out to the living room where he was still tied in the position she had left him. She knelt down next to him and removed his scarf. His face was still a mess. She reached over and pulled the top towel off of her couch and used it to wipe his face somewhat. He looked a bit better. Then she removed the rope binding his wrists to his ankles. His sigh of relief was audible as he bent his legs out straight. His elbows came next. He moaned with relief the moment they were free. Then finally his wrists. He struggled to pull his arms in front of him, rubbing them with his hands, flexing them over and over again to get them working.
She stood up again and looked down at him on the floor. “I suggest you get a bottle back into your mouth again and start drinking. Time is wasting!”
As Mel walked off to her bedroom, Chad slowly pulled himself up to his knees, and finally to his feet. His body still hadn’t recovered from the way she had used him, but he made his way back to the laundry basket where he had left his latest bottle and put it immediately to his mouth. But continuing on with the laundry was beyond him just then. He sat down on the floor, leaned his back against the washer, and just sat there, his eyes closed as he drank from the bottle. Had she really kissed him? Something about the tone of her last statement before she walked off made him seriously doubt it. But it was a nice dream.

Mel checked the clock more and more often as his deadline drew nearer. She knew he was drinking his bottles furiously to try to keep wetting, and she knew his diaper was indeed getting wetter and wetter. But she also knew that he wasn’t doing much of anything else. For once, she didn’t really care. With all her might, she silently wished him success. She didn’t want to beat him again tonight – especially when it was her fault if he failed. But she couldn’t relent in any way… or at least she couldn’t seem to. Was there a way to go easier on him, for once, without him knowing it?
With only five minutes to go, she saw him checking the clock more and more often too. She could actually see the strain on his face as he tried desperately to keep peeing – peeing enough to leak out of his diaper. She didn’t want to see him fail, yet she also didn’t want to make things easier on him. But she couldn’t stand it any longer – she could see how hard he had been trying. She just couldn’t punish him tonight for something that was really her fault – especially not after the way he had sent her into ecstasy earlier. She had everything already in place. He had done enough! “Sissy! Put your bottle down and come into my bedroom. Now!”
Chad was completely surprised. He glanced at the clock again, there was only a few more minutes to go. He looked down at his bare legs – no leaks. “But Mistress…”
“Don’t worry about it and get in here,” she commanded.
Chad had little choice but to do as he was told. Once he got to her room however, he was surprised to see that she had again spread plenty of protection all over her bed. Was he about to get whatever little pleasure she would allow him after what he had done for her? He could only hope.
“Lay down, Sissy. We’ve done this before.”
Chad laid down on his back on her bed. Mel quickly grabbed some of her rope and tied his wrists to the headboard. “We don’t want your hands getting in the way,” she said. As if he would! He expected her to tie his feet next, but she didn’t. Because of that, he expected her to remove his diaper… but she didn’t do that either. Instead, she pulled out the little bottle of glue remover and began painting it heavily all around his glued on breast forms. Chad felt like cheering. He couldn’t wait to get rid of the things. They were bulky, and heavy, and constantly in his way! How did women stand the things?
Little by little, Mel worked the glue loose on the breast forms, till finally they both released from his body. Chad immediately felt the pressure removed from his chest as the weight was lifted off of him. He felt the cool air against his nipples for the first time in a week. He breathed in heavily, enjoying the sudden sense of freedom. It was so much easier to breathe now. He wanted to rub and scratch at the area, but she had tied his hands out of the way. That would have to wait till later. Still, he was very happy to have them gone.
“They go back again tomorrow,” she said. “So don’t get used to it.”
Ugh!
He felt her undoing his diaper then, which surprised him all the more since she hadn’t been able to make it leak yet. Was she going to punish him now? He hoped not. He felt the cool air now touch his bare front as she pulled the sodden diaper down between his legs, preparing to pull it out from under him. But the moment the cool air hit him, he began peeing again.
Mel laughed a bit and pulled the diaper up a little more to make sure it caught everything. “Good baby,” she crooned in a teasing voice. Chad felt very embarrassed by it.
When it was safe enough, she removed the now wetter diaper from under him and left him alone, tied to her bed. She came back a few minutes later with a wet cloth that she used to wipe his chest where the breast forms had been, and then the area all around his chastity device. As she did so, she noticed that despite having the medium sized teeth in the device instead of the larger ones, he still seemed to be as small as ever. Perfect!
She spread some baby lotion over what she could reach on his front, then had him roll over – which wasn’t the easiest thing in the world for him to do with his hands tied as they were. She wiped his backside then and applied more baby lotion. As she rubbed it in, Chad was hoping that she would start playing with his backside again. The last time she had done that she had used a very interesting little toy on him. He’d wanted to see what it felt like again.
But instead of using her toy on him, Mel grabbed her jar of suppositories and removed the lid. “I hope these things are still working,” she said as she pretended to pull one out. A moment later she was rudely shoving her finger up into him as far as it would go, pretending to insert the imaginary suppository – that hopefully would work just as well as the real thing. Chad wasn’t at all pleased – even more so because it meant that she wasn’t going to play with him tonight. Darn!
She had him roll back over again and began fastening three of the thickest nighttime cloth diapers around him – the thickness adding lots of pressure against the inside of his crotch. Once the diaper pins were in place, she untied his hands. “You can get up now,” she said as she grabbed his plastic panties and held them out for him to put on.
Chad slowly got up from the bed. The pressure from the super thick diapers made moving more difficult. He had to struggle to pull the plastic panties on and then into place. And when he tried to walk, he was already waddling – and the diapers were still dry!
“Remember,” she said, “three more bottles before you go to sleep. And find yourself one of your onesies to wear to bed tonight.”
Three more bottles! But that was no surprise. That’s what she made him drink every night now. “Yes, Mistress,” he said as he attempted to curtsey in the super thick diapers.
Chad headed toward the door clad in only his diapers and plastic panties. He pulled the keys to his own apartment out of his purse and held them in his hand. He slung his purse over the crook of the same arm. He slung his diaper bag over his other shoulder. His clothes that he had removed earlier got slung over one of his arms, the shoes taking up one of his hands.
He didn’t know why, but he felt somehow sad and disappointed. Curtseying was pretty much impossible under the circumstances so he didn’t even try. “Goodnight, Mistress,” he said. Then he turned toward her door.
“Goodnight, Sissy,” she replied. “Sleep well, you’ve got a busy day tomorrow.”
Chad wanted to ask her what she had planned, but somehow, he didn’t think he wanted to know just yet. He would let the problems of tomorrow wait till tomorrow. He just nodded and opened her door. Then, walked out, clad in only his diaper and plastic panties. He softly closed the door behind him.
Mel stared at the back of the door as it closed. “Goodnight, Sissy,” she repeated softly. “Sleep tight.”