The Bet - Chapter 12 (Wednesday – week 2 Part 1)

The Bet
by Karen Singer

Chapter 12 (Wednesday – week 2 Part 1)

Sharp little pinpricks to his private area slowly seeped their way into his dreams, increasing in strength. He groaned for the hundredth time and came partially awake. He hadn’t slept hardly at all because of those pinpricks. He rolled over on his blow-up mattress as best he could since his diapers were so swollen that maneuvering was difficult – especially now with the chastity device she had locked onto him. That by itself was a nightmare to deal with – even when it wasn’t hurting him. Finding a comfortable position to lay in was even more challenging.
The pain of the pinpricks died away and he fell blissfully back to sleep, but only for a little while. His alarm clock began blaring loud music. He jolted back out of his sleep with a start, trying to comprehend the commotion. No, the device wasn’t hurting him just then. Finally he realized his alarm was signaling that it was time to get up. He pounded his fist on the bed and rolled into another semi-comfortable position, again. But the loud music was still there. Cursing under his breath, he got to his feet and turned the music off.
He stood there for a while just looking at the floor, totally fogged out, not even trying to make sense of anything. His diapers felt like one huge solid ball between his legs. But that was beginning to feel normal to him now. He wanted to go back to bed. To sleep, for a week – at least. But there was some reason why he couldn’t. What was it? Why couldn’t he go back to sleep? Finally the reason seeped through. Oh yeah, it was time for another baby bottle. Then he had to get ready for work. Ugh!
Walking into the kitchen was more like swinging one leg after another around the huge bulk of his diapers. But that too was feeling more normal to him. He didn’t even think about it. He opened his refrigerator, Mel had restocked it again yesterday. Way too many baby bottles – and nothing else. He grabbed one at random and put it into his mouth as he headed back to his mattress. Her lousy tea again. He was so used to it that he didn’t give it another thought. He just laid back on his back and held it to his mouth like a baby and drank. He was very well used to that too. It was almost comforting now in a way. But he was too tired to realize it.
As he drank, the need to pee seeped partially into his brain, he let it loose without thinking about it, just as he had all night so he could get at least some sleep. He began concentrating on the feeling of the pee rushing out of him. It was better than concentrating on other things that might make those little pinpricks come back again. The feeling of peeing felt good just then. He relaxed and enjoyed it. But all too soon it was over. He couldn’t tell one bit of difference to his diapers. They were that wet.
His foggy brain woke up a bit more as his bottle finished. He carefully rolled to his feet and carried it back out to the kitchen. There was a collection of empty bottles on his counter. This made bottle number five. Way, way too many.
He went back into his bathroom to shave and brush his teeth, not sure if he wanted Mel to be early so she could change him sooner, or late so he could go back to sleep.

Mel poured herself a cup of coffee and took her first sip. Mmm, it tasted good. She just hoped it would wake her up quickly. She thought for the thousandth time about Chad. Had he slept well? Had he slept at all? Did the device she locked onto him hurt him too much? She had no answers. She had worried about him all night. But the only way she was going to get those answers was to go see him. That time was approaching. She took another sip of her coffee and started to get ready, only throwing on some jeans and a t-shirt. She would take her time getting ready for the office later.
She grabbed her keys and went over to his apartment, unlocking his door with her copy of the key. She heard water running in the bathroom. At least he was up. She went to see him.
Chad turned his head while he was shaving and saw Mel standing in his bathroom doorway watching him. He hadn’t heard her come in. He realized that going back to sleep was out of the picture now. She was just standing there watching him. “Good morning, Mistress,” he said.
“Good morning, Sissy,” she replied.
Chad went back to what he was doing. When he had finished shaving she took his onesie off of him and helped him get his diapers off again. When he was finally naked, Chad looked down. It was his first glimpse of the device she had put on him last night. It was all clear plastic, totally covering every bit of his penis. There were small slits in it for cleaning or to let his pee out, but touching himself was obviously impossible. The way it was molded, it held his cock firmly straight down so it couldn’t go in any other direction.
There was a band wrapped tightly around his balls and the base of his cock that held it tightly to him. He reached down and touched it. It felt hard. He could feel nothing of the touch of his finger from inside. As he looked closer, he could just see the tiny little jagged spikes that dug so painfully into his skin the moment he got any larger than he already was. He suddenly felt the start of the pinpricks from those spikes again and took his hand away. The thing was a nightmare. An absolute nightmare. Sighing, he looked up at Mel who had been watching him.
“Ok, enough, into the shower now and get cleaned up.”
While Chad was in the shower, she picked out the clothes she wanted him to wear for the day, then she found his purse on the living room floor where he had dropped it last night and carried it into the bathroom. It was heavy since it held all of his makeup. A short time later, Chad was again diapered with a fresh suppository up inside of him, and once again wearing his all-in-one girdle with pantyhose over it. The girdle compressed his chastity device against him tightly, but surprisingly it helped to hold it in place so it was really no problem there. The thing that he really wasn’t used to now was that the chastity device held his penis straight down – permanently. He wasn’t used to that and it felt strange. There was a bit of an extra bump in the front of his girdle now but it didn’t appear to be too bad at all.
Once again it was makeup time. But this time Mel began by showing him how to apply his eyeliner. This was by far the most difficult thing he had tried yet. Over and over again he tried but he couldn’t get the lines exactly right. Finally Mel said, “Close enough. Leave it and do your mascara and eye shadow now.” Chad did as he was told although he wasn’t happy about it. Obviously Mel was going to require him to wear the eyeliner to work too. Why? She had to know that he was still washing it all off as soon as he got there.
“Put another coat on the mascara,” she instructed him before he finished with it. “I want it to be a bit more visible today.”
The little pinpricks were suddenly back again. He paused in what he was doing to let them settle back down a bit before he was capable of continuing. Then he went back to making his mascara a bit heavier. He still had to wonder why she was bothering.
When it was time for him to get dressed, Mel handed him another of his male shirts, then the navy blue female slacks he had bought a few days ago. He wasn’t happy to see them at all, but he knew to expect them since she had fixed it so he couldn’t get at any of his male pants.
The biggest surprise of the day though, was when Mel handed him the low heeled pumps that he had worn all last night instead of his male shoes. The pinpricks suddenly came back in a major way, and they didn’t seem to want to go away this time. He set the shoes down on the floor, but he had to back away from them. The device was hurting him too much. He waited, desperately wanting the pain to die down. It did finally, but not much.
Mel watched as Chad tried to deal with the pain of the device. She knew she had to be patient and just let him learn to deal with it. In a way, she felt sorry for him but she wasn’t going to back down now – for any reason. She knew without a doubt that what he was going through now was critical.
Chad’s pain finally reached a level where he could tolerate it, some. He approached the shoes and slipped his left foot into one. The pain started to come back again. He had to push hard to get his foot all the way into the shoe since it was a bit tighter than he liked. The shoe was on and there was now a partial ring of fire against the base of his cock. He had to pause, desperately willing the pain to go away again, but it stayed. Fighting through it, he put the other shoe on.
He was now wearing women’s shoes to go to work in… they went right along with the women’s pants he was also wearing… which also went all too well with the pantyhose and the all in one girdle and the makeup and the purse he would be carrying later. He was going to have to go to work again dressed like this. Just thinking about his situation was fueling his sexual need in a major way. His cock was desperately trying to get hard where it obviously couldn’t. The little amount of swelling it was trying to do now had those miserable spikes firmly dug deeply into him, causing him immense pain. He grabbed at his crotch uselessly, prancing around the room half doubled over. Why did he have to be so turned on by all of this?
It took him four or five full minutes to even begin to get the pain under control. He dared not look down at his shoes again because every time he did it acted like a signal to start the pain all over again. He tried desperately to not think about his situation, but that was impossible. Worse, even the pain was now fueling his need. Eventually, he was able to come to grips with what was left of the pain… at least enough to function.
Mel had stood back and watched the whole process with a resolute expression on her face. Chad had to know that despite the pain that he felt, she wasn’t going to release him. When it looked like he was finally recovered enough, she left him to prepare his diaper bag for the day. As she was putting the two fresh bottles in it, she glanced at the time, it was getting late. Too late. There wasn’t enough time left to give him another bottle before he left.
Chad had finally come out of the bathroom and was waiting in his living room for her. “You forgot your purse,” she said to him. He seemed to sigh a bit but he turned around to go get it. “Make sure you bring all your makeup with you today,” she called behind him. She got no response, but when he came back out again, she could see that his purse was still fairly full and heavy. She handed him his diaper bag. “Have a good day,” she told him as she opened his door for him.
He looked at her with an almost menacing expression on his face for a few moments before he turned and walked outside. As he walked further away she said softly, “And good luck!” She could have been soft on him this morning and not made him wear anything new after putting the chastity device on him, but she had been a lawyer too long. She looked at it the same as if she were grilling a hostile witness. You could be soft or hard and change your tactics in mid-stream, but once you made a little chink in their armor, not matter what, you never backed down. You just kept hammering at them till they finally cracked.

Chad forced himself to take one step after another as he headed down to his car. Just walking outside like he was had caused another flare up of the pain, but he was dealing with it better now. He got into his car and set his bags down on the passenger seat and closed his car door. He closed his eyes, trying to will the pain to go away. He sat there like that for a while before he was finally able to do anything else.
When he finally felt strong enough to drive, he realized that he didn’t have his keys, they were in his purse. He had to dig through tons of makeup to find them, a major nuisance. But finally he was able to start his car and drive straight to work. He didn’t have time to stop for breakfast on the way.
When he got there, he automatically reached into his console and pulled out the socks he had hidden there. It was difficult to do in the car, but he pulled one shoe off and slipped one of the socks on. Then he tried to put his shoe back on. It wouldn’t go. The shoe was simply too tight and his socks were just too thick. There was no way. But he continued to struggle anyway. The sudden loud knocking on his car door window made him jump, scared out of his wits. He turned and looked up and saw Robin standing there.
“Are you all right?” she asked through his closed car door.
He nodded. “Yeah, I’m all right.” He replied dejectedly.
She knocked again on his window. “Open up.”
Without thinking he opened his car door.
“Hi Chad,” she said. “I saw you struggling with something and I just thought I should check.”
He nodded to her again. But instead of answering he suddenly just laid his head against his steering wheel. “I’m not having the best of days,” he told her.
She didn’t say anything, but just stood there, waiting for him. Finally she asked quietly. “Are you going to show me what you’re wearing?”
Chad sat back in his seat. Knowing there was no avoiding it, he swung his legs out of the car. His one foot with the sock on it looked all too obvious in the bright morning light.
“What are you doing?” she asked.
“I was trying to cover up my pantyhose with these socks,” he explained, “but now I can’t get my shoes back on!”
She looked back at his feet. He hadn’t been wearing women’s shoes yesterday, but obviously he was today. “I don’t think you can wear those socks with those shoes,” she said. “And they don’t match anyway. Why would you want to?”
Chad just groaned and reached down and pulled his one sock off with a swift pull and threw it angrily onto the floor on the passenger side. Then he found his other shoe that was still off and slipped it on.
“There,” Robin said, “that looks much better. Ready to go to work now?”
Knowing that it was inevitable, Chad reached over and grabbed his purse. He opened it and pulled his cell phone out, then he grabbed his keys from the ignition and put his purse back on the seat again.
“Why don’t you carry it?” she asked.
Chad’s reply was filled with frustration. “Because this is all humiliating enough! That would only make it worse!”
“Then why are you doing it?” Chad didn’t answer. Instead he got out of his car and slammed his door shut.
“Oh for heaven’s sake!” Robin said. “Carrying a purse with the way you’re dressed right now can’t be that much worse! Grab the thing and get it over with!”
Almost angrily, he reopened his car door and grabbed his purse. Then he closed and locked the door. “Satisfied?” he asked with more annoyance than he should have.
“It’s not me who needs to answer that,” she said as she started walking towards the building.
Chad fell in beside her, feeling all the more foolish today about the way he was dressed than he did yesterday. “Sorry,” he said softly to her.
“Your purse looks a little heavy,” she noted. “What have you got in there?”
“All my makeup,” he replied.
“I noticed your eyes this morning.”
Chad grunted. “I’ll wash it off as soon as I get inside.”
“Why bother?”

The Bet - Chapter 11 (Tuesday – week 2 Part 5)

The Bet
by Karen Singer

Chapter 11 (Tuesday – week 2 Part 5)

When the laundry was done, and the television show Mel had been watching was finally over, she finally told him to get undressed so she could change him. He was more than ready for it. He was so messy and wet that he was beginning to get more than uncomfortable inside of the girdle he was wearing.
She took him into her bathroom and let him undress down to just his diapers, then she very carefully helped him remove them so as not to spread the mess any further than it already was. She surprised him at that point by sending him into her shower to fully clean off. The shower was followed by a nice warm and mostly relaxing bath – except for when she again shaved his entire body again, spending extra particular attention this time to his privates. When she was done shaving him, she left him to relax and soak for a few minutes while she went out to her bedroom. When she finally came back, she had him get out of the tub and dry himself off.
Chad fully expected her to diaper him again then, but he didn’t see any sign of his diapers at all. Instead, Mel came back with the scarf that she used to blindfold him and once again covered his eyes, tying it tightly behind his head so it wouldn’t easily slip off. He was getting nervous now, but there didn’t seem to be anything in Mel’s attitude that suggested that she might be angry about anything.
“Just follow me,” she said softly as she grabbed his arm and slowly led him into her bedroom.
Her touch was almost sensual as she led him by his arm. He kept reaching out with his other arm to try to feel where he was so he wouldn’t bump into anything, but she was careful to keep him well out of harm’s way. Finally, his free hand came in contact with something tall and round, he realized it was one of the bedposts on her bed. A moment later, she backed him up till his legs came into contact with the mattress behind him. “Lay down,” she said softly as she helped guide him onto her bed, then scooted him over till she got him into the position she wanted.
Chad said nothing through any of it. Was this his reward for making her a great dinner, or perhaps acting as her maid – or more probably both? He had been good. She had punished him before, maybe now she was rewarding him.
He felt her soft hands run lightly over his body, then up one of his arms, ever so gently pulling on it. “Shhh,” she said as she pulled a bit harder. Chad suddenly felt ropes being attached to that wrist, holding it tightly stretched up over his head. “Shhh,” she said again, calming him, relaxing him. Again her hand ran lightly over his chest, then it was gone.
He heard her walking around to the other side of the bed, climbing on top of it. Her hand was back again, running lightly over his chest and up his other arm, only to tie it as she had done with his first arm. He realized he was breathing heavier and heavier. His cock was getting bigger and bigger. Wow, could this woman make love! And she hadn’t even touched his good parts yet!
Once his arms were secure, Mel moved a lot faster to tie his ankles to the bottom bedposts so that he was spread out wide and helpless. His hairless body was obviously waiting for her. His cock was standing firmly at attention. She breathed a sigh of relief. She had done this to him on purpose. Unfortunately, for him, she had no intention of giving him what he wanted.
She opened the drawer of her nightstand and pulled out a twelve inch ruler that she had taken from her desk a little while ago. She figured that if her yardstick could do such a good job on his backside then this little ruler could do the same for his front. With a loud swish, she brought it down hard on his fully erect cock.
Chad’s body suddenly exploded in unexpected pain. What had happened? His cock suddenly felt like it was on fire. “Owww!” he cried as he jerked hard at the ropes that held him all too firmly. Then the horrible sting came again. “Owww! Shit, that hurts!” he protested.
“What did I tell you about using language like that,” Mel replied, then she hit his cock five more times in quick succession. Each time Chad’s body jerked hard against the restraining ropes. His cock was quickly growing smaller, which was exactly what she wanted to see.
“That hurts!” he complained loudly again.
“Good!” Mel replied.
“Why? What did I do?” he asked. “I thought you liked the dinner I made tonight.”
“I did,” she replied. “I loved it. This isn’t about punishing you for anything.” Then she brought the ruler down one more time and watched him jerk, although this time silently.
Chad was not only blind and helpless, now he was confused too. She wasn’t punishing him? That’s what she thought. She had no idea how much she was hurting him. He suddenly sensed her head very close to his ear.
“This is the next phase of your training,” she whispered to him. “Since you can’t pee when you’re hard, then we’re just going to have to teach you not to get hard anymore. Now doesn’t that sound like fun?”
“No!” Chad shouted in horror. He felt her moving away from him quickly and just as quickly came the next stinging blow to his cock. “Ow!” he said again as he thrashed one more time to get free.
“See, you’re nice and soft now. See how well that worked. But I’ll bet I can make it hard again. Shall I?”
Chad was about to say no, but suddenly he felt her hands on his cock again, massaging him, kneading him, and despite his wanting not to, making his hurting cock grow again.
“Do you have to pee yet, baby?” she asked softly in his ear. “Don’t worry if you do, I put several nice soft diapers underneath you, so go ahead if the urge hits you.”
“I don’t have to pee!” he said angrily.
“Aww. Too bad. But of course you can’t anyway, can you? Because you’re way too hard again.” She leaned even closer into his ear. “Here, let me fix that for you.”
Before Chad could protest, she was up and swinging at him again. “Ouch!” Chad screamed. She swung again. “Stop!” he pleaded. She swung again. “Please stop! You don’t know how much that hurts!”
Mel leaned down toward his ear again. “I really don’t care. I only want to make you soft again. The quicker you get soft, the sooner I stop.” She hit him hard one more time. Then once more for good measure. His cock was mostly limp by then. “See how well that works.”
Chad didn’t care about anything except the fact that she had finally stopped. His entire cock felt like it was on fire. But then he felt her magic hands back on it again, once again working it to make him hard. “No, please no!” he protested.
She stopped. “What is it? Before you wanted me to stop hitting you, now you want me to stop touching you? Which is it? You can’t have it both ways.”
“I don’t want either,” he declared.
“Awww. Too bad. I’m afraid I’m not done with you yet.” And with that she continued massaging him and trying to get him hard. It was a lot more difficult this time, but eventually she got him there and eventually she began beating his cock again with her ruler. His cock seemed to deflate this time like a balloon with a small hole. She almost laughed. “There now, that wasn’t so bad this time, was it?” But the only sound coming from Chad’s mouth was some muffled moaning through his clenched teeth.
Mel opened her nightstand again and took out all the pieces of the chastity device she had bought him. One by one, she began fastening them around his privates, removing pieces over and over again and replacing them with other pieces till she got just the fit she thought she wanted. Curiously, his cock was starting to grow a bit again.
Chad felt her playing with him again, but it felt more like she was putting things up against him and then taking them away again. “What are you doing?” Chad asked.
“Shhh. Don’t you worry about it… Or maybe you should worry about it. But I’ll let what I’m doing be a surprise for later.”
She picked up one of the Points of Intrigue and attached it to what she had already put on him. She purposely chose the longest most severe points so that he would feel them right away. Once it was in place, she pressed down on it.
“Ow!” Chad suddenly cried and jerked again at his bonds.
“Hurts, doesn’t it.” Mel said to him.
“Yeah! A lot!”
“Good! That’s what it’s supposed to do.” She pressed again and felt his body writhing in pain under her. His cock was suddenly a lot smaller. “I’d say that works pretty well, wouldn’t you?” She wasn’t at all surprised that she got no answer from him at all.
She took the longest spikes away and chose the medium ones and put them in place, adjusting them so that they were just where she wanted them. Then she picked up her ruler again and hit him three times in succession.
Chad suddenly felt the searing pain hitting his cock again. He screamed all over again. Now what was she doing? She was torturing him. That much was for sure!
Mel watched as his cock grew even smaller. “That helped,” she said. “Sorry, I just needed it a bit smaller, that’s all.” She put her ruler down and picked up the main part of the device that would contain his now flaccid penis. She had to push it onto him and it wasn’t all that easy.
Chad felt her grab his sore and aching cock. Then suddenly it felt like she was trying to stuff it into something hard. He realized that that was exactly what she was trying to do to him. And then it finally dawned on him… he suddenly realized exactly what she was really doing to him. She was putting some kind of a chastity device on him. And whatever it was, it felt like it was way too small… and it hurt! He desperately tried to buck her away, to stop her, but it wasn’t working. “No, no!” he cried, trying to get her to stop. But he was tied way too tightly. And she didn’t seem to be stopping!
Mel suddenly had to hold on to him as he started thrashing harder. His pitiful cries for her to stop meant nothing to her. Gradually his thrashing started to slow down. When it had slowed enough, she grabbed the lock that she had already opened, and still keeping her weight on him, slipped it into place. She snapped it shut with a very satisfying click.
Chad felt her fumbling around with him again despite all his thrashing. He heard the faint sound of the lock clicking shut and suddenly felt totally defeated.
Mel stood back up to catch her breath. “You can stop struggling now,” she said. “It’s locked on and it’s going to stay on.” His thrashing suddenly increased – a lot. He was angry she realized. She thought she heard him whimper as his struggles gradually slowed down, then finally stopped. She let him rest for a moment while she watched him to make sure he was going to be alright.
She left him and went into her kitchen. She pulled another baby bottle out of the refrigerator for him and brought it back to the bedroom. She sat down on the bed next to him and put the bottle to his lips. “Here, baby. Drink.”
Chad felt the nipple touch his lips and he automatically accepted it and started sucking on it. The cool liquid felt good against the back of his throat. Very good. But he was trying to drink it too fast and he started choking on it a little. She removed the bottle. “Slowly, baby. Slowly.” He felt the nipple come back again and he continued sucking – much more slowly this time. All too soon he felt the liquid in the bottle finishing, and then suddenly the nipple was gone. “Good baby,” she crooned into his ear. He felt her brush his face – almost lovingly.
Mel got back up again and took his empty bottle back to the kitchen. She walked slowly. She needed to catch her breath too. She wasn’t quite done with him yet.
She walked back into the bedroom and sat down on the bed next to him again. “Ok, baby. Let’s try this again.” Then she reached out and started trying to stimulate his privates all over again – although she really couldn’t do it very well, encased in the hard plastic like they were.
“No! Please don’t!” he pleaded once again. But she continued anyway. She kept a close eye on the clear plastic covering his penis and especially on the little sharp points that were beginning to dig into him again.
Suddenly he seemed to freeze, all his muscles locked tight. She stopped touching him. No sound came from his mouth for a moment, then he let out a long drawn out, “Owwww.”
She watched him as his breathing grew heavier, almost panting. Very slowly but surely, it calmed down again… as did he… as did any excitement to his cock. If anything, his cock appeared to be a little smaller. Fascinated, she continued to lay there as she watched him trying to calm himself. Gradually, very gradually, he became even smaller. His penis no longer filled the entire inside of the surrounding plastic. He was laying still, very still, resting. “Is it better now?” she asked. She got no answer. “Does it hurt anymore?”
His answer was very flat. “No.”
She nodded to herself in satisfaction. “It won’t hurt as long as you stay soft,” she replied. Gently, she touched the device. He stiffened quickly. “I’m only looking,” she assured him. He calmed down, but only a little. She looked as closely as she could. There were a few red marks she thought from the sharp points of the teeth, but no other damage as far as she could see.
Satisfied, she began picking up the rest of the pieces from the device and put them away.
“I have to pee,” he suddenly said.
She quickly picked up one of the cloth diapers that she had kept handy and wrapped it around his device. “Go ahead,” she said softly. Within moments, she felt the diaper in her hands growing warmer and wetter. But the thick material was more than enough for what came out of him. Not that it mattered. She had put protection under him anyway. His face was red. He was blushing. “Good baby,” she whispered again in his ear when he had finished.
Very carefully, she put baby lotion on him again and put another suppository up inside of him. Then she rediapered him in three disposables while he was still tied up.
It was time to release him. He was laying completely still, as if he was afraid to move. One by one she removed the ropes from his legs, then his arms. He still didn’t move, not for a few moments. Then, slowly, he brought his arms down, as if he were afraid to move them. He flexed them a bit. Then he tried moving his legs, just a tad, not much at all.
“Sit up,” she told him, and grabbed one of his arms. With her help, he rose to a sitting position. She took his blindfold off. He blinked and rubbed his eyes. She tried desperately to read the expression on his face, but she couldn’t tell anything.
Chad’s mind was in a total state of confusion. He didn’t know if he felt angry, or defeated, or even deep down sexually stimulated. All three he finally realized. She had put a cock restraint on him. Locked it on. His own cock was locked up in something that obviously wouldn’t even let him touch it. Slowly, he forced himself to look down at his crotch. All he could see were all the diapers that covered him. He didn’t even know what the thing looked like. He looked back up at Mel. “Why?”
She smiled. “To teach you.”
“To teach me what?” His question held a touch of anger.
“To teach you control.”
He wasn’t buying any of it. He looked down at his diapers again. Locked up. How was he going to manage? How was he going to do anything? He pressed down lightly on the front of his diapers, then a bit harder. He felt something hard inside. From the inside he felt nothing but a bit of pressure where the device was locked behind his balls. Nothing at all on his cock. He looked back up at Mel, totally bewildered. “What am I going to do?”
She smiled at him. “You’re going to learn, baby. You’re going to learn.”
Mel left him for a moment while she went out to the piles of clean laundry that were stacked in her living room. She came back a few minutes later with one of his onesies. She helped him put his plastic panties on, then she helped him step into the onesie, zipping it up the back and clicking the lock at the top shut with another distinct click. A moment later, Chad doubled over slightly and grabbed at his crotch as a small wave of pain lanced through him from the devilish points of the device.
Mel realized instantly what had happened. “You’re going to have to learn not to get hard anymore,” she said. “And it looks like you’re going to have to learn it fast.”
Through great effort, Chad controlled himself and the pain died away completely. How was he going to do it? How was he going to prevent himself from getting even the least bit hard? He couldn’t! There was no way! It was impossible! But with the device that she had locked onto him, he was going to be forced to learn. Just thinking about his situation brought the pain back again, and again he had to forcefully calm himself. He was going to have to learn, and he was going to have to learn fast! The damn thing hurt!
“Come on, baby,” Mel said, wrapping her arm lovingly around his shoulders. “Let’s put you to bed. Tomorrow is another day.”
Yeah, Chad thought, tomorrow is another day. Every day since this bet had begun had been worse than the day before. He was afraid now to face tomorrow, especially not if it was anything remotely like the day he had just had.
Tomorrow was another day? He was still trying to comprehend the day he had just had. The word tomorrow suddenly felt like a nightmare. He had enough nightmares right now.

The Bet - Chapter 11 (Tuesday – week 2 Part 4)

The Bet
by Karen Singer

Chapter 11 (Tuesday – week 2 Part 4)

Chad walked into his apartment and gratefully threw his pink bag and his purse down onto the floor. He had already had more than enough of them for a lifetime. He carried his meal from the fast food drive-thru to his kitchen counter to open the bag. He found a note from Mel there. In very neat print, he read:

Sissy,
As soon as you get this, sit down on the floor and drink another baby bottle! When you’re done, apply full makeup – and make sure it’s better than you’ve ever done! After that, put pantyhose in the breasts of your girdle to pad them out. I’ve laid out the clothes I want you to wear tonight. Call me as soon as you’re completely ready.
Your Mistress

Chad stuffed a hamburger into his mouth while he read it through a second time. It sounded easy enough. He just wasn’t sure about drinking the baby bottle part since he had just bought himself another drink. But he realized he should have expected that. He took a quick sip from the coke he had just bought then dumped the rest of it down the sink since he really didn’t want to drink any more fluids than he really had to – and he had no doubt that Mel would be pouring them down his throat again all night.
He went into his bedroom to see what clothes she had laid out for him. He found his short black skirt, and a white blouse hanging from his closet doorknob. His new black pumps were laid out underneath them. “Excellent,” he thought. The clothes would be nothing but comfortable and fun for him to wear.
Knowing that Mel would check for sure, he went back into the kitchen and grabbed a baby bottle from his refrigerator to drink while he finished the rest of his hamburger. He didn’t sit down on the floor though. He drank it standing up at his counter. When it was finally done, he went into his bathroom to start on his makeup.
Mel hadn’t shown him a lot yet about makeup, but he thought for once that he did a pretty good job with the bits that she had shown him. The rest of it, he knew wasn’t the greatest job, but it was the best he could do.
He was just about to start getting dressed though, when the suppository that Cassie had inserted, or maybe it was the combination of all the suppositories that had been put into him that day, did their work. He squirmed as they suddenly exploded inside his girdle. All the makeup he had just put on his face suddenly made him feel hot and sweaty. The mess came slowly out of him because of the pressure of the girdle and it spread out around him feeling positively awful. This was something he would never get used to – ever! The diapers by themselves were bad enough when he messed them, but with the girdle on top, it was nothing less than an absolute horror.
When it was all finally done, he went out to his bedroom to get dressed. Moving a bit more gingerly because of the mess in his backside, he slipped the skirt on and zipped it up. It felt a bit looser at the waist today than he ever remembered it feeling before. His blouse came next. He buttoned it slowly and awkwardly because the buttons were all backwards from what he was used to. Finally he slipped on his new shoes. They felt tighter than he was used to, but because of their lower heel, they were really very comfortable. Pleased, he went back into the bathroom to get some idea of how he looked in the mirror there. He couldn’t see much, but he hoped that Mel would approve. Now if she would just change his diapers for him as soon as she got home he’d be a lot happier.
Before he left his bedroom, he picked up the clothes he had worn all day. The shirt he stuffed into the box that he was using as a clothes hamper, but he usually wore his pants two or three days in a row since they never got very dirty. He opened his closet to hang them up and stopped and stared. Every pair of his male pants were pressed together, wrapped tightly inside of layer after layer of cling wrap. The only exposed place she had left was the hook of the hangers themselves. He couldn’t even touch his pants, only the outside of the thick package she had created out of them.
With a whimper, he reached for another hanger, and never once taking his eyes off of the package of his male pants, he hung up the female slacks that he had worn all day. Mel’s message was loud and clear. No more male pants. He felt very much like crying. With every passing day she seemed to find new heights to make his life more miserable. And curiously enough, through all his shock over what Mel had done now, he found that it too was stimulating his need. Damn the woman! She could be such a pain, while at the same time, she was so darn good! He finally closed his closet door so he wouldn’t have to think about that problem anymore.
Knowing that he was as ready as he was going to get, he pulled his cell phone out of his purse. Just doing that simple act seemed so odd to him. It was his purse. Not some woman’s. His! And his sexual excitement over it grew another notch.
He dialed Mel’s number. “Hi Mel, it’s me.”
“Who?”
“Me!”
“Who’s me?”
Chad sighed. “Hello Mistress. This is Sissy.”
“That’s better. Remind me to punish you later for calling me Mel again.”
Chad said nothing. He knew he probably deserved it this time.
“Ok, Sissy. Are you dressed like I wanted?”
“Yes Mistress.”
“Good. How is your makeup?”
“Not great, but better than usual.”
“At least you’re being honest about it. Did you drink the bottle?”
“Of course.”
“Good. So you’re all ready now?”
With more than a bit of trepidation, he answered, “Yes.”
“Good. Now listen carefully. Open the middle drawer of your kitchen counter. You will find a key in it. That’s the key to my apartment. Put all your makeup in your purse. Bring your empty baby bottle and make sure you bring your diaper bag too. There will be more instructions in my kitchen. I’ll see you in just a little while. And Sissy, I expect everything I tell you to do to be obeyed!”
Chad was a bit surprised at what she had just said. “Of course, Mistress,” he answered. And before he could say another word, he heard the line go dead. He realized that he was just very glad that he was only going next door to her apartment. It could have been much worse… it still could be much worse he realized.
He easily found the key she had left him. He was very surprised that she had left it. Was she starting to trust him? Having at least some idea of what was expected of him next, he gathered up everything he needed. His purse felt a lot heavier now with all the makeup in it. Knowing that he was as ready as he was ever going to get, he went out his door and over to her apartment.

Robin was driving back from the store when she passed the apartment project where Chad lived. He had been on her mind the entire time she was shopping. Just wanting to see where he lived again, she quickly turned into the driveway and drove toward his apartment. She stopped to look at it. It looked like a very nice place.
As she sat there for a moment, she suddenly saw his door open. She was more surprised to see him coming out of his apartment wearing a skirt and a white blouse. He again had his pink bag and was carrying his purse. She was even more surprised to see him go to the apartment right next door and unlock it to let himself in. “Now what was that all about?” she wondered aloud. Still unable to take her mind off of Chad’s strange behavior, she drove home.


Inside Mel’s apartment, Chad found another note left for him on her kitchen counter.

Sissy,
Time for another bottle. Get drinking – now! Before you read any more!

Ok, you had better be drinking! If I come in and find you reading this without a bottle in your hands you’re going to be very sorry!

Next. Make me dinner. What you prepare is completely up to you, but it had better be good. Make enough for both of us but don’t you dare set a place at the table for yourself. I should be home well before dinner is ready, but if I’m not, put your portion on a plate and stick it all into the refrigerator. Make sure you keep mine nice and warm!

When you finish the bottle you should be drinking during this, stick your pacifier in your mouth!

Remember, I’ll be checking on everything as soon as I get there!

So get busy!

This time the note wasn’t signed the way the last one was. He almost laughed over the tone of it, especially the part about getting a bottle to drink before he read the rest of the note. Still chuckling a little over it, he pulled a baby bottle out of the refrigerator and started drinking from it while he looked through all the food she had so he could figure out what he wanted to cook.


Mel took her time coming home from work, mostly to give Chad a chance to get further along preparing her dinner. When she walked through her door, she was pleasantly greeted by the delicious aroma of the meal he was making. Yeah, the guy could cook. That was a major bonus as far as she was concerned. The only problem with it as far as she could see was maintaining her weight. She wondered how he was at diet dishes.
As soon as she closed her door behind her, Chad came out of the kitchen to see if it was her. She stood there only a moment before he seemed to collect himself and say, “Hello, Mistress.” The phrase came out very garbled because of the pacifier in his mouth.
“You’re learning,” she said as she headed toward her kitchen. “Slowly, but you’re learning.”
Chad went back to preparing dinner while he watched her poking around at everything. She inspected his two empty baby bottles carefully. Then she went through and looked into each pot on the stove. He also noticed that she had looked him over carefully. She didn’t say anything so he was hoping that he had passed her inspection.
Mel went back into her living room to relax for a few minutes while Chad finished working. This was the life! And to make it better, she didn’t even have to worry about cleaning up later. That was his job. It had been a long day for her filled with frustrations, and successes. She leaned her head against the back of the chair and dreamed of having her personal servant forever. Soon. Very soon.
“Excuse me Mistress,” Chad’s voice broke her relaxed state. At least she was fairly sure that’s what he was trying to say through his pacifier. She opened her eyes and looked up. “Dinner is ready.” He told her.
She got up and went into the kitchen. The table was again set beautifully, but this time only for one. He had even lit the candle in the middle again. She was about to tell him how nice it all looked but she stopped herself. “And where’s your dinner?” she asked instead.
“I left it over here on the counter,” he replied through the pacifier.
Mel saw his plate on the far end of the counter. “Put it in the refrigerator till I tell you you can eat.” She told him. Chad seemed to sigh just a bit but he did as he was told. Mel sat down. The food looked and smelled good. She tasted some of it. Just as good as it smelled. Chad was standing in the kitchen watching her. He was being very good about it, but it bothered her a bit. A tiny fragment of the many things she had read about domination recently came to her mind. “Go stand in the corner till I need you,” she told him.
Chad’s eyes went wide. “In the corner?” Oh God! He looked around the room for a decent place.
“That corner,” Mel said, pointing to one at the far end of the living room. Not anywhere near her. “And face it!”
Chad dutifully did as he was told. But Mel wasn’t quite satisfied. “Further into it!” she commanded. I want your nose and shoulders touching it. Put your feet together! Put your hands down by your side and keep them there.” She waited till she was finally satisfied with his position. “Now don’t move!”
Feeling wonderful from the power of what she had just done, she went back to enjoying her dinner. And she did really enjoy it. She watched Chad while she was eating. Mostly he was obeying her very well. But the longer he stood there, the more she saw him fidgeting. She knew he was probably getting bored and tired from standing there. Well, he had to learn. She saw him move again, just shifting his weight really. “Stand still!” she ordered. “You move around too much!”
Chad wasn’t exactly enjoying himself. Yes, it had been a bit exciting at first, but the longer he stood in the corner the more tiring it got. He couldn’t really see anything either except the two blank walls that were making him cross-eyed. He had closed his eyes long ago because it was easier. And having to shove his whole body into the corner like this was certainly difficult to maintain. His legs were getting tired too.
He heard her finally getting up from the table. He hoped she enjoyed the meal he had made. He had actually enjoyed making it. He would have enjoyed it far more if he had been allowed to sit down and eat it with her. Now his food was getting cold in the refrigerator.
Mel walked up behind him. She stopped there and watched him for a few minutes. She knew that he was very much aware that she was there. She was just enjoying the power trip again. Finally she decided to release him. “Ok, Sissy. You can get your dinner now.”
Chad felt nothing but relief as he pulled himself out of the corner. His muscles and joints were beginning to go stiff. He went into the kitchen and pulled his plate out of the refrigerator. “On the floor again,” she told him. He sat down with his plate. He didn’t even ask about a fork, he knew he’d have to use his fingers. Mel reached down and pulled his pacifier out of his mouth before he could. He was actually grateful. Unfortunately, she immediately reached into the refrigerator and pulled out another baby bottle that she handed him. He was really getting tired of those things.
His meal was cold, but still very good. Despite eating on the floor with his hands, he actually enjoyed it. When he was done, Mel shoved the pacifier back into his mouth again and he began cleaning up the kitchen. He heard her turn the TV on out in the living room.
When he was done in the kitchen, she set him working on her laundry, then she sent him back to his house to get whatever clothes he needed cleaned too. He was actually very glad about that since he didn’t have a washer or dryer… yet. That was something else she was going to be buying him when this was all over.
Unfortunately, while the washer was running, Mel remembered that he still had one dirty diaper in the diaper bag in the bathroom. Once again, Chad had to scrub it by hand just the way he had done the others last weekend. But at least it was only one diaper this time.
All the while that he was cleaning, Mel mostly ignored him and watched television. “Just like her maid,” he thought. And he remembered that that was the very thing that she really wanted out of this bet. But she had better enjoy it now, because he knew that in the end, there was no way he could lose.

The Bet - Chapter 11 (Tuesday – week 2 Part 3)

The Bet
by Karen Singer

Chapter 11 (Tuesday – week 2 Part 3)

Lunchtime came all too soon for Chad, mostly because he knew he’d have to get up from the safety of his chair and parade himself out through all those people again. And this time there would be far more people around. He delayed a few moments, hoping the main rush would at least be over with before he left. He grabbed his cell phone and his keys and glanced up and down the hall. There were still people wandering in both directions, but there wasn’t much he could do about it. He hurried out towards his car. Fortunately, most of the people were heading in the same direction that he was so they wouldn’t notice his pants. At least the people in front of him. He didn’t want to think about anybody who might be behind him.
He realized that one good thing about having to carry his keys in his hand was that they were already out and ready for him to get quickly into his car. As soon as he closed the car door behind him, he breathed a sigh of relief. Why couldn’t he just die now? It would certainly be easier. He started his car and headed towards the gym to meet Cassie.

Robin closed her cell phone and was about to start her car to get some lunch when she saw Chad hurrying to his car. She saw him back out of his parking space and leave. On a whim, she followed him, she had to go somewhere for lunch anyway. A few blocks later, she saw him turn into the parking lot for a women’s gym that she had considered joining a while back, but never did. She drove past it and pulled into the driveway of the next building down. She didn’t really park, she just sat there and waited, watching Chad’s car.
She saw him get out and glance around quickly, then he reached into his car and pulled out a large pink bag that he slung over his shoulder. He appeared to pick something else up too before he closed his car door and headed towards the gym. She was shocked to realize that the other thing that he had picked up was a purse. What was in the big pink bag, gym clothes? And this was a ladies gym! Was he going in there to exercise?
More puzzled than ever, she drove off in search of something to eat. But the only thought on her mind was Chad.

Chad hurried into the gym. The receptionist recognized him immediately, which he wasn’t all that happy about. He saw her eyes immediately lock onto the purse he was carrying and he wasn’t happy about that either, just like he wasn’t happy about her looking straight at the women’s pants he was wearing. He suddenly realized that she was trying very hard to keep a straight face and was only barely succeeding. “Are you here to see Cassie again?” she asked, trying to stifle her chuckles.
“Yes please,” he replied, wondering how on earth he could ever hide the fact that he was carrying a purse from the rest of the room. He had only brought it in because he was very much afraid that Mel would ask Cassie if he had it. Yesterday’s questions had been all too uncomfortable.
“Can I ask your name please?” the receptionist asked.
Yeah, she was definitely trying hard to keep a straight face and was quickly losing the battle. “Why?” he asked. He didn’t really want to give her his new name.
“So I can tell her who’s here to see her. She’s pretty busy you know.”
“Can’t you please just tell her that I’m the same guy who was here yesterday.”
She shook her head. “No, I need to know who you are.”
She wasn’t backing down. Chad had no doubt at all that she was playing with him. She had heard Cassie call him Sissy yesterday and was probably wanting to know more. A bit red faced, he said quietly, “Please tell Cassie that Sissy is here to see her.”
The girl looked at him like she hadn’t been able to hear him well enough. “Who?”
“Sissy!” he said louder and with more than a bit of frustration.
The receptionist lost all control on her laughter and she practically sprayed Chad as it burst forth. “I’ll get her,” she replied as she left – in stitches. Chad looked very, very hard for a hole in the floor that he could crawl into.
His wait for the receptionist and Cassie was a bit longer than yesterday though and things got a bit more uncomfortable when two other women came in together to exercise. Since the receptionist wasn’t at her desk, they both stood there waiting – and looking all too closely at Chad – up and down. They didn’t laugh at him, but one of them had a distinct scowl on her face. “She’ll be right back,” Chad said, trying to sound calm. One of them just nodded, the other one seemed to scowl a bit harder at him. Neither of them took their eyes off of him.
The receptionist finally came back with Cassie right behind her. The two women went to the desk and signed in then left. Cassie just stood back, staring at Chad till they left. Finally, she shook her head and turned away. “Come on, Sissy. Let’s get you changed.”
Chad followed after her, staring mostly at the floor because he didn’t want to even look at anyone else in the room as he walked through. He was too ashamed.
Cassie again brought him back to the same office then closed the blinds. She turned around and let out a huge laugh. “Mel told me you’d be carrying a purse today, but I just had to see it to believe it! Oh, by the way, love your pants too.”
Chad was suddenly very glad that he decided to bring the purse in with him. He had no doubt now that Mel was checking up on him every step of the way.
Cassie was still laughing a bit when she took his diaper bag from him. “You can put your purse on the chair over there,” she said, then started to laugh all over again at him. Chad felt even more embarrassed. “Ok,” she finally said when she had gotten control of herself again. “Get undressed while I find your bottle for you.”
Chad would have much preferred that she undress him again like she did yesterday, but that didn’t seem to be the case today. As he was struggling to get his girdle over his soaked diapers, she said, “Don’t you get tired of wearing that thing?”
“More than you’ll ever know!” he answered as he finally got it down and pulled it off of his legs. She just nodded and pointed to the floor for him to lay down. She handed him one of the baby bottles and he automatically put it to his lips and began drinking.
“Just like a baby,” she commented. Then she pulled down his plastic panties. “You’re not messy again,” she said a few minutes later as she pulled open his diapers.
Chad really had no explanation this time. “What can I say,” he finally said. “I don’t have much control over what those suppositories do to me.”
“You are very wet,” she commented.
“Yeah, too wet.”
“Well, that’s what I’m here for,” she said, “so you can have nice fresh diapers for the afternoon.”
Chad felt her pull his diapers wide open, exposing him completely. She left him that way while she got his new diapers ready. Chad had visions of somebody coming in suddenly and seeing him, but fortunately it didn’t happen. She pulled the old diapers out from under him and slid the new ones in place. Then she grabbed more of the baby lotion from his diaper bag. That was the part Chad was really looking forward to. Once again she spread it over him, massaging him in ways that nobody had ever done. He soon closed his eyes as he sucked on his bottle. The feeling was that good. He was quickly growing hard. He could feel her skilled fingers doing things to him that he had never imagined before, he sucked harder and harder on his bottle the more excited he got. And then, suddenly, her hand was gone and he felt her shoving a suppository up inside of him again. The sensation was absolutely shocking after her previous work. Then, all too soon, she was pulling his diapers firmly into place – too firmly. He wanted to scream. One thing was for sure, when he was done here he was going to skip lunch and head straight back to the men’s room at work for some relief!
All too soon, Cassie had finished diapering him and had pulled his plastic panties back up. “Oh look,” she said as if she were talking to a baby, you’ve almost finished your bottle today.
Chad held his bottle up to look at it. It was almost gone. He had sucked on it that hard while she was working on him. It only took a few moments longer till he had finished it. “Good baby,” she said as she took it from him. Chad felt the mixed embarrassment and sexual thrill of her words – deeply. “Ok, get dressed,” she told him as she began packing his diaper bag back up again.
Chad dressed as quickly as he could. Not just to spare himself more embarrassment, but because his mind was firmly on getting into the men’s room again to get some relief. He fumbled with the backwards zipper a lot less this time. “Those slacks fit you very nicely,” Cassie commented as he finished fastening them.
“They should,” he replied. “I lost count of how many they made me try on last night.”
Cassie laughed just a bit. “I wish I was there!” Chad was just very glad that she hadn’t been.
When he was finally ready, Cassie again led him back through the room of exercising women. He looked around at only a few of them this time. Yeah, they were watching him for sure.
As soon as he could, he got back into his car and headed back to work. There was no way he could eat lunch just then, he had other parts of his body that needed the attention a whole lot more!

“Hi Mel. It’s Cassie.”
“Oh hi Cassie. How did it go today?”
“Great, just great. You warned me about him carrying a purse today and about the slacks, but I couldn’t believe it. Well, now I’m a believer!”
“Oh good! So he did carry the purse in with him?”
“Oh yeah! He sure did! And let me tell you, it was a real hoot to see. Oh, and the slacks were really nice too.”

“Great, I’m glad you liked them. He’ll be wearing them from now on. Of course he doesn’t realize that yet.”
Cassie laughed. “I can hardly wait.”
“Hey Cassie, did you happen to notice if he was wearing any mascara today?”
“Not that I noticed. Was he supposed to?”
“Yeah, I sent him out of the house wearing it. But I figured he’d probably wash it all off when he got to work. Looks like I was right.”
“Is there anything you want me to do about it?”
“No, that’s fine. I’ll check with you tomorrow about it, ok?”
“No problem. Hey Mel, I’ve got to tell you, I’m really enjoying this.”
“Good, I’m glad. So am I.”
“Well, I kinda figured that!”

Late in the day, Chad’s stomach began growling. He hadn’t had anything to eat since the breakfast he had bought that morning. And the last thing he had drank was the baby bottle when Cassie had changed him. He was hungry enough that he was seriously thinking about stopping to get something light before he went to Mel’s office. Just before quitting time, his cell phone beeped signaling a text message had come in. He opened the phone and read the message. It was from Mel, telling him to go straight home. He would find further instructions in his apartment. That was different, he thought. He had to wonder seriously what she had up her sleeve now.
When quitting time finally came a few minutes later, Chad stayed where he was for about five extra minutes to allow more workers to leave before he tried to walk out. Then, cautiously, he hurried through the hallways and out to his car. There were still some people around, but not as many as there would have been. He did see more than he was happy about that all seemed to be looking at him. But there was nothing he could do about it.
He felt very relieved when he finally got into his car and closed the door. It had been a long and horrifying day. And he was glad it was finally over. Now he just had to face whatever Mel had planned for him for the evening. But first, he really needed a snack!

Robin sat in her car talking with her husband on the phone before she drove out of the parking lot. She knew she had to stop at the store on the way home to get something for dinner and wanted to make sure that her husband was going to pick up their son from daycare. As she figured, he was happy to do it. He was a good father. As she was talking to him, she saw Chad come quickly out of the building and get into his car. He seemed to drive off just as fast.
Finally satisfied that her husband would take care of their son, and after getting a long list of things her husband wanted her to buy while she was at it, she left for the store. One of the many stop lights turned to red just before she reached it and she pulled to a stop to wait. Just before the light turned green, she saw Chad’s car pulling quickly out of the parking lot of the fast food place just ahead of her and head up the road. The light changed and she drove ahead, following him. She saw him finally turn into the parking lot of one of the nicer apartment projects along the way. Not knowing why she did it, she followed him.
The project was a maze of winding streets and buildings, but she didn’t have to go very far before she saw him pull into one of the parking spaces. She pulled into another one, way back from where he had parked. She saw him get out of his car and grab his pink bag again along with the purse she had seen him carrying earlier. He also appeared to have a bag from the fast food place in his hands. She saw him walk up the stairs and finally go into one of the apartments. “At least I know where he lives now,” she thought as she drove off to the store.

The Bet - Chapter 11 (Tuesday – week 2 Part 2)

The Bet
by Karen Singer

Chapter 11 (Tuesday – week 2 Part 2)

Chad drove into the drive-thru of his favorite fast food restaurant, not because Mel had told him to, not because he was hungry, but because he still hadn’t figured out how he was going to be able to go to work dressed the way he was. Stopping to get something to eat was more of a delaying tactic. Normally, he would have gone inside, but certainly not today. The drive-thru was busy, as it usually was and he found himself waiting in a long line of cars. That was just fine with him. When it was his turn, he ordered his usual meal. Then he inched his car forward waiting his turn at the pickup window. Fortunately, he remembered just before he got there that he couldn’t reach into his wallet and pull out a couple of bills like he usually did. His wallet was in his purse now. While the cars were all stopped, he quickly grabbed his purse and opened it. He easily found his wallet inside, but he had to shake a few coins off of it before he could pull it out. He pulled out enough money for his breakfast then put his wallet back in again and closed the purse. It was his turn at the window. He drove up to it praying that whoever was there wouldn’t notice his pants or his purse… or his diaper bag for that matter. But the girl there just handed him his coffee and took his money. She quickly made change and handed him that along with a bag containing the rest of his breakfast. And that was it. He drove off quickly and found a parking place to eat. The money the girl at the window had handed him he just dumped loosely into his purse. He figured he could put the bills into his wallet later.
As he sat and ate, he began to dread more than ever going into work. How could he ever explain wearing girl’s pants? The purse he figured he could leave in the car. That would be no problem. It was his pants he was worried about. That reminded him about his socks. As soon as he finished eating, he dug them out of the console and put them on. Just that simple act made him feel a little more confident, but only a very little. It was starting to get late. If he waited much longer he’d run into too many people on the way in. He drove to work.
Once his car was parked where he usually parked it, he grabbed his cell phone and his keys from his purse. He figured they would be the only things he would need. Then, holding his breath for courage, he opened his car door and walked much faster than normal into the building. He was not happy to see more people around than he usually saw. Not a lot, but to him it definitely seemed like more. Just inside the door, he passed two women walking the other way. One of them looked at him oddly and stopped, cocking her head. The other one stopped too. Chad hurried past them, not wanting to say anything at all. Why did his cubicle have to be so far from the door?
He continued hurrying through the hallways, making turn after turn. It seemed like more and more people were looking at him. Was he attracting too much attention because he was hurrying so fast? He realized he probably was, but there was no way he could slow down. Finally he reached his own cubicle and he quickly went in and sat in his chair. Why couldn’t he have an office with a door that he could close? But at least his cubicle was somewhat isolated. There weren’t many people around him. One of the cubicles next to him was even empty.
He had made it. He was at work, at his desk. And he was wearing women’s pants. He had no doubts at all that some people noticed it as he came in. He’d probably be the talk of the company before long. And then he remembered his mascara. He still needed to get to the men’s room to wash it all off. Another long walk. But that was going to have to wait. He didn’t have the courage yet to run into anyone else. Besides, if he waited a bit longer, most people would be hard at work and the men’s room would more likely be empty. He had major plans for another relief session and that would be easier on him too if he could be alone.
He realized he needed to pee again. Damn! He shouldn’t have drank the coffee with his breakfast. Not yet ready to make the walk to the men’s room he allowed himself to pee into his diapers again. That part at least had gotten a lot easier since this all started. It was almost second nature to him now.

Not giving it another thought, he got to work - work that was all too disturbed by the fact that he was wearing women’s pants and mascara – openly in front of everyone else. The more he thought about that, the more his sexual need raged inside of him. He began counting the minutes till he dared make the trip to get some relief.

Andrea looked up surprised as Mel came back into the office. “You’re back early,” she said. “What happened?”
“The judge postponed the Baxter case again till tomorrow.”
“Again?”
“Yeah. I figured he probably would. The other side is really only doing what I would have done. They know I’m going to win and they’re trying to delay it.”
Andrea nodded. It was really routine stuff. “There was a package in the mail for you today. I put it on your desk. I noticed it was marked for fast delivery.”
Mel beamed. “Good!” and hurried off toward her office.
“Something special?” Andrea called behind her. But the only answer she got was Mel turning around and flashing her an interesting, if not wicked, smile.
Mel found the package on the middle of her desk. She checked the labels. Yes, it was exactly what she hoped it would be. She had some extra time in her schedule now. She opened the package and dumped the contents out on her desk. A couple of small packages fell out. Most of them looked like plastic. One contained a package of tiny locks. She left the locks alone and opened one of the other packages. The biggest one.
Just looking at the object that she now held in her hands sent shivers down her spine. But she wasn’t sure if they were shivers of pleasure, anticipation, or of horror. Part of it was phallus shaped, sort of. The rest of it was obviously the Chinese puzzle that would attach it to Chad’s cock. She had watched a video on the internet about how to put it all together and she tried it now, fumbling more than a few times till she finally figured it out. There were so many pieces, all of which was made more complicated because there were various sizes of some of the pieces so that the right fit could be achieved. She practiced a few more times till she was sure she could do it with no trouble.
Then she opened one of the other small packages that had been included and dumped the contents out in front of her. Several very cruel looking pieces were on her desk. She picked one up and examined it. It was basically a half circle of fairly sharp teeth. She touched one. It was sharp enough, but really not all that bad. But she had no doubt that those teeth could really hurt a certain particular part of Chad.
She was a bit startled by someone knocking on her door. Andrea opened it and poked her head in. “The court clerk just called. Your next case has been postponed till next week.”
Mel rolled her eyes. “What is this, a conspiracy?” She sighed. “It looks like it’s going to be just one of those days.” She knew that things often went like this. In her business, you never knew.
She noticed Andrea looking curiously at the things on her desk. “Is there anyone in the office?” Mel asked, referring to possible customers.
Andrea shook her head. “Not today. You’re supposed to be at court all day, remember?”
Mel nodded, “Yeah, it just looks like none of it’s going to happen. Come on in then. I can see you’re dying to see this.”
Mel showed Andrea the device and how it worked. More than once, she saw Andrea blush. But there was no doubt that she was also terribly interested. As Mel showed her the part that looked pretty much like a cock, she said, “This is a new model. It’s made a lot shorter than most of the other ones. I picked it specially so he’d have less room to get hard in.”
“I thought it looked awfully short,” Andrea replied. “And what are those little things?” she finally asked, pointing at the small disks with teeth.
“Those are called Points of Intrigue. There actually designed to make sure that he can’t pull out of it, but they can have another affect too. I read where just the teeth alone hurt so much that the wearer learns a lot faster to not get a hard-on. The different sizes give me the choice of how cruel I want to be with it. But as long as he stays nice and soft, they shouldn’t hurt him at all. Unless he tries to remove this thing that is.”
Andrea didn’t know whether to laugh or feel sorry for Chad. “The poor guy,” she finally said. “But he did ask for it by making the bet with you, didn’t he?”
“You’ve got that right. And you know how I hate to lose!”
Andrea could only agree.
“That reminds me,” Mel said as she reached for her phone. She punched in the number and waited. “Hi Cassie,” it’s Mel. How are you?”
“Oh, I’m fine. I’m just about to start a class so I can’t talk right now.”
“That’s ok. Listen, when Sissy comes in today, do me a favor. Just make sure he’s carrying his purse. Ok?”
“A purse!”
“Yeah, from now on I want him carrying one.”
“Oh God! I can’t wait! Ok I got it. I got to go. Talk to you later.”
Mel hung up her phone. Andrea burst out laughing. “Oh Mel, this is getting better and better.”
With delight in her eyes, Mel said, “There’s more too.” She then filled Andrea in on all the things that happened last night and this morning. Andrea was in stitches.

Chad glanced at his watch. It was time. A minute past in fact. Did he dare do it? Did he dare leave the safety of his cubicle and go all the way down the hall to the men’s room? His need raged inside of him. He had to go.
Plucking up the courage, he got up from his seat and glanced down the hall. The coast was relatively clear. Taking that first step was difficult, but he did it. He walked quickly, but not too quickly, towards the men’s room at the end of the hall. One of his friends came out of his own cubicle with his hands full of papers. He barely glanced at Chad and just said hi to him. Relieved, Chad continued forward. He finally reached the bathroom door. Nobody else had seen him. He opened it and went inside.
He was relieved. It was empty, just liked he hoped it would be. He went straight to one of the stalls and was soon pulling his clothes off as fast as he could. Once again he masturbated over the images of what she had done to him, only today they seemed all that much more powerful. His orgasm was incredible. It had been a very long time since he had experienced one that strong.
He sat down on the toilet to wait and recover. When his breathing was back to normal again, he started to get up, but he suddenly heard someone else coming into the room. He sat back down again and decided to stay right where he was. His penis had finally grown soft again. He suddenly felt the need to pee. He peed sitting down. He heard whoever it was with him washing his hands, then leaving. He stood back up and got fully dressed again, fumbling awkwardly with the zipper on his slacks because it was backwards and he had to pull it with his other hand.
He left the stall and quickly washed his hands. Then he glanced quickly at the mirror. His mascara! He had forgotten all about it. He washed his face too. But it was taking too much time to get all the mascara off. Before he could finish, somebody else came into the men’s room too. Chad finished what he was doing as quickly as he could and hurried past the guy who was still standing in front of one of the urinals. Had he seen Chad’s all too feminine slacks? He doubted that the guy had noticed or he figured he would have said something. Feeling much more confident, he hurried back toward his cubicle.
But he didn’t make it. Robin, the woman who worked in the cubicle next to his, came out and headed straight towards him. She smiled when she saw him, then Chad saw her smile turn to puzzlement. He wanted to walk past her and not say anything. But she stopped dead in her tracks and was watching him approach.
“Chad?” she said as he got close enough to him. “Are they women’s pants you’re wearing?”
Chad slowed his walk and stopped. He was busted. He felt his face blushing and knew that she had noticed that too. There was no way out of it. “Yeah,” he finally said sheepishly.
“Why?” the she asked.
Chad just shook his head. “I…” but he didn’t have a good answer he could tell her. Instead he quickly left her and walked back to his cubicle. Someone knew. Someone knew for sure. What was he going to do?
He tried to work, but he couldn’t really concentrate. It was impossible, what was he going to do?
“Chad?”
He turned in horror to see Robin at the entrance to his cubicle. He felt himself blushing again. “Hi Robin,” he said sheepishly.
They just stared at each other for a moment. Chad wished desperately that she would just go away.
“Can I see them?” she finally asked.
That was not what he really wanted her to say.
“Please?” she asked, even though she noticed the almost pleading look in his eyes that said he didn’t want to.
Chad didn’t say anything, but slowly he stood up and moved his chair aside. Robin came all the way in. “I like them?” she finally said. “Turn around.” He did so. He realized he was suddenly getting ordered around by way too many women lately. “They certainly fit you very nice. I never noticed before how full your backside is. And you’ve lost some weight.”
Chad blushed deeper. There was no way he was ever going to tell her about the diapers too.
She was looking him in the eyes now, and was about to say something, when he saw the expression on her face suddenly change. “Wait a minute,” she said quickly. Then she hurried away, only to return a moment later with a tissue in her hand. Chad backed away as she started to bring the tissue up towards his face. “Hold still,” she said. “You’ve got mascara still smudged on one of your eyes.”
Chad wanted to groan and scream both, but instead he instinctively reached for his eyes. “Wait,” she said, “I’ll get it for you. You can’t see it by yourself.” Chad’s humiliation reached a whole new level as he felt her rubbing over and over again at the skin under his left eye. “There. That’s better now. If you’re going to wash it off, you’d better be more careful.”
“Thanks,” Chad replied sheepishly.
“So how come?” she asked again.
He opened his mouth to try to say something, but there were no words. He couldn’t tell her about any of it. “I don’t want to talk about it,” he finally said and then rudely pulled his chair back into place and sat down again, turning his back to her. He heard her sigh behind him and start to leave. He turned around again quickly. “Robin.” She turned back to him. “I’m sorry. Ok?” She just seemed to shrug her shoulders a bit and started to leave again. “Robin,” he added, “I seriously doubt this will be the last time.”
Her eyes went wide. “Why? What’s going on, Chad?”
But he just shook his head and turned away from her again. Busted!
Robin went back to her desk feeling more than a bit annoyed. He had actually been a bit rude to her. He had never been that way before. But then she had never seen him wearing women’s pants before either… and obviously he had been wearing makeup not too long ago too.
As she sat back down in her chair she couldn’t help but think about him. She had known him now for what, about six or seven years? And now suddenly this? She knew he was in the process of getting a divorce. But what did that have to do with this? More puzzled than ever and still feeling put out by the way he had acted, she tried to get back to work. But her thoughts kept returning to Chad. She thought he was at least somewhat of a friend.

The Bet - Chapter 11 (Tuesday – week 2 Part 1)

The Bet
by Karen Singer

Chapter 11 (Tuesday – week 2 Part 1)

Chad’s pink clock radio startled him awake again. He felt awful, mostly really tired. Reluctantly he got up and turned the loud music off and went back to sit on his blow-up mattress. What a night! The damn woman had made him drink so many baby bottles of her lousy tea that he had been peeing all night again. Only this time it seemed worse. He had been trying to hold back more and more all day yesterday to make sure he kept full control of himself, but halfway through the night it just got too difficult and he allowed himself to wet more freely so he wouldn’t have to wake up completely each time. It was the only way he could get any sleep.
Thinking about all the baby bottles she had made him drink, reminded him of her orders for him this morning. He stood up and waddled into the kitchen. His diapers were so thick it felt like he had a basketball strapped between his legs. The only good thing was that despite the two suppositories she had shoved up him again last night, he hadn’t messed himself at all – yet. In fact, despite the heavy meal he had eaten last night, he still felt no need. Thankfully! He grabbed a baby bottle at random from his refrigerator and carried it back to his mattress where he laid down and put it to his lips – the prune juice again – ugh!
When he finally finished his bottle he waddled back out to his kitchen again and put it with all the other empty bottles on his kitchen counter – a total now of five since she had left him last night. Way too many. He’d probably be peeing all day. A major nuisance. He made his way wide-leggedly into his bathroom where he brushed his teeth and shaved his face with his pink razor. He really missed using regular shaving cream. The soap and moisturizer she had him using just weren’t the same. Halfway through shaving, the suppositories decided to wake up too. And it was completely sudden. Chad had very little warning at all. Halfway through one scrape of his face, he realized it was about to happen, and then just as suddenly, he was filling his overly wet diapers helplessly – and a lot! Everything came out in one total rush. Fortunately, it was over with quickly. But like everything else, there was nothing he could do about it, so he went back to shaving his face.
When he was done, he went back to his mattress where he laid down dejectedly and closed his eyes again,

Mel’s alarm clock jolted her awake. She felt lousy. Between all the aches and discomforts from her period and staying up way too late, she could have really used a few more hours of sleep. Or a few more days of sleep would be even better. She made her way to her coffee pot where she put an extra scoop of coffee in it to help wake her up. She had no doubt she’d need it today.
She had stayed up way too late last night on the internet researching sissies and dominants. She even poured through websites about bondage. And all of it was stimulating her interest in ways she never imagined it would. She was quickly finding it all addictive. That was what had really kept her up all night. But today was back to reality – sort of. She had to go to work again, but there was also the matter of Chad – her fantasy. Today she was going to saddle Chad with some new things, none of which he was going to like – especially later. It was going to be an important day for him, and for her. Realizing all this woke her up a lot more. She nearly jumped into her shower.

Chad never heard his apartment door open, he had fallen sound asleep again. Mel walked in and saw all the empty bottles on his counter. She counted them, five… perfect. She walked into his bedroom and saw him sleeping. His legs were spread wide apart. She could tell even through his onesie how thick they were. She wondered briefly if they were at all uncomfortable that way… not that it really mattered to her. She very faintly smelled the results of the suppositories she had put in him last night and smiled. Another requirement accomplished. She walked over to his bed and looked straight down at him. Obviously he had already shaved… good. She kicked his blow-up mattress. “Wake up, Sissy.”
Chad jolted awake. He hadn’t meant to fall asleep, but it had just happened. She was standing over him, looking down at him, just waiting. “Good morning, Mistress,” he said from his back.
She smiled at him. “Good morning.” Then she walked away and headed towards his bathroom.
Chad got to his feet and tried to shake a few more cobwebs from his brain as he followed after her. She was holding out the key to his onesie. He turned around and let her unlock it, then he felt her pulling down the zipper in the back for him. “Finish getting cleaned up,” she told him.
Chad pulled the onesie off then struggled to pull his plastic panties off of his diapers. Yeah, his diapers were definitely much fuller today than they had ever been before. Very carefully he pulled the diapers off of him so as to make sure that none of his mess wound up on the floor. Then he quickly got into the shower where he peed almost as soon as the warm water hit him.
While he was drying himself off, Mel came back into his bathroom and began laying out his diapers. She again coated him front and back liberally with baby lotion, again spending more time than ever caressing his private parts in front. Chad loved it. He wanted it to never end. The slippery lotion, the soft motions of her hand… But suddenly her hand was gone again. He sighed dejectedly as he felt her pushing up his morning suppository. From ecstasy to horror. Such was his life. He couldn’t wait again till he could get to work where he could relieve himself.
Two diapers, plastic panties, an all-in-one girdle, and pantyhose. He was well used to the routine now. It was all beginning to feel completely normal. He also wasn’t the least bit surprised when she told him to do his makeup again. “A little bit better,” she told him when he had finished, “but only a very little bit. Wash it off and do your mascara again.”
He had really expected her to have him redo all the makeup over and over again, but she hadn’t. He had no doubts that she expected him to wear the mascara to work again too. Why? She had to know that he was only going to wash it off as soon as he could. But he dutifully applied just a very light coat of the mascara. “That much at least is starting to look a little better,” she declared. Chad really wondered why he felt so thrilled over such a tiny compliment.
“Wait here,” Mel told him as she walked out of his bathroom. She came back a minute later and handed him one of his shirts. “Wear this one today. I like it.” Chad certainly had no problem with that. He began putting it on. Mel left again while he was buttoning up the front. She was back a minute later with a pair of black pants for him. She handed them to him and Chad instantly realized that they were the new women’s slacks he had bought the night before.
“I can’t wear these!” he protested in sudden panic.
“Of course you can,” she replied. “That’s what you got them for, isn’t it? You told me yesterday you wanted some pants to wear to work that were a bit longer and wouldn’t show your ankles so much, and now you have them. I think they’re perfect for you.
“But they’re women’s pants!” he said.
“And you’re a sissy. So what’s the problem?”
“I can’t!”
Mel smiled wickedly at him. “Yes you can! And furthermore… you will!”
“But…”
“No buts!”
Chad was completely aghast. He couldn’t! But he had to! He stood staring at her for several moments and she just stared straight back at him with that evil grin on her face. Damn the woman. She couldn’t do this to him… could she? Reluctantly he pulled the women’s slacks up his legs and fastened them. They felt totally different than his men’s pants. The material was thinner, softer, the cut of them looked way too feminine. The only sign of any pockets were merely two fake pockets in the front with a bit of ribbing on top that weren’t even deep enough to get the full length of his fingers into. The zipper fastened backwards and there were no belt loops at all. He looked down at his feet. He could just barely see his red toenails in front, but the pants were long enough to just touch the floor in the back. Yeah, they were longer and wouldn’t expose his ankles too much… probably not at all, but still, this wasn’t what he wanted. The whole idea had only been a ruse yesterday to keep Mel from knowing that he had worn socks to work, and now it had blown up in his face. “They’re way too feminine,” he finally said as he continued to look at the slacks he was wearing. “Everybody will know.”
“Everybody is going to know soon enough anyway,” Mel replied.
Chad looked quickly up at her. What did she mean by that?
“I suggest you start getting used to that fact!” she added. “Put your shoes on now. You have another baby bottle to finish before you do anything else.” Chad groaned.
As Chad drank his baby bottle, he tried desperately to think of ways to get out of wearing the women’s pants to work, but no solutions were presenting themselves. Mel had seemed awfully determined, and he was feeling more and more trapped. Could he get fired for it? It was a serious consideration. Would Mel care about that? Reluctantly, he realized that she probably wouldn’t. Trapped! And what did she mean when she said that everybody was going to know soon anyway? As he drank the last few drops, he began to become more and more worried about his life.
When he was finally finished with his baby bottle, he carried it out to the kitchen where Mel was just putting two more into his diaper bag for him. Not exactly a welcome sight, but she had done the same for him yesterday too. She zipped the bag up and handed it to him. He immediately slipped it over his shoulder to carry. She glanced down at her watch. “It’s a little bit early, but I want you to stop and get yourself something to eat before you go to work… You will do that, won’t you?”
Chad realized it was really an order, not a question. “That’s what I usually do… when I have time,” he added. “I didn’t yesterday.”
“Good, you have plenty of time today. So you can leave now.”
Chad felt like he was being kicked out of his own apartment. He carried his diaper bag back into his bedroom to get his keys and wallet. Mel followed him. He picked up his keys and looked down at the pants he was wearing. Then he looked up at Mel, there was clearly frustration and annoyance in his eyes. “I have no pockets,” he said.
“Of courses not.” Chad couldn’t miss the look of absolute glee in her eyes.
“What am I supposed to do?”
“Isn’t that what purses are for? Are you that dense?”
“But I can’t!”
“Are we going to have to go through that again?”
Chad searched for something to say. This was getting to be way too much.
“You better get used to carrying a purse and quick. Because from now on, you’re not allowed to leave this apartment without one – for any reason! Ever!”
Chad wanted to scream. It was like every single day she went out of her way to humiliate him more and more and now she was out to totally destroy his life. As he stared at her, he searched for something to say. Any argument that might help. But Mel’s look of delight had turned now to determination. He was screwed and he knew it.
“You better get moving,” she finally said.
Reluctantly, Chad found the purse he had bought last night and opened it. He put his keys and wallet in it. Then he added his pocket comb, a handkerchief and his pen. All the things he usually carried in his pockets. He glanced at the little pile of change that was still on top of one of the cardboard set of drawers. “Put that in too,” Mel told him. He scooped the change into his hand and dumped it into the bag along with everything else. Mel picked up his cell phone and pulled it out of its case that connected to the belt clip he had for it. “You don’t need this anymore,” she told him as she handed it to him. Chad took it and found the pocket on the outside of his purse that was made for cell phones. He opened it and put the phone inside. Somehow, that simple act made him feel even more defeated.
“Ok, off to work now. And don’t forget to stop and get something to eat on the way.”
Chad was still too stunned by everything to reply. Silently, he walked toward his apartment door where he stopped. He couldn’t do this. He just couldn’t! He turned to say something to Mel.
“You don’t have a choice!” she told him in no uncertain terms before he could say anything to her. “You’re going to do whatever I tell you to do and that’s that! And believe me, I’m going to make darn sure that you do! So I suggest you start getting used to it.”
Chad shook his head. “But…” He stopped, still lost for words.
“No buts! Now go! And remember, I’ll be checking up on you.”
Slowly, Chad opened his door. He stopped again to collect his courage, and then he stepped outside. His diaper bag was over his right shoulder, his purse was in his left hand, he was wearing mascara, and his pants had no pockets. Women’s pants. With every step he took down to his car, his mind was screaming Sissy, Sissy, Sissy! He opened his car door and let the diaper bag fall off of his shoulder. He reached across and put it on the passenger seat, then he set his purse next to it. Before he got into the car, he looked back up at his apartment. Mel was still outside watching him. He couldn’t even sneak back up to change. He drove off trying to figure out how he was going to manage going to work wearing women’s pants and carrying a purse.

Mel had a sense of real satisfaction as she watched Chad driving off. It had gone easier this morning than she thought it would. She went back into Chad’s apartment. Now for the next part. She was taking some major steps today. A lot of them. But all of them were steps that had to be made. It was time. Knowing exactly what she wanted to do, she got busy.

The Bet - Chapter 10 (Monday – week 2 Part 3)

The Bet
by Karen Singer

Chapter 10 (Monday – week 2 Part 3)

Mel took them out to dinner that night at a nice steak restaurant. The part that Chad wasn’t very happy about was having to carry his big pink diaper bag in with him. Worse, Mel made him carry it over his shoulder so it could be seen better. “You should be proud to show off your new bag,” she told him. “It’s very pretty.” Chad had no comment.
When they ordered, Mel made sure that Chad got a large steak with plenty of extras while she got something a bit more in keeping with her diet that she wasn’t officially on. Chad was really glad about the steak. What he wasn’t glad about was having his drink poured into a baby bottle for him again. He just stared at it on the table in front of him, not wanting to touch it at all. “You better start drinking,” Mel told him, “because we’re not leaving here to you’ve finished every drop of what’s still in this glass here. Chad looked at the extra large drink she had ordered for him. The glass was still two thirds full. Very reluctantly, he reached out and picked up the bottle and brought it to his lips. This would be another restaurant he could never go back to again. Why did she have to be so cruel? But he realized that despite relieving himself of his sexual frustration twice earlier, that need was quickly growing again.
Once they were back in the car again, Mel asked him, “Where do you usually buy your clothes?”
“A lot of different places,” he told her.
“I know a good place where they have lots of nice quality things. It’s not too expensive either. Let’s go there.” Chad had no reason to not go with her suggestion. Besides, she was driving. But when they got there, Chad had immediate doubts about the store. From the outside it looked very nice and upper-class. The part that worried him was that he wasn’t sure if the store sold any men’s clothes. “Are you sure about this place?” he asked her as he pulled his diaper bag up onto his shoulder again.
“Oh yeah,” Mel answered. “I buy things here all the time.”
More worried than ever, Chad followed her into the store. He looked around when they got inside. “I don’t see the men’s department.”
“They don’t have one,” Mel replied as she led him toward the back of the store. Chad felt the beginnings of panic start to settle into his stomach again.
Mel strolled casually through the store, stopping here and there to look at something more closely. Finally, she led him into the Junior’s department where she started looking through the racks of slacks, wondering what size would be the best for him.
“I was really wanting some new men’s pants,” Chad commented.
“Nonsense!” Mel replied. “Why should you ever want to buy men’s clothes?”
“Like maybe for work!” he replied urgently.
“You’re a sissy, aren’t you?”
Chad hung his head, “Yeah,” he replied softly.
“So why should you be wearing men’s clothes?”
Chad had no doubt that whatever he said he was going to lose the argument, so he said nothing. He allowed himself to pee into his diapers instead.
Mel walked around lots of racks and picked up about five pairs of slacks that she thought might fit him. Then she led him over to the changing room where the attendant suddenly got a bad case of the giggles. Mel took his diaper bag from him and handed him the first pair of slacks. “Ok, put them on and let me see.”
Chad wasn’t all that happy about it, but at least that part of the store was set up so that not many other people would see him. He went into the dressing room and pulled his pants off and slipped the women’s slacks on. They fit over his diapers easily and were way too long. He poked his head out from behind the curtain. “They’re too big,” he said.
“Let me see,” Mel replied.
Chad walked out to show her. He noticed the attendant watching closely from the entrance to the changing area.
“Yeah,” Mel agreed, “they’re a bit big. I wasn’t sure about the best size because of your diapers so I had you try the biggest ones on first.” Chad saw the eyes of the attendant behind her grow wider. She handed him another pair of slacks to try on.
The next time Chad came out of the changing room, the attendant was standing right with Mel, talking to her. As far as he could tell, the only good part about his current situation was that there were no other customers around at the time. But that certainly wasn’t saying much.
Chad tried on pair after pair at Mel’s whim. Usually ones that the attendant had found somewhere out in the store and had brought back for him. Some were too big, some were too tight. Some were way too long. More than a few of them had a low-rise waist that showed off way too much of his girdle or could possibly show the top of his diapers underneath. But every pair that he tried on continued to fuel his growing sexual need once again. He couldn’t believe he was doing what he was doing. Trying on women’s clothes, with two women helping him… It was almost becoming too much. He was beginning to be glad for just how tight his girdle was to hide any signs of how excited he was becoming over it.
The attendant soon began taking more and more of an active role in trying to fit him. More than once she commented about how visible his girdle was or if she thought the fit or style was all wrong. Eventually she was running her hands over his the slacks to see how they fit. Chad was convinced she was really trying to feel the diapers he was wearing under his girdle. He also quickly realized that he wasn’t going to have a say about any of what he would be buying.
By the time they were finished, they had picked out three pairs for Chad to buy, one in black, one in light tan and one in dark blue. All three pairs were in different styles and very feminine. All three pair felt delicious to wear. None of them were anything close to what he could ever wear in public! And it had taken so long that Chad had wet himself two more times. He was just thankful that nobody would ever know.
When they were done, Mel thanked the attendant sincerely, and led Chad further into the store. Chad had thought they would be leaving, but Mel was showing no signs of that yet. As far as Chad was concerned, there was no place in the store that he would feel comfortable – especially toting around his pink diaper bag. He was even less comfortable when Mel started browsing through the racks of purses. “You need a purse!” she said to him flatly.
The word slipped out of his mouth before he realized it. “Why?”
Mel looked at him like he was crazy. “Because you can’t carry everything in your hands, of course! Silly question. Now start looking for one that you like that will be good for everyday use.”
Chad wasn’t exactly sure what constituted good for everyday use, but he looked over the purses without touching any of them. Mel watched him for a few moments. “You might want to pick up a few and look through them,” she told him with more than a bit of exasperation in her voice. “How else are you going to know how they’re made or what they can hold?”
Chad wasn’t sure he wanted to touch any of them, in fact, he was quite sure he didn’t want to touch them. He had already been branded as a sissy in the store by trying on all the women’s slacks, not to mention what his diaper bag said about him. But Mel was still watching him, waiting. Obviously she wasn’t giving him a choice in this matter either. He began looking through them more carefully. What would be a good one? Something that wouldn’t be noticed quite so much. He suddenly had visions of himself walking around carrying a purse and his sexual excitement jumped another huge notch. Tomorrow at work when he could relieve himself couldn’t come fast enough for him.
Finally he pulled one down that was all black leather. It was the plainest one he could see. He had to juggle all the slacks he was carrying to be able to open it and look through it. Plain, black.. it shouldn’t call too much attention to him… if he had to carry it, which the more he thought about it, the more likely it sounded. He held it up to show Mel. “How about this one?”
She shook her head. “You only looked at one! How do you know there isn’t something better? And it’s not exactly stylish. Does it even have a place for your cell phone?”
Chad hadn’t thought about that last part. He looked again. “No,” he admitted.
“Wouldn’t it be handy to have compartments for different things?” she asked.
“Yeah, I guess,” he replied as he put the purse back on the rack. He pulled a few down and looked through them. The problem was, the more practical they seemed, the more girly they looked to him. Not exactly what he wanted.
Mel realized after a while that he was really having a hard time picking one out, so she decided to help him. After all, she did have more experience than he did. They finally settled on a medium sized dark red alligator leather bag. It had various sized pockets on the outside as well as on the inside – including one that Mel declared would be perfect for his cell phone. The large silver clasp on it would hold it closed to keep the contents in and the two handles were just large enough that if he had to he could slip them over his shoulder. Actually, Chad didn’t decide on the bag at all, Mel talked him into it.
After that , Chad was really hoping they were finished and could finally go home, but Mel went to one more department in the store first – the shoe department. “But I have shoes,” Chad protested as she began looking through the selection.
“You need more,” Mel replied without even looking up.
Chad allowed himself to wet his diapers again as he watched Mel looking through the shoes. He realized that all the liquids she had made him drink were making him pee way too often again. It was a nuisance, but there was nothing he could do about it.
As he watched Mel, he was surprised to realize that she wasn’t looking at high heels for him. In fact, all the shoes she picked up had fairly low heels. “What size do you wear?” she asked.
“In women’s shoes? Usually a nine and a half.”
Mel nodded as if satisfied, then went back to examining what was available. Finally she seemed to settle on a fairly plain looking black pump with a wide one inch heel. She pointed to one of the chairs that were available. “Go sit down,” she instructed him. Chad did as he was told while Mel went in search of a saleswoman. When she found one, Chad saw her showing the saleswoman the shoe she had picked up, then Mel pointed at him. Even from where Chad sat he could see the woman blush. Chad realized that he was about to be in for more humiliation.
Mel walked back to Chad while the saleswoman was looking for the shoes and told him to take his shoes off while they waited. Chad set all his things down on another chair and did just that. Suddenly, his stocking clad feet and bright red toenails were on display for everyone to see. His sexual need was growing again, and rapidly. Although he wasn’t completely happy about it, he recognized that this was another dream come true for him – trying on shoes in the store. He had never done that before. The only thing he could have wished for was that the shoes could have been high heels instead. He was a bit puzzled over the low heeled shoes that Mel had picked out for him.
The saleswoman came back with three boxes of shoes that she set down on the floor next to Chad. Chad noticed that she looked very embarrassed. Not nearly as embarrassed over it as he was though. “I brought a few different sizes,” the woman said, “just in case.”
“Thank you,” Mel replied as she picked up the top box and looked at the size. The box said size ten. She selected the middle box and checked the size, then she opened it and handed Chad one of the shoes.
Chad slipped the black pump onto his left foot. It seemed to fit just fine. If anything maybe a bit loose. He was surprised to realize how comfortable it felt. “Nice,” he said with some surprise. “Really comfortable.”
“Let’s try the next size smaller,” Mel suggested. “We don’t want them to slip later.”
Chad removed the shoe he was wearing and handed it back to Mel, who handed him one from the next box down. He slipped it onto his foot. He had to pull a little harder to get it on, but it still went on fairly easy. “It’s a little bit tighter,” he declared.
“Is it too tight?” Mel asked.
Chad wiggled his foot a bit trying to decide. “It’s hard to tell.”
“Here try the other one on too.”
Chad was soon standing and walking around with both of the shoes on his feet. “They’re a little tight, but not too bad,” he finally declared. “The other size is definitely more comfortable.”
“We’ll take the ones he has on then,” Mel declared.
Chad wasn’t overly happy about that. Why buy shoes that were a bit tight? But again, he realized that he didn’t really have any choice.
Chad had to carry the new slacks he was buying, the purse, the shoe box, and his diaper bag from the back of the store all the way up to the front where the checkout counters were. He felt like a pack animal. Mel only carried her purse. There weren’t a lot of shoppers around as he was checking out, but he did fully expect Mel to ask again if he needed to wet his diapers. But she didn’t ask at all. He figured she had probably forgotten. Since she hadn’t asked, he wet himself again as they walked out through the door.
He was actually grateful to finally get back into Mel’s car and head back to her office where he picked up his own car. “Go back to your place,” she told him. “I’ll meet you there in a little while.”
Chad drove back to his apartment and lugged everything upstairs. He was grateful to be able to finally stop carrying around his big diaper bag. The thing wasn’t only too pink, but it was bulky and heavy and it tended to keep slipping off of his shoulder. What a pain!
Mel came in a little while later carrying a large plastic bag. She sat him down on the floor and reached into the bag and pulled out a baby bottle and handed it to him. Chad inwardly groaned. He was still peeing more than ever before. If he drank much more tonight, he’d never get any sleep. He sat and drank it while he watched Mel take bottle after bottle out of her bag and put them into his refrigerator.
After that, Mel emptied his diaper bag and went through the contents. Then she reloaded it, making sure that everything Chad would need for tomorrow was in there – except the baby bottles, those she would add in the morning.
As soon as Chad finished his drink, she had him try on again all the slacks he had just bought. She cut all the tags off for him before she allowed him to hang them up neatly in his closet. Finally, she changed his diapers for him, noting that he hadn’t messed himself again, and inserted two more suppositories before she taped them up and locked him into his onesie for the night.
“I’m leaving you now,” she told him. “But I’ll be back later to check on you. If I don’t make it back before you go to sleep, don’t worry, I have a key and I won’t wake you.”
Chad was surprised that she would be leaving him alone so soon. It was still a bit too early for bed.
“While I’m gone,” she continued, “I want you to drink four more bottles before you go to bed.”
“Four…” Chad protested.
“Four! And between each one, I want you to practice your makeup. Don’t let me come back and catch you goofing off!”
Chad groaned. “Yes Mistress.” What else could he do?
“Good,” she replied. “Tomorrow morning I’ll be coming here again instead of you coming to my place like you did this morning. I’ll be about twenty minutes earlier than usual so make sure you’re up and shaved before then. Oh… and make sure you’ve finished another baby bottle in the morning before I get here too.”
“Ugh,” Chad groaned aloud.
“What?” Mel’s eyes were suddenly showing fury.
“Sorry. I mean… Yes Mistress.”
“That’s better.”
Mel picked up her purse and left him. She really had no intention of coming back later, but he didn’t know that. Tomorrow was going to be another day. A busy day. And a day that neither of them was likely to ever forget! And she couldn’t wait!