The Bet - Chapter 32 (Tuesday – week 5 Part 3 of 6)

The Bet
by Karen Singer

Chapter 32 (Tuesday – week 5 Part 3 of 6)

Mel sat at the table and watched as Gloria threaded her way through the restaurant toward their table. She put a big smile on her face as her friend finally sat down.
“Whew! I think the traffic gets worse every day!” Gloria exclaimed.
“I know what you mean,” Mel replied. She stared awkwardly at her friend, not knowing what to say. The silence between them mounted since neither one of them knew quite where to start. Fortunately, the waitress was there quickly to take their order.
When the waitress had left, Gloria was the first to break the silence. “You didn’t order much,” she noted.
Mel shrugged. “Sissy will be cooking for me tonight. It’s always diet recipes, but I’m still afraid to eat much anywhere else. His cooking is always sooo good!” she added quickly. That statement brought the subject of conversation close enough to some of the things she wanted to tell Gloria. She blushed ever so slightly as she continued, “It’s not just the baby thing you were talking about yesterday,” she began. “Yeah, I do like it and it does turn me on… but that’s really more his thing than mine.”
“His thing? So what’s your thing?”
The waitress was suddenly back, setting cups of coffee down in front of each of them. Mel picked her cup up and sipped at it, more to delay and collect her thoughts than from want of something to drink.
“My thing?” Mel finally said. Her face seemed to light up as she pictured him the way she loved him in her mind – in his maid’s uniform. “My thing… It’s… It’s like having the perfect personal servant. One who’s absolutely attentive to my every little need. And he cooks… like a dream! And he cleans the house… like a dream! And he’s so sensitive. I mean, he really listens to me – as if he’s really interested in what I have to say. Most of the guys I’ve ever gone out with, in fact none of them, have never been like that.”
Gloria was suddenly feeling more than a bit jealous. Her description was more like every woman’s dream… except for him being a total flake! She wanted to ask again if Mel loved him, but she didn’t bother. No matter what the situation really was, Mel would only deny it. “So he makes the perfect little maid?” she finally replied.
Mel only nodded as she took another sip from her coffee.
“I know you don’t want to hear this Mel,” Gloria continued softly, “but that still isn’t any reason for me to do what you want me to do with him. And like I said before, I’m not going to do it.” She was afraid that Mel might get angry again. Fortunately, she only saw Mel take a deep breath.
“I know,” Mel replied sadly. “But still, there’s got to be some way you can help me.”
Gloria shook her head. “None that I can see. Are you going to let me have him to myself for a little while so I can put my own demons to rest?”
That was the last thing the Mel wanted. There was too much of a chance that Gloria would undo everything else that she had already done to him. She shook her head. “No. Can’t do it.”
“I was afraid of that,” Gloria replied disappointedly.
Mel didn’t walk out, and neither did Gloria, but they both pointedly stayed well away from any conversation that had anything to do with Chad for the rest of their lunch.

Chad approached the door to the gym and paused. Yesterday he had made his debut here as a complete and total sissy – acting in ways that he never imagined he ever would… or could. So many people had watched him – closely. He felt embarrassed just thinking about it now. Could he make himself go in there again? Ever? With a mental sigh, he knew he had no choice. There was no way around it. With a courage that he didn’t really possess, he grabbed the door handle and opened it, and forced himself to go inside.
The beaming look of joy on the receptionist’s face was almost more than he could stand. “Sissy!” she exclaimed excitedly. She was looking at him, waiting. He knew he had no other option. He dropped a courtesy and said, “Hello, how are you?”
“Much better now that you’re here,” she replied. Her face darkened slightly. “That curtsey wasn’t nearly as much fun as the ones you were doing yesterday.”
What? The ones he did yesterday? He wasn’t about to do one of those again – if he could help it. “Um… I’m dressed a bit differently today,” he replied.
Her lips puckered a bit in frustration. “Yeah, I can see that.” Her face brightened again. “But can’t you do one for me anyway? Just so I can see it again?”
Ugh! Why? He didn’t really want to do it.
She saw him pausing and added, “Cassie says that you’re supposed to do anything I tell you to.”
Double ugh! And worse, he knew without a doubt that if he didn’t do what she wanted then word would get back to Mel, and that would mean trouble! Big trouble! He instantly did his best to curtsey flamboyantly for her, despite the dress he was wearing and the purse over one arm and the diaper bag over his other shoulder. It just wasn’t the same. But he was happy to see her smiling and giggling anyway. He was about to ask if she would go find Cassie now, but he didn’t get the chance.
She leaned over toward him, then cast a quick glance around to see if anyone else was near. Her voice came out as a giggling whisper. “Can I see your diapers again?” she asked. Chad couldn’t believe it. She had really asked to see his diapers. And worse, he knew he had no choice but to show them to her. Dropping his diaper bag and purse down on the floor next to him, he quickly looked around then lifted his skirt, just far enough so that she could see the bottom of his pantyhose covered girdle underneath.
“Oh pooh!” she exclaimed. They’re all covered up.
He nodded. “Sorry,” he replied as he dropped his skirt back down.
“Maybe some other time,” the receptionist replied with a sigh. “I’ll go get Cassie for you.”
Chad was grateful that she was leaving. He had a feeling that she might become a major pain from now on.
“Hi Sissy,” Cassie said as she and the receptionist walked up.
“Hi Cassie,” Chad replied, dropping a polite curtsey to her before he picked up his purse and diaper bag again.
Cassie looked at him funny. “She said that she’s disappointed that she can’t see your diapers today,” Cassie said, referring to the receptionist and trying to prolong the conversation a bit.
Chad shrugged. “I’m dressed for work today.”
Cassie nodded knowingly. “Did Mel tell you that you can talk like that?” she asked.
Chad was flabbergasted! She wanted him to use sissy talk? Here? Again? Now? Unfortunately she was glaring at him all too seriously. He dropped his bags on the floor again and dropped another curtsey. “Sowwy, Cassie,” he replied contritely in his high-pitched sissy voice. The receptionist giggled uncontrollably.
Cassie felt satisfied. She hated making him do it, but Mel had called her to specifically ask her to watch out for how he was speaking. And she knew that Mel would call her later and follow up. “Okay, Sissy. “Let’s go get your diapers changed.”
As Chad picked up his bags again, he wished that Cassie hadn’t said out loud what she was going to do. It used to be so much more private and easier when nobody else knew. The thought of no way to deny it, rang through is head once again. So many people had seen for themselves!
As he followed Cassie back through the room of exercising women, a few of them waved at him. “Hi, Sissy,” one of them called teasingly. Chad didn’t stop walking but he did smile shyly at her and waved a few of his fingers. He was ever so glad to get out of sight again in the back office – with the door closed behind him.
“They’re still talking about yesterday,” Cassie said as he started to get undressed. “Nice dress by the way.”
Chad momentarily stopped what he was doing. “Thanks,” he replied, referring to his dress. “I’ve had a few nice comments about it today already. What are they saying about yesterday?”
Cassie shrugged. “Let’s just say they’re still pretty excited about it. You’re all the buzz.”
Ugh! “I can believe it!” But what could he do about it? Nothing!
Getting out of his dress, pantyhose, and girdle, took a few minutes, but he finally was able to carefully peel off his plastic panties to expose his diapers and lay down on the floor in front of her. She handed him one of the baby bottles full of Mel’s green tea that she had pulled out of his diaper bag. He put it to his lips automatically and started sucking on it.
Cassie started peeling off his diapers. “Wow, you’re wetter than usual today,” she commented as she pulled the tapes open on the second one.
“Too much to drink,” Chad said before he went back to working on his bottle.
Cassie cleaned him up quickly, noticing as she did so that his penis inside of his chastity device was still as tiny as it was last week. And still no reaction to all her attention to that area as she was cleaning him. No sense in even trying anything else with it. “Okay, roll over,” she said. “Let’s get your backside now.”
This was the part that Chad really enjoyed and looked forward to – lately. He didn’t know why, but he just accepted now that he did. He rolled over onto his stomach so that Cassie could play with his backside again.
Cassie cleaned his bottom, then poured a generous amount of baby lotion into her hands. The moment she began messaging it into his backside, Chad let out a small moan of pleasure. “Scrunch up,” she told him. Chad pulled his knees up under him, raising his backside up into the air where she could get at it better. She reached into a nearby desk drawer and pulled out the toy that she kept there for him now. A moment later, that too was well lubed with the baby lotion.
She pressed her well lubed finger up against his tiny asshole and saw him almost start to push back against her finger, but he stopped, waiting for her. She pushed harder and her finger slipped inside. Just a little bit at first. She worked that much around a bit, knowing that he was enjoying the sensation, then she pushed her finger all the way in. He shuddered and buried his head under his arms.
She grabbed the ribbed dildo she used on him and, slipping her finger out of him, gently pushed the tip of it up against his hole. He arched his back and pulled his head up, waiting for it… wanting it. She didn’t disappoint him. Gently and slowly, she pushed it forward into him.
One by one, Chad felt the ribs of her toy slowly pushing into him. He no longer cared about why he loved it so much, maybe it was because Mel had rendered him incapable of any other form of sex. He only knew that he loved the sensation. He felt her pulling it back out, ever so slowly, then pushing it back in again. More! He wanted more! And he wanted the sensation to go on forever!
Ever so gradually, Cassie increased the speed of her thrusts, till he was pushing and pulling right along with her, eventually doing most of the work while she held the toy still. She saw him trying harder and harder to gain even more pleasure from it, but there was no additional pleasure to be had. She saw him finally realize that and slow down, finally stopping. She pulled the dildo out of him and watched as he seemed to deflate under her, his knees still pulled up to his chest underneath him.
With a soft moan of frustration, he rolled back over again and grabbed his bottle. His eyes were shut against the frustration as he put the thing to his mouth and started drinking again. If only he could get there! If only he could get the kind of relief from his ever aching sexual frustration that he so desperately needed. But the more he thought about what it was that he was trying to do, and how he was trying to get that relief, the more he realized just how impossible it probably was. So disappointing!
Cassie opened the jar of suppositories and pretended to pull one out. She realized she probable didn’t even need to bother pretending because his eyes were shut. He wasn’t watching anyway. She stuck her finger up inside of him as if pushing one of the little devils up there. His eyes popped open momentarily. They closed again as soon as she pulled back out of him. There was a slight look of annoyance on his face. She couldn’t blame him.
Chad worked on his bottle, his mind now moving away from unpleasant thoughts to more positive ones… like finally getting something solid to eat. A hamburger! A big, juicy hamburger! That’s what he wanted. With a ton of fries and a drink that wasn’t in a baby bottle. As he felt Cassie pulling the second diaper into place and taping it closed he was trying to decide – where was the best place to get the biggest, juiciest, best hamburger in the city?

Gloria walked around the little room where she worked with most of her customers one-on-one. Dust cloth in hand, she wiped down the furniture and decorations that made the room warm and inviting. Her next client was due in any minute now, but working with another client wasn’t the foremost thing on her mind. Mel was. Actually, Mel and Chad.
Mel was still going to be her friend, no matter what. She realized that now and she was relieved. But their relationship was still very strained – because of Chad. Mel was still pushing her to hypnotize him and reset the desires within him that would ensure her to win their bet. She, herself, also wanted to hypnotize him, but for a totally different reason – she was still worried about what she had already done to him. She had gone along with Mel’s games gladly… willingly… in the beginning. But after finding out how hard Chad was fighting against them, she knew how wrong she had been to do any of it.
They both wanted to hypnotize him again, only for different reasons. Her question now was, how could she possibly get Chad alone for a while – to work with him, to get answers out of him. Answers that she desperately wanted to know. Could she call him somehow? Ask him to come in for a special session? But she didn’t even have his phone number. He was Mel’s friend and he always came with her. Besides, doing something like that would be like sneaking around behind Mel’s back. And that wasn’t right – either.
So how was she going to get her answers if Mel wasn’t going to let him be alone with her? The outer door opening brought her back to where she needed to be. She walked out to warmly greet her next client.

“Thanks Cassie. I owe you one,” Mel said just before hanging up her phone. She sat back in her chair and stared at her office ceiling. Just as she suspected, Chad had not used his new sissy voice when he went to the gym. Actually, she never once doubted that he would use his regular voice. But that wasn’t the point. This was more like yet another way to deny him something male. In this case, the use of his male voice… actually the use of anything except his very sissy voice since he wasn’t allowed to pronounce certain letters when he spoke. The thought of her denying him yet something else masculine sent a small thrill through her. Very small, but it was still there.
Her mind flashed back to the strained lunch she had shared with Gloria. Gloria was still unwilling to help. It would be so easy for her to simply hypnotize him again and make him believe that he really did want to be incontinent. And he did want it! She knew that for a fact. She just didn’t really understand why he was fighting it, and her, so hard.
Speaking of which, she had put him through a lot for the last few days. She liked her idea of putting him in only one diaper all the time and then giving him only two hours to make it leak. And since she had checked him continually to make sure he was wetting all the time, there was no way he could hold back at all. But was it working? Was it helping? Was it having any affect at all on him? She had no way of knowing.
Once again she thought of Gloria. Gloria could find out for sure. Hypnotized, he would certainly tell the truth. If he were hypnotized, she could find out for sure if all her measures were having any affect on him. She could find out if her methods were removing any of his control at all. But Gloria… Ugh! How was she going to get her stubborn friend to help?
She forced her mind back to Chad and the fact that he did not use his sissy voice at the gym today. She had been totally right in her figuring that he would speak normally there… as well as everywhere else, she was sure. Maybe she couldn’t control him at work, but there were other things she could do to enforce… or force him… to speak the way she wanted him to at other times.
And the first thing to do was to add some punishment! She opened up her email program and began typing.

Borrowed Time

Tomorrow, New Year’s Eve, will mark the one-year anniversary of my heart attack. Since then, my life has changed a lot.

Where my time to be Karen and write used to be early in the mornings, that time is now taken up with fairly strenuous exercise – exercise that slowly get’s more intense each week.
Our house no longer belongs to just my wife and I. We share it with family. Sometimes a lot of family!

And lately, I’ve been more aware of my own mortality than ever before. All the little aches and dizziness only serve to remind me that I’m living on borrowed time. But then for that matter, I guess we all are. I’m simply more aware of it now and I can appreciate more the love that is around me.


As to this latest story that we’re working on together (The Bet), it’s become something of an obsession for me. I think about it a lot. I dream about it at night too. I know there has been some discussion as to the length of the chapters, but I’m not going to be making any changes to the way I write it – what comes out, comes out.
I used to think that breaking a story like this up into small packages was not a good thing, but lately, I’ve kind of changed my mind. The story is long and complicated. And the small pieces that I post each week give readers something to look forward to that can be read in only a short sitting. Since I’ve started this project, I’ve only gone back and re-read three or four chapters back to back a few times – hoping that everything hangs together okay. I haven’t done that now for a very long time because I’m too busy writing to take that much time. So I’m hoping that everything is making sense – and I’m praying that I’m not forgetting too many details.
I still have sixty-five total chapters planned for this effort. So you’re not quite to the half-way point yet. It’s taken a very long time to write and post this much, so you all have a lot to look forward to in the future.


My mind does tire of the one story occasionally, and I sometimes have to abandon it temporarily to get some other ideas down in writing. I’ve been going through such a phase for the past month (don’t worry, I’m still way ahead of you as far as this story is concerned). In the past month, I’ve added several more chapters to the one book my wife knows I’m writing – book two of a sword and sorcery novel. I’ve started a new book that is based around an FBI investigation. And lately I’ve been delving deeply into another story that involves humiliation and high heels and… well, you get the picture. By my count, I am now writing six separate books! All of which are rolling around in my warped brain. It’s amazing that I can keep any of it separate! But the strange truth is, that the more I write, the more I want to write. In fact, I really don’t want to do anything else. Many times, I’ve resented having to stop writing to do something – important. Who would have ever guessed that I used to absolutely hate writing?


Anyway… back to my original topic. Since the year is coming to a close and so is the first anniversary of my brush with death, I wanted to take a moment to reflect back over the past year. I recommend that you all take a good look at what you’ve been through. The time we have on this earth is relatively short, and it grows shorter every day. As I said before, we’re all on borrowed time.

Therefore, I’d like to say a very special thank you to everyone who has stood by me, and sent me well-wishes, or even just hung around to read the tripe that I compose. You all mean the world to me. I only wish I could express my gratitude better.

So as this year draws to a close, my New Year wishes for all of you are:
To laugh heartier and more than ever before
To dare to dream bigger than ever before
To go after something you’ve always wanted, but never had the courage
To love more passionately than you’ve ever loved
To recognize the good things around you and stop to appreciate them
And to realize that life is a precious gift… and to appreciate that gift.

Bless you, each and every one!
Karen

The Bet - Chapter 32 (Tuesday – week 5 Part 2 of 6)

The Bet
by Karen Singer

Chapter 32 (Tuesday – week 5 Part 2 of 6)

Chad opened his desk drawer and put his purse inside before he sat down in his chair. He stared for a moment at the bouquet of flowers that Mel had sent to him last week. It looked different – smaller, and a lot less vibrant. What had happened to it? The roses in it were fully opened up now, but some of the other flowers looked like they were dying. He made a mental note to ask Robin about it when she came in. He hit the button on his computer to start booting it up.
“Hi Chad,” Robin’s voice called as she was walking past.
Chad turned around in his seat. “Hi Robin,” he replied.
She had stopped at the entrance to his cubicle and was staring at him. “Wait a sec. I’ll be right back,” she said. She disappeared and came back a moment later with nothing in her arms. “New dress?” she asked. “Stand up so I can see it better.”
Chad stood. “Yeah, I just got it. I kind of like it. What do you think?”
Robin stared at him for a moment. “I think that I wish I could afford some of your clothes. Very nice!” She stared at him for a moment more. “I think you could use some better jewelry with it. You always wear the same old necklace, but still, it looks really good.”
“Thanks,” Chad replied, feeling both relieved and happy as he sat back down. “Hey Robin, what happened to all the flowers?”
Robin glanced over at the bouquet on his desk. “Oh, they were looking kind of puny and some of them were obviously dying so I pulled those out. I also added some water for you. You really need to check that every day.”
Chad nodded. “Thanks,” he replied. I appreciate it. So how did things go yesterday?” he asked.
“Quiet, as usual,” she replied as she moved further into his cubicle and leaned up against his desk. “How was your day off? What did you do?”
It was all Chad could do to not choke at her question. There was no way he could ever tell her what he really did all day! “Oh… not much,” he replied, trying to find the quickest answer. She was still looking at him, waiting for more. “I… visited a few people,” he finally added. He was relieved when she seemed to be more satisfied. Visited people was right! His problem was just the way that he had visited them!
“I see you got your nails cut,” she said next. “Very pretty by the way.”
He held up his hands to look at them. The nails were still very long, but a lot shorter than they had been all last week. He still thought they looked pretty. Something inside of him was pleased by the sight of his fairly feminine looking hands. “Yeah,” he replied, still looking at them. “I think I kind of like them this length.”
“They’re still pretty long. Not exactly practical for working.”
“Maybe, but they’re a lot easier to deal with than the longer ones I had.”
“I don’t know why you ever got them so long in the first place! That was kind of silly.”
Chad couldn’t really tell her that he had no choice in the matter. “It wasn’t really my idea,” he replied cautiously. “But I think I learned something from it.”
“Learned something? I’m betting the idea of having nails like that just turned you on so much that you decided to try it. That’s why you had them done. And now… now you’ve seen what a pain they were and had them cut down a bit.”
“Well…” Chad started to reply.
“Don’t deny it!” she teased. “That’s why you’re dressing the way you do. You love it! Don’t you!”
Chad blushed. “Kind of,” he replied sheepishly. “Actually, it’s a bit more complicated than that.”
Robin threw her arms up in the air. “Complicated! Don’t hand me that crap again! You love it, so you’re doing it. Right?”
Chad stared at her for a moment. She really had no idea, and he meant to keep it that way. But deep down, she was also right. He did love it. “Yeah, I do,” he finally admitted blushingly. He was a sissy after all. Mel had made that point abundantly clear yesterday.
Robin nodded, more satisfied. “That’s better. Complicated? My ass! You’re dressing like a woman because you love it… it turns you on! Don’t try to hide behind some kind of other silly lame excuse.”
After Robin had left, Chad turned around again to face his computer. The login prompt was waiting for him. He reached for the keyboard and paused. Last week, he had been forced to teach himself to type with just his fingernails on the keys. But now his nails were shorter. He reached out to the keyboard with just one hand and experimented with touching a few keys. His nails were still too long to really let him use anything more than just his nails when he typed. Yes, he could slip the nail over top of the key, between the keys, but when he pressed down, the tip of his nails hit something underneath. So he still couldn’t really use anything but his nails to type with. Fortunately, he had gotten a lot of practice with it last week. As he typed in his password, he quickly realized that he was going to have to get used to it all over again. Yes, he still had to use only his nails, but now he had to get used to the shorter length. At least it seemed to be a lot easier and his nails felt stronger and less fragile now too.

Mel closed the folder and put it into her finished pile. She had a few minutes now to think about other things. And other things usually meant Chad. Only this time, instead of directly thinking about Chad, she was thinking instead about Gloria… and how she could get Gloria to help her again. One thing was for sure, in order to get Gloria’s help, she first had to talk to her. She picked up her phone and dialed the number. “Hi Gloria. It’s Mel.”
Gloria was almost hesitant in her answer. “Hi Mel,” she said simply. She was still very concerned after their last lunch meeting. In a way, she was just glad that Mel had called. At least it meant that they were still friends – she hoped.
“Are you game to try lunch again?” Mel asked.
Gloria hesitated again. Mel had walked out on her yesterday. But she was her friend and everything she had said to Mel had been the truth! “Are you sure? I’m not changing my mind.”
Mel wasn’t glad to hear that Gloria was determined to remain so stubborn. “Yeah, I’m sure. And I’m really sorry about yesterday.”
“Yeah, I am too Mel. But Mel… I meant everything I said then.”
Mel was silent for a moment. She knew that Gloria believed everything she had talked about was true, but she now knew that some of that was wrong… very wrong. But still… “Gloria, somehow we’ve got to get past this. Let’s just have lunch. Maybe we can talk about it a bit more… maybe. I promise not to run out on you again like last time.”
Gloria chuckled. “Okay Mel. We’ll just eat, and maybe talk a bit more. See you at lunch.”

Chad stared at his computer monitor. He had been working, but right now, work was the farthest thing from his mind. Instead, he was thinking about peeing… or rather not peeing. He was having a lot of trouble so far holding back. At first, he found himself continually peeing before he even knew he was going to do it. But now that he had that control back again, just holding back was still all too difficult. Of course, he had already had a lot to drink since he had gotten up. Not to mention all he had been drinking for the last three days. His system would have to readjust back to normal and that might take a while. But still, now that he could control himself again, he didn’t seem to be able to hold things back very long at all. He sighed. Try, try, try. It was the only way!
“Break time,” Robin’s voice called out from behind him, pulling him quickly out of his thoughts.
Did he want to go to break? Yes and no.
“They had some great new doughnuts yesterday,” Robin continued. “You should have been here.”
“They did?” The thought of something solid to eat, especially something as tasty as a doughnut, made up his mind for him. Besides, Robin would only egg him on till he went with her anyway. He pulled himself out of his chair and followed her down the hall.
“I really do love that dress,” Robin noted as they walked.
“Thanks,” Chad replied as he realized he was no longer able to hold back from peeing again. He glanced at his watch. Less than ten minutes. Not good.
The break room was filling up fast when they got there. Chad spied several boxes of doughnuts past the coffee pots and made a beeline straight for them. He grabbed one and a napkin and was eating it before he even grabbed a cup for his coffee. Mmmm! So good! Heaven!
“I told you they were good,” Robin said, noticing the look of joy on his face.
“You have no idea!” he replied. He certainly wasn’t going to tell her that he had eaten nothing but baby food for the last three days. He finished his doughnut before he even tried to pour himself some coffee. Then he joined the other women at their extra large table.
“Hey, we missed you yesterday, Sissy. Where were you?” one of them asked.
They missed him? Sure! “I took the day off,” he replied.
“Any special reason?” she asked.
He shook his head. There was no way he wanted to give any indication of what he had really done. “No, I just took a day to relax and visit a bit.”
“Recovering from your divorce!” another woman stated with certainty.
Chad was shocked. That wasn’t the real reason at all. “Um…” he searched for a good answer.
“It’s okay! Divorces can take their toll. I aught to know!” yet another woman chimed in. A few of the women laughed.
“Hey!” said still another one. “My sister called me last night. And she went to the mall yesterday, and you wouldn’t believe what she said she saw there.”
“What?” someone asked.
“Well, she said there was some guy there, dressed up as the most ridiculous sissy thing you could imagine! She even said she saw some diapers under his dress!”
Chad wanted to crawl into a big hole and hide.
“What was he doing there?” someone asked her?
“I don’t know. She just said that she saw him outside curtseying to everyone and then later walking through one of the big department stores. I don’t know anything else. But can you imagine someone dressing like that? In the mall of all places?” There were more than a few chuckles from around the table.
“One of your friends, Sissy?” one of the women asked Chad.
“Uh…” He shook his head. Lying was clearly the best option here. “Nobody I know,” he replied nervously.
“Well,” the woman replied, “probably not anyway. You at least dress a whole lot better. I like that dress by the way.”
Chad glanced down at his dress again. “Thanks.” Whew! He had hoped to never hear about his trip to the mall again. And now one of the women had brought it up here! He just hoped that nobody really connected him with being there.

Mel shook hands with her client and led him all the way to the outside door. She reassured him once again that everything would be fine and that she was on top of his situation. When the door had closed behind him, she turned back toward Andrea. “Business is definitely up,” she said as she shook her head. “It seems like everyone wants to sue everyone else.”
Andrea picked up some of the work folders on her desk that she had yet to work on. “You don’t have to tell me!” She dropped the folders and just let them fall back onto the pile. Then she pointed at some envelopes and a small box on her desk. “Mail’s in early today. I think that package you were still waiting for got here.”
Mel walked over and picked it up. It was covered with heavy plain wrapping, she could tell nothing. “Thanks,” she said as she grabbed both the box and the pile of mail that Andrea had left for her. She carried them back to her office where she closed the door. The pile of envelopes she dropped on her desk out of the way, the box she set right in front of her. She grabbed her scissors and began opening the package. Almost hesitantly, she peeled back the plain brown wrapping to see the box underneath. The word “Aneros” jumped out at her. With a last glance at her door to make sure it was closed, she set the box down and opened it. Inside, she found the oddly shaped device that was designed to make milking him easier. Unlike the “toys” she had received yesterday, this one inspired no sexual interest for herself, but she did wonder if he would receive any pleasure from it.
Odd, that he was becoming so responsive to being toyed with in his anal cavity. She had totally denied him any pleasure from the place where he should be receiving all his pleasure – his male appendage. She had totally denied him that ability. So was this new form of sex for him more like a female pleasure? She wasn’t him and she wasn’t male, so she had no way of really knowing. But just the act of him being penetrated instead of him doing the penetrating certainly seemed totally feminine. She wondered briefly if he could get multiple orgasms from this kind of sex – like a woman could from normal sex. Of course, to the best of her knowledge, he hadn’t had a single orgasm yet. She didn’t even know if such a thing was possible. But either way, it was another case of maleness denied. And that thought brought a tingle to her dampening sexual region.

Chad could barely hear Robin typing on her keyboard in her cubicle next door. She was busy. He opened the spreadsheet for the bet that he kept on his desktop. He found today’s date and stared at it. Thirty one days to go. Another month. One more full month before he would get the chance to prove that he could still control himself. Would he make it? He had to! A surge of confidence ran through him. He would make it! He was absolutely sure of that. She might play her little games with him on the weekends, but here at work he could work, and work hard, at not only maintaining, but also building that control that would let him win. She had no chance!
He looked at yesterday’s date – Monday. He had no timing to fill in there. He had never once been able to hold back a single second all day yesterday… or Sunday… or Saturday either. Or Friday night for that matter! No wonder he was having so much trouble today. He was fairly sure he remembered being able to hold back for twenty-nine minutes on Friday while he was at work though, so he filled in that space.
The three empty spaces where he had no time to fill in bothered him though. Three empty spaces that represented three very long, very hard, very humiliating days. He didn’t really want to think about those days, but he couldn’t help it. Three days wearing only a single diaper at a time with just two hours each time to make it leak. How had he managed it? Unbelievably, he had. Three days of acting all the time like the biggest sissy baby flake he could possibly imagine – Mel’s sissy vision of him. And having to use nothing but that stupid high-pitched voice? He was really glad he was at work now where he wouldn’t have to worry about it… at least not till he got home later tonight.
For three full days she had literally pounded sissyness into him. Forced him to act in ways he still couldn’t believe. Forced him to look at himself over and over again – and finally see himself for what he really was, a sissy. Because even though he “kind-of” labeled himself that in the past, deep down, he had always denied it. He had still clung desperately onto his male chauvinistic attitudes. But could he do that anymore? He thought again about his trip to the mall yesterday, not to mention his trip to the gym. No, he really couldn’t, or shouldn’t think of himself as a male anymore. So many people had seen him, up close, behaving like the total sissy that Mel had made him. Even though he had lied to the women in the break room, if anyone ever asked if that was him doing those things, there would be no way he could really deny it. He had done them. He was that sissy!
Could he ever think of himself as being a male again? His eyes caught sight of the skirt of his colorful dress. Disgusted with his thoughts, he quickly closed the spreadsheet. He didn’t dare think about it anymore.

The Bet - Chapter 32 (Tuesday – week 5 Part 1 of 6)

The Bet
by Karen Singer

Chapter 32 (Tuesday – week 5 Part 1 of 6)

She danced with him, and it felt so good to be held in his strong arms. Just being with him, she felt safe, secure… wanted, loved. He was everything she had always dreamed of – tall, handsome, strong… loving. She knew that sometime in the past he had done something heroic for her, something amazing. She knew that he had rescued her from something unimaginable, yet what that something was, never mattered, at least not anymore. She loved him unequivocally, and more importantly, he loved her – the same.
But something began to impinge upon the world of her dreams. Something that was not right. It was just a bit of a background nuisance at first, but it gradually grew and got worse. She wasn’t comfortable, her pillow felt all wrong. It wasn’t as soft as it should have been. But back in her dream, life was still beautiful…
She felt colder than she should have. While her mind was dancing and dreaming of her love, she reached for covers that she couldn’t find. It bothered her that they weren’t there. And later still, there was the smell. Kind of an awful smell – not terribly strong, but still irksome. It was still in the background of her dream, but it was becoming evermore distracting.
But her dream lover was still there, adoring her. And she adored him. So wonderful, so nice.
Darn her pillow! She rolled over further, off of something, and finally found a softer spot, she instantly felt better. Her dream lover was getting ready to make sweet love to her. She unconsciously reached for her covers again – and couldn’t find them. Darn! Where were they? It was disturbing her dream. And then there was that darn smell too. What was that? And something about the light wasn’t right… it was way too bright!
She awoke fully and opened her eyes. Realization of what had happened flooded over her. Oh geez! No! This was all wrong! She had fallen asleep with him still in her bed! No, no, no!
She shoved him a bit. “Sissy! Wake up!”
Chad startled awake quickly. “Huh?” It took him a second to get his wits about him. He was still in her bed.
“Go home!” she ordered.
He groaned, still half asleep. He glanced at the clock next to her bed – almost five in the morning. He had been there all night. Despite having slept in her bed, he felt stiff and tired. But then he had tried to hold her in his arms all night without moving. He yawned and rolled off of her bed onto his feet. It took him a moment to steady himself. His diaper was terribly huge again, and messy. Ugh!
He staggered a step forward, trying to get his bearings, trying to figure out what it was he needed to do. He was only wearing his diapers. Not even anything to cover the breast forms that were glued to his chest. His maid’s dress… Where was that? He found it on the floor and put it on. It was only then that he glanced back at her. She was sitting up in her bed, watching him. He slipped his shoes on. The huge bulkiness of his diapers made walking in them difficult – despite the low heel. He headed, with difficulty, toward her door.
Mel watched him walking so awkwardly. His diapers where so huge that they kept his legs spread wide apart. She nearly laughed at his predicament. She would have if she wasn’t still so tired… and angry at herself for falling asleep with him last night. A minute later, she heard her apartment door closing behind him. She breathed a sigh of relief. She glanced down at her bed. There were towels and open diapers strewn all over the top of it. She kicked most of them off onto the floor, then reached down to the bottom and pulled up her covers. She instantly felt better. She turned off the lamp on her nightstand and sank back into bed. Her dream, her beautiful dream. Where was it? For that matter, what was it? She only remembered that it had been really nice. What had she been dreaming about?
But the dream didn’t come back to her at all. Instead, she remembered that Sissy would be home now. She hadn’t left him a note with instructions for this morning. Darn! Of course, he didn’t really need a note. He should know perfectly well what to do by now. But her mind still continued to wrestle with him. Maybe he wouldn’t know what she wanted him to do. She had been making some changes.
She tried desperately to go back to sleep, but thoughts of Chad still impinged on her mind. Damn him! She had to go back to sleep! Thoughts of laying here with him in her bed last night filled her mind. She had fed him all three of his baby bottles last night while he laid here in her arms. Something about that amused her. It was kind of funny. But something about it also sent a tiny bit of thrill through her body. He had also made sweet love to her last night again. As a lover, he really was fantastic… even though she couldn’t allow him to really penetrate her in any way – other than with his tongue that is. His wonderful, talented, enchanting, exciting tongue. She inwardly giggled despite herself.
She rolled over again. Darn him! She couldn’t go back to sleep! She glanced again at her clock. Way, way too early. With a groan, she got up to make herself some coffee.

Chad collapsed onto his little blow-up mattress. He was so tired. He really wanted to sleep. But did he dare? He knew he’d have to get up fairly soon to start getting ready. But did he have to get up? What was he doing today? Work! It was Tuesday! He had to go to work later! Ugh! In a little while, he would have to start getting cleaned up and dressed for work. It had been a long weekend. Long and horrible… and thrilling! She had ridden him unmercifully all weekend long, forcing him to do some of the most embarrassing things ever! And then there was yesterday! Damn! Had he really gone into the mall dressed like that and acted like a total sissy? Not to mention the gym and Gloria’s and …
He rolled over uncomfortably on his little mattress. Not just uncomfortable from his diapers and breast forms, but uncomfortable from the memory of yesterday. He was a sissy! That much was for sure. There could never be any denying it now, not to himself, not even to anyone else. He had proved the fact, over and over again in public where so many people had seen him… and would remember him. What a jerk he was. What a fool. What a damn sissy!
He felt himself wetting his bloated diapers again. It felt good. The thought that he was doing it without thinking about it thrilled him. It really was kind of fun. Mel’s little diaper games that she had been forcing him to play all weekend had never once allowed him to hold back at all. He had been forced to drink so much and pee so much that it was all happening automatically now. So interesting. There was rarely any warning, rarely any buildup. He just suddenly found himself peeing. It was what he had always dreamed of experiencing.
She was doing it. She was succeeding. Mel was actually succeeding at making him incontinent. Or at least making him feel like he was. He knew better though. He knew his body better than she did. He could control himself perfectly – with a little bit of work. But it wouldn’t take long to get back all of his control. Why, on Friday he had even held it once for almost half and hour! Twenty-nine minutes before the pee had started leaking out! That was an incredible achievement. With control like that, Mel couldn’t win this bet… no matter what she made him do! And today he would be shooting to hold back even longer! Was an hour possible? Why not? He was going to win this bet!
He yawned and rolled over awkwardly again, trying to get comfortable – in a situation where that was nearly impossible. He closed his eyes. He was so tired, but he had to get up soon. His thumb unconsciously found his mouth and he started sucking on it. He was a sissy. Thoughts of what he had done in his sissy dress, in front of all those people yesterday raced through his mind again as he dozed. And something sexual excited him, just not in the one place it was supposed to. He was a sissy. Pieces of a previous dream began playing in his mind once again. He was a sissy. A happy, joyful sissy. He could embrace and enjoy all his sissy dresses and diapers and anything else that he wanted. He was a sissy.

Mel took the last cold sip from her coffee cup and turned her TV off. She had been watching – nothing! An infomercial! She didn’t need a diet plan like that. She seriously doubted that the diet was as fun and easy as they made it sound.
Her thoughts turned back again to Sissy. He had never really been far from her mind all morning. She still couldn’t believe that she had fallen asleep with him like that. Stupid! And wrong! Well, it would never happen again. She glanced at the clock. Still early, especially for her. But if she couldn’t sleep, then why should he? Besides, he had to get up fairly soon anyway – if he was sleeping that is. She kind of hoped that he wasn’t.
She picked up her cell phone to call him, then put it down again. Maybe it would be better to go over there in person and wake him up. No, she didn’t really feel like bothering. She picked the phone up again and punched in his number.

An odd sound from far away impinged on his lovely dreaming. It brought him quickly out of his slumber. His cell phone! Someone was calling him. He scrambled to his feet as fast as his bloated diapers would let him and fished the phone out of his purse. “Hello?”
“Sissy!” Mel’s voice came over the line. “Were you sleeping?”
“Yes, Mistress,” he answered.
“Well get up! You’ve had enough sleep for one night. Get yourself cleaned up and dressed. Make sure you drink three more bottles before you come over here. Oh, and wear one of your new dresses to work today. I think they look very nice.”
Chad’s groggy head was still trying to make sense of everything she was saying. It was all coming at him too fast for his partially asleep mind, so it took him a moment for everything to register fully. “Yes, Mistress,” he answered. “Three bottles. New dress.”
“Sissy!” Mel’s voice replied angrily. “Who ever gave you permission to speak in anything but your sissy voice? That’s already one demerit and I’m going to punish you severely for not answering the way you should! I told you I didn’t ever want to hear you speaking any other way again!”
“But Mistwess,” he replied, this time more awake and lapsing into the sissy mode of speech she was requiring, “I didn’t know who was calling.”
“It doesn’t matter who’s calling! You never need to speak any other way! Now get busy!”
Chad suddenly found himself holding onto his phone with nobody on the other end. How was he supposed to know who was calling? Okay, he could have easily looked at the display to see that it was her, but he had been in a hurry to answer it and was still half asleep! What did she expect, that he would use that voice all the time? Yeah, maybe she did. But it wasn’t exactly something that he would ever actually do.
He carried his phone over to his charger and plugged it in since it had been a while. Then he went to his refrigerator and pulled out the first of the three bottles that she had told him to drink. There was never any question of not doing it. He simply carried it to the only chair that he owned and sat down to drink it while he stared at his blank walls. Blank, blank, blank. A lot of nothing… except for the framed bet contract that she had hung on one of his living room walls. His eyes automatically averted whenever he happened to look that way. He didn’t want to really see it, much like his toilet that she had wrapped up in layer after layer of her plastic wrap so he couldn’t use it. He never looked at that either. It was too much of a reminder of what he was not longer permitted to do.
He looked around his living room. His whole apartment was a vast amount of emptiness. His only furniture was the one chair he was sitting in, his blow-up mattress on the floor of his bedroom, and a cheep cardboard dresser. There were a few boxes strewn about holding the rest of his things. Boxes that he hardly ever opened. But if he won this bet, what would his apartment look like? What could his apartment look like? He tried to picture a pool table right in the middle of the room. A large screen TV against one wall with an incredible sound system. And furniture – lots of nice stuff – expensive stuff. Everyone would be so impressed. They would congratulate him for what he was doing. All the humiliation he was going through would be worth it!
But what could his room really look like if he won… when he won? Because he had no doubt that he would. His eyes scanned the empty room again. Maybe he did need some help with picking things out and getting it all arranged the best way. But the only name that came to mind so far to get that help was Sandy, and Sandy was firmly on Mel’s side of this bet. But since he’d be paying her, would she do it for him? He still didn’t know. Did he dare ask? Or could that just lead to more trouble?
His bottle finished, he set it back on the kitchen counter. He suddenly felt himself peeing again as he moved about… without any warning again. So interesting! What a sensation! He knew he’d have to start controlling himself soon, but it was still early in the morning. Why not enjoy it while he still could? Besides, with all the bottles that Mel was making him drink, the liquid had to get out of him sometime. Better sooner than later. He headed to his bathroom to start cleaning himself up.
An hour and a half later, he was ready to head out the door. He stopped to check his image in the mirror. He was wearing two diapers again – finally! What a relief. He felt much more secure with two rather than one. Also, despite how tight and uncomfortable his all-in-one girdle was, having it on over top made him feel much more secure too. And talk about security, the darn waist cincher he was wearing under his girdle was a bit too secure… or was that just too tight? Pantyhose again. They were somewhat of a pain, but Robin had said his legs looked better with them than without and the colorful dress he was wearing today seemed to demand them.
As he looked in the mirror, his eyes made their way down his skirt. He could just see the tops of his knees. Further down, his pantyhose covered feet were strapped into a pair of three inch black heels that he thought would go well with the dress. He was happy because the shoes were fairly comfortable. His eyes rose up higher again, up past his waist. Between his waist cincher and his breast forms, he was fairly happy with the way his figure looked. Womanish. It still amazed him. The neckline of the dress was low cut enough to show off the pink stone of his necklace, that matched the pink stone in the ring on his hand. His watch that looked more like a piece of jewelry was on his other arm. His hair was done nicely with the curling iron and his makeup was in place and looked – fairly good he thought.
He smiled. It was amazing how much he had changed in the last month. Very amazing! Who would ever believe it? He grabbed his diaper bag, his purse, and a bag containing the three empty baby bottles he had finished already that morning and headed out his door for Mel’s apartment.

Mel was dressed and ready for work by the time she opened her door for him. She watched his curtsey and listened to his good morning greeting. Something inside of her thrilled again to witness it. “Good morning, Sissy,” she said as she let him inside. She took the bag of empty bottles from him as he set his other bags down on the floor. When he turned around again, she looked him over. She decided immediately that she liked the dress he was wearing. The colorful blotchy pattern was pretty… even on him. She spent a moment looking at his hair carefully. It was done nicely, but it was starting to look like it needed a trim or restyling. She made a mental note to talk to Cassie and Sandy about that.
Overall, she was pleased with the way he looked. Far more feminine than she would ever have imagined when this bet started. She had been denying him his masculinity more and more since they had started a month ago. Now she was really starting to see the results. Masculinity denied! And the very thought of it made her tingle inside.
“Up into your highchair, Sissy. I’ve got your breakfast all ready.”
Ugh! Chad made his way into the kitchen and climbed up into his highchair again. He wasn’t looking forward to another meal of baby food. That’s all he had eaten for days now. As Mel tied the bib around his neck and put the tray into place in front of him, he started dreaming about lunch. Lunch, the first meal he would have where he could get something solid to eat! Something normal! His stomach growled a bit just thinking of it.
Mel set his baby food cereal in place in front of him along with a tiny rubber coated baby spoon and another bottle. Yuck!

The Bet - Chapter 31 (Monday – week 5 Part 8 of 8)

The Bet
by Karen Singer

Chapter 31 (Monday – week 5 Part 8 of 8)

As Mel drove towards home, she kept glancing in her rear view mirror at him. He was still crying softly, feeling sorry for himself. She felt bad about that – in a way, but mostly, she felt like she had succeeded. There was no elation, just that sense of having gotten the job done.
She didn’t say a word as she drove home. When they got there, they both helped to carry all the bags up the stairs to her apartment. She was relieved to get there. She had taken a big chance with what she had just done, but she had gotten away with it… she hoped.
She turned to Sissy who was just starting to pull empty baby bottles out of one of the bags. “Go change into your uniform, Sissy. It’s time to get back to other things.”
Chad was grateful to get back into his maid’s dress. It made him feel a bit more grown up again. But the fact remained that he was still a big sissy. Having Mel remind him that he was working on yet another two hour time period to get his diaper leaking again didn’t help matters either.
Back in his own apartment, it took him only a few minutes to remove the sissy dress he had been wearing, slip into one of his maid’s dresses, slip the comfortable shoes on, and tie an apron neatly around his waist. He stared at his reflection in the mirror that was attached to his closet door. He dropped a little curtsey to himself. Sissy!
He fixed Mel a nice dinner that night, trying something new from his cookbook again. Dinner was mostly a success, he figured. She didn’t say anything. In fact, since they had gotten home, she had said very little. But that was just as well, he didn’t really feel much like talking, especially if he had to use the silly sissy voice that she was requiring. His dinner was yet more baby food, eaten from his highchair. How exciting.
Mel sat in one of her living room chairs while Sissy did the dishes. She had watched a show on TV, but had barely paid attention to it. She turned the set off. There was a slight air of somberness in the apartment. She could almost feel Sissy’s mood. Well, he had to be taught a lesson. But the question now was, did he learn the lesson she hoped he did? It was going to be hard to tell. Maybe the future would hold the answers. Maybe not.
She heard the water go off at the sink, then she watched as he wiped the counters down and put away the dish towel he had been using. He glanced around the kitchen and seemed satisfied. She followed his movements as he left the kitchen and started looking around. He straightened up some magazines, then checked the laundry. Both machines were off. He was looking for something to do. “Sissy,” she called. He came over to her. She could see the depression still on his face. Obviously, he had learned some kind of a lesson today.
He curtseyed. “Yes, Mistress?”
She smiled at his curtsey and greeting. Yes, this was living. This was what she loved. And dinner hadn’t been half bad either. She really loved seeing him in his maid’s uniform… totally subservient to her every whim. She didn’t understand how everyone else could be so bored by it. Yet she did understand the thrill they got from seeing him in his other sissy clothes.
“You wanted something?” he asked, since she didn’t answer.
She didn’t know what she wanted. She just wanted him near, where she could see him. “Is your diaper leaking yet?” she finally asked.
“No, Mistress, not yet. But I still have plenty of time,” he added quickly.
She nodded. “I know. Just let me know when it starts leaking.” She realized something then. Other than the bottle she had seen him drink with his dinner, she hadn’t seen him with any other bottles since they had gotten home. “Are you going to make it?” she asked.
This time, he nodded. “I’m fairly sure I will,” he replied.
“I haven’t seen you drinking much.”
He shrugged his shoulders. “I don’t think it matters anymore. I’m still wetting a little every few minutes.”
She nodded. “Let me know.”
He curtseyed again as he acknowledged that he would. His curtsey thrilled her again. It always did. There was just something about seeing a man do that… a man dressed like a woman… a subservient woman. All his male traits taken away, denied him. Submissive to her. Courteous to her. Attentive to her… and to her pleasure.
She watched as he started walking around her apartment again, looking for things that needed to be done, where nothing really needed attending to. She was tempted to have him stand on his perch again, but the words to order him to do so never left her mouth. He wandered and touched this, and did… nothing really. She could see that he did have something on his mind still. The lessons from earlier?
His dress was neat as a pin. The large white bow she had tied in his hair earlier was still there. She decided she liked the look with his uniform. With the breast forms glued to his chest, his shape was definitely more feminine than masculine – another male trait taken away. The only real indication that he was still male was in his shoulders, which really weren’t all that bad at all. His face too held a certain bit of masculinity, despite the makeup that covered it. She stared at his face as he walked around the room. It was a nice face. She knew it could show kindness… or love. His eyes alone could express so much. She adored the way he often looked at her with them. His lips, even covered in the bright lipstick, looked inviting, kissable. Overall, he was a very pleasing sight. Very.
She saw him suddenly jolt with surprise. He looked quickly down, then back up at her. He hurried over to stand in front of her. He curtseyed and she felt it stir those lovely sensations deep inside of her, sensations that were quickly starting to lead to other lovely sensations.
“I’m leaking,” he said quickly as he turned his leg sideways to see if any had dripped down below the hem of his skirt far enough that she could see it yet.
She didn’t really care anymore. She didn’t care if he had done it before his deadline was up or an hour later. The sight of him in his uniform had her ready to move on for the evening. She looked up into his beautiful sissy face. “Then let’s get you changed.”
Chad expected her to change him right there in the living room again, or perhaps in her bathroom, but she led the way instead to her bedroom. He was surprised to see her laying out protection on her bed so it wouldn’t get ruined in case he wet some more, which was now all too likely. She glanced at him. Did she want him to do something? But then she started adding yet more layers of protection to her bed. He realized then that she had something else in mind entirely. It took him only a moment to realize what that something else might be.
“Get that dress off, Sissy,” she ordered as she worked on her bed.
Finally stripped down to just his single leaking diaper – and his breast forms – she pulled his soggy diaper off of him before she had him lie down on her bed. Within moments, she had him rediapered in nothing but a single diaper again. He waited for her to tell him that he was on another two hour time limit, but she never mentioned it. Instead, she went over to her dresser and pulled out one of the scarves that she used to blindfold him with. A minute later, Chad could no longer see anything.
He heard her moving around, doing something. Probably undressing. She climbed up on the bed with him. He felt her lying down next to him, her naked body hugged his for a moment, then she backed away again. Blind and without direction, he didn’t know what to do. He felt her hand on the front of his diaper. She was pressing down… down on his chastity device underneath. She pressed it firmly into his groin, then suddenly the pressure and her hand was gone again. Her hand came back to the same place, her touch more gentle now, probing. What was she doing? She had to know he couldn’t get hard there – not with that chastity device in place – that is, if he could get hard there anymore.
Mel removed her hand. She didn’t even know why she had bothered to touch him there. Curiosity perhaps? Wishful thinking perhaps? But all she had felt inside his diaper was the hard plastic of the chastity device. And of course it felt exactly the same after she had pressed on it. He was denied that pleasure, but the thought of him being denied sent more tingles of pleasure through her.
She wanted to touch him. To feel him. She climbed on top of him, straddling his stomach. She ran her hands down the sides of his face, down his neck, down between his breasts, then rubbed them slightly on his stomach. Smooth and hairless. Beautiful. Did he feel anything from her touch? He couldn’t react where she knew he wanted to react, but how about anything else? She really hoped so. For his sake, she really did.
She rolled off of him, next to his naked form, and pulled on his body. “Hold me,” she whispered. “Make love to me.”
Two commands that Chad only dreamed he’d ever hear. He was once again denied his sight, but he could still feel her. He rolled over and climbed on top of her, just as she had been on top of him. He was denied any of the pleasure that might lead to sexual relief, but that didn’t stop any of the pleasure he could get from caressing her naked body – even if he couldn’t see it. He could feel her body, massage it, love it. And he did.
Mel writhed under his touch. Magic. And when he started massaging her breasts her breathing became deeper, almost panting as the pleasure and ecstasy mounted inside of her. She knew he couldn’t see her, but those magic hands of his certainly had no trouble making her feel good – all over. His hands went from massaging both her breasts to just her right breast. He squeezed it gently, massaged it. Then, he started leaning down toward it. She held her breath. She could feel his breath now against her nipple as he leaned down ever closer. Ever so gently, his lips reached out and kissed the nipple. She moaned aloud in pleasure. And when his tongue reached out and flicked that same nipple, she involuntarily arched her whole back, writhing beneath him from the wonderful sensation.
She wanted him. She wanted him badly. She wanted to feel him inside of her, filling her completely. But she had denied him that ability. Yet she still needed him. Needed his attentions. She pushed down on his shoulders, pushing him backwards, further and further till he was between her legs. Her waiting sex pushed upwards towards him over and over again. She grabbed his hair and pulled his head down, first gently, then harder. She was becoming more desperate now, she quickly got his head in the exact spot where she needed it and was instantly rewarded by the feel of his tongue flicking out and touching the very spot that craved it most. She wanted to scream with pleasure. Her legs closed around his head, trying to feel more of him in that region. His tongue came again, then again. Faster and faster. Then deeper and slower. Then deeper still. Licking, massaging, caressing, exciting. His hands squeezed against the sides of her butt. His tongue licked particularly hard, and she lost all sense as her body rocked beneath the orgasm that had been building for some time now.
Chad heard her moan, he heard her scream. He felt her body reacting to his touch in so many ways. He was glad he could afford her this pleasure. It made him feel good, like he was still worth something. And then there was the pleasure he received from just touching her naked body… her full round breasts, her smooth naked skin, her wet waiting sex. Touching her like this was something to always be remembered.
With his head pulled into her groin, he couldn’t lift it away, not that he wanted to. He could feel how much pleasure she was receiving from his tongue. He let his hands start wandering her body, caressing it wherever he could reach. He felt her mounting again toward another orgasm. This one seemed to last even longer than the last one. When it was done, he kept at it, kept teasing her with his tongue, but she didn’t keep him there but only a minute.
Mel felt wonderful. Her breathing was slowly calming down, and his little flicks of his tongue were again driving her wild. But she was ready for something else. Pulling gently on his hair that she had locked in her two hands, she pulled him up, further, further, till he was climbing on top of her. She guided his body till it was once again laying next to her. “Hold me,” she whispered. And he did. His gentle hands occasionally reached out to caress one part of her body or another. She did the same to him, occasionally gliding her hands over his body. Over and over again, she gently rubbed them over the breast forms glued to his chest. She toyed briefly with the fake nipples on each of the forms. Did he feel anything at all from her caressing there? She silently hoped that he did. Men had no idea what pleasures they were missing by not having breasts. But he wasn’t a man… well, he was… but he wasn’t. Not really.
She finally moved away from him, rolling off of the bed. “Stay,” she commanded softly. “I’ll be right back.” She watched till she saw him lay back, getting comfortable, ready to wait for her.
She left him and quickly went into her bathroom where she cleaned herself up and dried herself off. Then she donned her nightgown. Finally, she went back into her bedroom. He was still lying there, just as she had left him. “Don’t move,” she said softly. He only turned his head.
She found the package that held the collection of colorful dildos that had arrived in the mail. She opened it, and stared at the collection. Each one was in a different sherbet color. Each one had its own unique shape. There was one with a spiral corkscrew shape that seemed to catch her attention more than the others. She almost selected it, but then decided that maybe she would save that one for herself. She was tempted to grab the one that was ribbed like the one that Cassie had said that he seemed to like so much, but she didn’t. Instead, she grabbed the one with little tiny knobby bumps all over it. It too looked awfully interesting to her. Maybe someday. But today, she would see if he liked it.
She carried it to her bathroom where she tried to wash it off quickly, but there didn’t seem to be much of a point since it was already clean. She dried it off again. Time to play.
Chad heard her finally coming back. She had been gone for quite a while, well, away from her bed anyway. Could he take the blindfold off yet? He didn’t dare touch it or even ask. He was surprised to feel her removing the diaper she had just put on him such a short time ago. It was already wet – multiple times.
He felt her hands touching his chastity device, moving it slightly this way and that. Would she remove it? He hoped fervently that she would. But so far, she was leaving it in place. What was she doing?
Mel stared hard at his tiny penis, trapped inside of the hard plastic. She had tried playing with the device as best as she could, but as far as she could see, there was no reaction from him on the inside. None at all. Maybe something else would stir his interest. “Roll over,” she commanded gently.
Roll over? Chad was disappointed that she wasn’t going to remove the device. But he did as she told him and rolled over onto his stomach. He felt her caressing his backside for the briefest of moments, then he felt her wiping it with what felt like one of his diapers. Her hands came back. They lingered longer this time, then left again. He heard her doing something. He jumped as something cold hit his naked butt. Lotion. Then her hands were back again, rubbing it in, massaging it in. He nearly sighed out loud with pleasure as he let his body relax into the feeling. So nice.
Her head came down near his. “Pull your legs up,” she told him. He knew what was coming next… at least he hoped he did. It was definitely something that he wanted. He pulled his knees up under him, raising his backside up for whatever attentions he hoped she would give to it. He jumped as more coldness suddenly hit him, right on top of his anal hole. Then her finger was there, gently pushing, then firmer. He relaxed and with a wave of pleasure, allowed her finger to slide into him, spreading the lubrication all around. So wonderful. He hated feeling her finger leave him. But her finger was soon replaced by something harder. Something larger.
He felt her pushing firmly almost immediately. Not quickly, but firmly. Slowly she pushed it in. He nearly jumped when he felt the first little bump go past. What was she using on him? The first bump was quickly replaced by another one – in a different place. What the…? Then more, many more, all over. She continued to shove it in slowly, then she backed it out just as slow. He was constantly assaulted by the little bumps going in and out. Each one seeming to add so much to what he could feel, thereby increasing the pleasure he felt. Whatever she was using was different, but that’s the limit of what he was capable of thinking as she began pushing it in and out faster.
Within moments, he was pushing back and forth himself, trying to get even more out of the device than what he was capable of feeling. He wanted more. Much more.
Mel watched him reacting to her new toy. He seemed to like it. In a way, he was being used like a woman would be used by a man. Her thoughts turned again to the strap-on. Would he like it? It was without a doubt a bit bigger than what she was using on him now. But then he seemed to be taking that with no problem. But would he like it? Being fucked by her as if he was a woman? She considered trying it… strongly. But there was something about the act of doing it that she herself wasn’t quite ready for yet.
He was tiring, she could see it plainly. As he slowed, she slowed. She saw his fist pound against the mattress in frustration. No release. She felt sorry for him in a way, but she still wasn’t ready to release his penis from its prison. His denied ability to use that masculine appendage still meant too much to her. He stopped rocking completely. She stopped too. Then slowly she withdrew the toy. He didn’t move, he only continued to breath heavily, trying to catch his breath. “Roll over again,” she directed.
Chad heard her, but it was a moment before he found the will to do so. Slowly he rolled over onto his side, then onto his back. Still blindfolded, he felt her playing with his chastity device again. Would she take it off now? Now that they were finished?
Mel again looked hard at his tiny penis inside the chastity device. As far as she could see, it was still no bigger at all. She knew he had gained pleasure from her toy, but none of that pleasure had translated into a reaction from his primary pleasure point. Interesting!
He suddenly started peeing again and she quickly pulled one of the diapers over it to keep it from spreading. Did he even know he was going to pee? She could only hope not! “Stay here. I’ll be back in a few minutes,” she said.
Chad felt more then heard her leaving him. He was tired and frustrated… and glad for the break to just lay there and relax. Her bed felt good, far better than his little blow-up mattress. When she came back, she told him to raise his bottom up. He felt her sliding fresh diapers under him. A minute later, he felt her finger invading his backside yet again. The darn suppositories. He hated them. Why couldn’t she just forget them for once?
Mel pulled her finger out of him. She saw the look of displeasure on his face at having to have another of the suppositories. She smiled. What he didn’t know though, was that tonight marked the start of another piece of her master plan. Tonight was the first time he would be going to bed without one stuck up inside of him. She just needed him to think that it was there. Would he still mess himself like he usually did every night? She was fairly sure that he would. One at a time, she brought the disposable diapers up and pinned them in place. All four of them. Then she pulled the plastic panties onto him that she had grabbed from his diaper bag and pulled them up into place as well. He was now well padded. “Sit up,” she told him. When he was sitting, she finally removed his blindfold.
Chad blinked, then rubbed his eyes as soon as the scarf was removed from his head. He looked at Mel. She was dressed again – darn it! But then he had really expected that. “Stay here,” she told him. “I’ll be right back.” He watched her as she left the room yet again. He briefly wondered what she had in mind for him now. But he was mostly too spent to worry about it very much. He sat there on the edge of her bed and waited. She wasn’t too long. She came back with three baby bottles cradled in her arms.
“Sit up on the bed,” she told him.
He climbed back up on the bed and was surprised when she climbed up next to him. She set all three bottles on her nightstand, then sat up against the headboard. She stared at him for a moment, considering how she wanted to do this. “Lay down,” she said, then she patted her chest just above her breasts, “with your head right here.”
Chad wondered if she was planning on feeding him the bottles herself? That would be odd. Why? But he did as he was told and laid back with his head on her breast. He could at least dream of other, more pleasant, things. Of course, this was certainly pleasant. Very pleasant.
Mel grabbed one of the bottles and stuck it down into his waiting lips. She giggled a tiny bit as she did so. He took the bottle just like a baby. He was her baby. His eyes closed as he drank. She watched him nursing on the bottle for a very long time. When the bottle was finished, she replaced it with a fresh one. Gloria had been wrong. She had been wrong when she said that he wasn’t a baby that she could hold… or feed. Okay, so he wasn’t a real baby. But in all other ways, he was certainly close enough. Was this little action bringing out some of her maternal instincts? No, she didn’t think so… well, maybe some. But mostly no.
He was her baby in so many ways. Yet he wasn’t her baby at all… he wasn’t a baby at all. Which to her made the situation all the better. No, Gloria was definitely wrong about their relationship. It was just a fun relationship. Hopefully for him as much as it was for her. That was all she really needed it to be. Nothing more. But certainly nothing less.
When his second bottle was finished, she replaced it with the third one. He was drinking slower now, much slower. She yawned. She was tired, and sexually sated. Very sated. She felt wonderful. And holding him in her arms like that was nice. Very nice. His bottle was almost done. She was so tired. She pulled it out and set it on the nightstand. Still holding him, she scooted further down in the bed where she could be more comfortable. He didn’t move. Was he asleep? She needed to wake him and send him home, but she just didn’t feel like it yet. She’d do it in a few minutes. But one minute later, she was dozing herself.
Half asleep, she was too tired to get up. She was also tired of holding him. She shoved at him a bit to wake him. “Hold me,” she said. “It’s my turn.”
He woke out of his light slumber, surprised to still be there in her arms, surprised at her words. He shifted up higher in her bed and put his arm out. She laid her head on his shoulder and curled her body up into his. He couldn’t believe it. He was laying here in her bed, holding her while she slept. How did that happen? One thing he knew for sure though, he wasn’t about to do anything that might wake her. This was an experience to be remembered. This was an experience to be savored. He would hold her like this all night if he had too, and he would do it gladly.
Very slowly, he stretched his head down and lightly kissed the top of her hair. “Good night, Mistress,” he whispered softly. “Good night.”

The Bet - Chapter 31 (Monday – week 5 Part 7 of 8)

The Bet
by Karen Singer

Chapter 31 (Monday – week 5 Part 7 of 8)

Chad nearly died when he saw her turning into the mall parking lot. She didn’t really intend to take him in there, did she? Without realizing it, he started sucking on his baby bottle faster. The further into the parking lot they drove, the more panicked he felt. His baby bottle started sucking air. He discarded it and desperately grabbed his pacifier for comfort.
Mel was still trying to figure out how she wanted to do this. A small idea hit her. With a wicked smile on her face that he couldn’t see, she drove straight up to one of the entrances at the very end of the mall. She stopped the car right at the curb and turned around to face him in the back seat. He looked totally panicked. Good! Before he could protest, she started speaking. “Yes you are going in there… and you’re going in there just like that!” She thought she heard a small whimper from him, but he didn’t say anything.
“You’re going to show everybody exactly how much of a sissy you really are. And believe me, you better be convincing again or our next stop will be where you work.” She glanced at her watch. “And there’s still plenty of time to do the entire mall and get back to your company before they all leave for the day. And you know I won’t hesitate to take you there if I’m not happy.”
He nodded. It was the only answer he could give. He was too scared to speak. He certainly wasn’t looking forward to this.
Mel continued. “Maybe after we do a few more places like this today, you’ll think twice about being anything but respectful and submissive to anyone who talks to you… or asks you to do something. So I suggest you think about that carefully with every step you take in there. Got that?”
This time, Chad did manage to get a small “Yes, Mistress,” out of his mouth.
“Good! I don’t want you to ever get any ideas in that thick head of yours again that you’re anything but a sissy! You’ve been getting way too cocky lately, and I don’t like it! So remember, you’re a sissy! Sissies don’t argue – they do what they’re told! No questions!
“Now I want you to get out and stand right outside that entrance and curtsey to everybody who goes in or comes out till I get back from parking the car.”
Chad was horrified. Stand there? Alone? Why couldn’t he go with her to park the car? She couldn’t be serious about this! But she was just sitting there glaring at him menacingly.
“Out! Now! And I expect to see you proving to everybody that you’re nothing but a big sissy!”
Out? He still couldn’t believe it – she really wanted him to do this! Slowly, he unbuckled his seat belt amid the mass of ruffles that surrounded him. He glanced out the window before he opened the door. A few curious people had noticed him in the backseat of her car and stared as they walked by. What would they think when he got out of the car?
“I’m waiting!” Mel’s voice threatened.
Chad grabbed the door handle and opened it just a crack. Very slowly, he pushed it open wider… wider… then all the way. He slid around in his seat, letting his feet in their little girl shoes dangle down toward the ground. As he grabbed the door handle to help pull himself up, he saw two women just coming out of the mall, they stopped just past the doors and stared at him. He couldn’t blame them for staring. In a mass of ruffles, he got to his feet, outside of the car.
“Close the door,” Mel instructed.
Chad closed the car door with a clunk of finality. He was outside, exposed for everyone to see! He felt so embarrassed. He heard the front passenger-side window sliding down.
“I want to see a happy sissy,” Mel said. “Happy!”
Before Chad could react, the window was sliding back up again and Mel was driving off, leaving him standing there alone. He heard giggling behind him and he turned around. The two women had become several more, all scattered around the area in front of the entrance. Now what was he supposed to do? He couldn’t run… there was no place to run to. He would have to brave it out. He was stuck here, dressed as a total sissy for all the world to see. Mel had said to show everybody just how much of a sissy he was. Well, they could certainly see that for themselves by the way he was dressed. He didn’t know how far Mel would have to go to park the car, but he was sure that she would be coming back soon. She would be expecting much more from him than just standing where he was.
Doing his best to put a big smile on his face, he dropped one of his elaborate curtseys for all the people watching him, then he skipped away from the curb to stand in an area that was out of the way, yet where everyone could still see him. Mel didn’t say anything about singing or talking to the people, so he just dropped an occasional big curtsey to the people as they went past… or stopped to stare at him, as so many of them did.
How embarrassing! He felt like such a sissy! Of course, he was a sissy… for real. He just didn’t think he was this much of a sissy. He dropped another elaborate curtsey for another group of women. But maybe he really was this much of a sissy. He was standing here in a ridiculous dress, curtseying for everybody… in public. He couldn’t imagine anything being more sissyish than that. Of course, there was the wet diaper he was wearing under his dress too. That made him feel even worse.
Smile. Curtsey. Smile. Where was Mel?
“Love your dress,” someone teased as they walked past.
Curtsey. “Thank you,” he replied in his silly sissy voice.
“Is that a diaper he’s wearing under that thing?” someone else asked her friend.
“Must be. He is sucking on a pacifier, isn’t he?” her friend replied.
Curtsey. Smile. Mel, where are you? He was beginning to think she had left him alone there when he finally spotted her. But she wasn’t approaching. She was just standing and watching him from further down the sidewalk. Ugh! Curtsey for the nice people. Let them laugh. Curtsey again. What a fool he was. What a sissy!
He may have known that he was a sissy before… somewhere in the back of his mind. He may have even semi-admitted it consciously to himself. But he had never once thought of himself as this kind of a sissy… this much of a sissy. But here he was, smiling and curtseying like a fool to everyone that walked past. And he was really doing it. So if he was really doing it, then he must really be this much of a sissy. He was a sissy! A real sissy! A big, big sissy!
The embarrassment of that realization ran through him like an unwanted emotion. He wanted to cry, but he dared not. Mel said he had to be happy for everybody who saw him. He might be a big, big sissy, but he still didn’t want her to take him to work dressed like this. Curtsey for the nice ladies walking past and pointing. Did they see my diaper?
He finally saw Mel walking towards him. He was filled with relief at her approach. He curtseyed to her. “Am I doing okay?” he asked uncertainly. He really didn’t want her to take him to work like this.
“So far,” she replied. She stared at him for a moment. Should she? Should she really take him into the mall like that? She had been considering that very question as she had stood watching him. She still couldn’t make up her mind. “Are you learning your lesson yet?” she asked.
Curtsey again. “Yes, Mistress,” he replied. “I’m sorry I didn’t act right before.” Please take me home now, he prayed.
Mel glanced at the doors leading into the mall. Should she? She didn’t see any security guards there. Should she? Maybe just a quick trip! “Come along, Sissy. Time to go inside.”
Chad nearly died. It was bad enough behaving like this just outside this one entrance. But inside, there would be many more people.
With a deliberate, purposeful stride, Mel led the way right up to the doors and opened one. She held it open for him and waited till he passed through. They were now faced with another set of doors, the inner doors. This time, it was Chad who held the door for her… although he did so reluctantly. He really didn’t want to go inside like this.
Since they were at one end of the long mall, they entered straight into one of the big department stores – the men’s department. “Well, you certainly don’t belong here,” Mel stated as they walked through. Chad said nothing. The department was relatively deserted. A few people further away noticed them though and Chad noticed heads turning in his direction. A silly pink dress like he was wearing really stood out in the men’s department!
Mel led him along a winding path through the store. Fortunately, she wasn’t dawdling like she usually did, she kept moving. Department after department passed by. Then they were in the children’s department… little girls. “Now this is a much more appropriate spot for you. Isn’t it?” she asked as she stopped briefly.
Chad curtseyed. Actually, he never even gave curtseying a thought as he did it. “Yes, Mistress,” he replied in his silly voice. Mel smiled. Chad expected her to stop there and find some other way to humiliate him further, but she was off again with that same determined stride, as if she were heading somewhere and couldn’t wait to get there. He followed meekly as more and more heads turned to stare at him.
The further into the store they went, the more crowded it seemed to become. The women’s section was the worst.
“There he is!” Chad heard someone say as he followed Mel. “I can’t believe he’s actually in here!” Chad could only silently agree. He couldn’t believe it either.
The entrance to the mall interior was just ahead, just past the perfume. Chad half expected Mel to stop and do something awful to him, but she just kept going. Like a puppy on a leash, he continued to follow. Walking out of the store into the wide mall concourse was almost shocking. The number of people around seemed to increase. He no longer had narrow aisles stuffed with goods to hide behind. He was out in a fairly crowed large space where so many more people could see him. He wanted to run. He wanted to hide. His silly sissy dress was all too noticeable. The crazy ruffles that fluffed his skirt out so wide continually caressed his legs as he followed behind Mel, reminding him with every step just how much of a sissy he was – here in the heart of public exposure. If he wasn’t so scared, he would have cried. He did suck harder on his pacifier for comfort though.
Mel glanced around. No security guards as far as she could see. So far, so good. Did she dare take a chance with anything further? Throwing caution aside, she marched right into the heart of a large area where she had seen a small choir singing at Christmas time. She stopped there and turned to him. “Stand right there,” she instructed, “and face out into the mall.”
Chad turned around where he was. Why was she stopping here? He had been happier when they were moving quickly. He felt so exposed as more and more people stopped to look at him. He desperately wished for someplace to hide, but there was nothing around him.
“Curtsey for everybody,” Mel instructed from a few feet away. Hating having to do it, Chad dropped another of his overly silly curtseys. “Good,” Mel said. “Now sing ‘Mary Had a Little Lamb’ for everybody.”
She couldn’t be serious! But Chad knew she was all too serious. He really wanted to get out of there! He started singing, but quickly realized that he had forgotten about the pacifier in his mouth. How embarrassing… well, maybe not as embarrassing as everything else he was doing, but it was right up there. He pulled it out and started again. “Mawy had a wittle wamb…” He could easily see the looks of shock on the faces of all the people around him. Almost all movement stopped around him as he continued. All he could think about was how silly he had to look… how demeaning this was. And most of all, how much of a complete sissy he really had to be to be actually doing it! He hated himself.
Halfway through the song, he felt a slight tickling at the top of his leg that had nothing at all to do with the soft ruffles under his skirt. He realized he was peeing again and that his diaper was starting to leak. As he sang, he turned to Mel with a worried look on his face and held out that leg and shook it a bit. He was relieved to see a slight nod from Mel’s head.
He finished singing and curtseyed without being told to. He heard more than a few chuckles while one older man actually clapped – surprise! He dropped another curtsey to that nice gentleman.
“Okay, Sissy, let’s go,” Mel said.
Once again, Chad followed her determined stride as she made her way through the mall. So many people. So many people all witnessing how much of a sissy he really was. Did any of them see his diaper leaking? He hoped not!
Mel figured she was pushing her luck. It was time to get out of there. No security in the way yet, but she didn’t want to tempt fate. With Sissy in tow, she headed straight for the nearest exit. She felt nothing but relief as she walked out through the mall doors and into the bright sunshine. Now to find the car. Fortunately, it wasn’t all that long a walk back to it – shorter than if they had gone back through the mall. Sissy may have been the one on display, but she was the one responsible for him being there. She didn’t want either of them to come to any trouble over what she had just made him do. She breathed a sigh of relief at reaching the car. She glanced back the way they had come. No security or anyone else following them. Whew! Made it!
But now she had another piece of business to attend to… and somehow it felt perfectly right to take care of it right here and now. “Okay, Sissy. Let’s get that diaper changed before you get in the car again.”
Chad nearly died. Yes, he was leaking, but still… Here in the parking lot? Again? In very short order, he found himself standing between Mel’s car and another car, doing his best to hold his voluminous ruffles out of the way while Mel removed his soggy diaper and replace it with a dry one. The whole situation seemed to catch up to him. There was something about having his diaper changed, in public, while wearing that sissy dress, after what he had just done in the mall… that totally got to him. It started as a single tear escaping his eye. Then a small sob got past his pacifier. A moment later, he was crying softly as Mel finished with his diaper.
“What’s wrong?” Mel asked.
“I’m a sissy,” was all he was able to say. With head held down, he climbed into the back seat of Mel’s car. He was a sissy. He wasn’t a man anymore. No man would ever come close to doing anything that he had done today – all day. He was a sissy. He had done those things. Not a man.