The Bet - Chapter 26 (Wednesday – week 4 Part 1 of 6)

The Bet
by Karen Singer

Chapter 26 (Wednesday – week 4 Part 1 of 6)

Small. Insignificant. Worthless. Pathetic. Again and again his dreams hammered home how he felt about himself. Along with other emotions: unworthy, useless, stupid, perverted… defeated… unloved. He tossed and turned as much as his breast forms, chastity device, and overly bloated diapers would let him. Their constant confinement punctuated his dreams and increased his restlessness – as did the itchy irritation all across his backside from his diaper rash. Small, insignificant, pathetic. Unloved… Deserving of, and doomed to endure, the humiliation he felt even in his sleep… which now included the constant irritation and humiliation of diaper rash.
Yet despite his feelings of self-pity, the images of himself wearing skirts and heels… and diapers, filled his dreams… and excited him beyond belief. They pulled him, over and over again, to the brink of waking up. And over and over again, still mostly asleep, he drifted back deeply into his dreams once again. Because even in his dreams, he knew he had no hope of relief – or even obtaining any of the pleasure he used to associate with those feelings of want and need. No hope. No feeling. Numb.
Yet the need still resided throughout his entire body, driving his dreams relentlessly to show him, over and over again, the very things that fed his insatiable need. His unrelieved need was so great that it never let up. It was always present, at least in the background, of everything he could possibly dream. Unrelieved need. Raging excitement. All of it now leading to nowhere. No hope of the feelings he craved. No hope of relief. Only emotions that left him feeling nothing but insignificant and worthless. Restless sleep.
The shocking volume of loud rock music pulled him out of one last dream where he crawled at the feet some unknown woman – who bore a striking resemblance to Mel. He opened his eyes, totally disoriented for a moment as the images of that powerful woman erased themselves from his mind. The feeling of self-pity lingered however as he stared uncomprehending at his blank ceiling.
It was a moment before the irritating music made him realize that he had to do something about it. Wanting only blessed silence – and to go back to sleep again, he pulled himself to his feet where he could reach his pink clock radio and shut it off. The loud music suddenly ceased. Relief swept over him as silence returned. He glanced down at his blow-up mattress, wanting desperately to go back to it, but he was awake enough now to know that he couldn’t do that. It was another day. Another horrible day. Another day of servitude and total humiliation – from which he couldn’t escape.
As he stood there, pondering his life and trying to make sense of it all, he felt himself suddenly wetting his already overly wet and messy diapers. Damn! Why didn’t he realize he had to go? The answer was simple – it was because his body was still too much asleep. And if he didn’t get moving and wake himself up fully, then it might happen again… or worse. And part of him really didn’t care at all – because he didn’t really mind wetting himself uncontrollably – he loved it in fact. But there were reasons out there that spelled out why he didn’t want to do it. Reasons that at that moment he didn’t care much about, but he knew he would care about them later.
He suddenly realized that he had been unconsciously rubbing at the back of his diapers – trying desperately to quench the itch of the diaper rash that was invading his backside. But his diapers, even when dry, were far too thick for his rubbing to have any affect. And now… it was a totally useless motion. He concentrated on the itching under his soaked and messy diapers. It felt at least as bad as it did yesterday… possibly a bit worse. Probably because he had been wet and messy through most of the night.
He gave one more wishful glance at his blowup mattress and forced himself to walk away from it, out of his bedroom and into his kitchen. Had Mel left him another note? Most of him hoped so, but part of him hoped that she didn’t – because all too often her notes meant more humiliation for him. And he had enough of that in his life already.
Her note was right where it always was, right on his counter where he couldn’t miss it. It was very short. Three more bottles before he left for the morning, dress as usual, and one side note – from now on he had to include one of his waist cinchers as part of his normal everyday dress. Oh goody – Not!
Still feeling nothing but self-pity and loathing for his life, he grabbed a bottle of Mel’s foul tea from his refrigerator and carried it out to his one and only chair to sit and drink it. It wasn’t till he tried to put the nipple into his mouth that he realized that he was still sucking on his pacifier. Damn! He just knew it was going to be one of those days!

Mel woke up only minutes before her alarm buzzed. She turned it off before it could ring and swung her feet over the edge of the bed to sit on it. She breathed in deeply, feeling fairly good for once. She got to her feet and grabbed her robe, pulling it around her as she headed out to her kitchen. Fixing her morning coffee was so ingrained in her habits that she never gave it a moment’s thought. Instead, her mind was filled with thoughts that revolved around Sissy… or rather Chad… no, definitely Sissy!
She smiled at the thought of some of the things she and Cassie had researched on the internet last night… and she blushed at the thought of some of the things that Cassie had talked her into ordering later. Had she really spent money on them? And especially on one embarrassing thing in particular? What kind of woman was she? It was unthinkable! Yet as she pulled a fresh mug out of her cabinet to pour her coffee into, she chuckled to herself. Yes, she had really bought it… even though just thinking about it made her feel dirty… but in a way, excited.
With her coffee made, she poured herself a cup and carried it over to her desk. She sat in front of her laptop and took a sip. Mmmm. She powered up her computer and continued to sip at her coffee while she waited. She went into her email as soon as she could. Yes, there were the order confirmations. She opened each one, staring at the name of each item. Damn! She had really done it! She, the one who had always considered herself to be the “good” girl, had actually ordered each of those items. She checked the expected delivery dates on all of them. Since she was having them all delivered to her office so they wouldn’t sit exposed on her doorstep all day, she figured they would all arrive either Monday or Tuesday… an eternity to wait.
Her only problem with having the packages come to her office was Andrea. She was really too embarrassed by what would be in each package for Andrea to know about them. Was there any way she could keep it all secret? Of course there was – if she simply didn’t tell Andrea what was in them. But Andrea was her friend too. In a way, it wasn’t right. But in this case, it was probably more right to be closed-mouthed and not tell her… or more polite anyway.
Had she really ordered this stuff? The proof was right there in the emails in front of her. And further proof would be hers as soon as the packages arrived. She couldn’t wait!

Chad was as naked as he was capable of getting as he stood in front of his closet and stared into it. What should he wear? Deciding what to wear was always a problem, but he hadn’t counted on having a further dilemma today. While he had been in the shower, he had remembered that he only had one pair of pants left that he could wear this week. Only one pair of pants till next Monday! And it was only Wednesday! That would mean wearing skirts on Thursday, Friday, Saturday, and Sunday… four days in a row! But he could break that up a bit if he wore a skirt to work today instead of tomorrow. Would it be better? That was his dilemma. Should he? Or shouldn’t he? Did he want to wear a skirt today – rather than tomorrow? Or not?
The very thought of it, wearing a skirt to work again, made him nervous and scared – while at the same time it excited him immensely – which he didn’t really need. In the end, his choice came down to deciding to wear one four days in a row, or three. He finally decided that four days in a row was a bit much, even for a real woman. So he turned his attention in his closet to only his skirts. But now, what skirt outfit should he wear? His frustration built as he stared at what he had. He just wasn’t good at matching them up! He vowed that he’d ask Mel to help him with it later. But for now? He finally grabbed the same skirt and blouse outfit he had worn to work last Friday – only because he knew they were made to go together.
With that decision out of the way, he tried to turn his thoughts back to getting ready for work again, but he couldn’t get the fact that he was actually going to be wearing a skirt to work again out of his mind. His diaper rash felt much the same to him as it had last night. Obviously the cream that Mel had bought wasn’t doing much good. Of course he didn’t know how long he had been laying in messy diapers all night. He had no recollection of messing them at all – as usual. He carefully coated himself very liberally with the new ointment he had bought yesterday, praying all the while that it would work… and quickly!
Two disposable diapers, one with the cover slashed to let the wetness through, covered his rash and chastity device a few minutes later. A pair of plastic panties with nursery print characters all over it covered the diapers. The waist cincher was next, followed by another one of his all-in-one girdles. The girdle was so small and tight that it constantly pulled hard on his shoulders. It was a chore just to stand up straight in it.
His pantyhose would have been next, but he remembered how difficult they were to get on yesterday. He chose to work on his makeup and hair next instead, taking his time so as to delay both the ordeal with the pantyhose and the ordeal of wearing a skirt for the rest of the day – he still found it very hard to believe that he was about to go to work in one again.
With his hair still slightly damp from his shower, he rolled section after section around his curling iron and let them “cook.” Each time he removed the iron from his head, the hair sprang back into tight curls. Curls that spelled out “sissy” with each one that he created. But what was he going to do about it? It took a lot of time to do his entire head, but he was in no hurry. Sissy curls. Sissy curls. Sissy, sissy, sissy! He ignored the ever-present sexual urges that built up inside of him with each curl that he created as he worked to make himself even more of a sissy – because again, there was nothing he could do about it.
With his hair out of the way, he turned to his makeup, covering his face with this and that. Spreading and blending. Adding color and texture. Removing – maleness. Finally, he was down to just needing his lipstick. He twisted the tube of lipstick open and was about to add it to his lips, when he paused and stared at himself in his bathroom mirror. The lipstick was the most blatant color he would be adding to his face. A close match to his super-long fingernails. Why was he doing this? Why was he deliberately showing the entire world how much of a sissy he was?
It would have been easy to place the blame for that one on something like… because of the bet… or because Mel had ordered him to. But wallowing in self-pity as he had been all morning didn’t let him see anything but the plain truth. And the truth was, he was doing it all, because he had dreamed of doing it all his life. He had always dreamed of wearing girly clothes. And he had also dreamed of being in diapers and being helpless and babied. They were strange, conflicting yearnings that didn’t really belong together. Yet they all lived together deep inside of him. They had become so much a part of his very soul that it was impossible to separate his strange yearnings from the rest of him.
Bottom line? He was doing it all because he wanted to. As much as he could try to deny it, the simple truth was that he was doing it all, because deep down, he really wanted to. He sighed and stared at the lipstick in his hand. There was no use delaying the inevitable any longer. Feeling even more self-pity, he applied his lipstick, blotted it, and stared at the results. Sissy!
Battling with his pantyhose, actually proved to be a diversion from the thoughts that had invaded his brain while he had been doing his makeup. He had to fight to get the darn things on because his waist cincher wouldn’t let him bend easily enough to get them over his feet. How did women deal with wearing waist cinchers? Dumb question… they usually didn’t! It wasn’t till after he got the pantyhose on that he remembered thinking yesterday about not wearing pantyhose today. Too late now! He wasn’t about to try to take them off again – especially not after fighting so hard to get them on.
He could delay it no longer. He grabbed the skirt and pulled it on, zipping it up at the side easily… too easily. Just as with his pants, the skirt hung a bit lower than he thought it would because of his compressed waist. But the skirt wouldn’t drag on the ground the way his pants would, so he just left it to hang a bit below his knees. He pulled the matching top on and stared at his reflection in the mirror. Was it acceptable? He only hoped so.
He decided to go for at least one bit of comfort and slipped into his low-heeled shoes, noticing as he did so how really nice they felt compared to wearing much higher heels every day as he had been doing.
It was time for the finishing touches. He went in search of his jewelry.

Mel glanced at her clock and was a bit surprised. Where had the time gone? She had just sat down at her computer to work for a bit because she had had an idea about one of the cases she was working on… but that tiny idea had become a bigger idea, then it had blossomed into other ideas and areas. Now she had to hurry. It was almost time for Chad… or rather Sissy to get there.
She ran into her kitchen and quickly started preparing his baby-food breakfast. She had no doubt that he hated the stuff, but tough! She knew it humiliated him and she rather enjoyed watching him suffer through it. Besides, it certainly wouldn’t hurt him.
There was a small polite knock at her door. She glanced at her clock one more time as she ran to answer it. He was right on time. Good! She opened her door and got a bit of a surprise. While he was busy curtseying and greeting her, she noticed immediately that he was wearing a dress again. Wonderful! Although it was exactly the same outfit he had worn before. “Good morning, Sissy,” she returned happily as she stood back out of the way to let him in.
Chad entered her apartment and set his purse and diaper bag down in their usual places under the table by her door. Then he stood where she could “inspect” him. As she looked him over carefully, Chad couldn’t help but notice the broad smile on her face, he figured it was because of the dress he was wearing.
“You surprised me,” Mel said, as she turned and walked off toward her kitchen.
Chad immediately followed. “Why? Because I’m wearing a skirt again?”
“You got it!” she replied with a wicked look back over her shoulder toward him. “But I’m also surprised that you’re wearing the same outfit you wore last time. You’ve got lots of skirts and dresses in your closet. Why didn’t you pick something different?”
Chad shrugged. “I don’t know what blouse goes with what skirt?” he replied with more than a bit of frustration.
“What do you mean? You’ve got lots of possibilities there. We made sure of that when we were shopping.”
“Yeah, there’s lots of stuff, but what can I wear with what?”
Mel looked back at him as she continued to stir his baby cereal and just shook her head. She motioned toward his highchair. “Climb up.”
Chad took the tray off of his seat and set it on the floor, leaning it up against the chair. Then he climbed awkwardly up into it, trying to settle himself so his diaper rash wouldn’t hurt too badly.
Mel saw him wince and noticed his discomfort as she pulled one of his bibs out of a drawer. “Diaper rash still bad?”
Chad sighed. “Yeah. It’s no better than yesterday. Mistress, can’t I go without the suppositories… at least just for a few days… at least till this rash clears up?”
“No!” she answered flatly and final as she approached him with the bib.
Chad didn’t even try to protest any more as she tied the bib around his neck. A minute later, the highchair tray was back in place and he was spooning the first of many tiny spoonfuls of the cereal into his mouth. If she wouldn’t let him go without the suppositories, then how was he going to clear up his diaper rash? He looked up at her as another idea hit him. “How about letting me have less bottles to drink for a few days? That might help.”
“No!” Again her answer was plain and simple and final. “Just give it time and keep putting that ointment on it. It will clear itself up soon.”
Chad made no answer as he spooned another tiny batch of the lousy cereal into his mouth. Mel wasn’t going to budge – on anything. He had a feeling that he was going to be doomed to suffering with the diaper rash for a very long time – because so far, the cream they had been using had done nothing at all.
Mel stood behind her counter and watched him struggling with the tiny baby spoon to get the cereal into his mouth. Mostly, he was succeeding now. He was getting better than he used to be at using the infant spoon. “So you need some help sorting out some outfits to wear?”
He looked up. “Yes… please! I just don’t have a clue.”
She chuckled, “We’ll spend some time on it tonight.”
He actually felt relieved. She was going to help. But as he shoved more of the baby cereal into his mouth, he realized that feeling relieved over what she was going to be helping him with was really very odd. It was strange that he was happy because she was going to be helping him select skirts and dresses he could wear to work! And he would be wearing them to work… eventually! And while he was still scared about it, he was excited by the idea too. Damn he needed some relief!