The Bet - Chapter 15 (Saturday – week 2 Part 1)

The Bet
by Karen Singer

Chapter 15 (Saturday – week 2 Part 1)

In his dreams, he was awash inside of a desperate need. It seemed that everyone… make that everything, around him was in a constant state of orgasmic ecstasy… except him. He alone felt nothing. Numb! While all around him was in the deep throws of sensation, he desperately willed himself to feel something, anything. But no matter how hard he tried, all he felt was nothing.
A sudden sensation to the very part of him that was most numb suddenly came through to him and in his sleep he reveled in it. He realized he was peeing. The only feeling he was capable of feeling there now. He relished every bit of the feeling, concentrating on it more and more. As his peeing slowed down, the numbness began to return, till there was nothing again. The only thing he could feel anymore was gone again. He was angry that the feeling was gone. He wanted it back again, badly. It bothered him, more and more… till he awoke.
Sunlight streamed in past the shade drawn down on his window. His pink clock radio hadn’t gone off yet. He looked at the time – it was late. Surprisingly late. Mel usually told him what time to set it for at night, or she set it herself. Either way, his alarm wasn’t set. He quickly got up and waddled into the kitchen to see if she had left a note. She had.

Sissy,

You have most of the day to yourself today to do whatever you want – enjoy it. But while you’re off, make sure you buy at least five more packages of diapers.

I expect you here at three o’clock sharp!
Shave your legs
Two fresh diapers
Makeup
Girdle with padding
Pantyhose
The rest is up to you but don’t wear your low-heeled pumps.

For later -
Make sure your uniform and apron are clean and freshly pressed!
Make sure your low-heeled shoes are freshly shined!
Carry them with you when you come but don’t wear them.
I will be inspecting you later!

The rest of the day is yours to do with as you please.
Enjoy it and don’t call me!

Completely shocked, he continued to stare at the note without reading it. Most of the day off! It was so unexpected. Mel had never indicated anything like that. Other than the order by buy more diapers that he really needed, she hadn’t given him any instructions for anything till the time she had specified. Nothing at all. Not even a demand to drink another baby bottle. Thinking about the bottles, which had always been first on her list, he realized he was thirsty. Since he had nothing else in the house to drink, he went to his refrigerator and pulled one of the many bottles out and put it to his lips.
Sucking on it, he headed back towards his blow-up mattress to figure out what to do with his morning. His eyes fell on the maid’s dress that was still in the pile where he had dumped it when he came in last night. She had mentioned clean and pressed. The dress still had some faint creases from where it had been folded in the package. He didn’t even have an iron. As he sat down on his blow-up mattress with his bottle, he figured he could buy an iron. Heck, he probably needed one anyway. Buying an iron was something he would have had to do anyway since he had just moved in. Was there anything else he needed while he was at it? He decided to make a list.
He got up again and poked through some of the boxes that were stacked in his room till he found an old notebook to write on. He went out to the living room and pulled his pen out of his purse. Then he went back to his mattress again. Five bags of diapers. An iron. Then he realized that he’d probably have to get an ironing board to go with the iron, so he added that to the list. Mel had said he had to have his shoes freshly shined so he added shoe polish. But what else did he need? Nothing was coming to his mind right away so he nursed on his bottle while he tried to think of things.
He didn’t think that going to the store was going to take all that long so he also tried to figure out what else was he could do for the rest of the day? He had no ideas.

Mel rolled over in bed and stretched. It felt good to be lazy and sleep in for a change. The many orgasms she had enjoyed at Chad’s expense last night still left her feeling wonderful. The fact that her period was all but over wasn’t hurting either.
She thought about Chad and the note she had left him last night. She wouldn’t be seeing him today till much later. They had been stuck too closely together for a long time now. They both needed a little bit of space for a change. She thought again about what she had put into her note. Not much really. But hopefully, today Chad would start to realize that even in his freedom he was on a very short leash.
She needed some coffee. She got out of bed and headed towards her coffee maker, thinking about Chad in his maid’s uniform all the way.

Chad decided he was hungry and immediately thought about his favorite fast-food place. He had most of the day ahead of him, time to start making the most of it. He got up from his mattress and headed into the bathroom to clean up. He carefully removed his diapers and climbed into the shower to wash the mess off. He soaped himself up with the flowery scented soap that he had now and washed his hair with the equally fragrant shampoo. When he was done, he dried himself off, taking extra care around the chastity device that he couldn’t remove so as not to hurt himself by pulling on it too much.
He shaved with his pink razor using the moisturizer instead of shaving cream because it was all Mel allowed him to have. His legs! Mel had said he needed to shave them today! He had never done that before himself. He turned the shower back on and climbed back in, this time with his razor. He quickly discovered how difficult it was to shave his own legs. He bent over this way and that way, trying to reach different parts of his legs, sometimes feeling like he was going to drown from the constant shower water streaming over him. He put one leg up on the edge of the tub to reach places and then the other. It was difficult, not at all like trying to shave his face. And it took a whole lot longer.
When he finally finished, he got out of the shower again and re-dried himself off. Mel’s note had said that he could do whatever he wanted. As far as he could see, that included not wearing diapers, or anything else he didn’t want to wear. He didn’t have any underwear, but he could easily go without.
He left his bathroom and opened his bedroom closet. There was a very disappointing selection of clothing to choose from. The only male clothes in the closet that he could get to, were his shirts. No male pants or shoes or socks or underwear. Being able to wear what he wanted still didn’t leave him many options. Feeling a bit despondent over it and not having a whole lot of choice, he selected a shirt and a pair of women’s slacks. He put his shirt on and buttoned it up. It felt like total freedom. No girdle, not even a bra under it. Absolutely wonderful. He wasn’t as happy about pulling the women’s slacks on, especially with no underwear at all, but still, not wearing diapers felt like a tiny victory.
He stared down at the shoes. There was really no choice other than the low heeled pumps. All the others were high heels and today he was trying to be as male as he could, or at least less noticeably a sissy. The clothing choices available to him just weren’t helping.
As he was about to slip the shoes on, he suddenly felt the urge to pee and before he could react, he discovered that he was wetting himself. He ran back to the bathroom, still peeing all the way. It didn’t stop till he got to the middle of his bathroom floor. He stood still there, angry at himself for wetting like that. Why had he done it? Then another realization hit him. Why didn’t he stop it? That was totally stupid! He could have held it easily. Why didn’t he?
His slacks were soaked, as were his legs. He had to go back into the shower once again to rinse off. While he was in there, he realized that part of his problem was that Mel now had him so used to peeing constantly that he wasn’t holding back anymore. All his muscles were totally relaxed. He wasn’t even trying to control himself. He decided right then and there that he had to start controlling himself constantly now, no matter what Mel put him through.
He tried to tighten all those muscles, just to flex them. He hadn’t done it in a long time now… days probably! But he was having a problem doing it. It was like he couldn’t remember how to tighten them. There were muscles there, but his brain seemed to be looking in the wrong place to make them react. It actually took him a minute to figure out how to tighten his muscles again. He was only able to tighten them a little bit at first, but once he had done it a few times, it became almost normal again. The only problem now was that keeping them tight again didn’t feel normal, and it felt like it was difficult to do. It certainly wasn’t comfortable.
He couldn’t believe how affective all her baby bottles had become. Frighteningly affective! If he hadn’t caught himself now, he realized that she might just have won the bet, and all too quickly. But he was fighting back now, and he was more determined than ever. From his prior research, he knew that it took about three weeks for a person to really form new habits. But he was peeing unconsciously in his diapers now without ever giving it another thought, and it had only been two weeks. He found that thought, not only disconcerting, but strangely, arousing. Fortunately, his tiny little member made no effort to grow any bigger and he never felt any little pinpricks of pain from his chastity device.
When he got out of the shower again, he decided that it was easier to leave those muscles relaxed where they felt more comfortable and normal, and then he could always control himself only when the need arose. But because of that, he decided to err on the cautious side and wear just one diaper… just in case! As he pulled his second pair of women’s slacks on for the day, he was aware that even though he was wearing a diaper, the slacks felt more normal and comfortable because he had some kind of underwear on under them.
Just to be different, and to try to disguise the fact that his pants were women’s, he decided to try pulling his shirt out and leave it untucked. The tails of his button down shirt hung fairly low. It looked a bit sloppy, but overall, he was very pleased with the affect. Unfortunately, it was ruined a bit more as he finally slipped his low heeled pumps on. But what choice did he have? Other than high heels.
He headed for his door and picked up his purse. He was tempted to leave it behind, but he was only planning on going through the drive through, so nobody would actually see it. Hooking it over his arm, he walked happily out his door and down to his car.

Mel walked around her apartment wondering what to do with herself. Normally, before Chad, she would have spent several hours on either Saturday or Sunday, or both, doing laundry and cleaning her apartment. But she had Chad now to do that. It was wonderful, but now what was she supposed to do with her free time? She had some work that she had brought home with her that needed to be done, but she didn’t really feel like doing it just then. She could go shopping, but most of the stores probably wouldn’t be open for a little while yet.
She sat down in a chair in her living room and tried to figure out what she wanted to do. She had no idea. Her thoughts naturally turned to Chad. She wondered what he was doing.

Chad carried his fast-food breakfast up the steps along with his coffee, still in its cup. He let himself into his apartment and set it all down on the kitchen counter. He took a sip directly from the cup. No baby bottles! A distinct pleasure. He ate his sandwich greedily. With no suppositories in his system, he enjoyed it even more since there would be less of a chance of something else happening.
When he was done with his breakfast, he wandered around his apartment for a bit because he had nothing better to do. He wiped his kitchen counters down even though they really didn’t need it and he did the same with his bathroom. He would have cleaned his toilet but wrapped up in so many layers of Mel’s cling wrap, that was impossible. He only glanced at his toilet out of the corner of his eye. He always avoided looking at it because it made him feel funny. It was too much of a direct reminder of what he could no longer do.
Straightening up his apartment hadn’t taken very long so he went back to his living room and sat down in his one and only chair. He had no TV. He couldn’t do laundry because he didn’t have a washer or a dryer. He couldn’t get on the internet because he not only didn’t have an internet connection, but his wife – make that ex-wife, had gotten their laptop in the agreement. He briefly wondered if Mel might spring for a new laptop too when he finally won this bet.
The boredom finally got to him and he realized that he had been putting off leaving his apartment again. It was time to get the shopping over with. He got up and grabbed his purse again and stopped. Did he really need his purse? He only needed his keys and his wallet and his cell phone. But Mel had said that he always needed to carry his purse now. Just in case she might be looking out the window, he decided to carry the purse just to his car. Once he got to the stores, he could always just carry his wallet and keys in his hands.
He headed for his door and had to stop again as he felt the urge to pee come over him quickly. He was able to stop it, but not until some had already leaked out into his diaper. He was more glad than ever now that he had decided to wear the diaper. The thought that he had been able to control himself even somewhat, made him glad.
But he had another problem now, should he just pee into his diaper like he had been doing, or try to get undressed and pee into the tub instead. Unfortunately, the urge was quickly growing stronger… too strong. With a sigh of relief, he let it out into his diaper. Then, because he didn’t want to wear the wet diaper to go shopping, he went back to change it. The decision to change himself also gave him a reason to delay going out in public again. He was happy about that.
Once he was changed into a fresh diaper and fully dressed again, he had no further reason to put things off. He grabbed his heavy purse and went down to his car.
He stopped at a drug store first to get the five packages of diapers. He didn’t want to carry his purse inside so he just grabbed his keys, his wallet, and his cell phone. His hands were a bit full, but at least he wouldn’t be as noticeable or embarrassing. He got out of his car and headed into the store. As far as he knew, with his shirt untucked, the only thing really sissy that was visible about him was his shoes, oh, and his stupid electric pink fingernails. But hopefully, nobody would even notice.
There were a few customers in the store when he walked in, but it was early enough that there weren’t really very many. Something he was glad to see. He knew very well where the adult diaper aisle was and he headed straight for it. But when he got there, he discovered that they only had two bags of the diapers he needed. Nothing else in his size. Should he get the two bags or go somewhere else? He finally decided to get just the two bags.
With his keys and his wallet in his left hand and his cell phone in the other, he pulled out one package that was down on the bottom shelf. The large bag was awkward to carry with his hands full. He fumbled around with it till he got it stashed precariously under his left arm where he was carrying his keys and wallet. Then he tried to reach for the second bag. But the only hand he had to grab the bag with was only partially useful because he was still holding his cell phone. He finally nudged the bag out to where he could try to pick it up. It was a bit difficult to do, but he finally got it wedged between his body and his arm. He stood up and got halfway down the aisle, and the first bag slipped out from under his arm and fell to the floor. To pick it up, he transferred the bag in his right hand under his left arm where the fallen package had been. Then to make matters easier, he also carefully transferred his cell phone to his left hand too so that he would have all his fingers of his right hand available to help pick up and hold the second package. He found that it worked much better that way.
He was almost to the checkout counter though when he realized that he was having trouble holding onto his wallet, cell phone, and keys in one hand all at the same time. He didn’t have trouble long though, because his cell phone slipped out and fell to the hard tile floor. He stepped back to see where his phone had landed, and immediately saw that the cover had cracked at the hinge. He was so angry he wanted to kick the phone. But he controlled his anger as best he could. Feeling devastated by what he had just done, he dropped the two huge diaper bags on the counter and picked up his cell phone. He looked at it carefully. Broken! No doubt about it. He was going to have to get a new one.
He paid for the packages of diapers with his credit card so he wouldn’t have to deal with bills and change, and the clerk put each of the packages of diapers into a separate bag because the store didn’t have any bags big enough to hold more than one. Lugging the two big bags out to his car, he mentally cursed himself for dropping his phone, and for not carrying his purse which would have made it all easier, and finally for entering the bet in the first place. Unhappily, he drove out of the parking lot in search of another drug store that would carry the diapers he needed.