The Bet - Chapter 17 (Monday – week 3 - Part 1 of 3)

The Bet
by Karen Singer

Chapter 17 (Monday – week 3 - Part 1 of 3)

His dreams were total confusion. He was confused. The situations and images were confused. One minute he felt lost, alone, adrift, forgotten. The next he was overloading on sexual want and need, feeling the punishing pain of his chastity device even in the dreams of his sleep. Constantly changing dreams. Dreams where he was proud of himself. Followed by dreams where he was completely unnoticed. Followed by dreams of being stuck in high heels forever. Followed by dreams of playing pool on his new pool table. Followed by dreams where he was wetting himself uncontrollably. Back and forth the dreams flashed. Faster and faster. Exploring and changing emotion after emotion. The situations and feelings coming at him faster and faster, stronger and stronger, mixing the emotions so that he could hardly tell them apart. Until they all rolled themselves all up into one loud crashing crescendo… that was his pink alarm clock suddenly blaring loud rock music into his room to wake him up.

He awkwardly rolled over on his blow-up mattress and stared at the ceiling while he tried to clear his confused head. His chastity device was hurting him and he tried to figure out why. It must have been something he was dreaming. Pity he couldn’t remember it though. He struggled to his feet and turned off the music. It was Monday. He’d have to go to work… again.
The first thing that fully made it through to his sleep fogged brain was a question. What instructions had Mel left for him during the night? Only one way to find out. He began slowly waddling towards the kitchen. As soon as he began walking, the urge to pee hit him. He almost let it out without thinking, but he caught himself just in time and with a modicum of effort got it fully under control.
What a strange night last night had been. He had cooked dinner for the girls, and then they had ignored him… completely - as if he weren’t even there. No thanks, no praise, no acknowledgement of any kind! For hours! After they finally released him from his corner, he had cleaned up the kitchen and then just waited. They never even spoke to him. The only time anyone even looked at him was when Mel came through to get yet another bottle of wine. She didn’t even ask him to get it for her. As if he was nothing but an appliance in her kitchen that she didn’t need just then. Like a toaster.
And when Sandy and Cassie finally left, Mel sent him straight home too. She didn’t shove one of her stinking suppositories up his butt, heck, she didn’t even rediaper him or give him any instructions. Nothing! Just a “See you in the morning,” and that was it! Weird!
As he reached his kitchen he got huge shock. There was no note! Nothing! He searched the floor in case it might have fallen off but he couldn’t find anything. He felt panicked. She had never done this before! What was he supposed to do? He literally waddled in circles in his kitchen trying to figure it out. He couldn’t remember her telling him anything that he should have remembered. Should he get another baby bottle like he always did, or didn’t he have to bother? What clothes did he have to wear?
Fearful, because she always checked to make sure he had finished the required baby bottles, he pulled one out of his refrigerator and sat down with it in his living room chair. Once again, he felt ignored and adrift.

Mel woke up with her mouth tasting like dried cotton… well, maybe not that good. Her head felt like it was stuffed with wool. She dragged herself carefully out of bed and went into the bathroom to brush her teeth. Too much wine always did this to her. She hated herself for it. No matter how much fun she had the night before, she always paid for it then next morning. It was the wine… every time.
Brushing her teeth helped some, but not as much as she would have liked. She plodded to her coffee pot and turned it on. It wasn’t till she stood there watching it dripping into the pot that she finally thought about Chad. Dinner had been great last night. He had done really well. Everything had been perfect. He was really on his way to becoming her greatest fantasy. In some ways, he was already there. She loved seeing him in his formal maid’s dress. But Cassie and Sandy had been bored with it. Yeah, she understood that and yeah they were right. What an evening she had had buying him new outfits. She didn’t want to think about how much money she had spent last night. A small fortune probably. Of course she also couldn’t really remember what she had bought him either. She had been in too much of a hurry to bother printing anything out. Stupid! But she guessed that any packages that came in now would be like wonderful surprises. She’d just have to wait and see. That was always fun.
She suddenly remembered something else, she had forgotten to leave him a note with instructions last night. Stupid again! Too much wine! Well, she’d just have to see how he showed up later. If she didn’t like what he was wearing then it would really be her fault, not his. Of course, he didn’t have to know that. She could yell at him about it whether it was her fault or not.
Feeling a little bit happier, she poured herself some coffee.

Chad got out of the shower and dried himself off. Should he wear two diapers like she always told him, or didn’t it matter. Deciding to be cautious again, he went for the double diapers. Besides, he could worry a whole lot less about leaking that way. But how about everything else? Even though he was holding back now, he still had to do everything in his diapers. Heck, he didn’t even think about using a bathroom anymore – he sometimes found that very convenient! So he added the plastic panties because they provided a lot of added protection against leaking.
Did he need the all in one girdle? He looked down at the front of his diapers. They were a bit bulky and there was a bit of a bulge where his chastity device stuck out. Sighing he pulled the all-in-one girdle on too because it not only hid his chastity device further, but it also kept his diapers from being so obvious when they got wet.
Did he need the pantyhose too? He didn’t have any socks to wear with his shoes and he could easily go without. But the low-heeled shoes were a bit tight on his feet and the pantyhose made them easier to get on and a lot more comfortable… so he pulled the pantyhose on too.
Was there anything he could go without? He searched his closet. He glanced through the button down shirts that he usually wore to work. But before he selected one, he fingered the new blouses he had too. Heck, everything else he was wearing was female. Nobody would even care if he wore a blouse today instead of one of his male shirts. But wearing anything male was still a coveted privilege to him, so he opted for one of his old shirts instead.
There wasn’t much choice when it came to the pants or shoes. He wasn’t about to go to work in high heels – even though thinking about it slightly rekindled the fantasy he had lived with all day yesterday. He pulled on a pair of women’s pants and slipped into his low-heeled shoes.
But how about his makeup now? Would she let him go to work without it? She had been so adamant lately about him working on it and yesterday’s session with Sandy had really helped – as far as they got. It would be nice to go to work again without makeup, but he had also been wearing it all last week too. The way he was dressed already, he was guessing that by now he’d probably attract more attention at work if he wasn’t wearing any. He opted to go with just the foundation and eye makeup like he had last week, only he’d try to do a better job of it today.
When he was done with his makeup he looked at everything spread all over his bathroom counter. It looked like a lot of stuff, and he hadn’t really used that much. He thought of the things still in his purse. Nobody had told him what things he could leave home now. Deciding to lighten the load in his purse some, he began removing the items he never used and only put in the things he knew how to use. Then, just in case Mel might check, he added a couple of different lipsticks too, even though he wasn’t wearing any.
He had no male watch anymore so he struggled to attach his new one around his wrist and hook the security chain. Why did they have to make them so hard to fasten? Why did they have to make the dials so small too? Women had no sense of what was practical! Kind of like pockets in pants. Such a basic concept!
Finally, he wondered about his new necklace and ring. Did he really need them? He wasn’t sure. He hoped not. Just to be on the safe side, he pulled another baby bottle out of the refrigerator and drank it while he considered that very question.

Mel glanced at her clock. It was almost time for Chad to arrive. How bad would he be? Would he even bother to drink anything before he came? She seriously doubted it. The knock came on her door and she opened it immediately.
“Good morning, Mistress,” Chad said as he dropped a quick curtsey.
“Good morning, Sissy,” she replied as she always did before she let him in. Was it her imagination, or did he look a bit nervous and worried this morning. He probably was worried. She closed the door and began looking him over carefully. He appeared to be dressed suitably, much better than she expected… appeared to anyway. She took the plastic bag he was holding and opened it. Two empty baby bottles. The tape around the bottle caps was still intact. She wished it had been more bottles in the bag, but it was good enough. She looked up at him. “How many diapers are you wearing Sissy?”
“Two, Mistress,” he replied with a small curtsey.
Watching him curtsey with his answer sent an immediate thrill through her. “Are you wearing your girdle?” she asked.
“Yes, Mistress,” he replied with anther curtsey.
“Good.” But she reached out and pulled the neck of his shirt aside just to check. Yes, the girdle was there. But something else wasn’t! “Sissy! Where’s your necklace?” She checked his hand. “And your ring?”
Now he looked really nervous. “I left them home,” he replied with yet another curtsey.
She moved up right into his face. “I don’t ever want to see you without them!”
She saw the panic instantly increase in him and was pleased. She stood back shocked one more time. “And where, for heaven’s sake, is your pacifier?”
This time he didn’t curtsey. He was clearly panicking and worried. “I forgot it again,” he admitted.
“Go get them!” she said. “And don’t come back till you’re dressed properly!” She almost laughed as he practically flew out the door. She had been surprised, he had done really well all by himself with no instructions. In fact, pushing him a bit just then had been a lot of fun. Clearly he didn’t need as much close supervision anymore as he used to. Which meant that she had made more headway with him already than she had thought. She felt very satisfied about that. Of course, that also fell right in line with her plans for him for the week.
Chad came hurrying back in, this time with the ring on his finger, the necklace around his neck, and the ridiculous pacifier stuck in his mouth. As she closed the door behind him again, he dropped another curtsey, “I’m sorry, Mistress,” he mumbled through the pacifier.
“You should be!” she berated him. But inwardly, she was nothing but pleased.
Once again she subjected Chad to having to eat a bowl of baby cereal with the tiny baby spoon while sitting on her kitchen floor. Once she had finished putting two fresh baby bottles into his diaper bag, she stood in her kitchen and watched him trying to eat. She had to control her laughter as more and more of the cereal fell off the spoon and wound up dripping down from his face. If he wasn’t careful, he’d have to redo his makeup again.
She may have felt lousy from last night’s wine when she got up this morning, but watching Chad was definitely putting her in a much better mood.
When he finally finished his baby cereal, along with two more bottles of her tea,” she wiped his face off herself as if he was a child. A bit too much makeup did come off around his mouth. She glanced at her clock, there was plenty of time, but she decided on another idea. “Uh oh, Sissy! You’re such a messy eater that your makeup needs fixing now. But there’s not enough time to fix it here. You’ll have to do it when you get to work.”
“But I can do it quickly,” he protested.
“No, now go! I have other things to do this morning.”
“But… Can I fix it at my place?”
“No. It’s time you started to learn to do it while you’re out anyway. Why do you think I have you carry it all with you? You do have all the makeup you need, don’t you?”
“Yes, Mistress,” he replied.
But she was already heading for his purse in the living room. As Chad climbed to his feet, he really hoped she wouldn’t say anything about there being not as much makeup in it as there used to be.
She was already poking through his purse when he got there. “Remind me the next time we go shopping that you need a new wallet. This thing is ugly.” He didn’t answer. “I see you’ve cleaned a lot of stuff out, but it still looks like you’ve got at least the basics. So that will be all right.”
Chad felt a huge wave of relief. While she was closing his purse for him, he took a second to glance at his face in the mirror she had by her door. Yeah, he could see where the makeup had gotten smeared and needed fixing. It shouldn’t take much though.
She noticed him checking his face in the mirror and smiled. That was a good sign too. “Ok, Sissy. Off to work. And don’t forget to fix your makeup when you get there. I’ll ask Cassie about it later.”

Chad sat at his desk and stared at his computer screen. Even this morning, Mel hadn’t mentioned dinner last night. Wasn’t it good enough? Had he had picked the wrong recipe? He meant to ask her about it but had forgotten with everything else going on… ok, he had just chickened out!
He pulled up his calendar and looked at it. Two weeks of the bet were down and still a very long time to go. He couldn’t believe all the changes she had made in him already. But as to the terms of the actual bet… Well, he was seriously back on track now. If he was going to win this thing, then he had to find a way to keep on track and keep her from knowing it. She could dress him up and make him play her little maid games all she wanted, but in the end, she would be the one dishing out the money – and lots of it.
He spent a long time staring at the calendar on his screen and thinking about the terms of the bet. It would be so humiliating though to someday find himself completely incontinent and have to wear diapers all the time. So deliciously humiliating. So why didn’t he just do it? This was the perfect opportunity. He would really love it. But there just seemed to be something holding him back. Even though he wanted it badly, he just couldn’t do it.
It was the bet, he finally decided. If it wasn’t for that, he would probably be loving everything she was doing to him and more. But because of the bet he felt like he absolutely had to win. The odds were in his favor – heavily. And he was completely back on track now. But it had been close. He had been really shocked to find out this past weekend how much control he had already lost. Almost all of it. And that was after only two weeks! The odds might be heavily in his favor, but if he wasn’t careful, he could really lose!
He wanted it, but he didn’t want it. No, he wanted the humiliation of it, just as he was frightened of the humiliation. Which amounted to the same thing. Bottom line… his darn competitive nature didn’t like to lose. Just as he now knew that hers wouldn’t let her lose either. Very well, the bet was on and there was still a long way to go. He needed a plan. Something to keep him on track so he wouldn’t stray.
He opened his spreadsheet program and began entering a column of dates. The bet had started on the second day of the month. Thirty one days this month and thirty days next month. Sixty one days of hell before his “testing” would even begin. Almost nine weeks. Mel had tried to make it an even nine weeks but he had refused. He had suggested that they make it an even eight weeks but she had refused that. They had settled on the exact number of days of the months.
Once the dates were all in his spreadsheet, he started a “Days to Go” column that counted down the number of days left – 46 as of today.
In the next column, next to the date for yesterday, he entered fifteen minutes. Because that was how long he figured he had managed to hold back from peeing into his diapers yesterday. Not really very good, but compared to Saturday, it was an eternity. From now on, he would try to time himself and his best times would be recorded. His goal was to increase the time every single day to the end. He could do that easily, especially if he was careful to make sure that Mel never found out!