The Bet - Chapter 27 (Thursday – week 4 Part 1 of 6)

The Bet
by Karen Singer

Chapter 27 (Thursday – week 4 Part 1 of 6)

Bound and tied... Held captive… Completely helpless… Dark disturbing dreams, all with a common theme, played out in his mind all night long. For once, rarely anyway, did the dreams ever stimulate him sexually. That part of him only got a tiny token acknowledgement… as if his body had given up on it – mostly. Yet it did nothing to stem the restlessness of his dreams.
All of his dream emotions finally coalesced into one dream – one dream where he was Mel’s bound, captive slave. All through the dream he yearned for her touch, her attention, her acknowledgment… her love. And all through the dream, all she did was to treat him harsher and harsher, grinding him down further and further. Yet still he yearned for her and constantly strived for her. He continually tried to show her his devotion in whatever limited way he was able. Till finally… she looked down at him… and smiled at him… and reached out her hand for him… and the loud rock music from his pink clock radio blasted every shred of the dream from his being!
He woke up startled, trying desperately to make sense of anything. What had he been dreaming? As usual, he didn’t have a clue. He was being assaulted by the loud music now that threatened to peel the paint off of the walls. He rolled off of his blow-up mattress onto the empty baby bottles on the floor. Ouch! He scrambled to his knees and reached out for the button on the clock radio and quickly turned off the annoying music. And as blessed silence once again filled the room, he stopped right there and stared at his hand. It was free! There was no high-heeled shoe bound to it. He glanced at his other hand as he wiggled his fingers and felt relief washing through him. The shoes were gone from his hands. Sometime during the night, Mel had removed the shoes… and it hadn’t even wakened him. He felt the pain of his aching feet that were still strapped into the highest heels that he owned, and wished she had removed those shoes too.
Still on his knees, he took time to take stock of his situation. The breast forms glued to his chest under his baby-doll nightly still seemed to be just as tightly glued as ever. His fingernails were still incredibly long and polished a bright red. As usual, his diapers were unbelievably bloated, like a huge basketball… or more likely a bowling ball – because they were so heavy. He could tell that once again he was messy inside of them and not just wet. Again he didn’t remember doing that during the night. His diaper rash was obviously still there too, but was it any better today? He couldn’t tell yet. One thing he couldn’t feel as much, was his penis, totally encased inside the damn chastity device she had locked onto him. He couldn’t feel it, mostly because the device wasn’t hurting him this morning – a blessed relief! And finally, the high heeled shoes Mel had strapped to his feet last night were causing his feet to ache terribly.
First things first! He sat down on his blowup mattress and unstrapped the shoes, wiggling his toes and bending each foot in relief as he did so. Only then did he climb to his feet. It felt good to stand flat-footed again. She wouldn’t really try to train him so that he could only wear high heels? Would she? Damn! He knew without a doubt that she would do it… if she wanted to! It had been only a tiny little piece of some of his fantasies, yet it was a fantasy. And as such, the idea affected him. And as she had said last night, how many of his fantasies had she already brought to the realm of reality? A frightening number of them! And then some!
Taking a deep breath to steady himself against whatever the day might hold for him, he began making his way out to his kitchen to see if she had left him a note. His overly bloated and messy diapers caused him to waddle with an extreme wide legged gait all the way. Her note was there, but it was strange – sort of. There was nothing out of the ordinary at all, and obviously even she had realized it.

Sissy,

You know the rules. You know what you have to do – what you can do, and what you can’t do! See you for breakfast.

What a waste of time! Yet he was very glad too, because she had bothered to write it. Nothing new! For once, everything was normal… if you could call anything about his life “normal.” He waddled over to his refrigerator and pulled out the first of three baby bottles of her nasty tea that he would have to drink before he left for the morning. The bottle had tape wrapped around the top, sealing it so that he would have to drink it like the big baby that he was. He never even gave it a moment’s thought as he carried it out to his sole chair and sat in it. He raised the bottle to his lips and finally realized he was sucking on his pacifier. When had that gotten into his mouth? When he finished his bottles last night, he hadn’t been able to pick the thing up, even though he had tried. Mel. She must have given it to him when she removed the shoes from his hands last night. He mentally thanked her as he took his first sip from his bottle. But the thought of thanking her also sent a tiny bit of fuel to his overly unrelieved sexual feelings once again. Imagine – thanking her for giving him his pacifier to suck on. Damn he needed some relief!

Mel stared at the coffee dripping from the coffee maker into the pot. As usual, it was dripping all too slowly. Maybe she should invest again in a coffee maker that she could set up to automatically come on every morning. There were a ton of them on the market. She had owned several of them in the past. Money certainly wasn’t a problem. She sighed slightly as the coffee continued to drip. The problem was her! She wasn’t disciplined enough to set the darn thing up every night before she went to bed.
But now there was Sissy! He could do it for her. He could set it up as part of his mandatory duties every night. She smiled as she reached for a cup to pour the freshly brewed coffee into. In her mind she was seeing Sissy bringing her coffee in bed, waking her up with it every morning. Sissy! Her dream. And she had just found another way he could be even more useful. Just thinking about him, not to mention what she had done with him last night, brought feelings of joy to her whole body. But those feelings of joy were nothing compared to the feelings she had enjoyed last night. Wow she had been horny! What a night!
As she took her first sip of coffee, the pleasure of the liquid brought images to her mind of the pleasures she had enjoyed last night. Yes, she had had a good time… scratch that… make that a great time! And he had been so funny trying to push the vacuum cleaner with those stupid shoes taped to his hands. She’d have to remember that for the future.
But today was today… another day. It was Thursday. Tonight they had another appointment with Gloria where he would get even more of her hypnotic conditioning. By the way she figured things were going, it wouldn’t take much more at all till he was totally without control – and therefore – hers! She took another sip of her coffee. Mmmm! Sissy had lost! And he didn’t even know it yet!

Chad stared at the clothes in his closet for a moment. Usually they were carefully divided up by type of item, with all the pants in one place, all the blouses together, and all the skirts and dresses in their places. It was still a shock to him to open his closet and not see one piece of male clothing. But this morning, everything looked so different. Since Mel had rearranged things last night, there were skirts mixed in among his blouses. There was something about that that bothered his sense of organization – but what Mel had done for him was necessary – for now at least. He had a hard enough time figuring out what to wear every day. Her efforts were really a big help.
There was no question about what he would be wearing to work today. He had spent yesterday in a skirt and would have to wear a skirt to work tomorrow too. Today he would be wearing pants again… for the last time this week. Technically, there was one other pair of slacks in his closet, but they were a much longer length, and because of his now shrunken waistline, they were pretty much unwearable now - unfortunately.
He had already dressed himself in his usual two diapers, plastic panties, waist cincher, and all-in-one girdle. Today, for the first time, he left the pantyhose off. Trying to put them on while wearing the waist cincher had been too much of a chore. Mel had said he could do without them, at least for work – so he was doing without. It had been a long time since he had gotten dressed without wearing pantyhose. The slacks immediately felt strange as he pulled them up his legs. As he expected, they hung lower on his hips than he would have liked. He grabbed a top that he hadn’t worn before but he was sure would go with the slacks he had put on. The stretchy top fit tighter than he was happy about over his new breasts and stomach, but when he looked at it in the mirror, he didn’t think it looked too bad at all – kind of sexy in fact… if you could call anything about him sexy. Which he wasn’t! Still, for a moment, he enjoyed the sight of himself in the mirror. Damn! Was he really doing this? Going to work… in fact, living his life – dressed entirely as a woman? All the time? Unbelievably, the answer was yes! Damn!
His appearance needed something – like makeup, and his hair done, not to mention his jewelry. Time to get busy getting ready again.

Mel turned sideways as she continued to stare at her reflection in the mirror. She put her hands against her stomach and pushed slightly. Had he called her fat last night? He had said that he didn’t, but she wasn’t totally sure. Why would he ever think that she had worn a waist cincher before? She hadn’t! Ever! She continued to stare at herself and appraise herself. No, she wasn’t fat at all! Ok, so there was a bit of puffiness in her tummy, but it wasn’t that bad. Was that what he had seen? Or had he really not called her fat at all like he claimed?
She wasn’t a spring chicken anymore – not like the Robin woman probably was. But she wasn’t all that old either. Twenty-six wasn’t old? Was it? And yes, she supposed she did need to be exercising more. And ok, her arms were a tiny bit flabby underneath and could use some toning up. But there really wasn’t that much time in her day. She was a professional woman. She was too busy to be exercising all the time. But was she fat? Not as far as she could see! Ok, in her own opinion, she didn’t think she was.
As she grabbed her panties to put on, she wondered if it was worth asking Andrea about… or maybe Gloria… or Cassie. No! Not Cassie. Cassie would immediately try to sell her a gym membership that she didn’t have time for. Maybe just Andrea. Yeah, that would be ok… maybe.
Instead of putting on the skirt-suit she had selected, she put it back into the closet and pulled out her most slimming dress instead. And when she buckled the belt around her waist, she pulled it extra tight! No, she wasn’t fat! Not a bit! She ought to make Sissy eat twice as many meals of baby food for a while just for suggesting such a thing. That would probably teach him a lesson. Suggesting that she was fat! Ha! If he really had suggested it, that is.

Chad rang her doorbell right on time and Mel opened it with a smile on her face. “Good morning, Mistress,” he said as he dropped his usual curtsey.
“Good morning, Sissy,” Mel returned as she stood back to let him in. She watched as he dropped his bags under the table by the door. She took the bag full of empty bottles from him, but she didn’t bother to open it. She was more concerned with looking him over. Did he have to wear such a tight fitting blouse today? Since he had lost so much weight, and with the waist cincher too, his improving figure was becoming more and more noticeable. Did he wear that top just to emphasize how he looked now and to point out that she was getting fat? Ok, the thought itself was ridiculous. So why was she thinking it? Besides, his figure wasn’t that great!
Not wanting to dwell on something that she knew she was erroneously stressing over, she purposely turned away from him so she wouldn’t keep staring at him. “Ok, Sissy,” she said. “Breakfast time.” She purposefully walked ahead of him so she wouldn’t have to look at him and be reminded any further of the weight he had lost. But as she headed for the kitchen drawer to get his bib, she couldn’t help thinking – his figure wasn’t better than hers? Was it? No, that was a dumb thought. There was still no doubt at all that underneath the clothes and the hair and the makeup, Sissy was a man!
Chad pulled the tray off of his highchair, climbed up into it, and pulled the tray back in place. He hated his baby-food breakfasts. They were not only very demeaning, but they tasted awful. He held still for Mel as she tied the bib around his neck. Damn! Just like a baby. And worse, because she made him eat with that stupid baby spoon, he knew he needed the bib – like a baby!
As she walked away, he noticed her turning her head to look at him. Was there something about the look on her face that suggested she was angry with him? If she was, he had no clue as to why. He must have just imagined it.
Mel carried his bowl of baby cereal over to him and felt a tiny bit of relief as she did so. With his bib in place, she could no longer see his breasts sticking out under that tight top he was wearing. And in the highchair, the illusion of him as a baby was far more complete. Much more satisfying today than usual. She smiled at him now as she sipped her coffee and watched him struggling with his cereal. Plop! There went another tiny bit of cereal, off of his spoon, onto his chin, only to run down and fall on his bib. Delightful!