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!