The Bet - Chapter 40 (Wednesday – week 6 Part 1 of 6)

The Bet
by Karen Singer

Chapter 40 (Wednesday – week 6 Part 1 of 6)

He tossed and turned on his blow-up mattress for hours, trying vainly to fall asleep. At first he thought it was that he simply couldn’t get comfortable. His glued-on breast forms were bulky and uncomfortable, his chastity device was irritating, and the pins from the earrings in his ears kept sticking him. The only thing that he didn’t consider as bothersome was the bulk of his diapers, which ever so gradually grew all night long.
He was just beginning to finally doze off when the damn suppository she had stuck up inside of him suddenly went to work. He hadn’t felt that in quite a while now – not at night anyway. He hated the feeling so much that he was actually glad he never felt it when he slept anymore. After that, his bulky, and now messy diapers, did bother him. Why was it that Mel had been so tired and drunk last night that she wanted to go straight to bed, but not tired and drunk enough to skip putting the stupid suppository up inside of him?
The oblivion of sleep just didn’t seem to be possible for him. All night long his mind kept going over and over what had happened at the poker game. And one thought more than any other kept hammering at his brain – he was going to have to go out on a date with Derek!
Something in his brain recognized the fact that he had consumed way too much sugar from all the Cokes he had been forced to drink during the game – which also accounted for why he probably couldn’t sleep… not to mention why he also kept feeling himself peeing so much.
If he could just fall asleep! Then he wouldn’t have to worry about anything! At least not for a little while. And he needed sleep! He had to work tomorrow… or was it today?
Finally, without his conscious knowledge, he did drift off into a dream filled slumber. Yet his dreams echoed the worries that were foremost on his conscious mind. He saw himself wearing a tasteful feminine dress. In fact his whole outfit appeared tasteful. He felt wonderful in it – and very feminine. But the wonderful feelings of feeling pretty and feminine were overpowered by other feelings – disturbing feelings, feelings of awkwardness, feelings that everything was all wrong, and mostly… feelings of fear! Because in his dream, he was walking hand in hand with Derek, and he could feel the wrongness in the very pit of his stomach!
The wrongness grew as his dream progressed to an intimate dinner with Derek. It grew much worse as he dreamed of dancing with Derek. And then he was sitting in Derek’s lap, looking up at his face, looking up at his lips… knowing that a passionate kiss was coming.
Part of him actually wanted that kiss… yearned for it… wanted to experience it! Yet at the same time, the greater part of him was horrified by the thought. The feeling of wrongness became like a black undenying cancer that ate threw him – even though that tiny piece of him still wanted to feel the softness of Derek’s lips touching his own feminine lips.
He wanted that kiss, yet he wanted to run… to get away. Derek’s lips slowly drew nearer, closer to his own. And the closer their lips came, the more he could sense how Derek’s lips would feel touching his own. Slowly the distance closed till his whole world was Derek’s lips coming at him. The more they moved closer, the more he wanted that kiss… and at the same time, the more the feeling of wrongness and horror grew.
It was a nightmare! It was the most intimate pleasure! Both – all rolled up in one! He wanted to melt into the kiss, yet he wanted to scream in distress! And the moment Derek’s lips did finally touch his own… and he felt that soft pleasure… and he felt the overwhelming wrongness of it all boil over to where his body could no longer contain it… he screamed! Loudly! He screamed with every ounce of breath that his body could hold!
He woke up as his scream in the real world was still dying… still escaping his physical lungs. Yet as his breath ran out and the scream died, the sound of it still seemed to linger around him, then it seemed to change. As he panted, trying to catch his breath, he realized that the sound now surrounding him was the sound of the rock music being blared out by his pink clock radio. It was morning already. Ugh!
He felt like he hadn’t slept a wink! He struggled off of his blow-up mattress and killed the sound coming from the radio. For once, the sudden silence that filled the room wasn’t much better. Still trying to gather his wits, he stumbled and waddled out of his bedroom toward his kitchen – even as remnants of his dream still played thorough his head. He hated nights when he couldn’t sleep. He hated the mornings after even more. Fortunately, he was usually a very sound sleeper so it didn’t happen often.
As he entered the kitchen, he began looking on the counter for her note… but he didn’t see one. Had she left one? She always left one! She always came in while he was sleeping and left him a note with instructions for the morning! But even though he looked all around, he didn’t see one. Had she forgotten him? Abandoned him? More likely, she had just been too damn drunk to remember!
Well, there was rarely anything new in her notes anyway. His routine was supposed to be pretty much the same – he supposed. He went to his refrigerator and pulled out three baby bottles – two of her lousy green tea and one of apple juice. He headed for his lonely, solitary chair – the only piece of furniture he really owned – and he collapsed down onto it. He put the first bottle of tea to his mouth and began drinking. He barely saw the childish pictures on the wall in front of his eyes, instead, images and mostly feelings of dread from his dream played across his mind.
He had to go out on a date with Derek. She was going to ‘make’ him go out on a date with Derek. And it was sooooo wrong!

Mel groaned as she pulled her pillow tighter against her head. She felt sick! Her mouth tasted rancid! Okay, it was only four beers – or five… she thought. But it felt like she had drunk a whole keg because the aches and pains from her period only made things that much worse. Her clock radio had gone off a few minutes earlier and she had already turned it off and tried to go back to sleep. But now she had to pee so badly it was beginning to hurt! Why had she drunk so much last night? Hadn’t she promised herself before that she’d never touch another alcoholic drink again? Why the hell hadn’t she kept that promise?
Between the beer and the queasiness in her stomach from her period she felt nauseous! She rolled out of bed and hurried to the bathroom – bent nearly in two. Peeing helped, but not a lot. Her pad was a mess. She considered not changing it since she would be getting a shower soon, but the idea that a fresh pad might help her feel better won out. After that, she brushed her teeth – thoroughly! But she could still taste all the beer she swilled last night – and it didn’t taste good! Yuck!
She went back to her bedroom and grabbed her robe – not for warmth, but hoping it would provide her with at least a bit of comfort. It worked – sort of. Then she headed slowly out toward her kitchen, realizing as she went that her head felt wooly and stuffy. She promised herself yet again that she’d never touch another drop to drink as long as she lived! Unless it was coffee!
Making the coffee was automatic – she didn’t even have to think about it. Waiting for it to perk though was bothersome. As she waited, her head cleared enough to start remembering things from last night. Not all at once, but little scenes at a time. She remembered getting Sissy ready – and the outrageous outfit that she had made him wear. She almost laughed over it – even now, as bad as she felt. She remembered playing cards. She remembered making him go into George’s bathroom to clean it. She remembered the trouble he was having with his skirt continually riding up, exposing a piece of his ever growing diapers underneath – again she almost laughed. It seemed that just thinking about Sissy was making her feel better.
Her coffee finished enough that she could pour herself a cup. Mmmm! She breathed in deeply and closed her eyes. She would live – hopefully! Coffee, the elixir of life! Still thinking about the card game last night, she carried her cup out to the living room where she sat down in one of her softer chairs.
She remembered talking to the guys last night about Sissy’s voice – now his ‘girly’ voice. She didn’t like it as much as his sissy voice, but sometimes compromises had to be tolerated. Her eyes opened a bit wider as she remembered asking all the guys to pass the word around where he worked to keep reminding Sissy to use only his girly voice – effectively blocking him from ever using his male voice! And something within her cheered! She had done it! She had finally found a way to deprive him of yet another male trait! He could no longer speak in his male voice – or very soon he wouldn’t be able to… because she fully intended on following up on that little piece of work today – as soon as possible!
Despite the queasiness in her stomach, and despite the aches from her period and despite the wooliness in her head, she was starting to feel much better now. She was starting to feel positively great! Relatively speaking that is. It seemed that coffee combined with thoughts of Sissy were very affective in curing all her ills. Now if they could just cure her periods!
As she took another sip of her coffee, she remembered one more thing from last night. She had set up a double date with Sissy’s friends Ray and Derek! Okay, they were both hunks, but she seemed to remember that she liked Derek more because Ray was a lying womanizing sleaze! But had she really been that drunk? And somehow, since Derek was going to be “technically” out with Sissy, she almost felt like Sissy was the lucky one! Why couldn’t Derek have won last night instead of Ray? She stopped to think about that for a moment. Okay, she was still a bit out of sorts here this morning – for various reasons. But… was she actually jealous? Of Sissy? Impossible!
Not being able to stand that thought any longer, she quickly downed the rest of her coffee and headed straight for the shower to soak, and hopefully clear her stupid head.

Chad stared at his image in the mirror and tried desperately to take a mental inventory to make sure he had everything correct. He was so tired that he felt groggy and dimwitted. Two diapers – check. Plastic panties – check. Waist cincher – check. Overly tight all-in-one girdle over his diapers, waist cincher and supporting his glued on breasts – check. Pantyhose – check. Colorful dress – check. Strappy high heeled shoes – check. Woman’s watch – check. Wooden bracelet on his other wrist – check. Two of the three wooden necklaces around his neck – check. The clear earrings in his ears – check. The pink ring on his finger – check. Hair curled – check. Makeup right – check. And one other little item that came to mind… Chastity device – also check – unfortunately. Since it was locked on, he really didn’t have to think about that one. Did he have everything? He hoped so, because his brain didn’t want to function enough to think of anything else. You’d think that dressing like a woman wouldn’t be so involved – so much work! He knew better now.
Still wishing for more sleep, he grabbed his purse, his freshly stocked diaper bag, and the plastic bag containing the six empty baby bottles – three that he had finished last night before – trying – to go to sleep, along with another three he had just finished this morning. With a deep breath for courage and to try to wake himself up a bit more, he went out his door and headed to Mel’s apartment next door.

Mel half-heartedly stirred at the baby cereal in the pot on her stove. The doorbell rang and she looked up at the clock. He was right on time – darn it for once! She tried to pull herself together and gain a bit more enthusiasm as she headed to open her front door. She pulled it open and there he was – colorful this morning – in all his splendor… while she felt like shit! She watched his usual greeting and noted that it still sent waves of pleasure throughout her. Then she noticed the smile on his face. Shit. Obviously he felt better than she did… of that she was definitely jealous! “Hi Sissy,” she managed to get out pleasantly as she stood back out of the way to let him in.
She waited till he had set his purse and diaper bag down on the floor under her table by the door. She looked him over carefully. The colorful dress again today. Yes he did look good in it – don’t be jealous Mel – he doesn’t look that good! “I see you’re wearing the clear earrings today,” she noted out loud.
“I haven’t worn them yet so I thought I’d try them. I hope they’re okay.”
She nodded. “They’re fine. The colorful ones would have gone better with your dress, but those are just fine.” She really didn’t want to see any more. “Get yourself into the kitchen and up into your highchair. I’ve got your breakfast almost ready.”
A few minutes later, Chad sat, locked into his highchair, bib around his neck, eating baby cereal while he held the tiny baby spoon in his left fist. He was hoping that maybe eating something might wake him up more, but so far…
“How are you feeling today?” Mel asked as she leaned back with another cup of coffee against her counter.
Chad looked up at her and shook his head. “Lousy! I don’t think I got any sleep at all last night!”
Mel silently cheered. She wasn’t the only one feeling bad today. “Why not? You didn’t have any beer last night.”
Chad just shrugged. “I don’t know. Too hyped up I guess.”
“Over what?”
“Having to go out with Derek!”
Mel was surprised. “You’re looking forward to it that much?”
“No! I’m dreading it that much! Do you have any idea how wrong that is? And did it have to be Derek for heaven’s sake? I mean… he’s my friend! One of my best friends!”
Mel smiled. “Would you rather that it was Ray you were going with?”
“No!” Then he quickly changed his mind. “Yes! At least then it wouldn’t be with my best friend.”
Mel almost found it amusing that they were each going with the wrong guy. She’d rather be going with Derek, and he would be more comfortable with Ray. The luck of the cards… that’s all there was to it.