The Bet - Chapter 22 (Saturday – week 3 Part 1 of 6)

The Bet
by Karen Singer

Chapter 22 (Saturday – week 3 Part 1 of 6)

In the early morning hours, before it even began to get light, and long before she even started to become awake, she dreamed of a house. Her house. Her perfect, beautiful house. A house that everyone loved and envied her for. A house with a stone exterior set on acres of beautifully manicured grounds. The interior was furnished in a mixture of new things mixed with the things she had loved and saved from her parent’s home. Things that meant so much to her.
In her dream, she wandered through her house and touched those pieces that were special to her. Each touch brought her feelings of love and joy – as did Sissy, who stood quietly in the background, always awaiting her slightest wish.
She had dreamed about this house often, but this time, her dream was far more detailed, far more complete than it had ever been before. And it was so real that even in her sleep, she could almost touch it, smell it, have it.
Happily, she drifted out of the dream into a deep sleep once again, till hours later, she woke up feeling happy and fulfilled, still remembering odd remnants of her previous dream. A dream she wanted badly just then, just like she wanted some coffee!

No loud music blared into the room when Chad woke up. The full light of the sun seeped all around his shades, startling him for a moment before he remembered that it was Saturday. The weekend. No work – at least not for the company. Mel was another story.
He pried himself out of bed and looked at his pink clock radio. It was later than he thought. He stretched and yawned happily around the pacifier that was still in his mouth. It was good to get some extra sleep once in a while.
He fanned his fingers out on both hands and looked at his new nails. Huge claws. How was he supposed to live with them? He grabbed one of the nails and tugged on it. It seemed strong enough, yet it felt fragile too. Strange.
He waddled in his wet, messy diapers out to the kitchen and read the note Mel had left on his counter, his long red nails catching his eyes as much as the words on the paper.


Sissy,

It’s Saturday. You have the day off till three o’clock. Don’t be late!
While you’re off I expect you to make the most of your free time. You need at least two more packages of diapers and at least six more pairs of pantyhose. And make sure you stock up on anything else you’re running out of. This is your time to take care of those things. Don’t you dare buy anything for yourself that might be even partially thought of as masculine or I will punish you severely!

When you arrive at three, I expect you to be in a perfectly pressed uniform. I will inspect!

Don’t call me for anything before you arrive. The day is yours.


Chad read the note three times and finally sighed deeply. Another day off. He distinctly remembered last Saturday. What a pain that day had been. He had no doubt that today would be equally as bad. His mind quickly made note of two distinct things that made him panic slightly – first, he had no pants to wear so he would be in a skirt when he went out shopping, and the second thing was that he would be going out shopping with his super long red fingernails.
He placed his hand on the kitchen counter and pressed down with just his nails, as if testing their strength, trying to pop them up. They seemed strong enough, too strong maybe.
He waddled over to the refrigerator and pulled out one of the few bottles of tea that was still in there. It would be nice if he ran out and she didn’t replace them. He knew better though. He grabbed one because he wanted one and had nothing else to drink. He finally removed the pacifier that he had slept with all night and headed into his living room. He sat in the only chair he owned and stared at his blank walls while he nursed on his bottle and thought about his morning ahead.
He had to go shopping again. He needed to restock his supplies. Seemingly normal stuff. The problem was leaving the comfort of his apartment while dressed the way he knew he’d have to be. There would be no trying to hide anything today - not like last week. He quickly figured that things would undoubtedly go easier for him if he tried to look as much like a woman as possible. He hated the idea. He hated the idea even more because it added heaping amounts of fuel to his already over stimulated and under-relieved sexual need.
Damn. Was he really doing this? Was he really about to go out shopping dressed entirely as a woman again – only this time by himself? Unbelievably, the answer was yes. He never dreamed he could ever go out like he had been – or like he would be doing shortly. Never – ever – dreamed! Yet he was doing it. And dare he think it, loving it? Because way deep down, he really was living his fantasies. Damn he needed some relief!

Mel opened the larger of the two boxes that had been delivered yesterday. She removed the dress from the packaging and crammed it into her closet next to the one that had arrived before. Both of them had super-full skirts. Neither of them really fit in the closet and with both of them there, they took up way too much space. But she had no other place to hang them and she didn’t want to send them to Sissy’s apartment yet. In fact she didn’t even want him to know about the new dress yet. That was for later. So she just crammed both dresses together as best as she could. The shoes and the anklet socks she put in the closet on the floor. There wasn’t much room for them either.
She really needed a bigger closet. Thoughts of the house she wanted invaded her mind again. A really huge closet would be so nice. Just as soon as she had won this bet she would buy a house. With Sissy there to take care of it, she would have no worries. She wondered again if he realized yet that he had already lost. Maybe she should talk to a real-estate broker now and get things rolling. That was a pleasant thought. But no, it was still too soon. There was no need to rush things.
She finally turned to the smaller of the boxes that had arrived, his breast forms. She opened the box and pulled one out. It felt soft and a bit squishy… and all too real. It was also heavier than she expected. But then, weren’t her own breasts heavy? She smiled, her breasts might be heavy, but she lived with them and loved them. And she wouldn’t have it any other way. Now Chad could experience the same wonderful feeling too. Although she wasn’t really sure how wonderful he would feel about it. But then it was hard to tell, he was a sissy after all.
She put the breast form back into the box and pulled out the little spray can of glue. Would it really hold that well? She’d just have to see. She put the can back into the box and pulled out the printed instructions. One thing caught her eye that she hadn’t thought of before, the glue needed another product to soften it for removal. She hadn’t bought any. She’d have to look around in the stores to see if she could find some. She put the whole box into her closet and out of the way where he wouldn’t see it. The breast forms, like the new dress, were for later.
She wondered how he was getting along with his new nails and almost laughed. She knew how impossible nails half that length could be. She had no doubts that he was finding his situation interesting… to say the least. Between thinking about his new dress and the breast forms and him having to deal with those extra long nails, she was quickly becoming moist and sexually charged again. Tonight! Tonight for sure!

Chad stared at his closet. He had just finished hanging everything back up that had been on the floor, but his closet still looked empty. Seeing only feminine clothes in there now and no male clothing at all was both thrilling, and frightening. And if Mel had her way, he figured his collection of feminine things would be growing drastically. Which he wasn’t totally opposed to, he did like wearing them after all. He always had. He just didn’t want to do it permanently. But if he didn’t win this bet, then that’s just what might happen and the thought of it scared him. Fortunately, he was completely back on track again to win, and hopefully there would be no more episodes like he experienced yesterday. That had been troubling. But he was already doing much better than yesterday. His best time so far today was already up to sixteen minutes, a far cry from his best time of eleven minutes yesterday. But then yesterday had been weird. He was more determined now than ever to win this bet – no matter what! Self-respect, friends, and a life!
He had already showered and put on two fresh diapers. His girdle was already in place as were his pantyhose – although he almost left the pantyhose off completely. Putting them on with his super-long nails had been almost impossible. Just trying to roll them up with his nails had been impossible - he had ruined the first two pairs he tried to put on in the process, and if he had to wear a dress today then he couldn’t wear pantyhose with runs in them.
His makeup and hair were also done. His nails had been a major hindrance there too. He couldn’t believe how difficult it was to just open the eye shadow container. Major difficult. And try to pick up something tiny? Forget it!
More and more he found himself moving his fingers strangely because of the claws on his fingers. And because of it, he thought the end result was that he was having to move his hands more femininely. Not because he really wanted to, but because the nails were forcing him to. It was not only humiliating, but every little movement of his fingers now reminded him of his feminized predicament – and constantly refueled his huge sexual need. A need so great now that he wanted to make a fist and punch the walls… but of course, the nails wouldn’t even let him make a fist.
With his clothes finally hung up, it was time to get dressed. But what should he wear? He didn’t have another complete skirt and top set like he had worn yesterday. Without removing anything from the hanger this time, he sorted through item after item and looked at his choices carefully. Finally, he chose a dress that he had owned from long before he met Mel. He had always liked the dress and he thought he looked good in it – he hoped anyway. The simple dress was of a dark solid material that he hoped wouldn’t stand out too much, and it was belted in the middle which he hoped would make him look like he had more of a figure than he had. Perfect.
He padded the bra-part of his girdle with the two pairs of pantyhose that he had ruined earlier and slipped the dress on. But zipping it up the back with his long nails was nearly impossible! He twisted the dress this way and that as he struggled to grab the zipper with enough force to pull it all the way up. But finally he got it there. He wasn’t looking forward to having to unzip it again later.
With the belt finally fastened, he looked at all the shoes in his closet. He decided not to wear the low heeled pumps that went with his maid’s uniform. They would have been the most comfortable, but he didn’t think they would go as well with his dress as some of the others he had. He chose the most medium height heels he could and buckled them on, hoping that they went well enough with his dress.
He easily slipped his ring over his long nail and onto his finger, but his necklace and watch were almost impossible to fasten. He almost gave up on the necklace before he finally got it. The watch was only a little easier.
Not being able to see himself fully since he didn’t have a full length mirror, he checked what he could see in the bathroom mirror. He hoped it would be good enough because he really didn’t know what else he could do.
He found his pen and some paper and stated making a shopping list. Diapers, and pantyhose went on first. But trying to write them almost made him give up on creating the list. Just figuring out how to hold his pen with the nails he had now was difficult. Once he had written those first two items, he added razors and some more of the moisturizer that he used instead of shaving cream. He also added shampoo and conditioner and deodorant. He checked his makeup supply and decided that he was ok for now – thankfully. Finally, he added a full-length mirror to his list. The way things had turned now, he figured he needed it. And it would be interesting, if not helpful, to see how he looked whenever he got dressed.
He had a lot to do and it was time to get going… like it or not. He grabbed his purse and stopped for a moment and stared at his door. He took a deep breath for courage and finally opened his door and headed out. Just walking down to his car was nerve-wracking. But surprisingly, wearing the dress along with his new fingernails, he felt rather more feminine than ever. He was scared to death, but deep down he was enjoying it too.
His nails made him fumble with his purse as he tried to fish out his car keys, then they made him fumble more as he unlocked his car. In fact, they were making him fumble with everything. In reality, the nails were simply impossible! He had seen nails that long on a few women before, how did they get through life? He couldn’t even grip his steering wheel the way he usually did because of the nails, they were in the way of everything.