The Bet - Chapter 21 (Friday – week 3 Part 4 of 4)

The Bet
by Karen Singer

Chapter 21 (Friday – week 3 Part 4 of 4)

As per Mel’s text reminder, Chad hurried home after work and cleaned himself up quickly. It was Friday night, their usual night to have their nails done. He was surprised at how normal the routine seemed to him now. He dreaded it, yet it still seemed normal. He just hoped that this time the color would be a bit better than the electric pink that his nails were now, yet how odd that he had somehow gotten used to the bright color too.
As per her usual instructions, when he got dressed again, he left his pantyhose off. His bare legs looked all too pale and white in their naked state. Not nearly as good as they had looked before – he thought so anyway. He had been incredibly conscious of his exposed legs all day in the skirt. He had been horrified to have to wear it, yet deep down, he was excited by his situation too. His bare legs now felt so different against the colorful material of the skirt as it constantly moved around him. Where the pantyhose had accented some feelings, they had also muted others. Now, those muted sensations seemed all too prevalent – and sensual. He was thankful that he had shaved his legs so well that morning.
Once he was ready to go again, he glanced at the pile of clothes he had left on his bedroom floor from earlier that morning. Mel wasn’t there yet, so he picked up a dress that was on top of the stack and opened his closet door to get a hanger – and stopped dead. The first thing that he noticed was how much extra empty space his closet now had. The second thing that caught his eye was all the empty hangers that used to hold his male shirts. And the last thing that he noticed was that there was nothing in the closet at all that was wrapped up in Mel’s cling wrap. It was all gone – missing. Every piece of male clothing that had been in there was totally gone! Vanished! He stared at his empty closet in complete disbelief.
There was a quick knock on his door, but he didn’t move. He soon heard Mel using her key to open the door. “Sissy? Are you ready?” he heard her calling.
He turned toward her, still standing at the entrance to his closet, but he was still too much in shock to answer her.
“Sissy?” Mel called again as she walked quickly toward his bedroom. She found him there, with his mouth open in surprise, standing in front of his closet. She smiled as she realized what his problem was. “Come on now Sissy. We don’t have time for you to waste, gawking at nothing.”
“But…” Chad got out and pointed at his closet.
“Yes, I know,” she replied, “it’s all gone. Now get a move on so we won’t be late.”
As if in a dream, Chad dropped the dress that was in his hands back onto the pile on the floor and followed her out toward the door. Mel handed him his purse and diaper bag and led the way out. “Hurry up, stop dawdling!” she commanded, trying to get him to move faster.
Chad moved faster, but only a little as he followed her down the stairs and got into her car. “My clothes…” he started to say as Mel took off like a racecar driver from the parking lot.
“Yes, I know, they’re gone now,” Mel replied simply as she raced down the street.
“But…”
“But you don’t need them anymore.”
Chad wanted to protest, he wanted to argue, but there was nothing really to protest or argue about. “What did you do with them?” he finally asked.
“I put them somewhere where we both will have trouble getting at them.”
“Why?”
“So you won’t be thinking about them anymore. You don’t need them anymore. You’ve turned another corner, Sissy. It’s time to continue down the avenue.”
Chad wasn’t all that sure about her metaphor, or what she really meant, so he said nothing.
“So, how was your day?” she asked happily.
“Ugh!” he grunted. “One of the worst!”
Mel smiled delightedly. “Because of your little accident at the gym?”
“Oh God!” he replied. “That was awful! But it’s more than that. My whole day was terrible.”
“Why, because you had to wear a skirt today?”
He didn’t even have to think much about that one. “Definitely!”
“What do you mean?”
“Well, in some ways I guess I didn’t have a problem. I guess because I’ve been dressing too much as a woman already.”
“Too much? Not at all.”
He didn’t reply to that. “But in other ways, the skirt caused me nothing but problems!”
“Ok. So tell me.”
“Well, the worst of it was all the women at work. Geez! Would you believe they told me they had been taking bets on when I would start wearing skirts?”
Mel laughed. “I’ll bet they were. Did anybody win?”
“I don’t know and I don’t care.”
“Awww.”
“But that wasn’t really the bad thing. This afternoon they all descended on me in a mob and dragged me down to the break room with them.”
Mel laughed again. “So they kidnapped you?”
“Yeah! Exactly.”
Mel was really enjoying hearing about it. “And they took you to the break room? Why?”
“To humiliate me! What else? The kept making comments like, ‘you have good legs,’ or ‘I like your outfit.’ Then they made me sit down and wanted me tell them all about why I’m doing this.”
“So did you tell them?”
“Not on your life! No way!”
“Why not?”
“Don’t be ridiculous! I’m not going to tell them anything at all about this bet!”
Mel laughed again. “So what did you do?”
“I finally escaped and got out of there.”
Mel was delighted hearing about it all. But the only reply she could make just then was to teasingly say, “You really do have pretty good legs.”
“Ugh!”

The same nail technician was waiting for him when they walked into the salon. Before he could even say hi to her though, she was motioning him to follow her to the back. “Hurry up, we’ve got lots to do today,” she said, trying to get him to move a bit faster. “You look pretty today,” she said as he sat down in the chair to have his toenails done.
He wasn’t sure what to say, so he just said, “Thank you.”
“I like your hair that way,” she said as she unbuckled his shoes and slipped them off.
“That seems to be the general consensus,” Chad replied.
Chad was now familiar and comfortable with the procedures for having his toenails done and he sat back and relaxed while the technician did her job. He was happy to see a pretty red color being applied to his nails a few minutes later. It was certainly a lot better than the pink they had used on him last week.
A little while later, the technician led him over to a table where she started working on his fingernails. She seemed to be spending a lot more time cleaning them this week than she had before, then she began scuffing them up instead of polishing them. He was really surprised when she began gluing very long extensions onto the very tips of his nails. The plastic extensions had to be at least two inches long, and she had glued them onto the very edge of his nails. “What are you doing?” he asked as a wave of panic raced through him.
“Making your nails look better,” the nail technician replied. “You cut them last week. This week, Mel asked that we fix them.”
“But they’re so long!” Chad complained.
“Don’t worry, I still have to cut them back.”
Chad could only sit still and watch as she finished gluing the long claw-like extensions onto all his fingers before she finally cut them, but still leaving them horribly long. Then she began mixing some kind of glop that she used to fill in on top of his nails, and then over the new plastic nails, making them all look like natural, very long fingernails. It was a fascinating process. It just would have been a lot more fascinating if it were being done to somebody else. She was giving him long fingernails! Very long fingernails! The very sight of them panicked him again. Yet that panic also fueled his all too unrelieved sexual need. He had long feminine nails! Oh no! How horrible! And his chastity device began biting because it excited him so much.
He was glad when she picked up her file and began filing them, but all she did was to shape them better and not really shorten them at all. Finally, after what seemed like an eternity, she began applying the color, and a little while later, his fingernails matched his toenails.
He held his hands up and wiggled his fingers. So feminine looking! He tried to make a fist with them, but he couldn’t even get close. He had no doubt at all that the nails were about to make his life a whole lot more difficult.
This time, Mel had been finished long before he was and was waiting for him up front. “Let me see,” she said excitedly. He shyly held his hands out to show her. He heard a lot of giggling from the other women who were sitting in the waiting area, but he ignored them as best as he could. “Oooohhh,” Mel cooed. “They look so pretty now.” Then she giggled.
“But they’re so long,” Chad complained.
“That’s right!” Mel replied. “Next time, don’t cut your fingernails! Maybe this will help to remind you!”
Chad had no doubt that he was thoroughly stuck with the awesome looking claws now. The job was done and there would be no removing them for a while.
“Pay for your nails now Sissy so we can get some dinner.”
Chad dutifully went up to the cash register where the nail technician was waiting for him. The moment he started opening his purse was the moment that he really noticed the difference in his nails. They felt so strange as they got in the way. And when he dug out his wallet, the nails were even more of a hindrance. Handling the bills wasn’t too bad as he paid the woman, but he was very glad that he didn’t have to deal with any coins. He had a feeling that coins would have been impossible.

Mel drove them directly to a nice restaurant for dinner, one that he hadn’t been in before. The night before, Mel hadn’t made him use a baby bottle to drink from, but he had no illusions about being so lucky tonight. His whole day had been a disaster so far, so he wasn’t the least surprised when Mel pulled an empty bottle out and set it on the table even before they had ordered their drinks. She set the bottle off to the side of the table, but it was never out of Chad’s view.
When the waitress asked for their drink order, Mel asked him if he wanted coffee again. With another glance at the bottle, he shrugged his shoulders and agreed. The bottle would be hot to hold, but hopefully not too hot.
Mel saw him glance at the bottle and smiled. Then she began talking. “I remember back when I was in High School. I did a lot of babysitting then. It was fun and I loved making my own money. Did you ever do much babysitting?”
Chad was surprised at the question but replied that he had done some, but not a lot. Mel listened, then kept talking about her life back then and Chad mostly listened. Occasionally they compared experiences. Sometimes they laughed. And when the waitress finally brought their coffee, Chad again waited for Mel to pour it into the bottle on the table, but she never did. So eventually he picked up the cup, clumsily with his new fingernails, and began sipping from it.
It was another really pleasant meal filled with nice conversation. Mel told him quite a bit about her early life and he told her a little bit about his. He was surprised to find out that she came from a fairly well to do family. She wasn’t the least bit surprised to find that his upbringing was more middle class. But while her mother and father had been killed in a car accident a few years ago, he had only lost his mother. And although his father was still alive, he hadn’t seen him now in many years and didn’t even know where he was. His father had never been around all that much while he was growing up anyway, so he really didn’t even miss him. Mel found that to be terrible. She still missed both her parents desperately.
When dinner arrived, Chad had to deal with learning to hold his utensils with the longer nails. It was a major inconvenience, but nothing that he couldn’t manage and he didn’t even mention it while they continued to talk all through their dinner. Their conversation lasted a long time and they were really just enjoying each other’s company, no longer thinking about the way they lived outside of the restaurant.
By the time the waitress cleared away their empty plates, Chad didn’t even remember how many cups of coffee he had finished. He did know however that it was enough that he had wet himself twice before they got up to leave. He never bothered to time himself on holding back though. He had just held it a little then gave up. It was too much trouble to do anything else – under the circumstances.
The meal had been so pleasant that he felt sorry when they finally left. He watched Mel pick up the unused baby bottle and put it back in her purse. He was glad that she had decided to not make him use it. But the sight of it had kept him worried about it all during dinner. But just the act of getting up from the table and walking out brought back all the strangeness of his new life. The feel of his skirt on his bare legs and the weight of his purse on his arm left him no doubt that things were back to normal again. Dinner was unfortunately over.
On the way back to Mel’s apartment in the car, Chad remembered something important. “Mistress, I need to get some laundry done – badly. Can I start some when we get back?”
Mel shook her head. “No, Sissy. I’ve decided that from now on you can only do your laundry on the weekends. My things I may have you do anytime, but your clothes will have to wait till the weekend.”
He wasn’t exactly happy to hear that. “Why?” he asked.
“Because that’s the way I want it.”
Chad was quick to realize the implications of that. Since he only owned four pairs of slacks, that meant that there would be three days each week when he would be forced to wear skirts and there would be no way to avoid wearing them to work again. Not exactly a situation to make him happy. Yet, at the same time, he found his latest predicament sexually thrilling too. If only he could get some relief!
When they got back to Mel’s apartment, she had him carry another big box from her trunk up to her apartment along with a smaller box. After what had been in the box he had carried in last night, he was a bit afraid of her opening either of these boxes. But Mel just had him put them in the corner of her room and didn’t mention them again. And after last night, Chad was glad.
Mel seriously considered tying him up, blindfolding him, then using him again for her own sexual pleasure, but she decided against it. Not tonight. Not after the wonderful conversation they had both just enjoyed during dinner – a dinner that had lasted a surprisingly long time. For a sissy, the guy could be interesting to talk to. And for once, it was nice to have someone who was interested in hearing about her interests. So nice.
She finally decided to just send him home early. So she sat him down on the floor to drink one last baby bottle of her tea, then she removed his diapers and cleaned him up. She stuck another suppository up inside of him and rediapered him for the night. Then she took him home dressed just like that. She helped him into his baby-doll nighty and helped lay him down on his blow-up mattress. She got him two more bottles to drink and put his pacifier down next to him. She leaned over and kissed his forehead as he suckled on the first bottle. “Good night, Sissy. Sleep tight.”
She stopped at the door to his bedroom and turned out the light. She glanced back at him, still sucking on the bottle. She could just see him in the dim light that filtered around the shades on his window. She was making progress with him, good progress. She wondered if he even cared that he was losing this bet already. She turned away and left him. She would be back much later after he was asleep to leave him a few instructions for tomorrow. Tomorrow was going to be a busy day. She had big plans.

Chad sucked on his bottle while he watched her leave. He had really enjoyed dinner again. Not just the food, but mostly, just being with her. It was such a shame that he wasn’t the kind of person she would ever seriously consider going out with – especially now that she knew him so well. Such a shame.
He thought about her as he finished the first bottle, and all through his second one. And when he finally finished it, he put it down on the floor next to him. His eyes caught sight of the pacifier she had placed near him. He felt a strong desire to pick it up and suck on it, but he fought the urge. He rolled over instead and tried to go to sleep. A little while later, he woke up when something fairly hard and sharp scraped against his tongue and the roof of his mouth. He was surprised to find that he was sucking his thumb and the long nail on his thumb was in the way. Irritated, he pulled his thumb out. He opened his eyes and spied the pacifier on the floor. No, he didn’t want to suck on it… yes he did… no he shouldn’t. But what could it hurt? He reached out and picked it up awkwardly around his extra long nails. He put it into his mouth and sucked on it. Instantly he felt a wave of calming pleasure as he had been hypnotically programmed to do. He fell asleep, and dreamed of wetting his diapers.