The Bet - Chapter 32 (Tuesday – week 5 Part 2 of 6)

The Bet
by Karen Singer

Chapter 32 (Tuesday – week 5 Part 2 of 6)

Chad opened his desk drawer and put his purse inside before he sat down in his chair. He stared for a moment at the bouquet of flowers that Mel had sent to him last week. It looked different – smaller, and a lot less vibrant. What had happened to it? The roses in it were fully opened up now, but some of the other flowers looked like they were dying. He made a mental note to ask Robin about it when she came in. He hit the button on his computer to start booting it up.
“Hi Chad,” Robin’s voice called as she was walking past.
Chad turned around in his seat. “Hi Robin,” he replied.
She had stopped at the entrance to his cubicle and was staring at him. “Wait a sec. I’ll be right back,” she said. She disappeared and came back a moment later with nothing in her arms. “New dress?” she asked. “Stand up so I can see it better.”
Chad stood. “Yeah, I just got it. I kind of like it. What do you think?”
Robin stared at him for a moment. “I think that I wish I could afford some of your clothes. Very nice!” She stared at him for a moment more. “I think you could use some better jewelry with it. You always wear the same old necklace, but still, it looks really good.”
“Thanks,” Chad replied, feeling both relieved and happy as he sat back down. “Hey Robin, what happened to all the flowers?”
Robin glanced over at the bouquet on his desk. “Oh, they were looking kind of puny and some of them were obviously dying so I pulled those out. I also added some water for you. You really need to check that every day.”
Chad nodded. “Thanks,” he replied. I appreciate it. So how did things go yesterday?” he asked.
“Quiet, as usual,” she replied as she moved further into his cubicle and leaned up against his desk. “How was your day off? What did you do?”
It was all Chad could do to not choke at her question. There was no way he could ever tell her what he really did all day! “Oh… not much,” he replied, trying to find the quickest answer. She was still looking at him, waiting for more. “I… visited a few people,” he finally added. He was relieved when she seemed to be more satisfied. Visited people was right! His problem was just the way that he had visited them!
“I see you got your nails cut,” she said next. “Very pretty by the way.”
He held up his hands to look at them. The nails were still very long, but a lot shorter than they had been all last week. He still thought they looked pretty. Something inside of him was pleased by the sight of his fairly feminine looking hands. “Yeah,” he replied, still looking at them. “I think I kind of like them this length.”
“They’re still pretty long. Not exactly practical for working.”
“Maybe, but they’re a lot easier to deal with than the longer ones I had.”
“I don’t know why you ever got them so long in the first place! That was kind of silly.”
Chad couldn’t really tell her that he had no choice in the matter. “It wasn’t really my idea,” he replied cautiously. “But I think I learned something from it.”
“Learned something? I’m betting the idea of having nails like that just turned you on so much that you decided to try it. That’s why you had them done. And now… now you’ve seen what a pain they were and had them cut down a bit.”
“Well…” Chad started to reply.
“Don’t deny it!” she teased. “That’s why you’re dressing the way you do. You love it! Don’t you!”
Chad blushed. “Kind of,” he replied sheepishly. “Actually, it’s a bit more complicated than that.”
Robin threw her arms up in the air. “Complicated! Don’t hand me that crap again! You love it, so you’re doing it. Right?”
Chad stared at her for a moment. She really had no idea, and he meant to keep it that way. But deep down, she was also right. He did love it. “Yeah, I do,” he finally admitted blushingly. He was a sissy after all. Mel had made that point abundantly clear yesterday.
Robin nodded, more satisfied. “That’s better. Complicated? My ass! You’re dressing like a woman because you love it… it turns you on! Don’t try to hide behind some kind of other silly lame excuse.”
After Robin had left, Chad turned around again to face his computer. The login prompt was waiting for him. He reached for the keyboard and paused. Last week, he had been forced to teach himself to type with just his fingernails on the keys. But now his nails were shorter. He reached out to the keyboard with just one hand and experimented with touching a few keys. His nails were still too long to really let him use anything more than just his nails when he typed. Yes, he could slip the nail over top of the key, between the keys, but when he pressed down, the tip of his nails hit something underneath. So he still couldn’t really use anything but his nails to type with. Fortunately, he had gotten a lot of practice with it last week. As he typed in his password, he quickly realized that he was going to have to get used to it all over again. Yes, he still had to use only his nails, but now he had to get used to the shorter length. At least it seemed to be a lot easier and his nails felt stronger and less fragile now too.

Mel closed the folder and put it into her finished pile. She had a few minutes now to think about other things. And other things usually meant Chad. Only this time, instead of directly thinking about Chad, she was thinking instead about Gloria… and how she could get Gloria to help her again. One thing was for sure, in order to get Gloria’s help, she first had to talk to her. She picked up her phone and dialed the number. “Hi Gloria. It’s Mel.”
Gloria was almost hesitant in her answer. “Hi Mel,” she said simply. She was still very concerned after their last lunch meeting. In a way, she was just glad that Mel had called. At least it meant that they were still friends – she hoped.
“Are you game to try lunch again?” Mel asked.
Gloria hesitated again. Mel had walked out on her yesterday. But she was her friend and everything she had said to Mel had been the truth! “Are you sure? I’m not changing my mind.”
Mel wasn’t glad to hear that Gloria was determined to remain so stubborn. “Yeah, I’m sure. And I’m really sorry about yesterday.”
“Yeah, I am too Mel. But Mel… I meant everything I said then.”
Mel was silent for a moment. She knew that Gloria believed everything she had talked about was true, but she now knew that some of that was wrong… very wrong. But still… “Gloria, somehow we’ve got to get past this. Let’s just have lunch. Maybe we can talk about it a bit more… maybe. I promise not to run out on you again like last time.”
Gloria chuckled. “Okay Mel. We’ll just eat, and maybe talk a bit more. See you at lunch.”

Chad stared at his computer monitor. He had been working, but right now, work was the farthest thing from his mind. Instead, he was thinking about peeing… or rather not peeing. He was having a lot of trouble so far holding back. At first, he found himself continually peeing before he even knew he was going to do it. But now that he had that control back again, just holding back was still all too difficult. Of course, he had already had a lot to drink since he had gotten up. Not to mention all he had been drinking for the last three days. His system would have to readjust back to normal and that might take a while. But still, now that he could control himself again, he didn’t seem to be able to hold things back very long at all. He sighed. Try, try, try. It was the only way!
“Break time,” Robin’s voice called out from behind him, pulling him quickly out of his thoughts.
Did he want to go to break? Yes and no.
“They had some great new doughnuts yesterday,” Robin continued. “You should have been here.”
“They did?” The thought of something solid to eat, especially something as tasty as a doughnut, made up his mind for him. Besides, Robin would only egg him on till he went with her anyway. He pulled himself out of his chair and followed her down the hall.
“I really do love that dress,” Robin noted as they walked.
“Thanks,” Chad replied as he realized he was no longer able to hold back from peeing again. He glanced at his watch. Less than ten minutes. Not good.
The break room was filling up fast when they got there. Chad spied several boxes of doughnuts past the coffee pots and made a beeline straight for them. He grabbed one and a napkin and was eating it before he even grabbed a cup for his coffee. Mmmm! So good! Heaven!
“I told you they were good,” Robin said, noticing the look of joy on his face.
“You have no idea!” he replied. He certainly wasn’t going to tell her that he had eaten nothing but baby food for the last three days. He finished his doughnut before he even tried to pour himself some coffee. Then he joined the other women at their extra large table.
“Hey, we missed you yesterday, Sissy. Where were you?” one of them asked.
They missed him? Sure! “I took the day off,” he replied.
“Any special reason?” she asked.
He shook his head. There was no way he wanted to give any indication of what he had really done. “No, I just took a day to relax and visit a bit.”
“Recovering from your divorce!” another woman stated with certainty.
Chad was shocked. That wasn’t the real reason at all. “Um…” he searched for a good answer.
“It’s okay! Divorces can take their toll. I aught to know!” yet another woman chimed in. A few of the women laughed.
“Hey!” said still another one. “My sister called me last night. And she went to the mall yesterday, and you wouldn’t believe what she said she saw there.”
“What?” someone asked.
“Well, she said there was some guy there, dressed up as the most ridiculous sissy thing you could imagine! She even said she saw some diapers under his dress!”
Chad wanted to crawl into a big hole and hide.
“What was he doing there?” someone asked her?
“I don’t know. She just said that she saw him outside curtseying to everyone and then later walking through one of the big department stores. I don’t know anything else. But can you imagine someone dressing like that? In the mall of all places?” There were more than a few chuckles from around the table.
“One of your friends, Sissy?” one of the women asked Chad.
“Uh…” He shook his head. Lying was clearly the best option here. “Nobody I know,” he replied nervously.
“Well,” the woman replied, “probably not anyway. You at least dress a whole lot better. I like that dress by the way.”
Chad glanced down at his dress again. “Thanks.” Whew! He had hoped to never hear about his trip to the mall again. And now one of the women had brought it up here! He just hoped that nobody really connected him with being there.

Mel shook hands with her client and led him all the way to the outside door. She reassured him once again that everything would be fine and that she was on top of his situation. When the door had closed behind him, she turned back toward Andrea. “Business is definitely up,” she said as she shook her head. “It seems like everyone wants to sue everyone else.”
Andrea picked up some of the work folders on her desk that she had yet to work on. “You don’t have to tell me!” She dropped the folders and just let them fall back onto the pile. Then she pointed at some envelopes and a small box on her desk. “Mail’s in early today. I think that package you were still waiting for got here.”
Mel walked over and picked it up. It was covered with heavy plain wrapping, she could tell nothing. “Thanks,” she said as she grabbed both the box and the pile of mail that Andrea had left for her. She carried them back to her office where she closed the door. The pile of envelopes she dropped on her desk out of the way, the box she set right in front of her. She grabbed her scissors and began opening the package. Almost hesitantly, she peeled back the plain brown wrapping to see the box underneath. The word “Aneros” jumped out at her. With a last glance at her door to make sure it was closed, she set the box down and opened it. Inside, she found the oddly shaped device that was designed to make milking him easier. Unlike the “toys” she had received yesterday, this one inspired no sexual interest for herself, but she did wonder if he would receive any pleasure from it.
Odd, that he was becoming so responsive to being toyed with in his anal cavity. She had totally denied him any pleasure from the place where he should be receiving all his pleasure – his male appendage. She had totally denied him that ability. So was this new form of sex for him more like a female pleasure? She wasn’t him and she wasn’t male, so she had no way of really knowing. But just the act of him being penetrated instead of him doing the penetrating certainly seemed totally feminine. She wondered briefly if he could get multiple orgasms from this kind of sex – like a woman could from normal sex. Of course, to the best of her knowledge, he hadn’t had a single orgasm yet. She didn’t even know if such a thing was possible. But either way, it was another case of maleness denied. And that thought brought a tingle to her dampening sexual region.

Chad could barely hear Robin typing on her keyboard in her cubicle next door. She was busy. He opened the spreadsheet for the bet that he kept on his desktop. He found today’s date and stared at it. Thirty one days to go. Another month. One more full month before he would get the chance to prove that he could still control himself. Would he make it? He had to! A surge of confidence ran through him. He would make it! He was absolutely sure of that. She might play her little games with him on the weekends, but here at work he could work, and work hard, at not only maintaining, but also building that control that would let him win. She had no chance!
He looked at yesterday’s date – Monday. He had no timing to fill in there. He had never once been able to hold back a single second all day yesterday… or Sunday… or Saturday either. Or Friday night for that matter! No wonder he was having so much trouble today. He was fairly sure he remembered being able to hold back for twenty-nine minutes on Friday while he was at work though, so he filled in that space.
The three empty spaces where he had no time to fill in bothered him though. Three empty spaces that represented three very long, very hard, very humiliating days. He didn’t really want to think about those days, but he couldn’t help it. Three days wearing only a single diaper at a time with just two hours each time to make it leak. How had he managed it? Unbelievably, he had. Three days of acting all the time like the biggest sissy baby flake he could possibly imagine – Mel’s sissy vision of him. And having to use nothing but that stupid high-pitched voice? He was really glad he was at work now where he wouldn’t have to worry about it… at least not till he got home later tonight.
For three full days she had literally pounded sissyness into him. Forced him to act in ways he still couldn’t believe. Forced him to look at himself over and over again – and finally see himself for what he really was, a sissy. Because even though he “kind-of” labeled himself that in the past, deep down, he had always denied it. He had still clung desperately onto his male chauvinistic attitudes. But could he do that anymore? He thought again about his trip to the mall yesterday, not to mention his trip to the gym. No, he really couldn’t, or shouldn’t think of himself as a male anymore. So many people had seen him, up close, behaving like the total sissy that Mel had made him. Even though he had lied to the women in the break room, if anyone ever asked if that was him doing those things, there would be no way he could really deny it. He had done them. He was that sissy!
Could he ever think of himself as being a male again? His eyes caught sight of the skirt of his colorful dress. Disgusted with his thoughts, he quickly closed the spreadsheet. He didn’t dare think about it anymore.