The Bet - Chapter 40 (Wednesday – week 6 Part 4 of 6)

The Bet
by Karen Singer

Chapter 40 (Wednesday – week 6 Part 4 of 6)

Cindy wasn’t exactly pouting, but she wasn’t all that happy either. Cassie had said that she couldn’t watch Sissy being changed again today. That had been a real treat yesterday! She still couldn’t believe what she had seen… the stupid guy had been drinking from a baby bottle! And then there was that plastic thing locked all around his male part so that he couldn’t use it. She remembered touching the thing and even pulling on it – and how it had hurt him. That was when Cassie had suggested that she leave. Next time, she promised herself, she’d just watch – maybe then Cassie wouldn’t chase her away. And today, she couldn’t go in at all! Was Cassie mad because she had hurt him?
She saw his car pulling into the parking lot and her excitement grew – despite the fact that she couldn’t watch today. What could she say to him? How could she tease him? She absolutely felt like she had to tease him somehow… But how?
Chad paused a second before opening the door to the gym. Yesterday had been horrible. And he was sure that today, when he felt so miserable, things would probably be even worse. Was Cassie going to let the receptionist watch – or help again? This time, was she going to let her see – everything? He certainly hoped not. If it wasn’t for the fact that he needed his diapers changed, and that Mel required him to have Cassie do it for him every day, he would have avoided the gym altogether. Plucking up his courage, he opened the door and went in.
“Hi Sissy!” the receptionist called excitedly.
Her excitement didn’t bode as a good sign to Sissy. He knew he was going to have to do it, so he didn’t even bother waiting. He dropped one of his sissy curtseys to her and said hello in his sissy voice.
“I just love seeing you do that everyday,” Cindy said. “It’s so sweet.” Then she leaned across the counter a bit. “Would you like me to feed you your bottle today?” She immediately went into a fit of giggles.
“No thank you,” Sissy replied. “Can you please get Cassie for me?”
Cindy desperately searched for some other way to tease him, but today the ideas just weren’t coming. And there was a bit of a look about him that told her something was a bit off with him today. With a look of frustration, she left him to search for Cassie. Chad was glad! He was also glad that Cassie hadn’t been very far away. A minute later, he was following her back to their usual room.
Is she going to be joining us again today?” Chad asked as he started to get undressed.
“Not unless you want her to,” Cassie replied. “Shall I get her?”
“No! Please!” Chad replied quickly. He was glad that they would be alone again. Yesterday had been – upsetting. And he was upset enough as it was.
“You seem…” Cassie searched for a word, “tired today.”
“I am. I got no sleep at all last night.”
“Was Mel that rough on you?”
“Not… exactly.”
“So how come?”
“Worries!” Chad finally replied.
Cassie could see that he didn’t seem to want to talk about it. “Well lay down on the floor and drink your bottle. Maybe it will help you relax a bit.” After she said it, she wasn’t quite sure how much relaxing he was actually going to get to do!
Chad put the bottle to his mouth and began nursing on it. Sucking on it did bring him some measure of comfort – as it often did. Why, he didn’t know – or care. He did his best to ignore the feelings of Cassie removing his soaked diapers and cleaning him up. Ignoring what she was doing was actually very easy, he didn’t hardly have to try anymore. It was what she did to his other side that he couldn’t ignore very well – nor did he really want to.
“Okay, roll over,” Cassie finally said.
Chad put his bottle down and rolled over onto his stomach.
“I see the redness is all gone today,” Cassie noted as she quickly wiped off his backside.
“Fortunately,” Chad mumbled. A moment later, he stiffened at the freezing cold feeling of the lotion as Cassie started wiping it onto him. The feeling of intense cold didn’t last very long, and soon gave way to intense pleasure instead. Ahhhh! Without being told to for once, he hiked his knees up under him, raising his backside up into the air, making it a better target for what he hoped Cassie might do to it.
“Anxious today, huh?” Cassie said as she saw him get into position. “I guess you want it then.”
Chad said nothing, he was too interested in the feeling of Cassie’s finger as it played with the opening to his asshole. Yes he wanted it! He wanted it very much!
Cassie watched him closely as she started pushing her finger into him, then pulling it out again… over and over again… further and further in. She stopped when he started pushing and pulling against her finger himself. She quickly got her ribbed toy and lubed it up, then set the tip of it up against him. Ever so gently, she pushed on it till it started to slip inside.
Chad was in ecstasy. He didn’t know why he liked this so much, but he did! He just wished that it could grant him the ultimate release he craved so much. But evidently that was impossible. Still, it was just about the best feeling he was capable of experiencing anymore. In and out. In and out. Feeling the little ribs of her toy going past the entrance to his anal opening, only to be followed quickly by the next one. Delicious. He began gently rocking back and forth. As tired as he was, he still found the energy to enjoy this most wonderful treat. Back and forth, back and forth. In and out, in and out. He wasn’t going slower or faster today. Everything was staying at this one steady pace, and he didn’t really care. It just felt good!
Cassie watched him carefully as she held the toy in place, letting him set the pace and intensity. He had been at it for quite a while now and was usually fucking himself desperately on it by this point, but today he was still going slowly. Perhaps it was because he was so tired. She let him go on for a while more before she stopped him and pulled it all the way out. “I’ve got to get back to work soon!” she declared as she saw his head turn back towards her. She saw him just nod his head a little – was that in despair?
She grabbed his jar of suppositories and opened the lid. “We can’t forget these little things,” she said brightly. But he wasn’t paying the least bit of attention to her – as far as she could see. Since it was Wednesday, one of the days when he wasn’t supposed to actually get one now, she only pretended to pull one of the pills out of the jar. He never knew the difference when she stuck her finger way up inside of him as if she were really putting it there. “Do these things still work?” she asked. She saw his head turn back towards her. She also saw the bit of annoyance on his face as he nodded. “Every day?” she asked.
He nodded again. “Every damn day!”

“So did you talk to him yet?” Gloria asked as they waited for their lunch to be delivered.
Mel shook her head. “Not yet. There was no time last night.”
“But do things seem to be any better between you two?”
“As far as I can see.”
“Mel, you still really need to sit down and talk with him… seriously!”
Mel sighed. “I know. It’s just not that easy! Are you still going to hypnotize him tomorrow night?”
“You’re changing the subject! But I was still planning on it.”
“Good! Because I’ve still got to know how long he’s holding back now. I’m seeing definite signs now of further lack of control.”
“So you’re winning?”
“I think so, but I’m just not sure! One minute I think I am, then… I just don’t know!”
Gloria nodded. “I guess I can ask that question again. No problem. So how did the poker game go last night?” For the first time since they sat down to lunch, Gloria saw Mel smile broadly.

Chad couldn’t really hear anything at all coming from Robin’s cubicle next door. He knew she was there though because he had seen her going in after lunch. He was fairly sure she was working, so he felt safe enough to open the spreadsheet where he kept his progress for the bet.
He scrolled down to today’s date. Twenty-three days to go now. Getting smaller – but still a long way. He went up to yesterday’s date to fill in how long he had held back. He stopped to think about that a bit. He had only managed to hold back for twelve minutes yesterday. An improvement over the day before, but it was still an improvement. But actually, it had been a few seconds more than twelve minutes. Should he include that as well? No, just to be fair, he filled in twelve minutes – one whole minute longer than the day before. He had really been hoping for better yesterday, but it just didn’t happen – unfortunately. Still, it was progress.
Before he closed the spreadsheet, he again glanced at the column of reasons why he wanted to win the bet. The first three items, self-respect, friends, and a life still rang all too true. But he stopped looking as he started reading the rest of it. All too quickly the images of the pictures that Sandy had done for redecorating his apartment came to mind – both pictures. Troubled and not wanting to think any more about it, he closed the spreadsheet and went back to work again.

Robin’s cell phone rang while she was finally getting some work done. She really didn’t mind the interruption though. Thinking that it was probably her husband calling she answered it without looking to see who was calling. “Hello?” she said as she was still looking at the work on her computer monitor.
“Hello. Is this Robin?”
Robin was a bit startled to hear an unfamiliar voice. “Yes,” she said tentatively. “Who is this?”
“Hi. I’m Mel… Sissy’s friend.”
“Mel?” Robin exclaimed excitedly.
In the cubicle next door, Chad suddenly looked up. A feeling of horror ran right through him as he desperately tried to listen for more.
“You don’t know how much I’ve been wanting to talk to you!” Robin continued.
Mel was more than sure of that. The damn woman probably wanted to fish for ideas to turn Sissy away from her! “I’m sure,” Mel replied nicely, but she said it as if she was in a hurry. “Unfortunately, I’ve only got a second before I have to be in court,” she lied. She was really sitting at her own desk in her own office. “Listen, I just wanted to follow up on something I asked Derek to do for me – or rather to pass along for me. That is about Sissy using her new voice all the time.”
“Don’t worry!” Robin replied. “He told me. And I guess I kind of agree with you. If Sissy doesn’t practice, then he’ll never get it right. And using his male voice isn’t going to help matters at all.”
Mel had heard what Robin said, but there was something else there that bothered her. She just couldn’t put her finger on it. “Um… Great Robin. Thanks. I’m glad you understand. So you’ll keep after him then? And maybe ask the others to do the same?”
“Yeah sure. We can do that. It’s probably the best way we can really help him with it.”
Mel scowled, more likely… help him right into her arms! And that was when the other little thing clicked for Mel that had just bothered her. “Um… Listen, Robin. There’s something else too that I’d like you to do for me. Would you try to refer to her in only the female sense all the time? Stop referring to her as a him. If she’s going to experience what it’s like to be a woman than I think that she should kind of get used to being referred to in that sense too.”
Robin thought about that for a moment. “I guess. I can try at least. I don’t think it will be that easy to do though since we’re all kind of used to him being – the other gender. You know?”
“Yeah, I know,” Mel agreed. “It’s not that easy, but I think it will help.”
“Hey Mel, while I’ve got you on the phone, can I ask you a question?”
That was exactly what Mel wanted to avoid right now. “Uh oh!” she replied quickly. They’re calling us back. I’ve got to go. I’ll call you later when I’ve got more time. Okay?”
“Uh… Okay,” Robin relied. But by the time she finished saying it, the line quickly went dead. Still… She had managed to make contact with Mel. She had actually talked to her. And next time, she was sure she could finally get some answers!
“Did I hear you say that was Mel?” Chad asked from the entrance to her cubicle. Worry and panic had pulled him away from his own desk to try to hear as much as possible – which was really nothing at all.
Robin hadn’t even known that he was standing there. “Yeah. Would you believe it, she actually called me!”
“What did she say?” Chad asked desperately.
“She said that we should all keep on your case about not using your male voice – like right now!” She actually giggled a bit. “You’ve got to stop talking like a man, Sissy. You’re never going to learn to speak better – or to even pass properly if you don’t!”
Chad just looked embarrassed and stared down at the floor. “Thanks,” he mumbled in his male voice as he turned away from her. He didn’t really want to contemplate having to talk in that silly voice all the time.
“Say it right!” Robin called after him.
He turned back to her. “Say what right?” he asked in his usual male voice.
“Everything!” Robin exclaimed.

Mel stared at the cell phone in her hand. Operation Robin had now started. The silly slut was soon going to get her due! She could just picture her with Sissy… bleached blonde, small tiny waist – probably a size zero… her hands all over Sissy’s ass as they wandered through the hallways of that building together. Oh how she hated her! Okay, maybe Robin wasn’t quite that bad, but it was fun to think of her like that.
She attempted to put Robin on the back burner of her mind and think about Sissy instead. Things sounded very good for him to now be denied the use of his male voice. And what’s more, something she hadn’t really thought about before, if all went well, he would also be denied the right to be referred to as a male too. Okay, so maybe he wasn’t exactly a female, but the point was, nobody would be referring to him as a male anymore either – she hoped.
One by one, she was slowly denying him all of his male traits, or rights, or… whatever.