The Bet - Chapter 28 (Friday – week 4 Part 4 of 10)

The Bet
by Karen Singer

Chapter 28 (Friday – week 4 Part 4 of 10)

Andrea hung up the phone after telling one of their clients that Mel had just stepped out and would be back shortly. A common occurrence. Another client was due into the office shortly. The question was, who would get there first? No real problem either way.
The door opened and Andrea fully expected to see a man in the usual grey business suit walking in. Instead, she saw a large mass of color being pushed through the doorway. Surprisingly, Mel was the one carrying the mass of color – which turned out to be a very large bouquet of flowers.
Mel deposited the large colorful bouquet right on Andrea’s desk. “This is for earlier!” she explained, then walked off with a smile on her face.
Andrea put her nose up against the beautiful bouquet and breathed in deeply. Fabulous! All her favorite flowers. She loved getting flowers, they always made her feel so good. She noticed the card stuck in the bouquet near the top. She plucked it out and opened it. “Thanks for keeping my head straight – Mel” It was just like Mel. At times she could be a real bitch, other times she was simply driven. But when it counted, she could be the sweetest person in the world.
A thought struck her, she picked up her phone and dialed Mel’s extension. “Just don’t forget about Sunday!”
Mel laughed over the phone. “Not on your life!”
Mel hung up her phone feeling good. Flowers were a just the right touch sometimes. People didn’t send them often enough. Her thoughts turned once again back to Sissy. She was still angry, but she was also more determined than ever now. Could she really blame him for what he was doing? Damn! Yes she could… but at the same time, no she couldn’t. She wouldn’t be a good lawyer if she couldn’t try to understand her opponent’s position. But that certainly didn’t mean her opponent ever had to win… especially in this case!
Another thought suddenly struck her. Wasn’t today the day his divorce was supposed to be final? She wondered how he was handling it. Men! As far as she was concerned, most of them were uncaring bastards when it came to something important. But then, Chad was only partially a man. He was certainly still a bastard, but was it possible for him to feel anything else at all? A tiny wicked spark suddenly lit in her eyes. He was a sissy – for sure. Would he be embarrassed if… Or maybe he wouldn’t care at all… Or maybe he would really like it. Either way, it was probably the right thing to do in this situation. She picked up her phone again and dialed.

Chad glanced at the clock on his computer monitor. It was almost time for lunch. Time for him to go and get his diapers changed again. Hopefully, Cassie wouldn’t be a pain like she was yesterday and she would play with his asshole once again. That thought brightened his day.
The sound of voices in Robin’s cubicle suddenly caught his attention. He thought he heard someone say ‘Sissy.’
“Oh wow!” he heard Robin exclaim. “He’s right next door!”
Chad was shocked. Someone was looking for him? Under the name of ‘Sissy?’ He quickly got to his feet, just as a young guy turned the corner from Robin’s cubicle into his. He heard the guy saying, “Are you Sissy?” But Chad’s eyes were completely captured by the bouquet of flowers in a large vase that the delivery man held. Chad was stunned. Someone had sent him flowers?
“Never mind,” the delivery guy said as he set the vase down on Chad’s desk, “I can see that these obviously are for you.”
Chad finally pulled his shocked eyes away from the bouquet to look at the man. The poor guy was obviously a bit shocked to see who… and what… “Sissy” really was. He just continued to stare curiously at Chad, unable to take his eyes off him.
Chad felt very uncomfortable under the delivery guy’s scrutiny. He had never gotten flowers before and wondered if the guy was waiting for a tip or something. Was he supposed to tip the guy? He honestly had no clue. Getting flowers was a totally new experience for him.
The delivery guy finally shook his head and mumbled something about, “Enjoy them,” and left. Chad stared after him for only a moment before turning back to the colorful vase.
“Wow,” Robin exclaimed, “you’ve only been dressing like a woman for a few weeks, and already someone is sending you flowers! I wonder what I’ve been doing wrong all these years. Are they from a man?”
Chad was still trying desperately to wrap his mind around the concept that someone had sent him flowers, so it took a moment for Robin’s question to finally soak in. “What?... Oh, I don’t know. I can’t imagine why anyone would send flowers to me.” He took a moment to try to imagine a man sending them to him. The very concept of it made him feel funny inside.
“Isn’t there a card?”
“Oh. I didn’t think of that,” Chad replied as he searched the top of the bouquet for a card. He found it quickly and pulled it out. “Sorry about your divorce,” he read out loud. “Hope these help… Mel.” Mel had sent him flowers! Were they really her way of saying she was sorry for the way she had acted last night and this morning? Or was she truly sorry about his divorce? Or perhaps both?
“Mel? Isn’t that your makeup-lady friend?”
Chad was a bit confused by her question. Makeup lady? Then he remembered that that was the only thing that Robin really knew about Mel – that she was one of the ones teaching him how to do his makeup. “Um… She’s really just a friend,” he replied, reluctant to explain things any further than that.
“A very good friend… obviously.”
Chad stared again at the colorful bouquet. “Yeah. I guess so.”
Robin leaned over the bouquet and took a big sniff. “Mmmmm. They smell soooo good!” She looked closely at the flowers and touched a few of them. “Look, there’s even a few pink roses scattered around. I just love roses. Don’t you?”
Chad really didn’t care. “I guess so,” he replied.
Robin looked at him funny. “You guess so? What are you favorite flowers? Are any of them here?”
“My favorite? I don’t have a favorite. I can’t even tell you what most of the flowers in there are… other than the roses of course.”
Robin shook her head. “God!” she exclaimed. “You’ll never make a very good woman. There’s just too many things you don’t know!”

Gloria sat alone at one of the tiny tables in the sandwich shop that was within walking distance to her office. She took a few tiny bites from the sandwich in front of her, but mostly, she hardly realized that she was eating. Her mind was totally on Mel and Chad instead. What had she done? What should she do? Had she really done something wrong? Or was what she had done the right thing to do because Chad really wanted it?
Her dilemma was compounded because there was plenty of evidence to support all sides of every argument. So basically, she just didn’t know. And therefore – she worried about it. Plus… Mel was her friend. That made things even worse. Should she go along with Mel’s wishes – just because she was her friend? Something about that didn’t completely sound right… but still, it was very tempting.
So what should she do?
If she could just talk to him again… hypnotized of course. That would be the only way to really get at the truth. But she didn’t want Mel around when she did it. Mel would only make matters worse by insisting, probably all too hard, that she put the suggestions back into Chad’s head again. There was no way she would do that, unless she was clearly convinced that he really, really did want it. And the only way she could be convinced, was to hypnotize him and talk to him. But only without Mel!
Would Mel let her hypnotize him and talk to him… without her around? Somehow, she seriously doubted that. But there was only one way to know for sure. She would have to call Mel and ask her.
Still fretting over her dilemma, she took another bite of her sandwich. Suddenly, she wasn’t hungry anymore. Disgusted, she wrapped up what was left of her lunch and dumped it into the trash can on her way out of the sandwich shop.
As she walked back to her office, she decided for sure to call Mel. There was no harm in asking… was there?

Chad walked through the door to the gym and was immediately confronted by the receptionist staring at him expectantly. He stopped a few feet away and stared back. He knew she was waiting for him to curtsey for her, but he wasn’t going to do that. Not anymore!
“Aren’t you going to curtsey pretty for me?” she finally asked.
“No,” Chad replied quietly but firmly.
“Not even since it’s just me today?”
“No,” Chad reiterated, feeling very sure of himself.
“Oh poo! You’re no fun anymore!” she exclaimed and stomped off to find Cassie.
Chad felt proud of himself as he watched her walking off. He felt like he was much more in charge of himself again… like he should be! Did he dare not curtsey for Cassie? He was tempted, very tempted. But when Cassie finally walked up, he decided to stay on the safe side of things. Cassie was Mel’s friend after all… and she did change his diapers for him every day, not to mention doing other things to him that felt “oh-so-good!” He dropped his curtsey and greeted Cassie like he always did.
The receptionist looked up at Cassie with kind of a “darn-it!” look on her face. She seemed to be frustrated at Chad’s behavior.
Cassie just shrugged and said, “Don’t worry about it,” to her. Then she turned to Chad. “Come on, Sissy. Let’s get you into the back.”
Chad’s feeling of victory over the receptionist continued as he followed Cassie through the room full of exercise equipment and sweating women. While he knew they were all watching him closely as he walked past, he hardly gave them another thought anymore.
“I like your outfit today,” Cassie noted as they walked.
“Thanks,” Chad replied. “I kind of like it too. Although Robin kept trying to convince me that I should buy some blue pantyhose for it while I’m at lunch.”
Cassie opened the door to the office and let him go inside first. “Blue?” She looked him over carefully and nodded. “Yeah, blue would work very nicely with that outfit. Are you going to get some?”
Chad rolled his eyes as he started to get undressed. He didn’t really want to mess with pantyhose at all. He searched for an answer… “Um… They’re too much of a pain to put on with this darn waist cincher I’m wearing,” he finally explained.
“Oh, they are?”
Chad stopped undressing for a moment and looked at Cassie’s figure with her tiny waist. “I guess, like Mel, you’ve never worn one either.”
“Nope, not that I can remember.”
Chad began his chore of undressing again, and caught sight of his red toenails. “Besides, it’s Friday. Mel and I always get our nails done on Friday and she has me remove my pantyhose before we go so they can do my toes easier.”
“Ah!” Cassie exclaimed as she pulled a baby bottle out of his bag. “That makes sense… Hey! This bottle is empty!”
“Oh yeah! Mel wouldn’t let me into her apartment this morning. She usually puts the fresh bottles in while I’m there.
“She wouldn’t let you in? How come?”
Chad shrugged. “I don’t know. And last night she threw me out too. I haven’t a clue as to why.”
“Hmm.” Cassie grunted as she checked through the rest of his diaper bag. “Plenty of diapers here though,” she mumbled as she continued to paw through the bag’s contents. “So no problem there.” She pulled a few diapers out of the bag along with the baby lotion, some wipes, and the jar of suppositories. “Do you want me to fill one of these bottles with water for you?”
Chad was surprised by her question. “No thanks,” he replied. “I’ll be fine.”
“Are you sure? You know that Mel wants you to drink one every day.”
Chad knew. He also knew that one less bottle would make it all the more easier for him to control his peeing later. But Cassie was right, Mel did want it. Yet… “No thanks,” he said again. “I’m sure it will be okay.”
Cassie shrugged. She would have insisted – for Mel, but she was still haunted by what authority she really had over him. She made a mental note to call Mel and talk to her again about it later.
She waited till Chad finished undressing and laid down on the floor. And then she noticed something different. She sniffed the air slightly and smiled. “Hey, are you wearing perfume today?”
Chad blushed. “Yeah. Robin sprayed it on me.”
“The same Robin who thinks you should get some blue hose?”
“Yeah. Same one,” Chad replied rolling his eyes.
Cassie stored that information in the back of her mind as she went to work on Chad’s front side. As she spread the baby lotion around whatever wasn’t covered up by his chastity device, she again took particular notice of his tiny cock. Was it even smaller than yesterday? She wasn’t sure. But she was sure that it certainly wasn’t any bigger. She didn’t have a lot of knowledge about guy’s cocks, but from the two experiences she had had when she was younger, and from what she thought she knew from many other sources, a guy’s cock was certainly supposed to be a lot bigger than what she was looking at. Was it normal for a cock to be that small? She knew it used to be a lot bigger – all the time. Was it actually shrinking? She didn’t really think that was possible, but it sure seemed like it. Strange! But interesting!
Once again, nothing she did on his front side seemed to make his tiny cock even twitch a bit, let alone get any bigger. It might have been dead meat locked up inside of that plastic cover for all she could see. Trying to get any kind of reaction out of him was now a totally useless exercise. “Ok, Sissy, roll over. I think we’re done here… maybe forever!”
Chad wasn’t sure what she meant by that, but he dutifully rolled over and immediately brought his knees up under him too. This was the part he was looking forward to!
Cassie checked his backside as she started smoothing the baby lotion all over it. “It looks like your rash is about gone now,” she noted.
“Fortunately,” Chad replied, his voice muffled by his position. “It wasn’t a fun experience. I don’t want to go through that again!”
“Hmmm. If you continue to wear diapers, like it looks like you will be, you may have no choice about that.”
“The new baby lotion works pretty well,” he replied. “That should take care of it,” he replied with confidence. He closed his eyes and started concentrating on Cassie’s hands rubbing all over his backside – delicious… sensual… addictive! And when her finger finally touched directly on his asshole, this time it didn’t send lightning bolts through his system. Instead, it sent a huge surge of sexual passion and desire through him. He wanted it… he needed it! His desire for it was almost all consuming. And when he felt Cassie’s finger actually enter him, he moaned in pleasure despite himself. But by that time, he wasn’t really paying attention to anything except Cassie’s wonderful attentions to his backside.
Cassie stuck her finger a bit further into his tiny hole and wiggled it around a bit. She watched as he reacted. The poor guy was loving it so much, he almost appeared to be hurting. She pushed her finger in a little further, pulled it out and pushed it back in a few times, then pulled it totally out again. It was time for something bigger, much bigger. She grabbed her toy that she usually used on him and held it up against his waiting hole. The moment she touched it to him, she saw him shudder. She started to shove it gently into him, but faster than she could react, he suddenly pushed himself back against it… opening himself up to take as much as he could. Before she knew it, she was holding onto the plastic ribbed dildo for dear life as he bucked back and forth, fucking himself as hard and as fast as he could.
Chad was desperate. Desperately desperate! It felt so good, yet he needed more and he needed it badly. Faster, harder… it made no difference! Still he tried over and over again to reach that peak that he could never quiet reach… the peak that only came from sexual orgasm. Try! Try! Try! Try! Push! Pull! Squeeze! Relax! Nothing did any good. It felt great! It felt wonderful – almost like he could really get there if he just kept at it. But as good as it felt, he never really got close.
He was breathing hard and fast as he realized it – puffing in great huge gasps. But in the end, he finally realized that no matter what he did, he couldn’t get there… the “there” of sexual relief! He was still denied. Still a prisoner of Mel’s unique manipulations.
He slowed his breathing along with his motions… rocking back and forth now to a much slower, much calmer rhythm. Slowing, slowing, less tension, less pressure, less rocking… till he finally stopped for a split second, then collapsed fully to the floor. He felt Cassie pulling her toy out of him. It was impossible! As wonderful as it felt, it was just impossible for him to get off. For the briefest of moments, he considered not ever trying again, but he knew better. He would try, and try, and try with every chance he got. As far as he could see, it was his only chance for relief… at least till this bet was over with. Besides, he really did love it. Why should he quit or refuse to do it. It felt great! With a huge sigh of frustration, he rolled back over onto his back.
Cassie watched him carefully as he rolled back over. He had been like a wild animal today – trying so hard. She actually felt sorry for him. As he laid there, she quickly looked down directly at his cock. It wasn’t one tiny bit bigger than it had been earlier. Not one bit! Yet she was sure that what she was doing to him was somehow sexually stimulating for him. Somewhat anyway. By his actions, she had assumed that it had been very sexually stimulating. Yet he hadn’t grown the slightest bit – as far as she could see. Just dead meat. On an impulse, she reached out and flicked the plastic trap surrounding is penis with her finger. No reaction. None at all. Incredible! Did he even care? It was an interesting question.