Friday, December 9, 2011

The Bet - Chapter 45 (Monday – week 7 Part 3 of 7)

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 3 of 7)

Ray sorted through the pictures he had taken last night. He had sent them all on to Mel, but now… Now, it was just a shame that Derek wasn’t here this week. It really wasn’t as much fun, making fun of someone when they weren’t there – to receive the “benefit” of all his trouble. But, unfortunately, timing was everything. He selected one of the pictures of Derek kissing Sissy. One of them dancing together. One of them with the dessert for two between them. And finally, one of them holding hands together on the way out of the movie. He had more, but he was sure that these would be enough.
Now, who to send them to? Robin, of course, and he finally selected three other women from around the company that he knew would “spread” the gossip. Perfect. One click later and the pictures were sent. Now all he had to do was to sit back and listen to the office chatter. Poor Derek. It really was such a shame that he wasn’t here.

Robin cruised straight past Chad’s cubicle as she returned to her desk. She only noticed out of the corner of her eye that he was still in there. She still didn’t want to talk to him… if she ever talked to him again! Unfortunately, because of the other women in the company, she was going to have to – eventually.
She sat down at her desk and noticed that she had some emails. One of them was from Ray. What did he want? She opened the email – and was shocked to see a picture of Sissy kissing Derek! She didn’t quite know what to think about that. Then she realized there were more pictures in the email. As much as she didn’t want to look at them, she couldn’t not look. Last week, before she knew what was really going on, she would have swooned over the pictures and had a ton of fun with them. But now? Obviously, Sissy had had an interesting date Sunday night. Obviously! She just wasn’t sure she wanted to know any more about it.

Mel finished up with her client and immediately checked her email again. No message from Chad. No calls either. She didn’t know if that was good or bad. There was also the possibility that Robin was yelling at him right then and he hadn’t had time to write to her yet. But she figured that more likely, things were quiet where Chad was.
Knowing she shouldn’t put it off any longer, she sat down to write to him.


I doubt that Robin will continue avoiding you forever. I think you should be prepared for the fact that she’s probably going to be pretty upset at you and will probably show it. So be prepared to be yelled at… at least!

One more thing – and this is important! If she tells you to do something, then I suggest you follow her wishes and respect her needs. I can see several possibilities there. She may want you to explain more about what’s going on, or she may just want you to shut up and not say a word. Who knows? She may want something else entirely! I recommend you do whatever she wants and just let her vent. Just keep me informed as soon as possible.

Chad read Mel’s email and shook his head. Why did she even bother sending it? He was more than sure that – eventually – Robin would speak to him. And he was also fairly sure that Robin wasn’t going to exactly be nice to him when she did. And what else was he supposed to do except shut up if she wanted him to be quiet or to try to explain if that’s what she wanted instead. Dumb instructions! But at least he knew that Mel was watching and that she cared. That in itself was fairly comforting.

Ray stood outside the restaurant and waited for Mel to show up. He finally saw her arrive and pull into an empty parking space. He had to wonder about her. She was a lawyer, so she must make pretty good money. She drove a real nice car. So why didn’t she live in a more upscale place? Well, maybe it would make good conversation for lunch. He smiled as she came running up.
“Hi!” Mel said breathlessly. “I’m so sorry I’m late. Clients can be so… frustrating sometimes.”
“Don’t I know it,” Ray replied as he politely held the door to the restaurant open for her.
The restaurant was packed, but they still got a table right away. Wait staff were hurrying everywhere trying to take care of customers as fast as possible. Before they had a chance to start talking, a waiter was there to take their drink order. Since everything seemed so rushed, they each picked up a menu and read through it quickly before saying anything to each other. The waiter was back quickly with their drinks and they each ordered something light off of the menu. The waiter departed just as fast as he had arrived.
“So where would you like to go tomorrow night?” Ray asked as he leaned forward across the table.
Mel wondered if the look in his eyes was hunger for some lunch, or her.
“I don’t know. Surprise me!”
Ray smiled and started to lean back in his chair before speaking, but Mel added one more thing. “Maybe someplace nice where I can dress up again. I don’t get the chance all that often.”
Ray’s smile broadened. “How about dinner, then a club or two. I know you like to dance.”
“Sounds perfect!” Mel replied happily.
“So I was wondering,” Ray said, launching into his newest conversation topic. “You’re a lawyer, so I’m guessing you make a decent amount of money, and I noticed that you drive a nice car – real nice by the way, but the apartment you live in, while it’s nice, doesn’t seem to quite… suit you.” He was hoping he was polite enough by the way he posed the question.
Mel shrugged her shoulders. “I moved there right after college and… I guess I got comfortable. I am working on something right now though where I hope to be buying a new house very soon.” She didn’t add that that something was Sissy!
Ray figured that that explained things fairly well. She just got… lazy about it. She probably didn’t have the “drive” to want all the trappings that came with success. Either that, or she wasn’t all that successful. “So…” he began again, trying to find another topic that dealt with her. “How did you wind up as nursemaid to Sissy?”
Mel almost choked on the word “nursemaid.” Fortunately, she hid it quickly. As far as she could tell, Ray hadn’t heard any of the gossip that Robin was bound to be spreading – yet. And she hoped things would stay that way. “Um… Sissy moved in next door to me.”
“And you somehow discovered that he wanted to be a woman?”
Well, that wasn’t really correct but… She realized she was treading on dangerous territory here. “Um… Something like that.”
“So, how did it happen?”
Big red flags went up in Mel’s mind. “Um… We each got a bit too drunk.”
Something about her answer surprised Ray. “So, you actually went out with him and you both got drunk and he told you he wanted to be a woman?”
“Um… Not exactly. I bought some beer and we had it at my place.”
“So…” Ray continued, just trying to keep the conversation going, “was he dressed as a woman then?”
Mel really wished he’d get away from this line of questions. “No. It just kind of came out while we were blitzed.”
“And you encouraged him in it?” Ray asked incredulously.
Mel really had to get things away from this topic. Ray was asking all the wrong questions. “That wasn’t… quite what happened,” she replied. Then she tried to move things on to something else. “Let’s not talk about Sissy. Let’s talk about you instead. So, do you have something against Derek?” she asked.
Ray was clearly surprised by the question, let alone her changing the subject so abruptly. “No, not really.”
“But you clearly like teasing him.”
Ray smiled. “Who wouldn’t? Sometimes, the guy just asks for it.”
Mel wasn’t all that sure about that. She somehow had the impression that Ray was more like the big rooster in the henhouse, and he didn’t want any competition around. Fortunately, their lunch arrived just then and the conversation went back to their upcoming date tomorrow night. Mel was relieved!

Cindy watched almost angrily as Sissy drove into the parking lot and got out of his car carrying his big pink diaper bag with him. But she dared not make any fuss over the matter since Cassie was standing right next to her, also watching him approach. The reason she was angry, was because Cassie had just told her, in no uncertain terms, that she couldn’t even watch today. And Cassie had made it just as much a point to tell her not to argue about it. So now, she was a bit… miffed at.
Chad got through the gym door and was surprised to see Cassie already up front, waiting for him. But he and the receptionist were staring at him as if waiting for something. With a bit of a sigh, he curtseyed and greeted first Cassie, then he did it again for the receptionist. He was rewarded by seeing the look on the receptionist’s face change to one of delight and he heard her giggle.
“Come on Sissy,” Cassie said as soon as he finished. “Let’s get started.”
Chad couldn’t believe his luck, especially when he realized that the receptionist was staying behind. “She won’t be joining us today?” he asked quietly as they made their way past several women on the treadmills.
“Not today,” Cassie replied.
“Hi Sissy,” one of the women called to him as he walked past. She was very sweaty from her workout. He just waved his arm a bit in reply and kept walking. He really wished they would forget him there, but that was probably asking too much.
“How was your date?” Cassie asked a minute later as he started to get undressed.
“I got through it,” Chad replied.
“But did you have any fun?”
“Well… It was mostly, awkward,” Chad admitted. “Very awkward! But the movie was good!”
“Well, that’s something anyway,” Cassie replied as she started pulling supplies out of his diaper bag. A few minutes later, she peeled back his completely soaked diaper, exposing his chastity clad penis underneath. “So how are things going with your friend Robin today?” Cassie asked as she took a cloth to start wiping him off.
“I don’t know,” Chad replied as he briefly took his bottle out of his mouth. “She won’t speak to me. I don’t think I’ll have to worry about it very long though, because once she tells enough people, I figure I’ll get fired pretty quickly.”
That startled Cassie. “I hope not!” she replied with genuine concern.
“Me too. But I don’t see it not happening.”
“Pray. Maybe a miracle will happen.”
“It will have to be a big one!” Chad replied. He put his bottle back into his mouth and sucked on it worriedly.
Cassie was about to tell him to roll over so she could do his other side, when all of a sudden she saw a ton of pee rushing out of his chastity device. As she quickly grabbed the wet diaper still under him to pull it protectively back in place, she noticed the look on his face – as if he was totally oblivious to what he was doing. Was it possible?
Chad was startled as Cassie suddenly pulled his wet diaper back into place. The action interrupted his moody thoughts enough for him to see the surprised look on her face. He was about to ask what she was so startled about, when he finally realized he was peeing. Embarrassed, he apologized for what had just happened. Geez! He had to get with it and get control of himself again. He had been so worried about Robin and getting fired all morning that he had barely even tried to control himself.
Cassie finally pulled the wet diaper back a bit to check to see if he was done yet. There was still a tiny bit of pee dribbling out of the tip of the plastic device. She watched till it finished. She was just glad that she had noticed what was happening fast enough. Catastrophe averted! She once again wiped off his front side, then slid the now even more soaked diapers out from under him. Seconds later, she slipped fresh dry diapers back in their place. “Okay, roll over,” she finally said.
Chad removed the bottle from his mouth and set it aside as he rolled over, exposing his backside for Cassie to clean – and hopefully play with. The cleaning took only moments, but the luxurious feel of her hands massaging in the baby lotion all over him felt totally exquisite! He closed his eyes as he concentrated on the feel of her hands. His hopeful longings were rewarded when her fingers finally moved closer and closer to his little back hole, and finally into it. What a feeling! He didn’t know why he loved it so much, but he did. It simply felt – great! He enjoyed her finger moving in and out of him for a few moments, then he felt her hands leave him again. A moment later, something much larger and harder was pressed up against him. That made him really happy!
Cassie moved her toy slowly into him, then slowly out again, but it was only moments before he was actively trying to push and pull himself against it. Instead of trying to control it in him, she just held on and let him do all the work – and very soon she had to hold on tighter because he was doing an awful lot of work!
Chad pushed himself back and forth, over and over again against Cassie’s toy. It wasn’t just that it felt good, it was something much more, something… sexual. Maybe it was just that it had been so long now since he had been able to orgasm. Or maybe it was just that he was liking it more and more. He didn’t know and didn’t care. He simply couldn’t get enough of it. And it seemed like his enjoyment from it was more than ever before. But as usual, eventually he realized that all his effort was useless. He wasn’t going to orgasm from it. It was impossible. All he was doing was making himself even more frustrated. That was the big problem with his chastity device, it simply made some things totally hopeless. He slowed down and buried his head in his arms in frustration as he felt Cassie pulling the toy out of him. Hopeless! A moment later, he felt Cassie’s finger invading his backside once again as she pushed the inevitable suppository up inside of him. Hopeless!
Cassie smiled to herself. Once again she had only faked putting the silly little suppository up into him, and once again he obviously didn’t know it. Would he ever find out? She wondered what would happen if he did. Not that it would really matter. Mel would probably go back to making sure he got one every time – and she would probably have it done in such a way that he would know without a doubt that it was there!

1 comment:

sarah penguin said...

Yay more story! Poor Robin she's a stressed narrative bomb waiting to blow. Poor Chad, he's got to be developing ulcers about it. It's a good story though, eben though they are so upset. I don't often say this but, yay drama!