The Bet - Chapter 46 (Tuesday – week 7 Part 1 of 9)

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 1 of 9)

It was the most peaceful sleep she had had in a while. But that doesn’t mean her dreams were without conflict – which doesn’t mean that her dreams were without pleasure too. For in her dreams, she was in bed, making love to… Ray – at first. Because in the middle of her dream, where things were just starting to get hot and passionate between them, Derek showed up and ruined it all. But this time it was an angry Derek. Angry enough to grab Ray and pull him right off of her. She was frightened by Derek’s rage, but the fright didn’t last.
Ray and Derek argued – over her! As she laid back in her bed, watching the two hunks, she felt nothing but thrilled as they continued to argue about which one of them was going to make love to her. She wanted Ray to win because he was there first. She had already started with him. But… but there was just something special about Derek too. She really kind of liked him better for some reason. So, she was torn.
The argument turned from a very heated discussion into a fist fight! In her dream, she sat up on the bed to watch and cheer for… both of them. She felt so honored that each of them would want her so badly. So special! But then someone else climbed up onto the bed with her, someone she hadn’t expected. Sissy was suddenly at her side, holding her, kissing her, caressing her in the most intimate ways. And his touch felt so good, so arousing, so sensual.
She laid back on the bed and let Sissy make love to her while she kept watch on the two hunks fighting over her in the distance. How perfect could anything get?
But one of the two big men noticed what Sissy was doing and their fight stopped. Together they rushed at her… and Sissy. In their rage, they both tore Sissy from her grasp and threw him angrily away from her. Together they kicked and beat him horribly, chasing him further and further away from her, until finally, Sissy had no choice but to run away as fast as he could – never to be seen again.
She felt heartbroken. Victorious, the two big men returned to her bed together, and together they caressed her and made sweet love to her, but it was a bittersweet love. Despite them, her heart ached horribly for Sissy, and despite the two hunks lavishing their attentions on her, she yearned for him.
The alarm on her clock buzzed and she awoke. She felt like she had gained something – but in the process had lost something bigger. She just didn’t know what that something was. She reached over and turned off the alarm as she sat up on the side of the bed. Her need for coffee was so ingrained in her that she didn’t even think about it. She grabbed her robe as she got to her feet and slipped it on as she headed out toward her kitchen.
As she watched the freshly brewing coffee dripping into the pot, her mind remembered that she had a date tonight – with Ray. She was looking forward to that. She was really hoping that it would be fun… and hopefully, would lead to – something else! But later tonight was still a long way off and other things soon made their way into her consciousness. Things like – Sissy. He had been so great last night – again! Really, the little sissy had the most wonderful touch. And his tongue! She remembered that he was supposed to be going out with Sandy and Cassie later tonight to visit their friends. She had a feeling that that was going to be an interesting trip.
Her coffee finished brewing and she reached for the cabinet to get a cup, but she had to stop and correct herself as to which cabinet to open. She hated change, especially when it involved anything that she had to do before she had her coffee! A minute later, her coffee poured, she took a sip and carried it into her living room where she sat in her chair.
Thinking about Sissy, soon led her to think about Robin. Yesterday had been strange. Not at all what she had expected. And Robin had actually ordered Sissy to suck his thumb! At work? Amazing! Did that mean… she almost didn’t dare to think the thought… did that mean that Robin might become someone who she could count on to help with Sissy while he was at work? It seemed too remote a possibility to really give credit to. But… was it possible?

One minute he was sound asleep, the next, loud blaring rock music poured out of his pink clock radio, jarring him from a sound slumber into instant confused wakefulness. And he had been sleeping so good! As soon as he could collect his wits enough, he rolled over onto the floor from his blow-up mattress, scattering a few empty baby bottles in the process, and got to his knees, where he immediately reached over and turned the overly obnoxious music off. What a way to wake up every day! Ugh! But he had to admit, it certainly worked!
He took a deep breath and took stock of himself. His diapers were overly bloated as usual – messy too. His backside itched terribly because of the beating he had gotten last night. He hoped it wouldn’t turn into diaper rash. He had put a bra on before going to bed last night to help support his glued-on breast forms. They still hung heavily from his chest. Of course, his penis was locked away inside of a chastity device and had been for a long time now. It had become mostly… useless. And last night… last night she had taken him in the rear… and he had orgasmed that way. Unbelievably!
He climbed awkwardly to his feet, hampered by the thick diapers he was wearing. He resisted the urge to scratch a bit at his irritated backside as he stumbled awkwardly out toward the kitchen where she usually left him his note. Once again, the note was there, but it might as well have been the same one she left every day now. Except… this one had one extra line added. “Wear something with a full skirt today!” What did that mean? Why? Wearing a skirt was a given now – he had no other clothes anymore except women’s clothes. And the way things had worked out, dresses and skirts worked the best for him – they helped hide the bulk of his diapers. Not to mention that she had restricted the number and style of women’s pants that he could own anyway.
Having no clue why she should specify a full skirt, he gathered his three required baby bottles from his refrigerator and carried them out to his only chair. Gingerly, he sat down and put the first one to his mouth as his eyes wandered over the childishly colored pictures she had made him create in the restaurants. But he had seen those pictures enough now that he barely noticed them anymore. Why a full skirt? And… which one should he wear?

Mel stirred his baby cereal in the pot on her stove. She glanced at the clock. – it was almost time for him to be here. The knock on her door was actually two minutes early. She turned the stove off and went out to open it.
“Good mowning Mistwess,” Chad said in his sissy voice as he curtseyed for her.
“Good morning Sissy,” Mel replied as she stood back out of the way to let him inside. She waited till he deposited his diaper bag and purse under the table she kept by the door. Then she looked him over. His hair was styled – good enough. His makeup looked – acceptable. She noticed that he was wearing the pink ear studs again today along with the rest of his pink jewelry. She could tell from his shape that he was wearing the required two diapers, waist cincher, and all-in-one girdle under his clothes. His reddish brown blouse was frilled along the entire neckline and went well with the colorful pattern on his skirt. And on his feet he was wearing a pair of brown ankle strap heels. Overall, he looked… not too bad – for a guy wearing women’s clothes.
She reached out and pulled his skirt to the side, seeing how wide it would go. Very good.
“This is the fullest skirt I had,” Chad said in his sissy voice as she pulled it to the side. But the moment he opened his mouth to say it, she got mad and rushed off. Chad knew he had messed up before the words were completely out of his mouth. All he could do was to curtsey as she rushed back toward him, her thick yardstick in her hands. “I’m sorry Mistress,” he said in his sissy voice. “I forgot.” There was nothing he could do but to stand there and accept the blows from her stick as she hit him on different parts of his body.
“When are you going to learn to curtsey every time you open your mouth?” she said angrily as she hit him. Chad made no reply.
“One way or another, you’re going to learn!” she said as she offhandedly hit him two more times. “Now get in there and get up in your highchair!”
A few minutes later, Chad was trying to shovel horrible tasting baby cereal into his mouth, using a tiny baby spoon held in his left fist, while he was sitting in his highchair wearing a bib.
Mel poured herself another cup of coffee and leaned back against the counter to watch him like she usually did. “I’m glad things went better with Robin yesterday than you thought they would,” she said.
Chad looked up from his breakfast. “I’m not sure it was good at all! She was so angry – even when she left yesterday.”
“I would say that ‘not getting fired’ is something good.”
Chad nodded. “Yeah! That part is a big relief!” He dug another spoonful of the mush out of his bowl.
“I want you to keep telling me about every little thing she says and does with you today. Like yesterday, if anything happens, I can’t help you if I don’t know what’s going on.”
Chad shrugged, which caused him to spill a bit of the baby cereal already on his spoon. “That should be no problem… unless she makes me keep my thumb in my mouth all day again. It’s really hard to type like that! And I still don’t know why she did it!”
Mel wasn’t exactly sure either. “Just make sure you keep doing whatever she says! And don’t forget to apologize to her as soon as she gets there!”
Chad said nothing as he shoved a bit more of the lousy tasting cereal into his mouth. The apology she had made him practice over and over again last night. He still wasn’t sure he would really go through with it – at least not quite like Mel wanted him to.
As soon as he had finished his breakfast, Mel released him from his chair, but she didn’t let him go to work yet. “Let me see your apology for Robin again,” she ordered.
Chad inwardly groaned. He dropped a small quick curtsey to Mel first – just in case. Then he launched into his little “routine” for Robin. He grabbed his skirt with both hands and dropped into as nice a curtsey as he could…
“No! Spread that skirt as wide as it will possibly go. I want it flared as much as possible! That’s why I asked you to wear it in the first place! Now do it again!”
Chad grunted, then dropped yet another little curtsey for Mel – just in case, then he tried it again. He grabbed his skirt and dropped into his curtsey again – this time pulling wide with both arms as far as the skirt would let them go.
“Better!” Mel commented. “Much better!”
Chad bowed his head momentarily, then he rose up again and brought his feet right together next to each other and clasped his hands in front of him. Then he launched into his little speech. In his sissy voice he said, “I’m sorry Robin that I didn’t do exactly what you told me to do yesterday. I promise not to give you any more trouble and to do whatever you say from now on.” Once again, he dropped into another curtsey, spreading his skirt as wide as possible and bowing his head, before he got back to his feet again and put his hands together in front of him. He turned to Mel and curtseyed. “Was that good enough?” he asked.
“Do it again,” was Mel’s only comment. She made him go through it four more times, just to make sure he had it down perfectly. “Now don’t forget. You do it exactly like that. And this time, use your sissy voice too. No sense practicing it this way and then messing up by doing it differently. Got that?”
Chad curtseyed. “Yes Mistress.” What else could he say?
A few minutes later, Mel watched him driving off toward work. She went back into her house and turned on her laptop. As soon as it was ready, she opened up her email program and began working on an email for Robin. “Okay,” she said out loud to the empty room. “Now we’ll see what we’ll see! Let the games begin!” And with that, she made a little flourish with her hand, and hit the send button.

Robin parked her car, gathered up a load of different things into her arms that she “might” want during the day, and headed in toward the building. She didn’t see Chad’s car yet, but that didn’t mean that he wasn’t here already. Her problem this morning was that she still wasn’t sure what to do about him – or how she should go about even talking to him. She wasn’t even sure she really wanted to talk to him yet… if ever. So she wasn’t really looking forward to seeing him again.
She had made the stupid jerk spend several hours yesterday afternoon sitting with his thumb in his mouth. And the idiot had actually done it! Well, he had deserved it! He wanted to be a baby? Served him right! She had been in no mood to be played with yesterday. She still wasn’t, but she was at least thinking a bit clearer today. It still galled her what a stupid pervert the guy had turned out to be – and she never had a clue! Imagine, wanting to be somebody’s… slave! The idiot! And he wanted to be a baby too? The two just didn’t jive in her mind. Not that anything about him did anymore.
As she approached his cubicle, she slowed her steps a bit. With a rather angry look on her face she looked into his cubicle as she walked past – and breathed a sigh of relief. The jerk wasn’t in yet! Maybe he’d stay out the rest of the day… wishful thinking.
She dropped her load of things onto her desk. Rummaged through her bag till she found her mirror and checked her face and hair. Stowed her bag into her desk drawer, and turned on her computer. Just a normal day, she tried to tell herself. But she knew better.
It took a few minutes for her computer to fully boot up. When it did, she opened up her email program that she kept open all the time. She was surprised to see an email from Mel – already! What did the crazy woman want now? Did she dare open it? But opening it was a foregone conclusion.

Dear Robin

I’m just checking to make sure that Sissy really did apologize to you “properly” as soon as he arrived today.

Please let me know as soon as he does – or doesn’t!

As always, feel free to call or email me,
Mel

Apologize? Robin remembered from a previous email yesterday that she should expect a “proper” apology from him. Whatever “proper” meant. But so far, the jerk hadn’t showed up yet. Fortunately! She closed the email and opened up the internet to check the weather.

Chad knew he was running a few minutes behind, so he was fairly sure that Robin would be in already. He didn’t see her as he approached his cubicle, but that didn’t mean anything since her cubicle was beyond his. Treading lightly, he entered his cubicle. He wasn’t even aware of it, but he was trying to make as little noise as possible so as not to anger Robin, or even alert her that he was here. He stowed his purse in his desk drawer and closed it quietly. Then he sat down gently, as much from trying to be quiet as in difference to his still stinging backside. He started logged into his computer and was alarmed at how noisy the keys on his keyboard seemed to make.
“Sissy!” Robin’s voice called angrily over the wall between them. “I hear you in there! Are you supposed to apologize to me?”
Well, he knew he couldn’t avoid Robin forever. “I’m just booting up my computer,” he called back, looking for an excuse to delay things.
“According to your… mistress,” she spat, “you’re supposed to apologize – first thing! So by my book, that means first – before you do anything else!”
Chad gulped. She still sounded awfully angry. Would she make him sit here all day with his thumb in his mouth again? He hoped not. Instead of answering, he hurried out to see her.
Robin didn’t even know why she cared so much. Well, the jerk probably should apologize to her – for a multitude of things! Not that she was really in any mood to accept an apology from him. Still… She saw him coming around the corner and starting to enter her cubicle. “Stop right there!” she ordered quickly. “I don’t want you that close to me. Back up!”
Chad was surprised. Back up? But he backed away from her till he was just out of her cubicle.
“Further!” Robin ordered. “Like… the middle of the hallway, at least.”
Chad looked around, fortunately, he didn’t see anybody coming. He backed up further.
“Now. I guess I’m supposed to listen to some kind of stupid apology from you? So let’s have it so I can stop looking at you. Not that I’m probably going to believe anything that comes out of your mouth,” she muttered.
Chad was a little taken aback by her attitude, but he was supposed to apologize, so he figured he better apologize. He just didn’t see himself doing it quite the way that Mel wanted him to. Once again, he looked up and down the hall to see if anyone was coming – fortunately not. He wasn’t about to give her the full version, but he did drop a quick little curtsey for her as a start. “I’m sorry Robin,” he said in his girly voice, “for taking my thumb out of my mouth yesterday after you told me to keep it there.” Should he add any more? It was already more than he wanted to say, but he figured he better add one more little thing that was – sort of – what Mel wanted. “I promise I’ll try to do better and listen to what you want from now on.” Then, since he had no better way to show that he was finished, he dropped another quick little curtsey. He watched her just staring at him. Was it enough? Could he go back to his desk now?
“Huh!” Robin grunted as she shook her head. “Listen to what I want? I don’t want to see you! Get out of here!” She purposely turned her back to him, hoping he would get the point.
Chad was just glad it was over and hurried back to his desk. As soon as he was done logging into his computer, he decided he had better tell Mel about Robin’s reaction.