The Bet - Chapter 47 (Wednesday – week 7 Part 1 of 8)

The Bet
by Karen Singer

Chapter 47 (Wednesday – week 7 Part 1 of 8)

It was the strangest dream he ever had. He was supposed to be… a pony! He was almost entirely naked except for a leather harness that was strapped around his body. His arms were bound tightly behind his back to the harness – as if he had no arms at all. Another harness was strapped around his head with a metal bit stuck between his teeth. Long leather reigns were draped from the bit between his teeth, over the back of his head, and were held on the other end by Jillian, dressed as the trainer… or ringmaster. The harness on his head had a large white plume stuck on top of it. The only other thing that adorned his body were the very high heels on his feet.
Jillian, stood in the center of the ring wearing a white top hat and a white coat with tails. Her long legs were encased in nylons and she wore white heels on her feet. And in her hand, she carried a long cane that she used as a whip.
Round and round she made him trot. Every little hesitation or stumble resulted in another stinging flick of her whip. Round and round, prancing in his high heels.
“Higher!” she ordered.
And he did his best to raise his knees up higher with each step.
“Higher!”
But he didn’t think he could lift them any higher… not until her whip showed him just how possible it was.
There was a crowd all around them, watching, cheering. But they were all beyond the bright lights that were on him, so while he could hear them, they were nothing more than vague shadows beyond his ring.
Round and round, prancing, trotting. Her whip making sure that he never slowed down. Over and over it cracked, either against his legs, or just behind him – continually urging him on, and on, and on.
“Halt!”
He stopped, grateful for the chance to rest. But now he was more aware of the crowd beyond the bright lights. His eyes darted back and forth, from side to side like a hunted animal, trying to get a better view of the onlookers beyond his vision.
“Bow!”
He stuck his left leg straight out and bent his right knee a bit as he bowed forward at the waist. The applause came again followed by another crack from her whip telling him to straighten up.
And then she issued the oddest command of all. “Speak!”
He tried to speak, he tried hard, but with the metal bit in his mouth everything he tried to say came out totally unintelligible. His tongue was either under the bit or behind it and all that came out was mushy gibberish. The crowd laughed at him and he felt embarrassed by it.
“Louder!” she commanded gleefully with another crack of her whip.
He tried again, louder. But still had no better results and the crowd continued to laugh at him. The darn bit wouldn’t let him say anything properly!
“Louder!... Louder!... Louder!”
He was screaming now, his resulting voice starting to sound more and more like the bellow of a real horse. As the crowd broke into a wild applause, he felt tears rolling down his face. And then, like a horse, he felt himself letting loose uncontrollably with a strong gush of pee further below – straight onto the ground where everyone could see. And the crowd went wild!
Jillian, holding her whip high up into the air in triumph, took bow after bow as she circled the ring like some great conqueror.
He was only saved from further humiliation by the loud blaring rock music that suddenly jarred him out of his dream, out of sleep, and into the waking world where everything was normal again… or not so normal in his case.
Irritated by the violent music from his pink clock radio, he rolled off of his blow-up mattress, his legs knocking over empty baby bottles as he hit the floor. Struggling to his knees, he reached out and turned the music off, and sighed with relief. Whew! His alarm was just that – alarming!
He took the time to survey himself. All the diapers that Sandy had put on him last night were thoroughly soaked – as usual. He was messy too, as usual. His backside still itched and stung from the beating he had gotten last night. His left bra strap had slipped off of his shoulder during the night. He pulled it back up to better support his glued-on breasts. Other than that, he was naked except for the chastity device buried deep inside of his heavily bloated diapers. But he didn’t even think about that. What would be the point?
He struggled to his feet and began making his way out to the kitchen to check for the note Mel always left him, but when he got there, his counter top was empty. Panicking, he checked all over the floor in case it had slipped down. No note! None!
He remembered that she had a date last night with Ray. Had she come home at all afterwards? Her spending the night with Ray sounded all too logical. Chad was disappointed to think about it, but he had to understand. Mel certainly wasn’t about to get romantically involved with a sissy like him, so he was forced to understand – totally. But it still gnawed at him.
Knowing what would be expected anyway, he went to his refrigerator and extracted three baby bottles of Mel’s foul tea mixture and carried them back to his solitary chair where he sat down very gingerly with them because his backside still hurt so badly from the beating Jillian had given him last night. As he sat, he noticed that the mess in the back of his diapers felt a bit strange. More solid than usual? He was probably just imagining it because his backside still hurt so much. He put the bottle to his lips and half stared at the childish drawings that adorned his walls. Drawings that he had childishly colored in the restaurants. Drawings that used to make him feel funny to look at, but no longer mattered as much to him anymore.
He felt himself peeing yet again. As usual, there had been no notice beforehand. Later, after he got dressed for work, he would again start working on trying to hold back. But now, with three more bottles to drink, it would be a useless exercise. He always drank way too much in the mornings to even think about holding back. Better to let it out as much as possible, as soon as possible.
His thoughts drifted back once again to Mel. Did she come home last night? He knew it shouldn’t, but it still bothered him.

Mel pulled her robe around her as she walked out toward her coffee pot. Heading to get coffee was nothing more than a reflex, a habit. She didn’t even think about it. Her mind was mostly on last night with Ray.
It had been… wonderful! Mostly. The perfect date. A man with a perfect body. And he was certainly no slouch in bed either! Every move he made had been practiced, planned, perfected. And that was where her only problem was. Even now, in the light of day, after a night to think on it and relive it all – fondly, the one thing that she didn’t like was that it had all seemed too… artificial. She had the feeling that he used the same moves he made with every other woman. The sex had been great, but it still lacked… intimacy. If she went out with him again, would there be anything different? There had to be! But, the artificiality of it still bothered her. Of course, she wasn’t about to marry the guy, so why should she care? But, she did.
As the coffee dripped down into the pot, she thought about Sissy. She felt guilty about not leaving him a note, even though she had no reason to feel guilty at all. Sissy’s love making certainly didn’t lack for intimacy. In fact, it was all intimacy. But then, she couldn’t ever make love to him as if he were a real man. She almost laughed, she could however make love to him as if she were the man and he was the woman. She had already done that once and the pathetic little wretch had actually orgasmed from it. Amazingly!
Would Sissy drink his required bottles this morning like he always did – without being told in a note? She was fairly sure he would. Or… he had better! She wondered how his night went last night. Well, she would find out soon enough as soon as he got here.
Her coffee done, she poured herself a cup and took a sip. Mmmm!

Chad stared at his reflection in the mirror. He looked like… a woman? No! He only wished. He wished he looked like any one of the sexy beautiful women he saw every day. Or even like any of the not as sexy ones. But instead, despite how much more he looked like a woman than he used to, he still looked like… a sissy! Which unfortunately, he was. Totally! The fact that he was dressing this way for work certainly made that fact abundantly clear.
He had curled his hair and arranged it like Mel wanted it. His makeup was done like Mel wanted it. Today he had chosen his zebra print dress to wear with suntan pantyhose and black pumps adorning his feet. His jewelry consisted of a wooden necklace and matching bracelet with the clear studs in his ears today. Under it all, his glued-on breasts were supported by an all-in-one girdle that felt two sizes too small. His stomach was further diminished by the waist cincher he wore under the girdle. And also under the girdle was his plastic panties which encased the two disposable diapers he had put on – over the chastity device that encased his mostly useless penis. Dressed for work. Again. Like a sissy.
He loaded all his empty bottles from last night and this morning into a plastic bag and grabbed his purse and diaper bag. He was ready. Time for anther day of humiliation. His thoughts briefly turned toward Robin at work. He had no idea what had gotten into her. Things between them yesterday had turned downright – weird! And she wanted to be in charge now? Unfortunately, given his present state, he saw no way around that issue at all.
With a deep breath for courage, he opened his door and walked out, heading for Mel’s apartment next door. When he got there, he knocked. The door was opened after a few moments. He curtseyed. “Good morning Mistress,” he said in his sissy voice. He was pleased to see the smile on Mel’s face.
“Good morning Sissy, Mel replied as she stood back out of the way to let him inside. She started looking him over as he was still stowing his diaper bag and purse under her little table by the door. The zebra print dress today. She liked it on him. She waited till he stood up straight again before checking him over thoroughly. She smiled. She liked everything she saw. “Okay Sissy, up into your highchair. I’ve got your breakfast all ready.
She followed him into the kitchen, but she noticed that he was having more trouble than usual climbing into his chair. “Are you okay?” she asked, clearly concerned.
Chad blushed. “My bottom is still sore.”
“Your bottom?” Her thoughts turned immediately to the punishment she had given him two nights earlier. Could that still be… No, he hadn’t shown any sign of a problem with it yesterday. So… “Did you get punished last night?” she asked as she put the highchair tray in place, securing him into the chair.
Chad nodded sullenly. “Yeah.”
“And why was that?” she asked as she picked up his bib and tied it around his neck.
“I missed my first deadline,” he explained. Then as if to justify things he added, “Things were just too busy at first and I didn’t get enough to drink till later!”
Mel only smirked as she grabbed his breakfast of baby cereal off of the counter and put it down on his tray for him. “Deadlines are deadlines! So you deserved it. How many times did they hit you?”
“I don’t know. First Stacy had me over her lap, then Jillian chained me to the coffee table and had at me. And it just went on and on. And she hits hard! Especially with that paddle she has with the holes in it. The whip she used later wasn’t much fun either!” he added sullenly.
Mel’s eyebrows went up at the mention of the paddle, but the whip momentarily dropped her jaw. Sandy had said they were kinky, but that could have meant almost anything. She never thought they would be into something where they would have implements like that on hand.
“So you were both paddled and whipped because you were late?” she asked as she set a full baby bottle down on his tray for him to drink.
“Well, actually, the whip came later, when they were playing with me.”
“Playing with you? How did they play with you?”
Chad looked for a decent way to answer without revealing too much. “They kept trying to make me sound more babyish when I talk,” he replied.
Mel nodded. She well remembered Sandy’s baby language she had been teaching him. She was only surprised they would use a whip to encourage things along. But then, Sandy had said they were kinky.
She poured herself another cup of coffee and leaned back against the counter to watch him eating – like a child. He really did look ridiculous!

All the way to work, the uppermost thought on Chad’s mind was Robin. Robin and what he went though yesterday with her… and what would she be like today? Yesterday she had made him do that stupid apology over and over again, while she seemed to ignore him. Then she wanted him to use only sissy talk around her from now on. And finally, she decided she wanted to be totally in charge. But from the way she had been acting, he wasn’t really sure now what she wanted to be in charge of. Just the project? Or him? He guessed it was him because she had said to think of it as kind of the same relationship he had with Mel. Which meant… he now had another mistress! Which really surprised him because he never thought of Robin as being… that type!
He parked his car and headed into the building, exchanging an awkward good morning greeting with several of the other women heading in at the same time. When he got to his desk, he wondered if Robin was in yet, but he wasn’t really brave enough to want to find out. One thing she had pressed at him over and over again for the last few days was to leave her alone! She didn’t seem to really want to know that he was around. She didn’t want to see him or hear him. Would she be that way today? Between that choice and having her dominate him like Mel did, he wasn’t really sure which would be the better option.
He stowed his purse in his desk drawer and booted up his computer, still wondering what today would bring.