The Bet - Chapter 34 (Thursday – week 5 Part 1 of 6)

The Bet
by Karen Singer

Chapter 34 (Thursday – week 5 Part 1 of 6)

The bright sun luxuriously bathed her body as she lounged out by her pool – her big beautiful pool behind her big beautiful house. The sun was making her thirsty. Before she could summon refreshment, Sissy was there at her side, silver tray in hand, with an icy cold drink on it. So perfect. “Thank you, Sissy,” she said as she took the drink. She watched as he curtseyed in return and thrilled as his high-pitched sissy voice replied that she was welcome.
She stared up at him. His maid’s uniform was impeccable, right down to the pretty white apron and the white cap in his long hair that was tied back with a ribbon to match his uniform. The perfect picture of masculinity denied. And she was the one who had taken that masculinity from him – every little masculine trait she could find! The very thought of it sent waves of sexual pleasure throughout her body.
She glanced around at the rich opulent landscaping. Sissy had nothing at all to do with the upkeep there. She wouldn’t allow it. There was nothing at all about landscape maintenance that she considered even remotely feminine – it was all a task for men. And having him feel even the tiniest bit like a man was against everything that she wanted.
She watched him carefully as he made his way toward the shaded entertainment patio, his bottom wagging back and forth with every step. Certainly no sign of masculinity there. She knew that underneath his uniform… far underneath… he still had all of his male parts, completely untampered with… mostly. Other than the larger breasts she had installed on him, everything else was still there – including his one main masculine part. He just couldn’t use it in any kind of masculine way. Of course, he couldn’t touch it, or even see it either. It was locked away behind a shield that allowed him no access to it at all. He certainly knew it was still there, but for all intents and purposes, it wasn’t. Masculinity denied!
The thought of what she had done to him further aroused her sexual desire. She could feel the wetness beginning between her legs. As her excitement grew, her physical body began to react the same way her dream body did. She unconsciously rubbed her legs together, then her hands found that sweet tender spot and began rubbing through her panties. As her dream continued, she rubbed harder. Her physical fingers pulled aside the thin material and began touching her most sensitive of all places.
Her conscious mind was aware now of what she was doing, yet it too demanded that she hold onto her dream. Sissy, Sissy, Sissy. All the little things that excited her the most. Item after item of emasculating things she forced him to endure ticked through her dream, and each one increased the sexual pleasure that her physical self was experiencing. Her fingers were soaking wet now, but she didn’t care in the least. Her dream and the feelings were all that mattered. With one final thought of his total denied masculinity, her physical body exploded into an earth-shattering orgasm. She rode it as long as she could, then allowed herself to slowly come down from it.
Breathing hard, she opened her eyes. Vivid remnants of the dream stayed with her. Finally, she pulled her fingers away. Guilt and a tiny bit of disgust ran though her. Had she really just done what she knew she did? Damn! But she was mostly just surprised at the intensity of it.
She rolled over far enough to look at her clock. It was almost time to get up – fortunately. She definitely needed a shower now. With wet smelly fingers, she slipped out of bed. She paused long enough turn the alarm on her clock off before it could ring. Then she made her way to the bathroom where she carefully washed her hands. Her panties were soaked, as was the area under them. She carefully wiped up most of the dampness with some toilet paper after she relieved herself. She left the damp panties on for now.
Her next priority was coffee. She needed it – desperately. As she made her way into the kitchen, wonderful thoughts of Sissy still lingered on her mind. Wow, what a dream!

Chad sat in his only chair – the only real piece of furniture that he owned – and drank deeply from the baby bottle in his hands. Slowly, bit by bit, she was reducing him to the level of an infant. It wasn’t something his thoughts usually dwelled on, but the baby bottle in his hands seemed to migrate his thoughts in that direction. The blank walls of his apartment offered nothing to change his thinking either. The only object the walls held was the framed copy of their contract – the contents of which seemed to emphasize his current thoughts. He suddenly felt himself peeing – without warning – another reminder of his sinking status.
Drinking out of anything except a baby bottle now was becoming a rare opportunity - opportunities that he appreciated each and every time. Slowly, bit by bit. Deeper and deeper. Yet, in a way, he really didn’t mind at all. It excited him in ways he couldn’t describe. He was living the dream – in so many ways. Living the dream – and then some. All because of her.
His bottle finished, he got up from his chair. It was his final bottle before he went to see her – his third bottle so far this morning. He would have yet another one with the breakfast she would serve him – baby food. Yet another reminder of his sinking status into infancy.
He checked his image in the mirror on the back of his closet door. He was wearing the exact same outfit he had worn last Friday – almost. Mel had dictated in her morning note that he wear it today. His black skirt and the blue and white top. The difference today was that he was wearing blue pantyhose with it instead of going without any hose as he had last Friday. The reason he was wearing the blue pantyhose today with the outfit was because Robin had suggested it – and he had made the mistake of mentioning it to Mel. And because Robin was a woman, Mel seemed to think that he should try every suggestion that she made when it came to what he wore. Why, he didn’t really know. He had the underlying impression that Mel didn’t really think all that much of Robin. Again, he didn’t know why.
As he gazed at his reflection in the mirror, his eyes couldn’t help but to be drawn to his blue legs. In a way, he felt more like he was wearing pants with the outfit since his legs looked less bare. Yet in another way, he felt like the blue hose called all too much attention to his legs. Did they look good enough? He didn’t really know. Robin had said they were okay – for a guy.
Oddly enough though, for once, he was glad to be wearing a skirt instead of pants. Despite his super tight all-in-one girdle underneath, the pants he had worn to work yesterday had not been loose enough to hide his diapers when they got bloated, especially in the afternoon when they had been messy too. Like it or not, the skirts were now much safer for him to wear. The very thought of it sent a funny feeling all through him.
With a final look at his hair and makeup, he turned away and went in search of his purse.

The knock on Mel’s door came a few minutes early. Mel didn’t mind in the least. She was looking forward to seeing him again. She quickly opened the door and smiled at what she saw.
With his purse slung over one arm, his diaper bag over his other shoulder, and a bag full of empty baby bottles in one hand, Chad dropped the best curtsey he could under the circumstances. “Good mowning, Mistwess,” he said in his usual sissy voice that she required of him.
The sight of him curtseying like that sent a thrill all through her. She absolutely loved seeing it. “Good morning, Sissy,” she returned. She stood back out of the way while he came in and closed the door behind him. She waited while he set his purse and diaper bag down on the floor, then took the bag of empty bottles from him. Again she didn’t check it. She would open it later when she had more time. She knew without a doubt that it would contain the required number of bottles from last night and this morning – all of them still sealed with her tape so she would know that he had drank them through the bottle’s nipple like he was supposed to.
She stood back to inspect him again. It was the same outfit he had worn last Friday – plus the blue pantyhose. She hated to admit it, but Robin had been right, the blue hose did look better with it. The outfit looked much more interesting – something that most of his outfits usually lacked. She made a mental note to do something about that sometime. She walked all around him, then came back to stare at the front of him again. Yes, he really did look fairly good. More and more the perfect picture of what she had in mind for him. Yes, there was still a long way to go, but he really did look pretty good. “I like your outfit, Sissy. The blue hose do make a difference.”
Chad’s curtsey was mostly automatic, as was his response. “Thank you, Mistress.”
She giggled and another small wave of sexual pleasure ran through her – reminders of this morning’s dream. Oh, she loved seeing him do that, plus she figured that it must be incredibly embarrassing for him. She decided she wanted to see him do it again. “I really like your outfit today, Sissy.”
Chad was a bit confused. She had just said that. But he dutifully dropped another curtsey. “Thank you, Mistress,” he said again.
Mel felt another tiny sexual thrill as he did it and giggled again. She just had to see it one more time before she gave him his breakfast. “I just love seeing you do that,” she told him. “You really don’t look much like a man anymore. This ‘new you’ is so much better!” she said with a big smile on her face.
Chad didn’t quite know how to take that. Was it a compliment, or something else? She appeared to be waiting for something, so he decided to take it as a compliment. He curtseyed again. “Thank you, Mistress.”
The same thrill was still there, but not so much this time. She briefly wondered how he felt about not looking as much like a man anymore, but she didn’t pursue the question… it was one of those things that really didn’t matter, and there were other things that needed to be done now. “Okay, Sissy. Highchair time.”
Chad followed her into the kitchen. A few minutes later, he was stuck in his highchair with a bib around his neck, eating a large bowl of overly bland baby cereal with a tiny rubber-coated baby spoon. From the very first attempt to get the cereal into his mouth, the cereal fell off of the spoon and dripped down his chin. He was instantly reminded of his thoughts earlier this morning. He felt like such an infant – especially with Mel laughing at him like she was currently doing. To cover his embarrassment, he grabbed the baby bottle she had put on his tray and took a big drink. It was only while he was doing it that he realized that drinking from the bottle also made him look like an infant. Damn! There was just no winning!

Robin proudly carried her new gym bag into the office with her. She had it slung over one shoulder while the large bag she carried every day was hung over her other arm. As usual, both arms were loaded with other things in case she wanted to look through them during the day.
As she walked past Chad’s cubicle, she noticed that he was there ahead of her. She paused ever so slightly, then continued on to her own desk. She would come back to him in a minute. She dumped everything from her arms down onto her desk. Her new gym bag went under her desk. Her large bag finally landed on top of everything else she had just dropped from her arms. She opened her bag and pulled out her mirror and checked her face and hair. Everything looked good enough. She put the mirror away and left to see Chad. “Good morning, Sissy,” she called from the entrance to his cubicle.
Chad turned around in his chair at Robin’s greeting. For a brief moment, he almost replied, ‘Good morning, Mistress’ but he caught himself in time. “Morning, Robin,” he replied. He noticed that she seemed to be all smiles today. But then yesterday she had started the day that way too. It just hadn’t lasted.
“Sissy!” she said excitedly. “You’re wearing the same outfit you wore Friday, but with blue hose!”
Chad looked sheepishly down at his blue legs. “Yeah… well…”
“Well stand up so I can see it better,” she said expectantly.
Chad almost groaned, but he was getting fairly used to this now. He guessed that Robin probably should be excited because she was the one who had suggested the blue hose in the first place. He stood up and after a brief moment, slowly turned himself in a complete circle so she could see it all. He was ever so glad to see the look of excitement and joy still on her face when he got all the way back around again.
“Sissy, you look really good! I told you those blue hose would make a difference.”
Chad’s mind registered the compliment. Without thinking about it, he dropped a curtsey and his sissy voice said, “Thank you…” He caught himself before he got any further – he had almost said Mistwess. “Uh… Robin,” he finished.
She giggled. “You’re funny!”
Chad was so embarrassed by what he had just done that he was nearly beside himself. “Yeah, well…”
Fortunately, Robin didn’t seem to be making much of his curtsey and voice at all. “Did you wear that today just because I suggested it to you?”
Actually, that was the entire reason he was wearing it today. “Yeah. That’s it.”
Before he knew what was happening, she was hugging him firmly. “Oh, it’s so nice to see you listen for a change!”
Chad didn’t quite know what to do as she hugged him. It kind of felt good, but it felt awkward in a way too. He was actually relieved when she let him go and backed away from him again. He sat down where he felt safer. “Uh… You look good today too,” he said, trying to find something nice to say about her too. “In fact, you seem a bit happier than usual.”
“Thanks!” she fairly beamed at his compliment. “I guess I am a bit more excited today. I stopped by the gym last night and paid my money. So now I’m a full-fledged member – just like you!”
“Well, I don’t think they consider me a regular member,” he replied.
“Oh. Maybe not,” she corrected herself. “But the point is that I’m going to my first aerobics class tonight right after work!”
Chad wasn’t in the least happy to hear that. He had no doubt that by tomorrow he would be hearing all about what he had done there on Monday – only he’d be hearing it directly from her! And he could see no way to stop her.
“Hey, want to see my new exercise outfit?” she asked excitedly.
Chad found himself somewhat curious. “Sure, if you don’t mind.”
Robin dashed out and came back a moment later with a brightly colored flowered bag. She held the bag up for him to see. “Isn’t it gorgeous?” she asked, obviously proud of her find.
The tiny feminine side of Chad warred with the larger male side causing him to be hesitant about appearing too interested. And the truth was that he wasn’t that interested in her bag, but he was fairly interested in the clothes she had bought – the sissy side of him did go that far. He just didn’t want to appear too interested. “Uh, yeah! It’s real pretty,” he said about her bag.
Robin stared at it happily for a moment longer as she held it up high in her hand. “I just love it,” she declared. “But wait till you see the outfit I bought! I can’t wait to wear it tonight!” She finally set the bag down on his desk.
Chad got up so he could see better when she opened it.
She stood over the bag and paused, looking straight at him, a gleam in her eye. “Are you going to show me your gym outfit?” she asked.
Chad was shocked. How had they gotten back to his nonexistent gym outfit again? “I told you yesterday, no way!”
“Then I’m not going to show you mine,” she declared.
Chad was further shocked. “But you’ve got it right here!”
“So? If you won’t show me yours, then I’m not showing you mine!”
Chad thought she sounded awfully childish. “But why not?” he asked.
“Why won’t you show me your outfit?” she replied.
“Because mine is… embarrassing! Very embarrassing!” he stated flatly. “Is yours?”
“Nope! Not in the least. But it is real pretty,” she said with a sly smile on her face. “Are you sure you don’t want to see it?”
“Pretty? A work-out outfit?”
“Sure! Why not?” Her sly smile returned. “Is yours pretty?”
He shook his head. “Definitely not!”
“But it is embarrassing?”
“Yeah! You could say that! Very!”
“I still don’t see what could possibly be that embarrassing about it,” she replied, “but until I get to see yours, then you don’t get to see mine!”
Chad sat back down in his chair. There was no way he could ever tell her that the only thing he ever wore at the gym – when he was wearing anything at all – was diapers!
“So you’re not going to tell me?” she asked, disappointed.
“No way!” he replied.
“Then I’m still going to keep bugging you till I guess what’s on your t-shirt.”
Chad groaned out loud. “You’re not going to get it.”
“Then if you don’t want me bugging you about it, show it to me. I promise I won’t tell anyone.”
“I can’t!”
“Why not?”
“Because… It’s complicated!”
Robin nearly had a fit. “Bullshit!” she returned angrily. Then her demeanor changed completely. Sounding and acting totally justified, she said, “Then the pressure won’t let up at all. I’m going to keep trying to guess it till I find out. In fact, maybe the other ladies in the company will help me guess it too.” Her sly look returned. “Are you sure you want to put up with everybody calling you with guesses all day long?”
Chad was ready to have a fit. He could just imagine his phone ringing constantly with goofy women all trying to send him even goofier slogans. “No! Please!” he pleaded.
“Then tell me what it is.”
He shook his head. “I can’t!” he wailed.
Her smile went from sly to wicked. “Then prepare yourself for the onslaught!”
With one more wicked smile, she picked up her unopened bag and walked out. Chad could only stare at the empty cubicle entrance where she had disappeared.
Robin wasn’t exactly seething inside, but she was now more determined than ever. She had offered to show him her new outfit that she was so proud of, but he still wouldn’t show her his. Why did he have to be so stubborn about it? It couldn’t possibly be that bad! And once he had said that phrase – “it’s complicated,” she had nearly had a fit! Well, he deserved what he was about to get! That is, if everyone else would go along with her. And she was fairly sure they would.
Instead of calling all her friends, she opened up an email instead so he wouldn’t hear her. She began entering every name of every female that she was friends with in the company. When she was done, she began explaining what she wanted.