The Bet - Chapter 34 (Thursday – week 5 Part 4 of 6)

The Bet
by Karen Singer

Chapter 34 (Thursday – week 5 Part 4 of 6)

For Chad, the afternoon seemed to wear on interminably. He couldn’t quite get Cassie’s question out of his mind, and it bothered him. Was sex – if he could call it that – better the way that he got it now as opposed to the normal way? The way he was used to? It was a troubling question. One he would rather put out of his mind completely, but as usual, that kind of question always seems to linger and haunt you when you don’t want it to. Curiously, the only relief he got from thinking about it was the few phone calls he got from the women around the company, still trying to guess the slogan on his nonexistent t-shirt. And each guess proved to be a rather interesting relief.
“Break time, Sissy,” Robin’s voice called cheerfully from his cubicle entrance.
Chad turned around and leaned back in his chair. He had been checking his work on the project carefully all afternoon, searching for any problems. It was grueling work. That coupled with Cassie’s question weighing on his mind was starting to get to him. He took a deep breath for relief. “I think I need a break,” he declared as he turned back around and closed the programs he had been working with.
“I know what you mean,” Robin replied. “This part of the job is not much fun.”
“You can say that again!” Chad agreed as he followed her out of his cubicle.
“So has anybody come close yet?” Robin asked as they walked up the hallway.
Chad considered the question carefully. How could anybody come close if there wasn’t any slogan? “Not really,” he replied.
But Robin noticed how long he had taken to answer. “I’m betting that somebody got close! You just don’t want me to know it!”
Chad only grunted. “I’m not telling,” he replied teasingly.
But Robin seemed more excited than ever. “Oh come on! You’ve got to! It’s only fair.”
“No I don’t have to,” he teased back. “And it’s perfectly fair!”
The two of them had to stand in a short line to get coffee again. As they stood there, Chad wondered why he was even getting the coffee. He certainly didn’t want any more liquids in his system. He was still having more trouble holding back than ever. But not getting the coffee might look suspicious, so he followed right behind Robin and got himself a cup.
As he turned back around to follow her toward the women’s table again, he locked eyes with Derek who had been standing only two people behind him. He stopped at the unexpected meeting. “Sissy,” Derek greeted him in the way that guys usually do.
“Hey Derek,” he replied. “How are you?”
Derek nodded, “Doing fine.”
Chad felt awkward talking to him. He looked down at his coffee and then at the table of women. He was about to say that he had to go, but Derek spoke first.
“Do you want to join me for a change?”
Chad was somewhat flabbergasted at his offer. Join him? Was he serious? He looked quickly back at the table full of women again. Many of them now were watching him intently. He had no doubt that they were all waiting with more ridiculous guesses as to what was on his nonexistent t-shirt. Would Derek be a better alternative? Against his better judgment, he said, “Okay.”
He turned his back on the women and waited till Derek got his coffee. Then he followed his former friend to a table where the two of them sat by themselves. Derek lounged back into one of the chairs with his arm resting on another chair. Chad sat somewhat more demurely across from him. The two of them sat for a moment and sipped their coffee without saying anything. They both felt the awkwardness of the situation.
“So you’re in the office today?” Chad asked. He knew it was a lame question. Derek worked on network systems. If he wasn’t out somewhere working, then he was here.
“For now,” Derek replied. “You know how that goes.”
“Yeah, I do.”
Derek looked like he was about to say something else when Chad noticed his head turning to look at something. Chad turned to see what he was looking at. George, another old friend from the company was heading straight for their table.
“Derek!” George greeted him before he had even gotten to the table. Derek motioned for George to take a chair, but George declined. “Sorry, I can’t stay.” He looked over at Chad and nodded. “I’d ask how you’ve been, but I’m not sure what to say.”
“Don’t worry about it,” Chad assured him.
George just nodded and turned back to Derek. “Hey, the wife’s going to be away again next week and I’m trying to set up another poker game. You in?”
“When is it?” Derek asked.
“Tuesday night.”
Derek seemed to consider it for a moment. “Yeah, I’ll be there. Who else did you get?”
“Just you so far.” He turned toward Chad, looking a bit uncomfortable. “I’d ask you again, but…”
Chad waved his hand. “It’s okay. I’m busy anyway.”
George looked relieved. “Yeah, good.” He turned back to Derek. “So Tuesday then?”
“Yeah,” Derek replied. “Tuesday.”
Chad and Derek watched as George walked away. Chad breathed a small sigh of relief. He would have enjoyed the poker game – under different circumstances. But not now… not the way he was currently living. But when he won this bet… when he won he would have a place that would be perfect for the guys to hang out. He would hold his own poker games. And he was looking forward to it. All he had to do was make it through one more month!
“It’s a shame that you can’t play anymore,” Derek said, “I like having someone there that I can always beat.”
Chad knew that he was mostly joking. “What do you mean, always?” Then he stopped to think for a moment. “Well, okay, you win more often than I do.”
Derek laughed a bit. “Okay, so let’s say I ‘usually’ win! Do you miss doing things with the guys anymore?”
For Chad, this was turning into a day full of tough, and disturbing, questions. “Sometimes,” he admitted quietly. “Of course I didn’t get to do too much before since I was married.”
“But you’re still gung-ho over all this sex-change stuff?”
“I’m not getting a sex change!”
“No. It just looks like it!”
Chad was fairly exasperated, but what could he say? To all appearances it probably did look exactly like that. “I’m not getting a sex change,” he repeated, more softly this time.
“At least not yet.”
Chad only looked at him. His friend didn’t understand. How could he? Chad barely understood it all himself. They each sipped their coffee for a few minutes while Derek studied Chad. Chad only stared at the coffee cup in front of him, unable to meet Derek’s eyes.
“So are you planning on dating guys now?” he asked.
Chad was aghast. “No! Not at all.”
“But you’re still dressing and acting like a woman? What the heck for?”
Chad stared into his coffee again. “It’s complicated!” It was the only answer he could truthfully give. He suddenly swigged the rest of his coffee to finish it and stood up. “I’ve got to go,” he said. “I’ve got a lot of work to do.”
He didn’t stop at the table full of women on his way out. He barely looked over at them. They were all watching him. He strode purposely out of the room, trying not to look like he was hurrying at all, but his mood made him more aware than usual of the heals on his feet.
“Sissy! Wait up?” Robin’s voice called behind him.
He stopped, although he wasn’t really sure why, and turned back towards her. She was running to catch up.
“What’s wrong?” she asked.
“Nothing,” Chad replied as he continued walking again.
“Well, something must be wrong for you to leave like that!”
Chad just shook his head. “It really is nothing. I was just a bit… uncomfortable with him. That’s all.”
“Uncomfortable? What did he say?”
Trust a woman to want to know all the details. “Nothing much really. He still thinks I’m doing this as part of a sex change.”
“Well, you’ve got to admit, it does sort of look like it.”
“Yeah, I know. But it’s more complicated than that.”
“Stop that! It’s not that complicated!”
Chad didn’t say anything. Robin really had no idea at all.
“So what else did he say?”
“Not much. He asked if I was planning on dating men now.”
Robin was surprised. It was something she hadn’t even thought of before. “Well, are you?” she asked tentatively.
Chad looked over at her as they walked. “No! Not at all.”
They walked in silence for a few moments. “I wonder if he wants a date with you.” Robin mused.

Chad stood in front of his desk and stared at the flowers that were left from the bouquet he had gotten last week. It was looking fairly sick now, but then it only matched the way he was feeling since the suppository that Cassie had stuck up inside of him earlier was once again doing its work. Having no control of what was happening behind him at all, he forced himself to reach out and remove one of the withered stems from the bouquet. As the miserable mess filled his bottom and forced its way around his backside under the tight confines of his girdle, he removed a few more of the now dead flowers, trying to act as normal as possible under impossible circumstances.
The bouquet didn’t look so good anymore. It looked sparse and dull. Most of the bright colors were now gone. All that was left were flowers now on their last gasp of life. It somehow made him feel disappointed. He had rather enjoyed the colorful display. It added a lot of interest to his dull cubicle. He knew it was worthless to keep the bouquet much longer, but he was reluctant to part with all of it just yet.
He threw the now dead stems that he had removed into the trash. The suppositories seemed to be about done with their work now. He thought about sitting back down again, but somehow couldn’t bring himself to do it. It got that way sometimes.
He knew he really couldn’t blame Derek for asking the questions he had – and he didn’t blame him. Not at all! It was just that the questions were once again, uncomfortable – in an uncomfortable situation. He almost laughed. Just like the uncomfortable situation inhabiting his bottom just then. He knew he should call Derek and apologize for his behavior, but he couldn’t quite bring himself to do it… kind of like he couldn’t quite bring himself to sit down yet either.
He realized he was stalling. He had work to do and he had to sit down sometime. Gingerly, he forced himself back into his seat. Yuck! But he got quickly used to it. He got quickly used to it because it was something that he lived with every day now. Just another part of his new “normal” life. Realizing that he had now conquered one problem he was procrastinating over, he again thought of Derek. Derek had been trying to be his friend – still. He guessed he owed Derek something for that. He picked up the phone and tried to grab his courage. Apologies were so difficult.
“Hey Derek,” he said into the phone. “I just wanted to apologize for my behavior earlier. It was really uncalled for.”
“That’s okay, Cha… Sissy. I’m sure there are things that must be hard to handle.”
“Yeah, you really have no idea. It’s just that… well… it’s hard to explain some of these things to people who were… are my closer friends.”
“Well, if need be, I guess I can buy you a beer sometime and we can talk about it if you like.”
“No thanks. Besides, I don’t really drink beer.”
“Oh yeah, that’s right. Well, whatever you drink, if you need me, just ask.”
“Yeah. Thanks, Derek. I appreciate it. And like I said earlier, sorry about earlier.”
Chad hung up his phone and almost jumped out of his skin when Robin asked from the entrance to his cubicle, “Did I hear you say that Derek asked to buy you a beer?”
Chad hadn’t heard her there so he was still trying to recover from the shock of her question. “Uh… no. Not really… well, he did… but it was…”
“He is trying to ask you out! Wow! And I thought it was just this weird funny thought that I had.”
“No he’s not! And I wouldn’t! He’s just trying to be a friend – in case I want to talk about anything. That’s all!”
“Sounds like a date to me,” Robin replied excitedly – or teasingly. Chad really couldn’t tell which. “So, are you going to go?”
“No!”
Robin had a gleam in her eye as she headed back to her cubicle. “We’ll see, Sissy. We’ll see.”
Ugh! Women!

As soon as work was over, Robin happily grabbed her things, along with her new gym bag, and headed for the gym. She proudly walked in with her colorful new bag and showed her temporary membership card. She had only ten minutes to change before the aerobics class she was interested in started, but she wanted to check on something first. The receptionist behind the desk was one she didn’t recognize, but that didn’t mean anything. “Is Cassie still here?” she asked.
“I’m sorry, you just missed her,” the current receptionist replied. “She went home just a few minutes ago.”
Oh well, it didn’t really matter. It just would have been nice to see a familiar face before she got started. She thanked the receptionist and hurried to the locker room to change.
She felt good in her new exercise outfit as she walked from the locker room to the room where the class would be. Most of the other women were already there ahead of her and a few of them greeted her kindly, sounding like they were genuinely glad that she was joining their group.
It was about time to start, but she didn’t see an instructor yet. It wasn’t really her purpose in being there, but… well… she figured she might as well ask. What could it hurt? “Hey,” she said to a few of the women near her. “Have you heard about the guy who comes here at lunch time?”
“I think I heard something about that,” one of the women confirmed.
“Me too,” another one added. “And I think someone mentioned that something funny happened with him… or to him. I’m not sure which. But I don’t really know anything.”
Robin was immediately interested and wanted to press the woman harder for details, but just then the instructor came in and called the class to order. By the time class was over, Robin was in no condition to think about anything other than getting home and soaking in a nice warm relaxing tub!

The Bet - Chapter 34 (Thursday – week 5 Part 3of 6)

The Bet
by Karen Singer

Chapter 34 (Thursday – week 5 Part 3of 6)

Chad’s phone didn’t ring nearly as much after break, but it did ring occasionally. And the longer his morning wore on, the less it seemed to ring – something he was very grateful for. The women seemed to be running out of guesses – he hoped.
He glanced at the time on his computer screen. He still had a few minutes left before lunchtime. He thought he could hear Robin typing on her keyboard in the next cubicle. The timing seemed to be safe enough. He opened the spreadsheet on his desktop where he kept his progress toward the bet and quickly found today’s date. Twenty-nine days to go! Seeing the number finally reach less than thirty seemed like a major milestone and made the amount of time left seem even less. He would win this bet! He still had no doubt!
He moved up a row to yesterday’s date and filled in his best time that he remembered being able to hold back yesterday – only nineteen minutes! Two minutes less than the day before! Once again he was going backwards. It seemed like all the increased drinking along with Mel’s enforced diaper wetting games were taking a toll on him. If he didn’t get busy and manage to hold it longer again, then Mel might still have a chance! But still… nineteen minutes wasn’t so bad at all, was it?
His eyes caught sight of the column of things that he wanted – his reasons to win the bet. He had relayed many of them to Sandy last night so she could design his apartment for him when this was all over. He couldn’t wait to see what she came up with. It was going to be great! He glanced again at his best time for yesterday. Only Nineteen minutes! He quickly closed the spreadsheet before he could get disgusted with himself.

“Sissy!” the receptionist’s excited voice squealed the moment he walked through the door to the gym.
“Uh… Hi,” he returned.
She pouted. “Come on, you can do it nicer than that.” And then she giggled a bit even though she was trying to keep a stern look on her face.
Chad didn’t miss any of it. Knowing it was no use resisting, he dropped a curtsey and said, “Hewwo,” in his sissy voice.
The receptionist giggled uncontrollably. The look of absolute delight was all over her face. She leaned across the high counter as much as she could. “Can you lift your skirt so I can see what you’re wearing underneath?” She giggled again.
Chad mentally groaned. Why couldn’t she just go get Cassie for him? But he knew she probably wouldn’t let up till she got her way, so he pulled his skirt up high.
Her face registered nothing but disappointment. “I can’t see much of anything with those blue hose on today. They do look nice, by the way.”
“Uh… Thanks,” Chad replied as he smoothed his skirt back in place again. “Can you get Cassie for me now?”
But she didn’t leave just yet. “When do you ever wear anything where I can see your diapers?”
Chad was fairly shocked by her question. He shook his head. “Never. I’m almost always very well protected when I leave the house. Especially for work.”
The receptionist’s lips pursed in thought as if she was bothered by something. “Never?” she asked.
“Never!” Chad confirmed. “I’m afraid that Mel has some very strict requirements for me.”
“Mel is the woman who was with you on Monday?” She still looked bothered by something.
“Yeah.”
“You know. It’s a lot more fun when you talk silly instead of in your normal voice.”
Chad mentally groaned again. “Can you please just go get Cassie for me?”
“Not until you ask in your silly voice,” she teased. Her eyes suddenly glowed with interest.
Chad was getting frustrated. At the rate things were going, he’d be here all day before he got to see Cassie and get his diapers changed. “Can you pwease get Cassie fow me now?” he asked in his sissy voice.
Her eyes glowed with delight. “Now curtsey pretty as you ask me.”
Chad wasn’t sure if he wanted to run out the door or hit her. Having little choice however, he dropped his curtsey and repeated his request.
The receptionist giggled again with delight. “Oh, that’s so much better!” she teased. “Okay, I’ll find Cassie.”
“Thank you,” Chad said.
“Uh-uh! Curtsey please!”
Chad felt like hitting her more than ever! But instead, he curtseyed yet again as he repeated his thank you.”
Her eyes showed nothing but delighted mischief as she finally walked off to find Cassie.
Chad had to wait a few minutes before they returned. As he was waiting, two women came out to leave. Unfortunately, one of them recognized him right away. “Oh! Look who’s here!”
Chad’s face turned red as the two suddenly delighted women walked right up to him. “We so enjoyed your little visit the other day!” one of them said.
Chad just nervously nodded. “Thank you,” he replied, rather embarrassed.
“Are you coming back to do it again?” the other one asked hopefully.
Chad shook his head. “I hope not.”
The two women laughed a bit. “Well, we just wanted you to know how much we enjoyed it. It was quite a show you gave us.”
“I know I’ll remember it for a long, long time,” the other woman added.
That wasn’t exactly what Chad wanted to hear. “Thanks,” he mumbled yet again. He was ever so glad when the two women just said goodbye, one of them giving him a tiny wave with her fingers. Women! He watched them as they both walked out of the gym.
“You’ve made some friends,” Cassie’s voice said, causing him to turn quickly back around.
“Not really,” Chad replied.
“It sure looked like it to me. They didn’t complain about you, did they?”
“No.” Chad felt a bit of disappointment over the fact that they didn’t complain. “In fact, they both told me how delighted they were to see me.”
Cassie nearly laughed. “See, like I said, you’ve got some new friends.” Chad wasn’t so sure at all.
A little while later, Chad was drinking from another baby bottle while Cassie was removing his sodden diapers. As usual now, Cassie took careful note of the size of his penis inside his chastity device. Just as small as ever. “Does that thing ever get hard anymore?” she asked.
Chad stopped drinking only long enough to answer. “It can’t,” he replied. “That thing won’t let it.”
Cassie realized that she had only asked something obvious. “Well, does it ever get any bigger inside there?”
Chad stopped drinking again. That was a different question. “I don’t really know,” he replied. “It’s always covered up with my diapers. I can’t see it. All I can really tell you is that at least it doesn’t seem to hurt me like it used to. I don’t think about it as much anymore.”
Cassie nodded and went back to work on him as she tried to completely digest what he had just told her.
Chad was also trying to digest what he had told her, but from his point of view. What he had just said was the honest truth. He didn’t think about it that much anymore. Getting harder, or bigger, while wearing the chastity device was not an option, it only brought pain. He was so glad that he hadn’t felt any pain from there in a long time now. In fact, the chastity device didn’t allow him to feel much of anything from that part of his body anymore since the plastic cover prevented him, or anything else, from even touching his penis. The only thing he could say that he felt there anymore, was pressure. Not so much the pressure from where the device was locked onto him, but a deeper lingering pressure that was more inside of him. The pressure from having no sexual relief in such a long time. His entire life was nothing but major sexual stimulation, while he was entirely denied the reward of relief. Frustration! Pure and simple frustration!
“Okay,” Cassie said. “Roll over. Let’s do your other side now.”
Chad set his baby bottle aside and rolled over. A moment later, he was feeling the wonderful sensations of Cassie’s hands spreading the lotion all over his backside. Would she play with him again today? There hadn’t been time yesterday. He felt her hands leave him again.
“Scootch your knees up for me,” Cassie said.
Chad felt nothing but elation at her words. A moment later, he felt the hard tip of her toy as she placed it against him. He was a bit surprised that she didn’t start with her fingers today, but he really didn’t care. Her toy was the closest thing to having sex that he was capable of feeling – even if he couldn’t ever get any true release from it. The moment she started to push on it, he opened himself up and pushed back again. He wanted that toy inside of him. He wanted to feel it going in and out of him. He wanted to feel… excitement!
Cassie was a bit surprised at how fast he took her dildo today. She had purposely not worked her fingers into him before she used her toy. But today, he was obviously ready for it… and obviously wanted it. She had seen it many times before, but today he seemed to work himself up to a very excited state very quickly. “Does that feel good?” she asked.
Chad barely registered her question, he was too intent on the feelings in his bottom. “Uh huh,” he grunted as he kept up his pumping, trying desperately for the release he wanted.
“Is it as good as the way you used to have sex?” Cassie asked.
Her question floored him. His pumping slowed quickly as he thought about it. Then came to a stop altogether. He was glad that Cassie had left her toy up inside of him so he could still feel it. But her question bothered him. Did it feel better? Or not as good? He honestly didn’t know. Worse, he honestly couldn’t remember how it felt to have sex the other way… the normal way. Especially not with her toy still in him, still stimulating him. With her toy still there, that was the only part of him that felt any pleasure. It was too hard to think about anything else. “I don’t know,” he finally replied. “I honestly don’t know.”
Cassie wasn’t sure if she was surprised by his answer or not. In a way, she was sorry she had even asked the question, but in a way, she wasn’t. She had been genuinely curious. And whether he believed it or not, she honestly felt some sympathy for the poor guy. She felt him pulling away from the device she was still holding against him, then pushing slowly back into it again. He pumped himself a few more times then stopped, his head slumping to the floor as if he were defeated. She knew he was done and pulled it all the way out of him again. Had her question spoiled the fun for him? She hoped not. But then, why should it matter to her anyway? She told herself that it didn’t.
Frustrated, in so many ways, Chad rolled back over again so she could rediaper him and grabbed his baby bottle. There was a comfort that very few people probably knew about in sucking on a bottle – well, except for real babies that is. Cassie’s question haunted him. Did it feel better, what she was doing to him – or for him? Or was it better the old way, the normal way? And why couldn’t he really remember how it felt the old way? He tried to chase the question out of his mind by concentrating instead on the feeling of Cassie diapering him while he sucked on his bottle – like an infant. More and more of an infant. Exactly like he had been thinking earlier that morning.
Cassie watched him as she grabbed the jar of suppositories and opened the lid. He wasn’t watching her again. Instead, he seemed to be lost in his own thoughts. She didn’t even bother to take the lid all the way off this time. As she had done many times now, she stuck only her finger up inside of him, pretending to stick one of the little gems way up there. The look on his face as she did it was certainly not pleasure. She knew that he hated the darn things. But the strangest part was that he really couldn’t tell when she was faking putting one into him or not. “Do these things still work?” she asked.
Chad’s face registered nothing but disgust as he pulled the bottle out of his mouth. “Too well!” he replied, then stuck the bottle back in again.
“Do they work every day?” she asked, curious to know if there was a difference in the days when she only pretended to do it to him.
“Every damn day,” he replied, the frustration of it clearly in his voice. “Just once, could you try not putting one into me… and not tell Mel about it? Please?”
“Sorry, I can’t do that,” she replied. He made no answer, he only looked away from her again as he sucked on his bottle. He couldn’t tell when she wasn’t sticking them up into him, and now it looked like whether she did or not was having exactly the same result. Was Mel really winning here? She couldn’t be sure, but it looked like she might at least be making some headway.

“Thanks, Cassie. I appreciate it.” Mel hung up her phone and sat back to think for a minute. What Cassie had just told her really wasn’t anything new. Not really. But it did confirm her suspicions – or hopes – or both.
She found it odd though that he didn’t know if he ever got any bigger inside his chastity device than he seemed to be lately. She figured that guys, with their odd piece of flesh hanging off of them, would always know what it was doing. Especially since it was supposed to be so sensitive. But did the chastity device cancel out any of that sensitivity? She wasn’t a man, so she really didn’t have a clue.
And as to him not knowing if the anal sex was a good as his old ‘normal’ way, well, she was fairly sure that he knew the answer to that one too. Of course it wasn’t! Was he just trying some kind of ploy in hopes that she would relent and let him feel sex like a man again? If so, he was going to be very disappointed!
And as to the suppositories working whether or not they were in him, well, she pretty much already knew that. But it was nice to have some extra confirmation.
All in all, so far, things were going mostly pretty good. Now if only she could solve his peeing problem so he couldn’t hold back at all anymore. Of course, Gloria could probably solve that in a few minutes, but Gloria was refusing now. She had been forced to settle for a compromise with Gloria that she wasn’t really all that happy with.
She was trying to win this bet, and in some ways she knew that she was winning. She just wasn’t so sure about the one main part, the only part that really counted – making him completely incontinent.

The Bet - Chapter 34 (Thursday – week 5 Part 2 of 6)

The Bet
by Karen Singer

Chapter 34 (Thursday – week 5 Part 2 of 6)

Mel sat behind her desk thinking about Chad. Her dream this morning had been so unexpected. She knew that denying him the ability to be masculine in any way turned her on greatly, but she just hadn’t realized that it was going so far. She mentally ran through the list of what she had already done to him, from locking up his penis, to his clothes, to everything else. And now she was working on the latest piece – his voice. She giggled at the thought of him having to use his sissy voice all the time. Just making him talk in a higher pitched tone – more like a female – would have been fine, but she found that denying him the ability to use certain sounds and having to speak more like a toddler excited her even more.
Her thoughts ran quickly to yesterday. She had been forced to punish him last night because he answered the phone in his normal male voice. She had absolutely no doubt that he used his male voice at work all the time. She had no control over that and had no idea how she could get it – yet. But she would think about it. She could however control how he answered the phone whenever she called. In fact, maybe it was time to test things right now! She picked up her phone and punched in his number.
Chad was startled by the sound of his cell phone ringing. As quickly as possible, he opened his drawer and pulled it out of his purse. He was careful to check to see who was calling – Mel! Uh oh! He glanced around. He had to go somewhere where Robin wouldn’t hear him speaking! But where? If he ran towards the restrooms again like he did yesterday, Robin might check to see if he actually went in there.
He made a mad dash up the hallway in the opposite direction, pushing the button to receive the call at the same time. “Hello?” he said breathlessly in his sissy voice into the phone, careful to not speak too loudly.
“Sissy! What are you doing? Why did it take so long to answer me?”
Chad turned down one of the hallways toward the outer doors where he hoped he would be less likely to be heard. “I… I had to fish my phone out of my purse,” he finally replied.
“It shouldn’t take that long!”
“It was in my drawer!”
“It still shouldn’t take that long! And you sound like you’re running somewhere! I think you’re trying to hide from your friends again! Is that it? ”
Chad wasn’t really running, but he was certainly hurrying awfully fast. He slowed down and stopped where he was, fairly sure he wouldn’t be heard. “Um… It’s difficult to talk at my desk, Mistress,” he replied.
“That’s not an issue to me and you know it!” she replied. “The problem is that you still don’t want your friends to know! Well, that’s another demerit, Sissy! One way or another, you’re going to learn to do things right!” Mel quickly hung up the phone before he could say anything else. He was still trying to hide, which meant that she still wasn’t making any headway as far as him using his new voice all the time. But she still had no better solution to the problem than to give him a demerit and beat him for it later.
Chad headed slowly back to his desk. It wasn’t till he had taken several steps that he realized that Mel had never told him the main reason she had called in the first place. Now he not only had another demerit to worry about, he didn’t know if he had to worry about whatever it was that Mel had called him for!

Chad’s desk phone rang. He picked it up quickly figuring it would probably be Tom Robinson, his boss. “Hello?”
“Hi Sissy,” a female voice giggled softly from the other end. Chad thought he recognized the voice but he didn’t remember the woman’s name.
“Robin says we need to try to guess what’s written on your exercise shirt.”
Chad was shocked. “She said what?”
She giggled on the other end. “How about… ‘I hate being a man’?”
Chad was still trying to come to terms with the fact that Robin had actually gone through with her threat. He shook his head as he answered. “Trust me. Not even close.”
“Oh darn!” the voice on the other end giggled. “Now I have to think up another one! Bye!”
Chad hung up his phone and just stared at it. She had actually contacted one of her friends to help her with guessing.
“She didn’t get it?” Robin’s voice asked teasingly over the top of the wall separating them.
“Not even close!” Chad replied.
“Well, eventually one of us is bound to come up with it sooner or later.”
Ugh! His phone rang again. Please not another one! He didn’t get his wish. Instead, yet another woman guessed something embarrassing. Double ugh!

Gloria checked her watch. She had just a few minutes before her first client of the morning was due to arrive. Mel hadn’t called yet about lunch, but then she didn’t always. Plus, it was a bit early still. Since they had worked out their agreement concerning Chad yesterday, she wasn’t sure if Mel was still interested in having lunch again. But she did need to talk to Mel before tonight. It was important!
She picked up her phone and called Mel’s office, but she got only as far as Andrea before she had to leave a message and wait for Mel to call her back. She saw her client pulling open the door. She would have to check with Mel later.

Chad was slowly going through screen after screen on his computer, checking the work he and Robin had done. So far, it all looked really good. There were just one or two more little things that needed finishing. His phone had rung half a dozen times in the last hour with different women all trying to guess what was on his nonexistent gym shirt. It was aggravating to say the least, and the slogan’s they were guessing were also a bit embarrassing to think about. Embarrassing – but thrilling too! He would never admit it to anyone else, but he actually imagined himself wearing shirts with some of the slogans and could almost feel the embarrassment from it.
“Break time,” Robin called from the entrance to his cubicle. He turned toward her. He really didn’t want to go today. If he did, all the women would probably spend the entire break time trying to guess the slogan. “Um… I’m not sure I want to go today,” he replied.
Robin walked in and grabbed his arm and pulled. “Come on. You know I’m not going to let you stay here. Besides, you need to get out and talk to people once in a while.”
“More likely you mean that they want to talk to me,” he replied, resisting her pulling. “They’ll all be asking about my gym shirt!”
Robin giggled. “So all you have to do is tell us, and we’ll stop.”
Chad shook his head. “No way!”
“Then we’re all going to keep trying to guess.” She pulled on his arm again. “Now get out of that chair and come to break… or I’ll bring everybody down here to talk to you!”
With a groan, Chad got up and followed her. He wasn’t really looking forward to it, but maybe the women would all get their ridiculous guesses out of the way now and then they would leave him alone later.
As usual, the break room was filling up fast. A few of the women giggled and said good morning to him as he stood in line behind Robin waiting to get coffee. He was lucky enough to get one of the last doughnuts too which made him feel a bit better about things. Then he followed Robin over to the usual crowded table and pulled up a chair. Space magically seemed to appear for him as he did so. He had no trouble noticing that all eyes seemed to be on him. He also had no trouble noticing the look of absolute delight in the eyes of each and every woman. How many friends had Robin contacted? As he sat down, he felt like a lamb staked out in the midst of a pack of hungry lions. He took a bite of his doughnut and a sip of his coffee for courage as the onslaught quickly began.
“Hi Sissy,” one of the women giggled. “Hey, isn’t that the same outfit you wore last week?”
“Only with blue pantyhose today?” another woman added.
Chad was surprised that they would even notice. “Yeah,” he replied. “You all seemed to think that blue pantyhose with it would be a good idea.”
“So you’re not trying to wear something different every day?” Someone asked.
Chad took a sip from his coffee before replying. “Not purposely.”
“Well, the blue pantyhose do make it look a lot different,” someone else noted. “So it is a change.”
“I kind of like it,” someone else stated.
“Uh… Thanks,” Chad replied.
“So you’ve got some kind of embarrassing gym outfit, huh?” another one threw in.
“Tell us about it,” another one demanded.
“I’d rather not,” Chad replied as he took another bite of his doughnut.
“Why not?” someone asked.
“Because it’s embarrassing,” Chad said with his mouth still full. He noticed the conspiratorial looks the women seemed to give each other.
“So we’re going to be stuck guessing?” someone asked.
“You got it,” Chad replied as he picked up his coffee to wet his mouth. He heard a few of them giggling again.
“This is going to be a fun game,” someone said. Chad noticed that they all seemed to agree. The look of hungry lions was suddenly more pronounced.
“So what color is it?” one of them asked.
Chad was surprised by the question. He had just figured they would try to guess the slogan. “What color?”
“Yeah, what color?”
“Uh… Well...” He didn’t really wear any shirt. How could he answer? “Uh… I guess white,” he finally replied.
“You guess? What’s that supposed to mean?”
He realized he was getting himself in deeper and deeper. How could he answer? “Well, I guess it’s mostly white,” he replied.
“Mostly? You mean it’s white but the lettering is colored?”
There was no lettering. There was no shirt. But her question sounded like a good solution to his problem. “Uh… Yeah. Something like that.”
“So what color is the lettering?”
They weren’t letting up. But then, by now he didn’t expect them to. “Uh…”
“I’ll bet it pink!” someone stated. “Probably hot pink!”
He looked up at her, startled by the sureness of her guess.
“That’s it girls,” one of them stated. “Look at the look on his face.”
Chad was surprised. Now they were convinced that the lettering on his nonexistent shirt was pink.
“Wait a minute!” someone interjected. “You know, there could be some kind of picture on his shirt too.”
Chad stared at her aghast. Now they thought there might be a picture too? He was about to shake his head and tell them no, but someone else quickly noticed his surprised look. “Look at him,” she said, “you’re right! There’s probably something else on his shirt too.”
“He did say his shirt was ‘mostly’ white,” someone noted. The picture and the pink lettering could account for that.
“I’ve got it!” someone declared.
Chad nearly jumped at her exclamation. What could she possibly guess?
“Your shirt has the design of a bra on it… probably just like a real bra – all around. And it probably says something like… ‘I don’t ever go without my bra’.”
Chad just stared wide-eyed at her. He was trying to imagine something like it and his imagination was having no trouble picturing it. “Uh… no, that’s not it,” he finally replied.
“I’ll bet I’m not far off though,” the woman stated.
Chad just shook his head as the onslaught of guesses kept coming. His coffee was long gone before the break was over, but the guesses kept coming, even as he and Robin walked back to their desks.

It was a while before Mel could get back to Gloria when they both weren’t busy. “Hi Gloria, what’s up?”
“Hi Mel,” Gloria replied. “Hey, are we doing lunch today?”
Mel had to think about that a bit. “We can if you want. But it’s going to have to be a quick one. I’ve got to be in court this afternoon.”
“No problem. Really. We can skip lunch today. But I’ve got to talk to you about something before tonight.”
“Okay. So talk.”
“Listen, Mel, when you come in tonight, I’m going to have to spend a lot more time getting him ready to answer our questions than usual. I just wanted to warn you about that. In fact, most of the time tonight will probably be spent on that.”
“You are still going to ask the questions though?” Mel asked.
“Yes, definitely. I just don’t know how long we’re going to have after I finish getting him ready for the questions. I have another new client that’s coming in after you tonight so I can’t extend the session like I usually do.
“Just as long as you get the questions asked,” Mel replied. “So why will it take so much time?”
“Well, if we want to make sure he’s telling us the truth, then I’ve got to get his complete trust. And to do that, I’ve got to try some techniques I’ve never done before. Plus, I want to strengthen some triggers to make it go faster in the future.”
“Okay, you’re the expert. In fact, it sounds interesting. I can’t wait.”
“Well, I don’t know how interesting it’s going to be, but hopefully it will be affective!”
“Hopefully!”

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.

Quick Reminder

For anyone interested, I have the complete story (The Bet) so far (chapters 1 through33) available in a single document. Just email me at siskarensinger at yahoo dot you-know-where.

Smile at someone today,
Karen

The Bet - Chapter 33 (Wednesday – week 5 Part 8 of 8)

The Bet
by Karen Singer

Chapter 33 (Wednesday – week 5 Part 8 of 8)

Chad glanced at the clock as he finished cleaning up the kitchen. He still had a little over half and hour left for his diaper to start leaking. He was fairly sure he would be early again since he was wetting now every few minutes. What he found so interesting was that more and more often, he would simply start wetting before he knew he was going to. Not always, but sometimes. It was such an interesting feeling.
He glanced around the kitchen. Everything was clean and shining, just the way it should be. Mel was again in her living room chair, working on her laptop. He didn’t know how she could stand to work such hours. It never seemed to stop for her.
Not wanting to be told to stand in his corner again, he decided he had better find something else to keep busy with. He went directly to her clothes hamper and started pulling out her laundry. A few minutes later, he was watching as the washer began its job. He glanced back at Mel. As far as he could tell, she had never once even looked up to see what he was doing. The look on her face seemed to be only deep concentration.
With nothing left to do till the washer was done, he grabbed a dust cloth and started wandering around her apartment, making sure everything was in its place and dusted. As he was working on the table by her door, he suddenly realized he was going to pee again. It was only a second or two before his pee started coming out, and all too quickly the pleasant sensation ended. As he moved away from the table, toward the living room, he felt it. That tiny little tickle running down his leg. “Mistress. I’m leaking!”
Mel looked up from her work. She had a slight headache from the tension of what she was doing, but she was almost done for the night. Just a few more minutes and she could put it all away till tomorrow. She glanced over at the clock. He had made it again with time to spare. “You’re getting better at this,” she declared. “Maybe we should be giving you less time from now on.”
Chad was horrified. “Oh no, Mistress. Please don’t do that! I’m trying so hard, I really am!”
“And you’re succeeding very, very well.” She looked at him for a moment. “Okay, we won’t change your time… for now!” She looked back down at her work for a moment. She really needed to finish it. “Okay, Sissy. I need to finish this. I’ll be with you in a few minutes.” She paused, thinking again. “In the meantime, get everything ready for your punishment. And make sure you spread some protection on the floor in case you pee again!”
Punishment! Chad’s heart fell. He had made it, but this punishment was for the demerit he had gotten earlier in the day for not using his sissy voice on the phone. How could he talk that way when he was at work? He couldn’t! It wasn’t fair! He grabbed a stack of disposable diapers and carried them over to her usual punishment spot. He spread a few of the diapers out on the floor, covering as much as he thought might be necessary. He glanced at her yardstick leaning up against the corner. He didn’t dare touch it, even though he really wanted to throw it away somewhere… somewhere where she could never find it or use it again.
Mel was still working, so he waited… and waited. More pee ran down his leg. He was worried about it running down onto her floor so he stood on top of the diapers he had just spread out. And he continued to wait, silently.
With a huge sigh, Mel finally finished. She stared at her laptop for a few seconds more, then turned it off and closed the cover. She took a deep breath to bring herself back to life. It was time to get away from work for a while. Time to do something else. And Sissy was waiting. She didn’t really enjoy punishing him, but she was ready to do anything other than work, and punishing him was physical activity, and she felt the need to do something physical just then.
He was waiting patiently, standing on some spread-out diapers. When she saw how much pee had run down his leg, she was glad that he had done it. The skirt to his maid’s dress was still pulled high up around his torso, completely exposing his overly sodden diaper. Two seconds later, she removed that diaper and he was naked from the waist down… except for his shoes and chastity device. She looked at his penis inside that device. Tiny again. Totally! Just what she wanted to see.
She walked over to the corner and picked up her yardstick and swished it through the air a few times. She saw the look of fear in his face. Good! She got into her usual position and waited till he bent over with his arms on the back of the chair in front of him. His legs were slightly spread, but he had put enough diapers under him that he was still standing on them. It reminded her of something. She swung the yardstick through the air at his backside – hard!
The sudden blow to his bottom sent a shock wave throughout Chad. No matter how much he expected it, or tried to prepare himself for it, her stick always came as a surprise, and it always hurt… a lot! He stood up and curtseyed. “Thank you, Mistwess,” he said in his best sissy voice. Then he got back into position.
“You know, Sissy,” Mel said before she brought her stick back down again. “Since you’ve gone to all the trouble to protect the floor so nicely, I think we’re going to make a new rule.” She brought her stick down on him again.
Chad barely had time to register her statement about a new rule when the blow came, emphasizing the point. Pain! What new rule? What could she possibly want now? He stood up, curtseyed again and thanked her. Then bent back over again.
“From now on, Sissy,” she said, “every time you get punished, I expect to see you peeing on the floor.” Swish… Whap!
Again, Chad barely had time to register what she said before the stinging pain hit him. He was fighting back the tears and was mostly succeeding – mostly. Now she expected him to pee every time she punished him? That was crazy! Again he curtseyed and thanked her and got himself back into position.
Mel continued speaking. “In fact, Sissy. If I don’t see you peeing during your punishment, then I’m going to add another five swats. Every time!” Swish – Whap!
Ouch! Another five swats? His heart fell a bit more. How could she? But unfortunately, he wasn’t in charge, he wasn’t in charge of anything. All he could do about it was to stand back up, curtsey, and thank her one more time before getting back into position for another blow.
Ten swats. Ten very hard, very stinging swats. Ten curtseys. Ten times thanking her for punishing him. But no pee had come out of him during his punishment. So it continued. He wasn’t able to pee again till after the thirteenth blow. He jubilantly told her the moment he felt it starting, as he was bent over, waiting for blow number fourteen. Mel was happy and praised him. He started to get up, but she made him stay right where he was, bent over as if waiting. The peeing didn’t last very long and when it was over, he tried to stand up again, but she made him get right back into position. There were still two more swats to go. Chad was heartbroken to discover that no matter what, he would still receive the full extra five swats. He was already crying somewhat, but now he openly cried much harder.
When they were done, Mel rediapered him in one of the wet diapers he had been standing on. Her diaper job felt rushed and not as secure as she usually did it, but he said nothing. Maybe the diaper would leek faster this way.
“Clean this up and check the laundry,” she told him. “Let me know when you get the clothes into the dryer.”
Chad tearfully bent down to start picking up the diapers he had been standing on while Mel headed into her bedroom. He carefully folded them and put them away. He heard the washer finishing and moved the clothes into the dryer. She was still in her bedroom. It was time to let her know that he was done.
He walked to her bedroom doorway and poked his head inside. He saw her reading something. Her bed covers were pulled back and he saw the ropes out once again. Uh oh! “Mistress,” he said hesitantly. “The clothes are in the dryer now.”
She looked up. “Good. Go get those diapers you were standing on earlier so we can cover the bed with them.”
Chad took one more look at the ropes on her bed and went back to get the diapers. He brought them back to her and helped her spread them out over her bed. She made him get a few more to make sure everything was doubly protected. Then she asked him to take his dress off. After that, she removed the diaper he was wearing.
As soon as he was as naked as he was capable of getting, she had him climb up onto the bed, kneeling on it, on all fours. She tied the ropes to his wrists first, then to his ankles. It didn’t feel as secure as she usually did it, but he knew he wasn’t going anywhere.
She was doing something behind him. Far enough away that when he turned his head, he couldn’t see what it was. A moment later, she was liberally spreading lubricant on, and in, his tiny asshole. His spirits soared. This was what he wanted! She was going to use one of her toys on him again. He mentally prepared himself for the pleasure. He could almost feel the toy going in and out of him already.
He felt her approaching behind him again. He was ready. Something hard touched his asshole and a wave of pleasant anticipation ran through him. That something was pushing against him now, trying to invade his insides, and he wanted it there! He opened himself up to it and felt it going in. But it felt different, like nothing he had ever felt before. And even though it was still going into him, all of a sudden it felt like whatever part of it was at the opening, was much smaller, almost tiny.
And then he felt her manipulating the device inside of him. Yes, it felt good, but nothing like when it was being pushed and pulled in and out. What was she doing?
Very quickly, he felt the sensation, like he was about to pee, but a little bit different. And suddenly, he felt it coming out of him. His cum was almost pouring out of him. Lots of it! She was milking him again. And whatever she was using on him wasn’t nearly as much fun as what he hoped she would use.
Mel watched, fascinated, as his sperm leaked out through his chastity device. She kept manipulating the oddly shaped Aneros device inside of him and the sperm kept coming. More than she would imagine. Finally, it slowed down and stopped. She carefully pulled the device out of him again. “Well, that went well,” she declared.
Chad said nothing. He felt totally defeated. He was still horny as hell and he knew he would remain that way. But wasn’t that his usual situation? So nothing had really changed… except for the fact that he might be a little more comfortable now since she had milked the sperm our of him. For a while anyway, but only a little while. It was as if she had just removed any chance he might have had for an orgasm, even though he knew that the ability was beyond him. He suddenly felt the need to pee again and let it loose right there on her bed without caring one bit. The bed was well protected anyway.
Mel smiled as she saw him peeing. He seemed to be a bit upset, even though she couldn’t see his face all that well. She didn’t really care. From everything she had read, what she had just done was supposed to be healthy for him. Who would have ever thought? She untied his wrists and ankles, then removed the sodden diaper that had caught most of what had come out of him. She replaced it with another one. “Roll over now, Sissy. It’s time to work on your other side.”
His other side? Work on it? Chad wondered what she was talking about as he rolled over and laid down on his back. Was she going to remove the chastity device, now that she had thoroughly milked him?
Once again, Chad found his hands and ankles bound to the bed, only this time much tighter. He was actually glad when she unlocked his device and began removing it. The moment she pulled the main casing off of him, he felt the cool air on his cock. It felt strange. The touch of her hands as she removed the rest of the device felt strange too. And very nice. Mel left him for a while, and as he expected, came back with a warm wet washcloth that she used to clean him up with. The washcloth felt even better than the slight touch of her hands had earlier.
After cleaning him, Mel looked closer at his cock. There were some hairs starting to grow that needed shaving. She would get them in a few minutes. She could definitely see some light red marks from where the teeth of the device constantly touched him, but other than that, she could detect no other problems. She grabbed his tiny cock with her in her fingers and pulled it up, inspecting it underneath. The thing stretched a bit, but it didn’t’ seem to be growing at all – in the way that she knew it was capable of. As far as she could see, his cock looked perfectly fine. It was just tiny. Very tiny. And so far, her slight manipulations hadn’t made it grow one bit. “I’ll be right back,” she said as she headed off to find her razor.
Once again, Chad enjoyed her wet washcloth going over him. He enjoyed her shaving him there too, but only because the little manipulations of her hands felt very good. They were tiny and brief manipulations, but they still felt nice. They were the only sensations that part of his body had been allowed to feel in such a long time now. He was a bit surprised that he wasn’t responding sexually to her touch there, even though he wanted to. But then, after being milked like she had just done, he wasn’t sure if he would be able to. Actually, he realized that she was being careful to not really grab him or try to stimulate him too much at all – which was so disappointing.
All too soon she was done. He really enjoyed feeling her spreading some kind of cream all over him down there, but again, her attentions didn’t last long at all. And then he felt her fitting the device back onto him again. The feeling of utter disappointment felt like a lead weight in his stomach. Piece by piece he felt the device going back on.
Mel looked at the large teeth that had been in the device, then back at his cock. The teeth hadn’t hurt him at all, but there were some small red marks from them. She decided to change them out for the medium sized teeth instead. As she fitted them into the device, she wondered if he would start to get any bigger now. Only time would tell.
With a feeling of dread, Chad felt his cock once again being enclosed as the device was slipped over him. The feeling and sound of the tiny lock sent an awful feeling through him too. And then he felt her untying his ankles. He waited for her to release his hands as well, but she didn’t. Instead, he realized she was just getting ready to diaper him again.
Mel took one last look at his penis inside the device. It was still just as small as ever, but would it be that small the next time she saw it? She reached for the jar on her nightstand that held the suppositories and pretended to pull one out. She knew he was watching her. She clearly saw the look of displeasure as she pretended to put it up inside of him. He had no idea that she had put nothing but her finger up inside of him at all.
She diapered him then, heavily, in four disposable diapers that would last him the rest of the night. Finally, she released his hands. “Put your dress back on,” she told him. “Then clean my bed up and make it. And when you’re done, see to the laundry.” She walked away from him then. There was nothing more that she needed to say. She was the lady of the manor and he was only her maid. It felt so good!

The Bet - Chapter 33 (Wednesday – week 5 Part 7 of 8)

The Bet
by Karen Singer

Chapter 33 (Wednesday – week 5 Part 7 of 8)

It was later than usual as Chad drove home. He had waited extra long at work, pretending that he needed to finish something. By the time he finally braved walking to his car, there were very few cars left in the parking lot. Actually, by that time, he felt more like he was waddling to his car again. With the tighter pants, he was more conscious than ever of how full his diapers were. All the way home, he prayed that Mel wouldn’t notice how late he was.
But the minute he pulled into his parking space, he heard his phone ringing. He quickly fished it out of his purse and checked who was calling… Mel, of course. “Yes, Mistress?” he answered, carefully using his sissy voice.
“Why haven’t you called yet? I told you, the minute you got home!”
“I’m just parking my car now, Mistress,” he replied. “I had to work late tonight.”
Mel paused for a moment. There was a slight difference in the background sound. She realized that what she had heard was the sound of him turning off his engine. She certainly understood working late. She would be working a bit later tonight too. “You don’t do that often,” she noted.
“No, Mistress. But we’re coming up on an important deadline and I had to finish something.”
“I understand,” she replied. She glanced around at the paperwork still on her desk. She understood deadlines all too well. “Okay then, Sissy…” She checked her clock. “I know you haven’t had time to get cleaned up or changed yet, so I’m giving you two hours and fifteen minutes to get your diaper leaking – and not a minute more! You know the drill by now. One diaper only. Wear your uniform again – I like you in it. Cook something that you can keep warm in case I’m late tonight. I may be late, or I may not. I don’t know yet. Just keep busy – and keep wetting your diapers.”
“Yes, Mistress.” Chad replied. “I understand.”
“Good! See you later.”
Chad put his phone back into his purse. Just another typical day. His “new” typical days.”

Mel trudged wearily up the stairs from the parking lot to her apartment. She was later than usual, even for the days when she came home late. She turned the key in her lock and opened the door. She was immediately assaulted by the delicious aroma of something cooking. “This is living,” she thought. “This is why I really need him. It’s so nice to come home and have dinner already waiting – and something that smells good too!
Chad came hurrying around the corner of the kitchen toward the front door. The minute he spotted Mel, he stopped and dropped a cute curtsey. “Welcome home, Mistress.”
The sight of him curtseying in his uniform sent a wave of pleasure throughout her. Yes, this is how she wanted her life to be – the entire rest of her life. “Something smells good, Sissy.”
“Dinner is all ready. I just have to dish it out for you.”
“Go ahead. I was hungry before I came in, and now I’m even hungrier.” Mel made her way directly to the table that was already set for her and sat down while Sissy scampered around the kitchen. A few minutes later, she was forking the first bite of her dinner into her mouth. Um! So good! She glanced up at Sissy who was watching her from behind the kitchen counter. “Excellent!” she declared. “Now go to your corner.”
Chad’s face fell the moment he heard her command, even though he had been expecting it. At least she had told him this time that the food was good. That was something. He quickly took a long swig from his latest baby bottle and headed for his perch.
“Wait a minute!” Mel commanded. He turned back toward her. “I forgot about checking your diaper. Come over here where I can see it better.”
Chad walked hesitantly up to her and lifted his skirt so she could see.
“All the way up,” she commanded. “Like I had it yesterday.” She watched as he pulled his skirt up as high as it would go. She could easily see how soaked his diaper was already, but then, it should be by now. “Not much time left,” she noted as she glanced at the clock.”
“I know, Mistress,” I’m trying.
“Good,” she replied. “Now get to your corner.”
Chad, leaving his skirt hiked up the way it was, quickly grabbed his baby bottle for one more long swig before he made his way back to his corner, where he carefully put his feet over the bar of his perch, pushing him all too firmly into the crease of the corner. He put his arms down to his sides where she demanded that he keep them, and concentrated on standing still – once again. Still, and unwanted, and useless. Put away – like her vacuum cleaner.
Mel watched him as she ate. The food was delicious and gradually relaxed her and brought her back to life. She was feeling much better by the time she was finished. He was being good again, not moving at all as far as she could see. She briefly wondered what he thought about as he stood there, unable to move as she knew he wanted to – probably desperately. She glanced at the clock again, not much time for him. But would he make it this time? She knew that even though she had seemingly given him an extra fifteen minutes, because he still had to get cleaned up and changed, he probably was working with less than that. But she didn’t dare go easy on him.
She got up from the table. His dinner was on the counter – not in the refrigerator where she usually told him to put it. She’d have to watch that in the future. She grabbed her fork and knife and once again went to work on it.
Chad’s mind wasn’t blank, even though he was standing perfectly still in his corner without any outside stimulation at all. He was worried about what Mel might say about him asking Sandy to design his new apartment… and he was very worried about getting his diaper to leak on time. He knew it couldn’t take much more, but how long had he already been standing there? He had no way of knowing. Either way, he knew time was running out. What was Mel doing? Once again, it seemed like she was taking forever to eat.
And then, once again, he felt himself peeing – only a little bit as usual, but would it be enough? Nothing seemed to happen, leak-wise, by the time he finished. He felt disappointed and defeated. He had again tried so hard and he knew that his time had to be almost up. But just when he was sure he would be getting another beating because he hadn’t succeeded, he felt a tiny little something different at the top of his leg, just below the diaper. “Mistress,” he called quickly, knowing there couldn’t be much time left. “I’m leaking!”
Mel looked up from her task of cutting his food up into miniscule pieces. She glanced at the clock. Technically, time had run out half a minute ago, but she wouldn’t tell him that. It was close enough. “Excellent, Sissy. You just barely made it. Just stay there till I’m ready for you.” She went back to her task of making his dinner as difficult to eat, and as unrecognizable as possible. When she was satisfied with what she had done, she took his plate and personally put it into the refrigerator to cool till she was ready for it. “Okay, Sissy. Let’s get that diaper changed.”
Chad gratefully pried himself out of the corner and off of his perch. He stretched his ankles a bit before trying to walk. He saw Mel heading for her bathroom so he followed her there, grateful that she wasn’t going anywhere near her usual punishment spot. She changed him standing up again, the skirt of his uniform still pulled up high and out of the way.
“Two hours again Sissy,” she declared. “And I suggest you don’t miss that deadline because I haven’t forgotten yet about your demerit! You don’t want to make things worse, do you?”
Chad dropped a slight curtsey. “No, Mistress.”
“Good, then let’s get your dinner.”
Chad walked back into the kitchen toward his highchair. He noticed as he did so that the plate he had left on the counter earlier wasn’t there anymore. He correctly figured that she had put it into the refrigerator. A minute later, he was in his highchair, a bib was tied firmly around his neck, and Mel was pushing the tray back into place – for all intents and purposes locking him into the chair.
“So you want Sandy to design your apartment for you?” Mel asked as she turned away and headed for the refrigerator.
Chad had been worried about this. He was almost surprised by her casual attitude. “Yes, Mistress,” he replied… cautiously.
Mel pulled his plate out of the refrigerator. “And you really think you can win?”
It was a more difficult question to answer than he thought it would be. “I’ve thought so from the beginning,” he replied. Then before Mel could say anything more, he added, “I have to win!”
Mel stopped and just looked at him. “Why do you think you ‘have to’ win?”
Another difficult question, especially trying to explain it to her. How could he tell her about wanting self-respect again when he was sitting in a highchair with a bib around his neck? He shrugged a bit. “I just do, that’s all.”
“And you’re so sure you can win?”
It took him a moment to answer. “I hope so anyway.”
Mel caught the slight bit of uncertainty in his voice. She was glad to hear it because it meant that he was not so sure after all. She continued back to him with the plate in her hands. “I have to win too,” she stated – not unkindly, just as a simple fact. She set the plate down in front of him and headed back toward the counter again.
Chad stared down at his food. He died a little bit inside just looking at it. She had again cut everything up into the tiniest little bits that she possibly could and mixed everything all together. There was no way that he could get a proper sense of what anything tasted like. Every bite would taste exactly the same. Not to mention how hard it would be to eat since he noticed that she hadn’t giving him anything to eat with again. Having no other option, he stuck his hand into the plate and picked up a bunch of the mashed together food. Sticking it into his mouth without dropping any or getting any on his face proved to be impossible. He looked up as he heard Mel giggle. He felt like such an infant.
Mel set a fresh baby bottle full of juice on his tray, then poured herself another cup of coffee. She leaned against the counter and watched him trying to eat. There was no doubt how silly he looked. She could watch this all day! “So you’re really sure you want Sandy to design your apartment?” she asked.
Chad looked up as he tried to put more food into his mouth. “Yes, Mistress.” Most of the food this time wound up on his chin and bib.
Mel giggled again. “You want her to draw pictures for you, or something? Something you can see ahead of time?”
This time, Chad answered with no food in his hands. “That’s exactly what I want.”
Mel nodded. “You know, of course, those pictures will only be a reminder of what you’re going to lose.”
Chad shook his head. “No, they’re going to be a reminder of exactly what I’m going to gain! What I want!”
So that’s what it really was, he needed the extra inspiration. It wasn’t just that he was so sure he was going to win. But Chad didn’t know what Mel had asked Sandy to do along with his request. “Well, I don’t really mind, since I think it’s only going to show you exactly what you can’t have. And in the end, it’s only going to make you feel much worse.”
“Well, see,” he replied as he picked up his baby bottle for a quick drink.
She watched him trying to eat for a while before saying anything else. “I hear your friend Robin is trying to join the gym.”
Chad wasn’t at all surprised to hear that Mel had heard already. He was sure that Cassie called her every day. “Yeah. I don’t know what I’m going to do about it.”
“Do about it? What’s the problem?”
“If she joins, then she’ll talk to the other people there. She’ll find out about what I did on Monday! And worse… she’ll find out what I really do there every day.”
“So she still doesn’t know?”
“No! And I want to keep it that way.”
Mel shook her head. “I really think we should have taken you to work on Monday instead. I don’t know why I let you talk me out of it!” She was only teasing, but the idea was still rolling around in the back of her head.
“Thank you for not taking me in there,” Chad replied quickly. “I would have died!”
“You would have survived. It wouldn’t be the end of the world. And you wouldn’t be worried about Robin finding out about your little secrets now. By the way, just what is it that she doesn’t know yet?”
“About me wearing diapers.... or anything at all about this bet. She thinks I dress like a woman all the time now because I just want to do it!”
“Well, don’t you? Isn’t that part of your fantasies?”
Her question made him feel very funny inside. “Yeah,” he admitted sheepishly. “It is. Definitely!”
“So you’re really loving it?”
“Yeah,” he admitted again, unable to look her in the face. He shoved another bunch of food into his mouth.
“Is it just Robin you’re worried about?”
“No, it’s everybody. But I work with Robin all the time. She’s the only real friend I have. She’s really… nice.”
His last statement stung her just a bit. What did he consider that she was? She was his friend too! Or did he really hate her so much now? She hoped not. Either way, her dislike of Robin grew a tiny bit more. “She’s nice? So you like her a lot?”
He picked up his bottle for another drink. “Yeah, she’s a good person. She asks way too many questions though. She can be downright infuriating sometimes.”
That was a little better news about Robin. “Infuriating? How?”
Like today for instance. “She’s convinced that my diaper bag is really a gym bag…”
“And you didn’t tell her anything different?”
“I didn’t dare!”
“Go on…”
“Well, she thinks I wear some kind of shorts and a t-shirt outfit while exercising in there… and she thinks the t-shirt has some kind of embarrassing writing on it. And she’s been trying to guess it all day!”
“And you didn’t set her straight?”
“It’s a lot better for her to be thinking that than knowing the truth.”
Mel watched him picking up more of his food. “What made her so sure you’re wearing a t-shirt in the first place?”
“It was just a guess on her part.” He rolled his eyes. “You should have heard her first idea for what she thought I wear – a pink leotard and tights!”
Mel giggled.
“And then she went off on some wild tangent about adding a pink tutu to the outfit too! Geez! The t-shirt idea is at least a bit more sane.”
But all Mel could see at that moment was a picture in her mind of him in a pink leotard and tutu. But as she thought about it, she made a slight change, the tights went from pink to white. And so did the tutu! “I kind of like the leotard and tutu idea. Maybe we should get you one. Wouldn’t that be fun?”
“No thank you, Mistress. I’ll pass on that idea.”
But Mel was still having fun with the vision. “Then we could send you back to the gym for some real exercise, maybe right alongside your friend Robin. I’ll bet she’d really love seeing you that way.”
Chad felt sick at the very thought of it. He didn’t get to reply because they were interrupted by someone knocking on the door. As usual, a wave of fear raced through him. He was stuck in the chair with no way out. Whoever came in would see him. He sat perfectly sill as Mel went to the door and answered it. She came back a minute later with Sandy right behind her. Chad breathed a sigh of relief. It wasn’t some stranger. He noticed right away that Sandy was carrying some kind of professional case in her hand.
“Oooo, he’s having his dinner,” she said the moment she laid eyes on Chad. “Hi, Sissy.”
“Hewwo, Sandy,” Chad replied in his usual sissy voice.
“Ewww! What’s he eating?”
Mel smiled. “The same thing I had, only cut up in tiny pieces for a little baby.”
Sandy laughed. “I’m surprised you didn’t just put it in the blender, or a food processor or something.”
Mel looked startled. “I never thought of that!”
Sandy just giggled as she pulled out one of the kitchen chairs and sat down, setting her case down next to her.
“Do you want me to get him out of there so you can talk?” Mel asked.
“No. I love seeing him like that. I prefer it actually.” She looked at Sissy. “You just go ahead and finish eating while we talk. I’m ‘sure’ you’re still hungry!”
Chad rolled his eyes a bit a he dug a bit more food off of his plate and tried to get most of it into his mouth. A little bit fell on his bib and Sandy giggled.
Sandy pulled a big notepad out of her case and opened it on the table in front of her. “Okay, she said. “What ideas did you have for your apartment?”
“First thing is a pool table,” Chad replied.
“A pool table? Figures!” Sandy looked over at Mel for confirmation.
“Like I said earlier. The sky’s the limit. If he wants it, he can have it.”
Sandy shook her head. “Oookaaay,” she said, drawing the word out as she wrote pool table down on her pad. “What else?”
Chad went through the list he had memorized many times over from his spreadsheet. Sandy dutifully wrote everything down. She pulled out some fabric and paint samples and discussed a few of them with him, but she quickly realized that he basically had no concept of what colors he wanted or what kind of fabrics would be best.
When they were done, she looked at him a bit disappointed. “So basically, you want the ultimate “guy’s” hangout?”
“Yeah, kind of.
She shook her head. “I’m surprised. I would have thought that someone like you would want something at least a bit more… feminine.”
Chad sat and thought about that for a moment. “It’s another fantasy,” he replied. “And the truth is that I’d really love it. Really! But I want to have friends over, and something more feminine would raise too many questions.”
Sandy nodded. “I see,” she replied. “We could always do just your bedroom that way. Then you can just keep the door closed when you have company.”
Chad thought about that for a bit. “It sounds good, but in the end, somebody may still go in there and see it.”
“How about if we just do your bedroom a little bit feminine? Nothing over the top.”
Chad smiled. “Now that might be good.”
Sandy made another note on her pad. Basically, what he was asking for was easy. She did dozens of places like he wanted every year. She was just surprised that he would want it to look so masculine. He was willing to pay for it, so she would do her best to lay out something that would look great and he would love. But the project – as he wanted it – was basically easy and a bit boring for her. But what Mel had asked for… now that was a lot more interesting. She had never even thought of doing anything like what Mel wanted. And since Mel had mentioned it, her imagination had been running wild!
She closed her notepad and put it back into her case. “Okay. I’ll get started on it and let you know when it’s ready. Don’t look for it right away. This will probably take me a few days.”
“That’s fine,” Chad replied, happy that she was really doing it for him… not to mention that Mel was making no objections at all.
Sand stood up and took one more smiling look at Chad in his highchair. His face and hands were covered with food – as was his bib and the tray in front of him. The half-full baby bottle on the tray was a dirty mess from his messy hands. When she bent down a bit she could see the diaper he was wearing – which looked a bit wet. He looked so funny. So silly! And he was an adult! She shook her head. Thoughts of what he had asked her to design for him didn’t match at all with the person she saw in front of her. But Mel’s ideas…
“I’ve got to go now,” she finally said as she picked up her case. “I’ll let you know when it’s ready.”
Mel walked her out to the door. Chad never saw the conspiratorial look that the two women gave each other as they left the kitchen. He just went back to trying to finish his dinner, which was none too easy.