A Different Kind of Comment

Hi All,

I really just wanted to say thank you again to everyone who is reading this story. And I’d like to say a special thanks to the couple of people who have emailed me recently or left a comment in this blog – you know who you are! You don’t know how much I appreciate your response.

On the one hand, the comments let me know that someone out there is reading this and appreciates it, but on the other hand, what kind of comment can you really write? Mostly, I think everyone is enjoying the story so no comments are necessary and to tell the truth, I don’t expect any.

I’ve found a different way to gauge whether people are enjoying this story or not – the followers list at the side of the page. Over time, I’ve been steadily watching the number of followers going up and up. I can’t believe how many I have now! Thank you – all of you!

There is one more way that I’ve found to gauge this story. Blogspot has a stats page where I can go to look at how many hits this blog has had over varying periods of time. On a daily basis, I get between 200 and 600 hits. On a monthly basis the hits range from about 10,500 to 16,000. It actually fluctuates back and forth quite a bit. But overall, those numbers seem to be rising too.

So I am currently basking in the knowledge that there are a lot of people out there who are reading this story and enjoying it! That’s what it’s all about for me! Thanks to every one of you! Those numbers keep me going!

I guess while I’m here I should mention that I keep a text file of the completed posted chapters so far. You can email me at siskarensinger at yahoo dot you-know-where if you want a copy so you can catch up on anything you’ve missed without searching back through the entire blog.

I guess I should also mention again that the Baby Bobby story I wrote some time ago is still available too if you want it. Just email me and tell me what you want.

Oh yeah! I recently sent out a copy of my very old What’ll I Wear program to someone and he said he actually got it to work with no problem! If you’re interested, I guess I can send that too. I make no guarantees about it though.

So have a happy holiday season everyone. Please enjoy it to its fullest! And please stay safe !

Karen

The Bet - Chapter 44 (Sunday – week 7 Part 9 of 9)

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 9 of 9)

As they all stood up to exit the theatre, Mel “offered” to hold Sissy’s cup for him while he grabbed his purse and got to his feet. She noticed that the cup was now totally empty. Not even the ice remained! How perfect was that?
As Chad got to his feet, he immediately realized what he hadn’t realized before. His diapers were huge! Girdle or no girdle, he had peed so much during the movie that they were now super bloated. But were they leaking? He hoped not. As he struggled in his super high heels, with his legs now spread wider than before to get out of the aisle, he stumbled a bit and felt Derek’s strong hand grab his arm to help steady him. “Thanks,” he said as he turned back briefly. He was surprised that Derek continued to hold his arm to help steady him till he reached the end of the aisle. He expected Mel to give him back his empty cup so he could throw it away, but instead she just reached down and set it on the floor out of the way. The cleaning staff would have to deal with it later.
The trip down the steps was interesting for him. Between the super high heels and his super bloated diaper, negotiating the easy steps was more of a challenge than he thought it would be. But he made it. He only hoped that Derek – and everybody else, wouldn’t notice how oddly he was walking now. And… damn! Was that a bit of wetness he was feeling between his legs? Damn! He was leaking! And there was nothing he could do about it. Well, hopefully the girdle would keep that from showing too. He hoped.
Mel and Ray reached the bottom of the steps and “waited” for Sissy and Derek to catch up. Ray was going to lead the way out, but Mel held him back for a moment till Sissy and Derek could get in front of them. She wasn’t sure if she should be surprised or not at the tear tracks that were all too obvious on Sissy’s face he went past her. She quickly reached out and whispered into Sissy’s ear before he got past her, “Grab his hand!”
The command to grab Derek’s hand, on top of all the other things he was feeling just then was almost more than Chad could take, and he let out a bit of a cry at hearing it.
Derek stopped for a moment as he heard something from Sissy. “Damn! Are you still crying over that thing?” He looked back at Mel and noticed that her eyes were still a bit damp too. He shook his head. “Women!” He started walking again with Sissy by his side. “It’s just a silly movie,” he said, trying to get Sissy to stop crying.
“Yeah, I know!” Sissy replied with more emotion than he wanted. Actually, the emotion was mostly coming now from Mel’s order to grab Derek’s hand and hold it than from the movie. But having said that, he reached out his hand and grabbed Derek’s.
Oh brother! Derek couldn’t believe it. Sissy was actually needing some kind of comfort and hand holding? After just a silly movie? And he claimed he wasn’t on hormones… or whatever it was that Sissy’s kind took. But feeling like more of a sap than ever, he “allowed” Sissy to hold his hand to comfort him as they headed down the long hallway toward the lobby again. And over and over again, Ray’s little cell phone camera was snapping picture after picture behind them.
Sissy couldn’t believe it! Derek was actually holding hands with him. It was as if he was a real woman that Derek was out with. He couldn’t believe how strange he felt about that. He couldn’t even begin to explain it. One thing he could explain though was how much wetter and wetter he seemed to feel as they kept walking. His diapers had to be so soaked! But now he was worried about it showing up on the back of his skirt. Would anybody notice? He sure hoped not!
“Is it my imagination, or is Sissy walking funny?” Ray pointed out to Mel as they followed them.
Mel almost laughed. She had also noticed Sissy’s odd walk, and it had nothing to do with his high heels. But she couldn’t tell Ray that at all. “Those heels are probably killing him,” she explained.
“I’m not the least bit surprised,” Ray replied.
Once they reached the lobby, Derek was intent on heading straight for the car, but Mel stopped everyone. “I’m afraid I need to fix my face in the ladies room before we go home again. Coming Sissy?”
Chad gratefully dropped Derek’s hand and followed her into the ladies room – again. Wow, he hadn’t been in a bathroom so much in a very long time. And a bathroom was probably the right place to be going since his diapers were so wet. Unfortunately, he didn’t have his diaper bag and he knew without a doubt that there was going to be no “fixing” them till he got home.
Again, the room was fairly busy, but not as busy as before the show. While Mel went into one of the stalls again, Chad found the mirror closest to the corner and out of the way. Ugh! His face was a mess from the crying he had done. But was it worth trying to fix it all now? Well, there was probably no hope for it. Mel had said she was coming in to fix her face too. He carefully wiped his face, trying to preserve as much of Sandy’s makeup job as possible. Then he started in on fixing things as best as he could. Two minutes later, Mel was beside him doing the same thing. “Is this good enough?” Sissy finally asked.
Mel looked at him. He had done a fairly good job and quickly. At least he didn’t look a horror anymore. She smiled. “Good enough… except… I want you to add another really thick coating of lipstick.”
“More? But I just did that!”
Mel shook her head. “Make that two more coats! Heavy ones!”
Chad wanted to scream. But he went back to the mirror and added another “thick” coating of lipstick to his lips. Then he glanced up at Mel. “One more to go,” Mel said. Once again, he ran the lipstick “thickly” over his lips. They now felt so overly bloated with lipstick that he almost couldn’t stand it. He was starting to get tired of the “taste” too. It was simply too much.
Mel smiled. “Now we can go home.”
“Mistress…” Sissy quickly stopped her. Very quietly he said, “I’m leaking! Badly!”
Mel didn’t know whether to cheer or be worried about it. “Well, there’s nothing we can do about that here. We’ll just have to take care of it when we get home.” She paused for a second. “Wait a minute! Spray yourself with a bit more perfume. That will disguise any smell, just in case there is any.”
Chad wasn’t all that fond of the idea, but it did have some merit. Not that he wasn’t going to do as Mel told him anyway. He dug the perfume out of his purse and “carefully” sprayed his wrists again.
“Here, give me that,” Mel said as she took the perfume from him. She sprayed his neck with it too and also went behind him and sprayed a bit on the back of his skirt. “There, that should do it!”
“Is my skirt wet back there?” Chad asked.
“No. Not yet anyway.”
Chad was very relieved. For now.

Ray didn’t exactly take his time driving back to Mel’s apartment, something Derek was glad about. Sissy didn’t really mind it either. But Mel’s thoughts lingered mostly on Ray and the fact that she was determined that she wasn’t going to sleep with him – tonight – despite how she had felt in the theatre. Another day, well, that was a different matter. But she also knew that Ray was going to “push” the issue when they got home. Well, she would just have to refuse him. Tough if he didn’t like it! Her main concern tonight had to be Sissy! Winning this bet meant a lot more to her than a simple tumble in the sheets… well, even if it wasn’t just a simple little tumble.
Ray pulled into the same parking place he had used earlier and everyone got out of the car. Chad held back a bit and tried to grab his skirt in such a way the no one would realize what he was really doing. He pulled on it a bit and used his hands as if straightening the back of it, but what he was really doing was trying to feel if there were any wet spots. And… unfortunately… he was able to feel damp fabric fairly quickly. He hoped it hadn’t spread too much or was too noticeable.
Mel led the way up the stairs and Chad brought up the rear – walking a bit wide-legged and awkwardly in his heels. Mel reached her door and unlocked it, and pushed it open – slightly. Then she stopped and turned to Ray. “Thank you for such a great evening,” she said. “You have no idea how much I enjoyed it.”
Ray was surprised. “But… you’re not going to invite me in?”
Mel shook her head. “Not tonight. I have other things I have to do tonight, and you’ve still got to get Derek home again.”
“Yeah!” Derek chimed in.
“But…” Ray started to argue.
Mel just put her hand on his chest to stop him. “Not tonight!” Then she added a bit softer. “Call me tomorrow. Please!”
Ray, realizing he had just lost out, was very disappointed, not to mention a bit angry, but he held his anger back. “I had just hoped…”
“Not tonight,” Mel repeated. “But there’s still one more thing we have to do before you can go. Kiss me… please!”
“Damn!” Derek muttered in the background. He turned toward Sissy. “I was really hoping we could forget about this part.”
“Me too,” Chad agreed.”
Since Derek was going to have to kiss Sissy and he was going to get a goodnight kiss from Mel, Ray was at least feeling somewhat better about things. With a smile on his face, he looked down into Mel’s upturned face. He grabbed her face with both hands and lightly planted a kiss on her lips. Then, not really separating, he wrapped his arms around her and pulled her into him firmly, and kissed her so much more firmly – yet tenderly.
Mel was tempted to drag Ray inside with her during that kiss, but she held out and just enjoyed it. It had been a long time since anyone had ever kissed her like that. In fact, she couldn’t remember anyone ever kissing her so well. The kiss finally broke and before he could let her go she said, “Yeah, please call me tomorrow – for sure!”
Ray was a bit more pleased. “Don’t worry, I will,” he replied.
He let Mel go and turned toward Derek and Sissy. “Your turn,” he said tauntingly.
“Damn!” Derek said with a shake of his head. “I’m not doing this!”
Chad was actually relieved. “Good,” he added quietly.
“Sorry pal,” Ray said. “You’ve got to.”
“No I don’t! I think I’ve been a good enough sport tonight already. I went to dinner, I went to the movie. Heck, I even danced with him. But that’s as far as I go!”
Mel stepped forward, “Please,” she said. “You’ve got to.” Then she thought of another idea. “Pretend you’re kissing me,” she suggested. “In fact, think of it as an audition. Let me see how you would do it and then I’ll decide if I want you to call me or not.”
Derek just stared at her. Ray and been practically rubbing into his face the fact that he was dating Mel instead of him all night long. “Damn!” he exclaimed again.
Before Chad could react, Derek turned and grabbed him and pulled him into him. He wrapped his arms around him and held him tightly, lowering his head slowly toward Chad’s face. Chad barely had time to register that the kiss was coming before their lips met – softly. Ever so softly. As Derek’s arms closed tighter around him, the pressure increased on his lips till they were kissing firmly. As horrible as it was, Chad felt the breath go out of him from the passion of the kiss. Then he felt himself being grabbed tighter, and tighter, and… and Derek actually picked him up off of his feet and held him there while still kissing. Chad was feeling so many confusing emotions running all through him, including his body peeing into his leaking diapers again.
Derek lowered him back down and Chad quickly found his balance in the heels he was wearing so he could support his own weight. And just as softly as the kiss had started, Derek began to withdraw – slowly. Their lips parted, and Derek was still looking at him as he slowly drew his head away. Chad barely registered the fact that Derek’s mouth was covered in red lipstick – a lot of it. He felt dizzy for a moment. He had simply never expected anything like that. As if dazed, he just continued to stare back at Derek’s face.
“There! Now let’s get out of here,” Derek said as he turned and strode off toward the stairs.
Mel’s legs actually felt weak from watching the kiss. Wow! First the kiss she had gotten from Ray, and now that she had seen what Derek could do too… Where had these guys been all her life?
“I guess…” Ray started to say as he put his cell phone back into his pocket again.
“Go!” Mel said, interrupting him and giving him a little push. “Just don’t forget to call me tomorrow.”
With a nod and a smile, Ray turned and left too. Mel stared after both of them till Ray’s car drove out of sight. Only then did she turn back toward Sissy. His mouth had lipstick smeared all over the place. She had wanted it thick to make sure that Derek would wind up with a lot on him, and it looked like she certainly got her wish. She and Sissy just stared at each other for a moment. “Wow,” she finally said. “Both of them can really kiss!”
Chad still couldn’t speak. All he did was to nod.
Mel almost laughed. “Curtsey for me Sissy.”
Chad actually smiled as he curtseyed. “Yes, Mistress,” he said in his sissy voice. Only then did he take the time to realize, he had gotten through it. He had gotten through the whole date – kiss and all. And it hadn’t really hurt a bit – other than his aching feet. Whew!
Mel knew she could have stayed with Ray tonight, she knew she could have done it easily. The only real sticking point would have been getting Derek back home. But something could have been worked out for that. It was almost a matter of principal though, she and Sissy hadn’t been separated in the evening since this bet had started. And… she just wasn’t ready for it yet. Tending to Sissy had to be her first concern – a concern above all others. It was almost like… like having a baby. She almost chuckled at the thought. “Come on, Sissy, let’s get you changed for the night.”
A little while later, Chad was clad in four extra large cloth diapers. His plastic panties were stretched tightly over them. But Mel figured that he was probably going to need all that protection tonight – given the amount that he appeared to be still peeing. Mel had made sure to stuff another suppository up inside of him in the process. The one this afternoon had been faked, there was no way she was going to forget this one. Going without one twice in a row was coming up all too soon – tomorrow in fact. And Mel was actually worried about what might happen.
Wearing only the huge diapers, plastic panties, and a bra to hold up his glued-on breasts, Chad headed awkwardly for the door. He could hardly walk his diapers were so huge – and he had only wet them two or three times since Mel had started diapering him. It was going to be a long night. And tomorrow… tomorrow he would have to face Robin… and would probably get fired! He turned back toward Mel, and curtseyed. “Mistress, I’m worried about tomorrow.”
Mel shook her head. “We’ll worry about tomorrow – tomorrow.” She smiled then. “Did you have fun tonight?”
Chad thought about it. He almost spoke without curtseying again, but he remembered just in time. “Yes, Mistress. I actually did. And the movie was great!”
“Yeah, it was good, wasn’t it? Go home and dream about your date tonight Sissy. Dream about dancing with Derek… and kissing him. Just don’t forget to drink three more bottles before you go to sleep.”
Dream about Derek? And kissing him? Chad inwardly shuddered. Yet… it had been a more interesting experience than he thought it would be. And talk about intense! With a nod, he curtseyed one more time. “Goodnight, Mistress.” He grabbed both his old purse and his new clutch purse. He pulled his door key out and got it ready. He grabbed his high heeled shoes in his other hand. Everything else could stay. Everything else had to go into the wash – soon! And then he was out the door and heading home. Dream about Derek? She had to be kidding! Derek was one thing, but Robin and getting fired were another!
Mel stared at the door long after Sissy had closed it behind him. He was right to worry about tomorrow. He was right to be worried because of what she had done… a mistake she had made. And she had no idea how she could possibly fix it. “Good night Sissy,” she said softly into the empty room. “Good night… and good luck tomorrow.”

The Bet - Chapter 44 (Sunday – week 7 Part 8 of 9)

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 8 of 9)

The movie theatre was a large complex with lots of movies playing. Sissy felt like he stood out way too much since he and Mel were so obviously overdressed. But like everything else, there was nothing he could do about that.
Ray asked Mel if there were any movies that she was interested in seeing. But Mel had been so busy with other things in her life that she didn’t even know what most of the movies were about. Knowing that women preferred the romantic ones, Ray suggested several that he already knew were good. The fact that he had already seen them didn’t go unnoticed by Mel. She finally decided on a romantic comedy that she figured would be enjoyed by everyone – and that would be starting fairly soon. While Ray and Derek were buying the tickets, she dragged Sissy once again into the ladies room.
While Mel went into the stall again, Sissy had to add yet another layer of lipstick on top of his already overly coated lips. There were a lot more women in this restroom than Sissy ever had to deal with before, but he went to as far a corner as he could to work in front of one of the mirrors there. And as far as he knew, none of the other women in there noticed him… much. At least nobody said anything to him – fortunately.
Before they left the ladies room, Mel had a little more “advice” for Sissy. “Before we go into the movie, get yourself the largest drink you can. And I better see it finished before the movie ends!”
Sissy wanted to scream. More liquids! “Yes, Mistress,” he said softly.
Mel smiled at hearing him refer to her as Mistress, but she wasn’t quite done with him yet. “There’s just one other thing,” she said with a gleam in her eye. “From now on, whenever you and Derek are walking anywhere, I want to see you try to hold his hand!”
Sissy was shocked! As the realization of what she was saying sunk in, he thought his knees were going to buckle. Fortunately, he stayed upright. And then Mel turned around and headed for the door… and he had to follow.
Out in the lobby, Ray and Derek were just returning with the tickets. Mel glanced at Sissy as they all met up again. “Um… If you don’t mind,” Sissy said, “I’m going to get myself a drink before we go in.”
“You’re kidding!” Derek said. “You had enough iced-tea to drown a horse in the restaurant!”
Sissy just shrugged.
“Nerves!” Mel stated for him. And that seemed to explain it sufficiently to everyone.
Sissy was about to excuse himself to get the drink, when Derek rolled his eyes and asked. “What do you want? I’ll get it for you.”
Sissy couldn’t believe it! Derek was going to buy him his drink too? “Uh… Just a coke please… The largest one you can get!” he added quickly.
Derek looked at him like he was crazy – once again! “You’re not kidding?”
Sissy embarrassedly shook his head. “Please?” he said shyly.
Derek turned away and walked off toward the concession stand.
Not to be outdone, Ray quickly asked Mel if she would like anything, but Mel refused stating that she had already had more than enough.
When Derek came back with the drink, Sissy thanked him and took a quick sip, as if to show that he really wanted it. Then they started heading toward the theatre where their movie was supposed to be playing. For some unknown reason, this time, Derek and Sissy seemed to be in front, leading the way, while Ray and Mel followed. As he walked next to Derek, Sissy suddenly heard Mel loudly clearing her throat behind him. He doubted anyone else took much notice of it, but he did. He moved his drink to the other hand and ‘cautiously’ reached out his hand to touch Derek’s.
Derek was startled by Sissy’s hand touching his – as if he was trying to hold his hand! Startled, he quickly pulled his own hand away and looked over angrily at him. What the heck did he think he was doing?
Since Derek obviously wasn’t going to hold his hand, Sissy relaxed and just followed him into the theatre.
Once inside, Ray suggested moving toward the back – where it would be easier for him to see the whole screen. He got a dirty look from Derek for that suggestion, but they climbed up to the back of the theatre and all entered one of the rows together. Derek went in first, followed by Sissy, followed by Mel, and finally Ray. TV commercials were playing on the screen and Chad lamented the fact that even at the movies they could no longer get away from them.
Having no better place to put his purse, Sissy kept it in his lap. His drink was so large that it was easier to hold it with both hands and he rested it on top of his purse. He didn’t really want it at all since he already had way too much to drink. It was dark in the theater, and would be darker once the show started. Could he possibly get away with not drinking it at all? He could just leave the cup behind when they all walked out. His problem was, that knowing Mel, she would probably find some way to check on him when the movie was over. But would she? Unable to decide what to do, and not wanting to drink anything at all, he kept the cup in his lap and did his best to ignore it for a while.
While they waited for the movie to start, Ray quietly told Mel one or two things about the movie that he particularly liked. Mel was tempted to ask which woman he had seen it with already – or how many women he had seen it with – but she refrained in the name of being polite. What did she care how many women he went out with? Like everyone kept telling her, it wasn’t like she was going to marry him!
She glanced a few times toward Sissy and Derek. As usual, it appeared as if they were both ignoring each other. She didn’t see Sissy drinking anything, but that didn’t mean he wasn’t. Ray was still occupying most of her attention. As the lights dimmed further in preparation for the movie to start, she looked over again at Sissy. His cup was still in his lap as if he hadn’t tried to drink anything from it. She leaned over and quietly said, “I expect that drink to be finished before the movie ends. I’ll be checking it later!”
Chad now had the answer to his question. As Mel leaned back in her seat again, he brought the large cup up and started sipping from the straw. Ugh!
They had to sit through several movie trailers of upcoming movies before the movie actually started. Once it did, Ray leaned over one more time to speak to Mel. Before talking, he reached over and took her hand, as if to emphasize what he was about to say. “I think you’re going to love this movie,” he said. He leaned back again, but Mel was quick to notice that his arm was still in her lap, still holding her hand. Wow, what an operator! Surprisingly, she didn’t shake his hand away or even complain. She just let him hold her hand.
The movie was slow to start and Chad noticed Derek fidgeting more than once in boredom and frustration. He sipped slowly at his drink every few seconds as the movie continued. But the further into the movie they got, the more interesting it seemed to get, and Chad was so used to sipping liquid almost constantly now that he was doing it without thinking.
One of the love scenes began in the movie. Mel was riveted. She was riveted that is, until she suddenly felt Ray’s finger, from the hand that was still holding hers in her lap, begin to move… and poke… and lightly rub against her crotch under her thin dress. She should have stopped him. She should have! But she didn’t. The love scene became more torrid, and so did the manipulation of his single finger. She couldn’t believe he was doing it! She couldn’t believe it! She also couldn’t believe that she was actually letting him. And… she couldn’t believe how turned on she was getting. Unfortunately, when the love scene ended, so did the manipulation of his finger. She breathed a silent sigh of relief – and wondered if there would be more such love scenes.
Ray couldn’t believe his luck. She hadn’t stopped him! She hadn’t even given him the slightest clue that she wanted him to stop. That meant… later! How long did this sappy dumb movie last?
Derek couldn’t get into the movie at all, classifying it as a typical “chick flick.” So he sat and fumed over how he had gotten himself into this mess in the first place. Well, at least Sissy… or Chad… or… whatever, had made the effort to look – decent tonight. In fact, he had obviously gone all out. He guessed that it was all part of his sudden – and weird – desire to become a woman. And he was obviously getting better at it because, fortunately, he really didn’t look too bad. Fortunately! He almost felt like he had gotten through dinner just fine – no embarrassment – other than the dancing of course. That had been stupid! He could have definitely done without the dancing! Sissy said it wasn’t his idea? He “usually” did everything Mel told him to? Damn! Couldn’t the guy get a little backbone?
This was the first movie Sissy had been to in a long time, and he was thoroughly engrossed in it. But he was engrossed on two levels. Part of him was relating to the guy in the movie… or guys in this case, and since he had been dressing, and for the most part, living as a woman for the last two months, part of him also identified with the female character. Surprisingly, the movie was well enough written that both sides were accurately portrayed. He could both understand and feel what the guys in the movie felt, while at the same time, he could also understand things from the female perspective that he had never realized before – or at least he thought he could. He was so interested in it all, that when he suddenly started sipping air though his straw instead of coke, the resulting noise actually startled him. “Sorry,” he said softly to Derek who had quickly looked over in annoyance.
Mel heard the gurgle from Sissy’s cup too and it seemed to pull her right out of her interest in the movie – for a moment. She quickly realized what the sound was, and with a feeling of satisfaction that Sissy had done as he was told, allowed herself to get right back into the movie. She was particularly interested because she suspected that another little “love” scene might be coming up – and she hoped she was right. Ray’s little finger had been all she could think about since the first one!
Ray, of course, knew that the scene was coming. Would she let him “play” a little with his finger again? He hoped so, because this time he planned to do a lot more exploring with more than just his finger – if she let him. But he was now fairly confident that she would. He wished he dared look at his watch to see how much longer this stupid movie was supposed to last. But he couldn’t do that. He couldn’t give the least impression that he wasn’t really interested at all – at least, not in the movie.
Mel felt Ray’s finger moving again, and the characters hadn’t even gotten to the bedroom yet! And then something happened in the movie to delay the love scene, yet Ray’s finger was still working. Then something else happened and the scene was delayed yet again. The frustration was building quickly inside of Mel and she realized her panties were getting wet. Damn. But it also felt so good! Then still something else happened in the movie to delay the inevitable and her frustration grew again! But this time, the delay in the movie made her think a bit more about what was going on. She knew that Ray wanted to make love to her tonight. And okay, right now she was more than ready to go along with that idea! But not tonight! It couldn’t be tonight! She had definitely decided that she wasn’t going to do this with him tonight! Besides, they had all come in Ray’s car, how would Derek get home?
Not surprisingly, things suddenly worked out in the movie and the two main characters finally made it to the bedroom – and of course the bed. And at that point, Mel felt Rays hand leave hers and start to wander further… a lot further… and… she let him. Maybe it was because of the panting she was doing – and trying to keep silent. Panting that was definitely growing since his hand was now under her skirt and was pressing against her wet panties. Oh! Oh! Oh! But in the middle of her “enjoyment,” she once again remembered that sex – at least between Ray and her – had to be out for tonight. Didn’t he realize that? How could he keep doing this if he knew that? Maybe he just wanted to get her so hot and bothered that she wouldn’t hesitate at going out with him again. Damn! It was definitely working too! Well, two could play at that game!
Ray couldn’t believe his luck! She was letting him explore her in the most intimate way. Tonight! Tonight! Tonight! He couldn’t wait! And then… and then… he felt her arm moving. For a moment he thought she was going to finally stop him, but she didn’t. Her arm wandered all the way over from her lap – to his! And he felt her hand groping and rubbing at the top of his leg. And then, it was moving higher, right onto… Oh my! Oh yes! Mmmm! He couldn’t believe it, while he was groping under her skirt, her hand was now massaging him through his pants. Making him grow. Arousing him even more than he had been before. What a woman! When would this stupid movie ever end?
Okay, that last part had been pretty good, Derek realized. In fact, the whole last part of the movie seemed to be pretty good. Much better than he expected. Damn! And now he had been so touched by it that there were tears in his eyes! He cautiously rubbed them so as not to give away the fact that he was “emotionally touched.” He hoped the movie would be over soon – and he especially hoped there would be nothing else that might “affect” him like that. It was embarrassing! Damn! And… shit… was Sissy actually crying next to him? Well, he supposed that figured. The guy did want to become a woman. He now guessed there might be more to that desire than he thought.
Sissy wept softly. He couldn’t help it. Yes, he knew he was a guy – underneath – and guys don’t cry, especially not during a dumb movie. But, he still couldn’t help it. The tears just seemed to roll down his face as he tried to cry quietly. He really hoped that Derek didn’t hear him. That would be even more embarrassing. Or would it? Derek did think he was trying to become a woman, and what woman wouldn’t cry over something like this? He could even hear little sounds coming from Mel next to him. Of course, she was leaning over toward Ray so it was a bit harder to tell. But he could hear – something from over there.
Mel mewed softly. Between the emotion of the movie making her cry, and the emotion of sexual excitement from Ray, she didn’t know what she was doing. She could no longer keep “manipulating” him. She had to bring her hand back to help blot the tears falling from both eyes. And as she did, she kept pressing her legs closed over and over again against Ray’s hand, trapping it inside, then releasing it. Again, and again. Damn. She was in such a state. He would have to do this to her! And tonight… she couldn’t! She wouldn’t! Damn!
The movie ended and Ray quickly pulled his hand back before anyone could notice. He also hoped that nobody would “notice” the prominent bulge that now had to be in his pants. Damn this was a fine woman! He couldn’t wait to get her into bed! The house lights came up and he looked over at Mel. She was crying – as expected. But he also noticed that her legs were pressed awfully tightly together too. Well, that was to be expected too. Past Mel, he could see Sissy still sitting there staring at the screen, crying like a girl. Stupid! Well, he wanted to be a woman, so he supposed it was only right – now. He caught a quick glimpse of Derek looking over at Sissy. They locked eyes for just a moment and the usual male message was instantly transferred. Typical women! They’d cry over anything!
Sissy leaned over and chanced talking to Mel. “I can’t believe how much I enjoyed that,” he said as the tears still rolled down his face.
Mel almost laughed. “Me too!”

The Bet - Chapter 44 (Sunday – week 7 Part 7 of 9)

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 7 of 9)

Their meal came and Chad was pleasantly surprised to see how nice his salad was. He took some mental notes so he could do something like it at home sometime – not that he’d ever probably get to eat it. Baby food seemed to be his most likely dinner from now on.
Several times as he ate, he saw Mel glance and nod toward his glass of iced tea. He again got the message – drink, drink, drink! Ugh! And worse, since he was obviously drinking so much, the waiter kept coming by over and over again to refill his glass. He couldn’t even keep track of how much he was drinking! One thing he could tell though, was that his diapers were getting wetter and wetter. Well, hopefully, three diapers would be more than enough for tonight. Hopefully!
In the middle of their dinner, Mel started trying to make a conscious effort to involve Derek more in the conversation. But Derek’s replies seemed to be very few words and she quickly gave up. But Ray didn’t ever seem to run out of topics to talk about – with her.
They were just finishing dinner when Sissy saw Mel tapping her fingers against her lips again. He pulled his compact out of his purse and checked his face. Most of his face looked perfect, but this time there was no doubt he would have to refresh his lipstick. He had seen the lipstick stains all over his glass of tea and his fork had a fairly prominent showing of it too. He had tried to be careful with his napkin but that too was covered with red lip stains. He pulled the lipstick out and opened it. It wouldn’t have been so bad except that he saw Derek watching him intently. Under Derek’s scrutiny, he added a fresh layer of the bright red lipstick. He couldn’t believe how strange – and humiliated – he felt as he did it. Humiliated enough that he felt himself peeing in response – which only humiliated him even more.
Trying to make it seem totally normal, he finished up and put the lipstick and compact away. He saw Derek shaking his head a bit, then look away. Sissy wondered if he had done something wrong. Had he messed his lips up somehow? He opened his purse and quickly pulled his compact out to recheck his lips. Nope. As far as he could see in the tiny mirror, they looked just fine.
“You’ll have to excuse me,” Mel said to Ray. “But I need to make a quick trip to the ladies room.” She looked straight at Sissy. “Coming?”
Now Chad was more worried about his makeup than ever. He grabbed his purse and got up from the table and followed Mel toward the restrooms. Once inside, Chad didn’t quite know what to do with himself other than to check his face in the mirror. There was no way he was going to be able to use one of the toilets. While Mel went into one of the stalls, he checked his face closely. As far as he could tell, his face looked perfect – well, for what he was anyway.
Mel finally came out of the stall and checked her own face. As she pulled her own lipstick out, she said. “Put another coat of lipstick on.”
Chad was surprised, his lips definitely didn’t need it. “But…”
Mel looked quickly at him. “Don’t argue – just do it!”
Chad once again added another layer of the red lipstick. Then he put everything back in his purse again.
Mel was done with her own face before Chad was done with his. She waited till he was finished. “I want you to start talking more, especially to Derek. You two are so quiet it’s like you’re not even here!”
“But what am I supposed to say?”
“I don’t care. Just talk to him! Be the girl… and keep him happy!” She paused briefly and just looked at him for a moment. “Before we get out of here, I’m going to get Ray to dance with me one more time. Since I doubt that Derek is going to ask you, I want to hear you pleading with him to take you out on the dance floor!”
Chad’s knees almost buckled. “Dance with him?”
Mel just smiled wickedly in return and led the way back out into the restaurant.
When they got back to the table, Sissy noticed that his iced-tea glass was freshly filled once again. A never-ending source of tea – and too much liquid for his system. Talk to Derek? What the heck was he supposed to say? He knew perfectly well how Derek was feeling about this date! “We’re back,” he said cheerily to Derek as he sat down again.
“I noticed,” Derek replied as if he wasn’t very happy about it.
The waiter showed up then to ask if anyone wanted desert.
Ray looked around the table. “There’s still plenty of time before the movies start. How about it?” He looked directly at Mel. “And don’t tell me you don’t cheat on your diet at least once in a while!”
Mel laughed. “Well, maybe.” She was particularly interested because she wanted a reason to keep Sissy in the restaurant for a while longer so he could interact a bit more with Derek. She looked at Sissy. “What do you think?”
Chad was particularly surprised she would ask him – especially since he had only managed to finish half of the dinner he had gotten. Between his smaller compressed stomach and all the liquids in his system, he was lucky to have eaten that much. He smiled though as he replied, “Sounds great!” Actually, it was anything but great. He agreed with Derek. The sooner they got to a nice dark movie theater, the better!
The waiter cast another disapproving look at Sissy, then ignored him as he spoke to everyone else at the table, telling them about all the wonderful deserts they had available.
Mel was particularly interested in one of them but… “I’m not sure I can eat that much,” she complained.
“It doesn’t matter to me,” Ray replied. “Get it, and eat what you can.”
But Mel had a better idea. “Why don’t we get one and share it between the two of us?”
Ray smiled broadly at her. “I really like that idea.” He looked up at the waiter. “We’ll share one.”
The waiter nodded politely and turned to Derek.
“Nothing for me,” Derek told him.
Sissy saw Mel scowl a bit as Derek said it. He also saw her staring intently at him again – as if daring him not to order something. He was supposed to be talking to Derek. But he couldn’t! The waiter was looking at him now, waiting for his answer. The waiter didn’t look like he was smiling as much as he had when he spoke to everyone else. Oh well. Talk to Derek? “Derek,” he started, “why don’t we do the same?”
Derek looked over at him like he was crazy. “You go ahead and get what you want. I don’t want anything.”
Sissy saw Mel still staring intently at him. Then suddenly, he saw her glance her eyes quickly at Derek, then back again. Damn! She wanted him to keep trying. How? “Please?” he pleaded like a little girl to Derek.
Derek looked at him like he was even crazier. “I told you…”
“But… what could it hurt?” Sissy replied before Derek could finish.
Derek shook his head. “Oh, who cares!” He looked up at the waiter. “Bring one for us too. I probably won’t eat any of it though.”
The waiter nodded politely and was gone.
Mel seemed to be all smiles once again. “I saw a couple of deserts being brought out to some of the other tables. There’s no way I could ever eat all that! I think this is going to work out perfectly! Don’t you, Sissy?”
Chad was startled that she would even ask. “Oh… Oh yes. Perfectly!” But he was still more interested in getting out of the restaurant as soon as possible.
The musicians started in on another tune and Mel turned her head toward them. “Oh, I love that song!” She turned to Ray. “Let’s dance again!”
Her request came so fast that it caught Sissy off guard. He wasn’t ready for this! But he saw Mel staring at him as she got up out of her seat. Oh God he didn’t want to do this, but he turned to Derek. “Let’s dance,” he said.
Derek was clearly shocked. “What?”
“Let’s dance too.”
“You are crazy!”
Sissy shrugged. “Maybe… Probably… But so what? Let’s dance.”
“No!”
“Please!” Sissy pleaded.
Derek was clearly upset. “What the hell has gotten into you? I’m not dancing! At least not with you!”
Mel leaned over and spoke softly. “You’re raising your voice! Why don’t you just take her out and dance one dance, that’s all – before you bring more attention to yourself by arguing and causing a little scene.”
Derek looked up at her angrily. He wanted to yell. He wanted to argue! But, unfortunately she was probably right. He looked around at some of the other tables. A few people were looking at him. He threw his napkin angrily down at the table. “Oh, all right!” he grumbled in a much softer voice. He looked at Sissy. “Come on.”
Now it was Sissy’s turn to be shocked. He didn’t actually think that Derek would give in so quickly. And Derek clearly didn’t want to do this – just as much as he didn’t want to do it. But he got to his feet and “followed” everyone else down toward the dance floor. Fortunately, there were quite a few couples already dancing.
The music wasn’t slow, but it wasn’t fast either. Not fast enough that they could stand away from each other and just move around a bit. Everyone else on the floor seemed to be holding each other as they danced. Sissy had been aware of his super high heels with every step that he took, but the minute they touched the hard wood of the dance floor, he was more aware of them than ever. How was he supposed to do this? He couldn’t! He just couldn’t!
He and Derek just stared at each other for a moment, as if neither of them knew what to do. “Well, you wanted to do this,” Derek said as he held out his hand. Derek clearly wasn’t too pleased about it. Reluctantly, Sissy reached out his hand and allowed Derek to take it. It was his right hand that he had to reach out for Derek to take – the opposite hand he was used to using when he danced with his wife… make that ex-wife. Derek pulled him – a bit – closer… not too close. And they started trying to move to the music together. Derek was obviously trying to lead and Sissy was trying his best to follow, but he really didn’t know how. He felt so awkward and out of place.
The dance floor felt slippery under his super high heels. He had to be more aware than ever of trying to keep his balance. It was particularly hard since he was “supposed” to be moving which ever way Derek led him. He felt clumsy, clumsy, clumsy! And obviously Derek was having a harder time than usual too. “Sorry!” he said softly as he stumbled a bit and recovered his balance.
“Yeah, sure,” Derek replied noncommittally.
“Actually, this wasn’t really my idea,” Sissy told him.
“It wasn’t? You sure seemed to be awfully insistent back at the table.”
“Mel said I had to.”
Derek digested that for a moment. “Do you always do what Mel tells you to do?”
Sissy instantly thought about Robin and what she knew – now. “Usually,” he replied cautiously.
“Humph! Well, I guess she’s doing her best to make a woman out of you, but I think this part could have waited till later. A lot later!”
“I couldn’t agree more,” Sissy replied.
As they danced and talked, what they didn’t see was Ray continually snapping picture after picture with his cell phone. “You better make sure I get some of those,” Mel said to him.
“I’ll be glad to send them to you tomorrow,” Ray agreed.
The song ended and Derek was the first to leave the dance floor. Sissy had trouble keeping up with him in the heels he was wearing.
“You did good together,” Mel said to Derek and Sissy as she sat down at the table again.
“They make such a cute couple. Don’t they?” Ray added as he too sat down.
Derek rolled his eyes angrily, but made no other reply to Ray’s taunting.
Ice cream and brownies covered in chocolate sauce. Two huge bowls of it were delivered to the table, each one with two spoons already sticking out on opposite sides of the bowls. The waiter set one of them between Mel and Ray, and the other one between Derek and Sissy. The deserts looked so good, but Sissy didn’t feel much like eating any of it. He was about to reach for the spoon sticking out straight toward him when he was interrupted.
“Oh! Hey! Wait a minute,” Ray said as he got up from his seat.
Everyone looked up at him, waiting to find out what Ray wanted. Ray pulled out his cell phone. “I want a picture of this so we can all remember it!” It was the first time all night that he had brought out his phone to take a picture where Derek could see it.
“No!” Derek complained flatly, clearly not happy about it. “Don’t do it!”
“Oh come on!” Ray replied as he got the camera in the phone ready and held it up. “Lean in toward the desert a bit more,” he suggested.
“No!” Ray repeated firmly again.
“I’m going to take the picture anyway, so you might as well go along,” Ray told him. “Now lean in!”
Sissy, seeing Mel nod toward him, reluctantly leaned in – slightly – toward the elaborate dessert. Derek refused to move.
“Smile…” Ray prodded.
Derek’s jaw dropped wide open. “You can’t be serious!”
But Ray wasted no more time and snapped the picture.
“Can’t we just get out of here now?” Derek asked as Ray was sitting down.
“Why?” Ray replied. “We’ve still got plenty of time.” He happily picked up the spoon nearest him from his dessert and dug in. “Mmmm. So good!” he said.
Derek tried one bite of the dessert before sitting back and sulking about everything. Sissy ate a bit more, but not much. Ray and Mel on the other hand, ate a good bit of their dessert before Mel declared she couldn’t possibly eat another bite.
The waiter reappeared and asked if everything was going to be on one bill or separate. “The lady here and I are on one,” Ray replied.
Sissy was about to say that he would get his own, but Derek spoke up first. “I’ve got for us,” he said.
“Are you sure?” Sissy asked him. “I can pay for mine if you want.”
Derek shook his head. “No, you’re my date tonight. I’ve got it.”
“Thanks,” Sissy replied softly. He sat back and thought about it. He was the girl tonight, and even though it was only a little thing, Derek picking up the tab made him realize that fact all the more. How strange. And then he saw Mel giving him the signal to check his face again. Another layer of red lipstick had to be applied.

The Bet - Chapter 44 (Sunday – week 7 Part 6 of 9)

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 6 of 9)

Ray pulled his big Cadillac into one of the empty parking places as close as he could get to the stairs. “I guess this is it,” he said to Derek as he looked up at the apartments above. “Somehow I was expecting something a bit nicer since she’s supposed to be a lawyer.”
Derek wasn’t really the least bit interested. He wasn’t looking forward to this “date” at all. “Who cares,” he replied.
“Certainly not me,” Ray returned brightly.
They got out of the car, but before going upstairs, Ray opened the back door and pulled out a bunch of flowers along with a small white box.
“I still can’t believe you actually bought her flowers!” Derek said as Ray pushed the car door closed the again with his leg. “And what’s that, chocolates or something?”
Ray just smiled. “Or something.” He suddenly looked like he had a small problem. “Oh hey,” he said. “Can you hold this for a moment so I can lock the car?” He handed Derek the box while he pulled his keys out and locked the car. Derek tried to hand him back the box, but Ray asked him to please hold it for him till he could give Mel the flowers. Thinking nothing of it, Derek carried the box upstairs with him. He stood back while Ray knocked on the door. He really wasn’t looking forward this!

“I’ll bet that’s the guys now!” Mel said as she quickly removed the robe she had covered her dress with to keep it clean.
She took one more look at Sissy, then she smiled at Sandy who had been standing in the background watching. “Well don’t just stand there Sissy, our dates are waiting!”
Nearly shaking with dread, Chad went to the door and opened it… and got a bit of a shock. Ray was standing there, holding a bunch of flowers!
Ray was a bit surprised to see Sissy at the door. He had been expecting Mel to open it. “Uh… Is Mel here?” he asked as he stared somewhat surprised at Sissy. He was mostly surprised because Sissy looked – pretty good!
Chad started to curtsey automatically, and stopped himself halfway through. “Of course,” he replied as he stood back out of the way to let the guys in. Derek just stared at Chad as he followed Ray through the doorway. The problem was that Chad couldn’t tell anything from the look on Derek’s face. Derek didn’t smile, but at least he didn’t frown either. Finally, he saw Derek nod a bit and Chad felt a wave of relief.
“Are those for me?” Mel’s excited voice cut through the room as she saw the flowers in Ray’s hand.
“Of course,” Ray replied. “Beautiful flowers for a beautiful lady.” He bowed slightly as he held them out for Mel to take.
“Oh brother!” Sandy muttered half under her breath as she rolled her eyes.
As Mel took the flowers, she tried remember any date bringing her flowers before – and the only one she could think of was for her senior prom in high school – and that was a corsage. “They’re beautiful! Thank you.” She sniffed at the flowers. “And they smell so nice!”
Derek started to hand Ray the small white box he was still carrying. But Ray just looked at him like he didn’t understand. “What are you giving that to me for?” Ray said. “You brought that for Sissy.”
Now it was Derek’s turn to be confused. “But…”
“Just give it to her,” Ray encouraged as he pointed toward Sissy. “You don’t need my permission.
Confused, Derek automatically turned toward where he thought Sissy was standing, but Sissy had moved closer now so he could see the flowers that Mel had gotten. As Derek turned, the box hit Sissy’s arm and nearly fell out of his hand. “Oh! I’m sorry,” he said automatically.
Chad’s knees felt like they were buckling. “That’s… for me?”
Derek, still confused, started to turn back toward Ray.
“Just give it to her,” Ray said. “You brought it.”
“But I…”
“You brought something for me?” Chad asked, still trying to figure things out too.
“Um… I guess so,” Derek replied with more than a bit of annoyance. He handed the box to Sissy, then he looked back at Ray quizzically, but also with a bit of menace on his face.
Chad took the box and opened it. And got another shock. Inside, he saw a small grouping of white flowers. He removed them from the box and realized they were attached to a plastic armband. “Oh my God!” he exclaimed. “It’s a…”
“You brought her a wrist corsage!” Mel exclaimed. “How sweet!”
“But I didn’t…” Derek tried to say again.
“Well don’t just stand there, put it on her,” Mel coaxed.
“But…” Derek gave up and looked angrily at Ray again for a moment – who was smiling back broadly. Then he grabbed the flowers from Sissy. Sissy, his knees definitely shaking now, held out his left wrist and Derek pulled the plastic band wide and slipped it over Sissy’s arm. The minute he did so, a small click sounded from a few feet away as Ray quickly took a picture with his cell phone. As fast as he had pulled it out, Ray had his cell phone put away again and out of sight.
Chad stared at the flowers attached to his wrist – not believing that it had just happened. He felt so funny inside about it. Humiliated, yet… something else too. “Th… Thank you,” he stammered. Then, catching a glimpse of Mel out of the corner of his eye, he dropped a very nice curtsey and repeated, “Thank you.” When he stood up again, he noticed that Mel was smiling broader than before. Whew! He had found a way to get past that one!
“Why don’t I put those in water for you,” Sandy offered as she took the flowers from Mel. “You guys just go and have a good time tonight.”
Ray smiled broadly at Sandy. “Another beautiful lady in the apartment. I may have to think about moving here.”
Sandy rolled her eyes again. It looked like Mel was right about this guy. “Don’t bother,” she replied. “I’m spoken for.”
Ray just shrugged his shoulders as if he didn’t really care about that at all.
“You guys just go!” Sandy said, trying to ignore him. “You’re probably going to be late for dinner.”
“Good idea,” Mel replied as she headed toward the door. She glanced again up at Ray. He had brought her flowers, and she knew without a doubt that he had “arranged” for Derek to give the wrist corsage to Sissy. As she walked outside, she was reconsidering her feelings about Ray. He might be a two-timing sleaze, but he was also without a doubt very handsome. And after seeing how he had just manipulated Derek, she had a feeling that he might be more fun than she originally thought!
As Ray followed her through the door, he was immensely proud of himself for setting up Derek to give Sissy the flowers like he did. And seeing how Mel was dressed tonight, he was more determined than ever to get her alone in a “more intimate” setting.
As Sissy walked out behind Ray, he was still trying to come to grips with getting the flowers – and he still couldn’t believe he was about to go out on a date – with a guy! Derek no less! How was he supposed to do this?
And as Derek walked out, he berated himself for being such a sap and a pushover that he let Ray get him into this position in the first place! He just thanked his lucky stars that Sissy looked fairly good tonight – almost surprisingly so. At least he wasn’t dressed like a hooker again!

Mel sat with Ray in the front seat of his car while Derek and Sissy sat in the back – together. As Ray pulled the car out of the apartment project and into traffic, Derek said softly to Sissy, “Thanks for at least looking decent tonight. I appreciate it.”
“No problem,” Sissy replied, just as softly. “Actually, I’m much happier dressing like this than what I wore to the poker game.”
Derek grunted. “If nobody looks too closely, they might even think I’m out with a real woman tonight.”
Chad blushed. “Thanks,” he replied. “I’ll still be happier when it’s over.”
“Me too!”

The restaurant Ray drove them to was one of the nicer, more expensive restaurants in the city. “Isn’t this a bit much for just a dinner and movie date?” Mel asked as he parked his car.
“Not really,” Ray replied. “Besides, with the way you’re dressed, I figured you probably didn’t want to go to a movie anyway. From here we can go to a nice club somewhere and really enjoy ourselves.”
“Not on you life!” Derek called from the back. “I’m not going clubbing with Sissy as my date!”
“Now, now, be kind,” Ray replied. “I think Sissy looks pretty good tonight too.”
“Then you date him!”
“Ah, ah! A bet’s a bet! And you lost! Besides, I’m looking forward to showing off what a super dish Mel is.”
“No club!” Derek repeated firmly. “I want a nice, quiet, dark, movie theater!”
Mel put her hand on Ray’s arm. “I think it would be better if we all just went to a movie tonight like we planned. That’s all this bet was for. Maybe next time we can go somewhere else.”
“We can let Derek and Sissy go to the movie while we go someplace better,” Ray suggested to her.
Mel shook her head. She knew it was better tonight if she kept an eye on Sissy the whole time. Besides, she had some tiny little “plans” for him tonight. “Not tonight. Just a movie and that’s it.”
Ray was clearly disappointed. “Well, you went to a lot of trouble getting all dressed up just for a movie. I didn’t want to waste it.”
Mel smiled. “Think of it as giving you a reason to ask me out again.”
Ray smiled. “Now you’re talking!”
A small unintelligible grumble was heard out of Derek from the backseat.

Chad felt strange as he walked beside Derek, behind Mel and Ray, toward the door to the restaurant. His very high heels made a loud distinct clicking sound with every step he took – a lighter, more noticeable sound than Mel’s shoes made. The wrist corsage felt strange on his left arm. He had to be very aware of the flowers sticking up from it so he didn’t hurt them. His new clutch also felt strange in his other hand. It kept brushing the full skirt of his blue dress as he walked. Did he look enough like a woman tonight? Silly question. It didn’t really matter. Mel would make him go through this no matter what!
For the first time since before the guys arrived, he thought about his diapers. He had been so preoccupied that he hadn’t been noticing if he was wetting himself or not. He knew he had to be. He was sure his diapers were probably fairly wet already, but the huge bulk of all three diapers made it hard to tell anything at all. It was just another little something he would have to worry about later.
Since Sissy and Derek hung back a bit, behind Ray and Mel, the hostess didn’t really notice Sissy all that much when they walked in. As they were being led to their table, Mel noticed something that might be helpful, the waiters were going around and automatically refilling all the iced-tea glasses. She hung back a bit so she could whisper to Sissy. “Order the iced tea with your meal tonight!”
The table was square and Mel and Sissy wound up sitting across from each other. Chad was glad because it meant that Mel wouldn’t be able to lean over and whisper any more little commands to him. When the waiter came by with the menus, Ray ordered a glass of wine for everyone. Sissy looked questioningly at Mel, but Mel only brightened at the wine suggestion and said it sounded great. Sissy wasn’t sure, but he thought he heard Derek softly grumble again.
As they looked over their menus and waited for the wine, Sissy and Derek were both quiet, but Ray talked animatedly with Mel. If Chad didn’t know better, the way Ray was acting, he and Derek might not have even been there. The wine arrived, was approved by Ray, and was poured for everyone. They each took a small sip before the waiter began asking for their orders. There had been a lot of really interesting entries on the menu – all of them extremely high priced – and Sissy had been planning on ordering one of the steaks. Something like that to chew would have tasted great. He might not be able to finish it all, but it still sounded good.
The waiter started with Mel, who surprisingly ordered only one of the exotic dinner salads on the menu along with a cup of coffee. “That’s all you want?” Ray asked with some surprise. “You can have anything you want.”
Mel shook her head. “I still have to watch my figure,” she replied. Then she looked straight at Sissy as she added, “Everything on the menu sounds so good, and also so fattening!” Ray only chuckled, and said nothing else about it, but since she had been looking straight at Sissy when she said it, Sissy got the message clearly.
The waiter moved on to Sissy next, and for the first time looked at him more closely. It took him two seconds for his brain to register that there was something different about her. A moment later, total realization set in, and once he noticed it, he couldn’t help not seeing Sissy as a man dressed up like a woman. All further pretense went totally out the window when Sissy opened his mouth and spoke in his “girly” voice. Sissy ordered the same thing that Mel was having, except as Mel had dictated, he got iced tea instead of coffee. When he was done ordering, Sissy saw the waiter just staring at him for a moment. Un-approvingly? He wasn’t sure, but that’s the impression he got. Fortunately, the waiter moved on to Derek next and didn’t say anything else.
When the waiter left, Mel and Ray continued to talk while Sissy and Derek just listened. A few times, Derek and Sissy looked at each other, both of them silently acknowledging the awkwardness of the situation. Sissy kept sipping at his wine to help pass the time. As he did so, he couldn’t help but notice the red lipstick stain on the rim of his glass. Each time he picked it up, he tried to drink from the same spot so as not to spread the stain any further.
A few minutes after the waiter left, unexpected music filled the room. From where they all sat, they could just see two musicians up on a stage providing soft entertaining music. There was a woman playing an electronic keyboard, and a man with her who was accompanying her with a string bass. They both sang and together and they sounded surprisingly good. Sissy was glad to see the musicians. It gave him something else to concentrate on instead of the strange situation he was in. Not only that, but maybe everyone else in the restaurant would be paying more attention to the musicians too – and less attention to him. After a few minutes, Sissy noticed one of the couples closer to the musicians get up from their table and start dancing. He smiled. How nice. They were quickly joined by another couple from another table.
Sissy’s glass of wine was about three quarters done when he saw Mel looking at him again. Ray was talking and Mel appeared to be listening, but Sissy saw her rest her elbows on the table and her chin in her hands for a moment. Ray obviously thought nothing of it. But when Mel began tapping her finger against her own lips while looking at Sissy, Sissy got the message. Even sitting across the table from him, she was finding little ways to give him orders! He opened his purse and pulled out his compact and checked his face in the mirror. He decided everything still looked good, including his lipstick, so he put the compact away again. He saw Mel smile briefly at him. As far as he could tell, Derek hardly noticed – or at least he made no reaction. And Ray was still talking to Mel and probably never even saw him do it. Sissy picked up his wine glass and emptied it!
“Shall we dance?”
Mel was startled by the sudden suggestion. “Here? Now?”
“Why not?” Ray replied. “There’s plenty of room in front of where the band is playing.”
Mel looked and saw three or four couples dancing now. “Why not?” she suddenly decided and got up from her seat.
Sissy saw Ray look briefly back at Derek as if taunting him. Derek’s face didn’t look all that happy about it as he watched them heading toward the music. They were alone in the restaurant – together. Awkward! Awkward! Awkward!
Not wanting to watch Ray dancing with Mel, which would only be like him rubbing things in, Derek looked away from the dancers, which really left him only Sissy to look at.
“So far, so good,” Sissy said, trying to fill the awkward silence.
Derek grunted, but nodded his head. “Yeah, so far.”
Wanting to continue the conversation, Sissy added, “It’s a nice place. I’ve never been here before.”
Derek shrugged. “I’ve been a few times, but it’s been a while.”
Sissy didn’t know why, but he suddenly thought about Robin. Obviously, she hadn’t told anyone yet – or at least the word hadn’t gotten to Derek yet. “I’m more worried about tomorrow,” he said.
“Tomorrow?”
“At work. What’s everyone going to be saying?”
For the first time, Derek smiled. “I’m not going to have to worry about that, because I’m not going to be there. I’ll be flying out early tomorrow morning.”
“You’re lucky!”
Derek nodded. “About that anyway.”
“I’ll have to put up with all the women asking me tons of dumb questions.”
“You’re the one who wanted to be a woman! Don’t complain to me about that!”
Chad considered telling him how wrong he was, but all he could really do in the situation was to smile and say, “I guess your right.”
“You are getting better at it,” Derek said.
Chad felt himself blushing slightly. “Thanks. I’m trying.”
“But you’ve still got a long way to go!”
That kind of knocked the wind out of Chad a little. “Like I said, I’m trying.”
As they talked, they didn’t see Ray and Mel coming back from the dance floor and stopping a short distance away. Ray pulled out his cell phone again and took another quick picture as Mel giggled.
Derek and Sissy were saved from further conversation as Mel and Ray came back and sat down again. And once again Ray dominated the conversation – with Mel. Two minutes later, Mel was tapping her lips and Chad had to check his makeup again. Nothing had changed! How could it?

The Bet - Chapter 44 (Sunday – week 7 Part 5 of 9)

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 5 of 9)

Chad spent the afternoon thoroughly cleaning the apartment, doing laundry, and drinking more bottles than ever before. He was going crazy trying to get his diaper leaking faster. He had to! Mel had decided that she would only give him five swats from her stick for each minute over now, but if it looked like that wasn’t going to be enough, then she had no trouble raising it to ten.
While he was working, Mel was working too, but not on her computer. She had made tea yesterday, but he was going through the bottles so fast now that she had to make more to keep up. Not that she was that worried about the tea because he was also drinking a lot of water too.
As they both stayed busy, Mel kept her stick nearby – always. Whenever she thought he was least expecting it, she would order him to show his diaper, which always resulted in her giving him a quick stinging swat with her stick. And over and over again she pressed him to curtsey constantly. If he didn’t, then that brought another instant stinging swat.
Chad was getting more and more paranoid all afternoon. He kept a constant watch for Mel out of the corner of his eye. Just to avoid getting hit more, he started curtseying every time he saw her turn to him. She was already forcing him to curtsey every time he opened his mouth. And now he was doing it every time a conversation ended. It was very bothersome – to say the least.
He was fortunate to have his next diaper leaking on time. But he was only halfway through his next time limit when the stupid suppository, that he only thought Mel had put up inside of him, decided to go to work. Instead of changing him there, Mel sent him back to his own apartment to shower and make sure he was perfectly shaved all over before coming back again in a clean diaper. She wanted him freshly cleaned and shaved because the time to start getting ready for their date was getting closer.
When Chad came back, still in his maid’s uniform, he began worrying about what Mel intended as far as his diaper leaking later – during their date. Even if he got his current diaper leaking on time, which he was fairly sure he would, then what about the next one? By his estimation, the next one would have to be leaking sometime during the date. Surely she couldn’t expect him to have a leaky diaper then – could she? But then he remembered how obsessed she seemed to be about it lately – obsessed enough that he had been having trouble out in public on several occasions. And not always just a little trouble, at times it had been major trouble! So what was she expecting him to do tonight? He just couldn’t see himself having to change his diaper in front of Derek… or Ray either! If it came to that, he was sure he’d rather receive any punishment she might dish out, just so they wouldn’t know! If they didn’t know already. But that was another problem he had to worry about. Hopefully, Robin hadn’t told anyone yet. Hopefully.
So what did Mel expect for tonight? The thought bothered him so much that he finally approached her – and curtseyed as well as he was able to before he spoke. “Mistress…”
Mel looked up from her laptop. “Are you leaking?”
He curtseyed. “No, Mistress.”
“Show me your diaper!”
As fast as Chad could, he grabbed the skirt of his maid’s dress and pulled it up high. But by the time it was fully up, she was already coming out of her chair with her stick. He got a sharp slap on the side of his bare leg as punishment for being too slow before she sat down again.
“If you’re not leaking, then why are you bothering me?” she asked.
Chad pulled his dress down again and smoothed the skirt slightly before dropping yet another curtsey. “I… I was wondering about later,” he stammered.”
Mel was confused. “Later? We’re going out on a date later. What are you worried about?”
His curtsey was almost automatic. “My diaper leaking.”
“You’re worried you won’t make it?” Mel actually smiled. “Good! I’m glad you’re worried about it. Just make sure you get plenty to drink as often as you can tonight and… hopefully… you’ll be just fine. The restaurant really shouldn’t be much of a problem, but the movie theater… Maybe you should get an extra large drink before the movie starts.” She smiled broader. “In fact, I’m going to insist on it! Maybe Derek will even buy it for you!”
Chad actually shuddered at the thought. He almost spoke without curtseying again, but stopped himself long enough to complete the act just in time. “No, Mistress. That’s not what I meant. What happens when my diaper does leak?”
Mel’s face was still all smiles. “I’m so glad you’re actually planning on it. That makes me very happy! We’ll just have to wait and see what happens then… and deal with it… or not.”
Deal with it… or not? He couldn’t believe it. She was actually planning on him having a leaking diaper – during their date! He couldn’t! He just couldn’t! But… how was he going to prevent it? He was drinking so much already – and had been all day long. His system was so overloaded with fluids that even if he never drank another drop all night, he’d still probably be peeing constantly. And with the amount of time they were probably going to be gone, there was going to be no way to avoid it!” He actually shuddered at the thought as he dropped another curtsey and turned away from her in shock. He couldn’t believe it! He just couldn’t believe it! But what choice was he going to have? And then he realized that he had been set up. She had been pushing him extra hard all day, making him drink far more than ever. No matter what he did, there was no way he could avoid going out tonight and not having his diaper leak – probably over and over again. What were Derek and Ray going to think? What was he going to do? It was going to be… a disaster!
Mel continued to smile as she watched him walking away – obviously in shock. The funny thing was though, that he had asked the wrong question! She almost laughed. She was having so much fun today with him. Obviously, she was in a really wicked mood as far as Sissy was concerned. And she didn’t see any reason at all to stop.
An hour later, Chad looked up as he was folding laundry and saw Mel heading into her bedroom. What surprised him was that she closed the door behind her and he heard the faint sounds of her locking it too. He glanced at the clock and guessed that she was probably going in to get ready for tonight. Was he really going out on a date tonight? With Derek? As a girl? The thought still sent shudders down his spine. And what about his diaper leaking? He had purposely cut back on the amount he was drinking, but he was still peeing an awful lot and his diaper was getting awfully wet – already. Too soon in fact! He figured that it would be better if he was changed just before they left in order to put off leaking as long as possible. But if his diaper leaked too soon now, then what was going to happen?
He finished folding the clothes and looked around. He had a few things that he had just folded that needed to be put away in Mel’s room, but he couldn’t get there. The apartment was already spotless and even the kitchen was back in order again – the new order he had given it. So now what was he supposed to do? He was startled as Mel’s bedroom door suddenly opened and she walked out wearing only a full slip and headed toward the bathroom.
Mel paused on her way to the bathroom and saw Sissy just standing there near the laundry. But he wasn’t drinking anything and he didn’t appear to be working. “Show me your diaper!” she commanded quickly.
Chad raced to get his skirt up on time. But he knew before he started that he had failed. He especially knew it when he saw her hurrying to find her stick. A moment later, he was enduring not just one, but two hard stinging slaps from it. “What are you doing?” Mel asked. “I haven’t seen you drinking a bottle in a while now.”
Chad curtseyed. “I just finished folding the laundry,” he replied.
“And how about your bottle? You’re not leaking yet.”
Again he curtseyed. “I still have plenty of time,” he replied.
“I don’t care! Go get another bottle. What else are you doing?” she asked.
Chad curtseyed. “I just finished here,” he replied.
“Then get your bottle and get up on your perch and stay there till I’m ready for you. And your bottle better be long gone before then!” She glanced at the clock again. “We don’t’ have much time before we have to start getting you ready!” She saw him just stare at her for a moment. “Now go!” she commanded with a half-hearted swing of her stick that again caught him on the side of his leg. “And if you start leaking while you’re on that thing, just stay there and don’t bother me!”
Chad turned and started to hurry away, only to feel her stick hitting him one more time.
“You forgot to curtsey again before you left!” she yelled angrily.
Chad quickly dropped yet another curtsey, then hurried to the kitchen to get another bottle – of water this time. Mel was already in the bathroom by the time he emerged from the kitchen, bottle in hand. He was glad to see her gone! He reluctantly climbed up onto his perch and carefully brought the bottle up to his mouth. With his neck bent back and his body leaning into the corner, he started drinking again. Another bottle! How was he going to keep himself from leaking during the date? It was going to be impossible! He suddenly felt himself peeing again, but it had been such a short time since he had climbed up onto his perch that it held very little interest for him this time.
Having no other stimulation to occupy his mind, his thoughts naturally tuned toward the upcoming date. He was going as the girl this time. He was going out with Derek – his friend! At some point – possibly more than one time before they got back, his diaper was going to start leaking. And worst of all, before the date ended, he was supposed to kiss Derek goodnight – passionately! He couldn’t! He just couldn’t!

Mel left her dress and shoes off, but otherwise she was all ready. She walked out of her bedroom and straight over toward Sissy who was still in the corner on his perch. The empty bottle was still in his hand and down by his side where it belonged. She looked closely at the bottom of his diaper – it looked like it had just started leaking. Perfect!
Without saying a word to him, she left him and found her phone and punched in a number. “Hi Sandy? I just have to run and get him a few things from his apartment. If you want to come over in about fifteen minutes, we should be ready for you then… Great!”
Ignoring Chad completely, she threw a robe on over her slip, grabbed her keys out of her purse, and went out the door. The walk to his apartment was short and she was inside in only a minute. She went straight to his cardboard dresser where she got the few things she wanted. She was back home again a few minutes later. As far as she could see, he hadn’t moved. Actually, this time, she really didn’t care.
“Okay, Sissy. Let’s start getting you ready.”
Chad gratefully climbed off of his perch and stretched his ankles and legs for a moment. Then he went quickly into the kitchen to deposit his now empty baby bottle. He found Mel waiting for him in her bathroom – with another diaper for him. He wasn’t all that happy to see only one diaper in her hand again.
Mel had him remove his maid’s dress before she expertly removed his soggy diaper and did her best to clean him up. Then she added a layer of baby powder and smoothed it all over his front and backside. Then she finally pinned the fresh diaper in place. “An hour and forty-five minutes, Sissy,” she told him.
Chad still couldn’t believe it. What was he going to do? Especially since he realized he was peeing yet again. His dry diapers never stayed that way very long anymore! An hour and forty-five minutes! They would be in the middle of their date then. What would they be doing? Where would they be? He only hoped that they would be inside the movie theatre by then so that when it happened, nobody could see it in the dark. But what about after the movie – when his leaking would be much worse and that much more obvious? It was not a happy subject to dwell on.
“Sit on the toilet there,” Mel said as she pointed to it, “so I can do your hair.”
Chad was a bit surprised by that request, although it was only practical. It’s just that… he hadn’t done anything with a toilet – other than cleaning it – for a long time now. He put the lid down that Mel always kept up, and carefully lowered his already wet diapered bottom down on top of it.
Mel attacked his hair with her brush. It really wasn’t too bad at all, but she grabbed her curling iron and started reworking it anyway. Before she finished, she heard Sandy at the door. She left Sissy right where he was, holding the hot curling iron in place, and went to open the door. “Your timing is perfect,” she told Sandy as she let her inside.
Sandy came inside with a bag full of makeup. “Where is he?” she asked as she looked around.
“In the bathroom – sitting on the toilet.”
Sandy was startled. “He’s what?”
Mel laughed. “Don’t worry. He can’t do anything there. I’m just working on his hair.”
Sandy was a bit relieved. For a minute there she had thought that Mel might have let him out of his diapers! “So do you think he’ll need the smudge proof stuff this time?” she asked.
Mel considered that for a minute, then smiled. “No. In fact, I’d like him to be fussing with his makeup as much as possible tonight. So… lots of lipstick this time. And something that he can reapply often.”
Sandy giggled. “No problem!”
While Mel worked on his hair, Chad had to endure Sandy working on his face. Between the two of them, he didn’t know which way to move his head or where to look – or not look. He soon felt himself peeing yet again – which was really strange because for once he was sitting on the toilet while it happened. Unfortunately, he might as well have been sitting anywhere else, because with his diaper on, there was no place else for the pee to go. At the rate he was peeing now, how far into their date would he be before he started leaking?
Mel finished with his hair and sprayed it lightly with hairspray while Sandy stood back to check to see what still needed to be done. When Mel had finished, Sandy grabbed the lipstick one more time and put another coat on top of the two coats that were already there. She stood back again to eye him critically. Finally, she nodded. “There! I think that should do it!”
Mel was pleased. “Perfect!” she declared.
“Can I look?” Chad asked hesitantly from his seat on the toilet.
“Sure, have a look,” Mel replied.
Chad got up from where he was sitting and turned to look at his face in the mirror. He was actually a bit afraid to at first, but when he got there, he got a pleasant surprise, he looked… great! Well, fairly great anyway. As good a job as Sandy had done, when you looked close, there was no doubt at all that underneath it all he was still a guy. But still… he didn’t think he had ever looked this good before. Or… this sexy either. If you could call him that. Maybe it was just the makeup. With the bright red lipstick she had used, he thought he looked more like a girl heading out to a club somewhere than just to a movie.
Mel picked up the lipstick that Sandy had used on him a moment before. “Take a good look, because now you’ve got to keep it looking just like that, all night. I don’t want to see anything the least bit smudged or out of place – especially your lipstick. I want you checking it often, and refreshing it almost every time!”
Chad’s eyes went wide as he felt a tiny bit of stirring to his sexual excitement. He took the tube of lipstick that Mel was holding out for him. Fortunately, he didn’t have to use it yet.
“Are you ready to put his dress on him?” Sandy asked.
Mel stepped out of the bathroom to check the clock, then turned back again. “No, let’s wait a few minutes. There’s still almost half an hour till they’re supposed to get here.” She looked directly at Chad. “Plenty of time for you to have one more bottle!”
Chad nearly died. He was peeing so much now that he didn’t know what he was going to do during the date. He started out of the bathroom, but was stopped by Mel’s angry voice. “Sissy! You didn’t curtsey again!” She quickly looked around for her stick, but it was nowhere near. Instead, in the heat of the moment, she reached out to slap him, but stopped herself just in time. She didn’t want to mess up the makeup job that Sandy had so artfully done. “Remind me to punish you for it later! Now go get another bottle and get back up on your perch!” This time, Chad curtseyed before he hurried out – while Sandy giggled at him.
While Chad stood up on his perch in the corner, “reluctantly” drinking yet another bottle of water, Mel finally put her dress and shoes on to finish getting ready. Sandy appropriately ooed and ahd over it. But as soon as Mel was ready, she put her robe back on over her dress again to keep it clean. “Sissy…” she called. “Are you done with that bottle yet?”
“Almost, Mistress,” Chad called back from his corner.
“Well, we can’t wait any longer. You can finish it later. Get yourself over here right now.”
Chad gratefully pulled himself out of the corner and set his bottle down next to his perch. He hurried over to Mel and curtseyed. Mel pulled him into the bathroom again and had him lay down on the floor. While Chad was laying down, Mel got out three more disposable diapers and started preparing them while Sandy looked on. Chad was elated to see them. She wasn’t going to send him out in only one diaper after all! A few minutes later, Chad was once again happily well protected with three full layers of disposable diapers on him. Then Mel handed him one of the all-in-one girdles he wore to work every day, followed by a pair of pantyhose. A few minutes later, Chad was pulling his new blue dress on and fastening his new shoes on his feet.
Mel grabbed the perfume she had brought back from his apartment and sprayed a tiny dose on his neck and wrists. “There,” she teased, “Now Derek will find you irresistible!”
Sandy and Mel together loaded his new clutch purse for him with everything he should need, but instead of putting the tube of lipstick in it, she handed it to Sissy. “Your lips are all smeared from the bottle you just drank,” she told him. “Fix it!”
Chad curtseyed before he took the lipstick and hurried to the bathroom where he touched up his lips – which seemed to be already coated with more lipstick than he ever used.
Mel followed him back into the bathroom to watch. “Don’t forget,” she reminded him as he applied a fresh coat, “I want to see you checking your face and touching up your makeup all night!”
Chad half curtseyed again as he worked. “Yes, Mistress.”
Mel stared at his reflection in the mirror. “I guess tonight is going to be a bit different for you.”
Chad bent his knees a bit as he worked on his lips. “In what way?”
“Tonight… Tonight I want you to try to be as much of a woman as you can. Use your girly voice, don’t call me Mistress in front of your friends. Try to enjoy yourself. Forget you were ever a guy. You’re not anymore. Be the girl!”
Chad’s eyes went wide as he looked back at her in the mirror. He turned toward her and curtseyed. “I don’t know if I can,” he said nervously.
“Try,” Mel replied. She smiled at him. “You look very nice tonight.”
Chad curtseyed more nicely this time. “Thank you, Mistress.”
Mel smiled. “I really do love seeing you curtsy like that.” A sudden thought struck her. “In fact… I’ll bet Derek would like to see it too.”
Chad was horrified. Curtsey for Derek?
But Mel wasn’t done yet. “At least once tonight, I think you should curtsey nicely for Derek. And make sure I see you do it!”
The horror over that command was still registering when someone knocked on the door!
Mel smiled. “I’ll bet that’s the guys now!”

The Bet - Chapter 44 (Sunday – week 7 Part 4 of 9)

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 4 of 9)

He had only been six minutes late. Six minutes! That’s all. If she had kept his time limit at two hours he would have made it easily! But an hour and forty five minutes? It was too short! Sometimes he could make it, but sometimes his diapers could be awfully stubborn and decide not to leak in time. It wasn’t his fault, it was the diapers! The diapers and… the too short time limit. Maybe she just liked beating him? Maybe.
Chad finished spreading the diapers out on the floor to protect it just as Mel came walking up, her stick still in her hand. Not taking his eyes off of the stick, he curtseyed nervously, even though he didn’t have anything to say. He wasn’t looking forward to this – even though it wasn’t all that many swats that he would be getting.
Mel smiled at his nervous curtsey, even though he didn’t say anything. As far as she was concerned, the more he curtseyed, the better – reason or not. “Okay, Sissy. Get that diaper off. Let’s get this over with.”
Chad wasn’t sure if he needed to curtsey or not. He hesitated, than curtseyed – just in case. He pulled the skirt of his dress up high again and left it there. Then he started unfastening his diaper. As usual, it was soaked as it dropped heavily to the floor. But then, they were always soaked – thoroughly. He hated having to do it, but seeing Mel standing there waiting with her stick in her hands, he got into position, leaning up against the back of the chair. Hating this part even more, he braced himself and purposely raised his naked butt up as high as he could, making it an inviting target for her wicked stick. Unfortunately, he didn’t have to wait very long. He heard the swoosh of the stick just a bare second before he felt the stinging pain erupt across his backside. Ouch! That hurt! It was all he could do to keep his hands off of it and not rub it. He stood up and curtseyed. “Thank you, Mistress,” he said in his sissy voice. Then he got back into position for the next one. Ugh!
“You know, Sissy,” Mel said as she waited for him to get ready again. “I wonder if we’re being too easy on you.” She saw him raise his backside again. She swung her stick – hard! Smack! She had to wait till he stood up and thanked her.
Chad didn’t know what to think. Too easy? In what way? Not in any way that he could see. He curtseyed. “Thank you, Mistress.”
Mel watched him getting back into place. His backside already bore the distinct red marks from where she had hit him. “I’m thinking that one little stroke from my yardstick is not nearly enough to give you more incentive to try harder.” Swoosh… Smack!
It was all Chad could do to not cry out in pain as the stick made its stinging impression on his already flaming backside. Little stroke? That hadn’t been a little stroke at all! Not one bit. It hurt! What was she thinking – not enough incentive? “Thank you, Mistress,” he said in a rather husky sissy voice – after his curtsey. He was already fighting back the tears.
Mel saw the look of alarm on his face as he thanked her, then started getting into position again. Good. “I’m thinking that we need to double the number of strokes… No… I doubt that would be enough either.”
Chad was already panicking. Double? And even that wasn’t going to be enough? What was he going to do? It was already too much! Swoosh… Smack! Ouch!
“I wonder if five would be enough,” Mel mused out loud. She clearly saw the panic in his face as he stood up and curtseyed. His thank-you sounded even worse than usual since he actually stuttered as he tried to say it. “Five smacks from my stick for each minute that you’re late.” She watched as he got back into place again. “That would be… Let me see… For the six minutes this time… Thirty swats!” Swoosh… Smack!
Chad barely had time to register thirty swats before the stinging pain once again erupted on his tender backside. Five swats for each minute? It was way, way too much! He curtseyed again. “Thank you, Mistress,” he blubbered. But his thoughts were more on trying to contemplate five strokes for each minute over. Thirty swats?
But Mel was still musing things over to herself. Only she was doing it out loud. “Or maybe ten strokes for each minute would be better?” She paused as if to consider that idea. “Yes! I really like that number better.”
Panic was setting in full force inside of Chad as he raised his backside up for her to hit… which she did immediately. Swoosh… Smack! He wasn’t sure which registered worse, ten strokes for each minute, or the pain from her latest blow. He stood and curtseyed, noting that the tears were starting to leak out of his eyes. “Thank you, Mistress.”
Mel paused to look at him seriously. “By my count, that was six strokes already Sissy. What’s the rule? What didn’t you do?”
It took Chad a moment to realize what she was talking about. Unfortunately, he remembered all too soon. He almost spoke without curtseying again. But fortunately, he remembered just in time. “I didn’t pee during my punishment, Mistress. Five more strokes.”
Mel smiled. “That’s right! And don’t forget, I owe you four more for not curtseying earlier too.”
Four more too? That would make a total of… fifteen! And there was nothing he could do about it. He curtseyed before he said, “Yes, Mistress.”
Mel watched him getting back into place again, ready for his next set of swats. “I think I like this rule,” she said before delivering the next blow. Swoosh… Smack! “Five swats for not peeing during your punishment. Actually, I think that’s very reasonable of me. Don’t you?”
Chad curtseyed. “Yes, Mistress,” he stammered. “Thank you, Mistress,” he also squeaked out before getting back into place again.
Mel smiled. “Now… Now we just have to figure out, what should be the proper punishment for each minute that you go over. Five swats… or ten.” Swoosh… Smack!
By the time that Mel had delivered all fifteen strokes, Chad was crying uncontrollably. But the bigger issue on his mind was whether Mel would decide on five strokes for each minute over, or ten. She had only given him fifteen strokes this time and his backside was on fire. He didn’t need any more incentive. He was already doing everything he could to get his diapers to leak. What more could he possibly do? He stood up after her last stroke and curtseyed. He thanked her – sort of… What came out of his mouth wasn’t exactly intelligible. And then he realized that he was peeing again… way too late. He wanted to cry all over again just for that!

Chad stared at the corner – seeing… nothing. His backside still stung, but only a bit. It seemed to hurt worse because before she had put another diaper on him, she had stuck another miserable suppository up inside of him. Yuck! Just once he’d like to go without one! Just once!
He knew that Mel was in the kitchen eating the salad he had made for her. He had finished making it after she had diapered him again. And his own lunch? His lunch was already sitting out on the counter, waiting for him… sort of. Mel had made him pick out what he wanted to eat for lunch – from the baby food cabinet only – and put it all the jars out on the counter so she could approve them. By having to pick it out himself, he felt a bit like she was trying to make him humiliate himself.
And now… now he was stuck back in his corner again. His wonderful little corner… not! Stuck standing on his stupid “perch.” Perched… like a bird in a cage. Only there was no cage around him, just two walls that he couldn’t move away from. He guessed the walls formed a cage of sorts. He certainly couldn’t get away from them. Stuck!
There were so many other things he could be doing! Useful things! Necessary things! Like laundry! He was still way behind with that. And cleaning… cleaning anything and everything. But instead, here he was, put away. Out of sight and out of mind. Not allowed to move a muscle. Not allowed to make a sound. Not allowed to see anything. He supposed he was lucky that she didn’t put earplugs in his ears so he couldn’t hear either. He wasn’t about to mention that because it might give her ideas.
Stuck, where the only stimulation he had was what his body felt. Like how much his legs ached after a while. Or how much his toes ached after a while. Or… Oh! He was peeing again! Wonderful! And then the feeling was gone. He supposed that it was pretty bad when the most exciting thing you can possibly feel is when you wet yourself – and you’re looking forward to it! He wished he could feel it more often. Of course, if he did, then maybe his diapers would leak sooner. That would be a good thing. He knew that Mel would certainly like that. But he seriously doubted that his body was capable of peeing more often than he was now.
What was he supposed to do if she decided to raise the punishment level for not leaking on time? He was already doing everything possible. It was already killing him. He didn’t really want to contemplate such a thing. It would be bad! Very bad!

Mel watched him in his corner as she finished her lunch. He hadn’t moved a muscle – again – as far as she could see anyway. Amazing! Just what she wanted, but sometimes she wondered how he could do it.
She wondered what he thought about too as he stood there. With nothing else to look at but those two walls, thinking was about all he could really do. She’d probably never know what he thought about. Just like, hopefully, he would never know that she had once again faked putting the suppository up inside of him. As far as she could tell, it hadn’t made a bit of difference yet whether he knew or not. So far, the results had been the same. But would it continue to be the same? According to her plan, things were about to get more questionable as far as that went.
She finished her lunch and got up from the table. There were still things from the cabinets that needed to be put away, but not a lot of things. She wandered over and took a good look at what baby food he had picked out for himself. There were two jars of sweet-potatoes and squash – mixed together. Who came up with that combination? She picked up a brown jar. Beef! Yuck! Even in the jar it looked awful. She picked up a third jar. Strawberries. Well, that didn’t sound too bad. She wondered how it tasted. There was a second jar of strawberries as well and another jar of the brown beef mush. Six jars in all. While it sounded like a lot, she knew that for an adult it was really very little.
After glancing at him in his corner again, she began opening the jars and putting it all out on the plate for him. She got his bib out and took the tray off of his highchair. She was just about to call him to get his lunch when her phone rang. She hurried to answer it. “Hello?”
“Hi Mel.”
“Hi Sandy! What’s happening?”
“I just called to see if there has been any more fallout from what happened with his friend Robin yesterday.”
“Not yet. We won’t know till tomorrow.”
“Oh,” Sandy replied. “I don’t know if that’s good or bad.”
“Good – for now. We’ll take things as they come and deal with them.”
“That’s good. Say, are you two still going on that date tonight?”
“You bet! It should be lots of fun.”
“So what are you wearing?”
Mel laughed. “I bought three dresses yesterday. I still haven’t made up my mind as to which one to wear. Want to come over and help me pick one out?”
“You bet! I’ll be there in a few minutes!”
Mel hung up her phone and looked back at Sissy, still standing perfectly still in the corner. “Sissy… It’s lunch time. Get yourself into your highchair.”
Chad gratefully pulled himself off of his perch and out of the corner. He took a moment to flex his ankles so he could walk, then he headed for the kitchen where Mel was already waiting with the tray from his highchair in her hands. He got up into the chair and she fastened the tray in front of him, securing him into the chair. A bib followed. Then she brought over his plastic plate filled with all the mushy baby food and handed him a tiny baby spoon to eat it with. Finally, she pulled another baby bottle out of the refrigerator and set that on the tray too. Chad was already digging into the colorful mush in front of him and trying to eat it as best as he could. He had taken only two spoonfuls though when he heard someone at the door. He momentarily panicked before he remembered that Sandy was coming over.
A minute later, Mel ushered Sandy into the kitchen where he was eating. He saw her smile broadly at the sight of him. He kept on eating, shoving his little baby spoon into a pile of mush and carefully bringing it to his mouth. He was definitely getting much better at this. He didn’t think he had spilled any of it yet.
Without asking, Sandy walked over to him and pulled the spoon right out of his hand. She didn’t say anything to him as she walked over and set it in the sink. “He doesn’t really need that,” she said to Mel. “Babies like to use their hands more than the spoon. They like touching things.”
Mel just laughed. “Really? He’ll be such a mess!”
Sandy was grinning broadly as she mockingly shrugged her shoulders. “Aren’t they always a mess?”
Mel just shook her head and laughed again.
“Now where are those dresses?” Sandy asked, totally ignoring Chad who sat dumbfounded in his chair.
Mel and Sandy looked at all the dresses, including the blue one that Sissy was going to be wearing. It took a while, but they finally narrowed the selection down to one – that would go well with Mel’s wild new leopard print shoes. As Mel was putting the dresses back in her crowded closet, Sandy asked. “What about after your date, when you get home?”
“What do you mean?”
“I mean… You said these guys are both really good looking…”
Mel smiled. “Oh they are! Total hunks! Both of them!”
“So, I mean… it’s only natural that you’re going to want to… spend the night with one of them… or both if you like.”
Mel smiled and shook her head. “Not tonight. Besides, the guy who’s supposed to be my date tonight is really a two-timing son-of-a… you know what! And I’ve also got Sissy to worry about.”
“Sissy? Why? Just send him home… or… I can babysit if you like.”
Mel was a bit surprised. “Babysit? It’s probably going to be late when we get back.”
Sandy shrugged. “I don’t care. I can do it if you want. And what’s your big hang-up over this guy being a louse or not? I mean, you weren’t planning on marrying him, were you?”
Mel was shocked. “Heaven forbid! I was just so totally drunk when I suggested the date in the first place. If I wasn’t then this date wouldn’t be happening at all.”
“So still, what’s your problem? Get yourself a little fun. Let him tickle your bones.”
Mel shook her head. “Not tonight,” she sighed.
Sandy shook her head too. “Well, like I said, anytime you need me to babysit, just call.”
Mel smiled. “It won’t happen! But thanks for the offer anyway. I’ll let you know if I need you.” Mel did think of one other thing though, “Um… By the way… Would you like to come by later and help get him ready for tonight? You can do his makeup a whole lot better than I can, and I want him to look really good for tonight.”
“Well, I’d rather make him up to look like a baby… but I’d absolutely love to!”
As soon as Sandy left, Mel walked back into the kitchen and got a small shock. Sissy had baby food wiped all over everything! He was a total mess… as was his bib, highchair, and everything else within reach. “Did any of that food actually get into your mouth?” she asked.
Chad only shrugged. “Some!”
Mel shook her head. “Sandy may like you eating without the spoon, but I think we can do without this mess!”