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

The Bet
by Karen Singer

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

Chad felt fairly happy riding in Mel’s car to their usual Thursday evening restaurant. He felt happy because for once, Mel hadn’t had him wear only one diaper after work. So he was dressed in his usual two diapers, with plastic panties, underneath his usual waist cincher, overly tight girdle, and of course today’s blue pantyhose. He felt much more secure and comfortable with all the extra protection. It also made him happy because for once, Mel wouldn’t be forcing him to try to get his diaper leaking within her two-hour time limit. It felt like a night off! Almost a vacation!
And better still, not only did he not have to worry about cooking dinner, but tonight was relaxation therapy night – the one single best thing in his life now. He always came out of those sessions with Gloria feeling absolutely great!
He momentarily thought back to last Monday when Mel had made him go into Gloria’s office dressed like a super sissy – and acting like one. Gloria had laughed hysterically. But the question now was, how would she treat him tonight? He’d just have to wait and see. In the meantime, he had dinner to look forward to with Mel.
Mel parked the car and Chad started to get out, but Mel stopped him. “Wait a minute.” Chad looked back to her. “Grab one of your empty bottles and take it in with you.”
Chad wanted to protest. Last week she hadn’t made him use a baby bottle in this restaurant – and they had both had a really nice dinner. But the look on Mel’s face made him hold his tongue. Reluctantly, he dug one of his empty bottles out of his diaper bag and started to put it into his purse.
“Just hold it in your hand,” she instructed.
Chad’s eyes went wide with surprise. He wanted to protest again, but the look on Mel’s face told him that protesting would be useless. Feeling more foolish than usual, he grabbed his purse in one hand and the bottle in his other hand and got out of the car. He always hated hearing the finality of the car locks closing behind him. He wished his skirt was a bit fuller as he followed Mel toward the restaurant entrance. Maybe then he could hide the baby bottle in his hand inside the folds of his skirt. But unfortunately, that wasn’t going to happen either.
They had been to this restaurant quite a few times now. Chad couldn’t help but notice the interested looks he got from most of the staff as they went in. “Just two?” the hostess asked.
“Yes, please,” Mel answered. Chad was glad that she was the one doing the talking tonight. He would have hated using his sissy voice here. The hostess started to pick up two menus, but Mel quickly stopped her. “Can we have one child’s menu, please?”
The hostess looked around. “Still just the two of you?”
“That’s right. The child’s menu is for her.”
Chad felt very foolish as the hostess smiled and looked him over once again. Did she notice the baby bottle he held in his hand? Probably. He watched as she put one of the regular menus back then picked up a child’s menu. She then picked up a box of crayons and held them up for Mel to see.
“Definitely!” Mel replied to the obvious question. Chad felt more foolish than ever as he followed Mel and the hostess back to one of the booths. The hostess set the adult menu on one side of the table and the child’s menu with the crayons on the other side. Chad didn’t have to ask which side he was supposed to sit at.
The hostess waited as Mel and Chad sat down. Chad set his purse on the seat next to him, but the baby bottle… He couldn’t help but notice that the hostess was watching closely as he set it down on the table, as far back from the edge as possible – where he hoped it would be less visible.
“Your waitress will be right with you,” she said just before she departed.
“Give me that thing,” Mel said as she pointed toward his bottle. Chad pushed it across the table to her. Mel searched through her purse and finally pulled out a twenty dollar bill. She set the money near the edge of the table with the bottle right on top of it. Chad wasn’t happy about that at all! “You may as well start coloring,” Mel said as they waited for the waitress. “I’m sure you can do a really good job.”
Chad noticed the wicked smile on her face. Reluctantly, he reached for the small box of crayons and dumped them out on the table – all three.
The waitress that walked up to their table was one that Chad had never seen before. As she greeted them and gave them her name, Chad couldn’t help but notice that her eyes mostly seemed to travel back and forth between the baby bottle near the edge of the table and him with the crayons and child’s menu. “Can I get you anything to drink?” she asked, her eyes now focusing mostly on the baby bottle.
“I’ll have coffee,” Mel said. Then she picked up the bottle and the twenty dollar bill and held them out toward the waitress. “Milk for her. And I’d like you to make sure that this is never empty.”
The waitress seemed hesitant to take the bottle and the money. Mel continued to hold them out, waiting, and a second later, both were in the waitress’s hand. “Of course,” she replied just before she walked away.
Chad felt his heart sink the moment she took the bottle. He picked up a crayon because he knew that Mel wanted him to and opened the coloring book menu.
“Don’t bother worrying too much about staying in the lines,” Mel said. “But maybe if I like one of them enough, we can hang it on my refrigerator… and another one on your refrigerator too. Wouldn’t you like that?”
Chad wasn’t exactly crazy about the idea… not one bit. But he replied, “Yes, Mistress,” in his silly sissy voice.
“So how was your day today?” Mel asked as she watched him put a blue crayon to one of the pictures.
Chad didn’t even bother to glance up from his work. “The usual. Embarrassing.”
“Did Robin notice your blue pantyhose?”
Now Chad did look up. “Oh yeah!” he replied in his sissy voice. “Unfortunately, when she complimented me on my outfit I didn’t think about what I was doing and curtseyed when I said thank you. Talk about embarrassing! And then she hugged me!”
Mel’s dislike for Robin suddenly grew to a whole new height. She could just imagine Robin, the young bombshell, rubbing her double D sized breasts all over him. “And how did you like that?” she asked carefully.
Chad shook his head. “It felt … uncomfortable. I sat down right afterwards so she wouldn’t do it again.”
Mel instantly felt a little bit better. But still, it was obviously time to do something definite about the Robin woman! She seemed to be getting her claws further and further into him, and it had to stop! “I’m glad you curtseyed for her though. You should always do that, for everyone.” The moment Mel said it though, she wasn’t too sure she still wanted to include Robin in that group.
Purposely moving Robin to the back of her mind, she asked. “Anything else interesting happen today? Did you talk to anyone else besides Robin? Do you ever talk to anyone else besides Robin?”
Chad picked up another crayon. “Robin now has half the women in the company calling me, trying to guess what kind of slogan I have on my nonexistent t-shirt at the gym. So I talked to all of them.”
“You mean instead of the pink leotards and tutu?”
“Yeah. Geez! Some of the things those women can come up with. It’s embarrassing just to think about them. At break this morning they were all throwing guesses at me one after the other. It was crazy!”
“And I’ll bet you loved every single one.”
Chad stopped coloring. Sheepishly, he admitted, “Kind of.” Then he went back to his coloring. “This afternoon I sat with Derek again during the break so I wouldn’t have to listen to anymore wild guesses from the women again.”
“Derek? How is he?”
“Fine, I guess. George stopped by for a minute and invited him to a poker game he’s holding next week while his wife is away. George actually apologized to me for not asking me to play again – as if he had to. I told him I was busy anyway.” Chad picked up another crayon and attacked the book with it.
“A poker game? Have you done that before?”
“Yeah, a few times. George likes to set the games up every time his wife is out of town.”
“I’m only guessing here, but aren’t these kinds of things mostly just a lot of guys sitting around drinking beer?”
“And playing poker.”
“But I thought you didn’t drink beer.”
“I don’t. I usually bring my own drinks so George doesn’t have to worry about it.”
“That’s awfully kind of you,” Mel noted.
Chad stopped coloring again and looked at her. “After George left though, Derek decided to play the old ‘I’m still your friend’ game. He offered to buy me a beer anytime I felt I need to talk.”
“But you don’t drink beer.”
“And I don’t need to sit down to talk with Derek. Geez! Afterwards, Robin somehow got the idea that he wanted to date me! Can you believe it?”
Mel was shocked on several levels. On the one hand, she was surprised that Derek would make such an offer, while on the other hand, she could just imagine how pretty little Robin might feel about Sissy going out with anyone else but her! Once again she forced Robin to the back of her mind – just not quite so far back anymore. “How do you feel about that though, your friend asking you out?”
“He didn’t ask me out! I wouldn’t go anyway.”
Just then, the waitress finally came back with coffee for Mel and the baby bottle full of milk for Chad. She set the coffee in front of Mel first then she looked back and forth between Mel and Chad while still holding the bottle. “Do you want this, or should I just set it on the table for him… uh… her?”
Mel smiled. “You can just give it to her… unless you’d like to hold it while she drinks some of it.”
The waitress looked shocked, but she recovered fairly quickly and just set the bottle down in front of Chad. “Are you ready to order yet?”
Mel nodded and told her what she wanted. Then she looked over at Chad. “And how about you, Sissy. What do you want?”
Chad’s eyes went wide. “I don’t know yet. I didn’t bother to look to see what they have!” Chad saw the waitress step back a bit at the sound of his sissy voice.
Mel shook her head. “Just like a child. Do you need me to read it for you?”
Chad quickly looked over the short menu selections intended for children. Not much of anything interesting at all. He chose the best selection he could see. “I’ll have the chicken fingers and fries, please,” he said to the waitress, still using his sissy voice.
The waitress stood there staring at him for a moment, then nodded. “Got it.” She turned toward Mel, and I’ll keep checking his bottle for you too.”
“Thank you,” Mel replied. She watched as the waitress walked away, then turned back to Chad. “So, are you interested in going out with guys?”
“Definitely, not!”
Mel watched him for a moment as he picked up another crayon for the picture he was coloring. “I’d be working awfully hard on that bottle too if I were you. I don’t want to feel like I’m wasting the money I just gave to our waitress.”
Chad definitely wasn’t happy about that. But the intense stare that Mel was leveling at him was more than enough to force him to pick the bottle up and start drinking from it. He dared not let his gaze wander around to any of the other customers. Instead, he tried to focus his eyes down at the picture he was coloring. With one hand holding the bottle, he continued to color with his other hand. His double task made the coloring that much more difficult now because he had to keep his head up to drink from the bottle while trying to look down past the bottle to see what he was doing. Suddenly, staying in the lines became much more difficult.
“So you’re not interested in going out with guys?” Mel asked.
Chad shook his head, then realized that he couldn’t talk while drinking so he remove the bottle from his mouth for a moment. “Not at all.”
“But you want to experience… how can I put this... life from a woman’s point of view? If you know what I mean?”
Chad nodded and removed the bottle from his mouth again. Talking while drinking and coloring was getting difficult. “Yeah, but I’m not interested in dating guys.”
“Not at all? Wouldn’t that be part of being a woman? Experiencing something like that?”
Chad just stared at her with the bottle still stuck in his mouth. He tried to figure out just how he thought about the question. He finally shrugged and pulled the bottle away again. “I never really thought about it before. Dating guys is just something I’ve never been interested in. I guess I like women. They’re much more interesting. Maybe that’s why I like dressing like one.”
Mel thought about his answer as she watched him going back to coloring while drinking. Actually, she was pleased with his answer because it meant that he wasn’t gay, probably not at all. There was something very satisfying to her about knowing that. But still, she wondered how embarrassing it would be for him to have to go out on a date with a guy sometime… just a simple date. Like to the movies and dinner or something – no sex!
Chad was tired of talking about himself. Too many embarrassing questions. His entire day seemed to have been full of them. He briefly removed the bottle from his mouth again. “And how about your day? Was it bad?”
Mel found herself gradually relaxing more and more as she opened up and told him about how busy things were at work. Some of the cases she had were major problems, some were stupid things that never should have come to legal issues in the first place. To everything she said, Chad seemed to listen intently, offering just the right comments or replies to everything.
Before their dinner arrived, the waitress took his mostly empty bottle and refilled it for him. A few minutes later, Chad was able to put his coloring book aside so they could eat. The two of them continued to talk together while they ate – Mel in her normal friendly voice, Chad in his silly sissy voice. And Mel was surprised that even listening him talk like a ridiculous toddler, she still enjoyed talking with him… and just being with him too.
As they both got near to being finished with their dinners, the waitress came back again to refill his bottle. Chad wasn’t very happy about that because he had already had way too much to drink. Even with no two hour limit to worry about, he had way too much liquid in his system to hold back for very long. He was more glad than ever to be wearing double diapers and everything else to protect him from leaking.
“You still couldn’t finish everything,” Mel noted as she realized he hadn’t taken another bite in quite some time now. “Even from the children’s menu.”
Chad looked down at his plate. “I’m way too full. Too many bottles of milk. I’m nearly drowning!”
“Never too much to drink!” Mel replied. “Never! Are you ready? We’ve got to get moving.”
Chad nodded and started to get up. “Don’t forget your coloring book. And I suggest you do your best to finish that bottle before we get to Gloria’s.”
Chad looked at his bottle. It was still nearly full. He could never do it. But he reluctantly picked up the book he had been coloring in along with his mostly full baby bottle and followed Mel out. At least he would be back in the car in a few minutes where he would be out of sight – sort of.