The Bet - Chapter 16 (Sunday – week 3 Part 1)

The Bet
by Karen Singer

Chapter 16 (Sunday – week 3 Part 1)

Fitful dreams cause fitful sleep. And consequently, fitful sleep causes fitful dreams. He was inflicted by both. After starting to relearn to hold back all day, the three baby bottles of Mel’s special tea that he drank before he fell asleep re-stimulated his system… a system that was already trying to relearn how to sleep through it all. He tried to wake up to hold back each time, but it was just too difficult. He was getting no sleep at all. He finally abandoned himself to just letting it happen without holding back. It was his only choice. And just as he finally fell into a deeper sleep, he was woken up one more time when the suppositories in his system rudely decided to do their thing. He had no control over what the suppositories did - ever. That was impossible. He no longer even tried.
To mirror his troubled sleep, he dreamed. Strange disturbing dreams. He was a child again. His mother was unhappy with him and he didn’t know why. He asked her why over and over again, but she never would say. In his dreams, he felt crushed because he had disappointed her – his own mother. He ached for her forgiveness, but forgiveness never came.
There were tears in his eyes when his pink alarm clock went off. While the images and situations of the dream were quickly lost from his consciousness, the emotions were not. He wondered why he felt so depressed and chalked it up to not sleeping well. He literally dragged himself off his blow-up mattress and stood up. He turned the loud music from the clock radio off. It was later than he thought, yet it felt all too early.
He waddled awkwardly into the kitchen to see if she had left him another note with instructions. Of course she had.

Sissy,
First baby bottle!
Go buy yourself some breakfast.
Make sure your uniform is ready for inspection later, but don’t wear it.
Make sure you have a grocery list ready for this morning.
Pad the breasts of your girdle.
No makeup today!
The rest is up to you, but don’t forget your ring and necklace.
I’ll be looking you over when you arrive again.
Be here at ten o’clock – sharp! Ready to go! No excuses this time.
Second baby bottle before you get here!

The cookbook she had purchased yesterday was on the counter next to the note. He automatically went to his refrigerator and pulled out a bottle without ever thinking about not doing it. He grabbed the cookbook from his counter and went into his living room where he sat in the only chair that he had. His overly bloated diapers made it feel more like he was sitting on a big ball instead of the seat of the chair. He put the baby bottle to his lips and started browsing through the cookbook. The cold tea on his system triggered his need to pee again. He almost let it out without holding back again but he caught himself just in time. He held it as he began reading through the recipes. Almost a minute later, he couldn’t stand it anymore and released himself into his soaked diapers. Without realizing it, his depression melted away at the same time.

Mel rolled over in bed and opened her eyes. Without moving her head, she glanced at her clock. It was fairly late, but it was also Sunday. Her entire body felt loose and relaxed and just plain wonderful. It was amazing what Chad had done to her last night… or maybe it was more like what she had done to herself - with him. Either way, it had been wonderful. Wonderful enough that she felt no desire to even get out of bed. She rolled over lazily and closed her eyes. Smiling and thinking about Chad, she fell asleep again.

After he had shaved and cleaned himself up in the bathroom, Chad stared at his closet and tried to figure out what to wear. Really, for the most part, it boiled down to dressing like he had for work all last week – mostly. He would much rather wear the low-heeled shoes, but those shoes were now part of his uniform and once he reshined them this morning, then they’d only get messed up before Mel inspected him later. That left him with only a choice between several different pairs of high heels. He thought about work tomorrow, could he wear the low-heeled shoes to work? He prayed that he could!
His other clothing choices weren’t much better. The only male clothes he had now were his shirts. But now he had several new blouses hung up with them. He touched one of them and pulled it aside to look at it more closely. He could wear it, he was sure. He was also sure that Mel would really like that. In a way, it would be fun. Of course he could wear one of his skirts too… but not likely! Especially not since they were going out shopping again. He shuddered as he remembered his trip to the grocery store last week when she had made him wear a skirt. She had actually called the police on him before he got out of the car and gone into the store with her. No, no skirt today for sure! He pulled out one of his work shirts and a pair of the pants he had worn to work earlier in the week instead.
Two diapers, a pair of plastic panties, pantyhose, an all-in-one girdle, old pantyhose stuffing the breasts of his girdle, his button-down shirt, women’s slacks, and the same pair of relatively comfortable heels he had worn yesterday. He added his new necklace and ring. He had a lot of trouble trying to connect the clasp on his new watch and then fasten the extra security chain it had, but he finally got it. He looked in his bathroom mirror. What little of himself that he could see looked fine – if you didn’t count the breasts sticking his shirt out abnormally. With his shirt buttoned up far enough, it mostly hid the feminine necklace he was wearing. It was the rest of him that he couldn’t see in the mirror that he was worried about.
Knowing he had to get some breakfast, he grabbed his purse and headed for his favorite drive-through.

Mel held her coffee cup in both hands and took her first sip. It was good. A small wave of pleasure rippled through her body. Still in her nightgown and robe, she sat down in one of her living room chairs to enjoy it. She had some things she needed to be doing this morning before Chad came, but she just didn’t feel like it. Her hair needed washing, but she figured she could put that off till tomorrow too. Right then, relaxing and enjoying her coffee seemed much more important.
She was looking forward to going shopping with Chad again today. First, Sandy was going to help them look for more makeup and then they had grocery shopping to do. She well remembered last week’s grocery shopping trip. She had made him wear a skirt, and then had to fake calling the police to get him out of the car. She hadn’t demanded that he wear a skirt today. She knew he wasn’t ready for that yet. Not yet, but if things worked out like she planned, then he would be pulling the skirts out of his closet to wear very soon. That thought gave her another small wave of pleasure. She sipped at her coffee again.

Yeah, going through the drive-through was absolutely one of the best things he could do, he decided once again. This morning, the girl hadn’t even noticed anything odd about him at all – till he handed her his money and she saw his electric pink fingernails. He wasn’t sure if she had noticed the breasts protruding under his shirt after that or not. But it didn’t matter. Didn’t some guys wear nail polish now – kind of like a fashion statement? Ok, not usually bright pink!
He had been smart today, he didn’t get any coffee. Why make matters worse since he still had to drink another one of Mel’s stupid baby bottles of tea. He wolfed his breakfast sandwich down as he began drinking his second baby bottle of the morning instead of his usual coffee. He was less concerned about messing his diapers while he was out today. Since he was now diapering himself more often, he was getting less and less of those miserable suppositories stuck up inside of him. He wondered if Mel realized that fact. He wasn’t about to mention it to her.
As he headed back to his bedroom after breakfast to press his uniform for the day, he realized he was already holding back on peeing... and he hadn’t even realized that he had to go. He smiled to himself. Things were getting better and better!

Mel glanced at her clock, then went back to watching her door. He better not be late today! It was with a profound sense of excitement and relief when she heard him knocking – thirty seconds early. More excited than she realized she was, she quickly opened the door for him.
“Good morning, Mistress,” Chad said as he dropped a quick curtsey.
“Good morning, Sissy,” she replied as she stood back out of the way. Once again he was carrying his uniform and the shoes for it in his hands. She was a bit disappointed to see that he hadn’t worn his new slacks today, but that was only a very minor thing. She left the door wide open since Sandy and Cassie should be there any minute now too. “Go put your dress in my bedroom again,” she instructed.
When he came back again she had him stand near her door where she could look him over completely like she had done yesterday. “Are you wearing two diapers?” she asked.
“Yes, Mistress,” he said with a quick curtsey.
“Unbutton one of the buttons on your shirt! I can’t see enough of your necklace.”
He reached up and unbuttoned one more of the buttons on his shirt than he was used to. He suddenly felt all that much more exposed, even though he wasn’t really. The breasts sticking out from his shirt now forced the opening at his neck to go wider than he would have liked.
“Much better,” Mel stated, more to herself. This time she had no makeup job to inspect since she was sure that Sandy would want to see his bare skin. She suddenly stepped back with an angry expression on her face. “Where’s your pacifier?”
Chad was surprised and worried. He hadn’t even thought about it. He dropped another curtsey and said, “I’m sorry Mistress, I forgot it again.”
“This is happening too many times now and I keep forgetting to punish you for it…”
“Hi everybody!” Sandy’s cheerful voice interrupted from the doorway as she and Cassie stepped into the room.
“Is there a problem?” Cassie asked.
“Nothing we can’t sort out later!” Mel replied with an angry look at Chad. She turned back towards her two guests and smiled. “Are you two ready to go?”
“More than ready!” Cassie replied enthusiastically. “Are you still going grocery shopping when we’re done?”
“Yes, we need to.”
“Then we’ll take my car and meet you there,” Cassie replied.
“That reminds me,” Mel said as they all went out through her doorway, “Sissy, do you have your shopping list?”
“Yes, Mistress,” he replied, this time without the curtsey. “It’s in my purse.”

Mel followed Cassie’s car all the way to the mall and parked next to her. They all went in together into one of the major department stores. Chad had remained silent for the entire trip and stayed that way now as he followed a few steps behind the three women who were chatting together and mostly ignoring him. He had no doubt that he was in for more humiliation. But wasn’t going out dressed as he was right then humiliating enough? He certainly thought so.
The women were ignoring him like he wasn’t there. Would they miss him if he left and went back to the car? He really wished he could. Unfortunately, he knew better.
Sandy led them all the way through to the makeup section where she suddenly squealed again and took off faster for one of the counters. “Stacy! You’re still here!”
“Sandy!” her friend called from behind the counter. “What are you doing here? Need some makeup?”
“I always need makeup. You know that!” “Don’t we all,” Stacy agreed. But out of the corner of her eye, she noticed Chad for the first time.
“Uh… I see you’ve got some new friends.”
Sandy turned back towards Mel and Chad. “Yeah, that’s why we’re here. This time I need some makeup for him!”
“You’re kidding me, right?” But then she corrected herself before Sandy could answer. “No, I can see for sure that you’re not.” She shook her head. “Let me guess, you want me to do a full makeover on him, right?”
“No way!” Sandy replied. “Not till I get my claws into him first!” Stacy looked very surprised, if not disappointed while Sandy and Cassie laughed outright. “Stacy, this is Mel. She lives a few apartments down from us.”
“Hi Mel,” Stacy replied, but her eyes were still on Chad.
Sandy pointed at Chad. “And that’s Sissy.”
Chad turned another shade of red while Stacy just nodded her head, still trying to comprehend him. “Yeah, I can see that!”
“No, that’s his name now.”
“His name?” she asked.
“That’s it.” Cassie confirmed.
Chad could feel his face turning a darker shade of red.
Stacy shook her head. “Ok, sissy boy, climb up on the stool here and let’s get a better look at you… And if you don’t stop blushing, we’re never gonna’ figure out your skin tones!”
Chad did as he was told, but he did it slowly and cautiously. His heart was suddenly pounding along with the embarrassment he felt. Were there any other people watching him? He didn’t want to look to find out. He was sure there were at least some. He just hoped it wasn’t too many.
“Ok,” Stacy finally asked. “What are you interested in?”
“Well,” Sandy replied. “He’s got some things already, but…”
“Everything he has should be in his purse!” Mel interrupted.
Stacy looked at Chad. “Well, honey, you gonna’ lay it all out for us? We can’t help you if you don’t.”
Chad reluctantly opened the purse in his lap and began grabbing all the makeup out of it and putting it all on the counter in front of him. Stacy picked up each item and looked at it and sorted it all into different piles. “This is ok… this is junk… this is good, heck, I use it myself! It’s just as good as anything I got here and it’s cheaper! Good… good… ok… not so good… ok…”
When all the makeup was out, she and Sandy went through it all one more time. Most of it was ok, but clearly both Sandy and Stacy thought he needed more. “And where’s his moisturizer?” Stacy asked.
“Home,” Chad replied. “I shave with it.”
“You shave with it? Huh! I guess it’s as good as anything else.”
“Ok Sandy, what do you want first?”
“I think some concealing sticks and highlighter,” she replied.
Chad soon found his face being attacked by Sandy smearing one type of makeup after another on it then wiping it all off again. From there, they moved into more colorful and noticeable options that he was a lot less happy about. He also wasn’t happy to see the pile of things they wanted him to buy growing larger and larger. “Why so much?” he complained.
“Honey,” Stacy replied, “you need different stuff for different occasions. Not to mention different lighting. Come on, you gotta know that much!”
Chad didn’t say anything. His answer would have only made him look more foolish than he already felt. The longer they worked on him the larger the pile of things they wanted him to buy became. He had visions of his purse overflowing and breaking under the strain. “How am I going to get it all into my purse?” he asked at one point.
“Don’t worry,” Mel replied. “We’ll help you figure out which things you should have with you all the time and what you can leave at home.”
That was the only bit of comfort Chad got through the whole process. And it was a very tiny bit.
When they were done, Chad not only had a fairly large bag of makeup, but also several free gifts that came with it all, including some perfume that all the women seemed to think was heavenly. But to Chad, it smelled too flowery and made his stomach feel like it had butterflies in it constantly, since it had already been too long since he had had any sexual relief. Unfortunately, they had sprayed the stuff on his neck and both his wrists. There was no getting away from the smell!
The only good part as far as he was concerned, was that when he left, they had wiped all the makeup off of his face again. That alone felt like a minor victory.