The Bet - Chapter 10 (Monday – week 2 Part 3)

The Bet
by Karen Singer

Chapter 10 (Monday – week 2 Part 3)

Mel took them out to dinner that night at a nice steak restaurant. The part that Chad wasn’t very happy about was having to carry his big pink diaper bag in with him. Worse, Mel made him carry it over his shoulder so it could be seen better. “You should be proud to show off your new bag,” she told him. “It’s very pretty.” Chad had no comment.
When they ordered, Mel made sure that Chad got a large steak with plenty of extras while she got something a bit more in keeping with her diet that she wasn’t officially on. Chad was really glad about the steak. What he wasn’t glad about was having his drink poured into a baby bottle for him again. He just stared at it on the table in front of him, not wanting to touch it at all. “You better start drinking,” Mel told him, “because we’re not leaving here to you’ve finished every drop of what’s still in this glass here. Chad looked at the extra large drink she had ordered for him. The glass was still two thirds full. Very reluctantly, he reached out and picked up the bottle and brought it to his lips. This would be another restaurant he could never go back to again. Why did she have to be so cruel? But he realized that despite relieving himself of his sexual frustration twice earlier, that need was quickly growing again.
Once they were back in the car again, Mel asked him, “Where do you usually buy your clothes?”
“A lot of different places,” he told her.
“I know a good place where they have lots of nice quality things. It’s not too expensive either. Let’s go there.” Chad had no reason to not go with her suggestion. Besides, she was driving. But when they got there, Chad had immediate doubts about the store. From the outside it looked very nice and upper-class. The part that worried him was that he wasn’t sure if the store sold any men’s clothes. “Are you sure about this place?” he asked her as he pulled his diaper bag up onto his shoulder again.
“Oh yeah,” Mel answered. “I buy things here all the time.”
More worried than ever, Chad followed her into the store. He looked around when they got inside. “I don’t see the men’s department.”
“They don’t have one,” Mel replied as she led him toward the back of the store. Chad felt the beginnings of panic start to settle into his stomach again.
Mel strolled casually through the store, stopping here and there to look at something more closely. Finally, she led him into the Junior’s department where she started looking through the racks of slacks, wondering what size would be the best for him.
“I was really wanting some new men’s pants,” Chad commented.
“Nonsense!” Mel replied. “Why should you ever want to buy men’s clothes?”
“Like maybe for work!” he replied urgently.
“You’re a sissy, aren’t you?”
Chad hung his head, “Yeah,” he replied softly.
“So why should you be wearing men’s clothes?”
Chad had no doubt that whatever he said he was going to lose the argument, so he said nothing. He allowed himself to pee into his diapers instead.
Mel walked around lots of racks and picked up about five pairs of slacks that she thought might fit him. Then she led him over to the changing room where the attendant suddenly got a bad case of the giggles. Mel took his diaper bag from him and handed him the first pair of slacks. “Ok, put them on and let me see.”
Chad wasn’t all that happy about it, but at least that part of the store was set up so that not many other people would see him. He went into the dressing room and pulled his pants off and slipped the women’s slacks on. They fit over his diapers easily and were way too long. He poked his head out from behind the curtain. “They’re too big,” he said.
“Let me see,” Mel replied.
Chad walked out to show her. He noticed the attendant watching closely from the entrance to the changing area.
“Yeah,” Mel agreed, “they’re a bit big. I wasn’t sure about the best size because of your diapers so I had you try the biggest ones on first.” Chad saw the eyes of the attendant behind her grow wider. She handed him another pair of slacks to try on.
The next time Chad came out of the changing room, the attendant was standing right with Mel, talking to her. As far as he could tell, the only good part about his current situation was that there were no other customers around at the time. But that certainly wasn’t saying much.
Chad tried on pair after pair at Mel’s whim. Usually ones that the attendant had found somewhere out in the store and had brought back for him. Some were too big, some were too tight. Some were way too long. More than a few of them had a low-rise waist that showed off way too much of his girdle or could possibly show the top of his diapers underneath. But every pair that he tried on continued to fuel his growing sexual need once again. He couldn’t believe he was doing what he was doing. Trying on women’s clothes, with two women helping him… It was almost becoming too much. He was beginning to be glad for just how tight his girdle was to hide any signs of how excited he was becoming over it.
The attendant soon began taking more and more of an active role in trying to fit him. More than once she commented about how visible his girdle was or if she thought the fit or style was all wrong. Eventually she was running her hands over his the slacks to see how they fit. Chad was convinced she was really trying to feel the diapers he was wearing under his girdle. He also quickly realized that he wasn’t going to have a say about any of what he would be buying.
By the time they were finished, they had picked out three pairs for Chad to buy, one in black, one in light tan and one in dark blue. All three pairs were in different styles and very feminine. All three pair felt delicious to wear. None of them were anything close to what he could ever wear in public! And it had taken so long that Chad had wet himself two more times. He was just thankful that nobody would ever know.
When they were done, Mel thanked the attendant sincerely, and led Chad further into the store. Chad had thought they would be leaving, but Mel was showing no signs of that yet. As far as Chad was concerned, there was no place in the store that he would feel comfortable – especially toting around his pink diaper bag. He was even less comfortable when Mel started browsing through the racks of purses. “You need a purse!” she said to him flatly.
The word slipped out of his mouth before he realized it. “Why?”
Mel looked at him like he was crazy. “Because you can’t carry everything in your hands, of course! Silly question. Now start looking for one that you like that will be good for everyday use.”
Chad wasn’t exactly sure what constituted good for everyday use, but he looked over the purses without touching any of them. Mel watched him for a few moments. “You might want to pick up a few and look through them,” she told him with more than a bit of exasperation in her voice. “How else are you going to know how they’re made or what they can hold?”
Chad wasn’t sure he wanted to touch any of them, in fact, he was quite sure he didn’t want to touch them. He had already been branded as a sissy in the store by trying on all the women’s slacks, not to mention what his diaper bag said about him. But Mel was still watching him, waiting. Obviously she wasn’t giving him a choice in this matter either. He began looking through them more carefully. What would be a good one? Something that wouldn’t be noticed quite so much. He suddenly had visions of himself walking around carrying a purse and his sexual excitement jumped another huge notch. Tomorrow at work when he could relieve himself couldn’t come fast enough for him.
Finally he pulled one down that was all black leather. It was the plainest one he could see. He had to juggle all the slacks he was carrying to be able to open it and look through it. Plain, black.. it shouldn’t call too much attention to him… if he had to carry it, which the more he thought about it, the more likely it sounded. He held it up to show Mel. “How about this one?”
She shook her head. “You only looked at one! How do you know there isn’t something better? And it’s not exactly stylish. Does it even have a place for your cell phone?”
Chad hadn’t thought about that last part. He looked again. “No,” he admitted.
“Wouldn’t it be handy to have compartments for different things?” she asked.
“Yeah, I guess,” he replied as he put the purse back on the rack. He pulled a few down and looked through them. The problem was, the more practical they seemed, the more girly they looked to him. Not exactly what he wanted.
Mel realized after a while that he was really having a hard time picking one out, so she decided to help him. After all, she did have more experience than he did. They finally settled on a medium sized dark red alligator leather bag. It had various sized pockets on the outside as well as on the inside – including one that Mel declared would be perfect for his cell phone. The large silver clasp on it would hold it closed to keep the contents in and the two handles were just large enough that if he had to he could slip them over his shoulder. Actually, Chad didn’t decide on the bag at all, Mel talked him into it.
After that , Chad was really hoping they were finished and could finally go home, but Mel went to one more department in the store first – the shoe department. “But I have shoes,” Chad protested as she began looking through the selection.
“You need more,” Mel replied without even looking up.
Chad allowed himself to wet his diapers again as he watched Mel looking through the shoes. He realized that all the liquids she had made him drink were making him pee way too often again. It was a nuisance, but there was nothing he could do about it.
As he watched Mel, he was surprised to realize that she wasn’t looking at high heels for him. In fact, all the shoes she picked up had fairly low heels. “What size do you wear?” she asked.
“In women’s shoes? Usually a nine and a half.”
Mel nodded as if satisfied, then went back to examining what was available. Finally she seemed to settle on a fairly plain looking black pump with a wide one inch heel. She pointed to one of the chairs that were available. “Go sit down,” she instructed him. Chad did as he was told while Mel went in search of a saleswoman. When she found one, Chad saw her showing the saleswoman the shoe she had picked up, then Mel pointed at him. Even from where Chad sat he could see the woman blush. Chad realized that he was about to be in for more humiliation.
Mel walked back to Chad while the saleswoman was looking for the shoes and told him to take his shoes off while they waited. Chad set all his things down on another chair and did just that. Suddenly, his stocking clad feet and bright red toenails were on display for everyone to see. His sexual need was growing again, and rapidly. Although he wasn’t completely happy about it, he recognized that this was another dream come true for him – trying on shoes in the store. He had never done that before. The only thing he could have wished for was that the shoes could have been high heels instead. He was a bit puzzled over the low heeled shoes that Mel had picked out for him.
The saleswoman came back with three boxes of shoes that she set down on the floor next to Chad. Chad noticed that she looked very embarrassed. Not nearly as embarrassed over it as he was though. “I brought a few different sizes,” the woman said, “just in case.”
“Thank you,” Mel replied as she picked up the top box and looked at the size. The box said size ten. She selected the middle box and checked the size, then she opened it and handed Chad one of the shoes.
Chad slipped the black pump onto his left foot. It seemed to fit just fine. If anything maybe a bit loose. He was surprised to realize how comfortable it felt. “Nice,” he said with some surprise. “Really comfortable.”
“Let’s try the next size smaller,” Mel suggested. “We don’t want them to slip later.”
Chad removed the shoe he was wearing and handed it back to Mel, who handed him one from the next box down. He slipped it onto his foot. He had to pull a little harder to get it on, but it still went on fairly easy. “It’s a little bit tighter,” he declared.
“Is it too tight?” Mel asked.
Chad wiggled his foot a bit trying to decide. “It’s hard to tell.”
“Here try the other one on too.”
Chad was soon standing and walking around with both of the shoes on his feet. “They’re a little tight, but not too bad,” he finally declared. “The other size is definitely more comfortable.”
“We’ll take the ones he has on then,” Mel declared.
Chad wasn’t overly happy about that. Why buy shoes that were a bit tight? But again, he realized that he didn’t really have any choice.
Chad had to carry the new slacks he was buying, the purse, the shoe box, and his diaper bag from the back of the store all the way up to the front where the checkout counters were. He felt like a pack animal. Mel only carried her purse. There weren’t a lot of shoppers around as he was checking out, but he did fully expect Mel to ask again if he needed to wet his diapers. But she didn’t ask at all. He figured she had probably forgotten. Since she hadn’t asked, he wet himself again as they walked out through the door.
He was actually grateful to finally get back into Mel’s car and head back to her office where he picked up his own car. “Go back to your place,” she told him. “I’ll meet you there in a little while.”
Chad drove back to his apartment and lugged everything upstairs. He was grateful to be able to finally stop carrying around his big diaper bag. The thing wasn’t only too pink, but it was bulky and heavy and it tended to keep slipping off of his shoulder. What a pain!
Mel came in a little while later carrying a large plastic bag. She sat him down on the floor and reached into the bag and pulled out a baby bottle and handed it to him. Chad inwardly groaned. He was still peeing more than ever before. If he drank much more tonight, he’d never get any sleep. He sat and drank it while he watched Mel take bottle after bottle out of her bag and put them into his refrigerator.
After that, Mel emptied his diaper bag and went through the contents. Then she reloaded it, making sure that everything Chad would need for tomorrow was in there – except the baby bottles, those she would add in the morning.
As soon as Chad finished his drink, she had him try on again all the slacks he had just bought. She cut all the tags off for him before she allowed him to hang them up neatly in his closet. Finally, she changed his diapers for him, noting that he hadn’t messed himself again, and inserted two more suppositories before she taped them up and locked him into his onesie for the night.
“I’m leaving you now,” she told him. “But I’ll be back later to check on you. If I don’t make it back before you go to sleep, don’t worry, I have a key and I won’t wake you.”
Chad was surprised that she would be leaving him alone so soon. It was still a bit too early for bed.
“While I’m gone,” she continued, “I want you to drink four more bottles before you go to bed.”
“Four…” Chad protested.
“Four! And between each one, I want you to practice your makeup. Don’t let me come back and catch you goofing off!”
Chad groaned. “Yes Mistress.” What else could he do?
“Good,” she replied. “Tomorrow morning I’ll be coming here again instead of you coming to my place like you did this morning. I’ll be about twenty minutes earlier than usual so make sure you’re up and shaved before then. Oh… and make sure you’ve finished another baby bottle in the morning before I get here too.”
“Ugh,” Chad groaned aloud.
“What?” Mel’s eyes were suddenly showing fury.
“Sorry. I mean… Yes Mistress.”
“That’s better.”
Mel picked up her purse and left him. She really had no intention of coming back later, but he didn’t know that. Tomorrow was going to be another day. A busy day. And a day that neither of them was likely to ever forget! And she couldn’t wait!