The Bet - Chapter 29 (Saturday – week 4 Part 8 of 9)

The Bet
by Karen Singer

Chapter 29 (Saturday – week 4 Part 8 of 9)

Chad wasn’t happy. More shopping? For what? And his diaper was already awfully soggy! But Mel started wandering through the store, seemingly in no hurry at all. Chad was nervous about being seen in his maid’s dress, but that was nothing compared to wandering around with the pacifier in his mouth. Why couldn’t Mel just leave and go home?
Anytime he noticed anyone looking at him, Chad felt a major bolt of embarrassment and shame running through him. And every bolt of embarrassment seemed to reignite his huge sexual need, sending it into an almost physical frenzy. As he followed Mel around the store, he imagined he could actually feel Cassie’s toy stuck firmly up his backside, increasing his shame and his sexual pleasure with every step that he took.
Mel wandered around casually and slowly, taking her time to look over everything thoroughly. She was enjoying looking. She was also enjoying parading Sissy around the store where everyone could see him. She knew the stupid pacifier in his mouth had to be humiliating the shit out of him, but he had no choice but to endure it for as long as she wanted him to. And since they had taken her car, he couldn’t even leave.
As she shopped, she came across a few items that she liked that she picked up for herself. No sense in him having all the new things. But then she started walking through the underwear department. She looked at this and that for him, half searching for a proper corset, but she didn’t see one or anything else she was interested in – until she came to the socks. There, on a rack that displayed many different styles, were row after row of the frilliest anklet socks imaginable. Just perfect for his sissy dresses. She spent quite a while picking out two of the perfect pair to go with the two other dresses he didn’t have any for yet. Then, with a smile, she handed them to Sissy. “Here, you can carry these, since you’ll be buying them.”
Chad had watched her closely the whole time she was searching through the frilly socks. He just knew she would be buying them for him. And when she actually turned and handed him several pairs, he was torn between the humiliation and the excitement of it. Worse, he now had to carry the obviously overly feminine items around with him as she continued to wander slowly through the store. With the pacifier in his mouth loudly proclaiming him as the sissy baby that he was, he had even more reason to dread other people seeing him now.
Mel continued to wander slowly, looking at things here and there, but now her wandering had more direction to it. The socks had started a specific train of thought. She really wondered if the store might have what she had in mind. Probably not, but it was worth a try anyway. The department she was heading for was in sight now, but as she looked around at where they were, she suddenly stopped in one of the aisles. Nobody was really looking, although Chad probably wouldn’t realize that. “Lift your skit and let me check your diaper,” she ordered.
Chad’s eyes nearly bulged out of his head. Here? Now? She couldn’t mean it!
“I’m waiting!” Mel snapped angrily. “Shall I add another demerit? And just a polite reminder, I’m also expecting a curtsey before you lift your skirt.”
Chad was in shock. She did mean it! But he had already had enough punishment today that he would do almost anything to avoid getting any more. He quickly dropped a quick little curtsey as he mumbled more baby jargon. Then he grabbed the front hem of his skirt and feeling very foolish, lifted it up.
“Higher!” Mel demanded. I want to see your diaper clearly!”
Oh God! Chad pulled the hem of his skirt up as high as he could, totally exposing his soggy diaper underneath for all to see. He wanted to die of shame. He started sucking his pacifier furiously. Way past Mel, out in the aisle in the distance, he saw a woman stop and stare at them. What must she think? The answer to that was all too obvious.
Mel smiled. “Nice and soggy I see. Good! But no leaks yet.” She glanced at her watch, then pointed to it. “You’re running out of time. Better get busy!” Then she turned and continued her slow journey toward the department up ahead.
Chad knew he was running out of time. He also knew that the diaper he was wearing probably couldn’t hold much more – at least, he didn’t think it could. The diapers these days could hold so much that it was really impossible to tell what would make them leak. Then another thought struck him. Was that why Mel was going so slowly through the store? Was she waiting to see if his diaper could leak before they left? Unfortunately, he had no way to ask her since he was limited to just baby talk. How frustrating!
Mel led the way into the shoe section and began looking through the shoes seriously. What she really wanted, she was fairly sure she wouldn’t be able to find, but maybe they would have something else that might work. After searching briefly around, she knew that what she wanted wouldn’t be there, but she continued to just look to see what they had anyway. Besides, there were other people around and she was enjoying Sissy’s discomfort.
Then she turned a corner to look at one last aisle near the wall and her eyes locked onto a whole long row of shiny patent leather shoes. She smiled as she began looking through them closely. One pair quickly caught her eye and she headed straight for it. It was a pair of pumps similar to the patent leather heels that she owned only the heel looked even higher – if that was possible. She had once considered buying Chad a pair like the ones she had, but hadn’t gotten around to it. She picked up the shoe on display and looked at it carefully, but as she did so, her eyes caught sight of a shoe just a short distance away, and something in her head told her that it would be even better. The shoe was basically a variation of the mary-jane style but it had a very high heel and was shiny bright patent pink. A pair like that would not only go really well with his other sissy dresses, but she was sure they would probably embarrass him tremendously.
She picked up the display shoe and turned to look for a sales person, and that’s when she saw it. Way down near the end of the row of patent leather shoes, mixed in among a few more practical styles, was a pair that looked exactly like what she wanted. She hurried over to look more closely. Yes! Perfect! Black patent mary-janes with a perfect little-girl heel. Unbelievably! The pink high-heeled shoes might shout one type of sissy, but the little-girl style was exactly what she was looking for. Still… the pink high-heeled shoes seemed awfully interesting too. She made her decision. It was easy. She just figured what the heck! He was the one who would be buying them, not her. She’d make him get both! “Sissy!” she called. “Go find someone to help us!”
Chad’s knees nearly gave out. Find someone to help? She had to be kidding! And how was he supposed to talk to whoever he found? But Mel was staring at him, waiting. He quickly dropped a quick curtsey and turned to find some sales help.
“And I’ll be watching to make sure you behave properly!” Mel called behind him.
Ugh! It would be hopeless… not to mention how embarrassing it was about to be! He turned back around again and dropped yet another curtsey as he mumbled more nonsense through the pacifier in his mouth. What a situation!
Chad started wandering around looking for some help. He felt like he was now even more exposed than ever as he was forced to search among the women in the department for one who might be able to help them. But he wasn’t having much luck. In desperation, he finally headed toward the wall where he had seen a doorway heading back to the stock room. And there, coming out of the door, was a woman who was obviously attached to the department. Chad saw Mel watching him out of the corner of his eye. There would be no help for it. He dropped a curtsey to the woman and started speaking some baby talk.
“What?” the woman asked, obviously annoyed with him. “I can’t understand anything that you’re saying!”
Instead of repeating himself, Chad motioned desperately for her to follow him. And fortunately she did, all the way back to where Mel was waiting.
The saleswoman was obviously annoyed with Chad, but Mel didn’t care. “I’d like to see a pair of each of these for her,” she said as she pointed one of the shoes toward Chad.
The woman seemed to sigh a bit, but she checked the numbers on the shoes, got Chad’s size from Mel and went off in search of what they wanted. While she was gone, Mel had Chad remove the shoes he was already wearing. She checked her watch again. “You’re running out of time, Sissy.” It was all she had to say. Chad’s worry level went up another couple of notches. They had been in the store for a very long time now and he hadn’t been able to drink anything since the car ride here. He desperately tried to pee even harder.
When the saleswoman finally came back, she was carrying two shoe boxes. She set them down next to Chad and opened the top box. Inside were the pink high heeled shoes. “We had these in his size, but I couldn’t find a pair in the right size of the other ones, so I brought the largest size I could find. It’s one size smaller, but maybe you can make them work. Let me know if you need anything else.” And then she walked off to help some other customers.
Chad tried on the pink heels and Mel had him walk around a bit in them. He was guessing that the heels were about four inches high. Tall, but not a huge problem. The real problem was the color. The shiny pink absolutely screamed for people to look at them. They would be terribly embarrassing to wear.
“Curtsey for me in them,” Mel suggested as she stood back watching him. Chad did so and she smiled. “Yes, I like those a lot. They’re absolutely perfect for you. Okay, try on the others now.”
The low-heeled shoes felt very tight on his feet, almost too tight. But he did manage to get them on. Fortunately the rounded toes didn’t hurt him too much. The very low heels however felt awfully strange. The part that seemed to get to him the most though was how much they looked like little-girl shoes. That alone was embarrassing.
“Oh, I really like those too,” Mel said. “They’re another pair that’s perfect for a little sissy like you. And since you can still walk in them, I’m not worried at all about the smaller size. They’ll be good enough. In fact, I think I like them better in the smaller size since they make your feet look smaller. Maybe we should consider that for the other shoes too. Hmmm.”
While she stopped to consider the idea, Chad was horrified by the suggestion. The higher heels were already uncomfortable. Getting them in a smaller size would only make things worse!
“Tell you what,” Mel said, “before I have you go and find the saleswoman again, curtsey for me in those shoes too.”
Chad wasn’t exactly thrilled about having to find the saleswoman again, but he had curtseyed a million times already today. But just before he could drop another one, he suddenly felt himself peeing again. It startled him so much that he paused a bit too long.
“I’m waiting!” Mel said angrily.
Still peeing, Chad was galvanized into motion. He dropped into his curtsey, but before he could come back up again, he felt a strange tickling sensation on his leg. He froze! Then the sensation started continuing down his leg faster and faster. He couldn’t help it, it just came out. “Aaahhh!” he screamed as he looked down his leg. Pee was now pouring all the way down his leg, over the shoes he was wearing, and all the way down to puddle on the floor. He heard laughter and looked up to see Mel coming closer.
“You did it!” she said happily.
Chad would have curtseyed and mumbled more nonsense at her, but he was still too preoccupied with the pee that was still running down his leg, much slower now, but still there. He briefly looked around. Fortunately, it didn’t look like anyone had seen him, but now there was a small puddle of pee on the floor. Now what should he do?
Mel was looking around too now. It looked like nobody had seen. It was time to get out of there. “Change out of those shoes, quickly now,” she said. “And let’s get out of here.”
Chad was more than glad to comply. He was very careful as he unbuckled the new shoes and fastened his old ones back in place again. He didn’t want any more pee escaping out of his sodden diaper. But a little bit did escape. There was no way he could prevent it. Mel had him grab both boxes of shoes along with the frilly socks and they both headed for the checkout counter where they were holding the other clothes he was supposed to buy. As he walked, he figured it was a good thing he was wearing a dress with a skirt instead of pants. The skirt of his dress at least hadn’t gotten wet yet, as far as he knew. If he were wearing pants, the diaper leak would show for sure!
At the checkout counter, he had to pay for all his new clothes. He did so as quickly as possible so they could get out of there. As he signed the credit card receipt, he was struck by how much money he was spending on women’s clothes lately. An awful lot! But his other living expenses were very minimal so he had plenty of money. As they were walking out the door, Chad’s arms heavily loaded, Mel said, “That’s one more demerit for not curtseying and greeting the woman at the register! I didn’t tell you back there because I want to get out of here. But it’s still no excuse!”
Chad couldn’t believe it. Another demerit! Damn!
When they got back to Mel’s car, Mel had him dump all his purchases in the back seat, but she wouldn’t let him get into the car. “I don’t want you soaking my seats,” she explained. Chad wondered what he was supposed to do, run home? But Mel grabbed his diaper bag opened it up and pulled out another diaper. “Pull your skirt up,” she ordered.
Chad couldn’t believe it, was she going to change him? Here? In the parking lot? He was standing next to the car… actually between two cars. But still, anybody walking by would be able to see.
“I’m waiting!” Mel said sternly.
Chad slowly grabbed the hem of his skirt and pulled it up all the way.
“Now hold it there,” Mel instructed as she started removing his overly soaked diaper.
A moment later, Chad was naked from the waist down, out in public, holding his skirt up for all the world to see. He nervously looked around hoping that nobody would notice. What would happen if the driver of the car next to them suddenly came back?
Mel purposely took her sweet time putting the soaked diaper into a plastic bag that they kept in his diaper bag just for such things. Leaving him standing with his skirt up like that had to be humiliating for him. She looked up at his face. Yes, there was no doubt. “Aw, what’s the matter?” she teased. “Worried that someone might see you?”
Still holding his skirt up, Chad dropped another curtsey and mumbled more baby jargon.
“I don’t know what you should be worried about,” Mel continued. “As far as I can see, you’re just another baby getting changed. And there’s certainly nothing wrong with that.” She paused while a wicked grin entered her face. “Maybe next time we should just do it out in the middle of the store where more people can watch… baby.”
Chad wanted to die. And he was still standing there naked below his waist. Change him in the store? She wouldn’t! But then, he couldn’t believe she was actually changing him right here… out in the open… right where everybody parked their cars!
Mel finally rediapered him, making sure the new diaper was properly placed and nice and tight. She stood up and checked her watch again. “Okay, you’ve got two more hours.”
Chad almost fainted.