The Bet
by Karen Singer
Chapter 36 (Saturday – week 5 Part 2 of 8)
Chad stared at the shopping list he had made. He needed an awful lot of stuff. His makeup was running low, he needed shampoo and conditioner. He needed baby wipes and baby lotion. He needed pantyhose. And of course three more packages of diapers. It would take a long time to shop for all that stuff. Longer than he wanted to be out in public by himself, dressed as he was.
Today he was wearing pants again… but they were the tighter pants this time. With only one diaper on and knowing that he probably wouldn’t be wearing them for very long, they had seemed like his best option. It actually felt a bit strange wearing pants again, even with the high heels on his feet. He was also wearing his waist cincher to give himself a bit of a better figure. His shape wasn’t as good without the all-in-one girdle he usually wore too, but the waist cincher did help a lot. Naturally, he had added a bra and his breast forms too – at least they weren’t glued on to him today… yet. A simple casual top, his watch, ring, and necklace completed his outfit. Casual. Actually a lot more comfortable without the all-in-one girdle. It gave him a huge sense of freedom.
He checked his watch. Only a little over an hour to go before he would have to be at Mel’s apartment with a leaking diaper. His diaper was already getting very wet, but it still had a long way to go so he dared not hold back at all. Picking up his purse, he headed out the door and down to his car to start taking care of business.
His first stop of the morning was at the ATM machine to get a pile of cash to use during the week. The cash made life a lot easier, even though he no longer had the super long nails on his hands. As he punched the numbers into the machine with the tips of his nails, he was again struck by the strange purple color. Would he ever get used to them? They were kind of pretty though.
He needed diapers – three packages. But just thinking about shopping for them reminded him of the two girls who had been all too interested in him at his usual drug store for the last two weeks. Purposely, he avoided that store and went further down the road to the next one. The store was crowded as he went inside, but then he was a bit later getting there than he wanted to be this morning. He ignored all the other customers and went straight to the diaper aisle. He was glad to see that they were fully stocked this time. He pulled three big packages off the shelf, and holding two of them while trying to precariously balance the third, made his way to the checkout counter. He realized that the drug store probably also carried most of everything else on his list too, but he didn’t want to have to deal with buying all that along with the diapers. And just carrying it all would have been impossible anyway.
As he stood waiting in the short line, he saw some of the other customers glancing at him curiously. But at least none of them said anything or even looked overly long at him. He was glad. When it was his turn to pay, the saleswoman simply rang him up quickly, dumped all three bags of diapers into three different plastic bags, took his money, and gave him his change. Quick and simple. Just the way it was supposed to be. Things were definitely going better today – so far! He made a mental note to use this drug store all the time from now on.
He checked his watch again as he got back into the car – just over forty minutes to go. He was doing pretty good continuing to wet himself, but there were still no leaks. If he was going to make Mel’s deadline then he had to keep drinking – and he had to keep trying to wet. He drove further down the road to his favorite fast food restaurant and ordered a quick breakfast with a large cup of coffee through the drive-thru. He sat in his car the parking lot while he ate, then got back on the road again the minute he finished.
But where to go next? Time was running out before he had to be at Mel’s door with a leaky diaper. He could tell that his diaper was really wet, but he still hadn’t felt the telltale tickle of any leaks yet. He knew that someplace like Target or Wal-Mart would have everything else that he needed, but stopping at one of those stores would take too long. He turned back towards home instead to wait till after he could get changed before he continued his shopping. But halfway home, he noticed the drug store he had just stopped at a little while ago. The experience hadn’t been bad at all, and most of the things that he needed could be bought there. Trying to save a little time, he quickly pulled back into the store’s parking lot as he felt himself peeing yet again – but he still didn’t feel any leaks.
There were quite a few cars in the parking lot now, but he didn’t think it would be too crowded inside. He entered the store and grabbed a small handheld shopping basket from a stack near the door. At first glance, he was a bit worried about the number of people he saw inside, but he kept going anyway.
The makeup section was first – several long aisles of it. All of which had women looking closely at the various items – too many women for his comfort since he wasn’t all that sure about where to find what he was looking for anyway. He continued on to the next section instead and quickly found the shampoo, conditioner and other bath supplies that he needed. There were only two women in this section, but in the long aisle, that didn’t seem like too many at all. His basket started to fill up quickly, but as he turned from picking up one of the items, he noticed one of the women had been looking at him rather closely. Well, that was nothing new. At least she didn’t say anything. He glanced at his watch, time was running short. As he hurried to the checkout counter, he was pleased to feel himself peeing again – a lot – probably from the coffee he had just finished.
The store had two cash register lanes open now to handle all the customers, with a short line at each one. Chad chose the line that he hoped would get him out of there the quickest. He was aware, as usual, of all the stares from everyone around him, but fortunately, nobody said anything to him. But as he stood there waiting his turn, something suddenly felt odd… then grew more odd. The odd feeling was on his legs, just below his crotch, and it seemed to be expanding! He reached down casually and felt his pants just below his diaper. Wet! He was leaking, and the pants he had on were too tight to let any of it just drip down his leg. They were quickly becoming wetter and wetter as his diaper continued to leak!
He moved up in line, only one other person ahead of him now. He had a basket full of things to buy in his hand. He wanted to just drop the basket and run out, but he had come so far already. He heard someone grunt in surprise, then a moment later, someone giggled. He turned, two women were looking at him. Then someone else noticed him. That someone else grabbed her friend’s arm and pointed at him. Damn! Why didn’t he think about this when he got dressed this morning? His pants were too tight to let him get away with anything! Not only were the people noticing him because he was obviously a man dressed as a woman, but he was feeling extra embarrassed because he was now out with obviously wet pants, and the growing wet stains were letting everyone know that he had just wet himself! He was about to drop everything and just walk out, but just then, the person ahead of him finished and it was his turn to check out. He had come too far now to just leave.
As quickly as he could, he put everything up on the counter from his basket and waited while the cashier rang everything up. Fortunately, she couldn’t see his wet pants. But he had no doubt that everyone else in line was watching him. It took a few minutes to ring everything up, pay for it, receive his change, and wait till it all got bagged before he could finally leave. By then, there didn’t seem to be any use in hurrying too much. Everyone had already gotten an eyeful!
He didn’t dare to glance down at his pants to see how bad they were till he got out of the store and was standing next to his car. And what he saw was shocking. Just from what he could see, he had large wet splotches in several areas at the top of each leg, starting right at his crotch. Some of those wet splotches were starting to grow together. He couldn’t see behind him, but he could now feel how wet he was back there and it felt even worse than the front. He finally opened his car door and threw his bags across onto the passenger seat on top of the diaper bags. But as he started to get into the car, he stopped and noticed that there was a small wet area on the seat already. He had been leaking since before he went into the store and didn’t know it! No wonder some of the people in the store had been staring at him since he went in.
Not wanting to make his seat any wetter, he grabbed one of the large plastic bags that held his diapers and emptied the bag. He sat on the plastic all the way home. He left all his purchases on the seat of his car as he climbed the stairs up to Mel’s apartment and knocked on her door with just a few minutes left to spare. The door opened and he immediately dropped his usual curtsey and recited his sissy greeting.
Mel smiled. “You just made it!” But then she stopped and stared at his wet pants. “But by the looks of things, you could have been here earlier. Turn all the way around. Let me see how bad it is.” Still outside where everyone could see him, Chad slowly turned all the way around. “Why didn’t you come back sooner?” she asked.
“I was out shopping when it happened.”
“In the stores? With people around?”
“Yeah, the drug store.”
Mel smiled. “I hope you enjoyed yourself.”
That wasn’t exactly the way that Chad would have put it!
“Let’s go get you changed,” Mel said as she grabbed her keys from her purse and started toward his apartment. Chad followed behind, allowing Mel to unlock his apartment door for him since her key was already out.
“Did you get everything you need today?” Mel asked as he was removing his wet pants.
“Not yet,” he replied. “I still have to find some of the makeup I’m almost out of, and I need a few more pairs of pantyhose too.”
“Some of that makeup you’re only going to be able to get at the mall.”
He groaned audibly. “That’s the only place? Target or Wal-Mart won’t carry it?”
She shook her head. “Not that brand. You’ll have to go back to the makeup counter where you got it. Of course when you do, you can always ask for another demonstration again,” she teased.
Chad rolled his eyes as he pulled off his saturated diaper and let it drop to the floor. “No thanks. Not today,” he replied.
She smiled but said nothing as she waited for him to tape another fresh diaper in place. “Two hours, Sissy,” she said as she glanced at her watch.
Chad glanced at his own watch too. “Yes, Mistress,” he replied with a small sigh.
She paused before she left him. “Tell you what. I was thinking of going shopping today myself. I need a few things too. If you like, we can go to the mall together and you can get your makeup then.”
Chad thought about that for only a few seconds. It sounded like a better idea to him – despite what she might come up with along the way. Besides, if she was going shopping then he was probably going with her anyway. “Thanks,” he replied. “Maybe I’ll wait till then.”
Once Mel was gone, Chad went back to face his closet. Now what was he going to wear? Pants were obviously out! Since he wasn’t going shopping till later with Mel, he was tempted to stay in just his diaper till she came back at noon. And when Sandy arrived later, he had no doubt that she would have her own ideas on what she wanted him to wear today. But then he remembered that all the things he had bought earlier were still down in his car and they needed to be brought upstairs. He finally chose the most casual looking skirt and top that he could find and the low-heeled shoes that he wore with his uniform. He might as well be comfortable. Since he only had two more hours to go till he had to be leaking again, he pulled another baby bottle out of his refrigerator before going down to the car to get his purchases.
“I really appreciate this,” Sandy said as she opened the door to her apartment and she and Mel lugged the heavy highchair inside.
“No, it’s me who appreciates it,” Mel replied. “What do you have planned for him today?”
“I was thinking of a couple of things. But mostly, I’d like to start working on the way he does things… the way he moves. Babies don’t quite have the motor control we have, so they do things a bit differently. I’d like to try a few ideas on that line today.”
“Sounds interesting,” Mel replied. “Actually, that’s something I need to start working on with him too, although in a completely different way. He’s still got too many masculine mannerisms.”
Sandy giggled. “Well then, maybe between the two of us we can eliminate a few of them.” Mel giggled too.
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