The Bet - Chapter 51 (Sunday – week 8 part 2 of 8)

The Bet

by Karen Singer

Chapter 51 (Sunday – week 8 part 2 of 8)

     When his breakfast was over, Mel cleaned him up and brought him into her bedroom to get him dressed again.  But the first thing she did with him was to take the time to reglue his breast forms back onto him again.  She actually felt better as soon as she had done it.  It was one of those little masculine things that she was denying him.  She only hated that she had to take them off of him once in a while. 

     After that, she had him put his bra and socks on while she went to the closet and pulled out the same ruffled pink and white dress she had made him wear yesterday. 

     Chad groaned with terror the moment he saw the dress.  He didn’t want to believe that she would actually make him go out in it again, but he knew perfectly well that she would.  In fact, he knew that going out in it was probably a foregone conclusion!  A few minutes later, he was once again dressed in the silly frilly dress with his pink patent high heel shoes on his feet.

      “Okay, Sissy,” Mel said as she quickly led the way out of the room.  “Let’s get out of here!”

     Chad followed her out to the living room where he collected his purse and diaper bag.  Then, dreading going out in his stupid dress again, he followed her out the door and down to her car where he “crushed” his dress into the front seat and belted himself in place.  Mel handed him yet another baby bottle to drink as she drove, and they were off to the grocery store. 

     Drinking a baby bottle while driving around in her car was starting to feel normal – even though he was humiliated to death by everyone who saw him.  He figured he must be a major subject of conversation all around town by now.  And if he wasn’t, then the dress he would be wearing all through the grocery store in a few minutes would certainly make him one!

     His bottle wasn’t empty by the time Mel parked the car, so she made him carry it in with him – along with his diaper bag.  The moment he stepped out of the car, Chad was once again very embarrassed by his dress.  Getting inside the grocery store didn’t make things any better.  People were staring at him and pointing at him constantly.  Well, he couldn’t really blame them.  The fact that Mel was making him finish his bottle as he pushed the cart only made things worse.  The only thing he was hoping for now, was that they would get out of there before his diaper started leaking.  Despite having to glue on his breast forms, Mel had rushed him enough so that they were ahead of their usual schedule. 

     Pushing the cart, and pulling items off the shelves was difficult to do while being forced to drink from a baby bottle, but Mel was making sure he kept drinking.  While he was horribly embarrassed about it, he took a little comfort in the fact that so far, it was only his second bottle of the morning – a major change!  While he wasn’t peeing as often as he sometimes did – nowhere near like he had last night, because of his deadline, he was still peeing fairly regularly and frequently. 

     Pushing the shopping cart in that dress was its own nightmare.  In order to just push the cart, he had to crush the front of his skirt down against the cart a bit, which gave him the impression that the back of his skirt was raising up when it happened.  Was it?  In the mass of ruffles he was wearing, he wasn’t totally sure.  It was just another one of those things for him to worry about.  Could the other customers see his diapers?  Did it matter?  Unfortunately, while the reality was that it didn’t matter, it still mattered to him.

     Because of his dress, he was very aware of every other person in the store.  Involuntarily, he noticed whether any of them were looking at him.  And the answer was almost always a big fat yes!  But then the answer to that question couldn’t be anything else because the dress he was wearing absolutely screamed for everyone to look at him! 

     They hadn’t gone very far at all in the store when they came to a section that held the first item he needed.  Unfortunately, that item was on the very top shelf.  Things he wanted were often on the top shelf and he didn’t give it a moment’s thought before he started to reach for it.  One of the things he liked about wearing high heels was that it often made reaching up for things easier, but this shelf was beyond the range where he could just stand and reach up without his heels leaving the floor – even the four inch heels he was wearing then.  But he still didn’t think about it as he approached the shelf with his eyes locked on the jar he wanted.  He took one step closer… and his crazy skirt started crushing itself against the items on the shelf at waist level.  He reached up and stood on his toes, and the extra motion that got transmitted to his skirt, made it move enough to make some of the boxes on that shelf fall off.  He quickly stepped back again, which only threw more boxes down on the floor. 

      “Be careful!” Mel warned angrily. 

     He quickly bent down to get the small boxes, but just like the day before in the ladies room, his skirt was mostly in the way.  The best way for him to do it was to stand a bit straddle legged and push his skirt down first while he picked up the boxes and stacked them back on the shelf.  With each time he bent down to get something, he was aware that he was clearly showing off the diaper he was wearing underneath, but there was little he could do about it.  He heard Mel sniggering at him a few feet away. 

     Once everything was back on the shelf again, he still had to reach the item he needed.  This time he carefully approached the shelf, pushing down on the front his skirt with one hand to get it out of the way.  But despite all the crazy ruffles, pushing down on the front of his skirt made it rise up in the back a little.  He tried pushing the skirt down a few times and letting it up, which only sent his skirt into continuous motion. 

      “Stop playing with your dress and let’s keep moving!” Mel ordered.

     Having no other choice, Chad pushed his skirt down again in order to get close enough so that he could stand on his toes to reach the top shelf.  He got the item, but in the process he realized that his skirt was just wide and obtrusive enough that he would have to push it down every time he wanted anything off of any shelf.  Once again, the darn dress was a nightmare!

     They finished the first aisle and turned down the next one, both of them continually searching the shelves for anything they thought they might need.  Sissy, of course was also trying to push the cart with one hand while he finished his baby bottle with his other.  It made pushing the cart a bit more difficult, but the cart was still mostly empty so it wasn’t too bad.  Halfway down the aisle, he started sucking air.  He quickly opened the diaper bag and stuffed it inside, then he closed the bag again so he could keep shopping. 

      “You didn’t get another bottle?” Mel asked. 

     Chad didn’t need to ask if she wanted him to get one, he knew she did.  He opened the bag and grabbed a fresh bottle.  It was only his third one of the day, and it looked like Mel wasn’t going to let him go without one in his mouth as long as they were out.

     A few more items went into his cart on that aisle, and they turned the corner again and headed up the next one.  This one was a bit more crowded with shoppers and carts going in both directions.  Sissy was forced to keep his cart close to one of the shelves so others coming from the opposite direction could get through.  He was also forced to keep a close watch on his skirt so it didn’t rub on any of the shelves and knock anything off again.

     Halfway up the aisle, one of the women coming from the opposite direction needed to pass.  Sissy had already noticed that she had rarely taken her eyes off of him since he entered the aisle.  He made sure his cart was as far to the side as possible to give her plenty of room.  As usually happened, the closer someone came to him, the more embarrassed he felt about himself.  The woman steered her cart to the far side and started to pass.  Embarrassedly, Sissy looked away from her and down at the floor, his baby bottle held low by his side.  But the woman didn’t pass completely.  Instead, she stopped right next to him.

      “I just had to tell you,” she said excitedly, “I just love your dress.”  She was giggling slightly. 

     Sissy was shocked that she would even stop to speak to him.  He looked up quickly at her, half frightened by the exchange.

     But Mel had also noted the woman’s complement.  “Thank her properly, Sissy,” she ordered quietly.

     More embarrassed than ever, Sissy curtseyed and said, “Thank you,” in his sissy voice.

     The woman giggled louder.  Then she reached out and felt some of the ruffles on several areas of his dress.  “They’re so soft,” she commented.  “Wherever did you get this?”

     Chad looked uncertainly at Mel – who was only staring at him as if daring him to make a mistake.  Before speaking, he curtseyed yet again.  “It wath a gif fwom my mithdweth,” he lisped.

     The woman thought she knew what he had said but she asked, “A gift?  From your mistress?”  Then she looked at Mel for confirmation.  Mel just nodded her head to confirm it.  “Well, I think it’s adorable!” the woman gushed to Sissy.

     Chad curtseyed before saying “Thank you,” once again.

      “Why don’t you show her your pretty fingernails,” Mel suggested.

     Chad was already uncomfortable enough that it was all he could do to keep from running, but he brought his free hand up and held out his nails that now spelled “Sissy” on them.

      “Oooh,” the woman cooed.  “I think they’re so cute!”

      “Show her your other hand too, Sissy,” Mel said.

     Chad had been holding his baby bottle down at his side with his other hand.  He had to set it in the cart before holding out both hands to show off his nails. 

     The woman laughed and looked back at Mel.  “Which one is his name… and which one is what he is?”

     Her question sent Mel into a small fit of laughter.  “Take your pick!” she finally replied.  Then to Sissy she said, “Thank the nice lady again.”

     Again, Sissy had to curtsey and thank her.

     But the woman had noticed that he curtseyed before he spoke each time.  She turned to Mel, “So polite!” she commented.  “You don’t always encounter anyone so… polite, when you’re out shopping anymore.”

      “Almost never!” Mel agreed.

      “Such a shame,” the woman replied.  Then she turned back to Sissy.  “And I really do love your dress,” she said as she reached out to touch it one more time.  She giggled as she walked past him.  “Have a nice day!”

     Chad curtseyed yet again before thanking her even though she couldn’t see him doing it.

      “You see,” Mel said teasingly, “people do appreciate little things like you curtseying all the time.”

     Yeah right!  What they appreciated was a reason to laugh at him!

     But now two more people were pushing their carts in his direction, a woman first, followed by a man.  Chad could see that the woman had a very uncertain look on her face.  He couldn’t blame her.

     Mel noticed the carts heading in their direction too and moved off to the side so they could get through.  “I think it would be very nice,” she said softly to Sissy, “if you would curtsey for each of them and say good morning.  Don’t you think they would appreciate that?”

     Chad didn’t have to answer, because the woman started to pass.  He let go of his cart handle, curtseyed to the woman and said a sissy good morning to her.  The woman looked startled, if not a bit scared, but she smiled and returned a cautious good morning back before hurrying ahead.  The man following her saw what happened and tried not to slow down as he passed, but Chad’s curtsey and greeting made him pause slightly.  He nodded his head and smiled before quickly continuing past.  Neither of the shoppers stopped till they were gone from the aisle and out of sight.

      “There, did you see?” Mel said.  “You brought a smile to both of them.  People don’t have enough to smile about these days,” she added.  “Wouldn’t it be awfully nice if you tried to brighten up everyone’s day that you meet here?  I think you would be doing so much good for everyone.  And I’m sure that it would make you feel simply great to know how happy you’ve made so many people.  In fact, maybe you should also ask each of them if they would like to see your pretty fingernails too.  I’m sure a lot of people will absolutely love seeing them!”  Without another look, Mel walked on ahead.

     Chad just stood and stared at Mel’s back in disbelief for a few moments before he followed her.  She actually wanted him to curtsey and greet everyone in the store?  He wasn’t sure if this was worse than getting his diaper changed here last week or not.  In some ways, it was definitely worse!  Last week she had partially hid him behind the shopping cart when she changed him, but there would be no hiding if he was supposed to be greeting everyone today.  In fact, it would be just the opposite.  He would be going out of his way to be more noticed!  As if his stupid dress wasn’t enough!

     It wasn’t long before more shoppers turned onto the aisle they were in, which meant that it wasn’t long before Sissy was dropping another curtsey as the first man passed by.  “Would you like to see my fingernails?” he asked the first man.

      “Uh…  No thanks,” the man replied uncertainly.  It was obvious he just want to get past and away from Sissy.

     But Mel wasn’t quite satisfied with the way Sissy had asked about his nails.  “Make sure you ask if they want to see your ‘pretty’ fingernails,” Mel told him.  “Try it again on this next woman.

     As the woman passed, Chad dropped his curtsey and said his sissy good morning.  Then he asked if she would like to see his ‘pretty’ fingernails. 

     The woman was startled and uncertain.  But half of it was because of his silly lisping voice.  But she was now curious.  “Sure, I guess,” she replied. 

     Chad was forced to hold out his hands so she could examine his nails. 

     The woman actually held his fingertips with her own hands as she examined them.  “How… appropriate!” she finally said as she dropped his hands.  “Thank you.”  And then she moved on quickly.  She had decided to move to another aisle to shop.  She would come back to this one later – after the weirdo was gone!

      “See how nice that was!” Mel commented.  “Now I just know she really appreciated that.  You probably made her day!”

     That much Chad was sure of.  Yes, he had made her day, and she would probably be spreading the word about it to everyone she met – for months!  He remembered that odd little though he had earlier about being the talk of the town.  There was no doubt about it now!

      “Don’t forget the nice people who are following behind us too,” Mel noted.  “If you can see them, then I’m sure they can see you too.  And I just know they don’t want to be left out!”

     They could see him too?  Of course they could see him.  His crazy dress was practically a big neon sign drawing their attention! 

     As much as Mel was trying to hurry earlier, their shopping slowed down to a crawl as they had to wait while Sissy curtseyed, said good morning, and asked everyone if they wanted to see his fingernails.  Sometimes he wound up doing it to the same person two or three times as they passed in different parts of the store.  And when he wasn’t curtseying, Mel made sure he was still drinking his bottles!  And through all that, Chad still had to get the grocery items he needed!

      “Are you leaking yet?” Mel asked as they reached the half-way point through the store. 

     Chad was getting tired of curtseying constantly, but he had to do it yet again just to talk to Mel.  “No, Mistress,” he replied.  “There’s should still be plenty of time though.”

     Mel’s only reply was to look at her watch and then back at him again as she raised her eyebrows. 

     Chad suddenly had to wonder, how much time was really left?  He wasn’t wearing his watch today so he had no idea at all!  There had been plenty of time when they started, but grocery shopping was now taking longer and longer!  He started sucking on his latest bottle with renewed vigor! 

     A while later, they were coming to the end of the second to last aisle.  Sissy was working on his the last full bottle from his diaper bag.  Just before they turned the corner, he felt the first telltale tickle of a leak.  “Mistress,” he said excitedly, “I’m leaking!”  He was glad that he had made it on time – he hoped.  At least Mel hadn’t indicated that his deadline was past.  His worry now was if she would change him in the store again like she did last week.

     Mel looked at her watch, then up at Sissy.  “That was certainly close!” she said.  “But now we have to figure out how to change you.”  She looked around.  The store had become a lot more crowded since they had entered – something she had already noted by the frequency that Sissy was having to greet everybody.  She walked out of the aisle and glanced in both directions, the final aisle at the end of the store was much busier than anywhere else.  And not far from it was a tall bread rack that some worker had left out.  And it was still full!  Perfect!  She could hide him behind the bread rack and the cart both while she changed him.  Just as she was about to tell Sissy what she planned on doing, another thought hit her – and it ruined all he plans!  Darn it!  She turned to him.  “Sorry Sissy.  You’re just going to have to keep leaking till we get out to the parking lot.  If I take that diaper off of you in the store, then you’re all too likely to pee all over their floor!  And I know that nobody would like it!”

     Chad was surprised that she would say that.  Unfortunately, he knew it was also all too possible.  And… he was glad she wouldn’t be changing his diaper in the store – in front of anyone else!

     By the time Sissy had curtseyed and talked to everybody he saw in the final aisle, showing about half of them his fingernails that said “Sissy” on them, the leaking pee was running down both legs and the tops of his sissy socks were starting to get awfully wet.  His biggest worry was while they were standing in the checkout line waiting for the cashier to ring them up.  He worried that he would be making a mess on the floor if too much of it dripped past his socks and shoes.  Fortunately, the cashier only looked at his fingernails very briefly since she was busy, and he and Mel were back out in the parking lot before too long.  Once the groceries were out of the cart and the cart was put in the rack with the other empty carts, Mel stripped his soaked diaper off of him while he stood between her car and another one.  And a minute later, he was once again in a dry fresh diaper – with a fresh time limit to be leaking again!  He was more than ready to get home!