The Bet - Chapter 51 (Sunday – week 8 part 5 of 8)

The Bet

by Karen Singer

Chapter 51 (Sunday – week 8 part 5 of 8)

     Mel looked at the skirts again.  Now she needed some kind of top to go with them.  She started looking at the racks again, but when she reached the end of one of the rows, she saw a sale table not far away.  And the sale looked like a very good one.  She wandered over to check it out.  Unfortunately, the table appeared to be all clothes that didn’t sell last winter.  But one of the sweaters caught her eye.  She picked it up to look closer.  It was a short white angora wool sweater with a cute little pink bow in the middle of the neckline.  It was really too warm to wear now, but it was still pretty.  And even though she didn’t usually worry about the price, the sale made it all that much more attractive.  The fact that it was in his size and he could wear it with either skirt pretty much sealed the deal.  She carried both skirts and the sweater back to the changing rooms.

     Sissy was almost done with his bottle when the door suddenly opened and Mel came in.  He could see immediately that the skirts she had in her hand were short – very short. 

      “Okay Sissy,” Mel said as she held the blue check skirt out for him.  “Try this on.”

     Chad took the skirt and held it up briefly.  The thing really was short!  Sinfully short!  But with a feeling of excitement, he pulled it on and zipped up the tiny zipper in the back.  He turned toward the mirror.  Damn the thing was short – but exciting to wear.  Just as long as he didn’t have to actually wear it anywhere!

      “Here,” Mel said next as she held out the sweater.  “Try this on with it.”

     Chad was surprised at how thick the sweater was.  It looked more like something for winter.  But he pulled it on.  The sweater was fairly short too.  It didn’t even quite reach the top of his skirt.  A little bit of the waist cincher he was wearing underneath showed through.  And the darn thing itched… everywhere it touched his bare skin!  He was suddenly thankful for his waist cincher.  “It itches,” he complained.

      “Tough!” Mel replied as she looked him over.  She opened the changing room door.  “Go out and show Derek.”

     What?  Show Derek?  That wasn’t at all what he wanted to do – especially not in that outfit.  But Mel was holding the door wide open for him.  Sheepishly he went out.  Derek was standing a few feet away.  The salesgirl was a few feet further behind him.  The loud snort of laughter he heard came from the salesgirl.

      “Curtsey,” Mel ordered softly from the door to the changing room.

     Chad curtseyed to Derek, and once again he was too embarrassed to pull his eyes from the floor.

      “What do you think?” Mel asked Derek.

     Derek smiled.  “I think it will certainly up the attention he’s been getting.”

     Chad was amazed and horrified that Derek should say such a thing.

      “I want to try the other skirt on him too,” Mel told Derek.  “I’m not sure it will fit though.”

     A minute later, Chad was pulling off the blue plaid skirt and replacing it with the green and red plaid one.  This one was much tighter on his waist, but he did zip it up without too much trouble.  And he wasn’t sure, but he thought the thing was actually shorter than the first one.  He turned to Mel and curtseyed.  “I think it’s too small.”

      “I don’t know,” Mel replied.  “You didn’t have much trouble getting it on.  Go show Derek.  Let’s see what he thinks.”

     Once again, Chad sheepishly went out of the changing room to show Derek the outfit.  And once again, he curtseyed for him.  There was no snort of laughter from the salesgirl this time, but when he embarrassedly looked up a little, he could just see how wide-eyed with amazement she was.

      “What do you think?” Mel asked.  “I like the color on him better than the other one.”

     Derek nodded.  “I don’t know much about color,” he replied.  “But it looks to me like that one is even shorter than the other one.  He’ll certainly get even more attention with that one.  And maybe you’re right about the color.  It is brighter so I guess it will be noticed more.”

     Nothing Derek had said was anything that Chad wanted to hear!

     Mel turned to the salesgirl.  “We’ll take them.  And he’ll be wearing them now.  We just need some scissors to cut the tags off.”

     That also wasn’t something that Chad wanted to hear!  Not at all!

     Mel sent him back into the changing room to put his shoes back on and to get his clothes.  But when he came back out, she stopped him so she could take another good look at him.  She turned to Derek.  “Those shoes don’t go with that outfit at all.”

     Derek looked at Sissy’s tan high heels.  “I guess they don’t,” he replied.  “What do you suggest?”

     Mel looked at the Sissy in the outfit again.  “It’s kind of a schoolgirl outfit,” I guess.  “Isn’t that what you guys fantasize about?”

     Derek only raised his eyebrows in surprise.  He wasn’t about to answer the question out loud though. 

     The salesgirl returned with the scissors.  Mel turned to her.  “You wouldn’t happen to have any knees socks, would you?”

     The girl only smiled.  “Of course.  Right this way.”

      “Sissy, go take those shoes off again,” Mel told him.  “I’ll be right back.”

     Mel followed the salesgirl to the other side of the store where she was shown a selection of socks – all kinds of socks. 

      “We have a few more in here,” the girl said as she pulled open a drawer.  “But these may be too heavy to wear now.”

     Mel glanced into the drawer to see what the girl was talking about and immediately noticed how much thicker those socks in the drawer were.  But something red immediately caught her eye.  She reached into the drawer and grabbed them.  They were a pair of bright red woolen knee socks… and they would go perfectly with his skirt and his angora wool top!  “These will work nicely,” she declared.  She immediately turned and carried the socks back toward the changing room.

     Since he seemed to have time, Chad had just dug another baby bottle out of his diaper bag again.  But he barely started drinking it when Mel came in with some socks.  Red socks.  And they were knees socks!  And as soon as he pulled the first one on, he felt it itching his leg.  Wool socks!  Ugh!  With the heavy socks on though, he had a lot of trouble getting his heels back on.  And between them and his sweater, he wanted to claw at his skin all over.

     Once his shoes were back on, Chad thought he was ready to go – as embarrassing as his outfit was, but Mel had noticed something else she didn’t like.  “Take that waist cincher off,” she told him.  “It shows under your sweater.”

     Take it off?  The waist cincher was the only thing that was keeping the sweater from being unendurable!  But he removed the sweater, and then had to remove his skirt too to get the waist cincher off.  While he was removing his waist cincher, Mel removed the tags from his new clothes.  Then he got dressed again.  Only now he noticed how short the sweater really was.  When he bent or moved at all, the skin at his waist was definitely exposed between the sweater and his skirt.  And without the waist cincher, since the skirt was so tight at the waist, he had to move it up a bit higher on his waist to fasten it so that the top of his diapers wouldn’t be in the way.  Short skirt, short sweater… long socks.

      “Much better,” Mel declared happily. 

     Better?  As far as Chad was concerned things were much worse!  The sweater was really bothering him now.  As were the wool socks.  And he was suddenly much more aware of how warm everything was – well, maybe not the skirt.  But of course, part of that warmth could be from how frightened he was about having to wear them – out in the mall! 

     Mel led the way out toward the cash register so she could pay for the clothes.  Chad followed her carrying his diaper bag.  As he walked, he kept twisting his body, trying to do something about the horrible itching from his sweater.  But the darn thing clung so tightly that all his movement had no affect at all. 

     Derek brought up the rear as they headed over to where they could pay for everything.  As they walked, he noticed how Sissy kept jerking around a bit as if he was very uncomfortable.  He noticed something else too!

     Chad was glad that Mel had decided to pay for his things instead of having him pay for them himself, but as Mel was paying, he kept glancing out into the busy mall area again.  In just a minute he would have to go out there wearing… this!  The thought was horrifying, and humiliating… and exciting! 

     As soon as Mel had finished paying for everything, Mel ordered Sissy to lead the way again – and to make sure he went slowly, just like before!  Chad started walking from the cash register out toward the entrance to the store. 

      “You know,” Derek commented to Mel, who was again at his side.  “That skirt he’s wearing is so short that every time he moves or twitches too much, you can see a tiny bit of the white underneath from the diaper he’s wearing.  It’s a good thing that diaper isn’t any thicker!”

     Just then, Sissy twitched strongly again from the itching and Mel noticed the tiny little flash of white beneath it.  She stopped dead which stopped Derek too.  Sissy, not knowing they had stopped, kept going slowly out toward the mall.  He twitched again at the itching and again Mel saw the flash of white. 

      “Sissy!” Mel called.  “Stop right there!”

     Chad heard her and turned around.  They were just standing there looking at him.  Why?  Okay, he knew he looked ridiculous, but they already knew that.

     Mel, still staring at Sissy, said to Derek.  “You said that if his diapers were any thicker…”

      “What of it?”

     Mel shook her head.  “Darn you!  Okay I guess.  Just this once!”  She yelled to Sissy.  “Sissy, get back here!”

      “What did I do?” Derek asked. 

      “I didn’t really want to do this with him,” Mel explained.  “Not now since I’m trying to keep him on a time limit.  But…”  She looked up at him with a devilish look in her eye.  “I’m afraid I just can’t resist!”  She turned and led the way back to the changing room again. 

     Chad was very surprised to be going back to the changing room again.  Now what?  Maybe they decided his skirt was too short after all.  Or maybe they were going to take pity on him and find him something to wear other than the miserably itchy wool sweater he was wearing.  He could only hope. 

     Chad was surprised when Mel had him take his skirt off again and lay down on the floor.  She opened his diaper bag and pulled out a fresh baby bottle for him.  “You can start working on this,” she told him without telling him anything else.  He put the bottle to his mouth and started drinking.  He did have that leaking deadline!

     But then Mel did something that really surprised him.  She started cutting slits all over the diaper he was wearing.  And then she began preparing more of them.  A few minutes later, Chad was very surprised to find himself wearing not one, not two, and not three… but four layers of disposable diapers!  And then Mel pulled out a pair of his plastic panties and slipped them on top of everything else!

      “Those diapers had better be absolutely soaked by the time we get home!” Mel warned.  “Or so help me, I’ll have Derek beat you black and blue!”

     The threat of Derek beating him sunk home immediately.  Chad was allowed to get up and put his skirt back on.  But when he did, he immediately noticed two things.  First, as he moved, the plastic panties he was wearing made an awful lot of noise.  Whenever he wore plastic panties, they were usually covered up by his all-in-one girdle so they didn’t make any noise at all.  But now, nothing covered them.  And that was the second thing he noticed.  His skirt was so short that when he looked in the mirror, even he could just see the childish pattern on his plastic panties sticking out below the bottom of his too short skirt.  Mel intended on making him walk through the mall in not just this schoolgirl outfit, but showing off that he was diapered underneath too!

      “Much better!” Mel proclaimed as she looked him over.

     Much better?  Chad was totally horrified!  A few minutes later, he was again heading through the store out towards the mall area.  He wasn’t having to try so hard to walk slower this time because the four diapers he was wearing were making him waddle more than walk! 

     As he reached the store’s entrance and was about to take his first step out into the mall area, he paused to look back, both Mel and Derek were watching him closely.  Too closely!  And in a few moments, everybody else in the mall would be watching him too closely too. 

     Not having any other choice, he took that first step out into the mall… and kept going… waddling… slowly.  He felt so exposed!  More so than ever before!  The crazy skirt he was wearing was so short that he felt like his legs were totally exposed – which they really were.  And the knee socks only seemed to make things feel that much worse!  And then there was the fact that everybody could see the plastic panties.  That alone was horribly humiliating!  And on top of all that, the damn sweater and socks he was wearing itched horribly!  He wanted to scream!  And he couldn’t do anything about it!

     He immediately noticed how everyone he passed now looked him over – very closely.  So many of them now pointed at him.  So many of them actually laughed!  He couldn’t blame any of them one little bit.  He would have laughed too – if he were in their position.

      “I’d say he’s a lot more noticeable now,” Derek noted.  “Not to mention I’ll bet the little shit it embarrassed as hell!”

     Mel only smiled.  “We’re not done yet!”

      “Not done?”

      “Nope!  He still needs shoes to go with that outfit, and I think… a few accessories too.”

      “So where to now?” Derek asked. 

     Instead of answering him, Mel called ahead to Sissy.  “Sissy, there’s a big shoe store up ahead.  We’re going there!”

     Chad wanted to hurry into the shoe store – just to get out of the main mall area where there were all too many people.  But every time he tried to move any faster, Mel slowed him back down.  It was infuriating – like the miserable itching from his sweater and socks!

     The shoe store was big, and there were a lot of people in it, men and women – and kids.  Sissy instantly turned heads the moment he entered.  But still, there were a lot less people in the store than out of it!  Once Mel and Derek got to the store, Sissy again followed them around – closely.  Now that he was away from the main area of the mall again, things were quiet enough for him to once again hear the crinkling of his plastic panties.  There was just no getting away from all the little humiliations he had to endure.  Not to mention getting away from the horrible itching from his sweater and knee socks!  He figured it was a good thing he had his diaper bag and was carrying the bag that now held the clothes he arrived in, because they gave him something to grab and keep his hands busy.  Otherwise, he’d be clawing like crazy at his body under his sweater.

      “There!” Mel said after spotting what she wanted.

     Chad looked at the shoes she was heading for.  Black and white saddle shoes!  Mel handed him the display shoe and he was sent off to find a salesperson to get him the shoes in his size.  “And don’t forget to curtsey every time you open you open your mouth!” Mel called after him.  Ugh!  And worse, Chad had no doubt that both Mel and Derek would be watching him!

     Since the store was fairly busy, so were all the salespeople.  Chad had to wait up by the registers where they all seemed to be helping other customers.  But fortunately, the outfit he was wearing seemed to scream for attention and it wasn’t long before one of the salesmen came out to help him.  Chad forced himself to curtsey before he handed the guy the saddle shoe and told him his foot size.

     The guy looked dubiously at Chad for a moment before saying, “Of course!” as if he would have expected Chad to be wanting that particular shoe.  Chad followed him toward the store room just because it was further away from so many people.  A few minutes later, the man came out and handed Chad a box of shoes.  Chad carried them over to Mel and Derek where he was made to sit down and try them on.  Since they tied instead of buckled, they were a bit tight over the thick wool socks he was wearing, but not bad at all.  And as much as he liked heels, they were a lot more comfortable than the shoes he had just taken off.  In fact, as bright and noticeable as they were, they were the least humiliating thing he was wearing!