The Bet - Chapter 64 (Saturday – week 9 Part 3 of 7)

The Bet

By Karen Singer

Chapter 64 (Saturday – week 9 Part 3 of 7)

     Two cars pulled into the apartment project and followed each other around toward where Mel and Chad’s apartments were.  When they parked, right next to each other, Gloria got out of one and Andrea got out of the other.  “Hi Andrea,” Gloria called brightly as they met in front of their cars.

      “Hi Gloria,” Andrea returned happily.  “Are you ready for this?”

     Gloria held up the bag she was carrying.  “More than ready!  It’s long past time this bet was over with!”

      “I agree!” Andrea replied whole heartedly as she turned toward the stairs carrying her own bag. 

     Before they reached the top of the steps, both Sandy and Cassie came out on the landing to wait for them.  After exchanging a few pleasantries, Gloria looked around.  “I don’t see Robin yet.”

      “I guess we’re still waiting,” Sandy replied.  “It’s still a few minutes early.”

      “Maybe we should take this opportunity to go have a little chat with Chad,” Andrea suggested.  “He has to get ready, and that could take him a while.”

      “Good idea,” Gloria replied.  She looked to Sandy and Cassie.  “Want to come?”

      “At least one of us needs to wait here for Robin,” Cassie replied.  “I’ll stay here.”

      “I stay behind too,” Sandy agreed.  “You two can go break the bad news.”

     Andrea smiled.  “Bad news?  You never know, he may like it!”  They all laughed, but they all also knew that it might be true.  Maybe.  Before leaving, Gloria and Andrea handed their bags off to Sandy and Cassie.

     Mel checked the clock again.  Twelve twenty-five.  The minutes were starting to drag out interminably!  And still she didn’t have a clue what was going on in Chad’s head.  He was still wandering around with that same stupid coffee mug in his hand, staring at the floor – just as he had done all morning long! 

      “Damn!” Chad exclaimed as he suddenly stopped his wandering.

      “What?” Mel asked as she sat up quickly, thinking something was wrong.

     Sheepishly, Chad looked up at her.  “I have to go change.  I’m… leaking.”

     Mel’s face broke out into a broad smile.  She was definitely winning!  “Go right ahead,” she told him.  “And this is probably a good time since they’ll be here in another half-hour.”

     He nodded and headed for the door.  But the sudden sound of somebody knocking startled him completely. 

      “It’s too early for the ladies to be here yet,” Mel said as she quickly got to her feet. 
     Chad merely shrugged and opened the door – to find both Gloria and Andrea on the other side.

      “There you are!” Gloria said as she laid eyes on Chad.  “We checked your apartment but you weren’t there, so we figured you had to be here.”

      “Hi Gloria.  Hi Andrea,” Chad replied as he stepped back to let them in.  “Um… I was just leaving for a few moments.  But I’ll be right back.  You’re a bit early anyway.”  The truth was, he wasn’t glad to see them at all!

      “You’re early,” Mel said brightly as she came around the furniture to greet them.

      “Um… You’ll excuse me,” Chad said quietly as he started to walk through the door.

      “Wait!” Andrea stopped him.  “Stick around for a minute.  We’re only here to talk to you for a minute first.”

      “But I have to…  Um…”

     Andrea shook her head.  “You need to hear this first.  We’ve got some early instructions for you.”

      “Early instructions?” Mel asked.

     Ignoring her, Gloria spoke next.  “Chad… we know you’re not going to want to hear this, but we have some very good reasons for it.  And like it or not, you’re going to have to do it.”

     Chad was instantly worried.  “Do… what?”

     It was Andrea who replied.  “Dress like a girl… or a woman in your case.”

      “What?” both Chad and Mel exclaimed together.

     Gloria held up her hand.  “We have some very good reasons!” she insisted.  “Your job now is to go home and change.  And for your sake, I recommend that you try to look as much like a woman as you can.  But even if you don’t it won’t matter, except that you’ll probably just be a lot more humiliated by everything.”

      “But he may like that part,” Andrea added with a slight giggle.

     Gloria looked to her and shrugged.  “True.  He may.”

      “Chad,” Andrea said.  “We need you to wear a skirt… or a dress.  I think a skirt may work the best though.  And it needs to be one that’s not too long and that will be easy enough for us to lift up and check any time we want.”

      “A skirt?” Chad asked incredulously.

      “I know you have plenty!” Gloria told him.  “So don’t go acting like it’s any big deal.  You just spent the last two months wearing them and you went everywhere that way, so this should be a piece of cake for you!”

      “Besides,” Andrea added, “It looks like the clothes you’re wearing now don’t exactly fit very well anymore.”

     But Chad had picked up on something else.  “We’re… going somewhere?”

     It was Andrea who replied, with a rather sly look on her face.  “Perhaps.”

      “Uh… okay… I guess.” Chad replied.  He was quickly becoming more worried about his leaking diaper.  “Now if you’ll excuse me.  I guess I have to change.”

      “Oh!” Gloria exclaimed.  “If you feel the need, you can wear one diaper under your skirt.  Got that?  And bring a spare with you as well.”

      “Wear a diaper?” Chad asked, wondering if he had heard her right.

      “If you still feel like there may be some need for it,” Andrea replied.  She was a little surprised that he would question their offer to let him wear a diaper.  Maybe he really had gained all his control back already.

      “Got it,” Chad replied.  “One diaper – maybe.  And look like a woman.  Can I go now?”

      “Absolutely!” Gloria replied.  “And we’ve got to go as well.”

      “You can’t stay here?” Mel asked.

     Andrea shook her head.  “We’ll be back in a little while… at one o’clock.”

      “I’ll come with you then,” Mel said as she started to get her purse.

      “No!  You stay here,” Gloria told her.  “Like we said.  One o’clock.  We have some things to… discuss first.”  She turned to Chad.  “And you better hurry!  Don’t be late!”

     Chad nodded and hurried off toward his apartment.  As he got there, he saw Robin climbing up the stairs with a small bag in her hand.  “Hi Chad,” she called brightly. 

      “Hey Robin,” he returned quickly.  Then he opened his door and hurried inside.  He had only half an hour to get ready.  And what they had asked of him was the last thing he ever expected.  What did those conniving women have in mind?  More humiliation!  He was just betting on it!

     Well, he would show them!  He hoped.

      “Do you mind if I at least help Chad?” Mel asked as Gloria and Andrea got back outside.

      “I don’t have any problem with that at all,” Gloria replied.  “Maybe you can hurry him along.  We’re cutting this awfully close as it is.”

     Mel grabbed her purse and followed the two women out the door – straight to Chad’s apartment.  She didn’t bother knocking, she just used her key to let herself in.  “It’s just me!” she yelled as she went in through his door.

      “I’m in the bathroom!” Chad called.

     Mel was just in time to see him removing his totally soaked and now leaking diaper.  She couldn’t help it.  She giggled a bit.  “You really don’t have any control anymore!” she said teasingly. 

     Chad wanted to tell her to shut up, but instead he replied.  “I’ve got some!”

     Mel wanted to tell him that it looked like however much he had wasn’t going to be enough, but she held her tongue.  A few minutes later, she was in his closet with him, helping him decide what to wear. 

      “Anyone need a drink?” Sandy asked as the ladies all gathered around her kitchen table.  Everyone proclaimed that they were fine without one.

      “Do you have the backpack?” Gloria asked Cassie.  Cassie reached down behind the table and pulled one up from the floor.  “I think this should work pretty well.”

      “Excellent!” Gloria replied.  “Now… let’s see what we all brought.  With that, each woman dumped out the contents of the bags they had brought with them.  Sandy and Cassie, just brought theirs over from the kitchen counter.  The table was quickly covered with thin satiny panties.  Each of the women had agreed to purchase two pairs for the proceedings. 

     Andrea looked around at what each of them had bought, and she wound up staring at the panties in front of Sandy.  “Sandy!  You’re kidding, right?” she asked.  Almost all the panties on the table were very plain – purposely.  But the ones that Sandy had bought were nothing but frills.  Lots of frills.

      “What?” Sandy asked incredulously.  “I think they’re perfect – for him!”  Then she giggled.  Andrea simply rolled her eyes.

      “Okay ladies, let’s get these tags and things off them and get them into the backpack.”

     Together, Mel and Chad decided on a simple pullover top and a loose skirt that he had worn often.  For shoes he decided to wear the black pumps he wore with his maid’s uniform.  His aim was to go simple and comfortable – as few distractions as possible.  His bra and breast forms went under it.  He and Mel discussed the possible need for his waist cincher as well but they decided against it – mostly because Chad didn’t want the extra pressure of something pushing against his bladder. 

     Because of the lack of time, Mel did his hair for him – which was a major job and took most of their time.  She also helped just a bit with his makeup, but mostly, he handled that for himself.  He chose his blue earring studs to wear and his wooden bracelet and necklace.  He had to once again remove everything from his pants pockets and put it all back into his purse which he slung over his shoulder before heading to the door.

     Mel stopped him before he opened the door to leave.  “Let me look at you,” she said.  She stood back and took him in.  How many times had she inspected him when he arrived every morning?  Would she ever do that again?  He looked – good.  Good enough anyway.  She smiled.  “Welcome back Sissy.”

     He smiled as well.  “Thanks… I think.”

      “And listen,” she added, “good luck today.  And I really mean that.  Yes, I do want to win, but I’m also wishing you luck as well.”

     He looked at her for a moment before replying, “Thanks.”

      “Now let’s get back there before you’re late!”

     The women were late.  For the first time all day, Chad was in Mel’s apartment and he wasn’t pacing.  Instead, they were sitting next to each other on the couch.  And the longer they sat, the more their nervousness grew – for each of them.  And somehow, as they sat there, they wound up holding hands, perhaps for mutual support. 

     At exactly five minutes after one o’clock, someone knocked on Mel’s door.  Chad was on his feet in a flash and hurried to open it.  He stood back as he held the door open wide while Andrea, Gloria, Cassie, Sandy, and Robin all entered.  He closed the door behind them and went back to his seat on the couch next to Mel.  The two of them stared up at all the women standing in front of them.  And the nervousness that both he and Mel felt – doubled!

     Gloria took the lead with a smile as she looked at Chad.  “You look good Chad… or Sissy… whatever you prefer today.  Much better than you looked a little while ago.”

     Chad blushed.  “Thanks,” he managed to mumble.

      “Now I guess you’re wondering how this is going to work,” Gloria continued.  She turned toward Cassie a bit.  “Cassie here has a backpack.  And inside that backpack are ten pairs of panties that we all contributed to the cause.  And all of those panties are plain and thin.”

     “Well, most of them anyway,” Andrea added.  Sandy giggled. 

     Gloria continued, “In a little while, you’re going to have to put on the first pair.  Any wet spots on those panties will be very easy to see.  If that spot gets big enough, you’ll have to immediately change the panties for a fresh pair.  Ten pairs is an awful lot.  If you go through that many then… well, let’s just say that it won’t look very good toward our decision later.  We’re going to bring a spare diaper along for later as well – just in case! Hopefully, you won’t need it.”

      “Hopefully, he will need it!” countered Mel.

     Gloria nodded.  “Sorry, it was a bad way to phrase it.”  She continued.  “Now in order to give you a lot more incentive, we’re all going to the mall today.  You’ll get your first pair of panties as soon as we arrive.  And we’re going straight to the food court first so you can not only get lunch, but you’re going to have to get a regular medium sized drink as well – and you’re going to have to drink all of it – like a normal person.  In fact, every hour that we’re there, you’re going to have to drink another medium sized drink to make sure you have plenty of liquid in your system for you to exert some control over.  We’re hoping that the crowded mall will give you plenty of incentive to show us just how much control you can have – instead of running around in public with pee continuously dripping down your legs.      

      “I think you can now guess why we asked you to wear a skirt and to dress like a woman again.  We did that so that we can all check your panties anytime we want, and your skirt can be lifted for easy inspection.  All of us will be checking your panties any time we want – anywhere we want – no matter where we are or what we’re doing.  If we see a wet spot, you’ll have to change panties right then and there!  We may allow some very tiny wet spots to remain and you will be allowed to continue to wear those same panties, but that wet spot will be noted – and watched!”

     Chad wasn’t exactly liking anything he was hearing.  And the way things were going with him so far, this was sounding like it was going to turn out to be another marathon humiliation session for him at the mall!

     Gloria continued.  “And I’m sure you’re wondering about the bathrooms.  That’s another reason we asked you to dress as a woman today.  You will absolutely be allowed to use the restrooms anytime you feel the need.  And since we’re all women, we need to be able to see you peeing like a normal person – in a toilet.  So having you dress like a woman and using the ladies rooms will make that a whole lot easier.  Understand?”

     Chad nodded – nervously.  Then a thought struck him.  “But… if we’re going to the mall.  Some of those bathrooms are miles away from where we might be.”

     It was Sandy who replied.  “Don’t worry,” she said as she held up a pad of paper.  “I have a list of every bathroom in the entire mall, including the ones that nobody knows about.  And I’ve even contacted a number of the stores that have them and gotten permission in advance in case you have to use one.  One of my jobs today is to let you know at all times where the nearest bathroom is.  And if you can’t make it to one of those, then you’re not doing very well!”  She got a disapproving look from Gloria for her last comment.

     Gloria spoke again.  “When we’re done today, we’re all going to come back here and the five of us will meet at Sandy and Cassie’s apartment again to discuss what we observed.  Then we’ll let you know.  And don’t forget… you both agreed to abide by our decision – no matter what we decide!  Win or lose, we decide that, not you!”

     Both Mel and Chad nodded their agreements.  Mel’s nervousness was declining rapidly in favor of excitement.  Chad however felt nothing but doom!

     Mel got to her feet, wanting to get in her first argument in her favor.  “Oh…  Before you start, I want you all to know that he has no control of anything at all at night while he’s sleeping – nothing!  Not his peeing or anything else.”

     Gloria looked at her disapprovingly.  “We’ll take that into consideration, but we’re going to want to see how he does now for ourselves.”  She turned to Chad.  “Do you have that spare diaper?”

      “There’s plenty in the bathroom,” Mel told her.

      “A box of wipes might be a good idea as well,” Cassie added.

     As they were preparing to leave the apartment, Mel saw how worried Chad looked… and she could almost taste the victory.  And as she had done so often when questioning someone over a case, she knew that with victory in sight, it wasn’t the time to back off at all.  So she pressed for more advantage.  With a smile on her face, she walked over to Chad and put her arm around him, squeezing him in a one arm hug.  “Don’t worry Sissy,” she said, “just think, every time you wet your panties at the mall, everyone will see it and laugh.  And you know how excited you get from all that humiliation.  I can see you wanting to get as much fun as you can today.”

      “Stop that!” Gloria cautioned sternly.

      “What?” Mel asked innocently.

      “Stop trying to sway him.”

      “She was?” Robin asked, not understanding what was going on.

      “She was!” Gloria replied.  “She’s trying to play to his sexual desires instead of letting us find out how he’s doing for real!”  She turned to Mel again.  “One more comment like that and we’ll leave you here!  We don’t really need you for this.  You’re only coming along as a courtesy, nothing more.  You have no say in this at all!”

     Mel was shocked!  “I’m just trying…”

      “Don’t!” Gloria told her in no uncertain terms.