The Bet - Chapter 50 (Saturday – week 7 part 5 of 10)

The Bet
by Karen Singer

Chapter 50 (Saturday – week 7 part 5 of 10)

      “Can I take this with me now?” Sandy asked as she felt the fabric of Sissy’s pink baby dress. 
      “Sure,” Mel replied.  “Is there anything else you need?”
     Sandy looked a bit sheepish.  “Well… now that you mention it.  Do you think you can let me borrow some more bottles and more diapers too?”
      “More bottles?  Sure, do you want them empty or full?”
      “Full would be good,” Sandy replied.  “That way I don’t have to bother filling them later.”
      “How many do you think you want?”
     Again Sandy looked a bit sheepish as she answered.  “Um…  Do you think I could have… at least… maybe… a dozen?”
      “A dozen?” Mel asked shocked. 
     Sandy nodded embarrassedly.  “You said you need to keep him drinking and peeing.  So I plan to make sure he does just that.”
      “No problem at all,” Mel replied.  “It’s a good thing I’ve been making more tea.  We can fill his diaper bag with them if you like.”
      “That would be great,” Sandy replied.  “And instead of putting the diapers back in it, maybe I can just take a fresh package with me.”
     Again Mel was surprised.  “A whole package?”
     Sandy was again a bit embarrassed as she replied.  “I don’t want to run out.”
      “With a whole package of them, there’s little chance of that!  I just wish I could be there to see what you do with him!”
      “Tell you what,” Sandy replied.  “I was planning on taking some pictures.  But of course, you can always stop by yourself if you like.”
     Mel shook her head.  “Not if it’s the kind of place you say it is.  And it really doesn’t sound like the kind of place I want to bring a guy.”
     Sandy shook her head.  “That wouldn’t be the best idea.”
      “I’m afraid I’ll have to settle for some pictures again.  Let’s go pack the diaper bag.  We need to see how Sissy is doing on that floor anyway.”

     It was later in the afternoon when Mel’s phone rang again.  Sissy was back to doing laundry after being sent home for a quick shower after messing his diaper, and Mel had just been contemplating whether they had enough time to do another quick ballet practice before Sandy would be picking him up.  She picked up her phone to answer it.  “Hello?”
      “Hi Mel.”
      “Gloria!  What’s happening?  Are you still going out with Ray tonight?”
      “Oh yeah!  He even called earlier to confirm it!”
      “Well, I hope you have a great time with him.  I know I did!”
      “Yeah, I’m really looking forward to it.”  She paused for a moment.  “It’s been so long since I’ve been out with a man that I don’t know what to do?  How should I act?  What should I wear?  I mean… do you think I should dress real sexy, or kind of play it more mature and professional?  And what the heck should I talk about with him?  I don’t want to scare him off with a lot of my professional talk.”
     Mel laughed.  “I think you shouldn’t worry about it so much and just be yourself!  Dress however you want for him.  Trust me, he’s the type who will appreciate almost anything.” 
      “I just want him to like me.”
      “Don’t worry about it,” Mel replied.  “I’m sure he’ll like you.”  She didn’t add that Ray was the type who liked every woman he met – mostly just to get them in bed, which wasn’t exactly a bad thing in his case.  “If you’re that worried about it, go ahead and dress a bit sexy for him.  I know that will get his attention.”
      “You’re sure?”
      “Gloria, relax and enjoy it.  You’ll have a good time with him.  I promise!  What time is he picking you up?”
      “About seven.  Then we’re going to dinner.  How about you?  Are you still going out with Derek?”
      “Yeah, but he’s picking me up at five.”
      “Wow, that’s early.  What are you doing?”
      “I don’t know yet. He didn’t tell me.”
      “Well…  You have fun too,” Gloria said.  “We’ll compare notes on Monday.”
      “Sounds good Gloria.”
     Mel hung up her phone and reflected on the conversation she had just had.  That had not been like Gloria at all.  The calm, cool woman she knew was flustered over going out on a simple blind date.  She knew that Gloria didn’t date much – hardly at all.  But that was mostly because of her profession and the hours she worked.  One of the hazards of her job.  She supposed that Gloria had a right to be as excited as she was.   She had told Gloria about how great Ray was.  She just hoped that Ray would be half as great for Gloria as he had been last week with her.
     She looked at the clock again, then glanced over at Sissy who was still working on her laundry.  There wasn’t really much time left since she had arranged for Sandy to get him out of her way at four o’clock so she would have plenty of time to get ready for her date with Derek.  She decided to forgo dance practice for today.  He was doing pretty well anyway.
     Sandy was actually five minutes early when she knocked on Mel’s door.  The door was opened by Sissy who looked rather relieved to see that she was the one knocking.  She guessed she couldn’t blame him since he was only wearing a bra with his falsies stuck in it, a diaper, and his pink high heels.  He curtseyed and said hello to her in his silly sissy voice as she walked past him, hardly paying any more attention to him again.
      “Hi Sandy,” Mel greeted her as she came in.  “Are you ready for him?”
     Sandy was all smiles.  “That’s why I’m here.”  She turned to look Sissy over.  “Those shoes have to go though!  Where’s his other ones, the black ones that look more like little girl shoes?”
      “They’re in my closet,” Mel replied as she turned toward her bedroom. 
      “You got some socks for him too?”
      “They’re already out and on my bed.  He wore them this morning with his other dress.  Sissy!” she called without looking back.  “Come along!”
     Chad followed them into Mel’s bedroom.  It looked like he was going over to Sandy’s house again while Mel was out on her date with Derek.  He was glad he wasn’t going to be around when Derek came.  He didn’t want any chance of Derek seeing him.
      “Put your socks back on,” Mel said without turning around to look at him.  Then she opened her closet to look for his shoes.
      “And take your bra off too,” Sandy added.  “I don’t want it.”
     It only took a minute for Sissy to get everything off, leaving him in only his one single diaper.  He pulled the socks onto his feet and made sure they were turned down properly at the top.  Mel handed him his black shoes and he buckled them on.
      “What else?” Mel asked. 
      “That’s it for now,” Sandy said.  “He can stay that way for a while.  I’ll dress him later when I’m ready.  Oh, I almost forgot!  His night clothes.  Do you have any here, or should I stop at his place and get some.”
      “You’ll have to stop at his place,” Mel confirmed. 
      “No problem.”  Sandy turned to Sissy.  “Are you ready?”
     Chad wasn’t at all ready – mentally.  He was only wearing shoes and socks and one very wet diaper.  But he was sure that Sandy wasn’t going to allow him to put anything else on – even to go outside.  He curtseyed.  “Yeth,” he replied in his lisping sissy voice.
      “Let’s go then,” Sandy said brightly.  At Mel’s door, she picked up one of the packages of diapers that Chad had purchased earlier.  “You can carry your diaper bag,” she told him.  “It’s heavy and I don’t want to lug the thing.”
     Chad stuck his purse over one shoulder and picked up his diaper bag.  It was heavy!  Very!  But he had seen them packing it with some bottles earlier.  How many had they put in there?”
      “See you later,” Sandy said brightly to Mel as she opened the door and walked out. 
     Worried about going outside again dressed just as he was, Chad followed her.  He wasn’t at all surprised when she stopped first at his apartment door.  He unlocked it and they went inside.  Sandy set the package of diapers down on the floor and he set his diaper bag and purse down next to them.  He already knew Sandy would be looking for his night clothes so he led her straight into his bedroom.  He opened one of his cardboard drawers.  There were several onesies inside and several of his baby doll nighties too.  “Which one do you want?” he asked.
     Sandy looked through the drawer and pulled out one of the onesies and one of the baby dolls.  She threw the onesie back into the drawer.  “This will do,” she replied as she headed back out toward his door. 
     Chad saw her picking up the package of diapers she had carried in.  He had thought she would be leaving them at his apartment.  “You need the whole package?” he asked her.
      “There isn’t enough room in your diaper bag for them,” Sandy replied with a smile.  She waited till Chad had picked up his purse and his diaper bag again.  Then she frowned.  “Where’s your pacifier?” she asked.
     Without saying anything, Chad quickly dug it out of his purse and stuck the stupid thing in his mouth.
     But Sandy still wasn’t happy with what she saw.   “Leave your purse here,” she told him.  “You’re a baby.  Babies don’t need anything like that!  Just hand me your keys.  I’ll take care of them for you tonight.”
     Reluctantly, Chad handed over his keys and dropped his purse back to the floor.  He knew he was going to get the baby treatment again, but being called a baby the way she had just done seemed to deflate what little was left of his ego – by a lot.  Carrying only his heavy diaper bag and sucking on his pacifier, he followed her outside and over to her apartment.
     Sandy turned to him before she opened her door.  “Remember the rules,” she said.  “From this minute on, you’re a baby.  You’re nothing but a baby.  You don’t do anything at all that a little baby wouldn’t do.  You don’t even think anything that a baby wouldn’t think – for the rest of the night!”  She was about to open the door when she added one more thing.  “No matter what!”
     There was something about that last statement that sent a chill down Sissy’s spine.  But he had been here before and had done the baby bit with her several times.  It really wasn’t so bad.  He just had to relax and not worry about anything.
      “Set your bag down there,” Sandy said as she opened the door.  “From now on, unless I tell you, you can only crawl – as you should well know by now!”
     Chad set his bag down and crawled into her apartment while Sandy tugged his diaper bag in after her and closed the door.  Chad crawled off to her living room where she usually laid out a blanket full of baby toys on the floor for him.  Once again, the blanket was there.  He wondered if she would let him take a nap for once.  He could certainly use one.  He moved some of the toys aside and laid down with his head on his arm. 
     He was just getting comfortable when Sandy came back with a baby bottle.  “Don’t forget,” she said as she handed it to him.  You still have a deadline to meet.  And according to what Mel told me a little while ago, you’ve got just over half an hour to be leaking.  So I suggest you get busy!”
     Well, so much for nap time – for now.

The Bet - Chapter 50 (Saturday – week 7 part 4 of 10)

The Bet
by Karen Singer

Chapter 50 (Saturday – week 7 part 4 of 10)

     It was nearly lunch when Sandy found a parking place along the busy street.  She got out of her car and walked nearly a block before she got to her destination.  She looked up at the sign over the building – Greta’s.  She had never been here this early before.  She and Cassie always came at night when things were more… interesting.  She went in through the doors, noting as she did how different the place looked during the day than it did at night.  And there were very few customers inside, but then, it was early for much of a crowd.  The big crowds didn’t come to Greta’s bar until later in the evening. 
     She spotted Greta herself behind the bar moving bottles around.  “Hi Greta,” she said as she walked up. 
     Greta looked up.  She was a somewhat heavy woman with a very round belly.  She was somewhat older too.  Her bare arms looked almost muscular instead of just fat.  “Sandy!” she exclaimed.  “It’s kind of early for you, isn’t it?”
      “Kind of.  But I’m not here for a drink… yet.”
     Greta was confused.  “No drink?  So what’s up?”
     But now that she was there, Sandy was finding it hard to ask.  “Well… Um… I’m kind of…  Damn it!  I don’t know where to start!”
     Greta let out a short burst of a laugh and turned away toward her beer taps.  She filled two tall glasses with amber liquid and set one of them down in front of Sandy.  The other one she took a long sip from herself.  “Maybe you better start at the beginning.”

     Lunch was over, the apartment had been cleaned, the laundry was well under way, Mel had faked putting another suppository up inside of Sissy, and now she was working on making her third pot of tea when she heard her phone ringing.  She quickly found it and answered.  “Hello?”
      “Hi Mel!” Sandy’s excited voice replied.  “Are things still on for me to get Sissy tonight?”
      “Of course,” Mel replied. 
      “Great.  Because I think… at least I hope… I’ve found something great to do with him.”
      “Oh?”
      “Tell you what, I’ll tell you all about it in a few minutes.  I’m almost home now.”
      “Okay.  I’ll see you in a few then.”
      “Oh Mel!  Is there any way I can get you to take those breast forms off of him again.  They kind of don’t go with what I want to do tonight.”
     Mel laughed.  “No problem.  I never got around to gluing them back on.  I’ll wait till tomorrow to do it.”
      “Great!  See you in a few!”
     Mel put her phone down.  So Sandy had finally come up with an idea.  She couldn’t wait to hear what it was.  She only hoped she would get to see it this time!  But if she was going to be out with Derek tonight, then she didn’t know how that was going to be possible.  Once again, she was going to get left out!
     She was almost back to the kitchen when she heard her phone ringing again.  What had Sandy forgotten now?  She quickly went back to answer it, but instead of Sandy, this time it was Andrea calling. 
      “Okay, I took care of it,” Andrea said without evening saying hi.  “But you owe me fifty bucks and next week it’s going to cost you another hundred.”
     Mel smiled.  It would be worth it.  “No problem.  Tomorrow night soon enough for you?”
      “That’s fine,” Andrea replied with a slight giggle.  “I’m looking forward to it.”
      “And everything looks good?”
      “I think it should work out perfectly for you.  Just what you asked for.  The guy just wouldn’t let you have it for nothing.  He was trying to hustle me all the way.  I’m afraid I’m not much of a negotiator.  What he charged was the best I could do.”
      “No problem Andrea.   No problem at all.  If it works out, then it’ll be worth it.”
      “Yeah.  I hope so.  Anyway, I just wanted to let you know.  See you tomorrow.”
     Mel put her phone down again.  It was set!  Sissy’s public ballet was on!  The price was a bit more than she had expected, but still, to her it was small change.  It hardly mattered.  Sissy was going to be a sensation!  She just knew it!
     The knock at her door interrupted her thoughts.  Sandy had been faster than she thought.  “Sissy!  Get the door!” she said as she saw him standing there folding a towel with a worried look on his face.
     Dressed in only a diaper, bra, and pink heels, Chad cautiously opened the front door.  He was very relieved to see Sandy there.  He dropped her a quick curtsey and said a sissy hello as she came inside – mostly ignoring him. 
      “Hi Mel,” Sandy called as she came in. 
      “Hi Sandy,” Mel replied.  “Come on in the kitchen to talk.  Sissy is still busy with the laundry.”  They both entered the kitchen together.  Very softly so that Sissy couldn’t hear, Mel asked, “So you finally found something?”
     Sandy giggled.  “Yeah!” she replied, just as softly.  “I’m pretty sure at least.  Are you familiar with Greta’s?”
      “Greta’s?  Never heard of it.”
      “It’s kind of this bar… well, mostly it’s this hangout place.  Mostly for women… like Cassie and me…

     Chad was still busy with the laundry, but he was watching the time carefully.  It was coming up on his deadline for leaking.  Fortunately, he knew he was close – very close!  The two women were in the kitchen but they were speaking so softly he couldn’t hear them, other than some giggling of which there was more than a bit.
     He suddenly felt himself peeing again, a bit more than usual.  And a few seconds later…  “I’m leaking!” he called out excitedly.  He had made it once again!  He felt nothing but relief. 
      “Good!” Mel yelled back.  “Get in here then.”
     Since he was close to it, Chad grabbed his diaper bag before he went into the kitchen so Mel could change him. 
      “What did you bring that for?” Mel asked with more than a bit of annoyance.  “Did I ask you to bring it?”
     Chad curtseyed, but he was confused as he answered.  “But I’m leaking.  I thought you’d want it.”
      “Well I don’t!  Take it back and hurry up!”
     She didn’t want it?  She wasn’t going to change him?  But Chad did as he was told and carried the bag back out.
      “You’re not going to change him?” Sandy asked quietly as soon as he was gone. 
      “Not exactly.  But stick around, I’m hoping that this will be fun.”
     Chad went back to the kitchen and waited while Mel took the lid off of her pot of tea and stirred it before she put the lid back on again.  He didn’t see the wink she gave to Sandy before she came over and bent down to examine his diaper.
      “Yep, it’s leaking,” she declared happily.  “Very good.”  She reached out and pulled on the tapes on one side, opening it enough to let it fall down his legs to land with a heavy splat on the floor at his feet.  Chad stepped out of it.  Seal that in a plastic bag and put it in the trash,” Mel ordered.
     Diaperless, Chad went about picking up his soggy diaper.  But he was confused because Mel only poured herself a fresh cup of coffee and topped off the cup that Sandy had too.  She wasn’t making a move to get his diaper supplies. 
     As Chad was picking up his wet diaper, Mel was trying to make a decision.  She needed a number.  She just didn’t know what that number should be.  Five?  No, too low.  Ten?  Was that too high?  Twelve?  But twelve would mean…  So maybe six… or eight… or…  Oh hell!  Why not make it interesting!  Twenty!  She grabbed her coffee pot and refreshed her cup.  Then she brought it over to Sandy and refilled her cup.
      “Hey,” Sandy said as soon as Mel had topped off her coffee.  “What’s on his nails?  Some kind of decoration?”
     Mel smiled wickedly.  “Of a sort…”
     Chad’s task didn’t take long since everything he needed was right there in the kitchen.  When he was done, Mel called him over.  “Show Sandy your pretty nails.”
     Embarrassed by them, Chad walked over.  He could feel his face growing a bit red as he tentatively held out his left hand to show her his name spelled out on his nails.  He was rewarded by Sandy giggling.
      “Sissy?”
      “Both hands,” Mel ordered, and Chad brought up his other hand too.
     Sandy examined both hands, searching for something to say.  Finally, as she tried to restrain her giggling, she managed to get out, “How appropriate!”
      “Go stand in the middle of the floor now and wait till we’re ready for you.”
     Chad had no idea what Mel wanted to do, but he had a feeling he wasn’t going to like it very much.  He stood in the middle of her kitchen floor, just watching the two women and waiting.  Mel and Sandy were only paying a little bit of attention to him, only glancing at him occasionally.  He was getting more and more curious about what they wanted him to do, when he suddenly felt himself peeing again – on the floor – again!
      “Good!” Mel declared as soon as she saw what he had done.  “We can start now.”
     Start?  Chad had no idea what she was talking about.
     Mel looked up at the clock.  You now have exactly one hour!  In that hour, you’re going to pee on the floor twenty times and clean it up.  If you don’t make it to twenty, well, we’re going to work it like we do with your diaper leaking.  For every remaining time you didn’t pee, you’re going to get five swats from my stick!
     Chad was shocked.  Twenty times!  In only an hour?  He was sure there was no way he could possibly make that – even with as much as he was peeing now! 
      “Now get busy and clean that up!” Mel ordered as Sandy giggled next to her.
     Twenty times!  Twenty!  He had to pee twenty times in the next hour!  It was impossible!  And on the floor too, where they could see him do it!  He grabbed his cleaning supplies, but stopped to grab a fresh baby bottle before he started cleaning.  He was going to need that bottle!  With one hand, he held the bottle to his mouth and sucked on it, his head held up at an angle making it harder to see what he was cleaning, while his other arm was busy actually cleaning up his mess.  And all the while, he was doing his best to keep peeing again – just like he always did.  But twenty times?  In only one hour?  Impossible!  And it would be five swats now for each one he didn’t do!  Impossible! 
     He had grabbed the entire roll of paper towels and used one of them to soak up the pee.  Then he sprayed the spot with some cleaner and wiped it with another paper towel to finish.  He wasn’t being particularly picky though because he figured he would probably be cleaning the entire floor thoroughly again as soon as this little game was over – which hopefully would be only an hour from now.  That is, an hour plus the time it took her to punish him for failing!
     When he was done cleaning up the spot he threw the dirty paper towel into the trash and looked to Mel. 
      “Just stand there till you pee,” she said.  She looked up at the clock.  “Time’s wasting!  You haven’t even done one yet!”
     Chad looked at the clock.  It had only been two minutes since he had just peed.  And unfortunately, it looked like she wasn’t going to count that first one.  Pee!  Pee!  Pee!  It wasn’t till six minutes into the hour that he finally managed to pee again - on the floor – right in front of Mel and Sandy.  How embarrassing! 
      “That’s one,” Mel declared as Chad went back to work cleaning while he was still drinking furiously. 
     Half an hour into Mel’s little game, Chad had barely managed to pee five times.  Each time it was very little that came out, but at least Mel counted them.  He stood there drinking his bottle and trying furiously to pee.  He was rewarded to see a few more drops come out on the floor.  He got back down to clean it up.
      “I don’t think that’s enough to count!” Mel declared.  “Do you?” she asked Sandy.
      “I only saw a couple of drops,” Sandy agreed.  “In fact, I’m surprised you counted some of his other times.”
      “Doesn’t count!” Mel declared with finality. 
     Chad stood back up, more frustrated than ever and kept drinking and trying to pee.  It was two minutes more before he was rewarded with a little more.  He got back down to clean it up.  But before he was finished, he heard Mel declare.  “That’s seven!”  But by his count it should have been only six!  He looked down to see that he had just peed a little again while he was cleaning.  Good!  And at least he was down right where he needed to be to clean it up.  He kept cleaning, and drinking, and trying furiously to pee!  A little more came out. 
     He was peeing more often now.  Maybe because of his non-stop drinking.  Twice more he peed while he was still cleaning up from the previous time. 
      “He’s getting better at it,” Mel noted.  “But I don’t think he’s going to come close to making it.”
      “Instead of five spanks for each one he doesn’t make, you could always keep spanking him till he finishes his count,” Sandy suggested.
     Mel considered that.  “I like that idea, but I think that this time it would take too long.  And I have an early date to get ready for tonight.”
      “Yeah, that reminds me.  Why so early?” Sandy asked.
      “I don’t know,” Mel replied.  “He never said.”
      “And this is the other guy, the one you said you wanted to go out with to begin with?”
     Mel nodded.  “That’s him.  I think maybe it’s why I’m looking forward to this date so much.”
      “But you said the one from last week had been fantastic.”
      “I know, but there was just something…  I don’t know.  He was maybe too good.  My best friend Gloria is going out with him tonight instead.”  She looked at Sissy, he was peeing yet again.  She could never manage to pee that often no matter what.  “Twelve!” she declared.  “I don’t think you’re going to make it.  I guess I better get my stick ready.”
     Sandy giggled while Sissy got down and cleaned once again. 
      “Times up!” Mel declared all too soon. 
     Chad felt totally defeated.  But there was no way that anybody could ever pee twenty times in only one hour.  He couldn’t believe that he had actually made it to fourteen!  But he figured that he had been lucky because Mel had counted some that were very questionable. 
      “I guess it’s punishment time,” Mel said.  Chad was expecting to have to go prepare the floor where she usually punished him, but instead Mel turned to Sandy.  “Will you get my stick for me please?  It’s in the corner over there.”  She turned to Sissy.  “You’re not leaving the kitchen till you’re diapered again.  I don’t want you peeing all over the carpet.”
     A few minutes later, instead of leaning up against the chair in her living room, Chad was bent over leaning against the kitchen counter. 
      “You only managed fourteen,” Mel said, “which leaves six.  So it’s thirty swats.”  She waited till Chad raised his backside up higher, making it a more inviting target for her to hit.  She started to swing, and suddenly stopped herself.  “Wait a minute!  Starting from my first swat, I’m going to reduce the number I give you by… let’s say three for every time you pee while you’re being punished.  That way, you can keep trying just as hard as you have been while we’re doing this.”  She looked at Sandy.  “I think that’s fair.  Don’t you?”
     Sandy nodded.  “More than fair.  I wouldn’t even give him that!”
      “Yeah, well I think he needs the incentive to keep trying so hard even while he’s being punished.”  She turned back to Sissy.  “Backside up!”  A moment later, she swung her stick.  Swish!  Smack!
     Chad stood up and curtseyed and thanked her for hitting him, but the only thing really on his mind was to keep peeing.  The more he peed, the less he would get hit!  And he didn’t like getting hit!”  A few seconds later… he was thanking her again.  Pee!  Pee!
     He actually managed to pee twice during his punishment.  He had peed a third time, but unfortunately it came out as Mel was swinging her stick one last time.  He counted himself lucky.  Twenty four swats was more than enough for him.  He really hoped Mel was done with this game.  He didn’t like it and he didn’t ever want to play it again! 
     Mel looked at the kitchen floor.  There was a lot of pee where he had been standing and curtseying during his punishment.  It needed cleaning.  In fact, the whole floor probably needed cleaning again.  “Start cleaning this floor again,” Mel told him.  “All of it.  And make sure you do a thorough job this time!  I’ll get your diaper for you.  She looked up at the clock.  An hour and forty five from right now!” she declared.
     Sandy giggled, but it was a small giggle.  “You know what?  I was just thinking.  I wonder how many times he would pee again while he’s cleaning that floor?”
     Mel stopped right where she was and glanced all around the kitchen floor again.  “Now that’s an interesting idea.”  She looked at the floor and pointed to the far corner.  “You can start right there and work your way toward the living room.  Just don’t leave the kitchen till I get a diaper on you.”  She thought of just one other thing.  “And you can do it all on your hands and knees!  I don’t see any reason why you need a mop for this.  You can clean it thoroughly, and dry it too as you go, then back your way out till you’re finished.  And we’ll do our best to count how many times you pee.  Won’t that be fun?”
     Chad was horrified.  Fun?  Not to his way of thinking.  It took him a few minutes to grab and fill a bucket and more cleaning supplies and to also grab another baby bottle of tea.  Then got down on his hands and knees in the corner and began cleaning.  Just a few seconds later, he peed on the floor again right between his knees where he had just started cleaning. 
      “I see it,” Sandy declared from where she was sitting.  “That’s one!”
     Chad looked at his new pool of pee.  He had the distinct impression that he would probably be peeing on almost the entire floor by the time he got done.  And the two women were going to be watching him the whole time, so he dared not take any shortcuts with his cleaning.  This was not going to be fun!
      “Hey Mel,” Sandy said as she started to lose interest in watching Sissy clean.  “Did you manage to get his dress cleaned?”
      “Sure did!  We took it to the cleaner’s this morning.  Want to see what he wore all morning for our errands?”
      “Sure!”
     Chad was soon left alone to his task.  He stopped trying to pee so hard. He also stopped drinking and just kept his baby bottle close by in case they came back.  He had already drank so much that he felt like he was drowning.  Unfortunately, all that liquid in his system still had to come out, so every few minutes he found more and more little puddles of pee to clean as he went.  It was so embarrassing.

The Bet - Chapter 50 (Saturday – week 7 part 3 of 10)

The Bet
by Karen Singer

Chapter 50 (Saturday – week 7 part 3 of 10)

      “Are you leaking yet?” Mel asked, as they stowed the large diaper bags in the trunk of her car.
     Chad took a moment to try to feel how wet he was – which was very.  But he wasn’t leaking.  “Not yet,” he replied, “but I’m really wet.”
     Mel glanced at her watch.  “Better hurry!”
     Chad was trying to pee and leak once again.  But now that they were done with the drug store, he just wanted to get home!  In fact, leaking at home would be much preferable to leaking somewhere out in public.  He put his baby bottle back to his mouth to finish it as soon as he was again belted in the front seat.  Unfortunately, as soon as Mel got back on the road, he realized that Mel wasn’t heading home.
      “You must be starving,” Mel exclaimed as she drove up the road.  “I didn’t feed you breakfast this morning.  Why don’t we stop somewhere and get something.”
      “I’m okay,” Chad replied not wanting to go anywhere else in the crazy dress he was wearing. 
      “Nonsense!  You need your breakfast.  And I’m buying, so don’t argue!”
     As if he would – even though he really wanted to.  He was fairly sure that Mel’s main intention was to keep him out in public as long as possible in the silly dress he was wearing!  And he was close to leaking… he knew he was!
     Mel pulled into one of her favorite fast food restaurants, noting that the parking lot was fairly full, which didn’t surprise her since it was Saturday morning.  There were no parking spaces anywhere near the doors so she was forced to park fairly far away.  “Are you leaking yet?” she asked again as they got out of the car.
      “Not yet,” Chad replied.  “But I know I’m close.  Maybe we should go home first?”  The question was worth the try if nothing else.
      “We’re not going home yet.  You need some breakfast first.”  She glanced at her watch.  You better hurry.  It’s starting to look like you’re going to get another beating as soon as we do get home.”  She looked at him and grinned.  “Or maybe you’d rather I beat you here in front of all these people?  You do like to be humiliated!”
     Chad was shocked by her question!  She wouldn’t would she?  But she had been getting bolder and bolder lately about what she did with him around other people so he wasn’t at all sure what she would do.  “No please!” he pleaded.  “I’m trying hard, I promise!”  Another beating for being late was the last thing that Chad wanted – well, almost the last thing.  Unfortunately, the last thing that he really wanted was to be doing just what he was doing now – being out in this busy place dressed the way he was! 
     Heads turned fast as they walked in through the doors.  People stared, fingers pointed, people whispered, and more than a few laughed or exclaimed their surprise out loud.  Chad felt incredibly foolish, but there was nothing he could do about it.  And worse, since the place was busy, they were forced to stand in a long line of people while they waited to order.  And since they were in the line, everybody kept turning to look at them, which slowed things down even more.  Mel didn’t seem to mind at all.  In fact Chad got the distinct feeling that she was happy about how slow things were going.  But he wasn’t the least bit happy about it.  He was especially unhappy when five minutes after joining the line, he suddenly felt the telltale tickle of a little leak from his diaper.  He leaned over close to Mel.  “I’m leaking,” he whispered, hoping that nobody else could hear. 
     Mel heard him, but there was no way she was going to allow him to get away with speaking so softly.  “You’re what?” she asked loudly.  “And when are you going to learn to curtsey every time you speak?”
     Chad was horrified.  She couldn’t mean…  But he knew all too well that she did.  Shaking more than a bit from the embarrassment, he curtseyed to her.  “I’m leaking,” he said again in his sissy voice, but only a bit louder.  Again, he noticed a lot of heads turning to look at him strangely.
     But Mel still wasn’t satisfied.  “What’s leaking?” Mel asked.  “And speak louder so I can hear you clearly.  It’s bad enough trying to make sense of your sissy voice as it is.  I don’t stand a chance unless you speak up.”
     Chad was so embarrassed that he actually felt himself peeing again.  He curtseyed – which seemed to make his leak that much worse.  “My diaper is leaking,” he lisped in his sissy voice, loud enough that everyone around him could hear.  He noticed a few heads bending down to look under his skirt.  Could they actually see his diaper under there?  And then he noticed one boy pointing at him and whispering to somebody else.  The two of them started laughing.  He guessed that maybe they could see it.  The trickle of pee running down his leg felt awful as he waited to hear what Mel wanted to do.  Would she make him wait and keep leaking in the restaurant?  Or would she take him home now?
     Instead of speaking to Sissy, Mel spoke to the people around them.  “Excuse us,” she said as she backed out of the line of people.  It seems I have a baby with a diaper that needs changing before we can have our breakfast.”  Then she led the way back outside again, and Chad followed gratefully.  Home!  Yes!
     But Mel stopped at the car and only pulled his diaper bag out.  Then she turned and headed straight back into the restaurant again.  A horrified Chad was forced to follow at her heals.  She not only led him straight back into the restaurant, but straight back into the ladies room as well.  Chad couldn’t believe it, but he had to believe it because he was in there with her.
     Mel paused a short distance into the ladies room and looked carefully at the plastic baby changing table attached to the wall.  She turned to Sissy, “I guess we’ll have to use something else,” she said. 
     Chad looked at the changing table.  Since it was only about four feet long and looked like it would break under about half his weight, he was glad that Mel was only teasing… he hoped.  The three other women in the ladies room at the time stared hard in disbelief as he passed them.  Fortunately, the handicap stall was not being used and Mel led him straight into it.  Chad was very glad when she closed the door behind them.  Things were bad enough as they were.  He didn’t want that door left open where anyone could see him getting changed too.
      “Okay, hold that skirt up out of the way,” Mel told him.
     Chad did his best to gather as much of his skirt as he could and hold it up high, but there were so many separate ruffles in and under the skirt that he couldn’t really do much.  He felt Mel trying to get at his diaper under his dress, but she was having trouble seeing everything properly under all the ruffles that kept getting in the way.  “This thing is impossible!” she muttered at one point.  But finally, he felt the tapes on one side opening up, and then she let it simply slide down his remaining leg.  Cool air washed over him as soon as the warm wet diaper was gone. 
     He continued to stand there and hold his skirt up as Mel reached into his diaper bag to get a fresh diaper.  But unfortunately, as she did so, he suddenly realized he was peeing again.  He let out a quick sound of distress which instantly grabbed Mel’s attention.  He was peeing on the floor again.  In his panic over it, he noticed the toilet not two feet away.  He started to turn toward it so the remaining pee could go into it.
      “Don’t you dare!” Mel’s voice warned as she saw what he was going to do.  “You don’t use those things anymore!”
     Chad was forced to turn back toward her again.  But even if he had gotten to the toilet it would have been too late.  He was done peeing already.  And now there was a puddle on the floor that he just knew he would have to take care of. 
      “I think you enjoy doing that,” Mel teased as she started fitting the fresh diaper around him.  “Do you?  Do you like peeing on the floor like that?”
     Chad knew she was only teasing but…  “No Mistress,” he answered. 
     But Mel was all smiles as she fastened the first tape on his diaper.  “I don’t know.  I think you do like it!  In fact, I’ll bet you love doing it!  And… I’ve noticed that you’re doing it a lot lately.  Well, let me tell you, I don’t mind at all.  So if you like it, then please keep doing it.  I’m glad to see it.”
     Chad was sure she was glad to see it, even though it was humiliating for him.  She was glad to see it because it was just the proof she needed to see how much control he had already lost.  But the truth was, he simply couldn’t help it!  During these long weekends he had no chance to ever even try to hold back.  He spent absolutely every waking minute of his life trying hard to keep peeing in order to meet her never ending deadlines.  And the result was that now his body didn’t even warn him when he was going to pee.  It just happened – anytime, anywhere.  And if he just happened to be not wearing a diaper at the time, then the floor got wet!  And his problem was compounded because since he was trying to pee all the time, it usually came out in smaller amounts, but much more often. 
     He felt Mel finally get the last of the tapes fastened.  Then it took both of them to make sure all the ruffles from his dress were outside of the waistband.  And finally, he was ready.  Except… 
      “I’ll be out front waiting for you,” Mel said as she opened the door.  Make sure you do a good job of cleaning that up.  And whatever you do, don’t get that dress dirty!”  She turned and left him alone.  She didn’t see any reason at all to wait in a smelly restroom while he cleaned the floor!
     Chad stared down at the puddle he had to clean.  It wasn’t much really, but since he had moved a bit toward the toilet at one point, the wet areas on the floor were more than one little spot.  He didn’t have any of his regular cleaning supplies, so he pulled a bunch of toilet paper off of the roll and wadded it up in his hand.  Then he knelt down to get at the wet spots… or at least he started to.  When he got down, he realized that his darn skirt was so wide that he couldn’t really reach out to get at the spots without his skirt rubbing all over the dirty floor – and most likely getting in the wet spots too.  The last thing he needed was for his darn skirts to soak up all that pee!  He had to stand up and bend over at the waist while trying to keep his crazy skirt out of the way with one hand.  The four inch heels on his feet made the job that much more difficult and his legs were splayed wide as he tried to work. 
      “Oh! Excuse me!” a feminine voice suddenly exclaimed.
     Chad, still bent over at the waist, turned his head to see another customer standing and staring totally shocked in the door to the open stall.  Why hadn’t he thought to close it?  And worse, since his back was to her and he was bent over at the waist, the woman was staring straight at his diaper covered bottom!  He quickly stood up red faced.  “Excuse me,” he mumbled as he reached for the door to close it.  But the woman was now staring wide-eyed at the dress he was wearing.  He had to stand there for several moments with his hand on the door before she recovered enough to move out of the way.  Only after the door was firmly closed again did he go back to the arduous task of cleaning up his mess – the result of which wound up covering most of the stall floor since the wet areas spread as he wiped them. 
     When he was finally ready, he grabbed his diaper bag and purse and opened the door again.  There were two women standing out there waiting on a stall.  Both of them were startled by his appearance.  He walked straight past them to the sinks where he washed his hands thoroughly.  After cleaning up that mess, there was no way he was not going to wash his hands before leaving – crazy dress or not! 
     He found Mel sitting out at one of the tables waiting for him.  “Took you long enough,” she mumbled as she got to her feet.  Once again they joined the long line of people waiting to order their food, only this time Chad was in a fresh diaper with a new time limit, and he had his very embarrassing diaper bag slung over his arm.  Since it had taken him so long in the ladies room, everybody in line was different than the ones who had been there earlier – so he was just as much of a new surprise to all of them.
     It seemed to take forever for them to get to the cash register where they could order their food.  Chad figured that it would have seemed slow even if he wasn’t dressed as such an outrageous sissy.  He was very afraid that Mel was going to make him speak to the girl taking their orders, but Mel ordered for both of them – a child’s meal for him.  He was glad he didn’t have to speak, things were bad enough. 
     After ordering, they had to stand around and wait a little while for their food to get ready, which gave everyone even more time to gawk at him and stare unbelievingly.  He was very glad when they did finally get their food and he and Mel went back through the restaurant to find an empty table.  His skirt was again a problem as he tried to slide into the booth, but he barely gave it a thought.  At least sitting down in the booth hid part of his dress somewhat.  Probably the worst part of it. 
     Mel handed his breakfast over to him, but kept his drink on her tray.  “Do you have an empty bottle in your bag?”
     Chad opened his diaper bag and checked, but all the bottles in it were still full.  “No Mistress,” he replied.
      “Well then grab one of the full ones and drink that instead.  And hurry up with it because we can’t leave till you finish that plus this drink too.”
     Chad nearly grunted out loud.  Now she had him drinking from his baby bottle out in a really crowded place!  Once again, heads turned all around him as he put his baby bottle to his mouth to drink.  This had to be one of the most humiliating mornings ever!  And every time he put his bottle down to eat, Mel didn’t let him keep it down more than a few seconds.
      “Better hurry up and keep drinking,” she reminded him.  “We can’t leave till you finish both drinks.”
     He was forced to drink almost continually as he tried to eat.  And as soon as his bottle was empty, Mel grabbed it and poured the milk she had gotten for him into it.  And his bottle immediately went back into his mouth again.  His diaper was very noticeably wet by the time they finally left and got back into the car – where she made him get yet another bottle out of his bag and drink it while she drove.  Chad was frustrated!  She just never let up!
     From the fast food restaurant, Mel drove straight back to the dry cleaner.  But this time, before they went in, Mel handed Sissy the tickets for the laundry so he could get his dresses.  The same bald man was at the counter when they went in.  Chad had the impression that he was always the one at the counter.  The man saw them coming in and yelled something back to one of the workers in the other room as Chad approached the counter.  He held out the laundry tickets for the man to take.
      “Don’t just hand them to him,” Mel said.  “Be polite and ask him if they’re ready yet.”
     Be polite?  Unfortunately, Chad had a pretty good idea what she meant by that.  He curtseyed for the guy just as three of the workers came out from the back room – one of them holding his dresses wrapped in clear plastic.  “Aw my dwetheth weady yet?” he asked in his sissy voice.
     The man looked startled and glanced uncertainly at Mel.  “Are they ready?” he asked her uncertainly. 
     Mel only responded with a slight nod.
     He turned and took the dresses from one of his workers and hung them up on the long hook by his register.  Mel pulled up the plastic on the pink baby dress and examined it closely.  Clean and perfect!  “Excellent!” she exclaimed out loud.  “Thank you.”  She turned to Sissy.  “Make sure you thank him for the good work he did for you.”
     Chad dropped another curtsey before speaking.  “Danku fow cweanin my dwetheth tho wew fow me,” he said. 
The man just stared at him, not at all sure of what he had heard.  Instead of saying anything, he shook his head and punched in the total at the cash register. 
     Sissy paid the amount and started to reach to grab his dresses when he noticed that there were now five workers besides the man standing around watching him.  In the dress he was wearing, he had been nothing but a big show to everyone all morning long.  He dropped them all a curtsey before quickly grabbing his dresses and leaving. 
     Mel was totally dumbfounded at seeing him curtsey for everyone before he left.  What had gotten into him?  But… she wasn’t complaining one bit.  Wasn’t that the kind of thing she wanted him to be doing in the first place?
     Fifteen minutes later, Mel finally pulled into her parking space at home – just as Sissy finished his latest baby bottle.  Mel smiled as she turned her engine off.  “Now that’s what I call a satisfying morning,” she said.  “We got a lot accomplished!”
     Satisfying?  Maybe to her.  For Chad it was just plain humiliating!  But unfortunately, as much as he hated it, it was also the kind of humiliation he dreamed about.  But satisfying?  Maybe they had two different definitions of the word.
     As soon as they were back in her apartment, Mel had Chad remove his sissy dress to protect it.  She also had him remove his sissy socks.  But she told him to leave everything else on – which left him in just his bra with the breast forms stuck in it, his diaper, and his pink patent high heels.  While she went into the kitchen to put another pot of tea on the stove, she let Sissy get started on all the laundry and house cleaning that needed to be done. 

The Bet - Chapter 50 (Saturday – week 7 part 2 of 10)

The Bet
by Karen Singer

Chapter 50 (Saturday – week 7 part 2 of 10)

     Slowly and carefully because of the full dresses in his arms, he followed Mel down the steps and to her car.  She had the back door open and was waiting for him.  She took the dresses from him and laid them on the back seat.  Chad noticed that his diaper bag was already on the floor back there as well. 
     Mel was about to close the back door to her car, but she stopped as she remembered something.  She reached in and pulled out one of the baby bottles from his diaper bag first.  “Almost forgot this,” she said as she handed it to him.  “We can’t let that happen, can we?”
     Chad didn’t say it, but forgetting it was what he would much prefer to do!  Mel walked around to the driver’s side to get in and Chad opened the front door to the passenger side… and started to get in.  But he was faced with an odd problem.  His crazy ruffled skirt was so full and stuck out so far that he didn’t know how he was supposed to sit down in the car since the back of the skirt stuck out just as far as the rest of it all around.  Slowly and carefully, he had to force his way into the car first, his skirt folding and bending against the door and the seat as he got in.  As he sat down, he could feel the back of the skirt bunching up behind him.  He considered trying to fold the skirt under his bottom as he sat, but thought better of the idea and tried to pull it straight up behind him instead.  It worked – somewhat anyway.  At least he was in.  Buckling his seat belt around the skirt was another problem.  Finally, all he could do was to crush the crazy thing as he fastened and tightened the belt.  And as Mel pulled out of her parking space, he stuck his baby bottle into his mouth.  He still had a time limit to worry about, less than an hour to go now.  Would they still be out somewhere when he started leaking?  He hoped not… but with all three dresses… what did Mel have in mind?
     Many of his fears were put to rest as soon as Mel pulled into the parking lot where the dry cleaner was. 
     “Grab those dresses, Sissy,” Mel said as she got out of her car. 
     Chad unfastened his seat belt and opened his car door.  Getting out was definitely easier than getting into the car.  He expected the skirt of his dress to be a mess, but as soon as he was out and standing, the skirt seemed to automatically pop right back into place again perfectly.  He wasn’t totally sure if he was glad about that or not.  He opened the back door and fought a bit with his skirt as he pulled his other dresses out.  Then, feeling more worried with each step, he followed Mel into the dry cleaning store. 
     There was an older balding man behind the counter.  Chad couldn’t help but notice him because the man had such a shocked look on his face as he stared wide eyed directly at him. 
      “Holy smoke!” the man finally exclaimed, his eyes never once leaving Sissy.
     Chad could feel his face growing redder.  He could also see a few of the other workers poking their heads out to see what was going on.  None of them appeared interested in going back to work.
      “We need these cleaned as soon as possible,” Mel said as she took the dresses from Sissy. 
     Chad wasn’t sure he was glad to get the dresses out of his hands or not, because now the dress he was wearing was fully on display.  He really wanted someplace to hide, but he had nowhere to go. 
     It was almost a full minute more before the man could tear his eyes away from Sissy long enough to see the other dresses that Mel was holding out for him.  He took them and hung them up on a long hook and started looking them over.  He first noticed the baby food stains on the pink dress.  He poked at one of them for a second before turning to the blue dress.  That one he only glanced at. 
      “Can we get these back this morning?”
     The man raised his eyebrows for a moment before answering.  “Yeah, sure.  You want the one hour service?”
      “Yes please,” Mel confirmed.
     The man wrote out a couple of tickets, ripped off the ends and handed them to Mel. 
      “Thank you,” Mel said as she turned and led the way back outside. 
     Chad followed her, but not without noticing that every one of the employees in the store was still watching him.  As he got through the door and it closed behind him, he turned for a moment to look back.  He could just see through the window several of the employees gathered around his sissy dresses, pawing at them, probably not believing what they were seeing!  Walking the few steps back to the car was its own nightmare, because now that the other dresses were out of his arms and away from his body, his skirt was free to go crazy again.  He was relieved to force his way back into Mel’s car, crushing his skirt again in the process, and put his baby bottle back to his mouth.  At least sucking on the bottle was comforting.  Nothing else in his life certainly was!  And then another thought hit him.  They would be picking up his dresses from the cleaner in an hour – but he had less than an hour before he had to be leaking! 
     Chad had already guessed that their next stop would be the drug store, but he wasn’t happy to see that he was right.  Especially dressed the way he was again.  Would those two pain in the neck girls be there again?  He really hoped not, but somehow he had a feeling that they would be.  In fact, they would probably be there just to see him!  With one last pull on his baby bottle for courage, he grabbed his purse and forced himself to get out of the car. 
     Mel had started to lead the way into the store, but she paused for a moment to look back at him and let him catch up.  Something looked out of place – and she didn’t really like it.  Unfortunately, there wasn’t much she could do about that right now.  “Remind me later to get you a new purse!” she said.  “Something that looks a lot more sissyish to go with that dress.”
     Chad was embarrassed to even think about getting another purse – especially one that went better with what he was wearing.  He wasn’t even certain he could imagine what it might look like!  He didn’t get much of a chance to even try to imagine it because all too soon he was walking into the store.  The high pitched squeal of delight rang in his ears before he was fully through the door.
      “Ahhhh!  Don’t you just love it?”
     Chad didn’t take two steps before he was quickly attacked by both girls, pulling at his ruffles and feeling his dress all over.  He kept expecting to see the store manager again at any second, but so far, they were being left alone – by the manager at least.  A number of other customers walked over right behind the girls for a better look too.
      “I never thought I’d see anything like this!” one of the girls exclaimed as she pulled on his skirt.
      “I know!  I couldn’t believe the dress he wore last week!” the other one replied.
      “Half a dress, you mean,” the first one corrected her.  “Because it didn’t cover enough to be called a whole dress!”  Both girls broke out in peals of laughter again.
      “Yeah,” the second one finally agreed.  “You could see his diapers perfectly!”
      “And they were wet!”  Her statement only renewed their laughter. 
     Chad could feel his face growing very red with embarrassment.  But there was no place to hide so he was forced to stand there and endure it.  Where was that manager?
      “So do you have any more like this?” one of them asked him.
     But Chad was saved from answering by Mel.  “I think we should move away from the door so we aren’t blocking traffic,” Mel suggested.  “Why don’t we all go back to the adult diaper aisle again?  Okay?” 
     Neither of the girls replied.  They both just turned and led the way toward the back of the store as they talked and giggled together constantly.
      “It looks like your dress is a hit,” Mel stated as she and Sissy followed the two giggling girls. 
     Chad made no reply.  It was a hit alright.  Just not the kind of hit he would have preferred.  As they walked, he was very aware of the skirt on his dress swishing back and forth a bit.  He did his best to walk carefully and gingerly, but in four inch heels it was pretty much impossible.  His dress seemed to sensually caress him all the way to where they were going, forcing him to be more wary than ever of his chastity device hurting him.  As they reached the incontinence aisle, he noticed that some of the other customers had followed them too.
     Things were quieter back between the shelves by the adult incontinence supplies.  But not by much.  Especially once the girls started laughing and gushing over him again.  “Have you ever seen so many ruffles in your life?” one of them exclaimed.
      “I don’t think I’ve seen that many ruffles… with all the ruffles I’ve ever seen – in my entire life – combined!” the other one replied.
      “So, like I asked earlier,” the first girl said to Sissy, “do you have any more like that?”
     Chad really didn’t want to speak but since she had asked, he didn’t have any choice.  “Yeth” he replied, totally embarrassed by his lisping sissy voice. 
      “Curtsey before you answer, idiot!” Mel yelled quickly.
     Chad had to curtsey then repeat his silly one word answer.  The two girls started laughing all over again.  “Did you hear that?” one of them asked?
      “Tell them about your other dress, Sissy,” Mel prompted.
     Chad was forced to curtsey again before answering.  “My odda dweth ith bwoo, he told them.  “An it hab bwoo thoeth to go wid it.
     The girls looked a bit confused.  One of them looked at Mel.  “I think he said something about blue, but blue what?”
      “Shoes,” Mel replied.  “He has another dress kind of like this one only in blue and it has matching blue shoes.  His speaking takes a little time to get used to.”
     The girl let out an explosion of air through her teeth as she tried to stifle her laughter.  “You can say that again!”
     The other girl suddenly noticed something.  “Hey!” she exclaimed.  “Look at his nails!  What’s on them?”  She practically pulled one of Chad’s arms out of the socket as she grabbed it to look.  “Look!  Look what it says!”
     The other girl grabbed his other hand and held that out too so they both could see.  “They both say ‘Sissy,’” she managed to get out before they began laughing too hard again to speak.
     They held Chad’s arms out for a moment before the first one held up her hand so Chad could see it.  “See, I finally got my nails done real long like yours, just because I liked the way they looked so much.  Of course they’re only press on nails.  I can’t afford the ones like you get, but still, aren’t they great?”
     But before Sissy could answer, the other girl interrupted.  “But now his are shorter than yours!”
      “Yeah,” the first girl replied as she held her hand up against Chad’s to compare the length of their fingernails.  “But not by much.”
      “So now that you have nails like his were, are you going to get your name spelled out on them too?” the one girl asked her friend teasingly.
     The girl shook her head laughing.  “I don’t think so!”
      “Hey,” the other girl suddenly exclaimed as she thought of something else.  “Is he wearing diapers again?”
      “Of course silly,” the second girl replied.  She looked to Mel.  “He is, isn’t he?”
      “Of course,” Mel replied.
     The first girl bent over to look under Chad’s skirt.  “Yep!  They’re there alright.  And I can see that they’re wet again too.”
     Chad heard not only the giggling of the two girls but a few exclamations from the other customers nearby as well.
      “Speaking of diapers,” Mel said, “I think it’s time to get yours for the week.”
     To Chad, her announcement was like breaking up a party – and it was very welcomed!  He started pulling large packages of disposable diapers off the shelves. 
      “Here,” one of the girls said, “let me get that for you.”  Before Chad knew it, she had reached out and taken the package from him.  And when he pulled the second package out, the other girl took that one.
      “Don’t forget one for you to carry too,” Mel said.  Chad already knew that he would need three packages, especially with as many diapers as she was making him go through now.  He grabbed one more for himself.  But Mel didn’t seem to be satisfied.  “You know, maybe you better grab an extra package too, just to be safe!”
     They marched back to the checkout counter, each girl carrying one package each, and Chad with two.  He couldn’t really see how he could possible need more than three packages, but, well, maybe next week he wouldn’t need to buy quite so many. 
     There were no customers for once at the checkout, and the woman at the register took the time to appropriately Ooo and Ahh over Chad’s dress.  A few minutes later, he had paid for his purchases and was lugging large heavy bags out to Mel’s car as Mel waved goodbye to the two girls. 
      “They thought your dress was wonderful!” Mel exclaimed just before she reached the car.  “You should have thought to wear it for them before this!”
     Chad mentally shook his head.  Yeah right!  Not in this life!

The Bet - Chapter 50 (Saturday – week 7 part 1 of 10)

The Bet
by Karen Singer

Chapter 50 (Saturday – week 7 part 1 of 10)

It was the vision she had seen several weeks ago now – the vision of Derek kissing Sissy. A kiss so filled with passion it made her hot and tingly all over. The kind of kiss every woman yearns for. Yet he had only kissed… Sissy.
But her dream was able to take things further than real life ever could. In her dream, Derek turned away from kissing Sissy, his lips smeared horribly with all the lipstick she had made Sissy wear. Derek turned towards her. His eyes locked onto hers… and she felt weak. Helpless. There was something about the power of his gaze that riveted her. And then he was there, standing right in front of her, looking only at her, only into her eyes. His deep eyes… looking deeply into hers.
He reached out and grabbed her, tenderly, yet powerfully. He pulled her into him, holding her tightly to his body... his beautiful, powerful body. Very slowly, he brought his head down to meet hers. He kissed her lips, first softly, then stronger and stronger, more and more passionately, till she was writhing in his arms with desire. It was the same kiss he had given Sissy, only more so. A kiss that she could feel as much in her wet and aching sexual zones as in her lips. He seemed to be all hunger and need, just like she was. And when that kiss finally ended, he continued to hold her tightly to him, staring down into her eyes.
Ray and Sissy evaporated into nothing as he turned her toward her apartment, and led her slowly toward her bedroom… and her bed. He scooped her up in his arms and laid her down on top of her bed, ever so gently, and still fully dressed. Then he climbed on top of her and slowly began removing her clothes. His touch was so careful… so sensual! She writhed with pleasure as he released each fastener, removed each piece of clothing. She wanted him so much.
She was naked now, yet he was fully dressed. His hands played tenderly over her body, igniting feelings she had rarely ever felt in real life. Feelings that made her whimper in her sleep. And then he let go of her and grabbed his shirt and ripped it from his body. Somehow, that single motion removed every stitch of clothing he had been wearing so the two of them were naked on her bed – together. He had such a beautiful body, muscular and smooth. And down below, where it counted, he was just as impressive… and erect.
Ever so slowly, he brought his body back down to meet hers, but not putting any of his weight on her. Her nipples just barely touched his chest as he began sliding his body back and forth against her. Very slowly, he increased his weight on her, lowering his body down… down… till he was fully on her. And that’s when she felt his hand reaching down… down… between her legs, opening her up, making her ready – which she was. More than ready. She hungered for him.
She felt him lifting his hips, guiding his turgid manhood into her. And with one powerful thrust of his hips…
Her alarm buzzed, crashing its way into her dream world. Ripping her away from a dream so intense it hurt. She tried so hard to ignore the intrusion… tried so hard to hold onto the Derek in her dream… tried so hard to hold on to the wonderful erotic feelings her body craved… But the ever invasive alarm would not be denied. It was too powerful to be ignored. Too powerful to let her have the few minutes more she so desperately wanted. With an angry slap of her hand, she turned the darn thing off. Such a great dream – ruined! What a lousy way to start the day! Especially when it had almost been so good!
She sat up on her bed, aware of how moist her sex was. Darn it! She got to her feet, grabbing her robe at the same time, and put it on as she headed out toward her kitchen, and her coffee pot. Coffee! She didn’t even have to think about it. It was a given. Still, it would be nice to have someone deliver a freshly made cup to her in bed. Sissy would be doing that very soon. She hoped. But five minutes… It seemed so impossible!

Very gradually he became aware of things. He was lying on his blow up mattress. The huge bulk of his soggy and messy diapers kept his legs splayed wide apart. Perhaps the biggest thing he noticed, not to mention perhaps the biggest pleasure, was that his ever present breast forms weren’t there. None! Not even the bra he usually wore to bed to support them as he slept. It would only be for the one night he knew, but still, it felt so good!
Without thinking, he shifted the pacifier in his mouth a bit to yawn deeply. Then his lips closed back around it again. And that’s when he realized that it was morning. But was it time to get up yet? His alarm certainly hadn’t gone off as it always did. He remembered that today was Saturday, but still… Mel always set his alarm for him. Since he was awake, he rolled off of his mattress, more carefully than usual, only knocking down one empty baby bottle in the process. He got to his knees and turned to look at his pink alarm clock. As far as he could tell, it was way past time to get up! He looked at the clock more closely. The alarm hadn’t even been set! And that realization brought a new worry to his mind. Did Mel leave him a note last night? It didn’t look like it.
He forced his way to his feet and waddled out of his bedroom to his kitchen. Relief washed over him the moment he saw the little piece of paper there. So why hadn’t she set his alarm?
He read the note.

Sissy,

Three bottles before you clean up. As usual, call me the minute you get your one diaper on. I’ll have more instructions for you then.

More instructions. He could pretty much guess what they would be. But still, why not just put it all in the note?
He didn’t even have to think about it as he went to his refrigerator to remove three of the bottles that should be there, but he stopped as his hand reached out toward the bottles. His hand… or more accurately, his fingernails! His crazy fingernails that now spelled out Sissy – one letter on each nail – both hands! It was… crazy! He dreaded anybody seeing it. How could anybody notice his nails and not know immediately what he was? It was so… embarrassing! Purposely turning his hands so he couldn’t see his nails, he reached in and removed three of the bottles from his almost depleted supply. He carried them to his chair where he sat gingerly on his messy padded bottom and started drinking the first one. How was he going to get away with nails like this? He couldn’t see any way possible.

Mel kept glancing at her clock. No call from Sissy yet! Maybe she should have set his alarm after all. In fact, she should have set his alarm and not set hers! She was still a bit miffed over being awakened at exactly the wrong place in her beautiful dream. Question – would Derek be anything like that in person? She looked forward to finding out tonight!
So why hadn’t Sissy called yet? She knew he was a very sound sleeper – very sound! And she often pushed him fairly hard every day. She had worked with his little ballet till late last night again too. So the guy probably needed a little sleep. But still, he should be up by now!
She grabbed her phone angrily and dialed his number – and listened, and listened to it ringing without being answered! Where the hell was he?

Chad was in the shower when he thought he heard his phone ringing. He stuck his head out to be sure. Yes, darn it! The sound was heavily muted since his phone was in his purse, but he couldn’t mistake that ring. Dripping wet, he hurried for his purse to find his phone. He heard it stop ringing long before he got to it. Breathlessly, he pulled it out and checked to see who had called. Mel of course. Who else? He quickly dialed her number. “Hewwo Mithtweth,” he said in his sissy voice.
“Sissy! Where were you, still in bed?”
“No Mithtweth. In da showa.”
“Well, what’s taking you so long? I expected to hear from you long ago!”
“I slept late,” he replied in his silly sissy voice. “My alarm wasn’t set.”
“I know. I purposely didn’t set it. I was trying to be nice for a change, but I didn’t think you’d sleep this late!”
“Sorry, Mis… Oh shit!” he suddenly exclaimed. He had started to say he was sorry, when he noticed he was peeing on the floor – almost on his purse.
“What was that?” Mel asked angrily.
“Um… Sorry Mistress, it’s just that I… well… I just almost peed on my purse. Fortunately, it’s only on the floor and I can clean it easily.”
Mel almost laughed as the anger seemed to drain right out of her. She could just imagine! “Well, hurry up then,” she replied. “I’ll be expecting another call from you in a few minutes as soon as you get that diaper on. And don’t get dressed yet!”
“Yes, Mistress,” he said – into an already dead phone. He stared down at the puddle of pee at his feet. Geez! Why did it have to happen now?

Mel carried her phone with her as she headed back into the kitchen to pour a fresh cup of coffee. He had peed on the floor! And obviously, he hadn’t known he was going to do it! She really wished she could have been there to see it. Once again she had been left out – even if he was alone this time. But still, right now, that one sign seemed encouraging as far as their bet went. But she also knew that overall, it probably didn’t mean much.
She chuckled a bit again at how surprised he had been when it happened. Not to mention how bothered he probably was over having to clean it up. She stopped as an odd thought struck her. No, it was a totally dumb idea! Totally! But… Darn if she wasn’t going to try it later! At the worst it would be fun to watch!
She figured that by now he had to be getting ready to get his diaper on. With her phone in one hand and her cup of coffee in the other, she grabbed her keys and headed out the door. Her phone rang just as she was about to put her key into his door lock. Instead of answering it, she pushed his door open. She saw him standing not far away, his purse on the floor in front of him, his cell phone in his hand. “Don’t bother,” she said, “I’m already here.”
As she walked in, she could see where he had peed on the floor. It still hadn’t been cleaned up.
“Um…,” he said embarrassedly, “I haven’t had time to get that yet.”
“Don’t worry about it, you can take care of it in a few minutes,” she said as she headed straight for his bedroom.
She didn’t really like seeing the breast forms not glued on him, but it was starting to get late and she didn’t want to take the time to glue them on right now. In his bedroom, she went directly to his cheap set of cardboard drawers and opened the top one. Fortunately, it held just what she hoped it would. She pulled out one of his bras and handed it to him. She pointed at the forms that were lying on the floor nearby. “Don’t forget those.” As he was putting them on, she searched two more drawers before she found what she was looking for – jumbled in amid his many pairs of pantyhose. As soon as he was ready, she handed him a pair of his white sissy socks with pink lace around the top. She didn’t bother watching him put them on but went straight to his closet instead. There she pulled out his pink patent leather high heels. She had to hold them in her hand for a minute till he was finished with his socks, then she handed them to him. “When you’re ready, you can clean up your mess in the other room. Then drink another bottle and fix your makeup and hair. Don’t wear anything else. Bring all your empty bottles to my place as soon as you’re ready. I’ll see you there. And hurry up. We have a lot to do this morning!” She left him without another glance and went straight back to her apartment.
It was almost forty-five minutes before Sissy knocked on her door again. Actually, Mel figured that he had done fairly well to take care of all his makeup, hair, clean up the mess on his floor, as well as drink another bottle in that time.
As soon as their usual morning greeting was over at the door, Chad followed her straight back into her bedroom. Earlier, when she had handed him his frilly socks and told him to wear his pink patent heels, he had been afraid of what she wanted him to wear today. Last week she had made him go to the drug store wearing his pink baby dress. That had been horrible! Was she going to make him wear it again today? He certainly hoped not, but it was starting to look more and more like it.
He waited as she went into her closet. She pulled out his pink baby dress and held it up to look at it. His heart cringed more than a bit at the sight of it – especially when she laid it down on the bed. But then she went back to her closet again and pulled out his blue sissy dress. Was she going to switch this time and make him wear that one instead? But that dress also went on her bed on top of the pink one. She went back to her closet one more time, and brought out the last of his silly sissy dresses, the white one with the pink bodice. The one with so many ruffles that the skirt stood almost ridiculously straight out!
“Here,” she said as she handed it to him. “You can wear this one today.”
The dress was practically torture since it was loaded with ruffles all over. Would she really take him out in public wearing this monstrosity? Unfortunately, he knew the answer to that one was a big yes! She had taken him out wearing the baby dress last week, so he figured that Mel wouldn’t consider this one any worse at all. His hands were shaking a bit as he reached out to take the dress from her. But now he still had to get the darn thing on.
It had been a long time since he had last worn it, but the moment he started to pull it on, he quickly remembered the main problem with the dress – there were so many darn ruffles that the whole thing seemed to be alive! Every tiny little movement of his body seemed to translate into a bigger movement of the skirt – that was so full it stuck straight out. The satin material of the dress itself felt sensual against his skin, but it was nothing compared to the mounds and mounds of very soft ruffles that were layered over it and also supported the ruffled skirt as well. Ruffles that didn’t allow it to remain stiff, but instead let it move and sway all too sensually. The whole thing was a nightmare! And worse, once he had it on, the skirt stuck so far straight out that he couldn’t tell if it covered his diaper or not. And he had no way to tell one way or another. If he tried to reach down with his hand, he had to push the skirt down as well, so that didn’t tell him anything! Nightmare didn’t begin to describe the crazy thing.
Mel shook her head. “Why have we let that thing just sit in the closet for so long? I love it! I think it will be the perfect outfit for you today. Especially with everything we have to do.”
Chad didn’t love it. He was still trying to picture himself going out in the stupid thing. And worse, he was starting to worry about his darn chastity device hurting him again because of it! So far, so good, but he hadn’t taken more than two steps in the dress yet! What would happen when he had to keep moving?
Mel looked him over critically and smiled. Perfect! “Okay, Sissy, grab those clothes from the bed and get your purse. We have things to do and places to be.”
Just walking to the bed made his skirt swish back and forth alarmingly. As he picked up the two sissy dresses, he wondered what Mel had in mind for him today. Why would he need all three dresses? He followed Mel out to the living room where she was just checking his diaper bag. He saw her close it and pick it up herself.
“Grab your purse and let’s go,” she said just before she opened the door and walked out.
Chad paused a moment for courage. He was going outside in the silliest dress he could imagine – carrying two more dresses just as bad in his arms. He had to force himself to step out through her door – and close it behind him. Outside, in a mountain of ruffles, with more ruffles filling his arms. What a nightmare!