The Bet - Chapter 51 (Sunday – week 8 part 4 of 8)

The Bet

by Karen Singer

Chapter 51 (Sunday – week 8 part 4 of 8)

     Chad stared at his reflection in the full length mirror hung on the back of his closet door.  Derek knew!  He knew… everything!  And it wasn’t good.  And now they were going out to the mall.  Everyone.  Together.  The only good thing that Chad could find was that Mel hadn’t made him wear his crazy silly sissy dress.  Instead she had sent him home to change into something more… suitable.  And not his maids dress either – fortunately.

     But she had sent him home to change – after she had changed his leaking diaper, right in front of Derek!  The thought still sent chills down his spine.  And of course Derek had seen his damn chastity device.  But when Mel had asked him if he wanted to touch it or see it closer, he had backed away and declined.  Fortunately.  Things were bad enough as they were. 

     So now here he was, dressed like he would be for work, and ready to go shopping again.  Well, sort of like he would be for work. He was still wearing only one diaper with a time limit to get it leaking, and while he was wearing his waist cincher again, he wasn’t wearing his all-in-one girdle.  So it was really like she had him dress after work now, when they were going out.  And they were going out again, only this time Derek would be there too.  Would Mel make him curtsey to everyone and show off his humiliating fingernails like she had at the grocery store?  He hoped not.  But he could still see it happening.  What would Derek think when he saw him doing that?  But he was fairly sure that it wasn’t possible for Derek to think any less of him now than he already did, so what did it matter?  But at least he didn’t have to wear his silly sissy dress!

     He tore his gaze off of his reflection and walked away toward his door, stopping only long enough to pick up his purse.  This wasn’t going to be good and he knew it.  He opened his door and walked out.

     Sissy sat in the backseat of Derek’s SUV sucking on his baby bottle.  As far as he could tell, he was being ignored by both Mel and Derek in the front seat – and he was glad.  He was also glad that Derek’s SUV had heavily tinted windows.  He didn’t think anyone could see him drinking his bottle through those windows.  Well, maybe they could.  But he felt a little safer anyway. 

     As far as he could tell, Mel wasn’t going to hide anything from Derek, that’s why she had insisted he keep drinking from his bottles while they travelled to the mall.  He only hoped she wouldn’t keep pressing them at him while they were in the mall.  Unfortunately, he had noticed that his diaper bag was heavier than usual again when he carried it down to the car.  No doubt it was loaded down with extra bottles.  Thoughts of what he had gone through last night ran briefly through his head, but they were quickly drowned out by his worry over what was about to happen at the mall.

     Mel tried to reach for that comfortable feeling she had had with Derek last night, but it wasn’t there.  She missed it.  All the way to the mall, they each made bits of small talk, as if each of them were trying to get past the big obstacle between them, the obstacle that was embodied by Sissy sitting silently in the back seat.  But as far as Mel could tell, reaching that feeling of comfort again wasn’t happening for either of them.  Still, she appreciated that Derek seemed to be at least trying.  A few times, Derek asked little questions about Sissy and she did her best to explain, especially about how he craved the humiliation and that this whole side of his personality was like a drug, one he could never break free of and one he could never get enough of.  She could tell by Derek’s short answers that he didn’t believe a word of it.

     When they got to the mall, she let Sissy put his bottle away for now.  But she had him carry his diaper in bag with him.  “What if he leaks while we’re in there?” she explained to Derek.  “His time limit isn’t all that far off.”  Derek had said nothing.  She linked her arm thorough Derek’s as she had done at the art gallery the night before, trying again to find that level of comfort with him.  He let stay that way and she was glad.  Then, with Sissy following closely behind, they all walked into the mall together. 

     The mall was crowded as it usually was on Sundays around lunchtime.  People seemed to be everywhere.  But with her arm still linked in his, Mel realized that Derek seemed to be purposely setting a slower than usual pace, as if he too were trying to recapture the cozy feeling they had enjoyed together last night.  Purposely, she leaned in closer to him.  He responded by momentarily tightening his arm around hers.

     They sauntered like that for a few minutes before Derek looked back toward Sissy as if he were bothered by something.  Mel said nothing since Derek had only turned to look back briefly. 

     But a few minutes later, Derek turned to look back at Sissy again. 

      “He’s still there, isn’t he?” she asked. 

      “Oh yeah,” Derek replied softly, as if he were dissatisfied by it.

     Then, a few minutes later, he looked back again.

      “What’s wrong?” Mel asked.

      “I don’t like him following me.  I feel like I’m being stalked.  Isn’t there somewhere else he can walk?”

     “I guess he can walk in front of us instead,” she replied.  “Just as long as he stays within earshot so we can tell him where to go.”

      “I think I’d like that better.  It gives me the creeps to have someone like that following right behind me where I can’t see him.”

     A minute later, Chad was leading the way through the mall.  He felt much more exposed and on display now, and much more like he was at the mall on his own, which he wasn’t.  But that illusion was hampered by Mel continually telling him to walk slower so he wouldn’t get too far ahead.  Chad finally slowed down till he felt like he was barely moving. 

     Every time he looked back, he could see Mel with her arm linked through Derek’s arm, walking ever so casually as if they didn’t have a care in the world.  But then, they didn’t.  They had no need to hurry anywhere, which didn’t do him any good.  The slower he went, the more time it gave for people to look at him, and the more he noticed the other people in the mall giving him more than a casual glance.  It was much better when he could hide behind them.  He didn’t like leading the way at all.  And he didn’t even know where they were going!

     The comfortable feeling was starting to sink in once again.  Somewhat anyway.  Mel felt good walking through the mall with Derek.  A big strong handsome man on her arm was something she found she really liked.  And since Sissy was now in front where she could keep an eye on him, she felt more comfortable than ever.   

     Derek was enjoying being with Mel again, but he still couldn’t fathom Sissy.  He was still bothered by what he had found out earlier… but the more he watched Sissy as he walked in front of them, the more Derek started to wonder about something else.  “I just don’t get it,” he finally commented.  “Why do you dress him like that when you go out?”

      “Like that?  Like a woman?  I’ve been kind of systematically trying to remove… or deny him, every single male trait that I can.  So I keep him in women’s clothes all the time.”

      “No, I guess I get that.  But that’s not quite what I meant.  I mean… he’s supposed to be a sissy, right?”

      “And he is,” she assured him.  “A big one.”

      “Yeah, I have to agree.  You can imagine my shock.  I still can’t get over it!  But still, if I’m reading this situation right, then I would think you would want to flaunt that a bit more.  Make people realize what he is the moment they see him.  Right now, I don’t think anybody is paying all that much attention to him.”

     Mel watched Sissy for a few moments as well as the people around him.  There were one or two who gave him an odd look, but all too many just passed him by as if they didn’t notice anything out of the ordinary at all.  “You should have seen what I had him wear to the grocery store today.  Yesterday too.”  She laughed.  “You wouldn’t say that if you had seen it.  I was actually planning on having him wear it again to the mall today, but since you were with us, I decided maybe I better tone things down a bit.”

      “Thanks,” Derek replied.  “I appreciate it.”  They continued on for just a minute more before he added, “But I still would have thought you would do something more to make him… stand out.”

      “I don’t know what else I can do,” she replied.  “I don’t want to get arrested.  You have something in mind?”

      “I don’t know, I just thought you’d dress him more… different.  That’s all.”

      “Different?  Like what?”

     Derek watched Sissy for a few moments as they walked.  I don’t know.  Maybe dress him more… sexy or something”

      “Sexy?  Like I did for the poker game?”

      “You could, although to tell the truth, I didn’t find him all that sexy looking.”

     Mel stared up at him for a moment as they walked.  “But you have something else in mind, don’t you.”

     Derek thought about it.  “Not really.  I really don’t have a clue.”

     A short distance away, Mel spotted another woman – an obviously well dressed, beautiful woman that she was sure would turn most men’s heads.  “How about like her?” she asked.  She didn’t even bother pointing because she was sure Derek would notice her.  She wasn’t wrong.

     Derek shook his head.  “You’d never get Sissy to look like that!”

     Mel didn’t know if she should agree, or laugh, or feel slighted about the way he had obviously noticed the other woman when he was out with her.  “Then what?” she asked. 

     Derek looked around again.  “I don’t know,” he repeated.  He spotted a group of teenage girls up ahead, staring at one of the window displays.  “How about like them?”

     Mel looked.  “Them?  Girls?”

      “Yeah.  Maybe anyway.  Like I said, I really don’t know.”

     Mel looked at the girls closer.  While most of them wore jeans, several of them were wearing skirts so short they were positively sinful.  She looked from the girls back to Derek and punched his arm playfully.  “You would go for something like that!”

     Derek laughed, but it was a strained laugh.  “It was just a suggestion.  That’s all.”

     Mel looked at the girls again.  A moment later she figured that Derek could be right.  “It might work,” she mused. 

     Derek nodded, “Maybe.”  A moment later he asked, “So where do you find clothes like that?”

      “You mean… right now?  Buy him an outfit like that… today?”

      “Why not?  We’re not doing much of anything else.”

     Mel could only agree.  “Why not?”

      “So like I said, where do you find clothes like that?”

     Mel stopped and looked around.  “All over this place!  Most stores in the mall cater to girls that age.”

       “Okay, so pick one?”

     Mel looked around and spotted a perfect choice up ahead.  “Sissy,” she called ahead as she pointed to where she wanted to go, “head for that store over there!”

     Once he got inside, Chad was glad that he was out of the main stream of traffic and no longer where so many people would see him.  But now, in this store, he felt very out of place as he stared at the youngish style of clothes on all the manikins.  Nothing looked like Mel’s style at all, but then, he didn’t really know what Mel would be looking for.  Since he didn’t know where to go once they were all inside, he felt safe following them around again.

     Mel glanced around the store as soon as she walked in.  Where to go?  The entire store catered to the wild teen styles.  Things she would never consider wearing.  She wasn’t even sure she would have considered wearing some of them when she was a teenager herself.  Okay, yes she would – in fact, she did.  But that was a long time ago.

     She wandered back through the store with Derek behind her… and Sissy somewhere behind him.  She started looking more closely at the racks of clothes.

      “Can I help you with anything?” a young salesgirl asked as she seemed to pop out of nowhere.

      “No thanks,” Mel replied.  “We’re just looking.”  The girl moved away, but not before giving both Derek and especially Sissy a long look-over.

     As Mel pawed through the clothes, she noticed Derek just standing back in the aisle watching her.  “Don’t be afraid to look,” she suggested.

     Derek just held up his arms.  “Not me,” he replied.  “I don’t know the first thing about this stuff.”

     Mel smiled to herself.  She should have known!  She could have Sissy looking through the clothes too, but for once, she didn’t want him to know what she was looking for.  Two racks over, she found a selection of very short skirts.  One of them was a pleated style in a blue, black, and white plaid. She pulled it out to look at it more closely.  She glanced up at Sissy so she could get a better idea of how she thought it might look on him.  He was just sanding and looking around, not paying much attention to what she was doing. 

     Keeping that skirt in her hand, she found another pleated skirt not far away.  This one was more of a green, red, and white plaid.  She actually liked it better because it was more colorful, but when she looked at the size, she was afraid it would be too small.  She tried to find another one like it in a larger size, but that one skirt seemed to be all they had.  She was about to put it back, but she thought better of the idea.  He was still losing weight, maybe he could wear it.  She held one skirt in each hand and compared them.  She really liked them both.  So if one didn’t fit, the other probably would.

     She looked back at Sissy again.  He was still looking around at the teen styles without moving from where he had been standing.  She was fairly sure he would really like to look closer – and probably try them on.  Well, he was going to get his chance.  But first… 

     She didn’t have to look far to find the salesgirl.  She had only moved a few racks away and was still keeping a close eye on things.  “Can you open a changing room for us?” she asked.

     The girl was surprised that Mel would want a changing room.  She didn’t look at all like the kind of women – mostly girls – who usually tried things on in the store.  But with a smile she said, “Sure.  Right this way.”

     But Mel didn’t move.  Instead she turned to Sissy.  “Sissy!  Follow her to one of the changing rooms.  Take that blouse and skirt off.  I’ll be in shortly with some things for you to try on.  In the meantime, get working on another bottle!”

     The salesgirl was shocked.  Not only because it was going to be the idiot guy in drag that would be going in to change, but also because the woman had ordered him to do it.  And she had called him Sissy?  But what worried her the most was the part about working on another bottle.  “Um…” she started to say to Mel.  “The management doesn’t allow alcoholic beverages in the store.”

     Mel was confused, but only for a moment.  “Trust me,” she replied.  “We don’t have anything like that.  His bottles are… something else.”

      “Oh,” the salesgirl said, not at all sure she understood.  “Um…  The rooms are back this way.”

     Chad followed the girl toward the back of the store with a growing sense of unease.  Him?  In the changing room?  He wasn’t sure if he should be surprised or not that Mel was looking at things for him to wear instead of herself.  He was mostly surprised because Derek was there.  Once again, he realized that she didn’t appear to be holding anything back from him.

     In the changing room, Chad did as he had been told.  He removed his skirt and blouse and pulled his latest baby bottle out of his diaper bag and put it to his mouth.  Maybe it was a good thing that he could sit here and drink from his bottle.  Since Mel didn’t seem to be requiring him to drink them openly in the mall today, he needed all the drinking time he could get to meet his leaking diaper requirement.  And the best part was that nobody could see him drinking from it in the little closed room.

The Bet - Chapter 51 (Sunday – week 8 part 3 of 8)

The Bet

by Karen Singer

Chapter 51 (Sunday – week 8 part 3 of 8)

     Chad had to carry bag after bag of groceries up the steps while wearing his silly dress and four inch heels.  And whenever Mel noticed anyone in the parking lot looking at him, she made him curtsey for them too.  None of them were ever close enough for him to show them his pretty fingernails though. 

     As soon as the groceries were all into her apartment, Mel had Chad remove his silly dress.  “Hang it up and make sure it’s ready for later,” she told him.  “We need to go to the mall this afternoon and I know you’ll want to wear it.”

     Wear it?  To the mall?  She had to be kidding!  But somehow he knew she wasn’t.  After this morning’s little romp through the grocery store, Chad wasn’t at all sure he was ready for that!  He could just see himself curtseying non-stop for everyone in sight.  And the mall would be much more crowded and busy than the grocery store had been.  He had no doubt that he was in for a miserable trip for sure!

     As soon as all the groceries were put away, Mel let him get his laundry from his apartment and get started on it since he had so much that absolutely had to get done right away, including his now wet sissy socks that he had worn while grocery shopping.  So clad in just his bra holding up his glued-on falsies, one diaper, and his pink high heels, he got busy again. 

     He was actually glad to be home now and doing something… useful.  He was especially glad to not be out in public anymore.  After last night and now this morning, he had way too much of public exposure!  And now Mel wanted to go to the mall later too?  And she wanted him to wear that silly dress again?  He really would be the talk of the town soon!  What would be next, putting him on TV?

     Since it needed to be done, Mel let him work while she started making more batches of tea.  At the rate he was drinking now, it was starting to look like she would be doing this every day!  But she would gladly do that as long as he kept wetting like she needed him to. 

     It was later in the morning when Mel’s phone rang.  She had just been contemplating starting in on the dress rehearsal for his little ballet tonight.  She grabbed her phone to answer it first.  “Hello?”

      “I have pictures…” Sandy’s delighted voice spoke back.  “Lots of them!  And you don’t want to miss them!”

     Mel laughed.  “So I take it things went well last night?”

      “Real well!  Not quite what I had in mind, but it was certainly interesting!  And Cassie and I took pictures all night so you could see what happened.”

      “I can’t wait!  Do you want to bring them over now?”

      “That’s why I’m calling.  I can be there in a few minutes.”

      “Sounds good to me.  See you in then.”  Mel turned to Sissy.  “Sandy is on her way over.  I’m going to change into something better for dance practice.  Let her in when she gets here.”

     Chad curtseyed and said, “Yes, Mistress.”  He was betting that Sandy was coming over just to tell Mel all about last night.  Last night!  What a night!  In some ways, he wanted to forget it – forever!  But in other ways… it had been without a doubt the strangest and most humiliating experience he had ever had!

     It was actually a few minutes later when the knock came at the door.  “Tell Sandy I’ll be right out!” Mel called from her bedroom.

     Chad was just glad that it was Sandy who was coming over, because dressed the way he was in only a very wet diaper, his bra, and his pink high heels, he would be even more embarrassed than he already was.  He opened the door and started to curtsey his greeting for Sandy, but he stopped in total shock!  He couldn’t move!

      “What the hell!”

     Still frozen in place.  Chad couldn’t move or answer.

      “Sissy!  Let her in!” Mel called as she walked out of the bedroom.  Then she too stopped dead in shock.  “Derek!  What are you doing here?”

     Unable to take his eyes off of Sissy, Derek replied.  “Maybe I should be asking you that question!” he asked angrily.  “I just stopped by to see if you wanted to go out for a bit of a snack, but I can see that it was a big mistake to come here!  What the hell is going on?”

     Mel pulled Sissy back out of the way and moved between him and Sissy.  “Come on in,” she invited as she held the door wider for him.  “I’ll explain it all.”

     Derek stepped inside, but he was still looking angry – mostly at Sissy. 

     As Mel was closing the door, she spotted Sandy outside, hanging back a bit from the doorway.  She looked shocked.  Sandy just pointed back towards her own apartment.  Mel nodded.  She would see Sandy later.

     Once the door was closed, Mel was quick to realize that Derek had not only seen Sissy, but he had probably already guessed the worst.  And since he had, she needed to keep Sissy on the straight and narrow!  “Sissy!  Greet our guest – properly!”

     Chad was horrified.  Curtsey to Derek?  He looked at Mel, not believing what she had just said.

      “I know you heard me! Now do it!  The way you’re supposed to!”

     Shaking a bit with fear, Chad finally dropped a proper curtsey for Derek, but his eyes were downcast at the floor as he said, “Hewwo Dewek.”  He couldn’t remove his eyes from the floor if he tried.

     Derek looked back and forth between Mel and Sissy several times.  Angrily, he shouted, “What the hell is this?” 

     Mel could see how angry and confused Derek was.  The other thing she noticed was his balled fists!  She knew she had to take charge of everything – and fast!  It was the lawyer in her that took over.  She turned first to Sissy to get him out of the way.  “You!” she said.  “Go stand on your perch.  And take a fresh bottle with you.  We’re going to be busy for a while.  And if you start leaking, keep quiet about it.  I don’t have time right now.”  Then she turned to Derek.  “And you…” she pointed at the couch.  “Sit!”

     But Derek was too angry to be ordered around.  “What the…”

      “I said sit!” she shouted as she pointed at the couch again.  “I’ll explain all of it, but not till you’re sitting down!”

     Derek headed slowly and almost warily toward the couch.  But he looked back and forth still between Sissy and Mel.  He sat, but it was reluctantly. 

      “Good!” Mel declared.  But she couldn’t help but notice the tension still in Derek’s body.  He was a ticking time-bomb that had to be defused!  She turned toward Sissy who seemed to be barely moving.  “Hurry up!” she ordered.

     Chad grabbed a fresh bottle and ran to his corner where he climbed up onto his perch and… reluctantly… put the bottle to his mouth to start drinking it.  Derek had seen him!  Derek… his friend!  Or was it former friend now.  Most likely, former friend.  And now, Derek knew everything… or soon would.  And there was nothing he could do about it.  He leaned as far into the corner as possible while still drinking his bottle.  If he could have gone through the corner, he would have.

      “Now what’s…” Derek started to ask, but Mel held up her hand to silence him. 

      “I told you I would tell you, and I will.  All of it!  But you’re going to listen to it calmly and rationally!  You’ve already seen him.  You already know some… or you think you do.  But there’s more, and there’s a reason!”

     Derek looked dubiously at her.  “More?  And a reason?  This I gotta’ hear!”

     Mel knew he clearly didn’t believe there could be more… or a reason.  And maybe he was right – to a point.  But just as she had done with Robin, she decided she needed to start at the beginning.  She went to her desk and found her framed contract of the bet and carried it back over near the couch where she sat in a chair close to Derek.  “The day… Chad… moved in here, I accidentally found out some things about him that he never meant for anyone to ever find out.”

      “Yeah!  I can pretty much see what those things are!”

     Mel shook her head.  “Maybe, but you don’t know all of it.”

      “If there’s more, then I don’t think I want to know all of it!”

      “Yes you do!  Trust me!  For everyone’s sake!”

     Derek just glared at her.  “I’m listening.”

      “As I said, they were things he never meant for anyone to find out.  But I did.  And because of me, things have… well… escalated.”

      “Escalated?”

      “Let me continue!”

     Derek shut up, but he wasn’t sure if his curiosity was peeked, or if he just wanted to get out of there. 

      “That first day,” Mel continued, “I’m afraid I got him a little… drunk.  Well, we both got blitzed to tell the truth.”

      “I thought he didn’t drink?”

      “He doesn’t.   That was my fault for insisting.  But the result was that we wound up making a bet.  A very unusual bet, but a bet all the same.”

      “A bet?  This is all part of some kind of bet?”  Derek clearly didn’t believe it.

      “Yes and no!”  Mel took a deep breath before continuing.  “As I said, we got drunk that first day, but the ideas we talked about struck a chord in both of us, so the next day, we actually did made the bet between us.  And since I’m a lawyer, and contracts are the kind of thing I like to do the most, we… formalized it.”  She held out the framed copy of the bet for him to take.  “This is what it’s all really about.  As you can see at the bottom, we both signed it and had it notarized.”

     Derek looked at the bottom of the framed document and saw the raised seal and the signatures.  “Notarized?  For a bet?”

     Mel shrugged her shoulders.  “It’s what I do.”

      “So this thing is legal?”

     That was a really tricky question, the answer to which leaned more towards no, but that wasn’t anything she would tell Derek.  “Mostly,” she replied. 

     Derek rolled his eyes.  “I don’t believe it,” he muttered to himself as he looked back at the document, now bringing his eyes to the top of it to begin reading.  “What the hell is all this legal mumbo jumbo?” he asked as he tried to figure out the beginning of it.

      “I’m a lawyer.  It’s a legal document.  That’s how it’s done.”

      “Well I’m not a lawyer!” Derek replied as he handed the document back to Mel.  “You’ll have to explain it to me…  In English!”

     Mel took the document with a sigh.  Then, to the best of her ability, she started again at the beginning again, telling him all about Chad’s hidden quirky side, and all about the conditions of the bet.  And then she tried her best to explain to him how the bet had become so much more to both of them.  While she couldn’t really speak for Chad, she was pretty sure he felt the same way she did, that the bet had become their whole life.  That it meant so much for the future – for each of them. 

     Derek remained silent the whole time she was speaking. And when she was done, he continued to just stare at her for a bit… dubiously.  “So you’re telling me, he was pretty messed up in the head before all this started, and now things are ten times worse!”

      “That’s not exactly…  But… I guess it’s one way to look at it,” Mel agreed.

     Derek got up from the couch fast.  Mel noticed his balled fists again as he headed directly toward Sissy in the corner. 

      “Give me one good reason why I shouldn’t just shove my fist down your throat!” he roared at Sissy as he headed directly toward him.

     Mel stood quickly.  “No!  Don’t you dare!”

     Derek only looked back at her angrily as he stopped right next to Chad – still standing on his perch in his corner, holding an empty baby bottle by his side, cowering in fear, and now sobbing audibly.  Derek didn’t hit him, but he wanted to.  “You moron!” he yelled angrily at Sissy. 

     Mel watched carefully, but she didn’t approach.  She had hoped she had explained things well enough, but it wasn’t looking like she had.  At least Derek didn’t hit Chad… yet.  But her lawyer’s experience also told her that this confrontation had to happen between the two of them.  And for Sissy’s sake, it was probably better if he remained in just the position he was in… submissive, and silent!  Because otherwise, Derek really might shove his fist down his throat!

     Derek looked Sissy over.  He was wearing nothing but a diaper – an obviously very wet diaper!  But Mel had said this whole thing was over making him incontinent.  And hadn’t she said something earlier to him about leaking?  He saw the realistic looking breast forms inside of Sissy’s bra.  He could see how the weight of them pulled at his bra straps.  And the idiot liked that?  Then he looked down at Sissy’s feet – adorned in very high pink patent high heel shoes.  But Sissy was standing on some kind of bar that kept even those high heels off the floor.  It looked like it would be torture on his toes.  “Is that thing you’re standing on… comfortable?” he asked Sissy, his voice soft but dripping with threat.

      “He’s not allowed to speak when he’s up there,” Mel replied quickly.  While it wasn’t completely true, the last thing she needed was for Chad to say anything that might make things worse.  Chad’s only response was another audible sob as he tried to push himself even harder into the corner.

     Derek looked back at Mel, but only for a moment.  Then he turned to Sissy once again.  “So this is the kind of life you want?” he asked a bit softer, but it still held more than a hint of threat.

     Chad cautiously turned his head a little toward Derek.  How was he supposed to answer that question?  Not because he wasn’t supposed to speak, but because he didn’t know what to say. 

     But Derek didn’t really want an answer.  “Stick your face back in that corner, moron!” he yelled angrily.

     Chad buried his face fully back into the corner as fast as he could, even as more sobs started to escape him.

      “You want this kind of life?” Derek yelled angrily.  “Then you deserve this kind of life!  This and more!  You idiot!”  In disgust, Derek turned away from him.

     Chad was just glad it was over.  He hoped Derek would leave now – quickly.

     But Derek was just getting warmed up.  He turned right back to Chad again.  “I used to regard you pretty highly,” he said menacingly.  “You were my friend… at least I thought you were.  And then when you started showing up at work in dresses, my regard for you went way down.  Way down!  But now…  Now…  Now my regard for you has dropped a thousand percent!  I have no regard for you anymore!  My regard is less than zero.  It borders on total disgust!”

     Chad was sobbing uncontrollably now, almost as loudly at times as Derek’s voice.

      “You want this kind of life?” Derek continued.  “Then I hope you get everything you deserve!  Everything!  I’d still really like to ram my fist down your throat.  But I won’t.  I won’t because I can see that it would be nothing... nothing at all… nothing, next to what I sincerely hope you get out of this kind of life.  And I really hope you get it!”

     He turned away from Sissy in disgust.  He had meant every single word of what he had said.  He looked at Mel.  “I came here this morning because I thought we had made a connection last night.  I thought there might be something interesting between us.  I don’t know about you, but I had a good time last night.  A real good time.  I was going to see if you wanted to go out for lunch somewhere this afternoon.  But I can see that it was just a big mistake.  I’m sorry I came.”

     Mel watched as he stared toward the door.  But she stopped him quickly.  “Wait!”  She waited till he had turned to look at her again.  “I had a good time too.  A real good time.  And I thought we had a connection too.  I was… comfortable with you.  I didn’t want you to find out about… all this.  I’m sorry, but there’s nothing I can do about it now.  You know, and that’s all there is to it.  I was just hoping you would understand.”  She paused, but only for a moment.  “And…  And I’d really like to go out with you this afternoon.  If we can.”

     Derek stood there and stared at her.  Was she serious?  But he did still like her.  As much as he hated to admit it, he still liked her.  Last night he had liked her a lot!  “You want lunch?” he finally asked.

     She nodded.  “Yes…  But…  But you have to understand.  Sissy has to come with us too.  I can’t let him out of my sight right now.”

     Derek shook his head.  “Forget it!”  He turned to leave again.

      “Please!” Mel pleaded quickly.

     Derek stopped.  “I’m not buying him lunch!  I really don’t want him anywhere around!”

      “You don’t have to buy him lunch!  Me either!  Maybe we can just go somewhere where he can stay nearby.”

     Derek wasn’t too sure about that though.  “Like where?”

     Mel shook her head.  But then she remembered something.  “The mall!  I have to go to the mall this afternoon.  We could go there.  And Sissy can just… stay where I can keep an eye on him.”

     Derek wasn’t sure about it though.  “Why can’t he just stay here?”

      “Because I’m… doing things with him.  And because I don’t want to lose this bet!”

      “Doing things?  What’s that supposed to mean?”

     Mel’s face changed to a wicked smile.  “Take me to the mall and find out!”

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

The Bet

by Karen Singer

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

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

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

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

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

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

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

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

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

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

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

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

      “Be careful!” Mel warned angrily. 

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

     Again, Sissy had to curtsey and thank her.

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

      “Almost never!” Mel agreed.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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