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.