The Bet - Chapter 54 (Wednesday – week 8 Part 1 of 9)

The Bet

By Karen Singer

Chapter 54 (Wednesday – week 8 Part 1 of 9)

     Derek’s strong arms enveloped her as they laid on her bed.  His powerful kiss lingered on her lips.  Even in her sleep she thrilled to the luxury of his embrace.  He was all male… so much male.  And she of course was so much female. 

     For some reason, she happened to glance to the side, and her attention was caught by Sissy, just standing there quietly.  Watching them.  Making no sound, no movement.  He was just there.

     She went back to paying attention to Derek’s wonderful body, but memories of Sissy started invading her mind.  She wanted to pay attention to Derek, only Derek, but her mind refused to leave Sissy alone. 

     In her sleep, she turned to Sissy.  “Leave us!” she commanded.  Sissy didn’t curtsey, he simply nodded oddly and walked off.  She would have to speak to him later about not curtseying.  But at least he was gone.  She went back to making delicious love to Derek, but her mind refused to think only of Derek.  Her mind could not help but think about Sissy too. 

     Derek’s body felt so good.  His kisses felt so good.  His love making felt so good… and yet, her mind refused to let go of the one thing she didn’t want to think about.  Frustrated, she got out of bed, leaving Derek behind, to find Sissy and see what he was up to.  But he wasn’t out in the living room.  He wasn’t in the kitchen either.  He wasn’t in her apartment at all.

     She went outside, over to his apartment… but he wasn’t there either.  Where was he?  She knocked on door after door, asking if anyone had seen Sissy. But nobody had.  She went down to the parking lot and searched everywhere she could think of… but no Sissy. 

     Where was he?  What had become of him? 

     She remembered the way he had simply nodded his head when she had commanded him to leave.  Why had he done that?  And now she was afraid that making love to Derek had driven him away – permanently.  Her command telling him to go was the final straw.  He had gone – permanently. 

     In her despair, she wept.  She wanted Sissy in her life… as dumb and crazy as that sounded, she didn’t want him to be gone. 

     Something else was irritating her too.  But then Derek was there, by her side, trying to console her… trying to love her.  She was glad he was there.  She wanted him there.  She wanted his love and attention… but she wanted Sissy too.  Why couldn’t she have both?  The other irritation grew.  Was it just that Sissy was gone?  But now she had chased Sissy away – and it hurt.  It hurt a lot!  Far more than she ever thought it would.

     The irritating buzzing of her alarm clock finally reached all the way through to her sleepy brain enough to bring her fully awake.  Ugh!  She opened her eyes, but she was so tired that she only wanted to go back to sleep again – bad dreams or not.  It had been a long night last night – very long.  Wonderful… but long.

     Yawning, she forced herself to move enough to sit up on her bed.  Memories of the emotions from her dream lingered, but not much more.  Sissy!  And Derek!  And of course, she wasn’t going to forget Ray either… although right now, Ray seemed a lot less immediate – or interesting.

     She looked at her clock.  So early!  An hour earlier than usual.  But she had to get up early – because of Sissy.  She had to talk to him.  It was important.  She really should have talked to him last night, but she had put it off because of Derek.  And Derek had stayed last night because she wanted him to stay.  But in the process, she had failed in her responsibilities to Sissy. 

     As she headed out toward her coffee pot, she remembered letting Derek beat Sissy last night – and how he had hurt him.  She remembered the way Derek had tied Sissy to his perch last night – because he didn’t trust Sissy.  And she remembered how she had shown Derek the way she raped Sissy’s ass last night… and the way that Sissy had again orgasmed for her… or was it for both of them?  No matter. 

     She knew all last night that she was neglecting her responsibilities toward Sissy by not talking to him… but she had let Derek distract her.  And now she felt bad about it. 

     As she watched the coffee dripping down into the pot, she remembered Robin’s description of the way Sissy had been accosted at lunchtime yesterday.  That was one thing she should have never put off.  She really should have insisted with Robin that she talk to him on the phone right away… but she had put it off.  Not good. 

     And then there was the other thing… the email that Sissy had worked all day on because he had been forced to type with the heels from his shoes that were taped to his hands.  That thought brought a smile to her lips, but the content of the email didn’t.  Robin had said that she thought Sissy had some good points in there.  And she was right!

     Why couldn’t Sissy simply admit defeat in this bet?  Why?  It would make everything so much easier on both of them!  Well, her especially.  But ultimately, it would be easier on them both – because of her long range plans for him.  Plans she dare not reveal until after she won the bet.

     But she knew why he wouldn’t admit defeat.  It was really the same reason she herself would never admit defeat.  Neither of them liked to lose.  Plus… Sissy had come up with a pretty good list of reasons why he needed to win – friends, a life, and more importantly, self-respect.  He didn’t know that she knew those things and she had to make sure he would never know it.  They were all… obstacles she had to overcome.  Somehow.

     She poured herself some coffee and carried it into her living room to think… and wake up.  So how were they supposed to solve the problem of who won the bet if it was close?  That was the one thing that Sissy didn’t put in his email.  And she was fairly sure she knew why.  It was because the answer was all too obvious.  But that obvious answer wasn’t one that he would be happy with.  And she supposed she really couldn’t blame him. 

     So her job now would have to be to convince him.  And that wasn’t going to be easy.

     Sissy’s heart was pounding as he turned off the irritatingly loud music blaring out of his pink clock radio.  How could such a tiny box put out that much annoying sound?  On the outside, the box looked so sweet and innocent.  And yes, it was his sweet little clock radio.  Sweet on the outside, but it housed a monster on the inside. 

     He glanced around his still dark room.  Something seemed different, or felt different.  But what?  Nothing he could put his finger on.  Then his gaze again swept over his clock radio… the time!  He started at the time display, trying to figure out if he was seeing it wrong, but no!  It did read an hour earlier than usual.  Was it a mistake?  It had to be!  Mel!  She had come in last night so tired from her visit with Derek that she had made a mistake and woken him up an hour early!  Darn her!

     Angry about it, he started waddling his way out toward the kitchen to see if she had left him a note.  Did she bother?  At that point, he didn’t really care.  He would have been happier with another hour of sleep!  But the note was there on his kitchen counter, right where she always left it.

Sissy,

Dress normal for work today, but look nice!  Wear the same shoes you wore yesterday.

Don’t forget your usual three bottles before you get ready.

I need you here early in the morning so we can talk.  We have a lot to discuss.

     That was it.  He now knew why it was so early – she wanted to talk to him.  Probably about the email he had sent her yesterday over how they should decide who won the bet if it was close.  At least she was paying attention.  Despite the early hour, he was glad she was taking it seriously.  At least, he hoped she was.

     He grabbed his usual three bottles out of the refrigerator and carried them out to his one and only chair facing his wall of shaming pictures.  But he didn’t really see anything on that wall, his mind instead wrestled with how they should decide who won the bet.  The obvious way was definitely out!  So how else could they do it?

     A full hour earlier than usual, Chad checked his reflection in his bedroom mirror one more time.  He had chosen his colorful print dress again – because he liked it.  He would have much rather worn a more comfortable pair of shoes, but the ones he had on did look good with the dress.  Of course, they were sexy enough that they would look good with anything. 

     His hair looked – okay.  His makeup as well.  The jewelry he had chosen was the wooden necklace and bracelet again along with the clear studs in his ears.  Underneath it all, he could still feel the overall compression of his all-in-one girdle – over top of his waist cincher, three diapers, and his plastic panties.  And of course, his pantyhose over that. 

     He was dressed normal again – not like the “hooker” look he had gone to work in yesterday.  He was relieved about that!  Normal… for him… now.  He was a guy, dressing as a woman for work, with diapers hidden under his clothes.  Such a thing was anything but normal!  But for him… lately… it was.

     With one last sigh, he grabbed his plastic bag containing the three empty baby bottles he had drank last night along with the three he had finished this morning.  He grabbed his diaper bag and his purse.  Then he took one last big breath to steady himself before his day full of humiliation would begin again.  And he stepped out his door… on his way… to more humiliation. 

     He hated it!  He loved it!

     Mel was yawning and stirring his baby cereal when she heard him knocking at her door.  She hurried to answer it.

      “Good morning, Mistress,” Chad said in his lisping sissy voice as he curtseyed to her.

      “Good morning, Sissy,” Mel replied as she stood back to let him in.

     She started looking him over as he was putting his things under her little table.  His colorful dress again.  Good choice.  When he stood back up for her inspection, she quickly went from the top of his head down to his shoes.  Acceptable.  “Okay, Sissy, get up in your highchair.  I have your breakfast just about ready.”

     Five minutes later Chad was locked in his highchair with a big bib tied around his neck.  He was eating a large batch of lousy tasting baby cereal with a tiny rubber coated baby spoon held in his left fist.  The usual. 

     Mel poured herself a fresh cup of coffee before leaning back against her counter where she could see and talk to him easily.  “So tell me about yesterday,” she said.  “I particularly want to hear about you being attacked at lunchtime.”

     Chad stopped eating.  Attacked?  Yeah, that was as good a description of it as anything.  But just thinking about it brought back all too much nervousness.  He didn’t know where to start.

     Mel realized she was being too confrontational in her attitude.  She could easily see how nervous he was just thinking about it – and he hadn’t said a word yet.  She berated herself again for not speaking about this with him yesterday.  She pulled out one of the kitchen chairs and sat down near him.  “Just start at the beginning,” she said kindly.  “Why did you go there to begin with?”

     Chad forgot about eating.  “I needed water… to refill all the baby bottles I had finished earlier.  Robin makes me refill them all so I have plenty to drink all afternoon.”

     Mel was a little surprised at that because she had been sending him with six bottles for the last week.  “How many is she making you drink every day?”

      “Way too many.  Probably at least ten.  And that’s not even counting the full cups of coffee she makes me get on my breaks too!” he added quickly.  “It’s way too much!  All I do all day is drink bottle after bottle!”

     It sounded to Mel like Robin was doing more than her part as far as keeping him drinking – and wetting.  She made a mental note to thank Robin for it.  But she wasn’t the least bit interested in Sissy’s complaining about that.  She moved on.  “Have you stopped at that store before?” she asked.

     Chad nodded.  “Yeah.  Sometimes.  Mostly just lately since Robin has been making me drink so much.”

      “And have you ever had any problems there before?” Mel asked.

      “No.  Not really.  Everyone there just usually looks at me oddly, but they never say anything to me.  Kind of like most places.  But I’ve never been anywhere dressed like I was yesterday.”

     Mel had no doubt the problem had been the way he was dressed.  She just had to get all the facts.  “So what happened?” she asked.

      “I had just gotten my bottle of water and was heading back to the car with it, when these guys stopped me.  I tried to get away from them, but they grabbed me and started pulling me toward the end of the parking lot.  It tried to get away, but I couldn’t.  And then the police showed up – fortunately!  They let go of me and I ran back to my car and locked the door.  You wouldn’t believe how scared I was!”

     Mel had no doubt.  She’d be scared to death herself.  Any woman would.  “I do believe it,” she replied.  “I totally believe it.  You had good reason to be afraid.  How many of them were there?”

      “Three,” Chad replied.

     Mel nodded.  “Did they say anything to you?” she asked.  “Or did they just grab you?”

      “This one guy stopped me first.  He said something about not coming into his neighborhood dressed for business without doing what he wants… and he wanted me to go to work on him!  When I tried to get away, that’s when his two friends grabbed me and started pulling me toward their car.”

      “And then the police showed up?”

     Chad nodded.  “Yeah.  They let go of me real quick then.”

      “And the police only asked if you were okay?”

      “That’s all,” Chad replied. 

     Mel nodded.  It was pretty much the way Robin had told it.  The problem was, it was her fault.  She had unwittingly placed him in that dangerous position.  But she had never figured him to go anywhere other than to work and the gym – where she knew he would be safe.  She didn’t think about him going out to lunch or anywhere else.  For the future, she would have to keep his safety more in mind.  But before she made any bigger decisions, she would take the time to think seriously about all this first.

      “Do you ever have any problems when you’re dressed more normally… like you are now?” she asked.

     Normally?  But Chad knew what she meant.  He shook his head.  “Not really.  Like I said, usually everyone just looks at me funny but they rarely say much… usually anyway.  Sometimes they laugh.”

     Mel considered that.  “So normally, there’s no real problem?”

      “Only that it’s very embarrassing.”

     Mel smiled.  “That’s the point!  So you’re over what happened yesterday?  No problems now?”

     Chad had to think about that for a moment.  “I guess so.  I mean, I still get nervous just thinking about it, but what else can I do?  It’s over and I didn’t get hurt.  But if that policeman hadn’t arrived when he did…  I’d rather not think about what would have happened!”

     Mel nodded.  It could have easily become a very big problem – and ultimately for her too because she was responsible for him.