The Bet - Chapter 54 (Wednesday – week 8 Part 5 of 9)

The Bet

By Karen Singer

Chapter 54 (Wednesday – week 8 Part 5 of 9)

      “Champaign!” Mel squealed in delight as Gloria told how Ray had shown up at her office door last night.  “It’s positively romantic!”

      “It was romantic alright,” Gloria agreed.  “In more ways than one.  Do you know I think he prides himself on his bag of sexual tricks?”

      “I believe it!” Mel replied.  “I remember how he went through one after another with me.  Is that how he was on your first date?”

     Gloria shook her head and blushed a bit.  “I don’t think I ever gave him the chance.  I was too busy trying to go through all my own fantasies.  Which I have a lot of by the way.”

     Mel laughed.  “Well, we each went through some fantasies last night then,” she replied.

     Gloria became a bit more serious.  “Yeah, how’s that going by the way?  How does the relationship between you and Derek and Sissy seem to be?”

     Her question made Mel become a bit more serious too.  “It’s… going,” she finally replied.  “He seems to resent Sissy’s presence an awful lot.”

      “Can you blame him?”

      “Not really.  But I’ve been totally up front with him about it.  For now, I’ve got to keep Sissy on a really tight leash until this bet is finished.  The end is too close for me to let up in any way at all now.”

      “And naturally, Derek would rather be alone with you instead of having Sissy around all the time.”

     Mel nodded.  “Exactly.”

      “And how is Derek relating to Sissy… now that he knows all about him?”

     That question clouded Mel’s face even more.  “Awkward wouldn’t even come close.  As I said, he resents Sissy terribly.  He mentioned several times how he feels like Sissy… or Chad rather… betrayed him.  They used to be friends, and now… well, now that he knows the truth about Sissy, he can’t seem to feel anything except revulsion for him.  I know that eventually he’ll probably mellow out – at least a bit.  But for now, well, he still seems to hold a lot of anger toward him. 

      “So does Derek try to avoid Sissy?”

      “No, not really.  But while he’d rather Sissy wasn’t there, he says he’s determined to not let Sissy get in his way.  But I noticed that Derek doesn’t seem to mind taking his frustrations out on him.  Last night he was more than glad to punish Sissy – for me.  But he used his belt on him and he used it hard!  And he seems happiest about Sissy when Sissy is either enduring something horribly humiliating or horribly painful.  He thinks Sissy should get what he deserves – the more the better.” 

     Gloria nodded.  “So are you trying to avoid Derek in any way because of it?”

     Mel shook her head.  “No.  In fact, I think I keep finding myself wanting to see him.  But for now, I just can’t see him alone.  I need Sissy to be there too.  This bet means way too much to me.”

      “And how about Derek.  If you want to see him so badly, does he mean that much to you as well?”

     Mel was caught off guard by the question.  She had to think about it for a moment.  “I like Derek.  A lot!  An awful lot I think.  But…”  She shook her head.  “Right now he doesn’t mean nearly as much as wining this bet.”

     Gloria had guessed that.  In a way, she was sorry to hear it.  But it was the answer she would have guessed.

     Chad approached the gym door with a mix of trepidation and anticipation.  He was anticipating it, because he knew for a fact that he had managed to orgasm last night from Mel just using his backside.  The trepidation however was because he never knew what other humiliating thing he would be up against.  But if Cassie played with him again today – like he hoped she would, maybe now that the ice had been broken again last night by Mel, he would be able to orgasm again from Cassie’s playing.  If… she played with him again.  The thought of the receptionist changing him instead briefly crossed his mind.  She hadn’t changed him all week – yet.  That little embarrassment was getting way overdue!

     As he reached for the handle to open the door, he caught a tiny glimpse of his reflectin in the glass.  He was dressed normally again – for him.  His dress was back in place and the stupid hair bow Robin had made him wear backwards was gone.  He was once again dressed in the least humiliating way he possibly could be – anymore. 

     He opened the door and went inside, noticing the broad smile on the receptionist’s face.  That wasn’t a good sign!  He curtseyed – because he knew he could never get away with not doing it.  “Hewwo, Thindy,” he said in his sissy voice.  “Can you pweathe get Cathy fow me?”

     Cindy giggled.  It always sounded like he said Cathy instead of Cassie, but then the way he had to speak, they were basically one and the same.  But she ignored his question so she could speak with him for a few moments longer.  Cassie still wouldn’t let her change his diapers again yet, but that didn’t mean she couldn’t tease him a bit.  She leaned over the counter with excitement in her eyes.  “I couldn’t believe that outfit you wore yesterday!  I loved it!  But tell me, did you enjoy wearing it?  Cause I got to tell you, it looked like a really fun outfit to wear!”

     Chad had to think about that a bit.  “Yeah, some,” he admitted.  “But it was trouble too.  Lots of trouble!”

     Cindy giggled.  “Yeah!  I saw your diapers sticking out below your skirt.  I still can’t believe they got that way!”

      “That wasn’t the only problem,” Chad said.  “I got molested on the way back to work.”

     Cindy’s eyes went wide in shock.  “You’re kidding, right?  I mean… what do you mean by molested?”

      “I stopped at a store to buy some water and three guys grabbed me and tried to force me into their car at the end of the parking lot.”

     Cindy just stared at him.  “You’re not kidding, are you!”

     Chad shook his head.  “No, I’m not.  It happened.  Now will you please…”

      “No, wait!  So what happened?” Cindy asked.

      “The police showed up while they were dragging me down the sidewalk and chased them away.”

     The still wide-eyed Cindy had to ask.  “And what did the police say?”

      “They only asked if I was alright.”

     Cindy shook her head.  “Wow!  I’d be so scared!”

      “I was so scared!” Chad told her.  “Now would you…”

     Cindy held up her hand.  “Yeah, I’ll get her.  But her eyes were still locked on him in amazement as she started to slowly move.  Molested!  Three guys!  The police!  She’d be…  And then something about him caught her eye and she stopped and stared at it for a moment.  She came fully out from behind the counter to see him better.  She didn’t ask, she simply went up to him and grabbed his wrist and held it up so she could see his fingernails better.  And her jaw went wide with surprise, but only for a moment.  Her mood at hearing how he had been molested was quickly replaced by the joy of seeing SISSY spelled out on his fingernails.  And she laughed!

      “I love it!” she screamed.  “It’s so perfect for you.  I was too preoccupied with other things about you the last few days to really notice your nails.  Do you like them?”

     Chad wasn’t sure how to answer that.  On one hand, he found them horribly humiliating – which he loved, but on the other hand he simply found them horribly humiliating!  “Um…” he said searching for an answer.  “I guess they’re okay.”

     Cindy giggled, her voice dropped almost to a whisper.  “Do you find them embarrassing?”

     Chad ignored her question.  He needed to get his diapers changed.  “Will you please get Cassie for me?” he asked again.  “I’m afraid I’m going to leak all over the place if I don’t get changed soon.”

      “Are you that bad again?” Cindy asked in wide eyed curiosity.  “Can I see?”  Without asking she reached down and pulled up the hem of his dress, exposing his now overly bloated all-in-one girdle.  “Oh poo!  You’re not wearing the same girdle as yesterday.  I can’t see them!”

     Chad stepped back a bit and pushed his dress down.  “Please,” he said.

     Cindy finally nodded and left to find Cassie.

     Chad stared after her.  Yes, he was very embarrassed by having sissy spelled out on his nails, but today, he could have cared less about Cindy’s reaction to it.  He really just wanted to get in to see Cassie and have his diaper changed.  And… if she happed to be in the mood to play with him again…  Well, he really hoped she would!

     Five minutes later, he was back in the tiny office again undressing while Cassie pulled his things out of the diaper bag for him. 

      “Hey!” she said as she pulled the sixth bottle out of the bag.  “Every one of these is empty!  What happened?”

     Chad blushed, even though he really had no reason to.  “Robin had me drinking them all morning.  It was way too many bottles.  I guess she forgot to save one for you.”

     Cassie shook her head and got to her feet with one of the empty bottles.  “Well we can’t have you going without one,” she said.

      “But I drank so many this morning!” Chad complained.  “I’m sure Mel wouldn’t mind if we skipped it just this once!  Besides, this afternoon I…”  But he stopped himself right there.

      “What about this afternoon?” Cassie asked.

      “Robin told me to buy three of the largest size drinks with my lunch today and bring them back to the office.  That’s way more than six baby bottles can hold!”  He looked expectantly at Cassie.  “So you see, I really don’t need anything else!”

     Cassie actually considered it for a moment.  “Sorry,” she said as she headed for the door.  “I promised Mel.  And besides, I don’t know how much of those three drinks Robin will actually make you finish.”  She opened the door and left him to finish getting undressed while she went out to find a way to deal with the empty bottle.

      “Robin will make me drink all of them,” Chad said resignedly to himself as the door closed behind her. 

     When Cassie returned a few minutes later, Chad was clad in only his heavily bloated diapers and plastic panties.  He was relieved to see it was Cassie who had opened the door and not somebody else. 

      “Here,” she said as she handed him the now full bottle.  “I filled it with water from our stock bottles.”

     Already resigned to having to drink it, Chad took the bottle and laid down on the floor so Cassie could change him.

      “Wow, you really are wet!” Cassie said a minute later as she managed to peel the tight plastic panties off of him.  I guess Robin has been forcing the liquids on you.”

     Chad said nothing.  He didn’t think he needed to.  He simply continued to drink mindlessly from the latest in his never-ending string of baby bottles, mostly concentrating his thoughts on how he was going to manage to drink as much as he knew Robin was going to make him this afternoon.  They were not happy thoughts.  Since it took so much longer to drink from the bottles, he figured he’d be pretty much spending the whole afternoon with baby bottles in his mouth.  If he could even finish them then.

     Cassie carefully pulled back his overly sodden diaper.  She had to hold it up for a moment as she did so as she noticed a bit of pee still trickling out of his chastity device.  The moment she felt it was safe enough, she quickly pulled the wet diapers out from under him and slid the three new ones she had prepared under him again.  And as she let his legs back down, again she noticed a bit of pee coming out of him.  But the stream was so weak that she didn’t have to worry about pulling the diaper up to catch it.  She looked up at his face.  He was drinking his bottle and staring mindlessly at the ceiling while she worked on him.  Had he even known that he had just peed a little?  She had no way of knowing of course. 

     She took a baby wipe and carefully cleaned up his front side.  No reaction from his face at all.  For all the notice he seemed to take, she might not have been there at all!  Still watching his face, she grabbed his chastity device and started pulling on it a bit, trying to force a reaction to his tiny member trapped inside of it… but he still didn’t seem to notice what she was doing.  She cupped his balls and gently stroked them as well… and again, no reaction.  Didn’t he feel anything down there anymore? 

     Shaking her head, she said, “Okay, roll over.”

     Her words snapped Chad out of his dumb thoughts.  “Huh?” he startled.

      “I said, roll over!”

     Happily, Chad put his bottle down and rolled over so she could work on his rear end.  This was the part he was waiting for.  Would she play with him?  He was certainly hopeful.

     Cassie carefully cleaned his backside, then she started applying the lotion to him, spreading it over him and working it into his skin as her hands caressed that part of him.  Did he just let out a small sigh?  She kept going, now starting to play with her one finger against his tiny little hole.  Now he reacted.  There was no doubt about it that time.  Why was it that he no longer seemed to feel anything at all from his front side, the side he was supposed to react from, but he now seemed to be incredibly sensitive to everything happening on the other side of his body instead?  Oh well, hadn’t she herself been working on conditioning him to do just that?  Helping Mel to deny him his male reactions and replace them with… well… maybe not exactly female reactions, but certainly something closer to that than his normal male ones.

     She stuck her finger all the way inside of him and wiggled it around a bit before withdrawing it.  His backside tried to follow her hand back up, tried to find her finger after she had pulled it out.  She almost laughed to herself as she opened her desk drawer and pulled out her usual toy.  “Scooch your knees up, baby.”

     Chad could concentrate on one thing and one thing only, the delicious feelings Cassie was giving him in the place he wanted to feel them the most.  Delicious!  The minute he felt the tip of her toy applied to just the right place, he stopped breathing and tensed his body for the anticipated feelings he was waiting for.  He felt the pressure of her toy against him increase, and he totally opened himself up to receive it.  He felt it going in, just a little, then it went out again – but not all the way.  In, then out.  Back, and forth.  Going just a little bit deeper and deeper each time.  But he wanted more of it.  He kept trying to get more of it, but Cassie was only allowing him just so much of it at one time.  He would have to resign himself to what she was going to do with him and not what he wanted. 

     Further and further her toy entered him, the ribs on the sides of it adding greatly to his pleasure.  And finally, he felt her hand hitting his skin, signifying that she had buried its whole length up inside of him.  He shuddered just a bit, but it was a wonderful shudder. 

     Faster and faster now she pumped, and now he responded in kind, pushing and pulling as he had learned to do over the last two months.  More, more!  He wanted more!  Faster!  Harder!  He had to get there!  There was an end to this, a goal!  He knew it was possible to get there now.  He knew that for a fact!  But there was something missing again, something that was keeping him from getting where he wanted to be. 

     His mind wandered from the present to the past.  Even as he worked furiously to achieve what he wanted, his mind reverted to the memories of the night before – to the time when Mel had been doing this to him – with her strap on.  To the time when Derek had stood there and watched his total humiliation.  To the time when… but that was it!  That was the one missing ingredient.  Cassie was doing such wonderful things to him, but she wasn’t saying anything.  Mel talked to him as she did it.  Mel continuously fed humiliating thoughts straight into his brain.  The thoughts alone were the fabric his dreams were made of.  And coupled with the fantastic feelings of her strap-on, a monstrously humiliating thing in itself, it was more than enough to propel him over the edge. 

     But here?  Here he had the wonderful feelings, but nothing else.  Here, Cassie was quiet while she worked on him.  Here, he had no one relaying humiliating suggestions straight into his mind.  Here – he only had half the equation.  Here… he wasn’t going to get there.

     Defeated, he gave up.  It had been fun.  Tons of fun!  Fun he would gladly enjoy and look forward to every day.  But it was nothing but a desperate false hope.  Nothing more.  He wasn’t going to achieve his goal with Cassie.  He probably never would.  As much as he loved the feel of Cassie’s hands, he needed the full package instead.  He needed Mel… and the incredible things she did to him… and made him do.  He needed… it all.  He needed… Mel.

     Cassie watched him give up again.  Why did he try so hard?  She guessed she couldn’t blame him though.  To be denied the ability to have an orgasm… especially after being constantly sexually stimulated by everything he lived with and everything that was done to him.  It was a torture she herself could never endure.  But she had Sandy to help her with that.  And Sandy was more than willing to help her any time she wanted it.  But Sissy…  Once again she felt sorry for him. 

     She had noticed that all through his efforts he had again spurted little bits of pee several times out onto the fresh diapers below him.  Did he know he did that?  Again, no way to tell.  He certainly didn’t act like he knew it… or maybe he knew it and he just didn’t care.  Not that it mattered. 

     His bet with Mel would soon be over.  And there was a possibility that she herself might have to decide which of them won.  And the big question was… which of them did she prefer to see win?

The Bet - Chapter 54 (Wednesday – week 8 Part 4 of 9)

The Bet

By Karen Singer

Chapter 54 (Wednesday – week 8 Part 4 of 9)

      “My place,” Robin said as they walked past Chad’s cubicle on the way back from break. 

     Chad said nothing.  Of course, it was easier for him to say nothing since he had his thumb stuck in his mouth again.  Break had been less humiliating for him today than usual.  But after yesterday, anything would be less humiliating!

     Once in her cubicle, Robin went straight to his diaper bag and pulled out yet another baby bottle – his fourth one of the morning so far.  And he had just finished not only a full cup of coffee, but another baby bottle just before break as well.  It was too much!  “No…” he groaned out loud, not meaning to really say anything.

     Robin withdrew the bottle with a shocked, angry look on her face, “No?  What do you mean no?”

      “It’s too much,” Chad replied – without curtseying first.

      “You’re the one who made that silly bet!  You’re the one who wanted to see what it’s like to be incontinent!  You’re the one who gave up all say about everything – for the fun of it!  Don’t tell me no!  As I see it, you don’t have the right to tell anybody no!  About anything!  And once again you forgot to curtsey before you opened your stupid mouth!”

     Her sudden anger frightened Chad.  He was surprised enough that he couldn’t tell if she was really mad or was just pressing her point.  He might have messed up a bit, but not all that much.  He curtseyed.  “Thowwy Wobin,” he said contritely in his sissy voice before curtseying a second time. 

     Robin wasn’t exactly mad, but she wasn’t about to let him get away with anything either.  He was just like her son, if you wanted to get the point across about something, then you had to raise your voice to let him know how serious you were.  And once again Sissy was showing her how much like a child he was.  Children never knew what they really wanted – even when they thought they did.  Well, he thought he wanted it, so now she was going to make sure he got it!

     She pointed at the floor.  “Down!” she ordered.  “No, wait!” she reversed herself quickly.  “That dress is way too nice… too grown up for you.  Take it off first!”

     Take his dress off?  Get undressed?  Now?  Chad forced himself to not sigh so that she could notice, but he bent down to unfasten his shoes first. 

      “I didn’t say your shoes!” Robin said firmly.  “I know they’re probably very uncomfortable, so you can leave those on.  Just your dress.  Get it off!”

     She waited while Sissy stood back up and removed his dress, leaving his all-in-one girdle as his most prominent piece of clothing.  Robin again pointed at the floor.  “Now you can get down there.”  Once he was down – like a child – she handed him his baby bottle – which he took with no complaints this time.  You just had to know how to treat them! 

     She watched as he sat there on the floor sucking on his bottle.  So much like a child.  He deserved this for sure!  Without the dress, she found him much less normal, much more the way she preferred to deal with him.  And he did seem to need constant dealing with – like a child. 

     Once Mel was done with him and someday allowed him to get potty trained again, maybe then he would grow up and be more of an adult.  Maybe.  But for now, once again, all she could see in him was a child.  In many ways, nothing but a baby.  A big baby for sure, but nothing but a baby.  And you just had to know how to deal with them. 

     With a satisfied look on her face, she turned around and got busy with her work, seeming to ignore him for a while.  But like with her son, she could never really ignore him.  You had to watch children constantly!

     Chad stared at Robin’s back as he nursed on his bottle.  Another bottle!  He had already had way too much to drink today.  His diapers were soaked!  Major soaked. And major heavy!  Was she trying to make him leak before he went to lunch?  If so, she was doing a darn good job of it.

     He had felt himself peeing a few times this morning.  But those times were always brief.  And he knew for sure that most of the time he wasn’t even noticing it when he wet himself anymore.  And why should he?  His diapers were always so wet that it didn’t matter if he was adding more to them.  He did it so often that he couldn’t pay attention to it anymore.  It was even getting hard to detect now when he was trying to watch for it.  And the problem was that he was still getting too much to drink – way too much.  He didn’t stand a chance of controlling anything as long as he was drinking so much. 

     Something inside of him stirred with excitement at the thought that what he was experiencing might really be like true incontinence.  He was wetting himself uncontrollably for sure.  Messing himself too.  And as long as they kept pouring the liquids down his throat he stood no chance of controlling himself – like a baby.  Like a real baby. 

     And now Robin had made him take his dress off and made him sit on the floor while drinking from his baby bottle – like a baby.  He was living the dream – the dream that so many others, himself included, believed could never really happen in real life.  Yet here he was, doing it, in real life.  Living the dream… and then some. 

     Despite the amazing orgasm he had experienced last night, his under exercised sexual excitement grew a bit more just thinking about it.  He felt the pressure of his need, surprisingly more in his back end instead of in his penis – his primary sexual organ – once.  But his backside was the only place he was allowed to feel pleasure – now.  Thinking about that stirred his excitement as well.  He didn’t know why it excited him, he simply couldn’t help it.  His thoughts turned toward Cassie, hoping that she would play with him again during lunch.  Despite his orgasm last night, he wanted it again… badly.  Would he be able to cum again?  He certainly hoped so.

     His bottle finished before he knew it.  Since Robin seemed so fixated today on him keeping his thumb in his mouth, he replaced the bottle nipple with his thumb, while he waited for Robin to turn around and see that he was finished.

     Robin heard the small sound behind him and smiled, but she made no move to indicate that she had heard him finishing his bottle.  Let him sit there and wait till she was ready.  She kept working, but her mind was more on him behind her than on her work.  Finally, she turned around.  He was sitting there sucking his thumb – like a baby.  He looked so childish that she almost laughed.  Fortunately, she steeled herself into sternness.  “You’re done finally?  Do you want another one now, or are you going to behave a bit and wait a little while?”

     Chad had to stand up, remove his thumb from his mouth, and curtsey.  “I’d rather wait a bit,” he replied.  Then he had to curtsey, put his thumb back in his mouth again… and get back down on the floor. 

     Robin watched him the whole time.  Something inside of her was laughing at him – even though she was doing her best not to show that.  He looked so ridiculous!  Especially in nothing but his underwear.  Lots of underwear, but that’s still all that it amounted to.  He certainly didn’t look “normal” now.

     A tiny silly idea struck her.  She found his big multi-colored hair bow and held it on top of his head while she looked at it.  It was like playing with a big doll.  On a whim, she turned the hair bow backwards, so that the long streamers were hanging down in front of his face.  Giggling a bit to herself, she fastened the bow to his hair just that way. 

      “I know you’ve still got plenty of work to do,” she told him, “so you better get to it.  I’ll let you know when it’s time for your next bottle.”  What she wasn’t telling him, was that his next bottle time wasn’t very far away. 

     Chad stood up and looked at his dress.  The streamers from his hair bow were a nuisance as they blocked much of his vision and swayed across his face.  He took his thumb out of his mouth and curtseyed.  “Can I put my dress back on now?” he asked – before curtseying again and sticking his thumb back in his mouth.  He was afraid though that he knew the answer.

      “Not till later… maybe,” Robin replied with a smile. 

     With colorful streamers in his face, Chad pulled his thumb out again and curtseyed again.  Then he turned and went back to his own cubicle. 

     He sat down at his computer and pulled the streamers away from his face as if they were long strands of hair.  But the way the bow was designed made them move right back in place again as soon as he let go of them.  They were in his way.  He had trouble seeing around them.  How was he supposed to work with them blocking his vision? 

     He finally wound up holding them aside with one hand while he attempted to type with his other.  At least it was better than trying to type with the heels of his shoes like he had done yesterday.  Today, no matter how much his shoes hurt his feet, he was determined that they were going to stay on his feet and nowhere else!

     Fifteen minutes later he heard Robin calling over the wall.  “Bottle time!”

     He closed his eyes and shook his head.  Would it ever end?

     Mel stood carefully still as the seamstress marked and pinned the hem of her skirt.  The jacket she was wearing had a few chalk lines on it too, but not many.  Actually, other than the length of the skirt, the suit seemed to fit her perfectly… the seamstress just didn’t seem to think so.  So she stood there while her suit was marked and fitted to perfection – just as she had stood there a few minutes earlier and waited while her other suit was measured and marked as well. 

     The new suits were nice – really nice.  Expensive, but worth it.  But then, everything in this store was that way.  She looked at her reflection in the big mirror as she waited.  Outrageously expensive clothes.  Reminders of what her life used to be… before her parents died.  Reminders of what her life could be right now… if she would just let herself have it.  But a life like that was no life at all if she didn’t deserve it.  And she was determined that she would have it again, only she would have it because she deserved it.  She wouldn’t have anyone saying she was basically worthless because she had inherited everything.   

     Feinbaum’s little contract job though was not the ordinary fare for her.  This job required that she be taken more seriously than the little back-office lawyer she had been for a number of years now.  She just wished she didn’t feel so much like she was failing at what Feinbaum needed. 

     She would wear the clothes again.  She would walk the walk and talk the talk.  She would take the huge sum of money she would get for her tiny part in the proceedings.  But there was no way she could feel like she really deserved any of it.  No way she could feel like she once again belonged back up with the elite of society.  No way… because she knew she didn’t deserve it.  Not yet at least.  Maybe someday, but not yet.

     Five minutes later, she was back in the changing room putting her dress back on.  Her suits would be ready for her to pick up tomorrow morning at the latest.  She would have to make the time for it – despite all the work she knew she would be tied up with over the next version of the contract – which still hadn’t arrived yet. 

     As soon as she was dressed, she looked critically at herself in the changing room mirror.  Was she getting old?  Damn, she was.  But not too old!  Not yet!  But staying young was getting harder and harder… or at least looking young.  Her figure was… okay.  Not what it used to be.  But then, what about her was?  Her face looked… okay.  Older than she would like.  But still not too old!  Her hair…  She ran her fingers through her hair.  Should she take the time to have it cut and styled again?  She had just had it cut recently.  But restyled?  No, she really didn’t want to bother. 

     She pulled her hair back behind her head and held it there while she studied her face again.  Then she dropped her hair and smoothed it out.  Time to think about other things besides morbid thoughts! 

     She left the dressing room and headed out to her car.  It was still a little bit early for lunch.  She had a few minutes.  She drove to her bank instead of the restaurant.  Inside, she signed the register granting her access to one of her safe-deposit boxes.  This one held jewelry – mostly her mother’s old jewelry.  But it also held a few special pieces of hers as well.

     Once she was alone with the box, she opened it and sorted through the colorful pieces inside.  So many things.  So many expensive things – monstrously expensive things – as she was now mature enough to realize.  Once upon a time she had never thought twice about the price of something.  Like her mother, if she wanted it, she bought it.  Not now – even though she could well afford to be that way. 

     She reached in and pulled out several of her mother’s rings.  She finally selected one that was her favorite and set it aside on the table.  A necklace soon joined the ring… a thin bracelet as well. 

     And then, down in the bottom of the box, she saw another box.  A box that woke many memories in her – memories of her father.  The box contained a gift he had given her for her sixteenth birthday.  She pulled the box out and opened it, just so she could see it again – and remember.  Safely nestled in the velvet liner, was a large hair barrette – totally encrusted with diamonds – real diamonds.  The thing was worth a fortune.  She had worn it only a few times, but she treasured the gift from her father like nothing else he had ever given her.  She touched it briefly, then closed the lid on it again and put it back into the safe-deposit box.  She closed the lid on the safe-deposit box… then opened it again and pulled out the box containing her hair barrette.  It wasn’t really the right thing for the occasion, but she couldn’t help herself.  She would wear it anyway – in memory of her father – who she missed so much – especially lately.

     With her purse now containing a horde any thief would kill for, she went back out to her car and headed to the restaurant for lunch.  She couldn’t wait to hear the details from Gloria.  Ray had really been there last night?  Wow!

     It was nearly lunchtime and Chad was once again sitting on the floor of Robin’s cubicle drinking his sixth baby bottle of the morning.  His diapers were so bloated under his all-in-one girdle that he was afraid they would start leaking through everything.  In fact, he was amazed that they weren’t leaking already. 

     The streamers of his backwards bow were still in his way, but at least just drinking his bottle he didn’t have to look at anything – not like when he was trying to work – where he had to see his computer screen. 

     Robin turned around to look at him.  So ridiculous!  His bottle was nearly empty.  “Don’t forget you need to get something to refill all those bottles during lunch,” she said to him.  She waited for him to answer.  His head moved up toward her with the bottle still in his mouth, but the silly colorful streamers covered most of his face.  She guessed that he was declining to answer since answering was awkward for him.  “Are you planning on stopping at the same store where you were attacked yesterday?”

     Chad hadn’t really thought about it yet, but Robin did have a point.  And now that he thought about it, stopping at that place, perhaps forever, sounded like a bad idea.  He was forced to stand up, remove the bottle from his mouth and curtsey.  With the streamers blocking much of his vision, he replied.  “I think it would be better if I went somewhere else from now on.”  Then he curtseyed again, got back down on the floor, and put his bottle back in his mouth.

     Robin nodded.  “That sounds like a good idea.”  She had a sudden inspiration though.  “Maybe you can just buy several large size drinks with your lunch and bring them back here.  With six bottles, I would think that two really large drinks might fill them all.” 

     Chad thought about that.  It actually sounded like a good idea.  He removed the bottle from his mouth and stood up again, and curtseyed again.  “That sounds like a great idea,” he replied.  “I’ll try it.”  Curtsey, back down, bottle.  Ugh!

     Robin smiled.  “Yeah.  But I’m not sure if two drinks is going to be enough.  Tell you what, why don’t you buy three of the largest size drinks you can get with your lunch and try that.”

     Three?  That was way too much and he knew it.  Bottle out.  Stand up.  Curtsey.  “But…”

      “Three is an order!” Robin said sternly before he could get any further.  “And I’ll be checking on it when I get back.  I want to see three really large size drinks on your desk.  In fact, maybe you should bring your lunch back here and eat it at your desk like you did yesterday.  Pour the drinks into your baby bottles and drink from them.  I’ll be back early from lunch to check on you!  We’ll see how far those drinks go then.”

     Chad wanted to protest – vehemently.  Three drinks was way too much.  Especially if they were the extra-large size.  But he carefully controlled himself, curtseyed and said, “Yes, Robin.”  Curtseyed again and sank back down to the floor where he stuck his bottle back into his mouth to finish it.  Three drinks!  It was way too much!

The Bet - Chapter 54 (Wednesday – week 8 Part 3 of 9)

The Bet

By Karen Singer

Chapter 54 (Wednesday – week 8 Part 3 of 9)

     One client later, Mel was again back at her desk.  She picked up her phone and dialed Cassie’s number.  She had to leave a message for Cassie to call her back.  But just before she was about to tackle something else, Cassie returned her call. 

      “Hi Mel.  What’s up?” Cassie asked.  “More changes for Sissy?”

      “Not quite,” Mel replied.  “Actually, I’m looking for a favor – if we need it.”

      “What do you mean?”

      “Well, you know we’re getting closer and closer to the end of our bet.  And Sissy is worried about how we’re going to decide the winner if things are looking really close.  So we’re asking for judges to make the decision for us – if it looks like we need them.”

      “Um…  Yeah, I guess I can do it.  But Mel, I gotta warn you, I’m just as likely to side with Sissy on this thing if it looks close enough.  So you may not want me to do this.”

      “That’s just it, Cassie.  What we want, me included, is for the judges to be perfectly honest.  To call it like it really is and not base anything on how they feel about either of us.”

      “So you really want it to be fair.”

      “Yes.  Exactly.”

      “Then I guess I can do it.  When do you think it will be?”

      “A week from Saturday.”

      “I don’t see any problem.  I’ll try to make sure my schedule is clear that day, just in case.”

      “Thanks Cassie. Oh, and Cassie, I was going to ask Sandy too.  In fact, I’m trying to get as many people to decide this thing as I can.  That way we can lessen the impact of anyone who seems to be too impartial.”

      “I get it,” Cassie replied.  “You’re selecting another jury.”

      “Um… something like that.”

      “No problem.  Do you want me to ask Sandy for you?  Although, I’m not too sure how impartial she’s going to be.”

      “No, I better talk to her myself.  Thanks though.”

     Mel hung up her phone.  They now had two judges.  So who to talk with next?  Someone who knew about the bet… obviously.  So that left Sandy, Robin, and Derek.  Just thinking about Derek brought a smile to her face.  She picked up the phone again and dialed his number.  When he answered, it sounded like he was in his car somewhere.  “Hi Derek.  I’m glad I caught you.”

      “Hi Mel,” Derek replied.  “I was just thinking about you.”

     Mel smiled.  “Great minds think alike, I guess.”

     Derek laughed.  “What can I do for you?  Take you out somewhere… away from Sissyface?” 

      “Um…  No.  Nothing like that unfortunately.  What I’m calling about is something else altogether.  “I’m trying to set up some judges for our bet in case it’s too close for us to figure out ourselves.”

      “And you want me to be part of it?  Sure!  No problem!  I’ll be glad to be a judge and tell the little shit that he loses.”

      “But that’s just it, Derek.  I don’t want you to do that.  We need people who are going to be totally impartial.  People who can do it honestly, without regard for how they feel about either of us.”

     Derek thought about that for a moment.  “I seriously doubt I can do that.  In fact, I know I can’t.  Look… the little shit asked for it, and now he’s got it!  And I still hope he keeps getting it!  End of story!”

     Mel was disappointed.  “Thanks Derek, but I better pass.  If you can’t be fair, then we can’t use you.  Sorry.”

      “No problem,” Derek replied.  “But if you can’t use me for that, maybe you can think of some other way to use me… like the way you did last night?”

     Mel laughed.  “Who used who?  God!  What a night!  I’m still yawning, and I don’t know how many cups of coffee I’ve had today.”

      “Me too,” Derek replied, “but don’t tell anyone.  So how about tonight?  Any chance you’re willing to get away yet?”

      “Sorry Derek.  Like I said, not till this thing is over with.  Then we can do anything you want – without Sissy.  But you’re always welcome to stop by my apartment anytime you want.  I do have a lot of things I need to do tonight though, but you’re welcome to come anyway.”

      “Are any of those things that you need to do like what you did last night?”

      “No.  Not even close.  I need to get Sissy back into ballet training again.  I’ve put it off way too long.  He’s going to be performing next weekend – he just doesn’t know how or where yet.”

      “Ballet practice?  If you don’t mind, I think I’ll pass!”

      “But he’s adorable to watch!”

      “Maybe for you, but I’m not sure I want to stomach anything like that tonight.  Thanks anyway.”

      “No problem.  Another time then?”

      “You can count on it.”

     Mel hung up her phone.  Derek was definitely out!  But considering the way he still felt about Sissy, that was probably a good thing.  She was sure he would probably mellow over time, but for now Sissy still bothered him.

     Chad was sitting on the floor of Robin’s cubicle finishing up his third bottle since he had gotten to work.  Once again Robin had started him drinking again in well under an hour. 

     He knew that break time was coming up in a few minutes, but at least today he wasn’t dressed like a hooker.  In fact, the only thing about him that he expected any of the women might want to talk to him about was his fingernails, which still spelled out SISSY.  And since the women had already seen his nails for the last two days, maybe they might not even mention it. 

     The one thing he wasn’t looking forward to about break today, was getting another cup of coffee.  After drinking three bottles just since he had gotten to work, he didn’t need a cup of coffee on top of them.  His bottle emptied and he made a small sigh of relief – which unfortunately alerted Robin that he had finished.

     Robin glanced at the time.  It was still a little early for them to go to the break room – by about five minutes.  So what should she do with him?  She looked down at him to figure it out and noticed that his thumb wasn’t in his mouth again.  “Why aren’t you sucking your thumb?” she asked.

     Chad mentally groaned as he moved his thumb to his mouth.  It looked like Robin was going to be after him to keep his stupid thumb in his mouth all day. 

      “Stand up,” Robin directed and waited till he was on his feet.  “We still have a few minutes before we can leave for break.  So till then, you can practice curtseying and putting your thumb back in your mouth. 

     Ugh!  Chad removed his thumb and curtseyed.  “Yes Robin,” he replied, then he curtseyed again and put his thumb back in his mouth again.

      “Just like that!” Robin told him.  “You can even say ‘Yes Robin’ each time so you get used to it.”

     This was the last thing that Chad wanted to be doing, but he had little choice in the matter.  He removed his thumb, curtseyed, said “Yes Robin,” curtseyed, and stuck his thumb back in his mouth again.  Then he did it again… and again… and again…

     Robin giggled.  Even dressed so normally, she could make him do things that showed her what he really was – a sissy!  She would still rather he wasn’t dressed so normally though.  But unfortunately, now was not the time for more fun things.  She went back to finish up some last few bits of work before break… while Sissy droned on and on in the background.

     Five minutes later, she and Sissy left her cubicle together, heading for the break room.  Sissy though, had to keep his thumb firmly in his mouth.  He didn’t get to remove it till they turned the corner where it was more possible for someone else to see him.  Most of the women hadn’t arrived yet when they got there.  They each poured themself a cup of coffee, looked longingly at the doughnuts, and headed for the table where the others were just beginning to gather. 

      “I see you had more sense in what you wore to work today,” one of the women already at the table commented to Sissy as they approached. 

     Chad could feel himself blushing… and peeing.  “Yesterday was just…” but he didn’t know what he could say about the outfit he had worn to work yesterday.

      “A bad case of judgment!” the woman finished for him.  “I hope you got it out of your system now.  And if you ever get the urge to dress like that again, maybe what happened to you at lunch yesterday will make you think twice about it.”

      “Oh, I don’t know,” another woman spoke up.  “I thought it was really… interesting.  I’m kind of disappointed that he wore something we’ve all seen before.”  She leaned closer.  “So tell me, did Derek like your outfit?”  She giggled as soon as she had asked.

      “Um…”  Chad wasn’t sure how to reply to that one.  “He didn’t mention it,” he finally said.

      “I’ll bet he loved it!” another woman added. 

      “He must have!” yet another woman replied.  “Yesterday he dressed like a tart.  Then he went and got Derek a cup of coffee.  He’s done everything so far to get Derek’s attention… except kiss him!”

     The women at the table suddenly erupted in a loud round of laughter.  Chad however, just blushed.  “It’s not like that,” he tried to argue when the laughter had died down.

      “Oh Honey, we’re not stupid!” one of them replied.  “We saw what you did.  In fact, we’ve seen you and Derek a number of times now.  It’s as plain as can be!”

      “So tell us,” another woman asked.  “Do you like kissing him?”

     Chad was aghast at her question.

      “Of course he does!” another woman replied.  “Why else would he go to all the trouble to dress so sexy for him?”

     While Chad blushed, Robin sat back and listened, letting her mind roam.  And what it roamed about was…  was there any way she could get Sissy to kiss Derek in front of the other women?  She could just picture him sitting on Derek’s lap at one of the other tables, kissing him on the lips.  She giggled because she knew that Sissy would hate doing it.  But she was more sure of how much Derek would hate it.  So unfortunately, it was never going to happen.  But… it was still fun to think about.

     But if kissing him was out, was there any other way she could make Sissy show his affection for Derek – and make it look real?  It would have to be something that wouldn’t get Sissy killed by Derek!  That was the big problem. 

     When she had walked into the break room she had looked around to see if Derek was there. She hadn’t seen him and she hadn’t seen him entering since.  But then it was more usual for Derek to be here in the afternoons instead – if he was available to come.  Could she think of something funny for Sissy to do with Derek before break this afternoon – just in case Derek showed up? 

     She barely heard a word of what was being said at the table as she happily pondered that question.

      “Hi Sandy.  It’s Mel,” Mel said into her phone the moment Sandy had answered her call.

      “What’s up, Mel?  Are we still on for tonight to work on Sissy’s ballet?”

      “You bet!  In fact, I feel bad about putting it off this long.”

      “Hey, you had a guy over.  I understand completely – although a guy isn’t exactly my dream date – personally.  I’m much happier with Cassie.”

     Mel laughed.  “I understand – but thanks for being understanding of me.  But that’s not what I’m calling for.  I’m kind of looking for a favor – if you can do it.”

      “Sure.  Name it.”

     But Mel was suddenly less sure about how Sandy would be able to handle what she wanted.  “Um… I just talked with Cassie about this too and she agreed.”

      “Cassie?  Her too?  What’s up?  You know that if Cassie is willing to help you, then I’m more than willing too.  So what’s happening?”

      “Well…”  But with Sandy, Mel wasn’t sure how to start – so she plunged in at the beginning.  “You know that the bet between me and Sissy is getting close to the end now.”

      “Yeah, and?”

      “Well… just in case it’s close – too close for us to figure out ourselves…”

      “Too close?  You’ve got to be kidding!  The guy has no control at all!  You’ve already won!”

      “Thanks Sandy, but, well, he still thinks he’s going to win this thing… and to tell the truth, I don’t really know how incontinent he is.  I mean, I’m forcing him to keep peeing all the time.  But what happens when I let up and he has the chance to hold back again and be normal?”

      “Him?  Normal?  Somehow I can’t picture it.”

      “But… just in case… humor me maybe.”

      “Okay, let’s say he has a chance.  So what do you need from me and Cassie?”

      “We’re looking for judges.  People who can make the decision for us if we think it’s going to be close.”

      “Heck, that’s no problem!  You already know how I feel.  I’m not too sure about Cassie though.  If it’s close, I think she may side with Sissy instead.”

      “But that’s just it.  I don’t want either of you to side with either of us.  I can’t use you if you can’t be totally impartial about it.  We need you to not play favorites – one way or another!”

     Sandy had to think about that for a moment.  “You’re serious, aren’t you!”

      “Very!”

      “You really want someone else to judge this thing for you, like, for real?  Win or lose?”

      “Yes.  That’s exactly what I want… what we both want.  So the question is, do you think you can do it?  Cassie said she could and I believe her, but I also know that you’d probably just as soon see Sissy lose.”

      “Well, that much is true.  I’ve never really thought about the possibility that he could really win.  I mean, could he?  Is it possible?”

     Mel sighed.  “Sandy, the truth is, that as far as I can tell, he’s just as likely to win as I am.”

     Sandy had to think about that for another minute.  “Then… I guess if you’re really serious about this, then I can be serious too.  Especially if Cassie has agreed to call it like she sees it too.”

     Mel actually breathed a sigh of relief.  “You’re sure Sandy?”

      “Yeah, I’m sure.  I’ll be glad to help judge you guys.  But… does that mean I can’t have some fun in the meantime?  I mean, you’ve still got a few weeks, don’t you?”

      “A little more than a week.  That’s it.”

      “That’s not much anymore.”

      “No, it’s not.”

      “Don’t worry, Mel.  If you need me to be serious, then I can do it.  Just as long as you don’t mind me having some fun with him before that.”

      “Sandy, as far as I’m concerned, you can have all the fun you want!”

     One more down, Mel thought as she hung up her phone.  They now had three judges, a good number.  There could be no tie with three.  But she still had to call Robin.  For Sissy’s sake, she had to include Robin in her request as well.  It was only fair. 

     She looked at her clock.  Where was that contract from Feinsbaum?  It should have been here already!  And she had to leave soon to run some errands and stop in for the final fitting on her new suits.  Asking Robin would just have to wait till after lunch.