The Bet - Chapter 61(Wednesday – week 9 Part 1 of 8)

The Bet

By Karen Singer

Chapter 61(Wednesday – week 9 Part 1 of 8)

     She squirmed.  Her dream-self watched intimately as Sissy reamed his own ass with the penis shaped dildo.  “Deeper now!” she commanded – and watched as he pushed the phallic shaped toy all the way in to the hilt.  All the way in until the fake balls at the end of it were touching his shaved-bare backside.  And she squirmed again at the pleasure of the power she felt because she could literally force him to fuck himself.  She was getting so hot watching him – as even in her dream, she imagined the feelings that big toy would bring to her own wanting sex – the sex that toy was meant to pleasure.  But instead, she was forcing Sissy… a mere man… to debase himself with it.  She was superior.  She was his total master – or more appropriately, his total Mistress.  And he had no choice but to do anything at all that she commanded – for her pleasure alone.  And the very decadent thought of it aroused her physical body once again… and she squirmed in her sleep.

      “Faster!” she commanded.  And her dream-self laughed with delight at seeing him fuck himself faster and harder… trying vainly to get pleasure where only she could get it, not him.  But then of course, he was fucking himself in a place that was never meant for that purpose… a different place than her velvety moist vagina.  He could never experience the pleasure from it that she could.  Never!  And that made forcing him to do this to himself all the sweeter. 

      “Mel!” the deep voice boomed.

     The sound of her father’s voice ripped her away from focusing on Sissy.  “Daddy?”  She could see him in the distance, for some reason the dream made him look fuzzy and out of focus, almost as if he was made of fog. 

      “Did you find the problem yet?” her father asked accusingly.

      “No Daddy… I mean, yes!  We did!  I mean… I did!  I found it and took care of it.”

      “Good girl!” her father’s voice said with pride. 

     She felt happy basking in his approval.  From behind her she could once again hear Sissy trying desperately to pleasure himself in such an impossible way.  She turned back to watch him.  So funny.  And she again felt the sexual tension building inside of her.

      “And how about Sissy?” Her father’s voice boomed again.  And again she was forced to ignore Sissy and pay attention to him.  “How much did he do?”

     She suddenly felt terrified.  “He did… most of it,” she admitted, fearful of what he might say.

     Her father’s face turned red with rage.  “How could you let someone else do the most important work for you?  He deserves all the credit, not you!  A damn sissy is smarter than my daughter!”

      “No Daddy.  No!  It’s not like that,” she desperately pleaded.

      “Looks like it to me!”

      “No!  It’s not like that,” she repeated.  Her father was staring at her, disapprovingly.  “We… we worked together,” she explained.  “We did it together.  He did some and I did some.  We both did it… together!”

     Her father appeared only a little more appeased.  “Teamwork?” he grunted.

      “Yes, Daddy,” she admitted, as if that was a bad thing.

     Her father looked sternly at her.  “Do you work well together… as a team?”

      “Yes Daddy.  Very well!  You saw what we could do.”

     Her father nodded.  “And who was in charge of that team,” he asked.

      “I… I was, Daddy.  I was in charge.  Sissy can’t be in charge.  He’s too submissive.  Totally submissive.  He follows my every command.  And you know me Daddy.  You know me.  You know what I am like.  What I am.  I want to be in charge all the time.  I hate taking orders from anyone.  I… I’m too dominant.”

     Her father nodded.  Even from the distance she could see the look of satisfaction on his face.  “A good team… with you totally in charge,” he finally said.

      “Y… Yes Daddy.”

      “Sounds like a good plan!” her father finally said.  “Sounds like a good plan.”

     She watched as somehow… her father faded out and totally disappeared.  Sounds like a good plan.  A good team… with her completely in charge.  A good plan. 

     Once again, the sounds of Sissy pleasuring himself grabbed her attention. She watched again as he slid the big phallic toy in and out of himself.  And she smiled.  Her father approved.  She was totally in charge… just like she wanted to be.  It was a good plan.  

      “Deeper Sissy!  Faster!” she ordered… and her body thrilled again as she watched him carry out her order perfectly.  And the result?  Her body squirmed with pleasure.

     His apartment was crowded with friends, and he was amazing everyone with his expertise at his new pool table – something he had never been really that good at before.  As he played, he continually looked around the room… searching… for the one person he knew wouldn’t be there.  But never the less, he hoped to at least spot her.  But as usual, she was missing. 

     He sank another ball, and afterwards, his hand slid back and forth along the bottom of his pool cue, unnoticed by anyone else.  His mind imagined what that cue would feel like sliding in and out of his backside.  So good.  So good.  But it would be so much better if… but she wasn’t there.  She would never be there… as he always knew she would forever be gone from his life.  He had won the bet, and now Mel was nothing but a neighbor that he rarely ever saw – even from a distance. 

     He played an impossible banking shot and decisively sank yet another ball.  But his mind was no longer on the game, or his friends, or even on lost Mel.  His mind was on his sissy things… locked deeply away where nobody could ever find them.  So locked away that they were hard for him to get to.  But now, even in the midst of his party, with so many friends around, he yearned again for his sissy things… and even more for the sissy dream he once lived.  The sissy dream he wanted so badly – but had vowed he would never touch again.

     But he wanted that dream.  He needed that dream.  The need was building in him so much that it was becoming impossible to resist!  He took another shot… and missed! 

      “My turn!” his opponent declared and Chad was forced to stand back to watch his opponent play. 

     He watched the man’s cue stick rocking back and forth as he lined up his shot.  Forward and back… forward and back… as he carefully aimed.  And all Chad could think about was what that cue would feel like going back and forth in his own ass.  It had been so long now.  So long!  He hadn’t had any pleasure since the bet ended.  And he desperately needed that pleasure.  But he had vowed – never again!

     His opponent sank the ball easily and started lining up his next shot.  Forward and back… forward and back he rocked his cue stick once again before taking the shot.  And once again the motion of the stick stimulated the need inside of Chad. 

     He couldn’t take it anymore!  He had to get his things!  He had tried so hard to be normal, but he wasn’t!  He needed his sissy things!  He needed his sissy life!  No matter what he had vowed, he couldn’t go another minute without them! 

     He left the party in his living room and headed straight for his bedroom… and entered his bedroom closet.  There wasn’t a sign of anything sissy in sight.  He closed the closet door behind him and climbed up on a large box so he could reach the ceiling.  There he opened the trap door, and all his sissy things tumbled down onto the floor around him.  He found himself sitting amid a jumble of soft petticoats and high heels.  But among those things was also one of his most prized possessions… the dildo he had used with Mel.  He grabbed it and ran his hands lovingly over it… back and forth.  He slid his hands along its spiraled shaft.  He stuck it in his mouth and licked it and sucked on it.  But that wasn’t how he wanted to feel it.  That wasn’t how he needed it.

     His pants were somehow gone and he placed the tip of it right against his naked asshole… and he pushed.  It slid in so easily… so slippery… so sensually.  And he loved it.  Again and again he pushed it in and pulled it out, but while it felt so good, he simply couldn’t get what he needed from it… what he wanted from it.  And he never would.  It was why he had packed it all up in the first place and vowed to never touch any of it again.  Because… without Mel… none of it was any good.  And it never would be. 

     But still he tried.  In and out…  In and out.  And suddenly his attention was grabbed by the sound of someone talking – just outside his closet door!  His friends!  What were they saying?  He was forced to listen harder.

      “So come on down and select the car of your choice!  We’ve got every model in stock right now and we’re ready to deal.  You won’t find a better car deal then what we have right here!”

     Car deal?  What was that about?  And he suddenly realized that he was listening to his clock radio.  With a grunt of effort, he pulled himself out of his dream and into the waking world… where he promptly forgot everything he had been dreaming about. 

     As the pink clock radio played mindlessly in the background, he took a moment to collect himself.  He was laying on his back with his pacifier in his mouth.  The extra bulky cloth diapers Mel had put on him last night were now far more bulky.  He couldn’t bring his legs anywhere near each other if he tried… which he didn’t bother to do.  He had no doubt the diapers would be very heavy once he got to his feet.  The bra he was wearing that helped support the breast forms that were glued onto him, itched a bit at the side.  He scratched momentarily at it.  He briefly thought about the delightful baby doll nighties he sometimes wore to bed… but hadn’t bothered to wear in a while now.  Why not?  He also had some onesies that he could wear as well.  He hadn’t touched those in a while either.  Of course, the onesies were lockable!  Maybe that was the reason. 

     Forcing himself to roll over off of his blow-up mattress and onto the floor, he rolled to his knees where he reached over and turned off the radio.  He was grateful that the days of it waking him up with overly loud rock music were now past.  This was a much better way to wake up every morning.  He accidentally kicked over one of the empty baby bottles on the floor nearby as he forced himself wearily to his feet.  Yes, his diapers were super bulky and heavy.  Messy inside too… as usual. 

     He waddled out to his kitchen to get his required three baby bottles.  He only gave passing thought to the notes Mel used to leave him.  He still missed them, but like many other things, they were past that part as well.  In fact, they were past almost everything with the bet now.  They only had today, which was Wednesday, and tomorrow – Thursday, to go before he could go back to normal on Friday and regain all his control.  As he waddled back toward his solitary chair in his living room, he again wondered how long it would take him to regain all that control.  An hour?  Two hours?  Maybe as much as four?  The fact that he could go two full days without being able to regain that control was unthinkable.  Impossible!  Of course, that was the basis of their bet.  And no matter what his body was doing now.  It just couldn’t be done!

     As he sat in his one and only chair and stared mindlessly at the childishly colored pictures on the wall in front of him, he wondered how humiliating today would be.  Every day since this bet had started had been totally, impossibly humiliating.  Wonderfully humiliating.  He amended that thought.  Actually, the last few days hadn’t really been that bad at all.  He had done almost nothing in the last two or three days that was overtly humiliating… well, to him… now.  So what would today bring?  Would it be as easy as the last two days?  As much as he loved and yearned for all the humiliation, he silently hoped his day would be an easy one!

     It was very faint, but she could still smell the aroma of the coffee brewing out in the kitchen.  She opened her eyes and concentrated on it more.  Yes!  Fresh coffee!  Which could only mean that Sissy was out there just as he was supposed to be.  But how much longer would he be there for her?  Today… and tomorrow?  But what about the future… the future she was working so hard to make happen?

     She sat up in bed and called loudly for him, mentally reminding herself to invest in a small bell of some sort.  And a minute later she heard the sound of his shoes as he hurried toward her.  He appeared, fresh coffee in hand, dressed perfectly in his maid’s uniform… just as she wanted him to be.  Her maid.  Her personal servant… and so much more!  She thrilled as he curtseyed for her and said good morning.  She was just as thrilled as he curtseyed again afterwards.  She ordered her breakfast – in bed – and watched as he nearly ran out toward the kitchen.  So nice.  So nice.

     This was the life she was trying to get to.  This was what she wanted.  The only question now was… could she actually get it?  Could she win their bet and finally make all her dreams come true?  She had to!  She had to!  But even in the midst of her determination, that one nagging little thought made its presence known – was it really right for her to do with him what she planned?  Even though she worried about it, she forced the thought from her mind to concentrate on happier things… like the fresh cup of hot coffee she was now holding in her hands – while she still hadn’t even gotten out of bed!

     One egg sunny-side up, three strips of bacon, and a piece of toast spread with strawberry jam – all laid out nicely on the largest serving tray he could find in her cabinets- which was not really the right kind of tray to serve her breakfast in bed on, but he was doing the best he could with what he had.  Very carefully, he carried the tray into her bedroom, she was sitting up in bed waiting for him, her coffee cup still in her hands.  She set the cup on the nightstand next to her as he approached.  He curtseyed – carefully, and set the tray down on her lap. 

      “Thank you Sissy,” she said gratefully.  “Please bring me more coffee.”

Curtsey.  “Of course,” he replied before curtseying a second time.  A minute later, he brought her cup back, freshly filled.  He delivered it with another curtsey, then stood back out of the way. 

     Mel started eating, but there was one little problem.  “Don’t you have other things to do than to stand there watching me eat?” she asked.

     Chad curtseyed and hurried out of the room again to leave her alone.  Other things to do?  Like what?  While he waited for Mel, he decided to prepare his own baby cereal breakfast.  At least that way Mel wouldn’t have to do it and maybe she wouldn’t “forget” to feed him when she came out of her bedroom.

     Her breakfast finished, Mel set the tray away from her on the bed and got up.  She threw a light robe over her nightgown and headed for the bathroom.  One nice thing about having someone like Sissy as her servant, she would never have to worry about getting into the bathroom because he might be using it.  When she was finished, she went out to the kitchen to find him.  He was just standing there by the counter drinking from his bottle.  She noticed the bowl of baby cereal already poured out into his dish, waiting for him to be allowed to eat it.  But that wasn’t her first concern.  “How much time do you have before your leaking deadline?”

     Chad removed the bottle from his mouth and quickly checked the clock.  Then he curtseyed.  “Twenty four minutes,” he replied before curtseying again.

     Mel studied the clock as well.  “So you’ve only got another nine minutes to go before you lose your reward time,” she noted.

     Chad hated to admit it.  Curtsey.  “But I think my diaper is getting really close to leaking,” he replied before curtseying again. 

      “Let me see.”

     Chad pulled up the skirt of his uniform to show her how wet his diaper was.

     Mel studied his diaper.  “Turn around,” she commanded.  “Let me see the back too.”  As he turned for her, she saw that his diaper did indeed look like it was totally saturated, or at lest fairly close.  “Pull your skirt up all the way around and leave it up so we can watch it,” she told him.  She glanced at his breakfast on the counter.  “I don’t think it will hurt for you to wait a few minutes longer before you eat.  Let’s see if you can get that diaper leaking first.

     Chad grabbed his baby bottle and started drinking furiously again.  Leak!  Leak!

      “While we’re waiting,” Mel said, “go get my coffee cup and refill it for me.”

     Chad hurried off to the bedroom and grabbed not just her cup, but the whole tray from her breakfast.  As he came back, he saw Mel sitting down at the kitchen table.  As quickly as he could, he refilled her coffee cup and brought it to her.  Then he hurried to get his baby bottle back in his mouth again.  Leak!  Leak!

     Chad drank his bottle… and Mel drank her third cup of coffee for the morning.  A few minutes later, Chad’s bottle emptied and he grabbed another one from the large supply in her refrigerator.  Leak!  Leak!  Together they watched as the minute hand on the clock slowly worked its way toward his deadline.  Chad desperately kept feeling around the leg openings on his diaper, but there was still no indication of any wetness escaping… yet.  Chad watched in growing disappointment as the clock ticked through the final minute before he could still gain any reward time.  His heart fell as the final seconds wound past.

      “No reward this time,” Mel noted as she got up from her seat.  “Better luck next time.  Let’s just hope you don’t miss your real leaking deadline, or trust me, I’m going to make sure you really regret it!  This late in the game, there should be no excuse at all!  Ever!”  She removed the tray from his highchair so he could climb up into it.

     Chad had no doubt that she would be really mad if he didn’t manage to leak.  He could tell his diaper was close – so very close.  In fact, some of his diapers had leaked long before this state.  But this one was simply being stubborn.  As he started climbing up into his highchair, he felt something odd at his leg.  “Wait!” he said quickly before Mel could put the tray in place.  “I think I’m leaking!”  His fingers probed the spot where he had felt it.  “Yes!” he declared.  “Right here!”

     Mel looked, but she had to look hard to see it.  But… it was there – a tiny bit of a leak.  She smiled.  “Just missed, didn’t you,” she said with a chuckle. 

     Chad didn’t think it was that funny.  His thoughts were running more in the direction that the diaper had somehow done that purposely to him… just to tease him. 

      “Go change quickly now,” Mel told him.  “And as usual, your next time period has already started.”