The Bet - Chapter 53 (Tuesday – Week 8 Part 9 of 10)

The Bet

By Karen Singer

Chapter 53 (Tuesday – Week 8 Part 9 of 10)

      “Sissy!” Mel’s voice finally called from the kitchen.  “Get out of your corner and start preparing the floor of your punishment area!”

     While Chad was very grateful to finally be allowed out of his corner, he wasn’t glad about being punished.  What for?  And his biggest question was… who was going to do the punishing?  Having no choice, he quickly grabbed a stack of diapers and spread them out, protecting the floor as he usually did.  By the time he was finished, he heard Mel and Derek getting up from their seats at the table.  He stood back out of the way as they approached.

      “What are you doing?” Mel asked.  “Are we going to have to punish you because we had to wait for you to get undressed as well?”

     Still not knowing why he was getting punished, Chad started removing his clothes.  He soon stopped though when he realized that Derek was standing there watching him. 

      “What are you waiting for?” Mel asked.  “I told you to get undressed.”

     Chad resumed undressing.  His apron, his dress, his shoes … and after another slight pause, he removed his plastic panties, and finally his leaky overly soaked diaper – leaving him in only his waist cincher and the bra to support his glued on breast forms. 

     Mel walked over to the corner and retrieved her yardstick that she used to punish him.  Chad was actually glad to see her get it.  He didn’t want to be punished by Derek.  But as she turned around to bring it back, he felt his fear growing.  He didn’t want to be punished at all!  And just then, he heard an odd sound that startled him a bit.  He looked down… he was peeing on the floor!  He jumped back a bit because he was so surprised by it.  Well, at least he was standing on the part of the floor he had already protected.  He could tell that Derek looked simply disgusted.  Mel however, looked like she was going to laugh… which she didn’t.

      “Okay Sissy,” Mel said.  “You know how this works.  Assume your position!”

     Chad slowly moved over closer to the back of her chair and leaned his body against it, bracing himself against the chair with his hands.  Then, because he knew he had to, he raised his backside up, making it the perfect target for her yardstick.  And all too soon he heard the familiar swosh of her stick and felt the stinging slap as it connected painfully with his backend.  He straightened up and turned to Mel.  He curtseyed.  “Thank you,” he said in his sissy voice.  Then he got back in position again.

      “See how we do it?” Mel said to Derek.  She held the stick out toward him.  “Now it’s your turn.”

     But Derek shook his head.  “Not with that!  I’ll break it for sure!  Don’t you have anything… stronger?”

     “Not that I know of.  Can’t you just try not to break it?”

     Derek shook his head.  But an idea came to him.  Instead of taking her stick, he removed his belt instead.  “I’ll just use this,” he said.  “It should do the job nicely, and you won’t have to worry one little bit about your yardstick getting broken.”

     Mel raised her eyebrows for a moment, but said nothing.  She backed out of the way to give him room. 

     Derek folded his belt in half to make it easier to handle.  “You deserve this!” he muttered quietly but menacingly.  Then all too quickly he brought the belt up… and down hard!  The resulting slap was far louder than any sound Mel’s stick ever made.  The pain from his belt was far more as well.  Chad cried out in pain and surprise.  It took him a moment to recover enough to realize they were waiting for him.  Doing his best to not rub his sore backside, he slowly turned around.  They were both watching him.  Waiting for him.  Hesitantly, he curtseyed and said “Thank you,” to Derek.  Then he started getting back into place again.  But he wasn’t at all sure he could manage to endure another slap from Derek’s belt. 

      “This takes too long!” Derek grumbled.  He waited till Sissy had raised his backside up for him to hit, then he brought his belt down just as hard once again.  “Just stay there like that!” he demanded, “till I tell you to move!” 

     Chad was surprised, and hurting, but before he knew it, Derek had hit him again.  And then again!  He really needed to brace himself against the back of the chair now.  In fact, he was holding on for dear life!  Not just because of the force of the blows, but because the pain was so much he had to hold tight.  Derek kept hitting him… all too hard… and all too fast.  It was like there was no letting up.  He was crying before he knew it.

     And then Derek stopped.  “Now you can thank me, you stupid simpering jerk!”

     Crying, Chad straightened up.  His hands went immediately to his backside, but touching himself was painful.  He turned around and curtseyed.  “Thank you,” He said to Derek.  He just hoped he was finally done now.

      “That was for not getting me any beer when you went to the store earlier!”  Derek declared. 

     Not getting any beer?  Chad was shocked.  He didn’t know he should have… but then, he should have guessed.  But at least that was over with now.  “I’m sorry, Derek,” he managed to get out between his sobs.  “I’ll remember next time.”

      “You better!  Jerk!”

     Chad turned to Mel.  Can I get my diaper now?”

      “What?  We’re not nearly done.  We’ve only just started.  That was just for not getting him any beer.  Now we have my list of things you did wrong to deal with!”

     List? 

      “Tell you what, Derek,” Mel said, “you seem to be better at this than I am, I’ll let you administer the punishment for each item.”

     What list?”

      “With pleasure!” Derek growled. 

      “Back in position, Sissy!” Mel ordered.

     Chad would much rather have run away, but he knew without a doubt that he wouldn’t get very far… and that he would only get punished much worse if he did.  Once again he leaned over the back of the chair.  He was still crying from his last punishment… and Mel had a list?

      “First of all,” Mel said, “you were late getting home from work… which meant that dinner was late!  Just because you were afraid of your coworkers seeing your diapers!  Not good enough!  Derek, have at him!”

     Once again Chad was subjected to a serious of blows from Derek’s belt.  He was crying like a baby by the fourth one.  But Derek didn’t stop at four.  Chad couldn’t even count how many blows he got because they hurt so much.  And when it was finally over, he had to stand up and curtsey and thank Derek once again.  Then of course, he had to go all through it again.

     Late coming home…  Shoes not shined well enough…   Uniform not starched to perfection…  Wearing the wrong earrings with his uniform…  And being rude and interrupting them while they were eating.  Chad had no idea how many times he got hit with Derek’s belt.  He did know that Derek never seemed to ease up on how hard he was hitting.  He also knew that he was hurting like he had never hurt before, and was crying like he had never cried before.  And it seemed like each time he got up to curtsey to thank Derek, he felt pee splashing down on his feet from out of his chastity device, even though he was hurting far too much to even feel that he was even peeing each time.

     And then, after Chad had curtseyed the last time, Derek put his belt back on and said, “That’s only a tiny taste of what I’d really like to do to you… jerk!  Just pray I don’t really get a chance to hurt you!”

      “Now hurry and get your diaper on!” Mel ordered.  “You’ve only got an hour and forty-five minutes to be leaking again… starting two minutes ago!”

     Chad picked up one of the diapers from the floor – many of which he noticed were already decorated with some of his pee.  Standing, he put it on.  He winced with pain as it touched the skin of his backside.  Gingerly, he finally fastened it in place. 

      “Now go find yourself some dinner from the jars in your cabinet,” Mel told him.

     Chad curtseyed and left, but the act of curtseying made his diaper rub against his raw backside, causing him more pain. 

     He pulled several jars of baby food out for himself and dumped them out onto one of his plastic child plates.  Then he grabbed another bottle and took a good long drink from it.  He didn’t want to get punished later for not leaking on time – especially not after what Derek had just done to him.  The thought of sitting in his highchair just then wasn’t exactly appealing, so he stood at the counter and started shoveling the mushy food into his mouth with his tiny baby spoon.

     Mel walked back into the kitchen.  “What are you doing there?”

     Chad remembered to curtsey.  “Eating.  I was too afraid to sit down.”

     Mel couldn’t help but crack a big smile.  “Nonsense!” she replied laughingly.  “Climb up into your highchair.”

     Chad had several grave misgivings about that, mostly because of his burning rear end.  Reluctantly, he went over to his chair and climbed gingerly up into it.  The burning pain intensified greatly everywhere his bottom compressed against the seat.  He was about to slide off the chair again, but Mel quickly pushed the tray into place, locking him right where he was – trapped, in his highchair, on his horribly burning bottom.  He wiggled painfully trying to find some comfortable position to sit, but there was none.

     Mel brought his plate of baby food and his bottle over to his tray and set it down for him.  Then she went to the refrigerator and got him a second bottle of her green tea and set that down for him as well.  “That should keep you occupied for a few minutes,” she said.  With a smirk, she turned and left him.

     Chad no longer felt like eating.  And trapped as he was on his stinging bottom, there was no way for him to get even remotely comfortable.  His only chance to get out of it now was to finish his dinner and both bottles as soon as possible – and hope that Mel would release him sooner rather than later.

     Derek leaned over and kissed Mel on the lips.  The passion he was feeling was returned, but only until her phone ringing interrupted them.  A bit irritated at the intrusion, Mel got up and found her phone.  “Hello?”

      “Hi Mel.  What’cha doin?”

      “Hi Sandy.  What’s up?”

      “I thought you might like to go through some of the music I found for Sissy’s little performance next week.”

      “Oh…  I really need to, but…  I have… company right now.”

      “Oh, you do?”

      “Uh…  Yeah.”

      “Derek?”

      “Um… Yeah.”

     Sandy giggled.  “Why don’t we try again tomorrow night?”

      “That might be a better idea,” Mel agreed.  “See you then for sure.”

     Mel hung up her phone and glanced over at Sissy.  He was still in his highchair – of course he couldn’t get out of it – and was drinking one of his bottles.  It looked like he had already eaten his dinner and was now just finishing the second bottle she had given him.  “Sissy, are you about done now?” she asked.

      “Yes, Mistress,” Chad replied, anxious to get out of his highchair.  He immediately put his bottle back to his lips to finish it quickly.  He was still finishing it as he slid painfully off the chair.  And a moment later, the bottle was empty.  With a sigh he said, “All done.”

      “Good,” Mel replied.  “That was fast.  Now see how fast you can get the kitchen straightened up, even if you have to save a few things to clean tomorrow.”

     Chad immediately set to work, but there really wasn’t much to do since he had only cooked a few steaks and potatoes.  Twenty minutes later, the kitchen was spotless again.  But did he dare tell Mel?  She had seemed to be in a hurry about something though since she wanted him to clean everything up fast.  He glanced back into the living room and saw Mel and Derek once again locked in a kissing embrace.  Jealousy hit him hard.  But what should he expect, that she would like him enough to do what she was now doing with Derek?  He knew better.  He was nothing but a sissy.  A worthless sissy!

     Still…  He quietly went into the living room where he waited silently for their lengthy kiss to end.  Then he cleared his throat quietly to get their attention.

      “What is it Sissy?” Mel asked.

      “I’ve finished the kitchen,” he replied.  “Would you like me to go home now?”  He was actually hopeful.

      “Absolutely not!” Mel replied.  “It’s way too early.  Grab another bottle and get back up on your perch.  And please be quiet about it!  We’re… busy.”  She immediately went back to necking with Derek, who didn’t seem to be disappointed in the least.

     Chad didn’t want another bottle, especially not after he had just finished two of them with dinner.  But he got one anyway and once again climbed up on his perch and started drinking it.  He could hear the faint sounds of Mel and Derek making out on the couch a short distance away.  He just couldn’t see them – not with his head staring at nothing but the ceiling corner while he drank his bottle. 

     What was he doing with her?  Was it anything he had ever done with his wife… make that – ex-wife?  No, he was sure it wasn’t.  Because of his strange yearnings, he had never actually been that forward or physical with her.  It was just another one of his big failings – all because of what he was – a sissy!  No, Mel would never have anything to do with the likes of him… other than to ridicule and dominate him, which she seemed all too good at.  Fortunately.  But then, wasn’t that the life he really craved?  Wasn’t that what he always wanted?  Unfortunately, the answer was still a big yes.  He just always imagined it to be a bit less painful.  Not to mention he always imagined that he would get some kind of sexual release – at least once in a while. 

     What would happen if he didn’t win the bet – not that it could really happen – he knew that much for a fact!  But what would happen?  Would he ever feel sexual release again?  Knowing Mel, not if she could help it.  It was another reason why he really had to win this thing.  He really wanted some relief!

     His bottle emptied and he quietly lowered his bottle down by his side.  His head lowered too so that he was once again staring at the blank corner walls.  He closed his eyes and concentrated on the sounds coming from the couch.

      “Maybe we should continue this in the bedroom,” Mel suggested quietly as she ran her hand over the skin of Derek’s chest inside his shirt.

      “Sounds good to me,” Derek replied.  He started to get up from the couch, but he noticed Sissy in the corner.  “What about him?” he asked.

      “He’ll be fine.  He can just stay there like that.”

     Derek kept looking at Sissy.  “I don’t really trust him,” he said. 

     He walked over closer to Sissy.  Very close.  “Are you enjoying yourself there in your corner?” he asked.  “Have you enjoyed listening to us on the couch?”

     Chad started to turn his head to answer, but Derek noticed the movement.  “Don’t move!” he ordered angrily.  “I don’t want to hear anything you have to say!”

     Chad immediately buried his face in the corner once again as fear ran though him.  His burning stinging bottom was still an all too painful reminder to not cross Derek in any way.

      “That’s right,” Derek said, “you keep that stupid face of yours buried there where nobody can see it!  Don’t you dare turn it away from that corner!”

     He stared for a moment at the long dangling heart-shaped earrings hanging down from Sissy’s ears.  They were essentially odd shaped rings.  If there were some hooks attached to the walls, he could just hook them over them and they would hold Sissy’s head right there so he couldn’t move it.  But there were no hooks. 

     Derek looked back at Mel.  I’d rather not be interrupted by this clod,” he said.

      “Don’t worry,” Mel replied.  “He’s not going anywhere.” 

     Derek stepped away from Sissy and started for the bedroom.  But he stopped and turned back.  He shook his head.  “I just don’t trust the little jerk.  I can’t trust him anymore.  Not… anymore.”

      “He’s not going anywhere!” Mel repeated.

     Derek kept staring at Sissy up on his perch.  “I still don’t trust him,” he muttered.  Then a moment later he asked.  “Got any rope?  Robin has to tie him up to keep him in place at work.  Maybe that’s why I don’t trust him to stay there.”

     Mel rolled her eyes.  “He’s not going anywhere!” she insisted.  “But if you want…”  She went over to her bottom desk drawer and pulled it open.  “I’ve got plenty of rope here.  I use it on him… often.”

     Derek pulled a piece of the rope out of the drawer.  He had to untangle it but that was fairly easy.  He went over to Sissy and tied his hands behind his back.  Then he went back to the drawer and grabbed another piece of rope.  This one he used to tie Sissy’s ankles together, with much of the rope going under his perch so that Sissy’s feet were tied to it.

      “Now… he’s not going anywhere!” Derek proclaimed as he stood up again.  “Got anything I can use to gag him with so he doesn’t suddenly yell for one of us while we’re busy?”

     Mel went to Sissy’s purse and hunted around in it for a moment.  She found his pacifier and brought it back to him and stuck it in his mouth.  “There,” she said, “that should take care of it.”

     But Derek still wasn’t satisfied.  He grabbed a third piece of rope from Mel’s drawer and pushed it through the ring on Sissy’s pacifier.  Then he tied it tightly behind Sissy’s head.  “Now I feel better,” Derek replied as he headed for the bedroom with Mel.  “At least he won’t be bothering us for sure now.  But you should see what I’d like to do to him.”

      “What’s that?” Mel asked, knowing that everything that Derek had just done was totally unnecessary.

     Derek stopped and walked back to Sissy.  He pulled on one of Sissy’s earrings.  “See these?” he said to Mel as she walked over closer.  “All you’d have to do is to install a couple of hooks on the walls, then just slip them over the hooks.  He won’t be looking anywhere except the corner then!”

     Mel giggled.  “I wasn’t exactly worried about that anyway.  It’s never been a problem before.”

      “But I haven’t been around here much before,” Derek countered.

     Mel shrugged.  “Then if you want, find some hooks the next time you come.  I don’t care.”

     Derek nodded.  “I just might!”  He turned to go back to the bedroom, but he stopped once again and went back to Sissy.  “We’re going to be making some noise in the other room.  I expect you’ll be able to hear some of it through the wall.  I hope what we’re doing in there makes you so jealous you start to cry all over again – you stupid sissy!  Just don’t let me, in there, hear anything out of you in here, or I’ll whip your butt worse than before!”  With that, he finally left Sissy alone and took Mel into her bedroom – for some very delayed fun!