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

The Bet

By Karen Singer

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

     Chad knew they were gone.  He knew they were both in the bedroom.  He could hear them… sort of.  Well, actually he could hear some muffled noises coming through the wall.  What he hadn’t heard though, was the bedroom door closing. 

     Still staring into his corner, he moved his arms a bit behind his back.  But that was about all he could move.  There was no way he could move his feet at all.  Especially not tied to his perch the way he was.  He mentally steeled himself for a very long session right where he was.  His toes were not going to like it, but as with everything else in his life, there was nothing he could do about it. 

     He heard giggling coming through the wall.  He tried to listen harder  He turned his head to the side a bit so that he could put his ear closer up against the wall.  Since they were in there and couldn’t see him, he dared to actually move his head that much.  He certainly didn’t have to worry about moving anything else – he couldn’t! 

     He could hear that Mel and Derek weren’t talking much, but it did certainly sound like they were having fun – the kind of fun he couldn’t have.  The kind of fun that Mel had rendered him incapable of having.  The kind of fun that meant not only sexual stimulation, but more importantly, release.  The very thing his body yearned for – but couldn’t have.  All because she had rendered him incapable of it.  All because of what he was.  A sissy. 

     Derek was in there with her now.  A big, strong, handsome – virile man.  Confident!  Mentally secure!  Not only normal – but all male – totally.  Not like him.  Not like him at all. 

     And what was he?  A sissy! Nothing but a big sissy!  A bigger sissy than most in fact.  He wasn’t like Derek in any way.  He might be male – but biologically only.  None of those other traits applied to him at all – anymore.  Maybe they used to… sort of.  But he had never been the strong confident male that Derek was.  He didn’t deserve for women to like him.  He didn’t deserve… anything!  Except all the ridicule that he got – every day of his life – now.  All because he was nothing but a sissy.  A big, big, sissy!

     Maybe it was because of what Derek had said to him just before they went into the bedroom.  Maybe it was because of the self-degrading thoughts running through his head just then.  Or maybe it was because of the tiny things he could hear through the wall and could recognize what they were.  Or maybe it was all of that.  But as he listened to Mel and Derek’s little noises in the room on the other side of the wall – he cried again.  Not loudly, but for himself.  He couldn’t help it.  He was a sissy.  And there was nothing he could do about it. 

     Derek planted one last powerful kiss on Mel’s lips and rolled off of her.  “That was great!” he declared happily.  “But now I’ve got to pee!”  He quickly got out of bed, totally naked, and headed for her bathroom.  But as he approached the bedroom door, he stopped.  Sissy was out there – and he was naked!  He wasn’t sure if he wanted to worry over whether Sissy might see him naked or not.  He peeked his head out of the doorway – and saw Sissy – leaning up against his corner with his eyes closed.  The reason he could see Sissy’s eyes though, was because Sissy’s head was still turned to the side as he rested it against the wall. 

     As much as Derek needed to pee, he went back to Mel.  He put his fingers to his lips to caution her to be quiet.  Then he motioned her to look out the door toward Sissy.  Once she had seen he whispered.  “Now you know why I don’t trust him.”

      “It looks like he fell asleep like that,” she whispered back.

     Derek looked again and was surprised to realize that she might be right.  “I’ll be right back,” he whispered.  He quickly hurried to the bathroom to relieve himself, then still naked, he came back to the bedroom again and put his underwear and pants on.  Then he removed his belt from his pants. 

     Mel had slipped a robe on as she watched him.  She was surprised when Derek removed his belt but she said nothing about it.  She followed him as he went out toward Sissy.  Sissy never moved, even when they got close.  She could see that his eyes were closed and that he really was sleeping in that odd position.  Maybe he wasn’t as uncomfortable on his perch as she thought!

     Derek walked up behind Sissy, raised his belt, and slapped it hard against Sissy’s diapered backside.

     Sissy jolted awake at the unexpected blow to his already tortured rear end.  What had happened?  It took him only a moment to realize that Mel was right next to him and that Derek was there too… and that he wasn’t facing into the corner like he was supposed to.  It took him another moment to realize that he had actually fallen asleep there.  How long had he been up on his perch this time?  Not knowing what else to do, he quickly reburied his face in the corner.

      “That’s right!” Derek said behind him, “you better hide that stupid face!”

     Mel was tempted to tell Derek to ease up, but she didn’t.  “Untie him Derek,” she said instead, “while I go and get dressed.  And Sissy, once you get yourself off of that perch, get yourself another bottle!  I’ll be back in a few minutes.”  She turned and left them alone.

     Derek untied Sissy’s hands, then untied his feet.  He didn’t remove the rope holding Sissy’s pacifier in place till Sissy had managed to get himself off of the perch and stretch his aching legs and feet.  Then Sissy hurried off to the kitchen to get his bottle.  He had barely started drinking it though when Mel came back from the bedroom wearing some shorts and a t-shirt.

      “How much longer before you can send the little jerk home?” Derek asked.

     Mel smiled.  “Not quite yet.  He still has to get that diaper leaking… and then I had one other thing I was planning on doing with him tonight.  You can stick around and watch if you like.”

      “What’s that?” Derek asked.

     But Mel just smiled at him mischievously.

      “I guess I’ll stay,” Derek decided.

      “Good,” Mel replied.  “Maybe by that time you’ll be ready for a bit more exercise.”

      “I’ll definitely stay!” Derek declared.  “Sissy!  Get yourself two bottles!”

     Since Derek was planning on a little more sex with Mel after Sissy left, he didn’t bother getting dressed any more than he already was with just his pants and underwear.  He sat on the couch and turned the TV on while Mel retrieved her laptop so she could get some work done as she sat next to him.

     To keep Sissy occupied until he started leaking again, Mel had him stand right where they could easily see him and drink his bottles.  She positioned him where he could also see the clock.  Every minute that passed, Sissy had to stop drinking, curtsey, and softly announce whether he was leaking or not.  Then he could curtsey again and put his bottle back into his mouth to keep drinking.  When he needed another bottle, he had to run and get back again in the one minute time span between curtseys – and of course, announce whether he was leaking or not. 

     Mostly, Mel and Derek ignored him.  But every once in a while they did look over to watch him… Derek mostly during the commercials, and Mel whenever she reached a point where she needed to think about something. 

     Sissy, for his part, was doing everything he possibly could to make himself leak as soon as possible… just as he usually did.  It seemed like most of his life lately was one big effort to make his diapers leak.  A never ending effort! 

     It took Sissy nearly forty-five minutes to start leaking again, and when he did, his announcement was too excited to be anything but quiet.  “I’m leaking!” he suddenly declared with another curtsey.

      “It’s about time!” Derek grumbled. 

      “Good!” Mel said as she closed her laptop and set it aside.

      “Now what?” Derek asked.

      “Now?”  She turned to Sissy.  “Sissy, grab some of those diapers off the floor of your punishment area and protect the bed – thoroughly!  And hurry up!”

     Sissy grabbed a large stack of the diapers in his arms and quickly carried them into the bedroom.  Two minutes later, Mel’s bed was thoroughly protected under multiple layers of spread-out disposable diapers. 

      “Okay, Sissy,” Mel said.  “Up on the bed.”

     Chad wasn’t too sure what Mel had in mind for him, especially since Derek was there, but he climbed up on her bed and started laying down. 

      “No,” Mel said.  “Turn over, and stay on your knees.”

     Sissy didn’t really know what Mel had in mind for him, but he now had his suspicions.  What he hoped Mel was going to do with him was also something he didn’t want her to do – only because Derek was there.  But when Mel made him move up closer to the head of the bed and then started bringing out her ropes to make sure he stayed there, he became fairly certain of exactly what she had in mind. 

     The concept of Derek seeing him get raped in the rear end by Mel was horribly embarrassing.  Mel had been showing Derek all too much about what she did with him lately.  First Sunday, then tonight.  And now she wanted to top things off by showing Derek how she teased him sexually?  But he had nowhere to go to get away – as if he would… or could.  Especially once Mel had tied his wrists to the head of the bed and also to his knees, along with tying his ankles to the foot of the bed.  He wasn’t going anywhere.

     And all too soon he felt Mel unfastening his soggy leaking diaper and removing it.  His present position made that act seem all too embarrassing as well – even though Derek had seen him changed several times now.  As he felt how naked and exposed he was in front of Derek – knowing what Derek was about to see happening with him, he felt himself involuntarily peeing on the diapers he had used to protect Mel’s bed.  He was glad he had put several layers under him. 

      “Disgusting!” Derek muttered quietly. 

     Mel went to her drawer where she kept the strap-on toy.  With her back to Derek, she removed the end she would normally have put up inside of her and left that part in the drawer. 

     Derek couldn’t believe what he was seeing when he watched her buckling the large phallus onto her hips.  “What the heck?” he exclaimed.

     Mel just smiled.  “This is the only type of sex he’s allowed anymore.  And the most interesting part is… that he really likes it!”  She grabbed her lube from the nightstand and smeared it liberally over the fake penis sticking out from the front of her shorts.  Then, with a wry smile at Derek, she climbed up on the bed behind sissy.

     Derek watched open mouthed as Mel carefully lined the tip of her tool in place against Sissy’s backside, then with one hand still on it to help keep it aligned right, she began pushing it in with her hips.  The moment he realized the thing was actually going into Sissy, he felt a moment of increased revulsion.  What he watched as Mel now placed both hands on Sissy’s hips to steady herself was not sexually stimulating for him in the least.  In fact, he found it nothing but revolting.  And yet, since he still felt nothing but total contempt for his former friend, he hoped that Sissy was feeling just how humiliating the act really was.

     Incredibly, Derek watched as Mel slowly buried the entire length of her large strap-on shaft inside of him… and kept pushing to make sure it was completely buried.  Then she slowly began withdrawing it again.  He saw a small shudder run through Sissy’s body.  But was it a shudder from the horror of the act – or something else?  It was a minute later when he realized that Sissy was actively trying to push himself onto the thing just as much as Mel was guiding it in and out of him.  He realized that Sissy was loving it!  Unbelievable!  And then Mel started talking to Sissy!

      “You like this,” she said softly.  “You love it!  Show me how much you love it!  Are you going to show Derek how you can cum now from just this being done to you?  How you no longer even need that tiny little thing that you pee out of?  Show him how useless that thing is to you now.  Come on, show Derek how much you love this and no longer need your old tiny piece of equipment.”

     Showing Derek what was all too obvious now was the last thing that Chad really wanted to do – on one level.  But the stimulation coupled with the humiliation of what was happening was fueling his sexual need all too much to be denied.  He hated showing Derek how much he loved this, but he simply couldn’t help the way his body reacted.  Fortunately, he was now fairly sure that achieving orgasm had been a little twist of his imagination.  But damn, Mel talking to him like that while she was fucking him was making him so hot!

      “Do you like showing Derek the only way you’ll ever be able to have sex again?” Mel continued softly.  “Do you wish it was Derek doing this to you instead of me?”

     Off to the side, Derek grunted.  “No way I’m ever sticking my cock into his asshole!”

     Mel looked at him and scowled.  “Well then, maybe you’ll let Sissy have it some other way instead.  Would you like that Sissy?”

     It took a moment before Derek had any clue what Mel was talking about.  His suspicions were quickly confirmed though when Mel started talking to Sissy again.

      “Would you like that Sissy?” she said to Sissy again.  “Would you like sucking on Derek’s cock sometime?  Maybe you’d like sucking on it better than your pacifier.  Maybe you can suck on it and get him all nice and hard for me before I have sex with him.  You can get him in the mood so we both can have a good time while you… well, maybe while you stand helplessly on your perch knowing that he’s doing what you’ll never be able to do again.  But of course, I’m sure you’ll probably be wishing you were me instead of Derek.  You’ll be wishing Derek was having sex with you instead.  But that’s not going to happen I’m afraid.  Derek isn’t interested in having sex with you at all.  He only likes me. Too bad.  So about all you can do then is to get him all nice and hard and ready to have sex with me and then stand there and wait like a good little sissy while we have a good time.”

     Sissy didn’t know why, but the cruel images Mel was sending to his brain were making him hornier and hornier.  And in response he worked himself faster and faster against the artificial phallus she had buried inside of him. 

      “That’s it Sissy,” Mel coaxed.  “Show Derek how much of a sissy you really are.  Show him how much you love doing this.  Show him how much you no longer need having sex any other way.  Show him how you can cum from only doing this.  Prove to him that you’re not a man at all anymore.  Prove to him how much of a sissy you really are.”

     Chad’s body and brain were on fire.  He didn’t think he had ever been so aroused.  He couldn’t help himself.  The delicious feelings from her toy going in and out of him combined with the things she was saying were forcing him to go further than he had ever gone before in search of that elusive orgasm he knew he could never reach.  He worked himself harder and harder… faster and faster against her artificial cock – and it felt sooo good! 

     And then all of a sudden he was feeling things he couldn’t believe he was feeling.  Feelings that reached from his toes up to the hair on his head.  And unbelievably, he suddenly realized he was in the middle of a gigantic orgasm.  He was helpless to fight it… as if he even wanted to.  He worked himself furiously against Mel’s cock, trying to get everything he could out of what was happening to him. 

     Mel realized what was happening to Sissy.  She quickly looked to Derek and pointed down underneath.  “Did he get hard at all?” she asked quietly.

     Derek couldn’t believe what he saw was happening to Sissy, but he looked where Mel wanted – and couldn’t believe what he was seeing there either. A long stream of cum was running steadily out of Sissy’s chastity device.  Cum… not pee!  And Sissy’s tiny little penis was just as miniscule as ever.  As if all the sexual stimulation he was receiving no longer had any effect on that part of him at all!  He looked back up to Mel and shook his head.  “He never grew a bit!” he replied, the disbelief clearly in his voice.

     Sissy was winding down now, slowing down more and more.  He had made it!  He had actually made it!  It wasn’t his imagination at all.  As much as he tried with Cassie, maybe he just needed Mel to do it to him instead.  Mel… and her strap-on… and the things she said to him.  Maybe that had been the missing ingredient all along.  The wonderfully cruel things she said as she fucked him as if she were a real man… proving to him that he was no longer a real man.  Especially not if he could orgasm from it. 

     He didn’t know what Derek must think of him.  Was it any worse than what he had already thought about him?  There was no way it could ever be anything better, that much was for sure!  He just hoped that Derek wouldn’t say anything more to him now.  He had debased himself enough by this.  But he couldn’t help it.  His body and his overgrown needs had betrayed him… completely. 

     Mel pulled out of him and got down off the bed.  She removed the strap-on device from her hips and set it aside where it could be cleaned later.  She turned to Derek.  “You start untying his feet.  I’ll get his hands.” 

     A few minutes later, Chad was no longer tied the way he was.  He was lying on his back instead – while Mel refastened the ropes to wrists once again.  But Sissy was too worn out, too amazed at what had just happened to offer the least bit of resistance – as if he would anyway.

     Mel quickly wiped his front side off, but the cold wet cloth she used on him caused him to start peeing again.  She had to quickly grab one of the diapers off the bed to put over him till he stopped.  Then she wiped him off all over again. 

     She grabbed her jar of suppositories and held it up so Derek could see as she took one out.  Then she had him raise his legs, completely exposing his backside for her.  She wiped that down too before “pretending” to put the suppository up inside of him.  She saw Derek about to say something, but she quickly shook her head to silence him before putting the suppository back into the jar where Sissy couldn’t see her doing it.

     Then she proceeded to diaper him.  The inside diaper was the one she had just used to catch his latest bit of peeing.  She cut slits all over it once it was on him.  The second diaper was the one his cum had landed on a few minutes earlier.  She cut slits all over that one too after it was on him.  Then she added two more layers of diapers and wondered if she should add a fifth.  But she stopped at four.  Hopefully it would be enough.  If not, well, Sissy would have to do the wash anyway, not her.

     Five minutes later she sent Sissy home.  But not before he had to curtsey and thank Derek for punishing him earlier and for witnessing how much of a sissy he really was now.  As Sissy finally walked out and the door closed behind him, Mel stared at the back of the door.  What had Sissy really thought about Derek being there tonight?  What did he really think about Derek witnessing everything?  What did he think about having Derek punish him instead of her? 

     There were a lot of questions she couldn’t answer.  Not for sure.  But they were all questions she was very concerned about.  She had pushed the envelope with him again.  She kept doing that.  This time it was with Derek.  What would she be doing next with him?  She almost didn’t want to think about that because it scared her… but at the same time, it thrilled her too.  She really did get off on dominating him so much.  She really did get her kicks from forcing him to do the most stupid things.  She really did get so much joy and excitement out of having him as her total servant – in every little way she could think of. 

     She felt Derek putting his arm around her.  She looked away from the door and up at him.  “I hope I didn’t scare you too much with what I do with him,” she said.  “I can’t help it.  I really love pushing him like that.”

      “I’m still here,” Derek replied.  “I’m determined to not let that little shit-head get in my way.  I still think he deserves everything that happens to him.  He wanted it after all.  So now I’m glad to see him getting it!”

     Mel realized that she and Derek were looking at what happened to Sissy in two distinctly different ways.  Derek’s came more from anger than anything else.  Anger that she knew would eventually fade.  But what would it fade into?  While she?  Well, she just loved it.  She always would.  She had no doubt about that anymore. 

      “Shall we see if I can give you any pointers in the sex department?” Derek asked as he softly guided her back to the bedroom.”

     Mel almost laughed.  “Oh, I intend on taking very careful notes this time!”

     As Mel laid on her back on the bed once again and Derek moved on top of her, she thought once again of Sissy and what she had just done to him.  And as she felt Derek’s wonderful cock sliding into her once again she tossed one last thought to Sissy.  “Good night Sissy.  Sleep tight.”   

     All other thoughts of Sissy were quickly driven from her mind as Derek strove to drive her to distraction!  Something he had a lot less difficulty doing this time than any other time before.

     Gloria walked her last client of the evening to the door.  She shook hands with him and told him she was looking forward to seeing him again next week.  Then she opened the door and held it while he walked out.  But as she did so, she noticed that the parking lot held three cars, not two as there should have been.  And in the dim evening light, she could see a man leaning against one of the cars.  A momentary bout of fear ran through her. 

     She closed the door and waited just inside, keeping a careful watch on the stranger while her last client of the night started his car and left.  But the man leaning against his car didn’t leave.  Instead he seemed to push himself away from the car and walk closer.  He had something in his hand… a gun?  Her fear increased – until he got close enough to the light for her to see who it was.  Ray!  With a bottle in his hand!

     She was too surprised to see him to realize that she was no longer afraid.  She opened the door for him.  “Ray!  What are you doing here?”

     Ray held up the bottle of champagne he had brought with him.  “I found this lying around on the street corner and was wondering if it might be yours.”