The Bet - Chapter 58 (Sunday – week 9 Part 7 of 7)

The Bet

By Karen Singer

Chapter 58 (Sunday – week 9 Part 7 of 7)

     They were climbing the steps up to the apartment after returning from the restaurant when Chad felt the first noticeable sign that he was starting to leak.  He didn’t curtsey because while going up the steps it never even occurred to him.  “Um… Mistress,” he called to catch Mel’s attention.   He had to wait till she looked back at him.  “I’m leaking,” he told her as they all continued to climb.

     Mel checked her watch.  “Congratulations,” she replied as she reached the top of the stairs.  “You managed that in… maybe a whole minute less than an hour and a half.  So you’ve now got one minute of reward time coming.  Do you want to use that now or see if you can build on it for later?”

      “I think later would be better,” Chad replied, glancing at Derek. 

      “I kind of thought you’d say that.  I suggest you get that diaper changed and quickly since I’ve already started your next countdown!”

     Derek didn’t say anything, but he breathed a mental sigh of relief the moment he walked back into Mel’s apartment.  He had gotten through it – again – having dinner with Sissy present.  It was particularly bad this time since Mel had insisted on feeding him the baby food in the restaurant.  He found it very uncomfortable to sit there and eat while trying to act like nothing out of the ordinary was going on.  And everyone there had been constantly looking at him… well, mostly they all had looked at Chad and Mel, but he was sure they had wondered about him too.  It had been embarrassing!  And he wasn’t the one who really needed to be embarrassed!

     As he headed for the couch he saw Chad heading toward the bathroom to change his leaking diaper.  Thank God for small favors.  At least he hadn’t started leaking while they were in the restaurant.  The last thing he would have wanted to see was Mel changing her “baby” out in the middle of the floor of that place!

     Well, now they were back and there wasn’t much to do except watch TV… which wasn’t exactly what he really wanted to do with Mel.  But that reminded him of what he had recently found out about Mel and Ray being together last night.  Ray had something of a reputation among the ladies – a sexual reputation.  He couldn’t help but wonder how he himself stacked up in that department compared to Ray.  The thought bothered him a little.  Well, tonight he would just have to try a little harder with Mel to impress her – he guessed because he didn’t want to be considered second rate next to Ray.  But then, what did Ray have that he didn’t?  Nothing!  And… he had Mel!  That was one big thing in his favor!  Now if he could just get rid of Sissy!

     And speaking of getting rid of Sissy.  He stuck his hand into his pocket and extracted the cup hooks and earrings he had shown Mel earlier.  Was Sissy far enough done with all his housework yet that he could at least see if his idea worked?  Mel had gone into her bedroom as soon as they gotten back and hadn’t come out yet.  Instead of turning on the TV, he sat down on the couch again and waited for Mel.  Fortunately, he didn’t have to wait long.  She was back long before Sissy had his diaper changed.

     He opened his hand exposing the ugly jewelry he held.  “Do you think Sissy is done enough with his work now that we can try this… just to see if it works?

     Mel stared again at the items in his hand.  She had forgotten about Derek’s little idea.  “I’m sure he’s done enough,” she replied.  “And anything else he needs to do can certainly wait a little while.”

     Chad was back out of the bathroom a minute later.  “Sissy,” Mel told him, “get up on your perch for a while.”

     Chad was a bit stunned by the sudden order.  He didn’t really have all that much to do, but standing in the corner on his perch wasn’t anywhere near the top of his list.  Having little choice in the matter, he curtseyed a bit hesitantly and made his way to the corner.  He realized both Mel and Derek were watching him closely as he placed one foot at a time on his perch, climbing up onto it, forcing his feet to remain in position where they were very uncomfortable, and forcing his body to lean in closer to the blank walls of the corner where he could see almost nothing.  Back in the corner again.  Ugh!

     Derek went over to stand behind him and examine the corner and his position very closely.  He took one of the bent up cup hooks and placed the screw point against the wall about where he thought it needed to go.  He pushed hard making a small mark in the wall.  Then he did the same to the wall on the other side of Sissy’s head.  “Get out of there for a minute,” Derek told him.  “I need more room.”

     Sissy was glad to get off his perch again, but he was a bit afraid now as to why.  What had Derek done?  Nothing that he could see.  But a moment later he watched as Derek screwed one of the cup hooks into the wall very near to where his head would be.  As Derek moved to the other wall, Chad stared at the first hook Derek had installed.  It was bent almost straight up so that the cup part of the hook was more straight than circular and extended up probably less than half an inch.  As Derek stepped back, he saw that the second hook on the other side was bent the same way.

      “Okay Sissy.  You can get back there again.”

     Chad moved, but it was with growing apprehension.  A moment later, he was once again nearly blind as his eyes could see nothing but the walls of the corner – all too close to his head.  And with both Derek and Mel standing so close, he was extra careful to not move any part of his body even a fraction of an inch.   

     Derek held out the screw-on earrings to Mel.  “Do you want to do the honors?”

     Mel was surprised that he would ask, but she took the earrings out of his hand and examined them briefly.  Simple cheap screw-on earrings.  It was the silver chains attached to them that really made them ugly.  Obviously, whatever else had once decorated the earrings had been removed and the chains put in their place.  She grabbed one of them and approached Sissy’s left ear.  Putting it over his earlobe just above the blue stud of his pierced earring, she screwed it in place, being careful to screw it tight, but not too tight.  When it was on, she tugged on it a bit to make sure it was secure enough that it wouldn’t just slide right off.  She dropped it and let it dangle.  “Now what?” she asked.  “I just stick the chain over the hook?” 

      “That’s it,” Derek confirmed. 

     Mel did so, trying several links in the chain first so that when she finally released it, the chain was stretched somewhat tightly but only pulling his earlobe out a little.  She didn’t think it looked painful in any way at all for Sissy, but that was only one earring.  She also noticed that as she put it in place over the hook, since the hook was located slightly in front of Sissy’s ears, it had pulled his head even tighter into the corner than it had been. 

     Moving to the other side, she installed that earring as well.  This one she noticed put a small strain on both earlobes as she pulled the chain and managed to get it over the hook.  She also noticed that his head was now pressed even tighter into the corner.  Since the hooks were placed just forward of his ears, the tighter he kept his head pressed into the corner, the less the strain on his ears.  When she was done she stepped back for a better look.  There were now chains attached tightly from both of Sissy’s earlobes to the walls on either side.  Both his earlobes were pulled, but only a little.  She was fairly sure it wasn’t too uncomfortable for him at all… as long as he kept his face pressed tightly into the corner and didn’t move. 

      “Move your head,” she told Sissy.  “Let’s see how much room you’ve got.”

     Chad tried to turn his head, but it moved only a fraction of an inch before he felt the tug on both ears stopping him.  Being pressed so tightly into the wall hindered him as well.  He tried to pull back a bit and turn his head, but pulling his head back also pulled on the chains and didn’t allow him any more movement than the tiny bit of an inch that he had.  Basically, he couldn’t turn his head at all!  “I… can’t,” he finally replied, not knowing if he was more surprised or frustrated… or excited.

     Derek was all smiles.  “It worked just like I thought,” he pronounced proudly.  “Can you step off of that stand now?” he asked Sissy.

     Chad tried picking his left foot straight up to remove it from the perch, but with his head glued to the corner, as soon as he tried, his knee contacted the wall.  It was only with a lot of difficulty that he was able to turn his leg and finally pull his foot up high enough to get his foot over the top of the bar.  But trying to stretch his leg back to put his foot on the ground behind the perch quickly proved to be impossible.  Standing on only one foot on the perch was even worse than standing there with both feet, so he quickly reversed his course and started working his left foot back again.  “I can’t,” he replied with an even greater amount of frustration.

      “Perfect!” Derek declared happily, seeming to preen himself proudly in front of Mel.

      “It is rather ingenious,” Mel granted him.  “And it certainly makes sure he’ll stay tightly in place… and with a minimum amount of effort.”

      “I can’t move at all!” Chad complained in his sissy voice from the corner. 

      “You’re not supposed to!” Mel replied.

      “Now we just need a way to shut him up,” Derek commented a bit unhappily. 

     It took Mel only a moment to figure that one out.  “Wait a minute!” she told Derek as she ran off.  The closest place to find what she was looking for was Sissy’s purse.  A moment later she was back again.  But she couldn’t do what she wanted.  She had to remove one of the chains from the wall first.  Then she reached around to the front of his head.  “Here, take this,” she said as she eased his pacifier between the wall and his mouth.  The pacifier quickly was pulled into his mouth and she pulled the chain back over the hook on the wall.  “Problem solved,” she told Derek.

     Derek was looking closely into the corner, trying to see the pacifier in his mouth.  Sissy’s face was pressed so tightly into the corner that the back of the pacifier was actually contacting the walls on each side of the corner.  “Can you even spit that thing out?” he asked Sissy.

     Chad tried to spit the pacifier out, but it didn’t move much at all.  He even tried pulling his head back a bit, but he couldn’t pull it back far enough to get the thing totally out of his mouth.  Since the strain from pulling back was hurting his ears, he quickly went back to pressing his head tightly into the corner again, which relieved the strain on his earlobes but also pressed his pacifier tightly back into his mouth again.  He tried to tell Derek that he couldn’t remove the thing, but what came out was nothing but a muffled bit of noise.

     Derek stood back happily.  “As you said, problem solved.  Now if you just tie his hands a bit, we can be sure he won’t be going anywhere.”

     Mel only raised her eyebrows for a moment before pulling a length of rope out of her desk drawer and handing it to Derek – who immediately pulled Sissy’s hands behind his back and tied them there.  “Not going anywhere!” he declared as he finished.  He looked at Mel.  “He also can’t turn his head and he can’t interrupt us with any problems.”  He moved in closer to Mel and grabbed her shoulders lightly.  Lowering his head toward hers, he planted a passionate kiss on her lips.  Then he pulled her over to the couch where he sat next to her and kissed her even deeper. 

      “Shall we adjourn to the bedroom?” Mel asked suggestively, sensing his true intent.  As much sex as she had been through in the last few days, she was a little surprised that she would be so easily willing.

      “No,” Derek replied.  “Let’s do it right here in the living room.”  He looked up at Sissy in his corner.  “He can’t get out of that corner.  He can’t turn his head at all so he can’t see us.  And he can’t say anything with that plug in his mouth.  All he can do is stand there and listen.  And I want him to hear us.”  He raised his voice just slightly to make sure Sissy would hear everything he had to say.  “I want him to hear exactly what he’s missing by living the life he thinks he wants!”  He turned back to Mel.  “Now… where were we?”  He pulled her to him and planted another big kiss on her lips – as he slowly and gently lowered her from the couch all the way down to the floor.

     Derek’s words echoed in Chad’s mind as the small sounds of their lovemaking carried to his ears.  “Hear what he’s missing by living the life he wants!”  Over and over he heard Derek’s words in his head as he listened to the tiny sounds emanating from both of them.  Was he really dooming himself to a life of no sex?  At least no normal sex as a male?  Possibly no sex at all?  He had no idea what the future would hold, but the more he thought about what had happened to him in the last two months, the more possible at least one of those scenarios sounded.  Did he want a life where he couldn’t ever enjoy normal male sex again? 

     And how about the new kind of sex that Mel had introduced him to – anal penetration.  He had actually managed to have a mind-blowing orgasm that way.  Did that make up in any way for no normal male sex at all?  As possible as it sounded, he really didn’t think that it would. 

     And then there was his other problem… his stupid fascination for being totally denied sex as a male because he was a sissy.  The very thought of it excited him sexually.  But to actually have that sexual expression denied him for the rest of his life?  He simply wasn’t sure.  Not at all!  And over and over in the back of his mind, one faint thought seemed to hover all too close – without ever being formally thought of or examined – did he now have even more reason to win this bet?  Despite his uncertainty, his resolve increased… even though Derek’s words brought a longing within him for that very same denial. 

     The words “forever… for the rest of his life” hammered the sexual need within him into a raging state – yet it was a state that he could do nothing but passively feel deep inside of him.  His miserable chastity device made sure that no outward expression of that need could ever be felt.  And since he could no longer even move, stuck on his perch in the corner, all he could do was to listen to the sounds of normal adult love making between a man and a woman… and feel the raging need and humiliation within him… and savor the feeling of being helpless to do anything about those feelings.

     Helpless.  Humiliated.  Hating it.  Loving it.

     The brief feeling of pee pouring out of him in a larger amount than usual felt almost like sex to him.  If it had lasted a lot longer then maybe he would have orgasmed from it.  Doubtful, but it was a fun thought and it was all he had.  He was suddenly wishing for his bottle so maybe he could feel that little bit of pleasure again sooner – as he listened all too closely to the true pleasure of real lovemaking… the way it’s supposed to be done.

     The floor was hard underneath her and Derek’s body was heavy as he laid on top of her... both of them totally spent.  In her mind, Mel was putting this weekend down as the most sex she had ever experienced in one weekend in her life!  Maybe in one week!  A month?  Maybe not.  But what a weekend it had been! 

     Derek rolled off of her with a grunt and she breathed easier with his weight gone.  He leaned over and kissed her again.  “That was great,” he commented. 

     Before Mel could agree, he rolled over and got to his feet.  She watched as he headed straight for the bathroom.  She rolled her eyes as she watched him go.  Typical male.  Doesn’t bother to hang around afterwards to just cuddle and enjoy it.  Wham – Bam – Thank you Ma’am!  But… it had still been great.  Not as inventive as the many things that Ray had done with her last night, but it had still been far more honest and real. 

     With a bit of effort, she sat up on the floor, then forced herself all the way to her feet.  She looked over at Sissy, still on his perch, still unmoving.  But then he really couldn’t move anymore.  Cautious because she didn’t want him to see her naked… and realizing at the same time that the way his head was now held he couldn’t see anything but the blank walls of the corner, she crept up behind him.  “Are you okay there Sissy?” she asked softly. 

     Once again, the only reply Chad was capable of making was a muffled grunt. 

     Mel took that for a yes even though she really had no idea how he had responded.  “I’ll let you down soon,” she replied.  Still naked, she picked up her discarded clothing from the floor and started dressing her top half.  The minute Derek came out of the bathroom she carried everything else into the bathroom with her. 

     Derek’s eyes continually found Sissy as he dressed again.  As far as he could see, Sissy was in exactly the same position he had been in since they had put him in that corner.  But then, that was really the purpose of the earring thing he had come up with.  He was kind of proud of himself for thinking of it.  Even though something in the back of his mind told him it was very wrong, another part of his mind kept telling him that if this was what Sissy wanted, then this was what he deserved!  And then some!  The idiot!

     By the time Mel came out of the bathroom – fully dressed, Derek was also completely dressed.  But Mel ignored Derek and headed straight for Sissy still on his perch.  She immediately unscrewed the earrings from his ears, leaving them to dangle from the hooks in the walls they were attached to.  A moment later she had his hands untied as well.  “Go get yourself another bottle right away,” she told him.  “If you don’t get more to drink, you’re never going to get that diaper leaking in time.  And we’ve kept you away from the liquids long enough.”

     Gratefully, Chad extracted himself from the corner.  He not only moved his foot and leg muscles, but he also massaged his earlobes as well.  The perch in the corner had been bad enough, but now with those darn earring chains fastened to him it was an even bigger nightmare.  He wasn’t looking forward to going through that again.  Knowing that he needed another bottle… or two, he quickly curtseyed and hurried toward the kitchen.

      “I guess I should be going,” Derek said as Sissy ran off.

      “Already?” Mel asked, surprised that he would want to leave so soon after they had made love.

      “I probably better,” Derek replied.  “I have some things to take care of before work tomorrow that really can’t wait.”

      “Okay,” Mel replied.  The two shared one more quick kiss before Derek departed.  Mel closed the door behind him.  Just like a man.  They get the one thing that’s always on their mind and then they take off.  Men!  She unconsciously grouped Derek a little closer to the group of men she had mentally stuck Ray into earlier.  Not quite that far, but closer.

     Sissy did little except continually drink bottles and continually try to get his diaper to leak.  And despite having been stuck up on his perch for so long earlier, he managed to get it to leak once again in an hour and twenty nine minutes – granting him an additional one minute of reward time.  He now had two whole minutes.  Not much.  But the expectation of the reward play time was now enough to keep him trying extra hard all evening. 

     And hour and a half later, he actually managed to add another two minutes to that reward time and he was not only starting to look forward to it, he was feeling proud that he had managed it.  Four minutes!  But he knew without a doubt that it wasn’t going to be much to enjoy.  He expected Mel to start getting him ready to end the evening, but surprisingly she set him on another hour and forty-five minute time limit, so he kept at it.  He continually drank from his bottles as he puttered around her house, cleaning this, picking up that, doing a lot of things over and over again that didn’t really need to be done.  He just wanted to keep busy while he drank.  The thought of possibly going back to his perch again scared him a bit.  And of course, there was now the possibility of the reward time. 

     While Mel worked from her laptop and later watched TV, he kept drinking and wetting.  Somehow he managed to gain another two minutes by the end of his next time period so that he now had six total minutes to enjoy himself.  And this time, when he announced he was leaking, Mel told him to protect her bed and then she would change him.  A short while later, she had tied him firmly to the head and foot of her bed, fully restraining him – even as he was looking forward to not only having his diaper changed, but to the reward he had been promised.

     But he didn’t get that reward right away.  Instead, Mel started removing his chastity device and once it was off of him, took it away to clean it.  While she was gone, all Chad could think about was the small chance he had to relieve some of his sexual tension.  He couldn’t wait to feel Mel’s toy being shoved in and out of his backside.  Would she take him from behind with her strap-on like she had done before?  That would be the best!  He knew six minutes wasn’t going to be enough to get him off, but he was still hoping that maybe it would help.

     Mel was back a few minutes later and the chastity device, complete with the small set of nasty teeth, was locked back onto him again – once again making sure that his male appendage was rendered totally useless.  And finally Mel began untying him – without replacing his soggy diaper that was just barely covering his front side up to catch the tiny accidents that continued to happen.

     Mel opened her nightstand drawer and pulled out several of the toys she had bought since their bet had started.  She set them all out on top of the nightstand.  She looked at her watch.  “Okay Sissy,” she said, still watching her watch.  “You’ve got six minutes to enjoy yourself anyway you can.”

     Enjoy himself?  She wasn’t going to do anything for him?

      “Ready…  Go!”  Mel looked up from her watch to see him still lying on his back looking back up at her.

     Caught by surprise, it took him a moment to fully realize what she expected him to do.  Panicked over the time, he quickly looked over the selection of dildos and decided on the one with the swirls.  There was a bottle of baby lotion on the nightstand ready to use on him before he put his fresh diapers on.  He grabbed the bottle and squeezed a large amount out onto his hand and liberally coated both the phallic toy and his asshole.  Then he had to figure out the best way to go about doing what he was supposed to do. 

     Since he was already on his back, he raised his legs up to his chest and put the tip of the toy against his bottom hole.  Then with growing pressure, he slowly pressed the thing most of the way in.  Yes, it felt fantastic, but left to do it on his own this time it was far less stimulating than it had ever been before.  He pulled it partially out again.  In and then out.  Over and over.  Two minutes later, he rolled over and got to his hands and knees.  The position seemed to be better for him, but working the dildo in and out with his own hand was still difficult.  It did feel good though.  Very good!  And there was the humiliating element of her being there watching him… no… his mind imagined that she was making him do this to himself.  Faster and faster.  Harder and harder.  He had no illusions about ever getting an orgasm from it, it simply felt incredibly good.  But that didn’t mean he didn’t try – very hard.

      “Time!” Mel declared suddenly.

     Totally frustrated, Chad froze in mid stroke.  It was a moment before he could reluctantly pull the thing out of him.  Six minutes simply wasn’t enough.  It was nice, but since he had to do it to himself with no other stimulation, then he knew that the next time he would need more time to do it… much more time.  He thought about that as Mel cleaned him up and diapered him thickly for the night.  Maybe tomorrow he could manage to get more reward time.  Tomorrow he would make it a point to drink more starting as soon as he got up.  This morning he didn’t have any bottles so he didn’t get enough liquid in his system to start with.  Tomorrow would be much better… and he knew that tomorrow night – would be better still!

     A few minutes later, Mel personally ushered him to the door.  “You might want to be a little early tomorrow,” she suggested.  “I have to go to work and it’s going to be a big day for me.”

     Chad curtseyed.  “Yes Mistress,” he replied before curtseying again.  He briefly wondered what he would be doing while she was at work.

     Mel opened the door for him as he grabbed his keys out of his purse and slung the purse over one shoulder.  His diaper bag was in one hand and the rest of his clothes were bundled up over his other arm with his shoes in that hand.  He curtseyed again.  “Goodnight, Mistress,” he said in his silly sissy voice before curtseying one more time. 

      “Goodnight Sissy,” she said to him.  “See you in the morning.”  She watched as he walked, wearing just the very bulky diapers, down to his own door.  She saw him open it, then glance back one more time at her before he disappeared.  “Good night Sissy,” she said one more time, more for her benefit than anything else.  “Sleep tight.”