The Bet - Chapter 60 (Tuesday – week 9 Part 6 of 6)

The Bet

By Karen Singer

Chapter 60 (Tuesday – week 9 Part 6 of 6)

      “You wanted to talk to me about something?” Mel asked.

Derek suddenly looked decidedly uncomfortable.  “Yeah.  I had lunch with Ray yesterday.  Actually, it was more of a liquid lunch, if you know what I mean.”

      “One of those!” Mel assured him. 

      “Yeah, well, it was more liquid for Ray than for me.  Earlier in the day, he had said some really dumb things to me and basically acted like an asshole.  I’m afraid it pissed me off quite a bit.  So for lunch, I went to the bar for a beer and a sandwich and he was in there ahead of me… already pretty far gone.”

      “So you two talked in the bar.”

     Derek nodded.  “Sort of.  Mostly, I talked.”

      “So?”

      “So… well…  In the course of things, he finally asked me about Sissy.  And… I’m not sure, because I don’t think you really ever mentioned how much you wanted to keep quiet about your bet, but I’m afraid I may have told him pretty much everything.”

      “Everything?”

     Derek nodded again.  “Everything!”

      “Including what this is all about in the first place, the incontinence thing for him?”

      “Afraid so,” Derek confirmed.

     Mel thought about that for a minute.  “So?  I don’t see where it can cause any harm at all.  It’s pretty much amazing that everyone doesn’t know the whole story already.  It’s really been only Sissy that has been trying to hide that part.  Did you tell him about what Robin’s been doing with him?”

      “That was the one thing I absolutely steered away from.  But he’s pretty smart.  He can probably piece things together – if he remembers any of it.  Like I said, he was already pretty far gone when I got there, and he was far worse by the time I told him that stuff.”

     Mel considered it.  “The only thing I might be concerned about is for Robin.  But as for Sissy, I just don’t see how Ray knowing it all can make any difference to anything.”

      “I just thought… when this thing is over and he goes back to work… the others… if they all know, might make life too difficult for him.”

     Mel shook her head.  “I don’t think it would be much more difficult than things have been for him already since we started this.” 

     Derek shook his head.  “I don’t know.  Right now everyone there is convinced that he wants to have a sex change.  They’re tolerating it pretty remarkably so far… if you ask me.  But something like his incontinence thing as you called it, that’s starting to get really out there.  Most people would find it totally disgusting.  His life at work is bound to be hell!”

      “Possibly,” Mel admitted.  “But it still doesn’t make any difference.  He’s going to be bound by my wishes so it won’t matter what the others think.”

      “If you win,” Derek added.

     She looked him straight in the eye.  “Am I detecting a sign that you somehow think he’s going to win this bet and not me?”

      “No!  Of course not!” Derek replied quickly.  “But… you have to admit, I think the chances are pretty good that it could go either way.  Besides, afterwards, no matter what, he does still have to go back to work.”  He saw Mel’s face suddenly look troubled.  “What?” he asked.

      “Nothing,” she replied. 

     They continued eating in silence.  Mel didn’t watch Derek very much as he ate because she couldn’t believe how much of his sandwich he was able to stuff in his mouth with each bite.  It was positively disturbing… yet very manly as well.  And she was way too tired tonight for any further stimulating activity.

      “I’m leaking!” Sissy’s voice called from his solitary corner.

     Mel glanced up from her meal and immediately checked the clock.  Two minutes early again.  Excellent!  “Get yourself out of that corner and go change,” she called back.  “And your next time limit has just started!”

      “When we’ve finished here,” Derek mumbled through a mouthful of sub sandwich, “and he’s done changing, any chance we can put him back in his corner again for a while?”

      “Why?” Mel asked.  “He’s got to clean the kitchen and I still have to get him his dinner.”

      “I just thought that you and I could… you know… snuggle a bit again for a while.”

     Mel shook her head.  “Not tonight.  I’m too tired.  I told you that earlier.”

      “You can’t blame a guy for trying,” Derek replied with a grin.  He finished stuffing the last of his sandwich into his mouth.  “I guess that’s my cue to leave then,” he said as he wadded up the paper. 

      “Leave?  Already?  And don’t bother cleaning anything up.  That’s Sissy’s job.”

     Derek left the wrapper he had balled up on the table.  “You said you were too tired.  And after working all last night like you did, I believe it.” 

      “If you stick around for a little while, I’m planning on letting Sissy have some fun playing with a dildo up his ass for a while.  I’m sure you’ll find it amusing and I know he’d just love to have you there to watch him and cheer him on.”

     The large sandwich Derek had just finished momentarily threatened to make him sick.  Or was that the image of what Mel had just suggested?  “I think I’ll pass!” he replied as he got up from the table. 

     Mel walked him to the door where he planted a small kiss on her cheek to say goodnight.  “How can you stand doing some of the things you do with him?” Derek asked.

     Mel smiled.  “How can I stand it?  To tell the truth, turns out… I love it!”

     Derek shook his head and walked out.  Mel headed to the kitchen where she started pulling baby food out of the cabinet for Sissy’s dinner.

     One big baby highchair, one big bib, one plate full of colorful baby mush, one tiny rubber-coated baby spoon, one baby bottle of semi-lousy tasting green tea, and one big baby.  Roll all of it together into one picture and that was Chad as he sat locked into his highchair eating his dinner.  Baby food!  The only food he would get.  The only food he was supposed to be able to eat for the entire week!  But of course, he had gotten lucky last night with the pizza and again earlier this morning when Andrea had brought him breakfast at Mel’s office.  He was certainly grateful.  But… being reduced to eating nothing but baby food had its own appeal as well.  At least for him it did.  As he shoved another miniscule amount of green goo into his mouth with the tiny little spoon held in his left fist, he thought about how strange that sounded.  Only a sissy like him could take pleasure in being forced to eat nothing but lousy tasting baby food all the time.  Only a sissy!

     He had gained another two minutes to his reward time for later this evening.  By his estimate that was a total of six minutes now for today alone.  And that didn’t even count what he had racked up yesterday – if she let him have that time as well.  And there was still a chance that he could gain even more time tonight!  No, not just a chance, he “would” gain more before the evening was over with!  But would he be able to have an orgasm from it?  He was hopeful, very hopeful!  But he had no real illusions about it.  Most likely it would only be a very pleasant exercise in futility for him.  But any “pleasant” exercise would be reward enough.

     Mel was sitting staring blankly at her TV set when she heard Sissy calling her to tell her he was done eating.  She realized she had been watching it, but she was so tired she had totally zoned out and didn’t have a clue as to what had happened in the program.  She forced herself to her feet and went back to the kitchen to release him.  “Get the kitchen cleaned up,” she told him as soon as he was released.  “Then do you have anything else to keep you busy tonight?”

     Chad had a feeling that if he didn’t have anything to stay busy with he would be sent back to his perch in the corner.  He curtseyed.  “Yes, Mistress.  It wouldn’t hurt to get some of the laundry done again.  And…”  He paused.

      “And what?”

      “It wouldn’t hurt to make some more tea as well.”  Curtsey.

     Mel smiled.  “Get to it.  Just stay busy.  And don’t forget your deadline!  That’s more important than anything else!”

     Curtsey.  “Yes Mistress.”  Curtsey.

     Chad kept busy while Mel went back to watching TV again.  At one point when he walked from the kitchen to the little laundry area, he thought he heard soft snoring coming from Mel even though she was sitting up and appeared to be watching the TV.  He did his best to stay out of her way.  He also did his best to keep drinking from his bottles so he could gain a little more reward time.  He figured that every minute would count!

     As he worked between the laundry and making more of the green tea he wasn’t exactly fond of, he was constantly aware of how wet his diaper kept getting – even though he couldn’t always feel himself peeing.  Eventually, he figured that it would have to start leaking soon.  He glanced at the clock, the deadline for getting any reward time was running out.  Leak!  Leak!  He drank furiously from his bottle again as he continued to watch the clock.  Leak!  Leak!  He kept feeling around the leg openings of his diaper for the faintest sign of a leak, but nothing!  Leak!  Leak!  And finally, with a disheartening tick, the clock went past his reward deadline.  Some diapers!

     Angrily, he kept sucking on his bottle.  He now had fifteen minutes to get his darn stubborn diaper leaking so he wouldn’t get punished – something he really didn’t want.  He just hoped this diaper wouldn’t be too stubborn!  Leak!  Leak!

      “Mistress, I’m leaking!”

     Mel snapped out of her semi-sleep, realizing that she had dozed a bit in her chair.  She didn’t know why she bothered to have the TV on.  She wasn’t watching it anyway.  It was a moment before she had the mental capability to check the clock.  Darn!  Sissy was very close to getting punished instead of rewarded.  He had less than five minutes left, but at least he had made it.  She pried herself out of the chair and headed to the kitchen where he was.  “That was starting to get close,” she said.  “I thought you were drinking plenty of bottles!”

     Curtsey.  “I did!” Chad confirmed.  “It’s just that some diapers are harder to get leaking than others.  He curtseyed again… and immediately grabbed for his leg as he felt a string of pee rushing down from the leg opening.  He quickly grabbed a paper towel to wipe it with.

     Mel almost laughed.  The stupid diaper had probably been overflowing, but the way it had been bunched up, the pee must have simply collected in the bottom – until now.  “At least you won’t get punished,” she replied with a straight face.  “Go get changed.  I started your next time period the minute you called me.”

     Chad curtseyed – a little bit before hurrying off to change his very leaky diaper.  Hopefully, the next one wouldn’t be so bad.  Half an hour later, he was working on his second bottle since changing and Mel was once again snoring softly in her chair. 

     Pee! Pee!  Leak!  Leak!  He was trying as desperately as he could for any reward time he could possibly get.  As the time marched forward, he noticed Mel stirring once in a while.  She got up and got her own coffee several times, but once she got settled in her chair again in front of the TV, she seemed to settle down and drift off to sleep before long… only to startle awake a short while later.  Chad just kept drinking his bottles and trying to get his diaper leaking. 

     As his next reward deadline approached, he was once again trying to do everything he could to make his diaper leak.  He was about to give up on it again when he felt a tiny bit of something again starting to run down his leg.  “I’m leaking!” he called triumphantly the moment he noticed it.

     Mel snapped awake again and glanced up at the clock.  One minute she realized.  He had leaked early again, but only by one minute.  Still, it was a good sign.  Yawning, she forced herself to her feet and stood there, staring back in the direction of the kitchen.  “I give up!” she said tiredly, more to herself than for Sissy’s sake.  “Sissy!” she called.  “Go protect the bed!  Let’s get this over with.”  She saw Sissy hurrying toward the bathroom to get a stack of diapers to use on the bed.  She followed slowly after him. 

     Chad started spreading out the diapers all over one side of the top of her bed – several layers deep!  Finally he was going to be able to make use of his reward time – and he was ready for it.  He had been looking forward to it for two days now!  He glanced back at Mel before removing his diaper. 

      “Hurry up!” Mel told him tiredly.  Get undressed and get up there.  I want to get this over with so I can go to bed!”

     Chad had his maid’s uniform off quickly.  He removed everything except his bra that helped to support his glued-on breast forms.  As he was doing that, Mel opened her drawer and laid out her collection of colorful didoes that she had bought a month ago along with some lube.  Before Chad was even fully ready, she glanced at the clock.  She really wanted to get this over with and out of the way so she could go to sleep!  “Since you’ve been so good, I’m going to allow you some time for yesterday as well.  As of one minute ago you had fifteen minutes.  That’s down to fourteen now.  Better get started!”  She stood back out of the way to watch.

     Chad was still removing his diaper as she said it.  He let it fall all the way to the floor and jumped up on her bed as fast as he could.  He reached over to her nightstand and grabbed the first toy he could grab – the one he had used last time – the one he knew best.  Grabbing the bottle of lubricant, he quickly smeared some over the length of the whole thing, then grabbed another dollop for his backside and smeared that right into his asshole, which forced a bit of pee to eject from his chastity device on the other side of him. 

     Still on his knees, he put the toy right up against his hole, and slowly started pressing it in.  Slowly, gradually, he savored the feel as it slid easily inside of him.  He enjoyed all the little moving sensations as the swirled shape of it reamed around his back hole.  All the way in, then a little faster, he pulled it most of the way out before shoving it back in again.  In… and out.  In… and out.  Gradually working it faster and faster.  But the position was difficult for him since he had to work by himself.  With the toy still up inside of him, he rolled over on his back, pulled his knees up to his chest which made his backside stick up straight in the air, and he went back to work.

     Mel almost laughed out loud at Sissy’s antics as he desperately worked the dildo in and out of his backside.  It was one thing to do this to him, but it was a whole different world of fun to watch when he had to do it to himself.  And Derek didn’t understand how she could possibly enjoy all this?  He should have stuck around to see it.  Sissy was being downright hilarious! 

     She could see his chastity device still locked over his tiny penis.  As far as she could tell, he was totally ignoring that part of him as he penetrated himself over and over again – trying to get the closest thing to an orgasm he was capable of.  And it looked like he wanted it pretty desperately as he shoved and pulled… shoved and pulled!  He was getting his whole body into it now, sliding around trying to get as much stimulation as possible.  It was obvious he was enjoying himself greatly, but it was just as obvious that once he had reached a certain point, no matter what he did, he couldn’t seem to gain any more pleasure.  Before long, she started to notice wetness on his stomach and legs as his chastity device continued to leek onto anything that happened to be in the way.  She was fairly certain that Sissy wasn’t even aware of it.  Or if he was, it certainly wasn’t bothering him in the least.

     With five minutes left, she watched as Sissy changed dildos and positions.  But as before, he still couldn’t get what he seemed to want so desperately.  She thought she knew what he was missing, but she wasn’t about to give it to him.  Not tonight at least.  Besides, she was having too much fun watching him get more and more frustrated as he tried and tried to get himself off through penetrating himself.  All to no avail.  In fact, she enjoyed watching him so much that she gave him an extra two minutes.  But finally she called, “Time!” Sissy was still moving the toy in and out of himself – but slower now.  She walked up to him and had to forcibly yank the thing out of him to get him to stop.  When she did, his body shuddered, and he collapsed in exhaustion on the bed… and another tiny spurt of pee leaked out of his chastity device. 

      “I hope you enjoyed that,” Mel told him, “because I sure did.”  She got no answer from him.  He was laying there practically panting from the exertion.  His stomach was wet from pee as well as parts of his legs.  She had no doubt that the diapers under him were fairly wet as well.  He must have peed an awful lot during his exercise… which was exactly what she wanted to happen! 

     She grabbed some baby wipes and cleaned him up.  Then she pinned him into three of the thickest cloth diapers she had before struggling to get his plastic panties over the bulk.  She finally stood back.  “Okay Sissy.  Clean this up quickly now and go home.  I need to go to bed!”

     Chad rolled off her bed and landed on his feet.  The extreme bulk of his diapers quickly made its presence known, but that was something he was very well used to.  It took him only a few minutes to get everything cleaned up enough for the night.  Then he went out and grabbed his purse and his diaper bag. 

     With his maid’s uniform draped over his arm and wearing only his super thick diapers, his bra, and his shoes, he curtseyed.  “Goodnight Mistress,” he said before curtseying one more time.

      “Goodnight Sissy,” she replied tiredly.  “Sleep tight.”

     She watched as he walked out and the door closed behind him.  But would that door be soon closing behind him forever?  She fervently prayed that wouldn’t be the case.  She had to win this bet!  As much as it might be very wrong, she didn’t want to see him walking out on her forever. 

     She almost laid down on her bed still in her clothes, but she made herself put a light nightgown on first.  She went around her apartment turning off all the lights.  The light on her nightstand went out last.

     Bed!  At last!  She breathed a big sigh of relief at being able to finally lay down and get a good night’s sleep.  Her mind drifted back to Sissy again.  She only had tomorrow and Thursday with him, then he would be free to gain back his control again – or try to.  She really hoped he wouldn’t make it.  She really hoped!  As her mind succumbed to the slumber she so desperately needed, she once again played back the images of Sissy trying so hard to have an orgasm.  So much fun.  So much fun.

      “Good night Sissy,” her mind spoke silently one more time.  “Sleep tight.”

     Ray nearly screamed as Gloria got off of him once again – just before he could have an orgasm.  She had been doing this to him all night long, going from one thing to the next, totally insatiable, totally in command, while he was to the point now where all he could do was to try to keep up with her.  But while she had enjoyed several climaxes already, she had purposely kept him from having even one.  The result was that he was going crazy… and now she was moving him into yet another strange position that he had never heard of. 

     Desperate for relief, he could only do as she suggested and assume whatever demented position she had dreamed up this time.  Now she was behind him, firmly hugging him.  He felt her pulling his aching penis painfully back between his legs, only to feel the head of it sliding once again into her moist slippery cunt... behind him.  And now she was moving in and out, trying to keep it inside of her.  She couldn’t move far, but it was more than enough to start sending him toward the edge again.  Would he finally get there?  It felt so good!  The pressure from the different direction felt… amazing!  He was breathing heavily!  He was about to scream… when she pulled totally off of him one more time. 

     He nearly did scream!  How long had they been at it tonight?  He had no idea.  The tiger was definitely on the prowl… and she seemed to be out for blood!