The Bet - Chapter 62 (Thursday – week 9 Part 5 of 5)

The Bet

By Karen Singer

Chapter 62 (Thursday – week 9 Part 5 of 5)

     Boring!  That’s the best description Chad had for being once again stuck up on his perch in the corner.  Boring!  The afternoon had pretty much flown by and after carrying his male stuff up from her car and stacking the boxes back in his apartment, he had been allowed to shower and then change back into his maid’s uniform.  And then Mel had requested that he make one more nice meal for her.  So he had.  And now he was once again stuck up on his perch – perched like a bird – in his corner.  Out of the way while she ate. 

     But now his mind had more time to remember all the boxes he had carried back into his apartment.  As empty as his apartment still was, it was now much fuller than before – only because of the boxes that he had carried up but hadn’t been allowed to open yet.  What was in them?  He tried to remember.  His mind played with remembering all his male pants, and shirts, and shoes, and socks, and underwear of course.  Were they all still wrapped up in Mel’s plastic wrap as they had been before they were removed from his closet?  And what about his old male wallet, which box was that in?

     He was looking forward to exploring all those boxes that now occupied a bit more of the empty floor space in his apartment.  It would be like Christmas! 

     His attention was suddenly grabbed by the sound of Mel walking out of the kitchen, coming up behind him.  His attention remained riveted on her as she came up close.

      “Dinner was good again,” she said. 

     Chad immediately felt a touch of pride.  It was only lately that she had been passing him these little complements.

      “But I barely tasted it,” she finished.

     Chad’s joy suddenly turned to worry.  What had he done wrong?

      “Not because you did anything wrong,” she said, “but because I was too preoccupied with thinking.”

     Chad immediately wondered what she could have been thinking about.  And obviously the dinner he had prepared wasn’t good enough to hold her attention.

      “Thinking about you!” she finished. 

     Me?  Chad’s interest focused even harder. 

     Mel paced back and forth behind him for a few moments.  “Okay!” she finally said rather emphatically.  “I admit it!  I’m worried about you possibly winning.  Okay?  As much as I still think I’m going to win… or maybe hope I’m going to win… I’m still worried about what’s going to happen if I lose… and you win instead.”  Her voice quieted a bit.  “I can’t stop thinking about it… and worrying about it.”

     Worrying?  Chad turned his head to ask…

      “Don’t you move!” she lashed.  “Get that face buried back in that corner!”

     Chad immediately stuck his face back into the corner – harder than before!  Obviously, this was one of those times when she didn’t want an answer.

     It was a while before Mel found her voice again, and the time in-between held only a deathly, desperate silence.  “Let’s face it,” she finally said, “I’m going to miss you – if you win!  I’m going to miss all the crazy, stupid, oddball, idiotic, and downright weird things about you.  Not to mention your cooking and cleaning.  And… I’m afraid I’m going to miss pushing you around… forcing you to do the most stupid and outrageous things I can think of… all for my own amusement.  Who would ever think that I would come to love doing something like that?  Strange… I guess.”

     Silently, and unmoving, Chad listened to her every word carefully.  She was going to miss him?  She was going to miss dominating him?  But the overall theme that he was hearing was that she seemed to be admitting that there was a really good chance she would lose.  And that alone should have made him feel good.  But there was something about the way she was saying it that made him feel sad instead… for her… or for him?

     Mel went from pacing to wandering around the room as her thoughts roamed over all the little things that were taxing her brain.  Again, it was a while before any words tumbled out of her mouth.  “I don’t know why,” she finally said.  “I have no idea how it ever happened.  But somehow I started linking you to all my dreams for the future.  And I know… that’s crazy!  It’s stupid!  And there’s no real reason for it.  But… somehow, I did.”

     Chad had no idea what she was talking about.

      “Somehow, I started picturing you as my personal little servant.  And somehow, that image was enough to push me toward finally moving on with my life.  And yet, for some dumb reason I can’t explain, without you as that servant, I want nothing more than to stay right here – stay right here in the same old rut I’ve been in for years now.”

     Mel realized she had said too much.  And what she was saying to him probably made no sense at all.  But she simply felt the need to talk about it with someone… or in this case, to someone… and Gloria wasn’t around.  So maybe, she was just trying to make sense of it all to herself.  She paused in her thinking.  As long as she was spilling her guts where he could hear…

      “I want you to answer something for me.  Don’t turn your head when you speak, just keep it buried in that corner!  I don’t want to see your face, I just want to hear your words… and… I need an honest answer… please.” 

     She paused again to collect her thoughts.  “You’re not anything like I would expect someone like you would be.  For one thing… you’re not gay.  At least, I don’t think you are.  I guess we never really explored that, did we.  But you’re also kind… and sweet… and caring – more so than I ever would have imagined.  And… you’re smart!  That alone has me stumped.  How can someone who wants the things you seem to want, be so damn smart?  Don’t answer that!” she added quickly.  “That’s not my question.”

     Chad hadn’t even thought about answering that one.  He hadn’t even realized it was a question until she had told him not to answer.  But what was the purpose of all the complimentary things she was saying about him now?

      “It doesn’t add up,” she finally said a bit more quietly.  “It doesn’t add up.”  She took a big breath to calm herself.  “So what I guess I’m really asking now is…”  And how was she going to put this into words?  “I guess…  I guess I need to know if…  Damn it!  Tell me, is it right?  Is it morally right for me to turn you into a silly, stupid, simpering servant… hold you totally under my thumb that way for a very long time…  make you do the most stupid, outrageous things imaginable…  Is it right for me to do that to you?  Is it morally right?”

     She stared at his back, waiting for an answer.  But he remained silent.  She walked up behind him and put her hand lightly on his shoulder.  “Can you answer that honestly?  Can you tell me how you feel about it?  Is it right?  Is it morally right for me to do that to you if you lose?”

     Chad started to turn his head toward her, but he remembered she didn’t want him to do that so he snapped it right back into place in the corner and closed his eyes.  How was he going to answer that?  Morally right?  That was a tough question.  But he had a feeling, she wasn’t asking the right question.  “I think…” he finally said, “that ‘morally’ doesn’t fit.  It doesn’t apply.  You want to know if you should do it.  You want to know if you should be that dominant… and expect me to be that submissive as well.  And I guess, the answer is…”  And he paused as he tried to consider the best way to reply.

     Mel’s hand, still resting on his shoulder tightened, as if she was afraid to hear what he would have to say.

     It was Chad’s turn to take a deep breath before continuing.  “I’m submissive.  Very submissive I guess.  I’ve spent every day of my life trying to hide what I really am inside.  I’ve spent my whole life trying to act like everybody else… like everyone expects me to act.  And when you do it your whole life, I guess you get pretty good at it.  But the truth is, I guess I’m not like everybody else.  I have these… yearnings… these dreams… of something else.  Things that everyone else thinks are morally wrong.  But to me… to me…”  It was hard to admit.  “To me, these things are not wrong.  These are the things I dream about.  These are the things I yearn for.  These are the things… I want.  For these last two months, I’ve been doing what very few people get to do.  I’ve been living my dream.  You want to know if it’s morally wrong?  For everyone else it would be – without a doubt.  But we’re talking about me… you and me… and to me, it’s what I dream about.”

     Mel listened carefully to his words.  It took a few moments longer for all of it to sink into her… for her to make sure she fully understood.  Or at least, think she understood.  “She squeezed his shoulder one more time.  “So I don’t have to worry about being… cruel to you?”

     He started to turn his head in surprise, but he quickly turned it back again.  “Cruel?  I guess there are different definitions of that.  But basically, I’d say no, you don’t have to worry about that.  I… I guess I like all that part too.  It’s like… it’s all part of the package.  I guess… it all kind of goes with the territory.”

     He couldn’t see it, but she nodded.  She understood.  She thought.  “Thanks,” she said quietly.  She felt a bit more relieved – at least over everything she had put him through for the last two months.  But now… how about the future?  “So… if I win… and you lose… you won’t mind so much doing anything I order you to do?  Continuing on with this way of life… or worse?”

     He started to shake his head before stopping himself again.  “No, of course not.  It’s all part of the dream.”

     His dream.  But she remembered that he had other dreams as well that she knew about – and he didn’t know she knew.  He had dreams of being a normal person as well.  He had dreams of… self-respect.  Dreams of having friends.  And dreams of having a regular life!  And she didn’t know how to solve any of those mysteries for him to make him want to stay with her – no matter what. 

     And that left her facing her one biggest fear.  It was still very possible that she could lose this bet.  And consequently – lose him.  And right now, she didn’t want to think about that anymore.  “Get down off of that thing now,” she said quietly.  “I’ll get you your dinner.”

     It was the most intense evening either of them could imagine.  Not for what they did.  Not for what they said.  But for what they didn’t say… or do.  Chad ate his dinner and cleaned the kitchen, while Mel made sure he kept drinking from his bottles.  Chad did what laundry he could and straightened the house, while Mel made sure he kept drinking from his bottles.  All evening long, the only thing Mel seemed to be concerned with was keeping Chad drinking and getting his diapers to leak as soon as possible.  And every time they did start to leak, she gleefully added a few more minutes to the reward time total that he really cared nothing about anymore. 

     And all evening long, while there wasn’t something Chad could ever put his finger on, the tension in the air seemed to be so thick he could cut it with a knife!  And this time, the night went on… and on… and on.  Much longer than they usually went in the evenings.  Sixteen minutes of reward time became eighteen… then twenty… then twenty three.  An eternity of bliss.  An eternity that, for the first time, he still couldn’t care less about. 

     It was shortly after eleven when his reward time hit the twenty three minute mark.  And it was only then that Mel stared at him for what seemed like forever – right after he had announced that he was leaking again.  She glanced at the clock before looking back at him with a small smile on her face and announcing the additional three minutes.  Chad saw something in her face change again then, as if a massive weight of inevitability had just descended on her. 

      “It’s time,” she said quietly… and resignedly.  She nodded toward the bedroom.  “Go protect the bed.”

     Chad was slow to curtsey as he watched her face.  But he turned to carry out her wishes.  A short while later, he was removing his maid’s dress – for the last time, as Mel watched carefully.  Finally naked except for his chastity device and his bra covering his glued-on breast forms, he climbed up on the bed, expecting her to tie him up.  But she didn’t.  Instead, she opened her drawer and pulled out her colorful collection of dildos and placed them all out on her nightstand where he could reach them.  “You’ve got twenty three minutes,” she told him quietly.  “I know you’ll enjoy that.”

     Chad still didn’t care that much about the reward time he had.  But now something puzzled him… because it didn’t seem right.  “Mistress,” he started questioningly.  “How about you?  This is the last night, you don’t want me to pleasure you first?”

     A small smile crept to Mel’s lips.  Even now he was still thinking about her before he thought about himself.  “Not tonight Sissy.”  She shook her head.  “As wonderful as it sounds, I’m just… not in the mood.”

     Chad understood, or at least he thought he did.  It was the way she had been acting all day.  It was what the underlying tension had been about all evening as well.  Because in just a little while, it would all be over.

      “I don’t need this tonight either,” he replied. 

     Mel grunted a small laugh.  “But I want you to do it.  I want to remember seeing you do this one more outrageous thing.  And I want to remember seeing you doing it to yourself.”

     Chad stared back at her for a few more moments before accepting what she wanted.  One more tiny piece of humiliation.  He nodded.  “Has my time started yet?” he asked, knowing that it probably had.

      “Not until I say it’s started,” Mel replied.

     She was going to stretch this out.  He could see that now.  For a little while only, he still didn’t have much choice.  Fortunately, this was something that was very pleasurable for him… now.  This was something his body now craved.  He looked over the choice of “weapons” she had left him and selected one.  He lubed it up carefully and then took a moment to stick more lube inside his asshole.  Laying on his back, he pulled his legs up toward his chest and carefully lined up the dildo with his hole, and slowly pushed. 

      “Time starts now!” Mel suddenly said.

     Chad heard, but his focus was far more on the wonderful feelings of the intruder now slowly entering his sensitive rear end.  In… and out.  In… and out.  Wonderful feelings.  Fantastic feelings.  In… and out.  Faster and faster.  Harder and harder.  He was totally unaware of the building wetness that now covered his stomach from his almost continuously leaking penis… wetness that soon started dripping down his side onto the diapers protecting her bed.  In… and out.  He was soon lost in the ecstasy of the feelings as he worked and worked to bring his body to that place he knew he’d never be able to reach – without Mel helping him.

     Her eyes never left him.  He looked so… ridiculous.  Here was a man… sort of.  But not a man anymore.  She had made him… something else.  Something… less.  He no longer thought about his silly little man thing, his penis, as a sexual tool.  Instead, he was totally hooked on being fucked instead… even if it was in a place that was never meant for that kind of activity.  It was still the closest thing he could get to female style sex.  No longer allowed to be a man.  More female than male now.  And he was going crazy trying to achieve an orgasm from it.  Would he do it?  Would he make it on his own?  He had done it before, but only with her help – only with her whispering derogatory twisted thoughts into his brain while he was being fucked.  And since she was only being a bystander tonight, she was betting he wouldn’t make it.  But he still had a long time to keep trying.

     Chad once again got to that high level of desperation, and once again he knew he wasn’t going to get any further.  He kept at it though because it felt so good.  But eventually, the frustration simply got too much for him and he slowed down… almost to a stop.

      “Keep going!” Mel commanded.  “You’ve still got ten more minutes!”

     Chad shook his head, “It’s not…”
      “I said keep going!”

     She wasn’t allowing him to quit tonight – despite the fact that he couldn’t get there.  He took a moment to pull the tool out of him and select a new one.  Then he changed position so that he was on his hands and knees before he stuck the new one up inside of him.  If felt different, but as before, he knew that he wouldn’t be able to achieve the orgasm he now craved.  Not without Mel’s help.

     Slowly and almost methodically, Chad shoved and pulled on the toy up inside of him.  He enjoyed it greatly, but after a while, it all just became one muted feeling.  But Mel didn’t let him stop until he had used all of his twenty three minutes.  And by then, he was grateful to be able to pull the thing out of his ass and leave it out!

     He was a mess.  His entire chest was wet with pee.  His legs and arms were splattered with it.  And he could tell that the diapers under him were wet as well.  But he had been there for over twenty minutes, leaking fairly constantly, what else could he expect?  He was grateful though when Mel told him to lay on his back and she would clean him up. 

     Mel pulled a diaper through his legs then up and over him before she went to the bathroom to get a washcloth and towel to clean him with.  He was still peeing helplessly and somewhat profusely.  Almost lovingly, she washed most of his body – the splattered pee had gotten that far!  After drying him off, she pulled out the jar of suppositories again and opened it where he could see it.

     Chad rolled his eyes in frustration.  “Must you?” he asked.  “Why now?”

     Mel smiled wickedly.  “It’s not midnight yet.  You still belong to me.”  She had him pull his legs up, and once again she faked sticking one of the nasty little pills up inside of him.  When she was done, she pulled the diaper over him again and put the jar of suppositories away. 

     But before taping the diaper securely onto him, she grabbed one of her keys.  Piece by piece, she removed the chastity device from his tiny male appendage.  Her hands got sprayed with pee as she did it, but that was only to be expected… and in a way… hoped for. 

     One by one, Chad felt the pieces of the chastity device being removed.  This was the first time she had done it without tying him up.  And he realized, this would be the first time she would be diapering him again – without putting the device back on him.  Piece by piece, until he felt her pulling the main piece off of him, and he felt the cool air touching that part of him that never got touched.  He felt her grabbing him with her fingers and manipulating his penis a bit, bending it up and back, and around.  Her fingers felt strange there.  But feeling anything touching him there now would feel strange.  He also felt more wetness dripping off of him.  Wetness that she quickly wiped up, before she finally pulled the diaper more firmly over him… and taped it in place. 

     Grabbing her scissors, she cut slits all over the cover of that disposable diaper.  Then she did the same with several more before she put them on him – adding layer after layer of protection.  Only the last diaper was left whole.  Four layers of diapers.  He would need all that to get through the night without leaking – she hoped.

     But once the diapers were in place, she still had one more thing to do.  She removed his bra, then started to carefully remove the glued-on breast forms from his chest.  As usual, it took a while, but eventually, they were gone and she washed his chest where they had been as well. 

     She was done.  She looked at the clock.  It was nearly midnight.  “I guess that’s it Sissy,” she said.  “We’ve reached the end.”

     He nodded.  “Except for the testing.”

     It was her turn to nod.  And the total frustration and emotion of it suddenly washed over her.  “Why can’t you just lose?” she asked before she realized she was going to say it. 

     Chad was dumbfounded.  “I…”

      “If you would just lose, then we could get on with everything!”

      “But…”

     Mel waved her hand.  “Never mind.  I shouldn’t have said that.”

      “But…”

     Mel shook her head.  “I’m sorry!  Don’t answer that!”  She looked at the clock again.  “It’s over.  We’re done… with this part anyway.”

     He nodded and chanced answering.  “Except for the testing,” he repeated.

     She nodded.  “I guess we’ll soon see,” she replied.

     He nodded.  “Tomorrow.”

      “Or the next day,” Mel added a bit more hopefully.

      “Or the next day,” Chad repeated.

     She looked at him.  “Good night… Chad,” she said.

     Chad swung his legs off of the bed and got to his feet.  His penis felt strange inside of the thick layers of diapers he was wearing.  It felt strange again without the breast forms glued to his chest.  He picked up his clothes that were in a pile on the floor and walked toward the door to her bedroom.  He turned back to her.  “Good night,” he said in his old male voice… “Mel.”

     The two stared at each other for a few moments longer before he turned and walked off toward her apartment door.  He grabbed his purse and his diaper bag and opened the door.  For the last time, wearing only layers of diapers and nothing else, he walked the short distance to his apartment, where he fished his keys out of his purse and went inside.

     Mel sat on her bed staring at the empty doorway he had walked thorough only moments before.  She had listened as he left her apartment.  Was he gone… forever?  She didn’t even count the testing – because he wasn’t going to be – Sissy – then.  Was he gone… forever?

     She forced herself to undress and throw a light nightgown over her body before throwing all the protecting diapers off the bed into a pile on the floor.  She got into bed and turned out the light.  But sleep was a long time coming.  She was too concerned with the future.  Was he gone… forever?

      “I would kiss you till your body shudders… and you know how I feel about you.”

     Why can’t he just lose?

     Chad set his purse and diaper bag down on the floor of his apartment and closed the door.  He looked around.  All the new boxes.  All the things they held.  All of his old male life.  He was tempted to open one or two, but he didn’t.  He wasn’t really in the mood.  He headed to the kitchen instead where he automatically opened up his refrigerator.  His hand was reaching into it to grab one of the baby bottles of her tea when he stopped himself.  He no longer needed to drink any of the bottles before he went to bed.  It was all over now.  All over.  And he felt nothing but a crushing case of loss.

      “Why can’t you just lose?”  The words seemed to echo in his head.  And what was it that Andrea had suggested… that he purposely lose? 

     For a change, he grabbed the top to one of his babydoll nightgowns and threw that on.  He grabbed the pacifier he used every night and stuck it in his mouth – he knew he’d never manage to sleep without it. 

      “Why can’t you just lose?”

     He turned out the light and got down into his bed – his little bed with its little girl sheets on top of nothing more than a blow-up mattress. 

      “Why can’t you just lose?”  And Andrea suggesting that he should lose. 

     He stared at the dark ceiling for a very long time.  He tried closing his eyes, but sleep was hard to grasp.  He stared at the dark ceiling again.

      “Why can’t you just lose?”

     It was over.  The dream was over.  And sleep was a long time coming.