The Bet - Chapter 59 (Monday – week 9 Part 1 of 5)

The Bet

By Karen Singer

Chapter 59 (Monday – week 9 Part 1 of 5)

     His sexual need was all he could think about.  Even in his dream he could feel the dildo sliding sensually in and out of his backside.  In and out.  In and out.  Delicious!  But he was still frustrated.  While the dream toy felt incredibly good, it didn’t give him the fulfillment he really needed.  He pulled the toy out and picked up another one – the one Cassie used on him.  In and out.  In and out.  It felt so different than the one from Mel that he had used just before.  But again, this toy wasn’t going to give him what he needed either. 

     His dream-self thought again about his regular male appendage.  But that was totally useless now.  Totally!  In his dream, he wasn’t even wearing the darn chastity device.  He could touch it if he wanted to… but he didn’t.  What would be the point?  It no longer functioned.  It no longer gave him the release he wanted. 

     He was a sissy, and as such, normal sex as a male was no good for him anymore.  He had been changed.  Cursed!  Reduced!  Because he was a sissy, he was no longer allowed to pleasure himself with his penis anymore… and as such, he never even thought about getting pleasure that way… not anymore.  Instead, his backside now yearned continuously for the stimulation he had come to realize would be his only means to fulfillment.  No sex as a male every again!  The only way he could receive pleasure was to be penetrated… not to penetrate.  More like a woman than a man.  But the truth was… it was not sex like a woman… it was sex for a sissy.

     Denied!  Cursed!  Reduced!  And the intense feelings and emotions about it drove him continuously in his dream in search of anything that would grant him the release he so desperately wanted.

     Music and talking found their way into his dream... disturbing it… disturbing him… irritating him… to the point where he had to wake up to acknowledge the commercial that was now playing from his pink clock radio.  He opened his eyes.  It was another day.  Another day that would be full of sissy humiliation.  But his brain also realized something else.  Today would be different.  Today was Monday and he wasn’t going to work today. 

     That thought quickly led him to wonder… and worry… about what Mel had planned for him today.  She had said last night before he left her apartment that he should get there a little early today.  Why?  What did she have planned?  He knew she didn’t go into her office as early as he usually went to work, so what was going on?  Only one way to find out – he would have to go over to her apartment and wait till she told him what was going on.  Which was exactly what he would have to do anyway.  There was no getting around it. 

     He rolled off of his blow-up mattress and onto his knees, knocking over one of the empty baby bottles near his bed.  He reached up and turned his radio off.  Even on his knees, his legs were splayed wide apart because of the heavy super thick bulk of all the diapers he was wearing.  He didn’t even have to think about it to know he was not only soaked, but messy as well.  Struggling to his feet, he felt the breast forms that were glued to his chest pull a little bit.  The bra he was wearing helped to support them and helped to keep them from pulling worse, but he could still feel them. 

     Wide leggedly, he waddled out to his kitchen.  He was again disappointed to not see a note on his counter from Mel.  Unfortunately, they were past that point now.  He went directly to his refrigerator and pulled out three of the baby bottles he had stocked in there yesterday.  He carried them as he always did out to his one and only chair that faced his wall of shaming pictures. 

     He rarely really noticed those pictures anymore, but today he looked at them more closely.  It was amazing how much they looked like a real child had done them… scribbled them.  Scribbling that didn’t even stay in the lines… colors that were all wrong.  Childish!  And yet it was he who had colored them that way – out in public – out in the restaurants! 

     His eyes glanced down the wall further and fell on the plans that Sandy had drawn up for his apartment if he lost.  Plans that would essentially turn his entire apartment into one big girly nursery.  As he looked at those plans, he again felt a twinge of sexual need stirring within him.  But as usual, he was forced to ignore that need.  There was nothing he would be capable of doing about it.  Part of him was horrified by what those plans would mean if they got carried out… but an equal part of him yearned for it just as much.  He was a sissy.  There was no denying it, or the sexual need the thought of such a life brought to him.

     That need did remind him though about the new reward system that Mel had instituted yesterday.  He had been allowed to play with one of Mel’s toys in his backside for a few minutes.  But he had been forced to do it to himself while she watched.  And most disappointingly, he had only been able to do it for a very few minutes.  He remembered vowing to try to do better today to leak before the hour and a half point whenever possible.  That would rack up more minutes for him to play.  And the best way he could do that?  He was already doing it – drinking from his bottle… bottles!  The more the better! 

     Maybe tonight he could actually play with himself long enough to succeed!  Long enough to achieve an orgasm!  He seriously doubted it, but it was a goal he couldn’t get out of his mind.

      “No!  No!  No!”  Mel screamed as she again shoved at Ray’s big body.  “Get out!”  He went… again, and again she worried that he would come back.  He had been doing that over and over.  She would throw him out, and he would come back again.  And it was all she could do to keep Ray and Derek from fighting with each other.

     Money, money, money!  That was all Ray wanted!  And she suspected that Derek was only interested in her money as well.  She had to protect it.  She had to keep both of them from finding out how rich she really was.  But she wanted them both.  Both of them!  Each of them were big strong handsome hulking men!  And as aggravating as each of them were, it felt so good to be out with them – either of them… or both of them as she really wanted.  But it seemed now that all they were interested in was her money.  Neither of them loved her for herself. 

      “Are you rich?” Derek asked in her dream.  “Get out!” she yelled at him too.  Then she ran for the safety of her bedroom.  Sissy was there with her.  She sat down on her bed and he was instantly by her side… holding her… comforting her.  He alone wasn’t interested in her money.  He alone didn’t make any demands of her.  He alone was the one she controlled – completely! 

     And even in her dream, she remembered that was part of her problem – her usual problem with men.  All men!  She liked being in control too much.  It was all she could do sometimes to play the little Miss Muffin submissive woman that they all seemed to expect from her.  But she was more than that.  Much more.  She was smart!  She was powerful!  Very powerful! She yearned to display that power… yet the only one she really controlled was Sissy.  At least he didn’t make any demands of her she didn’t like.  He wasn’t allowed! 

     In her dream, her bedroom door nearly exploded as Ray kicked it in.  He was back again!  “Are you rich?” he demanded. 

      “No!  No!  No!  Get out!” she yelled once again! 

     And then Derek was there.  “Are you rich?” he demanded as well.

      “Get out!” she yelled at him too.  But neither of them left.  They didn’t love her for herself, they only wanted her money!  “Get out!” she yelled again as she felt her dream tears falling.  “Get out!  Get out!  Get out!”  But each repetition of the words came with less and less intensity.  In her self-pity, she finally collapsed on the bed… and Sissy held her in his arms. 

      “It’s all right,” Sissy said to her over and over again as she cried.  “It’s all right.” 

     The annoying buzzing of her alarm clock forced its way into her dream, pulling her out of it.  It removed all memory of what she had been dreaming about, but not the emotions of the dream.  She opened her eyes only knowing that she had been upset and crying in her dream, nothing more.  She took a deep breath to try to calm herself.  It was just a dream.  Just a dream – whatever it was that she had been dreaming about. 

     She rolled over and realized that she smelled fresh coffee brewing.  Sissy!  Once again Sissy was out there as he should be… her morning coffee was ready and waiting!  Perfect!  Perfect!  Perfect!

     Chad was concentrating on how wet his diaper might be when he heard Mel calling from her bedroom.  His diaper certainly wasn’t wet enough to be leaking yet, but then he had only had it on for a little over an hour now.  Still plenty of time to go.  Her voice calling his name – his sissy name – galvanized him into action.  Forgetting about his wet diaper, he quickly poured her a fresh cup of coffee and hurried with it into her bedroom.  She was sitting up on her bed… smiling at him, he was happy to see.  He curtseyed, careful not to spill the coffee.  “Good morning, Mistress,” he said in his stupid, silly sissy voice.  Then he carefully curtseyed again.

      “Good morning Sissy,” Mel returned as she looked him over carefully.  As she hoped, he was attired perfectly in his maid’s uniform again.  She took the offered cup of coffee and sipped at it.  Mmm.  So good!  And she didn’t even have to get out of bed to brew it or pour it into the cup.  Sissy had done all that for her and brought it to her only moments after she had called his name.  Perfect!  Perfect!  Perfect!  “Thank you, Sissy,” she said with a bit of a smile.  “I’ll just have a couple of pieces of toast for breakfast this morning.  Oh, and put some strawberry jam on it as well.  And I’ll have it right here in bed.”

     Chad curtseyed and hurried out of the room.  An easy breakfast to prepare.  A moment later, he was loading bread into her toaster. 

     The coffee helped kick start Mel’s brain to thinking.  Thoughts of how nice it was to finally have Sissy there and doing what she wanted him to be doing were interrupted by thoughts of her day ahead – specifically, the meeting with Feinbaum’s group over the contract.  Even now, after having been through the contract so carefully, there was still something that bothered her about it.  And yet, she could find no fault at all with the thing.  The contract was a massive piece of legal art… constructed by one of the best in the business.  And today they would be meeting with Green Growers to recommend that they sign the thing and finalize it tomorrow.  Hopefully, she would merely be attending and wouldn’t have to even open her mouth there.  What would she say anyway?

     This contract had come along at the wrong time!  It was seriously distracting her from what she needed to be doing with Sissy.  She had mostly cleared her schedule for all this week just so she could work closely with Sissy and make sure she would win the bet, but there had simply been no getting around this deal.  You don’t say no to Old Man Feinbaum!

     So what was she going to do with Sissy today?  Her thoughts were interrupted by him coming back into the room bearing a tray with a plate and two pieces of toast covered in strawberry jam.  She let him place the tray on her lap, then she handed him her coffee cup to refill.  As he hurried off, she went back to her planning.  What to do with Sissy?  Obviously, the best thing she could do with him today would be to take him into work with her and leave him with Andrea till she could get out of that meeting.  Then she would be free for the rest of the day to do what she liked with him… or to him as the case might be.  She actually giggled a bit at the thought. 

     She was still giggling to herself as he came back in with the fresh cup of coffee.  “Have you leaked at all yet?” she asked him as he curtseyed and offered the cup to her. 

     Chad curtseyed again.  “Not yet,” he replied in his silly voice, “but I still have plenty of time.”  Curtsey.

      “How much time?”

     He looked at the clock beside her bed.  Curtsey.  “About twenty minutes yet.”  Curtsey.

      “So in five more minutes your chance of gaining some reward time will expire,” she stated.

     Curtsey.  “Yes, Mistress…  But I think I’m getting really close already!”  Curtsey.

     Mel was glad to hear that.  “How many bottles have you finished so far this morning?”

     Curtsey.  “I’m working on number six,” he replied.  Curtsey.

      “So I take it you’re trying hard to rack up some of that reward time.”

     Curtsey.  “Very hard!”  Curtsey.

     Mel was pleased.  Very pleased.  It was exactly what she had hoped for… exactly what she wanted to hear.  Hopefully, the little bit of reward he might gain every day would keep him trying harder and harder to continuously wet himself – and in the process, would keep robbing him of any ability he might still have to hold back and control himself.  Hopefully!

      “Very good, Sissy,” she replied.  “I’m glad to hear that.  And I hope you manage to gain a lot of reward time today.”  She switched subjects… somewhat.  “Have you eaten anything yet this morning?”

     Curtsey.  “No, Mistress.”  Curtsey.

      “Good!  You’re not supposed to!” she replied authoritatively.  “Now go start making your breakfast while I’m eating.  I’m sure you know by now what you’re allowed to have.  I’ll be in soon to set you up in your highchair with it.”  She watched as he curtseyed and hurried off.  Yes, despite having to still worry about taking care of him and making him incontinent, it was going to be so great when this bet was over with and he would be locked into her service.  Then, all she had to do would be to find a way to make it permanent.  Unfortunately, her thoughts were clouded with the one thing she didn’t want to think about concerning Sissy… the one thing she still hadn’t found an answer to yet – self-respect, friends, and a life!

     Chad had already finished heating his baby cereal and had poured it into one of his childish bowls by the time Mel came out of her bedroom – wearing nothing but her nightgown with a light robe over it.  She saw that he had his breakfast ready, but her first concern was his diaper.  “Are you leaking yet?” she asked, knowing that the deadline for any possible reward was only a little over a minute away. 

     Chad quickly took a moment to try to figure out if he might be leaking.  Then he curtseyed.  “I don’t think so,” he replied uncertainly.  “But I have to be very close.”  Then he curtseyed again.

      “Oh well,” Mel replied.  “Close doesn’t count.  Up in your highchair now.”

     Chad was disappointed, he had been really trying since he had gotten out of bed.  He wanted that reward time – and technically, he did still have a few minutes left.  Reluctantly, he headed for his highchair, but he stopped just as he turned around and started to climb up into it.  He looked up at Mel hopefully.  “It’s possible that I might be leaking now,” he told her without bothering to curtsey.  “Or if not… I could be very soon.  If I get up into the chair, I might not be able to tell.”

      “Lift your dress,” she told him.  “Let’s see.”

     Chad pulled his skirt up high and started feeling around the leg openings of his diaper while Mel looked on closely. 

      “I don’t see anything yet,” Mel said.  “But you do look awfully wet.”

      “I know I’m really close!” Chad insisted.

     Mel shook her head.  “Okay Sissy.  Grab your bottle.”  She glanced at the clock.  “You’ve got thirty seconds.  If you’re not leaking by then, then you’ll just have to start your breakfast and hope that you’re leaking before the next fifteen minutes gets through.  Otherwise I’m going to paddle you good!”

     As wet as his diaper was, Chad was sure he would be leaking before his second deadline.  What he wanted though was to be leaking in the next few seconds.  He attacked his bottle furiously, sucking as hard as he could on it while Mel watched.  Twenty seconds later, he felt himself peeing again.  As always, it was only a tiny bit, but it was more added to his diaper.  Still drinking from his bottle, he began feeling around the bottom of his diaper again.  Leak!  Leak!  Leak!

     He glanced at the clock.  Ten more seconds!  Please pee again!  Please leak!  The time was ticking down.  Leak!  Leak!  And he thought he felt something moist at the bottom of his diaper!  “I’m leaking!” he proclaimed quickly. 

     Mel glanced at the clock and saw it ticking down the final few seconds.  With somewhat of a smirk on her face, she said, “It’s so close I shouldn’t give you anything at all.  But you tried so hard, I’ll grant you a whole minute – this time.  Don’t expect me to be so lenient again!”

     Chad didn’t care.  He had done it.  He had gotten his diaper leaking ahead of time and now had one whole minute of reward time coming. 

      “By the way,” Mel said to him.  “You might want to get that diaper changed pretty fast.  I started your time running the minute you told me you were leaking.”

     Once Chad’s diaper was changed, Mel locked him into his highchair and left him not only with his usual breakfast and baby bottle, but she also set out two more bottles for him to drink.  “That’s just to give you something to work on while I’m getting dressed,” she told him.  Then she left him alone knowing he wasn’t going anywhere till she came back to release him. 

     Now, what was she going to wear for this meeting?  It was a foregone conclusion that she would be wearing one of the two new suits she had just bought.  But which one?  She considered that while she showered and did her hair.  She was still considering it as she did most of her makeup.  In the end, she wore the same blue suit she had worn to the last meeting.  Since the room had been full of men, she doubted that anyone there would really remember what she had worn anyway.