The Bet - Chapter 62 (Thursday – week 9 Part 1 of 5)

The Bet

By Karen Singer

Chapter 62 (Thursday – week 9 Part 1 of 5)

     Her soft hands caressed his face.  Her beautiful flawless skin was smooth and soft against every part of his body that it touched.  And in his dream, she was completely naked.  She cuddled against him and he could feel her wonderful body pressing against his glued-on breast forms… almost as if his breasts were real breasts!  Her soft smooth legs entwined with his own smooth and hairless legs, rubbing slightly… sensually.  And her elegantly sexy hips pressed again and again against… the tremendous bulk of all the wet diapers he was wearing. 

     And best of all, she was naked and he wasn’t blindfolded.  He could see every perfect thing about her.  And it was as good, or better, than the image that his mind had created from just touching her. 

     She kissed him, and their tongues caressed, mimicking the sensual caresses between their two bodies.  It was magic!  He felt her hips pushing again against the bulk of his diapers, and he felt again the longing to have something shoved up his backside… something long and hard… something sexy!  Oh to feel that… while caressing her amazing body.  Because even in his dream, he dared not dream about that other, now useless, sexual appendage he used to use.  The one that he dared no longer allow to get hard.

     He let his hands roam at will over her smooth flawless skin, feeling the texture, worshiping its beauty.  And in return, he felt her hands roaming over every bit of exposed flesh that he owned as well, reciprocating the love he felt for her.  Returning the gift of sensual touch.  Showing him… that she cared for him as much as he cared for her.  It was enough to almost make him cry inside, although in his dream, she never knew. 

     It was simply a dream of love.  Tender, devoted, fully returned… love.  And his mind dwelled on every tiny aspect of it for a long, long time… as he dreamed, and dreamed, and dreamed.

     She dreamed of Larry.  She hadn’t dreamed or thought about him in years.  But she dreamed of him now.  He was the man she had first made love with, back while they were still in college.  He was the one she had given her virginity to.  But what she dreamed the most about him, was the way he had left her… cold, suddenly – only days after he had popped her cherry.  And in her dream, his leaving still hurt.

     One by one, her dreams filtered through the few men in her life.  Some better than others.  Some she made love with, others she hadn’t.  And one by one, she felt the pain of those relationships ending, some because she hadn’t really liked the man that much, more because her demanding personality had driven them away.

     And then there was Brad.  Her dream lingered a long time on him.  She had loved him dearly.  He had asked her to marry him.  She had said yes.  But from that moment on things had changed.  Her dreams started remembering the arguing, the fighting, the hurting, all because he claimed that she was, as he had put it, too bossy!  In her dream, she cried once again as in a fit of rage he had called off the wedding, proclaiming he never wanted to see her again.  And even in her dream, she realized that he hadn’t.  Ever!

     And after Brad, she dreamed of Ray.  In her dream, she didn’t make love to him, but instead she replayed that day when he had suddenly appeared at her door and she had discovered that he was only after her money.  He didn’t love her either!  And she had gotten so angry she had physically thrown him out of her apartment.  And as she closed the door behind him, she had turned, and there was Derek… and Sissy.  Both of them.

     Derek was everything a woman like her could want – tall, handsome, very well built, confident… the list seemed to go on and on.  And further in the background was Sissy, small, submissive, and possessing enough oddball needs to send any woman packing!  Two distinct contrasts.  One was perfect for her, the other… laughable.  And yet, even in her dream, she realized that she was drawn to both.

     Derek came to her and took her hand, and led her directly into her bedroom… and into her bed.  In her dream, she only knew that they made love, but there were no distinct details – other than how good his amazing body felt next to hers.  And suddenly, in her dream, they were done with the sex part, and Derek immediately got up from the bed and left her – just as soon as his own sexual needs were finished.  And she felt totally unfulfilled.  As if he too was abandoning her.  Gone!  Without the least bit of attention to her needs!  And she felt abandoned again… and especially hurt.

     And in her despair, Sissy came to her and comforted her.  He caressed her in that loving way of his that only he was capable of.  And she felt grateful to him… and loved by him.  In gratitude, she allowed him to make love to her as well… and she allowed him to do it like a man, not constrained as the sissy he was.  In her dream, there were no breast forms, no diapers.  Only his scrawny naked body… with its strangely miniscule penis.  She grabbed that tiny appendage and caressed it with her hands, trying to make it do what it was supposed to do – grow!  And finally, it did harden, yet for some unknown reason it refused to grow bigger than it was.  How was she supposed to make love with something like that to work with?

     But now Sissy was changing, he became more demanding… not like himself at all!  He rolled over on top of her and tried again and again to push that tiny little thing into her.  She did everything she could to accommodate him.  She pushed her hips desperately up toward him as he pushed down, but despite that, all she could feel was the tip of it barely entering her.  Not enough even for proper stimulation.  It was so frustrating!

     Despite that, the moment she felt his tiny “thing” just barely into her, he began rocking and thrusting forcefully for a few seconds, and then she felt him cumming… orgasming… while she could barely feel anything!  And only moments later, he was done.  Finished.  And she was left unsatisfied.  And now that he was done, she knew that he would return the effort and use one of those marvelous methods of his to show her his appreciation and to show her how much he loved her.  But instead, he rolled off of her and got to his feet.  And exactly as Derek had done earlier, he walked out.  Abandoning her.  Leaving her alone.  Not caring about her in the least. 

     Even Sissy, despite his flaws, was still nothing more than a stupid regular man.  And just like every other man who ever came into her life, he really only cared about himself and nothing more.  Even Sissy… walked out on her.  And it hurt!  It hurt bad!

     In her dream, she cried, feeling nothing but self-pity for herself.  Self-pity that refused to go away.  Self-pity that she deserved to feel… because she was unloved.  Self-pity that…  In her dream, something minor was suddenly distracting her, as if calling to her.  But she was too preoccupied with wallowing in her own pool of grief to figure out what it was.  She was alone, abandoned by every man in her life… even Sissy.  Especially Sissy.  They all walked out on her.  And… and there was that something distracting her again, making her take notice, forcing her to come up out of the deep well of emotions she was swimming in.  What was it? 

     She tried going back again.  Even Sissy walked out on her.  Even Sissy…  What was that?  Her brain suddenly processed the aroma of freshly brewed coffee that tickled her nose.  Coffee?  The smell was enough to distracted her much more, to cause her to forget what she had been dreaming about, even though the feelings of abandonment and self-pity still remained locked firmly in her mind.  She opened her eyes as those powerful lingering emotions still filled her.  Ugh!  What a way to wake up – although the smell of the fresh coffee was certainly nice.

     She sat up in her bed, trying to piece together what she had been dreaming about that made her feel so despondent.  But the smell of the fresh coffee soon became more important.  She needed that coffee, and she needed it soon! 

     “Sissy!” she called, hoping that he would hear her.  It was a few moments, but only a few before she heard his footsteps hurrying toward her.  And a split second later, he was there, in her bedroom, perfectly dressed as her maid… her own wonderful servant… and he held that first cup of freshly brewed coffee for her in his own darling hands.  Wonderful!

     She thrilled as he curtseyed and said good morning to her, before curtseying again and handing over the steaming cup of potent liquid for her to take.  Her eyes never left him as she raised the cup to her lips and took that first sip.  Hot, wet, wonderful!  “Thank you Sissy,” she said with the appreciation she truly felt.  She saw him smile at her, and curtsey again, and reply, and curtsey again.  And… she giggled.  His little curtseys where just too darling!  She couldn’t help it, she simply loved seeing him do that!

      “Go make me some breakfast,” she ordered.  “Same as yesterday.  And I’ll have it right here again.”

     Chad curtseyed again.  “Yes, Mistress,” he replied, lisping in his stupid, silly, sissy voice.  “Right away.”  Then he curtseyed one more time and hurried out.

     Mel watched him go, and something about watching him leave her again brought back the emotional feelings of abandonment again.  He too would leave her… if he could.  And her brain remembered those words he had spoken to her last night.  The words he had said when she thought they were both being not only passionate, but totally honest with each other.  “I would kiss you till your body shudders… and you know how I feel about you.”  And he had done exactly that! 

     But it had been later, when she had finally been brave enough to ask how he really felt about her that now had her confused.  Because it was what he hadn’t said that told her more than what he had said.  He hadn’t said that he wanted to stay with her no matter what happened.  He hadn’t said that…  He hadn’t said that he loved her!  He had never once used the word “love.”  The one word that meant everything!  He was just like all the rest.  Give them what they’re after and they’re out the door.  Walking away.  Leaving you flat.

     He was just like all the rest… or was he?  Everything he had told her last night had been wonderful.  And she thought she had believed it.  Was she reading too much into it?  Another thought suddenly pounded at her brain.  Why should she care?  He wasn’t what she needed in a man.  He wasn’t anyone she could ever marry.  It was laughable!  She’d be the laughing stock of… the whole world.  She couldn’t show up at a fancy party with him on her arm.  What would he be wearing, a stupid silly sissy dress?  Or perhaps a dress that might make her jealous?  No!  Why was she even bothering to worry about such things?  Why should she care if he loved her or not?  Why should she really care if he would ever leave her or not?  It made no sense at all.  Get a grip Mel!  Get a grip!

     Yes, he would be the perfect servant!  Perfect!  He was someone she could order around to her hearts content.  He was someone she could take out all her frustrations on… and he would love her all the more for doing it.  And… he was smart enough to easily run her entire estate for her… if she ever got around to buying one.  He would be capable of handling all of it… by himself! 

     But for heaven’s sake!  He wasn’t marrying material!  Get a grip Mel!  Get a grip!

     Besides, was it right for her to impose that kind of life on him?  Someone who had that kind of brain?  Was it right?

     It took a few more sips from her coffee before she was capable of forcing herself to think about other matters.  She hadn’t forgotten.  It was something that was so strongly on her mind that she didn’t need to concentrate on it… until now.  Today was Sissy’s last day before he would be free to regain all his control… or try to.  Today was her last day to insure his complete incontinence.  Today was her last possible day to do anything at all to win the bet between them.  And the one thing that bothered her the most, was that she didn’t have a single clue as to what more she could do with him to ensure that incontinence. 

     It was the one single thing that their bet was really all about.  The one single oddball thing.  As strange as it sounded, they had actually made the bet over it.  She claimed that she could make him totally incontinent in only two-month's time.  And he claimed that she couldn’t.  It was something that had been conceived in a moment of drunken fun.  But for some unknown reason, the idea had struck a note between the two of them.  And it had struck hard enough that in the sober light of day, they had not only agreed on going through with the bet, but she had drawn up a rather formal contract that they both had signed – and Andrea had notarized for them.  The most oddball bet she had ever heard of.  Yet they had done it. 

     And now that bet was drawing to a close.  Today was the last day of the normal bet period – the phase where she had absolute total control over him.  The phase where he was bound to do anything and everything she wanted – no matter what!  And the things she had forced him to do were… somewhat surprising, especially to herself.  And the most surprising thing of all was that she had discovered how much she liked it.  She had discovered how much fun she got out of making him do the most outrageous things.  She discovered how much enjoyment she got out of keeping him firmly under her thumb.  Very firmly! 

     And tomorrow?  Tomorrow all his servitude would be over with… unless he lost the bet as she hoped.  And if he did lose?  Then she would have him at her beck and call for another full year.  And after that?  Well, she was hoping that things would somehow work out and take care of themselves. 

     But if he won and she lost?  She knew without a doubt that her dream of buying a proper house would go back to being just a dream again.  She simply couldn’t conceive of having a whole big house again… with only herself to live in it.  Besides, she wasn’t all that found of housework.  And Sissy seemed to be awfully good at it… not to mention his talent in the kitchen!

     Somehow along the way, she had tied her dreams for the future around Sissy.  And having those dreams depended on only one thing – winning the bet… as weird as it sounded.  How had it happened?  She didn’t know… nor did she care.  Some things just had to be accepted.

     Chad loaded her tray with her breakfast and grabbed another cup and filled it with coffee for her.  Then he carefully carried it back to her bedroom.  She was still there, still in bed, still holding the first cup he had brought her.  As he approached, she set the now empty cup on her nightstand and he curtseyed slightly before setting the tray on her lap.  “I remembered to bring you another cup of coffee this morning,” he mentioned before stepping back and curtseying – properly this time. 

     She smiled.  “Thank you Sissy.  I appreciate that.  Just like I appreciate everything you do for me.”

     Chad beamed at the compliment.  He didn’t know why, but it seemed like for about the last week, she had been more complimentary towards him.  She had made him feel like he existed and not like he was something she didn’t care about at all.  And it made him feel good.  Of course, he wasn’t so sure about the time he always spent up on his perch in the corner.  But still, the compliment was more than welcomed.

     Mel was about to start eating, but she saw him standing there, watching her.  “Don’t you have something else to do?” she asked. 

     Chad was a bit crestfallen that she should send him away, but he quickly realized that he shouldn’t feel like that at all.  Nobody would want their maid standing there watching them eat breakfast in bed.  Nobody!  He was her maid!  He was… her sissy.  For now anyway.  He curtseyed and headed back out toward the kitchen. 

      “Get your own breakfast started!” Mel called after him.  “I’ll feed you when I’m done here.”

     Make his own breakfast!  A breakfast of baby cereal… eaten like a baby… while sitting in his highchair.  The very thought of how humiliating it was sent a sexual thrill through his body – even though he wasn’t looking forward to eating yet another bowl of that lousy tasting cereal.  But today was the last day.  Today was the last time he would ever have to eat the baby cereal again… unless he wanted to.  He was looking forward to it coming to an end… and he wasn’t.