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. 

The Bet - Chapter 61(Wednesday – week 9 Part 8 of 8)

The Bet

By Karen Singer

Chapter 61(Wednesday – week 9 Part 8 of 8)

     Chad wiped the counters off one more time.  They positively gleamed!  It was all he could do.  He was done.  He went out to the living room and stood in front of Mel, and curtseyed.  “I’ve finished,” he told her.  Then he curtseyed one more time.

     No matter how often she saw it, Mel still loved seeing him curtsey like that – a man – curtseying like a… a sissy.  And the double courtesy that he had picked up from Robin was an extra delight.  But would those delightful curtseys soon be gone?  Forever? 

     She had plans for him tonight.  Plans that had been building within her all day long.  From the time she took charge of things in Feinbaum’s office to the time she had left the mall, the heady rush of excitement she got from making him do the most outrageous things had quietly but steadily been building within her, fueling her sexual need.  The foot massage he had given her earlier hadn’t helped matters either.  That need had diminished a bit in the last few hours as the plain tasks of daily life had paraded around her, but they hadn’t fully gone away.  Did she dare act on those needs now… now while the night was still so young? 

     It took her only a moment to remember that she was still in charge.  She could have… or do anything she wanted.  He was hers to command – totally.  For now. 

      “Go put some protection on the bed,” she told him.  “And make sure you put plenty!  I don’t want to take a chance on you peeing on my bed – even accidentally!”

     Chad curtseyed and hurried off to her bedroom.  Protect her bed!  That could only mean one thing – she was going to grant him some of his reward time now.  He found it a bit odd that she would give it to him so early in the evening, but he wasn’t about to turn it down.  As if he had a choice. 

     After all the humiliation he had been through today, he was more than ready.  Every bit of that humiliation had fueled his sexual need.  But was that need fueled enough for him to actually achieve orgasm tonight… just by himself?  Without Mel’s help?  He really hoped so, even though he had no illusions that it would ever actually happen. 

     Of course, he also had no idea how much reward time he had coming to him.  Would it be enough?  All day long, especially at the mall, she had never told him about it.  He was sure he had gained some time, but how much?  Well, he would just have to enjoy whatever he could.  He was certainly ready… and looking forward to it!  He made extra sure to put more than enough protection over a wider area of her bed than he usually did before going back to the living room to curtsey and tell her that he was ready. 

     Mel set her laptop aside and got up.  “Okay Sissy, let’s go.” 

     Chad went back to the bedroom again where Mel had him strip down to just his wet diaper.  He climbed up onto her bed and laid down on his back, waiting for her to unfasten his diaper like she usually did.  But she walked off instead, heading for her dresser.  When she came back, he was surprised to see that she had one of her scarves in her hand that she used to blindfold him with.  The sight of the scarf annoyed him at first, but a moment later, his brain remembered what that had to mean – she wanted him to please her again.  Maybe she wasn’t going to grant him some of his reward time yet. 

      “Sit up,” Mel told him.  She waited till he was in a position where she could tie the scarf around his head easier.  As usual, she tied it as tight as she dared, hoping that it wouldn’t fall off during the ensuing activities.  She didn’t know what she would do if that happened.  Not that it would really be any problem… she just… for some unknown reason… didn’t want him to see her naked body.  But him ‘feeling’ her naked body?  That was a different question!

     Chad sat in the middle of the bed listening to the faint sounds in the room around him.  He could hear her moving around doing something… what?  Was she removing her clothes now?  His head followed the sound of her approaching the bed again.  He waited to feel the mattress move, but instead he heard the drawer of her nightstand opening.  He heard… faint sounds, then the drawer closed again. 

     He couldn’t see her but he could feel her… sort of.  His overactive imagination reached out and tried to feel her aura as she stood so close… so close, but not close enough to actually touch.  He knew she was there though, right there in front of him.  He knew it, yet she wasn’t coming any closer.  She was just standing there, waiting, or teasing him.  It didn’t matter.  He could smell the soft aromas coming from her body – she had to be naked now.  She had to be!  He could easily imagine the feel of her soft skin against his.  His whole body seemed to yearn for the touch of it.  His hands were ready to caress that smooth soft skin – all over her – from the tip of her head down to the bottom of her toes.  Her delightful pretty toes. 

     And a very wrong thought crossed his mind.  A thought that he knew was forbidden, but he couldn’t help thinking about it never the less.  Fortunately, it only existed in his imagination.  He imagined him leaning over top of her… feeling her beautiful naked breasts against his chest… leaning down… and planting a passionate kiss right on her wonderful, delectable lips.  Such a kiss.  Such ecstasy!  But as much as he hungered for it, he could never have it.  Some things weren’t allowed for the likes of him, things like actually seeing her naked body with his eyes.  Things like… the passionate kiss on her lips.  Some things weren’t allowed… because he was a sissy.  Nothing but a sissy. 

     She moved, and he felt the bed shake ever so slightly.  And her words, ever so soft and sensual reached his waiting ears.

      “Move over Sissy.  Give me some room.”

     He moved, carefully backing away to allow her to fully get up on the bed with him.  He felt the bed continuing to shake a little, then it stopped.  Then… everything stopped.  He waited.

     Mel stretched out luxuriously naked on her bed, writhing just a bit at the sensual pleasure of it.  Sissy was still sitting, waiting expectantly to be told what to do.  And she was more than ready.  But…  Instead…  “Sissy, no touching.  Tell me instead… what would you like to do to my naked body?”

      Huh?  Tell her?  He’d rather show her!  He didn’t need his eyes to see her, his mind fully remembered every wonderful bump and curve of her amazing body that his hands had fully explored.  It was that sensual naked picture of her that his imagination now held foremost in his mind.  She had denied him the sight of her, and now she was denying him his touch as well.  But that wouldn’t stop him from remembering her… from dreaming about her.  “I would start with the hair on the very top of your head,” he replied.  “I would run my fingers through it over and over again, pulling on it ever so gently, untangling it, loving it.”

     Inch by inch, his imagination worked its way down her body, describing in minute detail exactly what he’d like to do to her, how he’d like to make love to her.  And even though he wasn’t sure if it would be allowed or not, he described the tiny kisses he would plant all over her.  Every part of her. 

     Mel was going nuts… and he had never even touched her.  But his words certainly did.  She could just feel every single little thing he would do with her… do to her.  She was more than sexually wet, she was practically orgasming from just listening to him.  He was describing now how he would start again at her forehead and plant little tiny kisses, ever so soft and light, all over her skin.  Working his way down, down…  and she saw him pause… and sit back a bit, as if alarmed.  And his words stopped totally. 

      “What is it?” she asked.  “What’s wrong?”

      “I would do something I shouldn’t,” he said very softly. 

      “What?” she asked.

      “You won’t get mad at me if I just say it?” he asked uncertainly.

      “Of course not,” she replied.  “What is it that you would do?”  She was prepared for something rather horrible… especially in light of how she so often treated him.

     Chad took a moment to gather his courage to actually say it.  “I would kiss you… I would kiss you on the lips.  I would kiss you with all the passion I have… all the passion I could possibly make you feel.  All the…”  Passion seemed to be the wrong word suddenly.  Dare he say it?  Damn!  “… love I’m capable of feeling.”  He paused to see if she would say anything to let him know how angry she might be.  She said nothing, so he dared continue.  In for a penny, in for a pound!  “I would kiss you, till your body shudders… and you know how I feel about you.”

     He waited again, sorry he had spoken the words.  Would she yell at him?  No, more likely, she would laugh instead.  He was a sissy.  A damn sissy!

     Mel watched his face. Even the scarf covering so much of it couldn’t hide what she saw.  And more than anything now, now that he had said the words, she saw nothing but disappointment and rejection in that face.  But his words alone had been the kind of thing that every woman years to hear.  They were the essence of beauty… the essence of romance… the essence of… love.  And her writhing body was responding like never before. 

      “Don’t just sit there,” she finally said.  “Kiss me, damn you!”

     Her words shocked him.  But giving no other thought to it, he very slowly leaned his body over, not knowing where her mouth was exactly.  But guided by where he thought it was, he pursed his lips as his body sank closer… closer… closer.  His lips touched… her lips.  And her head rose slightly to press against his.  And just as he had described, he kissed her passionately, wrapping his arms around her now, holding her close to him.  And it was no time at all till he felt her have the first orgasm of the evening.  Their kiss lasted a long time before she finally broke it, her orgasm having ended an eternity earlier. 

      “Now,” she said softly.  “Everything you described you would do to me earlier… do it!  Do it now!” 

     And he did.

     There comes a point in prolonged lovemaking where, despite how good it feels, sanity finally creeps back in.  Did she want more?  Oh yes!  Much more!  But there were other things now that she needed to do… before she was no longer capable of doing them. Still, it was only with great effort that she said, “Enough!” 

     Chad felt her hand pushing against his forehead where his wet face was buried between her legs.  He pulled back.  He was tired, but he knew without a doubt that he had done a good job for her.  Would she appreciate the effort… the hard work he had put into it?  Would she?  Still blind, he moved out from between her legs. He knew he shouldn’t, but he allowed his worn out body to flop down on the bed next to her.  He should get up, he knew it.  He didn’t belong there.  But he stayed.  And miraculously, he felt her soft hand cup his face, and even better, he felt her lean over and plant a small kiss on his cheek just below the material of his blindfold.  And then… she was gone.  Off the bed.  And he laid there, panting slightly, trying to recover from his efforts. 

     She was gone a long time, to the bathroom he supposed, but he was still lying in exactly the same position when he heard her come back again.  Yet she didn’t say anything.  Nor did she climb on the bed.  Was she getting dressed?  He didn’t know.  He heard her by the side of the bed again.  He heard her nightstand drawer open again. 

      “Scoot over this way baby,” she said softly.  “I can’t reach you where you are.”

     Following  her command, he moved over closer to the side of the bed and laid on his back.  A moment later, he felt her unfastening his soggy and possibly leaking diaper.  He laid perfectly still as the cool air washed over every part of him that had been underneath that hot diaper.  Every part of him that is, except the part that was still covered – encased in the plastic of his chastity device.  Nothing ever touched that.  Especially not him.

     He felt her quickly pull the diaper back over him a little.  Was he peeing again?  He couldn’t feel it if he was.  Nor did he care.  He was a bit worn out just then.

      “Roll over and get to your hands and knees,” she said when she had pulled the diaper away again. 

     He did, and he felt her pulling the diaper completely away from him.  He didn’t know where she put it, and didn’t really care.  Now the cool air was caressing his backside as well. 

      “Turn this way,” she instructed from the side of the bed and waited till he was facing her, still on his hands and knees.  “It’s your turn,” she told him.  “Time for the reward you earned today.”

     He was glad.  He wanted it.  He needed it.  He just wished he wasn’t so worn out already! 

      “But since you’ve been so good, I’m going to help you a little this time.”

     His heart soared!  She was going to help!  How much, he didn’t know but anything would be better than him doing it all for himself.

      “Reach out your hand,” she said.  “What do you feel?”

     Totally blind, he reached out with his right hand… and reached… and reached… and found… nothing.  He heard her giggle.

      “Keep looking,” she teased. 

     He waved his hand a bit more, and connected with something hard!  Something that gave a bit when he hit it.  His hand closed on top of it, then over and around it.  She was giggling again.  It only took him a moment to realize that he was feeling the lifelike dildo that she must have strapped onto her body.  He shivered involuntarily – especially at the thought that that thing might be soon invading his backside. 

      “Are you happy?” she asked.  “Show me how happy you are.  Show me how much you want that thing.  Kiss it.  If I were a man, show me how you would make me all hard and ready to push this thing into you.”

     Every word she spoke, was only meant to humiliate him.  And every word seemed to hit him right in his sissy core.  He kissed the tip of it.  He licked the length of it.  He hated doing it more than anything.  Yet he still wanted it more than anything as well.  His double edged sword.  Or hers.

     And when she was satisfied, she repositioned him on the bed and grabbed a bit of lube from the nightstand.  A moment later, she was mounted behind him, placing the tip of her phallic toy right up against his tiny asshole.  And she could see that he was doing everything possible to make it easy for her to push it in.  He wanted it, of that she had no doubt at all.  But then, since she had now denied him any access at all to his old male method of having sex, this was now the only avenue available to him.  She figured that he should want it pretty badly. 

     Ever so slowly, she pushed with her hips, pushing it slowly into him, feeling the pressure at the same time as the opposite end of it, buried inside of her, reacted to those same pressures.  All the way in… then most of the way back out.  In, then out.  In, then out.  Forming a rhythm that seemed to gradually go faster and faster, more so because of his efforts and need than from hers.

     But he got just so far… and couldn’t seem to get any further.  And she wanted him to go further… this time.  And she remembered the one thing he seemed to always need.  The secret ingredient.  With a bit of effort, she leaned over him so he could hear her better.  “This is what you like now, isn’t it.  This is the way your body craves to have sex now isn’t it.  You no longer even think about having sex like a man anymore, do you?  You no longer even think of that tiny little silly growth on your front side when it comes to sex anymore, do you?”  She could tell that her words were reaching him now as his motions and effort increased in strength. 

      “This is what you want when it comes to sex now.  You really crave some big strong man to bury his massive cock right up inside your sissy little ass now, don’t you?  You no longer crave sex like a man anymore, you crave to be penetrated like a woman… but really… more like the silly little sissy that you are!”

     Her words were reaching right down into him.  Right down into all of his latent sissy humiliation fantasies.  Bringing them forth, mixing them with the amazing feelings he was getting from her strap-on fucking him in his backside.  And despite himself, he couldn’t help it, he could feel his sexual excitement growing to new levels!

      “You’re not a man anymore, are you?  In no way at all can I see how you can ever call yourself a man again!  I’ve removed every bit of maleness from you!  You’re going to be doomed to a lifetime now of high heels and skirts… and getting fucked in the rear instead of you fucking some poor woman with that laughably tiny thing you used to call a cock.  You can’t even think of using that poor excuse for a sex organ for anything more useful than to pee out of now… uncontrollably at that!  A lifetime of skirts, and dresses, and high heels, and getting fucked like a woman, and servitude… to me!  And you crave every single bit of it, don’t you?”

     The yell was totally involuntarily as her words and fucking finally sent him not just over the edge, but far over the edge.  His whole body seemed to lock up and respond in the most wondrous ways… from the tip of his toes to the top of his head – more like a woman would feel an orgasm, not a man.  And when it was finally over, he felt Mel slowing within him, or was he the one who was slowing instead.  He had done it.  He had gotten there again.  Amazingly.  And it had felt… unbelievable!  Not exactly like a man, but… maybe better.  It had lasted longer than he had felt it like a man, and it had seemed to affect every part of his entire body – not at all like a man.  It was simply… amazing!

     Panting from the effort now, he slowed to a stop.  His body still felt the sexual need.  It hadn’t really gone away at all.  But was it diminished at all?  He wasn’t sure.  He felt Mel pulling her strap-on toy out of him.  He stayed on his hands and knees though because he wasn’t interested in moving to any other position.  He could easily collapse on her bed, but right now, he might not get back up again.

     He felt her moving off the bed now, leaving him alone up there.  A moment later, he felt her hand caressing his head for a moment. 

     She didn’t have to ask if he enjoyed that, it was pretty obvious.  She knew the diapers under him, the ones protecting her bed, were damp with his leaking pee, some more than others.  There were no big puddles though.  Just a few drops at a time had flown out of him to land wherever they wanted.  No control at all… as far as she could see.  But would he be able to regain all that control when he was again allowed to try?  She had no idea.  But she hoped he wouldn’t.  Even though… what she was doing with him might not be the right thing to do at all.

     While he was still on his hands and knees, she kept her phallic toy still strapped around her with one end of it still buried inside of her – it actually felt pretty good as the front of it bobbed around and came into contact with different things.  She grabbed a wipe and cleaned his backside, almost laughing as the sudden cold made him arch his back.  “Lay down Sissy.  Let’s get some diapers on you now.”

     Using the diapers from her bed that were the most wet, she put four layers on him, taking the time to slice the outer cover of each one thoroughly before putting on the next layer.  A few minutes later, she was done.  “Move over a little,” she told him. 

     She almost laid down with the strap-on still attached, but at the last minute she decided to remove it.  “I’ll be back in a minute,” she told him.  “Stay there.”

     Still blindfolded, Chad heard her walking away, leaving.  For the bathroom again?  He wasn’t sure.  But he didn’t move.  He just laid there relaxing, enjoying the afterglow of what had just happened. 

     And then she was back.  He felt her climbing up onto the bed with him, laying right next to him. 

      “Turn in to me a little,” she told him.  “So I can see you.”

     Chad rolled over on his side.  She wanted to see him?  But he couldn’t see her.  He supposed it was more than fair… given what he was.

     Mel moved close to him, cuddling close.  She grabbed his arm and put it over her, and he held her.  And she watched his face – what she could see of it.  And she laid there like that for a very long time – not moving, not speaking, just staying and enjoying. 

     It was a long time before she found the courage to speak.  A long time before she could ask something she had been afraid to ask.  But tomorrow would be the last day.  After tomorrow, it might be all over.  She had to ask, and she had to ask it now.  So she did.  “Tell me,” she said.  “Tell me honestly.  Please.  This weekend, if I win the bet… and you lose… will you still honor our deal and serve me?  And more importantly, when this is over, either way it comes out… will you hate me?”

     It was what she had asked him before.  The questions he remembered she wouldn’t let him answer earlier.  But now it seemed she wanted to hear what he had to say, and she seemed to want his honest opinion.  “Will I honor our bet?” he said.  “Of course.  Absolutely.  Totally.  Completely.  You don’t have to worry about that.”

     Mel breathed somewhat a sigh of relief.  “And how about the other thing?” she asked.  “Do you hate me?  Do you, or will you despise me?”

     He was longer answering only because he was surprised at how afraid she was of his answer.  “I don’t hate you.  How could I?  I can’t imagine hating you.  Ever!”

      “Even after all the wild things I’ve made you do?  Even after I paraded you everywhere today and made you show off in the most embarrassing and ridiculous ways?  You still don’t hate me?”

     His answer was slow again, but not as slow as before.  “Never!  I still can’t imagine hating you.  You have no idea how wonderful I think you are.  You have been my Mistress for two months now.  Two of the most exciting, wonderful months of my life – despite how utterly frightened I’ve been since day one!  Because of you, I’ve not only lived a dream, I’ve lived far beyond my wildest fantasies ever!  Hate you?  How could I hate someone who has let me live a dream?”  He had said that badly he knew, but it was the best answer he was able to come up with on short notice like this.

     Mel heard all his words, but what her mind heard instead was the things he didn’t say.  It sounded like he still thought he was going to win their bet.  It sounded like he was planning on everything being over with after the bet was over.  What she heard was that he planned on walking away and leaving her if he won.  Forever.  Her body shivered.  She dared not ask anymore questions. 

     She laid there with him silently for a few more moments before getting to her feet and grabbing a robe to wrap tightly around her.  He was going to walk away when it was over – if he won.  Just like all the men in her life, he was going to leave.  She reached over onto the bed and grabbed his blindfold and pried the thing off of him.  “Get your things now Sissy,” she said as kindly as she could.  “Go home.  And don’t forget to drink your bottles before you go to bed.  I’ll see you in the morning.” 

     She walked out of the bedroom and into her kitchen where she poured herself a stale cup of coffee.  As she carried it into the living room, he was just coming out of the bedroom.  She sat in one of her chairs and watched as he grabbed his things and curtseyed before saying goodbye and walking out the door. 

     “I would kiss you, till your body shudders… and you know how I feel about you.”  It was what he had said to her earlier in bed, and yet later, after he had been allowed his orgasm, he had said nothing at all about wanting to stay with her.  She had gotten the distinct impression that he would walk away from her in an instant… if he could.  Just like every other man who had ever been in her life.  And just like always, it hurt.

      “Good night Sissy,” she said quietly one more time.  “Good night.”  And a tear fell off her cheek and landed unseen in her coffee cup.

      “Yyeeouch!” screamed Ray.  He had thought he was going to do it, he had been sure he was going to finally get to cum this time.  And right when it was about to happen, he had felt her hand wrap itself around the very base of his cock and she had squeezed for all she was worth.  And she was still squeezing!  “Yeouch!  That hurts!”

     Gloria giggled.  “I know!”  Quickly, she pulled him out of her and still holding tightly onto him, moved to a new position behind him.  With her hand still squeezing the base of his cock, she leaned over and began nibbling on his earlobe.  His back arched, he was quite sensitive there.  Of course, by now, he was quite sensitive everywhere.  “Are you going to give me anymore trouble asking about things that are none of your business?”

      “That hurts!” complained Ray.  “Let go… or at least ease up some!”

      “Nope!  Not till you promise to be a good boy from now on.”

     Geez!  The tiger was certainly out for blood again tonight!  Worse than before!  He suddenly felt her squeezing him harder.  Much harder.  After not getting to cum last time and then going through the same thing again tonight, his balls were killing him as it was.  And now she was pushing that pain and making it that much worse.  “Yes, whatever!  Just ease up!”

     Gloria eased her grip, but only a little.  “With her thumb and forefinger still circling the base of his cock, her remaining fingers reached out and cupped his balls, squeezing ever so slightly.  She felt him tense up.  “Do you promise to be good?” she asked again.

      “Yes, yes,” Ray agreed quickly, afraid of the pain she had already proven she could inflict. 

     Her fingers let go of his balls, but her hand kept tight hold of his cock.  She moved around in front of him, straddling his sitting body with her legs.  She leaned back on the bed, pulling him on top of her by the grip she maintained on his cock.  As he lowered himself down, her grip guided his large penis right inside of her again.  It had been there most of the last few hours and putting it in felt more like sliding the thing home.  She felt him stiffen again at the feel of being inside of her again.  But she still maintained her grip… preventing him from achieving the release he so desperately wanted… even as his body automatically began the wonderful pumping motion again. 

      “Do you promise?” she asked one more time.

      “Yes, I promise,” Ray replied, praying that she would finally let him cum.  The feel inside of her was exquisite! 

      “No more questions about the bet with Mel and Chad?”

      “No…  more…” Ray managed to pant as his body began to pump harder and try once again to reach what she continuously denied him.

      “No more questions about Mel’s money?” Gloria asked, her own body now raging close to another orgasm.

     Panting loudly now, Ray managed to get out… “No… more…”

      “Promise?” Gloria panted in return.

      “P…  Promise!” Ray grunted.

     Gloria felt her orgasm rising again.  Damn, this guy was without a doubt the best lover she had ever had!  Right at that point… she let go of his cock completely, letting him slam the whole length of it into her.  She screamed!

     He screamed as the violence of his pent-up orgasm released itself fully into her.  Damn!  What a woman!  What a tiger!  Damn!

      “Promise?” Gloria asked one more time as, totally spent, Ray collapsed on top of her. 

      “Promise!” Ray managed to grunt out.  He was totally wasted.

      “Good!  Because if you don’t, I’m going to make things much worse on you next time.

     Ray wasn’t sure if he would ever mention the subjects again, or… if he would now go out of his way more than ever to ask about them.  Damn, the woman was good!