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!