The Bet - Chapter 55 (Thursday – week 8 Part 1 of 9)

The Bet

By Karen Singer

Chapter 55 (Thursday – week 8 Part 1 of 9)

     Back… and forth… and back… and forth.  In his dreams, he was once again dressed as a baby… a baby girl of course.  Naturally, he was thickly diapered and sucking on a pacifier – mimicking his situation in real life.  But that of course wasn’t what his dream was about.  He was wearing a little-girl style dress – all pink and white lace with ribbons and bows everywhere.  The short skirt was puffed out very wide by all the petticoats underneath, displaying his diapers and plastic panties below.  And on his feet were lacy little girl socks and mary-jane shoes.  A little girl…  With overly thick diapers under her dress that did nothing to hide them.

     Back… and forth… and back… and forth.  He tried to remove the dress, but it was somehow locked onto him.  He tried to bend over to remove his shoes, the delicious petticoats hampering his efforts… but the shoes were locked on too.  He put his hands on the waist of his plastic panties and found them locked on as well.  Trapped!  In Everything!

     Back… and forth… and back… and forth.  People kept coming by and pointing at him… and laughing at him.  Back… and forth…  He loved the humiliation, he hated it.  But it was fueling his sexual fantasies.

     Back… and forth… and back… and forth.  But it wasn’t just the dress and the fact that others were laughing at him that was stimulating his sexual excitement so much…  Back… and forth…  It was something his mind was feeling in his backside.  Something that felt like it was stuck up inside of him – stimulating that now sensitive area that was trapped underneath all the layers of his thick wet diapers. 

     Back… and forth… and back… and forth.  As his dream continued, he wasn’t even aware that he was doing it.  But his body was pressing his backside down against his blowup mattress, trying to grab more stimulation from the pressure that translated to the imaginary something his dream thought was inside of him.  Back… and forth.  His hips pushed forward, but not to try to give any sexual stimulation to his completely encased penis on his front side.  No, it was only because his mind was trying to gain the stimulation from the toy his dreams had imagined was buried in his rear end. 

     Back… and forth… and back… and forth.  Dressed as a silly sissy baby.  Back… and forth… and back… and forth.  Trapped in all his clothes.  Back… and forth… and back… and forth.  Such wonderful humiliation.  Back… and forth… and back… and forth.  Sweet stimulation from the something buried up inside of him under his diapers.  Back… and forth… and back… and forth.  He could feel it somehow moving in and out as his dream-self waddled and paraded helplessly in front of so many people. 

     Back… and forth… and back… and forth.  As the stimulation seemed to grow, so did his awareness and the details of the clothes he was wearing.  Back… and forth… and back… and forth.  All of it sending him further and further toward his ultimate humiliation – that obviously was going to take place right in front of all those people! 

     Back… and forth… and back… and forth.  His excitement grew as his hands played with his frilly dress.  Back… and forth… and back… and forth.  It grew more as he thought about the sissy shoes stuck on his feet.  Back… and forth… and back… and forth.  He could feel it passing the point of no return as his dream mind was aware of everyone watching him so closely. 

     Back… and forth… and back… and forth. 

     Faster now.  Back… and forth… and back… and forth. 

     And faster.  Back… and forth… and back… and forth. 

     Whatever his mind had conjured up to fill his back end with was suddenly more real… more solid.  He felt the stimulation much stronger.  Instead of moving in and out of him, it almost seemed to be going only out instead – and for a very long time.  He felt his front side peeing uncontrollably in response.

     Back… and forth… and back… and forth. 

     His real-life body arched its back as his dream body whimpered in ecstasy.

     Back… and forth… and back… and forth. 

     And he climaxed in his dream… right in front of all those people!  How humiliating!

     He climaxed too in real-life.  But locked in his deliciously humiliating dream, he would never know that. 

     As the climax in his dream started to fade, his mind did everything it could to hold onto it as long as possible.  The most humiliating dreams and thoughts he had ever had were pulled desperately into his dream… just to prolong the already lost feeling just a little longer. 

     But as all dreams go, this one too faded into nothingness.  And when it was done, his body and mind both slept calmly for the rest of the night.  Until…

     The awful blaring music erupted from his pink clock radio pulled him viciously out of his sound slumber.  If it wasn’t so loud and annoying, he might have laid there for a moment to collect his wits before turning it off.  But the sound was so annoying that even thinking about doing so was out of the question.  He desperately rolled off his blow-up mattress onto the floor, scattering the usual collection of empty baby bottles in the process.  A moment later, his bedroom was again returned to blissful silence, even though a memory of the irritating loud music seemed to haunt the air. 

     He breathed with his eyes closed for just a moment, pretending he could go back to sleep just as he was… on his knees.  But as usual, that was out of the question.  He opened his eyes and saw the clock radio in front of him… it was set a half hour earlier than it had been yesterday… which had been a full hour earlier than usual!  No wonder he still felt so tired!  Why had Mel gotten him up so early?

     With a sigh, he forced himself to climb to his feet, his overly saturated and bloated diapers hindering him in the process.  Yes, they were heavy again, very heavy.  The thick cloth diapers seemed to get even heavier and more bloated than layers of disposable ones.  As he took his first waddling steps away from his blow-up mattress bed on the floor, he scratched for a moment at his bra that supported his glued on breast forms.  But he didn’t give that any other thought. 

     His mind felt extra foggy in the extra early morning as he stumbled wide-leggedly through the darkness and into his kitchen.  He fumbled along the wall to find the light switch and flipped it on.  Brightness assaulted him.  As soon as he could see clearly again, his eyes automatically focused on the short note she had left there… his first instructions for the day.

Sissy,

Don’t forget your usual three bottles first.  After that, get cleaned up and diapered for work – only one disposable today.

Do your hair, but don’t do your makeup.

Wear your diaper and a bra and nothing else when you come here – early!

The later you get here, the less you’re going to like it!

     He had to be dreaming!  The note made no sense!  How about getting dressed for work?  And what was the business about getting there early?  How early?  She hadn’t set an exact time for him to get there… just… early!  And of course, she must have meant it to threaten him like she did at the end. 

     Early?  Why?  Not for any reason he knew of.  And only one diaper?  This was a work day! 

     Bowing to the inevitable, he removed the pacifier from his mouth and grabbed his usual three bottles of her lousy tea from his refrigerator.  He carried them to his one and only piece of real furniture – his tired old chair facing his wall of shaming pictures.  But once again he didn’t see the pictures, especially since he closed his still sleepy eyes the moment he put his first bottle to his lips and started drinking. 

     Early?  What did early mean?  And more importantly… why?  And… did he dare let himself fall asleep in his chair as he drank?  Better not!

     Mel forced herself out of bed with an audible groan.  It was too early!  Way too early!  But early was the only way.  The only solution she had come up with. 

     She made it out of her bedroom with no trouble, but entering her living room, her hand had to swipe at the light switch on the wall since the sun was just now starting to come up.  The harsh light forced her to squint and blink till she got to the more dimly lit kitchen – where she purposely didn’t turn on another light.  She didn’t really need it, the light filtering in from the living room was more than enough.

     She prepared her coffee maker and turned it on… and closed her eyes as she stood sleepily right in front of it.  Early… too early!  She could easily fall asleep again on her feet.  She had stayed up too late last night trying to read that infernal contract!  Damn the thing!  It was interfering too much into her life right now.  She had other things she needed to be concentrating on instead – like winning the bet with Sissy.  She had even cleared most of her schedule next week just for that purpose.  But the damn contract…  And you don’t say no to Mr. Feinbaum.  Besides, it was a boatload of money.  Two boatloads!

     She pulled her cup out of the cabinet before the coffee was ready in hopes that somehow the action of having the cup ready would hurry the coffee-maker’s progress.  It didn’t.  The darn thing seemed to take twice as long instead, irritating her slightly.  But the moment she was able to sip at the hot liquid from the freshly made coffee, a small sense of bliss seemed to wash over her.  She took a deep breath holding the steaming coffee right under her nose so she could enjoy it’s aroma… before taking another much needed sip. 

     Instead of carrying the cup out to her living room to sit with it as she usually did, she carried it into her bedroom instead, where she forced herself to dress in a t-shirt and a pair of shorts.  Her coffee cup was mostly empty by the time she headed back out to the kitchen, feeling much more awake and with-it now.  She refilled the cup and gabbed one of her pots out of the bottom cabinet before reaching into the top cabinet to pull out a box of baby cereal.  Five minutes later, she was humming softly to herself as she stirred the mixture in her pot. 

     Chad had no idea what was going on.  None!  After wearing three diapers every day for a while now, getting ready for work with only one diaper felt strange… and a whole lot less secure.  Her note had said get diapered for work, so she must have meant that he would be wearing only the one diaper when he left.  But was it a mistake?  Somehow, he didn’t think so.

     He had done his hair as required.  But no makeup?  And worst of all, no clothes?  Why?  What did Mel have planned?  And the only thing his still sleepy brain could come up with was that it was going to be something humiliating.  But then, his whole life was humiliating.  Nonstop! 

     With nothing more to check, he grabbed his plastic bag full of empty baby bottles, along with his purse and his diaper bag.  He was glad it was so early since he would be going outside wearing only his diapers – one of the most humiliating things for him to wear out in public.  But at least it was only to go next door to Mel’s apartment.

     With nothing more to delay him, he went out his door and locked it behind him.  He silently braced himself for something humiliating as he knocked at her door.  After a moment he got no answer.  Was she even up yet at this hour?  He knocked again, and was rewarded when she opened it immediately. 

     He curtseyed.  “Good mowning Mithdweth,” he said in his stupid lisping sissy voice before curtseying again.

     Mel smiled.  “Good morning Sissy,” she replied as she stood back out of the way.  She took the bag of empty bottles from him as he walked in.  There was nothing much for her to inspect about him this morning so she waited for him to put his things under her little table before saying, “I’ve got your breakfast all ready.  You can get into your chair now.”

     Chad curtseyed again and headed for the kitchen… and his humiliating highchair that he always ate from whenever he was in her apartment.  Two minutes later, he was locked into the chair wearing just his one diaper and a bra.  The bib that Mel tied around his neck actually made him feel less like a baby – surprisingly.  He waited as Mel brought his breakfast of baby cereal over to him and set it on his tray along with another baby bottle and a tiny baby spoon.  He grabbed the spoon in his left fist like he always did now and started eating, doing his best to not spill any of the cereal and make himself look even more infantile than he already was.

     Would she tell him now why she had gotten him up so early?  Why he wasn’t dressed?

     His eyes watched her as he spooned the awful mush into his mouth.  They watched her as she grabbed his diaper bag and carried it over to her refrigerator where she removed the empty bottles and replaced them with fresh ones.  He watched her as she carried the bag out to the living room again where she was gone for a few minutes before coming back.  He watched her as she grabbed her coffee cup and refilled it and took a sip.  He watched her as she leaned back against the counter like she often did when she watched him eating… or to talk to him. 

     Now?  Was she going to tell him what was going on now?  But she just stood there and watched him eating… perhaps with more amusement on her face than he had seen for a while. 

     Why was it so early?  Why wasn’t she telling him?

     He finished his cereal… and she still hadn’t told him anything.  He grabbed what was left of his bottle and put that to his lips as well, watching her the whole time, waiting for her to speak the whole time.  But she just stood there and drank her coffee… and watched him back. 

     Why?

     And as soon as his bottle was done, she was immediately there to take it from him, wiping his face and hands with his bib and releasing him from the confines of his silly chair. 

     Would she tell him now?

     But instead she headed back out to the living room.  He followed her and found her grabbing her purse.  “Okay Sissy,” she said as she headed for the door.  “Let’s go.”

     Go?

     Nervously, Chad grabbed his purse and the now heavier diaper bag, and still wearing only his diaper and bra, followed her outside fearing that she intended on taking him to work dressed like he was.  They were certainly heading the right direction since the stairs down to their cars was straight ahead. 

     He was hugely relieved when she stopped at his apartment door instead and fished her key out of her purse.  She opened the door and he followed her inside.  She wasn’t going to send him to work dressed in just his diapers – hopefully.  But why didn’t she just tell him what she wanted him to wear earlier?  And why was it so darn early?

      “This way Sissy,” she said as she headed for his bathroom.  He dropped his bags on the floor near the door and followed her. 

      “I want to do your makeup first,” she told him. 

     Why hadn’t she had him do his own makeup this morning?  She had him sit down on the toilet while she studied his face for a moment before attacking it with the makeup.  Although it seemed like she wasn’t using nearly as much today as he usually did every morning.  Why?

     From the bathroom, he followed her into his bedroom where he expected her to tell him to get into his usual waist cincher and all-in-one girdle.  But she went straight back to his closet instead.  He watched as she looked inside at all his clothes for several moments before pouncing on something and proclaiming, “Aha!”

     And Chad’s knees went weak as she turned around.

      “Oh no!  No Mistress!  Please!  I can’t wear that to work.  Not to work!” 

      “Yes you can… and you will!” Mel replied forcefully as she ran her hand briefly over the material of his blue sissy baby dress.