The Bet - Chapter 55 (Thursday – week 8 Part 2 of 9)

The Bet

By Karen Singer

Chapter 55 (Thursday – week 8 Part 2 of 9)

     He started to shake with fear as he stared at the garment she was holding in her hands.

      “It’s so pretty!” Mel exclaimed as she fussed with the horrible garment.”

      “But…”

      “No buts Sissy!” Mel proclaimed as she removed the dress from its hanger. 

      “But I can’t!” he argued.

     Mel smiled wickedly at him.  “But you can!” she responded back, letting him know that there would be no getting out of it. 

     A few seconds later, Chad shivered as the material encased his body… well, his upper body anyway.  The pretty blue dress just barely hid his diaper underneath.  How was he going to manage this today?  He didn’t have a clue!  Five minutes later, he was also wearing the pretty white socks with all the blue lace on them and his blue Mary Jane shoes with the little colorful flowers that matched the dress.  He watched as Mel found his white hair bow and only moments later, she fastened it into his hair.  He mentally screamed with each new humiliating indignation that had been added to his body.  He couldn’t go to work like this!

     Mel looked him over and smiled delightfully.  “I love it!” she declared. 

     Chad didn’t bother curtseying, he was too upset.  “But how am I going to get through work like this?” he asked.  “I can’t!”

     Mel’s face clouded as she shook her head.  “First of all, I’m sure you’ll manage… somehow.  And secondly, you did so well curtseying last night before you spoke.  What happened now?  Do you need to be punished before I take you to work?  We have plenty of time!  But if I have to take that time, you might be less happy than you are now about going to work.”

     Chad quickly curtseyed.  “Sorry, Mistress,” he lisped.  “It’s just that I don’t know how I can do this?”

     Mel just smiled.  “Trust me, you will because you don’t have a choice.”  She noticed one last thing that seemed to be missing.  “Where’s your pacifier?”

     Chad curtseyed before rushing out to the kitchen where he had dropped it earlier.  He stuck it in his mouth and hurried back again… where he curtseyed.

     Mel smiled broadly, especially at his curtsey in the silly dress.  Perfect!  “Much better!” she declared.  “Now let’s get out of here before it gets any later.”

     Chad headed for the living room, not at all happy, but he suddenly realized something.  He turned back towards Mel… and curtseyed and removed his pacifier.  “But Mistress, it’s too early to go to work.”  Curtsey, pacifier back.

     Mel smiled with amusement at what he had just done.  “Would you rather wait around a while and go when there will be more people there to see you going in?”

     Chad nearly lost his pacifier as his jaw dropped open for a moment.  That was why she had gotten him up so early.  He had a chance!  Not much of one, but it was a chance.  But how about the rest of the day?  Not wanting to delay any further, he quickly grabbed his purse and diaper bag. 

     Mel watched him grabbing his things to go.  But something suddenly struck her as out of place.  “Wait a minute, Sissy.”  And then it hit her.  “That purse is no good with that dress.  Where’s your new one, your little sissy purse?” 

     A moment later, she watched as he transferred his cell phone, keys, and some of the things out of his wallet into his silly little girl purse.  The stupid thing was so small that he couldn’t put much else into it.  The handle on it was also so tiny that he couldn’t even carry it over his arm.  But that was certainly no problem – for her.  The brightly colored purse didn’t really go with the dress he was wearing – color wise, but the style certainly matched the silly childish style of the dress better.  “Now we can go,” she told him.

     Once again, Chad found himself outside of his apartment wearing one of his silly sissy dresses, only this time, he was going to work in it!

      “My car,” Mel said as she closed Chad’s apartment door behind them.  “I’ll drive you today.”

     Chad realized that she was making sure he was going to get there.  She wasn’t going to give him any way out at all.  It was almost like the first time he had worn this dress out in public, so many weeks ago now – the time she had driven him to work and threatened to make him go inside.  They had gone to the gym instead where he was forced to make a total fool of himself – as usual.  But Mel had been threatening to send him to work in this outfit ever since.  And now it looked like that day had arrived.

     He was nervous to begin with, but surprisingly, getting into her car didn’t actually increase that nervousness at all.  But pulling out onto the main road did.  Sighting his company’s building as they were still driving toward it increased his nervousness as well.  Pulling into the parking lot was much worse.  And when Mel stopped her car at the curb near the door his stomach felt like it was on a wild rampage.  “What am I going to do?” he asked desperately, as much to himself as to Mel.

      “You’re going to go in and go to work,” Mel replied with a grin on his face. 

      “No, I mean… how about the rest of the day?”

     Mel just smiled.  She and Robin had discussed much of this in detail yesterday.  Much of it though was going to be left up to Robin’s discretion.  But she didn’t want Sissy to know any of that.  “You’ll just have to do the best you can.  Now, since it’s so early, you have plenty of time to drink another bottle or two after you get inside.  And you probably better.  Robin is expecting to see you leaking by the time she arrives, so I suggest you work very hard on that.”  Mel’s smile turned wicked.  “I’m sure she’ll probably check that first when you curtsey for her out in the hallway when she arrives.  Wouldn’t it be fun if she had someone else there with her this morning to see you in your pretty dress?”

     No, it wouldn’t be fun!  Chad knew that Mel had to be teasing about someone else seeing him… which was all too possible… especially out in the hallway.  But he was still having a hard time coming to grips with the fact that now Robin was going to make sure he kept his diapers leaking as well!  Now he knew why Mel had made him wear only the one diaper this morning.  But with so much time still to go, he had no worries about leaking before Robin got there. 

      “Now it’s time…” Mel started to say.

      “Wait!” Chad stopped her quickly as a car pulled into the parking lot and pulled into a space right near them.  Chad could see two men in the front seat of the car.  “Can I at least wait till after they get into the building?”

      “Sure, if you like,” Mel replied. 

     They watched as two men got out of the car.  Deep in conversation, the men barely gave Mel’s car a second glance as they walked slowly into the building.  But they hadn’t even reached the door yet before another car pulled in. 

      “I can’t wait here forever, Sissy,” Mel said.  “Eventually, you’re going to have to go in.  One way or another.”

      “Just a little longer… please,” Chad begged.

     Mel said nothing.  They just watched as the second car parked near the first car and the driver headed from his car toward the doors.  This man wasn’t as distracted as the first men had been though and they saw him not only looking at Mel’s car, but he almost stopped for a closer look.  Chad was cringing inside as he realized the man had seen the silly blue dress he was wearing.  But he also realized that the man couldn’t see very much of it, so maybe he was okay.

      “The later it gets, the more people are going to be around,” Mel reminded him.

     Knowing she was right, Chad knew he had to go… and go soon, not to mention fast.  As soon as the man had entered the building, Chad got out of her car.  He opened the back door and grabbed his diaper bag as fast as he could.  Then, with his pacifier clamped between his teeth, at almost a dead run, his little girl purse seeming to fly around in his left hand, and his petticoats swishing all over the place, he ran for the cover of the building ahead.  He couldn’t believe he was doing this!  He couldn’t believe he was actually here… wearing this dress!  How was he going to manage this today?

     As he opened the door, he heard something and turned around.  Mel was driving off – stranding him here, leaving him no way to leave.  He shivered at the thought.  Then, because he knew things could only get worse the longer he delayed, he hurried though the empty hallways all the way to his desk.  Whew!  Now he just had to get through the rest of the day.  And what about breaks?  Not to mentions lunch… and going home?  Things did not look good!

     Robin was a few minutes early, but only a few.  She had hurried to work today only because she couldn’t wait to see what Sissy would be wearing.  Mel had told her she would put him in something “more interesting,” but she hadn’t said exactly what.  And Robin had assured her that she would “manage” a few of Mel’s concerns in return.

     She entered the building, saying hello to several women she knew, then traversed the hallways toward her desk.  What would he be wearing?  She really couldn’t wait to see.  She finally turned into the hallway where their cubicles were located… where Sissy should be waiting out in the middle of the hallway to curtsey and greet her.  Except that the hallway was vacant.  No Sissy.  Where was he?

     A head briefly popped out sideways from behind Sissy’s cubicle wall.  The white bow on top of the head grabbed most of her attention.  There he was!  But before she had a chance to even think anything else – like why wasn’t he already standing out in the hall waiting for her – he quickly came into view… and all ability to actually think left her as she stopped dead still where she was.  She stared, not really sure she was seeing what her eyes told her they saw.  And then, despite herself, she squealed with delight and nearly ran the rest of the way toward him.

     Chad nervously curtseyed as Robin got close.  He removed his pacifier.  “Good morning, Robin,” he lisped in his sissy voice.  Then he curtseyed again as he was required to with her and stuck his pacifier back in his mouth.

     But Robin barely noticed anything of what he had just done, she was too intent on examining his dress in minute detail.  “Oh God!  It’s gorgeous!” she gasped as she walked all the way around him. 

     Chad just wanted to get out of the hallway.  The longer he stood there, the more chance there was that someone else might notice him.  Besides, he had another problem that needed dealing with.

     Robin didn’t bother taking her bag to her desk, she simply set it down on the hallway floor off to the side before taking yet another tour all the way around him.  “Gorgeous!” her awed voice gasped once again as she got back to his front.  “And the shoes…  They’re darling!” she added.  “They absolutely make the outfit!”

     She stepped back away from him so she could see all of him better.  In that mockery of a childish little-girl outfit, there was no way she could ever see him as being anything but a sissy.  Mel had certainly come through with her promise to dress him in something more interesting!  “Is that the outfit you wore to the gym that day?” she asked, remembering what she had found out from her questions when she had first joined the gym.  She was still going to the gym twice a week.  She would be going tonight as well.  She just never asked about Sissy anymore.  What would be the use? 

     Chad removed his pacifier from his mouth and curtseyed.  “Yes,” he replied before curtseying again and sticking the pacifier back in his mouth again.  In the stupid outfit he was wearing, having to suck the pacifier seemed almost normal.  Of course, with Robin, she usually had him sucking his thumb instead, but surprisingly, he thought he preferred the pacifier.  Now if she would just let him out of the hallway!

      “Uh oh!” Sissy suddenly grunted, not bothering to curtsey.  Like it or not, he ran back to his cubicle. 

     Surprised and mystified Robin watched as he quickly grabbed a baby wipe that had been laying on his desk.  She nearly laughed as he bent down and wiped a line of pee that had descended most of the way down his left leg.  Then he fought with his underskirts a bit so he could wipe a little bit of his right leg as well up close to his diaper.

      “I take it you’re leaking,” Robin said with some amusement as she came into his cubicle.

     Chad didn’t feel like an answer was needed, but he set the wipe he had just used on his desk again and curtseyed.  Removing the pacifier he said, “I really need a diaper change,” then he curtseyed again, and stuck his pacifier back in his mouth.

      “Yes, I can see that,” she told him.  “Mel told me you could manage it yourself.  Can you?  Or do you need my help?”

      “I can do it,” Chad replied in the middle of his annoying curtsey routine.

     He paused for a moment to see if Robin would leave him to do it privately, but she didn’t. She just stayed right there with him.  Since he needed a change and she wasn’t going to leave, he reached into his diaper bag and grabbed a fresh diaper – along with another baby wipe.  He tried to pull his petticoats out of the way, but that didn’t work very well.  Having to do it by feel alone, he worked his way past the netting and carefully peeled open the tapes holding his soggy diaper in place.  Once the diaper was loose enough, he let the weight of it pull it slowly down his legs where he stepped out of it on the floor. 

     He reached over to his desk where he grabbed the baby wipe and wiped himself and his chastity device clean.  Because of all the netting under his skirt, he couldn’t really see what he was doing and he realized that there seemed to be one added advantage to all that netting, it was providing him with a tiny bit of modesty as he changed himself. 

     Then he grabbed the fresh diaper.  He heard a small giggle out of Robin as he was turning back again.  He had no doubt she was amused by all of this.  But when he looked at her, she was staring down at the floor.  “Damn!” he muttered softly to himself. 

     Robin only noticed it because she had been watching that part of him so intently as he went about trying to diaper himself with his dress still on.  She was amazed he had managed to do what he did.  But when she suddenly saw the weak spurt of pee come out of him to land on the tile floor, she couldn’t help giggling.  And his reaction made it obvious that he didn’t even know he had done it.  And he still thought he was going to win this bet?  Not as far as she could tell.

     She watched as he opened the diaper and, still standing, pulled it through his legs and up into his crotch.  But once again the skirts he was wearing were getting in his way.  “Here, let me help,” she said as she moved forward and grabbed some of his dress, gathering the skirt and netting and pulling one side of it up and out of the way. 

      “Thanks,” Sissy replied through the pacifier in his mouth as he quickly fastened the tapes on that side of his diaper. 

     Robin pulled the other side of his dress out of the way and he fastened the other side. She noticed that he did his best to pull the thing as tight as possible so it wouldn’t fall off.  She dropped his skirts.  “You did that pretty well,” she said approvingly.

     Chad was about to speak without curtseying, but figured that maybe he better – just in case.  Curtsey.  Pacifier.  “I’ve had lots of practice,” he replied.  Pacifier.  Curtsey

      “Yes, I’m sure you have,” Robin replied.  She took a moment to glance through his diaper bag.  The usual six bottles and more diapers than usual.  That was good.  She pulled one of the bottles out of his bag and handed it to him before picking up his entire diaper bag.  “My place,” she said as she walked out.  She grabbed her own bag from the hallway before entering her cubicle. 

     Chad was cautious enough to stick his head out to see if anyone was coming before quickly following her into her cubicle, where he soon found himself on her floor drinking yet another baby bottle of Mel’s lousy green tea. 

      “According to Mel,” Robin told him, “you’ve now got an hour and forty five minutes to be leaking again.  So make sure you drink as much as you need to.  Don’t wait for me to tell you to get one, just do it.  And don’t worry about running out.  I’ll make sure you get all the bottles you want.  I’ll even refill them myself for you.  Now won’t that be a big help?”

     Chad was actually surprised and… somewhat grateful.  Somewhat.  He didn’t say it, but since she was going to be refilling them, what was she going to be filling them with?