The Bet - Chapter 53 (Tuesday – Week 8 Part 7 of 10)

The Bet

By Karen Singer

Chapter 53 (Tuesday – Week 8 Part 7 of 10)

     Chad was growing tired.  He was making more and more fat-fingered – fat-heeled mistakes.  And he had only been back to work on the email for less than an hour.  His heel slipped off another key as he pressed down and struck a second key.  “Darn!” he muttered as he lined the heel of the shoe up over the backspace key to delete the letter.

      “Bottle time,” Robin suddenly announced as she came back into his cubicle. 

     Chad was so sick of trying to type with his shoe heels that he actually welcomed the break.  He wasn’t too sure about how much he welcomed having to drink another bottle though.  And it had been less than an hour since he finished his last one.  But a few seconds later, he was pulled away from his desk with the bottle held precariously between the two shoes taped to his hands.  He still didn’t seem to be getting any better at managing to hold the bottle between the shoes. 

     Robin checked on him twice before he finished the bottle.  And then she pushed him firmly back up against his desk again.  He felt himself peeing uncontrollably once again before he even began trying to type.  Why bother trying to hold back at all?  What good would it do?  He knew without a doubt that as soon as this bet was over with, he would regain everything he had lost very quickly.  Why not enjoy what he always wanted to experience while he could? 

     In the back of his mind he knew there were a lot of things wrong with that logic, but he didn’t let those thoughts come fully through to his consciousness.  What would be the point?

     Forty-five minutes later, he was starting to look forward to finishing his email – finally!  He was starting to push himself to finish it faster.  But he didn’t make it, because before he could finish, Robin came in with yet another bottle for him to drink.  Once again he was pulled away from his desk and had to fight to hold the bottle between the shoes taped to his hands.  He thought that by now it would get easier to manage, but it didn’t.  The shoes simply weren’t meant for gripping anything at all.  Maybe not even for gripping the ground when he walked in them – because walking in them was fairly precarious too. 

     Robin came in to check his progress twice again before he actually finished his bottle, and then she once again pushed him back into place at his desk.  “Send that to me when you’re done so I can check it before you send it to Mel,” she ordered.

     It took Chad less than ten minutes to finish what he had been trying to do all day.  As he finally managed to type Robin’s email address into the bar and send the thing to her, he breathed a small sigh of relief – but it was only a small sigh.  He’d feel much better once she okayed it and he could finally get it sent to Mel.

     But now that he was done, he was still tied to the chair and the shoes were still taped to his hands.  He knew he could push himself backwards a bit so he wasn’t so close to his desk, but did he dare?  What if she found an error and he had to fix something?  Which now that he thought about it, seemed all too likely knowing her.  So to be safe, he sat quietly right where he was.

     The wait seemed like forever, but it was only about five minutes before Robin came back to his cubicle.  “I’m impressed!” she declared as she entered his cubicle.  “I didn’t see one single error in the whole thing.”

      “So I can send it to Mel now and be done with it?” Chad asked.

      “Absolutely!  Just as soon as you finish your next bottle.”  With that, she pulled him away from his desk again and held the bottle out for him to take between the shoes taped to his hands.

     Another bottle!  When would it stop?  He reached out and precariously grabbed the bottle and started bringing it to his mouth, but his grip with the shoes was worse than usual and it slipped and fell to the floor.  Robin giggled and handed it back to him. This time he managed to get it all the way to his mouth.  He dared not take it out of his mouth till he finished because his lips worked like a third hand to help hold the darn thing in place. 

     With a smile, Robin left him again.  She figured by the time he finished that bottle, and then managed to send his email, it would be time for break.  This time, when she went back to check on him, she timed it better – she only had to wait a couple of minutes for him to finish the bottle.  She took it from him and pushed him back up against his desk.  This time she stayed to watch while he slowly and carefully typed in Mel’s email address – letter by careful letter.  While he didn’t make any mistakes as she watched him, she figured she had definitely found a way to slow his typing down.  Plus… she found it awfully funny to watch him.

     With the email to Mel finally sent, Robin untied him from the chair and removed the shoes from his hands.  As soon as Chad stood up, he pulled his skirt down again.  He could already feel how bloated his diapers were getting underneath and between his legs.  He hoped they weren’t showing yet.  Way too many bottles since lunch! 

     A few minutes later, they were walking through the halls together on their way to the break room.  The hallways were busier this time than Chad would have liked.  They got even busier the closer they got to the break room.  They were arriving at the same time as everyone else.  Before he knew it, a woman rushed up to him and walked along with him on the side opposite from Robin. 

      “So has it been fun?” the woman asked.

     Her question surprised him.  “Fun?”

      “You said earlier that you dressed for work that way because you thought it might be fun?  So has it?”

     Chad thought about that for a few moments.  There had been that bad bit during lunch.  That had been horrible!  But overall?  “Mostly,” he admitted.  “Mostly.”

      “Mostly?” the woman asked, wanting more details.  But just then they arrived at the break room door and pushed their way inside along with a host of others.  The line for coffee was long and they were in the middle of it.  “Mostly?” the woman asked again. 

     But it was Robin who answered for him.  “He had a rather frightening experience during lunch,” she said.  “I think we should wait till we get to the table.  Then we’ll tell you all about it.”

      “Frightening?” the woman asked, totally surprised.  “What happened?”

      “At the table,” Robin replied, knowing it would be much better to explain it all once rather than a dozen times.

     Chad wasn’t at all looking forward to reliving the experience.  He’d just as soon forget it.

     As they stood there, Robin noticed a group of men sitting at one of the tables in the back corner.  It looked like they had been there a while and the table was filled with paperwork.  It was common for working groups to use the break room tables to discuss business.  But there was one thing about this group that stood out from most others.  She leaned over and whispered to Sissy.  “Isn’t that Derek at that table?”

     Sissy looked.  Derek was there.  The one person he had hoped not to see today.  “Yeah,” he whispered back.  He turned his head away so he wouldn’t have to look at the table and hopefully Derek wouldn’t notice him.

     Robin finally got to pour her coffee, then she waited while Sissy poured his.  As soon as he was ready, she leaned in close to him and whispered.  “As soon as you set your coffee on the table, I want you to go over and ask Derek if you can get him some coffee too.”

     Chad was horrified.  Talking with Derek right now was the last thing he wanted to do, especially dressed like he was!  “Please!  I’d rather not,” he pleaded, trying to get out of it. 

     Robin only smiled.  “I’d rather you did.”  She led the way directly to their usual break table, which was now filling up quickly.

     The woman who had been asking the questions as they arrived was right behind them.  “So what happened?” she asked anxiously before any of them had even sat down. 

     Chad didn’t know what to do.  Answer the woman’s question or go see Derek like Robin wanted.  Since he didn’t really want to see Derek at all, he turned toward the woman.  “While I was out at lunch…”

      “Why don’t you let me start telling it,” Robin interrupted.  “I know how anxious you’ve been all today to see to Derek.”

     Chad got the hint – unfortunately.  Amidst a few gasps from the women at the table, he turned and headed for the back corner where Derek was.

     As Sissy left the table, Robin saw that the eyes of every woman there were firmly on him.  “So you want to know what happened during lunch?” she asked.

     Nobody took their eyes off of Sissy.  “Later girl,” one of them said.  “I’m thinkin’ we now know why he wore that outfit to work!”  It was all Robin could do to keep a straight face.

     Derek’s back was to him, so Chad was fairly confident that Derek hadn’t seen him yet.  With a growing sense of nervousness, he approached the table where all the men were intently working.  One at a time, each of the other men locked their eyes on him.  As they did, their expressions of disbelief were all too plain to read. 

     Finally, Derek noticed his friends and turned around.  His expression started off as disbelief, then quickly changed to anger.  “What do you want?” he asked nastily.

      “Um…  I just wanted to know if I can get you another cup of coffee.”

     Derek took the time to slowly look up and down Sissy’s entire body, from the top of his head to the shoes on his feet – and back again.  He wasn’t sure if he felt anger, or contempt, or pity for the “thing” standing in front of him… or guilt because Chad used to be his friend.  But there was still no way he could ever think of Chad as his old friend again.  All he saw now was someone… contemptible.  “Didn’t you wear that to the poker game?”

     Chad nodded.  “Some of it.”

     Derek shook his head before even considering Sissy’s question.  Finally he said.  “Sure.  Why not?  Sure, get me a cup of coffee if you want.  Black.”

     Chad nodded and hurried off to the coffee pots.  He had to wait behind three people before he could pour Derek’s coffee.  Then he carefully carried it back to Derek and set it on the table next to him.  Not knowing what else to say, it was all Chad could do to stop himself from curtseying.  “Um… anything else?” he finally asked.

      “No,” Derek replied.  “That’s it.”

     Again, it was all Chad could do to not curtsey.  He turned and left.  But before he took two steps Derek called, “Wait a minute!”  Chad turned around.  Derek looked to each of his friends.  “You all want another cup, don’t you?”  Not waiting for them to reply he turned back to Sissy.  “While you’re at it, you can get each of us a cup.”

     Chad wanted nothing better than to get back to his seat with the women… as strange as that sounded.  But he just nodded his head and turned toward the pots. 

      “Bring them separately!” Derek called after him. “So you don’t spill any!”

     Chad had to make a separate trip for each of the other three guys at the table.  He noticed as he did so, that not only were the guys watching him the entire time, so were all the women.  He felt so much on display he could hardly stand it.  But all he could do was to get the coffee for each of the guys, one cup at a time while the entire room watched him. 

     When he had finally delivered the last cup, he asked, “Anything else?”  Again, he was tempted to curtsey but he didn’t.

     Derek said, “No.  See you later.”  And he purposely turned his head away.

Chad finally walked back to the women’s table, noticing that every one of them was staring at him… still.  And was Robin laughing?  He noticed an awful lot of broad smiles on the faces of all the women as he sat down.

      “So tell me, Honey,” one of the women said. “You want to explain just what kind of fun you had in mind when you wore that outfit today?  And I think it’s pretty obvious to all of us now just who you wanted to have that fun with!”  There were some chuckles from all around the table.

     Chad just blushed.  But he realized that it was probably better for the women to think what they did instead of telling them just what kind of a sissy he really was.  But still…  “It’s not really like that,” he tried to explain.  “We’re just friends.”

      “Oh sure!” Another woman replied.  “I’m betting you’re very good friends!”  There were more than a few who laughed with her.

      “Okay,” the woman who had come in with them asked anxiously.  “So tell me what happened earlier.”

     Chad started again on his experience.  “This afternoon, while I was out to lunch, I stopped to buy a bottle of water…”

      “And he was attacked!” Robin finished for him since he was taking too long to tell it.  “Three guys grabbed him and tried to drag him away!”

     There were gasps of horror and shocked looks on the faces of everyone at the table. 

      “You’re kidding!  What did you do?” one of them anxiously asked.

      “I tried to get away, but two of them grabbed me again and started pulling me down to their car at the end of the parking lot,” Sissy replied.  “Fortunately, the police arrived and chased them off.  I was never so scared in my life!”

      “I’ll bet!” one of the women replied. 

      “What did the police say about you?”

     Sissy shook his head.  “That’s just it, he didn’t say anything except to ask if I was alright.  Of course, I was safely locked inside my car by the time he finished chasing them off so I’m not sure how much he saw.

      “Oh honey!  If he was able to see them attacking you, then I have no doubt that he saw plenty!”  There were general murmurs of agreement from all around the table.

      “Now you have another reason to think more carefully about what’s appropriate and what’s not appropriate to wear!” one of the women told him.  “Something like that may be fine for the bedroom, but not for anywhere else!”

     Chad could only agree, but there was no way he could tell them that what he was wearing was not his choice at all.

      “So are you and Derek planning some fun later tonight?” one of them asked mischievously. 

     Sissy heard Robin giggling.

      “Now that you’ve sent your email to Mel,” Robin said quietly as they walked back to their desks after break, “are you ready to try doing some real work again?”

     Chad almost curtseyed to her right there in the hallway in his excitement over getting to do some normal work.  Once again he had to force himself not to since they were still surrounded by all too many other people.  “Definitely,” he replied.

      “Good, because I’ve got plenty that you can get into now.  Just as soon as you finish your next bottle.”

     Ugh!

     Thirty minutes later, Chad was working on their project again.  His shoes were strapped to his feet where they belonged and he wasn’t even tied to his chair.  Normal!  But since Robin had taken so long developing everything she had created, she had left a large backlog of things for him to do. 

     And now that he was back to work normally again, that’s when the darn suppository that Cassie had shoved up inside of him decided to go to work – just like it normally did every day about this time.  He stood up to let the process go faster and easier, but today it seemed to be anything but faster – or easier.  In fact, it almost felt like what was coming out wasn’t totally liquid mush like it usually was.  He decided that it was probably because of the different girdle he was wearing. 

     When it finally finished, he sat down more gingerly than usual, but he noticed when he did that he could now see his plastic panties showing below his hiked up skirt – and the bottom of his girdle.  He figured it was a good thing that break was over already.  But how was he going to get back to his car after work without anyone noticing?  He mulled that problem over in his mind as he started in on the project again.

     

     Ray had heard of course that Chad had dressed “like a hooker” for work today, but he hadn’t seen him.  Actually, from the descriptions he had heard it sounded an awful lot like the way Sissy had dressed for the poker game – and he didn’t think he wanted to see that again. 

     As he was walking from one office to another, he happened to overhear a few of the women talking about Sissy – and Derek!  He slowed down, but he didn’t want to appear like he was eavesdropping so what he picked up didn’t make much sense since what little he heard seemed to be about Sissy dressing the way he did just for Derek. 

     Further into his journey, he noticed another group of women gossiping.  He slowed his steps and caught a few more snatches of the conversation, which seemed to be all about Sissy and Derek being like boyfriend and girlfriend.  

     No, he must have heard it wrong.  He knew Derek all too well.  Derek was his main rival for the women here at work.  Derek would never be interested in a flake like Sissy.  Still, it was odd that the women should all be talking about it.  And this was a rumor about Derek that he hadn’t even started! 

     As he continued on, he wondered if there was any way he could use that rumor against Derek.  But from everything he could already see, that job had already been done for him… and from the looks of things, all the women around didn’t exactly consider it a rumor! 

     Knowing Derek though, there had to be more to it than the little bits he had heard.  He wondered what Derek thought about it.  But did he dare ask him?  Definitely!  He just needed time to talk to him… and to find Derek of course.  That was often the biggest problem.

     It wasn’t till late in the day that he finally found Derek at his desk.  “Hey, lover boy,” he said as he walked into Derek’s office.  “What’s all the rumors I hear about you and Sissy being together now?”

     Derek had been feeling pretty good all day, but Ray’s jibe irritated him terribly.  It was all he could do to not yell back what an incredible imbecil he was!  With controlled anger in his voice he asked, “What do you mean?”

      “Oh, I just heard that you and Sissy were an ‘item’ now.”

      “An item?  The little shit used to be my friend!  Now he’s probably the biggest flake on the planet.  Get a grip!  You know I’d never date anyone like that!”  He paused and put a sly smile on his face.  “Besides, I’m going out with someone really nice right now.  In fact, she invited me to her place for dinner tonight.”

     Ray was startled, not to mention a bit jealous.  He still hadn’t found a date for tonight.  “Who?” he asked.

     Derek sat back in his chair and just smiled.  He decided not to tell Ray who it was he was dating.  Let Ray go crazy trying to figure it out – it would serve him right!  “Someone beautiful and worth my time,” he replied cockily.  “And that’s all you’re going to get!”

      “Come on, give me a hint,” Ray pleaded.

      “Nope!  Stew on it!”

     Ray walked out, but all he could think about for the rest of the day was finding out who Derek was dating now.  Someone in the company?  Maybe, but all the rumors about him and Sissy were way off track.  He had been sure of that before he talked to Derek.  So who was he dating?

     He was almost back to his desk when he spotted one of the women that he considered would probably know more about all the gossip going around the company than most others.  He stopped her for a moment.  “Who’s Derek dating now?” he asked.  “Have you heard?”

      “Have I heard!” the woman replied.  “I practically saw it!  He and Sissy are dating!”

     Ray thanked her and walked off.  No, whatever was going on between Derek and Sissy was something else… something he wasn’t sure he wanted to know about.  But Derek had been all too cocky in the way he had said he was dating someone, so Ray certain that Derek was seeing someone…and it certainly wasn’t Sissy!