The Bet - Chapter 53 (Tuesday – Week 8 Part 5 of 10)

The Bet

By Karen Singer

Chapter 53 (Tuesday – Week 8 Part 5 of 10)

     Carefully press down on the “shift” key with the left heel and don’t let it slip off… and even more carefully, press down on the “I” key with the other.  There!  An upper case “I” typed perfectly.  Now for the next letter.  Fortunately, he wouldn’t be typing any more upper case letters for a little bit.  Typing with the shoes once again taped to his hands was very difficult.  Any letters requiring him to use both shoes at the same time were much more difficult. 

     Of course, he didn’t appreciate it at all when Robin had deleted everything he had written before the break – just because he had been standing up when he typed.  So he was sitting down now and the angle made everything that much more difficult.  Hitting the “space” bar between words was the easiest thing he did. 

     He didn’t know where Robin had gotten off to.  After break, she had deleted what he had written, made him sit down, and taped the shoes to his hands again.  Then she had said she would be back in a few minutes, but that had been a while ago now.  He was fairly sure she hadn’t gone back to her desk, so he had no idea where she had gone.  Oops!  He had slipped while typing the letter “t.”  When he typed with his hands and missed like that, he usually called it “fat fingered.”  What did you call it when you were typing with the heels of your shoes?

     Robin was once again searching the inner reaches of the supply room.  She needed a way to keep Sissy in his seat so she wouldn’t have to worry about him getting up when she wasn’t watching.  Her first thought was to use the tape she usually used on him – that would have been easy.  But she knew the skirt he was wearing wasn’t his and the tape would ruin that – and those beautiful stockings he was wearing.  And today she didn’t want to mess up any of what he had on.

     So tape was out.  But what else was there?  She had been sure from the start that the supply room wouldn’t happen to have any decent rope lying around – yes she had checked for that first.  Now she was opening cabinet after cabinet – searching the shelves for… inspiration.  And in the dimmest part of the back of the room, she found what she needed – in the back of a lower shelf filled with… junk.  It was a ball of coarse twine like they used to use for tying up packages.  In fact, it looked so old that for a minute she thought that’s exactly what it had been used for.  But she grabbed it anyway and hurried back to their desks.

     Chad was so startled by Robin hurrying back into his cubicle that he fat fingered another letter – or was that fat heeled?  “Hold up for a minute,” Robins said a bit breathlessly as she started trying to figure out how she was going to tie him into his chair.  She pulled out the end of the string and tied it off to the arm of his chair.  Then she pulled it over his lap and under the other chair arm. 

      “This isn’t necessary,” Chad started to say. 

      “I didn’t ask you,” Robin replied.  “And knowing you, it’s entirely necessary.  So shut up and let me finish.”

     She brought the twine tightly around the bottom of the chair, up under the first arm, then tightly around his lap and down the other side.  She wrapped three layers before she tied it off to the same arm of his chair.  With his hands taped into his shoes, he wasn’t going to be able to untie the simple knots she had tied.  He was stuck there till she released him.  “There!” she declared.  “That should hold you for a while.” 

     She stood back to survey what she had done for a moment.  She hadn’t cut the twine off so that the rest of the twine ball was now laying on the floor under his chair.  As she was congratulating herself, she saw him push his chair back with his feet so he could look at her better.  And it bothered her that he did.

      “I wasn’t going anywhere,” he complained.

      “I didn’t ask you,” she replied.  “Besides, if it’s one thing I’ve learned about you in the last few weeks, you’re too childish to be trusted if left alone too long.”

     But the fact that he had pushed his chair back still bothered her.  She walked up to him and turned his chair back around again, facing his desk.  Then she grabbed the ball of twine from the floor.  Next she grabbed his right ankle.  She lifted his ankle as high up against the underside of the chair as she could and tied it off there with the twine.  Then she brought the twine back over his lap to the other side of the chair and did the same with his other ankle.  Then, just because she could, she tied the twine tightly between his two ankles.  Now he couldn’t get out of the chair… and he couldn’t even move the chair – not with his legs at least.  She pushed him – in his chair, tightly up against his desk.  “Now you can keep working – and I don’t have to worry about you getting up at all.”

     She surveyed her work for a minute and finally walked off happily.

     Chad was still stunned.  Robin seemed to have this thing for tying him up.  He hadn’t realized that about her before.  He wondered if she realized it herself – probably not.  It wouldn’t be the type of thing she was used to doing in her everyday life.  Or so he thought.  But now he was still faced with the task of copying what he had written to Mel earlier that morning – so quickly and easily with his hands.  Robin had pushed him tightly up against his desk.  Too tightly.  Tight enough that it made working more difficult.  He pushed with his arms a bit and managed to back his chair up a few inches.  Much better. 

     Once again he set about his task.  But he didn’t get far before Robin was back again.  She quickly pulled his chair away from his desk, and handed him another baby bottle to drink.  Just grabbing the bottle between both shoes was difficult – just as it was trying to get the thing up to his mouth properly and hold it there.  Robin left again, but not for long.  She came back a minute later with her cell phone and started taking picture after picture of him tied to his chair, while trying to hold onto his bottle with his hands taped inside his shoes. 

      “When you finish that thing, don’t go anywhere,” she teased.  “Just sit there quietly.  I’ll be back to check on you later.”  After watching him struggling with his bottle for a few moments, she finally left him alone and went back to her own desk.  Unlike him, she had work to get done.  And she had put it off way too long.

     Ray’s mind was on Mel, the rich lawyer woman, as he leaned back to take a small break.  She had put him off yesterday, but you don’t give up on a woman that fast – especially not if she’s rich – not to mention awfully good looking.  Without thinking any more about it, he picked up his phone and called Mel.  But he only got as far as Andrea.

      “I’m sorry, but she’s busy with clients.  And they’re all backed up.  I can have her call you when she gets a chance, but that’s all I can suggest today.”

     Ray was a bit angry that he couldn’t talk to Mel right away, but he understood.  She was a lawyer.  She had to be busy.  “Yeah.  Please.  First chance she gets.”  He hung up the phone.  She was busy.  Well, hopefully she would call back soon.

     It wasn’t till nearly lunchtime when he did hear from her. 

      “Hi Ray.  Sorry I couldn’t get back to you sooner.”

      “That’s all right,” Ray replied.  “I’d gladly sit around all day waiting on a beautiful sexy woman like you.”

     Mel actually blushed at his line – and he probably would wait around for a sexy woman.  But her?  “I’m afraid I’m really busy today,” she replied, trying to brush off his comment.  “What can I do for you?”

      “Go to lunch with me… or dinner… or anything!  Just do it soon!”

     Mel laughed, and at the same time, remembered Derek.  “Oh Ray, I’d love to, but I can’t.  Not now.  Probably not for another week – at least.  Things are just too… crazy right now.  I’m sure you understand.”

     Ray was disappointed, but he had tried.  “You know I’m going to keep bugging you till you do go out with me,” he said.

      “You shouldn’t have to bug me too much,” Mel replied.  “I want to go out with you.  It’s just that, right now, things are complicated.”

      “Sure they are,” Ray replied, not really believing it.  “But things are never too complicated to take a little while to enjoy yourself.”

     Mel grunted.  “You don’t know my secretary.  She can be a real slave driver!”  As she said that, she looked up to see Andrea in the doorway raising her eyebrows.  “Look Ray, I still want to go out with you, but I can’t right now.  That’s all I can say.”

      “Okay, I understand,” Ray replied.  “But I’m going to keep calling.”

      “Good!” Mel replied.  “Please keep trying.”

      “Slave driver?” Andrea asked as Mel hung up her phone and she walked into her office.

     Mel laughed.  “What would you call it?  I don’t know how many clients I talked to this morning, and I’m sure you’ve got just as many lined up for this afternoon.  Do I even have time for lunch today?”

     Andrea smiled, but it was a strained smile.  “Not really, but I booked you forty-five minutes anyway.”

      “Good!  Do me a favor, call Gloria for me and tell her to order lunch for me.  She’ll know what I like.  And warn her that I’ll be in a hurry.” 

      “You’ll be in even more of a hurry if you don’t get in with your next client!  Room number three!”

     Type, type, type.  Sort of.  Actually it was more like figure out which heel to use to hit which key, then try to do it without screwing up – too badly.  It was amazing how difficult Robin could make out of something that should be so easy.  But at least he was making progress – again.  Now if only Robin wouldn’t delete everything like she did before!

     He didn’t hear her coming.  He didn’t know she was even there till she strode into his cubicle and announced, “Bottle time.”  He suddenly felt his chair being pulled backwards again, away from his desk.  She held out his baby bottle for him and watched as he carefully manipulated the shoes on his hands to grab the thing.  “When you’re done with that,” she told him, “I’ll start untying you so you can go to lunch.”

     Chad watched her walk out again.  And then he watched the empty opening to his cubicle.  He watched the opening because his chair was turned in that direction and he had no way to move it.  What if someone else came in to see him?  He would be on total display for anyone to see.  And he couldn’t move or do anything about it.  Robin had definitely seen to that.  As he drank his bottle, he noticed himself peeing yet again.  Most of the time, he never realized he was doing it anymore.  Why should he?  With all the liquids he was getting all the time now, how could he possibly even think about holding back?  As far as he could tell, he had no control anymore – of anything.  At least while they kept forcing the liquids down his throat.  If they would stop for a while, he had no doubt he could get all his control back – and quickly!  He knew that for a fact!  At least… he hoped so.  Because if he couldn’t, then Mel would win this bet all too easily. 

     Fortunately, he knew the facts.  And more fortunately, he knew his own body – and how it would react.  It was impossible for Mel to win.  He hoped.

     Cindy saw Sissy’s car pull into the parking lot just as it always did each day at lunchtime.  But today, she didn’t even try to think of some way to tease him, or even something witty to say to him.  What would be the point?  Not as long as Cassie said she still couldn’t play with him… or rather change his diapers for him.  Maybe next week, but not this week. 

     Since he held a little less interest for her today, she wasn’t looking at the door when he opened it and walked in.  She didn’t look up till the door had already closed behind him.  And when she did look, her jaw dropped wide open.  “Oh… My… God!”

     Chad curtseyed and said hello to her.  “Will you please get Cassie for me?” he asked. 

     But Cindy was too fixated on staring at his outfit.  She hardly even heard him.  “I love it!” she declared.  “That outfit would be so perfect!”

     Chad wasn’t sure what his outfit would be perfect for.  He didn’t even really want to know.  “Um… Cassie,” he prompted. 

     But Cindy still wasn’t listening.  “Where did you get those garters?” she asked as she leaned forward over the counter so she could see better.  “My boyfriend would go absolutely wild over them!”  But then her expression changed as she noticed something odd.  “Um…  What’s hanging down below your skirt?”

     Chad looked down.  He had felt it as he walked from his desk to the car.  He had felt it during the short drive over from the office.  And he had felt it as he walked from his car into the gym.  He had no doubt as to what was showing.  He tried to pull his skirt down lower, but he quickly realized it wouldn’t go any lower.  Pulling it down would do no good.  “Um…”

      “Sissy… is that … your diapers showing below your skirt?”

      “Um…” 

      “How on earth can they hang down that low?”

      “Can you please just get Cassie?”

     But Cindy was already coming out from behind the counter.  Without bothering to ask, she immediately knelt down right in front of him, and after looking closer, pulled up on his very tight skirt – revealing the white open bottom girdle he was wearing underneath.  She was momentarily startled because it wasn’t what she was expecting to see under his skirt.  But it was obvious from just a quick look that she couldn’t pull the girdle up like she did his skirt.  She bent down to look up under the girdle opening better.  The entire space between his legs was packed with his plastic panties and diapers pushing down.  “My God!” she exclaimed.  “How did they get like that?”

     But instead of answering, Chad just backed away and pulled his skirt down into place again.  “Will you please get Cassie for me?  As you can see, I really need changing.”

     Cindy got up from her knees still in shock.  “You can say that again.  Wait right there!” 

     The receptionist was back with Cassie faster than usual.  They both looked like they had been hurrying.  But the moment Cassie caught sight of him, she stopped dead, unable to believe what she was seeing.  “Um… Wow!  What an outfit!” she finally exclaimed.  Then she seemed to get more control of herself.  “Cindy says that your diapers are about ready to explode if we don’t change you real soon.”

     Chad nodded.  “That’s pretty much the case.”

      “Well let’s get you back there then, and fast!”

     As Chad followed her back through the room full of exercising women, most of them stopped what they were doing just to look at him.  Two of them called, “Hi Sissy!” as he walked past.  He knew he was blushing furiously before he got back to the little office where Cassie changed him. 

     Cassie knelt down on the floor with his diaper bag to start unloading the supplies, but she glanced up at him as she was opening the bag, and she stopped… and stared again.  “Damn!  I can see your plastic panties hanging down below your skirt!  How can they do that?  Are your diapers falling off?”

     Instead of simply removing his skirt, since it was so tight, Chad pulled the bottom of it up to expose his open bottom girdle.  “No,” he replied.  “At least, not quite.  This girdle is so tight they can’t expand in any other direction except down.  And since the bottom is totally open, there’s nothing to stop them.”

     Cassie shook her head in disbelief.  “Amazing,” she muttered before going back to work.  “Do you need some help undressing?” she asked without looking up at him.

      “I think I can get it,” Chad replied.  “It may just take me a little longer.”  It actually took him almost twice as long as usual to get undressed, just to have his diaper changed.  But eventually, he was once again nursing on yet another bottle as Cassie marveled over how loaded, and misshapen, his diapers were. 

     She quickly inserted three fresh diapers under him before she cleaned him up.  Then she had him roll over so she could do his other side.  That was the part that Chad really liked.  And once again, he had very good reason to like it.  Between her initial teasing and the feel of her toy inside his backside, he was once again pumping for all he was worth, trying vainly to reach that unobtainable pinnacle called an orgasm.  That one peak that made every little bit of humiliation he went through worth it.  But as usual, he soon realized that the impossible was simply that.  Impossible!  He thought he had experienced it once with Mel, but now he was fairly certain he had imagined it.  Unfortunately.  Still, it was the closest thing to full sex that he was now capable of, especially since his old sex tool was still so totally locked up and denied to his touch.

     When he had finally stopped, Cassie pulled her toy out and again faked putting one of the suppositories up inside of him.  He never looked back at her.  He seemed to be that resigned to them.  All the easier for her to fool him. 

     As soon as he felt her finger coming out of him again after inserting one of the dreaded suppositories, he rolled back over – and got a small shock as he set his backside down on the fresh diapers.  They weren’t so fresh anymore!  He could feel that they were already a little damp – and they were disposable diapers!  How much had he wet them without knowing it while Cassie was playing with him?  He mused over that as Cassie began fastening the diapers and he once again nursed on his latest baby bottle.  He wasn’t sure if he was more worried that he hadn’t realized he was peeing, or that he didn’t seem to have any control at all anymore, or that the very thought that it had happened like it did seemed to stimulate his sexual excitement all that much more. 

     Getting dressed took longer than getting undressed.  Cassie was kind enough to help him attach his stockings in the back.  Chad was glad because lining up the seams so they were straight was particularly difficult if he did it by himself.  He immediately felt the relief of not having the huge heavy bulk of his diapers hanging down between his legs – at least not down further than usual. But he knew it was only a temporary feeling.  In a few hours he’d probably be worried about them showing once again.