The Bet - Chapter 11 (Tuesday – week 2 Part 2)

The Bet
by Karen Singer

Chapter 11 (Tuesday – week 2 Part 2)

Chad drove into the drive-thru of his favorite fast food restaurant, not because Mel had told him to, not because he was hungry, but because he still hadn’t figured out how he was going to be able to go to work dressed the way he was. Stopping to get something to eat was more of a delaying tactic. Normally, he would have gone inside, but certainly not today. The drive-thru was busy, as it usually was and he found himself waiting in a long line of cars. That was just fine with him. When it was his turn, he ordered his usual meal. Then he inched his car forward waiting his turn at the pickup window. Fortunately, he remembered just before he got there that he couldn’t reach into his wallet and pull out a couple of bills like he usually did. His wallet was in his purse now. While the cars were all stopped, he quickly grabbed his purse and opened it. He easily found his wallet inside, but he had to shake a few coins off of it before he could pull it out. He pulled out enough money for his breakfast then put his wallet back in again and closed the purse. It was his turn at the window. He drove up to it praying that whoever was there wouldn’t notice his pants or his purse… or his diaper bag for that matter. But the girl there just handed him his coffee and took his money. She quickly made change and handed him that along with a bag containing the rest of his breakfast. And that was it. He drove off quickly and found a parking place to eat. The money the girl at the window had handed him he just dumped loosely into his purse. He figured he could put the bills into his wallet later.
As he sat and ate, he began to dread more than ever going into work. How could he ever explain wearing girl’s pants? The purse he figured he could leave in the car. That would be no problem. It was his pants he was worried about. That reminded him about his socks. As soon as he finished eating, he dug them out of the console and put them on. Just that simple act made him feel a little more confident, but only a very little. It was starting to get late. If he waited much longer he’d run into too many people on the way in. He drove to work.
Once his car was parked where he usually parked it, he grabbed his cell phone and his keys from his purse. He figured they would be the only things he would need. Then, holding his breath for courage, he opened his car door and walked much faster than normal into the building. He was not happy to see more people around than he usually saw. Not a lot, but to him it definitely seemed like more. Just inside the door, he passed two women walking the other way. One of them looked at him oddly and stopped, cocking her head. The other one stopped too. Chad hurried past them, not wanting to say anything at all. Why did his cubicle have to be so far from the door?
He continued hurrying through the hallways, making turn after turn. It seemed like more and more people were looking at him. Was he attracting too much attention because he was hurrying so fast? He realized he probably was, but there was no way he could slow down. Finally he reached his own cubicle and he quickly went in and sat in his chair. Why couldn’t he have an office with a door that he could close? But at least his cubicle was somewhat isolated. There weren’t many people around him. One of the cubicles next to him was even empty.
He had made it. He was at work, at his desk. And he was wearing women’s pants. He had no doubts at all that some people noticed it as he came in. He’d probably be the talk of the company before long. And then he remembered his mascara. He still needed to get to the men’s room to wash it all off. Another long walk. But that was going to have to wait. He didn’t have the courage yet to run into anyone else. Besides, if he waited a bit longer, most people would be hard at work and the men’s room would more likely be empty. He had major plans for another relief session and that would be easier on him too if he could be alone.
He realized he needed to pee again. Damn! He shouldn’t have drank the coffee with his breakfast. Not yet ready to make the walk to the men’s room he allowed himself to pee into his diapers again. That part at least had gotten a lot easier since this all started. It was almost second nature to him now.

Not giving it another thought, he got to work - work that was all too disturbed by the fact that he was wearing women’s pants and mascara – openly in front of everyone else. The more he thought about that, the more his sexual need raged inside of him. He began counting the minutes till he dared make the trip to get some relief.

Andrea looked up surprised as Mel came back into the office. “You’re back early,” she said. “What happened?”
“The judge postponed the Baxter case again till tomorrow.”
“Again?”
“Yeah. I figured he probably would. The other side is really only doing what I would have done. They know I’m going to win and they’re trying to delay it.”
Andrea nodded. It was really routine stuff. “There was a package in the mail for you today. I put it on your desk. I noticed it was marked for fast delivery.”
Mel beamed. “Good!” and hurried off toward her office.
“Something special?” Andrea called behind her. But the only answer she got was Mel turning around and flashing her an interesting, if not wicked, smile.
Mel found the package on the middle of her desk. She checked the labels. Yes, it was exactly what she hoped it would be. She had some extra time in her schedule now. She opened the package and dumped the contents out on her desk. A couple of small packages fell out. Most of them looked like plastic. One contained a package of tiny locks. She left the locks alone and opened one of the other packages. The biggest one.
Just looking at the object that she now held in her hands sent shivers down her spine. But she wasn’t sure if they were shivers of pleasure, anticipation, or of horror. Part of it was phallus shaped, sort of. The rest of it was obviously the Chinese puzzle that would attach it to Chad’s cock. She had watched a video on the internet about how to put it all together and she tried it now, fumbling more than a few times till she finally figured it out. There were so many pieces, all of which was made more complicated because there were various sizes of some of the pieces so that the right fit could be achieved. She practiced a few more times till she was sure she could do it with no trouble.
Then she opened one of the other small packages that had been included and dumped the contents out in front of her. Several very cruel looking pieces were on her desk. She picked one up and examined it. It was basically a half circle of fairly sharp teeth. She touched one. It was sharp enough, but really not all that bad. But she had no doubt that those teeth could really hurt a certain particular part of Chad.
She was a bit startled by someone knocking on her door. Andrea opened it and poked her head in. “The court clerk just called. Your next case has been postponed till next week.”
Mel rolled her eyes. “What is this, a conspiracy?” She sighed. “It looks like it’s going to be just one of those days.” She knew that things often went like this. In her business, you never knew.
She noticed Andrea looking curiously at the things on her desk. “Is there anyone in the office?” Mel asked, referring to possible customers.
Andrea shook her head. “Not today. You’re supposed to be at court all day, remember?”
Mel nodded, “Yeah, it just looks like none of it’s going to happen. Come on in then. I can see you’re dying to see this.”
Mel showed Andrea the device and how it worked. More than once, she saw Andrea blush. But there was no doubt that she was also terribly interested. As Mel showed her the part that looked pretty much like a cock, she said, “This is a new model. It’s made a lot shorter than most of the other ones. I picked it specially so he’d have less room to get hard in.”
“I thought it looked awfully short,” Andrea replied. “And what are those little things?” she finally asked, pointing at the small disks with teeth.
“Those are called Points of Intrigue. There actually designed to make sure that he can’t pull out of it, but they can have another affect too. I read where just the teeth alone hurt so much that the wearer learns a lot faster to not get a hard-on. The different sizes give me the choice of how cruel I want to be with it. But as long as he stays nice and soft, they shouldn’t hurt him at all. Unless he tries to remove this thing that is.”
Andrea didn’t know whether to laugh or feel sorry for Chad. “The poor guy,” she finally said. “But he did ask for it by making the bet with you, didn’t he?”
“You’ve got that right. And you know how I hate to lose!”
Andrea could only agree.
“That reminds me,” Mel said as she reached for her phone. She punched in the number and waited. “Hi Cassie,” it’s Mel. How are you?”
“Oh, I’m fine. I’m just about to start a class so I can’t talk right now.”
“That’s ok. Listen, when Sissy comes in today, do me a favor. Just make sure he’s carrying his purse. Ok?”
“A purse!”
“Yeah, from now on I want him carrying one.”
“Oh God! I can’t wait! Ok I got it. I got to go. Talk to you later.”
Mel hung up her phone. Andrea burst out laughing. “Oh Mel, this is getting better and better.”
With delight in her eyes, Mel said, “There’s more too.” She then filled Andrea in on all the things that happened last night and this morning. Andrea was in stitches.

Chad glanced at his watch. It was time. A minute past in fact. Did he dare do it? Did he dare leave the safety of his cubicle and go all the way down the hall to the men’s room? His need raged inside of him. He had to go.
Plucking up the courage, he got up from his seat and glanced down the hall. The coast was relatively clear. Taking that first step was difficult, but he did it. He walked quickly, but not too quickly, towards the men’s room at the end of the hall. One of his friends came out of his own cubicle with his hands full of papers. He barely glanced at Chad and just said hi to him. Relieved, Chad continued forward. He finally reached the bathroom door. Nobody else had seen him. He opened it and went inside.
He was relieved. It was empty, just liked he hoped it would be. He went straight to one of the stalls and was soon pulling his clothes off as fast as he could. Once again he masturbated over the images of what she had done to him, only today they seemed all that much more powerful. His orgasm was incredible. It had been a very long time since he had experienced one that strong.
He sat down on the toilet to wait and recover. When his breathing was back to normal again, he started to get up, but he suddenly heard someone else coming into the room. He sat back down again and decided to stay right where he was. His penis had finally grown soft again. He suddenly felt the need to pee. He peed sitting down. He heard whoever it was with him washing his hands, then leaving. He stood back up and got fully dressed again, fumbling awkwardly with the zipper on his slacks because it was backwards and he had to pull it with his other hand.
He left the stall and quickly washed his hands. Then he glanced quickly at the mirror. His mascara! He had forgotten all about it. He washed his face too. But it was taking too much time to get all the mascara off. Before he could finish, somebody else came into the men’s room too. Chad finished what he was doing as quickly as he could and hurried past the guy who was still standing in front of one of the urinals. Had he seen Chad’s all too feminine slacks? He doubted that the guy had noticed or he figured he would have said something. Feeling much more confident, he hurried back toward his cubicle.
But he didn’t make it. Robin, the woman who worked in the cubicle next to his, came out and headed straight towards him. She smiled when she saw him, then Chad saw her smile turn to puzzlement. He wanted to walk past her and not say anything. But she stopped dead in her tracks and was watching him approach.
“Chad?” she said as he got close enough to him. “Are they women’s pants you’re wearing?”
Chad slowed his walk and stopped. He was busted. He felt his face blushing and knew that she had noticed that too. There was no way out of it. “Yeah,” he finally said sheepishly.
“Why?” the she asked.
Chad just shook his head. “I…” but he didn’t have a good answer he could tell her. Instead he quickly left her and walked back to his cubicle. Someone knew. Someone knew for sure. What was he going to do?
He tried to work, but he couldn’t really concentrate. It was impossible, what was he going to do?
“Chad?”
He turned in horror to see Robin at the entrance to his cubicle. He felt himself blushing again. “Hi Robin,” he said sheepishly.
They just stared at each other for a moment. Chad wished desperately that she would just go away.
“Can I see them?” she finally asked.
That was not what he really wanted her to say.
“Please?” she asked, even though she noticed the almost pleading look in his eyes that said he didn’t want to.
Chad didn’t say anything, but slowly he stood up and moved his chair aside. Robin came all the way in. “I like them?” she finally said. “Turn around.” He did so. He realized he was suddenly getting ordered around by way too many women lately. “They certainly fit you very nice. I never noticed before how full your backside is. And you’ve lost some weight.”
Chad blushed deeper. There was no way he was ever going to tell her about the diapers too.
She was looking him in the eyes now, and was about to say something, when he saw the expression on her face suddenly change. “Wait a minute,” she said quickly. Then she hurried away, only to return a moment later with a tissue in her hand. Chad backed away as she started to bring the tissue up towards his face. “Hold still,” she said. “You’ve got mascara still smudged on one of your eyes.”
Chad wanted to groan and scream both, but instead he instinctively reached for his eyes. “Wait,” she said, “I’ll get it for you. You can’t see it by yourself.” Chad’s humiliation reached a whole new level as he felt her rubbing over and over again at the skin under his left eye. “There. That’s better now. If you’re going to wash it off, you’d better be more careful.”
“Thanks,” Chad replied sheepishly.
“So how come?” she asked again.
He opened his mouth to try to say something, but there were no words. He couldn’t tell her about any of it. “I don’t want to talk about it,” he finally said and then rudely pulled his chair back into place and sat down again, turning his back to her. He heard her sigh behind him and start to leave. He turned around again quickly. “Robin.” She turned back to him. “I’m sorry. Ok?” She just seemed to shrug her shoulders a bit and started to leave again. “Robin,” he added, “I seriously doubt this will be the last time.”
Her eyes went wide. “Why? What’s going on, Chad?”
But he just shook his head and turned away from her again. Busted!
Robin went back to her desk feeling more than a bit annoyed. He had actually been a bit rude to her. He had never been that way before. But then she had never seen him wearing women’s pants before either… and obviously he had been wearing makeup not too long ago too.
As she sat back down in her chair she couldn’t help but think about him. She had known him now for what, about six or seven years? And now suddenly this? She knew he was in the process of getting a divorce. But what did that have to do with this? More puzzled than ever and still feeling put out by the way he had acted, she tried to get back to work. But her thoughts kept returning to Chad. She thought he was at least somewhat of a friend.