The Bet - Chapter 31 (Monday – week 5 Part 6 of 8)

The Bet
by Karen Singer

Chapter 31 (Monday – week 5 Part 6 of 8)

Andrea walked into Mel’s office with her arms full. “Mail’s in,” she said as she walked over to Mel’s desk and set the armload of packages and envelopes on it. I didn’t open the boxes because you said you were expecting some personal stuff. So I’m guessing these may be them?
Mel grabbed one of the packages and checked the return address, then she did the same with the second one. “I think so,” she said. “I’ll let you know if they aren’t.” She glanced back and forth between the two boxes. “This is it? I was expecting one more.”
“That’s all for today,” Andrea replied. “Unless they sent it some other way besides the mail.”
Mel nodded. “I wasn’t in that much of a hurry for the stuff, so I didn’t pay anything extra for shipping.”
Andrea stood there and stared at the two plainly wrapped packages for a moment. “Um… Are these for… you know who in there?”
Mel hated not telling her, but with the kind of items they held, it was probably better if Andrea didn’t know. “These are… personal this time,” she replied, letting Andrea know that she wasn’t about to tell her.
Andrea nodded as if satisfied and left, closing the door again behind her.
Mel stared at her closed office door for a few moments, as if making sure that Andrea wasn’t going to be coming back anytime soon. Then she dug her scissors out of a drawer and attacked the first package. With the plain outer wrapping barely pulled back enough so she could see, she stared at the cover of the inner box. The clear plastic packaging showed her four colorful phallic-shaped objects inside, each with a slightly different shape and a different color. She felt strange and a bit dirty just looking at them, yet something deep inside felt excited and curious about them too. She quickly pulled the wrapping back around the box and set it aside.
She picked up the second package and opened that one too. This one she had to pull the wrapping completely off of to see what was in the box inside. She pulled the box out and finally opened it. Black leather straps connected to a large plastic piece. And nestled down in the corner of the box was a long object wrapped in plastic. She hesitated to touch it before she realized she was being silly. She pulled it out of the box and pulled the object out of the plastic it had been packaged in. She was holding a black… and to her knowledge, very large and lifelike replica of a man’s penis in her hands. Well, one side of it anyway. She stared at the thing totally fascinated. She glanced back at the leather straps in the box again. Hopefully, the thing would mount fairly easily to that plastic piece attached to the straps. It was the strap-on!
She could sort of understand caving in to Cassie’s suggestion to buy the package of assorted dildos. But this? It was hard to believe she had actually gone ahead and bought the thing. Quickly she put it all away and stowed everything in her bag where nobody would see them. She sat back and tried to get back to work again, but her thoughts centered instead around the strap-on device. What would it feel like to have something like that sticking out from her nether regions? It was double sided so supposedly she could get some pleasure too. Would she get any pleasure from it? And what about Chad… Sissy. How would he feel about her… “raping” his backside with the thing? It looked pretty darn big. Could she even get it in him? And just how should she go about doing it?
With an extra effort, she forced all those questions from her mind – temporarily. For the rest of the afternoon, they kept creeping back in to haunt her – right alongside the haunting questions from Gloria that she was convinced didn’t bothered her so much.

Chad laid on the floor and colored in the coloring book. Surprisingly, he was enjoying himself. Between drinking from his bottle, and wetting his diaper, and coloring in his coloring book, it was kind of fun to feel like a child again. The play was easy. He didn’t have to worry about work problems. He didn’t have to worry about anything except continuing to wet his diaper… which was pretty much taking care of itself now.
He had scattered the other baby toys around the room a little bit as if he had played with them in case Mel came in and asked about them. But in truth, he had totally ignored them. The challenge was the coloring. What color should the princess’s dress be? What color should he make the trim? What color for her hair? What makeup should she be wearing? He supposed they were all questions that little girls thought about when they colored in books like this, and now he was continually asking those same questions too. Yeah, it was kind of fun.
He felt himself peeing yet again. Since he had been laying on his stomach for quite a while now, most of the pee in his diaper had gravitated to the front, underneath him. If he wasn’t careful, he would leak all over the rug – and maybe not even notice it. What could he do? Another disposable diaper came to mind. He could lay it out flat and then lay on top of it. Situation taken care of!
He got to his feet and went back to his diaper bag and pulled one out. He stretched it open wide and was about to lay it down on the floor when he suddenly felt the darn suppositories in his system kicking in. He supposed he shouldn’t have stood up! With absolutely no control, the foul mush slid quickly out of his backside and into his diaper. Yuck! Yuck! Yuck! With only one diaper and no plastic panties or even the girdle for extra cover, the smell hit him fairly quickly. But one quick thought did brighten his mood. At least he was here in Mel’s office and could get changed soon. He wouldn’t have to sit around with the mess glued to him all afternoon like he usually had to do.
He picked up the phone on the desk to call Andrea.

Mel’s inner office phone rang. She picked it up.
“Um… you’ve got a problem to take care of,” Andrea’s voice said over the line.
“A problem?”
“In the other office… And it’s a smelly one!”
“Oh!” Mel exclaimed as she finally realized what Andrea was hinting at. “Thanks. I’ll take care of it right away.” Mel wasn’t exactly fond of having to handle this little chore. But it was a small price to pay for all the advantages she got. She wasn’t used to having to change his smelly diapers during the afternoon, except perhaps on weekends. If it wasn’t for the fact that he was only wearing one diaper and nothing else, she might have let him go for a while more without bothering to change him. But unfortunately, keeping him in only the one diaper didn’t allow her that luxury. With a small sigh, she got up and headed for the spare office.

Chad tried to stand somewhat still while he waited for Mel to come in to change him. Wearing only the one thin diaper, especially with no plastic panties on top, made him too nervous to move around very much. He didn’t want any of the mess from the back of his diaper to leak out and drip on the floor. And with only one diaper, he knew that gaps formed around his legs each time he moved, and leaking was a distinct possibility. After wearing multiple diapers, along with plastic panties and the very tight all-in-one girdles on top of that for so long, he felt very insecure in only the single thin diaper.
He was very glad when the office door finally opened and Mel strode in. “Okay, Sissy,” she said, “Let’s get you taken care of.”
He waited while Mel spread out a few of his disposable diapers on the floor to contain any mess, then he laid down on top of them. In short order, she had his messy diaper removed and any of the mess still sticking to his backside cleaned up with baby wipes.
Mel was in the process of pulling the fresh diaper up between his legs, when her gaze lingered a bit longer on his chastity device. She had locked it onto him to deny him the ability to get hard, or even to receive any pleasure in that area. Now, looking at his tiny penis once again, she was struck by how small the little thing looked. Not really much there for him to get any pleasure with at all… if she allowed it that is. She poked the device with her finger a few times, but he acted as if he didn’t even know she had touched it. But then, that was mostly due to the plastic device, wasn’t it? She was reminded of how much he seemed to be reacting now to things being shoved in and out of his backside – almost like a woman reacting to her own vaginal sex… although as far as she knew, he certainly wasn’t orgasming from it. As far as she knew anyway. That thought of course led directly to the two packages she had just gotten. She had gotten them to use on him. How would he feel about them? How would all those twisted odd shapes feel going in and out of him. Would he like it? And especially the strange strap-on. How would he feel about that?
Shoving those thoughts aside for the moment, she finished her task. Tonight! Tonight she would try to make some time to experiment with him a bit further – at least with some of her new toys. She wasn’t at all sure about that strap-on yet.
She stood up and looked around the room. “It looks like you’ve been good and have been playing like you should.”
Chad was still getting up from the floor. “Yes, Mistress,” Chad said again for about the thousandth time that day, although he really hadn’t played with any of the toys except the coloring book. In fact, he was now looking forward to getting back to it again.
Mel saw the coloring book open on the floor, all the crayons scattered around it. She smiled. “I see you’re enjoying the coloring book too,” she said.
This time Chad curtseyed. “Yes, Mistress. Thank you for getting it for me. I’m enjoying it a lot.”
As he said it, Mel noticed a bit of a blush forming on his face. “I suggest you enjoy your childish fun while you can. Tonight you’ll be busy with more adult things.” She glanced at her watch to note the time. “Two hours, Sissy, till leaky diaper time. Don’t disappoint me.”
Chad’s curtsey and answer were becoming so automatic that he barely registered that he had done it. He watched as she walked out again, leaving him alone with the childish toys. He wasn’t exactly sure what she had meant by being busy with more adult things. Cooking and cleaning were certainly adult things. But then so was the way she used him for her sexual gratification. He had a sneaky suspicion that she would probably be getting back around to that again tonight. He tried to feel something from his trapped penis inside his diaper. But as usual now, he felt nothing. It was just as well. Mel wouldn’t let him get any pleasure from it anyway.
He plopped himself back down on the floor to figure out what color to do the next Princess’s hair. Maybe red this time.

Mel checked the time. Not bad, still pretty early. Much earlier than she usually left the office. She called Andrea. “Anything else come in that can’t wait?” she asked.
“Not yet,” Andrea replied.
“Good! Then if anybody else calls or stops in… I’m not here!”
Andrea giggled a bit. “I think I saw you leaving a few minutes ago.”
“Yeah, you did.”
Mel hung up the phone and went into the spare office where Chad was. He wasn’t playing with any of the toys, he wasn’t coloring in his book. He was just lying on his back on the floor and drinking another bottle. “What are you doing?” she asked.
Chad held up the baby bottle in his hand. “Trying to get my diaper to leak,” he said in his silly sissy voice.
Mel glanced at her watch. She had almost forgotten about that. “Well, you’ve only got about half an hour to go,” she reminded him.
Chad climbed to his feet. As he did so, Mel saw that he was laying on yet another spare diaper. He was going through a lot of them today. This time he did curtsey. “Yes, Mistress, I know. I’m working on it.”
“Good, but you better work faster because we’ve got other things to do today. We’re leaving now.”
Leaving? Going where? Home hopefully. He was really hoping for home when he remembered that the only thing that he had to wear, other than the baby doll nightie top that he was already wearing, was his silly sissy dress. And right now, he thought he preferred the nightie top. Unfortunately, Mel spoiled that idea when she told him to put his dress back on. “Yes, Mistress,” he said as he dropped another curtsey. Then he decided to ask. “Are we going home now?” He was very hopeful.
Mel looked at him, quite surprised. “Heavens no. I’m not done showing you off around town yet. And I still think you need to parade around at work to show all your friends just how much of a sissy baby you really are.” Chad’s knees felt like they wanted to buckle again. “Until you do that, then I really think you’re holding yourself back.”
Chad would much rather hold back. He would much rather that nobody knew anything at all about his sissy side... Well, at least not much more than they already did. Since he was already dressing as a woman all the time at work it was too late to keep anybody from knowing that much. “Please no, Mistress. I promise I’ve been good! Please don’t take me to work like this.”
Mel shook her head. “I said I wouldn’t as long as you keep doing everything I tell you to. And I do admit that you have been pretty good today. But to be honest, I’m still undecided about the whole issue. So if you stay real good, then we’ll just go other places instead.”
Chad felt relief right down to his toes. She wasn’t going to take him to work dressed like the silly sissy that he was… hopefully. But then the rest of what she had said sunk in. Other places? So where were they going? He was suddenly very fearful.

As she drove, Mel thought again about what it was that she was doing and what she had already made him do earlier that morning. Her primary purpose had been to punish him for the way he had been acting. Yet she didn’t feel in the least like she had accomplished that. He had been fighting back – working hard to not only maintain his control, but to actually increase it too. And in the process, he had started to find and assert his darn male macho pushiness – despite his being a sissy. His rudeness at the gym had been plenty evidence of that. Not just once, but on multiple occasions. That male assertiveness was probably responsible for how hard he had been working at increasing his control. And him increasing his control spelled trouble for her as far as winning this bet.
She had to punish him. She had to get rid of that darn male stubbornness that kept him trying so hard to win. She didn’t have a clue how to really do that, but she was hoping that by punishing him this way, making him see how much of a man he wasn’t, that it would at least put a big dent in that armor of his. So she had come up with this scheme of showing him off in public like this.
She had thought that the gym would be enough. And he really did behave exactly like she had wanted him to… and then some! But it was that “and then some” part that had her bothered. Somehow, she didn’t feel like he had really been punished very much at all. She didn’t feel like she had accomplished what she needed to do. So now she was desperate to try something else… something that would rip that stupid male pride right out of him.
She didn’t really like this idea that she was about to try, but she couldn’t think of any other options. She had to get him back on the straight and narrow again, and he had to see just how serious she really was. She had tried this morning, and hopefully she had at least succeeded somewhat. Her having to work most of the day had kind of ruined things a bit since she couldn’t reinforce any of the lessons she wanted him to learn. This time, she would have to be more direct.
There! Her destination was in sight. This had been one of those off-the-wall ideas that she had discarded earlier as too risky. But now she felt differently about it. She just prayed that he wouldn’t get arrested… that ‘they’ wouldn’t get arrested!