The Bet - Chapter 24 (Monday – week 4 Part 3 of 5)

The Bet
by Karen Singer

Chapter 24 (Monday – week 4 Part 3 of 5)

“He’s here,” the receptionist said to Cassie as she was coming out of the locker room. “Or maybe I should be saying “It’s here.”
Cassie smiled. She knew the problem. It was a bit hard to call Sissy a “him” since he was always dressed completely as a woman. Yet he wasn’t a woman either so the pronoun “her” didn’t apply at all. “I know what you mean,” she replied as she headed toward the front of the gym. “Nothing really sounds right.”
She spotted Sissy as she was half-way through the main part of the gym. He dropped a curtsey and greeted her formally as soon as she got all the way up front. Oh, he was a real joy sometimes. “Ok, Sissy. Let’s take you back there,” she said as she turned around and led the way back through the room full of exercising women.
She once again led him into the little office they always used and lowered the shade on the door. “How are you today?” she asked as he started to get undressed.
“Ok, I guess,” he replied.
She pulled his bottle out of his diaper bag and waited till he was down to just his diapers and plastic panties. She handed it to him as soon as he had laid down on the floor in front of her. She watched as he put it to his mouth and began sucking on it. She smiled. Such a joy to watch. Unbelievable! But still such a joy. And the damn guy could cook too! She really envied Mel just then. Maybe she could find someone like Sissy here. But then she thought of Sandy. No, Sandy more than fulfilled all the missing pieces in her life. She didn’t really need anyone else. As she pulled Sissy’s plastic panties off of him, she mentally wished Mel luck with her toy. She only hoped that together they would find the happiness that she had with Sandy.
She unfastened his diaper and put a fresh one underneath him. Then she grabbed the bottle of baby lotion and warmed a generous portion in her hands. “Ready?” she asked. He looked up at her. Only the slight crease between his eyebrows gave any indication that he was concerned. She began spreading the baby lotion all over the front of his groin… the parts that weren’t covered by his chastity device anyway. As she massaged him, she noticed that he seemed to be looking away somewhere in the distance, as if he wasn’t really thinking about what she was doing at all.
Chad sucked on his baby bottle without hardly thinking about it. His mind was on other things. Cassie was massaging him, trying to get a reaction that would be all too painful, but he was way past that point with what she was doing to worry about it. In fact, even with the new, bigger teeth in the device, the thing wasn’t even bothering him just then. Fortunately! As she rubbed him, his mind wandered back to this morning. He and Robin had sat and read women’s magazines together for most of the morning. They had even talked some. And he had done it as if it was the most normal thing in the world for a man to do. Ok, maybe he didn’t usually have a clue what she was talking about, but still… it had been kind of enjoyable. She hadn’t made fun of him or teased him in any way all morning. She hadn’t even called him Sissy all morning. It had been… really nice. How strange.
“Well, I can see that this is getting us nowhere!” Cassie said, interrupting his train of thought. “Roll over. Time for the other side.”
This was the part that Chad was more worried about… now. He put his bottle down and rolled over with his knees up under him and his head down… putting his backside up as a perfect target for her attentions. And as much as he hated the idea of it, he also was looking forward to it. If only he wasn’t wearing that damn chastity device! He felt her hands begin massaging his backside. He closed his eyes and gave into the wonderful sensations.
After a minute, he felt her finger begin to linger closer and closer around his tiny asshole. The very spot that now seemed to hold most of his sexual feelings. Why? It was another question he had no answer to. Because he was a sissy? Was there some physical reason for it just because he was a sissy? Again, no answer. But he thrilled the moment she began increasing the pressure with her finger on his asshole and began to press her finger inside. Yes! More! More! More!
Cassie added more baby lotion lubrication to her finger and slipped it back inside of him up to her knuckle. Then she started pumping him with it in just that far. She could see his back arch a bit from the pleasure. He was trying to push back against her now, trying to get more and more of her finger into him. After another minute, she allowed it… as far as her finger could go. Back and forth, over and over again he rocked and moaned slightly as he fucked himself against her finger.
Chad pumped over and over again, rocking his body as far as he could. Trying ever so hard to get more and more of her finger into him. He wanted it harder – her finger anyway. He wanted to feel more pressure. What he didn’t want was any pain from his chastity device. But so far, the only pain he was feeling from it was fairly mild… fairly anyway. At least he was able to control it somewhat. His bigger problem was that as usual, he wanted more from the feelings in his backside, but he wasn’t getting enough. Those feeling by themselves weren’t enough to get him any kind of orgasm. He needed to get hard in the one place that was now totally denied to him.
As he pumped more and more, faster and faster, his frustration grew greater and greater. More, he needed more! But there was no more. He felt Cassie pull her finger out completely, then fuss with something next to him, then put it back in again. The suppository. Yuck! He wished he didn’t have to have them, but Mel was still insisting. At least he wasn’t getting them all the time anymore, only at night and whenever Cassie diapered him.
He rolled over again as soon as he felt her removing her finger again.
“You did real well again,” Cassie said.
He shook his head. “I still wish I didn’t like that so much,” he replied.
“Why? There’s nothing wrong with that.”
“I don’t know. It’s just not right!” He stuck his bottle back into his mouth so he could finish it.
“But you love it.”
“I know.” He sighed dejectedly around the nipple in his mouth.
She smiled down at him. “I think you’d like it if I brought one of my toys to use on you instead of just my finger.”
He suddenly felt a lot more pain from his chastity device as he remembered what that would be like. He shook his head. “I don’t think so. It might hurt too much.”
She just smiled and finished diapering him. Maybe she would bring something with her tomorrow… if she remembered.

Mel trudged into her office late in the afternoon. It had been a miserable day at court… all day! And worse, nothing had really been accomplished there. But then that was the legal system. It usually moved at a snail’s pace.
She was glad to see there were no clients in her office as she walked in, just Andrea sitting at her desk. She plopped her legal case down on Andrea’s desk and gave her one of those looks to let her know how bad things went.
“You look like you’ve had a miserable day,” Andrea offered.
“You have no idea! That judge! He’s absolutely the worst! We got nowhere!”
Andrea smiled, although she was trying to repress a chuckle. “You’ve said that about him before.”
“Well, it’s true!”
“You just need something to brighten your day.”
“Like what?” Mel replied a bit more testily than she meant to.
“Like another little surprise came for you today. I put it in your office.”
“Another surprise?” Mel asked. Not really sure what she was talking about.
“Another package…” Andrea prompted.
“Oh!” Mel replied as she suddenly realized. “Something for Sissy?”
“At least that’s what I’m assuming it is.”
Mel finally smiled as she walked back toward her office. Andrea followed her. The box was on Mel’s desk. It wasn’t nearly as big as the other ones she had received so far, but she immediately attacked it with a pair of scissors to open it. She lifted the lid and stared. It was wrapped in plastic – naturally, but she could still see it perfectly. “Oh,” she said out loud, “it’s adorable!” She pulled the dress out of the box and held it up so Andrea could see it too. It was a very short dress in a pale pink and white check pattern. Mostly anyway. There were two white bows on the front of the dress at the waistline. The top was made to look like a frilly white under blouse, but it was actually attached. The whole think looked so babyish she couldn’t believe it.
“Oh,” Andrea exclaimed. “It is adorable! And it’s so short! Are you sure it will fit him?”
Mel looked at the dress. The shoulders and waist seemed more than wide enough since it wasn’t a fitted design. It just appeared to be very short. She smiled at Andrea. “Yeah, I think it will… although I’m betting his diapers will show under it for sure.”
Andrea laughed… and Mel joined her.

Chad couldn’t believe it. Not that he really minded, but Robin was back in his cubicle again and they were looking at more magazines. She had stopped and bought some new ones during lunch and now they were looking through them together. “What else are we going to do?” she had explained. He had to admit, she had a point. And as long as nobody else saw him, deep down, he was really enjoying looking through the magazines – as if he was getting away with something forbidden. And it was sort of nice to have somebody there that he could talk to about them… even if he was really too afraid and embarrassed to talk much.
But as they sat there looking through the magazines, just as it usually happened around that time of the afternoon, Chad felt the suppository that Cassie had put up inside of him starting to do its thing. Damn. And he knew very well that there would be no way at all to stop it. He was extra worried because sometimes it made a bit of noise and Robin was sitting right next to him. He needed to get rid of her, but how? And did he have enough time to get rid of her? That question was answered almost immediately as he felt the first bits of whatever was inside of him coming out and into his diapers. Yuck! Fortunately it was silent. As he continued to feel it coming out of him and spreading around his bottom, he prayed it would stay silent… not to mention that he prayed his new long-legged girdle would contain the smell as well as his old ones did. He squirmed several times as it kept happening. Fortunately, Robin was totally engrossed in the magazine she was reading.
“Hey Chad,” she suddenly spoke up as she turned to him.
Damn! She had sensed something.
“What do you think of this outfit? Do you think I could get away with wearing anything like this to work?”
Maybe she didn’t realize yet. He squirmed a bit more as he leaned forward to see what she was talking about, giving the mess on his backside more room to spread out. He looked carefully at the picture, but his mind was mostly on what was still coming out of him than on anything else. The picture showed a model in a very short print dress. How should he know if she could wear that to work? “Why not?” he replied. “You’d probably look good in it.”
“That’s what I thought,” she answered, as she sat back with the book again. “I just love all the clothes they have in this book.”
Was he safe? Had he gotten away with it? He hoped. A few minutes later, his problems with his backend seemed to be mostly over – finally. He was glad that he had eaten only a small lunch once again. It really did make his messes a lot smaller. He squirmed again in his chair, trying not to show what he was doing as a tiny bit more came out of him. A little while later, the mess inside his diapers had worked its way around as it usually did and was no different than on any other day. Robin was still engrossed in her magazine… and Chad breathed a mental sigh of relief. Thank God for the tight girdle and pantyhose that contained everything… especially the smell! He might be a bit more uncomfortable for the rest of the afternoon, but nobody would know… hopefully.

Chad hurried home after work. Mel had sent him a message telling him to be in uniform and to have dinner ready once again. She had also taken the time to add that there would be no visitors tonight… good! He cleaned himself up, taking a quick shower in the process to rid himself of the awful mess on his backside, then he rediapered himself as usual in two disposables. Somehow, just getting back into the diapers once again felt comforting. He just preferred them to be a bit wet though and almost couldn’t wait to wet himself again. The diapers might be miserable when he was messy, but he really loved them when they were wet. They felt so much more… interesting!
Why didn’t he wear diapers more often before this bet? His marriage! That was probably the main reason. If it wasn’t for his marriage then he might have learned the true pleasures of being in diapers a lot sooner. For the first time all day, he had a small reason to be glad about his upcoming divorce.
He fixed his makeup, fixed his hair, dressed quickly in his uniform, and quickly buffed his shoes to a gleaming shine. Since he didn’t wear them to work earlier, the shoes still looked very good to start with, so polishing them was almost no work at all. Another reason to smile. He went out the door to Mel’s apartment to start dinner.