The Bet - Chapter 18 (Tuesday – week 3 Part 7of 7)

The Bet
by Karen Singer

Chapter 18 (Tuesday – week 3 Part 7of 7)

“Ok, baby, just relax now and enjoy this,” she told him.
Relax? In this position? Not a chance! He suddenly felt her hands on his backside. Slippery hands. Massaging him as she did every day at lunchtime, only this time he was in a different position. And it felt great! “Mmmm,” he said unconsciously through his pacifier. He heard Sandy giggle softly. He didn’t care. Cassie’s hands felt great.
But then the hands started moving closer to his tiny hole again. Like they did yesterday. Closer and closer… then over it, again and again. Till one of her fingers rested very lightly over the exact spot. He wanted to scream with frustration. It felt so good, yet he was helpless. Her finger moved away, moving with the rest of them over his entire butt again, then it returned and stopped, ever so lightly, directly on his hole again. He wanted to feel her finger harder there. But she wasn’t giving it to him. Just the tiniest bit, he raised his backside up toward her finger, just to increase the pressure so he could feel it better.
Sandy’s eyes went wide. She looked up at Cassie for just a moment. He had actually moved toward her finger.
Cassie brought her other hand up near her lips to signal Sandy to stay quiet. Then she began messaging his backside again. Again, after a minute, she brought her finger back again and placed it harder against his tiny hole. And kept it there like that.

She was teasing him, he could tell. She wouldn’t press it hard enough. His sexual need was boiling over. He didn’t know why this should thrill him so much, but it did. Maybe because it was the only open avenue he had for any kind of sexual feeling.

Cassie waited, keeping her finger firmly against his little hole without putting it inside. She kept waiting. Then suddenly, she felt him pushing back against her again. Ever so slightly, but still harder and harder, till eventually the tip of her finger went inside. She saw his body tremble the instant it did. She looked up at Sandy, but Sandy’s eyes were locked on him. She kept the tip of her finger where it was, then she wiggled it, ever so slightly. He shuddered again. She removed her finger and began messaging his backside all over again.

Why did that feel so good? He hated the very thought of it, yet he couldn’t help it. And now she was teasing him again by rubbing his backside all over again. Letting him know she was still there, just not where he wanted her. His eyes were closed. In this position, he couldn’t really see anything anyway. And it was easier to concentrate on her hands more.

Cassie got Sandy’s attention and with one hand pointed to the bottle of baby lotion, then she pointed to the dildo she had brought out of her bedroom a few minutes ago. Sandy got the message and coated the dildo liberally with the baby lotion while Cassie continued to massage his backside. But instead of taking the dildo herself, Cassie motioned Sandy to do it.

Chad really liked the feel of Cassie’s hands on his backside, but he really wanted to feel her finger again on his asshole. He knew she would do it again. It was just a matter of waiting. He suddenly felt the pressure again, but both her hands were still massaging him. He arched his back at the strange sensation.

Sandy saw him react strongly the moment she placed the tip of the dildo up against him. She held it there, pressing only very softly so as not to push it in. A huge thrill washed through her as she suddenly realized he was pushing back against her. She held it in place firmer and watched as ever so slowly the tip began to penetrate him.

Something was different. He knew it right away, but he couldn’t tell exactly what. It had to be Sandy’s fingers there now since Cassie was still massaging him with both hands. But the feeling felt so much different. He pushed harder against her and was surprised when her finger seemed to open him up even more - putting more and more pressure against the muscles that always held him tightly closed. It felt odd. Something was wrong! He quickly moved away, or tried to. Whatever was inside him moved right along with him.

Sandy was surprised when he suddenly tried to move away from her. But because she was trying to push against him, when he moved away, her hands naturally followed him and it remained just as far in as it was before. She held the dildo firmly, even though he was no longer pushing back – leaving it right where it was. She looked quickly up at Cassie. Cassie’s eyes were as wide as saucers.

He panicked, and in doing so he tried to push it away which only inserted it all that much further. He felt it open him up much wider now. He quickly drew away from it again, but the darn thing didn’t seem to withdraw at all – as if it were somehow stuck inside of him. In his panic, he pushed back again and withdrew, which only seemed to imbed whatever it was even further inside of him. He stopped, scared, not knowing what to do.

Sandy suddenly felt like she was holding onto a bucking bronco for a moment as he thrashed under her. But since she was trying to hold the dildo still, his actions only shoved it further into him. When he stopped, she took a deep breath and adjusted her grip to keep holding it firm. She glanced again at Cassie then back down to watch him. What would he do next?

She was holding it still. Not pulling it out of him. He waited. Whatever it was felt so foreign, yet tantalizing. Finally, he gave an exploratory push, very slowly and gently. He felt whatever it was sliding even further into him. Then suddenly something felt different. For just a brief moment, it felt like it had gotten wider, then was back to its original width again. What was it? He withdrew again, and still the object came with him. He pushed back again, and again felt the same widening, as if a tiny bump had passed through him.

Sandy held her breath now as he slowly worked the dildo further inside of him. When the first rib on it passed through him, her already wide eyes opened even wider. And then the second rib went through, and the third, and the fourth!
Cassie watched it all just as wide eyed as Sandy. When she thought it was far enough in, she whispered very softly. Hold it still now. See what he does.
Sandy did as Cassie suggested, but he wasn’t moving again. Then, ever so slowly, he was pushing against her again, burying even more of it up inside of him. But this time, when he withdrew, she held the dildo back, so that it pulled halfway out of him.

Chad felt the ribs passing back out of him again, but they only withdrew just so far. He couldn’t pull away from it any further. He was confused. He didn’t know what to do so he kept perfectly still. It felt so good, yet it felt so foreign. He hated it… he loved it. It made him sick, yet he yearned for it. His conflicts raging, he continued to remain perfectly still.
Cassie’s head was suddenly close to his. “Go ahead, baby,” she whispered to him. “You know you want it. Enjoy it.”
Enjoy it? The very idea sickened him. Yet it also tantalized him, as if it was scratching the very surface of his huge sexual need. What should he do? He wanted it. He hated it. He wanted to cry. Cassie’s hands were still massaging him. Sandy was holding whatever it was perfectly still. Why should this feel so good? He wanted to scream! He took a deep breath, and very slowly pushed back again. One by one, he felt the tiny bumps go past his tight opening again, each one intensifying the feeling a hundred fold. Then, just as slowly, he withdrew again. Damn! He hated himself for what he had just done… what he was doing. He hated himself more because he started pushing back again, then out again.
Cassie’s hands suddenly left him, but he barely noticed. His concentration was far more focused between the tiny bumps sliding in and out of him… and his new self-hatred. He began pushing a little faster, as if willing more and more feeling to come from those tiny bumps. But as good as it felt, it wasn’t enough. Not nearly enough to mount him toward any kind of orgasm that he desperately needed.
There was a click and a bright flash of light. Then it came again. Before he could fully react, a third time. Cassie had taken his picture again! Damn! He couldn’t imagine how humiliating he must look. He froze again and refused to move. The humiliation of the pictures bringing his self-loathing further to the fore. He began crying softly into the blanket below him. What had he just done?

Sandy saw Cassie nod to her and she pulled the dildo all the way out. She couldn’t believe what she had just seen. He had been fucking himself on it. But now he was crying. Why? She leaned down and put her head close to his, her arm holding him over his back. “What’s wrong, baby?” she asked tenderly. He turned his head away from her. Not wanting to answer. She looked up at Cassie and just shrugged.
“Roll over again baby, let’s finish diapering you. Ok?” She pushed on him a little and he rolled over. But he kept his head turned away from her as the tears continued to fall from his eyes. Sandy pulled several cloth diapers out of the bag and got them ready for him. “Do we push another suppository up inside of him?” she asked.
“I think we’ve put enough up him for one night,” Cassie replied.
Sandy nodded and grabbed one of the super thick cloth diapers. She spread it open and had him raise his legs so she could stick it under him.
While she was doing that, Cassie rummaged through the bag and brought out yet another baby bottle, she gave it to him to drink while Sandy finished up. He put it to his lips and began nursing from it. At least his tears were finally drying up.
“Do we tell Mel about this?” Sandy asked as she worked on inserting the first diaper pin.
Cassie considered it. “I don’t think so. If he wants to tell her, then that’s fine. But I don’t see any need to tell her unless she asks us.”
Sandy nodded, then went to work trying to fasten a pin on the other side. A minute later, she was pulling his plastic panties up on him when he suddenly had a horrified look on his face and shouted, “Oh no!”
“Ah, ah, ah!” Sandy said quickly as she slapped his hands. “What did we tell you about speaking?”
He looked at her like she was crazy, but the truth of his problem became quickly apparent. The dildo going in and out of him, combined with his dinner and the bottles had finally triggered the suppository that Cassie had inserted into him that afternoon. There was no way to stop it and he didn’t even try.
“Ewww, gross!” Sandy proclaimed as she realized what he had just done. “I’ll let you clean him up.”
“Oh no. You’re the one who wanted to babysit. And I have to do this every day. It’s your turn!”
“Yuck,” she replied as she started pulling down his plastic panties again.
As she cleaned him up, Chad felt a small bit of satisfaction in the fact that he was getting back at her… for something.
This time, Sandy put two of the super thick diapers under him, then folded three of his regular cloth diapers into thirds and put them inside his diaper to act as an additional soaker. The material was so thick she had a much harder time getting the diaper pins in, but she finally succeeded. His plastic panties were far more stretched than they had been before.
When she was done, she had him sit on the blanket instead of laying down. Chad spent a few moments trying to figure out what to do with his legs, because the bulk in his crotch was now so thick he legs were forced wider than they had ever been. It was a bit uncomfortable.
Sandy kept him on the blanket and brought back a plastic bag from her room. She dumped it out on the blanket next to him. Small baby toys tumbled out. There were several dolls and small stuffed animals. A rattle and a teething ring. And some colorful plastic shapes that he really didn’t know what they were.
“Ok, baby, time for you to play like a good little baby,” Sandy told him.
He just looked up at her. Play? With this junk? How? He had no idea. He looked at the things around him. He picked up one of the colorful pieces. What was he supposed to do with it? He discarded it in favor of one of the dolls. He held it, but now what?
“What’s the matter, baby?” she asked, grinning widely. “You’re not happy? Happy babies talk to their toys all the time. Go ahead, talk to your toys. It will make you feel so much happier.”
Talk to them? She had to be kidding. He looked at her for a moment instead.
“You better start talking to your toys. You wouldn’t want Auntie Sandy to punish you!”
Geez! He looked back at the doll in his hand. “Ga ga,” he said tentatively. He looked up at her. She had one eyebrow raised, expecting him to do more. He picked up another toy and made more nonsense sounds. He looked back at her. She was finally smiling now.
“You just keep talking to your toys like that. That’s such a good little baby.”
He felt so ridiculous babbling to each of the different toys – constantly. And at the same time, what he was doing was still fueling his sexual need. Oh God he needed some relief! He needed it bad! And as he babbled away to the baby toys, Cassie’s camera started flashing again.
He didn’t know how long Sandy had made him sit there and “talk” to the toys. But she finally came in and told him it was bedtime. Sandy was holding his bag of diapers and bottles, and Cassie was holding his purse. They made him crawl to the door, before they helped him to his feet. His legs were spread so wide by all the diapers that he could hardly walk. Both girls laughed at him over it.
They took him back to his own apartment where they put him straight into his bed. Cassie handed him another baby bottle to drink while Sandy put his pacifier down on the floor next to him. She then made him hold his teddy bear while she pulled the covers over him.
“Goodnight, baby,” Sandy said as she kissed him on the cheek.
Cassie was next. “Goodnight baby,” she too said.
And he was suddenly left alone in the dark of his apartment. What a day it had been! Weird! He nursed his bottle while he thought about it and finally fell asleep.

Ugh! This was not fun! Not to her anyway. Why had she done this? Detective ‘Conceited’ was rooting with his big thing inside of her like a dog in heat and she was hating every minute of it.
She had purposely asked him inside after their date, knowing that he would take her to bed at the first opportunity. And she had wanted him to. Not because she liked him, but because she wanted to see what it was like once again to have a big manly cock inside of her. But Detective ‘Crappy’ had been the same as he ever was. No romance. No caring in the least about her and what she wanted or liked. Not even a touch of tenderness. He was all – do this! Do That! She was sure that his every thought was me, me, me! He had been the same way during dinner too. If he wasn’t trying to pry information out of her about her clients, then he was only talking about himself. Boring!!!
And now she had made the mistake of thinking she wanted to have sex with him. She was really just trying to compare it to what she had been experiencing with Sissy lately. And so far, it was no contest. Sissy was the clear winner – by a mile!
The more Detective ‘Butt Face’ pumped away at her, the more angry she got. She didn’t even feel like trying to fake an orgasm for him – she was that disgusted. She finally had enough! “Stop! Stop! Stop!” she screamed and started hitting him on his back.
He stopped humping her. “What’s wrong?”
“Get off me you jerk!”
“What?”
“I said get off!” she screamed.
He rolled off of her. “What’s your problem?”
“You! You conceited bastard. “Get out! Get out now! I don’t want you near me anymore!” She pulled the covers up over her naked body and held them tight around her neck while she glared at him.
“I don’t understand. You were loving it!”
“I was hating it, you jerk!”
“What the hell’s gotten into you?”
“You! You’re nothing but a big conceited slimy bastard. Now get out of here! And the next time you want to keep one of my clients in jail just to try to date me, he can stay there!”
She waited, her anger at him stayed fully ignited until he finally closed the door behind him. God, what an awful night. She jumped into the shower to get the last of Detective ‘Good for Nothing’ off of her then she got comfortable in her nightgown and robe. She made herself a cup of tea and tried to relax. And through it all, she wondered how Sissy’s evening had been. It couldn’t have been any worse than hers was!
It was late now. Very late. Hopefully he should be asleep. She went to her desk and wrote a quick note for him, then she went outside and over to his apartment. She peeked in at him. He was sleeping. In the dim light he could just make out the bow that was still tied into his hair. She was betting his night had been a lot of fun. There was an empty baby bottle on the floor – next to his pacifier. She was tempted to put the pacifier into his mouth, but she didn’t. She quietly set his clock radio to go off at the right time in the morning.
Ever so gently she knelt down next to him and planted just the barest whisper of a kiss on his forehead. “Sleep well baby. Sleep well.”