The Bet - Chapter 10 (Monday – week 2 Part 2)

The Bet
by Karen Singer

Chapter 10 (Monday – week 2 Part 2)

Mel hurried through her first client of the day as fast as she dared. When she was done, she told Andrea that she needed a little while to work undisturbed. Then, spreading out some pages that she had copied from the internet in front of her, she picked up her cell phone and dialed the number on the ordering page. The first question she asked was to make sure they had next day delivery available. Then she placed her order.
Chad wasn’t going to like it one bit, but the more she thought about it, the more the very idea of the thing was stimulating her. She hated the fact that she had just started her period. Otherwise she’d have Chad between her legs again as soon as they got home. Well, if she couldn’t get any, then she was going to be making extra sure that
Chad couldn’t either. The more she thought about it, the more she laughed to herself.
She was just about to turn her cell phone off and leave her office when her phone rang. “Hello?”
“Hey Mel, this is Cassie. I was just wondering if Sissy was going to be paying me a visit later.”
Mel laughed some more. “He sure is. At least he’s supposed to. I’ve packed everything he should need in his diaper bag for you.”
“Diaper bag?”
“Of course. You’ll love it, it’s bright pink!”
“I can’t wait!”
“Oh and Cassie, I put a couple of baby bottles in his bag for him. Can you make sure he drinks at least one of them?”
This time it was Cassie’s turn to laugh. “No problem. Like I said, I can’t wait!”
After Mel hung up from talking with Cassie, she finally went back to work. She didn’t get a chance to check her messages till almost lunchtime. When she did, she found one from her therapist, Gloria, asking her to call. She quickly dialed the number. “Hi Gloria, this is Mel.”
“Hi Mel. I just wanted to tell you that I got your message from the other night.”
“Yeah, I’m sorry about that, I was a bit angry at the time. Still, if there’s anything you could do along those lines, I’d be really appreciate it.”
“Well,” Gloria said, “it’s a bit unusual, but then so is this whole thing. It’s not at all in the direction I was planning to go, but I think I can work with it.”
“Gloria, if you can, that would be wonderful!” Mel replied.
“How have things gone with him this week?”
“It’s hard to say. I think it’s still too early to see any results.”
“Did he seem to notice in any way that I had hypnotized him?”
“Not that I could tell.”
“Good. I thought I had him under just far enough. I’m really glad that it worked. It would have been awkward otherwise. Hopefully, next week I can get him under even further and we’ll try some new things. Then we’ll just have to see what happens.”
“Thanks Gloria, you’re the best!”
“So what else have you been doing with him?”
Mel spent a few more minutes than she really had time for, filling in her friend on the last few days.

Chad left his desk at lunchtime and practically strutted to his car. He had wet his diapers twice during the morning just so that Mel would never know what he had done in the bathroom. It was only a few blocks to the gym where Cassie worked, and he found it easily. The parking lot was fairly full. He dreaded getting out of the car and carrying the big pink diaper bag in, but as with so many other things lately, he had no choice. No matter how he tried to carry it, the darn thing was just too noticeable. He wound up finally bunching up the strap in his hand to carry it inside.
Once in the door, he could see how busy the place really was. The receptionist was watching him closely. He wondered what she must think about him carrying a pink bag like he was – especially bringing it into a women’s gym. “May I help you?” she asked. “You know, this gym is for women only.”
Yeah, she was definitely eyeing his bag. “Um… yes, I know. I’m here to see Cassie.”
“Oh yeah, she mentioned she was expecting someone. Wait here. I’ll get her.”
While Chad waited, he set the bag down on the floor where he was hoping it would be less noticeable. If he could have found something to hide it behind he would have.
The receptionist came back a few minutes later with Cassie right behind her. “Hi Sissy,” Cassie said – all too loudly.
Chad saw the receptionist’s eyes bulge. She was suddenly looking at him a lot more closely. “Hi Cassie,” he replied softly.
“This way,” Cassie said with a crook of her finger. Then she led him back through the gym. As they walked, Chad was more than ever aware of the stares the women were giving him and his pink bag. Had any of them heard her calling him Sissy? He hoped not.
Cassie opened up one of the private offices and ushered him inside. The office had mini-blinds on the window of the door and she closed them. “There,” she said. “Now we won’t be disturbed.”
Chad was both nervous and excited over what was about to happen. He certainly wasn’t afraid of her punishing him in any way, but still, she was a complete stranger who was about to change his diapers. It was actually thrilling in a way, but still, he was nervous about it.
“I love your bag,” Cassie commented as she pushed a couple of chairs out of the way.
“It’s a bit too pink for my taste,” Chad replied, more convinced than ever about how noticeable the thing was.
“Nonsense. It suits you to a T!”
Chad said nothing to that since he realized that it probably did. He was fully expecting her to tell him to undress, but she didn’t. Instead, she came over and unbuckled his pants and pulled them down to his ankles herself. That surprised him more than he had expected. It also started arousing him a bit. One by one, she removed his shoes, his socks, his pants, pantyhose, and shirt – leaving him standing in just his all-in-one girdle. Her attention was like a cross between an unexpected lover and a mother changing her child. Either way, he was enjoying it. Then she started to pull down his all-in-one girdle. She didn’t get far. “Wow, that’s tight. Maybe you’d better get that thing off yourself.”
“Yeah, it is tight,” Chad confirmed as he started pulling the thing off of him. “Very! But it doesn’t seem to be nearly as bad as it used to. I think I’m losing weight.”
When he was just down to his diapers and plastic panties, she had him lay down on the floor where she pulled his plastic panties down to his ankles. Chad felt her pulling on the tapes that held the first diaper closed, then she pulled it open. He felt her pulling on the tabs for the second diaper, then suddenly he felt himself exposed as the cool air washed over that part of him. He couldn’t believe that this was actually happening to him. He had dreamed about it of course in his fantasies, but he never expected anything like this to actually happen.
“You’re not even messy,” she exclaimed, somewhat surprised.
Chad suddenly was worried that he had slipped up earlier. If it ever got back to Mel what he had done he’d really be in for it. “I don’t think there’s all that much left in my system anymore,” he replied. “I think it’s been taking longer and longer for the suppositories to do anything.” Fortunately, she seemed completely satisfied with his answer.
She opened his diaper bag and started going through it. “Mel really did put everything in here.” She pulled out a bottle and handed it to him. “Drink up… baby.”
Chad was aghast. Not another bottle! But he didn’t dare not drink it for fear of Mel’s anger. While he was drinking his bottle, he felt her wipe him off quickly with the baby wipes, then she pulled out and prepared two more diapers for him, slitting the crotch of one of them with a pair of scissors first. She slid the old diapers out from under him and slid the new ones in their place. Then she got one of the suppositories out of his bag and shoved that up him – a lot further than Mel ever did. “There,” she said, “it’s up there good now.” All too quickly, she had him taped up again and his plastic panties back in place. He was less than half-way through with his bottle.
“I think you better stay there like that and finish that thing before you get dressed again.”
Chad wasn’t sure if he had a choice in the matter or not.
“And you better hurry up – in case anyone else might want to use this office.” While Cassie waited for him, she stood up and opened the mini-blinds on the door window and looked out. “I wonder if maybe we shouldn’t just leave these open right now,” she said. “I’ll bet anybody walking by would love to see the big baby on the floor there drinking his bottle.”
That got Chad drinking as fast as he could. Fortunately, she closed the blinds again a few minutes later.
Finally he was finished and she put his bottle back in his pink bag again while he struggled with the all-in-one girdle. Finally he was totally dressed again and she opened the door for him. Once again he had to carry his big pink bag through the room of exercising women where they could see it all too clearly. “See you tomorrow,” she said as she left him at the door.
Once he was safely back in his car, Chad stopped to think about the experience. He had enjoyed it of course, but the truth was that it wasn’t nearly as fun or as exciting as he thought it would be. She had teased him a tiny bit of course, but mostly, she had just changed his diapers and that was it.
Feeling a bit let down, he drove off to get some lunch.

“Hi Mel, it’s Cassie.”
“Oh, Hi Cassie. Did Sissy make it there ok?”
“Oh yeah, and it went just fine.”
“Good. He wasn’t too much of a mess was he?”
“No! In fact he wasn’t messy at all. He said he thinks his system is probably all cleaned out.”
Mel had to think about that for a moment. “Yeah,” she admitted. “It probably is. I hadn’t thought about that.”
“He also mentioned that he thought he had lost a little weight too so it makes sense.”
“Yeah,” Mel agreed. “I guess I better start feeding him more. So everything went ok?”
“Like I said, no problem. I pretty much undressed him completely when we started – except for that girdle – wow that thing is tight. But afterwards I let him get dressed by himself again. I was going to make him sit down so I could put his shoes and socks on for him as if he was a toddler, but it took him so long to drink that bottle that I didn’t bother.”
“Oh good. I was going to ask about the bottle.”
“Yeah, he drinks from it real good. Just like a baby.”
They both laughed, but something that Cassie had said earlier finally sank in. “Cassie, you said you let him put his own shoes and socks back on?”
“Yeah. Why?”
“He was wearing socks?”
“Of course, why?”
“Oh nothing. Never mind.”
“Is there a problem?”
“No not at all. Thanks so much Cassie. I guess it’s ok to send him tomorrow too?”
“Sure. I’m expecting him every day now. Hey, it was fun.”
“Good. Thanks Cassie. Bye.”
Mel hung up her phone. He had found some socks. He thought he was getting away with something. She almost laughed. Well, let him for now. Let him think that he had won at least one tiny battle. There were bigger issues at stake. Besides, if things stayed according to her plans, he wouldn’t be wearing them much longer anyway. As she thought about her plans for the future for him, she really did start laughing.

Chad went back to work after lunch, but more and more his mind went back and dwelled on the diaper changing he had so recently experienced. It hadn’t been a problem at all in any way – other than having to carry in his embarrassing diaper bag. He had even fooled Cassie when he told her that he hadn’t messed himself because his system was empty. That thought brought him back to the pleasure he had experienced earlier that morning. The more he thought about it, the more he wanted it again. He realized that he could do it again. It had been a very long time since he’d been able to get himself off and there was still a lot of need built up in him. Once again he went into the men’s room to enjoy himself fully.
Chad didn’t dare use the toilet again all afternoon, knowing that it would be Mel who changed his diapers next time. Late in the afternoon, he even let the suppository do its nasty work in his diapers too. The tight confines of his girdle made that difficult, but the suppositories completely destroyed any mass that would have been inside him, turning everything into a runny mush that eventually escaped the pressure of the girdle and spread out around him. It was a horrible experience. Absolutely horrible! And when he was done, he couldn’t wait for his next diaper change.
After work, Chad again removed his socks and hid them before he drove to Mel’s office. When he got there, he carried his embarrassingly pink diaper bag inside with him. He knew better than to leave it in the car. As usual, there were several people waiting inside when he got there, he barely even glanced at them, but he was sure they all noticed the bag he was carrying. Andrea was certainly noticing it too since she couldn’t seem to take her eyes off of it. With a big smile she escorted him straight back to the usual empty office again. Chad expected her to go get him a cup of coffee like she usually did, but she didn’t. Instead, she took his diaper bag from him and opened it and sorted through the contents. She pulled out the remaining baby bottle that was still full and handed it to him. Chad sighed as he took it. He was getting tired of drinking everything only through the bottles. With another big smile, Andrea left him alone.
Chad was resting with his feet up on the couch, thinking about how great it was now that he had found a way to get relief, when Mel finally came in quite a while later. She closed the door behind her and just stood there with her arms crossed as if she were waiting for something. Chad sat up on the sofa, waiting for her to say or do something. But she didn’t. She just stood there looking at him. Finally it dawned on him. “Hello Mistress,” he finally said.
Mel’s face instantly changed to a broad smile. “You’re starting to learn,” she finally said. “Hello Sissy. Did you have a good day today?”
“Yes, very.” He replied.
Mel nodded. “How did you enjoy being changed by Cassie?”
Chad considered the question. “It’s funny,” he replied, “I was really expecting it to be more… thrilling I guess. But in reality, it wasn’t. Mostly, she just changed me and that was it.”
“That’s all she was supposed to do. What did you expect?”
Chad shrugged. “I don’t know.”
Mel grabbed his diaper bag and started pulling out the things she would need to change him. “I like you carrying this stuff around with you a lot better than me having to carry it all the time,” she noted. She picked up the empty baby bottle he had just finished and walked out of the room with it. A few minutes later she was back with it again, only now it appeared to be full of water. She set the bottle down and told him to start getting undressed.
Chad wasn’t at all happy to see the full baby bottle that he knew he’d be soon drinking. But he was more than happy to finally get changed again. As he was removing his clothes, Mel said, “Cassie said you weren’t messy at all when she changed you earlier.”
Chad looked up at her, worried that somehow she might know what he did. “No, I think my system was too empty.”
Mel nodded. “That’s probably my fault. How about now?”
Chad actually blushed. “I’m afraid I’m very messy now.”
“Good!” Mel replied, sounding much more satisfied. After she had rediapered him again she stood back while he finished his bottle of water. “So,” she started. “How did it go having no socks to cover your pantyhose again? Did anybody notice?”
Chad was suddenly very worried again. “I don’t know,” he admitted. “I hope nobody noticed. Mostly I sit at my desk where I don’t have to worry about it.” Did she know? Was there any way she could possibly know what he had done? He realized he had worn the socks when he saw Cassie at lunchtime. Did Cassie tell Mel that he was wearing socks earlier? He was suddenly very worried about that.
But Mel’s answer surprised him. “I was sure you wouldn’t have any trouble. Most people don’t notice things like that, do they?”
Chad was relieved. He had gotten away with it – clean. He thought of something else that might keep her off the track. “Uh, Mistress, I was wondering though, I need to get some new pants for work, especially since I seem to be losing a bit of weight lately.” He saw Mel smile at that. “Would it be ok if I went shopping for some tonight? I’d like to get a few pairs that are a little bit longer to make sure my ankles won’t show. I wouldn’t be gone all that long.”
Mel was surprised by his question, very surprised. She thought about her plan for him. The timing of his request couldn’t have been any better. She smiled at him. “Oh, I think that would be all right. In fact, why don’t we grab a quick dinner again tonight then we’ll both go together. I’ll buy the dinner, but you’ll be buying everything else!”
Chad was surprised that she had agreed so readily. He didn’t really need any new pants right now, but he did always try to keep nice looking clothes for work. It wouldn’t hurt him to have a few new pairs anyway. “Thank you, Mistress,” he replied happily. But as he finished getting dressed, he began to worry about going shopping with her again. The last time had been one of the most embarrassing times of his life.

What’s Happenin’

This entry is just a little catch-up on what’s happening in my life right now. And also a tiny bit of ranting.

But first of all, I’d like to say a very special thank you to everyone who left me comments. Thank you! I don’t really expect any comments about the story (although I really appreciate and love them) because when you’re trying to follow along on something like this that’s being dragged out forever, it’s very hard to get a full sense of the story line. You lose the emotions that are associated with each chapter, let alone the story as a whole.

I’m still working on the story and will be for a very, very long time. I have notes for every day of the story period about things that I plan to happen. When I started this story, I didn’t plan on it being one chapter per day – let alone writing nearly this much. It just sort of happened. Now it’s become something of a challenge for me, and I have to admit, so far I’m really loving it. I’m worried that some chapters might get a bit dull later, but my job is to try to keep them from being too dull. There is a definite conclusion to this story and it’s going to take every day that I have outlined to get there. So if I make it, it should only take another two thousand years or so to post it all.

Along with this story, I’m also writing three other stories now. Two of them are more for the legitimate market that I hope to someday publish (If I ever get off my ass and try to find an agent).

For those of you who have been concerned about my home life, another huge Thank You! We took my in-laws back to Louisiana about a month ago – they very suddenly demanded to go home even we all knew they couldn’t take care of themselves. We were thinking that they would probably stay there through the holidays, but last Friday night they called and said they wanted to come back right away. It was only a matter of five minutes between us not planning on getting them for a long time, till we were packing our bags to head out the door. So we have them again, this time probably for a long time – if not forever.

We have discussed nursing homes and long term facilities for them. We know that it’s going to probably be necessary at some point. But not yet. Especially since my wife is so adamant about taking care of them. My father in-law is getting more and more addle-headed and definitely much weaker. We’re now trying to find a very lightweight wheelchair to buy for him. He often asks the same question every ten or fifteen minutes.

Even though they’re in our house fulltime now, my wife considers that I have to be around all the time, or I’m being anti-social. We watch tons of TV, even though I can’t hear any of it. The reason I don’t hear any of it – even with the volume turned way up – is because my wife and her mother never ever stop talking. I sat and tried to time them two nights ago while we all watched TV. The longest my mother in-law was able to go without saying something was eleven seconds (from six thirty to ten o’clock). Then I tried it again last night, but the phone rang. As soon as my wife hung up the phone it rang again. Then again. And again. Between my wife and her mother they stayed on the phone for three and a half solid hours – while they watched TV. That’s very common here! All that talking is probably one of the reasons why my father in-law demands to go to bed so early.

My vacation from work is scheduled for later in October. I’m required to take a full five days in a row. My wife and I were planning on renting a house up in the mountains for a few days. Something we both love to do. We haven’t done it in a very long time now. We haven’t done anything in a very long time now. We were at the brink of booking something that would hold us and my wife’s parents for a few nights, but I backed down and stopped it at the last second. Why? Because I got scared. I got scared because of money.

We have three kids and six grandchildren and now one great grandchild between us. And I’m helping to support all too many of them. If it wasn’t for the grandkids, we’d tell our kids to fend for themselves. But how do you say no to kids who are hungry? On the positive side, my daughter is finally working again in a real good job and has had a paycheck! She’s doing much better and things will improve there over time. But the other two… the boys. One drives a truck and his company is barely hanging on. The other one is waiting on word that the plant he works in will be closing. They’ve already cut everybody in the plant down to 36 hours a week and things look real bad.

While I keep hearing about the economy getting better, all I see is that it’s getting worse. For the first time ever, the company I work for didn’t give a cost of living increase. That’s ok. I’m lucky I still have a job. My county taxes went up a whopping full seven hundred dollars this year. That bill is coming up soon. My insurance rates are going out of sight. All my utilities and other bills are going up. And have any of your checked the price of groceries lately? But fortunately Christmas is just around the corner.

I try to keep looking on the bright side and count my blessings. But sometimes things just overwhelm me. It’s difficult. But for my wife and family’s sake, I try to keep as bright an outlook as possible about everything and smile. Everyone looks to me as if I know the answers to everything and like I can solve anything. I guess I’ve done all right so far. But the truth is, I feel all too inadequate. A normal feeling I’m sure.

And so I turn to the only escapism I have. I write. In my fantasies, life is a lot more interesting. The pressures are different. In my mind I get to live someone else’s life. Some fantasies are total fun. Some are not. But all of them interest me enormously. I’m really glad that this blog is letting me share one of those fantasies with you. To me, it’s fun and challenging. I only pray that it’s providing a few others with a few moments of relief and escapism from the stresses of their lives too.

Thanks for being with me,
Karen

The Bet - Chapter 10 (Monday – week 2 Part 1)

The Bet
by Karen Singer

Chapter 10 (Monday – week 2 Part 1)

The blaring music was all too loud as Chad’s pink clock radio woke him up. Distressed by the sudden noise, he quickly got up and turned the darn thing off. He sat back down on his blowup mattress and rubbed his face. What a night it had been. He had spent several hours tied up in her bathroom with that dirty diaper over his head. Awful! And despite brushing his teeth over and over again last night, he could still taste the soap in his mouth. He got up and went into his bathroom. Halfway there, he felt the need to pee again. As he usually did, he released it immediately into his diapers without hardly thinking about it. It was becoming more of a reflex action. He realized that and reminded himself to start holding back a little more. She had him peeing so much now that he was becoming way too used to it - already. Time to start fighting back a little more.
He brushed his teeth again, hoping it would finally clear the last of the soap taste from his mouth. It helped… some. He left the bathroom, never once even glancing at his toilet or even thinking about it. He dared not. The way she had wrapped it up left him no way to use it at all. Looking at it was a terrible reminder of that fact. He walked into his empty kitchen and pulled a baby bottle out of the refrigerator, the first of two that she had commanded him to drink before he went to see her in a little while. The bottle had tape wrapped around the top so he couldn’t open it and pour it out. Still tired, he sat back down on his mattress and drank the fruit juice that was inside – apple this time, a pleasant surprise.

Mel’s alarm clock went off and she slapped at the snooze button to silence it. The noise was irritating. She felt irritated. But her period had started in the middle of the night and during those times she always felt that way. It was times like these that made her wish she had a job where she could just call in sick once in a while. But she didn’t. Sighing, she fixed the alarm so it wouldn’t go off again and got out of bed.
As she headed toward her coffee pot she thought about Chad. Had she done enough to him last night? Had she done too much? She didn’t know and probably never would. She started the coffee brewing and headed for her bathroom. As she sat to pee, she could still smell the lingering fragrance of all the air freshener she had sprayed in there yesterday. She wondered again about what she had done to Chad. Was she doing enough to keep him on track to win her bet? There was more she was trying to do with him than just make him incontinent. She had wonderful visions of him being her personal servant.
He had turned out to be a good cook. That had been a really nice surprise. But he certainly didn’t know his place as a servant yet. Not yet. Not by a long shot. But of course, teaching him that was all part of her plan - her ever spiraling plan for him that would eventually lead him down to her final vision for him. She hoped! She had completed the first rotation of that spiral now. Was it working in any way? She had no way of knowing. It was always hard to see any results at the beginning of a project.
As she got into her shower, she felt glad that she wasn’t going to his apartment this morning, not till later anyway. She had been able to sleep an extra half hour. It was time for Chad to start doing things a little bit more on his own – without her supervision. Tiny things at first, but she had to start somewhere.

Chad shaved his face, then drank his second bottle of the morning. He wanted a shower, but he was locked inside his onesie. Mel had told him he could use her shower when he was ready. When his bottle was done, he started collecting the things he needed to take to her apartment: his clothes for work, several disposable diapers, a fresh pair of plastic panties, one of his all-in-one girdles, pantyhose, the two empty baby bottles he had finished that morning, and a few of the makeup items she had specified the night before. He put them all into a plastic bag to carry. The last thing he grabbed before he went out his door was the pink diaper bag she had spent so long packing for him last night. Just touching the thing sent shivers through his body. He draped it over his shoulder – like a purse he thought. His cock gave another jolt of excitement inside his diapers. Damn he needed some relief!
Cautiously, he opened his door and looked out. It was still so early that nobody was around. Relieved, he went out and walked quickly to Mel’s apartment where he knocked softly on her door. He was relieved when she opened it promptly and he ducked inside. He set his things down on the floor and turned to her. She was just standing there looking at him, as if she were waiting for something. He wasn’t sure what to do so he stood there waiting himself. The awkward silence grew. “What?” he finally said.
“I’m waiting for something,” she said.
Chad searched his brain. He couldn’t remember anything she had told him he needed to do right away when he got there. He finally shook his head. “What?”
“Isn’t there something polite you should greet me with whenever you see me?”
He nearly groaned aloud. So she was playing that game this morning. At least he knew what she wanted. “Good morning Mistress,” he said to her.
She nodded. “That’s better! Good morning Sissy.”
He had an odd feeling every time she called him Sissy. He both hated it and loved it - and it always made his cock jump.
She came around behind him and unlocked his onesie for him. “There’s a clean towel in the bathroom for you. I’ll see you when you get out of the shower.” While Chad was busy in the bathroom, Mel found the two empty baby bottles he had brought with him and took them into her kitchen. She grabbed two fresh bottles filled with more of her green tea mixture from her refrigerator and put them both into his diaper bag for later. Since Cassie would be seeing him at lunchtime, she was sure that Cassie would make sure that he finished at least one of the bottles.
Chad gratefully soaked himself clean in her shower. The only shampoo he could find though smelled even more girly than the new shampoo she had bought for him, but he used it because it was all he could find. When he had dried himself off, she again applied some baby lotion and powder, purposely taking the time to fondle him in a way that she had never done before. He grew hard instantly and was about to start thrusting up into her hand when she pulled away from him, a mischievous smile on her lips. He nearly screamed with frustration. Aching with need more than ever, he laid back while she taped two fresh diapers on him and pulled up his plastic panties. He was a bit surprised that she only put two diapers on him. Her normal routine the week before was to use three. But then he knew he had to go to see Cassie at lunch today to get changed so his diapers wouldn’t have to be thick enough to last all day.
The all-in-one girdle followed next as well as his usual pantyhose. Then she stopped. “Ok, Sissy, makeup time.”
Chad got suddenly much more nervous. “Please Mistress, not for work.”
Mel shook her head. “Don’t worry about it. Putting on makeup is a part of every woman’s normal routine every time they go out. I want you to start learning to do the same.”
Chad felt very relieved. Once again he did his best with the makeup. Mostly it looked terrible. She had him wash it all off and just do his mascara, then she made him practice over and over again with the eye shadow before she declared that it was acceptable. “Ok, Sissy. Wash it all off,” she told him. Chad was glad to finally do that.
“Ok,” she finally said to him, “finish getting dressed.”
But Chad had one more problem. “Um… Mistress?”
Mel turned back to him. “Yes?”
Chad held up his hands to show her the nail polish still on his fingers. “I don’t have anything to take the polish off with.”
Mel just looked at his hands. “Oh…” She appeared to be thinking for a minute. “I’m afraid that I don’t have any either.”
Chad was suddenly panicking again.
“I get my nails done professionally every week. I really don’t have much need for nail polish remover.”
“But what am I going to do? I can’t go to work like this!”
“I really don’t see why not,” Mel replied calmly. Chad was clearly having a mental fit. Mel wanted to laugh, but she kept a straight face. “Tell you what. If you really have to, you can stop at a drug store on the way to work and get some.”
“You mean… go into a store… like this?”
“Why not? Look how you went shopping yesterday.”
“But I can’t.”
“Look Sissy, as I see it, you have only two choices. I don’t have any remover here, so you’re either going to have to stop and get some, or you’re just going to have to wear it to work. And to be honest with you, I think you should really consider wearing it. It is a very pretty color for you.”
Between his shock, his anger, and his frustration, Chad wanted to scream. But what could he do? He’d just have to go into a store somewhere on the way to work and get some, then take the polish off in his car.
“Oh, and Chad,” Mel continued. “Don’t you dare touch the polish on your toes.”
Chad just shook his head angrily. Darn the woman!
When Chad was finally dressed in his pants and shirt and ready to walk out the door, she brought him back into the bathroom again. “Let me see you do your mascara one more time,” she commanded.
Chad couldn’t believe it. It was getting late! He was starting to really worry about what time it was since he now had to stop to get nail polish remover – not to mention getting the polish off of his hands. He didn’t really want to be late for work. He quickly grabbed his mascara that was still on the counter and started on his lashes.
“Just a light coat,” she told him as he started.
Chad went over his lashes twice with the mascara.
“Good enough,” she declared sooner than he expected. He put the mascara down and started to wash it off. “Leave it!” she told him.
His eyes bulged. “But…”
“I said leave it!”
It was not exactly what he wanted to hear.
Suddenly, he found himself being pushed toward the door and she was handing him his diaper bag. “Now don’t forget about Cassie at lunch today.”
“I won’t,” he replied. And then he was outside with the door closed in his face. He felt silly carrying the diaper bag like it was a purse. Did it have to be so pink? He worried about how visible the mascara was on his eyes. He’d have to wipe that off later. He worried more about the bright red nail polish on his hands. That would be awfully hard to hide. Hurrying so fewer people could see him, he went down to his car.

Mel smiled to herself as she walked back into her bathroom. She opened the cabinet under her sink and poked around at some of the bottles in the back. There it is, she thought as she found the bottle of nail polish remover. It was completely full. She had had it for a while now and never opened it. Playing with Chad over it had been just too much to resist. She had no doubt that he would stop and get some on the way to work, which was kind of a shame because the color really was a good one for him. She smiled as she stood back up. All in good time. All in good time.

Chad drove like a madman to the drug store. But before he got out of his car, he found the socks he had stashed in the console and put them on. He was secretly proud that Mel would never have a clue about them. Then he ran into the store. He had been in there many times before. He had even bought nail polish remover there before, but never in an emergency. Fortunately it was still early enough that there weren’t many customers. He went straight to the polish removers and picked up a large bottle. Then he started toward the checkout, but changed his course as soon as he realized he needed something to use with it. Spying a box of tissues, he quickly picked them up too. The girl at the checkout made some odd faces when she saw his nails and he felt very uncomfortable about showing them off in front of her, but he had no choice in the matter since he needed the things he was buying. Fortunately, she only smiled at him and told him to have a nice day. Yeah right!
Chad spent way too long trying to get all the polish off his hands out in his car. The clear polish that the nail tech had used on top was making the job all that much more difficult, as were the many layers of the red color. He was becoming more and more frustrated about it, mostly because of the time it was taking to remove it all. Finally, he decided that they were good enough and he raced for work, getting there just barely in time. He was more than relieved.
As he walked from his car to his desk, he was very much aware of how much more comfortable his girdle was with only the two diapers on under it. In fact, while the entre thing was still terribly tight, it didn’t seem nearly as bad as it had last week. Maybe he was getting used to it. Possibly. But when he had fastened the belt on his pants earlier, he had pulled it another notch past where he usually did. He realized that all the suppositories she had been putting in him had probably made him lose weight. Still, it was really nice to be a lot more comfortable.
He was very much aware of the mascara on his eyes, but he was running so late that he didn’t have time to wash it off first. He prayed that nobody would notice it. He checked in, then went briefly to his desk and fired up his computer. He stayed there for a few minutes and pretended to work. Mostly though, his brain was reliving some of the highlights of the weekend – well, at least the parts that hadn’t been so painful. His cock was growing again. He finally stopped himself because he knew he was only making his frustration worse. He had to find a way to get some relief – and soon.
Hoping that by now the men’s room should be empty so that nobody would notice the mascara he was wearing, he hurried into it. He hadn’t been into the men’s room in a while now and it almost felt strange walking in there. In truth, he considered just going into it a major victory. The place was empty and he quickly washed the makeup off his eyes.
He was about to leave, when he thought about something else. His girdle wasn’t nearly as tight as it was last week. He was now very used to getting it on and off. Knowing he was about to score another major victory, he went into one of the stalls and closed the door. His pants, his girdle, his plastic panties, and his diapers were soon all down around his knees. All the things she had put him through were soon coursing through his mind as he stroked and massaged himself in absolute bliss. All too soon, he climaxed strongly. It wasn’t quite as strong as he had hoped for, but still, it had been really great. As he was standing there recovering, he realized something else, all the activity had triggered the darn suppository and it was about to do its job. Feeling better than ever, he sat back on the toilet and allowed himself the luxury. Mel had made a grave mistake and he had been smart enough to find it. Then, since his cock had finally gotten small enough, he allowed himself to pee into the toilet too – one hundred percent fully in control.
Feeling more confident than he had in a very long time, Chad finally went back to his desk and got to work.

The Bet - Chapter 9 (Sunday – week 2 Part 2)

The Bet
by Karen Singer

Chapter 9 (Sunday – week 2 Part 2)

Mel had remained silent through most of the store. He had too. She was still silent, and thoughtful, all the way home. When she got there she got out of her car and opened the trunk. “Start getting it all upstairs,” she said. Then she left him.
Chad knew that once again he would be making trip after trip, exposing himself to everybody that would be around that cared to see him. But he didn’t protest in the least for fear that whatever she had planned as a punishment for him might be even worse. He just wished that her apartment had been on the bottom floor instead of upstairs where the trips were much longer, not to mention harder in his high heels.
With each trip up the stairs, he kept expecting Sandy or Cassie to come out and laugh at him. He was relieved when he grabbed the last of the bags and neither of them had shown up. But as he finally closed Mel’s door behind him, his worry about what Mel would do to him increased. It was imminent now.

Mel watched as Chad closed her front door and set the last of the groceries down on her table. He looked worried. He should be, she thought. The problem was though, she still hadn’t decided how to handle him. So she said nothing to him, and just began putting everything away.
Chad just stood at the entrance to the kitchen and waited. She hadn’t told him to do anything since he finished bringing up the groceries. “How can I help?” he finally asked, very politely.
Mel said nothing at all to him. Instead she went directly to her refrigerator and brought out one of his bottles and handed it to him. She pointed to his usual spot on the floor and he sat. After that, she tried to pay as little attention to him as she could, knowing the affect that her silence alone might have on him.
Chad sat down and drank his bottle while he watched her. The worry over how she was going to punish him was still foremost on his mind. But she hadn’t said a single word to him since they had gotten home. He began to wish that she would say something, anything, even yell a bit. Just so he could know the eternal waiting was finally over. But she was still remaining silent.
When he finished his bottle, he held it up to show her. “I’m done.” She was busy pouring liquid from some of the drinks they had bought earlier into his baby bottles, something he was very glad to see since he hated the tea that she made. Mel glanced at him quickly as she finished filling another bottle. Then he watched as she screwed the nipple back on. She picked it up and walked over to him. Taking the empty bottle from his hand, she handed him the new one and walked away again without a word. Yeah, she was definitely pissed, he thought. He looked at the bottle she had handed him. Whatever was inside it looked terribly dark and almost brown. Ugh! He put it to his lips and tasted it. Awful! A bit sweet underneath, but not at all to his liking. “What is this?” he asked. Mel just looked at him sternly and walked away, leaving him alone on the kitchen floor with his bottle.

While Chad was finishing the bottle of prune juice she had just handed him, Mel went out and sat in the living room to think. She was still puzzled over what she was going to do with him. She knew that the fault was probably hers. Completely on impulse, she had deviated from the plan she had made. She had pushed him too far, too fast. She hadn’t planned on taking him out fully dressed for a while yet, but somehow she hadn’t been able to resist the urge earlier when she had dressed him. But the good part was that now she thought that he would realize that there was nothing she could not make him do. No matter how difficult things would be for him, he would always have the knowledge that he would be forced to endure it. That alone she considered a major step. So maybe she didn’t screw up so badly earlier after all. She would back off a bit though and try to get more back to her original plan.
And speaking of that plan, she had really screwed up by not making him drink and eat more before they went out. She had to get him back on track with that and fast. She wasn’t sure if he had wet his diapers even once while they were out, and that couldn’t be allowed to happen again. He was finishing his second bottle now. That was a good start, but she had to fill his stomach too. Thinking about food and eating just then made her stomach growl. She hadn’t eaten all day either. Time for lunch.
While Chad finished his baby bottle of prune juice, Mel made salads for each of them. It wasn’t much for him, but it would be plenty for her. Fortunately, she had a few other things she could have him eat to help fill him up later.
When Chad finally finished his bottle, she took it from him and handed him a bowl filled with his salad to eat. Then she went to the refrigerator and got him another bottle to go with it, this time it was apple juice. She handed it to him.
“I don’t have a fork,” he said from his position on the floor.
Mel sighed and broke her silence. “Babies eat with their fingers.” She was inwardly laughing a little as she sat in her chair at the table to eat. She enjoyed it even more watching him struggling on the floor with his meal, having to eat only with his fingers.
Chad hadn’t eaten much, but he was starting to get full. The two baby bottles he had just finished, and now this third one along with his salad had filled him up more than he thought they would. He was eating on the floor where she had made him drink his bottles like a child. Now he was eating with his fingers like a baby too. And like a baby, his fingers and face were a mess from the dressing on the salad. He felt the old familiar twinges in his cock again. Damn the woman could be fun sometimes. She was treating him just like a child and he was loving it. Unfortunately, he knew that later she probably would be punishing him in way’s he’d rather not think about. He was really wishing it would come sooner, just to get it over with.
When he finished his salad, Mel took the bowl away from him, but before she allowed him to get up, she handed him a banana to eat. “I’ve had enough,” he said as politely as he could.
“Eat it!” Mel said angrily. Then she left him alone again.
Chad sighed and began eating the banana. Curiously though, when he was done, he was slightly thirsty. He found himself wishing that he had just a little left from his last bottle to wash it down with. He put that thought from his mind quickly. A little thirst was not a problem he was going to worry about. “I’m finished,” he called again.
Mel still didn’t know what she was going to do with him. Every plan to punish him either sounded too extreme or not nearly enough. She sighed, there were other things he needed to be doing just then. “Ok,” she replied from the living room. “Get in here.”
Chad got to his feet immediately and walked into the living room. His fear over what she was about to do to him was once again growing.
“Get those clothes off!” she commanded.
Knowing the time for his punishment had finally arrived, he began to get undressed. He suddenly wished however that he had not just eaten. But when he was down to just his diapers and plastic panties, she stopped him. “Ok, that’s enough. Leave the diapers.” Chad was suddenly thoroughly confused. Mel got up and went to her purse and dug out his pacifier and shoved it into his mouth again. “Come on,” she said as she led the way into her bathroom.
Chad followed her into her bathroom, unsure what was going on or what to do. He was about to ask when she pointed towards the large plastic garbage bag in the corner and said, “Get busy!” Chad nearly fainted. The bag held all of the dirty cloth diapers he had been wearing for the last few days. This was not a task that he wanted to do at all! Why couldn’t she have let him just wear disposables all the time? Those all got thrown away instead of having to be cleaned.
He gingerly opened the bag and was immediately assaulted by the sharp acrid smell. He was close to gagging from it. “Rinse those in the toilet first,” Mel ordered. “Then run some water in the tub to scrub them by hand. I’ll get you some detergent and bleach.”
Mel left him quickly after that. He couldn’t blame her, the room was starting to smell terribly. Very gingerly, he reached into the bag and brought out the first mass of diapers. They were all stuck together. “Ewww,” he almost said aloud. He really did want to barf. This had to rank up there with the most disgusting things he had ever done. But he had to do it, so he began dunking the diapers in the toilet to pre-rinse them clean.
Mel walked back into her bathroom and set some detergent and bleach on the counter for Chad’s next phase in cleaning his diapers. She was immediately assaulted by the horrible odor in the room as soon as she walked back in. She quickly retreated to the doorway again where she could breath better to watch him. The longer she watched him, the more interesting she found it. Finally, she just had to say something… she just had to tease him about it a bit. “You know,” she began, “I find what you’re doing very ironic… and really funny in a way.”
Chad wanted to answer, but he said nothing and kept working.
“I guess you’re finding it interesting too, but more than that, I’d be willing to bet that you’re finding this sexually thrilling.”
Chad just looked at her like she was crazy. How could what he was doing be in any way anything but awful?
“I just find it funny,” she continued, “that from now on, the only use you’re ever going to have for a toilet again, is for exactly what you’re doing right now… and that’s it. For the rest of your life, you’re always going to be peeing and messing in your diapers and never again in a toilet. So the only way you’ll ever use a toilet again is for just what you’re doing right now.”
Chad’s eyes bulged. He had never thought of that. It was awful! But worse, now that she had said it, the very idea of it had his cock suddenly giving him major twinges. He pictured himself in the future, just as he was, pacifier in his mouth, clad in only diapers and plastic panties, totally incontinent, and the only use he would ever have for the toilet was to rinse his diapers. Oh God what a picture. He actually blushed. Damn the woman, only she could make a task like this sexually thrilling.
A few minutes later though, he wasn’t so excited as he leaned over the tub, scrubbing by hand each and every one of those diapers. Ugh! Finally though, just to make sure they were all clean, she had him put them in the washing machine. He almost felt defeated. Why had she bothered to make him do them all by hand first? The washer could have handled it easily. At least she let him put them in the dryer when they were done. He had visions of her handing him the blow dryer she used on her hair to dry them with.
Cleaning all the diapers had taken him most of the afternoon. The job had taken longer than it should have because Mel occasionally brought him bottles to drink or snacks to eat and made him sit on the floor till they were done each time. He was absolutely loving how much like a child she was treating him. He was also starting to pee over an over again. It had really been a welcome change earlier when he hadn’t had so much to drink and had actually gone for hours without peeing, not to mention having his diapers stay dry for so long.
He was still very worried about how she was going to punish him, but he had worried a lot less about it while he had something to do. Now though, he was finished and all his cloth diapers were neatly folded and either stashed away in her bathroom or stacked by her front door or for him to take back to his own apartment later. How was she going to punish him? She had really hardly said a word to him all afternoon – other than to tease him briefly or to give him directions. Otherwise, she had mostly ignored him while she tried to catch up on her office work that she had brought home. He really wasn’t sure if her ignoring him so much was getting to him or not, but since he had nothing better to do at the moment, he went into the living room where she was working on the couch. “What do you want me to do next?” he asked.
Mel looked up from her work and sighed. Sometimes she hated how much work she had to bring home. But she kept telling herself that that’s why she got the big bucks. She glanced at her watch and was surprised to see how late it was. Chad was standing in front of her, probably bored. No problem. “You said you can cook. There’s chicken in the kitchen. Make me some dinner. Oh, and make it something nice. Let’s see what you can do.” She purposely looked back down at her work again, seeming to ignore him completely, as if he were no longer there.
Chad was a bit bewildered. Make dinner? He guessed he could do that. He was still standing there in front of her, waiting for her to pay a little more attention to him, but she had gone right back to work. Sighing a bit, he went into the kitchen.
Dinner was really no problem, he had cooked dinner many times for his wife – make that ex-wife – and himself. He fixed the chicken and chopped vegetables and put them in pots on the stove. The only thing he really wished for were more spices, Mel’s kitchen was very lacking in that department.
When everything was prepared, he set the table for two. He poured her a glass of wine, then he started to pour himself a glass too. And he stopped. She wouldn’t really make him drink it from a baby bottle, would she? He sighed. Of course she would. But on the off chance she might not think of it, he finished pouring himself a glass.
Wanting to impress her, he even found a candle and put that on the center of the table and lit it. Everything was perfect, everything was ready. Now all he needed was her.
Mel’s stomach growled. The reason it growled was because whatever Chad was doing in the kitchen smelled awfully good. But she was still doing her best to ignore him and finish her work. She was actually glad when Chad came in to get her. “Dinner is ready,” he announced softly and politely.
She looked up. “It’s about time.” She got up from the couch and went into the kitchen. The table was set beautifully with a candle in the middle. He had even poured them each a glass of wine. Everything looked and smelled heavenly. This was living. This was what she wanted every day when she came home from working hard. This was life as it should be.
She sat down. The food was already on the plates and it looked as good as it smelled. She picked up her wine and she sipped it. Perfect. This was luxury. He was just sitting down, his bare chest and diapers looking very out of place at her beautifully set table. That bothered her – a lot. She glanced at his glass of wine. His glass? No, no, no!!! “Oh no you’re not!” she said quickly. “Get up!”
Chad was surprised and confused. She had seemed to like everything. What was wrong now? She walked over to his side of the table and picked up his plate and carried it back into the kitchen and set it on the floor. “Babies eat here!” she said, pointing to his usual spot. Then she opened the refrigerator and pulled out another baby bottle for him.
Chad sighed. All the work he had just done, and he was back on the floor to eat again. As he looked at his plate, he realized something else too, once again he would have to eat with his fingers. But at least what he was eating was better than anything he had had in a while. He glanced up at her. She was totally absorbed in the dinner he had prepared for her. There was no doubt she was enjoying it. That alone made him feel good. And even though he was eating with his fingers from the floor and drinking from a baby bottle, he was glad that for once he was having a proper meal. Something he had always believed was necessary – at least every once in a while.
After dinner, Mel went back to her couch to continue working. The meal that Chad had fixed had been great, better than anything she’d had in a while. As she sat back down, she could easily picture Chad serving her like that every night. Such a pleasant, wonderful dream. But the sound of Chad working in the kitchen brought her back to reality. If she wanted that dream, then first she had to win that bet, and that meant keeping Chad in his place. He had overstepped those bounds when he had tried to sit down to dinner with her. That was not in keeping with her idea of what she wanted from him. And those thoughts led her right back to the problem she had been wrestling with all day. How was she going to punish him? She had no doubt he was on pins and needles over it. Well, let him worry!

Chad busied himself cleaning up the kitchen. Mel was ignoring him again. He was sure she had enjoyed the meal he had prepared, yet she hadn’t said a single word about it. She just walked off. She hadn’t even told him to clean up. Yet here he was, washing the dishes and making her kitchen look spotless again. In truth, he was still worrying, more than ever, about how she was going to punish him. Cleaning up after dinner just seemed natural – plus, he didn’t want to give her least excuse to make his punishment worse.
He had just started scrubbing the pots he had used though, when he again felt the first signs that the last suppository she had put in him was about to do it’s job again. It had been a long time since he had messed himself this time. Another welcome change. But he could tell that that was about to change – and soon. It seemed to happen more and more now after he had eaten something. All that glycerin in him had him so well lubed that it was impossible to hold anything back and his system was staying mostly empty because of it. He did try to hold it back, some. But the runny mass was under too much pressure and was leaking out of him no matter what he did. Finally it became too much for him and with a loud grunt, he let it all go. Yuck! Major yuck! He began his very ginger waddling again.
Mel heard Chad grunt loudly in the kitchen. She actually turned her head around to see what his problem was. A minute later, she turned back to her work. A broad smile on her face.
A short while later, Mel looked at the papers strewn around her, then she looked over her notes, and finally realized she was done. Solving a major case problem always made her happy and this time it was no different. She got up to see how Chad was doing in the kitchen. Good timing, she thought as she watched him wiping the last of the counters down. She nearly laughed at his wide-legged waddle.
She was feeling good. Dinner and finishing her work had made her feel that way. She decided to take a bit of pity on the poor guy. “Come on,” she told him. “I’ll change your diapers.”
Chad was more than a bit surprised, not to mention really happy to hear that. He quickly followed her into her bathroom where she had him lay down on the floor. She removed his old diapers, cleaned him up, stuck another suppository up inside of him, and then rediapered him again. Heavenly. Heavenly. Heavenly. The large trash bag in the corner that she had been using to hold his soiled diapers wasn’t empty anymore. Chad wasn’t exactly happy knowing that eventually he would have to deal with that again, but he probably wouldn’t have to worry about that for a few days yet. She seemed to have a lot of those cloth diapers. But did her new pleasant mood mean she wasn’t going to punish him for not wanting to get out of the car earlier? He just didn’t know.
Mel went out and watched TV, leaving him alone in the bathroom with no orders to do anything. But her mind really wasn’t on the show. She was still trying to figure out what to do to punish him. She had to do something! But what?
The same question was eating away at Chad more and more. Was he going to get away with it? Or should he continue to worry. The more he thought about it, the more worried he was getting. Finally, he decided he had to ask her about it. Plucking up his courage, he walked into her living room where she was sitting in a chair staring at the TV screen. “Mel, please, I have to know…”
She suddenly looked up at him angrily. “What did you call me?”
He was so startled by her sudden anger that it took him a moment to regain his wits and realize what he had done. “Damn it!” he swore softly as he realized that he had forgotten to call her Mistress.
But before he could correct himself, she nearly jumped up off her couch. “Stop that!” she yelled.
Chad cringed and backed away a step from her sudden anger.
“I’m tired of hearing you swearing and using language you shouldn’t! I ought to…” In the middle of her sudden tirade, Mel stopped. What did she mean she “ought to?” She could do it. Furthermore… she should! Acting quickly, she grabbed his arm and pulled him back into the bathroom.
Chad knew only bewildered fear as he was suddenly being roughly dragged behind her. Her reaction had been so sudden that it had caught him totally off guard.
“Kneel down… Baby!” she ordered pointing to the middle of the floor. Chad dropped down to his knees, not just by choice, but because she was shoving him down too. “You want to act like a child, then I’m going to treat you like one!”
Mel grabbed the bar of soap that was next to her sink and began wetting it under the water. From his knees behind her, Chad had no idea what she was doing. She turned around and quickly grabbed his jaw, forcing his mouth open. All too late, Chad realized what she was about to do and before he knew it, she had shoved the wet bar of soap through his teeth, and firmly into his mouth.
Through his shocked state, he quickly realized that the sweet smelling soap that she kept on her counter tasted awfully strong in his mouth. The light flowery fragrance quickly became pungent and horribly strong under his current circumstances. All too fast, the soap in his mouth began tasting worse and worse, stronger and stronger. He began struggling against her, trying to pull her hands away from his face so he could get the bar out. The more he struggled, the more his tongue lathered up the soap inside his mouth, making things ever so much worse. The lather began sliding towards the back of his throat, causing him to gag. He struggled harder against her till she finally pulled the bar out again. Relieved, he quickly leaned over the edge of the tub to wretch and to try to let some of the soap suds drain out of his mouth. It had been horrible.
Mel left him there, but she was back again moments later while he was still bent over her tub. She roughly grabbed his arms and tied his wrists behind his back. Then she tied his ankles together, and finally tied his wrists to his ankles. She wasn’t done with him yet, not by a long shot!
She grabbed the soap again and again wet it under the sink. The look of fear in Chad’s eyes was obvious… and she was glad to see it. “I’m tired of you using language you shouldn’t. It’s not nice for grown-ups and it’s especially not appropriate for babies like you! So one way or another, you’re going to learn!” Once again she grabbed his jaw and forced his mouth open and shoved the soap inside. Chad squirmed again, but without the use of his arms he was a lot easier to handle.
Chad was going crazy. The awful soap was back in his mouth again. The horrible taste was all he could think about. He tried to struggle, but tied as he was there wasn’t much he could do. And she was just holding it there. There were real tears running down from his eyes when he finally felt her pull it out again.
“That was for using words that I never want to hear you use again!”
Chad wanted to spit out every bit of the foul liquid that was filling his mouth, but she was sitting on the edge of the tub right in front of him and she wasn’t yet letting go of his jaw. He had no choice but to keep the soapy liquid in his mouth. Through his misery, he realized she was still speaking to him.
“Next,” she said, “I told you I never want to hear you call me Mel again. But you couldn’t seem to remember that, could you? Mistress is the only thing I ever want to hear you call me. In fact, now that I think about it, I don’t hear it enough. I almost never hear it. So from now on, I want to hear you call me Mistress – every time you speak to me. Got that?”
But before Chad could answer, she shoved the bar of soap back into his mouth again. And again he went wild. The amount of soapy liquid had reached the point where he was forced to start swallowing it, making him feel even worse. Finally, she pulled the bar of soap out and put it back on the counter. Then she got up and left him there. Chad didn’t know what to do. He needed desperately to rinse the soap out of his mouth, but he was tied up and helpless. All he could do was to kneel there on the floor where she had left him. In his helpless, miserable state, he wet his diapers again, heavily, without hardly knowing beforehand that he was going to do it. He felt like such a child.
Mel left him and went to her kitchen where she filled one of his bottles with water. Then she went back to him in the bathroom. He looked miserable. Good! She held the bottle to his lips. “Drink!” she ordered.
Chad really wanted to rinse his mouth out, he just wasn’t really happy about having to swallow everything, but he had no choice, especially not then. He drank more and more greedily as the water in the bottle washed away more and more of the foul taste in his mouth. She was feeding him a bottle like a baby. And eventually he began loving that fact. But when the bottle was only half done, she took it away from him and set it down again.
“I hope you realize now that when I tell you to do something, you have to do it. You have no say or opinion at all in the matter. In any matter. You really made me angry at you today, and I can’t let that go unpunished. So for that, here’s your punishment.” And with those words, Mel grabbed his chin and shoved the soap back into his mouth again.
Chad couldn’t believe it. She had just rinsed his mouth out with the baby bottle and now she was starting all over again. This time though, he felt Mel moving the soap all around inside his mouth, as if she were trying to get it into every nook and cranny. Worse, his mouth was freshly coated with water so the soap was lathering up more and more. The soap suds were starting to run down the back of his throat. He could also feel them running down his chin. He struggled, but he was now so tired that there was little he could do about it. By the time she finally pulled the soap back out again, he mouth felt like it was completely full of absolutely horrible soapsuds. And he had no other way to get rid of them than to swallow them.
Once again Mel held the bottle to his lips and he drank greedily, trying to rinse the awful soap taste out of his mouth. But all too soon the bottle was empty, and it seemed like the water had removed only very little. Mel left him again. He prayed that she was filling up the bottle again. But when she came back, instead of another bottle, she roughly shoved his pacifier into his mouth again. Then he was shocked to find that she was tying it into his mouth by the long ribbon she had found for it. He was miserable. Totally miserable.
Mel looked over her handiwork and felt satisfied. That should give him something to think about. But she wasn’t ready to release him just yet. In fact, she decided that it would do him good to just stay where he was for a while to think about things. Almost kindly, she helped him lay down on his side. “Just stay there and think about what I told you,” she commanded him. Then she left him there and turned out the bathroom light and closed the door on him.
Chad laid on the hard floor in the darkness. He wanted desperately to get the pacifier out of his mouth and get something to rinse the awful taste away, but he was stuck. He could barely move. Resigned, he laid his head down on the hard floor and tried to close his eyes to get what rest he could. He was spending entirely too much time lately tied up. He didn’t like it at all.
Mel watched TV for a while, keeping Chad only in the back of her mind. But eventually, she realized she had a little problem. She had left Chad tied up in her bathroom, but now she needed to pee. And she wasn’t ready to release him yet. She should have put him somewhere else. She walked into the bathroom and turned on the light. He looked pitiful. A beautiful sight after the way he had pissed her off earlier. No, she couldn’t release him yet. But she did still have to pee. She’d just have to blindfold him too. But before she could leave to find a scarf to tie around his eyes, she spotted the large plastic bag that held his dirty diapers. She opened it and pulled out the messy diaper she had taken off of him earlier. Laughing a bit to herself, she draped it right over his head, making sure the really messy part was right in his face. He tried to jerk it away, but he couldn’t really make it move too far. “Keep that there!” she ordered. Then, keeping a very close watch on him to make sure he couldn’t see her, she lowered her shorts and panties and sat on the toilet and peed. But doing it, made her think of one more thing. “Can you hear that?” she said. “Can you hear what I’m doing? Don’t bother to answer because I know you can. “I’m doing the one thing you’re never going to be able to do again. I’m peeing like a grown-up into the toilet. But you’re a baby now. The only place you’re ever going to pee again is in your diapers. Isn’t that right? There’s something else for you to think about… Baby.
Chad had heard her peeing of course, but his main concern was the horrible mess that was now covering his face. He could breath, but every breath only brought him the foul smell of his dirty diaper. It was horrible. He heard Mel teasing him. The words sunk in, but there was nothing he could say or do just then. Finally he heard her leaving him, closing the door behind her again. She hadn’t removed the foul, messy diaper from his head. She was forcing him to endure yet another punishment. He peed into his diaper again… like a baby.

The Bet - Chapter 9 (Sunday – week 2 Part 1)

The Bet
by Karen Singer

Chapter 9 (Sunday – week 2 Part 1)

Mel stretched a bit as she padded her way to the coffee pot to start it brewing. She had slept later than she had in a long time. She thought about Chad next door and decided he could wait. He probably needed more sleep anyway. She had been hard on him all week, something she dared not ease up on now. But letting him get a little extra sleep wouldn’t hurt – either of them.
Once the coffee was brewing, she went to her desk and fired up her computer. She had a bit of research to do. Ever since Friday night when Chad had informed her that he couldn’t pee while he was hard, she had been trying to think of some way to keep him from ever getting hard. Her earlier research had left some vague possibilities in her mind, but now it was time to explore them further. A little while later, her coffee almost finished, she had made her decision. She had found, and easily, something she considered fairly diabolical. By all descriptions, Chad would have to learn to stay soft all the time, or he would suffer. She had planned on ordering something that morning, but a small notice on the ordering page had stopped her. If she placed the order by phone on Monday, then there were faster delivery options available, including overnight. She decided to place her order first thing Monday morning, and hopefully, by Tuesday evening she would no longer have that particular problem with Chad anymore. Chad? She smiled. She had to get used to calling him Sissy now. It wouldn’t do to make that mistake in front of him.

Chad felt himself have to pee again and allowed himself to do it. He opened his eyes. It felt later than usual. He sat up where he could see his pink clock radio and stared at it very much surprised. It was later. Much later. Gratefully, he laid back down and stretched and just rubbed his bare arms and legs on the sheet, trying to get his circulation moving a bit. As usual, his diapers were overly soaked and he couldn’t even begin to bring his legs anywhere near each other. He would have loved to remove them, but the lock on the back of his onesie prevented that. So frustrating. As was his need to get off that was also impossible.
Sighing, he got to his feet. Normally he would have gone straight into his bathroom to relieve himself, but that was impossible for him now too. As he waddled into his living room, the need to pee returned again. Once again he peed without hardly giving it another thought. His living room was empty except for the one chair that Mel had sat in yesterday. He wandered into his kitchen, also mostly empty. There were a few baby bottles filled with her lousy tea in the refrigerator, but that was all. Sucking on another baby bottle just then wasn’t exactly what he wanted to do, and he didn’t. Thinking about the bottles made him think about the pacifier he was supposed to be sucking on. He picked it up by the ribbon it was dangling from attached to his onesie. He just looked at it and let it fall again. Mel wasn’t around just then.
His apartment was empty. No TV, no nothing. As he looked around the room, he noticed where the connection for the cable TV came out of the wall. After everything the bitch was putting him through, he decided that one of the major things she was also going to buy him, was a new TV too, a nice one! Mel still hadn’t shown up. Where was she? Deciding to do the only thing he really could do, he went back to bed.

It was the middle of the morning by the time that Mel was finished getting ready. She was dressed casually, but nicely. Grabbing her purse she went out and locked her door behind her, she wasn’t planning on being back till much later.
Chad heard his front door open. “Finally!” he thought to himself as he got up off his mattress and went to make sure it was Mel who had just come in – who else?
“Did you get enough sleep?” Mel asked him as soon as she saw him.
“Yeah. Finally!” he replied.
“Did you sleep any better than you have been?”
That question puzzled him. “What do you mean?”
“I mean have you learned to wet yourself in your sleep yet?”
“Ha, not even close.” He replied. He didn’t think he was really lying since he did wake up every time he needed to pee, he just wasn’t bothering to come fully awake anymore. But she didn’t need to know that.
Mel walked over to him and suddenly slapped his face – hard.
“Ow! What was that for?”
Mel just reached down and picked up the pacifier that was dangling from his onesie and shoved it back into his mouth. “I told you to keep it there, didn’t I?” Chad said nothing.
As Mel got him cleaned up a few minutes later, she realized that there wasn’t as much of a mess in his diapers this time. Of course she should have expected that with all the suppositories she was shoving in him. His system was probably mostly empty now. Chad gratefully soaked his body clean first in his shower, then relaxing in his bathtub for a few minutes. Mel had added some flowery smelling bath beads to the water, but that only made him enjoy the sensation all the more. His cock began growing again at the very thought of it. He wanted to touch it so badly. He glanced quickly at Mel to see if she would notice, but she was watching him all too closely. “Don’t you dare!” she said. Chad sighed dejectedly and Mel made him get out of the water so she could rediaper him again.
Once she had diapered him in two of the thinner cloth diapers and had his plastic panties pulled up again, Mel had him pull one of his all-in-one girdles back on again. Chad hated the thing because it was so uncomfortably tight, but with only two diapers on under it instead of the four she usually used, it wasn’t nearly so bad down below.
When he went to shave his face, he quickly realized that the only razors he had were all pink, and he had no shaving cream at all. “I can’t shave with this,” he complained.
“You’re going to have to learn,” Mel answered, “because that’s all I’m going to allow you to use.”
“And there’s no shaving cream either.”
“Tough! Women don’t use it when they shave their legs. Rub some soap and some moisturizer on your face. Try that instead.”
Chad wasn’t exactly sure, but he tried it. The moisturizer he decided was definitely the most help.
“Ok,” she said when he was finally finished, “makeup time again. Let’s see if you can remember what I taught you yesterday about the mascara.” Mel finally allowed him to take his pacifier out again, but she held onto it for later.
Chad went to work with one of the mascaras. But of course she wasn’t happy with his first attempt, or his second attempt either. Fortunately, she decided that his third attempt was much better. “You’re finally starting to get the hang of it,” she told him. “But you should have been practicing more.”
“When?” he replied a bit put out. “You kept me busy all last night till you sent me to bed.”
“How about this morning? Don’t tell me you’ve been asleep the entire time till I got here.”
“No,” he admitted.
“And I’ll bet you haven’t had a single bottle this morning either, have you?”
“No… but you didn’t tell me to!”
“I shouldn’t have to!”
Chad kept his mouth shut after that for fear she might punish him again. He knew he had probably pushed his luck as it was.
Mel did the rest of his makeup for him again and then stuffed the pantyhose from last night back into the cups of his all-in-one. Then she had him put on the same black skirt he had worn before only this time with a different, more colorful top. “You really need some more clothes,” she commented. Then she handed him another pair of heels from his closet, fortunately, not his highest ones. She sighed as she looked him over, “still a long way to go,” but you’ll have to do.” Actually, she was fairly glad he looked as ridiculous as he did, it would only serve to humiliate him more – and excite her more.
“Ok, let’s go,” she said as she headed for the door.
Chad was terrified again, even though he had expected they were going out again. “Where to?” he asked.
“Grocery shopping,” she said as she pushed him towards the door. Chad reached for his keys and wallet on the way out but she stopped him. “Leave them, I’ve got a key, remember?” Then she added, “Remind me to get you a purse soon.” And with that she pushed him out and closed the door behind them.
Chad was completely terrified. She was taking him out shopping dressed the way he was and he had no way to get out of it. She had pushed him out the door without his keys or even his wallet. Without his keys, he couldn’t even get back into his own apartment. He was totally dependent on her. He felt so trapped. He was trapped! Completely!
All the way to the store he fretted. He had never been out in public in a skirt before – except for walking next door last night to Cassie and Sandy’s apartment, and he wasn’t really counting that – now. He realized that Mel was upping the ante, again! And this was almost more than he thought he could handle. But how was he going to get out of it?
All too soon they pulled into the parking lot. It was late enough in the morning that Chad could see that the store was getting crowded. Mel found a parking spot, not as close to the store as Chad would have liked, and got out. “Ok, Sissy. Let’s go,” she said as she got out of the car.”
Chad stayed where he was. There was no way he could find the courage to get out of the car just then.

Mel stopped at the back of her car as soon as she realized that Chad was still in it. “Come on!” she shouted. But Chad wasn’t budging. She walked over and opened his door. Chad was huddled in the car with his arms wrapped around his body. He was clearly terrified. “What are you doing? Get out of there right now!”
“I can’t.”
“I said… Out! Now!” But Chad just shook his head. Mel was at a loss for what to do and was getting angry. “Do you want to be punished again?”
He shook his head. “Nnnno.”
“Then get out of there!”
He shook his head again. “I can’t!”
Mel was really angry now. “Boy are you going to get it when we get home!” But she wasn’t ready to leave just yet. She needed to find some way to get him out of the car. She was a lawyer, she had resorted to drastic means before. “Ok smart ass!” She pulled out her cell phone. “Let’s see what the police will do with you when I call them!”
Chad looked up at her, aghast.
Mel opened her cell phone “Nine.” She pushed a button. “One.” She pushed another button. “One.” She put the phone to her ear.
“Mel, please!” Chad pleaded.
“Who?”
“I mean, Mistress, please don’t.” But Mel was already speaking.
“Yes,” she was saying. “I just came out of the store and I found some… pervert… sitting in my car and he won’t go away!... No, I’m not going to go near him! No, I don’t think he has a gun, at least I didn’t see one… Ok, I’ll be expecting them, and please tell them to hurry. I’ll be the one waving my arms for them up by the front entrance… Yes, yes, I’ll stay on the line.”
Chad looked up at her, she had called the cops. No matter what the actual reasons it would be really bad for him. He didn’t want to get arrested. He didn’t want to go to jail. He couldn’t imagine what someone dressed as he was would experience there. “Mistress please…” he said softly. But she was still talking onto the phone, describing him as if she were standing further away from him than she actually was. “Please…” he pleaded again. He had no choice, slowly, he extricated himself from the car. Exposing himself and the way he was dressed to the entire world. Mel looked please and closed her cell phone. Then she quickly slammed the car door shut behind him and hit the lock button on her key chain. “No way out,” he thought through his panicked brain. “No way out.”
“Come on,” Mel was saying as she started walking toward the door, glancing around as she walked. “We’d better get out of here before the police show up.” She stopped to wait for him to catch up. “That is, unless you really do want them to arrest you.”
Chad hurried after her. His heels making all too much noise, even over the other sounds around him. Exposed! Branded as a sissy. And now on view for the whole world to see what he really was. Deeply ashamed, he hurried after her, as if she would somehow keep him safe.

Mel was still furious, but she was also smiling that inward smile of satisfaction that she had whenever she scored big against an opponent. She hadn’t really dialed 911, she had only pressed the first three numbers of her own phone number. But the ruse had certainly worked. Her big problem now though, was what could she do to Chad later to really punish him? She had no doubt that his backside couldn’t stand much more of her yardstick so soon. Keeping that thought in the back of her mind, she went in and ordered Chad to grab a shopping cart.
Chad’s terror never diminished. In fact, all his senses seemed to be heightened. He had certainly worn women’s clothes before – lots of times, but only in the privacy of his own home. The only time he had ever worn them out of his house had been last night with Cassie and Sandy – and that was it. But now… He felt like such a fool! His overly aware senses noticed everybody who even might be looking at him. He could almost hear the clicking of his heels with each step he took. Each click sounding an alert to everybody else that said, “Look at me! Look at me!”
He was more aware than ever of how the heels felt on his feet, forcing his feet into an odd angle as he walked, his heels up off the ground, his toes forced tightly down, having to be more careful about how he placed each step so as not to twist his ankle because of the higher heel.
He was painfully aware of the mocking soft caress of his skirt as the hem brushed against his legs… his all too exposed legs. He was wearing a skirt – in public. How embarrassing. He even felt the embarrassment of having no pockets to hide his well manicured hands in.
His breasts stuck out far too plainly for his comfort too. But were they any bigger than any other woman? Not really he thought. In fact, probably smaller. But that fact didn’t really comfort him a bit.
He couldn’t see the makeup on his face, but he could taste his lipstick - an odd, yet interesting flavor. But with no wig, and on his face, the makeup alone shouted sissy to anyone who would see it.
He was doomed – forever. Exposed – forever. He felt so vulnerable. Afraid. And he had no choice but to follow Mel, one step after another, all through the terror-house called a grocery store. Why hadn’t there been a major earthquake last night? It would have been so nice. Now wouldn’t be a bad time for one either. Hurry Mel, please hurry. Or at least move a little faster. And curiously enough, he felt his cock start to grow again. Damn he needed some relief – and bad!

Mel was careful to walk calmly and slowly up and down each and every aisle. She knew that Chad behind her was scared. Really, she couldn’t blame him. But he had to know that this was coming. It was only logical. Besides, it was all part of his fantasy, wasn’t it? Not that it mattered in the end. He had signed away all his rights in favor of whatever she wanted him to do – with no say in the matter. And the truth was that making him squirm under her power was in reality very fulfilling to her.
She wondered only slightly what the other shoppers in the store thought about her… and Chad. She was sure that more than a few of them were put out by the sight of her with her sissy, but she was also sure that twice that many were secretly delighted. So she really cared even less about what everybody else thought.
She wasn’t used to doing a lot of grocery shopping. She usually just bought some diet TV dinners for herself to stick in the microwave. She could cook of course, but she knew she wasn’t really a good cook. She smiled, someday though, one way or another, Chad was going to be her “good cook.” But there were other things that had to come first.
She began picking up items that she didn’t often buy. Lots of salad fixings, a bottle of her favorite wine, even fruits and fresh vegetables. Did Chad know how to cook all the things she was buying? He could certainly learn, she decided. She wasn’t really a big beef fan, but some chicken breasts soon found their way into her cart as well.
She spent a very long time in the baby food aisle, looking over everything in it carefully. One of the reasons she spent so long was because she could almost feel Chad’s discomfort behind her. Was he getting hard again? She had no way of knowing. She almost hoped so – sort of. At the same time, she didn’t want him to be able to get hard either. It would be counter-productive. She had to remember that her pleasure was all that mattered, not his. She sighed, she was still new to all this. She knew she had a lot to learn. She wondered how she was stacking up against other doms – new ones anyway. Where did they learn the things they did? There were no classes in it anywhere that she knew of. All she knew was the little bit she had read on the internet – and her gut feelings. She wasn’t really planning on buying any baby food – yet, but she surrendered to her impulses and pulled down two boxes of baby cereal for him, smiling slyly at him as she did so.
In the drink aisle, she was careful to pull down lots of large bottles of things that she knew would keep him peeing. She bought three of the largest bottles of prune juice that she could find. Inwardly, she found that just looking at the stuff was revolting. She couldn’t imagine having to drink it – awful! But that wasn’t her problem. Chad would have to deal with that. Not Chad… Sissy!

Chad was ever so grateful as they finished the last aisle and headed for the checkout counters. Mel was certainly not hurrying, that was for sure. His cart was fully loaded and heavy. The heels he was wearing was making it harder to push. The amount of time they had spent in the store had dulled his fears, but only somewhat. The next hurdle would be getting through the checkout. But would she take him home after that? He certainly hoped so. Many of the things in his shopping cart were things that had to be put in the refrigerator right away. That fact alone gave him hope. He knew she was going to beat him again, he just no longer cared – that is, if she would just get him out of there and take him straight home.
But the long time in the store that had dulled his fears had also allowed his horniness to grow again too. Why did he have to have these peculiar needs? Not only had they cost him his marriage, but now his dignity too. Worse, the more he thought about them and about each and every little humiliation that Mel was putting him through, the more his need grew. There was no winning. He was thoroughly hooked and that was that. Doomed one way or the other. His name was Sissy now. A name that spelled out exactly what he was. And the more he dwelled on that, the harder his cock tried to get.
As they waited in line for the checkout, Chad was again all too aware of how close the other people around him were. Way too close for comfort. But then what distance would be a good distance? There wasn’t a good answer for that, not in public anyway.
He knew the question was coming as soon as he started unloading the groceries onto the conveyor belt. But she asked it softly. “Do you need to pee?”
He shook his head. “No, and I can’t anyway.” It was all he needed to say. In truth, he really didn’t need to pee. He had had almost nothing to drink or eat all day. Thankfully. But now he realized how hungry he really was. The nervousness in his stomach had kept him from feeling it earlier.
He expected Mel to be angry, but she only nodded her head and pulled out her credit card to pay for everything.
Walking back to the car and putting everything in her trunk was almost anticlimactic. He knew they were going home because they had things that had to be put away. More and more though, he began to worry about what she would do to him when they got there.

The Bet - Chapter 8 (Saturday – week 1 Part 2)

The Bet
by Karen Singer

Chapter 8 (Saturday – week 1 Part 2)

Mel kept Chad busy in his own apartment for the next few hours as she had him put everything in the bags away somewhere and started to make his place a bit more organized. At lunchtime, she went out and brought back some burgers for each of them and made him eat all of his, even though he was still full from all the donuts he had eaten earlier.
In his bathroom, Mel threw away every male item she could find and replaced it with something feminine instead. Suddenly, the only shampoo, deodorant, and razors that Chad had were now all female. And there were a lot of other feminine items on his counter too. The towels on his towel rack were now all pink as were the washcloths.
Chad had to put the little girl sheets on his blow-up mattress and the matching pillow case on his pillow. His blanket was neatly folded so as to leave no question about what kind of sheets were on the bed. His teddy bear was prominently propped up on his pillow.
The two cardboard chests were put together and all of Chad’s bras were place in one drawer while his pantyhose were placed in another. Mel took all of Chad’s male underpants, undershirts, socks, and the few pairs of panties he owned and put them together into a bag to take back to her apartment. Chad was devastated to see them go. Chad’s plastic panties went into the top drawer of the other chest, and the pink Barbie clock radio was displayed on top.
As Mel directed, Chad gradually rearranged his entire apartment to organize it better. Once most of the boxes were moved to better positions, the apartment began to look much better, but also a lot more empty.
Mel placed the only chair in his apartment in a more prominent place where she could always sit and watch him easier. Then she found the framed contract and handed it to him. Chad was more than surprised as soon as he saw what it was. He also wasn’t very happy about it. “Mel… why did you do that?” he said through his pacifier.
“Wait a minute, Chad,” she began.
Chad realized that he had complained again. Fearful of another beating, he quickly added, “I’m sorry! I didn’t mean to complain. It just surprised me, that’s all.”
But Mel held up her hand. Fortunately, she didn’t look all that upset. “Chad, don’t worry. There’s something else we need to discuss that I was going to bring up later, but right now is as good a time as any.”
Chad only relaxed slightly. “What?”
Mel took a deep breath. It felt like she was about to take another major step forward. Slightly frightening in a way. She looked at Chad, he was waiting. But she felt like she needed a more formal way to put across what she wanted to tell him. Just standing there with him felt all wrong. She walked over and sat in the chair and pointed to the floor in front of her. “Kneel down.”
With more trepidation than ever, Chad did as he was told and kneeled in front of her.
Mel felt a little like a queen sitting in that chair with her subject kneeling in front of her. “Chad,” she began. “I don’t think that it’s right that you call me Mel anymore. You’ve got to stop.” He looked at her questioningly. “From now on, I never want to hear you call me anything but Mistress. Got that? Mistress. No matter where you are or what you’re doing. Only Mistress.”
Chad took that in. It wasn’t so bad. In fact, it kind if made sense. Not only that, but it also fell right in line with all of his fantasies. He smiled up at her and said, “Yes, Mistress.”
“Good. Now I want that contract hung right in the middle of that wall where everyone can see it.”

When he was done, Chad looked around at his apartment. Now that it was organized, it looked a lot better. It also looked a lot emptier. The only thing about the living room that he wasn’t happy about was the contract that was now displayed prominently on his wall. With only one chair in the entire room, anyone coming in couldn’t miss it. The vast empty space did make it easier for him to visualize the pool table he would soon have though.
His bedroom and bathroom worried him a bit. They now looked way too feminine and embarrassing should anyone see them. In a way, it stimulated him greatly, but at the same time, he was worried about anyone seeing them.
He expected that now that they were done, that Mel would be taking him back to her place and he was bracing himself for the trip out the door. But instead, she took him into his bathroom and changed his diapers again – and again inserting another of the dreaded suppositories. But this time, she didn’t lock the onesie back on him again. Instead she made him put one of the all-in-one girdles on again. That was soon followed by pantyhose and the highest pair of heels that he owned.
Mel looked at him critically. “You need makeup,” she decided. She went into his bathroom where they had put all the makeup that they had bought into one of the drawers. She started to pull various items out to put on him, then she stopped herself and put it all back. She looked at him. “You’re a sissy. You must have done this before. Show me what you can do.” And with that she reached out and pulled his pacifier out of his mouth and set it on the counter.
Chad was so relieved to have the thing gone. For hours now he had been only keeping it in his mouth by lightly clamping down on it with his teeth. He stretched his jaws for relief and walked over to the drawer full of makeup.
He would have much rather had her put the makeup on him. He had played with makeup once or twice before, but only a very little bit. Tentatively, he looked through the various items in the drawer. So much stuff. He saw some eye shadow and figured that would be good to start with. As best as he could, he spread some out on his eyelids. Mascara, he thought, that should be next. He found some in the drawer. It seemed to take forever for him to put some on, and even then he couldn’t really see it. Finally, he grabbed one of the lipsticks and smeared that on his lips. He examined the overall affect in the mirror. But he didn’t have to say it, Mel said it for him. “Pitiful! Absolutely pitiful! Look at you, you didn’t bother with any foundation, you did the eye shadow all wrong, none of the colors work right together, and don’t even get me started on how badly you did the mascara. Pitiful! Just pitiful!”
“Um, I really haven’t had much practice with any of this,” he admitted.
“Well, it shows!” She stopped and looked at him for a moment, trying to figure out how to proceed. She was tempted to do it all for him, but the guy really needed to learn. “Ok, wash it all off, then we’ll start with something basic.” As soon as Chad’s face was clean again, Mel had him find all the mascaras that were in the drawer, three of them, just so he would know for sure what they were. Then she made him practice over and over again putting it on. But finally she had had enough. “Ok, that’s enough for today. I have other things I need to do. You can practice more later.” She left his latest mascara job alone and began making up his face – completely.
When she was done, Chad looked at himself in the mirror. Wow! She had done a great job. He couldn’t believe how different, and certainly much more feminine he looked. He turned towards Mel. “I can’t believe how different I look! Thank you.”
“You’d better start learning to do all that, and learn it fast!” Mel replied. “Now let’s finish getting you dressed.”
Mel stuffed a couple of pairs of pantyhose into the cups of his all-in-one girdle, then she pulled a black skirt and a white blouse out of his closet and had him put them on. “Almost acceptable,” she noted. “Of course, there’s a lot of stuff you still need and there’s no way that you could ever pass for a woman… yet. But I guess I can’t expect too much since it’s only been a week.” She sighed. He was about as ready as she could get him right now. It was time for something else. “Back to the living room,” she ordered as she picked up his pacifier and took it with her.
Mel once again sat in her chair and pointed to the floor. Chad immediately kneeled in front of her, all the while, wondering what she wanted next. Calling her Mistress certainly wasn’t bad at all. But if there was one thing he had learned in the past week, she could be full of surprises. That fact worried him.
“What’s my name?” she asked.
Chad knew what she wanted. “Mistress,” he answered immediately.
“Say it again.”
“Mistress.”
“Again.”
“Mistress.”
Mel actually liked the sound of it. Just hearing him call her Mistress gave her a lot of pleasure. But she knew he would be less happy about what she wanted now. “That’s right!” she answered him. “I’m your Mistress. And as your Mistress… and because our contract says I can… I have a new command for you.”
Chad listened intently, but very warily.
“From now on, your name is no longer Chad. I never… ever… want to hear you tell ANYONE that your name is Chad. From now on, the only name you may use is… Sissy!”
Chad was stunned. “Sissy?” he repeated quietly in shock.
“Sissy! If I ever hear you even say the name Chad again, I’ll have your name changed legally and permanently. And if you think I can’t do that, then just think about how easy it is for anyone to change their names whenever they want. Women change them all the time when they get married don’t they?”
“Yyyyyes,” he stuttered quietly.
“And remember, I’m a lawyer, I deal with that kind of thing all the time. So I know how to do it. So if you don’t want it changed legally… yet… then I suggest that you try very hard to remember just what I told you.” She paused for a few minutes while she watched him trying to digest that. “Now, who are you?”
“Sissy,” he answered quietly and ashamed.
“Louder. Who are you?”
“Sissy,” Chad said a bit louder.
“Tell me your name!”
“I’m Sissy,” he said faster and louder.
“Good. I just hope you remember that.” Mel knew that it wasn’t actually as easy to change someone’s name as she had said it was, but she was also betting that he wouldn’t know that.
Chad was having a very hard time digesting his new name. Could she really change it legally on him? The more he thought about it, the more he was sure that she could. That could cause him some major complications. In fact, even during the course of this bet, he had no doubt that it was going to cause problems. His new name was supposed to be
Sissy? How utterly embarrassing. Worse, he felt like some tiny part of himself had just been ripped away.
Mel got up from her chair and picked up her purse that she had left by the front door. She dropped his pacifier inside. “Ok, Sissy, there’s something I promised someone you would do for them, and now you’re going to have to do it.”
Chad got to his feet, suddenly very worried. Do something for someone? He was already dreading whatever it was going to be. Especially dressed the way he was.
“I want you to go knock on the door of the apartment next door and introduce yourself properly to the two women in there. And I’m going to be right behind you so don’t you dare do anything wrong!”
Chad was aghast. “You mean those two women who…”
“Yes, those two! Now get moving. And remember, if I ever hear you speak the name Chad again… well, you’ll be more than very sorry!”
Swallowing very hard, Chad headed for his front door. Mel opened it wide and held it open for him. Earlier that day he had been outside over and over again wearing the embarrassing onesie. Now he was wearing a skirt and made up more like a woman. It was another complete embarrassment. He heard Mel locking his door behind him. He didn’t even have a key to get back into his own apartment. Slowly, his heels clip-clopped their way towards the apartment past his. He was supposed to introduce himself with his new name. He had to tell someone that his name was Sissy now. How was he going to do it? There were major butterflies in his stomach.
He stopped at the door and looked back at Mel. She was waiting. Taking a deep breath, he reached out and knocked, softly. He was silently praying that nobody was home. But his prayer wasn’t answered. He heard someone coming to the door. And then it opened. The woman with the short dark hair was standing there. Before Chad could say a word, she screamed with delight. “Oh! Look at you! So precious!” Then she turned to yell behind her. “Sandy, come look. Quick! See who’s here.”
The woman with the lighter colored long hair walked out of the bedroom. “Ohhh!” she squeeled in delight.”
The dark haired one opened the door. “Come on in, come on in.”
Chad did as he was told. At least he wasn’t outside anymore. Mel followed right after him. “Hi Cassie. Hi Sandy,” she said casually to the two women.
“Hi Mel,” the longer haired one, who Chad now guessed was Sandy answered.
“You brought us a present,” Cassie said, walking slowly around Chad, examining him critically. “He’s adorable. Of course, watching him earlier running back and forth may just have been one of the highlights of my life!”
Chad was praying again. He was praying for the floor to open up and swallow him. A major earthquake should do it.
Mel laughed. “I just thought it was time you finally met your new neighbor – properly!” Chad didn’t miss the emphasis she had placed on the last word.
“Ooooo,” Sandy squeeled. “It’s about time.” She and Cassie quickly stood next to each other excitedly. Chad noticed that Sandy reached out and grabbed the other girl’s hand and was holding it tightly.
He looked at Mel, she was waiting. He looked back at the two girls, they were waiting too. Oh God! He didn’t want to do this! But he forced words out of his mouth. “I just wanted to say that I’m your new neighbor next door. And my name is,” the pause was every so slight, but it was definitely there, “Sissy.” He had done it now. He had actually told someone – make that two people - that his name was Sissy. He would forever be branded with that name now.
The two girls both started squealing with delight. “Oh Mel,” Cassie said. “I love it! You know I have a girlfriend who everybody calls Sissy. Of course she’s a girl.”
“Yeah,” replied Mel. “I thought of that. It’s a common enough name for a girl, but more importantly, it will forever serve as a reminder to him of exactly what he is.”
Chad was praying harder and harder for that earthquake to swallow him up.
“I see he’s finally wearing makeup,” Sandy noted as she finally let go of Cassie’s hand.
“Ugh!” Mel grunted. “You should see how awful the job he did himself was. I had to do that for him. I’m afraid he’s going to need a lot of practice.”
“Well, makeup can be hard,” Cassie replied in a slightly taunting voice, as if she were sticking up for him. “It’s one of the reasons why I don’t use much myself.”
The two girls laughed, although neither Mel nor Chad knew exactly what about.
“Anyway,” Cassie continued, “makeup is really more of Sandy’s thing.”
“Well let’s be honest,” Sandy replied. “You don’t really need a lot of makeup with your job. I do.”
“Yeah, but you’re good at it. Mostly, I just don’t care.”
“That’s ok. I like you just the way you are.” The two girls laughed again.
The familiarity between the two women was hard to miss, especially in their own apartment. Definitely lesbians, Mel thought. Without a doubt.
Mel picked up on something that Sandy had said. “What kind of job do you have?” she asked her.
But it was Cassie who answered, “Oh, she’s an interior decorator. And she’s great! She just doesn’t think so yet.”
“Well, I’m not great. But I do think I do a pretty good job.” Sandy retorted.
“Pretty good… Mel, look at this place. It looks great doesn’t it?”
Mel had to agree, it really looked fabulous. All except for one small work area that was incredibly cluttered. “Yes, it does look good,” she replied. “Really good!”
While the women talked, Chad inched his way out of the way more and just remained silent and in the background. As long as nobody was paying attention to him, he was a lot happier. He wondered if he dared to sit down. She had made him wear his highest heels and they were starting to hurt his feet. While he listened quietly, he learned that Cassie was an aerobics and dance instructor in a women’s gym. That explained why she didn’t need a lot of makeup in her job. Cassie spent a few minutes trying over and over again to convince Mel to join the gym, but Mel was just too busy with her job. Because he was just standing still, Chad’s feet were starting to hurt more and more. He decided to chance sitting down. Slowly, so as not to attract too much attention, he moved over to one of the chairs and sat, being careful to smooth his skirt out under him as he did so. The women each glanced at him quickly as he sat down, but they were busy talking and went right back to it. He breathed a sigh of relief. But unfortunately, his movement brought the conversation right back to him.
“And how is his training going?” Cassie asked.
Chad was suddenly aghast. These women knew? Suddenly all three of them were looking straight at him again.
Mel sighed. “Ok, I guess. I’ve been force feeding him bottles of a green tea mixture that I make up. It’s supposed to be a strong diuretic and I’ve been making it really strong hoping that it will make him have to pee more. And I think it’s working. At least I hope it is.”
They were suddenly all looking at him. He realized they were looking for an answer. “It is.” Chad said. “Believe me, it is.” But they just continued to look at him. Were they expecting more? “Sometimes I think I’m peeing almost every half hour. It’s especially bad at night because it keeps waking me up. I haven’t slept well all week!”
Mel smiled at him. “Like I told you, just think how much better it will be when you learn to sleep through it.” All three girls started laughing hysterically.
Mel suddenly looked troubled. “That reminds me,” she said in her no nonsense voice. She pulled the pacifier out of her purse and stuck it into his mouth again. “That stays there!”
Chad was aghast. One humiliation on top of another, and there was nothing he could do about it. Sandy and Cassie started laughing at him all over again.
“It’s his latest phase of training,” she told them. “I think he looks adorable sucking on it like a good sissy baby. Don’t you think?”
“Oh definitely,” Cassie replied. “Definitely.” All the women enjoyed a good long laugh.
Chad couldn’t understand why that earthquake he was praying for should be delayed so much. He sat and listened as Mel began telling them a little about the things she had been putting him through all week. Things that Chad really didn’t want to be reminded of. Way too many incredibly humiliating things. He couldn’t blame them for laughing, if he were in their position, he would laugh too. And despite how embarrassing it all was, it was making him horny again. It certainly didn’t seem to take much anymore. He really needed some relief.
He had been only half-listening for a while now, mostly lost in reliving the embarrassments he had been through over and over again. He was enjoying it because he was feeling his horniness as an internal warmth. A delicious warmth that he was surprisingly enjoying. But he was jolted back to reality when Cassie said, “Maybe I can help.”
Chad desperately tried to remember what they had been talking about. Oh yeah, Mel had mentioned she was going to be putting suppositories up his rear end with each diaper change for the foreseeable future. She had been planning on making him drive to her office every day at lunchtime to change him and put another suppository in him, but her schedule wasn’t exactly the best for doing it.
“Where does he work?” Cassie asked. Mel told him. “I think I know where that is, and it’s only a few blocks from the gym. Why don’t you have him come to the gym at lunch every day and I can change him for you.”
Mel looked very surprised. “Are you sure?” she asked tentatively. “You know, he’s going to be messy.”
Cassie scoffed at that. “Don’t worry, I’m not afraid of a little mess. You wouldn’t believe how many women barf all over everything while they’re exercising and I have to clean that up. I can’t imagine that he could possibly be much worse.”
Mel shook her head. Chad was sure she was going to decline and he was very glad about that. Things were bad enough for him already. But Mel didn’t decline. “Well, if you’re absolutely sure about it. It really would be a big help.”
“Mel, you know I’ll be glad to do it.”
“Ok then,” Mel replied. “Staring Monday, I’ll send him to you at lunchtime. And don’t worry, I’ll make sure he has everything you need.” She looked over at Chad then and suddenly he was more afraid than ever.

That night, Chad laid down on his blow-up mattress and began sucking on the first of the three baby bottles that Mel had left with him. They were all taped at the top so he couldn’t dump them out. The darn pacifier she had been making him suck on most of the day was now pinned by a pink ribbon to his onesie where he was supposed to start sucking on it as soon as the last bottle was finished. And she had been very clear that he was supposed to keep sucking on it all night long. Ugh!
He was so tired. Bone tired. It had been a very long day and he hadn’t slept much all week. The new sheets he was laying on felt very nice against his hairless legs. The pillow case felt nice too. They were just embarrassing to look at. He had placed his teddy bear on the floor where it would be out of his way while he slept. He had a feeling that Mel wouldn’t exactly approve, but she hadn’t said anything about it earlier.
He replayed the day over and over again in his head. He had to call himself Sissy now. His new name. A girl’s name. A name that all too well described exactly what he was. How utterly embarrassing. That thought alone began making him grow hard again inside his already wet diapers. And starting next week he was going to have to have his diapers changed at lunchtime. That part he was actually really happy about. It had been difficult going all day, peeing as much as he now did, without having his diapers changed. He realized that just the thought of somebody changing him like a baby was also fueling his need for release. He needed to pee again, but knew he couldn’t. He was too hard, even inside of his diapers. He desperately tried to rub himself through his baby-doll nighty and the onesie that was again locked on him. But it was no good. The diapers she had been put on him again for the night were way too thick. He had thought that the cloth diapers would be more fun than the disposables, but in truth, they were just different. With the cloth diapers he could always feel it when he was wet, which was now almost always. But he was wet so much that he had quickly gotten used to it. Being wet all the time was beginning to feel normal to him. How interesting he decided. His aching cock gave another twinge, begging for relief. His balls were aching horribly too. Something that he was sure that Mel would care nothing about. He tried desperately again to rub enough sensation through his thick diapers to get some relief. But again he was left denied. He was so incredibly frustrated over it – and that too was fueling his desire. He couldn’t win.
It had only been a week. A long and horribly humiliating week. Every day had seemed to bring humiliation after humiliation. He had hated it and loved it. What would next week bring? One thing was for sure, she couldn’t do much more to humiliate him than she already had. That thought alone was comforting.
One week gone out of the two month bet. As he drank his bottle of the horrible tea, he felt his need to pee growing. He couldn’t pee of course as hard as he was, but just the fact that he knew he needed to pee so much let him know that he still had total control. As much as she had put him through, she hadn’t stripped anything away from him at all. He was going to win that bet. Of that he had no doubt at all.