The Bet - Chapter 14 (Friday – week 2 Part 4)

The Bet
by Karen Singer

Chapter 14 (Friday – week 2 Part 4)

He could tell that Mel still wasn’t happy with him as they got back into the car again. He also figured that she’d take him out to dinner now and make him drink from his baby bottle in front of a lot of people again. He wasn’t looking forward to that at all. It was hugely embarrassing - one of the major things that made him want to crawl into a hole somewhere and stay there – forever. “Are we going to dinner now?” he asked, knowing that they probably were. “No,” Mel replied, “We have to go somewhere else first and I want to get there before the store closes.”
Chad didn’t know whether to be happy or scared. He was happy because he wouldn’t have to repeat the baby bottle thing in the restaurant, but he was scared of what Mel had in mind now. Her shopping trips could be miserable for him.
Mel drove quickly and determinedly towards the area where the store was supposed to be. As she got close, she started scanning the store fronts to try to spot it. There it was! She pulled into the parking lot of a row of stores. There were plenty of empty parking spaces right in front.
Chad looked up at the store in front of him as she pulled into the parking space. The brightly lit sign above the store said Uniforms. “Uh oh,” he thought to himself. He looked over at Mel, she was smiling wickedly at him as she pulled her keys out of the ignition.
“Leave your diaper bag, in the car again,” she said. “Now let’s go in and get you fitted.”
The saleswoman who greeted them as they walked through the door said a very nice hello to Mel, but she did a double take when she looked at Chad.
“Say hello,” Mel said quietly to Chad.
Chad dropped into a curtsey and said a simple, “Hello.”
The saleswoman looked like she was going to panic. She finally looked back at Mel. “May I help you?”
“Yes, I need a uniform for my maid here.”
The woman looked back at Chad again. Chad suddenly felt more embarrassed than ever.
“Okay…” the woman said, drawing the word out as she tried to compose herself. “What did you have in mind?” Then she quickly added. “We don’t carry any of that fancy French maid stuff. This is not a…” she was lost searching for the word.
“Don’t worry,” Mel reassured her. “I want something proper.”
The woman nodded, obviously reassured. “In that case, let me show you what we have.” She led the way to the back of the store where there was single rack in the wall with a lot of dresses hung on it. “We sell to a lot of caterers, and hotels, and any of these uniforms should work for most occasions.”
Mel started browsing through the uniforms. Chad saw mostly very plain looking dresses in a variety of colors. He saw Mel spending time considering a pink one, but then she moved on again. Finally, Mel reached the end of the dresses and started back through them again in reverse. She quickly pulled out one that was kind of a grayish black with white cuffs on the short sleeves and white lace all around the rounded neckline. Mel seemed to be really happy with it. “Oh, I like this one a lot,” she said as she held it up to inspect it closer. “Do you have one that he can try on?”
“Of course,” the woman replied. “What size does she… I mean he wear?”
Mel almost laughed. “I’m not sure. What do you suggest?”
Chad almost groaned. “He usually wore a size twelve and he knew that Mel knew that.”
The woman looked him over carefully, which Chad wasn’t too thrilled about. “I think we should try a ten, or perhaps a twelve.” She opened a closet in the wall and started sorting through a lot of dresses that were very closely packed together. She finally found what she wanted. “This dress isn’t exactly the same model, but we can use it to at least determine the right size.” She handed the dress to Chad who wasn’t really happy to take it. “There’s a dressing room right here,” the woman said, pointing to a door a few feet away.
Chad sighed and took the dress inside. He set his purse on the bench inside the room and began getting undressed. As he stepped into the larger of the plain looking dresses, he thought to himself. “Now I’m trying on maid’s dresses in a store. What will she have me doing next? And with that, he suddenly felt the little pinpricks irritating him again from his chastity device. He found the size label inside the dress – twelve. Good. At least she had handed him the right one first. He had to struggle to zip the dress up behind him, but it wasn’t too bad. But what was bad, was that trying the maid’s dress on was fueling his fantasies too much. And yet he could do nothing at all about it. It was so frustrating!
When he finally had the dress on right, he stepped out of the dressing room. He was glad that there were no other customer’s in the store just then.
“Oh, that’s very nice,” Mel said as soon as she saw him. But what was really interesting her, was that for the first time she was starting to really see her future vision for him. She walked over to him and started pulling on the dress in various places to see how it fit. “Is this the twelve?” she asked.
“Yeah,” Chad replied. “That’s what I usually wear.”
Mel’s angry look let Chad know quickly that he had messed up again. She continued to stare at him. He dropped a quick curtsey as he said again, “Yes, Mistress, it’s the twelve.” She seemed to be pleased again.
“I think I’d really like to see the other one.”
Chad was surprised, he always wore a twelve. But he took the other dress the saleswoman handed him and went back into the dressing room. He had to struggle a lot more to get it zipped up in back, but he finally got it. The whole dress fit him tighter. He could feel it pressing against his padded breasts. He could feel it hugging his entire body. He stepped out of the dressing room intent on letting Mel know that it was too small.
“Oh, that’s much better!” Mel said instantly. Chad was very surprised. Was she crazy?
“Yes,” the saleswoman agreed. This time she was the one who pulled on various parts of the dress to check the fit. “It fits almost perfectly.”
“Good!” Mel replied. “But do you have one in the style I want?”
The woman smiled and walked over to a drawer in the wall and pulled it out. The drawer was loaded with dresses folded and wrapped in plastic. “How many would you like?”
Chad realized that even Mel was surprised. “Just one for now. Then we’ll see about more later.”
The woman pulled out one of the packages and checked the label. She handed it to Mel. “Do you have any aprons to go with it too?”
“Of course,” the saleswoman replied. “We sell a lot of them. Do you want to pick one out while he changes back again?”
Mel just smiled and let her lead her away.
Chad headed back to the dressing room to change. As he pulled his own clothes back on again, he realized that the entire situation hadn’t been bad at all. A bit embarrassing for sure, but most of the things that Mel usually put him through were far worse. Before he left the shop, he had to curtsey and say thank you to the saleswoman one more time. Thankfully, there was no one else around.

As Mel drove along the busy street, she kept picturing Chad as he had looked in the maid’s dress. He hadn’t worn the one she had picked out, but it had been close enough – any maid’s dress would have been close enough. Now, as the busy Friday night traffic was all too thick, she suddenly couldn’t wait to see him in the dress she had just bought him – complete with the apron. But she had other places she needed to take him, other things she wanted him to buy. And they hadn’t even had dinner yet! But just seeing him in that dress… what it had done to her… was still doing to her. Cassie’s words were suddenly ringing very clearly in her ears. “If you’re not making a mess, you’re not having sex.” Right then, she wanted sex badly, very badly. All plans were off! She spotted a fast food restaurant right ahead of her and she turned in very quickly, almost too quickly.

Chad fully expected Mel to stop at another restaurant after buying the dress, but he was surprised when she pulled into a fast food restaurant and then went through the drive through, as if she couldn’t wait to get home again. He was more surprised to find out that that seemed to be exactly the case as he tried to carry his purse, his diaper bag, the bag with his new maid’s dress and apron, the bag containing their dinner, and the large size drink that she had ordered for him, up the stairs to her apartment – while she carried her purse and the other drink.
His hands were so full, that once he was in her apartment, he had to carefully juggle things to set everything down. Mel was at his side instantly with a pair of scissors. She grabbed the bag from the uniform store and pulled everything out of it. The item on top was a white apron, all folded and wrapped in heavy plastic like the dress. In moments she had cut the plastic from both the apron and the dress. She handed them to him. “Go to my bedroom and put this on.”
He took the dress and apron from her hands. Was it his imagination, or did she seem a bit flushed? Probably his imagination. He carried it into her bedroom and set the apron down on the bed. He spread the dress out open. It was a simple dress, but the white cuffs on the sleeves and the white lace around the collar made it seem much more interesting. For the first time he realized that the dress had two pockets in the front – not that they’d do him any good. He undressed, having to remove his shoes first because they were strapped onto his ankles.
He stepped into the dress and pulled it over his shoulders. As he did so, his chastity device once again began giving him little warning signs. He struggled to zip it up and then fasten the hook behind his neck. The dress felt tight against his body. He ran his hands down his body from just under his padded breasts to his thighs. The pinpricks of pain wanted to become much more, but he carefully controlled himself. He had to sit on the floor to buckle his shoes back on.
“What’s taking so long?” he heard Mel call from the living room.
“I’m almost ready!” he called back. He picked up the apron and shook it out. It was rounded on the bottom with a row of wide lace all along the edges too. He wrapped the wide straps around his waist and attempted to tie them in the back in a large bow. He was ready. He realized that he was about to show Mel her fantasy. He took a deep breath and walked out to the living room.
Mel was sitting on the sofa watching the door to her bedroom intently. There was food in the kitchen, but she wasn’t the least bit hungry, not for food anyway. Finally Chad walked out of the bedroom. He stood a few feet from the door and just stood there while they each stared at the other for a few moments. The excitement inside of Mel soared. She had done this! She had made him into her maid. He was standing there in front of her dressed as her maid because she had made him do it.
She got up from the sofa and walked around him. “The shoes are all wrong, but we can change that later,” she said. She stood back from him. “Thank me for your new dress, Sissy.”
Chad immediately dropped into a curtsey and said, “Thank you, Mistress.”
Mel had to press her thighs tighter together against the need that wanted to escape. “Sissy… you’re wearing a dress now. You can actually grab your skirt when you do that. I know we should have had you practicing that way before. I realize that now. But please try to remember to do it properly from now on.”
Chad had to fumble to grab the skirt of the dress as he dipped into another curtsey and said, “Yes, Mistress.”
Mel smiled at him. “It will get easier with practice. At least it better!” She turned her back on him and began sauntering merrily into the kitchen. “Sissy! I’ll have my dinner now!” She felt like a queen.
Chad immediately dropped another curtsey and said “Yes, Mistress.” Then he hurried ahead of her to the kitchen to get the burgers she had ordered out of the bag. He was about to set her burger in front of her, still in it’s wrapper, but luckily he stopped himself in time. He unwrapped it and set it out on a plate for her along with her fries. Her drink he poured into a much nicer glass than the one that it had come in. He set them all on the table in front of her and saw her smile.
“To your corner, Sissy.”
His heart dropped. He didn’t really want to go to the corner again while she ate, but he obediently went, slowly, and crammed himself in.
“Put your feet together!” her voice lashed from the kitchen. “Legs straight, not slouched!”
He quickly straightened himself up and tried to stay that way. He couldn’t see anything except the blank walls of the corner so he closed his eyes. He couldn’t hear anything either, she was being silent and was too far away. The seconds seemed to drag by. He had no idea how long he had already been standing there. How could it take her so long to eat just a burger? His feet were beginning to kill him in those shoes, the straps were digging in painfully. He moved one of his feet just a tiny bit to relieve the pain.
“Don’t move your feet!” her voice lashed out instantly.
Chad immediately brought his feet back to where they were. His whole body tense now in case she yelled again. But she didn’t, and he allowed the tension to drain away as the seconds ticked by slower than ever.
Mel had only been able to eat half her sandwich, she was too keyed up to eat anymore. She had him standing in the corner where she knew he didn’t want to be. He had moved slightly and after not moving for so long the tiny movement had been like a signal flare. She had put a stop to that quickly. And now she had him stuck there again. Glued to his corner like a child. Completely in her power.
She got up from the table and sat in one of the chairs in the living room where she could see him better. She suddenly wanted to see all of him better. “Turn around, Sissy,” she said. His whole body seemed to sigh with relief as he pulled himself out of the corner and faced him. “Back up into the corner and stay there,” she commanded. She could see the questioning look of surprise on his face, but he did as he was told. She made him stay there like that for a long time, just standing still in his corner.
Finally, she could take it no more. Her period be damned. It would probably be over with by tomorrow anyway. “If you’re not making a mess, you’re not having sex!” But he was in his maid’s dress and she didn’t want that to become a mess. “Sissy! Go take your dress off now. And hurry!”
Chad blinked in surprise. Now what? He tried to drop a quick curtsey where he was but he was too far into the corner and the walls got in the way. She hadn’t noticed anyway, she was fumbling around in her desk again. He headed for the bedroom.
“Sissy!” she called. He stopped and turned around. “Just wear your diapers and nothing else.”
“Yes, Mistress,” he replied with a better curtsey than last time, but she was back at her desk again.
By the time he came out again in just his diapers and plastic panties, Mel had completely covered half the sofa in towels. He was very surprised at that. She came up quickly behind him and grabbed his hands and tied them behind his back. He quickly became nervous. She positioned him in front of the couch and made him get down on his knees. But now Chad had a pretty good idea of what was going to come next. She tied his ankles together too, then left and came back with her scarf again. In moments, Chad was well blindfolded.
Mel walked around in front of Chad for a few moments, making sure he couldn’t see her. Then, tentatively, she began pulling her clothes off. The more clothes she removed, the faster off they came, till this time, she was completely naked in front of him. Knowing that he couldn’t see her. She sat on the couch in front of him, her desire growing fierce. “Ok, Sissy. Crawl forward.”
With great difficulty, Chad moved one knee forward. Mel felt her need rise a bit more. He swung his other knee forward, she started to breath in small gasps. He moved again, and she suddenly had clear visions of him in his maid’s dress. She wanted him to move faster now, but the wait was just as delicious. Another knee. He was turning his head now, trying to get a sense of where she was. “I’m right here, baby,” she said softly. He moved again in her direction. He was almost there. “Just a little more, baby.” Her voice helped to turn him in just the right direction. He moved one more time. She couldn’t wait anymore. She moved further onto the edge of the couch and grabbed his hair. Roughly she yanked him down into her waiting sex.
Chad let out a small scream of surprise as he suddenly felt her grab his head and yank him down. His face ended up right in her crotch. The force she had used hurt his nose a bit. He realized her crotch was very wet. The odor of her sex was almost overpowering. She was grinding herself against his face now. Wanting more. Tentatively, he reached out with his tongue and licked a tiny bit.
With the first touch of his head against her crotch, Mel almost came. It was wonderful. She needed more though, much more. And when she felt the almost tiny touch of his tongue licking her, she really did come… in one big gasping wave. But she had only just started. This was her dream. This was what she had always wanted. She was in full control. She didn’t have to worry about getting pregnant. She didn’t have to worry about anything. She had all the power. And he had nothing. He couldn’t get any kind of pleasure at all. She had fixed him so that he was totally denied. The power of what she had done drove her quickly to another orgasm. More, more, more!

Chad felt like his face was being abused badly as she thrashed around him. He could hardly breathe. She kept pulling him tighter and tighter into her, then she would back off slightly, only to do it all over again. And through it all, she was so wet! He was quickly becoming very tired. Not being able to breath wasn’t helping either. He tried to pull away, but her grip was too powerful, too fanatical. Helplessly tied as he was he had no leverage to fight against her. She was feeling orgasm after orgasm, and he wasn’t allowed to feel anything. She had locked him up. Completely. As great as his need was, he had no way to let it out. She was skyrocketing above him, using him to satisfy her utterly. And his need was locked away. The very thought of it refueled his wantings even more and he felt the pinpricks beginning again, but only for a moment. He was growing too tired. He tried to concentrate on his penis. Willing it to feel something in all this. He desperately wanted it to feel something. But locked up inside the device, he could feel nothing. Nothing at all. It was so frustrating. She orgasmed again. Wasn’t she done yet? It seemed not. But at least she was moving slower now, with less need.

Mel came down from another high, and slowly sanity began to creep its way back into her. Oh God it had been so good! She still rocked against him, feeling his wonderful face and tongue still stimulating her. Making her feel wonderful. She looked down. She could only see the hair on top of his head. He was still trying to lick her, but now that had become very weak. She pulled his head away from her, slightly, then all the way up. He was gasping for air, obviously very tired. She cared, but she didn’t care. It had been too good. His face was an absolute mess, not just wet with her sex, but red from her period too. The scarf around his eyes was probably ruined. She’d have to get another one.
She took a deep breath to calm herself, still holding onto his head with both hands. When she had calmed down enough, and she felt that he was stable enough and wouldn’t fall down, she got up and went to the bathroom. She wet a washcloth and brought it out to the living room and washed his face. She could tell he liked that, needed that. He looked better afterwards. She glanced at the couch. It was a good thing she had put down so many towels. They were a mess.
She grabbed Chad’s head softly in her hands. “Lay down Sissy.” And she helped him to lay on his side without hurting himself. “Stay there like that.” I’ll be back in a little while. She grabbed the towels from the couch and left him there. She went into the bathroom and peed, then she got into her shower and rinsed herself off thoroughly. She felt wonderful. Glowing.
She dressed quickly in jeans and a t-shirt and went out to him. He was sleeping, tied up where he was. He woke up as she started untying him. She took his blindfold off and helped him to his feet, then she led him into her bathroom where she removed his diapers. He wasn’t messy. He wasn’t even as wet as he usually was. She remembered that he hadn’t eaten or even had anything to drink all evening. His dinner was still on her kitchen counter.
She opened her cabinet and pulled out two of the super thick nighttime diapers and laid them under him. She spread the baby lotion over everything she could touch. She looked carefully at his penis, trapped inside of the device. So small, so denied. She had planned on taking the device off of him tonight to clean him thoroughly, but that was going to have to wait. She wasn’t up to it just then. She quickly shoved two more suppositories up inside of him and struggled to get the diaper pins through the extra thick diapers. Then she pulled his plastic panties up again. “Get dressed now,” she told him, “just wear what you wore to work earlier.” She left him and went back to her kitchen. Nothing had been cleaned up, she hadn’t given him time. She grabbed the large drink she had bought for him and found several empty baby bottles to pour it into.
Chad moved slowly as he dressed again. He was aching and sore all over, but fortunately, not too bad. The thick cloth diapers she had put on him felt strange, horribly bulky. He felt very tired just then. His stomach growled. She hadn’t even allowed him to eat. When he was dressed, he went out to find her.
“Where’s your dress?” she asked.
“I left it on the bed.”
“Get it. Bring it home with you.”
He turned around. Home? Already? He grabbed the maid’s dress and the apron that went with it and carried it back to her living room. She handed him a plastic bag with three baby bottles in it, filled with the drink she had bought for him. She also handed him his dinner that she had put back into the bag from the restaurant. “Go home now. I’ll leave a note for you later tonight like I usually do.”
Chad was bewildered. It almost felt like she was throwing him out. But she didn’t seem angry in any way. He grabbed the bags she handed him, grabbed his purse and diaper bag too. And with his apron and dress hung over his arm, he went back to his apartment. He switched on the light as he went in. The apartment seemed to echo its emptiness back at him. He set everything down in a pile on his floor, not even bothering to hang the dress up.
His stomach growled. He dug the food and the drinks out of the little pile he had created and carried them into the kitchen where he ate standing up at his counter. He didn’t know what to think. So he didn’t think. When he was finished, he got undressed down to just his diapers and plastic panties. Then, only because he thought he should, he put his baby doll nightie on. He laid down, and soon fell sound asleep. It had been a bit of a strange evening.
And in the middle of the night, the dreaded suppositories did their job on him.