The Bet - Chapters 16 And 17 free porn video

The Bet by Karen Singer Chapter 16 (Sunday - week 3) Fitful dreams cause fitful sleep. And consequently, fitful sleep causes fitful dreams. He was inflicted by both. After starting to relearn to hold back all day, the three baby bottles of Mel's special tea that he drank before he fell asleep re-stimulated his system... a system that was already trying to relearn how to sleep through it all. He tried to wake up to hold back each time, but it was simply too difficult. He was getting no sleep at all. He finally abandoned himself to just letting it happen without holding back. It was his only choice if he wanted to get any rest at all. And just as he finally fell into a deeper sleep, he was woken up one more time when the suppositories in his system rudely decided to do their thing. He had no control over what the suppositories did - ever. That was impossible and he no longer even tried. To mirror his troubled sleep, he dreamed - strange disturbing dreams. He was a child again. His mother was unhappy with him and he didn't know why. He asked her why over and over again, but she never would say. In his dreams, he felt crushed because he had somehow disappointed her - his own mother. He ached for her forgiveness, but forgiveness never came. There were tears in his eyes when his pink alarm clock went off. While the images and situations of the dream were quickly lost from his consciousness, the emotions were not. He wondered why he felt so depressed and chalked it up to not sleeping well. He literally dragged himself off his blow-up mattress and stood up. He turned the loud music from the clock radio off. It was later than he thought, yet it felt all too early. He waddled awkwardly into the kitchen to see if she had left him another note with instructions. Of course she had. Sissy, First baby bottle! Go buy yourself some breakfast. Make sure your uniform is ready for inspection later, but don't wear it. Make sure you have a grocery list ready for this morning. Pad the breasts of your girdle. No makeup today! The rest is up to you, but don't forget your ring and necklace. I'll be looking you over when you arrive again. Be here at ten o'clock - sharp! Ready to go! No excuses this time. Second baby bottle before you get here! The cookbook she had purchased yesterday was on the counter next to the note. He automatically went to his refrigerator and pulled out a bottle without ever thinking about not doing it. He grabbed the cookbook from his counter and went into his living room where he sat in the only chair that he had. His overly bloated diapers made it feel more like he was sitting on a big ball instead of the seat of the chair. He put the baby bottle to his lips and started browsing through the cookbook. The cold tea on his system triggered his need to pee again. He almost let it out without holding back again but he caught himself just in time. He held it as he began reading through the recipes. Almost a minute later, he couldn't stand it anymore and released himself into his soaked diapers. Without realizing it, his depression melted away at the same time. Mel rolled over in bed and opened her eyes. Without moving her head, she glanced at her clock. It was fairly late, but it was also Sunday. Her entire body felt loose and relaxed and just plain wonderful. It was amazing what Chad had done to her last night... or maybe it was more like what she had done to herself - with him. Either way, it had been wonderful. Wonderful enough that she felt no desire to even get out of bed. She rolled over lazily and closed her eyes. Smiling and thinking about Chad, she fell asleep again. After he had shaved and cleaned himself up in the bathroom, Chad stared at his closet and tried to figure out what to wear. Really, for the most part, it boiled down to dressing like he had for work all last week - mostly. He would much rather wear the low-heeled shoes, but those shoes were now part of his uniform and since he had quickly re- shined them already this morning, he didn't want them to get messed up before Mel inspected him later. That left him with only a choice between several different pairs of high heels. He thought about work tomorrow, could he wear the low-heeled shoes to work? He prayed that he could! His other clothing choices weren't much better. The only male clothes he had now were his shirts. But now he had several new blouses hung up with them. He touched one of them and pulled it aside to look at it more closely. He could wear it, he was sure. He was also sure that Mel would really like that. In a way, it would be fun. Of course he could wear one of his skirts as well... but not likely! Especially not since they were going out shopping again. He shuddered as he remembered his trip to the grocery store last week when she had made him wear a skirt. She had actually called the police on him before he got out of the car and gone into the store with her. No, no skirt today for sure! He pulled out one the shirts he often wore to work and a pair of the pants he had worn earlier in the week instead. Two diapers, a pair of plastic panties, pantyhose, an all-in-one girdle, old pantyhose stuffing the breasts of his girdle, his button- down shirt, women's slacks, and the same pair of relatively comfortable heels he had worn yesterday. He added his new necklace and ring. He had a lot of trouble trying to connect the clasp on his new watch and then fasten the extra security chain it had, but he finally got it. He looked in his bathroom mirror. What little of himself that he could see looked fine - if you didn't count the breasts sticking his shirt out abnormally. With his shirt buttoned up far enough, it mostly hid the feminine necklace he was wearing. It was the rest of him that he couldn't see in the mirror that he was worried about. Knowing he had to get some breakfast, he grabbed his purse and headed for his favorite drive-through. Mel held her coffee cup in both hands and took her first sip. It was good. A small wave of pleasure rippled through her body. Still in her nightgown and robe, she sat down in one of her living room chairs to enjoy it. She had some things she needed to be doing this morning before Chad came, but she just didn't feel like it. Her hair needed washing, but she figured she could put that off till tomorrow too. Right then, relaxing and enjoying her coffee seemed much more important. She was looking forward to going shopping with Chad again today. First, Sandy was going to help them look for more makeup and then they had grocery shopping to do. She well remembered last week's grocery shopping trip. She had made him wear a skirt, and then had to fake calling the police to get him out of the car. She hadn't demanded that he wear a skirt today. She knew he wasn't quite ready for that yet. Not yet, but if things worked out like she planned, then he would be pulling the skirts out of his closet to wear very soon. That thought gave her another small wave of pleasure. She sipped her coffee again. Yeah, going through the drive-through was absolutely one of the best things he could do, he decided once again. This morning, the girl hadn't even noticed anything odd about him at all - till he handed her his money and she saw his electric pink fingernails. He wasn't sure if she had noticed the breasts protruding under his shirt after that or not. But it didn't matter. Didn't some guys wear nail polish now - kind of like a fashion statement? Okay, not usually bright pink! He had been smart today, he didn't get any coffee. Why make matters worse since he still had to drink another one of Mel's stupid baby bottles of tea? He wolfed his breakfast sandwich down as he began drinking his second baby bottle of the morning instead of his usual coffee. He was less concerned about messing his diapers while he was out today. Since he was now diapering himself more often, he was getting less and less of those miserable suppositories stuck up inside of him. He wondered if Mel realized that fact. He wasn't about to mention it to her. As he headed back to his bedroom after breakfast to press his uniform for the day, he realized he was already holding back on peeing... and he hadn't even realized that he had to go. He smiled to himself. Things were getting better and better! Mel glanced at her clock, then went back to watching her door. He better not be late today! It was with a profound sense of excitement and relief when she heard him knocking - thirty seconds early. More excited than she realized she was, she quickly opened the door for him. "Good morning, Mistress," Chad said as he dropped a quick curtsey. "Good morning, Sissy," she replied as she stood back out of the way. Once again he was carrying his uniform and the shoes for it in his hands. She was a bit disappointed to see that he hadn't worn his new slacks today, but that was only a very minor thing. She left the door wide open since Sandy and Cassie were supposed to be there any minute now too. "Go put your dress in my bedroom again," she instructed. When he came back again, she had him stand near her door where she could look him over completely like she had done yesterday. "Are you wearing two diapers?" she asked. "Yes, Mistress," he said with a quick curtsey. "Unbutton one of the buttons on your shirt! I can't see enough of your necklace." He reached up and unbuttoned one more of the buttons on his shirt than he was used to. He suddenly felt more exposed, even though it wasn't much more than before. The breasts sticking out from his shirt now forced the opening at his neck to go wider than he would have liked. "Much better," Mel stated, more to herself. This time she had no makeup job to inspect since she was sure that Sandy would want to see his bare skin. She suddenly stepped back with an angry expression on her face. "Where's your pacifier?" Chad was surprised and worried. He hadn't even thought about it. He dropped another curtsey and said, "I'm sorry Mistress, I forgot it again." "This is happening too many times now and I keep forgetting to punish you for it!" "Hi everybody," Sandy's cheerful voice interrupted from the doorway as she and Cassie stepped into the room. "Is there a problem?" Cassie asked. "Nothing we can't sort out later!" Mel replied with an angry look at Chad. She turned back towards her two guests and smiled. "Are you two ready to go?" "More than ready!" Cassie replied enthusiastically. "Are you still going grocery shopping when we're done?" "Yes, we need to." "Then we'll take my car and meet you there," Cassie replied. "That reminds me," Mel said as they all went out through her doorway, "Sissy, do you have your shopping list?" "Yes, Mistress," he replied, this time without the curtsey. "It's in my purse." Mel followed Cassie's car all the way to the mall and parked next to her. They all went together directly into one of the major department stores. Chad had remained silent for the entire trip and stayed that way now as he followed a few steps behind the three women who were chatting together and mostly ignoring him. He had no doubt that he was in for more humiliation. But wasn't going out dressed as he was right then humiliating enough? He certainly thought so. The women were ignoring him like he wasn't there. Would they miss him if he left and went back to the car? He really wished he could. Unfortunately, he knew better. Sandy led them all the way through to the makeup section where she suddenly squealed again and took off nearly at a run for one of the counters. "Ashley! You're still here!" "Sandy!" her friend called from behind the counter. "What are you doing here? Need some makeup?" "I always need makeup. You know that!" "Don't we all," Ashley agreed. But out of the corner of her eye, she noticed Chad for the first time. "Uh... I see you've got some new friends." Sandy turned back towards Mel and Chad. "Yeah, that's why we're here. This time I need some makeup for him!" "You're kidding me, right?" But then she corrected herself before Sandy could answer. "No, I can see for sure that you're not." She shook her head. "Let me guess, you want me to do a full makeover on him, right?" "No way!" Sandy replied. "Not till I get my claws into him first! We just need some decent makeup for him to work with." Ashley looked a bit surprised... if not disappointed. "Ashley, this is Mel," Sandy added. "She lives a few apartments down from us." "Hi Mel," Ashley replied, but her eyes were still on Chad. Sandy pointed at Chad. "And this is Sissy." Chad turned another shade of red while Ashley just nodded her head, still trying to comprehend him. "Yeah, I can see that!" "No, that's his name now." "His name?" she asked. "That's it," Cassie confirmed. Chad could feel his face turning a darker shade of red. Ashley shook her head. "Okay, sissy boy, climb up on the stool here and let's get a better look at you. And if you don't stop blushing, we're never gonna figure out your skin tones!" Chad did as he was told, but he did it slowly and cautiously. His heart was suddenly pounding along with the embarrassment he felt. Were there any other people watching him? He didn't want to look around to find out. He was sure there were at least some people watching, he just hoped it wasn't too many. "Okay," Ashley finally asked, "what are you interested in?" "Well," Sandy replied. "He's got some things already, but..." "Everything he has should be in his purse!" Mel interrupted. Ashley looked at Chad. "Well, honey, you gonna lay it all out for us? We can't help you if you don't." Chad reluctantly opened the purse in his lap and began grabbing all the makeup out of it and putting it all on the counter in front of him. Ashley picked up each item and looked at it and sorted it all into different piles. "This is okay... this is junk... this is good, heck, I use it myself! It's just as good as anything I got here and it's cheaper! Good... good... okay... not so good... okay..." When all the makeup was out, she and Sandy went through it all one more time. Most of it was okay, but clearly both Sandy and Ashley thought he needed more. "And where's his moisturizer?" Ashley asked. "Home," Chad replied. "I shave with it." "You shave with it? Huh! I guess it's as good as anything else." "Okay Sandy, what do you want first?" "I think some concealing sticks and highlighter," she replied. Chad soon found his face being attacked by Sandy smearing one type of makeup after another on it then wiping it all off again. From there they moved into more colorful and noticeable options that he was a lot less happy about. He also wasn't happy to see the pile of things they wanted him to buy growing larger and larger. "Why so much?" he complained. "Honey," Ashley replied, "you need different stuff for different occasions. Not to mention different lighting. Come on, you gotta know that much!" Chad didn't say anything. His answer would have only made him look more foolish than he already felt. The longer they worked on him the larger the pile of things they wanted him to buy became. He had visions of his purse overflowing and breaking under the strain. "How am I going to get it all into my purse?" he asked at one point. "Don't worry," Mel replied. "We'll help you figure out which things you should have with you all the time and what you can leave at home." That was the only bit of comfort Chad got through the whole process - and it was only a very tiny bit. When they were done, Chad not only had a fairly large bag of makeup, but also several free gifts that came with it all, including some perfume that all the women seemed to think was heavenly. But to Chad, it smelled too flowery and made his stomach feel like it had butterflies in it. He put the reason for that down to it being so long since he had had any sexual relief. Unfortunately, they had sprayed the stuff on his neck and both his wrists. There was no getting away from the smell! The only good part as far as he was concerned, was that before they left, Ashley had wiped all the makeup off of his face again. That alone felt like a minor victory. As Chad rode with Mel toward the grocery store, he stretched and rubbed his face. After all the makeup they had put on him then taken off again, it tingled a bit. He loved the feeling of being out for a change without any makeup. But now he wished he could get rid of the ever-present perfume smell. There was just no winning anymore. And worse, the smell of the darn perfume was making him horny. The clothes he was wearing just then weren't stimulating his sexual need all that much, but the smell of the perfume - especially when it was coupled with the occasional sight of his pink fingernails, was sending electric thrills throughout his entire body. He had to pray that his chastity device wouldn't start hurting him again. Once again he followed Mel into the crowded store. Was there anyone there who would remember him from last week? Probably. He was sure that last week he had been a sight that was hard to forget. But how about this week? Yeah, he was still going to be hard to forget, but hopefully not quite as bad. As he grabbed a shopping cart and put his purse into the child seat of the basket, he paused for a minute to pull his grocery list out. He didn't really need it, but he knew that Mel would want to see him using it. Mel was waiting for him. He pushed his cart up to where she was waiting. She put her own purse into the cart next to his. Last week, he had timidly followed her around the store while she selected things to put into the cart. This time it was different. This time, it was more like two friends shopping together. Anything that Mel thought she might like, she put into the cart, but mostly, he was the one picking up things that he thought they might need. On one aisle, he picked up several kitchen utensils that he thought might be nice to have. She didn't protest at all. It was the same when they came to the spices, he added quite a few that he thought of as basic to every kitchen. Obviously, she didn't cook at all or she would have already had most of them. He noticed a difference in the people around him too. While he was certainly getting lots of interested looks, for the most part he didn't think he was getting nearly as many as he had last week. What a difference not wearing a skirt could make! He was very grateful for that. He had done enough shopping with Mel now that he was starting to become at least a little more comfortable with his silly image in public... to a point anyway. But the thought that he was actually becoming more used to it also frightened him a bit. While they had been buying makeup earlier, he had never once noticed that he was holding back from peeing until they were leaving the store. Now, as they reached the last aisle of the grocery store, he began to think ahead to the checkout counter. Would she ask if he had to pee again? He wasn't sure, but just to be safe, he let himself wet his diapers one more time while they were still shopping. He noticed that now he had to make himself relax to do it. Quite a difference from before, and he was glad. Especially since Mel would never know. "Do you have to pee, Sissy?" Mel asked as the clerk was ringing up their sale. Chad was too aware of the people around them suddenly listening more intently. "No, Mistress," he replied as he dropped a quick curtsey. He heard a few noises of laughter and surprise from the people around him. "I had to do it a few minutes ago." But Mel wasn't letting him off so easily. "You did what a few minutes ago?" "I wet my diapers a few minutes ago." He replied with one more curtsey. Fortunately, Mel looked satisfied as she pulled her wallet out. He was especially glad since there were definite chuckles from the people around them. Chad found himself wishing he was wearing lots of makeup again so it could hide how red he knew his face had to be. When they got home, Chad had to carry all the groceries up to Mel's apartment by himself while she busied herself with work on her laptop. He wouldn't have minded it so much, but going up and down the stairs so many times in his heels got tiresome after a while. In fact, he had been on his feet so much already that his feet were starting to ache constantly. After he put the groceries away, he was a bit surprised that Mel didn't want him to change into his uniform. Instead, she had him make both of them a small salad for lunch. Chad's naturally went into the refrigerator while she ate... and he once again had to stand in the corner. The longer he stood facing the wall, the more he realized he was concentrating on his feet and how his shoes were beginning to hurt. Why had he thought these heels were more comfortable? They didn't seem that way anymore. He yearned to take his shoes off for just a few seconds and stretch his feet. But every time he even fidgeted just a little, Mel yelled at him to stand still. Finally, he heard her getting up from the table. She walked into the room where he was and stood closely behind him. "Are your feet getting tired in those shoes?" she asked quietly. "Yes, Mistress," he said into the corner that was all too close to his face. "You like wearing heels like a girl, don't you." "Yes, Mistress." "But they're starting to hurt now, aren't they." "Yes, Mistress." "Don't worry sissy. You just need to get used to wearing them more. I'm glad they're hurting you. Think about this now while they're hurting you... think about how someday your feet are going to hurt, but they're only going to hurt when you're not wearing high heels. Won't that be fun? It's not very difficult you know. All we have to do is make you wear them all the time. Then, eventually your feet and leg muscles adjust, and bingo... you can't go without heels anymore. Wouldn't you like that? "It's kind of just like you're probably learning to wet yourself while you're sleeping, isn't it? And I'll bet you really are learning that now, aren't you?" Chad's only reply was to squirm in his corner a bit because her words sent chills throughout his body. He realized that what she had just said was all too true. He knew that he wasn't always waking up every time he had to go during the night anymore. "Isn't it better now, being able to sleep through your wetting? Doesn't it make you happy that you don't have to wake up anymore? Just think, soon it will be just as easy for you to wear high heels all the time too. I know that you'd like that. Wouldn't you? That is... if I decide to do that to you. It's not up to you now, is it? Everything to do with you is completely up to me and what I want. I don't think you've quite got that point yet, but we're making progress. Oh yes, we're definitely making progress. "Now, I want you to go and sit on the kitchen floor with your lunch. And the whole time your feet are hurting today, think about what I just said. Wouldn't it be wonderful if your heels didn't hurt you? Maybe I should have you beg me to do that to you. What do you think, should I do that... let you beg me to make you wear high heels all the time? Now go... eat your lunch... and think about that." Chad was mentally shuddering at Mel's words as he left his corner and went into the kitchen. The very thought of what she had said scared him... but at the same time it was thrilling him beyond belief. He could feel the tiny pinpricks of his chastity device digging in ever so slightly, but fortunately, that's as bad as they got as he willfully controlled himself. And his bigger problem was that he had to keep controlling himself, because just as she suggested, he constantly kept thinking about what she had said because his feet continued to hurt. He couldn't help it. Chad had just started cleaning the dishes from lunch when Mel's phone rang. He heard her answering it, but he couldn't hear anything else that she said into the phone. "Okay, Sissy. Sandy's waiting for us. Stop what you're doing and let's go." Chad turned the water at the sink off quickly and dried his hands. Mel was already waiting for him in the living room. "Get your purse and your new makeup, Sissy. We're going to their place." Chad did as he was told. Fortunately all his new makeup was all in one plastic bag that he had set by the door. He was just slightly surprised that they were going over to Cassie and Sandy's apartment instead of them coming here since he still had dinner to make later. Sandy opened their door before Mel had even finished knocking. "Come in, come in," she said quickly. She seemed way too excited for Chad's comfort. He noticed that she had set up a large lighted makeup mirror on her kitchen table. Sandy took his bag of new makeup from him and began putting it all out on the table. "You may as well get your other stuff out now too," she told him, "we're going to need it eventually anyway." As he opened his purse and again started pulling the makeup out, he tried to figure out how he really felt about it. Yes he was excited. Yes he was scared. Yes he felt humiliated. But yes, he was also very interested as well. Did that make him a sissy? He didn't have to answer that question. "Where's your moisturizer?" Sandy asked. "It's still home in my bathroom." "Well go get it girl. We're not going to do this without it!" Chad reluctantly went back to his apartment to get the moisturizer that he had been shaving with every day. Why should he need it? It wasn't doing him any good as far as he could see... other than to make shaving his face easier every day. Once he was back inside Sandy's apartment, Chad was very glad when she told him to sit down in front of the mirror. Now maybe his feet would stop hurting for a while and he could stop thinking about being only able to wear high heels - forever. "Okay," Sandy started. "I'm going to do everything to half your face, and you're going to do the other half. Got it?" Chad nodded. It seemed simple enough - he hoped. She started with his moisturizer and just as she said she would, applied it thoroughly to half of his face. Then she handed it to him. "Okay, your turn." She watched him for a few seconds. "Not so much. You don't need much, just a little. Then spread it out more." She produced a wet washcloth and let him wipe his face clean. "Now do your whole face this time, only don't use so much." When she was satisfied with the way he was doing his moisturizer, she moved on to the concealing makeup. It was a while before Chad realized that while what he was doing should have been humiliating, the way she was going about it didn't make it very humiliating at all. Sandy didn't seem to be trying to humiliate him in any way. None of the women were. They were all sitting around talking and offering suggestions and comments and having a good time. Girl-talk. And once Chad realized it, he was thrilled by it. It was a small thing, but it felt nice. It was mildly fun. Guys talked together all the time, but half the time it was boasting about this or that. With women it was different. He might be a sissy, but for once, he was enjoying himself. If only the feeling could last forever. But unfortunately everything got interrupted when Mel's cell phone rang. "Hello?" she said into her phone. "Again? . . . Yeah, I'll take care of it. . . . Just wait for me, don't do anything till I get there!" She hung up. "I've got to go. Very old client... very stupid kid." "Aw," Cassie replied, "we were having a good time. Does Sissy have to go too?" Mel looked at her watch. "It's probably best if he does go. He still has to cook our dinner later and there's a lot of cleaning he has to get done first!" "That reminds me," Cassie said, "what time do you want us there?" Mel looked at her watch again. "I don't know how long this will take. Hopefully not too long. Let's plan for seven thirty, okay?" "Sounds great!" Sandy replied. "I can't wait," Cassie agreed. Chad was the only one who wasn't sure. When Mel and Chad were outside alone again, she stopped to talk to him. "Sissy, I have to leave right away. I'm counting on you to make everything perfect tonight." "I'll try," Chad replied honestly. "Good. Don't forget to be in your uniform before then but don't get it dirty. I want you looking perfect. Oh, and see what more you can do with your makeup before then too. Now I gotta go. See you later!" And with that, she was running down the stairs and Chad was left on his own. Only this time, he had a lot of work to do before she got back. As he opened Mel's door, he thought about his shoes. He had been sitting down for a long time now and his feet didn't hurt so much. But he knew they probably would start hurting again very soon. Did he dare take his shoes off for a while? Once again, even though his feet weren't hurting, the fantasy of being unable to wear anything but high heels went through his mind. And once again, the tiny pinpricks from his chastity device were just barely there. But the fantasy was powerful enough to make him keep his heels on despite the pain and not take them off. Mel's apartment didn't really need much cleaning. He had done enough of that that he didn't really have to do hardly anything. After he had done some basic prep work for dinner, he started on Mel's laundry, which wasn't all that much. While that was in the washer, he went back to his apartment and got his laundry too. He was especially worried about washing the pants he had wet yesterday morning. He found that he was actually happy as he worked around her apartment. Occasionally he did a few things towards the dinner he was preparing, and at other times he straightened up the house or folded clothes. Even with Mel gone, he was enjoying himself. And as much as his heels eventually started to hurt, the fantasy kept him interested... even when he found himself sitting more and more often to rest his feet. When all of his own laundry was done, he took it home and put the things that needed to be hung up into his closet again. Then he went back to her apartment and looked around. All her laundry was done. Her apartment was clean. The table was set. He looked at her clock. It was time to start the final phases of cooking dinner. Everything was going perfectly. Mel stared across the table at the punk kid in front of him. God the kid was stupid. This was the second time in the last few months that he had been caught with drugs. Bad ones. The problem was that his parents were rich and he didn't care about anything. She knew his parents though, they were good people. Real good. They had been clients of hers for a very long time. One of the few clients she had that had stayed after her father had died and she became the sole legal partner. She owed these people a lot. "Wait here, and don't... say... anything!" she ordered. He held up the chain that was cuffed from the table to his wrist. "Like where the hell am I gonna go?" he asked smartly. She shook her head and left the room. Stupid kid! His parents were waiting anxiously out in the hall. She hated having to talk to them. She shook her head as she walked up to them. "I'm sorry," she said. "He was really stupid this time." "Isn't there anything you can do?" his father asked. She could see the pleading look on his mother's face. "Look," she told them. "Let me talk to the detective again. I'll see if there's anything at all that can be worked out. But I've got to warn you, it doesn't look very hopeful. He actually seems proud of what he did!" "Anything you can do, we'd appreciate," his mother told her. Mel nodded to them both and walked down the hall and went into one of the offices. Detective William Grey was sitting at his desk pounding on his keyboard with remarkable speed. She plopped herself down heavily in the chair in front of his desk. "Just a sec..." he said as he kept typing furiously. He hit one final key then clicked something with his mouse. "There! Done!" Finally he turned toward her. "Hi Mel. Long time no see." "Yeah," she laughed. "Like it's been almost two days now!" The truth was that they ran into each other frequently. Heck, she had even dated him a couple of times, but he really wasn't the type that she was interested in. In fact, all of their dates had left her flat. Too much business - among other problems. "So what do you think?" he asked, referring to the problem kid in the other room. "What a jerk! But he's my client and he's got good parents. It's definitely not their fault. All the other kids in the family are just fine... all except him!" "That doesn't help him though." "No, it doesn't." She looked at him for a few minutes. "Look, I'm betting you really don't want to keep this guy. Is there something we can work out? Like maybe where he's getting his stuff from?" He smiled. "You've been hanging around here too long. Let me see if I can reach the DA." She sat quietly and waited while he talked on the telephone. She tried to grasp as much of his conversation as she could, but she couldn't tell everything. He was a good looking guy. Big and confident. Too confident for her tastes though. Still, if she wasn't so hung up on Sissy just then she might consider asking him out. Yesterday had been kind of an eye-opener for her. It wasn't till then that she had realized how pitiful her social life really was. But that was part of the point. He was big and confident, and Sissy was... well... a sissy! And right now, Sissy was winning out - big time. He hung up the phone. "Okay, there's a couple of things here. First of all, he's got to spill everything... and... we've got to make a decent bust on it." She nodded. "That's good, what else?" "And," he continued, "you've got to let me take you to dinner." She burst out laughing. "Oh Will! You're too much!" "I'm serious! I don't need to let this kid go. We've got enough on him now, and anything else we get from this is probably going to be small potatoes too." "That's blackmail," she replied, still laughing. "That it is! But I'm sticking to it!" She still couldn't believe it, and she was still half laughing. "Okay, deal! Now let me talk to him again and see what we can get." Before she could get to the door again he stopped her, "Oh and Mel... when we go out... don't dress like you usually do when you're not working." Her eyes went wide. "What? You want me to wear a dress?" "Something like that." He sat back in his chair and laced his hands behind his head with a very satisfied look on his face. Mel shook her head as she went out. Way too confident and manipulative. No wonder she wasn't that keen on the guy. And she had just agreed to a date with him? Ugh! Oh, and he wanted her to dress up too? What would be next? Chad heard his cell phone ringing from his purse and ran to get it. "Hello?" he said quickly. "Hi Sissy, it's Mel. How's everything going?" "Perfect," he replied confidently. "Excellent. Look I should only be a few more minutes here, then I'll be home. Is dinner almost ready?" "Yes, it's all set. I was just about to put my uniform on." "Good. I'm looking forward to it. I should be there before Cassie and Sandy, but if not, I won't be long." "Okay," he replied. "See you then." So far, everything was going perfectly. He took the time to change into two fresh diapers before he redid his makeup and put his uniform on. For once, his makeup came out much better. The brushes that Sandy had shown him how to use along with the other things really helped. He was suddenly wishing that they had had time for her to show him more. As he slipped the low-heeled shoes on his feet, he was almost stunned by how comfortable they felt after wearing the high heels all day. But now with these new shoes on, he found himself thinking about the high- heel fantasy all over again. He tied his apron around his waist. He was ready. Dinner was ready to be dished out onto the plates as soon as everyone arrived. But there was still time. Mel wasn't even back yet... and he couldn't stop thinking about the high-heels! He picked his heels up... then put them down again. No, he shouldn't. Mel might be back at any minute. But he couldn't resist. He slipped his low-heeled shoes off and put the high heels on again. Why was he doing this? If Mel caught him... It was the darn fantasy. And damn! He really needed some relief but bad! That was it in a nutshell. Every little thing was piling up on him because he needed relief. And still he was reluctant to take the heels off. He wore them out to the kitchen to quickly check on dinner one more time before going back to take them off again. The fantasy played heavily in his mind while he did it. But before he could get back to the bedroom to remove them, Mel breezed in quickly. "Whew! I made it!" she declared happily as she came in. She sniffed, "Mmmm. Something smells good. Don't tell me what it is. Surprise me." She quickly looked him over as she set her purse on the table by the door. Then she stopped, totally surprised. "Sissy! You're wearing heels? Why?" Chad could feel himself blushing. "I was just going to change them." Mel walked up to him with a wicked smile on her face. "You like them, don't you!" "Yes, Mistress," he said nervously as he dropped a quick curtsey. "You've been thinking about what it would be like to not be able to wear anything but high heels, haven't you!" He dropped another quick curtsey. More nervous than ever, he repeated, "Y-yes, Mistress." Then her manner quickly changed. "Take them off! That decision is mine, not yours." Then she smiled wickedly at him. "I'll leave it up to you to worry about that for now. Will I? Or won't I?" She left to wash up in the bathroom. Why was it that almost everything she did lately turned him on so much? Even when she was being cruel, she was still fueling his fantasies unmercifully! A few minutes later there was a knock on the door. "Answer it Sissy," Mel called from the bedroom. Nervous and praying that it was Sandy and Cassie at the door, he opened it. Thankfully, it was. "Hi Cassie," he said with a quick curtsey. "Hi Sandy," he said with another curtsey. "Sissy, you look really nice tonight," Cassie said as she walked through the door. Sandy stopped in the doorway and peered closely at his makeup. "It's getting a lot better. It's a shame we didn't get much past your foundation though, but overall, I'd say we accomplished something earlier." She walked on in and he closed the door behind them. "Hi," Mel said as she came out of the bedroom. Chad headed for the kitchen while the women talked. Quietly and efficiently he dished everything out onto the plates and lit the candle on the table. He poured the wine for each of them and checked to make sure everything was as it should be. Perfect! He headed into the living room. At the first opportunity he interrupted them. "Dinner is ready." "Good, I'm starving!" Cassie declared. "It does smell good," Sandy noted as she got up from the couch. The three women sat down at the table and Chad went back by the sink to stand out of the way and watch in case they needed anything. "It all looks so good," Sandy said as she grabbed her fork. "And the best part is that it's something out of a diet cookbook I just bought," Mel replied. "Really?" Cassie exclaimed. "But it's so good!" "Mel, you are so lucky to have him," Sandy declared as she stuffed a fork full of food into her mouth. "Speaking of which!" Mel said, her voice holding and edge of sternness. She looked angrily over at Chad. "Sissy! Where do you belong?" Chad was taken totally by surprise. He couldn't believe that she wanted him in the corner again. But obviously she did. Reluctantly, he went back to his corner to stand scrunched into the wall. He could hear Cassie and Sandy laughing hysterically behind him. He couldn't really hear what they were saying anymore since he was so far away and facing the wall, but it didn't really matter. He was once again stuck in his boring old corner! He stood there for a long time with nothing to occupy his mind. He desperately tried to listen to what the women were saying, but mostly he had a very hard time of it since they weren't speaking directly to him. The most exciting part came for him when he realized that he had to pee again. That at least was something he could easily concentrate on. How long could he hold it? He couldn't look at his watch or a clock so he began counting seconds in his head. Mentally calculating how many seconds went into each minute that passed. It almost became a game for him as he stood there with his eyes closed trying to be still. As his counting passed the ten minute mark, he began to doubt his minute calculations. It seemed like a lot longer. They had to be finished with dinner soon! Unfortunately, it was getting harder and harder to hold back on his peeing - probably because it was all he had to think about it. Without thinking, he started struggling against it and in the process took a tiny step back to shift his weight and relieve his aching legs and feet. "Sissy! Stand still!" Mel yelled. She watched till she was satisfied that he was back in the corner the way he was supposed to be. Sandy and Cassie both turned around to look at him. "Don't ruin your dinner over him," Cassie cautioned. "This is too good for that." Mel smiled at her. "Are you kidding, yelling at him is my favorite part." All the women laughed again. As they gradually finished eating, they kept turning around more and more often to watch Chad standing in the corner. Every time he moved in the slightest, Mel would yell and he would get still again. Eventually, they were no longer eating and Mel had opened up a second bottle of wine that they were now working on. After a while, they all fell silent while they stared at Chad and drank their wine. "You know," Cassie finally said. "Please don't get me wrong about this, but while I really like the maid's outfit, to me, it gets boring pretty quick." Mel was surprised at that, but before she could say anything, Sandy added, "Yeah, I know what you mean. It's like... you know, last week when we watched him running back and forth in that cute little onesie, that was like one of the highlights of my life. But now... well, he looks great and all. Maybe too great. But it does get a bit boring." Mel wasn't sure what to say. Having Sissy as her maid had been her biggest dream for the last few days. She loved it! The three women stared at Sissy for a while more. She saw him move his feet again. "Sissy!" Quickly he put his feet back where they belonged again. But she finally realized that maybe Cassie and Sandy might be right - at least from their perspective. Sissy looked great like he was now, and she loved seeing him like that, but for Cassie and Sandy, that "something-special" spark seemed to be missing. "Maybe you're right," she finally admitted. "But what should I do about it?" "I don't know," Sandy replied, "but I really loved the baby outfit too. God, it must have been so humiliating. But this, what he's wearing now well, it's almost respectable." "Of course there's always the French maid thing," Cassie suggested. "Yeah," Sandy agreed, "guys are always hot for that kind of thing." "Yeah but French maids don't really turn me on," Mel replied. "But it is a good suggestion." "Why don't we check the internet," Sandy suggested. Mel brightened. "That's a great idea!" All three women picked up their wine glasses and headed into the living room where Mel set up her laptop on her desk. "Sissy," she finally said. "Go clean up the kitchen!" Chad was ever so glad to finally be able to move away from the corner again. He bent his knees painfully to get the circulation moving again. Thank God he wasn't wearing high heels! The darn women had sat at the table for an eternity while he stewed in the corner! Talk about cruel! He could hear them all laughing now as they sat around her computer. He wasn't at all sure he wanted to know what they were laughing about. "Oh! I love that one," Cassie squealed excitedly. "And you've got to get the shoes that go with it too!" Mel duly added everything they decided on to the website's shopping cart. When they were done, she entered her payment information and finalized the order. That was the third website they had bought things from for Sissy so far. The amount was adding up, but Mel didn't care. "Oh! You want to see what I've been looking at for a while now for him? I was planning on buying them later this week." She navigated to the web page she wanted. "Breast forms!" Sandy and Cassie screamed together. "Why wait?" Cassie asked. "Get them now!" Mel turned back to her computer and did just as Cassie had suggested. It was so much fun! Chad, in the kitchen, felt like he was forgotten, while at the same time not forgotten. He knew everything the girls were discussing was for him. He knew every bit of it would be painfully humiliating. But the only words he had heard clearly were "breast forms." He shuddered, but realized that it was only logical. She had been making him pad out the breasts of his girdle since the beginning anyway. So in reality, breast forms were no big deal. Forgotten, but not forgotten. He was the maid tonight. A fixture to be there and work, but not be in the way. Invisible. Alone. Used. He hated it. He loved it. The misery of the situation also fueled his fantasies. Damn he needed some relief! Unfortunately, he went back to thinking about Mel training him so that he could only wear high heels and nothing else. Why should he find that so appealing? Why did he find any of it appealing? He just did. He accepted it. He enjoyed it. All of it. The Bet Chapter 17 (Monday - week 3) His dreams were total confusion. He was confused. The situations and images were confused. One minute he felt lost, alone, adrift, forgotten. The next he was overloaded on sexual want and need, feeling the punishing pain of his chastity device even in the dreams of his sleep. Constantly changing dreams. Dreams where he was proud of himself... followed by dreams where he was completely unnoticed... followed by dreams of being stuck in high heels forever... followed by dreams of playing pool on his new pool table... followed by dreams where he was wetting himself uncontrollably. Back and forth the dreams flashed. Faster and faster. Exploring and changing emotion after emotion. The situations and feelings came at him faster and faster, stronger and stronger, mixing the emotions so that he could hardly tell them apart. Until they all rolled themselves up into one loud crashing crescendo... that was his pink alarm clock suddenly blaring loud rock music into his room to wake him up. He awkwardly rolled over on his blow-up mattress and stared at the ceiling while he tried to clear his confused head. His chastity device was hurting him badly and he tried to figure out why. It must have been something he was dreaming. Pity he couldn't remember it though. He struggled to his feet and turned off the music. It was Monday. He'd have to go to work... again. The next thing that fully made it through to his sleep fogged brain was a question. What instructions had Mel left for him during the night? Only one way to find out. He began slowly waddling towards the kitchen. As soon as he began walking, the urge to pee hit him. He almost let it out without thinking, but he caught himself just in time and with a modicum of effort got it fully under control. What a strange night last night had been. He had cooked dinner for the girls, and then they had ignored him... completely... as if he wasn't even there. No thanks, no praise, no acknowledgement of any kind! For hours! After they finally released him from his corner, he had cleaned up the kitchen and then just waited. They never even spoke to him. The only time anyone even looked at him was when Mel came through to get yet another bottle of wine. She didn't even ask him to get it for her... as if he was nothing more than an appliance in her kitchen that she didn't need just then. Like a toaster. And when Sandy and Cassie finally left, Mel sent him straight home too. She didn't shove one of her stinking suppositories up his butt, heck, she didn't even rediaper him or give him any instructions. Nothing! Just a "See you in the morning," and that was it! Weird! As he reached his kitchen he got huge shock. There was no note! Nothing! He searched the floor in case it might have fallen off but he couldn't find anything. He felt panicked. She had never done this before! What was he supposed to do? He literally waddled in circles in his kitchen trying to figure it out. He couldn't remember her telling him anything that he should have remembered. Should he get another baby bottle like he always did, or didn't he have to bother? What clothes did he have to wear? Fearful, because she always checked to make sure he had finished the required baby bottles, he pulled one out of his refrigerator and sat down with it in his living room chair. Once again, he felt ignored and adrift. Mel woke up with her mouth tasting like dried cotton... well, maybe not that good. Her head felt like it was stuffed with wool. She dragged herself carefully out of bed and went into the bathroom to brush her teeth. Too much wine always did this to her. She hated herself for it. No matter how much fun she had the night before, she always paid for it then next morning. It was the wine... every time. Brushing her teeth helped some, but not as much as she would have liked. She plodded to her coffee pot and turned it on. It wasn't till she stood there watching it dripping into the pot that she finally thought about Chad. Dinner had been great last night. He had done really well. Everything had been perfect. He was really on his way to becoming her greatest fantasy. In some ways, he was already there. She loved seeing him in his formal maid's dress. But Cassie and Sandy had been bored with it. Yeah, she understood that and yeah they were right. What an evening she had had buying him new outfits. She didn't want to think about how much money she had spent last night. A small fortune probably. Not that it mattered. Of course, she also couldn't really remember what she had bought him either. She had been in too much of a hurry to bother printing anything out. Stupid! But she guessed that any packages that came in now would be like wonderful surprises. She'd just have to wait and see. That was always fun. She suddenly remembered something else, she had forgotten to leave him a note with instructions last night. Stupid again! Too much wine! Well, she'd just have to see how he showed up later. If she didn't like what he was wearing then it would really be her fault, not his. Of course, he didn't have to know that. She could yell at him about it whether it was her fault or not. Feeling a little bit happier, she poured herself some coffee. Chad got out of the shower and dried himself off. Should he wear two diapers like she always told him, or didn't it matter. Deciding to be cautious again, he went for the double diapers. Besides, he would worry a whole lot less about leaking that way. But how about everything else? Even though he was holding back now, he still had to do everything in his diapers. Heck, he didn't even think about using a bathroom anymore - he sometimes found that very convenient! So he added the plastic panties because they provided a lot of added protection against leaking. Did he need the all in one girdle? He looked down at the front of his diapers. They were a bit bulky and there was a bit of a bulge where his chastity device stuck out. Sighing he pulled the all-in-one girdle on too because it not only hid his chastity device further, but it also kept his diapers from being so obvious when they got wet. He was fairly sure it also kept the smell contained a lot more if he happened to mess himself - which the more he thought about it, was quite likely. Did he need the pantyhose too? He didn't have any socks to wear with his shoes and he could easily go without. But the low-heeled shoes were a bit tight on his feet and the pantyhose made them easier to get on and a lot more comfortable... so he pulled the pantyhose on as well. Was there anything he could go without? He searched his closet. He glanced through the button down shirts that he usually wore to work. But before he selected one, he fingered the new blouses he had. Heck, everything else he was wearing was female. Nobody would even care if he wore a blouse today instead of one of his male shirts. But wearing anything male was still a coveted privilege to him, so he opted for one of his old shirts instead. There wasn't much choice when it came to the pants or shoes. He wasn't about to go to work in high heels - even though thinking about it slightly rekindled the fantasy he had lived with all day yesterday. He pulled on a pair of women's pants and slipped into his low-heeled shoes. But how about his makeup now? Would she let him go to work without it? She had been so adamant lately about him working on it, and yesterday's session with Sandy had really helped - as far as they got. It would be nice to go to work again without makeup, but he had also been wearing it all last week too. The way he was dressed already, he was guessing that by now he'd probably attract more attention at work if he wasn't wearing any. He opted to go with just the foundation and eye makeup like he had last week, only he'd try to do a better job of it today. When he was done with his makeup he looked at everything spread all over his bathroom counter. It looked like a lot of stuff, and he hadn't really used that much. He thought of the things still in his purse. Nobody had told him what things he could leave home now. Deciding to lighten the load in his purse some, he began removing the items he never used and only put in the things he knew how to use. Then, just in case Mel might check, he added a couple of different lipsticks too, even though he wasn't wearing any. He had no male watch anymore so he struggled to attach his new one around his wrist and hook the security chain. Why did they have to make them so hard to fasten? Why did they have to make the dials so small too? Women had no sense of what was practical! Kind of like pockets in pants. Such a basic concept! Finally, he wondered about his new necklace and ring. Did he really need them? He wasn't sure. He hoped not. Just to be on the safe side, he pulled another baby bottle out of the refrigerator and drank it while he considered that very question. Mel glanced at her clock. It was almost time for Chad to arrive. How bad would he be? Would he even bother to drink anything before he came? She seriously doubted it. The knock came on her door and she opened it immediately. "Good morning, Mistress," Chad said as he dropped a quick curtsey. "Good morning, Sissy," she replied as she always did before she let him in. Was it her imagination, or did he look a bit nervous and worried this morning. He probably was worried. She closed the door and began looking him over carefully. He appeared to be dressed suitably, much better than she expected... appeared to anyway. She took the plastic bag he was holding and opened it. Two empty baby bottles. The tape around the bottle caps was still intact. She wished it had been more bottles in the bag, but it was good enough. She looked up at him. "How many diapers are you wearing Sissy?" "Two, Mistress," he replied with a small curtsey. Watching him curtsey with his answer sent an immediate thrill through her. "Are you wearing your girdle?" she asked. "Yes, Mistress," he replied with anther curtsey. "Good." But she reached out and pulled the neck of his shirt aside just to check. Yes, the girdle was there. But something else wasn't! "Sissy! Where's your necklace?" She checked his hand. "And your ring?" Now he looked really nervous. "I left them home," he replied with yet another curtsey. She moved up right into his face. "I don't ever want to see you without them!" She saw the panic instantly increase in him and was pleased. She stood back shocked one more time. "And where for heaven's sake, is your pacifier?" This time he didn't curtsey. He was clearly panicking and worried. "I forgot it again," he admitted. "Go get them!" she said. "And don't come back till you're dressed properly!" She almost laughed as he practically flew out the door. She had been surprised, he had done really well all by himself with no instructions. In fact, pushing him a bit just then had been a lot of fun. Clearly he didn't need as much close supervision anymore as he used to. Which meant that she had made more headway with him already than she had thought. She felt very satisfied about that. Of course, that also fell right in line with her plans for him for the week. Chad came hurrying back in, this time with the ring on his finger, the necklace around his neck, and the ridiculous pacifier stuck in his mouth. As she closed the door behind him again, he dropped another curtsey, "I'm sorry, Mistress," he mumbled through the pacifier. "You should be!" she berated him. But inwardly, she was nothing but pleased. Once again she subjected Chad to having to eat a bowl of baby cereal with the tiny baby spoon while sitting on her kitchen floor. Once she had finished putting two fresh baby bottles into his diaper bag, she stood in her kitchen and watched him trying to eat. She had to control her laughter as more and more of the cereal fell off the spoon and wound up dripping down from his face. If he wasn't careful, he'd have to redo his makeup again. She may have felt lousy from last night's wine when she got up this morning, but watching Chad was definitely putting her in a much better mood. When he finally finished his baby cereal, along with two more bottles of her tea, she wiped his face off herself as if he was a child. A bit too much of his makeup came off around his mouth. She glanced at her clock, there was plenty of time for him to fix it, but she decided on another idea instead. "Uh oh, Sissy! You're such a messy eater that your makeup needs fixing now. But there's not enough time to repair it here. You'll have to do it when you get to work." "But I can do it quickly," he protested. "No, now go! I have other things to do this morning." "But... can I fix it at my place?" "No. It's time you started to learn to do it while you're out anyway. Why do you think I have you carry it all with you? You do have all the makeup you need, don't you?" "Yes, Mistress," he replied. But she was already heading for his purse in the living room. As Chad climbed to his feet, he really hoped she wouldn't say anything about there being not as much makeup in it as there used to be. She was already poking through his purse when he got there. "Remind me the next time we go shopping that you need a new wallet. This thing is ugly." He didn't answer. "I see you've cleaned a lot of stuff out, but it still looks like you've got at least the basics. So that will be all right." Chad felt a huge wave of relief. While she was closing his purse for him, he took a second to glance at his face in the mirror she had by her door. Yeah, he could see where the makeup had gotten smeared and needed fixing. It shouldn't take much though. She noticed him checking his face in the mirror and smiled. That was a good sign too. "Okay, Sissy. Off to work. And don't forget to fix your makeup when you get there. I'll ask Cassie about it later." Chad sat at his desk and stared at his computer screen. Even this morning, Mel hadn't mentioned dinner last night. Wasn't it good enough? Had he had picked the wrong recipe? He meant to ask her about it but had forgotten with everything else going on. Okay, he had just chickened out! He pulled up his calendar and looked at it. Two weeks of the bet were down and still a very long time to go. He couldn't believe all the changes she had made in him already. But as to the terms of the actual bet... well, he was seriously back on track now. If he was going to win this thing, then he had to find a way to keep on track and keep her from knowing it. She could dress him up and make him play her little maid games all she wanted, but in the end, she would be the one dishing out the money - and lots of it. He spent a long time staring at the calendar on his screen and thinking about the terms of the bet. It would be so humiliating though to someday find himself completely incontinent and have to wear diapers all the time. So deliciously humiliating. So why didn't he just do it? This was the perfect opportunity. He would really love it. But there just seemed to be something holding him back. Even though he wanted it badly, he couldn't seem to let himself go and just do it. It was the bet, he finally decided. If it wasn't for that, he would probably be loving everything she was doing to him... and more. But because of the bet he felt like he absolutely had to win. The odds were in his favor - heavily. And he was completely back on track now. But it had been close. He had been really shocked to find out this past weekend how much control he had already lost. Almost all of it. And that was after only two weeks! The odds might be heavily in his favor, but if he wasn't careful, he could really lose! He wanted it, but he didn't want it. No, he wanted the humiliation of it, just as he was frightened of the humiliation. Which amounted to the same thing. Bottom line... his darn competitive nature didn't like to lose. Just as he now knew that hers wouldn't let her lose either. Very well, the bet was on and there was still a long way to go. He needed a plan. Something to keep him on track so he wouldn't stray. He opened his spreadsheet program and began entering a column of dates. The bet had started on the second day of the month. Thirty one days this month and thirty days next month. Sixty one days of hell before his "testing" would even begin. Almost nine weeks. Mel had tried to make it an even nine weeks but he had refused. He had suggested that they make it an even eight weeks but she had refused that. They had settled on the exact number of days of the months. Once the dates were all in his spreadsheet, he started a "Days to Go" column that counted down the number of days left until his final testing would begin - 46 as of today. In the next column, next to the date for yesterday, he entered fifteen minutes. Because that was how long he figured he had managed to hold back from peeing into his diapers yesterday. Not really very good, but compared to Saturday, it was an eternity. From now on, he would try to time himself and his best times would be recorded. His goal was to increase the time every single day to the end. He could do that easily, especially if he was careful to make sure that Mel never found out! Mel checked her messages between clients and saw one from Will Grey. She had been waiting to hear from him about the case. She dialed his number. "Hi Will, it's me." "Mel! Hey listen, I just wanted you to know that we just made a sma