The Bet - Chapter 20 free porn video

The Bet by Karen Singer Chapter 20 (Thursday - week 3) In her dreams, she was a horrible monster, a Doctor Jekyll and Mrs. Hyde, whose split personalities were constantly at odds with each other. Part of her tried so hard to be kind and loving, while at the same time, the other half of her was committing atrocious acts of evil - acts that she delighted in completely. Her two halves battled for control, but more and more the evil half was winning. They were disturbing dreams - more so because even in her dreams, she realized that the evil held a distinct fascination for her. She felt confused, unable to help herself. Do one nice thing for someone, then turn around and do two things that were cruel! Over and over again. She hated it... she loved it... Evil wasn't what she wanted to be, yet she continued to commit act after act of cruelty - and she laughed at each one! Her alarm clock buzzed a long time before she came fully awake, chasing the evil dreams away, erasing them from her mind - fortunately. She didn't even bother throwing her robe on as she went into her kitchen. She only knew that she needed coffee. Was she becoming addicted to it? She didn't really care. She just wanted a cup to clear her brain! Chad's whole body jolted awake at the sound of the loud music blaring into his room from his pink clock radio. God! Morning already? What had happened to the night? It felt like he had just fallen asleep. He rolled over and struggled to his feet. He could feel that his diapers were over-loaded again, not just from wetting them, but from the damn suppository that Mel had shoved up inside of him. A horrible mess! He barely remembered waking up when it happened last night. But then he had to stop to think... after that, once he had finally fallen deeply asleep, he didn't remember waking up at all to wet himself. Not once. Yet his diapers felt like they were soaked to overflowing. That was a troublesome thought. For the second day in a row now, he had woken up with soaked diapers and didn't remember wetting himself that much. He also realized that as much as the idea of it thrilled him, it was going to cause him trouble with winning the bet. But he didn't know what he could do about it. He had to sleep at night, and Mel's stupid bottles of tea kept him peeing all too frequently. It was too early in the day to wrestle fully with that problem. He headed to his kitchen to see if she had left him a note. It was there, on the counter where he hoped it would be. His heart soared a bit at seeing it, even though he really didn't care much about what was in it. She had cared enough to leave it for him and that was all that mattered. Sissy, First bottle. Shower and shave (don't forget your legs - I'm not going to mention it again). Second bottle. Get dressed. Third bottle. Nothing. Nothing really at all. He realized now why she had stopped leaving the notes before, he no longer needed them. Yet he wanted them. For some unknown reason, they were important to him. Even notes like the one she had left for him today. He grabbed his first bottle and headed for his lonely chair to sit and drink it. As Mel's coffee began to kick in, so did her thinking about Chad and what had happened last night. Certainly not what she had intended. With her robe finally wrapped around her, she sat with her coffee in one of her living room chairs and pulled her legs up under her. She took another sip and leaned her head back. What was she going to do about him? That was her ultimate question. She pretty much knew what she wanted from him, but she knew more than ever now that even this kind of relationship was a two way street - perhaps even more so than a normal relationship. A relationship? Could she call it that? Yeah, it was a relationship for sure, just a type she had never thought of before. A week ago she had begun training him to never get hard so he could pee whenever the need hit him. In the process, she found that she really loved the unintended consequence of him being denied the basic ability to receive any pleasure at all - while she herself received all the pleasure. She smiled at the thought. It really was deliciously wicked - yet she loved it. But last night she had purposely tried to stimulate him... okay, she had left the damn device on him so he couldn't get hard just to see how he was really reacting to the anal play... but in the end, she had wound up completely ruining his ability to have an orgasm. She hadn't meant to and she felt bad about that - especially since she had promised him he could have one. Yet the fact that he couldn't orgasm at all seemed to hold such a huge fascination for her. So what was it that she really wanted? She realized that as of last night she was sending him mixed signals. That was never good - no matter how you tried to justify it. Mixed signals... not good... why was she doing it? She took another sip of her coffee. Why? Why? Why? That was always the one big question in her life. With Chad, there were lots of reasons why... too many. And that was part of her problem this morning, too many reasons and too many thoughts about Chad... all of them leading back to her original question. What did she, herself, really want with him? Chad faced his closet door, afraid to open it. Before, when he had started wearing the women's pants and shoes, Mel had taken their male equivalents away from him by wrapping them up in layer after layer of her cling wrap. Yesterday he had worn a blouse to work for the first time. Would his male shirts be taken away now? He hoped not. He hadn't noticed any more of her cling wrap in his closet after work yesterday. He opened the door and looked in carefully... and breathed a sigh of relief. All his male shirts were still hung up where he could get at them. Yesterday had turned out to be a nightmare after he had decided to wear the blouse. How was he supposed to know that the blouse he had selected needed that much padding in the cups of his girdle to make it look right? Okay, he should have realized it easily, but he hadn't. Because he could, he pulled down one of his male shirts to wear and put it on - he wasn't going to make the same mistake he did yesterday. But then he turned to his pants - women's slacks. He had only one pair left in his closet because all the rest were in Mel's laundry hamper. This pair was his new pair - the slacks with the longer length. As he pulled them on over his diapers and pantyhose, he noticed that they were way too long, he was standing on the bottoms of them. He slipped his low heeled shoes on and took a few steps. He quickly felt a slight tugging at his pants as his heel caught under the bottom of them. They were still too long for the shoes he was wearing. He had a feeling it would happen. It was why he had avoided wearing the new slacks before. They had to be worn only with higher heels... much higher heels. Having no other choice, for the first time, he put his low-heeled shoes back into the closet and selected a pair of his highest heels to wear to work because they were the only ones that would keep his pants legs from dragging on the ground. Once again, it felt like he had lost something. It also felt a bit like things had yesterday, when he had worn the blouse to work... it felt like he was taking a huge chance by doing it. Was he? Mel watched the clock, waiting for Chad to arrive. By her estimation, he should have only one pair of slacks left in his closet, the new ones. Would he be wearing his higher heels today? And how about a blouse? He had worn one for the first time yesterday. And for that matter, how about padding the cups of his girdle... and his makeup? Too many questions. Fortunately, there were only a few moments more till she would have some answers. The knock came at her door only a few seconds late. She opened it. "Good morning, Mistress," he said as he dropped his accustomed curtsey. She took in the entire sight of him quickly. Her face fell just a bit at the sight of his male shirt - but then she had been betting that he would choose one today. "Good morning, Sissy," she replied and stood back out of the way to let him in. She quickly noticed his new slacks, the heels on his feet, and the makeup on his face. She instantly felt much less disappointed. When she had closed the door, she took the bag of empty baby bottles from him and checked it - perfect, but then she didn't expect anything less. She turned her sight on him and started looking him over carefully. "It's about time you wore those slacks," she commented, trying hard to hide her amusement. He made no reply. For the first time, his makeup was fully done and actually looked pretty good. Maybe Sandy didn't need to teach him anything else. His male shirt was an obvious disappointment as was the lack of breast padding, but then she had never specified either of those for him. Those things were still his choice... but for how much longer? His jewelry was all in place and his hair was neatly combed - she made another mental note to talk to Cassie again about teaching him to fix it better, maybe tonight. Everything about him was perfect - except for one thing. "Where's your pacifier?" He rolled his eyes. "I'm sorry, Mistress," he said as he dropped another curtsey. "I forgot it again." She shook her head. "One of these days I'm going to remember to punish you good for forgetting it so much... maybe one day very soon!" "Yes Mistress," he replied with yet another curtsey. "Come on, Sissy," she said as she turned toward her kitchen. "It's breakfast time." Chad set his purse and diaper bag under her table by the front door and followed her. She walked straight to the highchair and pulled the tray off and waited for him. He stopped for a moment and stared at the chair. Ugh! He hated the thing - yet at the same time, he loved it! It was so demeaning to have to sit in to eat from, while at the same time, it fueled all too well his unrelieved fantasies. Having no other options, he climbed up into the chair and held his arms up out of the way while Mel replaced the tray. A moment later, she fastened the bib around his neck. "Wasn't it nice of Sandy to get you this pretty bib?" she asked. "I should have gotten you some before. I think it's much better than that nasty old dish towel we were using." He looked up at her and rolled his eyes slightly as he searched for a way to answer her. But he couldn't think of anything that would keep him out of trouble so he said nothing. A minute later, he was spooning awful tasting baby cereal into his mouth with the tiny rubber coated baby spoon. Mel leaned back against her counter and watched him eating. It was so much more rewarding seeing him eating now in the highchair and wearing the bib instead of having him sit on the floor. He looked all that much more ridiculous... and she loved it! She didn't really like being a cruel person, but damn it, they were his fantasies! She just happened to enjoy being on the other side of them. Robin hurried into work, technically a few minutes late - not that anyone would really care or even notice. As she hurried past Chad's desk, she quickly saw that he was still booting up his computer, so he hadn't been all that early either. "Hi Chad," she called as she hurried to her own desk. She dumped her big bag on her desk and pulled out her mirror to check her hair. She touched a few strands and returned her mirror to her bag and crammed the whole thing into her bottom desk drawer. She hit the power button on her computer so it could start booting up. While she waited, she wandered over to Chad's cubicle. "Hi Chad," she said again as, this time, she stopped for a minute to talk. Chad turned around in is seat and smiled. "Hi Robin. How's things today?" "Ugh! What a morning! The baby was up all night crying. I think he's coming down with a cold. He was a real handful this morning!" "Oh," Chad replied. "Sorry to hear that. Did you still take him to daycare?" "Yeah, I don't think he was all that bad this morning. I just hope I don't get a call from them later." She looked at him quizzically. "Hey Chad, why aren't you wearing a blouse today? You're back to your old stupid male shirts again." Chad looked down at his shirt and shrugged. "After yesterday, I thought this was a lot better. Besides, I don't have to worry about how much to pad my breasts." Robin laughed. "Okay, you've got a small point there, but it still looks dorky. Your makeup looks good today by the way. Much better! And new shoes?" Chad looked down at his feet and stretched his leg out a bit, showing more of his high heeled shoe. "Not really, just different. I've had these a while." "You have?" Chad blushed. Without meaning to, he had just confirmed that he had been into cross-dressing for a while now. "Yeah, sort of," he admitted sheepishly. "I had to wear these today because the pants I have on are too long without them." "Stand up and let me see." Chad got out of his chair and stood so she could see better. "I think I'd be happier with these pants if they weren't so long." "No, they're perfect. Very much in style. Have you had the pants for a long time too?" "No, I got these last weekend." Robin nodded. "Let me see you walk a bit so I can see it all better." Chad didn't really understand why, but at least she wasn't being too pushy today, just nice. He took a few steps out into the hallway, then walked back into his cubicle again. "Yeah, they're really a good length with those shoes," Robin stated, still watching his feet. She looked up at his face and smiled. "I see you really don't have much trouble walking in them. You must have had them for a while." Chad blushed again. "Yeah, well..." Robin chuckled a bit. "It's okay, Chad. I just wish you'd finally come out and say that you're doing all this because you like it and want to... instead of all this 'it's complicated' crap!" Chad sat back down in his chair. "Well, that's just it, Robin. The reason I'm really doing it all is complicated." "So explain it to me." He shook his head. "I can't." Robin just rolled her eyes. It was time to change the subject. "Hey, so have you heard any feedback on our project yet?" Mel handled several clients in her office, then had to run off to a mercifully short meeting with a judge before getting back to her office again - all of it well before lunchtime. When she got back to the office, Andrea pointed to a large brown box on the floor next to her desk. "That just came in for you a few minutes ago." Mel looked at the box as she set some paperwork on Andrea's desk. "What is it?" she asked. "I don't know. It's just got your name on it." Mel looked at the box quizzically. She didn't recognize the name of the company that had sent it. She picked it up, it wasn't all that heavy. She gave Andrea a wondering look and carried it back to her office. She set it on her desk and started attacking the box with scissors to open it. She finally pulled the lid of the box open and stared in disbelief as volumes of tightly packed white ruffles tried to escape out of the top of the box. She couldn't help it, she laughed out loud! Obviously, it was one of the things she had ordered over the internet with Cassie and Sandy last weekend. No wonder she didn't recognize the company. She had been a bit too drunk that night to care about what she was ordering, let alone who she was ordering from. She pulled at the ruffles to take everything out of the box. There were so many ruffles covering everything that it was hard to see what it was - let alone find the top. She held it at arms length - the only way she could even have a chance to see it clearly. Oh God! She couldn't wait to see how it would look on Chad! There was a small knock on her door, Andrea's knock. "Come in," she called as she turned around to face the door. Her door opened and Andrea started to come in. "Hey Mel, these papers..." But Andrea couldn't say anything else as Mel proudly held the garment up so Andrea could see it. Andrea's eyes were as wide as saucers and kept going back and forth from Mel's face to the huge mass of ruffles. "Obviously, that's for..." "Yeah," Mel replied trying to stifle her laughing again. "And I can't wait to see him in it!" Mel couldn't contain her laughter any longer and let it out fully. As did Andrea - to the point where they were both going to have to fix their makeup. Robin stopped at Chad's cubicle on her way past. "Hey Chad, I'm going to break. Do you want to come?" Chad turned around in his chair and shook his head. "No thanks. I don't think so." Robin shrugged. It was the reply she had expected, but she had wanted to try anyway. "Suit yourself," she replied and continued past. Chad turned back to his computer and stared at the project on his screen. After a few moments, when he was sure that Robin wouldn't be back anytime too soon, he minimized his work and opened up his spreadsheet for the bet. The count was down to forty-three days now. An eternity. But at least the number went down every day. He looked at the column where he was keeping track of how long he was able to hold back. Yesterday he had put down thirty minutes. His problem though, was that he didn't really know how long he had held it yesterday. He hadn't bothered to keep track at any time. Thirty minutes had been a conservative estimate though. So today he put down thirty-five. Feeling like he was still well on his way to ensuring that he couldn't lose, he closed the spreadsheet. But when he opened his work project again, he just stared blankly at the screen. He was wetting himself in his sleep now. That wasn't good - as far as the bet went. It wasn't really all that bad either. The bet stated that he had to be completely incontinent, and he was fairly sure that just wetting himself at night wouldn't let him lose - especially since he now had complete and perfect control during the day. Still, it was troubling... while at the same time, he found it fascinating and all too stimulating. He was wetting himself in his sleep now just like a baby - with no control at all. Mel had actually caused him to do that. She had really done it! But that alone wouldn't win the bet for her. It was a good thing that he was keeping track of everything else now or things would really get out of hand... and he could lose all too easily. It was hard to believe, but he supposed it could still happen. Forty-three days! Way too many! He would have to be very careful. He felt the slight need to pee hit him yet again. He had only drank five bottles of Mel's tea since he got up. The darn stuff kept him peeing constantly, which didn't help matters. He had just realized that he had to pee. This time he glanced at his watch and took note of the time. It was time to find out for sure how long he could hold it. Twenty minutes later, he couldn't stand the pressure anymore and had to let it out. He checked his watch. Not good! But then all those bottles of tea had to go somewhere. There was still probably too much of it in his system. He'd keep checking himself carefully all day. He knew he could do a lot better than that! It was almost lunchtime. Robin already had her bag out on top of her desk and was ready to go. Chad was going to that gym every day. She knew he was meeting with one of the trainers for a little while, but that was all she knew. Even the receptionist didn't know what they were doing. How could she find out more? Would he tell her if she asked? It was a thought that hadn't occurred to her before. Her face drooped a bit. He was all too closed-mouthed about everything odd in his life lately - which seemed to be his entire life. Still, what could it hurt to ask? She got up and walked around to his cubicle, he was just closing his project. "Hey Chad, want to go to lunch?" "No thanks," he replied. "Still the same date again?" she asked. He nodded - sheepishly she thought. "Look, Chad... I saw you going to the gym down the road yesterday. Is that where you're going again?" Chad was suddenly horrified. "You saw me there?" Robin was surprised. "Well, yeah. I mean, I had to drive right by it when I went to lunch!" There was no way she would admit to anything else. It made sense to Chad. Someone was bound to notice him eventually. But that didn't mean he had to tell her anything. Not really. "Yeah, I'm going there again." "But that's a women's gym. Isn't it?" "Yeah. So?" "So what are you doing there?" "Meeting someone. Okay?" he replied with a bit too much anger. She was prying too much again! As she suspected, he wasn't going to tell her. She just shrugged her shoulders. "Okay, I was just asking, that's all. See you later." Chad watched her walk off. He had been spotted now going into the gym. At least Robin didn't know what he was really doing in there. He wondered if Cassie could meet him somewhere else instead - like maybe his apartment. For that matter, maybe Mel would let him change his own damn diapers at lunchtime! Robin watched as Chad pulled out of the parking lot and headed towards the gym. She purposely turned the other way. She knew where some of her friends were having lunch and it was about time she started joining them again. But halfway there, she had an idea about Chad and the gym. Unfortunately, it was way too late to try it today. But tomorrow... And wait till she told her friends! "Hi Sissy!" the receptionist called as he walked in. "Hi," he replied simply. The receptionist looked at him with a mock pouting expression. He sighed and dropped a quick curtsey and said, "How are you today?" The receptionist immediately smiled brightly. "Much better now." She giggled as she went off in search of Cassie. It was little things like that, Chad realized, that were making his life all that much more complicated. "Hi Sissy," Cassie's voice called out, way too loudly for Chad's comfort, as she got to the front. He dropped yet another curtsey as he greeted her, then followed her to the office in the back. As soon as the door was closed behind them, he said, "One of my coworkers has spotted me coming in here." "So?" Cassie asked. "So what am I supposed to tell her?" "I don't know," Cassie replied. "That's up to you." "Is there anyway we can meet somewhere else to do this?" Chad asked. Cassie shook her head. "Sorry. We're lucky to have what little time we do. This is one of the busiest times of the day for me." Chad was disappointed, but he understood. At least he had asked. He started getting undressed while Cassie dug into his diaper bag and pulled out one of the baby bottles. The sight of it made him feel the need to pee again. He quickly checked his watch so he could start timing himself. A few minutes later, he was laying on his back, sucking on his bottle, and concentrating on Cassie's hands as they worked the baby lotion all over as much of the front of his groin as the chastity device he was wearing would allow. It really was a wonderful feeling. The tea he was drinking was increasing his need to pee, but laying on his back seemed to help take some of the pressure away. If he wasn't trying to hold back so much, he would have wet himself before she removed his already soaked diapers, but he was trying harder today so he hadn't. The good news today though, was that while Cassie's hands felt great, he wasn't having to work as hard to stay soft so the chastity device wouldn't hurt him. Maybe it was his growing need to pee that was helping. Cassie pulled her hands away and smiled. "You're doing real well again." He pulled the baby bottle away from his lips slightly. "Thanks. I think it's getting easier." She patted his hip. "Roll over and I'll play with the other side just a bit. Okay?" He knew she really wasn't giving him any choice. And as much as he hated what she was about to do, he also knew that he really wanted it too. So many changes in his life. Where would it all end? He rolled over and pulled his legs up under him with his head lowered toward the floor - making his backside an all too easy target. But that was just what he wanted... now. Cassie began again by massaging him with the baby lotion, relaxing him totally... and he loved it. It was really sensual. As fantastic as Mel's touch had been last night, Cassie was really much better. He suddenly felt her beginning to play closer to his asshole again and he waited breathless for her to move her attention fully to it. Finally, her finger was there, pushing, then harder. He felt her finger go in. Why did he love it so much? It was all wrong! But he did love it! He couldn't seem to help it. He was suddenly moving in and out while she was doing the same with her finger. Fantastic! But the need to pee in him was still building - invading his reverie all too much. He tried desperately to push the invading discomfort away, but it was getting more and more difficult, especially since he had just finished more than half of the baby bottle of tea that Cassie had just handed him. The position his body was in now wasn't helping either as it put all too much pressure on his insides. And then it happened - all too quickly, certainly faster than he could stop it. Cassie pushed harder than she had ever pushed her finger before, trying to arouse him more. But it was more pressure than his bladder could stand. "Aaiiieee!" he exclaimed quickly as he suddenly felt a bit of pee escaping from him. "Stop!" Cassie quickly pulled her hand away. "What wrong?" she asked, concerned that she had somehow hurt him. Chad was rolling over and reaching under him, trying to grab his penis to squeeze it to stop himself from peeing, but the darn chastity device completely foiled that idea. The pee was still coming out of him and he couldn't stop it. Cassie finally saw what was happening and burst out laughing as she quickly grabbed one of the diapers she had handy to catch the remaining pee that was still coming out. "Shit! I'm sorry," he said as she held the diaper over his chastity device for him to catch the liquid stream. "That's okay, baby," she replied, still highly amused. "I guess we should have expected little accidents like that to happen." He said nothing. Instead he just rolled completely onto his back and stuck his bottle back into his mouth as soon as she had wiped up his messy puddle. He wasn't really having a good day so far with holding back. But it was really all different circumstances that were giving him the problems. His troubling thoughts were momentarily interrupted as Cassie had him raise his bottom again and then she stuck another miserable suppository up inside of him. And that was another problem, he realized. How do you fight the damn suppositories? As far as he could tell, it was impossible! Mel was getting ready to leave for lunch when her cell phone rang. "Hi Mel," Cassie's voice came over the phone. "Hi Cassie," Mel replied. "How did everything go today?" Cassie started laughing a bit. "Oh Mel, you should have seen it. I was playing with his backside again, you know, trying to get a reaction from him, when all of a sudden he started peeing all over the floor!" Mel burst out laughing. "He did?" "Really!" "Oh Cassie, that's good news. I wish I had been there." Mel was really elated. It was the first real sign that she was actually winning the bet. "Hey Cassie, if you think that was funny, wait till you see what I got in the mail for him." "Did some of those outfits you ordered finally come in?" "Yeah, one of them anyway." "Oh, I can't wait to see it!" "How about tonight?" "Like I said, I can't wait." Mel remembered something then. "It's going to have to be a bit later though, we have an appointment to go to first." "That's fine, Mel. Whenever. Just let me know." "Great Cassie. Oh, and when you come over, do you think you can teach him how to fix his hair properly? I'll get him a curling iron before we go home tonight." "Sure thing, Mel. I'd love to." "Great! See you later." It was late in the afternoon when Robin stopped by Chad's desk to talk again. "Hey Chad," she said as she walked into his cubicle. "How much does that gym cost where you go?" "I don't know," he replied. "I'm just meeting someone there." "Oh, well I though you might know since you're there so often." "No. I have no idea, but I can probably get you some brochures or something if they have any." "Yeah, that would be great. Thanks," she replied as she leaned back against his desk, obviously not ready to leave. He turned all the way around in his chair and leaned back a bit. He had been working hard all day, and with taking no breaks, he was ready to clear his mind. "How's your baby doing?" he asked, knowing that small talk was probably on her mind. She smiled. "Well, at least I haven't had a call from his daycare - yet." She looked down at his legs and the shoes he was wearing. "How are you making out in those shoes today?" He glanced down and raised one of his legs slightly and rotated his foot. "My feet are aching. I wish I had picked a pair of shoes that didn't buckle so I could slip them off easier." Robin chuckled a bit. "Now you know what we girls have to put up with all the time for you guys!" He looked up and smiled. He almost laughed a bit himself. But his feet really were hurting. It would feel so good if, just once, he could flex them a bit in the other direction and curl his toes. "At least I get to sit down all day," he replied. "Otherwise, I think I'd really be in some pain." This time, they both laughed together. "So Chad," Robin said as soon as her laughter had died down somewhat. "When are we finally going to get to see you in a dress?" "Never, I hope!" he replied good-naturedly. "Oh come on," she replied. "I'll bet you'd look soooo good!" she said teasingly. He shook his head and actually laughed a little. "Not if I can help it!" "Want to get some coffee?" she finally asked. Chad shook his head. "Not today. I don't really want anything at all today." "Really? Not at all?" He shook his head again. "Not today," he replied confidently. She shrugged. "Okay, I'm just going to grab one last quick cup for myself. See you later." Chad watched her walk out. Coffee wouldn't be bad, but he was finally doing a lot better on holding back from peeing. All of Mel's too many baby bottles of tea had finally worked their way out of his system and the one bottle he had from lunch seemed to be out of the way now too. The last time he had to pee, he had timed himself at almost forty minutes. That was really doing well and he was proud of himself over it. He was going to win this bet. There was no doubt at all! He squirmed just a bit against the messy load in his diapers from where the suppository that Cassie had stuck up inside of him had done its job. At least it wasn't as bad as it sometimes was. But the question was, what could he do about it? Even though he wasn't getting as many suppositories every day as he had last week, he was still getting several every day. And there was just no fighting them! As per Mel's text message, Chad drove straight to her office after work. He was looking forward to their relaxation therapy session later - the one and only real bright spot in his life. As he walked into her building, Andrea looked up and put a big smile on her face. "Hi," she exclaimed. "Wow, you're looking better and better. You know that?" Chad was a bit shaken by her remark. "I am?" "Yeah, really!" "Uh, thanks, I guess." Andrea laughed. "Come on, I'll take you back." Once again, Chad followed her back to the same unused but beautifully appointed office. Mel came in a few minutes later with a big smile on her face. "Hi Sissy," she said as she walked in. Chad got up from the leather couch he was sitting on and dropped a quick curtsey. "Hi Mistress," he replied. Mel started digging through his diaper bag and pulled out the one still full bottle. She handed it to him. "Drink this and I'll be back later to change you." Chad wasn't at all happy to have to drink the bottle, but he had been expecting it. His record at holding back for the day was still under forty minutes. He took the bottle and put it to his lips as Mel walked out again. He sat back down on the comfortable couch. The minute he started drinking, the urge to pee hit him again. He checked the tiny dial on his watch to note the time. By the time that Mel came back, he had long finished his bottle and was now walking around the room, trying to keep from peeing. His need was so great that he couldn't sit still on the couch any longer. His discomfort was further emphasized by the mess still inside his diapers from the suppository earlier. "Okay, Sissy, let's get you changed," Mel said as soon as she came in. As she began pulling diapers out of his diaper bag for him, he began getting undressed, then he stopped. He really had to pee badly and didn't want to do it too soon in the fresh diapers. He let it out while he just stood still. The feeling was pure heaven and he closed his eyes. It felt so good that he decided that when this bet was over, he was still probably going to stay in his diapers. Maybe forever. But before he could seriously consider that, he had to win this bet first! "What are you doing?" Mel asked, seeing him standing there with his eyes closed and a big smile on his face. He quickly opened his eyes in surprise. He hadn't meant to be so obvious about it. "Sorry, Mistress," he replied. "I was peeing." Mel smiled broadly. "By the look on your face, it must have felt pretty good." He nodded quickly as he once again began undressing. "Yes, Mistress, really good!" As soon as he was down to just his diapers and was laying on the floor for Mel to change him, she asked, "So you really do like wetting yourself?" "Yeah," he admitted. "More than I ever thought I would. It's funny," he mused, "it seems like with each day that goes by, I like it more and more. It's so strange." Mel said nothing as she listened to him. She recognized Gloria's hypnotic suggestions taking stronger and stronger root in him, even if he didn't - which she hoped he had no idea of at all! "Maybe it's because I haven't been able to have any kind of sex," he continued as she finished wiping his messy bottom. "What do you mean?" "I don't know. It's almost like it's the closest thing to a physical sexual feeling that I can have - with this damn contraption on me." She chuckled a bit. "How about the anal play you seem to be getting so fond of lately?" He shook his head and she could see the confusion on his face. "I just don't know about that. It's really strange. I don't know what to make of it." "Why not?" she asked as she pulled the first diaper into place and taped it closed. "I don't know. I guess it's just too new. And it's troubling." "Why?" she asked as she started on his second diaper. "It just is. It's not right!" He paused as she was finishing up. Then asked, "What do you think about it?" She looked at him and smiled. "I think you should get dressed and then let's go get a nice dinner together. We can talk about it more then." Once again, Mel drove them to the same restaurant they had been to every week before their therapy session. Chad hated going in there because she always made him drink from one of his baby bottles in front of everybody while they ate. He always got way too many embarrassing stares from the surrounding people and he wasn't looking forward to doing it again. After they were seated, the waitress came by and set some menus on the table for them and asked what they wanted to drink. "Would you like some coffee?" Mel asked him. "Yeah, that would be good for a change," he replied. He just wished he wouldn't have to drink it out of the baby bottle. But at least one cup of coffee would be less to drink than a large coke that would fill his bottle two or three times. "So, tell me about your day," Mel asked while they waited for their drinks. Chad told her a little, and they talked a bit. It was mostly light conversation and fairly comfortable... if not enjoyable. And Mel seemed to be interested in listening to him - which was really nice. When the waitress brought their coffee a few minutes later, Mel ordered a large steak dinner for him and a salad plate for herself. Chad didn't touch his coffee since he knew she would pour it into one of the baby bottles. But instead, she just took a sip from her own cup and asked, "So your boss likes how your project is going so far? Does he ever come down and make any suggestions in person?" Chad shook his head - why wasn't she pulling out a baby bottle? "No, he never comes down at all. It's more like he purposely ignores us down there. We hardly ever see him." She had still made no move to get a bottle. He took a chance and picked up the cup and drank from it. Good coffee. Real good! Especially without the bottle. But would she realize that he wasn't drinking from a bottle now? As he talked about his day, Mel felt the old bits of annoyance every time he mentioned Robin, but she had braced herself for it. Did he realize that she was purposely letting him drink from the cup instead of the bottle this time? She was betting on it. But tonight she just needed to talk comfortably with him for a while, and not requiring him to use one of his bottles for a change would be a big help. It was helping already. The more he talked, the more relaxed about it he seemed to be getting. And she herself seemed to be relaxing and enjoying what was starting to become a really nice and pleasant conversation about more than just his work. By the time their dinner came, Mel found herself telling him about her horrible date with Detective Grey. She hadn't planned on telling him, but she even admitted to trying to sleep with him and then throwing him out. They both laughed over it. As they shared a final cup of coffee after dinner, she realized that it was one of the nicest dinners she had enjoyed in a very long time. She had enjoyed talking with him. He wasn't one of those guys that was only interested in himself. He was intelligent, funny, and seemed to be interested in whatever she had to say. A far cry from Detective Grey. Why, oh why did he have to be a flake? She glanced at her watch and gave a short exclamation. "Oh God! We're going to be late!" Mel phoned Gloria as soon as they got into the car to tell her they were still coming and to wait. She apologized again as soon as they got there. "It's okay," Gloria told them. "I know little things sometimes happen." Mel and Chad quickly got onto their usual couches and tried to get into the right frame of mind, but having to hurry from the restaurant made that a bit more difficult. But as Gloria slowly and calmly guided them, they were both soon feeling very good. This time, Mel didn't worry about when she needed to stop listening, she knew that Gloria would let her know. The relaxation therapy felt so good to her. She missed her weekly sessions when she could go through it fully, but right now, Chad was more important. By the time that Gloria tapped her on the arm to stop following, she realized she had gotten more out of it than she had in a while now. Chad was floating. Wonderfully floating. His mind was calm and carefree, his body was so relaxed - sooo relaxed. And it felt sooo good! Good enough that his mind and body yearned for even more. Certain phrases that Gloria said seemed to echo stronger than ever in his mind. Wonderful phrases that seemed to help him reach stages of being relaxed that he had never imagined before. He mentally reached for her voice, yearning for the suggestions she was giving him. Gloria noticed the tiny changes in Chad as she talked - little things that only she would notice since she was looking for them. She had him under, but she had to take him further, much further. Slowly and surely, she guided him into deeper and deeper levels of trance. Soon she began giving him tiny suggestions, reminding him of the triggers she had set before to help him relax further. All the little phrases that she used that resonated so wonderfully in his mind. Such relaxing phrases. Phrases he wanted to hear her speaking over and over again in her wonderfully relaxing voice. Like she had done before, Gloria started reminding Chad about his love of wearing diapers and how much he loved wetting them. It was his dream to be incontinent. Such a great and wonderful dream. A dream he could touch. A dream that he could really have. She concentrated for a long time on how wonderful it felt every time he wet himself. Pleasure that would continue to get even better with each wetting. Fantastic pleasure. Sexual pleasure. Almost like an orgasm every time he wet himself. As she planted these suggestions, she was surprised to see the huge grin of pleasure on his face. Something in what she had said must have really been getting through to him. She suddenly noticed Mel waving her arm to get her attention. "It's working!" Mel mouthed silently. Gloria nodded that she understood and went back to work. Mel breathed in fully. Chad had no idea that he was being hypnotized during these sessions. And obviously, it was working. There was no way in the world that Chad could win this bet. As far as she could tell, he had already lost. As she had planned, Gloria once again put Chad through the same muscle tightening and relaxing exercise she had put him through last week, telling him whenever those muscles were tight that it felt awful and it was too difficult for him to do. It was so hard that it wasn't worth the trouble. But whenever he was relaxed, she told him how wonderful it felt. Relaxed was totally normal and it was really the way he wanted to feel. Over and over again she had him doing it, but each time having him hate tightening them a little bit more, until finally she suggested that he hated tightening them so much that he would no longer want to remember how to tighten them. And since it was no longer anything he had to worry about, he no longer needed to remember how to tighten them. It felt so much better to be relaxed. Those feelings that controlled his muscles didn't exist anymore. No matter what, he would not be able to tighten those muscles and he would not want to be able to tighten them. As she did last week, she started a slow countdown, telling him that when she got to one he would try to tighten those muscles again, but this time he wouldn't be able to. She started at five and when she got to one, she said, "Tighten those muscles now." She saw no reaction from him at all this week. "Are they tight?" she asked. "No," he replied calmly. "I didn't want to try." She quickly began praising and relaxing him all over again. Once again she began trying to deepen his trance, making sure he was under as far as she could take him. Then, once again, she asked him to concentrate on the feel of his wet diapers and find those same feelings from when he was a baby. She asked him to think back to that time and tell her as soon as he remembered. She had almost given up on this last week, but he had come through in the end. This week, he remembered a lot faster. Once again, she asked him to remember his mother and how he felt about her. Then she had him overlay feelings for "Mommy Mel" on top of those feelings - replacing them so that whenever Mel was happy with him, he would feel happy. But whenever she was angry, he would react exactly the way he had when he was a baby. Then she reminded him that he wanted to be a baby again so reacting to everything the way a baby would was only right and natural. And since he wanted it so badly, there was no reason he couldn't have it. He could be that baby again, and it would feel so good! Gloria had one last little thing to add to this session. "Chad," she said softly. "When you were that little baby before, did you suck on a pacifier?" It was a moment before he could answer. Gloria got the impression that he was trying to remember his long distant past. He finally nodded his head and said, "Yes." "Good," she replied. "How about your thumb?" Again he nodded and said, "Yes." "Good, Chad. Very good. Now I want you to remember what it felt like to suck on your pacifier or your thumb back then. You needed them, didn't you?" "Yes," Chad admitted rather flatly after another moment of consideration. "Good, Chad. You were supposed to need them. They made you feel calm and comfortable. They made you feel good. Chad, the next time you have a pacifier in your mouth, it's going to feel very comforting to you, just like it did when you were a baby the first time. You're going to find that you really like it. It makes you feel good to suck on it. Can you do that?" She saw him nod. "Good. Now you like being a baby again, don't you?" He nodded again. "Good. And babies like sucking on things, don't they?" He nodded. "So since you like being a baby, then I want you to feel really good that you like sucking on things. You like sucking on your pacifier, you like sucking on your bottles, you even like sucking on your thumb. Just like a very happy baby. And sucking on things is going to make you feel very happy and calm and relaxed. You won't notice it so much at first, but the more you suck on your pacifier, the more you're going to find that you like it, and the more you're going to want it. And if you don't have it with you, you'll have no problem with sucking on your thumb instead. Both of them are going to feel so normal, so wonderful, so calming to suck on - just like when you were such a happy little baby, and just like the baby you can be again." Gloria finally motioned Mel to lay back again as she started bringing Chad up slowly out of his trance, telling him all the while that his subconscious would remember everything, but he would have no conscious knowledge of ever being hypnotized at all. All too soon for Mel, it seemed like the session was over. For Mel, she felt better than she had in a while. She had no doubt that Chad was feeling far better though. Chad felt like he was almost in a dreamlike state as he followed Mel out to her car. As he walked, he felt himself wetting himself. Oh God it felt good! So very good! He loved wetting himself like that. It was amazing that the rest of the world didn't feel that way. He didn't really care, he loved it and that's all that mattered. Mel drove them towards her office, but she stopped at a drug store on the way. "Come on in with me," she said as she turned the engine off. "We've got to get you something." Chad was still feeling really good after the therapy session. He happily followed her into the store, for once worrying less about how he looked. Mel led them down one of the aisles and began looking at curling irons for his hair. She picked one out with a very slim barrel and showed it to him. "I think this should be perfect for you. Go ahead and buy it." "Me?" "Yeah, you need it." "I do?" "Yes. Now don't argue with me!" Chad did a slight double-take. Argue with her? That wasn't really his intention. Some of the feelings of relaxation quickly left him. "I'm sorry, Mistress," he said quickly as he dropped a quick curtsey to her right in the store. "I didn't know I needed one. That's all." Mel smiled at his curtsey. Oh, she loved this. "Then go pay for it so we can go home." Chad took the curling iron to the counter and paid for it, having to endure the strange looks from the woman behind the counter. It wasn't very hard for him to imagine what she must think about him. What man would be buying a curling iron? Especially a man dressed like he was. No, he had no doubt at all what the woman must think of him. Mel drove him back to her office where he got into his own car and followed her home. He carried his things directly up to her apartment. Then Mel sent him back to her car to get a box out of the trunk and bring it up. While he was doing that, she phoned Cassie and told her that they were finally home. Chad had just reached the top of the steps with the box when Cassie and Sandy came out of their apartment. "Hi Sissy," Sandy said as they followed him all the way to Mel's apartment. "Whatcha' got there?" "Something for Mel," Chad replied as he awkwardly opened the door with the box in his hands. "Mistress," he called out, "Sandy and Cassie are here." Mel came out of her bedroom a moment later. "Hi girls," she said with a big smile on her face. Then she turned toward Chad. "Set the box on my bed." Chad headed into her bedroom and was a little surprised to see all the women following him. He set the box on the bed for Mel and turned around, but he had to immediately move out of the way as Mel headed straight for the box. "Are you ready for this?" she asked Cassie and Sandy with a big smile on her face. She opened the box and reached her hands into the mounds of ruffles and pulled the garment out. She quickly turned around and held it out at arm's length for them to see. "Ta-daaaa," she sang excitedly. Cassie and Sandy both began squealing while Chad's legs suddenly felt like Jell-O. "Oh, it's too much!" Sandy laughed delightedly. "Too much is right!" Chad thought, unable to take his eyes off of what he now realized was a dress - a dress from his worst - and best fantasies. Except for the pink bodice, it was all huge white ruffles. The skirt on it stood almost straight out all around - way out! He didn't get time to think about it as Mel quickly ordered him to get undressed. She expected him to wear that thing? Yeah, of course she did. He took one last look at the "dress" and began to slowly remove his clothes. As he did so, he felt the one thing that he didn't want to feel - the bite of the little teeth inside of his chastity device. He turned around so that, momentarily at least, he wouldn't have to look at the dress. All three women were watching him carefully and expectantly as he removed his clothes. He should have felt self conscious, but by now they had all seen him naked and in so many humiliating situations that their stares meant nothing to him. But the thought of the dress he was about to have to wear did! His little chastity device simply wouldn't stop hurting. All too soon he had removed his shoes, shirt, and pants. Mel had him keep everything else on. She grabbed a few pairs of pantyhose from her dresser and quickly stuffed them into the cups of his girdle, instantly giving him the illusion of breasts once again. Chad saw her pull down the zipper in the back of the dress, then she held it out for him to take. As he reached for it, the pain from his chastity device increased. It had to be all those ruffles he thought. The damn thing just looked so sissyish! Almost babyish! The ruffles felt incredibly soft against his hands. The pink bodice was all satin with a big pink bow in the front. The pain from his device increased as he carefully stepped into the dress. As he pulled it up higher on his body, his legs were caressed all the way up by the mounds and mounds of ruffles that not only were the skirt, but that supported the skirt from underneath - very soft, very full, very sensual ruffles. The smooth satin of the rest of the dress soon hugged his body as he pulled his arms through it. His arms were suddenly enclosed in their own version of the soft ruffles to just below his elbows. Mel came around behind him and zipped the dress all the way up in back. He was soon tightly hugged by the smooth pink satin - contrasting wonderfully with the soft sensual ruffles. His chastity device was killing him now. He took one step and felt the ruffles all around him moving as the skirt bobbed up and down a bit. The pain from the device increased yet again and he reached to grab himself down there, doubling over to try to make the pain go away, but as he tried to grab himself, all he got were handfuls of ruffles. There were so many ruffles under his skirt, supporting it, that he couldn't even get his hands near the device. He hadn't even reached the plastic panties on top of his diapers! "I think he likes it," he heard Cassie remark. "Without a doubt," Mel replied. "Really?" Sandy laughed, "Was there ever any doubt?" All three women broke out into peals of laughter. Chad tried to deal with the pain of the chastity device, but nothing was working. The feel of the dress moving around him kept at him all too sensually. He knew he had to look totally ridiculous in the dress, and that made things that much worse. Even when he tried to stand up straight and stand still with his hands down at his sides it didn't work because the skirt of the dress stuck out so straight that his hands wound up inside the mounds of ruffles in his skirt. That was when he realized how short the skirt really was. While it stuck out really, really far, it didn't drop down very far at all. He had to wonder if it even covered his diapers! He had no way to see if it did. "Put your shoes back on, Sissy," Mel ordered. Chad had to sit down on the floor and grab his shoes. But getting them onto his feet was a nightmare because the skirt of the dress didn't even allow him to see his feet as he got them close enough to his body to slip them on. And buckling them was even worse. He had to keep pressing down on the mounds of skirt ruffles to get past them, but as he pressed down in one place, they just puffed up all the more somewhere else. And his chastity device was killing him! Arggghhh!!! The women all laughed through his entire ordeal of trying to get his shoes back on. "Okay, Sissy. Model for us," Mel ordered. Model? What was he supposed to do? He stood up and turned all the way around, then stopped and faced them again. "Walk back and forth, Sissy." Mel told him. "And swing those hips, girl," Sandy added. Chad did as he was told, heading a short way across the room, but every step he took only sent the skirt of his dress moving more and more, back and forth, and up and down. The darn thing felt incredible all around him. Embarrassingly incredible. Enough so that there were tears in his eyes now from the pain his chastity device was giving him. He could feel his cock inside of it trying to grow harder and harder with each step that he took - despite the pain. As he turned around to walk back towards the women, the skirt of the dress swished back and forth a few times, emphasizing the feel of the ruffles that seemed to encase him. He was suddenly thankful the dress didn't come down much lower where he could feel it more against his pantyhose covered legs, it would only make the sensations that much worse. But the feel of the dress moving around him was more than enough for him. He let out a small whimper as he felt his cock straining against the tiny confines of his chastity device. It could grow no more. The pain from the tiny teeth felt like fire burning all around where they pressed into him. It had been a long time since he had had any real relief, over a week now. A time filled with nothing but stimulation to his fantasies. Despite all the progress he had made in learning to control his erections, the darn dress foiled everything. As much as he didn't want to get hard, the dress was giving him no choice - and his chastity device was also giving him no choice. He was caught between the proverbial rock and a hard place. Two opposing forces that wouldn't relent. And the only result for him was pain. His knees bent together as he reached down desperately into the pile of ruffles that covered his front - a futile gesture that solved nothing. "Oh, there's no doubt that he likes it," he heard Sandy saying through his pain. "Poor guy," Cassie added. "What guy?" Sandy replied. All three women began laughing at him all over again. "Come along now, Sissy," Mel ordered. "Standing there like that isn't going to help you any. Let's see if maybe some work can take your mind off of your little problem." Chad tried his best to stand up straight again, but he didn't quite make it. Still bent over a little, he headed out to the living room to the tune of all three women chuckling at him all over again. "Dust the furniture for us, Sissy," Mel ordered as she followed behind him. "And make sure you do a really good job this time. And you'd better be extra careful not to mess up that dress while you're working!" Hissing silently through his teeth against the pain, Chad dutifully found her dust cloth and furniture polish and headed for the small table she kept by the front door. But as he got close to it, the skirt of his dress got there first. He stopped and reached out. He couldn't even touch the table without compressing the skirt in front of him. He heard more peals of laughter from the women behind him. He forced his way closer to the table, crushing the ruffles in front of him tighter against him. He moved some of the items on the table and then sprayed the bare wood. Then he began wiping it. But the wiping motion set the ruffles in his skirt moving all too furiously - which set off the women's laughter all too furiously. "More elbow grease!" Mel called from behind him. He rubbed harder at the table which only made his skirt move all that much more. His hard-on began raging again, but he did his best to continue working despite the pain. He was doing every little mental trick he could think of to try to make himself grow smaller, but the darn dress was foiling everything he tried. He seriously doubted that any of the women had any idea how difficult it was for him or how much pain he was in. Slowly, he moved on to the end table next to the couch, then to the rest of the furniture in the room. When he finished, Mel let him put the dusting tools away and he thanked her profusely. "Can I take this thing off now, please?" he asked, dropping a very serious curtsey - which only made all the women laugh again. "No, of course not," Mel replied. "We're enjoying watching you in it too much." Chad felt a bit deflated, all he really wanted was to stop the endless swirling of the dress and get his chastity device to stop hurting him - or to have an orgasm which would be even better - not likely though. Despite his predicament, a sudden thought hit him. "Mistress," he said dropping yet another curtsey, "please, I really need to get some of my laundry done tonight. May I get some of it started in the washer?" "No, Sissy," Mel replied. "We have company right now. Not till later." He understood, but he remained worried. Everything that was bothering him lately was things that he couldn't do anything about. He'd just have to remind her later. Mel turned to Cassie. "Any chance you can show him how to fix his hair properly now?" Cassie smiled. "Of course, I'd love to. Let's do it in the bathroom." She turned to Sissy. "Do you have your curling iron and brush?" Chad retrieved the curling iron he had bought earlier and pulled it out of the package. Then he found a brush that he had bought but never used in his purse. He wasn't really all that happy about what he was about to learn - yet there was also that tiny stimulating fascination about it too - which also didn't help his pain. In the bathroom, Cassie began showing him how to brush his hair properly, then pull out sections and wrap them around the curling iron. All over his head she had him pulling wide sections of hair, rolling them carefully around the hot iron, and heating them up. When he was done, she had him brush it all again lightly, smoothing it to where it should be. As he looked at himself in the mirror, he could see how much fuller and thicker his hair looked - not to mention how much more feminine. Way more feminine! It was so embarrassing - especially since he was learning to do it for himself. He thought he was also learning now to fight through the pain of the chastity device a little better. Or at least he noticed that the device wasn't hurting him quite so much now. He was just glad for anything that would decrease the pain. "Okay, Sissy," Mel ordered, "start cleaning the kitchen now." Chad headed for the kitchen, all too conscious of not only his dress, but how his hair felt on his head. Parts of it tickled him as he moved now, especially the bangs that brushed his forehead. As Sandy watched Sissy heading for the kitchen, she said, "Mel, if you've got a minute, I've got something I'd like to show you." "Sure, Sandy. What's up?" Mel asked. Sandy giggled and pulled a piece of paper out and headed for Mel's desk where she spread it out. Speaking softly so Sissy couldn't hear her, she said, "this is what I've come up with for when he stands in the corner." Mel looked carefully at the drawing on her paper. "It looks like an upside down bird perch - sort of - except for the wide sides on it." Sandy giggled. "Yeah, I guess it does, doesn't it. But I think it will work perfectly. I've designed it to be narrow enough that it will be just wide enough for his feet if he keeps them together. The higher sides will keep him from moving his feet from side to side and off the ends." "Good idea," Mel replied. "I didn't think of that." "So shall I have my carpenter get started on it?" "Yeah, Sandy. Definitely. Go for it!" As Chad worked around the kitchen, the pain from his chastity device finally subsided somewhat and he was really relieved. The dress was still all too sensual, but the pain had dulled his ability to enjoy the dress the way he would have liked to. Without realizing he was going to, he suddenly felt himself peeing as he got soft enough to do it. The sensation was pure heaven and he breathed a deep sigh of pleasure. About the time he finished wiping things down in the kitchen, Mel ushered Sandy and Cassie out the door. Chad was actually glad to see them go. As soon as Mel had closed the door and turned around again, he dropped as nice a curtsey as he could and asked, "Please Mistress, can I start my laundry now?" "No, Sissy," Mel replied. "Not tonight. It's getting too late." "But Mistress..." "I said not tonight!" "But..." "I said no!" "Mistress, I need..." "I don't want to hear it. Not tonight!" "But..." "No! Now I don't want to have to tell you again!" "What am I going to..." "I said I don't want to hear it!" Chad reluctantly shut up. What was he going to do? He had no clean pants left for work tomorrow. "Now let's get you changed," Mel said as she headed for the bathroom. Chad was ready to be changed, but he followed her reluctantly. He would have much rather done some laundry for himself... even if he had to do it while wearing that dress! Mel helped him out of his new dress and took it to her closet while he finished removing everything else he was wearing. Then she removed his wet diapers and cleaned him up. She inserted another suppository and put three fresh diapers on him again, followed by his plastic panties. "Let's get you home now," Mel said as she headed for her bedroom. Chad followed her into her bedroom, intent on picking up his pants that he had left in there earlier, but by the time he got there, Mel already had his pants and shirt in her hand and was heading back out into the living room. "Coming?" she asked. Chad turned around and followed her. He was hoping that she would carry his clothes bac