The Bet - Chapter 26 free porn video

The Bet by Karen Singer Chapter 26 (Wednesday - week 4) Small. Insignificant. Worthless. Pathetic. Again and again his dreams hammered home how he felt about himself. There were other emotions as well: unworthy, useless, stupid, perverted... defeated... unloved. He tossed and turned as much as his breast forms, chastity device, and overly bloated diapers would let him. Their constant confinement punctuated his dreams and increased his restlessness - as did the itchy irritation all across his backside from his diaper rash. Small, insignificant, pathetic. Unloved... Deserving of, and doomed to endure, the humiliation he felt even in his sleep... which now included the constant irritation and humiliation of diaper rash. Yet despite his feelings of self-pity, the images of himself wearing skirts and heels... and diapers, filled his dreams... and excited him beyond belief. They pulled him, over and over again, to the brink of waking up. And over and over again, still mostly asleep, he drifted back deeply into his dreams once again. Because even in his dreams, he knew he had no hope of relief - or even obtaining any of the pleasure he used to associate with those feelings of want and need. No hope. No feeling. Numb. Yet the need still resided throughout his entire body, driving his dreams relentlessly to show him, over and over again, the very things that fed his insatiable need. His unrelieved need was so great that it never let up. It was always present, at least in the background, of everything he could possibly dream. Unrelieved need. Raging excitement. All of it now leading to nowhere. No hope of the feelings he craved. No hope of relief. Only emotions that left him feeling nothing but insignificant and worthless. Restless sleep. The shocking volume of loud rock music pulled him out of one last dream where he had been crawling at the feet some unknown woman - who bore a striking resemblance to Mel. He opened his eyes, totally disoriented for a moment as the images of that powerful woman erased themselves from his mind. The feeling of self-pity lingered however as he stared uncomprehending at his blank ceiling. It was a moment before the irritating music made him realize that he had to do something about it. Wanting only blessed silence - and to go back to sleep again, he pulled himself to his feet where he could reach his pink clock radio and shut it off. The loud music suddenly ceased. Relief swept over him as silence returned. He glanced down at his blow- up mattress, wanting desperately to go back to it, but he was awake enough now to know that he couldn't do that. It was another day. Another horrible day. Another day of servitude and total humiliation - from which he couldn't escape. As he stood there, pondering his life and trying to make sense of it all, he felt himself suddenly wetting his already overly wet and messy diapers. Damn! Why didn't he realize he had to go? The answer was simple - it was because his body was still too much asleep. And if he didn't get moving and wake himself up fully, then it might happen again... or worse. And part of him really didn't care at all - because he didn't really mind wetting himself uncontrollably - he loved it in fact. But there were reasons out there that spelled out why he didn't want to do it. Reasons that at that moment he didn't care much about, but he knew he would care about them later. He suddenly realized that he had been unconsciously rubbing at the back of his diapers - trying desperately to quench the itch of the diaper rash that was invading his backside. But his diapers, even when dry, were far too thick for his rubbing to have any affect. And now... it was a totally useless motion. He concentrated on the itching under his soaked and messy diapers. It felt at least as bad as it did yesterday... possibly a bit worse. Probably because he had been wet and messy through most of the night. He gave one more wishful glance at his blowup mattress and forced himself to walk away from it, out of his bedroom and into his kitchen. Had Mel left him another note? Most of him hoped so, but part of him hoped that she didn't - because all too often her notes meant more humiliation for him. And he had enough of that in his life already. Her note was right where it always was, right on his counter where he couldn't miss it. It was very short. Three more bottles before he left for the morning, dress as usual, and one side note - from now on he had to include one of his waist cinchers as part of his normal everyday dress. Oh goody! Not! Still feeling nothing but self-pity and loathing for his life, he grabbed a bottle of Mel's foul tea from his refrigerator and carried it out to his one and only chair to sit and drink it. It wasn't till he tried to put the nipple into his mouth that he realized that he was still sucking on his pacifier. Damn! He just knew it was going to be one of those days! Mel woke up only minutes before her alarm buzzed. She turned it off before it could ring and swung her feet over the edge of the bed to sit on it. She breathed in deeply, feeling fairly good for once. She got to her feet and grabbed her robe, pulling it around her as she headed out to her kitchen. Fixing her morning coffee was so ingrained in her habits that she never gave it a moment's thought. Instead, her mind was filled with thoughts that revolved around Sissy... or rather Chad... no, definitely Sissy! She smiled at the thought of some of the things she and Cassie had researched on the internet last night... and she blushed at the thought of some of the things that Cassie had talked her into ordering later. Had she really spent money on them? And especially on one embarrassing thing in particular? What kind of woman was she? It was unthinkable! Yet as she pulled a fresh mug out of her cabinet to pour her coffee into, she chuckled to herself. Yes, she had really bought it... even though just thinking about it made her feel dirty... but in a way, excited too. With her coffee made, she poured herself a cup and carried it over to her desk. She sat in front of her laptop and took a sip. Mmmm. She powered up her computer and continued to sip at her coffee while she waited. She went into her email as soon as she could. Yes, there were the order confirmations. She opened each one, staring at the name of each item. Damn! She had really done it! She, the one who had always considered herself to be the "good" girl, had actually ordered each of those items. She checked the expected delivery dates on all of them. Since she was having them all delivered to her office so they wouldn't sit exposed on her doorstep all day, she figured they would all arrive either Monday or Tuesday... an eternity to wait. Her only problem with having the packages come to her office was Andrea. She was really too embarrassed by what would be in each package for Andrea to know about them. Was there any way she could keep it all secret? Of course there was - if she simply didn't tell Andrea what was in them. But Andrea was her friend too. In a way, it wasn't right. But in this case, it was probably more right to be closed-mouthed and not tell her... or more polite anyway. Had she really ordered this stuff? The proof was right there in the emails in front of her. And further proof would be hers as soon as the packages arrived. She couldn't wait! Chad was as naked as he was capable of getting as he stood in front of his closet and stared into it. What should he wear? Deciding what to wear was always a problem, but he hadn't counted on having a further dilemma today. While he had been in the shower, he had remembered that he only had one pair of pants left that he could wear this week. Only one pair of pants till next Monday! And it was only Wednesday! That would mean wearing skirts on Thursday, Friday, Saturday, and Sunday... four days in a row! But he could break that up a bit if he wore a skirt to work today instead of tomorrow. Would it be better? That was his dilemma. Should he? Or shouldn't he? Did he want to wear a skirt today - rather than tomorrow? Or not? The very thought of it, wearing a skirt to work again, made him nervous and scared - while at the same time it excited him immensely - which he didn't really need. In the end, his choice came down to deciding to wear one four days in a row, or three. He finally decided that four days in a row was a bit much, even for a real woman. So he turned his attention in his closet to only his skirts. But now, what skirt outfit should he wear? His frustration built as he stared at what he had. He just wasn't good at matching them up! He vowed that he'd ask Mel to help him with it later. But for now? He finally grabbed the same skirt and blouse outfit he had worn to work last Friday - only because he knew they were made to go together. With that decision out of the way, he tried to turn his thoughts back to getting ready for work, but he couldn't get the fact that he was actually going to be wearing a skirt to work again out of his mind. His diaper rash felt much the same to him as it had last night. Obviously the cream that Mel had bought wasn't doing much good. Of course he didn't know how long he had been laying in messy diapers all night. He had no recollection of messing them at all - as usual. He carefully coated himself very liberally with the new ointment he had bought yesterday, praying all the while that it would work - quickly! Two disposable diapers, one with the cover slashed to let the wetness through, covered his rash and chastity device a few minutes later. A pair of plastic panties with nursery print characters all over it covered the diapers. The waist cincher was next, followed by another one of his all-in-one girdles. The girdle was so small and tight that it constantly pulled hard on his shoulders. It was a chore just to stand up straight in it. His pantyhose would have been next, but he remembered how difficult they were to get on yesterday. He chose to work on his makeup and hair next instead, taking his time so as to delay both the ordeal with the pantyhose and the ordeal of wearing a skirt for the rest of the day - he still found it very hard to believe that he was about to go to work in one again. With his hair still slightly damp from his shower, he rolled section after section around his curling iron and let them "cook." Each time he removed the iron from his head, the hair sprang back into tight curls. Curls that spelled out "sissy" with each one that he created. But what was he going to do about it? It took a lot of time to do his entire head, but he was in no hurry. Sissy curls. Sissy curls. Sissy, sissy, sissy! He ignored the ever-present sexual urges that built up inside of him with each curl that he created as he worked to make himself even more of a sissy - because again, there was nothing he could do about it. With his hair out of the way, he turned to his makeup, covering his face with this and that. Spreading and blending. Adding color and texture. Removing - maleness. Finally, he was down to just needing his lipstick. He twisted the tube of lipstick open and was about to add it to his lips, when he paused and stared at himself in his bathroom mirror. The lipstick was the most blatant color he would be adding to his face. A close match to his super-long fingernails. Why was he doing this? Why was he deliberately showing the entire world how much of a sissy he was? It would have been easy to place the blame for that one on something like... because of the bet... or because Mel had ordered him to. But wallowing in self-pity as he had been all morning didn't let him see anything but the plain truth. And the truth was, he was doing it all, because he had dreamed of doing it all his life. He had always dreamed of wearing girly clothes. And he had also dreamed of being in diapers and being helpless and babied. They were strange, conflicting yearnings that didn't really belong together. Yet they all lived together deep inside of him. They had become so much a part of his very soul that it was impossible to separate his strange yearnings from the rest of him. Bottom line? He was doing it all because he wanted to. As much as he could try to deny it, the simple truth was that he was doing it all, because deep down, he really wanted to. He sighed and stared at the lipstick in his hand. There was no use delaying the inevitable any longer. Feeling even more self-pity, he applied his lipstick, blotted it, and stared at the results. Sissy! Battling with his pantyhose, actually proved to be a diversion from the thoughts that had invaded his brain while he had been doing his makeup. He had to fight to get the darn things on because his waist cincher wouldn't let him bend easily enough to get them over his feet. How did women deal with wearing waist cinchers? Dumb question... they usually didn't! It wasn't till after he got the pantyhose on that he remembered thinking yesterday about not wearing pantyhose today. Too late now! He wasn't about to try to take them off again - especially not after fighting so hard to get them on. He could delay it no longer. He grabbed the skirt and pulled it on, zipping it up at the side easily... too easily. Just as with his pants, the skirt hung a bit lower than he thought it would because of his compressed waist. But the skirt wouldn't drag on the ground the way his pants would, so he just left it to hang a bit below his knees. He pulled the matching top on and stared at his reflection in the mirror. Was it acceptable? He only hoped so. He decided to go for at least one bit of comfort and slipped into his low-heeled shoes, noticing as he did so how really nice they felt compared to wearing much higher heels every day as he had been doing. It was time for the finishing touches. He went in search of his jewelry. Mel glanced at her clock and was a bit surprised. Where had the time gone? She had just sat down at her computer to work for a bit because she had had an idea about one of the cases she was working on... but that tiny idea had become a bigger idea, then it had blossomed into other ideas and areas. Now she had to hurry. It was almost time for Chad... or rather Sissy to get there. She ran into her kitchen and quickly started preparing his baby-food breakfast. She had no doubt that he hated the stuff, but tough! She knew it humiliated him and she rather enjoyed watching him suffer through it. Besides, it certainly wouldn't hurt him. There was a small polite knock at her door. She glanced at her clock one more time as she ran to answer it. He was right on time. Good! She opened her door and got a bit of a surprise. While he was busy curtseying and greeting her, she noticed immediately that he was wearing a dress again. Wonderful! Although it was exactly the same outfit he had worn before. "Good morning, Sissy," she returned happily as she stood back out of the way to let him in. Chad entered her apartment and set his purse and diaper bag down in their usual places under the table by her door. Then he stood where she could "inspect" him. As she looked him over carefully, Chad couldn't help but notice the broad smile on her face, he figured it was because of the dress he was wearing. "You surprised me," Mel said, as she turned and walked off toward her kitchen. Chad immediately followed. "Why? Because I'm wearing a skirt again?" "You got it!" she replied with a wicked look back over her shoulder toward him. "But I'm also surprised that you're wearing the same outfit you wore last time. You've got lots of skirts and dresses in your closet. Why didn't you pick something different?" Chad shrugged. "I don't know what blouse goes with what skirt?" he replied with more than a bit of frustration. "What do you mean? You've got lots of possibilities there. We made sure of that when we were shopping." "Yeah, there's lots of stuff, but what can I wear with what?" Mel looked back at him as she continued to stir his baby cereal and just shook her head. She motioned toward his highchair. "Climb up." Chad took the tray off of his seat and set it on the floor, leaning it up against the chair. Then he climbed awkwardly up into it, trying to settle himself so his diaper rash wouldn't hurt too badly. Mel saw him wince and noticed his discomfort as she pulled one of his bibs out of a drawer. "Diaper rash still bad?" Chad sighed. "Yeah. It's no better than yesterday. Mistress, can't I go without the suppositories... at least just for a few days... at least till this rash clears up?" "No!" she answered flatly and final as she approached him with the bib. Chad didn't even try to protest any more as she tied the bib around his neck. A minute later, the highchair tray was back in place and he was spooning the first of many tiny spoonfuls of the cereal into his mouth. If she wouldn't let him go without the suppositories, then how was he going to clear up his diaper rash? He looked up at her as another idea hit him. "How about letting me have less bottles to drink for a few days? That might help." "No!" Again her answer was plain and simple and final. "Just give it time and keep putting that ointment on it. It will clear itself up soon." Chad made no answer as he spooned another tiny batch of the lousy cereal into his mouth. Mel wasn't going to budge - on anything. He had a feeling that he was going to be doomed to suffering with the diaper rash for a very long time - because so far, the cream they had been using had done nothing at all. Mel stood behind her counter and watched him struggling with the tiny baby spoon to get the cereal into his mouth. Mostly, he was succeeding now. He was getting better than he used to be at using the infant spoon. "So you need some help sorting out some outfits to wear?" He looked up. "Yes... please! I just don't have a clue." She chuckled, "We'll spend some time on it tonight." He actually felt relieved. She was going to help. But as he shoved more of the baby cereal into his mouth, he realized that feeling relieved over what she was going to be helping him with was really very odd. It was strange that he was happy because she was going to be helping him select skirts and dresses he could wear to work! And he would be wearing them to work... eventually! And while he was still scared about it, he was excited by the idea too. Damn he needed some relief! "Hi Chad," Robin's voice called breathlessly as she hurried past his cubicle. She was running a bit late... not that anyone would really care. But before she got fully into her own cubicle, she stopped short. Had she noticed his bare legs again as she walked past? She had the distinct impression that she did. Of course, she had been hurrying and had just barely glanced. With her arms still heavily loaded, she took a few steps backwards till she could just see into his cubicle again, and this time she quietly took a closer look. "Sissy! You're all dressed up again. And that's the same outfit you wore last week." Chad turned around at the sound of her voice. He was startled because he hadn't heard her come back. "Hi Robin," he replied as he felt himself blushing. He looked briefly down at himself. "Is there something wrong with this outfit?" he asked, still unsure of himself. She stared at him, totally surprised at his question. "You're a guy, who wear's nothing but women's clothes every day, and you're asking if there's something wrong?" She shook her head. "For what you are, it's great!" She shook her head one more time and walked back to her own cubicle so she could unload all the things she had been carrying. Chad stared after her. For what he was? What did she mean by that? He got up and followed her around to her cubicle. She had set a large pile of things down on her desk and was just opening her big bag as he got there. "What do you mean, for what I am?" he asked. She pulled her big mirror out of her bag to check her face, but before she could look into it, she stared at him instead, totally annoyed by his question. "What do I mean? Well look at you, for God's sake! Obviously, you're one of those stupid transvestite people. Only one who seems to carry things further than most that I've read about." She looked at him more carefully. "Or are you really... what do they call themselves... transgendered or something? One of those men who are actually trying to change what sex they are. Because that's what you seem to be!" Now it was Chad's turn to be surprised. "Me? Transgendered? Is that what you think?" "Well what else am I supposed to think?" she asked testily. "It's not exactly normal for a guy to suddenly turn up in women's clothes and then that's all he wears from then on." Chad shook his head. He supposed what she thought only made sense. No doubt it was probably the impression he gave everyone. But because of the bet, he had no choice in the matter. "That's not exactly it," he said softly. "So what is it?" she asked, still agitated. He shook his head again. "It's complicated. I don't want to talk about it." She almost threw the mirror in her hand at him. "Get out of here!" Chad quickly retreated back to his own cubicle. What was eating her today? Okay, maybe she had a right to be angry at him, but he still couldn't explain anything to her. The last thing he wanted anyone else to know was about the diapers he had on under everything else... or even about the bet itself! He supposed he'd just have to keep giving everybody the impression that Robin already had. He smiled to himself. It was somewhat true. He did like wearing women's clothes... deep down. It was totally humiliating... but he did like it. He turned and faced his computer. The email this morning had still not contained anything about the project they had been working on. So what was he supposed to do with himself again all day? He leaned back and laced his hands behind his head... and noticed his skirt, and his pantyhose covered legs. Damn! He was actually doing it again! He was actually wearing a skirt - at work! He still found it hard to believe. He stood up and looked down at his clothes. If he leaned over far enough, he could see past his breasts and the hem of his skirt all the way down to the tips of his shoes. He swung his hips back and forth a few times to watch the skirt swish around him. It was fascinating to see how it moved... not to mention how odd it felt against his legs. "What are you doing?" Chad jumped at seeing Robin leaning around the edge of his cubicle. He immediately felt his face blushing a deep red. What could he tell her? "I'm just trying to get a feel for how this skirt moves," he replied. Well, it was the truth... mostly. She nodded. "Yeah, I can see that." She came all the way into his cubicle. "By the way. I'm sorry if I sounded angry earlier, the baby had kind of a rough night last night." Chad nodded. "Didn't get much sleep?" "Not really." "Diaper rash bothering him?" Chad asked... hopefully. Robin looked at him strangely. "Diaper rash! Not on your life. That's easy to fix. No, sometimes he still gets colicky and he can't sleep. He cries for hours." "Oh," Chad replied. "Sorry to hear that." He really wanted to ask her about how she fixed her baby's diaper rash, but he chickened out. Instead, he looked back down at his skirt, then back up at her. "So is there really anything wrong with wearing this again?" She shook her head. "Of course not. It's just the same thing you wore last week - the last and only other time you wore a skirt to work. I just would have figured you'd wear something different this time. That's all." "Oh," he replied as he pulled on his top, stretching it back down into place again after the swishing back and forth he had just done. "The truth is, I didn't know what else to wear today." "And you didn't want to wear slacks like you usually do?" "Um," how could he put it without giving anything else away... "not today." "Well, just to be different, you might try getting a few more skirts and dresses... if you're going to be wearing them, that is." He shrugged his shoulders. "Actually, I've got quite a few." "So why did you wear the same thing again?" He shrugged his shoulders. "I've got several skirts and a bunch of tops, but I don't know how to mix and match them together." He looked down at what he was wearing again. "I know these go together so there's no problem." Robin looked at him trying to figure out if he was serious or not. He certainly seemed serious. When you bought your other clothes, didn't you buy things that you had some idea what you'd be wearing with them?" Chad shook his head. "Not really." He couldn't tell her that it was Mel who had picked out most of the things he had now... except for the few things he had had from before. Robin shook her head. "You might want to think about that the next time you're out shopping." "Yeah, I'll do that," he agreed sheepishly. It was a thought, knowing in advance what would go with what. Even when Mel was picking them out. He sat down again in his chair. But instead of leaving, Robin moved all the way into his cubicle and leaned against his desk. "So what other clothes do you have... women's clothes that is?" Chad raised his eyebrows at her question. The last thing he expected to be discussing with her was the contents of his closet. "Well," he began, trying to find a place to start. "Do you have a lot?" she asked, interrupting him before he could get started. He shrugged. In the last month, Mel had made him buy a lot more than he had ever planned on. "I guess," he replied. "Wait a minute then," Robin said just before she hurried out. She came back a moment later, pushing her chair ahead of her. "I may as well sit down while we talk. This should be interesting." Chad was a bit surprised by her forwardness, but he shrugged it off and began describing the contents of his closet - purposely leaving out his maid's dresses and anything else he didn't want her to know about. With every item he tried to describe, Robin grilled him for more information as to style and color and in some cases, who the designer was. But she quickly learned that Chad knew nothing at all about the clothes he had. He couldn't even describe the colors or the prints properly. "Geez, for a sissy, you really don't know anything," she declared at one point, thoroughly disgusted and frustrated with his lack of knowledge. "For a sissy?" "Well, yeah. Don't most guys like you know a lot about this stuff? I thought they did anyway." "Obviously not," Chad replied. Despite her comment, and despite the awkward topic for him, he suddenly felt like a bit more of a failure. "I mean... geez! A four-year-old girl knows more about her clothes than you do. It's like talking to a complete baby!" Chad was completely taken by surprise by her statement. Especially the part where she practically called him a baby. Worse, he knew she was exactly right... more right than she even realized. "Uh," he said, trying to find some way to reply. "Look," Robin said. "I've got an idea. We've got nothing better to do anyway." She disappeared for a few moments, then came back again with a handful of magazines. She set them on his desk in front of them. "Let's go through these together. I'll point to some pictures, and then you tell me if you have anything even remotely similar. Okay?" Her idea startled Chad a bit. It also embarrassed him some. But he agreed to go along with her suggestion - mostly because he was truly interested... deep down inside somewhere. Besides, he had a feeling she wasn't exactly giving him a choice in the matter. Robin flipped through the pages of the magazines, stopping often to point at pictures and comment about the clothes the model was wearing. Despite having nothing to really say about the pictures she was pointing at, Chad found this far more interesting than just looking at the magazines on his own. Then, something about a skirt in one of the pictures caught his eye. "Wait a minute," Chad said, leaning forward to peer at the picture more intently. He pointed to the skirt the model was wearing. "I've got one that's almost just like that. But mine doesn't have a belt like that one." Robin peered closer at the skirt he had pointed to... happy that he had actually been looking for clothes that were similar to what he owned. "Yeah," she said with a lot of interest. "That's a nice one. Nice color too. It looks like a basic A-line skirt. You could probably wear that with almost anything." Chad felt glad that he had finally found a picture that was similar to something that he had. As Robin kept turning the pages, he had to stretch his imagination a bit to relate the clothes that he owned to anything in the pictures. But the process was really made a lot more difficult because he didn't remember much about most of his newer clothes since the only time he had ever worn them was in the dressing room at the store. Yet he tried his best to find matches for Robin to see. It was a while later, that he realized how interested and comfortable discussing the clothes and the fashions he had become with Robin. Surprisingly comfortable. And dare he say it, he was really enjoying himself. Was he finally getting to the point where he could enjoy talking about feminine things... or possibly just engaging in normal "girl-talk" without being embarrassed by it? He seriously doubted it. In fact, he knew he wasn't. It was only the situation right there with Robin that made it seem comfortable for him. Robin closed the magazine they were looking at and leaned back. "I need some coffee!" she declared. "Let's go get some." Chad checked his watch. It was just getting close to everyone's break time. "No thanks. Everybody will be heading to break right now." Robin looked at him and rolled her eyes. "Oh come on! Everybody's seen you in that dress before anyway." Chad shook his head. "No thanks." Robin stood up, then stopped. "You're being stubborn and stupid again," she declared. She reached out and grabbed his arm and pulled. "Come on! You're going whether you like it or not!" "Robin... No!" he replied, resisting her efforts to pull him out of his chair. "Look, if you don't go willingly with me, then I'll get everybody to come back here and drag you down there again!" "You wouldn't!" "I did it before, didn't I?" Chad looked up at her in horror. "You would, wouldn't you!" "You better believe it!" He shook his head. There was no winning with women... anytime. "I'd rather not," he said... trying to get out of it one more time. "Get up and walk!" she ordered as she pulled again on his arm. "Ugh!" he grunted in total frustration as he got out of his chair. He was heading for yet more humiliation that he didn't really need just then - or anytime for that matter. As he walked beside Robin toward the break room, he was more aware than ever of his exposed legs and the looseness of his skirt as it lightly brushed his legs. Just the fact that he was again wearing a skirt at work embarrassed him and made him feel extremely self-conscious. Despite the fact that his skirt was actually comfortable to wear, he felt very uncomfortable in it. He wasn't used to showing his legs in public like that - especially at work... around all too many people that he knew. He felt silly and embarrassed doing it. He realized that even though the pants he wore now were all women's pants, they brought him a lot of comfort just in the fact that his legs weren't so exposed. He was overly conscious of his skirt and his legs all the way to the break room. But halfway there, he was also aware that the humiliation from what he was wearing was again fueling his unrelieved sexual needs. Damn! And the closer he got to the break room and the people he imagined that would be there, the worse it got. He hated it! Yet he loved it! And his nervousness grew along with his sexual excitement as the break- room came into sight. Nervously, he entered right alongside Robin, as if she could somehow protect him from some of the humiliation he knew he was in for. There were a few people already in the break room, pouring coffee or sitting together at the tables. Chad followed Robin to the coffee pot, then to Robin's delight, further down where they each grabbed one of the donuts that were still left. Chad did his best to not look around the room while he got his refreshments... he didn't want to see who might be staring at him. But as soon as he had a donut in his hand, he had no choice but to turn and look around the room for empty places to sit. He wanted badly to go back to his desk, but instead he meekly followed Robin over to the large table where all the women congregated. As he and Robin started in on their donuts, they were joined by more and more women, who all seemed to make a point of saying "Hi Sissy," a lot louder than he liked. Of course, he knew they were all just trying to be friendly - friendly that is, if being a friend meant humiliating him. As they talked, Chad noticed other people in the break room out of the corner of his eye. He glanced quickly at them, then just as quickly glanced away. They were his friends too... or they used to be. They were the men who would no longer talk to him... not that he wanted them too. At least they all respected him enough to stay away from him - totally. He really couldn't blame them. If he were in their shoes, he wouldn't go anywhere near someone like him at all either. He couldn't help glancing quickly at some of the men in the room again. He inadvertently locked eyes with a man over by the coffee pot - a friend he had known very well... before. He saw his former friend scowl at him and purposely turn away, walking quickly out of the room. Chad couldn't blame him a bit. Seeing his reaction only made him feel that much worse about his situation than he already did. But unfortunately, there was nothing he could do about it. The conversation around him brought him back to where he was. It took him a moment to realize that Robin was telling everybody about what they had been doing all morning. Oh great! "Girl, you need some accessories!" one of the women declared. "It ain't about what top you wear with what skirt... it's all about what you dress it all up with!" As she said it, she pulled on her long necklace with one hand and held her other hand out, proudly showing off the rings covering each of her fingers. The women all laughed. "I don't have many... accessories - yet," Chad replied. The woman laughed. "You come shopping with me sometime, Honey. I'll find you lots of interesting things you can wear." Chad rolled his eyes a bit. "I have no doubt!" Fortunately, everyone around him, including the woman laughed heartily. "By the way," the woman continued, "how come you don't wear any earrings? I'm surprised by that, 'cause even guys are wearing them these days." Chad was totally surprised by the question. "I guess because I don't have any," he replied. "Why? You got something against them?" "No, not at all. I just don't have any... yet." The woman smiled and nodded her head. "Yet! You got to at least have the basics, girl. Now it's none of my business, but I'd think that someone like you would at least own a pair of earrings." "Um... maybe soon," Chad replied. Actually, he had mixed feeling about earrings. Yes the thought of them excited him greatly, but at the same time, earrings would be like another nail in his coffin. And he wasn't sure he really needed that. But should he get some? It was certainly a question worth considering... or dreaming about, which would be safer. As they talked, Chad still felt very awkward around the women, especially trying to talk about the things they were discussing - which was mostly clothes... and him! Girl-talk. It was so inviting. Yet he still couldn't bring himself to get fully into it or even allow himself to enjoy it. He had to wonder yet again, at what point in a sissy's life is it okay to just relax and let go... and truly let yourself enjoy something like girl-talk. At what point? He wanted to... he just wasn't there yet. Mel closed the cover of the folder she had been working in and set it aside on her desk. She picked up the next folder to work on and paused. She was working hard. Was Chad? What was he doing today? He had said that he still didn't have the go-ahead to get back to his project yet. Was he and the Robin woman spending all their time together again? The thought of it disturbed her. To take her mind off of it, she opened the folder in front of her and plunged back into her own work. But it didn't last. All she could see in her mind was Sissy and Robin talking together. Sissy, sitting and staring into the eyes of the beautiful, young Robin woman. She couldn't stand it! She closed the folder in front of her again and stared at, hardly seeing it. How could she keep him from spending all his time with Robin while he was at work? The problem was that he was supposed to be working with Robin. But they weren't working. Not just then anyway. Maybe that was the solution. She couldn't do anything about giving Robin any work that would keep her away from Sissy, but maybe she could give Sissy some work that would keep him away from Robin! But what? The hallways were crowded as Chad and Robin walked back to their desks from the break room. Chad still did his best to not look at any of the men, he was too embarrassed about himself for that. He was embarrassed about being seen by the women too, but somehow they didn't seem so bad to him just then. As he sat down in his chair again, he noticed that the irritation from his diaper rash didn't feel quite as bad as it did earlier. Was it finally clearing up? He could only hope. He glanced at his computer and noticed an email had come in. He opened it. "Oh Roooobiiiin," he called over the cubicle wall. "Check your email!" A minute later, he heard Robin's voice exclaim over top of the wall, "Finally!" Chad walked around to her cubicle where she was just reading the email. "It took them long enough," he declared as he walked in. But Robin was intent on reading the details of the email and didn't answer right away. "Did you read all of this though?" "Not yet," he answered. "They not only liked what we did, but now they're asking for more... a lot more!" "Okay," Chad replied as he leaned over her shoulder to read her screen. "I guess we're suddenly busy again." "I would say so," Robin replied. Mel paused while typing the email message and glanced at her watch, it was lunchtime... a little past actually. Darn! Chad wouldn't even be at his desk now. But that really wasn't a problem. He'd get his instructions as soon as he got back. She finished typing her email to him and hit the send button. There! That should do it! With a smile, she closed her computer and got up from her desk, wondering if Andrea would like to go to lunch with her for a change. Chad pulled into the parking lot at the gym feeling happier than he had all day. He wasn't happy because of what he was wearing. He was happy because he was definitely sure his diaper rash wasn't as bad now. It was still there, just not so bad. Even all the wetting he had done that morning hadn't made things worse. Now if he could just convince Cassie to not give him one of those suppositories... He walked through the door into the gym and was immediately greeted by the receptionist who called out, "Hello Sissy," all too loudly - and with a far bigger grin on her face than he was happy about. He immediately dropped a quick curtsey and said "Hi." Then he waited till she found Cassie for him. He again repeated his curtsey and greeting for Cassie, then followed her back to their usual private office. "How's your rash today?" she asked, as he began undressing and she was closing the blinds. "I think it's starting to get better now," he replied. "Well, that's good," she said. "It looked pretty bad yesterday. Chad waited until he had struggled to get his pantyhose off, then his girdle off before he asked. "Look, is there any way we can please skip the suppository today? The rash is getting better, but the mess from the suppository will only make it worse again." She looked at him and smiled. He had the distinct impression that she just might go along with him for once. "Nope! Sorry. Mel's instructions." His hopes were dashed once again! Cassie spent very little time working on the front of him - there just didn't seem to be any point in it anymore. Since the chastity device prevented her from touching his penis directly, he wasn't going to get any kind of a reaction at all as she worked on him there. He got very little of his bottle finished by the time she had him roll over onto his back and pull his knees up under him... exposing himself shamefully for her attentions. Attentions that he was now rather looking forward to - as long as she didn't mess with his diaper rash too much. As she carefully spread the ointment sensually over his red and blistered bottom, her hands still felt wonderful. Yes, the diaper rash was definitely better today - since he was getting that much pleasure from her rubbing her hands over it. Even still, she didn't spend long on it before he again felt the cold, hard tip of her toy playing with his asshole once again. He braced himself for it, and felt her pushing it into him, slowly... ever so slowly today. She was teasing him with it. He wanted to push himself forcefully onto it... impale himself fully. But this time, he restrained himself. He didn't push back at all. He simply waited and let her push it slowly into him, then pull it back again, then push it a bit further... teasing him with it. She was doing all the work today, not him. He closed his eyes and gave himself to the sensations he was feeling. Why did he have to love this so much? It wasn't right! It was wrong! Wrong! Wrong! He mentally sighed. It did no good to berate himself. He loved it, and that was all there was to it. He just did. But as Cassie played with him, the stimulating feelings grew inside of him. They finally reached a point where he could no longer be just the passenger. He had to have more! He finally pushed back, then pulled away, then pushed again... faster and faster... harder and harder... searching, desperately trying to find enough feeling and sensation to get over the hump - the hump that would grant him sexual release. But it just wasn't to be. No matter how hard he fucked himself against her toy, he just couldn't get there. He finally stopped, totally frustrated. He felt her pulling the toy out of him, then inserting her finger in him once again, pushing the suppository way up inside of him as far as her finger would go. He prayed that for once it wouldn't do anything so his rash could continue to get better. But he knew all too well what would probably happen. As she pulled her finger out again, he opened his eyes. In his present position, he could just barely see his chastity device. His penis inside of it was no bigger than it ever was anymore. Not one bit bigger. Since Mel had put the new teeth into the device, his penis stayed smaller and more insignificant than ever - always. It had to, or the pain would be awful. As he rolled over so Cassie could continue diapering him again, he tried to remember the last time he had felt any pain from those teeth - last night when Mel had dressed him in that ridiculous baby dress. The pain had been horrendous. He had no choice but to try to ignore his feelings of sexual stimulation so he could always remain small. Not just small, but tiny. And now, because he couldn't ever get hard, and because he was loving the sensations from his asshole so much, he was starting to associate that area of his body with pleasure instead of his penis. It was like another small blow against him to realize that his penis was now becoming totally useless to him for anything except to pee out of. No pleasure from it at all. No reaction from it could be allowed at all... no matter what stimulation they threw at him. More and more of his pleasure was coming from his asshole instead. Mel was slowly stripping yet another male trait away from him. And once again, the very thought of it thrilled him sexually inside... there was just no reaction from the very place where there should have been one... his penis. He picked his baby bottle back up again and sucked on it while Cassie finished with him. He barely registered what she was doing, his thoughts instead were locked on his more than ever useless appendage. Less of a male. More and more... less of a male. Mel seemed to be slowly winning the battle, at least in some areas. But how about the one big area that the bet was centered around - total incontinence? The thought of it made him realize that he had to pee again. He held it - purposely, even though most of him wanted to just give in completely. She had stripped everything else away from him anyway, why not just give up? Part of him wanted to, but another part of him made him still hold on. That part was still fighting back. Lost in his thoughts, laying on the floor in only his diaper, he was slow to finish his bottle. Self-respect, friends, and a life... not to mention relief... if he could still get any. He remembered how he had been last night, sitting in Sandy's living room, crying and sucking his thumb. He had lost so much. He had no choice but to fight back! He sucked harder on his bottle to finish it faster so he could get out of there now. Cassie was sitting there watching him, waiting on him. He finally began dressing again while he continued to finish his bottle. He had to fight back! Self-respect, friends, and a life! Chad sat in his seat again, gingerly, but still easier than he had before. His diaper rash was definitely improving. Robin wasn't back yet so he opened up the spreadsheet that he used to track his progress for the bet. Next to yesterday's date, he filled in twenty-six minutes. Only one minute longer than he had managed the day before. It was progress, but certainly not much. He promised himself he would try a lot harder today. He checked the number of days still to go - thirty seven. Still more than a month. An eternity in some ways. Yet it gave him more time to build up his strength at holding back. The only thing that really worried him was all the progress that Mel had made against him already in other areas. Surprising progress. Would he be able to keep his control - the control that would let him win the bet? He knew himself well. His body always regained everything quickly. But would he be able to make it? As far as the bet went, he was sure he could do it. His bigger question now was the other areas, especially his more and more useless penis when it came to sex. Would he ever get full use of it back too? That was a more troubling question. He noticed an email waiting for him so he opened it. He was surprised to see that it was from Mel. What did she want now? Sissy, Since you seem to have so much free time on your hands, I want you to put it to good use. You said you're having trouble deciding on outfits to wear. I want you to write me a fifteen hundred word paper - all about fashion and mixing clothes for different occasions. I expect you to email it to me before you leave work this afternoon. You can research everything on the internet. Do it, and don't disappoint me! Chad couldn't believe it - a fifteen hundred word paper? Something like that would probably take him all afternoon, and then some. He reread the email again, then went back to the first sentence. He realized that Mel thought the approval for his project hadn't come through yet. With a smile he opened a return message to Mel and explained that he and Robin now had the approval on their project and he was going to be too busy to do the paper for her. He happily pushed the button to send the message back to Mel. Then he put her whole paper out of his mind. One less thing to worry about! Half an hour later, he was busy working on part of the project, when he saw another email come in. He paused in his work to open it and was not surprised to see that it was from Mel. He was surprised however at the contents. Sissy, I don't care if you think you're busy. I gave you an assignment and you better carry it out - no matter what! If not, then your diaper rash will be giving you far greater torment - for a very long time! Chad stared at the email totally aghast. Far greater torment? He had no doubt that she'd whip him severely for not doing her assignment. He closed the email and deleted it. A fifteen hundred word paper. And he had no choice. He would have to do it... probably before he did anything else for his job... or more likely, he'd have to do it while he was doing his job - both things at the same time. He only hoped that Robin wouldn't notice what he would be doing. He held up his hands and stared at the long claws that were his fingernails. He was going to have to type an awful lot with those claws. It would take forever! His nails gave him even more reason to hate doing Mel's "assignment." With a dejected sigh, he opened up his web browser to start doing research. Only a few minutes later, his afternoon suppositories kicked in. As usual, he didn't bother to fight against the inevitable. What would be the use? He'd only be making himself more miserable. As the mess gradually slid out of him and around his diaper covered backside, his primary thoughts were not so much the paper he was writing for Mel, or even the work he was supposed to be doing for his job, he was mostly thinking about his diaper rash and how much worse it was about to get. It was the middle of the afternoon. Chad had his head buried in his computer screen, reading and rereading what he had already written for Mel. Surprisingly, he had managed to write quite a bit, almost enough already. But the truth was, despite how much he had written, he really hadn't learned anything. As far as he could tell, you could mix almost anything with anything else. It all depended on what "look" you wanted. He thought quite a bit about his personal "look." Actually, he wasn't sure he even had a personal "look" yet. He just did whatever Mel told him to do. Did she want him to develop his own look now? He hoped not. All his research had only confirmed that it wasn't as simple or as cut and dried as it seemed. However, it did seem interesting... all those different styles of clothes. It really looked like so much fun. As he looked at the many pictures, he often wondered what it would be like to dress and look like so many of those models. The old feeling of jealousy reared its head again because he wasn't born female and couldn't ever possibly have a body like they did. Sigh! "Hey Sissy, it's break time," Robin's voice called from the entrance to his cubicle. Suddenly panicked, Chad quickly minimized the report he had been writing for Mel so Robin couldn't see it. Had she seen it? He hoped not. He turned to face her. "I don't think I want to go right now," he replied. "I've got too much to do." "Oh come on. We don't exactly have a deadline on this stuff. You don't have to try to get it all done today." Chad smiled, more so because it sounded like Robin hadn't seen what he had been working on for Mel. "Yeah, I know. But sometimes when I'm going good, I don't want to stop." It wasn't exactly the truth, but things did go that way sometimes. Fortunately, he saw Robin smile in return. "I know what you mean. Have at it then." Chad was ever so glad she had agreed this time and wasn't going to drag him down for more humiliation. He expected her to leave, but she didn't. Instead, her face suddenly looked quizzical. "Hey Chad, I heard you doing an awful lot of typing today with those nails of yours. More than I've ever heard you type like that before. What's up?" Shock and fear ran through him. Of course his nails had made a lot more noise on his keys. He should have realized that Robin would have heard it. "Um..." He searched for an explanation. "Sometimes I have a lot of code to type. Today was one of those days. That's what I meant when I said I was going good and need to keep at it." It was a total lie, but it sounded good to him. In fact, it really could have been the truth - under other circumstances. "Oh, that makes sense," Robin replied. She smiled and finally said, "See ya'." And she was gone. Chad breathed a small sigh of relief as she left. He turned back to his computer and brought up his paper for Mel and started finishing it. Overall, the paper had gone faster than he had expected, but he was glad to be almost done with it now. He was surprised at how adept he was becoming at typing with his stupid long nails. In fact, it had actually been kind of fun... in a way. Well, different anyway. As he worked, he suddenly realized that he had to pee again. "Geez!" he thought. "It seems like I just went." As he glanced at his watch to start timing himself, he thought back through the afternoon. Despite having very little to eat and drink for lunch as he usually did now, he had been peeing more often. Much more. And as he thought back through the entire day, he realized that he had been peeing more often all day. Why? Having no answer, he went back to finishing up his paper for Mel. It didn't take him long to finish it, and with a few happy clicks of his mouse, he emailed it to Mel. He leaned back in his chair, happy to be done with it so he could get back to work... not to mention so that he could stop worrying about Robin finding out what he had been doing. The pressure on his bladder was getting fairly intense, but he held on tightly. "Hey Chad," Robins voice suddenly interrupted his thoughts. He looked up to see her standing at the entrance to his cubicle once again. "Yeah?" "We were talking during break, and everyone wants to know what kind diet you're on. We're all pretty impressed with how much weight you've lost... and so quickly." "What diet I'm on?" he asked, horrified at the question. Yes, he had lost a lot of weight since the bet had started, but he couldn't really explain to Robin why it looked like he had suddenly lost so much more weight. He didn't want to tell her at all about his waist cincher, or about how most of his meals had been nothing but baby food lately, or about a thousand other things. But he needed an answer. "Um..." he thought for a moment. "Like I said before, it's really just a lot of basics. Plus I'm not eating as much as I did before." "What basics?" Robin asked. "Well..." Chad thought for a moment. The pressure on his bladder was getting more severe. And then two thoughts hit him at once. The first was an answer to Robin's question, and the second was that the reason he was peeing more today was probably because of the darn waist cincher pushing against his bladder. He tackled Robin's question. "I got this new cookbook, all about diet cooking, and I've been doing a lot of that lately." "Really?" Robin asked excitedly. "Which book?" Chad told her. "Is it really that good?" He glanced down at his body in answer. "I guess it's working better than I thought it would." "How bad are the recipes? I mean how do they taste?" Chad smiled. "Most of them are really good. But a few..." he shook his head. "Isn't that the way it always is? Well, I got to tell you, they're sure working for you. Everyone was pretty impressed with how you're looking. You really should have been there this afternoon." Chad smiled once again. For once he had had a better excuse to avoid the humiliation. "No thanks. Besides, I did get a lot done while you were gone." "Glad to hear it," Robin replied with a smile. Then she rolled her eyes, "All that clicking from those stupid long fingernails of yours on the keys was about to drive me crazy!" It wasn't till very late in the afternoon that Mel had a chance to check her email and read the paper that Chad had sent her. She didn't really care much about the contents, she had been more interested in keeping Chad away from Robin. But did it? She could only hope so. It seemed like he had finished it fairly quickly, and overall, it was mildly disappointing, telling her that he really didn't know much about fashion - even after doing the paper. But that hadn't been her main goal anyway. She had told him that she would spend some time with him tonight, sorting out some outfits that he could wear to work. She'd discuss it more with him then. But sorting out outfits wasn't the only thing she had planned for tonight. She sat back in her chair and closed her eyes... and smiled. Yes, she was definitely looking forward to later. Opening her eyes again, she quickly began typing an email to him, relaying her instructions for the evening. Chad drove home with only one main thing on his mind - getting out of his wet and messy diapers and getting cleaned up! He had been peeing more than usual all day. He realized now that that was because of the waist cincher and all the extra pressure it was keeping on his bladder. At least the total amount that he had peed didn't seem to be any worse than usual. Not as far as he could tell anyway. He was just doing it more often. Mel's instructions for the evening were exactly what he had expected - get cleaned up and into his uniform and get dinner started. For once, he was looking forward to a normal evening, one where he wouldn't be subjected to humiliation after humiliation - he hoped. Mel unlocked her apartment door and opened it to the smell of something delicious cooking. Even before she stepped inside, she closed her eyes and breathed in the delicious smell fully. "Mmmm." Continuing in, she dropped her purse and laptop bag on the table by the door and walked into the kitchen. Sissy was there, in uniform of course, working on dinner. His back was to her as he was working at the stove. "Smells good," she said as a way of announcing herself. Chad turned his body as he was in the process of tasting some sauce from the wooden spoon in his hand. He quickly dropped the spoon back into the pot and turned around. Dropping a curtsey as he was supposed to, he said, "Welcome home, Mistress." Mel smiled with delight. Oh how she loved this! "How's dinner coming?" she asked. "Almost done. Just a few more minutes." "No hurry," she replied with a small wave of her hand as she turned and walked out. "Just let me know when it's ready." As she walked off, she thought again about Chad. Yes, he was really getting to be perfect. A man... a man that she was forcing to act more and more totally like a woman... all the time. And not just a woman, but her maid! And... the darn guy was a great cook! Yes, perfect! And the thought of it sent a small wave of sexual excitement though her... which immediately set her to thinking about - later. Mel savored the flavor of the food in her mouth - delicious! Her eyes were focused mostly on Sissy who was standing as usual in his corner, on his bar. He hadn't moved hardly at all the whole time she had been eating. He was really getting much better at it. She wondered briefly what he must think about as he stood there with nothing else to do and no other stimulation at all. Not her problem. But it was certainly her delight to see it. With her meal finally done, she picked up her drink and wandered into the living room. Instead of releasing him, she selected a chair where she could sit and watch him better. She had no doubt he knew she was no longer at the table. But she was pleased to see him not moving anyway. Did the bar he was standing on hurt as much as she thought it did? He was certainly tolerating it well enough. She thought again about his fantasy of being trained so that he could wear nothing but high heels all the time. Should she do it? His perch was certainly good training for that. Just keeping him in heels all the time would probably do it. But heels weren't practical shoes for a maid and the work a maid needed to do. But was his work that difficult anyway? Would it matter? She really wasn't sure. It was something she'd have to think about a bit more. Chad stood on his perch with his eyes closed, trying extra hard to not move at all. He had heard Mel come out and sit down near him... he guessed anyway. Why wasn't she releasing him? There was work to be done. Dishes to clean. Not to mention the fact that he was getting really hungry. Just eating baby food for breakfast, then a really light lunch had left him very hungry. And he hadn't eaten a lot of solid dinners lately. Baby food just wasn't very satisfying. Come on, Mel. Release me! His toes were aching from standing on the bar. His calf muscles were aching from standing on the bar. He wanted to move his feet and legs so badly, but the damn bar prevented that. His whole body wanted to move, but he dared not, especially with Mel so close by. Come on, Mel! Release me! He suddenly felt the need to pee again. Timing himself wasn't really an option just then since he couldn't glance at his watch, so he let it out. Pleasure, pure pleasure. Not to mention a brief distraction from his corner predicament. Unfortunately, it was too brief a distraction. "Okay, Sissy, get your dinner." The words were like a gunshot, breaking the silence in the room and actually startling him a bit. But they were very welcome words. He painfully extricated himself from his corner perch and flexed his ankle and leg muscles a bit before heading back into the kitchen. He pulled his dinner out of the refrigerator and carried it over to the table and set it down. He might have had to keep it in the refrigerator while Mel was eating so it would no longer be hot, but even cold, it would be a very welcome change from all the baby food he had eaten lately. Very much aware of Mel's scrutiny, and knowing she wouldn't approve of him sitting at the table with it, he pulled the tray off of his highchair, climbed up into it, and pulled the tray back in place. But with the big tray in the way, locking him into the chair, he couldn't reach his plate of food that he had left on the table. "Um... Mistress," he called. "I seem to have a problem." Mel got up from her chair and headed toward the kitchen mildly amused. "Aw... Does the baby need some help?" "Yes, please." He felt so childish sitting in the highchair, unable to even put his own dinner on the tray in front of him. Mel picked up his plate and set it on the highchair tray so he could start eating. But instead of going back into the living room, she chose another chair at her table to sit down where she could watch him. His hands and face were quickly becoming a mess since he had to eat everything with only his fingers. He quickly looked more juvenile than ever, despite the fact that he was wearing his maid's dress instead of one of his more babyish outfits. She felt a slight tingling in her sexual regions just from watching him. Later, later, later... but not much later. She doubted she could hold out that long. "So did you get to spend much time with Robin this afternoon?" she asked. That was the primary question on her mind. Did her assignment do the one thing she wanted it to? He looked at her, his face and hands incredibly messy from his din